A black reactive dye and its preparation method and use

Abstract

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 a component A composed of one or more compounds in the compound of formula (I), a component B composed of one or more compounds in the compound of formula (II), a component C composed of one or more compounds in the compound of formula (III), and an optional auxiliary agent. 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 perspiration resistance, and is an environmentally friendly reactive black dye that can meet the needs of high-end customers.

Description

Technical Field

[0001] The invention belongs to the field of fine chemicals, and in particular relates to a reactive black dye composition, a preparation method thereof and applications thereof. Background Art

[0002] In cotton fiber dyeing, black accounts for almost 40-50%, and the direct dyes and sulfur dyes that are used more are banned and restricted due to environmental issues. Single-color reactive black KN-B is used in large quantities due to its low price, good fastness, high fixation rate and easy washing, and no environmental issues including AOX. However, it also has defects such as poor lifting power and insufficient blackness, which limits its widespread use.

[0003] As customers have higher and higher requirements for reactive dyes, composite reactive dyes are used more and more widely. Mixing different reactive dyes can play a synergistic role. At present, some patents for composite reactive black dyes have made significant progress in improving the friction fastness and blackness of reactive black dyes, such as the public patents CN 1111073341A, CN1110079123A, CN 104830097A, etc. However, due to the recent decline in the benefits of the printing and dyeing industry and the increasingly fierce competition in the reactive dye market, it is urgent to develop dyes with excellent comprehensive performance, especially reactive dyes with good washing fastness, staining fastness and dyeing reproducibility, high lifting power and fixation rate. It is becoming more and more important. Summary of the invention

[0004] The invention provides a black reactive dye composition, which has a high color fixation rate and excellent color fastness properties such as water resistance and staining resistance, is suitable for printing and dyeing fibers or textile materials thereof, and is an environmentally friendly reactive dye.

[0005] The present invention provides a black reactive dye composition, which comprises a component A composed of one or more compounds of formula (I), a component B composed of one or more compounds of formula (II), a component C composed of one or more compounds of formula (III), and an optional auxiliary agent:

[0006]

[0007]

[0008] Among them, a, b, and c are each independently hydrogen, or -SO3M3, methoxy, or methyl; R1, R2, R3, R4, R5, and R6 are each independently -CH=CH2 or -C2H4OSO3M4, alkyl, or H; R7 is (C1~C4)-alkyl, R8 and R9 are each independently hydrogen, (C1~C3)-alkyl, or (C1~C3)-alkoxy; M1, M2, M3, and M4 are each independently potassium, sodium, or lithium.

[0009] Preferably, the above-mentioned black reactive dye composition is characterized in that the component A is selected from one or more compounds of formula (I-1) to (I-16),

[0010]

[0011]

[0012]

[0013]

[0014] Preferably, in the above-mentioned black reactive dye composition, the component B is selected from one or more compounds of formula (II-1) to (II-12):

[0015]

[0016]

[0017]

[0018]

[0019] Preferably, in the above-mentioned black reactive dye composition, the component C is selected from the compounds of formula (III-1) to (III-2):

[0020]

[0021]

[0022] After the composition is formed into a dye, the synergistic effect of the components makes it have the advantages of high color fixation rate, good lifting power, good fastness properties, etc., especially excellent staining fastness and washing fastness, which meets the requirements of modern high-end reactive dyes. The composite dye is used for printing and dyeing of cellulose fiber materials, such as cotton, linen, viscose fiber and textiles thereof, and is also suitable for printing and dyeing of wool, silk and wool fabrics and printing and dyeing of cotton-wool blended fabrics.

[0023] In the present invention, there is no particular limitation on the selection of the auxiliary agent, which may be a conventional auxiliary agent. Preferably, the auxiliary agent is selected from one or more of a dispersant, a filler, and other performance-improving auxiliary agents.

[0024] Preferably, the dispersant is selected from one or more of methylnaphthalenesulfonic acid formaldehyde condensate (dispersant MF), naphthalenesulfonic acid formaldehyde condensate (NNO), and benzylnaphthalenesulfonate formaldehyde condensate (diffuser CNF).

[0025] Preferably, the filler is industrial sodium sulfate (sodium sulfate).

[0026] Preferably, the other performance improving additives are selected from one or more of dust suppressants, solubility improving agents, alkali resistance additives, surfactants, buffers, and dyeing accelerators.

[0027] Preferably, in the above black dye composition, the content of 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 more preferably 45 to 65 parts by weight;

[0028] Preferably, in the above black dye composition, the content of 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 more preferably 1 to 14 parts by weight;

[0029] Preferably, in the above black dye composition, the content of component C is 5 to 50 parts by weight, preferably 10 to 45 parts by weight, more preferably 15 to 40 parts by weight, and more preferably 20 to 35 parts by weight;

[0030] Preferably, in the above 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 more preferably 0 to 50 parts by weight.

[0031] The present invention also provides a method for preparing the above-mentioned black reactive dye composition, characterized in that it comprises mixing component A, component B, component C and optional auxiliary agents. During the mixing process, each dye monomer compound can exist in the form of powder, granular or aqueous solution, and can be made into a liquid dye product as required, or the liquid dye product can be made into a solid product through an optional drying process, or the solid dye powders of each component can be directly mixed.

[0032] In the present invention, there is no particular limitation on the equipment used for mixing the dry powder. Preferably, a conical, drum or pear knife mixer is used for mixing. After the mixture is evenly mixed, the mixture is tested and analyzed to be qualified before packaging. In addition, there is no particular limitation on the mixing method of the slurry. Preferably, the mixture is stirred and mixed in a container. In addition, the present invention also has no particular limitation on the equipment used in the drying process. Preferably, a spray tower, drying room or flash dryer is used for drying to obtain a granular or powdered product.

[0033] In another aspect, there is provided use of the black reactive dye composition as a black reactive dye.

[0034] Optionally, the black reactive dye composition is used for printing and dyeing cellulose fibers, protein fibers, polyamide fibers or textiles and blended fabrics thereof.

[0035] Optionally, the cellulose fibers include cotton fibers, hemp fibers, and regenerated fibers.

[0036] Optionally, the protein fibers include wool, silk and fleece.

[0037] Optionally, the black reactive dye composition is used for printing and dyeing hydroxyl-containing or nitrogen-containing fiber materials such as cellulose fibers and protein fibers. Optionally, the printing and dyeing includes dyeing or printing.

[0038] The black reactive dye composition of the present invention has the following advantages: high color fixation rate, good lifting power, and excellent color fastness such as water resistance, friction resistance, and perspiration resistance. The black reactive dye composition of the present invention is suitable for printing and dyeing of cellulose fiber materials, such as cotton, linen, regenerated fiber and textiles thereof, and is also suitable for printing and dyeing of protein fiber, polyamide fiber and textiles thereof and blended fabrics. DETAILED DESCRIPTION

[0039] The present invention is further described below in conjunction with specific embodiments, but the protection scope of the present invention is not limited thereto.

[0040] The black reactive dye composition of the present invention, the component A represented by formula (I), the component B represented by formula (II), and the component C represented by formula (III) used can be conveniently synthesized in a manner well known to those skilled in the art, such as by conventional synthesis methods, or commercially available products can be used.

[0041]

[0042]

[0043] Example 1

[0044] 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 sodium sulfoxide are dry-mixed by a mixer to obtain composition 1. The composition is used as a black reactive dye to print and dye cotton fabrics in black.

[0045]

[0046]

[0047] Example 2

[0048] A dye pulp containing 66.8 parts by weight of component A of formula (I-1) on a dry basis, a dye pulp containing 4.3 parts by weight of component B of formula (II-1) on a dry basis, and a dye pulp containing 28.9 parts by weight of component C of formula (III-1) on a dry basis are uniformly stirred and dried in a drying room to obtain composition 2. The composition can be used as a reactive black dye to print and dye cotton fabrics in black.

[0049]

[0050]

[0051] Comparative Example 1

[0052] 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 of component (IV) and 8.8 parts by weight of sodium sulfoxide are dry-mixed by a mixer to obtain composition 3. The composition can be used as a reactive black dye to print and dye cotton fabrics in black.

[0053]

[0054]

[0055] Comparative Example 2

[0056] 66.7 parts by weight of component A of formula (I-1), 5.9 parts by weight of component B of formula (II-1) and 27.4 parts by weight of sodium sulfoxide are mixed by a mixer to obtain composition 4. The composition can be used as a black reactive dye to print and dye cotton fabrics in black.

[0057]

[0058]

[0059] Comparative Example 3

[0060] 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 sodium sulfoxide are dry-mixed by a mixer to obtain composition 4. The composition can be used as a black reactive dye to print and dye cotton fabrics in black.

[0061]

[0062]

[0063] Performance Testing

[0064] The compositions obtained in Examples 1 to 2 and Comparative Examples 1 to 3 were respectively prepared according to the national standard GB

[0065] / 2387-2003 "Determination of color and intensity of reactive dyes" for printing and dyeing tests, and the fabric samples were tested for color fixation rate, friction resistance, washing resistance and perspiration resistance according to GB / T2391-2014, GB / T 3920-2008, GB / T 3921-2008 and GB / T 3922-2013. The results are as follows:

[0066] Table 1

[0067]

[0068] The results show that the product performance of the black reactive dye composition of the present invention is higher than that of the traditional products, with higher color fixation rate, better lifting power, and better performance indicators, especially excellent color fastness such as resistance to washing, resistance to friction, and resistance to sweat stains. It is an environmentally friendly reactive black dye that can meet the needs of high-end customers.

Claims

1. A black reactive dye composition, which is composed of component A consisting of one or more compounds of formula (I), component B consisting of one or more compounds of formula (II), component C consisting of one or more compounds of formula (III), and optional auxiliary agents: in, a, b, c are each independently hydrogen; R1, R2, R3, R4, R5, R6 are each independently -C2H4OSO3M4; R7 is (C1~C4)-alkyl, R8 is (C1~C3)-alkyl, R9 is (C1~C3)-alkoxy; M1, M2, M3, M4 are each independently potassium, sodium or lithium.

2. The black reactive dye composition according to claim 1, characterized in that The component A is selected from one or more compounds of formula (I-1) to (I-4), 3. The black reactive dye composition according to claim 1, characterized in that The component B is selected from one or more compounds of formula (II-1) to (II-5) and (II-7):

4. The black reactive dye composition according to claim 1, characterized in that The component C is selected from the compounds of formula (III-1) to (III-2):

5. The black reactive dye composition according to any one of claims 1 to 4, characterized in that: The auxiliary agent is selected from one or more of a dispersant, a filler and other auxiliary agents for improving performance.

6. The black reactive dye composition according to claim 5, characterized in that: The dispersant is selected from one or more of dispersant MF, dispersant NNO, and diffusant CNF, the filler is sodium sulfate, and the other performance improving additives are selected from one or more of dust suppressants, solubility improvers, alkali resistance additives, surfactants, buffers, and dyeing accelerators.

7. The black reactive dye composition according to any one of claims 1 to 4, characterized in that: The content of component A is 30 to 80 parts by weight. The content of component B is 1 to 20 parts by weight; The content of component C is 5 to 50 parts by weight; The content of the auxiliary agent is 0 to 80 parts by weight.

8. The black reactive dye composition according to claim 7, characterized in that: The content of component A is 35 to 75 parts by weight.

9. The black reactive dye composition according to claim 7, characterized in that: The content of component A is 40 to 70 parts by weight.

10. The black reactive dye composition according to claim 7, characterized in that: The content of component A is 45 to 65 parts by weight.

11. The black reactive dye composition according to claim 7, characterized in that: The content of component B is 1 to 18 parts by weight.

12. The black reactive dye composition according to claim 7, characterized in that: The content of component B is 1 to 16 parts by weight.

13. The black reactive dye composition according to claim 7, characterized in that: The content of component B is 1 to 14 parts by weight.

14. The black reactive dye composition according to claim 7, characterized in that: The content of component C is 10 to 45 parts by weight.

15. The black reactive dye composition according to claim 7, characterized in that: The content of component C is 15 to 40 parts by weight.

16. The black reactive dye composition according to claim 7, characterized in that: The content of component C is 20 to 35 parts by weight.

17. The black reactive dye composition according to claim 7, characterized in that: The content of the auxiliary agent is 0 to 70 parts by weight.

18. The black reactive dye composition according to claim 7, characterized in that: The content of the auxiliary agent is 0 to 60 parts by weight.

19. The black reactive dye composition according to claim 7, characterized in that: The content of the auxiliary agent is 0 to 50 parts by weight.

20. A method for preparing the black reactive dye composition according to any one of claims 1 to 19, comprising mixing component A, component B, component C and optional auxiliary agents.

21. The preparation method according to claim 20, characterized in that: During the mixing process, each dye monomer compound exists in the form of powder, granules or aqueous solution.

22. The preparation method according to claim 20, characterized in that: The liquid dye product is prepared, or the liquid dye product is subjected to an optional drying process to prepare a solid product, or the solid dye powders of each component are directly mixed to obtain the product.

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, characterized in that The black reactive dye composition is used for printing and dyeing cellulose fiber, protein fiber, polyamide fiber or their textiles or blended fabrics.

25. The use according to claim 24, characterized in that The cellulose fibers include cotton fibers, hemp fibers and regenerated fibers.

26. The use according to claim 24, characterized in that The protein fibers include wool and silk.

27. The use according to claim 24, characterized in that The printing and dyeing includes dyeing or printing.

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