CN113755027A - Active yellow dye composition, yellow dye, and preparation method and application thereof - Google Patents
Active yellow dye composition, yellow dye, and preparation method and application thereof Download PDFInfo
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- CN113755027A CN113755027A CN202111113132.1A CN202111113132A CN113755027A CN 113755027 A CN113755027 A CN 113755027A CN 202111113132 A CN202111113132 A CN 202111113132A CN 113755027 A CN113755027 A CN 113755027A
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- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 239000001043 yellow dye Substances 0.000 title claims abstract description 32
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000000975 dye Substances 0.000 claims abstract description 24
- 238000004043 dyeing Methods 0.000 claims abstract description 18
- 239000000985 reactive dye Substances 0.000 claims abstract description 16
- 238000005917 acylation reaction Methods 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims description 16
- 239000002002 slurry Substances 0.000 claims description 14
- 239000000835 fiber Substances 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000012954 diazonium Substances 0.000 claims description 10
- 239000011521 glass Substances 0.000 claims description 10
- 239000005457 ice water Substances 0.000 claims description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 10
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
- 150000001989 diazonium salts Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 229910052744 lithium Inorganic materials 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 239000011591 potassium Substances 0.000 claims description 8
- 238000007639 printing Methods 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 239000004753 textile Substances 0.000 claims description 6
- 239000012752 auxiliary agent Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 235000010288 sodium nitrite Nutrition 0.000 claims description 5
- 150000007514 bases Chemical class 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 2
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000010933 acylation Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000009980 pad dyeing Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- WQHQCQSAAOGHQP-UHFFFAOYSA-N formaldehyde;2-methylnaphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WQHQCQSAAOGHQP-UHFFFAOYSA-N 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- C09B67/006—Preparation of organic pigments
- C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
-
- 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
- C09B67/0072—Preparations with anionic dyes or reactive dyes
- C09B67/0073—Preparations of acid or reactive dyes in liquid form
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
The invention discloses a reactive yellow dye composition, a yellow dye, a preparation method and an application thereof, relating to the field of fine chemical engineering, wherein the yellow reactive dye composition comprises a component A consisting of one or more compounds in a compound shown as a formula (I), and a component B consisting of one or more compounds in a compound shown as a formula (II); the component A accounts for 50-100 parts by weight, the component B accounts for 0-50 parts by weight, and the preparation method of the yellow dye comprises the following steps: j acid acylation and raw materials containing R1 and R2 are coupled, and finally, the reactive yellow dye is obtained by hydrolysis. The dye does not generate three wastes during production and use, meets the current strict environmental protection requirement, and has good compatibility and fixation in the dyeing application of the reactive dyeHigh rate, excellent comprehensive performance of various color fastness application performances;
Description
Technical Field
The invention relates to the field of fine chemical engineering, in particular to a reactive yellow dye composition, a yellow dye prepared from the reactive yellow dye composition, a preparation method and a preparation process thereof, and printing and dyeing application of the prepared yellow reactive dye in fibers or textiles thereof.
Background
With the increasing living standard, people have higher and higher requirements on textile products, so that the requirements on various properties of the reactive dyes for dyeing textiles are more and more strict. The reactive dye not only has excellent dyeing fastness and dyeing performance, but also meets the requirement of environmental protection. The reactive yellow dye is used as a variety with a large market share, and is required to have good washing fastness and dyeing reproducibility and high lifting power and color fixing rate. In order to improve the dyeing performance of the dye and enable the dye to have good dyeing effect, a plurality of active yellow dye patents appear in the industry.
Disclosure of Invention
In order to overcome the defects of poor color fastness, poor dyeing performance and the like of yellow dyes in the prior art, a yellow dye composition and a yellow dye prepared by the composition are provided. The dye composition has good promotion, high fixation rate and excellent color fastness performances such as washing resistance, friction resistance, perspiration resistance and the like, is suitable for printing and dyeing of fibers or textile materials thereof, and is an environment-friendly reactive dye.
The first purpose of the invention is to provide a reactive yellow dye composition, which comprises 50-100 parts by weight of component A and 0-50 parts by weight of component B.
The component A is selected from at least one dye monomer A compound shown in the following formula (I):
wherein R is1And R2Are respectively H and-SO3M2、-OCH3and-CH3One of (1), M2Is one of hydrogen, potassium, sodium, lithium and ammonium; r3is-SO2CH＝CH2or-SO2C2H4OSO3M3，M3Is one of hydrogen, potassium, sodium, lithium and ammonium;
the component A is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
wherein the dye monomers of formula (I) may each independently be present, preferably in the form of a powder, a synthetic solution or an aqueous solution thereof.
The component B is at least one of dye monomer B compounds shown in the following formula (II);
wherein R is4Is H, -SO3M2、-OCH3and-CH3One of (1), M2Is one of hydrogen, potassium, sodium, lithium and ammonium; r5is-SO2CH＝CH2or-SO2C2H4OSO3M4，M4Is one of hydrogen, potassium, sodium, lithium and ammonium.
The component B is preferably 0 to 40 parts by weight, and is preferably selected from one of the following formulas or a mixture of two or more thereof in any ratio:
preferably, the preparation method of the component A comprises the following steps:
step S1: adding ice water into a glass cup, then adding J acid and maleic anhydride, and carrying out primary acylation reaction at the temperature of 10-20 ℃ and under the condition that the pH value is 3.0-6.5 to obtain compound slurry of the formula (2), wherein the molecular structural formula of the formula (2) is as follows:
step S2: adding ice water into a glass cup, adding the formula (3) and sodium nitrite, then adding hydrochloric acid, and carrying out diazo reaction at 015 ℃ to obtain the diazonium salt of the formula (4), wherein the molecular structural formulas of the formula (2) and the formula (3) are as follows:
step S3: adding the formula (2) into a synthesized diazonium salt formula (4), and carrying out coupling reaction under the conditions of an acid-binding agent, the temperature of 0-10 ℃ and the pH value of 6.5-8.5 to obtain compound slurry of a formula (5), wherein the structural formula of the compound of the formula (5) is as follows:
step S4: adding a basic compound into the dye shown in the formula (5), heating to 60-80 ℃, and carrying out hydrolysis reaction under the condition that the pH value is 9-10 to obtain the finished dye shown in the formula (I).
Preferably, the preparation method of the component A comprises the following steps:
step S1: adding 100-200 parts by mass of ice water into a glass cup, then adding 10-30 parts by mass of J acid and 5-20 parts by mass of maleic anhydride, and carrying out primary acylation reaction for 2-5 hours at the temperature of 10-20 ℃ and the pH value of 3.0-6.5 to obtain the compound slurry of the formula (2), wherein the molecular structural formula of the formula (2) is as follows:
step S2: adding 100-200 parts by mass of ice water into a glass cup, adding 20-40 parts by mass of formula (3), adding 7-10 parts by mass of sodium nitrite, adding 50-70 parts by mass of hydrochloric acid, and carrying out diazo reaction at 015 ℃ for 23 hours to obtain diazonium salt of formula (4), wherein the molecular structural formulas of formula (2) and formula (3) are as follows:
step S3: adding the formula (2) into a synthesized diazonium salt formula (4), and carrying out coupling reaction for 3-7 hours under the conditions of an acid-binding agent, the temperature of 0-10 ℃ and the pH value of 6.5-8.5 to obtain compound slurry of the formula (5), wherein the structural formula of the compound of the formula (5) is as follows:
step S4: adding a basic compound into the dye of the formula (5), heating to 60-80 ℃, and carrying out hydrolysis reaction for 3-6 hours under the condition that the pH value is 9-10 to obtain a finished dye of the formula (I). In the step S3, the acid-binding agent is preferably baking soda, soda ash, a mixed solution of Na CO and CH COONa, or an inorganic ammonium salt. In step S4, the basic compound is preferably a liquid alkali.
Preferably, the component B is prepared by performing acylation reaction on J acid and maleic anhydride at 10-20 deg.C and pH of 3.0-6.5. The acylation reaction is carried out for 2-5 hours.
A second object of the present invention is to provide a yellow dye which comprises any of the above-mentioned reactive yellow dye compositions in addition to conventional auxiliaries commonly used in the art, selected from one or more of dispersants, fillers and other performance-improving auxiliaries. The auxiliaries are preferably fillers. The dispersant may preferably be one selected from dispersant MF and dispersant NNO. The filler may be preferably selected from one or more of anhydrous sodium sulfate, methyl naphthalene sulfonic acid formaldehyde condensate, sodium hexametaphosphate, naphthalene sulfonic acid formaldehyde condensate. The other performance-improving adjuvant may be preferably selected from one or more of a dust-proofing agent, a solubility-improving agent, an alkali-resistant adjuvant, a surfactant, and an accelerating agent. The auxiliaries are preferably present in the form of a powder and/or a solution. The addition amount of the auxiliary agent is preferably 10-50% of the total weight of the product
The third purpose of the invention is to provide a preparation method of yellow dye, which is prepared by mixing 50-100 parts by weight of the active yellow dye composition and 0-50 parts by weight of auxiliary agent. Specifically, the component A is prepared by mixing 50-100 parts by weight, the component B is prepared by mixing 0-50 parts by weight and the auxiliary agent is prepared by mixing 0-50 parts by weight, and the content of the component A is preferably 50-90%. The mixing mode adopts the mode of mixing liquid slurry and then spray drying or mixing monomer powder. The liquid slurry blending time is at least 2 hours; when the powder is mixed, the lower material is returned to the upper material for at least 2 times, and the total mixing time is at least 2 hours.
The fourth purpose of the invention is to provide the application of the yellow reactive dye composition as a yellow reactive dye. Preferably applied to the printing of fibres or textiles thereof, optionally including dyeing or printing. Furthermore, the yellow reactive dye composition is preferably used for printing and dyeing cellulose fibers, protein fibers, polyamide fibers or woven fabrics or blended fabrics of the cellulose fibers, the protein fibers and the polyamide fibers. Optionally, the cellulose fibers include cotton fibers, hemp fibers, and regenerated fibers; optionally, the protein fiber includes wool, silk and wool fabric; optionally, the yellow reactive dye is used for printing and dyeing cotton fibers or regenerated fibers.
The above-mentioned preferred conditions can be arbitrarily combined to obtain the embodiments of the present invention without departing from the common general knowledge in the art.
Compared with the prior art, the invention has the positive improvement effects that: the dye prepared by the dye composition has excellent color fastness and dyeing performance, is very suitable for printing and dyeing of cellulose materials, and has excellent promotion, excellent various color fastness and dark and dense color.
Detailed Description
Example 1:
the formula (1) is prepared by adopting the following synthesis mode
(1) Adding 100-200 parts by mass of ice water into a glass cup, then adding 10-30 parts by mass of J acid and 5-20 parts by mass of maleic anhydride, and carrying out primary acylation reaction for 25 hours at the temperature of 1020 ℃ and the pH of 3.06.5 to obtain compound slurry of the formula (2), wherein the molecular structural formula of the formula (2) is as follows:
(2) adding 100-200 parts by mass of ice water into a glass cup, adding 20-40 parts by mass of formula (3), adding 7-10 parts by mass of sodium nitrite, adding 50-70 parts by mass of hydrochloric acid, and carrying out diazo reaction at 015 ℃ for 23 hours to obtain diazonium salt of formula (4), wherein the molecular structural formulas of formula (3) and formula (4) are as follows:
(3) adding the formula (2) into a synthesized diazonium salt formula (4), and carrying out coupling reaction for 3-7 hours under the conditions of an acid-binding agent, the temperature of 0-10 ℃ and the pH value of 6.5-8.5 to obtain compound slurry of the formula (5), wherein the structural formula of the compound of the formula (5) is as follows:
(4) adding an alkaline compound into the dye of the formula (5), heating to 60-80 ℃, and carrying out hydrolysis reaction for 3-6 hours under the condition that the pH value is 9-10 to obtain a finished dye of the formula (I) for later use.
Example 2:
(1) adding 100-200 parts by mass of ice water into a glass cup, then adding 10-30 parts by mass of J acid and 5-20 parts by mass of maleic anhydride, and carrying out primary acylation reaction for 25 hours at the temperature of 1020 ℃ and the pH value of 3.06.5 to obtain compound slurry.
(2) Adding 100-200 parts by mass of ice water into a glass cup, adding 20-40 parts by mass of para-ester, adding 7-10 parts by mass of sodium nitrite, adding 50-70 parts by mass of hydrochloric acid, and carrying out diazo reaction at 015 ℃ for 23 hours to obtain para-ester diazonium salt for later use.
(3) And (3) acylating the J acid and adding the J acid into the synthesized para-ester diazonium salt, and performing coupling reaction for 3-7 hours at the temperature of 0-10 ℃ and under the condition that the pH value is adjusted to be 6.5-8.5 by using acid-binding agent baking soda to obtain coupling compound slurry.
(4) Adding an alkaline compound into the coupling compound, heating to 60-80 ℃, and carrying out hydrolysis reaction for 3-6 hours under the condition that the pH value is 9-10 to obtain a finished dye product of the formula (1) for later use.
Example 3:
according to the data shown in the table 1, the component A, the component B, the cosolvent and water are mixed by adopting liquid slurry, and after uniform mixing, the mixture is prepared by spray drying or powder mixing, wherein the mixing time is 2 hours.
Table 1: the dye raw material composition of experiment numbers 1-7 comprises the following components:
dyeing Property test
Weighing 2g of the composition dye obtained according to experiment numbers 1-7 and an anti-migration agent (sodium alginate paste 5%) 20ml/l of water to prepare a solution of 20 g/l; pouring the pure cotton woven fabric into a dyeing tank, and carrying out two-dipping and two-rolling (at the temperature of 25 ℃, the rolling residual rate is 60-65%); pre-baking (70 deg.C); drying (150 ℃ for 2 min); pouring prepared alkali liquor (200 g/l of anhydrous sodium sulphate, 20g/l of soda, 5g/l of caustic soda and S1g/l of dye-resistant salt) into a pad dyeing tank, putting the fabric into the pad dyeing tank, and carrying out two-dipping and two-pad alkali dipping (25 ℃ and 80% of pad allowance); then steaming for fixation (102-105 ℃ for 45-90 s); then washing with water, and soaping at 98 ℃ for 10min (2g/l of soap chips); finally, the resultant was washed with water and dried to measure the color fastness, hue and the like, and the results are shown in Table 1.
TABLE 1
As can be seen from the above table, when the yellow reactive dye composition of the present invention is used as a yellow reactive dye, the yellow reactive dye composition has good performance indexes, especially excellent fastness to washing, perspiration and rubbing, and high color fastness ratio, and is an environmentally friendly yellow reactive dye capable of meeting the requirements of high-end customers, the above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and any modification, equivalent replacement, change, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A reactive yellow dye composition characterized by: comprises 50-100 parts by weight of component A and 0-50 parts by weight of component B;
the component A comprises at least one of dye monomer A compounds shown in the following formula (I):
wherein R is1And R2Are respectively H and-SO3M2、-OCH3and-CH3One of (1), M2Is one of hydrogen, potassium, sodium, lithium and ammonium; r3is-SO2CH＝CH2or-SO2C2H4OSO3M3，M3Is one of hydrogen, potassium, sodium, lithium and ammonium;
the component B comprises at least one of dye monomer B compounds shown in the following formula (II);
wherein R is4Is H, -SO3M2、-OCH3and-CH3One of (1), M2Is one of hydrogen, potassium, sodium, lithium and ammonium; r5is-SO2CH＝CH2or-SO2C2H4OSO3M4，M4Is one of hydrogen, potassium, sodium, lithium and ammonium.
2. The reactive yellow dye composition according to 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 reactive yellow dye composition according to claim 1, wherein: the component B is 0 to 40 parts by weight and is selected from one of the following formulas or a mixture of more than two of the following formulas in any proportion:
4. the reactive yellow dye composition according to claim 1, wherein: the preparation method of the component A comprises the following steps:
step S1: adding ice water into a glass cup, then adding J acid and maleic anhydride, and carrying out primary acylation reaction at the temperature of 10-20 ℃ and under the condition that the pH value is 3.0-6.5 to obtain compound slurry of the formula (2), wherein the molecular structural formula of the formula (2) is as follows:
step S2: adding ice water into a glass cup, adding the formula (3) and sodium nitrite, then adding hydrochloric acid, and carrying out diazo reaction at 015 ℃ to obtain the diazonium salt of the formula (4), wherein the molecular structural formulas of the formula (3) and the formula (4) are as follows:
step S3: adding the formula (2) into a synthesized diazonium salt formula (4), and carrying out coupling reaction under the conditions of an acid-binding agent, the temperature of 0-10 ℃ and the pH value of 6.5-8.5 to obtain compound slurry of a formula (5), wherein the structural formula of the compound of the formula (5) is as follows:
step S4: adding a basic compound into the dye shown in the formula (5), heating to 60-80 ℃, and carrying out hydrolysis reaction under the condition that the pH value is 9-10 to obtain the finished dye shown in the formula (I).
5. The reactive yellow dye composition according to claim 1, wherein: the component B is prepared by performing acylation reaction on J acid and maleic anhydride at 10-20 deg.C and pH of 3.0-6.5.
6. A yellow dye characterized by: the dye comprises the reactive yellow dye composition as claimed in any one of claims 1 to 5 and an auxiliary agent.
7. The method for preparing a yellow dye according to claim 6, wherein: the reactive yellow dye is prepared by mixing 50-100 parts by weight of the reactive yellow dye composition and 0-50 parts by weight of an auxiliary agent.
8. The method for preparing a yellow dye according to claim 7, wherein: the mixing adopts a mode of mixing liquid slurry and then spray drying or mixing monomer powder.
9. Use of the yellow reactive dye composition according to any one of claims 1 to 5 as yellow reactive dye.
10. Use according to claim 9, characterized in that the yellow reactive dye composition is used for printing and dyeing of fibers or textiles thereof.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117343555A (en) * | 2023-10-07 | 2024-01-05 | 浙江亿得新材料股份有限公司 | A composite reactive yellow dye composition capable of preventing and removing whitening and its application |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1333313A (en) * | 1970-12-12 | 1973-10-10 | Hoechst Ag | Water-soluble reactive metal complex monoazo dyestuffs and a process for their manufacture |
| US3873513A (en) * | 1968-08-06 | 1975-03-25 | Us Agriculture | Methylolated reaction product of a hydroxy carbamate and a cellulose-dyeing azo dyestuff containing a chlorotriozinyl group |
| CN111334086A (en) * | 2020-04-10 | 2020-06-26 | 浙江瑞华化工有限公司 | Maotai-red reactive dye composition and preparation method and application thereof |
| CN111607250A (en) * | 2020-06-15 | 2020-09-01 | 江苏德旺数码科技有限公司 | High-fastness reactive orange dye composition |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3873513A (en) * | 1968-08-06 | 1975-03-25 | Us Agriculture | Methylolated reaction product of a hydroxy carbamate and a cellulose-dyeing azo dyestuff containing a chlorotriozinyl group |
| GB1333313A (en) * | 1970-12-12 | 1973-10-10 | Hoechst Ag | Water-soluble reactive metal complex monoazo dyestuffs and a process for their manufacture |
| CN111334086A (en) * | 2020-04-10 | 2020-06-26 | 浙江瑞华化工有限公司 | Maotai-red reactive dye composition and preparation method and application thereof |
| CN111607250A (en) * | 2020-06-15 | 2020-09-01 | 江苏德旺数码科技有限公司 | High-fastness reactive orange dye composition |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117343555A (en) * | 2023-10-07 | 2024-01-05 | 浙江亿得新材料股份有限公司 | A composite reactive yellow dye composition capable of preventing and removing whitening and its application |
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