CN106065199B - It is a kind of suitable for active orange of low temperature dyeing and preparation method thereof - Google Patents
It is a kind of suitable for active orange of low temperature dyeing and preparation method thereof Download PDFInfo
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- CN106065199B CN106065199B CN201610391752.4A CN201610391752A CN106065199B CN 106065199 B CN106065199 B CN 106065199B CN 201610391752 A CN201610391752 A CN 201610391752A CN 106065199 B CN106065199 B CN 106065199B
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- acid
- aniline
- dyeing
- preparation
- active orange
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Classifications
-
- 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/08—Disazo dyes in which the coupling component is a hydroxy-amino compound
- C09B33/10—Disazo dyes in which the coupling component is a hydroxy-amino compound in which the coupling component is an amino naphthol
-
- 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8219—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and amide groups
Abstract
The invention discloses a kind of suitable for active orange of low temperature dyeing and preparation method thereof.The structural formula of the active orange is as shown in Equation 1:In the formula 1 of formula 1, R1And R2One of them be NH2, another is H.The active orange of the present invention can be applied to low temperature dyeing(40 DEG C or so), reactivity worth is stable, and good level-dyeing property, tinctorial yield is high, easily cleans, and reduces energy consumption.
Description
Technical field
The invention belongs to Dyestuff synthesis field, and in particular to a kind of active orange and its system suitable for low temperature dyeing
Preparation Method.
Background technology
Environmental pollution and protection have become today's society significant problem, and dye industry is then faced with baptism, society
The step that can advance can not stop, and enterprise wants length and inspires exhibition in the new situation, and product quality must reach a new height.
Existing dyestuff, synthesis technique is complicated, and produces all multi-pollutants, is thrown into environment and pollutes.Moreover, mesh
Preceding conventional dyestuff, its dyeing temperature is at 60-70 DEG C, to reach higher tinctorial yield and degree of fixation.Dyeing temperature height will necessarily
Increase the energy consumption of dyeing.
The content of the invention
In order to reduce environmental pollution, the active orange responded in national energy-saving emission reduction policy, the present invention is broken the normal procedure
Dyed using lower temperature, more stable compared with traditional handicraft product reactivity worth, production cost is cheaper, solve traditional orange work
Property the problems such as dyestuff level-dyeing property is poor, raffinate is more, with production cost is low, reactivity worth stabilization, good level-dyeing property, degree of fixation it is high, it is molten
Xie Du is good, the advantages of quantity of wastewater effluent is few.
The active orange suitable for low temperature dyeing of the present invention, it is adaptable to low temperature dyeing, reactivity worth is stable, level dyeing
Property is good, and 5 grades of light fastness, fastness to wet rubbing reach 4 grades, and degree of fixation reaches more than 87%, and enhancing rate is up to 10%, dyeing residual liquid
It is few, belong to low temperature environment-friendly energy-saving dyestuff, meet national energy-saving emission reduction policy.This product is except for traditional cellulose
Beyond stock-dye, continuous knot dyeing, discharge printing and brocade/cotton one-bath dyeing are more suitable for.
The active orange suitable for low temperature dyeing that the present invention is provided, structural formula is as shown in Equation 1:
Formula 1
In formula 1, R1And R2One of them be-NH2, another is H.
The present invention also provides the preparation method of above-mentioned active orange, comprises the following steps:
1)By aniline 2,5- disulfonic acids carry out diazo-reaction with hydrochloric acid and sodium nitrite in aqueous solution, obtain aniline 2, and 5- is double
Sulfonic acid diazonium compound;
2)J acid or γ acid are mixed with water, after mashing dissolving, and regulation pH value is 6 ~ 7.5, standby after clarification;
3)Step 1)Obtained aniline 2,5- disulfonic acids diazonium compound and step 2)Obtained J acid or γ aqueous acids enters
Row reacts to obtain a conjugates;
4)Sulfonation para-ester carries out diazo-reaction with hydrochloric acid and sodium nitrite in aqueous solution, obtains sulfonation para-ester diazonium
Thing;
5)Step 4)Obtained sulfonation para-ester diazonium thing adds step 3)In an obtained conjugates react
To secondary conjugates, filter, be drying to obtain.
Preferably, step 1)For aniline 2,0-3 DEG C is cooled to after adding hydrochloric acid, stirring in 5- disulfonic acids, nitrous is added
Acid sodium aqueous solution, in 3-7 DEG C of reaction, obtains aniline 2,5- disulfonic acid diazonium compounds.
Preferably, step 2)In pH value is adjusted as 6 ~ 7.5 using sodium hydroxide or sodium acid carbonate.
Preferably, step 3)For by step 1)Obtained aniline 2,5- disulfonic acid diazonium compounds are added to step 2)Obtain
J acid or γ aqueous acids in, control 0-3 DEG C of temperature, with sodium bicarbonate dry powder adjust pH=3 ~ 4, progress react once to be coupled
Thing.
Preferably, step 4)Added for sulfonation para-ester after being stirred in hydrochloric acid, be cooled to 0-5 DEG C, add natrium nitrosum
The aqueous solution, in 3-7 DEG C of reaction, obtains sulfonation para-ester diazonium thing.
Preferably, step 5)For by step 4)Obtained sulfonation para-ester diazonium thing adds step 3)Obtained once coupling
In thing, pH=6.5 ~ 7.5 are adjusted with sodium bicarbonate dry powder, 10-15 DEG C of temperature is controlled, reaction obtains secondary conjugates, and filtering, drying are
.
Preferably, aniline 2,5- disulfonic acids:J acid or γ acid:Mass ratio=250 ~ 260 of sulfonation para-ester:234~241:
360~380。
The present invention also provides the application of the above-mentioned active orange suitable for low temperature dyeing, the active orange
For cellulose dyeing, continuous knot dyeing, discharge, stamp and brocade/cotton One Bath Dyeing Process.
Preferably, the dyeing temperature of the active orange is 35 ~ 45 DEG C.
The present invention has the characteristics that suitable for the active orange of low temperature dyeing:
1)Production technology cleaning, environmental protection:Synthesis uses spray drying after finishing, and quantity of wastewater effluent is few.
2)Low temperature dyeing(40 DEG C or so), reactivity worth is stable, and good level-dyeing property, tinctorial yield is high, easily cleans, and reduces energy consumption.
3)Solubility is high, and multiple sulfonic acid groups are contained in this dye structure, can be widely used in cellulose dyeing,
Continuous knot dyeing and discharge, resisting printing.
4)It is adapted to bright and beautiful cotton One Bath Dyeing Process.
5)Enhancing rate is good:Enhancing rate reaches 10%.
6)Degree of fixation is high:This dye fixing rate is up to 87%, and low temperature dyeing raffinate is few, can mitigate dyeing environmental protection pressure
Power, meets national energy-saving emission reduction policy.
Embodiment
The present invention is further explained below by some preferred embodiments, these embodiments are only to the present invention
Explain, rather than any limitation is formed to protection scope of the present invention.
Raw material used is that in the market is common in dyestuff preparation method following examples 1-5 of the present invention, these embodiments
Industrial chemicals.
Raw material number in following examples each means mass fraction.
Embodiment 1
1)Aniline 2,5- disulfonic acid diazonium:54 parts of hydrochloric acid are added in 251 parts of aniline 2,5- disulfonic acids(In terms of hydrogen chloride)
It is on the rocks after stirring 3 hours to cool in 0-3 DEG C, add 72 parts of sub- sodium(Being made into the aqueous solution that mass percent concentration is 30% makes
With), aniline 2,5- disulfonic acid diazonium compounds are obtained within 4 hours in 3-7 DEG C of maintenance reaction;
2)J acid dissolvings:236 parts of J acid are added to the water, at 15-20 DEG C, mashing is dissolved for 1 hour, then molten with sodium hydroxide
Liquid adjusts pH value to be 6.5;
3)Once it is coupled:Aniline 2,5- disulfonic acid diazonium compounds are added in J acid solutions, control 0-3 DEG C of temperature, reaction
4 hours, a conjugates are obtained after adjusting pH=3.5, reaction completely with sodium bicarbonate dry powder;
4)Secondary diazonium:361 parts of sulfonation para-esters 43 parts of hydrochloric acid of addition are on the rocks after stirring 2 hours to cool in 0-5 DEG C, then adds
Enter 69 parts of sub- sodium(It is made into 30% solution), sulfonation para-ester diazonium thing is obtained within 3 hours in 3-7 DEG C of maintenance reaction;;
5)Secondary coupling:Sulfonation para-ester diazonium thing is added in a conjugates, pH=7.0, control are adjusted with sodium bicarbonate dry powder
10-15 DEG C of temperature processed, carries out reaction 6 hours, with profit circle method detection terminal, and terminal is to obtaining secondary conjugates, after reaction is complete
It is filtered and carries out spray drying again and packs to obtain product(1), it has following structure:
(1)
It is computed, yield is 97%, purity is 88%.
Embodiment 2
1)Aniline 2,5- disulfonic acid diazonium:54 parts of hydrochloric acid are added in 251 parts of aniline 2,5- disulfonic acids(In terms of hydrogen chloride)
It is on the rocks after stirring 3 hours to cool in 0-3 DEG C, add 72 parts of sub- sodium(It is made into 30% solution), obtained within 4 hours in 3-7 DEG C of maintenance reaction
Aniline 2,5- disulfonic acid diazonium compounds;
2)γ acid dissolvings:236 parts of γ acid are added to the water, at 15-20 DEG C, mashing is dissolved for 1 hour, then uses sodium hydroxide
Solution adjusts pH value to be 6.5;
3)Once it is coupled:Aniline 2,5- disulfonic acid diazonium compounds are added in γ acid solutions, control 0-3 DEG C of temperature, instead
Answer 4 hours, a conjugates are obtained after adjusting pH=3.5, reaction completely with sodium bicarbonate dry powder;
4)Secondary diazonium:361 parts of sulfonation para-esters 43 parts of hydrochloric acid of addition are on the rocks after stirring 2 hours to cool in 0-5 DEG C, then adds
Enter 69 parts of sub- sodium(It is made into 30% solution), sulfonation para-ester diazonium thing is obtained within 3 hours in 3-7 DEG C of maintenance reaction;
5)Secondary coupling:Sulfonation para-ester diazonium thing is added in a conjugates, pH=7.0, control are adjusted with sodium bicarbonate dry powder
10-15 DEG C of temperature processed, carries out reaction 6 hours, with profit circle method detection terminal, and terminal is to obtaining secondary conjugates, after reaction is complete
It is filtered and carries out spray drying again and packs to obtain product(2), it has following structure:
(2)
It is computed, yield is 97%, purity is 85%.
Embodiment 3
1)Aniline 2,5- disulfonic acid diazonium:55 parts of hydrochloric acid are added in 253 parts of aniline 2,5- disulfonic acids(In terms of hydrogen chloride)
It is on the rocks after stirring 2 hours to cool in 0-3 DEG C, add 70 parts of sub- sodium(It is made into 30% solution), obtained within 3 hours in 3-7 DEG C of maintenance reaction
Aniline 2,5- disulfonic acid diazonium compounds;
2)γ acid dissolvings:239 parts of γ acid are added to the water, at 15-20 DEG C, mashing is dissolved for 1 hour, then uses sodium hydroxide
Solution adjusts pH value to be 7.0;
3)Once it is coupled:Aniline 2,5- disulfonic acid diazonium compounds are added in γ acid solutions, control 0-3 DEG C of temperature, instead
Answer 5 hours, a conjugates are obtained after adjusting pH=4.0, reaction completely with sodium bicarbonate dry powder;
4)Secondary diazonium:365 parts of sulfonation para-esters 43 parts of hydrochloric acid of addition are on the rocks after stirring 2 hours to cool in 0-5 DEG C, then adds
Enter 69 parts of sub- sodium(It is made into 30% solution), sulfonation para-ester diazonium thing is obtained within 4 hours in 3-7 DEG C of maintenance reaction;
5)Secondary coupling:Sulfonation para-ester diazonium thing is added in a conjugates, pH=7.2, control are adjusted with sodium bicarbonate dry powder
10-15 DEG C of temperature processed, carries out reaction 7 hours, with profit circle method detection terminal, and terminal is to obtaining secondary conjugates, after reaction is complete
It is filtered and carries out spray drying again and packs to obtain product(2).
It is computed, yield is 95%, purity is 83%.
Embodiment 4
1)Aniline 2,5- disulfonic acid diazonium:55 parts of hydrochloric acid are added in 253 parts of aniline 2,5- disulfonic acids(In terms of hydrogen chloride)
It is on the rocks after stirring 2 hours to cool in 0-3 DEG C, add 70 parts of sub- sodium(It is made into 30% solution), obtained within 3 hours in 3-7 DEG C of maintenance reaction
Aniline 2,5- disulfonic acid diazonium compounds;
2)J acid dissolvings:239 parts of J acid are added to the water, at 15-20 DEG C, mashing is dissolved for 1 hour, then molten with sodium hydroxide
Liquid adjusts pH value to be 7.0;
3)Once it is coupled:Aniline 2,5- disulfonic acid diazonium compounds are added in J acid solutions, control 0-3 DEG C of temperature, reaction
5 hours, a conjugates are obtained after adjusting pH=4.0, reaction completely with sodium bicarbonate dry powder;
4)Secondary diazonium:365 parts of sulfonation para-esters 43 parts of hydrochloric acid of addition are on the rocks after stirring 2 hours to cool in 0-5 DEG C, then adds
Enter 69 parts of sub- sodium(It is made into 30% solution), sulfonation para-ester diazonium thing is obtained within 4 hours in 3-7 DEG C of maintenance reaction;
5)Secondary coupling:Sulfonation para-ester diazonium thing is added in a conjugates, pH=7.2, control are adjusted with sodium bicarbonate dry powder
10-15 DEG C of temperature processed, carries out reaction 7 hours, with profit circle method detection terminal, and terminal is to obtaining secondary conjugates, after reaction is complete
It is filtered and carries out spray drying again and packs to obtain product(1).
It is computed, yield is 96%, purity is 86%.
Embodiment 5
1)Aniline 2,5- disulfonic acid diazonium:55 parts of hydrochloric acid are added in 260 parts of aniline 2,5- disulfonic acids(In terms of hydrogen chloride)
It is on the rocks after stirring 2 hours to cool in 0-3 DEG C, add 73 parts of sub- sodium(It is made into 30% solution), obtained within 3 hours in 3-7 DEG C of maintenance reaction
Aniline 2,5- disulfonic acid diazonium compounds;
2)J acid dissolvings:241 parts of J acid are added to the water, at 15-20 DEG C, mashing is dissolved for 1 hour, then molten with sodium hydroxide
Liquid adjusts pH value to be 7.0;
3)Once it is coupled:Aniline 2,5- disulfonic acid diazonium compounds are added in J acid solutions, control 0-3 DEG C of temperature, reaction
4 hours, a conjugates are obtained after adjusting pH=4.0, reaction completely with sodium bicarbonate dry powder;
4)Secondary diazonium:380 parts of sulfonation para-esters 45 parts of hydrochloric acid of addition are on the rocks after stirring 2 hours to cool in 0-5 DEG C, then adds
Enter 73 parts of sub- sodium(It is made into 30% solution), sulfonation para-ester diazonium thing is obtained within 4 hours in 3-7 DEG C of maintenance reaction;
5)Secondary coupling:Sulfonation para-ester diazonium thing is added in a conjugates, pH=7.0, control are adjusted with sodium bicarbonate dry powder
10-15 DEG C of temperature processed, carries out reaction 8 hours, with profit circle method detection terminal, and terminal is to obtaining secondary conjugates, after reaction is complete
It is filtered and carries out spray drying again and packs to obtain product(1).
It is computed, yield is 98%, purity is 90%.
Following table is that dyestuff of the present invention mainly applies index(At a temperature of 40 DEG C, dyeing is carried out):
Embodiment described above is only the preferred embodiment to absolutely prove the present invention and being lifted, protection model of the invention
Enclose not limited to this.Equivalent substitute or conversion that those skilled in the art are made on the basis of the present invention, in the present invention
Protection domain within.Protection scope of the present invention is defined by claims.
Claims (10)
1. a kind of active orange suitable for low temperature dyeing, it is characterised in that structural formula is as shown in Equation 1:
Formula 1
In formula 1, R1And R2One of them be-NH2, another is H.
2. the preparation method of the active orange described in claim 1, it is characterised in that comprise the following steps:
1)By aniline 2,5- disulfonic acids carry out diazo-reaction with hydrochloric acid and sodium nitrite in aqueous solution, obtain aniline 2,5- disulfonic acids
Diazonium compound;
2)J acid or γ acid are mixed with water, after mashing dissolving, and regulation pH value is 6 ~ 7.5, standby after clarification;
3)Step 1)Obtained aniline 2,5- disulfonic acids diazonium compound and step 2)Obtained J acid or γ aqueous acids carries out anti-
A deserved conjugates;
4)Sulfonation para-ester carries out diazo-reaction with hydrochloric acid and sodium nitrite in aqueous solution, obtains sulfonation para-ester diazonium thing;
5)Step 4)Obtained sulfonation para-ester diazonium thing adds step 3)In an obtained conjugates react obtaining two
Secondary conjugates, filter, are drying to obtain.
3. the preparation method of active orange according to claim 2, it is characterised in that step 1)For aniline 2,5- pairs
0-3 DEG C is cooled to after hydrochloric acid, stirring are added in sulfonic acid, sodium nitrite in aqueous solution is added, in 3-7 DEG C of reaction, aniline 2 is obtained,
5- disulfonic acid diazonium compounds.
4. the preparation method of active orange according to claim 2, it is characterised in that step 2)In with sodium hydroxide
Or sodium acid carbonate regulation pH value is 6 ~ 7.5.
5. the preparation method of active orange according to claim 2, it is characterised in that step 3)For by step 1)
The aniline 2 arrived, 5- disulfonic acid diazonium compounds are added to step 2)In obtained J acid or γ aqueous acids, temperature 0-3 is controlled
DEG C, to adjust pH=3 ~ 4 with sodium bicarbonate dry powder, a conjugates are reacted to obtain in progress.
6. the preparation method of active orange according to claim 2, it is characterised in that step 4)For sulfonation para-ester
Add after being stirred in hydrochloric acid, be cooled to 0-5 DEG C, add sodium nitrite in aqueous solution, in 3-7 DEG C of reaction, obtain sulfonation para-ester weight
Nitrogen thing.
7. the preparation method of active orange according to claim 2, it is characterised in that step 5)For by step 4)
The sulfonation para-ester diazonium thing arrived adds step 3)In an obtained conjugates, pH=6.5 ~ 7.5, control are adjusted with sodium bicarbonate dry powder
10-15 DEG C of temperature processed, reaction, obtains secondary conjugates, filters, is drying to obtain.
8. the preparation method of the active orange according to any one of claim 2 ~ 7, it is characterised in that aniline 2,5- is double
Sulfonic acid:J acid or γ acid:Mass ratio=250 ~ 260 of sulfonation para-ester:234~241:360~380.
9. the application of the active orange suitable for low temperature dyeing described in claim 1, it is characterised in that the reactive orange
Color dyestuff is used for cellulose dyeing, continuous knot dyeing, discharge, stamp and brocade/cotton One Bath Dyeing Process.
10. application according to claim 9, it is characterised in that the dyeing temperature of the active orange is 35 ~ 45
℃。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4069218A (en) * | 1974-04-10 | 1978-01-17 | Ciba-Geigy Corporation | Water-soluble fiber-reactive disazo dyestuffs |
CN101117449A (en) * | 2007-09-04 | 2008-02-06 | 大连理工大学 | High-concentration composite reactive dye |
CN101671487A (en) * | 2009-08-18 | 2010-03-17 | 天津德凯化工股份有限公司 | Method for synthesizing red reactive dye |
CN102898868A (en) * | 2012-10-31 | 2013-01-30 | 无锡润新染料有限公司 | Reactive orange dye and preparation method thereof |
CN103554989A (en) * | 2013-10-24 | 2014-02-05 | 浙江亿得化工有限公司 | Low-temperature composite activated black dye and application thereof |
-
2016
- 2016-06-06 CN CN201610391752.4A patent/CN106065199B/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4069218A (en) * | 1974-04-10 | 1978-01-17 | Ciba-Geigy Corporation | Water-soluble fiber-reactive disazo dyestuffs |
CN101117449A (en) * | 2007-09-04 | 2008-02-06 | 大连理工大学 | High-concentration composite reactive dye |
CN101671487A (en) * | 2009-08-18 | 2010-03-17 | 天津德凯化工股份有限公司 | Method for synthesizing red reactive dye |
CN102898868A (en) * | 2012-10-31 | 2013-01-30 | 无锡润新染料有限公司 | Reactive orange dye and preparation method thereof |
CN103554989A (en) * | 2013-10-24 | 2014-02-05 | 浙江亿得化工有限公司 | Low-temperature composite activated black dye and application thereof |
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