CN111484754A - Disperse blue-to-black dye composition and dye product - Google Patents

Disperse blue-to-black dye composition and dye product Download PDF

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Publication number
CN111484754A
CN111484754A CN202010284183.XA CN202010284183A CN111484754A CN 111484754 A CN111484754 A CN 111484754A CN 202010284183 A CN202010284183 A CN 202010284183A CN 111484754 A CN111484754 A CN 111484754A
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component
formula
dye composition
disperse blue
black dye
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CN111484754B (en
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陈东
卢邦义
孟明
陶建国
苏建军
方叶明
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ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
Zhejiang Longsheng Dye Chemical Co ltd
Zhejiang Longsheng Group Co Ltd
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ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
Zhejiang Longsheng Dye Chemical Co ltd
Zhejiang Longsheng Group 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
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • 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
    • 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
    • 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
    • D06P1/19—Nitro 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
    • 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
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8214—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups

Abstract

The invention discloses a disperse blue-to-black dye composition, which comprises a component A, a component B and 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 (III) and/or (IV). The invention provides a disperse blue-to-black dye setThe compound and the dye product have the characteristics of low dyeing cost, excellent friction resistance, washing resistance, sublimation resistance and the like when being applied to dyeing of hydrophobic fiber materials.

Description

Disperse blue-to-black dye composition and dye product
(I) technical field
The invention relates to a disperse blue-to-black dye composition and a dye product.
(II) background of the invention
Due to the increasing requirements on the aspect of dyeing of terylene and spandex materials in recent years, particularly along with the development of terylene/spandex blended fibers, a dye which has consistent or less difference in various dyeing performances such as washing fastness, rubbing fastness, dye uptake, lifting force and the like when applied to the fibers is urgently needed in the market. Especially when dyeing deep and dark color, if the blue-black dye variety is widely applied, people have higher requirements on the dyeing performance and various fastness, while the difference of the fastness of the common disperse dye is larger when dyeing common terylene and spandex fabrics, and particularly in the aspect of washing fastness, the grade difference can reach one grade or more.
At present, from the market situation, the existing products have some defects. Therefore, the development of a class of economic compound dyes with excellent dyeing performance is a main subject of the current dye industry.
Disclosure of the invention
In order to solve the problems, the invention provides a disperse blue-black dye composition and a dye product, which have the characteristics of excellent color fastness, good dyeing economy and the like when being applied to dyeing or printing of hydrophobic fiber materials.
The technical scheme adopted by the invention is as follows:
a disperse blue to black dye composition comprises a component A, a component B and a component C, wherein the component A is selected from one or more compounds shown in a formula (I), the component B is selected from one or more compounds shown in a formula (II), the component C is selected from one or more compounds shown in a formula (III) and/or (IV), in the disperse dye composition, the mass percentage of the component A is 35-90%, the mass percentage of the component B is 1-45%, and the mass percentage of the component C is 1-20%:
Figure BDA0002450026550000011
Figure BDA0002450026550000021
in formula (I):
X1is halogen;
R1、R2each independently is C1～C4An alkyl group;
R3、R4each independently is-CH2COOK1or-C2H4COOK2In which K is1、K2Each independently is C1～C4An alkyl group.
In the formula (II):
X2、X3each independently is hydrogen or halogen; preferably a halogen.
R5、R6Each independently is C1～C4Alkyl or substituted C1～C4Alkyl, said substituted C1～C4The substituent of the alkyl group is selected from-CN, -OCOC6H5、-C6H5Or C1～C4An alkoxy group; preferably-CN or-OCOC6H5Substituted C1～C4An alkyl group.
In the formula (III):
X4、X5each independently Cl, H or-NO2(ii) a preferably-NO2。
R7、R8Each independently is C1～C4Alkyl of-C2H4OCOCH3、-C2H4CN、-C2H4OCOC6H5(ii) a Preferably C1～C4Alkyl or-C2H4OCOC6H5。
In the above formulas (I) to (III), 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. Halogen is preferably Cl or 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:
Figure BDA0002450026550000031
preferably, the component B is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
Figure BDA0002450026550000032
Figure BDA0002450026550000041
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:
Figure BDA0002450026550000042
as a further preference, the disperse blue to black dye composition comprises:
component A is selected from formula (I-1) and/or formula (I-2)
Component B is selected from the group consisting of formula (II-1) and/or (II-3)
Component C is selected from the group consisting of formula (III-1) and/or (III-2)
Based on the components A to C, the mass percentage of the component A is 35-90%, the mass percentage of the component B is 1-45%, and the mass percentage of the component C is 1-20%.
Furthermore, the disperse blue-to-black dye composition comprises a component A, a component B and a component C, wherein based on the component A to the component C, the mass percentage of the component A is 35-90%, the mass percentage of the component B is 1-45%, and the mass percentage of the component C is 1-20%.
The disperse blue-black dye composition can further comprise a component D, wherein the component D is one or more selected from compounds shown in a formula (IV), and the mass percentage of the component D is not more than 30% of the total weight of the components A-C.
Figure BDA0002450026550000051
X6is-COOC2H4OC2H4OCH3、-SO2-C6H5or-CH2O-C6H5，R9Is C1～C4An alkyl group.
Preferably, component D is selected from dyes of at least one of the following formulae:
Figure BDA0002450026550000052
Figure BDA0002450026550000061
preferably, in the blue-to-black disperse dye composition, the mass percentage of the component A is 40-90%, the mass percentage of the component B is 1-40%, the mass percentage of the component C is 1-15%, and the mass percentage of the component D is not more than 25% of the total weight of the components A-C.
Preferably, the disperse blue to black dye composition consists of component a, component B, component C and component D.
As a further preference, the blue to black disperse dye composition consists of component a, component B, component C and component D, wherein:
the component A is selected from at least one of formulas (I-1) to (I-4);
the component B is selected from at least one of formulas (II-1) to (II-5);
the component C is selected from at least one of formulas (III-1) to (III-4);
the component D is at least one selected from formulas (IV-1) to (IV-5).
It should be emphasized that the blue-to-black disperse dye composition of the present invention, the dye coupled at the ortho position of the pyridone hydroxyl group generally exists in the form of quinone hydrazone structure, that is, the dye of the general formula (IV) substantially has the quinone hydrazone structure shown in the following formula (IVa), and in consideration of the writing habit of those skilled in the art, the writing form of azo body is still adopted in the summary and the examples section of the present invention, which does not affect the essence of the present invention:
Figure BDA0002450026550000071
wherein X6、R9The same as defined above for the compound of formula (IV).
The disperse blue to black dye composition of the invention usually needs to be added with conventional auxiliary agents in the commercial process. Therefore, the invention also provides a disperse blue-black dye product, which contains the disperse blue-black dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse 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 (lignin 85A, lignin 83A, etc.), alkylnaphthalenesulfonic acid-formaldehyde condensates (such as methylnaphthalenesulfonic acid-formaldehyde condensate (dispersant MF)), naphthalenesulfonic acid-formaldehyde condensate (dispersant NNO), benzylnaphthalenesulfonic acid-formaldehyde condensate (dispersant CNF), anhydrous sodium sulfate, etc.
The preparation method of the disperse blue-black dye product comprises the following steps: mixing the dye monomer compounds (crude dyes) according to a ratio, 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; alternatively, the dye monomer compound may be subjected to a pulverization 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 a certain proportion. The disperse blue to black dye preparations according to the invention, which are liquid after grinding with a sand mill or a grinding mill, can be in the form of powder or granules after spray drying, are known to the person skilled in the art, and since 100% removal of water is not possible during spray drying, even in the case of dye preparations in powder or granules, a certain amount of water is still allowed, preferably not more than 10% of the total weight of the dye preparation.
In addition, when the dye product is applied to printing and dyeing of textile fibers, the technical characteristics which contribute to the improvement of the dyeing effect are mainly characterized in the components and the proportion of the dye contained in the product.
The disperse blue-black dye composition provided by the invention can be further compounded with other dyes to be synergistic to prepare a new blue, navy blue or black composition, for example, C.I. disperse blue 281, C.I. disperse blue 284, C.I. disperse red 167, C.I. disperse violet 93, C.I. disperse red 145 and the like are added.
In the present invention, the dye compounds represented by the formulae (I), (II), (III) 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 invention provides application of the disperse blue-black dye product in dyeing or printing hydrophobic fiber materials.
The dye prepared by the dye composition can dye hydrophobic fiber materials (such as polyester and blended fabrics thereof, such as polyester/polyurethane blended fabrics) in a conventional mode in the industry, such as a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be used for direct printing. Wherein, the common dip-dyeing method comprises the steps of pretreating the 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, reducing, washing and drying; the direct printing is to carry out dyeing pretreatment, drying and setting on the fabric, print disperse dye color paste on a printing machine, then carry out steaming, fix the color of the dye on the fabric by using a steaming mode, finally wash and tenter setting.
The disperse blue-black dye composition and the dye product provided by the invention have the characteristics of low dyeing cost, excellent friction resistance, washing resistance and sublimation fastness and the like when being applied to dyeing of hydrophobic fiber materials.
(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:
75 g of a compound of a formula (I-2), 15 g of a compound of a formula (II-1), 10 g of a compound of a formula (III-1) and 180 g of a dispersing agent MF are mixed with 800 g of water, and then the mixture is ground, dispersed and spray-dried to obtain a finished product, wherein the finished product can provide blue tone of polyester and blended fabrics thereof.
Figure BDA0002450026550000081
Figure BDA0002450026550000091
Example 1:
65 g of a compound of a formula (I-2), 25 g of a compound of a formula (II-3), 10 g of a compound of a formula (III-1) and 165 g of a dispersing agent MF are mixed with 800 g of water, and then the mixture is ground, dispersed and spray-dried to obtain a finished product, wherein the finished product can provide deep blue tone of polyester and mixed textile thereof.
Figure BDA0002450026550000092
Example 3:
55 g of a compound of a formula (I-2), 30 g of a compound of a formula (II-1), 15 g of a compound of a formula (III-1), 10 g of a compound of a formula (IV-1), 160 g of a dispersant MF, 20 g of a dispersing agent NNO and 1000 g of water are mixed, ground, dispersed and spray-dried to obtain a finished product, and the finished product can provide black tone of polyester and blended fabrics thereof.
Figure BDA0002450026550000093
Figure BDA0002450026550000101
Examples 4 to 25
According to the method described in the examples 1-3, except that the structure and weight of the component A, the component B, the component C and the component D in the table 1 are adopted, 200 g of the auxiliary agent (150 g of the dispersing agent MF and 50 g of the sodium lignosulfonate) is added, 1000 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 blue to black color tones with excellent fastness properties for polyester and blended fabrics thereof.
TABLE 1
Figure BDA0002450026550000102
Figure BDA0002450026550000111
Example 26:
55 g of a compound of a formula (I-2), 20 g of a compound of a formula (II-1), 5 g of a compound of a formula (III-1), 15 g of a compound of a formula (IV-1), 5 g of C.I. disperse red 145, 250 g of a dispersing agent MF, 850 g of water are added for blending, grinding and dispersing are carried out, and spray drying is carried out to obtain a finished product, wherein the finished product can provide black tone for polyester and blended fabrics thereof.
Figure BDA0002450026550000112
Figure BDA0002450026550000121
Comparative example:
example 4 in CN 106800798A was taken as comparative example 1 and example 11 was taken as comparative example 2.
Comparative example 1:
Figure BDA0002450026550000122
comparative example 2:
Figure BDA0002450026550000123
dyeing example:
respectively weighing 2 g of the disperse dye prepared in the examples 1-26 and the dyes in the comparative examples 1 and 2, 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 percent 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, drying and cooling to 70 ℃ according to a conventional method, and taking out. Observing the color of the sample cloth, adopting international standards ISO105-X12 and AATCC 61-2A, ISO 105-P01 to respectively test the fastness to rubbing, washing and sublimation, and providing a uniform dark blue to black dyed fabric with good fastness performance, as shown in Table 2:
TABLE 2
Figure BDA0002450026550000131
Figure BDA0002450026550000141
Therefore, when the blue-to-black disperse dye composition provided by the invention is applied to dyeing of polyester/spandex fabrics, the color fastness is obviously improved compared with that of the existing disperse dye.

Claims (10)

1. A disperse blue to black dye composition comprises a component A, a component B and a component C, wherein the component A is selected from one or more compounds shown in a formula (I), the component B is selected from one or more compounds shown in a formula (II), the component C is selected from one or more compounds shown in a formula (III) and/or (IV), in the disperse dye composition, the mass percentage of the component A is 35-90%, the mass percentage of the component B is 1-45%, and the mass percentage of the component C is 1-20%:
Figure FDA0002450026540000011
in formula (I):
X1is halogen;
R1、R2each independently is C1～C4An alkyl group;
R3、R4each independently is-CH2COOK1or-C2H4COOK2In which K is1、K2Each independently is C1～C4An alkyl group.
In the formula (II):
X2、X3each independently is hydrogen or halogen;
R5、R6each independently is C1～C4Alkyl or substituted C1～C4Alkyl, said substituted C1～C4The substituent of the alkyl group is selected from-CN, -OCOC6H5、-C6H5Or C1～C4An alkoxy group.
In the formula (III):
X4、X5each independently Cl, H or-NO2；
R7、R8Each independently is C1～C4Alkyl of-C2H4OCOCH3、-C2H4CN、-C2H4OCOC6H5。
2. A disperse blue to black dye composition according to claim 1, wherein said component a is selected from at least one of the following formulas:
Figure FDA0002450026540000021
3. a disperse blue to black dye composition according to claim 1, wherein said component B is selected from at least one of the following formulas:
Figure FDA0002450026540000022
Figure FDA0002450026540000031
4. a disperse blue to black dye composition according to claim 1, said component C being selected from at least one of the following formulae:
Figure FDA0002450026540000032
5. a disperse blue to black dye composition according to claim 1 comprising component a, component B and component C, wherein:
component A is selected from formula (I-1) and/or formula (I-2)
Component B is selected from the group consisting of formula (II-1) and/or (II-3)
Component C is selected from the group consisting of formula (III-1) and/or (III-2)
Based on the components A to C, the mass percentage of the component A is 35-90%, the mass percentage of the component B is 1-45%, and the mass percentage of the component C is 1-20%.
6. The disperse blue to black dye composition according to claim 1, which comprises component A, component B and component C, wherein based on the components A to C, the mass percent of the component A is 35 to 90%, the mass percent of the component B is 1 to 45%, and the mass percent of the component C is 1 to 20%.
7. A disperse blue to black dye composition according to claim 1, further comprising a component D selected from one or more compounds of formula (IV), wherein the weight percentage of component D does not exceed 30% of the total weight of components a to C.
Figure FDA0002450026540000041
X6is-COOC2H4OC2H4OCH3、-SO2-C6H5or-CH2O-C6H5，R9Is C1～C4An alkyl group.
8. A disperse blue to black dye composition according to claim 7 wherein component D is selected from at least one of the following formulas:
Figure FDA0002450026540000042
Figure FDA0002450026540000051
9. a disperse blue to black dye composition according to claim 8 consisting of component A, component B, component C and component D.
10. A disperse blue-to-black dye product comprising the disperse blue-to-black dye composition of claim 1 and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5: 1.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113563737A (en) * 2021-06-30 2021-10-29 浙江龙盛集团股份有限公司 Blue-to-black disperse dye composition and dye product

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