CN102604426A - Compound disperse black azo dye - Google Patents
Compound disperse black azo dye Download PDFInfo
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- CN102604426A CN102604426A CN201210018403XA CN201210018403A CN102604426A CN 102604426 A CN102604426 A CN 102604426A CN 201210018403X A CN201210018403X A CN 201210018403XA CN 201210018403 A CN201210018403 A CN 201210018403A CN 102604426 A CN102604426 A CN 102604426A
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Abstract
The invention discloses a compound disperse black azo dye which mainly comprises one or more than one component A shown in the structural formula (I), one or more than one component B shown in the structural formula (II) and one or more than one component C shown in the structural formula (III). The compound disperse black azo dye can be used for dying in a form of macroparticle liquid and emulsifiable paste or powder and granules obtained after the compound disperse black azo dye is dried by a spray drying process. When the compound disperse black azo dye is used for printing and dyeing a polyester fiber material, a dark black died fabric with bright color and luster, good levelling property and dispersibility, good sun-proof and washable performances, perspiration resistance and other excellent performances can be obtained by adjusting the proportions of different components.
Description
One technical field
The present invention relates to a kind of Compositional type and disperse black azoic dyestuff and preparation method thereof, belong to the chemical material preparing technical field.
Two background technologies
Azoic dyestuff (azo dyes; The azo-group two ends connect one type of organic cpds of aryl) be fabric clothing most widely used one type of synthetic dyestuff in dyeing and printing process; The dyeing and the stamp that are used for multiple natural and synthon, also be used to paint, plastics, rubber etc. painted.Advantage such as that azoic dyestuff has is bright-colored, fastness is good, color and luster is various in style.Wherein black azo dispersion dyes purposes is very extensive, but often there are shortcomings such as depth, lifting force is not enough, and fastness is relatively poor in the dispersed black dye of one-component, during especially for textile printing, can cause white background staining serious.
Method about the public reported of improvement in performance has U.S. Pat 6159249, Korean Patent KR0156834, KR95029349, KR2000060609, Taiwan patent TW444047B, Chinese patent CN100503740C and Chinese patent CN1304490C etc.; The technical scheme that wherein adopts is the composite of one group of azoic dyestuff; The application performance of the composite black disperse dye that obtains makes moderate progress, but still has the shortcoming of level-dyeing property difference.
Three summary of the invention
The object of the present invention is to provide a profit to have the composite dispersed black dye of excellent dyeing behavior.
The technical solution that realizes the object of the invention is: a kind of Compositional type disperses black azoic dyestuff, mainly is made up of suc as formula the component C shown in (III) suc as formula the B component shown in (II) and one or more structures suc as formula the component A shown in (I), one or more structures one or more structures; Based on described component A, B component and component C, the quality percentage composition of component A is 30-90%, and the quality percentage composition of B component is 1-35%, the quality percentage composition 5-50% of component C; Here, the connotation of " mainly " is that this Compositional type disperses black azoic dyestuff to be constituted or mainly be made up of component A, B and C by component A, B and C, but also possibly contain other components that some auxiliary agent or a spot of impurity etc. do not influence its main tone;
In the formula (I): X
1, Y
1Be respectively nitro, cyanic acid or halogenic substituent;
Z
1For-NHCOR
3Or OR
4, R wherein
3, R
4Be C
1-C
4Alkyl;
R
1, R
2Be respectively C
1-C
4Alkyl, C
2-C
4Thiazolinyl, hydroxyl, cyanic acid or substituted alkyl, the substituting group of said substituted alkyl is-OCOR
5,-COOR
6, wherein, R
5, R
6Be C
1-C
4Alkyl;
W is hydrogen or C
1-C
4Alkoxyl group; When W is hydrogen and Z
1For-NHCOR
3The time, R
1, R
2Be merely C
1-C
4Substituted alkyl, the substituting group of said substituted alkyl is-OCOR
5Or-COOR
6, wherein, R
3, R
5, R
6Be C
1-C
4Alkyl;
In the formula (II): X
2, Y
2Be respectively nitro, cyanic acid or halogenic substituent;
Z
2Be C
1-C
4Alkyl or-NHCOR
7, R wherein
7Be C
1-C
4Alkyl;
R
9, R
10Be respectively C
1-C
4Alkyl, C
2H
4COOCH
3, C
2H
4COOC
2H
5Or cyanic acid;
In the formula (III): X
1, Y
1Be respectively nitro, cyanic acid or halogenic substituent;
Z
3Be hydrogen, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, hydroxyl or halogen;
R
11, R
12Be respectively C
1-C
4Alkyl or substituted alkyl, the substituting group of said substituted alkyl is cyanic acid or benzoyloxy.
Preferably, based on described component A, B component and component C, the quality percentage composition of component A is 15-85%, and the quality percentage composition of B component is 1-35%, and the quality percentage composition of component C is 5-50%.
More preferred, based on described component A, B component and component C, the quality percentage composition of component A is 15-80%, and the quality percentage composition of B component is 2-32%, and the quality percentage composition of component C is 5-40%.
Preferably, described a kind of Compositional type disperses black azoic dyestuff to be made up of component A, B component and component C, and the quality percentage composition of component A is 10-80%, and the quality percentage composition of B component is 2-32%, and the quality percentage composition of component C is 5-40%.
Said formula (I), formula (II) and (III) in, said halogen atom is respectively chlorine or bromine.
Said component A is preferably one of following or two or more mixture wherein:
Said B component is preferably one of following or two or more mixture wherein:
Said component C is preferably one of following or two or more mixture wherein:
More preferred; Described a kind of Compositional type disperses black azoic dyestuff to be made up of compound (I-1), compound (II-1) and compound (III-1); The mass percent of compound (I-1) is 15-80%; The mass percent of compound (II-1) is 2-12%, and the mass percent of compound (III-1) is 5-40%;
Because the singularity of dye industry is difficult to also there is no need to process pure article, can have some impurity usually in the preparation process, the black azoic dyestuff of composite dispersion of the present invention also allows to contain the physics impurity of a spot of moisture and trace when processing finished product.
When preparing the black azoic dyestuff of dispersion of the present invention, employed dye monomer: component A and B component can be synthesized by mode well known to those skilled in the art easily, and wherein component A and B component can prepare with reference to the method described in the patent EP563975.In addition, component A, B component and component C all can purchase the commercial goods.
Compositional type of the present invention disperses black azoic dyestuff, generally needs to add auxiliary agent during application and disperses.After mixing by above-mentioned proportioning like the azo cpd that structural formula (I), structural formula (II) and structural formula (III) is represented, in the presence of auxiliary agent, water or other wetting agent, carry out corpusculed with disintegrating apparatus such as sand mill or ball mills; Azo cpd that in addition also can structural formula (I), structural formula (II) and structural formula (III) is represented is carrying out mixing by above-mentioned proportioning after corpusculed is handled with disintegrating apparatus such as sand mill or ball mills respectively in the presence of auxiliary agent, water or other wetting agent.Usually, auxiliary agent is 0.8-5 with the ratio of azo cpd quality: 1.
Described auxiliary agent is Dispers ozoic dyestuff dispersion agent commonly used, diffusant etc. when composite, one of preferred following or wherein any several kinds mixture: anionic dispersing agents such as naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic formaldehyde condensation compound, sulfonated lignin.Particularly; Naphthalene sulfonic acidformaldehyde condensation product such as dispersing agent NNO; Alkyl naphthalene sulfonic acid formaldehyde condensation products such as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde); Benzyl naphthalene sulfonic formaldehyde condensation compound such as dispersing agent CNF etc., sulfonated lignin such as sodium lignosulfonate (like commercial dispersants Reax 83A, Reax 85A) etc.
Disperse black azo dyes based on Compositional type of the present invention, can adopt common dip method to dye, also can be used for direct printing.Wherein, common dip method is as carrying out pre-treatment with polyester textile, and after putting into dye vat and contaminating, to neutral, strand is done, and carries out reduction clearing again with cold wash, oven dry; Direct printing is as dying pre-treatment with fabric, and oven dry is finalized the design, and seal dispersed dye mill base evaporates again on printing machine, vapour steaming colour fixing, washing at last, stentering forming.
Compositional type of the present invention disperses black azoic dyestuff, the liquid state after can corpusculed, emulsifiable paste attitude or with spray-drying process etc. carry out dried powdery, graininess is supplied with dyeing.When disperseing black azo dye printing and dyeing Polyester Fibers,, can obtain to have that beautiful in colour, good dispersivity, level-dyeing property are excellent through the adjustment proportion among different with Compositional type of the present invention, the aterrimus dyeing and weaving thing of premium propertiess such as sun-proof, washable, perspiration resistance.
Four description of drawings
Accompanying drawing is the schema that a kind of Compositional type of the present invention disperses black azoic dyestuff preparation.
Five embodiments
Below in conjunction with specific embodiment the present invention is further described, these embodiment only are clear open the present invention, but protection scope of the present invention is not limited in this.
Embodiment 1
With the B component of the component A of 23.1 gram formulas (I-1), 9.4 gram formulas (II-1), the component C of 8.0 gram formulas (III-1), the sodium lignosulfonate of 85 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.This dyestuff can provide fabric each item fastness ability good aterrimus.
Embodiment 2
With the B component of the component A of 23.1 gram formulas (I-1), 9.4 gram formulas (II-1), the component C of 8.0 gram formulas (III-1), the Dispersant MF of 85 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.This dyestuff can provide fabric each item fastness ability good aterrimus.
Embodiment 3
With the B component of the component A of 23.1 gram formulas (I-1), 9.4 gram formulas (II-1), the component C of 8.0 gram formulas (III-1), the dispersing agent CNF of 85 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 4
With the B component of the component A of 22.1 gram formulas (I-1) and 2 gram formulas (I-7), 9.4 gram formulas (II-1), the component C of 8.0 gram formulas (III-1), the dispersing agent CNF of 85 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 5
With the B component of the component A of 22.1 gram formulas (I-1) and 2 gram formulas (I-3), 9.4 gram formulas (II-1), the component C of 8.0 gram formulas (III-1), the Dispersant MF of 85 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 6
With the B component of the component A of 23.1 gram formulas (I-1), 9.0 gram formulas (II-1), the component C of 8.0 gram formulas (III-1), the Dispersant MF of 90 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 7
With the component C of B component, 6.0 gram formulas (III-1) and the 2 gram formulas (III-2) of the component A of 23.1 gram formulas (I-1), 9.4 gram formulas (II-1), the xylogen 83A of 95 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 8
With the B component of the component A of 22.1 gram formulas (I-1) and 2 gram formulas (I-6), 9.4 gram formulas (II-1), the component C of 8.0 gram formulas (III-1), the Dispersant MF of 85 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 9
With the B component of the component A of 22.1 gram formulas (I-1), 9.0 gram formulas (II-1), the component C of 9.0 gram formulas (III-1), the Dispersant MF of 85 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 10
With the B component of the component A of 24.1 gram formulas (I-1), 9.5 gram formulas (II-1), the component C of 7.5 gram formulas (III-1), the Dispersant MF of 90 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 11
With the B component of the component A of 45.0 gram formulas (I-2), 1.5 gram formulas (II-3), the component C of 3.5 gram formulas (III-2), the dispersing agent NNO of 90 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 12
With the B component of the component A of 20.0 gram formulas (I-4), 10.0 gram formulas (II-6), the component C of 35.0 gram formulas (III-3), the dispersing agent CNF of 85 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 13
With the B component of component A, 2.5 gram formulas (II-1) and the 5.5 gram formulas (II-3) of 23.0 gram formulas (I-1), the component C of 9.0 gram formulas (III-1), the xylogen 83A of 32 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 14
With the B component of the component A of 22.1 gram formulas (I-12) and 2 gram formulas (I-8), 5.0 gram formulas (II-1), the component C of 12.0 gram formulas (III-4), the dispersing agent NNO of 70 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 15
With the B component of the component A of 20.0 gram formulas (I-9), 4.0 gram formulas (II-2), the component C of 12.0 gram formulas (III-1), the Dispersant MF of 180 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 16
With the B component of component A, 3.0 gram formulas (II-1) and the 3.7 gram formulas (II-4) of 35.0 gram formulas (I-10), the component C of 3.0 gram formulas (III-4), the xylogen 83A of 140 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 17
With the B component of the component A of 35.0 gram formulas (I-11), 7.0 gram formulas (II-5), the component C of 11.0 gram formulas (III-4), the dispersing agent NNO of 140 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 18
With the B component of component A, 5.0 gram formulas (II-5) and the 2.5 gram formulas (II-8) of 35.0 gram formulas (I-13), the component C of 12.0 gram formulas (III-4), the dispersing agent NNO of 110 grams, after adding water and mixing, to grind with shredder and to disperse, spraying drying gets product.
Embodiment 19
With the B component of component A, 2.5 gram formulas (II-5), 2.5 gram formulas (II-7) and the 2.5 gram formulas (II-9) of 25.0 gram formulas (I-4) and 10.0 gram formulas (I-6), the component C of 12.0 gram formulas (III-4), the dispersing agent NNO of 110 grams; After adding the water mixing; Grind dispersion with shredder, spraying drying gets product.
Embodiment 20
Component C, the dispersing agent NNO of 50 grams and the Dispersant MF of 30 grams with B component, 6.0 gram formulas (III-1) and the 2.0 gram formulas (III-2) of component A, 2.5 gram formulas (II-1) and the 2.5 gram formulas (II-4) of 25.0 gram formulas (I-10); After adding the water mixing; Grind dispersion with shredder; Spraying drying gets product.
Embodiment 21
Respectively get 0.5 gram and implement the dispersed black dye that row 1-20 makes and be dispersed in 500 ml waters, mixes with 60 milliliters water after drawing 20 milliliters, use acetate accent dye bath PH is 5; Putting into 2 gram trevira when being warming up to 60 ℃ dyes; In 45 minutes, be warming up to 130 ℃, be incubated 60 minutes, take out under dyeing finishes to be cooled to 90 ℃ and dye appearance; Cold water cleans and reduction clearing, oven dry.Observe an appearance cloth coloured light, adopt GB GB/T3920-1997, GB/T3921-1997, GB/T3922-1997, GB/T8427-1998 to test fastness to rubbing >=4 grade, fastness to washing >=4-5 level, fastness to perspiration >=4-5 level, sun-resistant fastness >=6 grade respectively.
Embodiment 22
Earlier, remove the finish and the slurry that add in the weaving process, and carry out heat setting type the polyester piece good pre-treatment of dyeing; Seal dispersed dye mill base, control PH4-6.5 on printing machine, temperature 160-185 ℃ direct printing 4-15 minute, the high temperature vapour steaming colour fixing; Washing then, oven dry, stentering forming.Wherein, dye paste 100 grams are formed by the sodium alginate paste modulation of black 6 grams of above-mentioned dispersion, urea 1 gram, nitrobenzene sodium sulfonate 0.5 gram, SODIUM PHOSPHATE, MONOBASIC 0.5 gram, p-phenyl phenol 2 grams and 90 grams.According to implementing its each item colour fastness excellent property of method test described in the row 21.
Claims (12)
1. a Compositional type disperses black azoic dyestuff, it is characterized in that: be made up of suc as formula the component C shown in (III) suc as formula the B component shown in (II) and one or more structural formulas suc as formula the component A shown in (I), one or more structural formulas one or more structural formulas; Wherein the quality percentage composition of component A is 15-85%, and the quality percentage composition of B component is 1-35%, and the quality percentage composition of component C is 5-50%;
In the formula (I): X
1, Y
1Be respectively nitro, cyanic acid or halogenic substituent;
Z
1For-NHCOR
3Or OR
4, R wherein
3, R
4Be C
1-C
4Alkyl;
R
1, R
2Be respectively C
1-C
4Alkyl, C
2-C
4Thiazolinyl, hydroxyl, cyanic acid or substituted alkyl, the substituting group of said substituted alkyl is-OCOR
5,-COOR
6, wherein, R
5, R
6Be C
1-C
4Alkyl;
W is hydrogen or C
1-C
4Alkoxyl group; When W is hydrogen and Z
1For-NHCOR
3The time, R
1, R
2Be merely C
1-C
4Substituted alkyl, the substituting group of said substituted alkyl is-OCOR
5Or-COOR
6, wherein, R
3, R
5, R
6Be C
1-C
4Alkyl;
In the formula (II): X
2, Y
2Be respectively nitro, cyanic acid or halogenic substituent;
Z
2Be C
1-C
4Alkyl or-NHCOR
7, R wherein
7Be C
1-C
4Alkyl;
R
9, R
10Be respectively C
1-C
4Alkyl, C
2H
4COOCH
3, C
2H
4COOC
2H
5Or cyanic acid;
In the formula (III): X
1, Y
1Be respectively nitro, cyanic acid or halogenic substituent;
Z
3Be hydrogen, C
1-C
4Alkyl, C
1-C
4Alkoxyl group, hydroxyl or halogen;
R
11, R
12Be respectively C
1-C
4Alkyl or substituted alkyl, the substituting group of said substituted alkyl is cyanic acid or benzoyloxy.
2. a kind of Compositional type according to claim 1 disperses black azoic dyestuff; It is characterized in that: based on described component A, B component and component C; Wherein the quality percentage composition of component A is 15-85%, and the quality percentage composition of B component is 1-35%, and the quality percentage composition of component C is 5-50%.
3. a kind of Compositional type according to claim 2 disperses black azoic dyestuff; It is characterized in that: based on described component A, B component and component C; Wherein the quality percentage composition of component A is 15-80%, and the quality percentage composition of B component is 2-32%, and the quality percentage composition of component C is 5-40%.
4. a kind of Compositional type according to claim 1 disperses black azoic dyestuff; It is characterized in that: said dyestuff is made up of component A, B component and component C; Wherein the quality percentage composition of component A is 15-80%; The quality percentage composition of B component is 2-32%, and the quality percentage composition of component C is 5-40%.
5. a kind of Compositional type according to claim 1 disperses black azoic dyestuff, it is characterized in that: formula (I), (II) and (III) in, said halogen atom is respectively chlorine or bromine.
6. disperse black azoic dyestuff according to the described a kind of Compositional type of one of claim 1-5, it is characterized in that: said component A is one of following or two or more mixture wherein:
7. disperse black azoic dyestuff according to the described a kind of Compositional type of one of claim 1-5, it is characterized in that: said B component is one of following or two or more mixture wherein:
8. disperse black azoic dyestuff according to the described a kind of Compositional type of one of claim 1-5, it is characterized in that: said component C is one of following or two or more mixture wherein:
9. a kind of Compositional type according to claim 1 disperses black azoic dyestuff; It is characterized in that: said dyestuff is made up of compound (I-1), compound (II-1) and compound (III-1); The mass percent of compound (I-1) is 15-80%; The mass percent of compound (II-1) is 2-32%, and the mass percent of compound (III-1) is 5-40%;
10. a Compositional type disperses black azoic dyestuff, and it contains the described azo cpd of claim 1 of 10-60% mass percent and the dispersion agent of 40-90% mass percent.
11. the production method based on the described dye preparations of claim 10 is characterized in that, in the presence of dispersant, the azo-compound of claim 1 is ground in water respectively, mixes then, or mixes and dry.
12. the working method of dye preparations according to claim 10 is characterized in that, in the presence of dispersion agent, the azo cpd of claim 1 is ground in water, carries out drying then.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210018403XA CN102604426A (en) | 2012-01-20 | 2012-01-20 | Compound disperse black azo dye |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210018403XA CN102604426A (en) | 2012-01-20 | 2012-01-20 | Compound disperse black azo dye |
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|---|---|
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|---|---|---|---|
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103275512A (en) * | 2013-05-28 | 2013-09-04 | 江苏之江化工有限公司 | Blue monoazo dye |
| CN104087010A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Disperse dye mixture |
| CN104087017A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Preparation method of orange disperse dye |
| CN105602278A (en) * | 2016-01-28 | 2016-05-25 | 俞杏英 | Blue disperse dye monomeric compound and preparation method and application thereof |
| CN106590027A (en) * | 2016-12-30 | 2017-04-26 | 浙江闰土研究院有限公司 | Disperse dye composition, and preparation method and application thereof |
| CN106928748A (en) * | 2017-03-10 | 2017-07-07 | 温州德业化工有限公司 | A kind of disperse dyes |
| CN108929566A (en) * | 2018-08-07 | 2018-12-04 | 江苏之江化工有限公司 | A kind of high washing fastness dispersed black dye mixture |
| CN109401359A (en) * | 2018-10-26 | 2019-03-01 | 浙江龙盛集团股份有限公司 | It is a kind of blue to black disperse dye composition and dye preparations |
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| CN104087010A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Disperse dye mixture |
| CN104087017A (en) * | 2013-05-16 | 2014-10-08 | 上海安诺其纺织化工股份有限公司 | Preparation method of orange disperse dye |
| CN103275512A (en) * | 2013-05-28 | 2013-09-04 | 江苏之江化工有限公司 | Blue monoazo dye |
| CN105602278A (en) * | 2016-01-28 | 2016-05-25 | 俞杏英 | Blue disperse dye monomeric compound and preparation method and application thereof |
| CN106590027A (en) * | 2016-12-30 | 2017-04-26 | 浙江闰土研究院有限公司 | Disperse dye composition, and preparation method and application thereof |
| CN106590027B (en) * | 2016-12-30 | 2020-05-01 | 浙江闰土研究院有限公司 | Disperse dye composition and preparation method and application thereof |
| CN106928748A (en) * | 2017-03-10 | 2017-07-07 | 温州德业化工有限公司 | A kind of disperse dyes |
| CN106928748B (en) * | 2017-03-10 | 2019-03-15 | 绍兴金祥惠纺织印染有限公司 | A kind of disperse dyes |
| CN108929566A (en) * | 2018-08-07 | 2018-12-04 | 江苏之江化工有限公司 | A kind of high washing fastness dispersed black dye mixture |
| CN109401359A (en) * | 2018-10-26 | 2019-03-01 | 浙江龙盛集团股份有限公司 | It is a kind of blue to black disperse dye composition and dye preparations |
| CN109401359B (en) * | 2018-10-26 | 2020-06-16 | 浙江龙盛集团股份有限公司 | Blue-to-black disperse dye composition and dye product |
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