CN116355438A - Black reactive dye composition and preparation method and application thereof - Google Patents
Black reactive dye composition and preparation method and application thereof Download PDFInfo
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- CN116355438A CN116355438A CN202111616583.7A CN202111616583A CN116355438A CN 116355438 A CN116355438 A CN 116355438A CN 202111616583 A CN202111616583 A CN 202111616583A CN 116355438 A CN116355438 A CN 116355438A
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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
- C09B67/0047—Mixtures of two or more reactive azo dyes
- C09B67/005—Mixtures of two or more reactive azo dyes all the reactive groups being not directly attached to a heterocyclic system
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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
- C09B67/0071—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
- D06P1/384—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 reactive group not directly attached to heterocyclic group
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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
A black reactive dye composition, and its preparation method and application are provided. The black reactive dye composition comprises a component A shown in a formula (I), a component B shown in a formula (II), a component C shown 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
Technical Field
The invention belongs to the field of fine chemical industry, and particularly relates to a black reactive 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, CN 1687244a 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 shown in a formula (I), a component B shown in a formula (II), a component C shown in a formula (III) and optional auxiliary agents;
wherein A, B are each independently hydrogen or-SO 3 M 1 ；R 1 、R 2 Each independently is-ch=ch 2 or-C 2 H 4 OSO 3 M 1 ；R 3 Is that
R 4 Is hydrogen or-COOM 2 ；R 5 And R is 6 Each of which is a single pieceindependently-SO 3 M 2 、
R 7 Is H, (C) 1 -C 5 ) Alkyl (preferably (C) 1 -C 2 ) -alkyl), (C 1 -C 5 ) Alkoxy (preferably (C) 1 -C 2 ) -an alkoxy group); r is R 8 Is H, (C) 1 -C 5 ) Alkyl (preferably (C) 1 -C 2 ) -alkyl), or (C 1 -C 5 ) Alkoxy (preferably (C) 1 -C 2 ) -an alkoxy group); r is R 9 is-CH=CH 2 or-C 2 H 4 OSO 3 M 3 ；R 10 、R 13 Each independently is-ch=ch 2 or-C 2 H 4 OSO 3 M 2 ；R 11 、R 12 Each independently is hydrogen or SO 3 M 2 ；
M 1 、M 2 、M 3 Each independently is hydrogen, potassium, sodium or lithium.
Preferably, in the black reactive dye composition, the component A is selected from one or more of the compounds of the formulas (I-1) to (I-15),
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-4):
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-7):
in the present invention, the choice of the auxiliary agent is not particularly limited, and may be a conventional auxiliary agent. Preferably, the auxiliary agent is at least one selected from the group consisting of a dispersant, a filler, and other performance improving auxiliary agents.
Preferably, the dispersant is at least one selected from the group consisting of methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF), naphthalene sulfonic acid formaldehyde condensate (NNO), and 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 agent is selected from at least one of a dust-proofing agent, a solubility improving agent, an alkali resistance auxiliary agent, a surfactant, a buffer, and an accelerating agent.
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 0 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. Optionally, during mixing, each dye compound is present in the form of a powder, granulate or aqueous solution; alternatively, a liquid dye product is produced, or a solid product is produced by subjecting the liquid dye product to an optional drying process, or a direct mixing of solid dye powders according to the components.
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, the present invention provides 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
61.5 parts by weight of component A of formula (I-1), 17.8 parts by weight of component B of formula (II-1), 6.2 parts by weight of component C of formula (III-1) and 14.5 parts by weight of anhydrous sodium sulphate 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
60.4 parts by weight of component A of formula (I-1), 15.2 parts by weight of component B of formula (II-2), 10.7 parts by weight of component C of formula (III-1) and 13.7 parts by weight of anhydrous sodium sulphate 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.
Example 3
58.2 parts by weight of component A of formula (I-15), 20.0 parts by weight of component B of formula (II-3), 12.3 parts by weight of component C of formula (III-2) and 9.5 parts by weight of anhydrous sodium sulphate are mixed by a mixing machine to obtain composition 3, and the composition is used as black reactive dye to print cotton fabric into black.
Example 4
62.0 parts by weight of component A of formula (I-6), 18.9 parts by weight of component B of formula (II-4), 8.6 parts by weight of component C of formula (III-4) and 10.5 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.
Comparative example 1
61.8 parts by weight of component A of formula (I-1), 10.2 parts by weight of component B of formula (II-2), 7.2 parts by weight of component C of formula IV and 20.8 parts by weight of anhydrous sodium sulfate are mixed by a mixing machine to obtain composition 5, and the composition is used as black reactive dye to print cotton fabric into black.
Comparative example 2
And (3) mixing 66.9 parts by weight of component A of formula (II-1), 21.6 parts by weight of component B of formula (II-2), 1.1 parts by weight of component C of formula V and 10.4 parts by weight of anhydrous sodium sulfate by a mixing machine to obtain a composition 6, wherein the composition is used as a black reactive dye, and cotton fabric can be printed to black.
Comparative example 3
65.7 parts by weight of component A of formula (I-1), 6.9 parts by weight of component B of formula (III-1), 15.1 parts by weight of component C of formula (VI) and 12.3 parts by weight of anhydrous sodium sulfate are mixed by a mixing machine to obtain a composition 7, and the composition is used as a black reactive dye to print cotton fabric into black.
Performance testing
The compositions obtained in examples 1 to 4 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 Table 1 below:
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 (10)
1. A black reactive dye composition comprising 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 an auxiliary agent:
wherein,,
A. b are each independently hydrogen or-SO 3 M 1 ；R 1 、R 2 Each independently is-ch=ch 2 or-C 2 H 4 OSO 3 M 1 ；
R 3 Is that
R 4 Is hydrogen or-COOM 2 ；R 5 And R is 6 Each independently is-SO 3 M 2 、
R 7 Is H, (C) 1 -C 5 ) Alkyl (preferably (C) 1 -C 2 ) -alkyl), (C 1 -C 5 ) Alkoxy (preferably (C) 1 -C 2 ) -an alkoxy group); r is R 8 Is H, (C) 1 -C 5 ) Alkyl (preferably (C) 1 -C 2 ) -alkyl), or (C 1 -C 5 ) Alkoxy (preferably (C) 1 -C 2 ) -an alkoxy group); r is R 9 is-CH=CH 2 or-C 2 H 4 OSO 3 M 3 ；
R 10 、R 13 Each independently is-ch=ch 2 or-C 2 H 4 OSO 3 M 2 ；R 11 、R 12 Each independently is hydrogen or SO 3 M 2 ；
M 1 、M 2 、M 3 Each independently is hydrogen, potassium, sodium or lithium.
2. The black reactive dye composition according to claim 1, wherein component a is selected from one or more of the compounds of formulae (I-1) to (I-15):
3. the black reactive dye composition according to any of claims 1 to 2, wherein component B is selected from one or more of the compounds of formulae (II-1) to (II-4):
4. a black reactive dye composition according to any of claims 1 to 3, wherein component C is selected from one or more of the compounds of formulae (III-1) to (III-7):
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;
optionally, the dispersing agent is selected from one or more of methyl naphthalene sulfonic acid formaldehyde condensate, naphthalene sulfonic acid formaldehyde condensate and benzyl naphthalene sulfonate formaldehyde condensate;
optionally, the filler is anhydrous sodium sulfate;
optionally, the other performance improving auxiliary is selected from one or more of dustproof agent, solubility improving agent, alkali resistance auxiliary, surfactant, buffer and accelerating agent.
6. The black reactive dye composition according to any of claims 1 to 5, wherein the content of component a is 10 to 90 parts by weight, preferably 20 to 90 parts by weight, more preferably 30 to 90 parts by weight, more preferably 40 to 90 parts by weight;
preferably, 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, still more preferably 10 to 35 parts by weight;
preferably, the content of the component C is 1 to 30 parts by weight, preferably 0 to 25 parts by weight, more preferably 1 to 20 parts by weight, still more preferably 1 to 15 parts by weight;
the content of the auxiliary 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, still more preferably 0 to 50 parts by weight.
7. A process for the preparation of a black reactive dye composition according to any one of claims 1 to 6, comprising mixing component a, component B, component C and optionally an auxiliary agent;
optionally, during mixing, each dye compound is present in the form of a powder, granulate or aqueous solution;
alternatively, a liquid dye product is produced, or a solid product is produced by subjecting the liquid dye product to an optional drying process, or a direct mixing of solid dye powders according to the components.
8. Use of a black reactive dye composition according to any of claims 1 to 6 as a black reactive dye.
9. The use according to claim 8, wherein the black reactive dye composition is used for dyeing and printing cellulose fibers, protein fibers, polyamide fibers or textiles and blend fabrics thereof;
optionally, the cellulosic fibers include cotton fibers, hemp fibers, and regenerated fibers;
optionally, the protein fibers include wool, silk, and wool fabrics.
10. Use according to claim 8 or 9, wherein the black reactive dye composition is used for dyeing or printing hydroxyl-containing or nitrogen-containing fibre materials such as cellulose fibres, protein fibres and the like, optionally including dyeing or printing.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4749380A (en) * | 1985-07-16 | 1988-06-07 | Sumitomo Chemical Company, Limited | Aqueous liquid sulphato-ethylsulphonyl reactive dye composition containing small amount of buffer for storage stability at high and low temperatures |
| CN1513036A (en) * | 2001-06-02 | 2004-07-14 | ����־��˹���֯Ʒ��Ⱦ�����Ϲ�˾ | Dye mixture of fiber-reactive azodyes and use thereof |
| CN101283054A (en) * | 2005-10-05 | 2008-10-08 | 德意志戴斯达纺织品及染料两合公司 | Azo-reactive dyes and mixtures of fiber-reactive azo dyes, their preparation and their use |
| WO2013021352A2 (en) * | 2011-08-10 | 2013-02-14 | Colourtex Industries Limited | Black mixtures of fibre reactive azo reactive dyestuffs |
-
2021
- 2021-12-27 CN CN202111616583.7A patent/CN116355438A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4749380A (en) * | 1985-07-16 | 1988-06-07 | Sumitomo Chemical Company, Limited | Aqueous liquid sulphato-ethylsulphonyl reactive dye composition containing small amount of buffer for storage stability at high and low temperatures |
| CN1513036A (en) * | 2001-06-02 | 2004-07-14 | ����־��˹���֯Ʒ��Ⱦ�����Ϲ�˾ | Dye mixture of fiber-reactive azodyes and use thereof |
| CN101283054A (en) * | 2005-10-05 | 2008-10-08 | 德意志戴斯达纺织品及染料两合公司 | Azo-reactive dyes and mixtures of fiber-reactive azo dyes, their preparation and their use |
| WO2013021352A2 (en) * | 2011-08-10 | 2013-02-14 | Colourtex Industries Limited | Black mixtures of fibre reactive azo reactive dyestuffs |
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