CN105778561A - Black active dye composition and preparation method and use thereof - Google Patents

Black active dye composition and preparation method and use thereof Download PDF

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Publication number
CN105778561A
CN105778561A CN201610153397.7A CN201610153397A CN105778561A CN 105778561 A CN105778561 A CN 105778561A CN 201610153397 A CN201610153397 A CN 201610153397A CN 105778561 A CN105778561 A CN 105778561A
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component
black
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weight portions
dye composition
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CN105778561B (en
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杨国旗
柳长江
陆军
方岩波
陶莉莉
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Zhejiang Ruihua Chemical Coltd
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Zhejiang Ruihua Chemical Coltd
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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
    • C09B67/004Mixtures of two or more 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
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046Mixtures of two or more azo dyes
    • C09B67/0047Mixtures of two or more reactive azo dyes
    • C09B67/005Mixtures of two or more reactive azo dyes all the reactive groups being not directly attached to a heterocyclic system
    • 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
    • D06P1/384General 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
    • 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
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/14Wool
    • D06P3/148Wool 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
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/24Polyamides; Polyurethanes
    • D06P3/248Polyamides; Polyurethanes 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
    • D06P3/666Natural or regenerated cellulose using reactive dyes reactive group not directly attached to heterocyclic group

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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

Black active dye composition and a preparation method and use thereof are provided. The black active 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 an optional acid. The black active dye composition is suitable for dyeing various fiber materials, is high in color fixing rate and excellent in color fastness and thereby has excellent comprehensive performances.

Description

A kind of Black reactive dye composition and its production and use
Technical field
The present invention relates to reactive dyestuff field, in particular it 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.Currently, the yield of black and active dye accounts for more than half of whole reactive dye yield, and therefore black and active dye exploitation is always up the focus of dye industry.The Black reactive dye composition of prior art such as CN1730566A, CN1687244A, it is difficult to have concurrently the combination properties such as strong degree of fixation, good rub resistance, water-fastness and colour fastness to perspiration, extremely lack the black and active dye of high comprehensive performance, therefore, it is badly in need of developing the black and active dye kind that a kind of performance is better, can meet above-mentioned characteristic requirements simultaneously.
Summary of the invention
Various performance indications after fiber printing and dyeing are difficult to reach the defect that people require by the present invention in order to overcome existing black and active dye to exist, there is provided a kind of degree of fixation high, the Black reactive dye composition that every color fastness such as rub resistance, water-fast and perspiration resistance are excellent, and the preparation method of said composition and purposes.
A first aspect of the present invention, a kind of Black reactive dye composition is provided, it is characterized in that, including the component A of one or more compounds composition in formula (I) compound, the component C of one or more compounds composition and optionally auxiliary agent in the component B of one or more compounds composition, optional formula (III) compound in formula (II) compound:
Wherein, M1、M2、M3It is each independently hydrogen, potassium, sodium, lithium or ammonium;R1、R2It is each independently-CH=CH2Or-C2H4OSO3M1, R3、R6It is each independently (C1~C4) alkyl or (C1~C4) alkoxyl, R4、R5Wherein there is one for-CH=CH2, another be-C2H4OSO3M2, R7For-CH=CH2Or-C2H4OSO3M3
Preferably, above-mentioned Black reactive dye composition, wherein, described component A is selected from one or more in formula (I-1)~(I-10) compound.
Preferably, above-mentioned Black reactive dye composition, it is characterised in that described component B is selected from one or more in formula (II-1)~(II-6) compound.
Preferably, above-mentioned Black reactive dye composition, it is characterised in that described component C is selected from one or more in formula (III-1)~(III-9) 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 Black reactive dye composition, it is characterised in that described auxiliary agent at least one in dispersant, filler and 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.
Preferably, in above-mentioned Black reactive dye composition, the content of 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;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 0~50 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 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 second aspect of the invention, it is provided that the preparation method of above-mentioned Black reactive dye composition, including being mixed in proportion prepared by component A, component B, optional component C and optional auxiliary agent.
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 optional component C or slurry and the mixing of optional auxiliary agent, being prepared by optional dry run.
More preferably, described preparation method includes the dry powder of component A, the dry powder of component B, the dry powder of optional component C and the mixing of optional auxiliary agent being prepared in proportion, or more preferably, described preparation method includes, in proportion by the slurry of component A, the slurry of component B, the slurry of optional component C and the mixing of optional auxiliary agent, being prepared 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 present invention is to carrying out described dry equipment also without special restriction, it is preferred to use spray tower, drying room or flash dryer etc. are dried and obtain granular or powdery Black reactive dye composition.
The third aspect of the invention, it is provided that above-mentioned Black reactive dye composition is as the purposes of reactive black dye.
Preferably, in above-mentioned purposes, described reactive black dye is for the printing and dyeing of fiber or its yarn fabric.
Preferably, in above-mentioned purposes, described reactive black dye is for the printing and dyeing of Fypro, cellulose fibre, protein fibre or their yarn fabric;It is highly 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.
The Black reactive dye composition of the present invention, has the advantage that degree of fixation is high, and dye-uptake is high, people's cotton good hand touch, and every color fastness such as rub resistance, water-fastness and perspiration resistance is excellent.The Black reactive dye composition of the present invention is suitable for stamp or the dyeing of cellulosic fibre material, such as stamp or the dyeing of cotton, fiber crops, regenerated fiber and yarn fabric thereof, is also applied for stamp or the dyeing of Fypro, protein fibre and yarn fabric thereof in addition.
Detailed description of the invention
The present invention is described in detail by the following examples.It should be appreciated that being merely cited for property of embodiments herein the present invention will be described, be not used to limit the invention.
Formula (II-1) compound used in following embodiment 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;
null(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,Then 0 DEG C-10 DEG C are cooled to,It is slowly added into liquid caustic soda,Maintain temperature 0 DEG C-10 DEG C,Maintain pH10~13,React 1~2 hour and stablize to pH,PH to 4~7 is adjusted back with hydrochloric acid,Formula (II-1) compound is prepared after spray drying.
Additionally, compound shown in the formula (I-1) that uses in following embodiment, (III-1), (III-7), (IV), (V) can synthesize by mode well known to those skilled in the art easily, as prepared by diazotising conventionally, couling process, it is possible to adopt commercially available prod.
Embodiment 1
The component A of 60 weight portion formulas (I-1), the component B of 20 weight portion formulas (II-1) and the component C of 20 weight portion formulas (III-1) are carried out dry powder blend by blender, obtain compositions 1, using described compositions as reactive black dye, cotton dyeing can be become black.
Embodiment 2
The component A of 60 weight portion formulas (I-1), the component B of 20 weight portion formulas (II-1) and the component C of 20 weight portion formulas (III-7) are carried out dry powder blend by blender, obtain compositions 2, using described compositions as reactive black dye, cotton dyeing can be become black.
Embodiment 3
The component A of 40 weight portion formulas (I-1), the component B of 20 weight portion formulas (II-1) and the component C of 20 weight portion formulas (III-1) and 20 weight portion formulas (III-7) are carried out dry powder blend by blender, obtain compositions 3, using described compositions as reactive black dye, cotton dyeing can be become black.
Embodiment 4
The component B of the component A of 56 weight portion formulas (I-1), 44 weight portion formulas (II-1) is carried out dry powder blend by blender, obtains compositions 4, using described compositions as reactive black dye, cotton dyeing can be become black.
Comparative example 1
The component C of the component A of 79.5 weight portion formulas (I-1) and 20.5 weight portion formulas (III-1) is carried out dry powder blend by blending machine, obtains compositions 5, using described compositions as reactive black dye, cotton dyeing can be become black.
Comparative example 2
The component A of 76.9 weight portion formulas (I-1), the compound as shown in formula (IV) of 21.6 weight and the Matrii Sulfas Exsiccatus of 1.5 weight portions are carried out dry powder blend by blender, obtain compositions 6, using described compositions as reactive black dye, cotton dyeing can be become black.
Comparative example 3
Compound shown in the component A of 72.5 weight portion formulas (I-1), the component C of 18 weight portion formulas (III-1) and 9.5 weight portion formulas (V) is carried out dry powder blend by blending machine, obtain compositions 7, using described compositions as reactive black dye, cotton dyeing can be become black.
Comparative example 4
The Matrii Sulfas Exsiccatus of the compound shown in the component A of 60.9 weight portion formulas (I-6), 13 weight portion formulas (III-1), the component C of 8.7 weight portion formulas (III-7), 4.4 weight portion formulas (V) and 13 weight portions is carried out dry powder blend by blender, obtain Black reactive dye composition 6, using described compositions as reactive black dye, cotton dyeing is become black.
Dye test
To the Black reactive dye composition 1-4 obtained by embodiment 1-4 and the comparative example 1-4 each 2g of the Black reactive dye composition 5-8 obtained 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 again 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.Respectively according to GB/T2391-2014, GB/T3920-2008, GB/T3921-2008 and GB/T3922-2013 method carry out testing its degree of fixation, rub resistance, water-fastness and colour fastness to perspiration, 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 4 (component I-1+ component II-1) and comparative example 2 (component I-1+ component IV) 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 compositions of the present invention, when being applied to dye as reactive black dye, degree of fixation is high, and every fastness properties is excellent, hence it is evident that be better than the similar competing product in market;From table two, table three, when intensity under standard control is 100%, the compositions of the present invention, when being applied to dye as reactive black dye, cost performance is compared height, can obtain from the data above, the present invention often produces 1 ton of dyestuff and can economize in raw materials cost 462.8 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 (IV), thus has comparatively excellent combination property.
The preferred embodiment of the present invention described in detail above; but, the present invention is not limited to the detail in above-mentioned embodiment, in the technology concept of the present invention; technical scheme can being carried out multiple simple variant, these simple variant belong to protection scope of the present invention.

Claims (10)

1. a Black reactive dye composition, it is characterized in that, including the component A of one or more compounds composition in formula (I) compound, the component C of one or more compounds composition and optionally auxiliary agent in the component B of one or more compounds composition, optional formula (III) compound in formula (II) compound:
Wherein, M1、M2、M3It is each independently hydrogen, potassium, sodium, lithium or ammonium;R1、R2It is each independently-CH=CH2Or-C2H4OSO3M1, R3、R6It is each independently (C1~C4) alkyl or (C1~C4) alkoxyl, R4、R5Wherein there is one for-CH=CH2, another be-C2H4OSO3M2, R7For-CH=CH2Or-C2H4OSO3M3
2. Black reactive dye composition according to claim 1, it is characterised in that described component A is selected from one or more in formula (I-1)~(I-10) compound.
3. Black reactive dye composition according to claim 1 and 2, it is characterised in that described component B is selected from one or more in formula (II-1)~(II-6) compound.
4. the Black reactive dye composition according to any one of claim 1-3, it is characterised in that described component C is selected from one or more in formula (III-1)~(III-9) compound.
5. the Black reactive dye composition according to any one of claim 1-4, it is characterised in that described auxiliary agent at least one in dispersant, filler and 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.
6. the Black reactive dye composition according to any one of claim 1-5, 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 0~50 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 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.
7. the preparation method of the Black reactive dye composition according to any one of claim 1-6, including being mixed in proportion prepared by component A, component B, optional component C and optional auxiliary agent;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 optional component C or slurry and the mixing of optional auxiliary agent, being prepared by optional dry run;More preferably, described preparation method includes the dry powder of component A, the dry powder of component B, the dry powder of optional component C and the mixing of optional auxiliary agent being prepared in proportion, or more preferably, described preparation method includes, in proportion by the slurry of component A, the slurry of component B, the slurry of optional component C and the mixing of optional auxiliary agent, being prepared by optional dry run.
8. according to any one of claim 1-7 compositions as the purposes of reactive black dye.
9. purposes according to claim 8, it is characterised in that described reactive black dye is for the printing and dyeing of fiber or its yarn fabric.
10. purposes according to claim 8 or claim 9, it is characterised in that described reactive black dye is for the printing and dyeing of Fypro, cellulose fibre, protein fibre or their yarn fabric;It is highly 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.
CN201610153397.7A 2016-03-17 2016-03-17 A kind of Black reactive dye composition and its production and use Active CN105778561B (en)

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Publication number Priority date Publication date Assignee Title
CN106566281A (en) * 2016-09-14 2017-04-19 浙江科永化工有限公司 Reactive navy blue-to-black dye composition and dye product
CN106948191A (en) * 2017-03-30 2017-07-14 绍兴市天基印刷材料厂 The black printed slurries of SM
CN112679987A (en) * 2020-12-26 2021-04-20 浙江科永化工有限公司 Active navy blue to black dye composition and dye product
WO2022134535A1 (en) * 2020-12-26 2022-06-30 浙江科永化工有限公司 Active navy-blue-to-black dye composition and dye article
WO2022134532A1 (en) * 2020-12-26 2022-06-30 浙江科永化工有限公司 Reactive dye compound, preparation method therefor and use thereof

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WO2013021352A2 (en) * 2011-08-10 2013-02-14 Colourtex Industries Limited Black mixtures of fibre reactive azo reactive dyestuffs
CN103013175A (en) * 2013-01-05 2013-04-03 江苏德美科化工有限公司 Reactive dye mixture and applications thereof
CN104059387A (en) * 2014-07-10 2014-09-24 浙江瑞华化工有限公司 Compound black reactive dye composition, and applications thereof and fiber or fiber textile made thereby
CN104073024A (en) * 2014-07-10 2014-10-01 浙江瑞华化工有限公司 Black active dye composition and application thereof

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Publication number Priority date Publication date Assignee Title
CN1745147A (en) * 2003-02-05 2006-03-08 西巴特殊化学品控股有限公司 Mixtures of reactive dyes and their use
CN101117449A (en) * 2007-09-04 2008-02-06 大连理工大学 High-concentration composite reactive dye
WO2013021352A2 (en) * 2011-08-10 2013-02-14 Colourtex Industries Limited Black mixtures of fibre reactive azo reactive dyestuffs
CN103013175A (en) * 2013-01-05 2013-04-03 江苏德美科化工有限公司 Reactive dye mixture and applications thereof
CN104059387A (en) * 2014-07-10 2014-09-24 浙江瑞华化工有限公司 Compound black reactive dye composition, and applications thereof and fiber or fiber textile made thereby
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106566281A (en) * 2016-09-14 2017-04-19 浙江科永化工有限公司 Reactive navy blue-to-black dye composition and dye product
CN106948191A (en) * 2017-03-30 2017-07-14 绍兴市天基印刷材料厂 The black printed slurries of SM
CN112679987A (en) * 2020-12-26 2021-04-20 浙江科永化工有限公司 Active navy blue to black dye composition and dye product
WO2022134533A1 (en) * 2020-12-26 2022-06-30 浙江科永化工有限公司 Active navy blue-to-black dye composition and dye product
WO2022134535A1 (en) * 2020-12-26 2022-06-30 浙江科永化工有限公司 Active navy-blue-to-black dye composition and dye article
WO2022134532A1 (en) * 2020-12-26 2022-06-30 浙江科永化工有限公司 Reactive dye compound, preparation method therefor and use thereof

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