CN110387143A - A kind of Yellow active dye composition and its preparation method and application - Google Patents

A kind of Yellow active dye composition and its preparation method and application Download PDF

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Publication number
CN110387143A
CN110387143A CN201910663237.0A CN201910663237A CN110387143A CN 110387143 A CN110387143 A CN 110387143A CN 201910663237 A CN201910663237 A CN 201910663237A CN 110387143 A CN110387143 A CN 110387143A
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weight
parts
component
reactive dye
yellow
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CN110387143B (en
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陆军
陶彬彬
陶莉莉
张明省
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Zhejiang Ruihua Chemical Coltd
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Zhejiang Ruihua Chemical Coltd
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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
    • C09B67/0052Mixtures of two or more reactive monoazo dyes
    • C09B67/0053Mixtures of two or more reactive monoazo dyes all the reactive groups being directly attached to a heterocyclic system
    • 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
    • C09B67/0072Preparations with anionic dyes or reactive 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
    • D06P1/38General 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 reactive 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
    • D06P1/44General 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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/673Inorganic compounds
    • D06P1/67333Salts or hydroxides
    • D06P1/6735Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
    • 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
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/14Wool
    • D06P3/148Wool using reactive 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
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/66Natural or regenerated cellulose using reactive dyes

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

Abstract

The present invention provides a kind of Yellow active dye composition and its preparation method and application, and the Yellow active dye composition includes component X shown in formula (I), component Y and optional auxiliary agent shown in formula (II);Its degree of fixation is high, and the items fastness properties such as rub resistance, water-fastness and perspiration resistance are excellent, and has refrigeration performance good, and solubility is high.

Description

Yellow reactive dye composition and preparation method and application thereof
Technical Field
The invention relates to the field of reactive dyes, in particular to a yellow reactive dye composition, and a preparation method and application thereof.
Background
Reactive dyes are important synthetic dyes which are fixed by chemical reaction of reactive groups in the chemical structure with cellulose fibers, and are also called reactive dyes, and the reactive dyes are mainly used for improving application performance by selecting novel reactive groups. With the increasing requirements of people on wearing comfort and ecological health, textile products are increasingly concentrated on cotton and cotton-type fabrics, and the demand of reactive dyes is also increased year by year, which is called one of the most widely applied synthetic dyes at present. However, the combined effect of many yellow reactive dyes developed at present is difficult to reach the expectation of people, and the combined effect can not meet the increasing market demand, such as the commercial product P-2R yellow:
the dye belongs to a monochlorotriazine active monoazo active dye, has good color light, but has poor solubility and refrigeration performance, and cannot meet the requirements of high-grade printing at present. In view of the disadvantages of the structure of the commercially available P-2R yellow, there are many reports on the improvement of the structure, but no ideal reactive dye has been reported so far. Therefore, the development of reactive yellow dye varieties with better performance and more advantageous cost has more and more important significance.
Disclosure of Invention
The invention provides a yellow reactive dye composition, a preparation method and application thereof, wherein the yellow reactive dye composition has the advantages of high color fixation rate, excellent color fastness performances such as friction resistance, washing resistance, perspiration resistance and the like, good refrigeration performance and high solubility. The invention provides a yellow reactive dye composition, which comprises a component X shown in a formula (I), a component Y shown in a formula (II) and optional auxiliary agents;
wherein,
A. each B is independently (C)1-C4) -an alkyl or amino group;
Re1is composed of
Re2Is composed ofX1、X3、X4、X5、X6、X7、X8Each independently is halogen;
X2is (C)1~C4) Alkoxy, amino, -NHR3OH or-NHR3SO3M1
Each R is3Each independently is CnH2n(n is 1 or 2);
R1、R2each independently is H, -SO3M2、-COOM2Or R4-X9
R4Is CnH2n(n is 1 or 2),
X9is H, halogen or amino;
each M1Each M2Each independently is an alkali metal, hydrogen or ammonium;
alternatively, the alkali metal is selected from lithium, sodium, potassium;
optionally, the halogen is fluorine, bromine, chlorine.
Optionally, the yellow reactive dye composition is characterized in that the component X is selected from one or more compounds of formulas (I-1) to (I-7).
The yellow reactive dye composition is characterized in that the component Y is selected from one or more compounds in formulas (II-1) to (II-17).
Preferably, in the yellow dye composition, the content of the component X is 5 to 80 parts by weight, preferably 5 to 75 parts by weight, more preferably 5 to 70 parts by weight, and still more preferably 10 to 70 parts by weight.
Preferably, in the yellow dye composition, the content of the component Y is 10 to 90 parts by weight, preferably 10 to 85 parts by weight, more preferably 10 to 80 parts by weight, and still more preferably 20 to 80 parts by weight.
Preferably, in the yellow dye composition, the content of the auxiliary agent is 0 to 80 parts by weight, preferably 0 to 75 parts by weight, more preferably 0 to 70 parts by weight, and still more preferably 0 to 65 parts by weight.
In the present invention, the selection of the above-mentioned auxiliary is not particularly limited, and may be a conventional auxiliary. Preferably, the above-mentioned auxiliary agent is selected from one or more of a dispersant, a filler, and other performance-improving auxiliary agents.
Preferably, the dispersant is selected from one or more of dispersant MF and dispersant NNO.
Preferably, the filler is anhydrous sodium sulphate.
Preferably, the other performance-improving auxiliary is one or more selected from a dust-proofing agent and a solubility-improving agent.
The invention also provides a preparation method of the yellow reactive dye composition, which comprises the following steps: the dry powder or slurry of the component X, the dry powder or slurry of the component Y and the optional auxiliary agent are prepared by direct mixing or an optional drying process according to the proportion.
In the present invention, the apparatus for mixing the dry powder is not particularly limited, and preferably, the dry powder is mixed by a conical, roller or pear cutter type mixer, mixed uniformly, and then packaged after test analysis is qualified. The method for mixing the slurry is not particularly limited, and preferably, the slurry is stirred and mixed in a vessel. In the present invention, the equipment used in the drying process is not particularly limited, and it is preferable to dry the product in the form of granules or powder by using a spray tower, a drying room, a flash dryer, or the like.
The invention also provides the application of the yellow reactive dye as a yellow reactive dye,
optionally, the yellow reactive dye is used for printing and dyeing of fibers or textiles thereof, wherein the printing and dyeing comprises dyeing and/or printing.
Preferably, the yellow reactive dye is used for printing and dyeing of cellulose fibers, protein fibers, polyamide fibers or textiles thereof.
Preferably, the cellulose fiber comprises cotton fiber, hemp fiber and regenerated fiber. The protein fiber includes wool, silk, and artificial protein fiber.
The yellow reactive dye composition has the following advantages due to the synergistic effect of the component X and the component Y: high color fixing rate, excellent color fastness properties such as rubbing resistance, washing resistance, perspiration resistance and the like, good refrigeration performance and high solubility. The yellow reactive dye composition is suitable for printing and dyeing cellulosic fiber materials, such as cotton, hemp, regenerated fibers and textiles thereof, and is also suitable for printing and dyeing protein fibers, polyamide fibers and textiles thereof.
Detailed Description
The present invention will be further described with reference to the following specific examples, but the scope of the present invention is not limited thereto.
The yellow reactive dye compositions according to the invention, component X and component Y, may be conveniently synthesized in a manner known to those skilled in the art, for example by conventional diazotization and coupling processes, or by commercially available products.
Example 1
The composition 1 is obtained by dry powder mixing of 36 parts by weight of the component X of the formula (I-1), 57 parts by weight of the component Y of the formula (II-1) and 7 parts by weight of anhydrous sodium sulphate through a mixing machine, and the composition is used as yellow reactive dye and can dye and dye cotton fabrics into yellow.
Example 2
And (2) carrying out dry powder mixing on 40 parts by weight of the component X shown in the formula (I-1), 55 parts by weight of the component Y shown in the formula (II-15) and 5 parts by weight of anhydrous sodium sulphate by a mixing machine to obtain a composition 2, wherein the composition is used as a yellow reactive dye and can be used for printing and dyeing wool fabrics into yellow.
Example 3
The composition 3 is obtained by dry powder mixing of 35 parts by weight of the component X of the formula (I-1), 55 parts by weight of the component Y of the formula (II-16) and 10 parts by weight of anhydrous sodium sulphate through a mixing machine, and the composition is used as yellow reactive dye and can dye and dye wool fabrics into yellow.
Example 4
42 parts by weight of the component X of the formula (I-1), 50 parts by weight of the component Y of the formula (II-17) and 8 parts by weight of anhydrous sodium sulphate are mixed by a blending machine to obtain a composition 4, and the composition is used as a yellow reactive dye and can dye and dye cotton fabrics into yellow.
Example 5
And (2) carrying out dry powder mixing on 45 parts by weight of the component X shown in the formula (I-5), 50 parts by weight of the component Y shown in the formula (II-1) and 5 parts by weight of anhydrous sodium sulphate by a mixing machine to obtain a composition 5, wherein the composition is used as a yellow reactive dye and can be used for dyeing and printing the cotton fabric into yellow.
Example 6
And (2) mixing 45 parts by weight of the component X shown in the formula (I-6), 45 parts by weight of the component Y shown in the formula (II-1) and 10 parts by weight of anhydrous sodium sulphate by a mixing machine to obtain a composition 6, wherein the composition is used as a yellow reactive dye and can be used for printing and dyeing cotton fabrics into yellow.
Example 7
42 parts by weight of the component X of the formula (I-7), 50 parts by weight of the component Y of the formula (II-1) and 8 parts by weight of anhydrous sodium sulphate are mixed by a blending machine to obtain a composition 7, and the composition is used as a yellow reactive dye and can dye and dye cotton fabrics into yellow.
Comparative example 1
70 parts by weight of the component X of the formula (I-1) and 30 parts by weight of anhydrous sodium sulphate are mixed by a blending machine to obtain a composition 8, and the composition is used as a yellow reactive dye and can dye and dye cotton fabrics into yellow.
Comparative example 2
And (2) mixing 75 parts by weight of the component Y in the formula (II-1) and 25 parts by weight of anhydrous sodium sulphate by a mixing machine to obtain a composition 9, wherein the composition is used as a yellow reactive dye and can be used for printing and dyeing cotton fabrics into yellow.
Comparative example 3
70 parts by weight of the component X of the formula (I-1) and 30 parts by weight of anhydrous sodium sulphate are mixed by a blending machine to obtain a composition 10, and the composition is used as yellow reactive dye to dye and dye wool fabrics into yellow.
Comparative example 4
And (2) carrying out dry powder mixing on 75 parts by weight of the component Y shown in the formula (II-1) and 25 parts by weight of anhydrous sodium sulphate by a mixing machine to obtain a composition 11, wherein the composition is used as a yellow reactive dye and can be used for printing and dyeing wool fabrics into yellow.
Comparative example 5
And (3) carrying out dry powder mixing on 75 parts by weight of the component Y shown in the formula (II-15) and 25 parts by weight of anhydrous sodium sulphate by a mixing machine to obtain a composition 12, wherein the composition is used as a yellow reactive dye and can be used for printing and dyeing wool fabrics into yellow.
Printing and dyeing examples
The printing test is carried out according to the national standard GB/2388-:
TABLE 1
The dyeing test is carried out according to the general condition regulation of dye dyeing determination of the national standard GB/2374-:
TABLE 2
Testing solubility and refrigeration performance:
the yellow reactive dye compositions obtained in examples 1 to 7 and comparative examples 1 to 5 were subjected to solubility testing according to the method of GB/T3671.1-1996.
15g of each of the yellow reactive dye compositions 1 to 7 obtained in examples 1 to 7 and the yellow reactive dye compositions 8 to 12 obtained in comparative examples 1 to 5 are dissolved in 85ml of hot water at 75 ℃, the mixture is stored at a low temperature of 5 ℃ after the dye is fully dissolved, and whether the solution is precipitated or not is observed for 2 hours, 4 hours, 8 hours, 24 hours and 48 hours. The test results are shown in table 3:
TABLE 3
The results in tables 1 to 3 show that the yellow reactive dye composition has the advantages of high product performance, high color fixing rate, excellent color fastness properties such as friction resistance, washing resistance, perspiration resistance and the like, and good refrigeration performance and high solubility compared with the traditional products.

Claims (9)

1. A yellow reactive dye composition is characterized by comprising a component X shown in a formula (I), a component Y shown in a formula (II) and optional auxiliary agents;
wherein,
A. each B is independently (C)1-C4) -an alkyl or amino group;
Re1is composed of
Re2Is composed of
X1、X3、X4、X5、X6、X7、X8Each of which is independently a halogen atom,
X2is (C)1~C4) Alkoxy, amino, -NHR3OH or-NHR3SO3M1
Each R is3Each independently is CnH2n(n is 1 or 2);
R1、R2each independently is H, -SO3M2、-COOM2or-R4-X9
R4Is CnH2n(n is 1 or 2),
X9is H, halogen or amino;
each M1Each M2Each independently is an alkali metal, hydrogen or ammonium;
alternatively, the alkali metal is selected from lithium, sodium, potassium;
optionally, the halogen is fluorine, bromine, chlorine.
2. The yellow reactive dye composition according to claim 1, wherein the component X is selected from one or more compounds of formulae (I-1) to (I-7);
3. the yellow reactive dye composition according to claim 1 or 2, wherein the component Y is selected from one or more compounds of formulae (II-1) to (II-17);
4. the yellow reactive dye composition according to any one of claims 1 to 3, wherein the component X is present in an amount of 5 to 80 parts by weight, preferably 5 to 75 parts by weight, more preferably 5 to 70 parts by weight, and still more preferably 10 to 70 parts by weight; the content of the component Y is 10-90 parts by weight, preferably 10-85 parts by weight, more preferably 10-80 parts by weight, and still more preferably 20-80 parts by weight; the content of the auxiliary agent is 0 to 80 parts by weight, preferably 0 to 75 parts by weight, more preferably 0 to 70 parts by weight, and further preferably 0 to 65 parts by weight.
5. Azo-type reactive dye according to any one of claims 1 to 4, wherein the auxiliary agent is selected from one or more of dispersants, fillers and other performance-improving auxiliary agents;
preferably, the dispersant is selected from one or more of dispersant MF and dispersant NNO, the filler is anhydrous sodium sulphate, and the other performance improvement auxiliary agent is selected from at least one of dust-proof agent and solubility improvement agent.
6. A process for the preparation of a yellow reactive dye composition according to any one of claims 1 to 5 which comprises mixing directly or optionally drying a dry powder or slurry of component X, a dry powder or slurry of component Y and optionally auxiliaries in proportions.
7. Use of the yellow reactive dye composition according to any one of claims 1 to 5 as a yellow reactive dye.
8. Use according to claim 7, characterized in that the yellow reactive dyes are used for dyeing and printing of fibres or textiles thereof, including dyeing and/or printing.
9. The use according to claim 8, characterized in that the yellow reactive dyes are used for printing and dyeing cellulose fibers, protein fibers, polyamide fibers or textiles thereof;
preferably, the cellulosic fibers include cotton fibers, hemp fibers, and regenerated fibers; the protein fiber includes wool, silk, and artificial protein fiber.
CN201910663237.0A 2019-07-22 2019-07-22 Yellow reactive dye composition and preparation method and application thereof Active CN110387143B (en)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4851011A (en) * 1987-04-16 1989-07-25 Ciba-Geigy Corporation Process for the preparation of concentrated aqueous dye formulations of water-soluble organic dyes by membrane separation and with cross-flow micro-filtration to remove suspended or colloidal solids
CN1076706A (en) * 1992-03-06 1993-09-29 曾尼卡有限公司 Composition and compound
US5403360A (en) * 1993-02-05 1995-04-04 Ciba-Geigy Corporation Process for dyeing or printing cellulosic fiber materials
CN101597435A (en) * 2008-06-03 2009-12-09 上海雅运纺织化工有限公司 Yellow active dye composition and application thereof
CN102433030A (en) * 2011-10-28 2012-05-02 浙江瑞华化工有限公司 Active yellow dye composition
CN102977638A (en) * 2012-11-30 2013-03-20 浙江瑞华化工有限公司 Composition, preparation method and application thereof, textile and textile product
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US5403360A (en) * 1993-02-05 1995-04-04 Ciba-Geigy Corporation Process for dyeing or printing cellulosic fiber materials
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