CN110387143B - Yellow reactive dye composition and preparation method and application thereof - Google Patents
Yellow reactive dye composition and preparation method and application thereof Download PDFInfo
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- CN110387143B CN110387143B CN201910663237.0A CN201910663237A CN110387143B CN 110387143 B CN110387143 B CN 110387143B CN 201910663237 A CN201910663237 A CN 201910663237A CN 110387143 B CN110387143 B CN 110387143B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
- C09B67/0052—Mixtures of two or more reactive monoazo dyes
- C09B67/0053—Mixtures of two or more reactive monoazo dyes all the reactive groups being directly attached to a heterocyclic system
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/673—Inorganic compounds
- D06P1/67333—Salts or hydroxides
- D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- D06P3/148—Wool using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural 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 invention provides a yellow reactive dye composition, a preparation method and application thereof, wherein the yellow reactive dye composition comprises a component X shown in a formula (I), a component Y shown in a formula (II) and optional auxiliary agents; the color fixing rate is high, and the color fastness properties such as rubbing resistance, washing resistance and perspiration resistance are excellent, and the cold storage property and the solubility are high.
Description
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 the content of the first and second substances,
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 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 (22)
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 the content of the first and second substances,
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 CnH2nWherein n is 1 or 2;
R1、R2each independently is H, -SO3M2、-COOM2or-R4-X9，
R4Is CnH2nWherein n is 1 or 2,
X9is H, halogen or amino;
each M1Each M2Each independently is an alkali metal, hydrogen or ammonium.
2. The yellow reactive dye composition according to claim 1, wherein the alkali metal is selected from the group consisting of lithium, sodium, and potassium.
3. The yellow reactive dye composition according to claim 1, wherein the halogen is fluorine, bromine, chlorine.
4. 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);
5. the yellow reactive dye composition according to claim 1 or 4, wherein the component Y is selected from one or more compounds of formulae (II-1) to (II-17);
6. the yellow reactive dye composition according to claim 1, wherein the content of the component X is 5 to 80 parts by weight; the content of the component Y is 10-90 parts by weight; the content of the auxiliary agent is 0-80 parts by weight.
7. The yellow reactive dye composition according to claim 6, wherein the content of the component X is 5 to 75 parts by weight.
8. The yellow reactive dye composition according to claim 7, wherein the content of the component X is 5 to 70 parts by weight.
9. The yellow reactive dye composition according to claim 8, wherein the content of the component X is 10 to 70 parts by weight.
10. The yellow reactive dye composition according to claim 6, wherein the content of the component Y is 10 to 85 parts by weight.
11. The yellow reactive dye composition according to claim 10, wherein the content of the component Y is 10 to 80 parts by weight.
12. The yellow reactive dye composition according to claim 11, wherein the content of the component Y is 20 to 80 parts by weight.
13. The yellow reactive dye composition according to claim 6, wherein the content of the auxiliary agent is 0 to 75 parts by weight.
14. The yellow reactive dye composition according to claim 13, wherein the content of the auxiliary agent is 0 to 70 parts by weight.
15. The yellow reactive dye composition according to claim 14, wherein the content of the auxiliary agent is 0 to 65 parts by weight.
16. The yellow reactive dye composition according to any one of claims 1, 6 and 13 to 15, wherein the auxiliary agent is selected from one or more of a dispersant, a filler and other performance improving auxiliary agents.
17. The yellow reactive dye composition according to claim 16, wherein the dispersant is one or more selected from the group consisting of a dispersant MF and a dispersant NNO, the filler is anhydrous sodium sulphate, and the other performance improvement auxiliary agent is at least one selected from the group consisting of a dust control agent and a solubility improvement agent.
18. A process for the preparation of a yellow reactive dye composition according to any one of claims 1 to 17 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.
19. Use of the yellow reactive dye composition according to any one of claims 1 to 17 as a yellow reactive dye.
20. Use according to claim 19, characterized in that the yellow reactive dyes are used for dyeing and printing of fibres or textiles thereof, including dyeing and/or printing.
21. Use according to claim 20, characterized in that the yellow reactive dyes are used for printing and dyeing cellulose fibres, protein fibres, polyamide fibres or textiles thereof.
22. Use according to claim 21, characterized in that the cellulose fibres comprise cotton fibres, hemp fibres and regenerated fibres; the protein fiber includes wool, silk, and artificial protein fiber.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9204905D0 (en) * | 1992-03-06 | 1992-04-22 | Ici Plc | Compositions and compounds |
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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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