CN114773876B - Disperse red dye composition and product thereof - Google Patents

Disperse red dye composition and product thereof Download PDF

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Publication number
CN114773876B
CN114773876B CN202210543228.XA CN202210543228A CN114773876B CN 114773876 B CN114773876 B CN 114773876B CN 202210543228 A CN202210543228 A CN 202210543228A CN 114773876 B CN114773876 B CN 114773876B
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Prior art keywords
component
disperse red
red dye
dye composition
following formulas
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CN202210543228.XA
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Chinese (zh)
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CN114773876A (en
Inventor
朱鹏飞
陈立锋
何峰
魏沁
黄久强
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ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
Shanghai Hongyuan Xinchuang Material Technology Co ltd
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ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
Shanghai Hongyuan Xinchuang Material Technology 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
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008Preparations of disperse dyes or solvent dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046Mixtures of two or more azo dyes
    • C09B67/0051Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • 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)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

The invention provides an environment-friendly disperse red dye composition which comprises a component A, a component B, a component C and a component D, wherein the component A is at least one of the following formulas (I), the component B is at least one of the following formulas (II), the component C is at least one of the following formulas (III), and the component D is at least one of the following formulas (IV), and has the characteristics of good lifting property, leveling property, compatibility, washing fastness, rubbing fastness, perspiration fastness and the like when being applied to dyeing of hydrophobic fiber materials.

Description

Disperse red dye composition and product thereof
Field of the art
The invention relates to a disperse red dye composition, in particular to an environment-friendly disperse red dye composition suitable for dyeing and printing hydrophobic fiber materials and a product thereof.
(II) background art
With the progress of society and the improvement of living standard of people, people pay more and more attention to environment and self health condition, and higher requirements are put forward on economy and ecological environmental protection of textile chemicals, and for dye industry, pollution-free dyes, high-color-development-strength dyes and high-fastness dyes are developed, so that the dye consumption is saved, the waste water emission is reduced, disperse red dyes are a type of color with wider application range, namely single-color application and compound synergy of blue and black, and red dyes with excellent color fastness on the market are very limited.
(III) summary of the invention
In order to solve the problems, the invention provides an environment-friendly disperse red dye composition which has the characteristics of good lifting property, leveling property, compatibility, excellent washing fastness, rubbing fastness, perspiration fastness and the like when being applied to dyeing of hydrophobic fiber materials.
The technical scheme adopted by the invention is as follows:
a disperse red dye composition comprises a component A, a component B, a component C and a component D, wherein the component A is selected from at least one of the following formulas (I), the component B is selected from at least one of the following formulas (II), the component C is selected from at least one of the following formulas (III), the component D is selected from at least one of the following formulas (IV), the mass percent of the component A is 5-85%, the mass percent of the component B is 5-85%, the mass percent of the component C is 5-85%, and the mass percent of the component D is 1-50% based on the components A, B, C and D.
In formula (I):
R 1 is hydrogen or-NHCOR 11 Wherein R is 11 Is C 1 ~C 4 An alkyl group;
R 2 、R 3 each independently is C 1 ~C 4 Alkyl being optionally substituted by-CN, -OCOR 12 C substituted with-OH 1 ~C 4 Alkyl, wherein R is 12 Is C 1 ~C 4 An alkyl group;
in formula (II):
R 4 is hydrogen or-NHCOR 13 Wherein R is 13 Is C 1 ~C 4 An alkyl group;
R 5 、R 6 each independently is C 1 ~C 4 Alkyl being optionally substituted by-CN, -OCOR 14 、-COOR 15 Substituted C 1 ~C 4 Alkyl, wherein R is 14 、R 15 Each independently is C 1 ~C 4 An alkyl group;
in formula (III):
R 7 is C 1 ~C 4 An alkyl group;
R 8 、R 9 each independently is-OCOR 16 or-COOR 17 Substituted C 1 ~C 4 Alkyl, wherein R is 16 、R 17 Each independently is C 1 ~C 4 An alkyl group;
in formula (IV):
x is hydrogen or halogen;
R 10 is C 1 ~C 4 Alkyl, C substituted by-CN or phenyl 1 ~C 4 An alkyl group.
In the invention, the C 1 ~C 4 The alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.
Further, the component A is preferably selected from one of the following formulas or a mixture of two or more of them in any proportion:
further, the component B is preferably selected from one of the following formulas or a mixture of two or more of them in any proportion:
further, the component C is preferably selected from one of the following formulas or a mixture of two or more of them in any proportion:
further, the component D is preferably selected from one of the following formulas or a mixture of two or more of them in any proportion:
preferably, the disperse red dye composition consists of 20-70% by mass of a component A, 20-70% by mass of a component B, 10-50% by mass of a component C and 1-40% by mass of a component D based on the component A, the component B, the component C and the component D.
Still further, the disperse red dye composition of the present invention is preferably composed of a component a, a component B, a component C and a component D, wherein:
component A is selected from at least one of formulas (I-1) to (I-4);
the component B is at least one selected from formulas (II-1) to (II-4);
the component C is at least one selected from formulas (III-1) and (III-2);
the component D is at least one selected from formulas (IV-1) to (IV-4);
based on the components A, B, C and D, the mass percentage of the component A is 20-70%, the mass percentage of the component B is 20-70%, the mass percentage of the component C is 10-50%, and the mass percentage of the component D is 1-40%.
The disperse red dye composition of the invention can be further added with orange or red toning components such as C.I. disperse orange 25, C.I. disperse orange 31, C.I. disperse red 145 and the like, wherein the total weight of the components A-D is not more than 20 percent.
The disperse red dye composition can be directly sold as a commodity or can be sold as a commodity after adding a conventional auxiliary agent or applied to coloring textile materials. Therefore, the invention also provides a disperse red dye product which mainly comprises the disperse red dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-5:1. Preferably, the disperse red dye product consists of the disperse red dye composition and an auxiliary agent. The auxiliary agent is a dispersing agent, other surfactants and the like which are commonly used in disperse dye compounding, and is preferably one or a mixture of more than two of the following components in any proportion: naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate [ such as methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF) ], naphthalene sulfonic acid formaldehyde condensate (dispersant NNO), benzyl naphthalene sulfonic acid formaldehyde condensate (dispersant CNF), sodium lignin sulfonate (lignin 85A, lignin 83A), sodium sulfate (sodium sulfate), and the like.
The preparation method of the disperse red dye product provided by the invention comprises the following steps: mixing dye monomer compounds (raw dyes) forming the disperse red dye composition according to a proportion, and then carrying out micropellet formation by using a grinder such as a sand grinder or a grinder in the presence of an auxiliary agent, water or other wetting agents; alternatively, the dye monomer compounds may be subjected to a fine particle formation treatment by a pulverizer such as a sand mill or a grinding machine in the presence of an auxiliary agent and water, respectively, and then mixed in proportion. The disperse red dye product is liquid after being ground by a sand mill or a grinding machine, can be powder or granular after being spray dried, and is a preparation method well known to a person skilled in the art.
In the present invention, the dye compounds of the formulae (I) to (IV) can be conveniently synthesized in a manner known to those skilled in the art, and can be prepared by the method described in patent CN106752081A, US3956270A, CN108047751A, CN106800798A or the like, and commercially available products can be used.
The dye product prepared by the dye composition can be used for dyeing hydrophobic fiber materials (such as polyester and blended fabrics thereof) in a conventional manner in industry, such as dyeing by a common dip dyeing method or a high-temperature high-pressure dyeing method, and can also be directly used for printing. Among them, common dip dyeing methods are as follows: pretreating a hydrophobic fiber material, putting the pretreated hydrophobic fiber material into a dye vat for dip dyeing, washing the dye vat with cold water until the dye vat is neutral, wringing the dye vat to dryness, and then carrying out reduction washing and drying; direct printing such as: and (3) carrying out dyeing pretreatment on the fabric, drying, shaping, printing disperse dye color paste on a printing machine, steaming, fixing the color of the dye on the fabric by utilizing a steaming mode, washing with water, and tentering and shaping.
The disperse red dye composition and the dye product provided by the invention have the characteristics of good lifting property, leveling property, compatibility, excellent washing fastness, friction resistance, perspiration fastness and the like when being applied to dyeing of hydrophobic fiber materials, and can meet the requirements of Oeko-Tex standard 100.
(IV) detailed description of the invention
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto.
Example 1:
35 g of component A of the compound of formula (I-1), 35 g of component B of the compound of formula (II-1), 25 g of component C of the compound of formula (III-1), 5 g of component D of formula (IV-1) and 250 g of dispersing agent MF are added with 650 g of water for blending, and then are ground, dispersed and dried to obtain a finished product, and the dye can provide red with various fastness properties for polyester fabrics.
Example 2
30 g of a component A of a compound of a formula (I-1), 30 g of a component B of a compound of a formula (II-1), 25 g of a component C of a compound of a formula (III-1), 5 g of a component D of a formula (IV-1), 10 g of a dispersant MF of a formula (V) and 250 g of a dispersant MF, adding 850 g of water, blending, grinding, dispersing and drying to obtain a finished product, wherein the dye can provide red with excellent fastness properties for polyester fabrics.
Examples 3 to 30:
according to the method of example 1, except that the structures and weights of components A to D in Table 1 are adopted, 250 g of an auxiliary agent (200 g of dispersing agent MF and 50 g of sodium lignin sulfonate) is added, 800 g of water is added and mixed to prepare slurry, grinding and dispersing are carried out, and drying are carried out, so that a finished product is obtained, and the dye can provide red color tone with excellent fastness properties for polyester fabrics:
TABLE 1
Dyeing examples:
the disperse dyes prepared in examples 1 to 30 were selected and tested for their respective fastness to washing, perspiration and rubbing according to the standards ISO 105-C10, ISO 105-E04, ISO105-X12, with the results given in Table 3 below:
TABLE 3 Table 3
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In conclusion, the disperse red dye composition provided by the invention has good washing fastness, perspiration fastness and rubbing fastness, and can meet the printing and dyeing requirements of fabrics with high fastness.

Claims (10)

1. A disperse red dye composition comprises a component A, a component B, a component C and a component D, wherein the component A is selected from at least one of the following formulas (I), the component B is selected from at least one of the following formulas (II), the component C is selected from at least one of the following formulas (III), the component D is selected from at least one of the following formulas (IV), the mass percent of the component A is 5-85%, the mass percent of the component B is 5-85%, the mass percent of the component C is 5-85%, and the mass percent of the component D is 1-50% based on the components A, B, C and D.
In formula (I):
R 1 is hydrogen or-NHCOR 11 Wherein R is 11 Is C 1 ~C 4 An alkyl group; r is R 2 、R 3 Each independently is C 1 ~C 4 Alkyl being optionally substituted by-CN, -OCOR 12 C substituted with-OH 1 ~C 4 Alkyl, wherein R is 12 Is C 1 ~C 4 An alkyl group;
in formula (II):
R 4 is hydrogen or-NHCOR 13 Wherein R is 13 Is C 1 ~C 4 An alkyl group; r is R 5 、R 6 Each independently is C 1 ~C 4 Alkyl being optionally substituted by-CN, -OCOR 14 、-COOR 15 Substituted C 1 ~C 4 Alkyl, wherein R is 14 、R 15 Each independently is C 1 ~C 4 An alkyl group;
in formula (III):
R 7 is C 1 ~C 4 An alkyl group; r is R 8 、R 9 Each independently is-OCOR 16 or-COOR 17 Substituted C 1 ~C 4 Alkyl group, whereinR 16 、R 17 Each independently is C 1 ~C 4 An alkyl group;
in formula (IV):
x is hydrogen or halogen; r is R 10 Is C 1 ~C 4 Alkyl, C substituted by-CN or phenyl 1 ~C 4 An alkyl group.
2. The disperse red dye composition according to claim 1, wherein C 1 ~C 4 Alkyl is methyl or ethyl.
3. The disperse red dye composition according to claim 1, wherein the component A is selected from one of the following formulas or a mixture of two or more of them in any proportion:
4. the disperse red dye composition according to claim 1, wherein the component B is selected from one of the following formulas or a mixture of two or more of them in any proportion:
5. the disperse red dye composition according to claim 1, wherein the component C is selected from one of the following formulas or a mixture of two or more of them in any proportion:
6. the disperse red dye composition according to claim 1, wherein the component D is selected from one of the following formulas or a mixture of two or more of them in any proportion:
7. the disperse red dye composition of claim 1, consisting of component a, component B, component C and component D.
8. The disperse red dye composition of claim 7, wherein:
component A is selected from at least one of formulas (I-1) to (I-4);
the component B is at least one selected from formulas (II-1) to (II-4);
the component C is at least one selected from formulas (III-1) and (III-2);
component D is selected from at least one of formulas (IV-1) to (IV-4).
9. A disperse red dye product comprises an auxiliary agent and the disperse red dye composition of claim 1, wherein the weight ratio of the auxiliary agent to the disperse red dye composition is 0.2-5:1, and the auxiliary agent is a dispersing agent, a dispersing agent or other surfactants commonly used in disperse dye compounding.
10. Use of the disperse red dye composition of claim 1 or the disperse red dye article of claim 9 for dyeing polyester and blends thereof.
CN202210543228.XA 2022-05-20 2022-05-20 Disperse red dye composition and product thereof Active CN114773876B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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DE3738062A1 (en) * 1986-11-12 1988-05-19 Ciba Geigy Ag Storage-stable suspension of dyes which are insoluble to sparingly soluble in water
US5207804A (en) * 1989-09-12 1993-05-04 Hoechst Aktiengesellschaft Multi-component mixtures of bright red disperse azo dyestuffs
US5332404A (en) * 1991-12-13 1994-07-26 Hoechst Mitsubishi Kasei Co., Ltd. Disperse dye mixtures
JPH07229073A (en) * 1993-12-21 1995-08-29 Mitsubishi Kasei Hoechst Kk Method for dyeing hydrophobic yarn in black
CN101967307A (en) * 2010-09-18 2011-02-09 浙江万丰化工有限公司 Disperse dye composite
CN101982510A (en) * 2010-09-18 2011-03-02 浙江万丰化工有限公司 Composite of dispersed dyes
CN102924975A (en) * 2012-11-12 2013-02-13 浙江闰土股份有限公司 Disperse dye composition and disperse dyes, and preparation method and purpose thereof
CN105111787A (en) * 2015-07-30 2015-12-02 杭州吉华江东化工有限公司 Disperse dye mixture and application thereof
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CN109535769A (en) * 2018-12-19 2019-03-29 浙江龙盛化工研究有限公司 A kind of dispersion red dye composition and dye preparations
CN111518414A (en) * 2020-04-29 2020-08-11 约克夏(浙江)染化有限公司 Red disperse dye composition, red disperse dye and preparation method and application thereof
CN112679990A (en) * 2020-12-29 2021-04-20 浙江闰土股份有限公司 Disperse dye composition, disperse dye, preparation method and application thereof

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* Cited by examiner, † Cited by third party
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DE3542232A1 (en) * 1985-11-29 1987-06-04 Bayer Ag AZO DYES
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US5207804A (en) * 1989-09-12 1993-05-04 Hoechst Aktiengesellschaft Multi-component mixtures of bright red disperse azo dyestuffs
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JPH07229073A (en) * 1993-12-21 1995-08-29 Mitsubishi Kasei Hoechst Kk Method for dyeing hydrophobic yarn in black
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