CN114806212A - Brilliant blue disperse dye compound, mixture, composition, preparation method and application thereof - Google Patents

Brilliant blue disperse dye compound, mixture, composition, preparation method and application thereof Download PDF

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Publication number
CN114806212A
CN114806212A CN202210371006.4A CN202210371006A CN114806212A CN 114806212 A CN114806212 A CN 114806212A CN 202210371006 A CN202210371006 A CN 202210371006A CN 114806212 A CN114806212 A CN 114806212A
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brilliant blue
disperse dye
formula
blue disperse
compound shown
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陶国来
陶安迪
牟忠岳
徐叙明
胡效奎
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Leping Safely Pharmaceutical Co ltd
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Leping Safely Pharmaceutical 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
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0074Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0077Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
    • C09B29/0081Isothiazoles or condensed isothiazoles
    • 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
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/06Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08Amino benzenes
    • C09B29/0805Amino benzenes free of acid groups
    • C09B29/0807Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • C09B29/0811Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
    • C09B29/0813Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
    • 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
    • C09B67/0079Azoic dyestuff preparations
    • 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
    • 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
    • D06P3/8223Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • D06P3/8228Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
    • D06P3/8233Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye using dispersed dyes

Abstract

The invention discloses a brilliant blue disperse dye compound, a mixture, a composition, a preparation method and application thereofThe application is as follows. The brilliant blue disperse dye compound is a compound shown as a formula I, wherein R is selected from one or a combination of two of methyl, ethyl, n-propyl, isopropyl, allyl, methoxyethyl, ethoxyethyl, acetyl, chloroacetyl, benzoyl and cyclohexylformyl. The invention also discloses a brilliant blue disperse dye mixture, a composition, a preparation method and application thereof. The brilliant blue disperse dye compound has the color light close to that of disperse blue 56, can replace the disperse blue, has high sublimation fastness, has smaller color change when being used for dyeing by a polyester-cotton one-bath method, has small wastewater discharge in the production process, and greatly reduces the production cost. The invention provides more preferable choices for the substitute product of disperse blue 56.

Description

Brilliant blue disperse dye compound, mixture, composition, preparation method and application thereof
Technical Field
The invention relates to a blue disperse dye, in particular to a brilliant blue disperse dye compound, a mixture, a composition, a preparation method and application thereof.
Background
The disperse blue 56 is one of disperse dyes, has bright color and high light fastness, is widely applied to dyeing of terylene and terylene blended fabrics, and can also be applied to printing of the terylene and terylene blended fabrics, and the like. However, the sublimation fastness of the disperse blue 56 is low, the disperse blue 56 belongs to anthraquinone dyes, the synthetic route is long, the production process is complex, a large amount of wastewater is generated in the production process, and the cost is extremely high. Under the current environment-friendly situation, the productivity of the anthraquinone dye is greatly influenced, and the condition of serious goods shortage in the market can occur. Therefore, the development of a dye which is similar to the color light, can replace disperse blue 56, has high sublimation fastness, small wastewater discharge in the production process and low production cost is a problem to be solved urgently in the dye industry.
Disclosure of Invention
The invention aims to provide a brilliant blue disperse dye compound, a mixture, a composition, a preparation method and application thereof. The brilliant blue disperse dye compound has the color light close to that of disperse blue 56, can replace the disperse blue, has high sublimation fastness, has smaller color change when being used for dyeing, has small wastewater discharge in the production process, and greatly reduces the production cost.
The technical scheme of the invention is as follows: the brilliant blue disperse dye compound is a compound shown as the following formula I,
Figure BDA0003588612350000011
wherein R is selected from one or two of methyl, ethyl, n-propyl, isopropyl, allyl, methoxyethyl, ethoxyethyl, acetyl, chloroacetyl, benzoyl and cyclohexylformyl.
The preparation method of the brilliant blue disperse dye compound comprises the following steps,
a. dissolving a compound shown as a formula II in sulfuric acid, dripping nitrosyl sulfuric acid at the temperature of 0-10 ℃, and preserving heat for 2-4 hours to obtain a diazo liquid;
b. dissolving the compound shown in the formula III in water, adding sulfuric acid while stirring, adding sulfamic acid, cooling to 0-5 ℃, adding diazo liquid, and reacting at 0-5 ℃ to obtain the compound shown in the formula I.
Figure BDA0003588612350000021
A brilliant blue disperse dye mixture comprising two or more compounds of formula I as defined in claim 1.
The brilliant blue disperse dye mixture comprises two or three compounds shown as the formula I in claim 1.
A brilliant blue disperse dye composition, comprising a dye component and an auxiliary component, wherein the dye component consists of one or more than two compounds shown in a formula I in claim 1.
In the above brilliant blue disperse dye composition, the auxiliary component includes a dispersant and a surfactant.
In the brilliant blue disperse dye composition, the weight ratio of the dye component to the auxiliary agent component is 1: 0.5-3.
In the brilliant blue disperse dye composition, the dye component comprises a compound shown as a formula I-1 and a compound shown as a formula I-2, and the weight ratio of the compound shown as the formula I-1 to the compound shown as the formula I-2 is 1: 1.
Figure BDA0003588612350000022
The preparation method of the brilliant blue disperse dye composition comprises the steps of taking the dye component, adding the auxiliary agent component and water, adding the grinding medium, sanding and drying to obtain a finished product.
The brilliant blue disperse dye compound is applied to dyeing and printing of terylene and terylene blended fabrics.
Compared with the prior art, the brilliant blue disperse dye compound has the color light close to that of disperse blue 56, can replace the disperse blue 56, has high sublimation fastness, and has smaller color change when being used for dyeing polyester cotton by a one-bath method. The brilliant blue disperse dye compound has the advantages of short synthetic route, simple production process, greatly reduced wastewater discharge and greatly reduced production cost. The production process of the brilliant blue disperse dye compound is economic and environment-friendly, and the obtained finished product is low in price. The brilliant blue disperse dye compound is close to disperse blue 56, has better performance and lower cost, and provides more and better choices for substitute products of the disperse blue 56.
Detailed Description
The present invention is further illustrated by the following examples, which are not to be construed as limiting the invention.
Example 1. 80 g of 98% sulfuric acid was added to a 250 ml four-necked flask, 19.7 g of 98% 3-amino-5-nitro-2, 1-benzisothiazole was added with stirring, and dissolved by stirring, followed by slowly dropping 33 g of 40% nitrosylsulfuric acid at 0 to 10 ℃. Keeping the temperature for 3 hours to obtain the diazo liquid to be coupled. To a 2000 ml beaker was added 800 ml of water and 19.3 g (in hundred) of N-ethyl-N-methoxyethyl m-toluidine. 10 g of concentrated sulfuric acid was slowly added with stirring to dissolve, and 1 g of sulfamic acid was added. Simultaneously adding a proper amount of crushed ice into the cup, cooling to 0-5 ℃, starting to dropwise add the diazo liquid, keeping the temperature at 0-5 ℃ for reaction until the diazo component disappears, filtering and washing with water to be neutral. The weight of the filter cake in dried dye was about 35.9 g. Measurement of dye dissolution in butyrolactoneAbsorption wavelength of lambda max 626 nm. The structural formula is as follows:
Figure BDA0003588612350000031
due to the particularity of the dye industry, the pure product is difficult to prepare and is not necessary to prepare, and impurities in the preparation process are usually carried, and the brilliant blue disperse dye compound disclosed by the invention also allows trace impurities to exist.
Examples 2 to 11. The procedure described in example 1 was followed, except that the corresponding groups in the coupling component N-ethyl-N-methoxyethyl-m-toluidine were replaced with coupling components containing the desired groups (i.e., the R group in formula III was replaced with the desired group), to give the corresponding brilliant blue disperse dye compounds, which had the corresponding absorption maxima (. lamda.) max See table 1.
TABLE 1 examples 2-11 Brilliant blue disperse dye Compounds and disperse blue 56. lamda max
Figure BDA0003588612350000041
Example 12. The procedure described in example 1 was followed, except that the coupling component N-ethyl-N-methoxyethyl-m-toluidine was replaced with a coupling component in which N-ethyl-N-methoxyethyl-m-toluidine and N-ethyl-N-ethoxyethyl-m-toluidine were mixed in a weight ratio of 1:1, to give a brilliant blue disperse dye mixture which had an absorption maximum of lambda measured in butyrolactone max 627nm, the structural formula is as follows:
Figure BDA0003588612350000042
example 13. 10 g of each of the brilliant blue disperse dye compounds or the brilliant blue disperse dye mixtures (dye components) obtained in examples 1 to 12 were ground with 10 g of dispersing agent MF (auxiliary component), 10 g of surfactant sodium lignosulfonate, 45 g of water and 1000 g of zirconium beads until the degree of dye diffusion reaches 4 to 5, and the dye slurry was rapidly dried to obtain the brilliant blue disperse dye compositions obtained by the brilliant blue disperse dye compounds or the brilliant blue disperse dye mixtures obtained in examples 1 to 12.
Example 14. The brilliant blue disperse dye composition prepared in the example 13 and a commercial disperse blue 56 disperse dye product of a comparative example are used for dyeing polyester fabrics by a conventional high-temperature high-pressure dyeing method, the dyeing depth (o.w.f) is controlled to be 1.0 percent, the bath ratio is 1:40, the pH value of a dye bath is 4-5, the polyester fabrics are dyed at room temperature, the temperature is increased to 130 ℃ at 1 ℃/min, the polyester fabrics are kept for 45min, the polyester fabrics are reduced, cleaned, washed and dried by a conventional method, the polyester fabrics are shaped at 180 ℃ for 30 seconds, and the sublimation fastness is tested by a test method of the dry heat (except hot pressing) color fastness of a national standard GB/T5718 and 1997 textile color fastness test, and the test results are shown in Table 2. Then, the brilliant blue disperse dye composition prepared in example 13 and a commercial disperse blue 56 disperse dye product of a comparative example are used as dyes, a polyester-cotton one-bath dyeing process and a conventional high-temperature high-pressure dyeing process are respectively adopted to dye polyester fabrics, the dyeing depth (o.w.f) is controlled to be 1.0%, the bath ratio is 1:40, 2 g of soda and 60 g of anhydrous sodium sulphate are prepared into 1 liter of aqueous solution in the polyester-cotton one-bath dyeing process, the pH value of the conventional high-temperature high-pressure dyeing bath is adjusted to be about 4.5 by using acetic acid, the polyester-cotton one-bath dyeing process is dyed at room temperature, the temperature is increased to 130 ℃ at 1 ℃/min, the temperature is kept for 45min, the polyester-cotton one-bath dyeing process is subjected to reduction cleaning, water washing and drying according to a conventional method, each dye is standardized by using the cloth of the conventional high-temperature high-pressure dyeing process, the cloth of the polyester-cotton one-bath dyeing process is used as a sample, and the color measurement rating of the standard and the sample is obtained by using a computer color measurement instrument, and the specific color light rating is shown in table 2.
TABLE 2 Brilliant blue disperse dye compositions and associated Properties of disperse blue 56
Figure BDA0003588612350000051
Figure BDA0003588612350000061
As can be seen from the sublimation fastness of Table 2, the comparative example (disperse blue 56) has a sublimation fastness of only 3 to 4 degrees at 180 degrees. The sublimation fastness of 180 degrees of the brilliant blue disperse dye composition prepared by the brilliant blue disperse dye compound or the brilliant blue disperse dye mixture in the examples 1-12 is 4-5 grade and 5 grade, so that the sublimation fastness of the brilliant blue disperse dye composition is greatly higher than that of the comparative example, color running is less prone to occurring during setting, and the brilliant blue disperse dye composition has wider compatibility with other dyes. As can be seen from the color tone ratings of Table 2, the color difference and color tone ratings of the fabrics dyed by the conventional high-temperature high-pressure dyeing method and the polyester-cotton one-bath dyeing process in the comparative example (disperse blue 56) are 3 to 4, and the color difference and color tone ratings of the fabrics dyed by the brilliant blue disperse dye composition prepared by the brilliant blue disperse dye compound or the brilliant blue disperse dye mixture in the examples 1 to 12 by the two dyeing processes are mostly 4 to 5.
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.

Claims (10)

1. A brilliant blue disperse dye compound is characterized in that: is a compound shown as the following formula I,
Figure FDA0003588612340000011
wherein R is selected from one or two of methyl, ethyl, n-propyl, isopropyl, allyl, methoxyethyl, ethoxyethyl, acetyl, chloroacetyl, benzoyl and cyclohexylformyl.
2. The method for preparing a brilliant blue disperse dye compound as defined in claim 1, wherein: comprises the following steps of (a) carrying out,
a. dissolving a compound shown as a formula II in sulfuric acid, dripping nitrosyl sulfuric acid at the temperature of 0-10 ℃, and preserving heat for 2-4 hours to obtain a diazo liquid;
b. dissolving the compound shown in the formula III in water, adding sulfuric acid while stirring, adding sulfamic acid, cooling to 0-5 ℃, adding diazo liquid, and reacting at 0-5 ℃ to obtain the compound shown in the formula I.
Figure FDA0003588612340000012
3. A brilliant blue disperse dye mixture is characterized in that: comprising two or more compounds of formula I according to claim 1.
4. The brilliant blue disperse dye mixture of claim 3, wherein: comprising two or three of the compounds of formula I according to claim 1.
5. A brilliant blue disperse dye composition is characterized in that: comprising a dye component consisting of one or more than two compounds of formula I according to claim 1 and an auxiliary component.
6. The brilliant blue disperse dye composition according to claim 5, characterized in that: the auxiliary agent component comprises a dispersing agent and a surfactant.
7. The brilliant blue disperse dye composition according to claim 5, characterized in that: the weight ratio of the dye component to the auxiliary agent component is 1: 0.5-3.
8. The brilliant blue disperse dye composition according to claim 5, characterized in that: the dye component comprises a compound shown as a formula I-1 and a compound shown as a formula I-2, wherein the weight ratio of the compound shown as the formula I-1 to the compound shown as the formula I-2 is 1: 1.
Figure FDA0003588612340000021
9. The method for preparing brilliant blue disperse dye composition according to any one of claims 5 to 8, characterized in that: taking the dye component, adding the auxiliary agent component and water, adding the grinding medium, sanding and drying to obtain a finished product.
10. The use of the brilliant blue disperse dye compound of claim 1 in dyeing and printing of polyester and polyester blend fabrics.
CN202210371006.4A 2022-04-11 2022-04-11 Brilliant blue disperse dye compound, mixture, composition, preparation method and application thereof Pending CN114806212A (en)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2030163A (en) * 1978-07-19 1980-04-02 Basf Ag Benzisothiazole-azo dyes
CN101143969A (en) * 2007-09-12 2008-03-19 蓬莱华茂精细化工有限公司 Azo type heterocyclic blue dispersion dyes
CN101445667A (en) * 2008-12-30 2009-06-03 浙江龙盛染料化工有限公司 Nitrobenzoisothiazole dye monomer compound, application thereof and disperse dye composition
CN104727164A (en) * 2013-12-20 2015-06-24 上海安诺其集团股份有限公司 Use of disperse dye mixture for alkaline dyeing
CN104725895A (en) * 2013-12-20 2015-06-24 上海安诺其集团股份有限公司 Preparation method of disperse dyes mixture capable of alkaline dyeing
CN104725896A (en) * 2013-12-20 2015-06-24 上海安诺其集团股份有限公司 Disperse dyes mixture capable of alkaline dyeing
CN106118118A (en) * 2016-06-16 2016-11-16 蓬莱嘉信染料化工股份有限公司 Blue disperse dye and combinations thereof thing, preparation method and application
CN110698880A (en) * 2019-10-29 2020-01-17 杭州维昂化工有限公司 Disperse blue dye composition, disperse blue dye, preparation method of disperse blue dye and fabric

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2030163A (en) * 1978-07-19 1980-04-02 Basf Ag Benzisothiazole-azo dyes
CN101143969A (en) * 2007-09-12 2008-03-19 蓬莱华茂精细化工有限公司 Azo type heterocyclic blue dispersion dyes
CN101445667A (en) * 2008-12-30 2009-06-03 浙江龙盛染料化工有限公司 Nitrobenzoisothiazole dye monomer compound, application thereof and disperse dye composition
CN104727164A (en) * 2013-12-20 2015-06-24 上海安诺其集团股份有限公司 Use of disperse dye mixture for alkaline dyeing
CN104725895A (en) * 2013-12-20 2015-06-24 上海安诺其集团股份有限公司 Preparation method of disperse dyes mixture capable of alkaline dyeing
CN104725896A (en) * 2013-12-20 2015-06-24 上海安诺其集团股份有限公司 Disperse dyes mixture capable of alkaline dyeing
CN106118118A (en) * 2016-06-16 2016-11-16 蓬莱嘉信染料化工股份有限公司 Blue disperse dye and combinations thereof thing, preparation method and application
CN110698880A (en) * 2019-10-29 2020-01-17 杭州维昂化工有限公司 Disperse blue dye composition, disperse blue dye, preparation method of disperse blue dye and fabric

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