CN105694533A - 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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- CN105694533A CN105694533A CN201610153314.4A CN201610153314A CN105694533A CN 105694533 A CN105694533 A CN 105694533A CN 201610153314 A CN201610153314 A CN 201610153314A CN 105694533 A CN105694533 A CN 105694533A
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- 0 Cc(cc(*)cc1)c1N=Nc(c(N)c1N=Nc2ccc(*)cc2)c([*+])cc1N Chemical compound Cc(cc(*)cc1)c1N=Nc(c(N)c1N=Nc2ccc(*)cc2)c([*+])cc1N 0.000 description 4
Classifications
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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
- C09B67/004—Mixtures of two or more reactive dyes
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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
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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
- 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
-
- 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
- D06P3/02—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
- D06P3/666—Natural or regenerated cellulose using reactive dyes reactive group not directly attached to heterocyclic group
Abstract
The invention discloses a black reactive dye composition and a preparation method and application thereof. The composition comprises a component A composed of one or more compounds in the formula (I), a component B composed of one or more compounds in the formula (II), a component C composed of one or more compounds in the formula (III), and an optional auxiliary. The black reactive dye composition is applicable to printing and dyeing of various kinds of fibers and textile fabrics thereof, high in relative color fixation rate, good in color fastness and excellent in comprehensive performance.
Description
Technical field
The present invention relates to a kind of Black reactive dye composition and its production and use。
Background technology
In cotton fiber dyeing, black almost accounts for 40～50%, more direct dyes and sulfur dye disabled due to environmental issue and limited use。The resultant effect of the active black dye composition of prior art such as CN104804470A is difficult to reach the expected value of people, it is necessary to further improve, such as existing defects in every color fastness。
Summary of the invention
The advantages such as the present invention provides a kind of Black reactive dye composition, and described compositions has cost performance height, and relative degree of fixation is high, and every fastness properties is excellent。It addition, the preparation method that present invention also offers described compositions。
The present invention provides a kind of Black reactive dye composition, it component C including in formula (I) compound one or more compounds composition in the component B of one or more compounds composition, formula (III) compound in the component A of one or more compounds composition, formula (II) compound and optional auxiliary agent:
Wherein, M1、M2、M3It is each independently hydrogen, potassium, sodium, lithium or ammonium；R1、R2It is each independently-CH=CH2Or-C2H4OSO3M1；R3For (C1～C4) alkyl or (C1～C4) alkoxyl；R4、R5It is each independently-CH=CH2Or-C2H4OSO3M2；R6For-CH=CH2Or-C2H4OSO3M3；R7And R8One of them is-OH, and another one is-NH2。
Preferably, above-mentioned Black reactive dye composition also includes the component D of one or more compounds composition in formula (IV) compound:
Wherein, M4For hydrogen, potassium, sodium, lithium or ammonium；R9For (C1～C4) alkyl or (C1～C4) alkoxyl；R10For-CH=CH2Or-C2H4OSO3M4。
For above-mentioned formula (III) or formula (IV) compound, it is possible to be the product being simultaneously generated in formula (I) or formula (II) compou nd synthesis process respectively, it is also possible to be the component that it is possible to additionally incorporate。
Preferably, in above-mentioned Black reactive dye composition, described component A is selected from one or more in formula (I-1)～(I-10) compound:
Preferably, component B described in above-mentioned Black reactive dye composition is selected from one or more in formula (II-1)～(II-15) compound:
Preferably, in above-mentioned Black reactive dye composition, described component C is selected from one or more in formula (III-1)～(III-10) compound:
Preferably, in above-mentioned Black reactive dye composition, described component D is selected from one or more in formula (IV-1)～(IV-10) compound:
In the present invention, the selection of described auxiliary agent is not particularly limited, it is possible to for conven-tional adjuvants。Preferably, above-mentioned auxiliary agent at least one in dispersant, filler, other performance improvement auxiliary agents。
Preferably, above-mentioned dispersant at least one in Dispersant MF, dispersant NNO。
Preferably, above-mentioned filler is Matrii Sulfas Exsiccatus。
Preferably, other performance improvement auxiliary agents above-mentioned at least one in dust-proofing agent, dissolubility improving agent。
Preferably, in above-mentioned black dye composition, the content of described component A is 10～90 weight portions, it is preferred to 20～90 weight portions, is further preferably 30～90 weight portions, more preferably 40～90 weight portions。
Preferably, in above-mentioned black dye composition, the content of described component B is 1～50 weight portion, it is preferred to 2～48 weight portions, is further preferably 3～46 weight portions, more preferably 4～44 weight portions。
Preferably, in above-mentioned black dye composition, the content of described component C is 1～15 weight portion, it is preferred to 1～14 weight portion, is further preferably 1～13 weight portion, more preferably 1～12 weight portion。
Preferably, in above-mentioned black dye composition, the content of described component D is 0～10 weight portion, it is preferred to 0～9 weight portion, is further preferably 0～8 weight portion, more preferably 0～7 weight portion。
Preferably, in above-mentioned black dye composition, the content of described auxiliary agent is 0～80 weight portion, it is preferred to 0～75 weight portion, more preferably 0～70 weight portion, is further preferably 0～65 weight portion。
The preparation method that the present invention also provides for a kind of above-mentioned Black reactive dye composition, it is characterised in that include preparing the mixing of component A, component B, component C, optional component D and optional auxiliary agent。
Preferably, above-mentioned preparation method, including: in proportion by the dry powder of component A or slurry, the dry powder of component B or slurry, the dry powder of component C or slurry, the dry powder of optional component D or slurry and the mixing of optional auxiliary agent, prepared by optional dry run。
Preferably, above-mentioned preparation method, including: in proportion the dry powder of component A, the dry powder of component B, the dry powder of component C, the dry powder of optional component D and optional auxiliary agent are mixed to get product。
Preferably, above-mentioned preparation method, including: in proportion by the slurry of component A, the slurry of component B, the slurry of component C, the slurry of optional component D and optionally auxiliary agent mixing, prepare product by optional dry run。
In the present invention, there is no particular limitation for the equipment described dry powder mixed, it is preferable that adopting the blender of taper, drum-type or pears blade to mix, after mix homogeneously, test analysis is qualified packs again。It addition, to the mixed method of described slurry, there is no particular limitation, it is preferable that is stirred mixing in a reservoir。It addition, the equipment that described dry run is adopted by the present invention is also without special restriction, it is preferred to use spray tower, drying room or flash distillation dryer etc. are dried and obtain granular or powder product。
The present invention also provides for the above-mentioned black dyes active compound purposes as reactive black dye。
Preferably, above-mentioned reactive black dye is for the printing and dyeing of fiber or its yarn fabric。
It is further preferred that above-mentioned reactive black dye is for the printing and dyeing of Fypro, cellulose fibre, protein fibre or their yarn fabric。
It is further preferred that above-mentioned cellulose fibre includes cotton fiber, flaxen fiber, wool fiber, regenerated fiber。
Again it is further preferred that above-mentioned printing and dyeing include dyeing and/or stamp, above-mentioned cotton fiber includes synthetic cotton, and above-mentioned reactive black dye is used for synthetic cotton stamp。
The Black reactive dye composition of the present invention, has the advantage that cost performance is high, the advantages such as relative degree of fixation is high, and compatibility is good, and every fastness properties is excellent。The Black reactive dye composition of the present invention is suitable for the printing and dyeing of cellulosic fibre material, such as the printing and dyeing of cotton, fiber crops, regenerated fiber and yarn fabric thereof, is also applied for the printing and dyeing of Fypro, protein fibre and yarn fabric thereof in addition。
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is described in detail。It should be appreciated that being merely cited for property of detailed description of the invention described herein illustrate, but protection scope of the present invention is not limited to this。
Formula (I-1) compound that adopts in following embodiment, formula (II-1) compound, formula (II-4) compound, formula (V) compound can be obtained by following approach:
Formula (I-1) can synthesize by existing method, it is possible to adopts commercially available prod。
Formula (II-1) can be prepared by the following method:
(1) 4B acid (formula (a-1)) that percentage amount is 18.7 grams is pulled an oar with suitable water and ice, after ice grinds about 1 hour, add hydrochloric acid (being 3.8 grams containing HCl percentage amount) and appropriate ice, stir 5-10 minute, add the sodium nitrite being completely dissolved that percentage amount is 7.0 grams, maintain temperature 0 DEG C～15 DEG C, keep Congored test paper vivid blue, the micro-indigo plant of potassium iodide starch paper, stirring reaction 1 hour, eliminate excessive nitrite with sulfamic acid, obtain 4B acid diazol；
(2) it it is 15.2 grams consoluet 3 by percentage amount, 5-diaminobenzoic acid (formula (b-1)) solution is added dropwise in above-mentioned 4B acid diazol, within 2 hours, drip off, stir 4～6 hours, temperature keeps 0 DEG C～10 DEG C, react and disappear to 4B acid diazol, obtain acid coupling thing；
(3) para-ester (formula (c-1)) that percentage amount is 56.2 grams is pulled an oar with suitable water and ice, ice grinds 2 hours, add hydrochloric acid (being 7.6 grams containing HCl percentage amount) and appropriate ice, stir 20-40 minute, add the sodium nitrite being completely dissolved that percentage amount is 13.8 grams, maintain temperature 0 DEG C～15 DEG C, keep Congored test paper vivid blue, the micro-indigo plant of potassium iodide starch paper, stirring reaction 1～2 hour, excessive nitrite is eliminated with sulfamic acid, obtain para-ester diazol, it is quickly put in the described acid coupling thing of step (2), keep temperature 0 DEG C～10 DEG C, pH4～7 are maintained with sodium bicarbonate (sodium bicarbonate), react to diazol disappearance, carry out spray drying, obtain formula (II-1) compound。
Formula (II-4) formula (II-1) compound cools to 0 DEG C～10 DEG C, is slowly added into liquid caustic soda, maintains temperature 0 DEG C～10 DEG C, maintain pH10～13, react 1～2 hour and stablize to pH, adjust back pH to 4～7 with hydrochloric acid, prepare after spray drying。
Formula (V) can be prepared by the following method:
(1) orthanilic acid suitable quantity of water and ice that percentage amount is 68.0 grams are pulled an oar, add hydrochloric acid (being 15.5 grams containing HCl percentage amount) and appropriate ice is cooled to 0 DEG C, add the sodium nitrite solution being completely dissolved that percentage amount is 27.1 grams, maintain temperature 0 DEG C～15 DEG C, keep Congored test paper vivid blue, the micro-indigo plant of potassium iodide starch paper, stirring reaction 2 hours, eliminate excessive nitrite with sulfamic acid, obtain orthanilic acid diazol；
(2) it it is 59.8 grams be completely dissolved and mix up pH value 3 by percentage amount, 5 diaminobenzoic acids are added drop-wise in the described orthanilic acid diazol of step (1), and temperature keeps 0 DEG C～10 DEG C, and stirring reaction 4 little Su arrives to coupling terminal, it is cooled to 0 DEG C～5 DEG C, obtains single even thing；
(3) being pulled an oar with suitable water and ice by the para-ester that percentage amount is 220.9 grams, ice grinds about 1 hour。Add hydrochloric acid (being 28.7 grams containing HCl percentage amount) and appropriate ice, stir 20-40 minute, add the sodium nitrite solution being completely dissolved that percentage amount is 54.2 grams, maintain temperature 0 DEG C～15 DEG C, keep Congored test paper vivid blue, the micro-indigo plant of potassium iodide starch paper, stirring reaction 2 hours, eliminate excessive nitrite with sulfamic acid, obtain para-ester diazol and treat coupling；
(4) step (3) described para-ester diazol is quickly put in the described single even thing of step (2), keep temperature 0 DEG C～10 DEG C, pH4～7 are maintained with sodium bicarbonate, reaction to diazol disappears for terminal, adding percentage amount is that 7.8 grams of liquid caustic soda solution adjust pH to be 6-8, adding percentage amount after stable is 10.0 grams of glucoses, carries out spray drying and namely obtains formula (V) compound。
Embodiment 1
The component C of the component B of the component A of 78.5 weight portion formulas (I-1) and 20.5 weight portion formulas (II-1) and 1 weight portion formula (III-1) is carried out dry powder blend by blender, obtain Black reactive dye composition 1, using described compositions as reactive black dye, cotton dyeing is become black。
Embodiment 2
The component C of the component A of 80 weight portion formulas (I-1) and the component B of 15 weight portion formulas (II-1), 5 weight portion formulas (III-2) is carried out dry powder blend by blender, obtain Black reactive dye composition 2, using described compositions as reactive black dye, cotton dyeing is become black。
Embodiment 3
The component A of 77 weight portion formulas (I-1) and the component B of 20 weight portion formulas (II-1), the component C of 1 weight portion formula (III-1) and the component D of 2 weight portion formulas (IV-1) are carried out dry powder blend by blender, obtain Black reactive dye composition 3, using described compositions as reactive black dye, cotton dyeing is become black。
Embodiment 4
The component A of 80 weight portion formulas (I-1) and the component B of 10 weight portion formulas (II-4), the component C of 7 weight portion formulas (III-2) and the component D of 3 weight portion formulas (IV-2) are carried out dry powder blend by blender, obtain Black reactive dye composition 4, using described compositions as reactive black dye, cotton dyeing is become black。
Comparative example 1
The Matrii Sulfas Exsiccatus of the component B in the component A of 76.9 weight portion formulas (I-1), embodiment 1 is replaced to 21.6 weight portions the compound as shown in formula (V) and 1.5 weight portions carries out dry powder blend by blender, obtain Black reactive dye composition 5, using described compositions as reactive black dye, cotton dyeing is become black。
Comparative example 2
The component B of the component A of 80 weight portion formulas (I-1) and 20 weight portion formulas (II-1) is carried out dry powder blend by blender, obtains Black reactive dye composition 6, using described compositions as reactive black dye, cotton dyeing is become black。
Dye test:
To each 2g of Black reactive dye composition 1-6 obtained by embodiment 1-4 and comparative example 1-2 respectively with in each 1000g of the dye liquor that 45g sodium chloride is made, it is separately added into 100g bafta, after being warmed up to 60 DEG C with 1 DEG C/minute, adding 100g concentration in each dye liquor is the sodium carbonate liquor of 20g/L, and dye 1 hour at this temperature, then dyeing and weaving thing is rinsed, post rinse drying after soaping 15 minutes with nonionic detergent。Carrying out testing its relative degree of fixation, rub resistance, water-fastness and colour fastness to perspiration according to GB/T2391-2014, GB/T3920-2008, GB/T3921-2008 and GB/T3922-2013, result is table one such as:
Table one
Cost performance compares:
The cost of the reactive black dye of the embodiment of the present invention 1 and comparative example 1 is respectively in Table two and table three, and data are produce cost (unit) needed for one ton of each component of dyestuff (intensity under standard control is 100%)。
Table two
Table three
As shown in Table 1, the Black reactive dye composition of the present invention, when being applied to dye as reactive black dye, compared with comparative example, relative degree of fixation and every fastness properties are better, and are substantially better than the similar competing product in market。In addition, from table two, table three, when intensity under standard control is 100%, the Black reactive dye composition of the present invention, when being applied to dye as reactive black dye, cost performance is compared height, often produce 1 ton of dyestuff can economize in raw materials cost 644.5 yuan, batch production will significantly improve economic benefit, hence it is evident that is better than the reactive black dye being colorant match component with component (V), thus has comparatively excellent combination property。
Claims (10)
1. a Black reactive dye composition, it component C including one or more compounds composition in the component B of one or more compounds composition, formula (III) compound in the component A of the composition of one or more compounds in formula (I) compound, formula (II) compound and optional auxiliary agent:
Wherein, M1、M2、M3It is each independently hydrogen, potassium, sodium, lithium or ammonium；R1、R2It is each independently-CH=CH2Or-C2H4OSO3M1；R3For (C1～C4) alkyl or (C1～C4) alkoxyl；R4、R5It is each independently-CH=CH2Or-C2H4OSO3M2；R6For-CH=CH2Or-C2H4OSO3M3；R7And R8One of them is-OH, and another one is-NH2。
2. Black reactive dye composition according to claim 1, it is characterised in that described Black reactive dye composition also includes the component D of one or more compounds composition in formula (IV) compound:
Wherein, M4For hydrogen, potassium, sodium, lithium or ammonium；R9For (C1～C4) alkyl or (C1～C4) alkoxyl；R10For-CH=CH2Or-C2H4OSO3M4。
3. Black reactive dye composition according to claim 1 and 2, it is characterised in that described component A is selected from one or more in formula (I-1)～(I-10) compound:
4. the Black reactive dye composition according to any one of claims 1 to 3, it is characterised in that described component B is selected from one or more in formula (II-1)～(II-15) compound:
5. the Black reactive dye composition according to any one of Claims 1 to 4, it is characterised in that described component C is selected from one or more in formula (III-1)～(III-10) compound:
6. according to the Black reactive dye composition described in any one of Claims 1 to 5, it is characterised in that described component D is selected from one or more in formula (IV-1)～(IV-10) compound:
7. the Black reactive dye composition according to any one of claim 1～6, it is characterised in that described auxiliary agent at least one in dispersant, filler, other performance improvement auxiliary agents；Preferably, described dispersant at least one in Dispersant MF, dispersant NNO；Preferably, described filler is Matrii Sulfas Exsiccatus；Preferably, other performance improvement auxiliary agents described at least one in dust-proofing agent, dissolubility improving agent。
8. the Black reactive dye composition according to any one of claim 1～7, it is characterised in that in described Black reactive dye composition, the content of component A is 10～90 weight portions, it is preferably 20～90 weight portions, is further preferably 30～90 weight portions, more preferably 40～90 weight portions；The content of component B is 1～50 weight portion, it is preferred to 2～48 weight portions, is further preferably 3～46 weight portions, more preferably 4～44 weight portions；The content of component C is 1～15 weight portion, it is preferred to 1～14 weight portion, is further preferably 1～13 weight portion, more preferably 1～12 weight portion；The content of component D is 0～10 weight portion, it is preferred to 0～9 weight portion, is further preferably 0～8 weight portion, more preferably 0～7 weight portion；The content of auxiliary agent is 0～80 weight portion, it is preferred to 0～75 weight portion, more preferably 0～70 weight portion, is further preferably 0～65 weight portion。
9. the preparation method of the Black reactive dye composition according to any one of claim 1～8, it is characterised in that include the mixing of component A, component B, component C, optional component D and optional auxiliary agent being prepared in proportion；Preferably, described preparation method includes, in proportion by the dry powder of component A or slurry, the dry powder of component B or slurry, the dry powder of component C or slurry, the dry powder of optional component D or slurry and the mixing of optional auxiliary agent, being prepared by optional dry run；It is highly preferred that described preparation method includes the dry powder of component A, the dry powder of component B, the dry powder of component C, the dry powder of optional component D and the mixing of optional auxiliary agent being prepared in proportion；Or it is highly preferred that described preparation method includes, in proportion by the slurry of component A, the slurry of component B, the slurry of component C, the slurry of optional component D and the mixing of optional auxiliary agent, being prepared by optional dry run。
10. according to any one of claim 1～8 compositions as the purposes of reactive black dye；Preferably, described reactive black dye is for the printing and dyeing of fiber or its yarn fabric；It is highly preferred that described reactive black dye is for the printing and dyeing of Fypro, cellulose fibre, protein fibre or their yarn fabric；It is further preferred that described cellulose fibre includes cotton fiber, flaxen fiber, wool fiber and regenerated fiber；Further preferred, described printing and dyeing include dyeing and/or stamp, and described cotton fiber includes synthetic cotton, and described reactive black dye is used for synthetic cotton stamp。
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| CN201610153314.4A CN105694533A (en) | 2016-03-17 | 2016-03-17 | Black reactive dye composition and preparation method and application thereof |
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