CN105733292A - Preparation method of acid black ACE - Google Patents
Preparation method of acid black ACE Download PDFInfo
- Publication number
- CN105733292A CN105733292A CN201610057982.7A CN201610057982A CN105733292A CN 105733292 A CN105733292 A CN 105733292A CN 201610057982 A CN201610057982 A CN 201610057982A CN 105733292 A CN105733292 A CN 105733292A
- Authority
- CN
- China
- Prior art keywords
- acid
- acid black
- liquid
- coupling
- amino
- 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
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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of an acid black ACE. The method comprises the following steps: (1) diazotizing 2-amino-4-sodium ortho-nitrophenolate to obtain a diazo liquid; (2) directly adding N-phenyl-2-amino-5-phenol-7-sulfonic acid to the diazo liquid, firstly, carrying out acid coupling, and then adding alkali to adjust the pH value for alkaline coupling to obtain a coupled liquid; (3) adding chromium acetate to an acid black 172 conjugate for 1:1 complexing, so as to obtain a 1:1 complexing liquid of acid black 172; and (4) adding the 1:1 complexing liquid of the acid black 172 to the coupled liquid, carrying out secondary complexing, and adding the 1:1 complexing liquid of the acid black 172 in batches, so as to obtain an acid black ACE dye with relatively good color light performance. The production technology is simple; a secondary diazo coupling one-pot method is high in production efficiency and few in side reaction and impurity; the product quality is good; the product is free of heavy metal chromium; salting is not needed; the product is directly dried in a spraying manner; and the production cost is low.
Description
Technical field
The invention belongs to metal complex azo dye field, the preparation method of a kind of acid black ACE.
Background technology
Acid stain great majority contain sulfonate sodium, can be dissolved in water, and lovely luster, chromatograph are complete.It is mainly used in the dyeing such as Pilus Caprae seu Ovis, silkworm silk and chinlon, it is possible to for aspects such as leather, paper, inks.1: 2 premetallized dye is divided into K-type (without sulfonic group), S type (single sulfonic group), M type (disulfonic acid base), and wherein the comprehensive quality index (vividness, level-dyeing property, wet colour fastness) of S type (being also called asymmetric) dyestuff is fine.Acid black ACE is suitable for deep colour dyeing in chinlon, all has good pile-on properties on different classes of nylon fabric, bright-colored, chromatograph is broad, has the good compatibility, medium migration property, excellent wet fastness, is particularly suitable for brocade/cotton dyeing.
Acid black ACE is exactly asymmetric 1: 2 premetallized dye of typical black, after general technology process is 2-Amino-4-nitrophenol diazotising, respectively under the conditions of acid and alkalescence with N-phenyl-2-amino-5-naphthols-7-sulfonic acid coupling, obtain azo A and azo B；6-nitro-1,2,4-acid oxysome and beta naphthal coupling obtain azo C；Azo C and chromium oxide complex reaction obtain complex D；Complex D reacts in the basic conditions with azo A, azo B and obtains asymmetric 1: 2 premetallized dye of black (acid black ACE).
Current most of techniques are all diazo couplings respectively, obtain three kinds of conjugates, after product reaction completely, owing to reaction is complete or proportioning is forbidden, in addition it is also necessary to the step such as saltout；Product yield is relatively low, and side reaction and impurity are more；Production cost is higher, and production efficiency is relatively low, and discharging of waste liquid amount is big, and environmental pollution is serious, and treatment cost is higher；Wherein it is mainly in salting-out step and produces substantial amounts of oxo-compound analysis, the operations such as the dyestuff filter-cakes concurrently separated out is also performed to dry, pulverizing.
Summary of the invention
Present invention aim to overcome that the deficiencies in the prior art, it is provided that a kind of production technology is simple, 2 diazo coupling one kettle ways, production efficiency is high, side reaction and impurity are few, good product quality, heavy metal free chromium in product, without saltouing, the direct spray drying of product, the preparation method of the acid black ACE that production cost is low.
The preparation method of a kind of acid black ACE, comprises the steps:
(1), diazotising:
Coupling pot adds water, hydrochloric acid, 2-Amino-4-nitrophenol sodium, stirs 10～20 minutes, adds 2000～3000kg ice is cooled to 0～5 DEG C, add sodium nitrite solution, holding temperature 5～10 DEG C in 10～20 minutes.After sodium nitrite adds, keep the micro-excess of sodium nitrite, now the detection micro-indigo plant of starch potassium iodide paper, be subsequently adding sulfamic acid 8～12 DEG C of insulation reaction 1～1.5 hours, eliminate the sodium nitrite of excess；Obtain diazo liquid；
(2), coupling:
In coupling pot diazo liquid, add N-phenyl-2-amino-5-phenol-7-sulfonic acid dry powder carry out acid coupling, after stirring evenly, the most naturally heat up, when temperature rises the most naturally, slowly start to heat with hot-water coil pipe, within 20～30 minutes, it is warmed up to 35 DEG C, 35～42 DEG C of insulation reaction 4～6 hours, add 5000～7000kg ice is cooled to 3～5 DEG C, start to drip 30% liquid caustic soda and carry out alkaline coupling, the most slowly adding liquid caustic soda with 4～6 hours adjusts pH value to 11.0～11.5, during adding liquid caustic soda, first 3 hours, control couple temperature 3～10 DEG C, after 3 hours, control couple temperature 8～12 DEG C, after terminal arrives, obtain coupling solution；
(3), the 1:1 complexation of acid black 172 conjugates:
After acid black 172 conjugates terminal arrives, being cooled to 80～90 DEG C, with salt acid for adjusting pH value to 1～2, be subsequently adding chromium acetate solution, 80～90 DEG C of insulation reaction 3～4 hours, pH value keeps to 1～2.Obtain the 1:1 complex liquid of acid black 172；(4), secondary complexation:
Coupling solution is warmed up to 90 DEG C, the 80～90% of the 1:1 complex liquid of addition acid black 172, at 89～91 DEG C, insulated and stirred 1.5～3 hours, with 2～3 hours, the most slowly add liquid caustic soda, adjust pH value to 6.8～7.0, again add acid black 172 1:1 complex liquid 5～10%, heat up 90～95 DEG C, stirring 30～60 minutes, slow tune adds liquid caustic soda, adjusts pH value 6.8～7.0,90～95 DEG C of insulation reaction 0.5～1 hour, add the 1:1 complex liquid of remaining acid black 172, adjust pH value 6.8～7.0, insulation reaction 0.5～1 hour；After confirming that terminal arrives, sampling detection, direct spray drying after coloured light, dissolubility detection are qualified, obtain acid black ACE dry powder.
2-Amino-4-nitrophenol sodium described in described step (1): hydrochloric acid: water: the mass ratio of sodium nitrite is 1:1.35～1.70:2.70～3.4:0.38～0.42；Described sodium nitrite solution Sodium Nitrite, the mass ratio of water are 1:2；The addition of sulfamic acid is the 1% of 2-Amino-4-nitrophenol sodium quality.
N-phenyl-2-amino-5-phenol-7-sulfonic acid described in described step (2) is N-phenyl-2-amino-5-phenol-7-sulfonic acid dry powder.
2-Amino-4-nitrophenol sodium described in described step (2): the mass ratio of N-phenyl-2-amino-5-phenol-7-sulfonic acid is 1:0.85～0.90.
Acid black 172 conjugates described in described step (3), the mol ratio of chromium acetate are 1:1.02；2-Amino-4-nitrophenol sodium, the mol ratio of acid black 172 conjugates are 1:0.95～1.
Reaction equation:
(1) diazotising
(2) acid coupling
(3) alkaline coupling
(4) the 1:1 complexation of acid black 172 conjugates
3,1:1Cr closes
(5) secondary complexation
Compared with prior art, beneficial effects of the present invention is embodied in:
(1), acid coupling and alkaline coupling use one kettle way, high-temperature acidic coupling and low-temperature alkali even summation.Completely, side reaction is less in reaction.
(2), coupling uses and is directly added into N-phenyl-2-amino-5-phenol-7-sulfonic acid dry powder, it is not necessary to dissolve, and can reduce reactions steps and reduce cost.Also the generation of side reaction can be reduced.
(3), the strict temperature controlling complexation and pH value and the ratio of three kinds of conjugates, the 1:1 complex liquid of acid black 172 uses and is dividedly in some parts, and improves the quality of product.
Detailed description of the invention:
Embodiment 1
(1), diazotising:
1177kg water, 588kg hydrochloric acid, 436kg2-Amino-4-nitrophenol sodium is added in coupling pot, stir 10～20 minutes, add 2000～3000kg ice is cooled to 0～5 DEG C, in 10～20 minutes, add sodium nitrite solution (165kg sodium nitrite+330kg water), holding temperature 5～10 DEG C.After sodium nitrite solution adds, keep the micro-excess of sodium nitrite (detection: the micro-indigo plant of starch potassium iodide paper), be subsequently adding 4.5kg sulfamic acid 8～12 DEG C of insulation reaction 1～1.5 hours, eliminate the sodium nitrite of excess.Obtain diazo liquid；
(2), coupling:
In coupling pot diazo liquid, add 370kgN-phenyl-2-amino-5-phenol-7-sulfonic acid dry powder carry out acid coupling, after stirring evenly, the most naturally heat up, when temperature rises the most naturally, slowly start to heat with hot-water coil pipe, within 20～30 minutes, it is warmed up to 35 DEG C, 35～42 DEG C of insulation reaction 4～6 hours, add 5000～7000kg ice is cooled to 3～5 DEG C, start to drip 30% liquid caustic soda and carry out alkaline coupling, the most slowly adding liquid caustic soda with 4～6 hours adjusts pH value to 11.0～11.5, during adding liquid caustic soda, first 3 hours, control couple temperature 3～10 DEG C, after 3 hours, control couple temperature 8～12 DEG C, after terminal arrives, obtain coupling solution.
(3), the 1:1 complexation of acid black 172 conjugates:
After 1033kg acid black 172 conjugates terminal arrives, being cooled to 80～90 DEG C, with salt acid for adjusting pH value to 1～2, be subsequently adding chromium acetate solution (containing chromium acetate 539kg), 80～90 DEG C of insulation reaction 3～4 hours, pH value keeps to 1～2.Obtain the 1:1 complex liquid of 5000kg acid black 172.
(4), secondary complexation:
Coupling solution is warmed up to 90 DEG C, add the 1:1 complex liquid of 4000kg acid black 172, at 89～91 DEG C, insulated and stirred 1.5～3 hours, with 2～3 hours, the most slowly add liquid caustic soda, adjust pH value to 6.8～7.0, again add the 1:1 complex liquid of 600kg acid black 172, heat up 90～95 DEG C, stirring 30～60 minutes, slow tune adds liquid caustic soda, adjusts pH value 6.8～7.0,90～95 DEG C of insulation reaction 0.5～1 hour, add the 1:1 complex liquid of remaining acid black 172, adjust pH value 6.8～7.0, insulation reaction 0.5～1 hour.After confirming that terminal arrives, sampling detection, direct spray drying after coloured light, dissolubility detection are qualified, obtain 2050kg acid black ACE dry powder.
Embodiment 2
(1), diazotising:
1482kg water, 741kg hydrochloric acid, 436kg2-Amino-4-nitrophenol sodium is added in coupling pot, stir 10～20 minutes, add 2000～3000kg ice is cooled to 0～5 DEG C, in 10～20 minutes, add sodium nitrite solution (183kg sodium nitrite+366kg water), holding temperature 5～10 DEG C.After sodium nitrite solution adds, keep the micro-excess of sodium nitrite (detection: the micro-indigo plant of starch potassium iodide paper), be subsequently adding 4.5kg sulfamic acid 8～12 DEG C of insulation reaction 1～1.5 hours, eliminate the sodium nitrite of excess.Obtain diazo liquid；
(2), coupling:
In coupling pot diazo liquid, add 392kgN-phenyl-2-amino-5-phenol-7-sulfonic acid dry powder carry out acid coupling, after stirring evenly, the most naturally heat up, when temperature rises the most naturally, slowly start to heat with hot-water coil pipe, within 20～30 minutes, it is warmed up to 35 DEG C, 35～42 DEG C of insulation reaction 4～6 hours, add 5000～7000kg ice is cooled to 3～5 DEG C, start to drip 30% liquid caustic soda and carry out alkaline coupling, the most slowly adding liquid caustic soda with 4～6 hours adjusts pH value to 11.0～11.5, during adding liquid caustic soda, first 3 hours, control couple temperature 3～10 DEG C, after 3 hours, control couple temperature 8～12 DEG C, after terminal arrives, obtain coupling solution.
(3), the 1:1 complexation of acid black 172 conjugates:
After 1087kg acid black 172 conjugates terminal arrives, being cooled to 80～90 DEG C, with salt acid for adjusting pH value to 1～2, be subsequently adding chromium acetate solution (containing chromium acetate 567kg), 80～90 DEG C of insulation reaction 3～4 hours, pH value keeps to 1～2.Obtain the 1:1 complex liquid of 5000kg acid black 172.
(4), secondary complexation:
Coupling solution is warmed up to 90 DEG C, add the 1:1 complex liquid of 4500kg acid black 172, at 89～91 DEG C, insulated and stirred 1.5～3 hours, with 2～3 hours, the most slowly add liquid caustic soda, adjust pH value to 6.8～7.0, again add the 1:1 complex liquid of 250kg acid black 172, heat up 90～95 DEG C, stirring 30～60 minutes, slow tune adds liquid caustic soda, adjusts pH value 6.8～7.0,90～95 DEG C of insulation reaction 0.5～1 hour, add the 1:1 complex liquid of remaining acid black 172, adjust pH value 6.8～7.0, insulation reaction 0.5～1 hour.After confirming that terminal arrives, sampling detection, direct spray drying after coloured light, dissolubility detection are qualified, obtain 2150kg acid black ACE dry powder.
Embodiment 3
(1), diazotising:
1300kg water, 650kg hydrochloric acid, 436kg2-Amino-4-nitrophenol sodium is added in coupling pot, stir 10～20 minutes, add 2000～3000kg ice is cooled to 0～5 DEG C, in 10～20 minutes, add sodium nitrite solution (175kg sodium nitrite+350kg water), holding temperature 5～10 DEG C.After sodium nitrite solution adds, keep the micro-excess of sodium nitrite (detection: the micro-indigo plant of starch potassium iodide paper), be subsequently adding 4.5kg sulfamic acid 8～12 DEG C of insulation reaction 1～1.5 hours, eliminate the sodium nitrite of excess.Obtain diazo liquid；
(2), coupling:
In coupling pot diazo liquid, add 380kgN-phenyl-2-amino-5-phenol-7-sulfonic acid dry powder carry out acid coupling, after stirring evenly, the most naturally heat up, when temperature rises the most naturally, slowly start to heat with hot-water coil pipe, within 20～30 minutes, it is warmed up to 35 DEG C, 35～42 DEG C of insulation reaction 4～6 hours, add 5000～7000kg ice is cooled to 3～5 DEG C, start to drip 30% liquid caustic soda and carry out alkaline coupling, the most slowly adding liquid caustic soda with 4～6 hours adjusts pH value to 11.0～11.5, during adding liquid caustic soda, first 3 hours, control couple temperature 3～10 DEG C, after 3 hours, control couple temperature 8～12 DEG C, after terminal arrives, obtain coupling solution.
(3), the 1:1 complexation of acid black 172 conjugates:
After 1050kg acid black 172 conjugates terminal arrives, being cooled to 80～90 DEG C, with salt acid for adjusting pH value to 1～2, be subsequently adding chromium acetate solution (containing chromium acetate 550kg), 80～90 DEG C of insulation reaction 3～4 hours, pH value keeps to 1～2.Obtain the 1:1 complex liquid of 5000kg acid black 172.
(4), secondary complexation:
Coupling solution is warmed up to 90 DEG C, add the 1:1 complex liquid of 4250kg acid black 172, at 89～91 DEG C, insulated and stirred 1.5～3 hours, with 2～3 hours, the most slowly add liquid caustic soda, adjust pH value to 6.8～7.0, again add the 1:1 complex liquid of 500kg acid black 172, heat up 90～95 DEG C, stirring 30～60 minutes, slow tune adds liquid caustic soda, adjusts pH value 6.8～7.0,90～95 DEG C of insulation reaction 0.5～1 hour, add the 1:1 complex liquid of remaining acid black 172, adjust pH value 6.8～7.0, insulation reaction 0.5～1 hour.After confirming that terminal arrives, sampling detection, direct spray drying after coloured light, dissolubility detection are qualified, obtain 2100kg acid black ACE dry powder.
Embodiment 4
(1), diazotising:
1177kg water, 600kg hydrochloric acid, 436kg2-Amino-4-nitrophenol sodium is added in coupling pot, stir 10～20 minutes, add 2000～3000kg ice is cooled to 0～5 DEG C, in 10～20 minutes, add sodium nitrite solution (170kg sodium nitrite+340kg water), holding temperature 5～10 DEG C.After sodium nitrite solution adds, keep the micro-excess of sodium nitrite (detection: the micro-indigo plant of starch potassium iodide paper), be subsequently adding 4.5kg sulfamic acid 8～12 DEG C of insulation reaction 1～1.5 hours, eliminate the sodium nitrite of excess.Obtain diazo liquid；
(2), coupling:
In coupling pot diazo liquid, add 375kgN-phenyl-2-amino-5-phenol-7-sulfonic acid dry powder carry out acid coupling, after stirring evenly, the most naturally heat up, when temperature rises the most naturally, slowly start to heat with hot-water coil pipe, within 20～30 minutes, it is warmed up to 35 DEG C, 35～42 DEG C of insulation reaction 4～6 hours, add 5000～7000kg ice is cooled to 3～5 DEG C, start to drip 30% liquid caustic soda and carry out alkaline coupling, the most slowly adding liquid caustic soda with 4～6 hours adjusts pH value to 11.0～11.5, during adding liquid caustic soda, first 3 hours, control couple temperature 3～10 DEG C, after 3 hours, control couple temperature 8～12 DEG C, after terminal arrives, obtain coupling solution.
(3), the 1:1 complexation of acid black 172 conjugates:
After 1080kg acid black 172 conjugates terminal arrives, being cooled to 80～90 DEG C, with salt acid for adjusting pH value to 1～2, be subsequently adding chromium acetate solution (containing chromium acetate 560kg), 80～90 DEG C of insulation reaction 3～4 hours, pH value keeps to 1～2.Obtain the 1:1 complex liquid of 5000kg acid black 172.
(4), secondary complexation:
Coupling solution is warmed up to 90 DEG C, add the 1:1 complex liquid of 4300kg acid black 172, at 89～91 DEG C, insulated and stirred 1.5～3 hours, with 2～3 hours, the most slowly add liquid caustic soda, adjust pH value to 6.8～7.0, again add the 1:1 complex liquid of 600kg acid black 172, heat up 90～95 DEG C, stirring 30～60 minutes, slow tune adds liquid caustic soda, adjusts pH value 6.8～7.0,90～95 DEG C of insulation reaction 0.5～1 hour, add the 1:1 complex liquid of remaining acid black 172, adjust pH value 6.8～7.0, insulation reaction 0.5～1 hour.After confirming that terminal arrives, sampling detection, direct spray drying after coloured light, dissolubility detection are qualified, obtain 2080kg acid black ACE dry powder.
Claims (5)
1. the preparation method of an acid black ACE, it is characterised in that: comprise the steps:
(1), diazotising:
Coupling pot adds water, hydrochloric acid, 2-Amino-4-nitrophenol sodium, stirs 10～20 minutes, adds 2000～3000kg ice is cooled to 0～5 DEG C, add sodium nitrite solution, holding temperature 5～10 DEG C in 10～20 minutes；After sodium nitrite adds, keep the micro-excess of sodium nitrite, now the detection micro-indigo plant of starch potassium iodide paper, be subsequently adding sulfamic acid 8～12 DEG C of insulation reaction 1～1.5 hours, eliminate the sodium nitrite of excess；Obtain diazo liquid；
(2), coupling:
In coupling pot diazo liquid, add N-phenyl-2-amino-5-phenol-7-sulfonic acid dry powder carry out acid coupling, after stirring evenly, the most naturally heat up, when temperature rises the most naturally, slowly start to heat with hot-water coil pipe, within 20～30 minutes, it is warmed up to 35 DEG C, 35～42 DEG C of insulation reaction 4～6 hours, add 5000～7000kg ice is cooled to 3～5 DEG C, start to drip 30% liquid caustic soda and carry out alkaline coupling, the most slowly adding liquid caustic soda with 4～6 hours adjusts pH value to 11.0～11.5, during adding liquid caustic soda, first 3 hours, control couple temperature 3～10 DEG C, after 3 hours, control couple temperature 8～12 DEG C, after terminal arrives, obtain coupling solution；
(3), the 1:1 complexation of acid black 172 conjugates:
After acid black 172 conjugates terminal arrives, being cooled to 80～90 DEG C, with salt acid for adjusting pH value to 1～2, be subsequently adding chromium acetate solution, 80～90 DEG C of insulation reaction 3～4 hours, pH value keeps to 1～2；Obtain the 1:1 complex liquid of acid black 172；
(4), secondary complexation:
Coupling solution is warmed up to 90 DEG C, the 80～90% of the 1:1 complex liquid of addition acid black 172, at 89～91 DEG C, insulated and stirred 1.5～3 hours, with 2～3 hours, the most slowly add liquid caustic soda, adjust pH value to 6.8～7.0, again add acid black 172 1:1 complex liquid 5～10%, heat up 90～95 DEG C, stirring 30～60 minutes, slow tune adds liquid caustic soda, adjusts pH value 6.8～7.0,90～95 DEG C of insulation reaction 0.5～1 hour, add the 1:1 complex liquid of remaining acid black 172, adjust pH value 6.8～7.0, insulation reaction 0.5～1 hour；After confirming that terminal arrives, sampling detection, direct spray drying after coloured light, dissolubility detection are qualified, obtain acid black ACE dry powder.
2. according to the preparation method of a kind of acid black ACE described in claim 1, it is characterized in that, the 2-Amino-4-nitrophenol sodium described in described step (1): hydrochloric acid: water: the mass ratio of sodium nitrite is 1:1.35～1.70:2.70～3.4:0.38～0.42；Described sodium nitrite solution Sodium Nitrite, the mass ratio of water are 1:2；The addition of sulfamic acid is the 1% of 2-Amino-4-nitrophenol sodium quality.
3. according to the preparation method of a kind of acid black ACE described in claim 1, it is characterised in that the N-phenyl-2-amino-5-phenol-7-sulfonic acid described in described step (2) is N-phenyl-2-amino-5-phenol-7-sulfonic acid dry powder.
4. according to the preparation method of a kind of acid black ACE described in claim 1, it is characterised in that the 2-Amino-4-nitrophenol sodium described in described step (2): the mass ratio of N-phenyl-2-amino-5-phenol-7-sulfonic acid is 1:0.85～0.90.
5. according to the preparation method of a kind of acid black ACE described in claim 1, it is characterised in that the acid black 172 conjugates described in described step (3), the mol ratio of chromium acetate are 1:1.02；2-Amino-4-nitrophenol sodium, the mol ratio of acid black 172 conjugates are 1:0.95～1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610057982.7A CN105733292A (en) | 2016-01-28 | 2016-01-28 | Preparation method of acid black ACE |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610057982.7A CN105733292A (en) | 2016-01-28 | 2016-01-28 | Preparation method of acid black ACE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105733292A true CN105733292A (en) | 2016-07-06 |
Family
ID=56246889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610057982.7A Pending CN105733292A (en) | 2016-01-28 | 2016-01-28 | Preparation method of acid black ACE |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105733292A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111171594A (en) * | 2019-12-31 | 2020-05-19 | 恒升化工有限公司 | Preparation method of metal complex dye with low residual chromium ions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1831045A (en) * | 2006-01-26 | 2006-09-13 | 浙江龙盛集团股份有限公司 | Bisdiazo metal complex dye and its prepn. method |
-
2016
- 2016-01-28 CN CN201610057982.7A patent/CN105733292A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1831045A (en) * | 2006-01-26 | 2006-09-13 | 浙江龙盛集团股份有限公司 | Bisdiazo metal complex dye and its prepn. method |
Non-Patent Citations (2)
| Title |
|---|
| 唐沛兰: "酸性黑ACE合成研究", 《染料与染色》 * |
| 孙桂春: "金属络合染料酸性黑ACE的合成", 《染料与染色》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111171594A (en) * | 2019-12-31 | 2020-05-19 | 恒升化工有限公司 | Preparation method of metal complex dye with low residual chromium ions |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105694524B (en) | A kind of preparation method of acid black 172 | |
| CN101235216B (en) | Orange reactive dyestuffs and preparation method thereof | |
| CN105733292A (en) | Preparation method of acid black ACE | |
| CN105273437B (en) | Red reactive dye as well as preparation method and application thereof | |
| CN101705019B (en) | Red reactive dye for wool and preparation method thereof | |
| CN103351645A (en) | Reactive blue dye and preparation method thereof | |
| CN101704770B (en) | Method for preparing purple reactive dye | |
| CN101792613B (en) | Yellow reactive dye for wool and preparation method and application thereof | |
| CN101481522B (en) | Preparation of red reactive dye for fur | |
| CN105440728A (en) | Red reactive dye and preparation method thereof | |
| CN101735655B (en) | Red reactive dye for wool and preparation method thereof | |
| CN102433025A (en) | Black active dye and preparation method thereof | |
| CN101709044B (en) | Preparation method of purple active dye for wool | |
| CN101735657B (en) | Method for preparing active dye for purple wool | |
| CN101735652B (en) | Red reactive dye and preparation method thereof | |
| CN101735653B (en) | Red reactive dye for wool and preparation method thereof | |
| CN102391675A (en) | Azo reactive dye and preparation method thereof | |
| CN101481525B (en) | Preparation of reactive red GN dye for fur | |
| CN101735656B (en) | Red reactive dye for wool | |
| CN101723863B (en) | Preparation method of purple active dye | |
| CN101724292B (en) | Wool orange reactive dye and preparation method thereof | |
| CN101735654B (en) | Reactive dye for wool and preparation method thereof | |
| CN101705017B (en) | Orange reactive dye for wool and preparation method thereof | |
| CN103284419A (en) | Method for optimizing seawater pearl color | |
| CN101906256A (en) | Orange reactive dye and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20160706 |