TWI863879B - Dye composition - Google Patents

Abstract

The subject of the present invention is to provide a dye composition that can dye fibers into various hues at high concentrations and has excellent dyeing fastness to light, sublimation, washing, etc., a fiber dyeing method, a fiber obtained by dyeing by the dyeing method, and a compound. The present invention provides a dye composition comprising at least one of the compounds of general formulas (A) to (G) and a non-ionic dispersant, a fiber dyeing method, a fiber obtained by dyeing by the dyeing method, and a compound.

Description

Dye composition

The present invention relates to a dye composition, a fiber dyeing method, a fiber dyed by the dyeing method, and a compound.

Polyolefin resins such as polypropylene resin and polyethylene resin are crystalline thermoplastic resins with excellent properties such as low price, easy processing, high strength, high chemical resistance, high friction resistance, high bending resistance, light weight, low moisture absorption, low thermal conductivity, and high anti-static properties.

On the other hand, polyolefin resins are high molecular weight compounds whose main chains and side chains are all composed of hydrocarbons. They have low affinity and compatibility with conventional dye compounds and do not have functional groups that are effective for chemical reactions. Therefore, it is considered extremely difficult to dye them at high concentrations and with high fastness.

Therefore, most of the colored polyolefin resins on the market are prepared by adding colored pigments during the manufacturing stage of polymer particles, etc., and then spinning, forming, etc. are performed to form the desired shape.

This coloring method requires the color to be determined at the initial stage of the resin product manufacturing process. In addition, if cost-effectiveness is considered, it is necessary to produce more than a certain amount of one color, resulting in limited freedom in color selection.

Furthermore, when changing the color of a resin product, it is necessary to replace the previous color of the colored resin remaining in the resin product manufacturing device with the next color of the colored resin, which will generate a large amount of waste resin and cause problems such as wasting time and energy.

As described in non-patent document 1, polypropylene resin and polyethylene resin are four major general-purpose synthetic resins along with polyvinyl chloride resin and polystyrene resin, and are used in a wide range of fields.

However, the use of polypropylene resin and polyethylene resin as synthetic fibers is very limited.

The reason is believed to be that, as mentioned above, it is extremely difficult to dye polypropylene resin fibers and polyethylene resin fibers with high concentration and high fastness, and the only effective coloring method, namely the solution coloring method using colored pigments, requires that the single yarn fiber density be increased and the freedom of color selection is limited.

Prior to this, in order to dye polyolefin resin fibers by water-based dyeing, attempts were made to change the molecular structure of the dye. Patent documents 1 to 5 proposed dyes for dyeing polyolefin resin fibers.

Patent Document 1 describes a production example of a red dye and a violet dye obtained by introducing a phenoxy group having an alkyl group or a cycloalkyl group having 3 to 12 carbon atoms as a substituent into an anthraquinone-based dye, and an example of dyeing polypropylene resin fibers using the same.

However, it is difficult to dye polyolefin resin fibers with these anthraquinone red dyes or anthraquinone violet dyes at high concentrations. Furthermore, regarding the form of the dyes used for dyeing, it is described that these anthraquinone red dyes are dissolved in alcohol or acetone as an organic solvent and used, which is not environmentally friendly.

Patent Document 2 describes a production example of a blue dye obtained by introducing a phenoxy group having an alkyl group, cycloalkyl group or halogen group having 1 to 9 carbon atoms as a substituent into an anthraquinone-based dye, and an example of dyeing polyester fibers, polyamide fibers and polyolefin-based resin fibers using the same.

However, it is difficult to dye polyolefin resin fibers with these anthraquinone blue dyes at high concentrations, and there is no specific description of the dyeing fastness of the dyed products obtained. Furthermore, regarding the form of the dyes used for dyeing, it is described that these anthraquinone blue dyes are dissolved in alcohol or acetone as an organic solvent, which is not environmentally friendly.

Patent Document 3 describes a production example of a blue dye obtained by introducing a phenoxy group having an alkyl group having 1 to 9 carbon atoms or a halogen group as a substituent into an anthraquinone-based dye, and an example of dyeing a polyolefin-based resin fiber using the same.

However, it is difficult to dye polyolefin resin fibers with these anthraquinone blue dyes at high concentrations, and there is no specific description of the fastness of the dyed products obtained. Furthermore, regarding the form of the dye used for dyeing, it is described that these anthraquinone blue dyes are ground together with a suitable dispersant such as sodium dinaphthyl methanesulfonate, but the specific grinding method is not described. In addition, as another form, it is described that the dyes are dissolved in alcohol or acetone as organic solvents, etc., and it is difficult to say that they are environmentally friendly.

Patent Document 4 describes an example of dyeing polyolefin resin fibers using a blue dye obtained by introducing an alkylamine group or a cycloalkylamine group into the α-position of an anthraquinone dye.

However, it is difficult to dye polyolefin resin fibers with these anthraquinone blue dyes at high concentrations, and there is no specific record of the fastness of the dyed products obtained.

Patent Document 5 describes a production example of a red dye obtained by introducing a phenoxy group having two substituents selected from the group consisting of a sec-butyl group, a sec-pentyl group, and a tert-pentyl group into an anthraquinone-based dye, and an example of dyeing a polypropylene resin fiber using the same.

However, it is difficult to dye polyolefin resin fibers with these anthraquinone red dyes at high concentrations, and there is no specific description of the dyeing fastness of the dyed products obtained. Furthermore, regarding the form of the dye used for dyeing, it is described that these anthraquinone red dyes are used in a slurry state, but there is no description of the specific method for producing the dye slurry. In addition, as another form, it is described that the dye is dissolved in dimethylformamide as an organic solvent and then used, which is difficult to say that it is environmentally friendly.

Patent Document 6 describes the production examples of monoazo dyes having long-chain alkyl groups and the dyeing examples of fine denier polyester fibers using the same. However, there is no description of dyeing polyolefin fibers using the same. Furthermore, regarding the form of the dyes used for dyeing, it is described that the monoazo dyes are used in a slurry state using an appropriate dispersant, but there is no description of the specific production method of the dye slurry.

In addition, in order to improve the dyeability of polyolefin resin fibers, various studies have been conducted on the modification of polyolefin resin fibers.

As modification techniques, various techniques are known, such as blending with dyeable resin components such as polyester, copolymerization with vinyl monomers having dyeable groups, blending with dyeing accelerators such as stearic acid metal salts, etc.

Although the dyeability of these modified polyolefin resin fibers is improved, there is a problem that the yarn strength is reduced due to the dyeing process, and the strength becomes insufficient when used in clothing and the like.

If a method of dyeing polypropylene resin fibers and polyethylene resin fibers with high concentration and high fastness is put into practical use, it will be possible to dye uncolored, low-cost ordinary yarns with small single-filament yarn density without limiting the color value, and it is expected that new uses will be developed in fields requiring higher design, such as clothing or vehicle interior materials, where polypropylene resin fibers and polyethylene resin fibers are not currently used. Previous technical literature Patent literature

Patent document 1: Japanese Patent Publication No. 38-10741 Patent document 2: Japanese Patent Publication No. 40-1277 Patent document 3: Japanese Patent Publication No. 41-3515 Patent document 4: British Patent No. 872,882 Patent document 5: US Patent No. 3,536,735 Patent document 6: Japanese Patent Publication No. 55-152869 Non-patent document

Non-patent literature 1: Yamamoto Hiroshi, Journal of the Fiber Society, 61 (2005), 319-321.

[The problem that the invention wants to solve]

Therefore, the purpose of the present invention is to provide a dye composition that can dye fibers into various hues at high concentrations and has excellent dyeing fastness to light, sublimation, washing, etc., a fiber dyeing method, fibers obtained by dyeing using the dyeing method, and a compound. [Technical means to solve the problem]

The present invention is a dye composition comprising at least one of the compounds of the following general formulae (A) to (G) and a non-ionic dispersant.

Formula (A)

[In formula (A), _XA represents a nitro group, _YA represents a halogen atom, _RA1 , _RA2 and _RA3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 and _RA3 is an alkyl group having 4 to 14 carbon atoms), and _RA4 represents an alkyl group having 1 to 4 carbon atoms]

Formula (B)

[In formula (B), R _B1 , R _B2 and R _B3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms)]

Formula (C)

[In formula (C), _XC and _YC represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, or a hydrogen atom and a hydrogen atom; R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms)]

Formula (D)

[In formula (D), _XD and _YD each independently represent a hydrogen atom, a halogen atom, or a cyano group, _RD1 represents an alkyl group having 1 to 14 carbon atoms, and _RD2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN (wherein at least one of _RD1 and _RD2 is an alkyl group having 4 to 14 carbon atoms)]

Formula (E)

[In formula (E), _XE and _YE each independently represent a halogen atom, and _RE represents an alkyl group having 4 to 18 carbon atoms]

Formula (F)

[In formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms]

Formula (G)

[In formula (G), _RG represents an alkyl group having 7 or 10 to 18 carbon atoms]

Furthermore, the present invention provides a fiber dyeing method, which includes the step of using the dye composition of the present invention to dye the fiber in an aqueous manner.

Furthermore, the present invention provides a fiber dyed by the dyeing method of the present invention.

The present invention also provides a compound of any one of the following general formulas (A) to (G).

Formula (A)

[In formula (A), _XA represents a nitro group, _YA represents a halogen atom, _RA1 , _RA2 and _RA3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 and _RA3 is an alkyl group having 4 to 14 carbon atoms), and _RA4 represents an alkyl group having 1 to 4 carbon atoms]

Formula (B)

[In formula (B), R _B1 , R _B2 and R _B3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms)]

Formula (C)

[In formula (C), _XC and _YC represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, or a hydrogen atom and a hydrogen atom; R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms)]

Formula (D)

[In formula (D), _XD and _YD each independently represent a hydrogen atom, a halogen atom, or a cyano group, _RD1 represents an alkyl group having 1 to 14 carbon atoms, _RD2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN (wherein at least one of _RD1 and _RD2 is an alkyl group having 4 to 14 carbon atoms)]

Formula (E)

[In formula (E), _XE and _YE each independently represent a halogen atom, and _RE represents an alkyl group having 4 to 18 carbon atoms]

Formula (F)

[In formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms]

Formula (G)

[In formula (G), _RG represents an alkyl group having 7 or 10 to 18 carbon atoms] [Effects of the invention]

The dye composition of the present invention can dye fibers into various hues at high concentrations, and the dyed products have excellent fastness to light, sublimation, washing, etc.

The inventors of the present invention have found that dyes containing the following specific compounds have improved affinity for fibers and can dye fibers at high concentrations into various hues, thereby completing the present invention.

<Compounds of general formula (A) to (G)> The compounds of general formula (A) to (G) contained in the dye of the present invention are as follows.

Formula (A)

[In formula (A), _XA represents a nitro group, _YA represents a halogen atom, _RA1 , _RA2 and _RA3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 and _RA3 is an alkyl group having 4 to 14 carbon atoms), and _RA4 represents an alkyl group having 1 to 4 carbon atoms]

Formula (B)

[In formula (B), R _B1 , R _B2 and R _B3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms)]

Formula (C)

[In formula (C), _XC and _YC represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, or a hydrogen atom and a hydrogen atom; R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms)]

Formula (D)

[In formula (D), _XD and _YD each independently represent a hydrogen atom, a halogen atom, or a cyano group, _RD1 represents an alkyl group having 1 to 14 carbon atoms, and _RD2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN (wherein at least one of _RD1 and _RD2 is an alkyl group having 4 to 14 carbon atoms)]

Formula (E)

[In formula (E), _XE and _YE each independently represent a halogen atom, and _RE represents an alkyl group having 4 to 18 carbon atoms]

Formula (F)

[In formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms]

Formula (G)

[In formula (G), _RG represents an alkyl group having 7 or 10 to 18 carbon atoms]

In the above formula (A), formula (C), formula (D) and formula (E), the halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and suitable examples include a fluorine atom, a chlorine atom and a bromine atom.

In the above formulae (A) to (D), the alkyl group having 1 to 14 carbon atoms may be, for example, a linear or branched alkyl group having 1 to 14 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, iso-pentyl, sec-pentyl, t-pentyl, 2-methylbutyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, and 1-ethyl-1-methylpropyl. As the above alkyl group having 1 to 14 carbon atoms, an alkyl group having 1 to 12 carbon atoms is preferred, and an alkyl group having 1 to 8 carbon atoms is more preferred.

In the above formula (A), the alkyl group having 1 to 4 carbon atoms may be, for example, a linear or branched alkyl group having 1 to 4 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc. The alkyl group having 1 to 4 carbon atoms is preferably an alkyl group having 1 to 2 carbon atoms, and more preferably an alkyl group having 1 carbon atoms.

In the above formulae (A) to (D) and (F), the alkyl group having 4 to 14 carbon atoms may be, for example, a straight-chain or branched alkyl group having 4 to 14 carbon atoms, such as n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, iso-pentyl, sec-pentyl, t-pentyl, 2-methylbutyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, and 1-ethyl-1-methylpropyl. The above alkyl group having 4 to 14 carbon atoms is preferably an alkyl group having 4 to 12 carbon atoms, and more preferably an alkyl group having 4 to 8 carbon atoms.

In the above formula (E), the alkyl group having 4 to 18 carbon atoms includes, for example, straight-chain or branched-chain alkyl groups such as n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, iso-pentyl, sec-pentyl, t-pentyl, 2-methylbutyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, and 1-ethyl-1-methylpropyl. As the above alkyl group having 4 to 18 carbon atoms, an alkyl group having 4 to 12 carbon atoms is preferred, and an alkyl group having 8 to 12 carbon atoms is more preferred.

In the above formula (G), the alkyl group having 7 to 18 carbon atoms includes, for example, straight-chain or branched alkyl groups having 7 to 18 carbon atoms, such as n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1,1-dimethylpentyl, 2,2-dimethylpentyl, and 3,3-dimethylpentyl. The alkyl group having 7 to 18 carbon atoms is preferably an alkyl group having 11 to 18 carbon atoms, and more preferably an alkyl group having 15 to 18 carbon atoms.

<Compounds of general formula (A)>

Formula (A)

Compounds of the general formula (A) In the formula (A), _XA represents a nitro group, _YA represents a halogen atom, _RA1 , _RA2 and _RA3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 and _RA3 is an alkyl group having 4 to 14 carbon atoms), and _RA4 represents an alkyl group having 1 to 4 carbon atoms.

The compound of the above formula (A) is a blue dye compound.

In the above formula (A), _YA is preferably a bromine atom from the viewpoints of dyeing density, light fastness, sublimation fastness, etc.

Furthermore, in the above formula (A), from the viewpoints of dyeing density, light fastness, sublimation fastness, etc., it is preferred that _RA1 , _RA2 and _RA3 are each independently an alkyl group having 4 to 14 carbon atoms, or _RA1 and _RA2 are each independently an alkyl group having 4 to 14 carbon atoms, and _RA3 is an alkyl group having 1 to 4 carbon atoms, or _RA3 is an alkyl group having 4 to 14 carbon atoms, and _RA1 and _RA2 are each independently an alkyl group having 1 to 4 carbon atoms.

Furthermore, in the above formula (A), from the viewpoints of dyeing density, light fastness, sublimation fastness, etc., it is preferred that Y _A is a bromine atom, _RA1 , _RA2 and _RA3 are each independently an alkyl group having 4 to 14 carbon atoms, or _RA1 and _RA2 are each independently an alkyl group having 4 to 14 carbon atoms and _RA3 is an alkyl group having 1 to 4 carbon atoms, or _RA3 is an alkyl group having 4 to 14 carbon atoms and _RA1 and _RA2 are each independently an alkyl group having 1 to 4 carbon atoms.

<Compounds of general formula (B)>

Formula (B)

Compounds of Formula (B) In Formula (B), R _B1 , R _B2 and R _B3 each independently represent an alkyl group having 1 to 14 carbon atoms, wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms.

The compound of the above formula (B) is a blue or purple dye compound.

In the above formula (B), from the viewpoints of dyeing density, light fastness, sublimation fastness, etc., it is preferred that _RB1 , _RB2 and _RB3 are each independently an alkyl group having 4 to 14 carbon atoms, or _RB1 and _RB2 are each independently an alkyl group having 4 to 14 carbon atoms and _RB3 is an alkyl group having 1 to 4 carbon atoms, or _RB3 is an alkyl group having 4 to 14 carbon atoms and _RB1 and _RB2 are each independently an alkyl group having 1 to 4 carbon atoms.

<Compounds of general formula (C)>

Formula (C)

Compounds of the general formula (C) In the formula (C), _XC and _YC represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, or a hydrogen atom and a hydrogen atom, and R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms).

The compound of the above formula (C) is a red or purple dye compound.

In the above formula (C), from the viewpoints of dyeing density, light fastness, sublimation fastness, etc., _XC and _YC preferably represent any combination of a hydrogen atom and a chlorine atom, a bromine atom and a nitro group, a bromine atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, or a hydrogen atom and a hydrogen atom.

In the above formula (C), from the viewpoints of dyeing density, light fastness, sublimation fastness, etc., it is preferred that _XC and _YC represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, a hydrogen atom and a hydrogen atom, and R _C1 , R _C2 and R _C3 are independently an alkyl group having 4 to 14 carbon atoms, or R _C1 and R _C2 are independently an alkyl group having 4 to 14 carbon atoms and R _C3 is an alkyl group having 1 to 4 carbon atoms, or R _C3 is an alkyl group having 4 to 14 carbon atoms and R _C1 and R _C2 are independently an alkyl group having 1 to 4 carbon atoms.

<Compounds of general formula (D)>

Formula (D)

Compounds of the general formula (D) wherein X _D and Y _D independently represent a hydrogen atom, a halogen atom, or a cyano group, _RD1 represents an alkyl group having 1 to 14 carbon atoms, and _RD2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN (wherein at least one of _RD1 and _RD2 is an alkyl group having 4 to 14 carbon atoms).

The compound of the above formula (D) is an orange or red dye compound.

In the above formula (D), from the viewpoints of dyeing density, light fastness, sublimation fastness, etc., it is preferred that _XD represents a hydrogen atom, a chlorine atom or a bromine atom, and _YD represents a hydrogen atom, a chlorine atom, a bromine atom, or a cyano group.

In the above formula (D), preferably, _XD and _YD each independently represent a hydrogen atom, a halogen atom, or a cyano group, _RD1 represents an alkyl group having 4 to 14 carbon atoms, and _RD2 represents an alkyl group having 4 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN.

<Compounds of general formula (E)>

Formula (E)

Compounds of the general formula (E) In the formula (E), _XE and _YE each independently represent a halogen atom, and _RE represents an alkyl group having 4 to 18 carbon atoms.

The compound of the above formula (E) is an orange dye compound.

In the above formula (E), from the viewpoint of dyeing density, light fastness, sublimation fastness, etc., _XE and _YE preferably represent a chlorine atom.

In the above formula (E), from the viewpoints of dyeing density, light fastness, sublimation fastness, etc., it is preferred that _RE is an alkyl group having 4 to 12 carbon atoms.

In the above formula (E), from the viewpoints of dyeing density, light fastness, sublimation fastness, etc., it is preferred that _XE and _YE represent chlorine atoms, and _RE is an alkyl group having 4 to 12 carbon atoms.

<Compounds of general formula (F)>

Formula (F)

Compounds of the general formula (F) In the formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms.

The compound of the above formula (F) is a purple dye compound.

In the above formula (F), from the viewpoints of dyeing density, light fastness, sublimation fastness, etc., it is preferred that _RF1 and _RF2 each independently represent an alkyl group having 4 to 12 carbon atoms.

<Compounds of general formula (G)>

Formula (G)

Compounds of the general formula (G) In the formula (G), _RG represents an alkyl group having 7 or 10 to 18 carbon atoms.

The compound of the above formula (G) is a yellow dye compound.

In the above formula (G), from the viewpoints of coloring density, light fastness, sublimation fastness, etc., _RG is preferably an alkyl group having 11 to 18 carbon atoms.

<Method for producing the compound of general formula (A)> The method for producing the compound represented by the above formula (A) is described.

The compound represented by the above formula (A) is obtained by coupling a diazo compound of a 4-nitroaniline derivative represented by the formula (aD) (in the formula (aD), _XA represents a nitro group and _YA represents a halogen atom) with a compound represented by the formula (aC) (in the formula (aC), _RA1 , _RA2 and _RA3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 and _RA3 is an alkyl group having 4 to 14 carbon atoms), and _RA4 represents an alkyl group having 1 to 4 carbon atoms).

(i) Diazotization of the compound of formula (a-D) First, the compound of formula (a-D) is diazotized in an inorganic acid or an organic carboxylic acid using a nitrosating agent or nitrosylsulfuric acid in the presence of additional water as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. Examples of the inorganic acid include hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is a nitrite of an alkaline metal, such as sodium nitrite in a solid state or in an aqueous solution.

The reaction temperature of the diazotization is preferably -10 to 40°C, more preferably 0 to 40°C.

Furthermore, the compound represented by formula (a-D) is generally widely used as a raw material for azo disperse dyes.

(ii) Coupling with a compound of formula (a-C) For example, a solution of a diazo compound of formula (a-D) is added to a solution or suspension of a compound of formula (a-C) in an alcohol (e.g., methanol) at a temperature range of -5 to 10°C to obtain a compound of formula (A).

The pH value of the solution or suspension of the compound represented by formula (a-C) is preferably weakly acidic. Adding a buffer such as triethylamine or sodium acetate is advantageous in the coupling reaction.

The water content of the compound of the general formula (A) may be within a range capable of producing an aqueous dispersion, for example, it may be adjusted to 60% by mass or less, preferably 40% by mass or less for dyeing.

(iii) Method for producing the compound of formula (a-C) The compound of formula (a-C) as a raw material can be produced by the following method.

Using N,N-dimethylformamide (DMF) as a solvent, a compound represented by formula (a-C1) (in formula (a-C1), _RA4 represents an alkyl group having 1 to 4 carbon atoms) and a carboxylic acid halide represented by _RA3 -COX ( _RA3 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom) are reacted to obtain a compound represented by formula (a-C2).

Next, the compound represented by formula (a-C2) is nitrated using concentrated nitric acid and concentrated sulfuric acid to obtain the compound represented by formula (a-C3).

The compound represented by formula (a-C3) is reduced using tin in a hydrochloric acidic alcohol (such as methanol) to obtain a compound represented by formula (a-C4).

Using DMF as a solvent, the compound represented by formula (a-C4) is reacted with alkyl halides represented by _RA1 -X and _RA2 -X ( _RA1 and _RA2 are independently alkyl groups with 1 to 14 carbon atoms, and X is a halogen atom) to obtain formula (aC). Alternatively, the compound represented by formula (a-C4) can be reacted with alkyl halides represented by _RA1 -X ( _RA1 is an alkyl group with 1 to 14 carbon atoms, and X is a halogen atom), and then _RA2 ( _RA2 is an alkyl group with 1 to ₁₄ carbon atoms) can be introduced according to a known reaction. For example, _RA2 can be introduced using ( _RA2 ) _2SO4 .

<Method for producing the compound of general formula (B)> The method for producing the compound represented by the above formula (B) is described.

The compound represented by the above formula (B) is obtained by coupling a diazo compound of 3-amino-5-nitro-2,1-benzoisothiazole represented by the formula (bD) with a compound represented by the formula (bC) (in the formula (bC), _RB1 , _RB2 and _RB3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of _RB1 , _RB2 and _RB3 is an alkyl group having 4 to 14 carbon atoms)).

(i) Diazotization of the compound of formula (b-D) First, the compound of formula (b-D) is diazotized in an inorganic acid or an organic carboxylic acid using a nitrosating agent or nitrosylsulfuric acid in the presence of additional water as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. Examples of the inorganic acid include hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is a nitrite of an alkaline metal, such as sodium nitrite in a solid state or in an aqueous solution.

The reaction temperature of the diazotization is preferably -10 to 15°C, more preferably -5 to 10°C.

Furthermore, the compound represented by formula (b-D) is generally widely used as a raw material for azo disperse dyes.

(ii) Coupling with a compound of formula (b-C) For example, a solution of a diazo compound of formula (b-D) is added to a solution or suspension of a compound of formula (b-C) in an alcohol (e.g., methanol) at a temperature range of -5 to 10°C to obtain a compound of formula (B).

The pH value of the solution or suspension of the compound represented by formula (b-C) is preferably weakly acidic, and the addition of a buffer such as triethylamine or sodium acetate is advantageous in the coupling reaction.

The water content of the compound of general formula (B) may be within a range capable of producing an aqueous dispersion, for example, it may be adjusted to 60% by mass or less, preferably 40% by mass or less for dyeing.

(iii) Method for producing the compound of formula (b-C) The compound of formula (b-C) as a raw material can be produced by the following method.

Using DMF as a solvent, m-nitroaniline is reacted with a carboxylic acid halide represented by _RB3 -COX ( _RB3 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom) to obtain a compound represented by formula (b-C1).

Next, the compound represented by formula (b-C1) is reduced using tin in a hydrochloric acidic alcohol (such as methanol) to obtain a compound represented by formula (b-C2).

Using DMF as a solvent, the compound represented by formula (b-C2) is reacted with a halogenated alkyl represented by _RB1 -X and _RB2 -X ( _RB1 and _RB2 independently represent an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom) to obtain formula (bC).

Alternatively, the compound represented by formula (b-C2) may be reacted with a halogenated hydrocarbon represented by _RB1 -X ( _RB1 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom), and then _RB2 ( _RB2 represents an alkyl group having 1 to 14 carbon atoms) may be introduced according to a known reaction. For example _{, RB2} may be introduced using ( _RB2 ) _2SO4 .

<Method for producing the compound of general formula (C)> The method for producing the compound represented by the above formula (C) is described.

The compound represented by the above formula (C) can be obtained by coupling a diazo compound of a 4-nitroaniline derivative represented by the formula (cD) (in the formula (cD), _XC and _YC represent any combination of a hydrogen atom and a halogen atom, a halogen atom and a nitro group, a halogen atom and a cyano group, a cyano group and a cyano group, a nitro group and a cyano group, or a hydrogen atom and a hydrogen atom) with a compound represented by the formula (cC) (in the formula (cC), R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 or more carbon atoms)).

(i) Diazotization of the compound of formula (c-D) First, the compound represented by formula (c-D) is diazotized in an inorganic acid or an organic carboxylic acid using a nitrosating agent or nitrosylsulfuric acid in the presence of additional water as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. Examples of the inorganic acid include hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is a nitrite of an alkaline metal, such as sodium nitrite in a solid state or in an aqueous solution.

The diazotization temperature is preferably -10 to 40°C, and more preferably 0 to 35°C. Furthermore, the compound represented by formula (c-D) is generally widely used as a raw material for azo disperse dyes.

(ii) Coupling with a compound of formula (c-C) For example, a solution of a diazo compound of formula (c-D) is added to a solution or suspension of a compound of formula (c-C) in an alcohol (e.g., methanol) at a temperature range of -5 to 10°C to obtain a compound of formula (C).

The pH value of the solution or suspension of the compound represented by formula (c-C) is preferably weakly acidic, and the addition of a buffer such as triethylamine or sodium acetate is advantageous. The water content of the compound of general formula (C) can be within the range capable of producing an aqueous dispersion, for example, adjusted to 60% by mass or less, preferably 40% by mass or less for dyeing.

(iii) Method for producing the compound of formula (c-C) The compound of formula (c-C) as a raw material can be produced by the following method.

Using DMF as a solvent, m-nitroaniline is reacted with a carboxylic acid halide represented by R _C3 -COX (R _C3 represents an alkyl group having 1 to 14 carbon atoms, and X is a halogen atom) to obtain a compound represented by formula (c-C1).

Next, the compound represented by formula (c-C1) is reduced using tin in a hydrochloric acidic alcohol (such as methanol) to obtain a compound represented by formula (c-C2).

Using DMF as a solvent, the compound represented by formula (c-C2) is reacted with a halogenated alkyl represented by _RC1- X and _RC2- X ( _RC1 and _RC2 independently represent an alkyl group having 1 to 14 carbon atoms, and X is a halogen atom) to obtain formula (cC).

Alternatively, the compound represented by formula (c-C2) may be reacted with a halogenated carbon represented by R _C1 -X (R _C1 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom), and then R _C2 (R _C2 represents an alkyl group having 1 to 14 carbon atoms) may be introduced according to a known reaction. For example, (R _C2 ) ₂ SO ₄ may be used to introduce R _C2 .

<Method for producing the compound of general formula (D)> The method for producing the compound represented by the above formula (D) is described.

The compound represented by formula (D) is obtained by coupling a diazo compound of a 4-nitroaniline derivative represented by formula (dD) (in formula (dD), _XD and _YD each independently represent a hydrogen atom, a halogen atom, or a cyano group) with a compound represented by formula (dC) (in formula (dC), _RD1 represents an alkyl group having 1 to 14 carbon atoms, _RD2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted with CN; wherein at least one of _RD1 and _RD2 is an alkyl group having 4 to 14 carbon atoms).

(i) Diazotization of the compound of formula (d-D) First, the compound represented by formula (d-D) is diazotized in an inorganic acid or an organic carboxylic acid using a nitrosating agent or nitrosylsulfuric acid in the presence of additional water as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. Examples of the inorganic acid include hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is a nitrite of an alkaline metal, such as sodium nitrite in a solid state or in an aqueous solution.

The diazotization temperature is preferably -10 to 40°C, and more preferably 0 to 30°C. The compound represented by formula (d-D) is generally widely used as a raw material for azo disperse dyes.

(ii) Coupling with a compound of formula (d-D) For example, a solution of a diazo compound of formula (d-D) is added to a solution or suspension of a compound of formula (d-C) in an alcohol (e.g., methanol) at a temperature range of -5 to 10°C to obtain a compound of formula (D).

The pH value of the solution or suspension of the compound represented by formula (d-C) is preferably weakly acidic, and the addition of a buffer such as triethylamine or sodium acetate is advantageous.

The water content of the compound of general formula (D) may be within a range capable of producing an aqueous dispersion, for example, it may be adjusted to 60% by mass or less, preferably 40% by mass or less for dyeing.

(iii) Method for producing the compound of formula (d-C) The compound of formula (d-C) as a raw material can be produced by the following method.

Using DMF as a solvent, aniline is reacted with a halogenated alkyl group represented by R _D1 -X and R _D2 -X (R _D1 represents an alkyl group having 1 to 14 carbon atoms, R _D2 represents an alkyl group having 1 to 14 carbon atoms or an alkyl group having 1 to 14 carbon atoms substituted by CN; wherein at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms; and X is a halogen atom) to obtain formula (dC).

Alternatively, aniline may be reacted with a halogenated carbon represented by R _D1 -X (R _D1 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom), and then R _D2 (R _D2 represents an alkyl group having 1 to 14 carbon atoms) may be introduced according to a known reaction. For example, R _D2 may be introduced using (R _D2 ) ₂ SO ₄ .

<Method for producing compounds of general formula (E)> The method for producing the compound represented by the above formula (E) is described.

The compound represented by the above formula (E) is obtained by coupling a diazo compound of a 4-nitroaniline derivative represented by the formula (eD) (wherein _XE and _YE represent a halogen atom) with a compound represented by the formula (eC) (wherein _RE represents an alkyl group having 4 to 18 carbon atoms).

(i) Diazotization of the compound of formula (e-D) First, the compound represented by formula (e-D) is diazotized in an inorganic acid or an organic carboxylic acid using a nitrosating agent or nitrosylsulfuric acid in the presence of additional water as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. Examples of the inorganic acid include hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is a nitrite of an alkaline metal, such as sodium nitrite in a solid state or in an aqueous solution.

The diazotization temperature is preferably -10 to 40°C, and more preferably 0 to 30°C. Furthermore, the compound represented by formula (e-D) is generally widely used as a raw material for azo disperse dyes.

(ii) Coupling with a compound of formula (e-C) For example, a solution of a diazo compound of formula (e-D) is added to a solution or suspension of a compound of formula (e-C) in an alcohol (e.g., methanol) at a temperature range of -5 to 10°C to obtain a compound of formula (E).

The pH value of the solution or suspension of the compound represented by formula (e-C) is preferably weakly acidic, and the addition of a buffer such as triethylamine or sodium acetate is advantageous.

The water content of the compound of the general formula (E) may be within a range capable of producing an aqueous dispersion, for example, it may be adjusted to 60% by mass or less, preferably 40% by mass or less for dyeing.

(iii) Method for producing the compound of formula (e-C) The compound of formula (e-C) as a raw material can be produced by the following method.

Using DMF as a solvent, 2-phenyl-1H-indole represented by formula (e-C1) is reacted with a halogenated alkyl represented by _RE1 -X ( _RE1 represents an alkyl group having 4 to 18 carbon atoms, and X is a halogen atom) to obtain formula (eC).

<Method for producing the compound of general formula (F)> The method for producing the compound represented by the above formula (F) is described.

The compound represented by the above formula (F) is obtained by coupling a diazo compound of 3-amino-5-nitro-2,1-benzoisothiazole represented by the formula (fD) with a compound represented by the formula (fC) (in the formula (fC), _RF1 and _RF2 independently represent an alkyl group having 4 to 14 carbon atoms).

(i) Diazotization of the compound of formula (f-D) First, the compound represented by formula (f-D) is diazotized in an inorganic acid or an organic carboxylic acid using a nitrosating agent or nitrosylsulfuric acid in the presence of additional water as appropriate to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. Examples of the inorganic acid include hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is a nitrite of an alkaline metal, such as sodium nitrite in a solid state or in an aqueous solution.

The diazotization temperature is preferably -10 to 15°C, and more preferably -5 to 10°C. The compound represented by formula (f-D) is generally widely used as a raw material for azo disperse dyes.

(ii) Coupling with a compound of formula (f-C) For example, a solution of a diazo compound of formula (f-D) is added to a solution or suspension of a compound of formula (f-C) in an alcohol (e.g., methanol) at a temperature range of -5 to 10°C to obtain a compound of formula (F).

The pH value of the solution or suspension of the compound represented by formula (f-C) is preferably weakly acidic, and the addition of a buffer such as triethylamine or sodium acetate is advantageous. The water content of the compound of general formula (F) can be within a range capable of producing an aqueous dispersion, for example, adjusted to 60% by mass or less, preferably 40% by mass or less for dyeing.

(iii) Method for producing the compound of formula (f-C) The compound of formula (f-C) as a raw material can be produced by the following method.

Using DMF as a solvent, aniline is reacted with a halogenated alkyl represented by _RF1 -X and _RF2 -X ( _RF1 and _RF2 independently represent an alkyl group having 4 to 14 carbon atoms, and X is a halogen atom) to obtain the compound of formula (fC).

Alternatively, aniline may be reacted with a halogenated carbon represented by _RF1 -X ( _RF1 represents an alkyl group having 1 to 14 carbon atoms, and X represents a halogen atom), and then _RF2 ( _RF2 represents an alkyl group having 1 to ₁₄ carbon atoms) may be introduced according to a known reaction. For example, _RF2 may be introduced using ( _RF2 ) _2SO4 .

<Method for producing the compound of general formula (G)> The method for producing the compound represented by the above formula (G) is described.

The compound represented by formula (G) is obtained by reacting 5-aminoanthraquinone [9,1-cd] isothiazol-6-one represented by formula (g) with a carboxylic acid halide represented by _RG -COX ( _RG represents an alkyl group having 7 to 18 carbon atoms, and X is a halogen atom) in an inert solvent such as toluene, xylene, or chlorobenzene.

The reaction temperature is preferably 80°C to 140°C, more preferably 110 to 140°C. The compound represented by formula (g) is generally widely used as a raw material for polycyclic disperse dyes.

The water content of the compound of the general formula (G) may be within a range capable of producing an aqueous dispersion, for example, it may be adjusted to 60% by mass or less, preferably 40% by mass or less for dyeing.

<Dye composition> As described above, the dye composition of the present invention comprises at least one of the compounds of general formulae (A) to (G) and a non-ionic dispersant.

Examples of the nonionic dispersant include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene aryl phenyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene aryl aryl ethers, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene acetylene glycols, polyvinyl alcohols, polyvinyl pyrrolidone, oxyethylene-oxypropylene copolymers, etc. Among them, it is preferred to use at least one selected from polyoxyethylene alkylphenyl ethers, polyoxyethylene aryl phenyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene aryl aryl ethers, and oxyethylene-oxypropylene copolymers, more preferably at least one selected from polyoxyethylene aryl phenyl ethers, polyoxyethylene aryl aryl ethers, and oxyethylene-oxypropylene copolymers, and further preferably at least one selected from polyoxyethylene aryl phenyl ethers and oxyethylene-oxypropylene copolymers.

The polymerization form of the above-mentioned oxyethylene-oxypropylene copolymer is not limited and can be any one of a random polymer, a block polymer, etc. Furthermore, in order to use the dye composition in the form of a powder rather than a liquid aqueous dispersion by spray drying, etc. using a non-ionic dispersant, it is preferred that both polyoxyethylene aryl phenyl ether and oxyethylene-oxypropylene copolymer are contained in the non-ionic dispersant.

The amount of the nonionic dispersant used is preferably 20 to 200% by mass, more preferably 20 to 100% by mass, relative to the mass of the compound represented by formula (A) to (G), in order to maintain good dispersion stability of the compound represented by formula (A) to (G).

Viscosity regulators, surface tension regulators, pH regulators, humectants, water-soluble additives, metal ion blocking agents, preservatives, anti-mold agents, defoaming agents, etc. may be added to the dye composition of the present invention as needed without hindering the purpose of the present invention.

The dye composition of the present invention may further contain additives. Examples of the additives include: coloring agents, dispersants, fillers, stabilizers, plasticizers, crystallization nucleating agents, modifiers, foaming agents, ultraviolet absorbers, light stabilizers, antioxidants, antibacterial agents, mold inhibitors, antistatic agents, flame retardants, inorganic fillers, and elastomers for improving impact resistance.

The dye composition of the present invention is preferably an aqueous dispersion from the viewpoint of ease of handling and safety. The compounds represented by formulas (A) to (G) have high lipophilicity, so in order to obtain a dye composition in the form of an aqueous dispersion, the above-mentioned dispersant must be used together with a dispersion machine such as a bead mill to perform a microparticle dispersion treatment.

Furthermore, the dye composition of the present invention may be in the form of a liquid aqueous dispersion in which the compound represented by formula (A) to (G) is micronized and dispersed in an aqueous dispersion medium using a non-ionic dispersant, or in the form of a powder in which the dispersion medium of the liquid aqueous dispersion is removed by spray drying or the like. From the viewpoint of product life, the powder form is preferred.

The content of the compounds represented by formulae (A) to (G) in the dye composition of the present invention may be within a range that allows easy handling during dyeing, preferably 5 to 40% by mass, more preferably 10 to 30% by mass.

The preferred method for producing the dye composition of the invention is as follows. (1) Various additives such as a non-ionic dispersant and a viscosity adjuster as required are added to water and stirred to prepare a dispersant solution. (2) Compounds represented by formulas (A) to (G) are added to the dispersant solution of (1) and stirred to prepare an aqueous slurry. (3) The aqueous slurry of (2) is subjected to a microparticle dispersion treatment using a wet disperser such as a bead mill until the volume median particle size of the compounds represented by formulas (A) to (G) becomes less than 1.0 μm, preferably less than 0.5 μm. (4) Add water to the fine particle dispersion treated product of (3) to adjust the concentration and obtain a liquid water-based dispersion. (5) Add various additives such as a dispersant to the liquid water-based dispersion of (4) as needed and stir the mixture, remove the dispersion medium by spray drying or the like, and obtain a powdered dye composition. The obtained (4) liquid water-based dispersion or (5) powdered dye composition can be used to perform water-based dyeing of fibers by dip dyeing, printing and dyeing, etc.

The compounds of general formula (A) to (G) contained in the dye composition for dyeing fibers of the present invention have blue, purple, red, orange, or yellow colors. The dye composition may contain the compounds of general formula (A) to (G) alone or contain two or more of them. When the dye composition contains two or more compounds of general formula (A) to (G), a dye for dyeing fibers into various hues or black can be obtained.

The dye composition for dyeing the fiber into black preferably comprises: at least one purple or blue compound selected from the group consisting of compounds of general formula (A), compounds of general formula (B), compounds of general formula (C), and compounds of general formula (F), at least one red compound selected from the group consisting of compounds of general formula (C) and compounds of general formula (D), and at least one yellow or orange compound selected from the group consisting of compounds of general formula (D), compounds of general formula (E), and compounds of general formula (G), more preferably Preferably, the compound comprises at least one purple or blue compound selected from the group consisting of compounds of general formula (A), compounds of general formula (B) and compounds of general formula (F), a red compound of compounds of general formula (C), and at least one orange compound selected from the group consisting of compounds of general formula (D) and compounds of general formula (E), and more preferably, the compound comprises a blue compound of compounds of general formula (A), a red compound of compounds of general formula (C), and an orange compound of compounds of general formula (D).

[Table 1] A dye composition used to dye fibers black. Purple or blue compounds Red compound Yellow or orange compounds Better Compounds of general formula (A) Compounds of general formula (B) Compounds of general formula (C) Compounds of general formula (F) Compounds of formula (C) Compounds of formula (D) Compounds of general formula (D) Compounds of general formula (E) Compounds of general formula (G) Better Compounds of general formula (A) Compounds of general formula (B) Compounds of general formula (F) Compounds of formula (C) Compounds of general formula (D) Compounds of general formula (E) The better Compounds of general formula (A) Compounds of formula (C) Compounds of formula (D)

The composition of the compounds in the dye composition for dyeing the fiber into black is preferably a mixing ratio of the purple or blue compounds in the range of 30 to 70 mass %, a mixing ratio of the red compounds in the range of 5 to 25 mass %, and a mixing ratio of the yellow or orange compounds in the range of 15 to 55 mass %, and more preferably a mixing ratio of the purple or blue compounds in the range of 40 to 60 mass %, a mixing ratio of the red compounds in the range of 5 to 25 mass %, and a mixing ratio of the yellow or orange compounds in the range of 25 to 45 mass %.

[Table 2] About Mixing Ratio Purple or blue compounds Red compound Yellow or orange compounds Compounds of general formula (A), Compounds of general formula (B), Compounds of general formula (C), Compounds of general formula (F) Compounds of formula (C) Compounds of formula (D) Compounds of general formula (D) Compounds of general formula (E) Compounds of general formula (G) Better 30 to 70% by mass 5 to 25 mass% 15 to 55 mass% Better 40 to 60% by mass 5 to 25 mass% 25 to 45% by mass

Examples of the fiber to be dyed in the present invention include polyester fiber, polyolefin fiber, acrylic fiber, etc., preferably polyolefin fiber.

The polyolefin fiber may be, for example, a fiber formed from a polymer selected from the following substances: homopolymers of α-olefins such as propylene, ethylene, 1-butene, 3-methyl-1-butene, 4-methyl-1-pentene, 1-octene, etc.; copolymers of these α-olefins; or copolymers with other unsaturated monomers that can copolymerize with these α-olefins. In addition, the types of copolymers may include, for example, block copolymers, random copolymers, graft copolymers, etc. Specific examples of the above-mentioned polymers include: polypropylene resins such as propylene homopolymer, propylene-ethylene block copolymer, propylene-ethylene random copolymer, propylene-ethylene-(1-butene) copolymer, etc.; polyethylene resins such as low-density polyethylene, medium-density polyethylene, high-density polyethylene, linear low-density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, etc.; poly-1-butene, poly-4-methyl-1-pentene, etc.

The above polymers can be used alone or in combination of two or more to form polyolefin fibers.

The polyolefin fiber is preferably formed of a polypropylene resin and/or a polyethylene resin, and more preferably formed of a polypropylene resin.

The polyolefin fiber may be in the form of a block (molded product, etc.), a film, a fiber (cloth (woven fabric, knitted fabric, nonwoven fabric, etc.), a filament (filament, machine-spun yarn, slit yarn, rip yarn, etc.), etc.), preferably a fiber.

The polyolefin fiber may be a fiber formed by blending polypropylene resin and/or polyethylene resin with other polymer components and performing bonding, etc. The polyolefin fiber may also be a fiber formed by blending polypropylene fiber with other fibers such as polyester.

<Fiber dyeing method> As described above, the present invention provides a fiber dyeing method, which includes the step of using the dye composition of the present invention to dye the fiber in an aqueous manner.

Furthermore, the dyeing step is preferably at least one selected from the group consisting of immersion dyeing, printing dyeing, inkjet dyeing, transfer dyeing, and continuous dyeing, more preferably at least one selected from immersion dyeing and printing dyeing, and more preferably printing dyeing. When the dyeing step is immersion dyeing, the dyeing step is performed, for example, by immersing the dyed article in the dye composition of the present invention under pressure at preferably 80° C. to 130° C., more preferably 90° C. to 120° C. for preferably 30 minutes to 60 minutes.

When the fiber is polyolefin, the dyeing step is preferably performed at 80° C. to 130° C. The dyeing step is preferably performed for 30 minutes to 60 minutes.

When the fiber is polypropylene, the dyeing step is preferably performed at 110° C. to 130° C. The dyeing step is preferably performed for 30 minutes to 60 minutes.

When the fiber is polyethylene, the dyeing step is preferably performed at 90° C. to 110° C. The dyeing step is preferably performed for 30 minutes to 60 minutes.

When the dyeing step is printing and dyeing, the dyeing step is performed by, for example, printing a printing and dyeing paste prepared by mixing the dye composition of the present invention in a paste such as a natural paste (e.g., guar gum, etc.) or a processed paste (e.g., carboxymethyl cellulose, etc.) on the dyed material, and then performing a steam treatment at, for example, 90° C. to 200° C. for 1 minute to 20 minutes, or a dry heat treatment for 20 seconds to 5 minutes.

When the fiber is polyolefin, the dyeing step is preferably performed by steam treatment at 80°C to 130°C for 1 minute to 10 minutes.

When the fiber is polypropylene, the dyeing step is preferably performed by steam treatment at 110° C. to 130° C. for 1 minute to 10 minutes.

When the fiber is polyethylene, the dyeing step is preferably performed by steam treatment at 90° C. to 110° C. for 1 minute to 10 minutes.

When the dyeing step is inkjet dyeing, the dyeing step is, for example, to prepare inkjet printing ink by adding a low-volatile water-soluble organic solvent such as glycerin or diethylene glycol to the liquid dye composition of the present invention, and printing the ink using an inkjet printer on a cloth or fiber that has been pre-applied with a paste by pressure dyeing or the like, or the formed fiber, and then performing a steam treatment at, for example, 90°C to 200°C for 1 minute to 20 minutes, or a dry heat treatment for 20 seconds to 5 minutes.

In the case of immersion dyeing, the concentration of the dye of the present invention relative to the above-mentioned fiber is, for example, 0.001% o.m.f. to 10% o.m.f., preferably 0.001% o.m.f. to 5% o.m.f.. In addition, o.m.f. means on the mass of fiber.

In the case of printing and dyeing, the concentration of the dye of the present invention relative to the above-mentioned printing and dyeing paste is, for example, 0.001% o.m.p. to 5% o.m.p., preferably 0.001% o.m.p. to 2% o.m.p.. In addition, o.m.p. means on the mass of paste.

The present invention provides a fiber dyed by the dyeing method of the present invention. The fiber can be used for clothing, underwear, hats, socks, gloves, sportswear and other clothing, seat cushions and other vehicle interior materials, carpets, curtains, cushions, sofa covers, cushion covers and other indoor products, etc.

The present invention is further described in detail below by way of examples, but the present invention is not limited thereto. [Examples]

(Synthesis Example 1) [Synthesis of blue dye compound (A-1)] The blue dye compound (A-1) was produced according to the following process.

1-A. Synthesis of coupling agent compound (C1) and preparation of coupling agent component solution (Step 1) Dissolve p-anisidine (purchased as a commercial product) (24.6 g) in DMF (35 g) and add pyridine (19 g) dropwise. Add n-octyl chloride (purchased as a commercial product) (34.2 g) dropwise, heat to 110°C, and stir for 1 hour. After cooling to room temperature, add 2 M hydrochloric acid (150 ml) to precipitate. The mixture is separated by filtration, washed with water, and dried to obtain N-(4-methoxyphenyl)octylamide (53.1 g, yield 106.5%) represented by the following formula (C1a) as a crude product.

Formula (C1a)

(Step 2) N-(4-methoxyphenyl)octanamide (12.5 g) obtained in the above step 1 was slowly added to concentrated sulfuric acid (30 g) cooled to 5°C at 5 to 10°C. Concentrated nitric acid (4.57 g) was added dropwise to the mixture at 5 to 10°C over 1 hour, and then stirred at the same temperature for 1 hour. The reaction mixture was blown into ice water (150 g), ethyl acetate (100 g) was added, and the organic phase was extracted. After washing the extract with saturated saline water, the solvent was distilled off under reduced pressure to obtain N-(3-nitro-4-methoxyphenyl)octanamide (16.9 g, yield 114.8%) represented by the following formula (C1b) as a crude product.

Formula (C1b)

(Step 3) The mixture of N-(3-nitro-4-methoxyphenyl)octanamide (16.9 g), tin (8.9 g) and methanol (7.5 g) obtained in the above step 2 was cooled to 5°C. After 1 hour, concentrated hydrochloric acid (31.4 g) was added dropwise to the mixture, and the temperature was raised to 75 to 80°C and stirred for 40 minutes. After the reaction mixture was cooled to 10°C, a 48% aqueous sodium hydroxide solution (55.2 ml) was slowly added at a temperature of 10 to 20°C. The mixture was separated by filtration, washed with water and dried to obtain N-(3-amino-4-methoxyphenyl)octanamide (9.19 g, yield 69.5%) represented by the following formula (C1c).

Formula (C1c)

(Step 4) A mixture of N-(3-amino-4-methoxyphenyl)octanamide (13.2 g), triethylamine (15 g), DMF (15 g) and 1-bromooctane (purchased as a commercial product) (38.6 g) obtained in the above step 3 was heated to 120°C and stirred at the same temperature for 3 hours to obtain N-[3-(N,N-dioctylamino)-4-methoxyphenyl]octanamide represented by the following formula (C1). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C1).

Formula (C1)

1-B. Preparation of diazo component solution (Step 5) 2-bromo-4,6-dinitroaniline (13.1 g) represented by the following formula (D1) was slowly added to a mixture of concentrated sulfuric acid (16 g) and 43% nitrosylsulfuric acid (12.8 g) at 25 to 30°C. The mixture was stirred at 30 to 40°C for 2 hours to obtain a diazo component solution.

Formula (D1)

1-C. Synthesis of blue dye compound (A-1) by coupling reaction (step 6) Triethylamine (84 g) was appropriately added to the coupling agent component solution obtained in the above step 4 at 0 to 10°C, and the diazo component solution obtained in the above step 5 was added dropwise over 2 hours to carry out coupling reaction. After the mixture was stirred at 0 to 10°C for 30 minutes, the product was separated from the reaction mixture by filtration, washed with methanol, and then washed with water, and dried at 60°C until the water content was 1.0 mass % or less, to obtain a blue dye compound represented by the following formula (A-1) (5.93 g, yield 15.5%). The structure of the blue-dyed compound was confirmed by LCMS analysis (m/z 761 (M ⁺ )).

Formula (A-1)

(Synthesis Example 2) [Synthesis of blue dye compound (A-2)] The blue dye compound (A-2) was produced according to the following process.

2-A. Synthesis of coupling agent compound (C2) and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 1, pentanoyl chloride (25.3 g) was used instead of n-octanoyl chloride. The same operation as steps 1 to 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-dioctylamino)-4-methoxyphenyl]pentanoylamide represented by the following formula (C2). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C2).

Formula (C2)

2-B. Synthesis of blue dye compound (A-2) by coupling reaction (step 2) As the coupling agent component solution, the compound of formula (C2) obtained in step 1 was used instead of the compound of formula (C1). The same operation as steps 5 and 6 of Synthesis Example 1 was performed to obtain a blue dye compound represented by the following formula (A-2) (8.03 g, yield 22.3%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 719 (M ⁺ )).

Formula (A-2)

(Synthesis Example 3) [Synthesis of blue dye compound (A-3)] The blue dye compound (A-3) was produced according to the following process.

3-A. Synthesis of coupling agent compound (C3) and preparation of coupling agent component solution (Step 1) In Step 1 of Synthesis Example 1, propionyl chloride (19.4 g) was used instead of n-octyl chloride. The same operation as Steps 1 to 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-dioctylamino)-4-methoxyphenyl]propionamide represented by the following formula (C3). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C3).

Formula (C3)

3-B. Synthesis of blue dye compound (A-3) by coupling reaction (step 2) The same operation as steps 5 and 6 of Synthesis Example 1 was performed except that the compound of formula (C3) obtained in step 1 was used instead of the compound of formula (C1) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (A-3) (5.85 g, yield 16.9%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 691 (M ⁺ )).

Formula (A-3)

(Synthesis Example 4) [Synthesis of blue dye compound (A-4)] The blue dye compound (A-4) was produced according to the following process.

4-A. Synthesis of coupling agent compound C4 and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 1, 2-ethylhexanoyl chloride (34.2 g) was used instead of n-octyl chloride. The same operation as steps 1 to 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-dioctylamino)-4-methoxyphenyl]-2-ethylhexanoylamide represented by the following formula (C4). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C4).

Formula (C4)

4-B. Synthesis of blue dye compound (A-4) by coupling reaction (step 2) The same operation as steps 5 and 6 of Synthesis Example 1 was performed except that the compound of formula (C4) obtained in step 1 was used instead of the compound of formula (C1) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (A-4) (9.63 g, yield 25.3%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 761 (M ⁺ )).

Formula (A-4)

(Synthesis Example 5) [Synthesis of blue dye compound (A-5)] The blue dye compound (A-5) was produced according to the following process.

5-A. Synthesis of coupling agent compound C5 and preparation of coupling agent component solution (Step 1) In step 4 of Synthesis Example 1, N-(3-amino-4-methoxyphenyl)acetamide (purchased as a commercial product) (9.0 g) was used instead of N-(3-amino-4-methoxyphenyl)octanamide. The same operation as step 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-dioctylamino)-4-methoxyphenyl]acetamide represented by the following formula (C5). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C5).

Formula (C5)

5-B. Synthesis of blue dye compound (A-5) by coupling reaction (step 2) The same operation as steps 5 and 6 of Synthesis Example 1 was performed except that the compound of formula (C5) obtained in step 1 was used instead of the compound of formula (C1) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (A-5) (20.3 g, yield 60.0%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 677 (M ⁺ )).

Formula (A-5)

(Synthesis Example 6) [Synthesis of blue dye compound (A-6)] The blue dye compound (A-6) was produced according to the following process.

6-A. Synthesis of coupling agent compound (C6) and preparation of coupling agent component solution (Step 1) In step 4 of Synthesis Example 1, 1-bromododecane (49.8 g) was used instead of 1-bromooctane, and N-(3-amino-4-methoxyphenyl)acetamide (9.0 g) was used instead of N-(3-amino-4-methoxyphenyl)octamide. The same operation as step 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-di(dodecyl)amino)-4-methoxyphenyl]acetamide represented by the following formula (C6). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C6).

Formula (C6)

6-B. Synthesis of blue dye compound (A-6) by coupling reaction (step 2) As the coupling agent component solution, the compound of formula (C6) obtained in step 1 was used instead of the compound of formula (C1). The same operation as steps 5 and 6 of Synthesis Example 1 was performed to obtain a blue dye compound represented by the following formula (A-6) (19.3 g, yield 48.9%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 789 (M ⁺ )).

Formula (A-6)

(Synthesis Example 7) [Synthesis of blue dye compound (A-7)] The blue dye compound (A-7) was produced according to the following process.

7-A. Synthesis of coupling agent compound C7 and preparation of coupling agent component solution (Step 1) In step 4 of Synthesis Example 1, 1-bromoethane (27.3 g) was used instead of 1-bromooctane. The same operation as step 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-diethylamino)-4-methoxyphenyl]octanamide represented by the following formula (C7). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C7).

Formula (C7)

7-B. Synthesis of blue dye compound (A-7) by coupling reaction (step 2) As the coupling agent component solution, the compound of formula (C7) obtained in step 1 was used instead of the compound of formula (C1). The same operation as steps 5 and 6 of Synthesis Example 1 was performed to obtain a blue dye compound represented by the following formula (A-7) (7.71 g, yield 26.0%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 593 (M ⁺ )).

Formula (A-7)

(Synthesis Example 8) [Synthesis of blue dye compound (A-8)] The blue dye compound (A-8) was produced according to the following process.

8-A. Synthesis of coupling agent compound C8 and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 1, 4-ethoxyaniline (27.4 g) was used instead of p-methoxyaniline. The same operation as steps 1 to 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-dioctylamino)-4-ethoxyphenyl]octanamide represented by the following formula (C8). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C8).

Formula (C8)

8-B. Synthesis of blue dye compound (A-8) by coupling reaction (step 2) The same operation as steps 5 and 6 of Synthesis Example 1 was performed except that the compound of formula (C8) obtained in step 1 was used instead of the compound of formula (C1) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (A-8) (4.50 g, yield 11.6%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 775 (M ⁺ )).

Formula (A-8)

(Synthesis Example 9) [Synthesis of blue dye compound (B-1)] The blue dye compound (B-1) was produced according to the following process.

9-A. Synthesis of coupling agent compound C9 and preparation of coupling agent component solution (Step 1) Except for using 3-nitroaniline (27.6 g) instead of p-anisidine, the same operation as Step 1 of Synthesis Example 1 was performed to obtain N-(3-nitrophenyl)octanamide (53.6 g, yield 101.4%) represented by the following formula (C9a) as a crude product.

Formula (C9a)

(Step 2) Except for using N-(3-nitrophenyl)octylamide (13.2 g) instead of N-(3-nitro-4-methoxyphenyl)octylamide, the same operation as Step 3 of Synthesis Example 1 was performed to obtain N-(3-aminophenyl)octylamide (9.48 g, yield 80.9%) represented by the following formula (C9b).

Formula (C9b)

(Step 3) Other than using N-(3-aminophenyl)octanamide (11.7 g) instead of N-(3-amino-4-methoxyphenyl)octanamide, the same operation as Step 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-dioctylamino)phenyl]octanamide represented by the following formula (C9). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C9).

Formula (C9)

9-B. Preparation of diazo component solution (Step 4) 3-amino-5-nitro-2,1-benzoisothiazole (8.15 g) represented by the following formula (D2) was slowly added to a mixture of concentrated sulfuric acid (29 g) and 43% nitrosylsulfuric acid (12.7 g) at a temperature between 0 and 5°C. 80% acetic acid (10 g) was slowly added dropwise to the mixture at a temperature between 0 and 5°C, and the mixture was stirred at the same temperature for 2 hours to obtain a diazo component solution.

Formula (D2)

9-C. Synthesis of blue dye compound (B-1) by coupling reaction (step 5) Triethylamine (43 g) was added appropriately to the coupling agent component solution (C9) at a temperature of 0 to 10°C, and the diazo component solution (D2) was added dropwise over 2 hours to carry out coupling reaction. After stirring at a temperature of 0 to 10°C for 20 minutes, the product was separated from the reaction mixture by filtration, washed with methanol, and then washed with water, and dried at 60°C until the water content was 1.0 mass % or less to obtain a blue dye compound represented by the following formula (B-1) (20.9 g, yield 62.9%). The structure of the blue dye compound was confirmed by LCMS analysis (m/z 665 (M ⁺ )).

Formula (B-1)

(Synthesis Example 10) [Synthesis of blue dye compound (B-2)] The blue dye compound (B-2) was produced according to the following process.

10-A. Synthesis of coupling agent compound C10 and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 9, pentanoyl chloride (25.3 g) was used instead of n-octanoyl chloride. The same operation as steps 1 to 3 of Synthesis Example 9 was performed to obtain N-[3-(N,N-dioctylamino)phenyl]pentanoylamide represented by the following formula (C10). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C10).

Formula (C10)

10-B. Synthesis of blue dye compound (B-2) by coupling reaction (step 2) As the coupling agent component solution, the compound of formula (C10) obtained in step 1 was used instead of the compound of formula (C9). The same operation as steps 4 and 5 of Synthesis Example 9 was performed to obtain a blue dye compound represented by the following formula (B-2) (9.47 g, yield 30.4%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 623 (M ⁺ )).

Formula (B-2)

(Synthesis Example 11) [Synthesis of blue dye compound (B-3)] The blue dye compound (B-3) was produced according to the following process.

11-A. Synthesis of coupling agent compound C11 and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 9, propionyl chloride (19.4 g) was used instead of n-octyl chloride. The same operation as steps 1 to 3 of Synthesis Example 9 was performed to obtain N-[3-(N,N-dioctylamino)phenyl]propionamide represented by the following formula (C11). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C11).

Formula (C11)

11-B. Synthesis of blue dye compound (B-3) by coupling reaction (step 2) As the coupling agent component solution, the compound of formula (C11) obtained in step 1 was used instead of the compound of formula (C9). The same operation as steps 4 and 5 of Synthesis Example 9 was performed to obtain a blue dye compound represented by the following formula (B-3) (13.4 g, yield 45.0%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 595 (M ⁺ )).

Formula (B-3)

(Synthesis Example 12) [Synthesis of blue dye compound (B-4)] The blue dye compound (B-4) was produced according to the following process.

12-A. Synthesis of coupling agent compound C12 and preparation of coupling agent component solution (Step 1) In step 3 of Synthesis Example 9, 3'-aminoacetylaniline (7.50 g) was used instead of N-(3-aminophenyl)octanamide. The same operation as step 3 of Synthesis Example 9 was performed to obtain N-[3-(N,N-dioctylamino)phenyl]acetamide represented by the following formula (C12). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C12).

Formula (C12)

12-B. Synthesis of blue dye compound (B-4) by coupling reaction (step 2) The same operation as steps 4 and 5 of Synthesis Example 9 was performed except that the compound of formula (C12) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (B-4) (20.3 g, yield 69.9%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 581 (M ⁺ )).

Formula (B-4)

(Synthesis Example 13) [Synthesis of blue dye compound (B-5)] The blue dye compound (B-5) was produced according to the following process.

13-A. Synthesis of coupling agent compound C13 and preparation of coupling agent component solution (Step 1) In step 3 of Synthesis Example 9, 1-bromododecane (49.8 g) was used instead of 1-bromooctane, and 3'-aminoacetaniline (7.50 g) was used instead of N-(3-aminophenyl)octanamide. The same operation as step 3 of Synthesis Example 9 was performed to obtain N-[3-(N,N-di(dodecyl)amino)phenyl]acetamide represented by the following formula (C13). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C13).

Formula (C13)

13-B. Synthesis of blue dye compound (B-5) by coupling reaction (step 2) As the coupling agent component solution, the compound of formula (C13) obtained in step 1 was used instead of the compound of formula (C9). The same operation as steps 4 and 5 of Synthesis Example 9 was performed to obtain a blue dye compound represented by the following formula (B-5) (9.81 g, yield 28.3%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 693 (M ⁺ )).

Formula (B-5)

(Synthesis Example 14) [Synthesis of blue dye compound (B-6)] The blue dye compound (B-6) was produced according to the following process.

14-A. Synthesis of coupling agent compound C14 and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 9, propionyl chloride (19.4 g) was used instead of n-octyl chloride, and in step 3 of Synthesis Example 9, 1-bromodecane (49.8 g) was used instead of 1-bromooctane. The same operation as steps 1 to 3 of Synthesis Example 9 was performed to obtain N-[3-(N,N-di(dodecyl)amino)phenyl]propionamide represented by the following formula (C14). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C14).

Formula (C14)

14-B. Synthesis of blue dye compound (B-6) by coupling reaction (step 2) The same operation as steps 4 and 5 of Synthesis Example 9 was performed except that the compound of formula (C14) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (B-6) (5.73 g, yield 16.2%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 707 (M ⁺ )).

Formula (B-6)

(Synthesis Example 15) [Synthesis of blue dye compound (B-7)] The blue dye compound (B-7) was produced according to the following process.

15-A. Synthesis of coupling agent compound C15 and preparation of coupling agent component solution (Step 1) In step 3 of Synthesis Example 9, 3'-aminoacetylaniline (7.50 g) was used instead of N-(3-aminophenyl)octanamide, and 1-bromo-2-ethylhexane (38.6 g) was used instead of 1-bromooctane. The same operation as step 3 of Synthesis Example 9 was performed to obtain N-[3-[N,N-di(2-ethylhexyl)amino]phenyl]propionamide represented by the following formula (C15). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C15).

Formula (C15)

15-B. Synthesis of blue dye compound (B-7) by coupling reaction (step 2) The same operation as steps 4 and 5 of Synthesis Example 9 was performed except that the compound of formula (C15) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (B-7) (4.72 g, yield 16.2%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 581 (M ⁺ )).

Formula (B-7)

(Synthesis Example 16) [Synthesis of blue dye compound (B-8)] The blue dye compound (B-8) was produced according to the following process.

16-A. Synthesis of coupling agent compound C16 and preparation of coupling agent component solution (Step 1) In step 3 of Synthesis Example 9, 1-bromoethane (27.3 g) was used instead of 1-bromooctane. The same operation as steps 1 to 3 of Synthesis Example 9 was performed to obtain N-[3-(N,N-diethylamino)phenyl]octanamide represented by the following formula (C16). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C16).

Formula (C16)

16-B. Synthesis of blue dye compound (B-8) by coupling reaction (step 2) As the coupling agent component solution, the compound of formula (C16) obtained in step 1 was used instead of the compound of formula (C9). The same operation as steps 4 and 5 of Synthesis Example 9 was performed to obtain a blue dye compound represented by the following formula (B-8) (23.2 g, yield 93.4%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 497 (M ⁺ )).

Formula (B-8)

(Synthesis Example 17) [Synthesis of red dye compound (C-1)] The red dye compound (C-1) was produced according to the following process.

17-A. Preparation of diazo component solution (Step 1) Add 2-chloro-4-nitroaniline (8.65 g) represented by the following formula (D3) to a mixture of concentrated sulfuric acid (16 g) and 43% nitrosylsulfuric acid (15.6 g) at 30 to 35°C, and stir at the same temperature for 2 hours to obtain a diazo component solution.

Formula (D3)

17-B. Synthesis of red dye compound (C-1) by coupling reaction (step 2) The preparation of a coupling agent component solution composed of a compound of formula (C9) is carried out in the same manner as steps 1 to 3 of Synthesis Example 9. Triethylamine (28 g) is appropriately added to the above coupling agent component solution at a temperature in the range of 0 to 10° C., and the above diazo component solution obtained in step 1 is added dropwise over 2 hours to carry out a coupling reaction. After stirring at 0 to 10°C for 20 minutes, the product was separated from the reaction mixture by filtration, washed with methanol, then washed with water, and dried at 60°C until the water content was 1.0 mass % or less to obtain a red dye compound represented by the following formula (C-1) (24.3 g, yield 75.7%). The structure of the red dye compound was confirmed by LCMS analysis (m/z 642 (M ⁺ )).

Formula (C-1)

(Synthesis Example 18) [Synthesis of red dye compound (C-2)] The red dye compound (C-2) was produced according to the following process.

The same operation as steps 1 and 2 of Synthesis Example 17 was performed except that the compound of formula (C10) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a red dye compound represented by the following formula (C-2) (10.4 g, yield 34.7%). The structure of the red dye compound was confirmed by LCMS analysis (m/z 600 (M ⁺ )).

Formula (C-2)

(Synthesis Example 19) [Synthesis of red dye compound (C-3)] The red dye compound (C-3) was produced according to the following process.

The same operation as steps 1 and 2 of Synthesis Example 17 was performed except that the compound of formula (C11) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a red dye compound represented by the following formula (C-3) (12.9 g, yield 45.1%). The structure of the red dye compound was confirmed by LCMS analysis (m/z 572 (M ⁺ )).

Formula (C-3)

(Synthesis Example 20) [Synthesis of red dye compound (C-4)] The red dye compound (C-4) was produced according to the following process.

The same operation as steps 1 and 2 of Synthesis Example 17 was performed except that the compound of formula (C12) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a red dye compound represented by the following formula (C-4) (23.4 g, yield 83.9%). The structure of the red dye compound was confirmed by LCMS analysis (m/z 558 (M ⁺ )).

Formula (C-4)

(Synthesis Example 21) [Synthesis of red dye compound (C-5)] The red dye compound (C-5) was produced according to the following process.

The same operation as steps 1 and 2 of Synthesis Example 17 was performed except that the compound of formula (C13) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a red dye compound represented by the following formula (C-5) (25.3 g, yield 75.5%). The structure of the red dye compound was confirmed by LCMS analysis (m/z 670 (M ⁺ )).

Formula (C-5)

(Synthesis Example 22) [Synthesis of red dye compound (C-6)] The red dye compound (C-6) was produced according to the following process.

22-A. Synthesis of coupling agent compound C17 and preparation of coupling agent component solution (Step 1) In step 3 of Synthesis Example 9, 3'-aminoacetylaniline (7.50 g) was used instead of N-(3-aminophenyl)octanamide, and 1-bromobutane (27.4 g) was used instead of 1-bromooctane. The same operation as step 3 of Synthesis Example 9 was performed to obtain N-[3-(N,N-dibutylamino)phenyl]acetamide represented by the following formula (C17). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C17).

Formula (C17)

22-B. Synthesis of red dye compound (C-6) by coupling reaction (step 2) The same operation as steps 1 and 2 of Synthesis Example 17 was performed except that the compound of formula (C17) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a red dye compound represented by the following formula (C-6) (19.6 g, yield 87.9%). The structure of the above red dye compound was confirmed by LCMS analysis (m/z 446 (M ⁺ )).

Formula (C-6)

(Synthesis Example 23) [Synthesis of red dye compound (C-7)] The red dye compound (C-7) was produced according to the following process.

The same operation as steps 1 and 2 of Synthesis Example 17 was performed except that the compound of formula (C16) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a red dye compound represented by the following formula (C-7) (16.6 g, yield 70.0%). The structure of the red dye compound was confirmed by LCMS analysis (m/z 474 (M ⁺ )).

Formula (C-7)

(Synthesis Example 24) [Synthesis of orange dye compound (D-1)] The orange dye compound (D-1) was produced according to the following process.

24-A. Synthesis of coupling agent compound C18 and preparation of coupling agent component solution (Step 1) Except for using aniline (4.66 g) instead of N-(3-amino-4-methoxyphenyl)octanamide, the same operation as step 4 of synthesis example 1 was performed to obtain N,N-dioctylaniline represented by the following formula (C18). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C18).

Formula (C18)

24-B. Preparation of diazo component solution (Step 2) Add 2,6-dichloro-4-nitroaniline (10.4 g) represented by the following formula (D4) to a mixture of concentrated sulfuric acid (17 g) and 43% nitrosylsulfuric acid (14.7 g) at 25 to 30°C, and stir at the same temperature for 2 hours to obtain a diazo component solution.

Formula (D4)

24-C. Synthesis of orange dye compound (D-1) by coupling reaction (step 3) Triethylamine (20 g) was appropriately added to the coupling agent component solution composed of the compound of formula (C18) obtained in step 1 at 0 to 10°C, and the diazo component solution obtained in step 2 was added dropwise over 2 hours to carry out coupling reaction. After stirring at 0 to 10°C for 20 minutes, the product was separated from the reaction mixture by filtration, washed with methanol, and then washed with water, and dried at 60°C until the water content was 1.0 mass % or less, to obtain an orange dye compound represented by the following formula (D-1) (23.1 g, yield 86.4%). The structure of the orange dye compound was confirmed by LCMS analysis (m/z 535 (M ⁺ )).

Formula (D-1)

(Synthesis Example 25) [Synthesis of orange dye compound (D-2)] The orange dye compound (D-2) was produced according to the following process.

25-A. Synthesis of coupling agent compound C19 and preparation of coupling agent component solution (Step 1) Except that aniline (4.66 g) was used instead of N-(3-amino-4-methoxyphenyl)octanamide and 1-bromodecane (49.8 g) was used instead of 1-bromooctane, the same operation as step 4 of synthesis example 1 was performed to obtain N,N-di(dodecyl)aniline represented by the following formula (C19). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C19).

Formula (C19)

25-B. Synthesis of orange dye compound (D-2) by coupling reaction (step 2) The same operation as steps 2 and 3 of Synthesis Example 24 was performed except that the compound of formula (C19) was used instead of the compound of formula (C18) as the coupling agent component solution to obtain an orange dye compound represented by the following formula (D-2) (14.1 g, yield 43.6%). The structure of the above orange dye compound was confirmed by LCMS analysis (m/z 647 (M ⁺ )).

Formula (D-2)

(Synthesis Example 26) [Synthesis of orange dye compound (D-3)] The orange dye compound (D-3) was produced according to the following process.

26-A. Synthesis of coupling agent compound C20 and preparation of coupling agent component solution (Step 1) Except that aniline (4.66 g) was used instead of N-(3-amino-4-methoxyphenyl)octanamide and 1-bromobutane (27.4 g) was used instead of 1-bromooctane, the same operation as step 4 of synthesis example 1 was performed to obtain N,N-dibutylaniline represented by the following formula (C20). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C20).

Formula (C20)

26-B. Synthesis of orange dye compound (D-3) by coupling reaction (step 2) The same operation as steps 2 and 3 of Synthesis Example 24 was performed except that the compound of formula (C20) was used instead of the compound of formula (C18) as the coupling agent component solution to obtain an orange dye compound represented by the following formula (D-3) (10.2 g, yield 48.2%). The structure of the above orange dye compound was confirmed by LCMS analysis (m/z 423 (M ⁺ )).

Formula (D-3)

(Synthesis Example 27) [Synthesis of yellow dye compound (G-1)] The yellow dye compound (G-1) was produced according to the following process.

A mixture of sulfinyl chloride (14.3 g) and toluene (20 g) was added dropwise to a mixture of 2-hexyldecanoic acid (30.8 g) and toluene (30 g). A mixture of pyridine (9.49 g) and toluene (30 g) was slowly added dropwise to the mixture over 1 hour, and the mixture was heated to 110°C and stirred for 1 hour. After cooling to room temperature, a mixture of 5-aminoanthraquinone [9,1-cd] isothiazol-6-one (25.2 g) and toluene (30 g) was added dropwise. The mixture was heated to 110°C and stirred for 2 hours, and the solvent was distilled off under reduced pressure, and methanol (100 g) was added to precipitate. The mixture was separated by filtration, washed with methanol, and then washed with water, and dried at 60°C until the water content was 1.0 mass % or less to obtain a yellow dye compound represented by the following formula (G-1) (36.7 g, yield 74.7%). The structure of the yellow dye compound was confirmed by LCMS analysis (m/z 491 (M ⁺ )).

Formula (G-1)

(Synthesis Example 28) [Synthesis of yellow dye compound (G-2)] The yellow dye compound (G-2) was produced according to the following process.

After adding n-octyl chloride (19.5 g) dropwise to a mixture of 5-aminoanthraquinone [9,1-cd] isothiazol-6-one (25.2 g), toluene (120 g) and pyridine (9.49 g), the mixture was heated to 110°C and stirred for 1 hour. After the mixture was cooled to room temperature, methanol (150 g) was added to precipitate. The mixture was separated by filtration, washed with methanol and dried to obtain a yellow dye compound represented by the following formula (G-2) (31.8 g, yield 83.9%). The structure of the yellow dye compound was confirmed by LCMS analysis (m/z 379 (M ⁺ )).

Formula (G-2)

(Synthesis Example 29) [Synthesis of purple dye compound (F-1)] The purple dye compound (F-1) was produced according to the following process.

The preparation of the coupling agent component solution composed of the compound of formula (C18) was carried out in the same manner as step 1 of Synthesis Example 24, and the preparation of the diazo component solution derived from the compound of formula (D2) was carried out in the same manner as step 4 of Synthesis Example 9. Triethylamine (35 g) was appropriately added to the above coupling agent component solution in the range of 0 to 10°C, and the above diazo component solution was added dropwise over 2 hours to carry out coupling reaction. After stirring in the range of 0 to 10°C for 20 minutes, the product was separated from the reaction mixture by filtration, washed with methanol, and then washed with water, and dried at 60°C until the water content was 1.0 mass% or less, to obtain a purple dye compound represented by the following formula (F-1) (13.0 g, yield 49.6%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 524 (M ⁺ )).

Formula (F-1)

(Synthesis Example 30) [Synthesis of orange dye compound (D-4)] The orange dye compound (D-4) was produced according to the following process.

30-A. Preparation of diazo component solution (Step 1) Add 4-nitroaniline (6.91 g) represented by the following formula (D5) to a mixture of concentrated sulfuric acid (17 g) and 43% nitrosylsulfuric acid (14.7 g) at 30 to 35°C, and stir at the same temperature for 2 hours to obtain a diazo component solution.

Formula (D5)

30-B. Synthesis of orange dye compound (D-4) by coupling reaction (step 2) The preparation of the coupling agent component solution composed of the compound of formula (C18) is carried out in the same manner as step 1 of Synthesis Example 24. Triethylamine (20 g) is appropriately added to the above coupling agent component solution at a temperature of 0 to 10° C., and the above diazo component solution obtained in step 1 is added dropwise over 1 hour to carry out a coupling reaction. After stirring at 0 to 10°C for 20 minutes, the product was separated from the reaction mixture by filtration, washed with methanol, then washed with water, and dried at 60°C until the water content was 1.0 mass % or less to obtain an orange dye compound represented by the following formula (D-4) (12.5 g, yield 53.5%). The structure of the orange dye compound was confirmed by LCMS analysis (m/z 467 (M ⁺ )).

Formula (D-4)

(Synthesis Example 31) [Synthesis of orange dye compound (D-5)] The orange dye compound (D-5) was produced according to the following process.

31-A. Preparation of diazo component solution (Step 1) Add 2,6-dibromo-4-nitroaniline (14.8 g) represented by the following formula (D6) to a mixture of concentrated sulfuric acid (17 g) and 43% nitrosylsulfuric acid (14.7 g) at 25 to 30°C, and stir at the same temperature for 2 hours to obtain a diazo component solution.

Formula (D6)

31-B. Synthesis of orange dye compound (D-5) by coupling reaction (step 2) The preparation of a coupling agent component solution composed of a compound of formula (C18) is carried out in the same manner as step 1 of Synthesis Example 24. Triethylamine (25 g) is appropriately added to the above coupling agent component solution at a temperature of 0 to 10° C., and the above diazo component solution obtained in step 1 is added dropwise over 1 hour to carry out a coupling reaction. After stirring at 0 to 10°C for 20 minutes, the product was separated from the reaction mixture by filtration, washed with methanol, then washed with water, and dried at 60°C until the water content was less than 1.0 mass %, to obtain an orange dye compound represented by the following formula (D-5) (27.6 g, yield 88.6%). The structure of the above orange dye compound was confirmed to be the following formula (D-5) by LCMS analysis (m/z 623 (M ⁺ )).

Formula (D-5)

(Synthesis Example 32) [Synthesis of orange dye compound (D-6)] The orange dye compound (D-6) was produced according to the following process.

The same operation as steps 1 and 2 of Synthesis Example 31 was performed except that the compound of formula (C20) was used instead of the compound of formula (C18) as the coupling agent component solution to obtain an orange dye compound represented by the following formula (D-6) (22.8 g, yield 89.2%). The structure of the above orange dye compound was confirmed by LCMS analysis (m/z 511 (M ⁺ )).

Formula (D-6)

(Synthesis Example 33) [Synthesis of orange dye compound (E-1)] The orange dye compound (E-1) was produced according to the following process.

33-A. Synthesis of coupling agent compound C21 and preparation of coupling agent component solution (Step 1) A mixture of 2-phenyl-1H-indole (9.67 g), triethylamine (7.5 g), DMF (15 g) and 1-bromooctane (11.6 g) was heated to 120°C and stirred at the same temperature for 3 hours to obtain N-octyl-2-phenylindole represented by the following formula (C21). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C21).

Formula (C21)

33-B. Synthesis of orange dye compound (E-1) by coupling reaction (step 2) The preparation of the diazo component solution derived from the compound of formula (D4) was carried out in the same manner as in Synthesis Example 24. Triethylamine (20 g) was appropriately added to the above-mentioned coupling agent component solution obtained in step 1 at a temperature of 0 to 10°C, and the above-mentioned diazo component solution was added dropwise over 1 hour to carry out coupling reaction. After stirring at a temperature of 0 to 10°C for 20 minutes, the product was separated from the reaction mixture by filtration, washed with methanol, and then washed with water, and dried at 60°C until the water content was 1.0 mass % or less, to obtain the orange dye compound represented by the following formula (E-1) (11.3 g, yield 43.2%). The structure of the orange dye compound was confirmed by LCMS analysis (m/z 523 (M ⁺ )).

Formula (E-1)

(Synthesis Example 34) [Synthesis of orange dye compound (E-2)] The orange dye compound (E-2) was produced according to the following process.

34-A. Synthesis of coupling agent compound C22 and preparation of coupling agent component solution (Step 1) Except for using 1-bromobutane (7.53 g) instead of 1-bromooctane, the same operation as Step 1 of Synthesis Example 33 was performed to obtain N-butyl-2-phenylindole represented by the following formula (C22). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C22).

Formula (C22)

34-B. Synthesis of orange dye compound (E-2) by coupling reaction (step 2) As the coupling agent component solution, the compound of formula (C22) was used instead of the compound of formula (C21). The same operation as steps 1 and 2 of Synthesis Example 33 was performed to obtain an orange dye compound represented by the following formula (E-2) (14.5 g, yield 62.1%). The structure of the above orange dye compound was confirmed by LCMS analysis (m/z 467 (M ⁺ )).

Formula (E-2)

(Synthesis Example 35) [Synthesis of red dye compound (D-7)] The red dye compound (D-7) was produced according to the following process.

35-A. Preparation of diazo component solution (Step 1) Add 2-cyano-4-nitroaniline (8.15 g) represented by the following formula (D7) to a mixture of concentrated sulfuric acid (7.5 g), acetic acid (15 g) and 43% nitrosylsulfuric acid (14.9 g) at 20 to 25°C, and stir at the same temperature for 2 hours to obtain a diazo component solution.

Formula (D7)

35-B. Synthesis of red dye compound (D-7) by coupling reaction (step 2) The preparation of a coupling agent component solution composed of a compound of formula (C18) was carried out in the same manner as in Synthesis Example 24. Triethylamine (30 g) was appropriately added to the above coupling agent component solution at a temperature in the range of 0 to 10°C, and the above diazo component solution obtained in step 1 was added dropwise over 1 hour to carry out a coupling reaction. After stirring at a temperature in the range of 0 to 10°C for 20 minutes, the product was separated from the reaction mixture by filtration, washed with methanol, and then washed with water, and dried at 60°C until the water content was 1.0 mass % or less, to obtain a red dye compound represented by the following formula (D-7) (16.9 g, yield 68.9%). The structure of the red dye compound was confirmed by LCMS analysis (m/z 492 (M ⁺ )).

Formula (D-7)

(Synthesis Example 36) [Synthesis of purple dye compound (C-8)] The purple dye compound (C-8) was produced according to the following process.

The preparation of the coupling agent component solution composed of the compound of formula (C16) was carried out in the same manner as step 1 of Synthesis Example 16, and the preparation of the diazo component solution derived from the compound of formula (D1) was carried out in the same manner as step 5 of Synthesis Example 1. Triethylamine (32 g) was appropriately added to the above coupling agent component solution in the range of 0 to 10°C, and the above diazo component solution was added dropwise over 2 hours to carry out coupling reaction. After stirring in the range of 0 to 10°C for 20 minutes, the product was separated from the reaction mixture by filtration, washed with methanol, and then washed with water, and dried at 60°C until the water content was 1.0 mass% or less, to obtain a purple dye compound represented by the following formula (C-8) (6.14 g, yield 21.8%). The structure of the purple dye compound was confirmed to be the following formula (C-8) by LCMS analysis of molecular weight (m/z 563 (M ⁺ )).

Formula (C-8)

(Synthesis Example 37) [Synthesis of purple dye compound (C-9)] The purple dye compound (C-9) was produced according to the following process.

The same operation as in Synthesis Example 36 was performed except that the compound of formula (C9) was used instead of the compound of formula (C16) as the coupling agent component solution to obtain a purple dye compound (12.1 g) represented by the following formula (C-9). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 731 (M ⁺ )).

Formula (C-9)

(Synthesis Example 38) [Synthesis of purple dye compound (C-10)] The purple dye compound (C-10) was produced according to the following process.

A mixture of sodium bromide (5.92 g), triethylamine (0.50 g), and DMF (80 g) was stirred at 35 to 40°C for 15 minutes, and cuprous cyanide (5.0 g) was added and stirred at the same temperature for 15 minutes. A purple dye compound (C-9) (34.3 g) was added to the mixture, and the mixture was heated to 110°C and stirred for 1 hour. After cooling to 80°C, a mixture of water (190 g) and sodium hypochlorite (18 g) was added, and the mixture was stirred at 70 to 80°C for 1 hour, and then cooled to room temperature. The product was separated by filtration from the reaction mixture, washed with water, and dried at 60°C until the water content was less than 1.0 mass %, thereby obtaining a purple dye compound represented by the following formula (C-10) (20.4 g, yield 64.2%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 678 (M ⁺ )).

Formula (C-10)

(Synthesis Example 39) [Synthesis of purple dye compound (C-11)] The purple dye compound (C-11) was produced according to the following process.

39-A. Preparation of diazo component solution (Step 1) 2-bromo-6-cyano-4-nitroaniline (11.1 g) represented by the following formula (D8) was added to a mixture of concentrated sulfuric acid (10.7 g) and acetic acid (28.8 g) at a temperature between 20 and 25°C. 43% nitrosylsulfuric acid (15.6 g) was added to the mixture at a temperature between 20 and 25°C, and the mixture was stirred at the same temperature for 2 hours to obtain a diazo component solution.

Formula (D8)

39-B. Synthesis of purple dye compound (C-11) by coupling reaction (step 2) The preparation of the coupling agent component solution composed of the compound of formula (C9) is carried out in the same manner as steps 1 to 3 of Synthesis Example 9. Triethylamine (20 g) is appropriately added to the above coupling agent component solution at a temperature of 0 to 10° C., and the above diazo component solution obtained in step 1 is added dropwise over 2 hours to carry out the coupling reaction. After stirring at 0 to 10°C for 20 minutes, the product was separated from the reaction mixture by filtration, washed with methanol, then washed with water, and dried at 60°C until the water content was less than 1.0 mass %, to obtain a purple dye compound represented by the following formula (C-11) (16.0 g, yield 45.0%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 711 (M ⁺ )).

Formula (C-11)

(Synthesis Example 40) [Synthesis of purple dye compound (C-12)] The purple dye compound (C-12) was produced according to the following process.

40-A. Synthesis of coupling agent compound C23 and preparation of coupling agent component solution (Step 1) In step 3 of Synthesis Example 9, 1-bromobutane (27.4 g) was used instead of 1-bromooctane. The same operation as steps 1 to 3 of Synthesis Example 9 was performed to obtain N-[3-(N,N-dibutylamino)phenyl]octanamide represented by the following formula (C23). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C23).

Formula (C23)

40-B. Synthesis of purple dye compound (C-12) by coupling reaction (step 2) The same operation as step 2 of Synthesis Example 39 was performed except that the compound of formula (C23) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a purple dye compound represented by the following formula (C-12) (5.99 g, yield 20.0%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 599 (M ⁺ )).

Formula (C-12)

(Synthesis Example 41) [Synthesis of purple dye compound (C-13)] The purple dye compound (C-13) was produced according to the following process.

The same operation as step 2 of Synthesis Example 39 was performed except that the compound of formula (C12) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a purple dye compound represented by the following formula (C-13) (23.5 g, yield 75.0%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 627 (M ⁺ )).

Formula (C-13)

(Synthesis Example 42) [Synthesis of purple dye compound (C-14)] The purple dye compound (C-14) was produced according to the following process.

The same operation as step 2 of Synthesis Example 39 was performed except that the compound of formula (C16) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a purple dye compound represented by the following formula (C-14) (10.8 g, yield 39.8%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 543 (M ⁺ )).

Formula (C-14)

(Synthesis Example 43) [Synthesis of purple dye compound (C-15)] The purple dye compound (C-15) was produced according to the following process.

In Synthesis Example 38, except that the purple dye compound of formula (C-13) (31.4 g) was used instead of the purple dye compound of formula (C-9), the same operation as Synthesis Example 38 was performed to obtain a purple dye compound represented by the following formula (C-15) (26.9 g, yield 93.7%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 574 (M ⁺ )).

Formula (C-15)

(Synthesis Example 44) [Synthesis of purple dye compound (C-16)] The purple dye compound (C-16) was produced according to the following process.

In Synthesis Example 38, except that the purple dye compound of formula (C-14) (27.2 g) was used instead of the purple dye compound of formula (C-9), the same operation as in Synthesis Example 38 was performed to obtain a purple dye compound represented by the following formula (C-16) (22.0 g, yield 89.8%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 490 (M ⁺ )).

Formula (C-16)

(Synthesis Example 45) [Synthesis of yellow dye compound (G-3)] The yellow dye compound (G-3) was produced according to the following process.

In Synthesis Example 28, except that 2-ethylhexanoyl chloride (19.5 g) was used instead of n-octanoyl chloride, the same operation as Synthesis Example 28 was performed to obtain a yellow dye compound represented by the following formula (G-3) (33.1 g, yield 87.3%). The structure of the yellow dye compound was confirmed by LCMS analysis (m/z 379 (M ⁺ )).

Formula (G-3)

(Synthesis Example 46) [Synthesis of yellow dye compound (G-4)] The yellow dye compound (G-4) was produced according to the following process.

In Synthesis Example 28, except that nonanoyl chloride (21.2 g) was used instead of n-octanoyl chloride, the same operation as Synthesis Example 28 was performed to obtain a yellow dye compound represented by the following formula (G-4) (31.0 g, yield 78.9%). The structure of the yellow dye compound was confirmed by LCMS analysis (m/z 393 (M ⁺ )).

Formula (G-4)

(Synthesis Example 47) [Synthesis of blue dye compound (B-9)] The blue dye compound (B-9) was produced according to the following process.

The same operation as step 5 of Synthesis Example 9 was performed except that the compound of formula (C23) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (B-9) (9.12 g, yield 33.0%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 553 (M ⁺ )).

Formula (B-9)

(Synthesis Example 48) [Synthesis of blue dye compound (B-10)] The blue dye compound (B-10) was produced according to the following process.

48-A. Synthesis of coupling agent compound C24 and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 9, 2-ethylhexanoyl chloride (34.2 g) was used instead of n-octyl chloride. The same operation as steps 1 to 3 of Synthesis Example 9 was performed to obtain N-[3-(N,N-dioctylamino)phenyl]-2-ethylhexanoylamide represented by the following formula (C24). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C24).

Formula (C24)

48-B. Synthesis of blue dye compound (B-10) by coupling reaction (step 2) The same operation as steps 4 and 5 of Synthesis Example 9 was performed except that the compound of formula (C24) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (B-10) (19.0 g, yield 57.1%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 665 (M ⁺ )).

Formula (B-10)

(Synthesis Example 49) [Synthesis of orange dye compound (D-8)] The orange dye compound (D-8) was produced according to the following process.

The same operation as in Synthesis Example 24 was performed except that N,N-diethylaniline (7.45 g) was used as a coupling agent instead of the compound of formula (C18), to obtain an orange dye compound represented by the following formula (D-8) (15.2 g, yield 82.8%). The structure of the above orange dye compound was confirmed by LCMS analysis (m/z 367 (M ⁺ )).

Formula (D-8)

(Synthesis Example 50) [Synthesis of orange dye compound (D-9)] The orange dye compound (D-9) was produced according to the following process.

The same operation as in Synthesis Example 31 was performed except that N,N-diethylaniline (7.45 g) was used as a coupling agent instead of the compound of formula (C18) to obtain an orange dye compound represented by the following formula (D-9) (18.2 g, yield 80.0%). The structure of the above orange dye compound was confirmed by LCMS analysis (m/z 455 (M ⁺ )).

Formula (D-9)

(Synthesis Example 51) [Synthesis of orange dye compound (D-10)] The orange dye compound (D-10) was produced according to the following process.

The same operation as in Synthesis Example 30 was performed except that N,N-diethylaniline (7.45 g) was used as a coupling agent instead of the compound of formula (C18) to obtain an orange dye compound represented by the following formula (D-10) (9.35 g, yield 62.5%). The structure of the orange dye compound was confirmed by LCMS analysis (m/z 299 (M ⁺ )).

Formula (D-10)

(Synthesis Example 52) [Synthesis of orange dye compound (D-11)] The orange dye compound (D-11) was produced according to the following process.

52-A. Synthesis of coupling agent compound C25 and preparation of coupling agent component solution (Step 1) A mixture of aniline (18.6 g), acetic acid (50 g), cuprous chloride (1.3 g), and acrylonitrile (20 g) was heated to 110°C and stirred for 3 hours. After cooling to room temperature, toluene (100 g) and 10% sodium carbonate aqueous solution (150 g) were added to extract the organic layer. After washing the extract with saturated brine, the solvent was distilled off under reduced pressure to obtain N-cyanoethylaniline represented by the following formula (C25a) (28.7 g, yield 98.2%) as a crude product.

Formula (C25a)

(Step 2) The mixture of N-cyanoethylaniline (28.7 g), triethylamine (15 g), DMF (15 g) and 1-bromooctane (14.5 g) obtained in the above step was heated to 120°C and stirred at the same temperature for 3 hours to obtain N-cyanoethyl-N-octylaniline represented by the following formula (C25). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C25).

Formula (C25)

52-B. Synthesis of orange dye compound (D-11) by coupling reaction (step 3) The same operation as in Synthesis Example 30 was performed except that the compound of formula (C25) was used instead of the compound of formula (C18) as the coupling agent component solution to obtain an orange dye compound represented by the following formula (D-11) (10.6 g, yield 52.0%). The structure of the above orange dye compound was confirmed by LCMS analysis (m/z 408 (M ⁺ )).

Formula (D-11)

(Synthesis Example 53) [Synthesis of red dye compound (C-17)] The red dye compound (C-17) was produced according to the following process.

53-A. Synthesis of coupling agent compound C26 and preparation of coupling agent component solution (Step 1) Except that 3'-aminoacetylaniline (7.50 g) was used instead of N-(3-amino-4-methoxyphenyl)octanamide and 1-bromoethane (27.3 g) was used instead of 1-bromooctane, the same operation as step 4 of synthesis example 1 was performed to obtain N-[3-(N,N-diethylamino)phenyl]acetamide represented by the following formula (C26). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C26).

Formula (C26)

53-B. Synthesis of red dye compound (C-17) by coupling reaction (step 2) As a coupling agent compound, the compound of formula (C26) was used instead of the compound of formula (C9). The same operation as in Synthesis Example 17 was performed to obtain a red dye compound represented by the following formula (C-17) (11.8 g, yield 60.5%). The structure of the above red dye compound was confirmed by LCMS analysis (m/z 390 (M ⁺ )).

Formula (C-17)

(Synthesis Example 54) [Synthesis of purple dye compound (F-2)] The purple dye compound (F-2) was produced according to the following process.

The same operation as in Synthesis Example 29 was performed except that N,N-diethylaniline (7.45 g) was used as a coupling agent instead of the compound of formula (C18) to obtain a purple dye compound represented by the following formula (F-2) (10.6 g, yield 59.6%). The structure of the purple dye compound was confirmed by LCMS analysis (m/z 356 (M ⁺ )).

Formula (F-2)

(Synthesis Example 55) [Synthesis of blue dye compound (B-11)] The blue dye compound (B-11) was produced according to the following process.

Except that the compound of formula (C26) was used as the coupling agent compound instead of the compound of formula (C9), the same operation as steps 4 and 5 of Synthesis Example 9 was performed to obtain a blue dye compound represented by the following formula (B-11) (11.9 g, yield 57.6%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 413 (M ⁺ )).

Formula (B-11)

(Synthesis Example 56) [Synthesis of blue dye compound (A-9)] The blue dye compound (A-9) was produced according to the following process.

56-A. Synthesis of coupling agent compound C27 and preparation of coupling agent component solution (Step 1) A mixture of N-(3-amino-4-methoxyphenyl)octanamide (13.2 g), acetic acid (15 g), cuprous chloride (0.32 g), and acrylonitrile (5.0 g) obtained in Step 3 of Synthesis Example 1 was heated to 110°C and stirred for 3 hours. After cooling to room temperature, toluene (50 g) and 10% sodium carbonate aqueous solution (75 g) were added to extract the organic layer. After washing the extract with saturated saline water, the solvent was distilled off under reduced pressure to obtain N-(3-cyanoethylamino-4-methoxyphenyl)octanamide (9.05 g, yield 57.0%) represented by the following formula (C27a) as a crude product.

Formula (C27a)

(Step 2) The mixture of N-(3-cyanoethylamino-4-methoxyphenyl)octanamide (15.9 g), DMF (15 g) and diethyl sulfate (11.6 g) obtained in the above step was heated to 90°C and stirred at the same temperature for 2 hours to obtain N-(3-N-ethyl-N-cyanoethylamino-4-methoxyphenyl)octanamide represented by the following formula (C27). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C27).

Formula (C27)

56-B. Synthesis of blue dye compound (A-9) by coupling reaction (step 3) The same operation as steps 5 and 6 of Synthesis Example 1 was performed except that the compound of formula (C27) was used instead of the compound of formula (C1) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (A-9) (9.70 g, yield 31.4%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 618 (M ⁺ )).

Formula (A-9)

(Synthesis Example 57) [Synthesis of blue dye compound (A-10)] The blue dye compound (A-10) was produced according to the following process.

57-A. Synthesis of coupling agent compound C28 and preparation of coupling agent component solution (Step 1) A mixture of N-(3-cyanoethylamino-4-methoxyphenyl)octanamide (15.9 g), DMF (20 g), triethylamine (12.6 g) and 1-bromooctane (29.0 g) obtained in Step 1 of Synthesis Example 56 was heated to 120°C and stirred for 8 hours to obtain N-(3-N-octyl-N-cyanoethylamino-4-methoxyphenyl)octanamide represented by the following formula (C28). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of formula (C28).

Formula (C28)

57-B. Synthesis of blue dye compound (A-10) by coupling reaction (step 2) The same operation as steps 5 and 6 of Synthesis Example 1 was performed except that the compound of formula (C28) was used instead of the compound of formula (C1) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (A-10) (5.52 g, yield 15.7%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 702 (M ⁺ )).

Formula (A-10)

(Synthesis Example 58) [Synthesis of blue dye compound (A-11)] The blue dye compound (A-11) was produced according to the following process.

58-A. Synthesis of coupling agent compound C29 and preparation of coupling agent component solution (Step 1) A mixture of N-(3-amino-4-methoxyphenyl)octanamide (13.2 g) obtained in Step 3 of Synthesis Example 1, DMF (15 g), triethylamine (15 g) and 2-bromoethyl methyl ether (27.8 g) was heated to 110°C and stirred for 8 hours to obtain N-[3-N,N-(2-dimethoxyethyl)amino-4-methoxyphenyl]octanamide represented by the following formula (C29). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of formula (C29).

Formula (C29)

(Step 2) The same operation as Steps 5 and 6 of Synthesis Example 1 was performed except that the compound of Formula (C29) was used instead of the compound of Formula (C1) as the coupling agent component solution to obtain a blue dye compound represented by the following Formula (A-11) (6.58 g, yield 20.2%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 653 (M ⁺ )).

Formula (A-11)

(Synthesis Example 59) [Synthesis of blue dye compound (A-12)] The blue dye compound (A-12) was produced according to the following process.

59-A. Synthesis of coupling agent compound C30 and preparation of coupling agent component solution (Step 1) Except that N-(3-amino-4-methoxyphenyl)acetamide (purchased as a commercial product) (9.0 g) was used instead of N-(3-amino-4-methoxyphenyl)octanamide and 1-bromobutane (27.4 g) was used instead of 1-bromooctane, the same operation as step 4 of synthesis example 1 was performed to obtain N-[3-(N,N-dihexylamino)-4-methoxyphenyl]acetamide represented by the following formula (C30). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of formula (C30).

Formula (C30)

59-B. Synthesis of blue dye compound (A-12) by coupling reaction (step 2) The same operation as steps 5 and 6 of Synthesis Example 1 was performed except that the compound of formula (C30) was used instead of the compound of formula (C1) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (A-12) (14.1 g, yield 49.9%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 565 (M ⁺ )).

Formula (A-12)

(Synthesis Example 60) [Synthesis of blue dye compound (A-13)] The blue dye compound (A-13) was produced according to the following process.

60-A. Synthesis of coupling agent compound C31 and preparation of coupling agent component solution (Step 1) Except that N-(3-amino-4-methoxyphenyl)acetamide (purchased as a commercial product) (9.0 g) was used instead of N-(3-amino-4-methoxyphenyl)octanamide and 1-bromohexane (33.0 g) was used instead of 1-bromooctane, the same operation as step 4 of synthesis example 1 was performed to obtain N-[3-(N,N-dihexylamino)-4-methoxyphenyl]acetamide represented by the following formula (C31). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C31).

Formula (C31)

60-B. Synthesis of blue dye compound (A-13) by coupling reaction (step 2) The same operation as steps 5 and 6 of Synthesis Example 1 was performed except that the compound of formula (C31) was used instead of the compound of formula (C1) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (A-13) (10.7 g, yield 34.5%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 621 (M ⁺ )).

Formula (A-13)

(Synthesis Example 61) [Synthesis of blue dye compound (A-14)] The blue dye compound (A-14) was produced according to the following process.

61-A. Synthesis of coupling agent compound C32 and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 1, pentanoyl chloride (25.3 g) was used instead of n-octanoyl chloride, and in step 4, 1-bromoethane (27.3 g) was used instead of 1-bromooctane. The same operation as steps 1 to 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-diethylamino)-4-methoxyphenyl]pentanoylamide represented by the following formula (C32). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C32).

Formula (C32)

61-B. Synthesis of blue dye compound (A-14) by coupling reaction (step 2) The same operation as steps 5 and 6 of Synthesis Example 1 was performed except that the compound of formula (C32) was used instead of the compound of formula (C1) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (A-14) (24.1 g, yield 87.5%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 551 (M ⁺ )).

Formula (A-14)

(Synthesis Example 62) [Synthesis of blue dye compound (A-15)] The blue dye compound (A-15) was produced according to the following process.

62-A. Synthesis of coupling agent compound C33 and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 1, lauryl chloride (45.9 g) was used instead of n-octyl chloride, and in step 4, 1-bromoethane (27.3 g) was used instead of 1-bromooctane. The same operation as steps 1 to 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-diethylamino)-4-methoxyphenyl]dodecylamide represented by the following formula (C33). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C33).

Formula (C33)

62-B. Synthesis of blue dye compound (A-15) by coupling reaction (step 2) The same operation as steps 5 and 6 of Synthesis Example 1 was performed except that formula (C33) was used instead of formula (C1) as the coupling agent component solution to obtain a blue dye compound represented by the following formula (A-15) (26.8 g, yield 82.6%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 649 (M ⁺ )).

Formula (A-15)

(Synthesis Example 63) [Synthesis of red dye compound (C-18)] The red dye compound (C-18) was produced according to the following process.

63-A. Synthesis of coupling agent compound C34 and preparation of coupling agent component solution (Step 1) In step 3 of Synthesis Example 9, 1-bromohexane (33.0 g) was used instead of 1-bromooctane, and 3'-aminoacetaniline (7.50 g) was used instead of N-(3-aminophenyl)octanamide. The same operation as step 3 of Synthesis Example 9 was performed to obtain N-[3-(N,N-dihexylamino)phenyl]acetamide represented by the following formula (C34). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C34).

Formula (C34)

63-B. Synthesis of red dye compound (C-18) by coupling reaction (step 2) The same operation as in Synthesis Example 17 was performed except that the compound of formula (C34) was used instead of the compound of formula (C9) as the coupling agent component solution to obtain a red dye compound represented by the following formula (C-18) (20.1 g, yield 80.1%). The structure of the red dye compound was confirmed by LCMS analysis (m/z 502 (M ⁺ )).

Formula (C-18)

(Synthesis Example 64) [Synthesis of orange dye compound (D-12)] The orange dye compound (D-12) was produced according to the following process.

64-A. Synthesis of coupling agent compound C35 and preparation of coupling agent component solution (Step 1) Except that aniline (4.66 g) was used instead of N-(3-amino-4-methoxyphenyl)octanamide and 1-bromohexane (33.0 g) was used instead of 1-bromooctane, the same operation as step 4 of synthesis example 1 was performed to obtain N,N-dihexylaniline represented by the following formula (C35). Methanol (30 g) was added to the reaction mixture and cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C35).

Formula (C35)

64-B. Synthesis of orange dye compound (D-12) by coupling reaction (step 2) The same operation as in Synthesis Example 24 was performed except that the compound of formula (C35) was used instead of the compound of formula (C18) as the coupling agent component solution to obtain an orange dye compound represented by the following formula (D-12) (13.5 g, yield 56.4%). The structure of the above orange dye compound was confirmed by LCMS analysis (m/z 479 (M ⁺ )).

Formula (D-12)

(Synthesis Example 65) [Synthesis of orange dye compound (D-13)] The orange dye compound (D-13) was produced according to the following process.

The same operation as in Synthesis Example 30 was performed except that the compound of formula (C35) was used instead of the compound of formula (C18) as the coupling agent component solution to obtain an orange dye compound represented by the following formula (D-13) (16.4 g, yield 79.8%). The structure of the above orange dye compound was confirmed by LCMS analysis (m/z 411 (M ⁺ )).

Formula (D-13)

(Synthesis Example 66) [Synthesis of blue dye compound (A-16)] The blue dye compound (A-16) was produced according to the following process.

66-A. Synthesis of coupling agent compound C8 and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 1, 4-butoxyaniline (33.0 g) was used instead of p-methoxyaniline, and propionyl chloride (19.4 g) was used instead of n-octyl chloride. The same operation as steps 1 to 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-dioctylamino)-4-butoxyphenyl]propionamide represented by the following formula (C36). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C36).

Formula (C36)

66-B. Synthesis of blue dye compound (A-16) by coupling reaction (step 2) As the coupling agent component solution, the compound of formula (C36) obtained in step 1 was used instead of the compound of formula (C1). The same operation as steps 5 and 6 of Synthesis Example 1 was performed to obtain a blue dye compound represented by the following formula (A-16) (6.45 g, yield 17.6%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 733 (M ⁺ )).

Formula (A-16)

(Synthesis Example 67) [Synthesis of red dye compound (C-19)] The red dye compound (C-19) was produced according to the following process.

67-A. Synthesis of coupling agent compound C37 and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 9, propionyl chloride (19.4 g) was used instead of n-octyl chloride, and in step 3 of Synthesis Example 9, 1-bromohexane (33.0 g) was used instead of 1-bromooctane. Except for this, the same operation as steps 1 to 3 of Synthesis Example 9 was performed to obtain N-[3-(N,N-dihexylamino)phenyl]propionamide represented by the following formula (C37). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C37).

Formula (C37)

67-B. Synthesis of red dye compound (C-19) by coupling reaction (step 2) As the coupling agent component solution, the compound of formula (C37) obtained in step 1 was used instead of the compound of formula (C9). The same operation as steps 1 and 2 of Synthesis Example 17 was performed to obtain a red dye compound represented by the following formula (C-19) (17.6 g, yield 68.2%). The structure of the above red dye compound was confirmed by LCMS analysis (m/z 516 (M ⁺ )).

Formula (C-19)

(Synthesis Example 68) [Synthesis of red dye compound (C-20)] The red dye compound (C-20) was produced according to the following process.

The same operation as steps 1 and 2 of Synthesis Example 30 was performed except that the compound of formula (C12) was used instead of the compound of formula (C18) as the coupling agent component solution to obtain a red dye compound represented by the following formula (C-20) (23.0 g, yield 87.7%). The structure of the red dye compound was confirmed by LCMS analysis (m/z 524 (M ⁺ )).

Formula (C-20)

(Synthesis Example 69) [Synthesis of blue dye compound (A-17)] The blue dye compound (A-17) was produced according to the following process.

69-A. Synthesis of coupling agent compound C38 and preparation of coupling agent component solution (Step 1) In step 1 of Synthesis Example 1, pentanoyl chloride (25.3 g) was used instead of n-octanoyl chloride, and in step 4, 1-bromohexane (33.0 g) was used instead of 1-bromooctane. The same operation as steps 1 to 4 of Synthesis Example 1 was performed to obtain N-[3-(N,N-dihexylamino)-4-methoxyphenyl]pentanoylamide represented by the following formula (C38). Methanol (30 g) was added to the reaction mixture, and the mixture was cooled to 5°C to obtain a coupling agent component solution composed of the compound of formula (C38).

Formula (C38)

69-B. Synthesis of blue dye compound (A-17) by coupling reaction (step 2) As the coupling agent component solution, the compound of formula (C38) obtained in step 1 was used instead of the compound of formula (C1). The same operation as steps 5 and 6 of Synthesis Example 1 was performed to obtain a blue dye compound represented by the following formula (A-17) (15.3 g, yield 48.4%). The structure of the above blue dye compound was confirmed by LCMS analysis (m/z 663 (M ⁺ )).

Formula (A-17)

The structural formulas of the dye compounds described in the synthesis examples and known dye compounds are shown in Tables 3 to 9.

[Table 3] Formula (A)

[Table 4] Formula (B)

[Table 5] Formula (C)

[Table 6] Formula (D)

[Table 7] Formula (E)

[Table 8] Formula (F)

[Table 9] Formula (G)

<Production Examples of Dye Compositions> Dye compositions of the compounds listed in Tables 3 to 9 were produced for water-based dyeing. The production examples are shown below. In the present production examples, the dye composition is a liquid water-based dispersion or a powder. Specifically, dye composition production examples 1 to 105 are production examples of liquid dye compositions, and dye composition production examples 106 to 141 are production examples of powder dye compositions. In addition, the volume median particle size of the compounds in the dye composition was measured by the dynamic light scattering particle size distribution measuring device LB-500 of Horiba, Ltd.

(Dye composition preparation example 1) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound A-5 dye composition with a volume median particle size of 0.17 μm and a concentration of 20% by mass.

(Dye composition preparation example 2) 4 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 76 g of water. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound A-5 dye composition with a volume median particle size of 0.20 μm and a concentration of 20 mass %.

(Dye composition preparation example 3) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and a compound A-5 dye composition with a volume median particle size of 0.16 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 4) 30 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 50 g of water. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and a compound A-5 dye composition with a volume median particle size of 0.19 μm and a concentration of 20% by mass was obtained.

(Dye composition preparation example 5) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 50 g of water, and then 10 g of propylene glycol was dissolved. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill, and a compound A-5 dye composition with a volume median particle size of 0.19 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 6) 20 g of tristyrylphenol-ethylene oxide 50 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and a compound A-5 dye composition with a volume median particle size of 0.19 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 7) 20 g of tribenzylphenol-ethylene oxide 23 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and a compound A-5 dye composition with a volume median particle size of 0.15 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 8) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-3 dye composition with a volume median particle size of 0.12 μm and a concentration of 20 mass %.

(Dye composition preparation example 9) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide and 10 g of 50 mol adduct of tristyrylphenol-ethylene oxide as dispersants were dissolved in 60 g of water. 20 g of compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound A-3 dye composition with a volume median particle size of 0.14 μm and a concentration of 20% by mass.

(Dye composition preparation example 10) 10 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of tribenzylphenol-ethylene oxide 23 mol adduct as dispersants were dissolved in 60 g of water. 20 g of compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound A-3 dye composition with a volume median particle size of 0.12 μm and a concentration of 20% by mass.

(Dye composition preparation example 11) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide and 10 g of sodium lignin sulfonate as dispersants were dissolved in 60 g of water. 20 g of compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound A-3 dye composition with a volume median particle size of 0.16 μm and a concentration of 20% by mass.

(Dye composition preparation example 12) 10 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of sodium sulfate of tristyrylphenol-ethylene oxide 29 mol adduct as dispersants were dissolved in 60 g of water. 20 g of compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, to obtain a compound A-3 dye composition with a volume median particle size of 0.15 μm and a concentration of 20 mass %.

(Dye composition preparation example 13) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound A-1 obtained in Synthesis Example 1 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound A-1 dye composition with a volume median particle size of 0.27 μm and a concentration of 20 mass %.

(Dye composition preparation example 14) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound B-4 obtained in Synthesis Example 12 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and a compound B-4 dye composition with a volume median particle size of 0.22 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 15) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water, and then 10 g of propylene glycol was dissolved. 20 g of compound B-4 obtained in Synthesis Example 12 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill, and a compound B-4 dye composition with a volume median particle size of 0.20 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 16) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound B-3 dye composition with a volume median particle size of 0.17 μm and a concentration of 20% by mass.

(Dye composition preparation example 17) 20 g of tristyrylphenol-ethylene oxide 50 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound B-3 dye composition with a volume median particle size of 0.15 μm and a concentration of 20 mass %.

(Dye composition preparation example 18) 20 g of tribenzylphenol-ethylene oxide 23 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and a dye composition of compound B-3 with a volume median particle size of 0.16 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 19) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 50 g of water, and then 10 g of propylene glycol was dissolved. 20 g of compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill, and a compound B-3 dye composition with a volume median particle size of 0.16 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 20) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound B-1 obtained in Synthesis Example 9 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and a compound B-1 dye composition with a volume median particle size of 0.22 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 21) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound B-10 obtained in Synthesis Example 48 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound B-10 dye composition with a volume median particle size of 0.24 μm and a concentration of 20 mass %.

(Dye composition preparation example 22) 4 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 76 g of water. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-4 dye composition with a volume median particle size of 0.29 μm and a concentration of 20 mass %.

(Dye composition preparation example 23) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-4 dye composition with a volume median particle size of 0.24 μm and a concentration of 20 mass %.

(Dye composition preparation example 24) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-4 dye composition with a volume median particle size of 0.22 μm and a concentration of 20 mass %.

(Dye composition preparation example 25) 30 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 50 g of water. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-4 dye composition with a volume median particle size of 0.24 μm and a concentration of 20 mass %.

(Dye composition preparation example 26) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water, and then 10 g of diethylene glycol was dissolved. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill, and a compound C-4 dye composition with a volume median particle size of 0.20 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 27) 20 g of tristyrylphenol-ethylene oxide 50 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-4 dye composition with a volume median particle size of 0.25 μm and a concentration of 20 mass %.

(Dye composition preparation example 28) 20 g of tribenzylphenol-ethylene oxide 23 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-4 dye composition with a volume median particle size of 0.24 μm and a concentration of 20 mass %.

(Dye composition preparation example 29) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-3 dye composition with a volume median particle size of 0.25 μm and a concentration of 20 mass %.

(Dye composition preparation example 30) 20 g of tristyrylphenol-ethylene oxide 50 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and a compound C-3 dye composition with a volume median particle size of 0.26 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 31) 20 g of tribenzylphenol-ethylene oxide 23 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-3 dye composition with a volume median particle size of 0.25 μm and a concentration of 20 mass %.

(Dye composition preparation example 32) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 50 g of water, and then 10 g of ethylene glycol was dissolved. 20 g of compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill, and a compound C-3 dye composition with a volume median particle size of 0.24 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 33) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound C-1 obtained in Synthesis Example 17 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-1 dye composition with a volume median particle size of 0.20 μm and a concentration of 20 mass %.

(Dye composition preparation example 34) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound D-3 obtained in Synthesis Example 26 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound D-3 dye composition with a volume median particle size of 0.10 μm and a concentration of 20 mass %.

(Dye composition preparation example 35) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water, and then 10 g of dipropylene glycol was dissolved. 20 g of compound D-3 obtained in Synthesis Example 26 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill, and a compound D-3 dye composition with a volume median particle size of 0.10 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 36) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound D-1 obtained in Synthesis Example 24 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound D-1 dye composition with a volume median particle size of 0.27 μm and a concentration of 20 mass %.

(Dye composition preparation example 37) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound D-6 obtained in Synthesis Example 32 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound D-6 dye composition with a volume median particle size of 0.12 μm and a concentration of 20% by mass.

(Dye composition preparation example 38) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water, and then 10 g of ethylene glycol was dissolved. 20 g of compound D-6 obtained in Synthesis Example 32 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill, and a compound D-6 dye composition with a volume median particle size of 0.10 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 39) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound D-5 obtained in Synthesis Example 31 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and a compound D-5 dye composition with a volume median particle size of 0.26 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 40) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound D-4 dye composition with a volume median particle size of 0.13 μm and a concentration of 20 mass %.

(Dye composition preparation example 41) 4 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 76 g of water. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound D-4 dye composition with a volume median particle size of 0.20 μm and a concentration of 20% by mass.

(Dye composition preparation example 42) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound D-4 dye composition with a volume median particle size of 0.11 μm and a concentration of 20% by mass.

(Dye composition preparation example 43) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water, and then 10 g of propylene glycol was dissolved. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill, and a compound D-4 dye composition with a volume median particle size of 0.13 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 44) 10 g of 58 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound D-4 dye composition with a volume median particle size of 0.15 μm and a concentration of 20% by mass.

(Dye composition preparation example 45) 10 g of tristyrylphenol-ethylene oxide 50 mol adduct as a dispersant was dissolved in 70 g of water. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound D-4 dye composition with a volume median particle size of 0.15 μm and a concentration of 20 mass %.

(Dye composition preparation example 46) 10 g of tribenzylphenol-ethylene oxide 23 mol adduct as a dispersant was dissolved in 70 g of water. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and a compound D-4 dye composition with a volume median particle size of 0.18 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 47) 10 g of 40 mol adduct of tribenzylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, and a compound D-4 dye composition with a volume median particle size of 0.16 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 48) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound G-1 obtained in Synthesis Example 27 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound G-1 dye composition with a volume median particle size of 0.23 μm and a concentration of 20% by mass.

(Dye composition preparation example 49) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water, and then 10 g of polyethylene glycol (average molecular weight 400) was dissolved. 20 g of compound G-1 obtained in Synthesis Example 27 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill, and a compound G-1 dye composition with a volume median particle size of 0.30 μm and a concentration of 20 mass % was obtained.

(Dye composition preparation example 50) 20 g of formalin condensate of sodium naphthalenesulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed and a dye composition was not obtained.

(Dye composition production example 51) 20 g of sodium lignin sulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed and a dye composition was not obtained.

(Dye composition production example 52) 20 g of sodium sulfate of tristyrylphenol-ethylene oxide 29 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed and the dye composition was not obtained.

(Dye composition production example 53) 20 g of formalin condensate of sodium naphthalenesulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed and a dye composition was not obtained.

(Dye composition production example 54) 20 g of sodium lignin sulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads having a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed and a dye composition was not obtained.

(Dye composition preparation example 55) 20 g of sodium sulfate of tristyrylphenol-ethylene oxide 29 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed and the dye composition was not obtained.

(Dye composition production example 56) 20 g of formalin condensate of sodium naphthalenesulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads having a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed.

(Dye composition production example 57) 20 g of formalin condensate of dye phenol oil sodium sulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed.

(Dye composition production example 58) 20 g of sodium lignin sulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads having a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed and a dye composition was not obtained.

(Dye composition production example 59) 20 g of formalin condensate of sodium naphthalenesulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads having a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed.

(Dye composition preparation example 60) 20 g of formalin condensate of dye phenol oil sodium sulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed.

(Dye composition production example 61) 20 g of sodium lignin sulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed and a dye composition was not obtained.

(Dye composition production example 62) 20 g of sodium sulfate of tristyrylphenol-ethylene oxide 29 mol adduct as a dispersant was dissolved in 60 g of water. 20 g of compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed and the dye composition was not obtained.

(Dye composition production example 63) 10 g of formalin condensate of sodium phenol sulfonate and 10 g of sodium lignin sulfonate as dispersants were dissolved in 60 g of water. 20 g of compound D-1 obtained in Synthesis Example 24 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed and the dye composition was not obtained.

(Dye composition production example 64) 20 g of formalin condensate of sodium naphthalenesulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads having a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed.

(Dye composition production example 65) 20 g of formalin condensate of sodium methylnaphthalenesulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads having a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed.

(Dye composition production example 66) 20 g of sodium lignin sulfonate as a dispersant was dissolved in 60 g of water. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads having a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed.

(Dye composition production example 67) 10 g of formalin condensate of sodium naphthalenesulfonate and 10 g of sodium ligninsulfonate as dispersants were dissolved in 60 g of water. 20 g of compound G-1 obtained in Synthesis Example 27 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment using 200 g of glass beads having a diameter of 0.3 mm by a vertical bead mill. However, microparticle dispersion could not be performed and the dye composition was not obtained.

(Dye composition preparation example 68) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound A-13 obtained in Synthesis Example 60 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-13 dye composition with a volume median particle size of 0.15 μm and a concentration of 20 mass %.

(Dye composition preparation example 69) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound A-17 obtained in Synthesis Example 69 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-17 dye composition with a volume median particle size of 0.17 μm and a concentration of 20% by mass.

(Dye composition preparation example 70) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound A-2 obtained in Synthesis Example 2 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using a vertical bead mill using 200 g of glass beads with a diameter of 0.3 mm, thereby obtaining a compound A-2 dye composition having a volume median particle size of 0.19 μm and a concentration of 20% by mass.

(Dye composition preparation example 71) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound A-16 obtained in Synthesis Example 66 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-16 dye composition with a volume median particle size of 0.18 μm and a concentration of 20 mass %.

(Dye composition preparation example 72) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound B-2 obtained in Synthesis Example 10 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound B-2 dye composition with a volume median particle size of 0.19 μm and a concentration of 20% by mass.

(Dye composition preparation example 73) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound C-19 obtained in Synthesis Example 67 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-19 dye composition with a volume median particle size of 0.23 μm and a concentration of 20 mass %.

(Dye composition preparation example 74) 20 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 60 g of water. 20 g of compound C-20 obtained in Synthesis Example 68 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-20 dye composition with a volume median particle size of 0.24 μm and a concentration of 20 mass %.

(Dye composition preparation example 75) 10 g of 24 mol adduct of distyrylphenol-ethylene oxide as a dispersant was dissolved in 70 g of water. 20 g of compound D-13 obtained in Synthesis Example 65 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 20 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound D-13 dye composition with a volume median particle size of 0.13 μm and a concentration of 20% by mass.

(Dye composition preparation example 76) 4 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 66 g of water. 20 g of compound A-13 obtained in Synthesis Example 60 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-13 dye composition with a volume median particle size of 0.16 μm and a concentration of 20% by mass.

(Dye composition preparation example 77) 4 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 66 g of water. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-5 dye composition with a volume median particle size of 0.17 μm and a concentration of 20% by mass.

(Dye composition preparation example 78) 4 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 66 g of water. 20 g of compound A-5 obtained in Synthesis Example 5 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-5 dye composition with a volume median particle size of 0.15 μm and a concentration of 20 mass %.

(Dye composition preparation example 79) 4 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 66 g of water. 20 g of compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-3 dye composition with a volume median particle size of 0.15 μm and a concentration of 20% by mass.

(Dye composition preparation example 80) 4 g of distyrylphenol-ethylene oxide 58 mol adduct and 10 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 66 g of water. 20 g of compound A-3 obtained in Synthesis Example 3 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-3 dye composition with a volume median particle size of 0.15 μm and a concentration of 20% by mass.

(Dye composition preparation example 81) 4 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 66 g of water. 20 g of compound A-2 obtained in Synthesis Example 2 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-2 dye composition with a volume median particle size of 0.18 μm and a concentration of 20 mass %.

(Dye composition preparation example 82) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (360 mol)-propylene oxide (70 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound A-4 obtained in Synthesis Example 4 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-4 dye composition with a volume median particle size of 0.18 μm and a concentration of 20 mass %.

(Dye composition preparation example 83) 8 g of distyrylphenol-ethylene oxide 58 mol adduct and 8 g of ethylene oxide (360 mol)-propylene oxide (70 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound A-1 obtained in Synthesis Example 1 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound A-1 dye composition with a volume median particle size of 0.20 μm and a concentration of 20 mass %.

(Dye composition preparation example 84) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound B-4 obtained in Synthesis Example 12 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound B-4 dye composition with a volume median particle size of 0.22 μm and a concentration of 20% by mass.

(Dye composition preparation example 85) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound B-3 obtained in Synthesis Example 11 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound B-3 dye composition with a volume median particle size of 0.19 μm and a concentration of 20% by mass.

(Dye composition preparation example 86) 4 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 66 g of water. 20 g of compound B-2 obtained in Synthesis Example 10 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound B-2 dye composition with a volume median particle size of 0.23 μm and a concentration of 20% by mass.

(Dye composition preparation example 87) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound B-2 obtained in Synthesis Example 10 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound B-2 dye composition with a volume median particle size of 0.22 μm and a concentration of 20 mass %.

(Dye composition preparation example 88) 8 g of distyrylphenol-ethylene oxide 58 mol adduct and 8 g of ethylene oxide (360 mol)-propylene oxide (70 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound B-1 obtained in Synthesis Example 9 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound B-1 dye composition with a volume median particle size of 0.20 μm and a concentration of 20 mass %.

(Dye composition preparation example 89) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound B-10 obtained in Synthesis Example 48 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound B-10 dye composition with a volume median particle size of 0.24 μm and a concentration of 20 mass %.

(Dye composition preparation example 90) 4 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 66 g of water. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-4 dye composition with a volume median particle size of 0.24 μm and a concentration of 20 mass %.

(Dye composition preparation example 91) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound C-4 obtained in Synthesis Example 20 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-4 dye composition with a volume median particle size of 0.23 μm and a concentration of 20 mass %.

(Dye composition preparation example 92) 4 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-3 dye composition with a volume median particle size of 0.25 μm and a concentration of 20 mass %.

(Dye composition preparation example 93) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound C-3 obtained in Synthesis Example 19 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-3 dye composition with a volume median particle size of 0.25 μm and a concentration of 20 mass %.

(Dye composition preparation example 94) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound C-2 obtained in Synthesis Example 18 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-2 dye composition with a volume median particle size of 0.22 μm and a concentration of 20% by mass.

(Dye composition preparation example 95) 8 g of tristyrylphenol-ethylene oxide 50 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound C-1 obtained in Synthesis Example 17 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-1 dye composition with a volume median particle size of 0.20 μm and a concentration of 20 mass %.

(Dye composition preparation example 96) 4 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound C-20 obtained in Synthesis Example 68 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound C-20 dye composition with a volume median particle size of 0.18 μm and a concentration of 20 mass %.

(Dye composition preparation example 97) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (160 mol)-propylene oxide (60 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound D-3 obtained in Synthesis Example 26 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound D-3 dye composition with a volume median particle size of 0.14 μm and a concentration of 20% by mass.

(Dye composition preparation example 98) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound D-1 obtained in Synthesis Example 24 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound D-1 dye composition with a volume median particle size of 0.23 μm and a concentration of 20% by mass.

(Dye composition preparation example 99) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (160 mol)-propylene oxide (60 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound D-6 obtained in Synthesis Example 32 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound D-6 dye composition with a volume median particle size of 0.14 μm and a concentration of 20% by mass.

(Dye composition preparation example 100) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound D-5 obtained in Synthesis Example 31 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound D-5 dye composition with a volume median particle size of 0.24 μm and a concentration of 20% by mass.

(Dye composition preparation example 101) 4 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 66 g of water. 20 g of compound D-13 obtained in Synthesis Example 65 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound D-13 dye composition with a volume median particle size of 0.18 μm and a concentration of 20% by mass.

(Dye composition preparation example 102) 4 g of distyrylphenol-ethylene oxide 24 mol adduct and 10 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 66 g of water. 20 g of compound D-4 obtained in Synthesis Example 30 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound D-4 dye composition with a volume median particle size of 0.20 μm and a concentration of 20 mass %.

(Dye composition preparation example 103) 8 g of tribenzylphenol-ethylene oxide 40 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound E-1 obtained in Synthesis Example 33 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound E-1 dye composition with a volume median particle size of 0.24 μm and a concentration of 20 mass %.

(Dye composition preparation example 104) 8 g of tribenzylphenol-ethylene oxide 23 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound F-1 obtained in Synthesis Example 29 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound F-1 dye composition with a volume median particle size of 0.24 μm and a concentration of 20 mass %.

(Dye composition preparation example 105) 8 g of distyrylphenol-ethylene oxide 24 mol adduct and 8 g of ethylene oxide (300 mol)-propylene oxide (55 mol) copolymer as dispersants were dissolved in 64 g of water. 20 g of compound G-1 obtained in Synthesis Example 27 was added thereto and stirred to prepare an aqueous slurry. The aqueous slurry was subjected to a microparticle dispersion treatment for 24 hours using 200 g of glass beads with a diameter of 0.3 mm by a vertical bead mill to obtain a compound G-1 dye composition with a volume median particle size of 0.23 μm and a concentration of 20% by mass.

(Dye composition preparation example 106) To 50 g of the compound A-13 dye composition with a concentration of 20 mass % described in the dye composition preparation example 76, 33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound A-13 with a concentration of 20 mass %.

(Dye composition production example 107) To 50 g of the compound A-5 dye composition with a concentration of 20 mass % described in the dye composition production example 77, 33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound A-5 with a concentration of 20 mass %.

(Dye composition production example 108) To 50 g of the compound A-5 dye composition with a concentration of 20 mass % described in the dye composition production example 77, 33 g of formalin condensate of sodium methylnaphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound A-5 with a concentration of 20 mass %.

(Dye composition preparation example 109) To 50 g of the compound A-5 dye composition with a concentration of 20 mass % described in the dye composition preparation example 77, 33 g of formalin condensate of sodium phenol oil sulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound A-5 with a concentration of 20 mass %.

(Dye composition preparation example 110) To 50 g of the compound A-5 dye composition with a concentration of 20 mass % described in the dye composition preparation example 77, 33 g of sodium lignin sulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition with a concentration of 20 mass % of compound A-5.

(Dye composition preparation example 111) To 50 g of the compound A-3 dye composition with a concentration of 20 mass % described in the dye composition preparation example 79, 33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound A-3 with a concentration of 20 mass %.

(Dye composition production example 112) To 50 g of the compound A-3 dye composition with a concentration of 20 mass % described in the dye composition production example 79, 33 g of formalin condensate of sodium methylnaphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound A-3 with a concentration of 20 mass %.

(Dye composition preparation example 113) To 50 g of the compound A-2 dye composition with a concentration of 20 mass % described in the dye composition preparation example 81, 33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound A-2 with a concentration of 20 mass %.

(Dye composition preparation example 114) To 50 g of the compound B-3 dye composition with a concentration of 20 mass % described in the dye composition preparation example 85, 32 g of formalin condensate of sodium naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound B-3 with a concentration of 20 mass %.

(Dye composition preparation example 115) To 50 g of the compound B-2 dye composition with a concentration of 20 mass % described in the dye composition preparation example 87, 32 g of formalin condensate of sodium naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound B-2 with a concentration of 20 mass %.

(Dye composition production example 116) To 50 g of the compound B-2 dye composition with a concentration of 20 mass % described in the dye composition production example 87, 32 g of formalin condensate of sodium methylnaphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound B-2 with a concentration of 20 mass %.

(Dye composition production example 117) To 50 g of the dye composition of compound B-2 with a concentration of 20 mass % described in dye composition production example 87, 32 g of sodium lignin sulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound B-2 with a concentration of 20 mass %.

(Dye composition preparation example 118) To 50 g of the dye composition of compound B-1 with a concentration of 20% by mass described in dye composition preparation example 88, 32 g of formalin condensate of sodium naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound B-1 with a concentration of 20% by mass.

(Dye composition preparation example 119) To 50 g of the compound B-10 dye composition with a concentration of 20 mass % described in the dye composition preparation example 89, 32 g of formalin condensate of sodium naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition with a concentration of 20 mass % of compound B-10.

(Dye composition preparation example 120) To 50 g of the compound C-4 dye composition with a concentration of 20 mass % described in the dye composition preparation example 90, 33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound C-4 with a concentration of 20 mass %.

(Dye composition preparation example 121) To 50 g of the compound C-4 dye composition with a concentration of 20 mass % described in the dye composition preparation example 90, 33 g of formalin condensate of sodium methylnaphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound C-4 with a concentration of 20 mass %.

(Dye composition preparation example 122) To 50 g of the compound C-4 dye composition with a concentration of 20 mass % described in the dye composition preparation example 90, 33 g of formalin condensate of sodium phenol oil sulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound C-4 with a concentration of 20 mass %.

(Dye composition preparation example 123) To 50 g of the compound C-4 dye composition with a concentration of 20 mass % described in the dye composition preparation example 90, 33 g of sodium lignin sulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition with a concentration of 20 mass % of compound C-4.

(Dye composition preparation example 124) To 50 g of the compound C-3 dye composition with a concentration of 20 mass % described in the dye composition preparation example 92, 33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound C-3 with a concentration of 20 mass %.

(Dye composition preparation example 125) To 50 g of the compound C-3 dye composition with a concentration of 20 mass % described in the dye composition preparation example 92, 33 g of formalin condensate of sodium methylnaphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound C-3 with a concentration of 20 mass %.

(Dye composition preparation example 126) To 50 g of the compound C-20 dye composition with a concentration of 20 mass % described in the dye composition preparation example 96, 33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound C-20 with a concentration of 20 mass %.

(Dye composition preparation example 127) To 50 g of the compound C-20 dye composition with a concentration of 20 mass % described in the dye composition preparation example 96, 33 g of formalin condensate of sodium phenol oil sulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound C-20 with a concentration of 20 mass %.

(Dye composition preparation example 128) To 50 g of the compound D-1 dye composition with a concentration of 20 mass % described in the dye composition preparation example 98, 32 g of formalin condensate of sodium naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound D-1 with a concentration of 20 mass %.

(Dye composition preparation example 129) To 50 g of the compound D-1 dye composition with a concentration of 20 mass % described in the dye composition preparation example 98, 32 g of formalin condensate of sodium methylnaphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound D-1 with a concentration of 20 mass %.

(Dye composition preparation example 130) To 50 g of the dye composition of compound D-1 with a concentration of 20 mass % described in dye composition preparation example 98, 32 g of sodium lignin sulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound D-1 with a concentration of 20 mass %.

(Dye composition preparation example 131) To 50 g of the compound D-5 dye composition having a concentration of 20% by mass described in the dye composition preparation example 100, 32 g of formalin condensate of sodium naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition having a concentration of 20% by mass of compound D-5.

(Dye composition preparation example 132) To 50 g of the compound D-5 dye composition with a concentration of 20 mass % described in the dye composition preparation example 100, 32 g of formalin condensate of sodium methylnaphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound D-5 with a concentration of 20 mass %.

(Dye composition preparation example 133) To 50 g of the compound D-5 dye composition with a concentration of 20 mass % described in the dye composition preparation example 100, 32 g of sodium lignin sulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition with a concentration of 20 mass % of compound D-5.

(Dye composition preparation example 134) To 50 g of the compound D-13 dye composition with a concentration of 20 mass % described in the dye composition preparation example 101, 33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound D-13 with a concentration of 20 mass %.

(Dye composition preparation example 135) To 50 g of the compound D-4 dye composition with a concentration of 20 mass % described in the dye composition preparation example 102, 33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound D-4 with a concentration of 20 mass %.

(Dye composition production example 136) To 50 g of the compound D-4 dye composition with a concentration of 20 mass % described in the dye composition production example 102, 33 g of formalin condensate of sodium naphthalenesulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound D-4 with a concentration of 20 mass %.

(Dye composition production example 137) To 50 g of the compound D-4 dye composition with a concentration of 20 mass % described in the dye composition production example 102, 33 g of sodium lignin sulfonate and 17 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition with a concentration of 20 mass % of compound D-4.

(Dye composition production example 138) To 50 g of the compound E-1 dye composition with a concentration of 20 mass % described in the dye composition production example 103, 32 g of sodium lignin sulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition with a concentration of 20 mass % of compound E-1.

(Dye composition preparation example 139) To 50 g of the compound F-1 dye composition with a concentration of 20 mass % described in the dye composition preparation example 104, 32 g of formalin condensate of sodium naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound F-1 with a concentration of 20 mass %.

(Dye composition production example 140) To 50 g of the compound G-1 dye composition with a concentration of 20 mass % described in the dye composition production example 105, 32 g of formalin condensate of sodium naphthalenesulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound G-1 with a concentration of 20 mass %.

(Dye composition preparation example 141) To 50 g of the dye composition of compound G-1 with a concentration of 20% by mass described in dye composition preparation example 105, 32 g of formalin condensate of sodium phenol oil sulfonate and 18 g of water were added and stirred for 20 minutes. The dye dispersion was spray dried to obtain a powdered dye composition of compound G-1 with a concentration of 20% by mass.

As for the dispersant used to make the compound of the present invention into a dye composition, effective ones are non-ionic dispersants such as distyrylphenol-ethylene oxide adducts, tristyrylphenol-ethylene oxide adducts, tribenzylphenol-ethylene oxide adducts, ethylene oxide-propylene oxide copolymers, etc. described in Dye Composition Preparation Examples 1 to 49 and 68 to 105.

On the other hand, the anionic dispersants such as formalin condensate of sodium naphthalenesulfonate, formalin condensate of sodium phenol oil sulfonate, sodium lignin sulfonate, etc. described in Dye Composition Preparation Examples 50 to 67 cannot make the compound of the present invention into a dye composition with the desired particle size (volume median particle size of less than 1.0 μm) when used alone.

<Dyeing Example> (Exhaust dyeing of polypropylene fiber 1) Using only one of the dye compositions of the compounds listed in Tables 3 to 9 or the disperse dye compounds previously used for dyeing polyester fibers and the like as shown in Tables 3 to 9, polypropylene fibers are dyed by exhaust dyeing.

(Dyeing Example P1) Water and acetic acid were added to 1.5 g of the blue compound A-5 dye composition (dye concentration 20 mass%) obtained in Dye Composition Preparation Example 1 to prepare a dye bath with a total amount of 2000 g and a pH value of 4.5. 100 g of polypropylene fiber was immersed in the above dye bath and dyed at 120°C for 40 minutes (0.3% o.m.f.), then fully washed with water and dried to obtain a blue polypropylene fiber dyed product.

(Dyeing Examples P2 to P22) Dyed polypropylene fiber dyed products were obtained by the same dyeing sequence as Dyeing Example P1 except that the dye composition of the blue compound A-5 described in Dyeing Example P1 was changed to the dye composition of the compounds in Tables 10 to 14.

(Dyeing Example P26) 95 g of water was added to 5.0 g of the powdered dye composition (dye concentration 20% by mass) of the blue compound A-13 obtained in Dye Composition Preparation Example 106 and stirred to prepare a dye dispersion. Water and acetic acid were added to the dye dispersion to prepare a dye bath with a total amount of 2000 g and a pH value of 4.5. 100 g of polypropylene fiber was immersed in the above dye bath and dyed at 130°C for 60 minutes (1.0% o.m.f.), followed by reduction washing, water washing and drying to obtain a blue polypropylene fiber dyed product.

(Dyeing Examples P27 to P37) Dyeing polypropylene fiber dyed products were obtained by the same dyeing sequence as Dyeing Example P26 except that the powdered dye composition of the blue compound A-13 described in Dyeing Example P26 was changed to the powdered dye composition of the compounds in Tables 10 to 14.

The compounds used in Staining Examples P1 to P22 and Staining Examples P26 to P37 are shown in Tables 10 to 14.

[Table 10] Formula (A)

[Table 11] Formula (B)

[Table 12] Formula (C)

[Table 13] Formula (D)

[Table 14] Formula (G)

The polypropylene fiber dyed products obtained in the dyeing example were subjected to dyeability evaluation, light fastness test, sublimation fastness test, washing fastness test, perspiration fastness test, rubbing fastness test and fastness to heat pressing test.

(1) Dyeability evaluation Dyeability is evaluated by using the Total K/S value obtained by colorimetric measurement of the dyed fabric. The colorimetric measurement of the dyed fabric is performed using an integrating sphere spectrophotometer Color-Eye 5 (manufactured by GretagMacbeth). The dyed fabric is pasted on white paper and the measurement is performed under a light source of D65 and a 2-degree field of view.

(2) Light fastness test The light fastness test is conducted by the ultraviolet carbon arc lamp method in accordance with JIS L0842:2004. The test method is outlined as follows. Using the ultraviolet fading tester U48 (manufactured by Suga Test Instruments Co., Ltd.), the dyed fabric is exposed to light for 20 hours at a black panel temperature of 63±3℃, and the fading is determined.

(3) Sublimation fastness test The sublimation fastness test is conducted in accordance with JIS L0854:2013. The test method is outlined as follows. The dyed cloth is sandwiched between nylon cloth and kept at 120±2℃ for 80 minutes under a load of 12.5 kPa. The fading and contamination of the nylon cloth are then determined.

(4) Washing fastness test The washing fastness test is conducted in accordance with JIS L0844:2011 (A-2). The test method is outlined as follows. The dyed fabric is attached to a multi-fiber interwoven fabric and washed for 30 minutes at 50±2°C in the presence of soap to determine discoloration and contamination of the cotton and nylon parts of the multi-fiber interwoven fabric. In addition, the contamination of the residual liquid after washing is determined.

(5) Sweat fastness test The sweat fastness test is conducted in accordance with JIS L0848:2004. The test method is outlined as follows. The dyed fabric is attached to a multi-fiber interwoven fabric and immersed in acidic artificial sweat or alkaline artificial sweat for 30 minutes. After being kept at 37±2℃ for 4 hours under a load of 12.5 kPa, it is dried below 60℃ to determine whether the fabric is discolored or not and whether the cotton and nylon parts of the multi-fiber interwoven fabric are contaminated.

(6) Friction fastness test The friction fastness test is conducted in accordance with JIS L0849:2013. The test method is outlined as follows. Using a friction fastness tester RT-300 (manufactured by Daiei Scientific Instruments Manufacturing Co., Ltd.), a load of 2 N is applied to a dry cotton cloth or a wet cotton cloth and the dyed cloth is rubbed back and forth 100 times to determine the coloration of the cotton cloth.

(7) Fastness test to heat pressing The fastness test to heat pressing is conducted in accordance with JIS L0850:2015 (A-2 drying). The test method is briefly described as follows. The dyed cloth is overlapped on the cotton cloth and kept on a heating plate at 150°C under a load of 4±1 kPa for 15 seconds. The fading and contamination of the cotton cloth are then determined.

The evaluation results of the dyeing examples of the compound of formula (A) are shown in Table 15.

[Table 15] Staining Example P1 P2 P3 P26 P27 P28 Synthesis Example 5 3 - 60 3 2 Dye compounds A-5 A-3 A-X3 A-13 A-3 A-2 Dye composition production example 1 8 - 106 111 113 X _A NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO _{2 Y} Br Br Br Br Br Br R _A1 C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H _{5 C6H13 ​} C ₈ H ₁₇ C ₈ H _{17 R} C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H _{5 C6H13 ​} C ₈ H ₁₇ C ₈ H _{17 R} CH ₃ C ₂ H ₅ CH ₃ CH ₃ C ₂ H ₅ C ₄ H _{9 R} CH ₃ CH ₃ CH ₃ CH ₃ CH ₃ CH ₃ Dye compounds 0.3% omf 0.3% omf 0.3% omf 1.0% omf 1.0% omf 1.0% omf Dyeability Total K/S 110 111 twenty three 134 176 190 Light fastness Less than Level 3 Less than Level 3 No rating 3 Less than Level 3 Less than Level 3 Sublimation fastness 4-5 4-5 No rating 4-5 4-5 4 Wash fastness Faded 5 5 No rating 5 4-5 5 pollute Cotton 4-5 5 No rating 5 5 5 Nylon 5 5 No rating 5 5 5 Residual liquid pollution 4 4-5 No rating 4 4 4 Sweat fastness (acid) Faded 5 5 No rating 5 5 5 pollute Cotton 5 5 No rating 5 5 5 Nylon 5 5 No rating 5 5 5 Sweat fastness (alkaline) Faded 5 5 No rating 5 5 5 pollute Cotton 5 5 No rating 5 5 5 Nylon 5 5 No rating 5 5 5 Friction fastness Dry 3 4 No rating 3-4 4-5 4 Wet 3 3-4 No rating 3-4 4-5 4-5 Hot Press 5 5 No rating 5 5 5

Regarding the dyeing properties of the compound of formula (A), the compounds used in Dyeing Examples P1, P2, and P26 to P28, in which _RA1 , _RA2 , and _RA3 are independently alkyl groups having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 , and _RA3 is an alkyl group having 4 to 14 carbon atoms), have good dyeing properties. The disperse dye used in Dyeing Example P3, i.e., the compound in which _RA1 , _RA2 , and _RA3 are all alkyl groups having 3 or less carbon atoms, has poor dyeing properties.

In addition, regarding the fastnesses of the compounds of formula (A), the compounds in which _RA1 , _RA2 and _RA3 used in dyeing examples P1, P2 and P26 to P28 are independently alkyl groups having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 and _RA3 is an alkyl group having 4 to 14 carbon atoms) have good sublimation fastness, washing fastness, perspiration fastness, rubbing fastness and fastness to heat pressing.

The evaluation results of the dyeing examples of the compound of formula (B) are shown in Table 16.

[Table 16] Staining Example P4 P5 P8 P29 P30 P31 Synthesis Example 12 11 - 11 10 48 Dye compounds B-4 B-3 B-X1 B-3 B-2 B-10 Dye composition production example 14 16 - 114 115 119 R _B1 C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H ₄ OCH ₃ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _B2 C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H ₄ OCH ₃ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _B3 CH ₃ C ₂ H ₅ CH ₃ C ₂ H ₅ C ₄ H ₉ Ethyl-pentyl Dye compounds 0.3% omf 0.3% omf 0.3% omf 1.0% omf 1.0% omf 1.0% omf Dyeability Total K/S 51 79 17 157 184 146 Light fastness Less than Level 3 Less than Level 3 No rating 4 4 4 Sublimation fastness 4-5 4-5 No rating 4-5 4-5 5 Wash fastness Faded 4-5 5 No rating 4-5 5 5 pollute Cotton 5 5 No rating 4 4 4-5 Nylon 4-5 5 No rating 4-5 5 5 Residual liquid pollution 4 4-5 No rating 4 4 4 Sweat fastness (acid) Faded 5 5 No rating 5 5 5 pollute Cotton 5 5 No rating 5 5 5 Nylon 5 5 No rating 5 5 5 Sweat fastness (alkaline) Faded 5 5 No rating 5 5 5 pollute Cotton 5 5 No rating 5 5 5 Nylon 5 5 No rating 5 5 5 Friction fastness Dry 2-3 2-3 No rating 2 2 2 Wet 3 2-3 No rating 2 2-3 2-3 Hot Press 5 5 No rating 5 4-5 5

Regarding the dyeing properties of the compound of formula (B), the compounds used in Dyeing Examples P4 to P7 and P29 to P31, in which R _B1 and R _B2 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms), have good dyeing properties. The disperse dye used in Dyeing Example P8, i.e., the compound in which R _B1 or R _B2 is not an alkyl group having 1 to 14 carbon atoms, which is previously used for dyeing polyester fibers, has poor dyeing properties. In addition, regarding the fastnesses of the compounds of formula (B), the compounds in which R _B1 and R _B2 used in dyeing examples P4 to P7 and P29 to P31 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms) have good fastness to light, fastness to sublimation, fastness to washing, fastness to perspiration, and fastness to heat pressing.

The evaluation results of the dyeing examples of the compound of formula (C) are shown in Table 17.

[Table 17] Staining Example P10 P12 P32 P33 P34 Synthesis Example 19 - 20 19 68 Dye compounds C-3 C-X2 C-4 C-3 C-20 Dye composition production example 29 - 120 124 126 X _C Cl Cl Cl Cl H Y _C H H H H H R _C1 C ₈ H ₁₇ C ₂ H ₄ OCOMe C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _C2 C ₈ H ₁₇ C ₂ H ₄ OCOMe C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H _{17 C3} C ₂ H ₅ C ₂ H ₅ CH ₃ C ₂ H ₅ CH ₃ Dye compounds 0.3% omf 0.3% omf 1.0% omf 1.0% omf 1.0% omf Dyeability Total K/S 73 17 160 176 123 Light fastness 4 No rating 4 6 3-4 Sublimation fastness 4 No rating 4 4 4-5 Wash fastness Faded 3-4 No rating 4-5 5 5 pollute Cotton 5 No rating 5 5 5 Nylon 5 No rating 5 4-5 4-5 Residual liquid pollution 4 No rating 3-4 3-4 3-4 Sweat fastness (acid) Faded 5 No rating 4-5 5 5 pollute Cotton 5 No rating 5 4-5 5 Nylon 5 No rating 5 5 5 Sweat fastness (alkaline) Faded 5 No rating 4-5 5 5 pollute Cotton 5 No rating 5 4-5 5 Nylon 5 No rating 5 5 5 Friction fastness Dry 4 No rating 3 3-4 3-4 Wet 4 No rating 3-4 3-4 3-4 Hot Press 5 No rating 5 5 5

Regarding the dyeing properties of the compound of formula (C), the compounds used in Dyeing Examples P9 to P11, and P32 to P34, in which R _C1 , R _C2, and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2, and R _C3 is an alkyl group having 4 to 14 carbon atoms), have good dyeing properties. The disperse dye used in Dyeing Example P12, i.e., the compound in which at least one of R _C1 , R _C2, and R _C3 is an alkyl group having 3 or less carbon atoms, which is previously used for dyeing polyester fibers, has poor dyeing properties.

In addition, regarding the fastness of the compounds of formula (C), the compounds in which R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms) are generally good.

In addition, regarding the fastnesses of the compounds of formula (C), the compounds in which R _C1 , R _C2 and R _C3 used in Dyeing Examples P9 to P12 and P32 to P34 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms) have good fastnesses.

The evaluation results of the dyeing examples of the compound of formula (D) are shown in Table 18.

[Table 18] Staining Example P13 P14 P15 P16 P17 P18 P19 P20 P35 P36 Synthesis Example 26 twenty four 32 31 30 - - - 65 30 Dye compounds D-3 D-1 D-6 D-5 D-4 D-X1 D-X2 D-X3 D-13 D-4 Dye composition production example 34 36 37 39 40 - - - 134 135 _XD Cl Cl Br Br H Cl Br H H H _Y Cl Cl Br Br H Cl Br H H H R _D1 C ₄ H ₉ C ₈ H ₁₇ C ₄ H ₉ C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H ₄ CN C ₂ H ₅ C ₂ H _{5 C6H13 ​} C ₈ H ₁₇ R _D2 C ₄ H ₉ C ₈ H ₁₇ C ₄ H ₉ C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H ₄ CN C ₂ H ₄ CN C ₂ H ₄ CN _{C6H13 ​} C ₈ H ₁₇ Dye compounds 0.3% omf 0.3% omf 0.3% omf 0.3% omf 0.3% omf 0.3% omf 0.3% omf 0.3% omf 1.0% omf 1.0% omf Dyeability Total K/S 41 53 29 52 98 5 8 5 232 243 Light fastness 4-5 3 5 3-4 3-4 No rating No rating No rating 5 5 Sublimation fastness 2-3 3-4 3 4 3 No rating No rating No rating 2 2-3 Wash fastness Faded 4 4-5 4 4-5 5 No rating No rating No rating 5 5 pollute Cotton 4-5 5 5 5 5 No rating No rating No rating 4-5 5 Nylon 4 5 4 5 5 No rating No rating No rating 4 4-5 Residual liquid pollution 2-3 4 2-3 4 3 No rating No rating No rating 2 2-3 Sweat fastness (acid) Faded 3-4 5 4 5 5 No rating No rating No rating 5 5 pollute Cotton 5 5 5 5 5 No rating No rating No rating 5 5 Nylon 4-5 5 5 5 5 No rating No rating No rating 5 5 Sweat fastness (alkaline) Faded 3-4 5 4 5 5 No rating No rating No rating 5 5 pollute Cotton 5 5 5 5 5 No rating No rating No rating 5 5 Nylon 4-5 5 5 5 5 No rating No rating No rating 5 5 Friction fastness Dry 4-5 4-5 4 5 4-5 No rating No rating No rating 4 4-5 Wet 4 4-5 3-4 4-5 4-5 No rating No rating No rating 4 4 Hot Press 4-5 5 5 5 5 No rating No rating No rating 5 5

Regarding the dyeing property of the compound of formula (D), the dyeing property of the compound in which R _D1 and R _D2 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms) used in dyeing examples P13 to P17, and P35 and P36 is good. However, in the case of disperse dyes previously used for dyeing polyester fibers, etc., used in dyeing examples P18 to P20, the dyeing property is poor when the alkyl groups of R _D1 and R _D2 each have an alkyl group having 1 to 3 carbon atoms.

In addition, regarding the fastness of the compound of formula (D), the larger the carbon number of R _D1 and R _D2, the better.

The evaluation results of the dyeing examples of the compound of formula (G) are shown in Table 19.

[Table 19] Staining Example P21 P22 P37 Synthesis Example 27 - 27 Dye compounds G-1 G-X5 G-1 Dye composition production example 48 - 140 R _G Hexyl-nonyl C ₃ H ₇ Hexyl-nonyl Dye compounds 0.3% omf 0.3% omf 1.0% omf Dyeability Total K/S 20 6 60 Light fastness 3-4 No rating 3 Sublimation fastness 4-5 No rating 4-5 Wash fastness Faded 5 No rating 5 pollute Cotton 5 No rating 5 Nylon 5 No rating 5 Residual liquid pollution 4 No rating 3 Sweat fastness (acid) Faded 5 No rating 5 pollute Cotton 5 No rating 5 Nylon 5 No rating 5 Sweat fastness (alkaline) Faded 5 No rating 5 pollute Cotton 5 No rating 5 Nylon 5 No rating 5 Friction fastness Dry 5 No rating 4-5 Wet 4-5 No rating 4-5 Hot Press 5 No rating 5

Regarding the dyeing properties of the compound of formula (G), the compounds in which R _G is an alkyl group having 7 or 10 to 18 carbon atoms used in Dyeing Examples P21 and P37 have good dyeing properties. The disperse dye used in Dyeing Example P22, i.e., the compound in which R _G is an alkyl group having 3 carbon atoms, which is previously used for dyeing polyester fibers, has poor dyeing properties.

With regard to the fastness properties of the compounds of formula (G), the compounds in which _RG is an alkyl group having 7 or 10 to 18 carbon atoms used in dyeing examples P21 and P37 are good.

(Dyeing of polypropylene fibers 2) Using a dye composition in which two or more of the compounds listed in Tables 3 to 9 are mixed, polypropylene fibers are dyed in the same manner as in Dyeing Example P1. The polypropylene fiber dyed products obtained are subjected to dyeability evaluation, light fastness test, sublimation fastness test, washing fastness test, perspiration fastness test, rubbing fastness test, and fastness to heat pressing test. Furthermore, dyeability is evaluated using the Total K/S value and L ^* value, a ^* value, and b ^* value obtained by color measurement of the dyed cloth. Furthermore, the color measurement of the dyed cloth is performed using an integrating sphere spectrophotometer Color-Eye 5 (manufactured by GretagMacbeth Co.), with the dyed cloth pasted on white paper, under an observation light source of D65 and a 2-degree field of view.

Table 20 shows the evaluation results of dyeing examples using dye compositions in which two or more of the compounds listed in Tables 3 to 9 are mixed.

[Table 20] Staining Example P23 P24 P25 P38 P39 P40 Dye compounds (dye composition production example) A-2 (81) 3.18% omf A-3 (8) 1.40% omf 1.10% omf 1.10% omf A-3 (79) 1.68% omf 3.23% omf B-10 (89) 1.68% omf C-3 (29) 0.10% omf 0.20% omf 0.20% omf C-4 (90) 0.13% omf 0.18% omf D-1 (36) 0.70% omf D-4 (40) 0.50% omf D-4 (102) 0.64% omf 0.64% omf 0.64% omf D-5 (39) 0.70% omf Dye compounds total 2.0% omf 2.0% omf 2.0% omf 4.0% omf 4.0% omf 4.0% omf Dyeability L* 24.2 29.1 29.8 20.9 20.5 22.0 a* 4.7 4.1 4.3 3.7 3.5 2.9 b* -6.0 -5.6 -5.3 -2.1 0.6 1.2 Total K/S 300 213 203 458 501 445 Light fastness 3 4 3-4 5-6 4-5 3-4 Sublimation fastness No rating No rating No rating 3-4 3-4 4 Wash fastness Faded 4 4-5 4-5 4-5 5 5 pollute Cotton 5 4-5 5 4-5 4-5 4 Nylon 5 5 5 4-5 4 4 Liquid pollution 3-4 3-4 3-4 2 2-3 2-3 Sweat fastness (acid) Faded 5 4-5 4-5 4-5 5 5 pollute Cotton 5 5 5 4-5 5 5 Nylon 5 5 5 4-5 5 4-5 Sweat fastness (alkaline) Faded 5 4-5 4-5 4-5 5 5 pollute Cotton 5 5 5 4 4 3 Nylon 5 5 5 4 4-5 4-5 Friction fastness Dry 3-4 3-4 3-4 1-2 2 1-2 Wet 3 3-4 3 2 2-3 2 Hot Press No rating No rating No rating 4-5 5 4-5

As shown in Table 20, when the orange dye, red dye, and blue dye obtained in the present invention are used in combination, a black dyed cloth having good dyeability and generally good fastness can be obtained.

(Dyeing of polyethylene fiber 1) Dyeing of polyethylene fiber by the dip dyeing method is performed using only one of the dye compositions of the compounds listed in Tables 3 to 9 or the disperse dye compounds previously used for dyeing polyester fibers and the like as shown in Tables 3 to 9.

(Dyeing Example E1) Water and acetic acid were added to 1.5 g of the dye composition of the blue compound A-5 obtained in Dye Composition Preparation Example 1 (dye concentration 20 mass%) to prepare a dye bath with a total amount of 2000 g and a pH value of 4.5. 100 g of polyethylene fiber was immersed in the above dye bath and dyed at 100°C for 40 minutes (0.3% o.m.f.), then fully washed with water and dried to obtain a blue polyethylene fiber dyed product.

(Dyeing Examples E2 to E22) Dyeing of polyethylene fibers was obtained by the same dyeing sequence as in Dyeing Example E1 except that the dye composition of the blue compound A-5 described in Dyeing Example E1 was changed to the dye composition of the compounds in Tables 21 to 25.

(Dyeing Example E26) 95 g of water was added to 5.0 g of the powdered dye composition (dye concentration 20% by mass) of the blue compound A-13 obtained in Dye Composition Preparation Example 106 and stirred to prepare a dye dispersion. Water and acetic acid were added to the dye dispersion to prepare a dye bath with a total amount of 2000 g and a pH value of 4.5. 100 g of polyethylene fiber was immersed in the above dye bath and dyed at 110°C for 60 minutes (1.0% o.m.f.), then fully washed with water and dried to obtain a blue polypropylene fiber dyed product.

(Dyeing Examples E27 to E37) Dyeing polyethylene fiber dyed products were obtained by the same dyeing sequence as in Dyeing Example E26 except that the powdered dye composition of the blue compound A-13 described in Dyeing Example E26 was changed to the powdered dye composition of the compounds in Tables 21 to 25.

The compounds used in Staining Examples E1 to E22 and Staining Examples E26 to E37 are shown in Tables 10 to 14.

[Table 21] Formula (A)

[Table 22] Formula (B)

[Table 23] Formula (C)

[Table 24] Formula (D)

[Table 25] Formula (G)

The polyethylene fiber dyed product obtained in the dyeing example was subjected to dyeability evaluation, light fastness test, washing fastness test, perspiration fastness test, and rubbing fastness test in the same manner as the polypropylene fiber dyed product obtained in the above (dyeing of polypropylene fiber 1).

The evaluation results of the dyeing examples of the compound of formula (A) are shown in Table 26.

[Table 26] Staining Example E1 E2 E3 E26 E27 E28 Synthesis Example 5 3 - 60 3 2 Dye compounds A-5 A-3 A-X3 A-13 A-3 A-2 Dye composition production example 1 8 - 106 111 113 X _A NO ₂ NO ₂ NO ₂ NO ₂ NO ₂ NO _{2 Y} Br Br Br Br Br Br R _A1 C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H _{5 C6H13 ​} C ₈ H ₁₇ C ₈ H _{17 R} C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H _{5 C6H13 ​} C ₈ H ₁₇ C ₈ H _{17 R} CH ₃ C ₂ H ₅ CH ₃ CH ₃ C ₂ H ₅ C ₄ H _{9 R} CH ₃ CH ₃ CH ₃ CH ₃ CH ₃ CH ₃ Dye compounds 0.3% omf 0.3% omf 0.3% omf 1.0% omf 1.0% omf 1.0% omf Dyeability Total K/S 101 78 12 71 38 110 Light fastness Less than Level 3 Less than Level 3 No rating 3-4 Less than Level 3 3 Wash fastness Faded 5 5 No rating 4-5 4-5 4-5 pollute Cotton 5 5 No rating 4 5 5 Nylon 4-5 5 No rating 4-5 5 5 Residual liquid pollution 4 4 No rating 4 4 4 Sweat fastness (acid) Faded 5 5 No rating 4-5 5 4-5 pollute Cotton 5 5 No rating 4 5 5 Nylon 5 5 No rating 4-5 5 5 Sweat fastness (alkaline) Faded 5 5 No rating 4-5 5 4-5 pollute Cotton 5 5 No rating 4 5 5 Nylon 5 5 No rating 4-5 5 5 Friction fastness Dry 5 5 No rating 2 2 2-3 Wet 4-5 4-5 No rating 3 3 3-4

Regarding the dyeing properties of the compound of formula (A), the compounds in which R _A1 , R _A2 and R _A3 used in Dyeing Examples E1, E2 and E26 to E28 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _A1 , R _A2 and R _A3 is an alkyl group having 4 to 14 carbon atoms) have good dyeing properties. The disperse dye used in Dyeing Example E3, i.e., the compound in which R _A1 , R _A2 and R _A3 are all alkyl groups having 3 or less carbon atoms, has poor dyeing properties.

In addition, regarding the fastnesses of the compounds of formula (A), the compounds in which _RA1 , _RA2 and _RA3 used in dyeing examples E1, E2 and E26 to E28 are independently alkyl groups having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 and _RA3 is an alkyl group having 4 to 14 carbon atoms) have good wash fastness, perspiration fastness and rubbing fastness.

The evaluation results of the dyeing examples of the compound of formula (B) are shown in Table 27.

[Table 27] Staining Example E4 E5 E8 E29 E30 E31 Synthesis Example 12 11 - 11 10 48 Dye compounds B-4 B-3 B-X1 B-3 B-2 B-10 Dye composition production example 14 16 - 114 115 119 R _B1 C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H ₄ OCH ₃ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _B2 C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H ₄ OCH ₃ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _B3 CH ₃ C ₂ H ₅ CH ₃ C ₂ H ₅ C ₄ H ₉ Ethyl-pentyl Dye compounds 0.3% omf 0.3% omf 0.3% omf 1.0% omf 1.0% omf 1.0% omf Dyeability Total K/S 33 48 7 63 81 71 Light fastness 3-4 4-5 No rating 5 6 6 Wash fastness Faded 4 5 No rating 4 4-5 4-5 pollute Cotton 4-5 5 No rating 4-5 4-5 4-5 Nylon 4-5 5 No rating 5 5 5 Residual liquid pollution 4 4-5 No rating 4-5 4 4 Sweat fastness (acid) Faded 4-5 5 No rating 4-5 5 5 pollute Cotton 5 5 No rating 5 4-5 5 Nylon 5 5 No rating 5 5 5 Sweat fastness (alkaline) Faded 4-5 5 No rating 4-5 5 5 pollute Cotton 4-5 5 No rating 5 4-5 5 Nylon 5 5 No rating 5 5 5 Friction fastness Dry 2-3 5 No rating 2 1-2 2 Wet 3 4-5 No rating 3-4 3 3

Regarding the dyeing properties of the compound of formula (B), the compounds used in Dyeing Examples E4 to E7 and E29 to E31, in which R _B1 and R _B2 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms), have good dyeing properties. The disperse dye used in Dyeing Example E8, i.e., the compound in which R _B1 or R _B2 is not an alkyl group having 1 to 14 carbon atoms, has poor dyeing properties.

In addition, regarding the fastnesses of the compounds of formula (B), the compounds in which R _B1 and R _B2 used in dyeing examples E4 to E7 and E29 to E31 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms) have generally good fastnesses to light, washing, perspiration and rubbing.

The evaluation results of the dyeing examples of the compound of formula (C) are shown in Table 28.

[Table 28] Staining Example E10 E12 E32 E33 E34 Synthesis Example 19 - 20 19 68 Dye compounds C-3 C-X2 C-4 C-3 C-20 Dye composition production example 29 - 120 124 126 X _C Cl Cl Cl Cl H Y _C H H H H H R _C1 C ₈ H ₁₇ C ₂ H ₄ OCOMe C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _C2 C ₈ H ₁₇ C ₂ H ₄ OCOMe C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H _{17 C3} C ₂ H ₅ C ₂ H ₅ CH ₃ C ₂ H ₅ CH ₃ Dye compounds 0.3% omf 0.3% omf 1.0% omf 1.0% omf 1.0% omf Dyeability Total K/S 36 9 128 100 78 Light fastness 5 No rating 6 6 6 Wash fastness Faded 4-5 No rating 5 5 4-5 pollute Cotton 5 No rating 3-4 4 3-4 Nylon 5 No rating 4-5 4-5 4 Residual liquid pollution 3-4 No rating 3-4 3-4 3 Sweat fastness (acid) Faded 4-5 No rating 5 5 5 pollute Cotton 5 No rating 4 4 4 Nylon 5 No rating 4-5 4-5 3-4 Sweat fastness (alkaline) Faded 4-5 No rating 5 5 5 pollute Cotton 5 No rating 3-4 4 3 Nylon 5 No rating 4-5 4-5 3-4 Friction fastness Dry 4-5 No rating 2 2-3 2 Wet 4 No rating 3 3 3

Regarding the dyeing properties of the compound of formula (C), the compounds used in Dyeing Examples E9 to E11, and E32 to E34, in which R _C1 , R _C2, and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2, and R _C3 is an alkyl group having 4 to 14 carbon atoms), have good dyeing properties. The disperse dye used in Dyeing Example E12, i.e., the compound in which at least one of R _C1 , R _C2, and R _C3 is an alkyl group having 3 or less carbon atoms, has poor dyeing properties.

In addition, regarding the fastness of the compound of formula (C), the light fastness, perspiration fastness, and rubbing fastness of the compound in which R _C1 , R _C2 and R _C3 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms) are generally good.

In addition, regarding the fastnesses of the compounds of formula (C), the compounds in which R _C1 , R _C2 and R _C3 used in Dyeing Examples E9 to E11, and E32 to E34 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms) have good fastnesses.

The evaluation results of the dyeing examples of the compound of formula (D) are shown in Table 29.

[Table 29] Staining Example E13 E14 E15 E16 E17 E18 E19 E20 E35 E36 Synthesis Example 26 twenty four 32 31 30 - - - 65 30 Dye compounds D-3 D-1 D-6 D-5 D-4 D-X1 D-X2 D-X3 D-13 D-4 Dye composition production example 34 36 37 39 40 - - - 134 135 _XD Cl Cl Br Br H Cl Br H H H _Y Cl Cl Br Br H Cl Br H H H R _D1 C ₄ H ₉ C ₈ H ₁₇ C ₄ H ₉ C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H ₄ CN C ₂ H ₅ C ₂ H _{5 C6H13 ​} C ₈ H ₁₇ R _D2 C ₄ H ₉ C ₈ H ₁₇ C ₄ H ₉ C ₈ H ₁₇ C ₈ H ₁₇ C ₂ H ₄ CN C ₂ H ₄ CN C ₂ H ₄ CN _{C6H13 ​} C ₈ H ₁₇ Dye compounds 0.3% omf 0.3% omf 0.3% omf 0.3% omf 0.3% omf 0.3% omf 0.3% omf 0.3% omf 1.0% omf 1.0% omf Dyeability Total K/S 25 45 15 58 55 5 8 5 153 156 Light fastness 5 5 5 4-5 5 No rating No rating No rating 5-6 5 Wash fastness Faded 4 4 4 5 4-5 No rating No rating No rating 5 5 pollute Cotton 4 5 4-5 5 5 No rating No rating No rating 4-5 4-5 Nylon 3-4 4-5 4 5 5 No rating No rating No rating 4-5 5 Residual liquid pollution 2 3 3 3 2 No rating No rating No rating 3 3-4 Sweat fastness (acid) Faded 4-5 5 4 5 5 No rating No rating No rating 5 5 pollute Cotton 4 5 4 5 5 No rating No rating No rating 4-5 4-5 Nylon 4 5 4 5 5 No rating No rating No rating 5 4-5 Sweat fastness (alkaline) Faded 4-5 5 4 5 5 No rating No rating No rating 5 5 pollute Cotton 3-4 5 4 5 5 No rating No rating No rating 4-5 4-5 Nylon 3-4 5 4 5 5 No rating No rating No rating 4-5 4-5 Friction fastness Dry 3 4-5 2-3 5 4-5 No rating No rating No rating 4-5 4-5 Wet 3-4 4-5 3-4 4-5 4 No rating No rating No rating 4 4

Regarding the dyeing property of the compound of formula (D), the dyeing property of the compound in which R _D1 and R _D2 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms) used in dyeing examples E13 to E17, and E35 and E36 is good. However, in the case of disperse dyes previously used for dyeing polyester fibers, etc., used in dyeing examples E18 to E20, the dyeing property is poor when the alkyl groups of R _D1 and R _D2 each have an alkyl group having 1 to 3 carbon atoms.

In addition, regarding the fastness of the compound of formula (D), the larger the carbon number of R _D1 and R _D2, the better.

The evaluation results of the dyeing examples of the compound of formula (G) are shown in Table 30.

[Table 30] Staining Example E21 E22 E37 Synthesis Example 27 - 27 Dye compounds G-1 G-X5 G-1 Dye composition production example 48 - 140 R _G Hexyl-nonyl C ₃ H ₇ Hexyl-nonyl Dye compounds 0.3% omf 0.3% omf 1.0% omf Dyeability Total K/S 20 6 51 Light fastness 6 No rating 5 Wash fastness Faded 5 No rating 5 pollute Cotton 5 No rating 5 Nylon 5 No rating 5 Residual liquid pollution 4 No rating 3-4 Sweat fastness (acid) Faded 5 No rating 5 pollute Cotton 5 No rating 5 Nylon 5 No rating 5 Sweat fastness (alkaline) Faded 5 No rating 5 pollute Cotton 5 No rating 4-5 Nylon 5 No rating 5 Friction fastness Dry 5 No rating 5 Wet 4-5 No rating 4-5

Regarding the dyeing properties of the compound of formula (G), the compounds in which R _G is an alkyl group having 7 or 10 to 18 carbon atoms used in dyeing examples E21 and E37 have good dyeing properties. The disperse dye used in dyeing example E22, i.e., the compound in which R _G is an alkyl group having 3 carbon atoms, which is previously used for dyeing polyester fibers, has poor dyeing properties.

With regard to the fastness properties of the compounds of formula (G), the compounds in which _RG is an alkyl group having 7 or 10 to 18 carbon atoms used in dyeing examples E21 and E37 were good.

(Dyeing of polyethylene fiber 2) Using a dye composition in which two or more compounds listed in Tables 3 to 9 are mixed, polyethylene fiber is dyed in the same manner as in Dyeing Example E1. The obtained polyethylene fiber dyed product is subjected to dyeability evaluation, light fastness test, washing fastness test, perspiration fastness test, and rubbing fastness test in the same manner as the polypropylene fiber dyed product obtained in the above (Dyeing of polypropylene fiber 2).

Table 31 shows the evaluation results of dyeing examples using dye compositions in which two or more of the compounds listed in Tables 3 to 9 were mixed.

[Table 31] Staining Example E23 E24 E25 E38 E39 E40 Dye compounds (dye composition production example) A-2 (81) 2.96% omf A-3 (8) 1.40% omf 1.10% omf 1.10% omf A-3 (79) 1.60% omf 2.96% omf B-10 (89) 1.60% omf C-3 (29) 0.10% omf 0.20% omf 0.20% omf C-4 (90) 0.24% omf 0.24% omf D-1 (36) 0.70% omf D-4 (40) 0.50% omf D-4 (102) 0.80% omf 0.80% omf 0.80% omf D-5 (39) 0.70% omf Dye compounds total 2.0% omf 2.0% omf 2.0% omf 4.0% omf 4.0% omf 4.0% omf Dyeability L* 53.4 45.4 41.7 29.1 22.2 27.0 a* 5.6 1.6 3.8 4.7 6.4 8.7 b* -7.1 -6.8 -4.7 -2.4 -1.9 -2.6 Total K/S 50 86 104 242 387 264 Light fastness 6 6 6 6 6 6 Wash fastness Faded 5 5 4-5 5 5 5 pollute Cotton 3-4 3-4 3-4 4 4 4 Nylon 4 4 4-5 4-5 4 4 Liquid pollution 3-4 3-4 3-4 3-4 3-4 3-4 Sweat fastness (acid) Faded 5 5 5 5 5 5 pollute Cotton 4-5 5 4-5 5 4-5 4 Nylon 4-5 5 4-5 5 4-5 4-5 Sweat fastness (alkaline) Faded 5 5 5 5 5 5 pollute Cotton 4-5 4-5 3 5 4-5 4 Nylon 4-5 5 5 5 4-5 4-5 Friction fastness Dry 1-2 2 1-2 1-2 1-2 1-2 Wet 2-3 3 2-3 3 3 3

As shown in Table 31, when the orange dye, red dye, and blue dye obtained in the present invention are mixed and used, a black dyed cloth with good dyeability and generally good fastness can be obtained.

(Printing and dyeing of polypropylene fibers 1) Dyeing of polypropylene fibers is performed by a printing and dyeing method using only one of the dye compositions of the compounds listed in Tables 3 to 9 or the disperse dye compounds previously used for dyeing polyester fibers, etc., as shown in Tables 3 to 9.

(Dyeing Example PP1) 5.8 g of carboxymethyl cellulose, 0.3 g of sodium chlorate, and 0.3 g of tartaric acid were added to 73.6 g of water and stirred to obtain paste A. 18.5 g of water was added to 1.5 g of the dye composition (dye concentration 20 mass%) of the blue compound A-13 obtained in Dye Composition Preparation Example 76 and stirred, and the obtained dye dispersion was added to the above-mentioned paste A and stirred to obtain a printing and dyeing paste (0.3% o.m.p.). The above-mentioned printing and dyeing paste was printed on polypropylene fiber, and after being dry-dried at 110℃ for 3 minutes, the color was developed at 130℃ for 6 minutes using an H.T. steamer, and then the color was reduced, washed, and dried to obtain a blue polypropylene fiber dyed product.

(Dyeing Examples PP2 to PP12) Dyed polypropylene fiber dyed products were obtained by the same dyeing sequence as in Dyeing Example PP1 except that the dye composition of the blue compound A-13 described in Dyeing Example PP1 was changed to the dye composition of the compounds in Tables 32 to 36.

(Dyeing Example PP13) 5.8 g of carboxymethyl cellulose, 0.3 g of sodium chlorate, and 0.3 g of tartaric acid were added to 73.6 g of water and stirred to obtain paste A. 18.5 g of water was added to 1.5 g of the powdered dye composition (dye concentration 20 mass%) of the blue compound A-5 obtained in Dye Composition Preparation Example 107 and stirred, and the obtained dye dispersion was added to the above-mentioned paste A and stirred to obtain a printing and dyeing paste (0.3% o.m.p.). The above-mentioned printing and dyeing paste was printed on polypropylene fiber, and after being dry-dried at 110℃ for 3 minutes, the color was developed at 130℃ for 6 minutes using an H.T. steamer, and then the color was reduced, washed, and dried to obtain a blue polypropylene fiber dyed product.

(Dyeing Examples PP14 to PP19) Dyed polypropylene fiber dyed products were obtained by the same dyeing sequence as in Dyeing Example PP13 except that the powdered dye composition of the blue compound A-5 described in Dyeing Example PP13 was changed to the powdered dye composition of the compounds in Tables 32 to 36.

[Table 32] Formula (A)

[Table 33] Formula (B)

[Table 34] Formula (C)

[Table 35] Formula (D)

[Table 36] Formula (G)

The polypropylene fiber dyed product obtained in the dyeing example was subjected to dyeability evaluation, light fastness test, sublimation fastness test, washing fastness test, perspiration fastness test, rubbing fastness test and fastness to heat pressing test in the same manner as the polypropylene fiber dyed product obtained in the above (dyeing of polypropylene fiber 1).

The evaluation results of the dyeing examples of the compound of formula (A) are shown in Table 37.

[Table 37] Staining Example PP1 PP2 PP3 PP13 Synthesis Example 60 3 2 5 Dye compounds A-13 A-3 A-2 A-5 Dye composition production example 76 79 81 107 X _A NO ₂ NO ₂ NO ₂ NO _{2 Y} Br Br Br Br R _{A1 C6H13 ​} C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H _{17 R C6H13 ​} C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H _{17 R} CH ₃ C ₂ H ₅ C ₄ H ₉ CH _{3 R} CH ₃ CH ₃ CH ₃ CH ₃ Dye compounds 0.3% omp 0.3% omp 0.3% omp 0.3% omp Dyeability Total K/S 147 115 144 168 Light fastness Less than Level 3 Less than Level 3 Less than Level 3 3 Sublimation fastness 5 4-5 5 5 Wash fastness Faded 5 5 5 4-5 pollute Cotton 4-5 4-5 5 4-5 Nylon 5 5 5 3-4 Residual liquid pollution 4 4 4 5 Sweat fastness (acid) Faded 5 5 5 5 pollute Cotton 5 5 5 5 Nylon 5 5 5 5 Sweat fastness (alkaline) Faded 5 5 5 5 pollute Cotton 5 5 5 5 Nylon 5 5 5 5 Friction fastness Dry 3 3-4 4-5 3 Wet 3-4 3-4 4-5 4 Hot Press 5 5 5 4-5

Regarding the dyeability of the compound of formula (A), the compound in which _RA1 , _RA2 and _RA3 used in Dyeing Examples PP1 to PP3 and PP13 are independently an alkyl group having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 and _RA3 is an alkyl group having 4 to 14 carbon atoms) has good dyeability.

In addition, regarding the fastnesses of the compound of formula (A), the compound in which _RA1 , _RA2 and _RA3 used in dyeing examples PP1 to PP3 and PP13 are independently an alkyl group having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 and _RA3 is an alkyl group having 4 to 14 carbon atoms) has good sublimation fastness, washing fastness, perspiration fastness, rubbing fastness and fastness to heat pressing.

The evaluation results of the dyeing examples of the compound of formula (B) are shown in Table 38.

[Table 38] Staining Example PP4 PP5 PP14 Synthesis Example 11 10 10 Dye compounds B-3 B-2 B-2 Dye composition production example 85 87 115 R _B1 C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _B2 C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _B3 C ₂ H ₅ C ₄ H ₉ C ₄ H ₉ Dye compounds 0.3% omp 0.3% omp 0.3% omp Dyeability Total K/S 118 119 179 Light fastness 3-4 3-4 4-5 Sublimation fastness 5 5 4-5 Wash fastness Faded 4-5 4-5 5 pollute Cotton 4-5 4-5 3 Nylon 5 5 4-5 Residual liquid pollution 4 4 3-4 Sweat fastness (acid) Faded 5 5 5 pollute Cotton 5 5 5 Nylon 5 5 5 Sweat fastness (alkaline) Faded 5 5 5 pollute Cotton 5 5 5 Nylon 5 5 5 Friction fastness Dry 3 3 3 Wet 3-4 3 3-4 Hot Press 5 5 5

Regarding the dyeability of the compound of formula (B), the compound in which R _B1 and R _B2 used in Dyeing Examples PP4 to PP6 and PP14 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms) has good dyeability.

In addition, regarding the fastnesses of the compounds of formula (B), the compounds used in dyeing examples PP4 to PP6, in which R _B1 and R _B2 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms), have good fastnesses.

The evaluation results of the dyeing examples of the compound of formula (C) are shown in Table 39.

[Table 39] Staining Example PP7 PP8 PP9 PP15 PP16 Synthesis Example 20 19 68 20 68 Dye compounds C-4 C-3 C-20 C-4 C-20 Dye composition production example 90 92 96 120 126 X _C Cl Cl H Cl H Y _C H H H H H R _C1 C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _C2 C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H _{17 C3} CH ₃ C ₂ H ₅ CH ₃ CH ₃ CH ₃ Dye compounds 0.3% omp 0.3% omp 0.3% omp 0.3% omp 0.3% omp Dyeability Total K/S 134 123 108 165 133 Light fastness 6 6 5 6 5-6 Sublimation fastness 4-5 4-5 4-5 4 4 Wash fastness Faded 5 5 5 5 5 pollute Cotton 4 4 3-4 4-5 3-4 Nylon 4-5 4-5 4 4-5 4 Residual liquid pollution 3 3-4 3 3-4 3 Sweat fastness (acid) Faded 5 5 5 5 5 pollute Cotton 5 5 5 5 5 Nylon 5 5 5 5 5 Sweat fastness (alkaline) Faded 5 5 5 5 5 pollute Cotton 5 5 5 5 5 Nylon 5 5 5 5 5 Friction fastness Dry 3-4 4 4 3 3-4 Wet 3-4 4 3-4 3-4 4 Hot Press 5 5 5 5 5

Regarding the dyeability of the compound of formula (C), the compounds in which R _C1 , R _C2 and R _C3 used in Dyeing Examples PP7 to PP9, PP15 and PP16 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms) have good dyeability.

In addition, regarding the fastnesses of the compounds of formula (C), the compounds in which R _C1 , R _C2 and R _C3 used in Dyeing Examples PP7 to PP9, PP15 and PP16 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms) have good fastnesses.

The evaluation results of the dyeing examples of the compound of formula (D) are shown in Table 40.

[Table 40] Staining Example PP10 PP11 PP17 PP18 Synthesis Example 65 30 30 31 Dye compounds D-13 D-4 D-4 D-5 Dye composition production example 101 102 135 131 _XD H H H Br _Y H H H Br R _{D1 C6H13 ​} C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _{D2 C6H13 ​} C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ Dye compounds 0.3% omp 0.3% omp 0.3% omp 0.3% omp Dyeability Total K/S 138 159 182 122 Light fastness 5-6 5-6 5 5 Sublimation fastness 3 3-4 3 4-5 Wash fastness Faded 5 5 5 4-5 pollute Cotton 5 5 5 5 Nylon 4-5 5 4-5 4-5 Residual liquid pollution 3 3 3-4 3-4 Sweat fastness (acid) Faded 5 5 5 5 pollute Cotton 5 5 5 5 Nylon 5 5 5 5 Sweat fastness (alkaline) Faded 5 5 5 5 pollute Cotton 5 5 5 5 Nylon 5 5 5 5 Friction fastness Dry 4-5 4-5 3-4 4 Wet 4 4-5 4-5 4-5 Hot Press 5 5 5 5

Regarding the dyeability of the compound of formula (D), the compounds in which R _D1 and R _D2 used in Dyeing Examples PP10, PP11, PP17 and PP18 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms) have good dyeability.

In addition, regarding the fastnesses of the compounds of formula (D), the compounds in which R _D1 and R _D2 used in dyeing examples PP10, PP11, PP17 and PP18 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms) have good fastnesses.

The evaluation results of the dyeing examples of the compound of formula (G) are shown in Table 41.

[Table 41] Staining Example PP12 PP19 Synthesis Example 27 27 Dye compounds G-1 G-1 Dye composition production example 105 140 R _G Hexyl-nonyl Hexyl-nonyl Dye compounds 0.3% omp 0.3% omp Dyeability Total K/S 32 52 Light fastness 4 3 Sublimation fastness 5 4-5 Wash fastness Faded 5 5 pollute Cotton 5 4-5 Nylon 5 5 Residual liquid pollution 4 4 Sweat fastness (acid) Faded 5 5 pollute Cotton 5 5 Nylon 5 5 Sweat fastness (alkaline) Faded 5 5 pollute Cotton 5 5 Nylon 5 5 Friction fastness Dry 5 4-5 Wet 5 4-5 Hot Press 5 5

Regarding the dyeing properties of the compound of formula (G), the compounds in which _RG is an alkyl group having 7 or 10 to 18 carbon atoms used in Dyeing Examples PP12 and PP19 have good dyeing properties.

With regard to the fastness properties of the compounds of formula (G), the compounds in which _RG is an alkyl group having 7 or 10 to 18 carbon atoms used in dyeing examples PP12 and PP19 are good.

(Printing and dyeing of polypropylene fibers 2) Using a dye composition containing two or more of the compounds listed in Tables 3 to 9, polypropylene fibers were dyed using a 1.2% o.m.p. printing and dyeing paste according to dyeing example PP1.

Furthermore, using a dye composition in which two or more of the compounds listed in Tables 3 to 9 were mixed, polypropylene fibers were dyed according to Dyeing Example PP13 using a 1.8% o.m.p. printing paste.

The obtained polypropylene fiber dyed product was subjected to dyeability evaluation, light fastness test, sublimation fastness test, washing fastness test, perspiration fastness test, rubbing fastness test and fastness to heat pressing test in the same manner as the polypropylene fiber dyed product obtained in the above (dyeing of polypropylene fiber 2).

The results are shown in Table 42.

[Table 42] Staining Example PP20 PP21 PP22 Dye compounds (dye composition production example) A-2 (81) 0.96% omp A-3 (79) 0.48% omp 0.89% omp A-3 (111) B-2 (115) B-10 (89) 0.48% omp C-4 (90) 0.07% omp 0.05% omp C-4 (120) D-4 (102) 0.24% omp 0.24% omp 0.19% omp D-4 (134) Dye compounds total 1.2% omp 1.2% omp 1.2% omp Dyeability L* 24.2 23.6 28.1 a* 3.1 4.6 2.3 b* -4.7 -7.3 -5.8 Total K/S 346 344 265 Light fastness 5 3-4 3-4 Sublimation fastness 4-5 4-5 4-5 Wash fastness Faded 5 5 5 pollute Cotton 4 4-5 4-5 Nylon 5 4-5 4-5 Liquid pollution 3 3 3-4 Sweat fastness (acid) Faded 5 5 5 pollute Cotton 5 5 5 Nylon 5 5 5 Sweat fastness (alkaline) Faded 5 5 5 pollute Cotton 5 5 5 Nylon 5 5 5 Friction fastness Dry 1-2 2-3 2-3 Wet 4 3 3 Hot Press 5 5 5

As shown in Table 42, when the orange dye, red dye, and blue dye obtained in the present invention are mixed and used, a black dyed cloth with good dyeability and good fastness can be obtained.

(Printing and dyeing of polyethylene fibers 1) Dyeing of polyethylene fibers by a printing and dyeing method is performed using only one of the dye compositions of the compounds listed in Tables 3 to 9 or the disperse dye compounds previously used for dyeing polyester fibers, etc., as shown in Tables 3 to 9.

(Dyeing Example EP1) 5.8 g of carboxymethyl cellulose, 0.3 g of sodium chlorate, and 0.3 g of tartaric acid were added to 73.6 g of water and stirred to obtain paste A. 18.5 g of water was added to 1.5 g of the dye composition (dye concentration 20 mass%) of the blue compound A-13 obtained in Dye Composition Preparation Example 76 and stirred, and the obtained dye dispersion was added to the above-mentioned paste A and stirred to obtain a printing and dyeing paste (0.3% o.m.p.). The above-mentioned printing and dyeing paste was printed on polyethylene fiber, and after being dry-dried at 110℃ for 3 minutes, the color was developed at 110℃ for 6 minutes in an H.T. steamer, and then the product was reduced, washed, and dried to obtain a blue polyethylene fiber dyed product.

(Dyeing Examples EP2 to EP12) Dyeing polyethylene fiber dyed products were obtained by the same dyeing sequence as in Dyeing Example EP1 except that the dye composition of the blue compound A-13 described in Dyeing Example EP1 was changed to the dye composition of the compounds in Tables 43 to 47.

(Dyeing Example EP13) 5.8 g of carboxymethyl cellulose, 0.3 g of sodium chlorate, and 0.3 g of tartaric acid were added to 73.6 g of water and stirred to obtain paste A. 18.5 g of water was added to 1.5 g of the powdered dye composition (dye concentration 20 mass%) of the blue compound A-5 obtained in Dye Composition Preparation Example 105 and stirred, and the obtained dye dispersion was added to the above-mentioned paste A and stirred to obtain a printing and dyeing paste (0.3% o.m.p.). The above-mentioned printing and dyeing paste was printed on polyethylene fiber, and after being dry-dried at 110℃ for 3 minutes, the color was developed at 110℃ for 6 minutes in an H.T. steamer, and then the product was reduced, washed, and dried to obtain a blue polyethylene fiber dyed product.

(Dyeing Examples EP14 to EP19) Dyeing polyethylene fiber dyed products were obtained by the same dyeing sequence as in Dyeing Example EP13 except that the powdered dye composition of the blue compound A-5 described in Dyeing Example EP13 was changed to the powdered dye composition of the compounds in Tables 44 to 47.

[Table 43] Formula (A)

[Table 44] Formula (B)

[Table 45] Formula (C)

[Table 46] Formula (D)

[Table 47] Formula (G)

The polyethylene fiber dyeing obtained in the dyeing example was subjected to dyeability evaluation, light fastness test, washing fastness test, perspiration fastness test and rubbing fastness test in the same manner as the polypropylene fiber dyeing obtained in the above (dyeing of polypropylene fiber 1).

The evaluation results of the dyeing examples of the compound of formula (A) are shown in Table 48.

[Table 48] Staining Example EP1 EP2 EP3 EP13 Synthesis Example 60 3 2 5 Dye compounds A-13 A-3 A-2 A-5 Dye composition production example 76 79 81 107 X _A NO ₂ NO ₂ NO ₂ NO _{2 Y} Br Br Br Br R _{A1 C6H13 ​} C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H _{17 R C6H13 ​} C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H _{17 R} CH ₃ C ₂ H ₅ C ₄ H ₉ CH _{3 R} CH ₃ CH ₃ CH ₃ CH ₃ Dye compounds 0.3% omp 0.3% omp 0.3% omp 0.3% omp Dyeability Total K/S 28 27 41 130 Light fastness Less than Level 3 Less than Level 3 Less than Level 3 Less than Level 3 Wash fastness Faded 4-5 4-5 5 5 pollute Cotton 5 5 5 4-5 Nylon 5 5 5 5 Residual liquid pollution 4 4 4 3-4 Sweat fastness (acid) Faded 5 5 5 5 pollute Cotton 5 5 5 5 Nylon 5 5 5 5 Sweat fastness (alkaline) Faded 5 5 5 5 pollute Cotton 5 5 5 5 Nylon 5 5 5 5 Friction fastness Dry 4 5 5 4 Wet 4 4-5 4-5 4-5

Regarding the dyeability of the compound of formula (A), the compound in which _RA1 , _RA2 and _RA3 used in Dyeing Examples EP1 to EP3 and EP13 are independently an alkyl group having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 and _RA3 is an alkyl group having 4 to 14 carbon atoms) has good dyeability.

In addition, regarding the fastnesses of the compounds of formula (A), the compounds in which _RA1 , _RA2 and RA3 used in dyeing examples EP1 to EP3 and _EP13 are independently alkyl groups having 1 to 14 carbon atoms (wherein at least one of _RA1 , _RA2 and _RA3 is an alkyl group having 4 to 14 carbon atoms) have good wash fastness, perspiration fastness and rubbing fastness.

The evaluation results of the dyeing examples of the compound of formula (B) are shown in Table 49.

[Table 49] Staining Example EP4 EP5 EP14 Synthesis Example 11 10 10 Dye compounds B-3 B-2 B-2 Dye composition production example 85 87 115 R _B1 C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _B2 C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _B3 C ₂ H ₅ C ₄ H ₉ C ₄ H ₉ Dye compounds 0.3% omp 0.3% omp 0.3% omp Dyeability Total K/S 27 34 86 Light fastness 3 3 Less than Level 3 Wash fastness Faded 4-5 5 5 pollute Cotton 5 4-5 5 Nylon 5 5 5 Residual liquid pollution 4 4 4 Sweat fastness (acid) Faded 4-5 5 5 pollute Cotton 5 5 5 Nylon 5 5 5 Sweat fastness (alkaline) Faded 4-5 5 5 pollute Cotton 5 5 5 Nylon 5 5 5 Friction fastness Dry 5 4 3 Wet 4-5 4 4

Regarding the dyeability of the compound of formula (B), the compounds in which R _B1 and R _B2 used in Dyeing Examples EP4 to EP6 and EP14 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms) have good dyeability.

In addition, regarding the fastnesses of the compounds of formula (B), the compounds in dyeing examples EP4 to EP6 and EP14, in which R _B1 and R _B2 each independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _B1 , R _B2 and R _B3 is an alkyl group having 4 to 14 carbon atoms), have good fastnesses.

The evaluation results of the dyeing examples of the compound of formula (C) are shown in Table 50.

[Table 50] Staining Example EP7 EP8 EP9 EP15 EP16 Synthesis Example 20 19 68 20 68 Dye compounds C-4 C-3 C-20 C-4 C-20 Dye composition production example 90 92 96 120 126 X _C Cl Cl H Cl H Y _C H H H H H R _C1 C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _C2 C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H _{17 C3} CH ₃ C ₂ H ₅ CH ₃ CH ₃ CH ₃ Dye compounds 0.3% omp 0.3% omp 0.3% omp 0.3% omp 0.3% omp Dyeability Total K/S 41 41 32 125 120 Light fastness 6 5-6 6 4 3-4 Wash fastness Faded 5 4-5 4-5 5 5 pollute Cotton 5 5 5 5 5 Nylon 5 5 5 5 5 Residual liquid pollution 3-4 3-4 4 3-4 3 Sweat fastness (acid) Faded 5 5 5 5 5 pollute Cotton 5 5 5 5 5 Nylon 5 5 5 5 5 Sweat fastness (alkaline) Faded 5 5 5 5 5 pollute Cotton 5 5 5 5 5 Nylon 5 5 5 5 5 Friction fastness Dry 4-5 4-5 4-5 4 4 Wet 4 4 4 4-5 4

Regarding the dyeability of the compound of formula (C), the compounds in which R _C1 , R _C2 and R _C3 used in Dyeing Examples EP7 to EP9, EP15 and EP16 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms) have good dyeability.

In addition, regarding the fastnesses of the compounds of formula (C), the compounds in which R _C1 , R _C2 and R _C3 used in dyeing examples EP7 to EP9, EP15 and EP16 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _C1 , R _C2 and R _C3 is an alkyl group having 4 to 14 carbon atoms) have good fastnesses.

The evaluation results of the dyeing examples of the compound of formula (D) are shown in Table 51.

[Table 51] Staining Example EP10 EP11 EP17 EP18 Synthesis Example 65 30 30 31 Dye compounds D-13 D-4 D-4 D-5 Dye composition production example 101 102 135 131 _XD H H H Br _Y H H H Br R _{D1 C6H13 ​} C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ R _{D2 C6H13 ​} C ₈ H ₁₇ C ₈ H ₁₇ C ₈ H ₁₇ Dye compounds 0.3% omp 0.3% omp 0.3% omp 0.3% omp Dyeability Total K/S 69 70 113 87 Light fastness 5-6 5-6 3-4 3-4 Wash fastness Faded 5 4-5 5 5 pollute Cotton 5 5 5 5 Nylon 5 5 5 5 Residual liquid pollution 3 3-4 3-4 3-4 Sweat fastness (acid) Faded 5 5 5 5 pollute Cotton 5 5 5 5 Nylon 5 5 5 5 Sweat fastness (alkaline) Faded 5 5 5 5 pollute Cotton 5 5 5 5 Nylon 5 5 5 5 Friction fastness Dry 5 5 5 5 Wet 4 4 4-5 5

Regarding the dyeability of the compound of formula (D), the compounds in which R _D1 and R _D2 used in dyeing examples EP10, EP11, EP17 and EP18 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms) have good dyeability.

In addition, regarding the fastnesses of the compounds of formula (D), the compounds in which R _D1 and R _D2 used in dyeing examples EP10, EP11, EP17 and EP18 independently represent an alkyl group having 1 to 14 carbon atoms (wherein at least one of R _D1 and R _D2 is an alkyl group having 4 to 14 carbon atoms) have good fastnesses.

The evaluation results of the dyeing examples of the compound of formula (G) are shown in Table 52.

[Table 52] Staining Example EP12 EP19 Synthesis Example 27 27 Dye compounds G-1 G-1 Dye composition production example 105 140 R _G Hexyl-nonyl Hexyl-nonyl Dye compounds 0.3% omp 0.3% omp Dyeability Total K/S 16 26 Light fastness 5 3-4 Wash fastness Faded 5 5 pollute Cotton 5 5 Nylon 5 5 Residual liquid pollution 3-4 4 Sweat fastness (acid) Faded 5 5 pollute Cotton 5 5 Nylon 5 5 Sweat fastness (alkaline) Faded 5 5 pollute Cotton 5 5 Nylon 5 5 Friction fastness Dry 5 5 Wet 4-5 5

Regarding the dyeing properties of the compound of formula (G), the compounds in which _RG is an alkyl group having 7 or 10 to 18 carbon atoms used in dyeing examples EP12 and EP19 have good dyeing properties.

With regard to the fastness properties of the compounds of formula (G), the compounds in which _RG is an alkyl group having 7 or 10 to 18 carbon atoms used in dyeing examples EP12 and EP19 are good.

(Printing and dyeing of polyethylene fibers 2) Using a dye composition containing two or more of the compounds listed in Tables 3 to 9, polyethylene fibers were dyed using a 1.2% o.m.p. printing paste according to Dyeing Example EP1.

Furthermore, polyethylene fibers were dyed using a dye composition in which two or more compounds listed in Tables 3 to 9 were mixed, according to Dyeing Example EP13, using a 1.8% o.m.p. printing paste.

The obtained polyethylene fiber dyeing was subjected to dyeability evaluation, light fastness test, washing fastness test, perspiration fastness test and rubbing fastness test in the same manner as the polypropylene fiber dyeing obtained in the above (dyeing of polypropylene fiber 2).

The results are shown in Table 53.

[Table 53] Staining Example EP20 EP21 EP22 Dye compounds (dye composition production example) A-2 (81) 0.89% omp A-3 (79) 0.48% omp 0.89% omp A-3 (111) B-2 (115) B-10 (89) 0.48% omp C-4 (90) 0.07% omp 0.07% omp C-4 (120) D-4 (102) 0.24% omp 0.24% omp 0.24% omp D-4 (134) Dye compounds total 1.2% omp 1.2% omp 1.2% omp Dyeability L* 35.6 36.4 38.1 a* 6.9 9.9 9.4 b* -3.3 -6.6 -3.6 Total K/S 152 135 123 Light fastness 5 5-6 5 Wash fastness Faded 4-5 5 5 pollute Cotton 5 5 5 Nylon 5 5 5 Liquid pollution 3-4 3-4 3-4 Sweat fastness (acid) Faded 5 5 5 pollute Cotton 5 5 5 Nylon 5 5 5 Sweat fastness (alkaline) Faded 5 5 5 pollute Cotton 5 5 5 Nylon 5 5 5 Friction fastness Dry 2-3 2-3 2-3 Wet 3 3-4 3-4

As shown in Table 53, when the orange dye, red dye, and blue dye obtained in the present invention are mixed and used, a black dyed cloth with good dyeability and good fastness can be obtained.

As mentioned above, the present invention is not limited to the above-mentioned embodiments, and the present invention also includes embodiments in which the configurations of the embodiments are appropriately combined or replaced.

Furthermore, based on the knowledge of the industry, the combination or order of steps in the implementation form may be appropriately reorganized or various design changes may be made to the implementation form, and the implementation form with such changes may also be included in the scope of the present invention. [Industrial Applicability]

The present invention can be used to dye polyolefin fibers used in clothing, underwear, hats, socks, gloves, sportswear and other clothing, seat cushions and other vehicle interior materials, carpets, curtains, cushions, sofa covers, cushion covers and other indoor supplies.

without

without

Claims (1)

A compound, which is a compound of the following general formula (F), Formula (F): [In formula (F), R _F1 and R _F2 each independently represent an alkyl group having 4 to 14 carbon atoms].