CN108504138A - A kind of preparation method of the reactive black dye of cellulose fiber Wesy - Google Patents
A kind of preparation method of the reactive black dye of cellulose fiber Wesy Download PDFInfo
- Publication number
- CN108504138A CN108504138A CN201810453673.0A CN201810453673A CN108504138A CN 108504138 A CN108504138 A CN 108504138A CN 201810453673 A CN201810453673 A CN 201810453673A CN 108504138 A CN108504138 A CN 108504138A
- Authority
- CN
- China
- Prior art keywords
- reaction
- reaction mixture
- preparation
- black dye
- reactive black
- 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.)
- Pending
Links
- 0 C*c1nc([Cl+])nc(*)n1 Chemical compound C*c1nc([Cl+])nc(*)n1 0.000 description 3
- ZSYHHLNYBBDVLZ-UHFFFAOYSA-N CCC1=[N]=CCC(C)=NC(C)=N1 Chemical compound CCC1=[N]=CCC(C)=NC(C)=N1 ZSYHHLNYBBDVLZ-UHFFFAOYSA-N 0.000 description 1
- ADVXAMGGIRUOKU-UHFFFAOYSA-N CCc1nc(Cl)nc(Cl)n1 Chemical compound CCc1nc(Cl)nc(Cl)n1 ADVXAMGGIRUOKU-UHFFFAOYSA-N 0.000 description 1
- SRWCSZKDJASTLO-MRWCJKGFSA-N CN/C=C(/C=C\C(N)=C)\S(O)(=O)=O Chemical compound CN/C=C(/C=C\C(N)=C)\S(O)(=O)=O SRWCSZKDJASTLO-MRWCJKGFSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N Cc(c(N)c1)ccc1N Chemical compound Cc(c(N)c1)ccc1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo 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
- 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
- D06P1/382—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 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
- D06P3/663—Natural or regenerated cellulose using reactive dyes reactive group directly attached to heterocyclic group
Abstract
The invention discloses a kind of preparation method of the reactive black dye of cellulose fiber Wesy, general structure is as follows:Wherein M is hydrogen or alkali metal, and preparation method includes:1) makeHydrogen chloride and alkali metal nitrites salts react in water, obtain the first reaction mixture;2) it is added into the first reaction mixture in the presence of auxiliary agentReaction, obtains the second reaction mixture;Auxiliary agent is the composition of naphthalenesulfonate formaldehyde condensation compound and fatty alcohol polyoxyethylene ether;3)
Description
Technical field
The invention belongs to textile printing and dyeing fields, and in particular to a kind of preparation side of the reactive black dye of cellulose fiber Wesy
Method.
Background technology
Reactive dye, also known as chemically-reactive dyes, for a class of dyes in dyeing with fiber chemically reactive.Reactive dye
As the representative of modern dye industry, faster development is obtained in recent years, at present Reactive Dye for Cellulose Fibre in the world
Annual output accounts for 20% or more of world's dyestuff annual output up to 200,000 tons or more, but as the mankind in terms of environmental protection to wanting
It asks and is increasingly promoted, traditional reactive dye reactive black dye especially therein, there is such as degree of fixation low, depth is not
Height needs the shortcomings of high-alkali dyeing with high salt, greatly limits the application of reactive dye, therefore develops one group with Gao Gu
The reactive dye that color rate, high dying color, less salt alkali dye are the pursuits of those skilled in the art, wherein the active black of following structures
Dyestuff can have preferable coloring:
Wherein,
M is hydrogen or alkali metal;
Although the dyestuff of above structure is applied to dyeing, relatively low, purity that there are still yields at present
The shortcomings of relatively low and preparation process sewage yield is big, it is difficult to be applied on a large scale.
Invention content
The technical problem to be solved by the present invention is to overcome the deficiencies of the prior art and provide a kind of work of cellulose fiber Wesy
Property black dyestuff preparation method, can be realized under relatively mild reaction condition in high yield, high-purity the advantages that, and prepared
The sewage flow rate that journey generates greatly reduces, and is conducive to the requirement instantly to environmental protection.
In order to solve the above technical problems, the technical solution adopted by the present invention is as follows:
A kind of preparation method of the reactive black dye of cellulose fiber Wesy, the structural formula of the reactive black dye are:
Wherein,
M is hydrogen or alkali metal, and the preparation method includes the following steps:
(1) makeHydrogen chloride and alkali metal nitrites salts react in water, obtain the first reaction mixture;
(2) it is added into first reaction mixture in the presence of auxiliary agentReaction, obtains
Second reaction mixture;Wherein, the auxiliary agent is the composition of naphthalenesulfonate formaldehyde condensation compound and fatty alcohol polyoxyethylene ether;
(3) makeIt reacts in water, obtains third reaction mixture;
(4) hydrogen chloride, alkali metal nitrites salts are added into the third reaction mixture, it is anti-to obtain the 4th for reaction
Answer mixed solution;
(5) second reaction mixture and the 4th reaction mixture are mixed, reaction, obtains the 5th reaction
Mixed solution;
(6) ammonium hydroxide is added to the 5th reaction mixture, the reactive black dye is made in reaction;
The preparation method also includes selectively step (7):Acidification step.
In the present invention, being added for hydrogen chloride can be realized by the way that aqueous solution, that is, hydrochloric acid of hydrogen chloride is added.
In the present invention, the alkali metal nitrites salts can be sodium nitrite, potassium nitrite or lithium nitrite etc..
A specific aspect according to the present invention, when M is hydrogen, the preparation method further includes the step (7).Acidification
It can be carried out by the way that hydrochloric acid etc. is added.
Some preferred aspects according to the present invention, the naphthalenesulfonate formaldehyde condensation compound and the fatty alcohol polyoxyethylene ether
Molar ratio be 1 ︰ 0.75-0.9.
Some preferred aspects according to the present invention, the auxiliary agent with it is describedMolar ratio
For 0.02-0.04 ︰ 1.
Some preferred aspects according to the present invention in step (1) and step (3), control the reaction at 0-5 DEG C respectively
It carries out.
Some preferred aspects according to the present invention in step (2) and step (4), control the reaction at 5-10 DEG C respectively
Lower progress.
Some preferred aspects according to the present invention in step (5), control the reaction and are carried out at 10~15 DEG C;With/
Or, in step (6), controls the reaction and carried out at 45~55 DEG C.
Some preferred aspects according to the present invention in step (5), control the reaction and are carried out in the case where pH value is 6-6.5.
Some preferred aspects according to the present invention, in step (5), the pH value, which passes through, to be added alkali metal hydrogencarbonate and carries out
It adjusts.Some specific aspects according to the present invention, the alkali metal hydrogencarbonate can be sodium bicarbonate, saleratus etc..
Some preferred aspects according to the present invention, in step (1), the inventory of the hydrogen chloride and alkali metal nitrites salts
It is relatively described respectivelyIt is excessive.
Some preferred aspects according to the present invention, it is described in step (2)With in step (1)
It is describedMolar ratio be 0.96-0.98 ︰ 1.
Some preferred aspects according to the present invention, it is described in step (3)With it is describedFeed intake
Molar ratio is 1 ︰ 0.92-0.98.
Some preferred aspects according to the present invention, in step (4), the inventory of the hydrogen chloride and alkali metal nitrites salts
Respectively with respect to described in step (3)It is excessive.
Some preferred aspects according to the present invention, in step (6), by being passed through water into the 5th reaction mixture
Steam controls the temperature that the reaction carries out.
Some preferred aspects according to the present invention, the preparation method further include post-processing step, the post-processing step
Including:By step (6) or step (7) reaction after reaction solution be filtered, then by gained filtrate be dried processing to get
The reactive black dye of the solid cellulose fiber Wesy.
Due to the use of above technical scheme, the present invention has the following advantages that compared with prior art:
The preparation method of the reactive black dye of cellulose fiber Wesy provided by the invention, can be in relatively mild reaction item
The advantages that high yield, high-purity are realized under part, and the sewage flow rate that preparation process generates greatly reduces, and especially meets instantly to ring
High standards in terms of the protection of border.
Specific implementation mode
Said program is described further below in conjunction with specific embodiment;It should be understood that these embodiments are for illustrating
The basic principles, principal features and advantages of the present invention, and the present invention is not by the scope limitation of following embodiment;It is used in embodiment
Implementation condition further adjustment can be done according to specific requirement, the implementation condition being not specified is usually the item in routine experiment
Part.
In following, unless otherwise specified, all raw materials are both from conventional method system commercially available or by this field
It is standby and obtain.
Embodiment 1
(1) will(253g, 1mol) is added to the water dissolving, and it is 3 ± 1 DEG C to keep temperature, and hydrochloric acid solution is added
(it be the hydrogen chloride content that is calculated of process to select a concentration of 33% hydrochloric acid solution, molar ratio, containing hydrogen chloride 75g,
Sodium nitrite solution (containing sodium nitrite 75.9g, 1.1mol) 2mol) is added afterwards, reacts 3 hours, obtains the first reaction mixing
Solution;
(2) it is added into first reaction mixtureIt (306.3g, 0.96mol) and helps
Agent is stirred to react 5 hours at 8 ± 1 DEG C, obtains the second reaction mixture, the auxiliary agent is by naphthalenesulfonate formaldehyde condensation compound
(7.4g creates chemical industry purchased from Shaoxing Zhejiang) and fatty alcohol polyoxyethylene ether (15.9g is purchased from Hai'an petrochemical industry) composition;
(3) will(184.5g, 1mol) is added in trash ice and water and stirs, and it is 3 ± 1 DEG C to keep temperature, willReaction 2 hours is added in (173g, 0.92mol), obtains third reaction mixture;
(4) hydrochloric acid and sodium nitrite are added in the third reaction mixture, are reacted 3 hours at 7 ± 1 DEG C,
The 4th reaction mixture is obtained, (it is the chlorine by being calculated to select a concentration of 33% hydrochloric acid solution, molar ratio to the hydrochloric acid
Change hydrogen content) and sodium nitrite inventory respectively with respect to described in step (3)It is excessive;
(5) second reaction mixture is added in the 4th reaction mixture, sodium bicarbonate is added and adjusts pH
Value reacts 3 hours at 12 ± 1 DEG C to 6.2 ± 0.1, obtains the 5th reaction mixture;
(6) ammonium hydroxide is added in the 5th reaction mixture, is passed through steam and is warming up to 48 ± 2 DEG C, keeps thermotonus
10 hours, obtain the 6th reaction mixture;Ammonium hydroxide is with respect to described in step (3)It is excessive to feed intake;
(7) the 6th reaction mixture is filtered, filtrate is taken to be dried, you can.
The reactive black dye structure of preparation is as follows:
Yield is 89.6%, purity 93%.
Embodiment 2
(1) will(253g, 1mol) is added to the water dissolving, and it is 4 ± 1 DEG C to keep temperature, and hydrochloric acid solution is added
(it be the hydrogen chloride content that is calculated of process to select a concentration of 33% hydrochloric acid solution, molar ratio, containing hydrogen chloride 93.75g,
Sodium nitrite solution (containing sodium nitrite 75.9g, 1.1mol) 2.5mol) is added afterwards, reacts 3 hours, it is mixed to obtain the first reaction
Close solution;
(2) it is added into first reaction mixtureIt (312.6g, 0.98mol) and helps
Agent is stirred to react 5 hours at 8 ± 1 DEG C, obtains the second reaction mixture, the auxiliary agent is by naphthalenesulfonate formaldehyde condensation compound
(9.8g creates chemical industry purchased from Shaoxing Zhejiang) and fatty alcohol polyoxyethylene ether (22.3g is purchased from Hai'an petrochemical industry) composition;
(3) will(184.5g, 1mol) is added in trash ice and water and stirs, and it is 3 ± 1 DEG C to keep temperature, will178.6g, 0.95mol) reaction 4 hours is added, obtain third reaction mixture;
(4) hydrochloric acid and sodium nitrite are added in the third reaction mixture, are reacted 2 hours at 7 ± 1 DEG C,
The 4th reaction mixture is obtained, (it is the chlorine by being calculated to select a concentration of 33% hydrochloric acid solution, molar ratio to the hydrochloric acid
Change hydrogen content) and sodium nitrite inventory respectively with respect to described in step (3)It is excessive;
(5) second reaction mixture is added in the 4th reaction mixture, sodium bicarbonate is added and adjusts pH
Value reacts 5 hours at 13 ± 1 DEG C to 6.4 ± 0.1, obtains the 5th reaction mixture;
(6) ammonium hydroxide is added in the 5th reaction mixture, is passed through steam and is warming up to 50 ± 2 DEG C, keeps thermotonus
12 hours, obtain the 6th reaction mixture;Ammonium hydroxide is with respect to described in step (3)It is excessive to feed intake;
(7) the 6th reaction mixture is filtered, filtrate is taken to be dried, you can.
The reactive black dye structure of preparation is as follows:
Yield is 90.2%, purity 92.5%.
Embodiment 3
(1) will(253g, 1mol) is added to the water dissolving, and it is 2 ± 1 DEG C to keep temperature, and hydrochloric acid solution is added
(it be the hydrogen chloride content that is calculated of process to select a concentration of 33% hydrochloric acid solution, molar ratio, containing hydrogen chloride 75g,
Potassium nitrite solution (containing potassium nitrite 93.6g, 1.1mol) 2mol) is added afterwards, reacts 3 hours, obtains the first reaction mixing
Solution;
(2) it is added into first reaction mixtureIt (306.3g, 0.96mol) and helps
Agent is stirred to react 5 hours at 8 ± 1 DEG C, obtains the second reaction mixture, the auxiliary agent is by naphthalenesulfonate formaldehyde condensation compound
(8.4g creates chemical industry purchased from Shaoxing Zhejiang) and fatty alcohol polyoxyethylene ether (17.9g is purchased from Hai'an petrochemical industry) composition;
(3) will(184.5g, 1mol) is added in trash ice and water and stirs, and it is 3 ± 1 DEG C to keep temperature, willReaction 3 hours is added in (173g, 0.92mol), obtains third reaction mixture;
(4) hydrochloric acid and potassium nitrite are added in the third reaction mixture, are reacted 3 hours at 7 ± 1 DEG C,
The 4th reaction mixture is obtained, (it is the chlorine by being calculated to select a concentration of 33% hydrochloric acid solution, molar ratio to the hydrochloric acid
Change hydrogen content) and potassium nitrite inventory respectively with respect to described in step (3)It is excessive;
(5) second reaction mixture is added in the 4th reaction mixture, saleratus is added and adjusts pH
Value reacts 4 hours at 14 ± 1 DEG C to 6.2 ± 0.1, obtains the 5th reaction mixture;
(6) ammonium hydroxide is added in the 5th reaction mixture, is passed through steam and is warming up to 52 ± 2 DEG C, keeps thermotonus 8
Hour, obtain the 6th reaction mixture;Ammonium hydroxide is with respect to described in step (3)It is excessive to feed intake;
(7) the 6th reaction mixture is filtered, filtrate is taken to be dried, you can.
The reactive black dye structure of preparation is as follows:
Yield is 92.6%, purity 93.5%.
Comparative example 1
Substantially with embodiment 1, difference lies in, not adding assistant in step (2), yield 75%, purity 86%.
Comparative example 2
Substantially with embodiment 1, difference lies in naphthalenesulfonate formaldehyde condensation compound is only added in (2) in step, and yield is
78%, purity 87%.
Comparative example 3
Substantially with embodiment 1, difference lies in, only it is added fatty alcohol polyoxyethylene ether in step (2), yield 80%,
Purity is 88%.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar cans understand the content of the present invention and implement it accordingly, and it is not intended to limit the scope of the present invention, all according to the present invention
Equivalent change or modification made by Spirit Essence, should be covered by the protection scope of the present invention.
Claims (10)
1. a kind of preparation method of the reactive black dye of cellulose fiber Wesy, the structural formula of the reactive black dye are:
Wherein, M is hydrogen
Or alkali metal, which is characterized in that the preparation method includes the following steps:
(1) makeHydrogen chloride and alkali metal nitrites salts react in water, obtain the first reaction mixture;
(2) it is added into first reaction mixture in the presence of auxiliary agentReaction, obtains second
Reaction mixture;Wherein, the auxiliary agent is the composition of naphthalenesulfonate formaldehyde condensation compound and fatty alcohol polyoxyethylene ether;
(3) makeIt reacts in water, obtains third reaction mixture;
(4) hydrogen chloride, alkali metal nitrites salts are added into the third reaction mixture, it is mixed to obtain the 4th reaction for reaction
Close solution;
(5) second reaction mixture and the 4th reaction mixture are mixed, reaction, obtains the 5th reaction mixing
Solution;
(6) ammonium hydroxide is added to the 5th reaction mixture, the reactive black dye is made in reaction;
The preparation method also includes selectively step (7):Acidification step.
2. the preparation method of the reactive black dye of cellulose fiber Wesy according to claim 1, which is characterized in that the naphthalene
Sulfonate and formaldehyde condensation product and the molar ratio of the fatty alcohol polyoxyethylene ether are 1 ︰ 0.75-0.9.
3. the preparation method of the reactive black dye of cellulose fiber Wesy according to claim 1 or 2, which is characterized in that institute
State auxiliary agent with it is describedMolar ratio be 0.02-0.04 ︰ 1.
4. the preparation method of the reactive black dye of cellulose fiber Wesy according to claim 1, which is characterized in that step
(1) and in step (3), the reaction is controlled respectively and is carried out at 0-5 DEG C;And/or
In step (2) and step (4), the reaction is controlled respectively and is carried out at 5-10 DEG C.
5. the preparation method of the reactive black dye of cellulose fiber Wesy according to claim 1, which is characterized in that step
(5) it in, controls the reaction and is carried out at 10~15 DEG C;And/or in step (6), control it is described reaction at 45~55 DEG C into
Row.
6. the preparation method of the reactive black dye of cellulose fiber Wesy according to claim 1 or 5, which is characterized in that step
Suddenly it in (5), controls the reaction and is carried out in the case where pH value is 6-6.5.
7. the preparation method of the reactive black dye of cellulose fiber Wesy according to claim 6, which is characterized in that step
(5) in, the pH value is adjusted by the way that alkali metal hydrogencarbonate is added.
8. the preparation method of the reactive black dye of cellulose fiber Wesy according to claim 1, which is characterized in that step
(1) in, the inventory of the hydrogen chloride and alkali metal nitrites salts is relatively described respectivelyIt is excessive;And/or
It is described in step (2)With it is described in step (1)Molar ratio be
0.96-0.98 ︰ 1;And/or
It is described in step (3)With it is describedMolar ratio be 1 ︰ 0.92-0.98;And/or
In step (4), the inventory of the hydrogen chloride and alkali metal nitrites salts is respectively with respect to described in step (3)It is excessive.
9. the preparation method of the reactive black dye of cellulose fiber Wesy according to claim 1, which is characterized in that step
(6) in, the temperature that the reaction carries out is controlled by being passed through vapor into the 5th reaction mixture.
10. the preparation method of the reactive black dye of cellulose fiber Wesy according to claim 1, which is characterized in that described
Preparation method further includes post-processing step, and the post-processing step includes:By the reaction solution after step (6) or step (7) reaction
It is filtered, processing then is dried to get the reactive black dye of the solid cellulose fiber Wesy in gained filtrate.
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2945021A (en) * | 1956-09-14 | 1960-07-12 | Ciba Ltd | Monoazo and disazo triazine dyes |
US3190872A (en) * | 1961-05-23 | 1965-06-22 | Ciba Geigy Corp | Water-soluble disazo dyestuffs |
DE3623154A1 (en) * | 1986-07-10 | 1988-01-14 | Bayer Ag | Process for the preparation of azo dye solutions |
US4801693A (en) * | 1984-06-01 | 1989-01-31 | Basf Aktiengesellschaft | Substituted sulfobenzene and triazine-containing reactive dyes |
CN101037548A (en) * | 2007-05-10 | 2007-09-19 | 湖北华丽染料工业有限公司 | Black dye mixer and preparation method and application thereof |
CN101565559A (en) * | 2009-04-14 | 2009-10-28 | 丽源(湖北)科技有限公司 | Navy reactive dye mixture and preparation and application thereof |
-
2018
- 2018-05-14 CN CN201810453673.0A patent/CN108504138A/en active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2945021A (en) * | 1956-09-14 | 1960-07-12 | Ciba Ltd | Monoazo and disazo triazine dyes |
US3190872A (en) * | 1961-05-23 | 1965-06-22 | Ciba Geigy Corp | Water-soluble disazo dyestuffs |
US4801693A (en) * | 1984-06-01 | 1989-01-31 | Basf Aktiengesellschaft | Substituted sulfobenzene and triazine-containing reactive dyes |
DE3623154A1 (en) * | 1986-07-10 | 1988-01-14 | Bayer Ag | Process for the preparation of azo dye solutions |
CN101037548A (en) * | 2007-05-10 | 2007-09-19 | 湖北华丽染料工业有限公司 | Black dye mixer and preparation method and application thereof |
CN101565559A (en) * | 2009-04-14 | 2009-10-28 | 丽源(湖北)科技有限公司 | Navy reactive dye mixture and preparation and application thereof |
Non-Patent Citations (1)
Title |
---|
沈永嘉主编: "《有机颜料 品种与应用》", 31 July 2001, 北京:化学工业出版社 * |
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