CN112708287B - Disperse yellow dye composition, and product and application thereof - Google Patents

Disperse yellow dye composition, and product and application thereof Download PDF

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Publication number
CN112708287B
CN112708287B CN202011614231.3A CN202011614231A CN112708287B CN 112708287 B CN112708287 B CN 112708287B CN 202011614231 A CN202011614231 A CN 202011614231A CN 112708287 B CN112708287 B CN 112708287B
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component
dye composition
disperse yellow
yellow dye
disperse
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CN112708287A (en
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何旭斌
杨日升
孟明
何豪华
吴赳
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ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
Shaoxing Shangyu Jinguan Chemical Co ltd
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ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
Shaoxing Shangyu Jinguan Chemical 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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008—Preparations of disperse dyes or solvent 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
    • C09B67/0033—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
    • 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
    • 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
    • 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
    • D06P3/82—Textiles which contain different kinds of fibres

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

Abstract

The invention discloses a disperse yellow dye composition, and a product and application thereof. The disperse yellow dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one of compounds shown in a formula (I), the component B is selected from at least one of compounds shown in a formula (II), the component C is selected from at least one of compounds shown in a formula (III), and based on the component A, the component B and the component C, the mass percent of the component A is 5-85%, the mass percent of the component B is 5-85%, and the mass percent of the component C is 5-60%. The invention provides a disperse yellow dye composition and application of a product in printing and dyeing of a hydrophobic fiber material, and the disperse yellow dye composition has the characteristics of good pH dependency, excellent light fastness, sublimation fastness, washing fastness and the like.

Description

Disperse yellow dye composition, and product and application thereof
(I) the technical field
The invention relates to a disperse yellow dye composition, a product thereof and application in printing and dyeing of hydrophobic fiber materials.
(II) background of the invention
The yellow disperse dye has more structural types, such as bisazo type disperse yellow 23 which is forbidden due to easy decomposition of carcinogenic aromatic amine 4-aminoazobenzene; the nitro diphenylamine has good color fastness and is suitable for various fibers, and the dyeing property needs to be improved; the quinoline-based disperse yellow 54 has a vivid color, and recently, the amount thereof is increasing with the prohibition of the disperse yellow 23. The three-branch disperse dye can be colored under the condition of weak alkalinity, but is sensitive to strong alkali.
The polyester fabric is subjected to alkali decrement (alkali boiling) before dyeing, and then a large amount of water is used for washing off residual alkali, and because the washing is not thorough, the residual alkali is brought into a dye bath to cause frequent printing and dyeing accidents. Although the disperse yellow dye introduced in patent CN107603273A has good pH dependency, the light fastness thereof still needs to be further improved to meet higher printing and dyeing requirements.
Disclosure of the invention
In order to solve the problems, the invention provides an environment-friendly disperse yellow dye composition, a product and application thereof in printing and dyeing of hydrophobic fiber materials, wherein when the composition is applied to printing and dyeing of hydrophobic fiber materials, the composition has the characteristics of good pH dependency, excellent fastness to sunlight, sublimation and washing and the like.
The technical scheme adopted by the invention is as follows:
a disperse yellow dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one of compounds shown in a formula (I), the component B is selected from at least one of compounds shown in a formula (II), the component C is selected from at least one of compounds shown in a formula (III), and based on the component A, the component B and the component C, the mass percent of the component A is 5-85%, the mass percent of the component B is 5-85%, and the mass percent of the component C is 5-60%;
Figure BDA0002875730130000011
Figure BDA0002875730130000021
in formulae (I) to (III):
X 1 is 1 or 2C 1 ～C 4 Alkyl radical, R 1 Is C 1 ～C 4 Alkoxy-substituted C 1 ～C 4 Alkyl or benzyl;
X 2 is-SO 2 NHR 8 ，R 8 Is C 1 ～C 18 Straight or branched alkyl of R 2 Is C 1 ～C 4 Alkyl radical, X 3 Is hydrogen, methyl or bromine;
R 3 、R 4 each independently of the other being hydrogen, halogen or nitro, R 5 、R 6 One is C 1 ～C 4 Alkyl, cyanoethyl, benzyl or phenethyl, the other is methoxycarbonylmethyl or methoxycarbonylethyl, preferably R 5 、R 6 One is ethyl or benzyl and the other is methoxycarbonylmethyl.
In the present invention, said C 1 ～C 4 The alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl. Said C 1 ～C 4 The alkoxy group may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy.
Preferably, the component A is one of the following formulas or a mixture of two or more of the following formulas in any proportion:
Figure BDA0002875730130000022
Figure BDA0002875730130000031
Figure BDA0002875730130000041
further, component A is at least one selected from the group consisting of formulas (I-1) to (I-5).
Still further, component A is selected from formula (I-1).
Preferably, the component B is one of the following formulas or a mixture of two or more of the following formulas in any proportion:
Figure BDA0002875730130000042
Figure BDA0002875730130000051
further, component B is selected from at least one of formulae (II-1) to (II-7).
Still further, component B is selected from (II-1).
Preferably, the component C is one of the following formulas or a mixture of two or more of the following formulas in any proportion:
Figure BDA0002875730130000061
further, component C is selected from at least one of formulas (III-1) to (III-3).
Preferably, the disperse yellow dye composition comprises a component A, a component B and a component C, wherein based on the component A, the component B and the component C, the mass percent of the component A is 20-85%, the mass percent of the component B is 5-75%, and the mass percent of the component C is 5-50%. Further, based on the component A, the component B and the component C, the mass percentage of the component A is 30-85%, the mass percentage of the component B is 5-65%, and the mass percentage of the component C is 5-45%.
Further, the disperse yellow dye composition is composed of a component A, a component B and a component C.
Furthermore, the disperse yellow dye composition comprises a component A, a component B and a component C, wherein based on the component A, the component B and the component C, the mass percent of the component A is 20-85%, the mass percent of the component B is 5-75%, and the mass percent of the component C is 5-50%.
The disperse yellow dye composition preferably comprises a component A, a component B and a component C, wherein:
the component A is at least one selected from formulas (I-1) to (I-5);
the component B is at least one selected from formulas (II-1) to (II-7);
the component C is selected from at least one of formulas (III-1) to (III-3);
based on the component A, the component B and the component C, the mass percentage of the component A is 20-85%, the mass percentage of the component B is 5-75%, and the mass percentage of the component C is 5-50%.
Or the disperse yellow dye composition of the invention preferably consists of a component A, a component B and a component C, wherein:
the component A is at least one selected from formulas (I-1) to (I-5);
the component B is selected from at least one of formulas (II-1) to (II-7);
the component C is at least one selected from formulas (III-1) to (III-3);
based on the component A, the component B and the component C, the mass percentage of the component A is 20-85%, the mass percentage of the component B is 5-75%, and the mass percentage of the component C is 5-50%.
In addition to the above components a, B and C, the disperse yellow dye composition of the present invention may further include other dye components that do not substantially affect the properties of the disperse yellow dye composition, such as c.i. disperse yellow 246 and c.i. disperse orange 61, if necessary.
The disperse yellow dye composition can be directly sold as a commodity, or can be sold as a commodity after being added with a conventional auxiliary agent or applied to coloring textile materials. Therefore, the invention also provides a disperse yellow dye product, which comprises the disperse yellow dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5. Preferably, the disperse yellow dye product consists of the disperse yellow dye composition and an auxiliary agent. 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 of the following or a mixture of two or more of the following in any proportion: 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), polycarboxylates, and the like.
The preparation method of the disperse yellow dye product comprises the following steps: mixing the dye monomer compounds (crude dyes) which form the disperse yellow dye composition according to a ratio, and then micronizing by a grinder such as a sand mill or a grinding mill in the presence of an auxiliary agent and water; alternatively, each of the dye monomer compounds may be subjected to a pulverization treatment in the presence of an auxiliary agent and water by a pulverizer such as a sand mill or a grinder and then mixed in a ratio. The disperse yellow dye product of the present invention is liquid after being ground by a sand mill or a grinder, and can be powdery or granular after being spray-dried, which is a preparation method well known to those skilled in the art.
In the present invention, the dye compounds of the formulae (I), (II) and (III) can be conveniently synthesized in a manner known to those skilled in the art, and commercially available ones can also be used.
The dye composition and the dye product can dye hydrophobic fiber materials (such as polyester and blended fabrics thereof) in a conventional mode in the industry, such as a common dip dyeing method, a high-temperature high-pressure dyeing method or a low-temperature carrier 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, after dyeing, washing the hydrophobic fiber material to be neutral by cold water, wringing the hydrophobic fiber material, then 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.
When the disperse yellow dye composition and the dye product provided by the invention are applied to dyeing of hydrophobic fiber materials, the disperse yellow dye composition and the dye product have the characteristics of good pH dependence, excellent sunlight resistance, sublimation resistance, washing fastness and the like.
(IV) detailed description of the invention
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1:
45 g of the compound of the formula (I-1), 30 g of the compound of the formula (II-1), 25 g of the compound of the formula (III-1) and 250 g of the dispersing agent MF are mixed with 2500 g of water, and then the mixture is ground, dispersed and dried to obtain the finished product, wherein the dye can provide yellow tone for polyester and blended fabrics thereof.
Figure BDA0002875730130000081
Figure BDA0002875730130000091
Examples 2 to 32:
according to the method described in example 1, except that the components A-C in Table 1 are adopted in structure and weight, 250 g of auxiliary agent (200 g of dispersant MF and 50 g of sodium lignosulfonate) is added, 3000 g of water is added to be mixed to prepare slurry, and the slurry is ground, dispersed and dried to prepare the finished product, wherein the dye can provide yellow hue to polyester and blended fabrics thereof:
TABLE 1
Figure BDA0002875730130000092
Figure BDA0002875730130000101
Comparative example 1:
example 1 in CN109021616A was taken as comparative example 1, and the dye composition was as follows:
Figure BDA0002875730130000102
Figure BDA0002875730130000111
pH dependence experiment:
0.5 g of the disperse dyes prepared in the embodiments 1 to 32 and the comparative example 1 are respectively weighed and dispersed in 500 ml of water, 20 ml of the disperse dyes are absorbed and then mixed with 60 ml of water to prepare dye liquor, acetic acid or sodium carbonate solution is used for adjusting different pH values (the pH values are 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0 and 10.0), 2 g of polyester fabric is put into the dye liquor, the temperature is raised to 70 ℃, the temperature is raised to 130 ℃ by a gradient of about 2 ℃/min, the heat preservation dyeing is carried out for 40 minutes, after the dyeing is finished, the heating is stopped, the temperature of a dye bath is lowered to below 80 ℃, the cloth is taken out, the cloth is fully washed by water, dried, and dried or aired at the temperature of below 100 ℃. The dyed fabric samples under different pH conditions were compared with each other using the shade and intensity of the dyed fabric samples at pH =5 as criteria, and the shade was < 0.5 and the intensity was 100% ± 5% as acceptable, i.e., the dyeing was adapted under the pH conditions, and the results are shown in table 2 below (acceptable is indicated by "√" and unacceptable is indicated by "×"):
TABLE 2
Figure BDA0002875730130000112
Figure BDA0002875730130000121
Dyeing example:
the disperse dyes prepared in the above examples 1-32 and comparative example 1 were respectively selected and tested for light fastness, color fastness to washing and sublimation fastness according to the standard AATCC 16-2004 (40 AFU), AATCC 61-2A and ISO 105-X11, and the results are shown in Table 3 below:
TABLE 3
Figure BDA0002875730130000122
Figure BDA0002875730130000131
In conclusion, the disperse yellow dye composition has good pH dependency, better sunlight resistance, sublimation resistance and washing fastness than the existing similar disperse dyes, and can meet the printing and dyeing requirements of medium-high grade polyester and blended fabrics thereof.

Claims (10)

1. A disperse yellow dye composition comprises a component A, a component B and a component C, wherein the component A is selected from at least one of compounds shown in a formula (I), the component B is selected from at least one of compounds shown in a formula (II), the component C is selected from at least one of compounds shown in a formula (III), based on the component A, the component B and the component C, the mass percent of the component A is 5-85%, the mass percent of the component B is 5-85%, and the mass percent of the component C is 5-60%,
Figure FDA0002875730120000011
in formulae (I) to (III):
X 1 is 1 or 2C 1 ～C 4 Alkyl radical, R 1 Is C 1 ～C 4 Alkoxy-substituted C 1 ～C 4 Alkyl or benzyl;
X 2 is-SO 2 NHR 8 ，R 8 Is C 1 ～C 18 Straight or branched alkyl of R 2 Is C 1 ～C 4 Alkyl radical, X 3 Is hydrogen, methyl or bromine;
R 3 、R 4 each independently of the other being hydrogen, halogen or nitro, R 5 、R 6 One is C 1 ～C 4 Alkyl, cyanoethyl, benzyl or phenethyl, and the other is methoxycarbonylmethyl or methoxycarbonylethyl.
2. A disperse yellow dye composition according to claim 1, wherein: consists of a component A, a component B and a component C.
3. A disperse yellow dye composition according to claim 1 or 2 wherein component a is selected from one of the following formulae or a mixture of two or more thereof in any proportion:
Figure FDA0002875730120000021
Figure FDA0002875730120000031
4. a disperse yellow dye composition according to claim 1 or 2, wherein the component B is selected from one of the following formulae or a mixture of two or more thereof in any proportion:
Figure FDA0002875730120000032
Figure FDA0002875730120000041
5. a disperse yellow dye composition according to claim 1 or 2 wherein component C is selected from one of the following formulae or a mixture of two or more thereof in any proportion:
Figure FDA0002875730120000042
Figure FDA0002875730120000051
6. a disperse yellow dye composition according to claim 1 or 2, wherein: based on the component A, the component B and the component C, the mass percentage of the component A is 20-85%, the mass percentage of the component B is 5-75%, and the mass percentage of the component C is 5-50%.
7. A disperse yellow dye composition according to claim 3, wherein component a is at least one member selected from the group consisting of formulae (i-1) to (i-5).
8. A disperse yellow dye composition according to claim 4, wherein component B is at least one member selected from the group consisting of formulae (II-1) to (II-7).
9. The disperse yellow dye composition according to claim 5, wherein component C is at least one selected from the group consisting of formulae (III-1) to (III-3).
10. A disperse yellow dye product, which contains the disperse yellow dye composition as claimed in claim 1 and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5.
CN202011614231.3A 2020-12-31 2020-12-31 Disperse yellow dye composition, and product and application thereof Active CN112708287B (en)

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CN109957259A (en) * 2019-03-02 2019-07-02 浙江龙盛集团股份有限公司 It is a kind of yellow to orange disperse dye composition and dye preparations
CN112708286A (en) * 2020-12-31 2021-04-27 浙江龙盛染料化工有限公司 Blue-to-black disperse dye composition and dye product

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JP6162165B2 (en) * 2014-03-31 2017-07-12 富士フイルム株式会社 Colored composition, cured film, color filter, method for producing color filter, solid-state imaging device, image display device, organic electroluminescence device, pigment and method for producing pigment

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109957259A (en) * 2019-03-02 2019-07-02 浙江龙盛集团股份有限公司 It is a kind of yellow to orange disperse dye composition and dye preparations
CN112708286A (en) * 2020-12-31 2021-04-27 浙江龙盛染料化工有限公司 Blue-to-black disperse dye composition and dye product

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