CN116554706B - A black reactive dye and its preparation method and use - Google Patents
A black reactive dye and its preparation method and use Download PDFInfo
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- CN116554706B CN116554706B CN202310314582.XA CN202310314582A CN116554706B CN 116554706 B CN116554706 B CN 116554706B CN 202310314582 A CN202310314582 A CN 202310314582A CN 116554706 B CN116554706 B CN 116554706B
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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
- C09B67/0055—Mixtures of two or more disazo dyes
- C09B67/0057—Mixtures of two or more reactive disazo dyes
- C09B67/0059—Mixtures of two or more reactive disazo dyes all the reactive groups are not 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
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- 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
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- 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
- D06P3/10—Material containing basic nitrogen containing amide groups using reactive dyes
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- 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
- D06P3/24—Polyamides; Polyurethanes
- D06P3/248—Polyamides; Polyurethanes 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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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
本发明提供一种黑色活性染料组合物及其制备方法和用途，属于活性染料领域。所述染料组合物包括包括由式(I)化合物中一种或以上化合物组成的组分A、式(II)化合物中一种或以上化合物组成的组分B、式(III)化合物中一种或以上化合物组成的组分C以及任选的助剂组成。本发明所述黑色活性染料组合物性能优异，适用于纤维素纤维、蛋白质纤维等含羟基或含氮纤维材料染色或印花，具有良好的固色率，提升力好，各项性能指标好，特别是耐水洗、耐摩擦、耐汗渍等色牢度特别优异，是一种能满足高端客户需求的环境友好型活性黑染料。 The present invention provides a black reactive dye composition and a preparation method and use thereof, belonging to the field of reactive dyes. The dye composition comprises component A composed of one or more compounds in formula (I), component B composed of one or more compounds in formula (II), component C composed of one or more compounds in formula (III), and optional auxiliary agents. The black reactive dye composition of the present invention has excellent performance, is suitable for dyeing or printing hydroxyl-containing or nitrogen-containing fiber materials such as cellulose fibers and protein fibers, has good color fixation rate, good lifting power, good various performance indicators, especially excellent color fastness such as water washing resistance, friction resistance, and sweat resistance, and is an environmentally friendly reactive black dye that can meet the needs of high-end customers.
Description
Technical Field
The invention belongs to the field of fine chemical engineering, and particularly relates to a reactive black dye composition, a preparation method and application thereof.
Background
In cotton fiber dyeing, the black color almost accounts for 40-50%, and more direct dyes and sulfur dyes are forbidden and limited to be used due to environmental protection. The monochrome active black KN-B has high dosage because of low price, good fastness, high fixation rate and easy washing property, and no environmental protection problems including AOX. But also has the defects of poor lifting force, insufficient blackness and the like, thereby limiting the wide application of the material.
Along with the higher and higher requirements of customers on reactive dyes, the composite reactive dye has wider and wider application, and different reactive dyes are mixed to play a role in synergy. At present, some patents of composite reactive black dyes have made obvious progress in improving the rubbing fastness and the blackness of the reactive black dyes, such as the publication patent CN 1111073341A, CN 1110079123A, CN 104830097A and the like. However, as the benefits of the dyeing industry are gradually reduced and the market competition of the reactive dye is gradually vigorous, the development of the dye with excellent comprehensive properties is urgent, and particularly the reactive dye variety with good washing fastness, staining fastness and dyeing reproducibility and higher lifting force and fixation rate has more and more important significance.
Disclosure of Invention
The invention provides a black reactive dye composition, which has high fixation rate and excellent color fastness properties such as water washing resistance, staining resistance and the like, is suitable for dyeing and printing of fibers or textile materials thereof, and is an environment-friendly reactive dye.
The invention provides a black reactive dye composition, which comprises a component A composed of one or more compounds in a formula (I), a component B composed of one or more compounds in a formula (II), a component C composed of one or more compounds in a formula (III) and optional auxiliary agents:
Wherein a, b, C are each independently hydrogen, or-SO 3M3, methoxy, methyl, R 1、R2、R3、R4、R5、R6 are each independently-CH=CH 2 or-C 2H4OSO3M4, alkyl, or H, R 7 is (C 1～C4) -alkyl, R 8、R9 are each independently hydrogen, (C 1～C3) -alkyl, or (C 1～C3) -alkoxy, and M 1、M2、M3、M4 are each independently potassium, sodium, or lithium.
Preferably, the black reactive dye composition is characterized in that the component A is selected from one or more of the compounds of the formulas (I-1) to (I-16),
Preferably, in the black reactive dye composition, the component B is selected from one or more of the compounds of formulas (II-1) to (II-12):
Preferably, in the black reactive dye composition, the component C is selected from compounds of formulas (III-1) to (III-2):
After the composition forms the dye, the synergistic effect of the components ensures that the composition has the advantages of high fixation rate, good lifting force, good fastness performances and the like, and particularly has excellent color fastness and washing fastness, thereby meeting the requirements of modern high-grade reactive dyes. The composite dye is used for dyeing cellulosic fiber materials, such as cotton, hemp, viscose and textiles thereof, and is also suitable for dyeing wool, silk and wool fabrics and dyeing cotton-vinylon blended fabrics.
In the present invention, the choice of the auxiliary agent is not particularly limited, and may be a conventional auxiliary agent. Preferably, the above-mentioned auxiliary agent is selected from one or more of dispersing agent, filler, other performance improving auxiliary agent.
Preferably, the dispersant is selected from one or more of methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF), naphthalene sulfonic acid formaldehyde condensate (NNO), benzyl naphthalene sulfonate formaldehyde condensate (dispersant CNF).
Preferably, the filler is industrial sodium sulfate (anhydrous sodium sulfate).
Preferably, the above-mentioned other performance improving auxiliary agents are selected from one or more of dust-proofing agents, solubility improving agents, alkali resistance auxiliary agents, surfactants, buffers, and accelerating agents.
Preferably, in the black dye composition, the content of the component A is 30 to 80 parts by weight, preferably 35 to 75 parts by weight, more preferably 40 to 70 parts by weight, and even more preferably 45 to 65 parts by weight;
preferably, in the black dye composition, the content of the component B is 1 to 20 parts by weight, preferably 1 to 18 parts by weight, more preferably 1 to 16 parts by weight, and even more preferably 1 to 14 parts by weight;
preferably, in the black dye composition, the content of the component C is 5-50 parts by weight, preferably 10-45 parts by weight, more preferably 15-40 parts by weight, and even more preferably 20-35 parts by weight;
in the black dye composition, the content of the auxiliary agent is preferably 0 to 80 parts by weight, more preferably 0 to 70 parts by weight, still more preferably 0 to 60 parts by weight, and still more preferably 0 to 50 parts by weight.
The invention also provides a preparation method of the black reactive dye composition, which is characterized by comprising the step of mixing the component A, the component B, the component C and optional auxiliary agents. In the mixing process, each dye monomer compound can exist in the forms of powder, granule or aqueous solution, and can be prepared into a liquid dye product according to the needs, or can be prepared into a solid product by an optional drying process, or can be directly mixed according to the solid dye powder of each component.
In the present invention, the apparatus for mixing the dry powder is not particularly limited, and preferably, a conical, drum-type or pear blade-type mixer is used for mixing, and after uniform mixing, the test analysis is passed and then the package is carried out. The method for mixing the slurry is not particularly limited, and it is preferable to mix the slurry in a vessel with stirring. In the present invention, the equipment used in the drying process is not particularly limited, and it is preferable to dry the material in a spray tower, a drying room, a flash dryer, or the like to obtain a granular or powdery product.
In another aspect, there is provided the use of the above black reactive dye composition as a black reactive dye.
Alternatively, the black reactive dye composition is used for printing and dyeing cellulose fibers, protein fibers, polyamide fibers or textiles and blended fabrics thereof.
Optionally, the cellulosic fibers include cotton fibers, hemp fibers, and regenerated fibers.
Optionally, the protein fibers include wool, silk, and wool fabrics.
Optionally, the black reactive dye composition is used for dyeing and printing hydroxyl-containing or nitrogenous fiber materials such as cellulose fibers, protein fibers and the like, and optionally, dyeing or printing.
The black reactive dye composition has the advantages of high fixation rate, good lifting force, excellent color fastness such as water resistance, friction resistance, perspiration resistance and the like. The black reactive dye composition of the invention 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 and blended fabrics thereof.
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.
The black reactive dye composition of the present invention may be prepared by using the component A of the formula (I), the component B of the formula (II) and the component C of the formula (III) in a manner well known to those skilled in the art, for example, by a conventional synthesis method, or by using commercially available products.
Example 1
56.9 Parts by weight of component A of formula (I-1), 4.9 parts by weight of component B of formula (II-1), 23.4 parts by weight of component C of formula (III-1) and 14.8 parts by weight of anhydrous sodium sulfate are mixed by a mixing machine to obtain composition 1, and the composition is used as black reactive dye to print cotton fabric into black.
Example 2
The composition 2 is obtained by uniformly stirring the dye primary pulp of the component A containing 66.8 parts by weight of the dye primary pulp of the formula (I-1), the dye primary pulp of the component B containing 4.3 parts by weight of the formula (II-1) and the dye primary pulp of the component C containing 28.9 parts by weight of the formula (III-1), and drying in a drying room, wherein the composition is used as a reactive black dye, and cotton fabrics can be dyed into black.
Comparative example 1
62.1 Parts by weight of component A of formula (I-1), 5.6 parts by weight of component B of formula (II-1), 23.5 parts by weight of component (IV) and 8.8 parts by weight of anhydrous sodium sulphate are mixed by a mixing machine to obtain composition 3, and the composition is used as reactive black dye to print cotton fabrics into black.
Comparative example 2
And (3) mixing 66.7 parts by weight of component A of the formula (I-1), 5.9 parts by weight of component B of the formula (II-1) and 27.4 parts by weight of anhydrous sodium sulfate by a mixing machine to obtain a composition 4, and using the composition as a black reactive dye, so that the cotton fabric can be printed and dyed black.
Comparative example 3
63.4 Parts by weight of component A of formula (I-1), 7.4 parts by weight of component B of formula (II-1), 15.9 parts by weight of component (V) and 13.3 parts by weight of anhydrous sodium sulphate are mixed by a mixing machine to obtain composition 4, and the composition is used as black reactive dye to print cotton fabric into black.
Performance testing
The compositions obtained in examples 1 to 2 and comparative examples 1 to 3 were referred to the national standard GB, respectively
The dyeing test is carried out according to the 'method for measuring the dyeing color light and the intensity of reactive dye', the color fixation rate, the friction resistance, the water washing resistance and the perspiration resistance of cloth samples are tested according to GB/T2391-2014, GB/T3920-2008, GB/T3921-2008 and GB/T3922-2013, and the results are shown in the following table:
TABLE 1
The result shows that the black reactive dye composition has high color fixing rate, good lifting force and good performance indexes compared with the performance of the traditional product, particularly has excellent color fastness such as washing resistance, friction resistance, perspiration resistance and the like, and is an environment-friendly reactive black dye capable of meeting the requirements of high-end clients.
Claims (27)
1. A black reactive dye composition consisting of a component a consisting of one or more compounds of formula (I), a component B consisting of one or more compounds of formula (II), a component C consisting of one or more compounds of formula (III) and optionally auxiliaries:
Wherein a, b, C are each independently hydrogen, R 1、R2、R3、R4、R5、R6 is each independently-C 2H4OSO3M4;R7 is (C 1～C4) -alkyl, R 8 is (C 1～C3) -alkyl, R 9 is (C 1～C3) -alkoxy, and M 1、M2、M3、M4 is each independently potassium, sodium or lithium.
2. The black reactive dye composition according to claim 1, wherein the component A is one or more selected from the group consisting of compounds of the formulae (I-1) to (I-4),
3. The black reactive dye composition according to claim 1, wherein the component B is one or more selected from the group consisting of compounds of formulae (II-1) to (II-5) and (II-7):
4. The black reactive dye composition according to claim 1, wherein the component C is selected from compounds of formulae (III-1) to (III-2):
5. a black reactive dye composition according to any of claims 1 to 4, wherein the auxiliary is selected from one or more of dispersants, fillers and other performance improving auxiliary.
6. The black reactive dye composition according to claim 5, wherein the dispersant is one or more selected from the group consisting of dispersant MF, dispersant NNO, and dispersant CNF, the filler is anhydrous sodium sulfate, and the other performance improving auxiliary is one or more selected from the group consisting of dust-proofing agent, solubility improving agent, alkali resistance auxiliary, surfactant, buffer, and accelerating agent.
7. A black reactive dye composition according to any of claims 1 to 4, wherein the component A is contained in an amount of 30 to 80 parts by weight,
The content of the component B is 1-20 parts by weight;
the content of the component C is 5-50 parts by weight;
the content of the auxiliary agent is 0-80 parts by weight.
8. The black reactive dye composition according to claim 7, wherein the content of the component A is 35 to 75 parts by weight.
9. The black reactive dye composition according to claim 7, wherein the content of the component A is 40 to 70 parts by weight.
10. The black reactive dye composition according to claim 7, wherein the content of the component A is 45 to 65 parts by weight.
11. The black reactive dye composition according to claim 7, wherein the content of the component B is 1 to 18 parts by weight.
12. The black reactive dye composition according to claim 7, wherein the content of the component B is 1 to 16 parts by weight.
13. The black reactive dye composition according to claim 7, wherein the content of the component B is 1 to 14 parts by weight.
14. The black reactive dye composition according to claim 7, wherein the content of the component C is 10 to 45 parts by weight.
15. The black reactive dye composition according to claim 7, wherein the content of the component C is 15 to 40 parts by weight.
16. The black reactive dye composition according to claim 7, wherein the content of the component C is 20 to 35 parts by weight.
17. The black reactive dye composition according to claim 7, wherein the content of the auxiliary agent is 0 to 70 parts by weight.
18. The black reactive dye composition according to claim 7, wherein the content of the auxiliary agent is 0 to 60 parts by weight.
19. The black reactive dye composition according to claim 7, wherein the content of the auxiliary agent is 0 to 50 parts by weight.
20. A process for the preparation of a black reactive dye composition according to any of claims 1 to 19, comprising mixing component a, component B, component C and optionally an auxiliary agent.
21. The method of claim 20, wherein each of the dye monomer compounds is present in the form of a powder, granules or an aqueous solution during the mixing.
22. The method of claim 20, wherein the liquid dye product is produced, or wherein the liquid dye product is produced as a solid product by an optional drying process, or wherein the solid dye powder according to the components is directly mixed.
23. Use of the black reactive dye composition according to any one of claims 1 to 19 as a black reactive dye.
24. The use according to claim 23, wherein the black reactive dye composition is used for dyeing and printing cellulose fibers, protein fibers, polyamide fibers or textiles or blends thereof.
25. The use according to claim 24, wherein the cellulose fibers comprise cotton fibers, hemp fibers and regenerated fibers.
26. The use according to claim 24, wherein the protein fibres comprise wool, silk.
27. The use according to claim 24, wherein the printing comprises dyeing or printing.
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| CN114181545A (en) * | 2021-10-29 | 2022-03-15 | 浙江科永化工有限公司 | Reactive blue-to-black dye composition and dye product |
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| DE102005047391A1 (en) * | 2005-10-05 | 2007-04-12 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Dyes and dye mixtures of fiber-reactive azo dyes, their preparation and their use |
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| CN114181545A (en) * | 2021-10-29 | 2022-03-15 | 浙江科永化工有限公司 | Reactive blue-to-black dye composition and dye product |
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