CN110358325A - A kind of disperse black dye composition and dye preparations - Google Patents

A kind of disperse black dye composition and dye preparations Download PDF

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Publication number
CN110358325A
CN110358325A CN201910496502.0A CN201910496502A CN110358325A CN 110358325 A CN110358325 A CN 110358325A CN 201910496502 A CN201910496502 A CN 201910496502A CN 110358325 A CN110358325 A CN 110358325A
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China
Prior art keywords
component
formula
dye composition
black dye
disperse black
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CN201910496502.0A
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CN110358325B (en
Inventor
杨日升
何豪华
杨伟军
袁文炳
王江峰
李建勋
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Zhejiang Longsheng Group Co Ltd
Zhejiang Longsheng Dyestuff Chemical Co Ltd
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Zhejiang Longsheng Group Co Ltd
Zhejiang Longsheng Dyestuff Chemical 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
    • 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
    • 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

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

Abstract

The invention discloses a kind of disperse black dye composition and dye preparations.The disperse black dye composition includes component A, component B and component C, wherein component A is selected from one of compound shown in formula (I) or a variety of, component B is selected from one of compound shown in formula (II) or a variety of, and the component C is selected from least one of compound shown in formula (III).The disperse black dye composition also can further include component D, and the component D is selected from least one of compound shown in formula (IV).Also a kind of dispersed black dye product of the present invention, contains the disperse black dye composition and auxiliary agent, and the weight ratio of auxiliary agent and disperse dye composition is 0.2~5:1.Dispersed black dye product application of the present invention has the characteristics that low dyeing cost and rub resistance, water-fastness and fastness to sublimation are excellent in hydrophobic fiber material dyeing or stamp.

Description

A kind of disperse black dye composition and dye preparations
(1) technical field
The present invention relates to a kind of disperse black dye composition and dye preparations.
(2) background technique
It is all the fashion in the market at home and abroad containing spandex stretch fabric.This kind of product elasticity with higher and excellent time It is elastic can, soft, comfortable and easy to wear, easy absorbing sweat and the advantages that electrostatic will not be generated.Wash/main the use of ammonia stockinette dyeing Disperse dyes, since affinity of many disperse dyes to spandex is high, stainability is good, disperse dyes are tight to the contamination of spandex Weight.In fastness test, the disperse dyes being infected on spandex are easy to migrate out from fiber, influence polyester fibre/spandex weaving The wet colour fastness of product.Many disperse dyes have good rub resistance, washable and color fastness to light on terylene, but in spandex On fastness, can only achieve medium level, so that there are biggish in dyeing process to the demanding product of color fastness Problem.ZL 200910156655.7, ZL 200910156654.2 have developed the dyestuff that can meet above-mentioned requirements, but still have had Improved space.
(3) summary of the invention
To solve the above problems, being applied to hydrophobic the present invention provides a kind of disperse black dye composition and dye preparations Property fibrous material dyeing or when stamp, have the characteristics that color fastness is excellent and it is good to dye economy.
The technical solution adopted by the present invention is that:
A kind of disperse black dye composition, including component A, component B and component C, wherein component A is selected from formula (I) shownization One of object or a variety of is closed, component B is selected from one of compound shown in formula (II) or a variety of, and the component C is selected from formula (III) at least one of compound shown in, based on the component A, component B and component C, the mass percentage of component A It is 35~95%, the mass percentage of component B is 1~35%, and the mass percentage of component C is 1~35%:
In formula (I):
X1For halogen;
R1、R2Respectively stand alone as C1~C4Alkyl;
R3、R4Respectively stand alone as-CH2COOK1Or-C2H4COOK2, wherein K1、K2Respectively stand alone as C1~C4Alkyl;
In formula (II):
R5、R6Respectively stand alone as C1~C18Alkyl.
In formula (III):
R7For cyano or nitro;
R8For hydrogen or C1~C4Alkoxy;
R9For C1~C4Alkyl;
R10、R11Respectively stand alone as C1~C4Alkyl or replace alkyl, it is described replace alkyl substituent group be-OCOK3Or- COOK4, wherein K3、K4Respectively stand alone as C1~C4Alkyl.
In above-mentioned formula (I), (II) or (III), the C1~C18Alkyl can be methyl, ethyl, linear chain or branched chain Propyl, the butyl of linear chain or branched chain, the hexyl of linear chain or branched chain, the octyl of linear chain or branched chain, linear chain or branched chain dodecyl, The octadecyl etc. of linear chain or branched chain.The C1~C4Alkyl can be methyl, ethyl, the propyl of linear chain or branched chain, straight chain or The butyl of branch.The C1~C4Alkoxy can be methoxyl group, ethyoxyl, the propoxyl group of linear chain or branched chain, linear chain or branched chain Butoxy.Halogen is preferably Cl or Br.
Preferably, component A is selected from the mixture of one of following formula or in which two or more arbitrary proportions:
Preferably, the component B is selected from the mixture of one of following formula or in which two or more arbitrary proportions:
Preferably, the component C is selected from the mixture of one of following formula or in which two or more arbitrary proportions:
As a further preference, the black disperse dye composition includes component A, component B and component C, wherein Component A is (I-2), and component B is (II-1), and component C is at least one of (III-1), (III-2), (III-7).
Preferably, the mass percentage of component A is 40~90% in the black disperse dye composition, The mass percentage of component B is 1~30%, and the mass percentage of component C is 5~35%.
Preferably, the black disperse dye composition is made of component A, component B and component C, wherein component A Mass percentage is 35~95% (preferably 40~90%), the mass percentage of component B be 1~35% (preferably 1~ 30%), the mass percentage of component C is 1~35% (preferably 5~35%).
As a further preference, the black disperse dye composition is made of component A, component B and component C, Middle component A is (I-2), and component B is (II-1), and component C is at least one of (III-1), (III-2), (III-7);It is described Black disperse dye composition in, the mass percentage of component A is 40~90%, and the mass percentage of component B is 1 The mass percentage of~30%, component C are 5~35%.
Disperse black dye composition of the present invention, also can further include component D, and the component D is selected from formula (IV) At least one of shown compound, in the dye composite, the mass percentage of the A is 35~95%, component B's Mass percentage is 1~35%, and the mass percentage of component C is 1~35%, the mass percentage of component D is 1~ 35%,
In formula (IV):
R12For-C3H6OCH3、-C3H6OC2H5、-C3H6OC2H4OCH3
Preferably, the component D is selected from the mixture of one of following formula or in which two or more arbitrary proportions:
Preferably, in the disperse black dye composition, the mass percentage of component A is 40~95% (preferably It is 40~85%), the mass percentage of component B is 1~30% (preferably 5~30%), and the mass percentage of component C is 5~35% (preferably 5~30%), the mass percentage of component D are 1~30% (preferably 1~25%).
Preferably, the disperse black dye composition is made of component A, component B, component C and component D.
As a further preference, the disperse black dye composition is made of component A, component B, component C and component D, Wherein:
Component A is at least one of formula (I-1)~(I-4);
Component B is at least one of formula (II-1)~(II-7);
Component C is selected from least one of formula (III-1)~(III-8);
Component D is selected from least one of formula (IV-1)~(IV-3).
The particularly preferred disperse black dye composition is made of component A, component B, component C and component D, in which:
Component A is formula (I-2);
Component B is formula (II-1);
Component C is selected from formula (III-1), (at least one of III-2, (III-7);
Component D is selected from least one of formula (IV-1), (IV-3).
It is emphasized that dispersed black dye compound of the present invention, in the dyestuff of pyridone hydroxyl ortho position coupling Exist usually in the form of quinone hydrazone body, that is, the dyestuff of logical formula (II) substantially has quinone hydrazone body structure shown in following formula (IIa), considers To the writing style of those skilled in the art, the written form of azo body is still used in summary of the invention and embodiment part, this Have no effect on essence of the invention:
Wherein R5、R6It is identical as the definition in above-mentioned formula (II) compound.
Disperse black dye composition of the present invention usually requires in commercialization that conven-tional adjuvants are added.Therefore, The present invention also provides a kind of dispersed black dye product, contain the disperse black dye composition and auxiliary agent, auxiliary agent and point The weight ratio for dissipating dye composite is 0.2~5:1.Preferably, the dispersed black dye product is by the black dye of dispersion Feed composition and auxiliary agent composition.The auxiliary agent is that common dispersing agent, diffusant and other surfaces are living when disperse dyes compound Property agent etc., preferably is selected from one of following or in which two or more mixture: lignosulfonates (lignin 85A, lignin 83A Deng), alkyl naphthalene sulfonic acid formaldehyde condensation products (such as condensation compound of methyl naphthalene sulfonic acid and formaldehyde (Dispersant MF)), naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent NNO), benzyl naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent CNF), anhydrous sodium sulphate etc..
Dispersed black dye product of the present invention the preparation method is as follows: the dyestuff that disperse black dye composition will be formed After monomeric compound (former dyestuff) mixes according to the ratio, carried out in the presence of auxiliary agent, water with pulverizers such as sand mill or grinders Corpusculed;It in addition can also the crushing such as sand mill or grinder in the presence of auxiliary agent, water respectively by dye monomer compound Machine is mixed in proportion after carrying out corpusculed processing.Dispersed black dye product of the present invention, with sand mill or grinding It is liquid after machine grinding, can is powdery, graininess after spray drying, this is well known to those skilled in the art preparation method, by It can not be by the removing of moisture 100%, so even being in powdery or granular dye preparations, still in spray-drying process Allow that there are a certain amount of moisture, preferably more than the 10% of dye preparations gross weight.
In addition, it is necessary to which explanation makes the promotion of dyeing effect when dye preparations are applied to the printing and dyeing of textile fabric Contribution is technically characterized in that dye component contained in the product and ratio.
Disperse black dye composition of the present invention also allows that new indigo plant is made with the further compound synergic of other dyestuffs The compositions such as color, navy or black.
In the present invention, formula (I), (II), (III), dye composition is convenient to by those skilled in the art shown in (IV) Mode known to member synthesizes, and can also use commercial goods.
The present invention provides application of the dispersed black dye product in hydrophobic fiber material dyeing or stamp.
It, can be by ways customary in industry to hydrophobic fiber material using dyestuff made of dye composite of the invention (such as polyester and its blended fabric such as wash/ammonia intertexture) is dyed, and common dip method or high-temperature and high pressure dyeing process are such as used It is dyed, it can also be used to direct printing.Wherein, common dip method such as pre-processes hydrophobic fiber material, is put into dye It is disseminated in cylinder, dye finishes, and cold water wash to neutrality squeezes out, and restores again cleaning, dries;Direct printing such as by fabric into Row dye pre-treatment, is dried, and setting prints disperse dyes mill base on printing machine, then evaporated, and is made on fabric in the way of decatize Dye fixing, finally wash, stentering forming.
Disperse black dye composition and dye preparations provided by the invention, when being applied to hydrophobic fiber material dyeing, tool There is the features such as dyeing at low cost and rub resistance, water-fastness and fastness to sublimation is excellent.
(4) specific embodiment
The present invention is described further combined with specific embodiments below, but protection scope of the present invention is not limited in This:
Embodiment 1:
By 65 grams of formula (I-2) compounds, 20 grams of formula (II-1) compounds, 15 grams of formula (III-1) compounds, 200 grams of point Powder MF, after adding 1000 grams of water blendings, grinding distribution is spray-dried to get finished product, which can provide polyester and its blended knit Object black tone.
Embodiment 2:
By 55 grams of formula (I-2) compounds, 20 grams of formula (II-1) compounds, 10 grams of formula (III-1) compounds, 15 grams of formula (IV- 1) compound, 180 grams of Dispersant MF, after adding 650 grams of water blendings, grinding distribution is spray-dried to get finished product, the finished product energy Polyester and its blended fabric black tone are provided.
Embodiment 3:
By 48 grams of formula (I-2) compounds, 30 grams of formula (II-1) compounds, 10 grams of formula (III-1) compounds, 5 grams of formula (III- 7) compound, 180 grams of Dispersant MF, after adding 600 grams of water blendings, grinding distribution is spray-dried to get finished product, the finished product energy Polyester and its blended fabric black tone are provided.
Embodiment 4~40
According to method described in embodiment 1-3, the difference is that using the knot of component A, component B, component C, component D in table 1 Structure and weight are added 200 grams of auxiliary agent (Dispersant MF is 150 grams, and sodium lignin sulfonate is 50 grams), make after adding 1000 grams of blendings of water At slurries, grinding distribution, dry, finished product, which can be supplied to polyester and its blended fabric items fastness ability is excellent Black tone.
Table 1
Embodiment 41:
By 50 grams of formula (I-2) compounds, 20 grams of formula (II-1) compounds, 10 grams of formula (III-1) compounds, 15 grams of formula (IV- 1) compound, 5 grams 82,250 grams of C.I. disperse red of Dispersant MF, after adding 200 grams of water blendings, grinding distribution, spray drying, i.e., Finished product is obtained, which can provide polyester and its blended fabric black tone.
Comparative example 1:
By embodiment 1 in CN 101735663A as a comparison case 1.
Comparative example 2:
By embodiment 1 in CN101760046A as a comparison case 2.
Dyeing Example:
The dyestuff for weighing disperse dyes made from 2 grams of Examples 1 to 41, comparative example 1 and 2 respectively, using conventional high temperature height It is padded color method processing and washs/ammonia intertexture, in treatment process, control dye level (o.w.f) 4.0%, bath raio 1: 50 adjusts dye bath pH Value 4~5, room temperature enter dye, are warming up to 130 DEG C with 1 DEG C/min, keep the temperature 45min, restore washing, washing, drying by well-established law, cooling It is taken out to 70 DEG C.Sample cloth coloured light is observed, the ISO105-X12 that adopts international standards, AATCC 61-2A, ISO 105-P01 are surveyed respectively Its rub resistance, water-fastness, color fastness to sublimation are tried, can provide uniformly and the good black dyeing and weaving object of fastness ability, specifically be shown in Table 2:
Table 2
Disperse black dye composition provided by the present invention, it is low in cost compared to the disperse dyes of comparative example 1 and 2, Can be reduced respectively by contaminating one ton of fabric by 700~800 yuan of cost, produce apparent economic benefit, and be applied to wash/polyurethane fabric dye When color, the fastness ability of dyestuff of the present invention is more excellent, can further compound with pinkish red, dark blue disperse dyes, enrich dye species.

Claims (10)

1. a kind of disperse black dye composition, it is characterised in that: the disperse black dye composition includes component A, component B and group Divide C, wherein component A is selected from one of compound shown in formula (I) or a variety of, and component B is selected from compound shown in formula (II) One or more, the component C is selected from least one of compound shown in formula (III), based on the component A, component B With component C, the mass percentage of component A is 35~95%, and the mass percentage of component B is 1~35%, the matter of component C Measuring percentage composition is 1~35%:
In formula (I):
X1For halogen;
R1、R2Respectively stand alone as C1~C4Alkyl;
R3、R4Respectively stand alone as-CH2COOK1Or-C2H4COOK2, wherein K1、K2Respectively stand alone as C1~C4Alkyl;
In formula (II):
R5、R6Respectively stand alone as C1~C18Alkyl.
In formula (III):
R7For cyano or nitro;
R8For hydrogen or C1~C4Alkoxy;
R9For C1~C4Alkyl;
R10、R11Respectively stand alone as C1~C4Alkyl or replace alkyl, it is described replace alkyl substituent group be-OCOK3Or- COOK4, wherein K3、K4Respectively stand alone as C1~C4Alkyl.
2. disperse black dye composition as described in claim 1, it is characterised in that: the disperse black dye composition is by group Divide A, component B and component C composition, wherein the mass percentage of component A is 35~95% (preferably 40~90%), component B's Mass percentage is 1~35% (preferably 1~30%), and the mass percentage of component C is 1~35% (preferably 5~35%).
3. disperse black dye composition as described in claim 1, it is characterised in that: the disperse black dye composition is into one Step includes component D, and the component D is selected from least one of compound shown in formula (IV), in the dye composite, the A Mass percentage be 35~95%, the mass percentage of component B is 1~35%, and the mass percentage of component C is 1 The mass percentage of~35%, component D are 1~35%,
In formula (IV):
R12For-C3H6OCH3、-C3H6OC2H5Or-C3H6OC2H4OCH3
4. disperse black dye composition as claimed in claim 3, it is characterised in that: the disperse black dye composition is by group Divide A, component B, component C and component D composition, wherein the mass percentage of the A is 35~95%, the quality percentage of component B Content is 1~35%, and the mass percentage of component C is 1~35%, and the mass percentage of component D is 1~35%.
5. the disperse black dye composition as described in one of claim 1-4, it is characterised in that: the component A be selected from following formula it One or in which two or more arbitrary proportions mixture:
6. the disperse black dye composition as described in one of claim 1-4, it is characterised in that: the component B be selected from following formula it One or in which two or more arbitrary proportions mixture:
7. the disperse black dye composition as described in one of claim 1-4, it is characterised in that: the component C be selected from following formula it One or in which two or more arbitrary proportions mixture:
8. disperse black dye composition as described in claim 3 or 4, it is characterised in that: the component D be selected from one of following formula or The mixture of two of them any of the above ratio:
9. the disperse black dye composition as described in one of claim 1-4, it is characterised in that: the disperse black dye composition In:
Component A is formula (I-2);
Component B is formula (II-1);
Component C is selected from formula (III-1), (at least one of III-2, (III-7);
Component D is selected from least one of formula (IV-1), (IV-3);
10. a kind of dispersed black dye product, containing disperse black dye composition and auxiliary agent described in one of claim 1-4, The weight ratio of auxiliary agent and disperse dye composition is 0.2~5:1.
CN201910496502.0A 2019-06-10 2019-06-10 Disperse black dye composition and dye product Active CN110358325B (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113072820A (en) * 2021-04-07 2021-07-06 江苏华尔化工有限公司 Dark blue to black disperse dye composition and preparation method thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62169167A (en) * 1986-01-22 1987-07-25 Ricoh Co Ltd Green toner for electrophotography
US5038415A (en) * 1989-01-10 1991-08-13 Sumitomo Chemical Company, Limited Disperse dye composition useful for dyeing of printing hydrophobic fiber materials: mixture of pyridone mono-azo dyes and optionally a quino-phthalone
CN101735663A (en) * 2009-12-31 2010-06-16 上虞市金冠化工有限公司 Composite black disperse dye
CN101760046A (en) * 2009-12-31 2010-06-30 上虞市金冠化工有限公司 Dispersive black dye composition
KR20130130966A (en) * 2012-05-23 2013-12-03 공명도 Black and navy blue disperse dye composition having excellent moisture resistance

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62169167A (en) * 1986-01-22 1987-07-25 Ricoh Co Ltd Green toner for electrophotography
US5038415A (en) * 1989-01-10 1991-08-13 Sumitomo Chemical Company, Limited Disperse dye composition useful for dyeing of printing hydrophobic fiber materials: mixture of pyridone mono-azo dyes and optionally a quino-phthalone
CN101735663A (en) * 2009-12-31 2010-06-16 上虞市金冠化工有限公司 Composite black disperse dye
CN101760046A (en) * 2009-12-31 2010-06-30 上虞市金冠化工有限公司 Dispersive black dye composition
KR20130130966A (en) * 2012-05-23 2013-12-03 공명도 Black and navy blue disperse dye composition having excellent moisture resistance

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113072820A (en) * 2021-04-07 2021-07-06 江苏华尔化工有限公司 Dark blue to black disperse dye composition and preparation method thereof

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