CN111423741A - Disperse yellow dye and synthetic method thereof - Google Patents

Disperse yellow dye and synthetic method thereof Download PDF

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Publication number
CN111423741A
CN111423741A CN202010373438.XA CN202010373438A CN111423741A CN 111423741 A CN111423741 A CN 111423741A CN 202010373438 A CN202010373438 A CN 202010373438A CN 111423741 A CN111423741 A CN 111423741A
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disperse yellow
yellow dye
dye
butyl
structural formula
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李百春
陈望全
钱军良
贺建斌
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Hangzhou Fulai Anthracite Technology Co ltd
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Hangzhou Fulai Anthracite Technology 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
    • C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • 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
    • 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
    • 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
    • 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/14—Wool
    • D06P3/143—Wool using dispersed 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/26—Polyamides; Polyurethanes 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
    • D06P3/34—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
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/6033—Natural or regenerated cellulose using dispersed dyes
    • D06P3/6041—Natural or regenerated cellulose using dispersed dyes using specified dyes

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

Abstract

The invention discloses a disperse yellow dye and a synthesis method thereof, belonging to the field of dyes, and the disperse yellow dye comprises one or more than two structures shown as a formula (I)The components shown in the specification;
Figure DDA0002479217230000011
in the formula (I), R1Is C1～C4Alkyl of R2Is C1～C4The alkyl has the advantages of low cost, good washing fastness, sublimation fastness and light fastness.

Description

Disperse yellow dye and synthetic method thereof
Technical Field
The invention relates to the field of dyes, in particular to a disperse yellow dye and a synthetic method thereof.
Background
The yellow disperse dyes have more structural varieties, wherein the disperse yellow RGF L has good compatibility with other dyes and bright color light, and is widely applied to low-temperature three primary colors with good performance often formed by disperse red 3B and disperse blue 2B L N, however, as the disperse yellow RGF L is easy to decompose carcinogenic substances and is listed in forbidden disperse dyes, various countries in the world vigorously research and develop other substitute disperse yellows, and more disperse yellow 114 is adopted at present.
Disperse yellow 114 (disperse yellow 6GS L; disperse brilliant yellow 6GS L; Schumaron brilliant orange H4R) with the structure shown below, also named as Suchongdan, ethiocarb granule, pirimicarb, sulpirimicarb, 2- [ (ethylthio) methyl]Phenyl methyl carbamate, 2- (ethylthiomethyl) phenyl N-methyl carbamate or chlorpheniramine maleate with molecular formula C20H16N4O4S, molecular weight 408.43.
Figure BDA0002479217220000011
The chemical properties are as follows: is yellow powder, and has no change in color when it is dyed with calcium and magnesium ions, reddish color when it is dyed with iron ions, and dark color when it is dyed with copper ions, and has no alkali resistance when it is dyed and printed, and suitable pH value is 3-7.
The disperse brilliant yellow 6GS L is suitable for dyeing terylene by a high-temperature high-pressure method and a hot melting method, is not suitable for dyeing terylene by a carrier method, can be directly printed on terylene fabrics, but can not be used as a ground color for discharge-proof printing, is also used for dyeing terylene-cotton blended fabrics by a hot melting method of chemical book, has good compatibility with other disperse dyes and bright yellow colored light, can be used as a main color or a color matching in light color, has good dyeing performance on diacetate fibers and triacetate fibers, and is not suitable for dyeing polyamide fibers.
The production method comprises the following steps: the m-benzenesulfonic ester aniline and 1, 4-dimethyl-3-cyano-6-hydroxy-2-pyridone are used as raw materials, the former is firstly diazotized and then coupled with the latter to obtain a product, and the product is filtered, ground and dried to obtain a finished product.
However, the preparation process of the disperse yellow 114 is complex, the amount of generated sewage is large, and the use cost is high.
Disclosure of Invention
1. Technical problem to be solved
Aiming at the problems in the prior art, the first purpose of the invention is to provide a disperse yellow dye which has the advantages of low cost, good washing fastness, sublimation fastness and light fastness;
the second purpose is to provide a synthetic method of disperse yellow dye, compared with the existing preparation process of disperse yellow 114 in life, the production process of the disperse yellow dye has simpler steps, greatly reduces the production cost and is convenient to popularize and apply.
2. Technical scheme
In order to solve the above problems, the present invention adopts the following technical solutions.
A disperse yellow dye comprises one or more than two components with the structure shown in formula (I);
Figure BDA0002479217220000021
in the formula (I), R1Is C1～C4Alkyl of R2Is C1～C4Alkyl of (C)1～C4The alkyl group of (b) may be one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.
Further, said R1Is C3～C4Alkyl group of (1).
Further, said R1Is n-butyl, and has the following structural formula:
Figure BDA0002479217220000031
further, said R2Is C1～C2Alkyl or butyl of (a).
Further, theR2Is n-butyl, and has the following structural formula:
Figure BDA0002479217220000032
further, said R1Is n-butyl, the R2Is n-butyl, and has the following structural formula:
Figure BDA0002479217220000033
further, said R2Is CH3The structural formula is as follows:
Figure BDA0002479217220000041
further, said R2Is C2H5The structural formula is as follows:
Figure BDA0002479217220000042
further, the disperse yellow dye is formed by mixing a component A shown in a structural formula (VI) and a component B shown in a structural formula (VII) in any proportion.
Figure BDA0002479217220000043
Further, the mass ratio of the component A to the component B is 6: 2.5 to 4.
Further, the mass ratio of the component A to the component B is 6: 3.
a synthetic method of a disperse yellow dye comprises the following steps:
s1: performing diazotization reaction on sulfanilamide and sodium nitrite or nitrosyl sulfuric acid under an acidic condition to obtain diazonium salt;
s2: performing coupling reaction on the diazonium salt obtained in the step S1 and a pyridone solution to obtain a coupling product;
s3: and (4) carrying out post-treatment on the coupling product obtained in the step S2 to obtain the disperse yellow dye.
Further, in step S1, the molar ratio of sulfanyl butylamine to sodium nitrite or nitrosyl sulfuric acid is 1: 1 to 1.58.
3. Advantageous effects
Compared with the prior art, the invention has the advantages that:
firstly, the disperse yellow dye has the advantages of low cost, good washing fastness, sublimation fastness and light fastness and the like.
Compared with the existing preparation process of disperse yellow 114 in life, the synthetic method adopted by the scheme has the advantages of simpler steps, greatly reduced production cost and convenient popularization and application.
Detailed Description
The technical scheme in the embodiment of the invention is clearly and completely described below; obviously; the described embodiments are only some of the embodiments of the invention; but not all embodiments, are based on the embodiments in the invention; all other embodiments obtained by a person skilled in the art without making any inventive step; all fall within the scope of protection of the present invention.
R1Preferred test examples of (a):
Figure BDA0002479217220000061
in the formula (I), R1Is C1～C4Alkyl of R2Is C1～C4Alkyl group of (1).
R is as defined above1C in (1)1～C4The alkyl group of (a) may be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group or a tert-butyl group.
Figure BDA0002479217220000062
Analyzing the above table when R2Is a methyl group, and the compound is,R1each methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, preferably R1Is C3～C4Wherein R is most preferred1Is n-butyl, and so on, when R is2The tests were carried out with ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, respectively, the most preferred combinations being R1Is n-butyl, to which only R is attached2Table for methyl.
R2Preferred test examples of (a):
Figure BDA0002479217220000071
in the formula (I), R1Is C1～C4Alkyl of R2Is C1～C4Alkyl group of (1).
R is as defined above2C in (1)1～C4The alkyl group of (A) may be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group or a tert-butyl group, since R is obtained from the above test examples1Is most preferably n-butyl, when R is used1Is n-butyl, to R2A preference test was performed.
Figure BDA0002479217220000072
Analyzing the above table when R1Is n-butyl, R2When R is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, respectively, R is preferably R2Is C1～C2Alkyl or butyl of (1), wherein R is most preferred2Are methyl and n-butyl.
Preferred test examples of dyes:
the dye is divided into two cases, one is only composed of a component with the structure shown in the formula (I), and the other is composed of more than two components with the structure shown in the formula (I);
the first dye and the second dye are preferably the first dye shown in the structural formula (VI) and the second dye shown in the structural formula (III-1);
Figure BDA0002479217220000081
applying the first dye and the second dye to the same fabric, where the polyester fabric is selected, respectively, to obtain the following table:
Figure BDA0002479217220000082
analysis of the table above reveals that dye two dyes are the most preferred because they give better color than dye one.
Secondly, in the latter case, the component A shown in the structural formula (VI) and the component B shown in the structural formula (VII) are mixed in any proportion, and the mass ratio of the component A to the component B is preferably 6: 2.5 to 4.
Figure BDA0002479217220000091
Component A Component B Fastness to washing Color fastness to sunlight Fastness to sublimation
6 2.5 4-5 4 3-4
6 2.8 4-5 4 4
6 3.0 4-5 4 4-5
6 3.2 4-5 4 4
6 3.8 4-5 4 4
6 4 4-5 4 3-4
Analytically above table, most preferably the mass ratio of component a and component B is most preferably 6: 3, at which washing fastness, light fastness and sublimation fastness are optimum, so that the component a represented by the structural formula (VI) and the component B represented by the structural formula (VII) are mixed in a ratio of 6: 3, namely dye three, and applying dye three to a polyester fabric (the fabric here is the same fabric as the first dye and the second dye so as to facilitate the comparison between the second dye and the third dye), to obtain the following table:
Figure BDA0002479217220000101
in summary, the effect of the second dye and the third dye is consistent after the second dye and the third dye are applied to the fabric, so that the second dye and the third dye are both the optimal dyes, but the manufacturing cost of the third dye is lower than that of the second dye, so that the third dye is the optimal dye.
Synthesis examples:
a synthetic method of a disperse yellow dye comprises the following steps:
s1: under the acidic condition, diazotization reaction is carried out on sulfanilamide and sodium nitrite to obtain diazonium salt;
s2: performing coupling reaction on the diazonium salt obtained in the step S1 and a pyridone solution to obtain a coupling product;
s3: and (4) carrying out esterification reaction on the coupling product obtained in the step (S2) and benzene sulfonyl chloride, and carrying out post-treatment after the reaction is completed to obtain the disperse yellow dye.
In step S1, the molar ratio of sulfanilamide to sodium nitrite is 1: 1 to 1.58.
Dyeing example:
the disperse yellow dye prepared by the scheme and the disperse yellow 114 in the prior art are respectively applied to various fabrics such as cotton, chinlon, polyester, terylene and wool, and the washing fastness, the light fastness and the sublimation fastness of the fabrics are tested, and the results are shown in the following table:
Figure BDA0002479217220000102
Figure BDA0002479217220000111
analysis shows that the disperse yellow dye has good washing fastness, light fastness and sublimation fastness effects after being printed on various fabrics.
Comparative example:
the most preferred dyes of the present invention, component a represented by structural formula (VI) and component B represented by structural formula (VII), are mixed in 6: 3, the dye III formed by mixing is applied to the same fabric with the disperse yellow 114 in the prior art, and compared with the best effect of the preferred dye and the disperse yellow 114 on the fabric:
Figure BDA0002479217220000112
in analysis of the above table, comparing the best preferred dye of the present invention with the disperse yellow 114, we find that the best preferred dye of the present invention has a color close to that of the disperse yellow 114 after dyeing, and the best preferred dye of the present invention has good washing fastness, sublimation fastness and light fastness, more importantly, the best preferred dye of the present invention has better sublimation fastness than the disperse yellow 114, and the best preferred dye of the present invention has lower cost and simpler preparation process, thus being convenient for popularization and application.
The above; but are merely preferred embodiments of the invention; the scope of the invention is not limited thereto; any person skilled in the art is within the technical scope of the present disclosure; according to the technical scheme and the improvement concept of the invention, equivalent substitutions or changes are made; are intended to be covered by the scope of the present invention.

Claims (10)

1. A disperse yellow dye is characterized by comprising one or more than two components with the structure shown in formula (I);
Figure FDA0002479217210000011
in the formula (I), R1Is C1～C4Alkyl of R2Is C1～C4Alkyl group of (1).
2. According to the claimsA disperse yellow dye as described in claim 1, wherein R is1Is C3～C4Alkyl group of (1).
3. A disperse yellow dye according to claim 2, wherein R is1Is n-butyl, and has the following structural formula:
Figure FDA0002479217210000012
4. the disperse yellow dye according to claim 1, wherein R is2Is C1～C2Alkyl or butyl of (a).
5. A disperse yellow dye according to claim 4, wherein R is2Is n-butyl, and has the following structural formula:
Figure FDA0002479217210000021
6. a disperse yellow dye according to claim 4, wherein R is2Is CH3The structural formula is as follows:
Figure FDA0002479217210000022
7. a disperse yellow dye according to claim 4, wherein R is2Is C2H5The structural formula is as follows:
Figure FDA0002479217210000023
8. the disperse yellow dye according to claim 1, wherein the disperse yellow dye is prepared by mixing a component A shown in a structural formula (VI) and a component B shown in a structural formula (VII) in any proportion.
Figure FDA0002479217210000031
9. The disperse yellow dye according to claim 8, wherein the mass ratio of the component A to the component B is 6: 2.5 to 4.
10. A synthetic method of a disperse yellow dye is characterized by comprising the following steps:
s1: under the acidic condition, diazotizing sulfanilamide and sodium nitrite or nitrosyl sulfuric acid to obtain diazonium salt;
s2: performing coupling reaction on the diazonium salt obtained in the step S1 and a pyridone solution to obtain a coupling product;
s3: and (4) carrying out post-treatment on the coupling product obtained in the step S2 to obtain the disperse yellow dye.
CN202010373438.XA 2020-05-06 2020-05-06 Disperse yellow dye and synthetic method thereof Pending CN111423741A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060293405A1 (en) * 2004-07-09 2006-12-28 Fuji Photo Film Co., Ltd. Pyridone azo compound, tautomer thereof, and colorant-containing curable composition, color filter and manufacturing method thereof
JP2012042898A (en) * 2010-08-23 2012-03-01 Nippon Shokubai Co Ltd Colorant composition for color filter
CN109957259A (en) * 2019-03-02 2019-07-02 浙江龙盛集团股份有限公司 It is a kind of yellow to orange disperse dye composition and dye preparations
CN110373043A (en) * 2019-06-10 2019-10-25 浙江龙盛染料化工有限公司 It is a kind of blue to black disperse dye composition and dye preparations
CN110922786A (en) * 2019-12-13 2020-03-27 约克夏(浙江)染化有限公司 Black disperse dye composition, disperse dye, preparation method and application thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060293405A1 (en) * 2004-07-09 2006-12-28 Fuji Photo Film Co., Ltd. Pyridone azo compound, tautomer thereof, and colorant-containing curable composition, color filter and manufacturing method thereof
JP2012042898A (en) * 2010-08-23 2012-03-01 Nippon Shokubai Co Ltd Colorant composition for color filter
CN109957259A (en) * 2019-03-02 2019-07-02 浙江龙盛集团股份有限公司 It is a kind of yellow to orange disperse dye composition and dye preparations
CN110373043A (en) * 2019-06-10 2019-10-25 浙江龙盛染料化工有限公司 It is a kind of blue to black disperse dye composition and dye preparations
CN110922786A (en) * 2019-12-13 2020-03-27 约克夏(浙江)染化有限公司 Black disperse dye composition, disperse dye, preparation method and application thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
张淑芬等: "对苯磺酰烷基胺偶氮吡啶酮系聚丙烯用黄色染料的合成及应用 ", 《染料工业》 *

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