CN115537037B - Black reactive dye and preparation method and application thereof - Google Patents

Black reactive dye and preparation method and application thereof Download PDF

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Publication number
CN115537037B
CN115537037B CN202211030521.2A CN202211030521A CN115537037B CN 115537037 B CN115537037 B CN 115537037B CN 202211030521 A CN202211030521 A CN 202211030521A CN 115537037 B CN115537037 B CN 115537037B
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reactive dye
dye composition
black reactive
component
parts
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CN115537037A (en
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陆军
陶莉莉
阮方平
柳长江
连张杰
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Zhejiang Ruihua Chemical Co ltd
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Zhejiang Ruihua Chemical 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
    • C09B67/0055Mixtures of two or more disazo dyes
    • C09B67/0057Mixtures of two or more reactive disazo dyes
    • C09B67/0059Mixtures of two or more reactive disazo dyes all the reactive groups are not 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
    • 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
    • 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
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Abstract

The invention provides a black reactive dye composition, a preparation method and application thereof, and belongs to the field of reactive dyes. The dye composition comprises a component A consisting of one or more compounds in a formula (I), a component B consisting of one or more compounds in a formula (II), a component C consisting of one or more compounds in a formula (III) and optional auxiliary agents. The black reactive dye composition disclosed by the invention is excellent in performance, is suitable for dyeing or printing hydroxyl-containing or nitrogenous fiber materials such as cellulose fibers and protein fibers, has good fixation rate and color fastness, and has relatively excellent comprehensive performance after dyeing.

Description

Black reactive dye and preparation method and application thereof
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 is almost 40-50%, and more direct dyes and sulfur dyes are used and are forbidden and limited due to environmental protection. Active black KN-B has high dosage because of low price, good fastness, high fixation rate and easy washing property, and no environmental protection problem including AOX. But also has the defects of poor lifting force, insufficient blackness and the like, thereby limiting the wide application of the material.
Currently, some patents of composite reactive black dyes have made remarkable progress in improving the lifting power and the blackness of the reactive black dyes, such as the publication patent CN 1730566A, CN1687244a and the like. However, as the benefits of the printing and dyeing industry are gradually reduced in recent years, the market competition of the reactive dyes is increasingly strong, and the cost performance requirements of the reactive dyes are increasingly high. The development of reactive dye varieties with good washing fastness, perspiration fastness and dyeing reproducibility, higher lifting force and fixation rate and more cost advantage 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, friction resistance, perspiration 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 3 M 3 Methoxy, methyl; r is R 1 、R 2 、R 3 、R 4 、R 6 、R 7 Each independently is-ch=ch 2 or-C 2 H 4 OSO 3 M 4 Alkyl, or H; r is R 5 Hydrogen, sodium or potassium; each R is 8 Each independently is-SO 3 M 6 、(C 1 ~C 4 ) Alkoxy or (C) 1 ~C 4 ) Alkyl of (a); x is X 1 Is oxygen, sulfur or-NR -, and R Is hydrogen or (C) 1 ~C 4 ) -alkoxy, hydroxy, sulfo, cyano; x is X 2 is-NH-X ,X Is hydrogen, (C) 1 ~C 4 ) Alkyl or R of (2) SO 3 M 7 ,R Is (C) 1 ~C 4 ) Alkyl of (a); m is M 1 、M 2 、M 3 、M 4 、M 5 、M 6 、M 7 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-9):
preferably, in the black reactive dye composition, the component C is selected from one or more of the compounds of formulas (III-1) to (III-15):
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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 properties and the like, and meets 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 10 to 90 parts by weight, preferably 20 to 90 parts by weight, more preferably 30 to 90 parts by weight, and even more preferably 40 to 90 parts by weight;
preferably, in the black dye composition, the content of the component B is 1 to 50 parts by weight, preferably 4 to 45 parts by weight, more preferably 7 to 40 parts by weight, and even more preferably 10 to 35 parts by weight;
preferably, in the black dye composition, the content of the component C is 1 to 30 parts by weight, preferably 1 to 25 parts by weight, more preferably 1 to 20 parts by weight, and even more preferably 1 to 15 parts by weight;
preferably, in the black dye composition, the content of the auxiliary agent is 0 to 80 parts by weight, preferably 0 to 70 parts by weight, more preferably 0 to 60 parts by weight, and even 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 provided by the invention has the following advantages: the color fixing rate is high, the lifting force is good, and the color fastness such as water resistance, friction resistance, perspiration resistance and the like are excellent. 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
68.5 parts by weight of component A of formula (I-6), 28.8 parts by weight of component B of formula (II-1), 1.2 parts by weight of component C of formula (III-1) and 1.5 parts by weight of anhydrous sodium sulfate are mixed by a mixing machine to obtain a composition 1, and the composition is used as a black reactive dye to print cotton fabric into black.
Example 2
68.5 parts by weight of component A of formula (I-1), 28.8 parts by weight of component B of formula (II-1), 1.2 parts by weight of component C of formula (III-1) and 1.5 parts by weight of anhydrous sodium sulfate are mixed by a mixing machine to obtain composition 2, and the composition is used as black reactive dye to print cotton fabric into black.
Comparative example 1
73 parts by weight of component A of formula (I-1), 23.5 parts by weight of component (IV) and 3.5 parts by weight of anhydrous sodium sulphate are mixed by a mixing machine to obtain a composition 3, and the composition is used as a reactive black dye to print cotton fabric into black.
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Comparative example 2
73 parts by weight of the component A of the formula (I-1), 18 parts by weight of the component (IV) and 9 parts by weight of the component of the formula (III-1) are mixed by a mixing machine to obtain a composition 4, and the composition is used as a reactive black dye to print cotton fabrics into black.
Comparative example 3
71 parts by weight of component A of formula (I-1), 20 parts by weight of component III-1 and 9 parts by weight of component V are mixed by a mixing machine to obtain a composition 5, and the composition is used as a reactive black dye to print cotton fabric into black.
Performance testing
The compositions obtained in examples 1 to 2 and comparative examples 1 to 3 were respectively subjected to printing and dyeing tests with reference to national standard GB/2387-2003 "method for measuring reactive dye dyeing color light and intensity", and cloth samples were subjected to color fastness tests of fixation rate, rubbing resistance, washing resistance and perspiration resistance 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 (25)

1. A black reactive dye composition comprising a mixture of a component a of a compound of formula (I-6), a component B of a compound of formula (II-1), a component C of a compound of formula (III-1), and optionally an auxiliary agent:
2. a black reactive dye composition comprising a mixture of a component a of a compound of formula (I-1), a component B of a compound of formula (II-1), a component C of a compound of formula (III-1), and optionally an auxiliary agent:
3. a black reactive dye composition according to claim 1 or 2, wherein the auxiliary is selected from one or more of dispersants, fillers and other performance improving auxiliary.
4. A black reactive dye composition according to claim 3, wherein the dispersant is selected from one or more of dispersant MF, dispersant NNO, benzyl naphthalene sulfonate formaldehyde condensate, the filler is anhydrous sodium sulphate, and the other performance improving auxiliary is selected from one or more of dust-proofing agent, solubility improving agent, alkali resistance auxiliary, surfactant, buffer, and accelerating agent.
5. The black reactive dye composition according to claim 1 or 2, wherein the content of component a is 10 to 90 parts by weight based on the total weight of the black reactive dye composition;
the content of the component B is 1-50 parts by weight;
the content of the component C is 1-30 parts by weight;
the content of the auxiliary agent is 0-80 parts by weight.
6. The black reactive dye composition according to claim 5, wherein the component A is contained in an amount of 20 to 90 parts by weight based on the total weight of the black reactive dye composition.
7. The black reactive dye composition according to claim 6, wherein the component a is contained in an amount of 30 to 90 parts by weight based on the total weight of the black reactive dye composition.
8. The black reactive dye composition according to claim 7, wherein the component a is contained in an amount of 40 to 90 parts by weight based on the total weight of the black reactive dye composition.
9. The black reactive dye composition according to claim 5, wherein the component B is contained in an amount of 4 to 45 parts by weight based on the total weight of the black reactive dye composition.
10. The black reactive dye composition according to claim 9, wherein the content of the component B is 7 to 40 parts by weight based on the total weight of the black reactive dye composition.
11. The black reactive dye composition according to claim 10, wherein the content of the component B is 10 to 35 parts by weight based on the total weight of the black reactive dye composition.
12. The black reactive dye composition according to claim 5, wherein the component C is contained in an amount of 1 to 25 parts by weight based on the total weight of the black reactive dye composition.
13. The black reactive dye composition according to claim 12, wherein the component C is contained in an amount of 1 to 20 parts by weight based on the total weight of the black reactive dye composition.
14. The black reactive dye composition according to claim 13, wherein the component C is contained in an amount of 1 to 15 parts by weight based on the total weight of the black reactive dye composition.
15. The black reactive dye composition according to claim 5, wherein the auxiliary is contained in an amount of 0 to 70 parts by weight based on the total weight of the black reactive dye composition.
16. The black reactive dye composition according to claim 15, wherein the auxiliary is contained in an amount of 0 to 60 parts by weight based on the total weight of the black reactive dye composition.
17. The black reactive dye composition according to claim 16, wherein the auxiliary is contained in an amount of 0 to 50 parts by weight based on the total weight of the black reactive dye composition.
18. A process for the preparation of a black reactive dye composition according to any one of claims 1 to 17, comprising mixing component a, component B, component C and optionally an auxiliary agent;
during the mixing process, the individual dye monomer compounds are present in the form of powder, granules or in the form of an aqueous solution.
19. A process for the preparation of a black reactive dye composition according to claim 18, wherein the components are mixed to form a liquid dye product, or the liquid dye product is subjected to an optional drying process to form a solid product, or the solid dye powders according to the components are directly mixed.
20. Use of a black reactive dye composition according to any of claims 1 to 17 as a black reactive dye.
21. The use according to claim 20, wherein the black reactive dye composition is used for dyeing and printing cellulose fibers, protein fibers, polyamide fibers or textiles or blends thereof.
22. The use according to claim 21, wherein the cellulose fibers comprise cotton fibers, hemp fibers and regenerated fibers.
23. The use according to claim 21, wherein the protein fibres comprise wool, silk and wool fabrics.
24. Use according to any one of claims 20 to 23, characterized in that the black reactive dye composition is used for the dyeing of cellulose fibres, protein fibres.
25. The use according to claim 24, wherein the printing comprises dyeing or printing.
CN202211030521.2A 2022-08-26 2022-08-26 Black reactive dye and preparation method and application thereof Active CN115537037B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116102900A (en) * 2023-02-13 2023-05-12 湖北华丽染料工业有限公司 Reactive dark black dye and application thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102898869A (en) * 2012-09-28 2013-01-30 浙江亿得化工有限公司 Composite dark black reactive dye
CN104610776A (en) * 2005-10-05 2015-05-13 德司达染料分销有限公司 Azo reactive dyes and mixtures of fiber-reactive azo dyes, their preparation and their use
CN112574592A (en) * 2020-12-26 2021-03-30 浙江科永化工有限公司 Active navy blue to black dye composition and dye product

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104610776A (en) * 2005-10-05 2015-05-13 德司达染料分销有限公司 Azo reactive dyes and mixtures of fiber-reactive azo dyes, their preparation and their use
CN102898869A (en) * 2012-09-28 2013-01-30 浙江亿得化工有限公司 Composite dark black reactive dye
CN112574592A (en) * 2020-12-26 2021-03-30 浙江科永化工有限公司 Active navy blue to black dye composition and dye product

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