CN111718599B - A kind of disperse turquoise blue dye composition and dye product - Google Patents
A kind of disperse turquoise blue dye composition and dye product Download PDFInfo
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- CN111718599B CN111718599B CN202010619859.6A CN202010619859A CN111718599B CN 111718599 B CN111718599 B CN 111718599B CN 202010619859 A CN202010619859 A CN 202010619859A CN 111718599 B CN111718599 B CN 111718599B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
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Abstract
本发明公开了一种分散翠蓝染料组合物及染料制品，所述分散翠兰染料组合物包含30‑75质量份的组分A、20‑65质量份的组分B和1‑20质量份的组分C，所述组分A选自下式(I)所示化合物中的至少一种，所述组分B选自下式(II)所示化合物中的至少一种，所述组分C选自下式(IV)所示化合物中的一种或多种。所述分散翠兰染料制品包括所述的分散翠蓝染料组合物和助剂。本发明的分散翠蓝染料制品应用于疏水性纤维材料染色时，具有色光艳丽、耐升华、耐摩擦和耐水洗牢度优异等特点。 The invention discloses a disperse turquoise blue dye composition and a dye product. The disperse turquoise blue dye composition comprises 30-75 parts by mass of component A, 20-65 parts by mass of component B and 1-20 parts by mass Component C, the component A is selected from at least one of the compounds represented by the following formula (I), the component B is selected from at least one of the compounds represented by the following formula (II), and the component Part C is selected from one or more of the compounds represented by the following formula (IV). The disperse turquoise blue dye product includes the disperse turquoise blue dye composition and an auxiliary agent. When the disperse turquoise blue dye product of the present invention is applied to the dyeing of hydrophobic fiber materials, it has the characteristics of bright shade, sublimation resistance, rubbing resistance and washing fastness. 
Description
One, the technical field
The invention relates to a disperse turquoise blue dye composition and a dye product, in particular to a high-fastness disperse turquoise blue dye composition and a dye product which are suitable for printing and dyeing hydrophobic fiber materials.
Second, background Art
Turquoise blue, a color which is more bluish than blue, is a dye with wider application, and is one of the indispensable main colors of lake blue, light green and the like. Because the disperse turquoise blue 60 is seriously stained on spandex fabrics, the disperse turquoise blue dye for the polyester-ammonia fabric in the current market still has the problems of insufficient bright color, poor washing, sublimation and rubbing fastness of the dye and the like, and patents such as CN102732061A, CN107383936A and the like provide a disperse turquoise blue dye, but the performance of the disperse turquoise blue dye still needs to be further improved to meet the changing customer requirements.
Third, the invention
The invention aims to provide a disperse turquoise blue dye composition and a dye product, which have the characteristics of bright color, sublimation resistance, friction resistance, excellent fastness to washing and the like when being applied to dyeing of hydrophobic fiber materials, and are particularly suitable for dyeing of polyester/spandex stretch fabrics with higher requirements on the fastness.
The technical scheme adopted by the invention is as follows:
the invention provides a disperse turquoise blue dye composition, which comprises 30-75 parts by mass of a component A, 20-65 parts by mass of a component B and 1-20 parts by mass of a component C, wherein the component A is selected from at least one compound shown in a formula (I), the component B is selected from at least one compound shown in a formula (II), and the component C is selected from one or more compounds shown in a formula (IV);
in formula (I):
R1is H, C1～C4Alkyl of (C)1～C4Alkoxy or CF of3；R2、R3Each independently is C1～C8Alkyl group of (i), (ii), (iii), (iv) and (iv)2)m-OK1、-(CH2)n-Ph; wherein Ph is phenyl, K1Is selected from C1～C4M, n are each independently 2 or 3;
in the formula (II):
R4is C1～C4Alkyl or C1～C4An alkoxyalkyl group of (a);
in the formula (IV):
R7is-COOC2H4OC2H4OCH3Or SO2NHR9，R8、R9Each independently is C1～C18An alkyl group.
In the present invention, said C1～C4The alkyl group may be methyl, ethyl, linear or branched propyl, or linear or branched butyl. Said C1～C4Alkoxy can be methoxy, ethoxy, linear or branched propoxy, linear or branched butoxy. Said C1～C18The alkyl group may be methyl, ethyl, linear or branched propyl, linear or branched butyl, linear or branched hexyl, linear or branched octyl, linear or branched dodecyl, linear or branched octadecyl, and the like. The halogen can be F, Cl and Br.
Preferably, the component A is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
still more preferably, component A is at least one of the compounds represented by the formulae (I-1) and (I-2).
Preferably, the component B is selected from one of the following formulas or a mixture thereof in any ratio:
preferably, the component C is R7is-COOC2H4OC2H4OCH3At least one of the compounds (IV) and/or R7Is SO2NHR9At least one of the compounds (IV) of (1).
Preferably, the component C is selected from one of the following formulas or a mixture of two or more of the following formulas in any ratio:
more preferably, component C is at least one of the compounds represented by (IV-1), (IV-2), (IV-6) and (IV-8).
Preferably, in the disperse turquoise blue dye composition, the mass percentage of the component A is 30-75% (preferably 35-75%), the mass percentage of the component B is 20-65% (preferably 25-65%), and the mass percentage of the component C is 1-20% (preferably 1-15%).
As a further preference, the disperse turquoise blue dye composition comprises a component a, a component B and a component C, wherein:
the component A is at least one of compounds shown as formulas (I-1) and (I-2);
the component B is at least one of compounds shown as formulas (II-1) and (II-2);
the component C is at least one of compounds shown in formulas (IV-1), (IV-2), (IV-6) and (IV-8).
As a further preference, the disperse turquoise blue dye composition consists of a component a, a component B and a component C, wherein the mass percentage of the component a is 30-75% (preferably 35-75%), the mass percentage of the component B is 20-65% (preferably 25-65%), and the mass percentage of the component C is 1-20% (preferably 1-15%).
As a further preference, the disperse turquoise blue dye composition consists of a component a, a component B and a component C, wherein:
the component A is at least one of compounds shown as formulas (I-1) and (I-2);
the component B is at least one of compounds shown as formulas (II-1) and (II-2);
the component C is at least one of compounds shown in formulas (IV-1), (IV-2), (IV-6) and (IV-8).
The mass percentage of the component A is 30-75% (preferably 35-75%), the mass percentage of the component B is 20-65% (preferably 25-65%), and the mass percentage of the component C is 1-20% (preferably 1-15%).
The disperse turquoise blue dye composition can also comprise at least one of a compound (III) and a compound (V),
in the formula (III):
R5is C1～C4An alkyl group;
R6is-O (CH)2)p-R, p is 0-4, R is H or-Ph-K2Ph is phenyl, K2Is H or C1～C4Alkyl or C1～C4Alkoxy or halogen, and when R is H, p is not 0;
in the formula (V):
R10is methyl or ethyl.
Preferably, in the disperse turquoise blue dye composition, the mass part of the component A is 30-75 parts, the mass part of the component B is 20-65 parts, the mass part of the component C is 1-19 parts, and the total mass part of at least one of the component C + compound (III) and the compound (V) is 2-20 parts.
Further preferably, the content by mass of the component A is 30 to 75% (preferably 35 to 75%), the content by mass of the component B is 20 to 65% (preferably 25 to 65%), the content by mass of the component C is 1 to 19% (preferably 1 to 15%), and the total content by mass of at least one of the component C + the compound (III) and the compound (V) is 2 to 20% (preferably 2 to 15%).
Preferably, R6Is C1～C4Alkoxy or-O (CH)2)p-Ph-K2Wherein Ph is phenyl, p is 0 or 1 or 2, K2Is H or C1～C4Alkyl or C1～C4Alkoxy or halogen. More preferably-O (CH)2)p-Ph-K2is-O (CH)2)p-Ph-H or-O-Ph-K2Wherein Ph is phenyl, p is 1 or 2, K2Is C1～C4Alkyl radical, C1～C4Alkoxy or halogen.
Particularly preferred compounds (III) according to the invention are one of the following compounds:
particularly preferred compounds (V) according to the invention are one of the following compounds:
the disperse turquoise blue dye composition of the invention also allows the addition of not more than 5% by weight, preferably not more than 3% by weight of a toning component, such as the addition of trace amounts of c.i. disperse yellow 54, c.i. disperse yellow 64, c.i. disperse yellow 119, c.i. disperse yellow 143, c.i. disperse yellow 182, c.i. disperse orange 25, c.i. disperse orange 33, c.i. disperse orange 61, c.i. disperse red 73, c.i. disperse red 80, c.i. disperse red 145, c.i. disperse red 158 and the like.
In the above scheme, c.i. refers to the dye index number (COLORINDEX), which is a compilation of international dye and pigment varieties published by the british dyers association (SDC) and the american association of textile chemists and dyers (AATCC). The "dye part" refers to a dye cake (crude dye) which does not include any finishing auxiliary agent, but is allowed to contain a small amount of impurities brought about in the synthesis, the impurities do not affect the service performance of the dye, and the mass percentage or the mass part of the dye is calculated by the dry weight of the dye cake.
It should be emphasized that the disperse turquoise blue dye compounds of the present invention, the dyes coupled at the ortho position of the pyridone hydroxyl group, generally exist in the form of quinone hydrazone, that is, the dyes of the general formulas (III) and (IV) substantially have the quinone hydrazone structures shown in the following formulas (IIIa) and (IVa), and in consideration of the writing habit of those skilled in the art, the writing form of azo is still adopted in the summary and the examples, which does not affect the essence of the present invention:
R5、R6、R7、R8、R9the same as defined above for the compounds of the formulae (III) and (IV).
Due to the particularity of the dye industry, the pure product is difficult to prepare and is not necessary to prepare, and impurities in the preparation process are usually carried, so that the disperse turquoise blue dye composition provided by the invention is also allowed to contain a small amount of water and a trace amount of physical impurities when prepared into a finished product.
The disperse turquoise blue dye composition provided by the invention is sold as a commodity or directly applied to textile material coloring, and a conventional auxiliary agent is usually required to be added. Therefore, the invention also provides a disperse turquoise blue dye product which is sold as a commodity or directly applied to textile material coloring, and the disperse turquoise blue dye product comprises the disperse turquoise blue dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse turquoise blue dye composition is 0.2-5: 1. The auxiliary agent is a dispersing agent, other surfactants and the like which are commonly used in the process of compounding disperse dyes, and is preferably selected from one or a mixture of more than two of the following components: lignosulfonates (e.g., sodium lignosulfonate (lignin 85A, lignin 83A)), alkylnaphthalenesulfonic acid-formaldehyde condensates (e.g., methylnaphthalenesulfonic acid-formaldehyde condensate (dispersant MF)), naphthalenesulfonic acid-formaldehyde condensate (dispersant NNO), benzylnaphthalenesulfonic acid-formaldehyde condensate (dispersant CNF), anhydrous sodium sulfate (sodium sulfate), and the like.
The disperse turquoise blue dye product can be prepared by the following method: mixing the raw dye contained in the disperse turquoise blue dye composition according to the proportion, and then carrying out microparticulation by a grinder such as a sand mill or a grinding machine in the presence of an auxiliary agent and water; the crude dye contained in the disperse turquoise blue dye composition may be subjected to a microparticulation treatment using a pulverizer such as a sand mill or a grinder in the presence of an auxiliary agent or water, and then mixed in the above-mentioned ratio. The disperse turquoise blue material product can be liquid after being ground by a sand mill or a grinding machine, and can be powdery and granular after being spray-dried.
Preferably, the disperse turquoise blue dye product consists of the disperse turquoise blue dye composition and an auxiliary agent.
In the present invention, the dye compounds represented by the formulae (I), (II) and (IV) can be conveniently synthesized in a manner well known to those skilled in the art, and commercially available products can also be used.
The dye product prepared by the disperse turquoise blue dye composition can dye hydrophobic fiber materials such as polyester fibers and terylene/spandex fabrics in a conventional mode in the industry, such as dyeing by a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be directly used for printing. Wherein, the common dip dyeing method comprises the following steps: pretreating a hydrophobic fiber material, putting the hydrophobic fiber material into a dye vat for dip dyeing, washing the hydrophobic fiber material to be neutral by cold water after dyeing, wringing, carrying out reduction washing, and drying; direct printing is as follows: the method comprises the steps of carrying out dyeing pretreatment on the fabric, drying, setting, printing disperse dye color paste on a printing machine, carrying out steaming, fixing the color of the dye on the fabric by using a steaming mode, finally washing, and tentering and setting.
The disperse turquoise blue dye product provided by the invention is applied to dyeing of polyester and polyester blended fabric, especially dyeing of polyester and polyurethane blended fabric, and has the characteristics of bright color, rubbing fastness, washing fastness, excellent sublimation fastness resistance and the like.
(IV) detailed description of the preferred embodiments
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1:
55 g of a compound of a formula (I-1), 35 g of a compound of a formula (II-2), 6 g of a compound of a formula (IV-8), 2 g of a compound of a formula (IV-1), 2 g of a compound of a formula (V-1) and 200 g of a dispersing agent MF are mixed with 1000 g of water, and then the mixture is ground, dispersed and spray-dried to obtain a finished product, wherein the finished product can provide turquoise blue color tone of polyester and blended fabrics thereof.
Example 2:
55 g of a compound of a formula (I-1), 35 g of a compound of a formula (II-1), 6 g of a compound of a formula (IV-8), 2 g of a compound of a formula (IV-1), 2 g of a compound of a formula (V-1) and 200 g of a dispersing agent MF are mixed with 1000 g of water, and then the mixture is ground, dispersed and spray-dried to obtain a finished product, wherein the finished product can provide turquoise blue color tone of polyester and blended fabrics thereof.
Examples 3 to 22
According to the method described in the examples 1-2, except that the structure and weight of the component A, the component B and the component C in the table 1 are adopted, 200 g of the auxiliary agent (150 g of the dispersing agent MF and 50 g of sodium lignosulfonate) is added, 1000 g of water is added for blending to prepare slurry, and the slurry is ground, dispersed and dried to prepare the finished product, and the dye can provide turquoise blue color tone with excellent fastness performance for polyester and blended fabrics thereof.
TABLE 1
Example 23:
61 g of a compound of a formula (I-1), 25 g of a compound of a formula (II-2), 10 g of a compound of a formula (IV-8), 4 g of C.I. disperse yellow 82 and 250 g of a dispersing agent MF are mixed with 1200 g of water, and then the mixture is ground, dispersed and spray-dried to obtain a finished product, wherein the finished product can provide turquoise blue color tone of polyester and blended fabrics thereof.
Example 24:
61 g of a compound of a formula (I-1), 30 g of a compound of a formula (II-2), 5 g of a compound of a formula (IV-8), 4 g of C.I. disperse yellow 54 and 250 g of a dispersing agent MF are mixed with 1200 g of water, and then the mixture is ground, dispersed and spray-dried to obtain a finished product, wherein the finished product can provide turquoise blue color tone of polyester and blended fabrics thereof.
Comparative example:
example 1 and example 8 in CN102732061A were used as comparative example 1 and comparative example 2.
Example 1 in CN107383936A was taken as comparative example 3.
Dyeing example:
respectively weighing 2 g of the disperse dye prepared in the examples 1-24 and the dye prepared in the comparative examples 1-3, treating the polyester/ammonia mixed fabric by adopting a conventional high-temperature high-pressure dyeing method, controlling the dyeing depth (o.w.f) to be 4.0% and the bath ratio to be 1: 25, adjusting the pH value of a dyeing bath to be 4-5, dyeing at room temperature, heating to 130 ℃ at 1 ℃/min, keeping the temperature for 45min, reducing, cleaning, washing and drying according to a conventional method, and carrying out heat setting at 200 ℃ for 30 seconds. The sample cloth color is observed, and the fastness to rubbing, washing and sublimation is respectively tested by adopting international standards ISO105-X12 and AATCC61-2A, ISO105-P01, and the results are shown in Table 2:
therefore, when the turquoise blue disperse dye composition provided by the invention is applied to dyeing of polyester/spandex fabrics, the turquoise blue disperse dye composition is more excellent in performance compared with the existing disperse turquoise blue dye after heat setting finishing.
Claims (12)
1. A disperse turquoise blue dye composition characterized by: the disperse turquoise blue dye composition comprises 30-75 parts by mass of a component A, 20-65 parts by mass of a component B and 1-20 parts by mass of a component C, wherein the component A is selected from at least one compound shown in the following formula (I), the component B is selected from at least one compound shown in the following formula (II), and the component C is selected from one or more compounds shown in the following formula (IV);
in formula (I):
R1is H, C1～C4Alkyl of (C)1～C4Alkoxy or CF of3；R2、R3Each independently is C1～C8Alkyl group of (i), (ii), (iii), (iv) and (iv)2)m-OK1、-(CH2)n-Ph; wherein Ph is phenyl, K1Is selected from C1～C4M, n are each independently 2 or 3;
in the formula (II):
R4is C1～C4Alkyl or C1～C4An alkoxyalkyl group of (a);
in the formula (IV):
R7is-COOC2H4OC2H4OCH3Or SO2NHR9，R8、R9Each independently is C1～C18An alkyl group.
2. The disperse turquoise blue dye composition of claim 1, wherein: the component A is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
3. the disperse turquoise blue dye composition of claim 1, wherein: the component B is selected from one of the following formulas or a mixture of the following formulas in any proportion:
4. the disperse turquoise blue dye composition of claim 1, wherein: the component C is R7is-COOC2H4OC2H4OCH3At least one compound of formula (IV) and/or R7Is SO2NHR9At least one compound of formula (IV).
5. The disperse turquoise blue dye composition of claim 1, wherein: the component C is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
6. the disperse turquoise blue dye composition of claim 1, wherein: in the disperse turquoise blue dye composition, the mass percentage of the component A is 30-75%, the mass percentage of the component B is 20-65%, and the mass percentage of the component C is 1-20%.
7. The disperse turquoise blue dye composition of claim 1, wherein: in the disperse turquoise blue dye composition, the mass percent of the component A is 35-75%, the mass percent of the component B is 25-65%, and the mass percent of the component C is 1-15%.
8. The disperse turquoise blue dye composition of claim 1, 6 or 7, wherein: the disperse turquoise blue dye composition comprises a component A, a component B and a component C, wherein:
the component A is at least one of compounds shown as formulas (I-1) and (I-2);
the component B is at least one of compounds shown as formulas (II-1) and (II-2);
the component C is at least one of compounds shown in formulas (IV-1), (IV-2), (IV-6) and (IV-8);
9. the disperse turquoise blue dye composition of claim 1, wherein: the compound shown in the formula (IV) contains a quinone hydrazone structure shown in the following formula (IVa),
in the formula (IVa), R7、R8The same as defined above for the compound of formula (IV).
10. A disperse turquoise blue dye product comprising the disperse turquoise blue dye composition as claimed in claim 1 and an auxiliary, wherein the weight ratio of the auxiliary to the disperse turquoise blue dye composition is 0.2 to 5: 1.
11. The disperse turquoise blue dye preparation of claim 10, wherein: the disperse turquoise blue dye product consists of the disperse turquoise blue dye composition and an auxiliary agent.
12. A disperse turquoise blue dye preparation according to claim 10 or 11, wherein: the auxiliary agent is selected from one of the following or a mixture of more than two of the following: lignosulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate, benzyl naphthalene sulfonic acid formaldehyde condensate and anhydrous sodium sulphate.
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| CN102732061A (en) * | 2012-06-18 | 2012-10-17 | 绍兴奇彩化工有限公司 | Blue disperse dye compound |
| CN103408968A (en) * | 2013-09-10 | 2013-11-27 | 江苏亚邦染料股份有限公司 | Blue disperse dye mixture |
| CN103613953A (en) * | 2013-11-08 | 2014-03-05 | 浙江长征化工有限公司 | Disperse blue dye composition, disperse dye, and preparation method and application of disperse dye |
| CN103740136A (en) * | 2013-12-29 | 2014-04-23 | 浙江龙盛集团股份有限公司 | High-fastness turquoise blue disperse dye composition |
| CN105860581A (en) * | 2016-04-14 | 2016-08-17 | 浙江欧亚化工有限公司 | Disperse dye composition and preparing method thereof |
| CN106752086A (en) * | 2016-12-09 | 2017-05-31 | 菲诺染料化工(无锡)有限公司 | Disperse bright blue dye composite and disperse bright blue dyestuff |
| CN107383936A (en) * | 2017-07-13 | 2017-11-24 | 浙江龙盛化工研究有限公司 | One kind disperses bright blue dye composite and dye preparations |
| KR101984771B1 (en) * | 2018-02-07 | 2019-05-31 | 대영산업 주식회사 | Black disperse dye composition for textile printing |
| CN108727866A (en) * | 2018-05-29 | 2018-11-02 | 绍兴金绿洲新材料科技有限公司 | A kind of economical admixture of disperse dyes |
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