CN109679373B - Disperse dye composition, disperse dye, and preparation method and application thereof - Google Patents

Disperse dye composition, disperse dye, and preparation method and application thereof Download PDF

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CN109679373B
CN109679373B CN201811573511.7A CN201811573511A CN109679373B CN 109679373 B CN109679373 B CN 109679373B CN 201811573511 A CN201811573511 A CN 201811573511A CN 109679373 B CN109679373 B CN 109679373B
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disperse dye
component
formula
dye composition
disperse
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CN109679373A (en
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顾伟娣
谢子平
陶彬彬
王孝青
阮梦宇
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Zhejiang Runtu Co Ltd
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Zhejiang Runtu Co Ltd
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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
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • 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
    • 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
    • C09B67/0082—Preparations of disperse dyes or solvent 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
    • D06P1/16—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 dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo dyes
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Abstract

A disperse dye composition, a disperse dye, a preparation method and an application thereof. The disperse dye is suitable for dyeing and printing terylene and blended fabrics thereof, and has good fastness, especially excellent washing fastness and sublimation fastness.

Description

Disperse dye composition, disperse dye, and preparation method and application thereof
Technical Field
The invention relates to a disperse dye composition, a disperse dye, a preparation method and application thereof. The disperse dye is suitable for dyeing and printing terylene and blended fabrics thereof.
Background
Dark brown, coffee and khaki are increasingly favored by people in recent years due to natural and simple color tones, such as clothes, curtains, sofas and the like, but the varieties of disperse dyes used for dyeing the colors are very few, and only a few varieties cannot be used for dyeing high-grade fabrics due to insufficient depth and insufficient fastness. How to solve the problems and meet the market demand is a problem which needs to be solved urgently.
Disclosure of Invention
The invention provides a disperse dye composition, a disperse dye, a preparation method and application thereof, wherein the disperse dye composition has high cost performance, good fastness of various items, and particularly has great advantages in washing fastness and sublimation fastness.
Means for solving the problems
The invention provides a disperse dye composition, which comprises the following components:
one or more than two components A shown in formula (1),
Figure BDA0001916168270000011
in the formula (1), the reaction mixture is,
R1、R2each independently is C1～C4The substituent is-OCOR3or-COOR4Wherein R is3、R4Is C1～C4Alkyl groups of (a);
one or more than two components B shown in a formula (2),
Figure BDA0001916168270000021
in the formula (2), the reaction mixture is,
X1is cyano or a halogen atom; r7、R8Each independently is C1～C4The substituent is-OCOR5、-COOR6、-CH＝CH2-OH or-CN, wherein R5、R6Is C1～C4Alkyl groups of (a);
and a component C represented by the formula (3),
Figure BDA0001916168270000022
in the formula (3), the reaction mixture is,
X2、X3each independently of the other being halogen, -H, -NO2、-COOC2H4OC2H4OCH3or-OSO2-Ph, wherein X2、X3When not H, Ph represents phenyl; r9Is C1～C4Alkyl group of (1).
According to the disperse dye composition, the component A is one or more than two of the following compounds:
Figure BDA0001916168270000023
Figure BDA0001916168270000031
according to the disperse dye composition, the component B is one or more than two of the following compounds:
Figure BDA0001916168270000032
Figure BDA0001916168270000041
according to the disperse dye composition, the component C is one or more than two of the following compounds:
Figure BDA0001916168270000042
Figure BDA0001916168270000051
the disperse dye composition according to the present invention comprises, based on the total weight of the disperse dye composition:
20 to 89 percent by weight, preferably 40 to 77 percent by weight of the component A,
10 to 50 wt%, preferably 15 to 35 wt% of component B,
1-30% by weight, preferably 8-25% by weight of component C.
In practice, the dye components of the present invention may often carry some by-products and other impurities without affecting the practice of the present invention.
The invention also provides a disperse dye, which comprises the disperse dye composition and auxiliary materials; preferably, the auxiliary materials comprise an auxiliary agent and water; more preferably, the auxiliary agent comprises one or more of a surfactant, a bactericide or a dye dispersant; further preferably, the dye dispersant comprises one or a combination of two or more of the following: naphthalene sulfonic acid formaldehyde condensates (e.g., dispersant MF, dispersant CNF, dispersant NNO), lignosulfonates (e.g., lignin 85A, lignin 83A), or anhydrous sodium sulphate.
According to the disperse dye, the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5: 1; preferably, the disperse dye is liquid after being ground by a sand mill or a grinding machine, and the solid content is 20-50%, or the disperse dye is powdery or granular after being spray-dried, and the solid content is 87-96%.
The invention also provides a method for preparing the disperse dye, which comprises the following steps:
mixing the dye components, and then carrying out granulation treatment by using a sand mill or a grinding machine in the presence of auxiliary materials; or granulating the dye components by a sand mill or a grinding machine in the presence of auxiliary materials, and mixing.
The invention also provides the use of the disperse dyes according to the invention for dyeing and printing textiles; preferably, the fabric is terylene and blended fabric thereof.
The invention also provides a fabric, which is prepared by dyeing and printing the disperse dye; preferably, the fabric is terylene and blended fabric thereof.
ADVANTAGEOUS EFFECTS OF INVENTION
The disperse dye composition is very suitable for dyeing and printing terylene and blended fabrics thereof, has good fastness, has outstanding advantages in particular in the aspects of washing fastness and sublimation fastness, and is an rare disperse dye composition with medium and deep color.
Detailed Description
The present invention is further illustrated by the following examples, but the scope of the invention is not limited thereto.
In the examples, the component A, B, C of the present invention is mixed with the assistant and water according to a certain proportion, and then ground and dispersed by a sand mill to prepare slurry, or further spray-dried to prepare the dye.
The component A, B, C is a known dye compound and is either commercially available or can be prepared by existing methods.
The preparation or source of the specific compounds used in the examples are as follows.
A process for producing a compound of formula (1-1): diazotizing 2, 6-dichloro-4-nitroaniline and coupling with m-acetamido-N, N-dipropionic acid methyl ester aniline to obtain the compound shown in the formula (1-1).
A process for producing a compound of formula (1-2): diazotizing 2, 6-dichloro-4-nitroaniline and coupling with m-acetamido-N, N-diacetic acid methyl ester aniline to obtain the compound shown in the formula (1-2).
A process for producing a compound of formula (1-3): diazotizing 2, 6-dichloro-4-nitroaniline and coupling with m-acetamido-N, N-diacetoxyethylaniline to obtain the compound shown as the formula (1-3).
The compound of formula (2-1) is c.i. disperse blue 79 produced by zhejiang leata gmbh: 1.
the compound of formula (2-2) is c.i. disperse blue 79 produced by zhejiang leata gmbh.
A process for producing a compound of formula (2-3): diazotizing 2, 4-dinitro-6 chloroaniline and coupling with 2-methoxy-5-acetamido-N-methyl acetate-N-cyanoethylaniline to obtain the compound shown as the formula (2-3).
The compound of formula (2-4) is C.I. disperse blue GW of Zhejiang Runfiang GmbH 1.
A process for producing a compound of formula (2-5): diazotizing 2, 4-binitro-6-bromoaniline and coupling with 2-methoxy-5-acetamido-N-methyl acetate-N-allylaniline, and then cyaniding to obtain the compound shown in the formula (2-5).
The compound of formula (3-1) is c.i. disperse yellow 114 produced by zhejiang leata gmbh.
The compound of formula (3-2) is c.i. disperse yellow 119 produced by zhejiang leata gmbh.
The compound of formula (3-3) is c.i. disperse yellow 211 produced by zhejiang leata gmbh.
A process for producing a compound of formula (3-4): diazotizing p-nitroaniline, and coupling with N-methyl-3-cyano-4-methyl-6-hydroxy-2-pyridone to obtain the compound shown as the formula (3-4).
Example 1:
62 g of the compound of the formula (1-2), 23 g of the compound of the formula (2-1), 15 g of the compound of the formula (3-1), 35 g of lignin 85A and 365 g of water are added, stirred uniformly and ground to be dispersed to prepare the liquid disperse dye.
Comparative example 1:
the procedure of example 1 was repeated, replacing the compound of formula (1-2) of example 1 with the compound of the following formula (4), and the remainder was unchanged.
Figure BDA0001916168270000071
The liquid disperse dyes of example 1 and comparative example 1 were subjected to a performance test.
The specific test method is as follows:
referring to GB/T2374-2007, GB/T2395-2003 and GB/T5718-1997, 100g/L printing paste is prepared from the disperse dyes of example 1 and comparative example 1 respectively, the rest is printing paste and water, after printing by a printing machine, drying, fixing, washing and shaping are carried out to prepare printed textiles, and the washing fastness, the light fastness and the sublimation fastness are measured according to GB/T3921-2008 and GB/T8427-2008, and the test results are shown in Table 1.
TABLE 1
Name of the embodiment Fastness to washing Color fastness to sunlight Fastness to sublimation
Example 1 4 7 4-5
Comparative example 1 3-4 6 4
Examples 2 to 10
Mixing the component A, the component B, the component C and the auxiliary agent with water according to the table 2, grinding to prepare liquid dye or spray drying to prepare the disperse dye.
TABLE 2 (Unit: gram)
Figure BDA0001916168270000091
Note: water is the moisture content of the final commercial product in table 2.
1.0 g of the disperse dye prepared in each of examples 2 to 10 was placed in 500ml of water to prepare a disperse dye suspension. Absorbing 40ml of disperse dye suspension, mixing with 60ml of water, adjusting the pH value of a dye bath to 5 by using acetic acid, then heating to 60 ℃, simultaneously respectively adding 2g of polyester fiber for high-temperature high-pressure dyeing, heating to 130 ℃ within 35 minutes, preserving heat for 45 minutes, cooling to 80 ℃ and sampling.
The sublimation fastness and washing fastness of the dye are measured according to GB/T5718-1997 and GB/T3921-2008, and the test results are shown in Table 3.
TABLE 3
Examples Fastness to sublimation Fastness to washing
2 4 5
3 4-5 5
4 4-5 5
5 4-5 5
6 4-5 5
7 4-5 5
8 4 5
9 4-5 5
10 4-5 5

Claims (16)

1. A disperse dye composition characterized by comprising:
one or more than two components A shown in formula (1),
Figure FDA0002698316840000011
in the formula (1), the reaction mixture is,
R1、R2each independently is C1～C4Alkyl or substituted C of1～C4The substituent is-OCOR3or-COOR4Wherein R is3、R4Is C1～C4Alkyl groups of (a);
one or more than two components B shown in a formula (2),
Figure FDA0002698316840000012
in the formula (2), the reaction mixture is,
X1is cyano or a halogen atom; r7、R8Each independently is C1～C4Alkyl or substituted C of1～C4The substituent is-OCOR5、-COOR6、-CH＝CH2-OH or-CN, wherein R5、R6Is C1～C4Alkyl groups of (a);
and a component C represented by the formula (3),
Figure FDA0002698316840000013
in the formula (3), the reaction mixture is,
X2、X3each independently of the other being halogen, -H, -NO2、-COOC2H4OC2H4OCH3or-OSO2-Ph, wherein X2、X3When not H, Ph represents phenyl; r9Is C1～C4Alkyl groups of (a);
based on the total weight of the disperse dye composition, comprising:
20 to 89 weight percent of component A,
10-50 wt% of component B,
1-30 wt% of component C.
2. The disperse dye composition according to claim 1, wherein the component A is one or more of the following compounds:
Figure FDA0002698316840000021
3. a disperse dye composition according to claim 1 or 2, wherein the component B is one or more of the following compounds:
Figure FDA0002698316840000031
4. a disperse dye composition according to claim 1 or 2, wherein the component C is one or more than two of the following compounds:
Figure FDA0002698316840000041
5. the disperse dye composition according to claim 1 or 2, comprising, based on the total weight of the disperse dye composition:
40-77 wt% of component A,
15-35% by weight of a component B,
8-25% by weight of component C.
6. A disperse dye, which is characterized by comprising the disperse dye composition according to any one of claims 1 to 5 and an auxiliary material.
7. A disperse dye according to claim 6, wherein the auxiliary materials comprise auxiliaries and water.
8. The disperse dye according to claim 7, wherein the auxiliary agent comprises one or a combination of two or more of a surfactant, a bactericide or a dye dispersant.
9. The disperse dye according to claim 8, wherein the dye dispersant comprises one or a combination of two or more of the following: naphthalene sulfonic acid formaldehyde condensates, lignosulfonates, or anhydrous sodium sulfate.
10. A disperse dye according to any one of claims 7 to 9, wherein the weight ratio of the auxiliary to the disperse dye composition is from 0.2 to 5: 1.
11. A disperse dye according to claim 10, wherein the disperse dye is liquid after being ground by a sand mill or a grinder and has a solid content of 20 to 50%, or the disperse dye is powdery or granular after being spray-dried and has a solid content of 87 to 96%.
12. A process for preparing a disperse dye according to any one of claims 6 to 11, comprising the steps of:
mixing the dye components, and then carrying out granulation treatment by using a sand mill or a grinding machine in the presence of auxiliary materials; or granulating the dye components by a sand mill or a grinding machine in the presence of auxiliary materials, and mixing.
13. Use of a disperse dye according to any one of claims 6 to 11 for dyeing and printing textiles.
14. Use according to claim 13, characterized in that the fabric is dacron and its blend fabrics.
15. A fabric, characterized in that it is prepared by dyeing and printing with a disperse dye according to any one of claims 6 to 11.
16. The fabric of claim 15, wherein the fabric is polyester and blends thereof.
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2681831T3 (en) * 2009-12-23 2018-09-17 Colourtex Industries Limited Scattered azo dyes
CN101974255B (en) * 2010-10-28 2014-03-19 浙江闰土股份有限公司 Black-blue disperse dye composition
CN102229757B (en) * 2011-04-29 2013-08-14 浙江闰土股份有限公司 Disperse dye composition with a color range of yellow to golden yellow
CN106893358B (en) * 2017-01-26 2019-06-18 浙江龙盛化工研究有限公司 It is a kind of blue to black disperse dye composition, dye preparations and application

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