CN116144197A - Combination and application of disperse brilliant blue dye - Google Patents

Combination and application of disperse brilliant blue dye Download PDF

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Publication number
CN116144197A
CN116144197A CN202211498817.7A CN202211498817A CN116144197A CN 116144197 A CN116144197 A CN 116144197A CN 202211498817 A CN202211498817 A CN 202211498817A CN 116144197 A CN116144197 A CN 116144197A
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Prior art keywords
dye
brilliant blue
component
combination
disperse
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Inventor
陶国来
陶安迪
陶安妮
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
    • 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
    • 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
    • C09B67/0084Dispersions of dyes
    • C09B67/0085Non common dispersing agents
    • C09B67/0086Non common dispersing agents anionic dispersing agents
    • 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

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

Abstract

A disperse brilliant blue dye mixture is formed by mixing two parts of dye and auxiliary agent; the dye comprises a component A and a component B, wherein the compound general formula of the mixed dye of the component A and the component B contains ether bonds, the affinity with polyester fibers is good, the dyeing leveling property is good, the lifting force is high, the ether bonds are relatively stable, the dye is not easy to hydrolyze, particularly stable under alkaline conditions, the dye can dye under alkaline conditions, the problem of poor alkali resistance of a disperse blue 284 product is solved, the obvious advantages of bright color, good leveling property and high lifting force are maintained, the price is low, the production process is economic and environment-friendly, and the dye composition is an unprecedented disperse brilliant blue dye composition with good performance.

Description

Combination and application of disperse brilliant blue dye
Technical Field
The invention relates to the field of printing and dyeing, in particular to a combination and application of a disperse brilliant blue dye.
Background
The disperse brilliant blue 284 is a disperse dye variety with bright color, larger light absorption coefficient, higher dyeing strength and higher lifting rate, is mainly used for dyeing and printing terylene and blended fabrics, and has wider application range. Although the dispersion brilliant blue 284 has excellent performance, the tail group is an ester group, so that the alkali resistance is extremely poor, the dyeing cannot be performed under the alkaline condition, and the application range of the product is greatly limited. Therefore, development of a disperse brilliant blue dye with brilliant color, excellent performance and color light similar to that of the disperse brilliant blue 284 is a problem to be solved in the dye industry.
Summary of the invention
The invention provides a disperse brilliant blue dye mixture, which solves the defect of poor alkali resistance of the existing disperse brilliant blue 284 product, maintains the obvious advantages of bright color, good leveling property and high lifting force, and has low price and economic and environment-friendly production process.
In order to achieve the above purpose, the invention adopts the following technical scheme: a disperse brilliant blue dye mixture is formed by mixing two parts of dye and auxiliary agent; the dye comprises a component A and a component B,
the component A is a disperse dye with a structure shown in a formula (I),
Figure BDA0003965924020000011
the component B is a disperse dye with a structure which is shown as a formula (II),
Figure BDA0003965924020000021
wherein:
r is selected from any one of methyl, ethyl, 2-methoxyethyl and 2-ethoxyethyl;
R 1 、R 2 any one or two of ethyl, 2- (2-methoxyethoxy) ethyl and 2- (2-ethoxyethoxy) ethyl;
the combination of the disperse brilliant blue dye is characterized in that: the component A at least contains one of the following structures:
Figure BDA0003965924020000022
the combination of the disperse brilliant blue dye is characterized in that: the component B at least contains one of the following structures:
Figure BDA0003965924020000031
the weight percentage of the pure dye of the following structural formula of the dye part is as follows: the weight percentage of the pure dye of the following structural formula of the dye part is as follows: 40-95% of the A-component dye with the structure shown in the formula (I), and 1-50% of the B-component dye with the structure shown in the formula (II).
The weight ratio of the auxiliary agent to the combination of the disperse brilliant blue dye is 0.5-6: 1.
the auxiliary agent is selected from any one or more than two of lignosulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate and naphthalene sulfonic acid formaldehyde condensate.
The combination of the disperse brilliant blue dyes is applied to dyeing or printing of hydrophobic fiber materials. The design concept and beneficial effects of the invention are as follows: the mixed dye conforming to the chemical structural general formula (I) and the chemical structural general formula (II) contains ether bonds, has good affinity with polyester fibers, good dyeing leveling property and high lifting force, is stable, is not easy to hydrolyze, is particularly stable under alkaline conditions, and can be dyed under alkaline conditions.
The brilliant blue disperse dye composition solves the problem of poor alkali resistance of disperse blue 284 products, keeps the obvious advantages of bright color, good leveling property and high lifting force, has low price and economic and environment-friendly production process, and is an unprecedented disperse brilliant blue dye composition with good performance.
Detailed Description
The present invention will be further described with reference to specific examples, but the scope of the present invention is not limited thereto.
Example 1:
the preparation method of the disperse dye compound comprises the following steps of dissolving a compound 3-amino-5-nitro-2, 1-benzisothiazole with sulfuric acid in a structure shown in a formula (III), dripping nitrosylsulfuric acid at 0-10 ℃, and preserving heat for 3 hours to obtain a diazonium solution; adding water into a compound with a structure shown in a formula (IV), adding sulfuric acid for dissolution under stirring, adding sulfamic acid, cooling to 0-5 ℃, adding diazonium solution, reacting at 0-5 ℃, filtering after the reaction is completed, washing with water to be neutral, and drying to obtain the compound with the structure shown in the formula (I). Formula (III): nitrosylsulfuric acid: the molar ratio of formula (IV) is 1:1.05:1.
Figure BDA0003965924020000041
the preparation method of the disperse dye compound comprises the following steps,
adding sulfuric acid into 2, 6-dibromo-p-nitroaniline with a structure shown in a formula (V) for dissolving, dripping nitrosylsulfuric acid at 0-10 ℃, and preserving heat for 2-4 hours to obtain diazonium solution; adding water into a compound with a structure shown in a formula (VI), adding sulfuric acid under stirring for dissolution, adding sulfamic acid, cooling to 0-5 ℃, adding diazonium solution, reacting at 0-5 ℃, filtering after the reaction is completed, washing with water to be neutral, and drying to obtain the compound with the structure shown in the formula (VII). Formula (v): nitrosylsulfuric acid: the molar ratio of formula (VI) is 1:1.05:1.
and then adding DMF (dimethyl formamide) into the dried product of the formula (VII) for dissolution, adding cuprous cyanide, heating to 80-100 ℃ for cyanide reaction, adding methanol for complete reaction, cooling, separating out, filtering, washing with methanol, and drying to obtain the compound with the structure shown in the formula (II). Formula (VII): the molar ratio of cuprous cyanide is 1:2.1.
Figure BDA0003965924020000051
the R group of the component A adopts CH2CH2O-CH3 to obtain a compound of a formula (I-1), the R1 and R2 groups of the component B adopt CH2CH3 to obtain a compound of a formula (II-1), 31 g of the compound of the formula (I-1), 7.5 g of the compound of the formula (II-1) and 161.5 g of a dispersing agent MF are mixed together by adding 300 g of water to prepare a slurry, the solid content of the slurry is controlled to be preferably 35-45%, and the slurry is ground, dispersed and spray-dried to obtain a finished product, wherein the finished product can provide blue color of fabrics.
Examples 2 to 12:
the method of example 1 was followed except that the slurry was prepared by blending the components A and B in the weight ratios and auxiliaries shown in Table 1 with water, and the slurry was suitably controlled to have a solids content of 35 to 45%, and the resulting slurry was subjected to grinding dispersion and spray drying to obtain a final product which was capable of providing a uniform blue shade with good fastness properties to the fabric. The auxiliary agent is methyl naphthalene sulfonic acid formaldehyde condensate (dispersing agent MF), naphthalene sulfonic acid formaldehyde condensate (dispersing agent NNO), sodium lignin sulfonate (lignin NA, 83A) and the like.
Comparative example 1: the commercial disperse blue 284 commodity was taken as a comparative example, and the depth of the dyed cloth samples was identical to that of the dyed cloth samples of examples 1-12.
Table 1: proportion of dye
Figure BDA0003965924020000061
Performance test:
the disperse dyes prepared in the above examples 1 to 12 and the disperse blue 284 disperse dye of comparative example 1 are treated by a conventional high-temperature high-pressure dyeing method, and in the treatment process, the dyeing depth (o.w.f) is controlled to be 1.2%, and the bath ratio is controlled to be 1:40, the pH value of the dye bath is regulated to 4-5, the dye is added at room temperature, the temperature is increased to 130 ℃ at 1 ℃/min, the heat is preserved for 45min, and the dye is recovered, washed, dried and cooled to 70 ℃ and taken out according to a normal method. Based on the dyeing method, respectively regulating the pH value of the dye bath to be 7,9 and 10, taking a cloth sample dyed with the pH value of the dye bath to be 4-5 as a standard, testing the coloring rate condition of the dye at different pH values, and judging the pH value capable of dyeing normally, wherein the specific reference is shown in Table 2:
TABLE 2 dye color Rate at different pH' s
Different disperse dyes Dye uptake at ph=7 Dye uptake at ph=9 Dye uptake at ph=10
Example 1 100.1% 99.8% 95.5%
Example 2 99.9% 100% 95.6%
Example 3 100.7% 100.1% 95.2%
Example 4 99.5% 98.9% 94.2%
Example 5 100.3% 99.9% 96.1%
Example 6 100.2% 100% 96.3%
Example 7 99.8% 98.8% 95.4%
Example 8 100.5% 100% 96.7%
Example 9 100.2% 100.3% 96.1%
Example 10 101.3% 100.5% 96.3%
Example 11 100.1% 100% 94.8%
Example 12 100.8% 100.3% 95.7%
Comparative example 1 67.7% 67.0% 3.2%
As can be seen from the color ratios at different pH values in table 2, the color ratio of comparative example 1 was 67.7% at ph=7, 67.0% at ph=9, and 3.2% at ph=10, whereas the color ratios of the cloth samples of examples 1 to 12 after dyeing at ph=7, and the color ratio of the cloth sample after dyeing at ph=9 were all 98.8% or more, and 94.2% or more after dyeing at ph=10, so that the dyeing pH range of the dye of example was significantly higher than that of comparative example 1, the pH requirement was wider at dyeing, and the dyeing was more stable in use.
The above embodiments are provided to illustrate the technical concept and features of the present invention and are intended to enable those skilled in the art to understand the content of the present invention and implement the same, and are not intended to limit the scope of the present invention. All equivalent changes or modifications made in accordance with the spirit of the present invention should be construed to be included in the scope of the present invention.

Claims (7)

1. The combination of the disperse brilliant blue dye is formed by mixing two parts of dye and auxiliary agent, wherein the dye comprises a component A and a component B, and is characterized in that:
the component A is one or two compounds with the structure shown in the formula (I),
Figure FDA0003965924010000011
the component B is one or two compounds with the structure shown in the formula (II),
Figure FDA0003965924010000012
wherein:
r is selected from any one of methyl, ethyl, 2-methoxyethyl and 2-ethoxyethyl;
R 1 、R 2 selected from any one or two of ethyl, 2- (2-methoxyethoxy) ethyl and 2- (2-ethoxyethoxy) ethyl.
2. A combination of disperse brilliant blue dyes according to claim 1, characterized in that: the component A contains at least one group of the following structures:
Figure FDA0003965924010000013
Figure FDA0003965924010000021
3. a combination of disperse brilliant blue dyes according to claim 1, characterized in that: the component B contains at least one of the following structures:
Figure FDA0003965924010000022
4. a combination of disperse brilliant blue dyes according to claim 1, characterized in that: the weight percentage of the pure dye of the following structural formula of the dye part is as follows: 40-95% of the A-component dye with the structure shown in the formula (I), and 1-50% of the B-component dye with the structure shown in the formula (II).
5. A combination of disperse brilliant blue dyes, comprising a combination of disperse brilliant blue dyes according to any one of claims 1-4 and an auxiliary agent, the weight ratio of auxiliary agent to combination of disperse brilliant blue dyes being 0.5-6: 1.
6. a combination of disperse brilliant blue dyes according to claim 5, wherein: the auxiliary agent is selected from any one or more than two of lignosulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate and naphthalene sulfonic acid formaldehyde condensate.
7. Use of a combination of disperse brilliant blue dyes according to any one of claims 1 to 4 or a combination of disperse brilliant blue dyes according to any one of claims 5 to 6 for dyeing or printing hydrophobic fibre materials.
CN202211498817.7A 2022-11-28 2022-11-28 Combination and application of disperse brilliant blue dye Pending CN116144197A (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60246885A (en) * 1984-05-22 1985-12-06 合成染料技術研究組合 Alkali resist style method
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
CN104088166A (en) * 2013-12-25 2014-10-08 上海安诺其纺织化工股份有限公司 Application of navy blue or black disperse dye
CN104087018A (en) * 2013-12-25 2014-10-08 上海安诺其纺织化工股份有限公司 Preparation method for navy blue or black disperse dye
CN104087019A (en) * 2013-12-25 2014-10-08 上海安诺其纺织化工股份有限公司 Navy blue or black disperse dye composition
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 (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60246885A (en) * 1984-05-22 1985-12-06 合成染料技術研究組合 Alkali resist style method
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
CN104088166A (en) * 2013-12-25 2014-10-08 上海安诺其纺织化工股份有限公司 Application of navy blue or black disperse dye
CN104087018A (en) * 2013-12-25 2014-10-08 上海安诺其纺织化工股份有限公司 Preparation method for navy blue or black disperse dye
CN104087019A (en) * 2013-12-25 2014-10-08 上海安诺其纺织化工股份有限公司 Navy blue or black disperse dye composition
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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