CN102911526A - Turquoise blue reactive dye and preparation method thereof - Google Patents
Turquoise blue reactive dye and preparation method thereof Download PDFInfo
- Publication number
- CN102911526A CN102911526A CN 201210362081 CN201210362081A CN102911526A CN 102911526 A CN102911526 A CN 102911526A CN 201210362081 CN201210362081 CN 201210362081 CN 201210362081 A CN201210362081 A CN 201210362081A CN 102911526 A CN102911526 A CN 102911526A
- Authority
- CN
- China
- Prior art keywords
- temperature
- adjust
- hour
- hours
- holding temperatures
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Abstract
The invention relates to a turquoise blue reactive dye and a preparation method thereof, wherein the turquoise blue reactive dye has following structural formula; the invention provides a preparation method of the turquoise blue reactive dye; the turquoise blue reactive dye manufactured by the invention is suitable for dyeing fibers such as cotton, hemp, wool and the like, and particularly for inkjet printing.
Description
Technical field
The present invention relates to a kind of reactive dyestuffs and preparation method thereof, especially a kind of turquoise blue reactive dyestuffs and preparation method thereof.
Background technology
Reactive dyestuffs claim again chemically-reactive dyes, contain the active group of chemical in the molecule, can form the dyestuff of covalent linkage in the aqueous solution with fiber-reactives such as cotton, fiber crops, hairs, reactive dyestuffs can obtain particularly wet fastness of high-caliber every strong performance with dyeing and the simple dying operation of economy.The chromatogram of reactive dyestuffs is wide, lovely luster, excellent performance, suitability are strong, and its form and aspect and performance adapt with the requirement of market to fiber and dress material basically.
In reactive dyestuffs, the turquoise blue reactive dyestuffs take CuPc as parent are of less types.
Summary of the invention
Technical problem to be solved by this invention is, a kind of brand-new molecular structure, lovely luster, full turquoise blue reactive dyestuffs and preparation method thereof are provided, and is applicable to the dyeing of the fibers such as cotton, fiber crops, hair, is particularly useful for ink-jet printed.
In order to solve the problems of the technologies described above, the technical solution used in the present invention is: a kind of turquoise blue reactive dyestuffs have following general structure (I)
CuPc represents CuPc in the formula
R Wei – SO
2NH-C
2H
4OCOCH
3Or-SO
2NH-C
2H
4OSO
2NH
2
The present invention also provides a kind of preparation method of said structure formula I turquoise blue reactive dyestuffs, comprises the steps:
A, chlorosulphonation
In retort, add chlorsulfonic acid (CAS number: 7790-94-5), control 40～50 ℃ of temperature.2 hours consuming time with CuPc (CAS number: 147-14-8) add. adjust 110～140 ℃ of temperature, 110～140 ℃ of holding temperatures were reacted 4 hours, adjust 65～70 ℃ of temperature, 65～70 ℃ of holding temperatures added sulfur oxychloride in 2 hours consuming time, 65～70 ℃ of holding temperatures were reacted 2 hours, adjusted 90 ℃ of temperature, 90～95 ℃ of holding temperatures, reacted 1 hour, and adjusted 105 ℃ of temperature, 105～110 ℃ of holding temperatures, reacted 1 hour, and got the chlorosulphonation feed liquid;
Adjust 20～25 ℃ of temperature, 2 hours consuming time, the chlorosulphonation feed liquid of gained is joined in the retort that frozen water is housed, 0～20 ℃ of holding temperature stirred 1 hour, and the gained feed liquid is carried out solid-liquid separation, to filtrate pH=4～5, collect filter cake with-5～5 ℃ of cold water washing filter cakes;
B, esterification
In retort, add Monoethanolamine MEA BASF (CAS number: 141-43-5), 15～20 ℃ of control temperature, (CAS number: 64-19-7) adding adds sulfuric acid (CAS number: 7664-93-9), stir with Glacial acetic acid in 45～60 minutes, reflux lower, adjust 120～150 ℃ of temperature, 120～150 ℃ of holding temperatures were reacted 5 hours, adjust 5～10 ℃ of temperature, for subsequent use;
C, condensation
A step gained material is added in the b step gained material, adjust 5～10 ℃ of temperature with frozen water, (CAS number: 1310-73-2) solution is kept pH=9～12 with 10～40% sodium hydroxide, stirring reaction 1～3 hour, adjust 35～50 ℃ of temperature, 35～50 ℃ of holding temperatures, pH=9～12, stirring reaction 1～3 hour.
D, neutralization reaction
The reaction solution of c step is adjusted to pH=6～7.5 with 30% hydrochloric acid soln;
E, aftertreatment
The feed liquid that the d step is obtained is refining, be the finished product dyestuff after the drying.
Further, in the step c of aforesaid method, add ammoniacal liquor.
As another embodiment of the present invention: the preparation method of said structure formula I turquoise blue reactive dyestuffs comprises the steps:
A, chlorosulphonation
In retort, add chlorsulfonic acid, 40～50 ℃ of control temperature.100～120 ℃ of temperature were adjusted in the CuPc adding in 2 hours consuming time, 100～120 ℃ of holding temperatures were reacted 1 hour, adjusted 120～140 ℃ of temperature, and 120～140 ℃ of holding temperatures were reacted 3～6 hours, got the chlorosulphonation feed liquid;
Adjust 20～25 ℃ of temperature, 2 hours consuming time, the chlorosulphonation feed liquid of gained is joined in the retort that frozen water is housed.0～20 ℃ of holding temperature stirred 1 hour, and the gained feed liquid is carried out solid-liquid separation, used-5～5 ℃ of cold water washing filter cakes to filtrate pH=4～5; Collect filter cake.
B, condensation
In retort, add Sulfamic acid, 2-aminoethyl ester(H
2NCH
2CH
2OSO
2NH
2; CAS number: 10042-77-0), a step gained material is added, adjust 5～10 ℃ of temperature with frozen water, (CAS number: 1310-73-2) solution is kept pH=9～12 with 10～40% sodium hydroxide, stirring reaction 1～3 hour is adjusted 35～50 ℃ of temperature, 35～50 ℃ of holding temperatures, pH=9～12, stirring reaction 1～3 hour;
C, neutralization reaction
The reaction solution of b step is adjusted to pH=6～7.5 with 30% hydrochloric acid soln.
D, aftertreatment
The feed liquid that the c step is obtained is refining, be finished product after the drying.
Further, in the step b of aforesaid method, add ammoniacal liquor.
The present invention also provides the application performance of said structure formula I dyestuff in dyeing.
The sodium hydroxide solution that summary of the invention part of the present invention and embodiment partly mention, hydrochloric acid soln, the related percentage concentration of ammoniacal liquor are mass percent concentration.
The beneficial effect that the present invention has:
The turquoise blue reactive dyestuffs that the present invention makes are applicable to the dyeing of the fibers such as cotton, fiber crops, hair, are particularly useful for ink-jet printed.
Embodiment
The invention will be further described below in conjunction with specific embodiment, but do not limit protection scope of the present invention.
Embodiment 1
A kind of preparation method of turquoise blue reactive dyestuffs comprises the steps:
A, chlorosulphonation
In retort, add 1750 kilograms of chlorsulfonic acids, 40～50 ℃ of control temperature.2 hours consuming time with 350 kilograms of addings of CuPc. and adjust 128 ℃ of temperature, 128～130 ℃ of holding temperatures were reacted 4 hours.Adjust 65～70 ℃ of temperature, 65～70 ℃ of holding temperatures, 2 hours consuming time with 595 kilograms of addings of sulfur oxychloride.65～70 ℃ of holding temperatures were reacted 2 hours.Adjust 90 ℃ of temperature, 90～95 ℃ of holding temperatures were reacted 1 hour.Adjust 105 ℃ of temperature.105～110 ℃ of holding temperatures were reacted 1 hour, got the chlorosulphonation feed liquid.
Adjust 20～25 ℃ of temperature, 2 hours consuming time, the chlorosulphonation feed liquid of gained is joined in the retort that frozen water is housed.0～20 ℃ of holding temperature stirred 1 hour.The gained feed liquid is carried out solid-liquid separation.With-5～5 ℃ of cold water washing filter cakes to filtrate pH=5.Collect filter cake;
B, esterification
In retort, add 73.1 kilograms of Monoethanolamine MEA BASFs, the circulating water cooling.15～20 ℃ of control temperature with 71.9 kilograms of addings of Glacial acetic acid, added 3 kilograms in 98% sulfuric acid in 45～60 minutes, stir, and refluxed lower, adjusted 120～150 ℃ of temperature, and 120～150 ℃ of holding temperatures were reacted 5 hours.Adjust 5～10 ℃ of temperature, for subsequent use;
C, condensation
A step gained material is added in the b step gained material, adjust 5～10 ℃ of temperature with frozen water, keep pH=9～10 with 20% sodium hydroxide solution, stirring reaction 3 hours.Adjust 35～40 ℃ of temperature, 35～40 ℃ of holding temperatures, pH=9～10, stirring reaction 3 hours.
D, neutralization reaction
The reaction solution of c step is adjusted to pH=6～6.5 with 30% hydrochloric acid soln.
E, aftertreatment
The feed liquid that the d step is obtained is refining, be finished product after the drying.Get following formula structure turquoise blue reactive dyestuffs.
Embodiment 2
A kind of preparation method of turquoise blue reactive dyestuffs comprises the steps:
Step a, b are with embodiment 1 step a, b
C, condensation
A step gained material is added in the b step gained material, adjust 5～10 ℃ of temperature with frozen water, add 25% ammoniacal liquor (CAS number: 1336-21-6) 83 kilograms, keep pH=9～10 with 10% sodium hydroxide solution, stirring reaction 3 hours.Adjust 35～50 ℃ of temperature, 35～50 ℃ of holding temperatures, pH=9～10, stirring reaction 3 hours.
Steps d, e get following formula structure turquoise blue reactive dyestuffs with embodiment 1 steps d, e.
Embodiment 3
A kind of preparation method of turquoise blue reactive dyestuffs comprises the steps:
A, chlorosulphonation
In retort, add 2100 kilograms of chlorsulfonic acids, 40～50 ℃ of control temperature.2 hours consuming time with 350 kilograms of addings of CuPc. and adjust 118 ℃ of temperature, 118～120 ℃ of holding temperatures were reacted 1 hour.Adjust 138 ℃ of temperature, 138～140 ℃ of holding temperatures were reacted 4 hours, got the chlorosulphonation feed liquid.
Adjust 20～25 ℃ of temperature, 2 hours consuming time, the chlorosulphonation feed liquid of gained is joined in the retort that frozen water is housed.0～20 ℃ of holding temperature stirred 1 hour.The gained feed liquid is carried out solid-liquid separation.With-5～5 ℃ of cold water washing filter cakes to filtrate pH=4.Collect filter cake.
B, condensation
Add Sulfamic acid in retort, 166 kilograms of 2-aminoethyl ester add a step gained material, adjust 5～10 ℃ of temperature with frozen water, keep pH=9～10 with 10% sodium hydroxide solution, stirring reaction 3 hours.Adjust 35～40 ℃ of temperature, 35～40 ℃ of holding temperatures, pH=9～10, stirring reaction 3 hours.
C, neutralization reaction
The reaction solution of b step is adjusted to pH=6～6.5 with 30% hydrochloric acid soln.
D, aftertreatment
The feed liquid that the c step is obtained is refining, be finished product after the drying.Get following formula structure orange turquoise blue reactive dyestuffs.
Embodiment 4
A kind of preparation method of turquoise blue reactive dyestuffs comprises the steps:
Step a is with the step a of embodiment 3
B, condensation
Add Sulfamic acid in retort, 2-aminoethyl ester166 kilogram adds a step gained material, adjusts 5～10 ℃ of temperature with frozen water, adds 83 kilograms of 25% ammoniacal liquor, keeps pH=9～10 with 10% sodium hydroxide solution, stirring reaction 3 hours.Adjust 35～40 ℃ of temperature, 35～40 ℃ of holding temperatures, pH=9～10, stirring reaction 3 hours.
Step c, d are with the step c of embodiment 3, and d gets following formula structure turquoise blue reactive dyestuffs.
Embodiment 5
A kind of preparation method of turquoise blue reactive dyestuffs comprises the steps:
A, chlorosulphonation
In retort, add 1750 kilograms of chlorsulfonic acids, 40～50 ℃ of control temperature.2 hours consuming time with 350 kilograms of addings of CuPc. and adjust 110 ℃ of temperature, 110～115 ℃ of holding temperatures were reacted 4 hours.Adjust 65～70 ℃ of temperature, 65～70 ℃ of holding temperatures, 2 hours consuming time with 595 kilograms of addings of sulfur oxychloride.65～70 ℃ of holding temperatures were reacted 2 hours.Adjust 90 ℃ of temperature, 90～95 ℃ of holding temperatures were reacted 1 hour.Adjust 105 ℃ of temperature.105～110 ℃ of holding temperatures were reacted 1 hour, got the chlorosulphonation feed liquid.
Adjust 20～25 ℃ of temperature, 2 hours consuming time, the chlorosulphonation feed liquid of gained is joined in the retort that frozen water is housed.0～20 ℃ of holding temperature stirred 1 hour.The gained feed liquid is carried out solid-liquid separation.With-5～5 ℃ of cold water washing filter cakes to filtrate pH=5.Collect filter cake.
B, esterification
In retort, add 36.6 kilograms of Monoethanolamine MEA BASFs, the circulating water cooling.15～20 ℃ of control temperature with 36. kilograms of addings of Glacial acetic acid, added 1.5 kilograms in 98% sulfuric acid in 45～60 minutes, stir, and refluxed lower, adjusted 140～150 ℃ of temperature, and 140～150 ℃ of holding temperatures were reacted 5 hours.Adjust 5～10 ℃ of temperature.
C, condensation
A step gained material is added in the b step gained material, adjust 5～10 ℃ of temperature with frozen water, keep pH=11～12 with 20% sodium hydroxide solution, stirring reaction 1 hour.Adjust 45～50 ℃ of temperature, 45～50 ℃ of holding temperatures, pH=11～12, stirring reaction 1 hour.
D, neutralization reaction
The reaction solution of c step is adjusted to pH=6～6.5 with 30% hydrochloric acid soln.
E, aftertreatment
The feed liquid that the d step is obtained is refining, be finished product after the drying.Get following formula structure turquoise blue reactive dyestuffs.
Embodiment 6
A kind of preparation method of turquoise blue reactive dyestuffs comprises the steps:
Step a, b are with embodiment 5 step a, b
C, condensation
A step gained material is added in the b step gained material, adjust 5～10 ℃ of temperature with frozen water, add 41.5 kilograms of 25% ammoniacal liquor, keep pH=11～12 with 20% sodium hydroxide solution, stirring reaction 1 hour.Adjust 45～50 ℃ of temperature, 45～50 ℃ of holding temperatures, pH=11～12, stirring reaction 1 hour.
Steps d, e get following formula structure turquoise blue reactive dyestuffs with embodiment 5 steps d, e.
Embodiment 7
A kind of preparation method of turquoise blue reactive dyestuffs comprises the steps:
A, chlorosulphonation
In retort, add 2100 kilograms of chlorsulfonic acids, 40～50 ℃ of control temperature.2 hours consuming time with 350 kilograms of addings of CuPc. and adjust 100 ℃ of temperature, 100～102 ℃ of holding temperatures were reacted 1 hour.Adjust 120 ℃ of temperature, 120～122 ℃ of holding temperatures were reacted 4 hours, got the chlorosulphonation feed liquid.
Adjust 20～25 ℃ of temperature, 2 hours consuming time, the chlorosulphonation feed liquid of gained is joined in the retort that frozen water is housed.0～20 ℃ of holding temperature stirred 1 hour.The gained feed liquid is carried out solid-liquid separation.With-5～5 ℃ of cold water washing filter cakes to filtrate pH=5.Collect filter cake.
B, condensation
Add Sulfamic acid in retort, 2-aminoethyl ester83 kilogram adds a step gained material, adjusts 5～10 ℃ of temperature with frozen water, keeps pH=11～12 with 40% sodium hydroxide solution, stirring reaction 1 hour.Adjust 45～50 ℃ of temperature, 45～50 ℃ of holding temperatures, pH=11～12, stirring reaction 1 hour.
C, neutralization reaction
The reaction solution of b step is adjusted to pH=6～6.5 with 30% hydrochloric acid soln.
D, aftertreatment
The feed liquid that the c step is obtained is refining, be finished product after the drying.Get following formula structure turquoise blue reactive dyestuffs
Embodiment 8
A kind of preparation method of turquoise blue reactive dyestuffs comprises the steps:
Step a is with embodiment 7 step a
B, condensation
Add Sulfamic acid in retort, 83 kilograms of 2-aminoethyl ester add a step gained material, adjust 5～10 ℃ of temperature with frozen water, add 41.5 kilograms of 25% ammoniacal liquor, keep pH=11～12 with 40% sodium hydroxide solution, stirring reaction 1 hour.Adjust 45～50 ℃ of temperature, 45～50 ℃ of holding temperatures, pH=11～12, stirring reaction 1 hour.
Step c, d get following formula structure turquoise blue reactive dyestuffs with embodiment 7 step c, d
The turquoise blue reactive dyestuffs of the present invention's preparation dye hair (pad dyeing) application performance table
Product of the present invention and method are described by specific embodiment.Those skilled in the art can use for reference the links such as content appropriate change raw material of the present invention, processing condition and realize corresponding other purpose, its relevant change does not all break away from content of the present invention, all similar replacements and change will become apparent to those skilled in the art that and all be deemed to be included within the scope of the present invention.
Claims (5)
1. turquoise blue reactive dyestuffs, it is characterized in that: these reactive dyestuffs have following formula I general structure
R Wei – SO
2NH-C
2H
4OCOCH
3Or-SO
2NH-C
2H
4OSO
2NH
2
2. the preparation method of the described structure formula I of claim 1 turquoise blue reactive dyestuffs is characterized in that: comprise the steps:
A, chlorosulphonation
Add chlorsulfonic acid in retort, 40～50 ℃ of temperature of control added CuPc in 2 hours consuming time, adjust 110～140 ℃ of temperature, 110～140 ℃ of holding temperatures were reacted 4 hours, adjust 65～70 ℃ of temperature, 65～70 ℃ of holding temperatures added sulfur oxychloride in 2 hours consuming time, 65～70 ℃ of holding temperatures were reacted 2 hours, adjusted 90 ℃ of temperature, 90～95 ℃ of holding temperatures were reacted 1 hour, adjusted 105 ℃ of temperature, 105～110 ℃ of holding temperatures were reacted 1 hour, got the chlorosulphonation feed liquid;
Adjust 20～25 ℃ of temperature, 2 hours consuming time, the chlorosulphonation feed liquid of gained is joined in the retort that frozen water is housed, 0～20 ℃ of holding temperature stirred 1 hour, and the gained feed liquid is carried out solid-liquid separation, to filtrate pH=4～5, collect filter cake with-5～5 ℃ of cold water washing filter cakes;
B, esterification
Add Monoethanolamine MEA BASF in retort, 15～20 ℃ of control temperature added Glacial acetic acid in 45～60 minutes, added sulfuric acid, stir, reflux lower, adjust 120～150 ℃ of temperature, 120～150 ℃ of holding temperatures, reacted 5 hours, and adjusted 5～10 ℃ of temperature, for subsequent use;
C, condensation
A step gained material is added in the b step gained material, adjust 5～10 ℃ of temperature with frozen water, keep pH=9～12 with 10～40% sodium hydroxide solutions, stirring reaction 1～3 hour is adjusted 35～50 ℃ of temperature, 35～50 ℃ of holding temperatures, pH=9～12, stirring reaction 1～3 hour;
D, neutralization reaction
The reaction solution of c step is adjusted to pH=6～7.5 with 30% hydrochloric acid soln;
E, aftertreatment
The feed liquid that the d step is obtained is refining, be the finished product dyestuff after the drying.
3. the preparation method of described reactive dyestuffs according to claim 2 is characterized in that: add ammoniacal liquor in step c.
4. the preparation method of the described turquoise blue reactive dyestuffs of claim 1 is characterized in that: comprise the steps:
A, chlorosulphonation
Add chlorsulfonic acid in retort, 40～50 ℃ of control temperature were adjusted 100～120 ℃ of temperature with the CuPc adding in 2 hours consuming time, 100～120 ℃ of holding temperatures were reacted 1 hour, adjusted 120～140 ℃ of temperature, 120～140 ℃ of holding temperatures were reacted 3～6 hours, got the chlorosulphonation feed liquid;
Adjust 20～25 ℃ of temperature, 2 hours consuming time, the chlorosulphonation feed liquid of gained is joined in the retort that frozen water is housed, 0～20 ℃ of holding temperature stirred 1 hour, and the gained feed liquid is carried out solid-liquid separation, and-5～5 ℃ of cold water washing filter cakes of usefulness are to filtrate pH=4～5; Collect filter cake;
B, condensation
In retort, add Sulfamic acid, 2-aminoethyl ester, a step gained material is added, adjust 5～10 ℃ of temperature with frozen water, keep pH=9～12 with 10～40% sodium hydroxide solutions, stirring reaction 1～3 hour, adjust 35～50 ℃ of temperature, 35～50 ℃ of holding temperatures, pH=9～12, stirring reaction 1～3 hour;
C, neutralization reaction
The reaction solution of b step is adjusted to pH=6～7.5 with 30% hydrochloric acid soln;
D, aftertreatment
The feed liquid that the c step is obtained is refining, be finished product after the drying.
5. the preparation method of described reactive dyestuffs according to claim 4 is characterized in that: add ammoniacal liquor in step c.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210362081.0A CN102911526B (en) | 2012-09-25 | 2012-09-25 | turquoise blue reactive dye and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210362081.0A CN102911526B (en) | 2012-09-25 | 2012-09-25 | turquoise blue reactive dye and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102911526A true CN102911526A (en) | 2013-02-06 |
| CN102911526B CN102911526B (en) | 2017-06-30 |
Family
ID=47610116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210362081.0A Active CN102911526B (en) | 2012-09-25 | 2012-09-25 | turquoise blue reactive dye and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102911526B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103554982A (en) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | Turquoise blue reactive dye and preparation method thereof |
| CN104530746A (en) * | 2014-12-23 | 2015-04-22 | 浙江劲光化工有限公司 | Turquoise blue water-soluble dye and preparation method thereof |
| CN105295437A (en) * | 2015-12-02 | 2016-02-03 | 天津德凯化工股份有限公司 | Turquoise blue dye for inkjet printing and preparation method thereof |
| CN105331143A (en) * | 2015-12-02 | 2016-02-17 | 天津德凯化工股份有限公司 | Turquoise blue dye and preparing method thereof |
-
2012
- 2012-09-25 CN CN201210362081.0A patent/CN102911526B/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103554982A (en) * | 2013-09-29 | 2014-02-05 | 天津德凯化工股份有限公司 | Turquoise blue reactive dye and preparation method thereof |
| CN103554982B (en) * | 2013-09-29 | 2017-10-24 | 天津德凯化工股份有限公司 | A kind of Turquoise blue reactive dye and preparation method thereof |
| CN104530746A (en) * | 2014-12-23 | 2015-04-22 | 浙江劲光化工有限公司 | Turquoise blue water-soluble dye and preparation method thereof |
| CN105295437A (en) * | 2015-12-02 | 2016-02-03 | 天津德凯化工股份有限公司 | Turquoise blue dye for inkjet printing and preparation method thereof |
| CN105331143A (en) * | 2015-12-02 | 2016-02-17 | 天津德凯化工股份有限公司 | Turquoise blue dye and preparing method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102911526B (en) | 2017-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102911526A (en) | Turquoise blue reactive dye and preparation method thereof | |
| CN1152930A (en) | Reactive monoazo dyestuffs | |
| CN102504585A (en) | Blue active dye, preparation method and application thereof | |
| CN102876073A (en) | Turquoise blue reactive dye and preparation method thereof | |
| CN102911523A (en) | Blue reactive dye and preparation method thereof | |
| CN101880465B (en) | Production method for acid dye finished product | |
| CN103554982A (en) | Turquoise blue reactive dye and preparation method thereof | |
| CN107163615B (en) | A kind of environment-friendly type Weak acid red dyestuff and preparation method thereof | |
| CN101955682A (en) | Method for preparing high-performance organic pigment PR176 | |
| CN104725898A (en) | Cyanide and copper removal method during production process of cyaniding dye | |
| CN102391675A (en) | Azo reactive dye and preparation method thereof | |
| CN102260417B (en) | Method for preparing reactive brilliant blue | |
| CN102337044A (en) | Reactive dye and preparation method thereof | |
| CN102321387A (en) | Nylon reactive yellow dye and preparation method thereof | |
| CN102504584A (en) | Azo type blue reactive dye, and its preparation method and application | |
| CN102911522A (en) | Blue reactive dye | |
| CN102876077A (en) | Black reactive dye and preparation method thereof | |
| CN110878176B (en) | Reactive dye compound and preparation method thereof | |
| CN102504586A (en) | Blue reactive dye and its preparation method | |
| CN102433027A (en) | Azo blue active dye and preparation method thereof | |
| CN102391684A (en) | Yellow reactive dye for dyeing nylon and preparation method thereof | |
| CN109594358B (en) | Reactive dye ink and preparation method thereof | |
| CN106810905A (en) | A kind of active red dye and its preparation and application | |
| CN103602099A (en) | Blue reactive dye | |
| CN101481535B (en) | Preparation of dye brilliant blue KN-R |
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 | ||
| PP01 | Preservation of patent right |
Effective date of registration: 20230131 Granted publication date: 20170630 |
|
| PP01 | Preservation of patent right |