CN112048190B - Disperse blue-to-black dye composition and dye product thereof - Google Patents

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

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CN112048190B
CN112048190B CN202010994554.3A CN202010994554A CN112048190B CN 112048190 B CN112048190 B CN 112048190B CN 202010994554 A CN202010994554 A CN 202010994554A CN 112048190 B CN112048190 B CN 112048190B
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disperse blue
dye composition
formula
black dye
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CN112048190A (en
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杨日升
陶建国
孟明
陈玉良
魏沁
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Zhejiang Longsheng Dye Chemical Co ltd
Zhejiang Longsheng Group Co Ltd
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Zhejiang Longsheng Dye Chemical Co ltd
Zhejiang Longsheng Group Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046Mixtures of two or more azo dyes
    • C09B67/0051Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008Preparations of disperse dyes or solvent dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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
    • D06P1/18Azo dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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
    • D06P1/19Nitro dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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
    • D06P1/20Anthraquinone dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters using dispersed dyestuffs
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82Textiles which contain different kinds of fibres
    • D06P3/8204Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8214Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups

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

Abstract

The invention discloses a disperse blue-to-black dye composition and a dye product thereof. The disperse blue-black dye composition comprises a component A, a component B, a component C and a component D, 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 the component D is selected from one or more compounds shown in a formula (IV). The invention 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. When the dye product is applied to dyeing or printing of hydrophobic fiber materials, the dye product has the characteristics of good lifting force, excellent color fastness and the like.

Description

Disperse blue-to-black dye composition and dye product thereof
(I) technical field
The invention relates to a disperse blue-to-black dye composition and a dye product, in particular to a disperse blue-to-black dye composition and a dye product which are suitable for hydrophobic fiber materials and blended fabrics thereof.
(II) background of the invention
The blue-black series disperse dye is the variety with the largest use amount in the dyeing of polyester fibers and fabrics. Although conventional disperse deep blue and disperse black such as disperse blue ECO, disperse black ECT and disperse black S-4BL are relatively low in price, the promotion is general, and for orders with high requirements for blackness, the dye consumption is increased, the production sewage amount is increased, so that the sewage treatment cost is increased, adverse effects on environmental protection are caused, and the requirements cannot be met in color fastness. With the increasing requirements of people on textile products, the disperse dye product with higher washing fastness and sublimation fastness has great market potential.
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 good lifting force, excellent color fastness 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, a component C and a component D, 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), the component D is selected from one or more compounds shown in a formula (IV), in the disperse dye composition, the mass percent of the component A is 5-90%, the mass percent of the component B is 5-90%, the mass percent of the component C is 1-50%, and the mass percent of the component D is 1-50%;
Figure BDA0002692092800000021
in formula (I):
R1is hydrogen or CONH2
In the formula (II):
X1is H or halogen;
R2、R3each independently is C1~C4Alkyl or allyl;
in the formula (III):
X2is H or halogen;
R4、R5each independently is C1~C4Alkyl, allyl or benzyl;
in the formula (IV):
X3、X4each independently is hydrogen or halogen; r6、R7Each independently is C1~C4Alkyl or substituted alkyl, the substituent of the substituted alkyl is cyano, phenyl, -OCO-Ph or-OCOK1Wherein, K is1Is C1~C4An alkyl group.
In the above formulas (I) to (IV), said C1~C4The alkyl group may be methyl, ethyl, straight or branched propyl or butyl. The halogen is preferably Cl or Br.
In the disperse blue to black dye composition of the present invention, component A is preferably selected from one of the following formulas or a mixture of two of the following formulas in any proportion:
Figure BDA0002692092800000031
the component B is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
Figure BDA0002692092800000032
Figure BDA0002692092800000041
the component C is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any ratio:
Figure BDA0002692092800000042
Figure BDA0002692092800000051
the component D is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any ratio:
Figure BDA0002692092800000052
Figure BDA0002692092800000061
further, the disperse blue-to-black dye composition comprises a component A, a component B, a component C and a component D, wherein the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, the mass percentage of the component C is 1-40%, and the mass percentage of the component D is 1-40%.
Further, the disperse blue-to-black dye composition comprises a component A, a component B, a component C and a component D, wherein the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, the mass percentage of the component C is 1-40%, and the mass percentage of the component D is 1-40%.
The disperse blue to black dye composition according to the invention preferably comprises component a, component B, component C and component D, wherein:
the component A is at least one of formulas (I-1) to (I-2), and is more preferably (I-2);
the component B is at least one of formulas (II-1) to (II-4), more preferably at least one of (II-3) and (II-4);
the component C is at least one of formulas (III-1) to (III-8), and more preferably at least one of (III-1) and (III-2);
the component D is at least one of formulas (IV-1) to (IV-5), more preferably at least one of (IV-1) and (IV-3);
the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, the mass percentage of the component C is 1-40%, and the mass percentage of the component D is 1-40%.
The disperse blue to black dye composition of the invention preferably consists of component a, component B, component C and component D, wherein:
the component A is at least one of formulas (I-1) to (I-2), and is more preferably (I-2);
the component B is at least one of formulas (II-1) to (II-4), more preferably at least one of (II-3) and (II-4);
the component C is at least one of formulas (III-1) to (III-8), and more preferably at least one of (III-1) and (III-2);
the component D is at least one of formulas (IV-1) to (IV-5), more preferably at least one of (IV-1) and (IV-3);
the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, the mass percentage of the component C is 1-40%, and the mass percentage of the component D is 1-40%.
The disperse blue-black dye composition provided by the invention is also allowed to be further compounded with other dyes to be synergistic to prepare a new blue or black composition, for example, C.I. disperse blue 60, C.I. disperse blue 73, C.I. disperse blue 77, C.I. disperse blue 148 and the like are further added, and the content of the other dyes is preferably not more than 30% of that of the disperse blue-black dye composition.
The disperse blue-black dye composition provided by the invention usually needs to be added with conventional auxiliaries in the process of commercialization or application. Therefore, the invention also provides a disperse blue-black dye product which can be directly used as a commodity or directly applied, and the disperse blue-black dye product comprises 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. Preferably, the disperse blue-black dye product consists of the disperse blue-black 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 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 dye monomer compounds (crude dyes) for forming the disperse blue-black dye composition according to a ratio, and then carrying out microparticulation by using 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 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.
It should be noted that, 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 the components and the proportion of the dye contained in the product.
The dye product 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 invention provides a disperse blue-black dye composition and a dye product, which have the characteristics of good lifting force, excellent friction resistance, washing resistance and sublimation fastness and the like when being applied to dyeing of hydrophobic fiber materials.
(IV) description of the drawings
FIG. 1 is a graph showing the lifting force curves of the dyes obtained in examples 1 to 3 and comparative example 1.
(V) 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:
mixing 10 g of a compound of a formula (I-2), 40 g of a compound of a formula (II-3), 20 g of a compound of a formula (III-1), 30 g of a compound of a formula (IV-1) and 280 g of a dispersing agent MF with 1000 g of water, grinding, dispersing and spray drying to obtain a finished product, wherein the finished product can provide black tone of polyester and blended fabrics thereof.
Figure BDA0002692092800000091
Example 2:
15 g of the compound of the formula (I-2), 60 g of the compound of the formula (II-4), 10 g of the compound of the formula (III-2), 15 g of the compound of the formula (IV-1) and 250 g of the dispersing agent MF are mixed with 1000 g of water, and then the mixture is ground, dispersed and spray-dried to obtain the finished product, wherein the finished product can provide navy blue color tone of polyester and blended fabrics thereof.
Figure BDA0002692092800000101
Examples 3 to 28
According to the method described in the embodiment 1-2, 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, 1200 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 BDA0002692092800000102
Figure BDA0002692092800000111
Example 29
10 g of a compound of a formula (I-2), 40 g of a compound of a formula (II-3), 20 g of a compound of a formula (III-1), 30 g of a compound of a formula (IV-1), 5 g of C.I. disperse blue 60 shown in a formula (V-1), 250 g of a dispersing agent MF, 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 BDA0002692092800000121
Example 30
10 g of a compound of a formula (I-2), 40 g of a compound of a formula (II-3), 20 g of a compound of a formula (III-1), 30 g of a compound of a formula (IV-1), 5 g of C.I. disperse blue 148 shown in a formula (V-2), 250 g of a dispersing agent MF, 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 BDA0002692092800000131
Example 31
10 g of a compound of a formula (I-2), 40 g of a compound of a formula (II-3), 20 g of a compound of a formula (III-1), 30 g of a compound of a formula (IV-1), 5 g of C.I. disperse blue 77 shown in a formula (V-3), 250 g of a dispersing agent MF, 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 BDA0002692092800000132
Figure BDA0002692092800000141
Comparative example 1:
example 1 in patent CN102516812A patent was taken as comparative example 1.
Figure BDA0002692092800000142
Dyeing example:
selecting the disperse dyes prepared in the above examples 1-31 and comparative example 1, treating the polyester fabric by a conventional high-temperature high-pressure dyeing method, controlling the dyeing depth (o.w.f) to be 4.0% and the bath ratio to be 1: 25, adjusting the pH value of a dyeing bath to be 4-5, dyeing at room temperature, heating to 130 ℃ at a speed of 1 ℃/min, keeping the temperature for 45min, reducing, cleaning, washing and drying by a conventional method to obtain a blue-to-black dyed fabric. Sublimation, rub and wash fastness were tested according to ISO105-P01, ISO105-X12, ISO105-C10, respectively, and the results are given in Table 2 below:
TABLE 2
Figure BDA0002692092800000151
Figure BDA0002692092800000161
Lifting force example:
the dyes of examples 1 to 3 and comparative example 1 were subjected to high-temperature high-pressure dyeing at dyeing concentrations of 0.5%, 1.0%, 2.0%, 4.0%, 6.0%, and 8.0%, respectively, according to the method of GB/T2397-2012, and the lifting force performance was evaluated, and the results are shown in fig. 1.
Therefore, the disperse blue to black dye composition disclosed by the invention is excellent in various fastness properties, wherein the lifting power and the washing staining fastness are superior to those of comparative example 1, and the printing and dyeing of fabrics with high fastness requirements can be met.

Claims (10)

1. A disperse blue-to-black dye composition comprises a component A, a component B, a component C and a component D, 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), the component D is selected from one or more compounds shown in a formula (IV), in the disperse dye composition, the mass percent of the component A is 5-90%, the mass percent of the component B is 5-90%, the mass percent of the component C is 1-50%, and the mass percent of the component D is 1-50%;
Figure FDA0002692092790000011
in formula (I):
R1is hydrogen or CONH2
In the formula (II):
X1is H or halogen;
R2、R3each independently is C1~C4Alkyl or allyl;
in the formula (III):
X2is H or halogen;
R4、R5each independently is C1~C4Alkyl, allyl or benzyl;
in the formula (IV):
X3、X4each independently is hydrogen or halogen; r6、R7Each independently is C1~C4Alkyl or substituted alkyl, the substituent of the substituted alkyl is cyano, phenyl, -OCO-Ph or-OCOK1Wherein, K is1Is C1~C4An alkyl group.
2. Disperse blue to black dye composition according to claim 1, characterized in that: the disperse blue-to-black dye composition comprises a component A, a component B, a component C and a component D, wherein based on the component A to the component D, the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, the mass percentage of the component C is 1-40%, and the mass percentage of the component D is 1-40%.
3. Disperse blue to black dye composition according to claim 1, characterized in that: the disperse blue-to-black dye composition comprises a component A, a component B, a component C and a component D, wherein based on the component A to the component D, the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, the mass percentage of the component C is 1-40%, and the mass percentage of the component D is 1-40%.
4. Disperse blue to black dye composition according to any of claims 1 to 3, characterized in that: the component A is selected from one of the following formulas or a mixture of two formulas in any proportion:
Figure FDA0002692092790000021
5. disperse blue to black dye composition according to any of claims 1 to 3, characterized in that: 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 FDA0002692092790000031
6. disperse blue to black dye composition according to any of claims 1 to 3, characterized in that: the component C is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
Figure FDA0002692092790000041
Figure FDA0002692092790000051
7. disperse blue to black dye composition according to any of claims 1 to 3, characterized in that: the component D is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
Figure FDA0002692092790000052
8. disperse blue to black dye composition according to any of claims 1 to 3, characterized in that:
the component A is at least one of formulas (I-1) to (I-2);
the component B is at least one of formulas (II-1) to (II-4);
the component C is at least one of formulas (III-1) to (III-8);
the component D is at least one of formulas (IV-1) to (IV-5);
Figure FDA0002692092790000061
Figure FDA0002692092790000071
Figure FDA0002692092790000081
9. the disperse blue to black dye composition according to claim 8, wherein:
the component A is (I-2);
the component B is at least one of (II-3) and (II-4);
the component C is at least one of (III-1) and (III-2);
the component D is at least one of (IV-1) and (IV-3).
10. A disperse blue-black dye product, which comprises the disperse blue-black 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: 1.
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