CN116656151A - Disperse red dye composition, dye product and application thereof - Google Patents

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

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Publication number
CN116656151A
CN116656151A CN202310411906.1A CN202310411906A CN116656151A CN 116656151 A CN116656151 A CN 116656151A CN 202310411906 A CN202310411906 A CN 202310411906A CN 116656151 A CN116656151 A CN 116656151A
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China
Prior art keywords
component
disperse red
red dye
dye composition
formula
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Granted
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CN202310411906.1A
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Chinese (zh)
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CN116656151B (en
Inventor
何旭斌
朱鹏飞
方叶明
陈立锋
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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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Publication of CN116656151A publication Critical patent/CN116656151A/en
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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
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008Preparations of disperse dyes or solvent 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
    • C09B67/0033Blends 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
    • 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
    • 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
    • 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 red dye composition, a dye product and application thereof. The disperse red dye composition comprises a component A, a component B and a component C, wherein the component A is selected from one or more of compounds shown in a formula (I), the component B is selected from one or more of compounds shown in a formula (II), and the component C is selected from one or more of compounds shown in a formula (III). The invention provides a disperse red dye product, which contains the disperse red dye composition and an auxiliary agent, whereinThe weight ratio of the auxiliary agent to the disperse red dye composition is 0.2-5:1. The invention also provides application of the disperse red dye product in dyeing or printing of hydrophobic fiber materials, and the disperse red dye product has bright color and excellent fastness of washing resistance, sublimation resistance, friction resistance and the like.

Description

Disperse red dye composition, dye product and application thereof
Technical Field
The invention relates to the field of disperse dyes, in particular to a disperse red dye composition, a dye product and application of the dye product in dyeing or printing of hydrophobic fiber materials, particularly polyester and blended fabrics thereof.
Background
In recent years, polyester-polyurethane blended fabrics are popular in the market because of better elasticity, wrinkle resistance, skin affinity and sweat absorption. Meanwhile, the cleaning condition of the blended fabric is not high, and the blended fabric can be cleaned by hand, machine and dry, so that the fabric is not damaged, and the requirements of sportswear and other middle-high-end clothing fabrics are met. At present, the blended fabric has the defects of poor stability and easy fading compared with pure polyester fabric. Therefore, the dye has higher requirements for coloring, wherein the disperse red dye is used as a color species with wider application, namely, can be used for monochromatic application and can be used for the compounding synergy of dark dye varieties. The color fastness of the red monochromatic and compound dye used for the polyester-polyurethane blended fabric in the market is required to be further improved.
Disclosure of Invention
In order to solve the problems, the invention provides a disperse red dye composition, a dye product and application thereof, wherein the dye product is used for dyeing or printing hydrophobic fiber materials, particularly polyester-spandex blended fabrics, and has bright color light and excellent fastness to washing, sublimation, friction and the like.
The technical scheme adopted by the invention is as follows:
in a first aspect, the invention provides a disperse red dye composition, which comprises a component A, a component B and a component C, wherein the component A is selected from one or more of compounds shown in a formula (I), the component B is selected from one or more of compounds shown in a formula (II), the component C is selected from one or more of compounds shown in a formula (III), the mass percentage of the component A is 1-97%, the mass percentage of the component B is 1-97%, and the mass percentage of the component C is 1-97%:
in the above formula (I):
R 1 is hydrogen or C 1 ~C 4 Alkoxy groups of (a);
R 2 is C 1 ~C 4 Alkyl of (a);
m is 1 or 2;
in the above formula (II):
R 3 、R 4 each independently is C 1 ~C 4 Alkyl, -R 6 OCOR 6’ 、-R 7 CN、-R 8 OCOPh, wherein R 6 、R 7 、R 8 Each independently is C 1 ~C 4 Alkylene group, R 6’ Is C 1 ~C 4 Is phenyl;
R 5 is hydrogen or C 1 ~C 4 Alkyl of (a);
in the above formula (III):
R 9 、R 10 each independently is C 1 ~C 4 Alkyl, -R 12 OCOR 13 、-R 14 CN、-R 15 OCOPh, wherein R 12 、R 14 、R 15 Each independently is C 1 ~C 4 Alkylene group, R 13 Is C 1 ~C 4 Is phenyl;
R 11 is hydrogen or C 1 ~C 4 Is a hydrocarbon group.
In the above formulae (I) to (III), the above C 1 ~C 4 The alkyl group may be methyl, ethylA group, a linear or branched propyl group, a linear or branched butyl group, said C 1 ~C 4 The alkoxy group of (C) may be methoxy, ethoxy, straight or branched propoxy, straight or branched butoxy, said C 1 ~C 4 The alkylene group of (a) may be methylene, ethylene, straight or branched propylene, straight or branched butylene.
Preferably, in the disperse red dye composition, the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, and the mass percentage of the component C is 5-90%; more preferably, the mass percentage of the component A is 20-90%, the mass percentage of the component B is 5-75%, and the mass percentage of the component C is 5-75%.
Preferably, the disperse red dye composition disclosed by the invention comprises at least one component A selected from the following formulas (I-1) to (I-7):
further preferably, component A is at least one of the formulae (I-1) and (I-2).
Preferably, the disperse red dye composition disclosed by the invention comprises at least one component B selected from the following formulas (II-1) to (II-5):
further preferably, component B is at least one of the formulae (II-1) and (II-2).
Preferably, the disperse red dye composition disclosed by the invention comprises at least one component C selected from the following formulas (III-1) to (III-8):
further preferably, component C is at least one of formulas (III-1) to (III-4).
As a still further preference, the disperse red dye composition comprises a component a, a component B and a component C, wherein:
component A is at least one of the formulas (I-1) and (I-2);
the component B is at least one of the formula (II-1) and the formula (II-2);
the component C is at least one of the formulas (III-1) to (III-4);
in the disperse red dye composition, the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, and the mass percentage of the component C is 5-90%.
As still further preferred, the disperse red dye composition consists of a component a, a component B and a component C, wherein:
component A is at least one of the formulas (I-1) and (I-2);
the component B is at least one of the formula (II-1) and the formula (II-2);
the component C is at least one of the formulas (III-1) to (III-4);
in the disperse red dye composition, the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, and the mass percentage of the component C is 5-90%.
The disperse red dye composition provided by the invention also allows the disperse red dye composition to be further compounded and synergized with other dyes to prepare a new dye variety, for example, C.I. disperse red 183, C.I. disperse red 356 and the like are added, and the addition amount is not more than 20% of the total amount of the dye.
The disperse dye compositions according to the invention, in which the dyes of the formulae (I) to (III) are known dyes, can be synthesized commercially available or by conventional methods, for example by means of customary diazotisation and coupling reactions using the appropriate components known to those skilled in the art and using the necessary proportions, or by reference to the process or analogous processes in patent CN108410204A, GB1324235A, JP 62158764A.
The disperse red dye composition of the invention generally requires the addition of conventional auxiliary agents during commercialization or direct application. Thus, in a second aspect, the present invention also provides a disperse red dye preparation which can be directly used as a commodity or directly applied, comprising the disperse red dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse red dye composition is 0.2-5:1. Preferably, the disperse red dye product consists of the disperse red dye composition and an auxiliary agent. The auxiliary agent is a dispersing agent, other surfactants and the like which are commonly used in disperse dye compounding, and is preferably one or a mixture of more than two of the following components: lignosulfonate (lignin 85A, lignin 83A, etc.), alkyl naphthalene sulfonic acid formaldehyde condensate (such as methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF)), naphthalene sulfonic acid formaldehyde condensate (dispersant NNO), benzyl naphthalene sulfonic acid formaldehyde condensate (dispersant CNF), anhydrous sodium sulfate, etc.
The preparation method of the disperse red dye product provided by the invention comprises the following steps: mixing dye monomer compounds (raw dyes) forming the disperse red dye composition according to a proportion, and then carrying out micropellet formation by using a pulverizer such as a sand mill or a grinding machine in the presence of an auxiliary agent and water; alternatively, the dye monomer compounds may be subjected to a fine particle formation treatment by a pulverizer such as a sand mill or a grinding machine in the presence of an auxiliary agent and water, respectively, and then mixed in proportion. The disperse red dye preparation according to the invention is liquid after grinding by a sand mill or a grinding machine, and can be in powder or granule form after spray drying, which is a preparation method known to the person skilled in the art, since 100% removal of moisture is not possible during spray drying, a certain amount of moisture is allowed to exist in the dye preparation even in powder or granule form, preferably not more than 10% of the total weight of the dye preparation.
In addition, when the dye product is applied to dyeing of textile fibers, the technical feature contributing to the improvement of dyeing effect is the components and proportions of the dye composition contained in the product.
In a third aspect, the invention also provides the use of the disperse red dye article in dyeing or printing hydrophobic fibre materials.
The dye product prepared by the dye composition can be used for dyeing hydrophobic fiber materials (such as polyester and blended fabrics thereof, such as polyester/ammonia fabrics) in a manner conventional in industry, such as dyeing by a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be used for direct printing. The common dip dyeing method can be operated as follows: pretreating a hydrophobic fiber material, putting the pretreated hydrophobic fiber material into a dye vat for dip dyeing, washing the dye vat with cold water until the dye vat is neutral, wringing the dye vat to dryness, and then carrying out reduction washing and drying; direct printing may be operated as follows: and (3) carrying out dyeing pretreatment on the fabric, drying, shaping, printing disperse dye color paste on a printing machine, steaming, fixing the color of the dye on the fabric by utilizing a steaming mode, washing with water, and tentering and shaping.
Compared with the prior art, the invention has the beneficial effects that: the disperse red dye composition and the dye product provided by the invention are applied to dyeing or printing of hydrophobic fiber materials, and have the characteristics of bright color, excellent fastness such as water washing resistance, sublimation resistance, friction resistance and the like.
Detailed Description
The invention will be further described with reference to the following specific examples, but the scope of the invention is not limited thereto:
example 1:
40 g of component A composed of a compound of a formula (I-1), 30 g of component B composed of a compound of a formula (II-1), 15 g of component C composed of a compound of a formula (III-1) and a compound of a formula (III-2) and 250 g of dispersing agent MF are mixed together by adding 2000 g of water, and then are ground, dispersed and dried to obtain a finished product, wherein the finished product can provide polyester and the red color tone of blended fabrics thereof.
Example 2:
30 g of component A consisting of a compound shown in a formula (I-1), 30 g of component B consisting of a compound shown in a formula (II-1), 20 g of a compound shown in a formula (III-3) and 20 g of a compound shown in a formula (III-4) and 200 g of sodium lignin sulfonate are mixed with 2000 g of water, and then ground, dispersed and dried to obtain a finished product, wherein the finished product can provide polyester and the red color tone of blended fabrics of the polyester.
Examples 3 to 30
According to the method described in example 1 or 2, except that 200 g of an auxiliary agent (150 g of dispersing agent MF and 50 g of sodium lignin sulfonate) and 2000 g of water were added to the composition and weight of the components A to C shown in Table 1, and the mixture was blended to prepare a slurry, and the slurry was ground, dispersed and dried to prepare a finished product, the following dyes were capable of providing polyesters and their blended fabrics with red hues excellent in various fastness properties.
TABLE 1
Example 31
40 g of component A consisting of the compound shown in the formula (I-1), 30 g of component B consisting of the compound shown in the formula (II-1), 20 g of component C consisting of the compound shown in the formula (III-1), 10 g of C.I. disperse red 356 and 250 g of dispersing agent MF are mixed together by adding 2000 g of water, and then are ground, dispersed and dried to obtain a finished product, wherein the finished product can provide polyester and the red color tone of the blended fabric of the polyester.
Dyeing examples:
2g of the disperse red dye prepared in examples 1-30 is weighed respectively, the polyester-spandex knitted fabric is treated by a conventional high-temperature high-pressure dyeing method and a heat setting method, in the treatment process, the dyeing depth (o.w.f) is controlled to be 4.0 percent, the bath ratio is 1:40, the pH value of a dyeing bath is regulated to be 4-5, the dyeing is carried out at room temperature, the temperature is increased to 130 ℃ at 1 ℃/min, the dyeing is carried out for 30min, and the red dyed fabric is obtained by washing, reduction cleaning (flake alkali 2g/L, sodium hydrosulfite 3g/L and 85 ℃ for 20 min), acid washing neutralization (acetic acid 2g/L and 40 ℃ for 15 min), washing and drying and heat setting at 180 ℃ for 30 seconds according to the conventional method. The fastness to rubbing, to sublimation and to washing were measured according to ISO 105-X12, ISO 105-P01, ISO 105-C10, respectively, and the results are shown in Table 2 below.
TABLE 2
Therefore, the disperse red dye composition and the dye product thereof have excellent fastness, particularly excellent washing fastness, and can meet the high-fastness requirement of fabric printing and dyeing.

Claims (10)

1. A disperse red dye composition characterized by: the disperse red dye composition comprises a component A, a component B and a component C, wherein the component A is one or more of compounds shown in a formula (I), the component B is one or more of compounds shown in a formula (II), the component C is one or more of compounds shown in a formula (III), the mass percent of the component A is 1-97%, the mass percent of the component B is 1-97%, and the mass percent of the component C is 1-97%;
in the above formula (I):
R 1 is hydrogen or C 1 ~C 4 Alkoxy groups of (a);
R 2 is C 1 ~C 4 Alkyl of (a);
m is 1 or 2;
in the above formula (II):
R 3 、R 4 each independently is C 1 ~C 4 Alkyl, -R 6 OCOR 6’ 、-R 7 CN、-R 8 OCOPh, wherein R 6 、R 7 、R 8 Each independently is C 1 ~C 4 Alkylene group, R 6’ Is C 1 ~C 4 Is phenyl;
R 5 is hydrogen or C 1 ~C 4 Alkyl of (a);
in the above formula (III):
R 9 、R 10 each independently is C 1 ~C 4 Alkyl, -R 12 OCOR 13 、-R 14 CN、-R 15 OCOPh, wherein R 12 、R 14 、R 15 Each independently is C 1 ~C 4 Alkylene group, R 13 Is C 1 ~C 4 Is phenyl;
R 11 is hydrogen or C 1 ~C 4 Is a hydrocarbon group.
2. The disperse red dye composition of claim 1, wherein: in the disperse red dye composition, the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, and the mass percentage of the component C is 5-90%.
3. The disperse red dye composition of claim 2, wherein: in the disperse red dye composition, the mass percentage of the component A is 20-90%, the mass percentage of the component B is 5-75%, and the mass percentage of the component C is 5-75%.
4. A disperse red dye composition according to any one of claims 1 to 3, wherein: the component A is selected from at least one of the following formulas (I-1) to (I-7):
5. a disperse red dye composition according to any one of claims 1 to 3, wherein: the component B is at least one selected from the following formulas (II-1) to (II-5):
6. a disperse red dye composition according to any one of claims 1 to 3, wherein: the component C is at least one selected from the following formulas (III-1) to (III-8):
7. the disperse red dye composition of claim 1, wherein: the disperse red dye composition comprises a component A, a component B and a component C, wherein:
component A is at least one of the formulas (I-1) and (I-2);
the component B is at least one of the formula (II-1) and the formula (II-2);
the component C is at least one of the formulas (III-1) to (III-4);
in the disperse red dye composition, the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, and the mass percentage of the component C is 5-90%;
8. the disperse red dye composition of claim 7, wherein: the disperse red dye composition consists of a component A, a component B and a component C, wherein:
component A is at least one of the formula (I-1) or the formula (I-2);
the component B is at least one of the formula (II-1) or the formula (II-2);
the component C is at least one of the formulas (III-1) to (III-4);
in the disperse red dye composition, the mass percentage of the component A is 5-90%, the mass percentage of the component B is 5-90%, and the mass percentage of the component C is 5-90%.
9. A disperse red dye article comprising the disperse red dye composition of any one of claims 1-3 and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse red dye composition is 0.2-5:1.
10. Use of the disperse red dye article according to claim 9 for dyeing or printing hydrophobic fibre materials.
CN202310411906.1A 2023-04-18 2023-04-18 Disperse red dye composition, dye product and application thereof Active CN116656151B (en)

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CN109971215A (en) * 2019-03-21 2019-07-05 浙江龙盛集团股份有限公司 A kind of dispersion red dye composition and dye preparations
KR20190096125A (en) * 2018-02-08 2019-08-19 (주)경인양행 Disperse dyes composites and methods of dyeing fiber using the same
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Publication number Priority date Publication date Assignee Title
US5529586A (en) * 1993-08-26 1996-06-25 Sumitomo Chemical Company, Limited Compositions containing a benzodifuranone compound and methods for coloring hydrophobic materials using the same
JPH09105082A (en) * 1995-10-04 1997-04-22 Canon Inc Ink jet printing and printed product
CN1648170A (en) * 2004-12-28 2005-08-03 浙江龙盛集团股份有限公司 Disperse red dye composition
CN101333343A (en) * 2008-07-30 2008-12-31 浙江闰土股份有限公司 Red disperse dye composition of comprehensive high-fastness series
CN101974251A (en) * 2010-07-30 2011-02-16 江苏亚邦染料股份有限公司 Disperse red dye with high washing fastness
CN101983993A (en) * 2010-07-30 2011-03-09 江苏亚邦染料股份有限公司 Dispersed scarlet dye composite with high washing fastness
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KR20190096125A (en) * 2018-02-08 2019-08-19 (주)경인양행 Disperse dyes composites and methods of dyeing fiber using the same
CN111511981A (en) * 2018-02-08 2020-08-07 京仁洋行股份有限公司 High-fastness disperse dye composition and method for dyeing fibers by using same
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CN109971215A (en) * 2019-03-21 2019-07-05 浙江龙盛集团股份有限公司 A kind of dispersion red dye composition and dye preparations
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