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 PDF

Info

Publication number
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
Authority
CN
China
Prior art keywords
acid
aniline
dyeing
preparation
active orange
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201610391752.4A
Other languages
Chinese (zh)
Other versions
CN106065199A (en
Inventor
崔孟元
梦文
熊建平
朱训杰
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
HUALI DYE INDUSTRY Co Ltd HUBEI
Original Assignee
HUALI DYE INDUSTRY Co Ltd HUBEI
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by HUALI DYE INDUSTRY Co Ltd HUBEI filed Critical HUALI DYE INDUSTRY Co Ltd HUBEI
Priority to CN201610391752.4A priority Critical patent/CN106065199B/en
Publication of CN106065199A publication Critical patent/CN106065199A/en
Application granted granted Critical
Publication of CN106065199B publication Critical patent/CN106065199B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C09B33/00Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/02Disazo dyes
    • C09B33/08Disazo dyes in which the coupling component is a hydroxy-amino compound
    • C09B33/10Disazo dyes in which the coupling component is a hydroxy-amino compound in which the coupling component is an amino naphthol
    • 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
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/66Natural or regenerated cellulose 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
    • D06P3/82Textiles which contain different kinds of fibres
    • D06P3/8204Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8219Textiles 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

It is a kind of suitable for active orange of low temperature dyeing and preparation method thereof
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 ℃。
CN201610391752.4A 2016-06-06 2016-06-06 It is a kind of suitable for active orange of low temperature dyeing and preparation method thereof Active CN106065199B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610391752.4A CN106065199B (en) 2016-06-06 2016-06-06 It is a kind of suitable for active orange of low temperature dyeing and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610391752.4A CN106065199B (en) 2016-06-06 2016-06-06 It is a kind of suitable for active orange of low temperature dyeing and preparation method thereof

Publications (2)

Publication Number Publication Date
CN106065199A CN106065199A (en) 2016-11-02
CN106065199B true CN106065199B (en) 2017-10-31

Family

ID=57421067

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610391752.4A Active CN106065199B (en) 2016-06-06 2016-06-06 It is a kind of suitable for active orange of low temperature dyeing and preparation method thereof

Country Status (1)

Country Link
CN (1) CN106065199B (en)

Citations (5)

* Cited by examiner, † Cited by third party
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

Patent Citations (5)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
CN106065199A (en) 2016-11-02

Similar Documents

Publication Publication Date Title
EP2248859B1 (en) A black reactive dye and the preparation thereof
CN1330712C (en) Process for preparing solutions of anionic organic compounds
CN102838883A (en) Preparation method for C.I. paratonere 49:1
CN102408743B (en) Production process of direct blending navy blue D-R dye
CN107828240B (en) A kind of preparation method and application of dark blue reactive dye mill base
CN104403349B (en) A kind of industrialized preparing process of pigment yellow 97
CN106065199B (en) It is a kind of suitable for active orange of low temperature dyeing and preparation method thereof
CN105647221B (en) Method for preparing C.I. pigment red 185
JP3567135B2 (en) Red reactive dye having monochlorotriazine group and acetoxyethyl sulfone group
CN104004379B (en) A kind of production method of direct blended spinning yellow dye
CN101531831B (en) Production method of direct blended brown D-RS dye
CN102898867A (en) Composite reactive yellow dye and preparation method thereof
CN105273437B (en) Red reactive dye as well as preparation method and application thereof
CN102504594B (en) Reactive red dye composition
CN101955682A (en) Method for preparing high-performance organic pigment PR176
CN102504588A (en) Turquoise blue active dye, as well as preparation method and application thereof
CN104725898A (en) Cyanide and copper removal method during production process of cyaniding dye
CN101735657B (en) Method for preparing active dye for purple wool
CN102911127A (en) Preparation method for low-triazine fluorescent whitening agent
CN109651841A (en) A kind of preparation method of composite active black dye
CN101704770A (en) Method for preparing purple reactive dye
CN101671487A (en) Method for synthesizing red reactive dye
CN101709044B (en) Preparation method of purple active dye for wool
CN102433025A (en) Black active dye and preparation method thereof
CN105860580A (en) Preparation method of orange reactive dye

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant