CN104497617A - Vat dye brown GG and preparation method thereof - Google Patents
Vat dye brown GG and preparation method thereof Download PDFInfo
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- CN104497617A CN104497617A CN201410702950.9A CN201410702950A CN104497617A CN 104497617 A CN104497617 A CN 104497617A CN 201410702950 A CN201410702950 A CN 201410702950A CN 104497617 A CN104497617 A CN 104497617A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 239000000984 vat dye Substances 0.000 title claims abstract description 19
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims abstract description 29
- -1 anthraquinone compound Chemical class 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- 238000010792 warming Methods 0.000 claims description 22
- 238000009413 insulation Methods 0.000 claims description 20
- 239000003513 alkali Substances 0.000 claims description 19
- 238000004140 cleaning Methods 0.000 claims description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 16
- 239000000835 fiber Substances 0.000 claims description 16
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 16
- 239000007790 solid phase Substances 0.000 claims description 15
- 238000007670 refining Methods 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 229940040526 anhydrous sodium acetate Drugs 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 239000011775 sodium fluoride Substances 0.000 claims description 8
- 235000013024 sodium fluoride Nutrition 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- 238000006482 condensation reaction Methods 0.000 claims description 7
- 239000006210 lotion Substances 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 208000005156 Dehydration Diseases 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 238000005204 segregation Methods 0.000 claims description 5
- 238000005507 spraying Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 235000013877 carbamide Nutrition 0.000 claims description 3
- PLUFITIFLBGFPN-UHFFFAOYSA-N 1,2-dichloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1 PLUFITIFLBGFPN-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 5
- 238000004043 dyeing Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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Abstract
The invention provides a vat dye brown GG and a preparation method thereof. The vat dye brown GG which can be directly synthesized belongs to an anthraquinone compound; the properties such as color and light accord with the quality standard of vat brown GG which is spliced and mixed; meanwhile, the preparation method of the vat dye brown GG provided by the invention is simple in process, and short in production cycle; and the prepared dye is good in dyeing property.
Description
Technical field
The invention belongs to preparation of dyestuff technical field, relate to a kind of vat dyes palm fibre GG and preparation method.
Background technology
Vat Brown GG is also known as intellectual circle palm fibre GG, and outward appearance is dark brown powder, water insoluble, is mainly used in the dyeing of cotton fabric.Vat Brown GG used in the market is formed by Vat Brown 3GR and Vat Olive R blending, and its blending ratio is: Vat Brown 3GR 72%, Vat Olive R 28%.Two kinds of raw materials need be produced respectively, complex process, and it is necessary for strengthening the research of Vat Brown GG, and the preparation method for Vat Brown GG dyestuff need further exploitation.
Summary of the invention
The object of the present invention is to provide a kind of vat dyes palm fibre GG that can directly synthesize, the performances such as its coloured light all meet the quality standard of the Vat Brown GG of blending, there is provided the preparation method of vat dyes of the present invention palm fibre GG, technique dyeing performance that is simple, with short production cycle, that obtain is good simultaneously.Vat dyes palm fibre GG of the present invention, belong to anthraquinone analog compound, principal constituent structural formula is:
The preparation method of the present invention above-mentioned vat dyes palm fibre GG, step is:
1) condensation poach: 1,5-dichloroanthraquinone and 1-aminoanthraquinone, under the existence of copper powder, take anhydrous sodium carbonate as acid binding agent, carry out solid phase condensation reaction, generate three anthraquinone imines, by heating poach, the inorganic salt in three anthraquinone imines crude products are removed, thus obtain refining three anthraquinone imines.
1,5-dichloroanthraquinone, 1-aminoanthraquinone, copper powder and anhydrous sodium carbonate are mixed, 100 ~ 120 DEG C of dehydrations more than 40min, 1.5 ~ 4h are warming up to 260 ~ 265 DEG C, carry out solid phase condensation reaction, insulation 8h, cooling, pulverize, generate three anthraquinone imines crude products, three anthraquinone imines crude products are added to the water, stir, be warming up to 90 ~ 95 DEG C, insulation 1h, add water and be cooled to less than 60 DEG C, filter, be washed to neutrality, drying, to moisture content≤1%, generates refining three anthraquinone imines.
1,5-described dichloroanthraquinone: 1-aminoanthraquinone: copper powder: anhydrous sodium carbonate: the mass ratio of water is 100 ~ 150:150 ~ 200:100 ~ 120:3 ~ 10:3000.
Described cool-down method is: Temperature fall 0.5h, cold water cooling 4h.
2) ring-closure reaction: refining three anthraquinone imines carry out ring-closure reaction in the ring structure closed loop agent of urea, Sodium Fluoride, sodium acetate, anhydrous, aluminum chloride.
In temperature lower than at 50 DEG C, urea, Sodium Fluoride, sodium acetate, anhydrous and aluminum chloride and refining three anthraquinone imines are added in reactor, batch mixing heat temperature raising, outer temperature is risen to 190 ~ 260 DEG C and carries out foamable reaction by 45 ~ 65min gradually, when being warming up to 180 ~ 200 DEG C in solid phase, insulation 10 ~ 40min, is cooled to less than 60 DEG C, pulverize, obtain closed loop material.
Described refining three anthraquinone imines: urea: Sodium Fluoride: sodium acetate, anhydrous: aluminum chloride mass ratio is 80 ~ 100:60 ~ 100:20 ~ 50:4.5:200.
Described cool-down method is: Temperature fall 0.5h, cold water spraying cooling 3 ~ 5h.
3) to emanate alkali cleaning: segregation under certain acidity also removes a large amount of ring structure agent and copper, iron (wherein impurity iron is brought into by steel bomb) and obtain material of emanating with alkaline rinse washing.
Under stirring, closed loop material is added to the water, then adds sulfuric acid, be warming up to 90 ~ 95 DEG C, insulation 1h, then thin up be cooled to less than 60 DEG C, filters, is washed to neutrality, then adds the washing lotion of water preparation at the bottom of liquid caustic soda and alkali cleaning, alkali cleaning, then be washed to neutrality, dry, obtain vat dyes palm fibre GG.
Described closed loop material: water: sulfuric acid: liquid caustic soda: the mass ratio of water at the bottom of alkali cleaning is 350:3000:73 ~ 110:300 ~ 400:3500.
Described washing lotion compound method is: under stirring, be slowly added to the water by liquid caustic soda, and after stirring 15min, be warming up to 60 ~ 70 DEG C, alkali cleaning is for subsequent use, described liquid caustic soda concentration >=30%.
Described sulfuric acid concentration is >=92.5%.
A kind of vat dyes palm fibre GG and preparation method, relative to prior art, have the following advantages:
1) can directly synthesize, do not need other dyestuff blendings, the performances such as its coloured light all meet the quality standard of the Vat Brown GG of blending, and colour fastness is better.
2) technique is simple, with short production cycle, and obtained dyeing performance is good.
3) utilize solid phase condensation and ring-closure reaction, not with an organic solvent, reduce production cost, decrease three waste discharge, meet environmental requirement.
Embodiment
Below in conjunction with embodiment and comparative example, advantage of the present invention is described further.
Table 1 reaction raw materials and specification
Embodiment 1
1) condensation poach: by 1,5-dichloroanthraquinone 120kg, 1-aminoanthraquinone 160kg, copper powder 4kg and anhydrous sodium carbonate 105kg mix, and 110 DEG C of dehydrations 1h, 3h are warming up to 260 DEG C, carry out solid phase condensation reaction, 260 ~ 265 DEG C of insulations 8h, Temperature fall 0.5h, cold water cooling 4h, pulverize, generate three anthraquinone imines crude products, three anthraquinone imines crude products are added in 3000kg water, stir, be warming up to 90 ~ 95 DEG C, insulation 1h, adds water and is cooled to 60 DEG C, filters, be washed to neutrality, drying, to moisture content≤1%, generates refining three anthraquinone imines.
2) ring-closure reaction: at 45 DEG C, in solid phase reactor, add urea 75kg, Sodium Fluoride 30kg, sodium acetate, anhydrous 4.5kg, aluminum chloride 200kg and refining three anthraquinone imines 85kg batch mixings, heat temperature raising, outer temperature is risen to 190 DEG C by 1h gradually, foamable reaction is carried out in 190 ~ 250 DEG C, when being warming up to 190 ~ 250 DEG C in solid phase, insulation 20min, Temperature fall 0.5h, cold water spraying cooling 3.5h, be cooled to 60 DEG C, pulverize, obtain closed loop material.
3) segregation alkali cleaning: under stirring, closed loop material 350kg is added in 2200kgkg water, then add the sulfuric acid 85kg of 95%, be warming up to 90 DEG C, insulation 1h, the 800kg that then adds water dilutes and is cooled to less than 60 DEG C, filter, be washed to neutrality, then add the washing lotion of 65 DEG C prepared by water 3500kg at the bottom of concentration 35% liquid caustic soda 350kg and alkali cleaning, alkali cleaning, then be washed to neutrality, dry, obtain vat dyes palm fibre GG, sampling detects, and dark brown powder, purity is 98.5%.
Embodiment 2
1) condensation poach: by 1,5-dichloroanthraquinone 120kg, 1-aminoanthraquinone 190kg, copper powder 8kg and anhydrous sodium carbonate 110kg mix, and 105 DEG C of dehydrations 50min, 3.5h are warming up to 260 DEG C, carry out solid phase condensation reaction, insulation 8h, Temperature fall 0.5h, cold water cooling 4h, pulverize, generate three anthraquinone imines crude products, three anthraquinone imines crude products are added in 3000kg water, stir, be warming up to 90 DEG C, insulation 1h, adds water and is cooled to 50 DEG C, filters, be washed to neutrality, drying, to moisture content≤1%, generates refining three anthraquinone imines.
2) ring-closure reaction: at 40 DEG C, in solid phase reactor, add urea 80kg, Sodium Fluoride 45kg, sodium acetate, anhydrous 4.5kg, aluminum chloride 200kg and refining three anthraquinone imines 90kg batch mixings, then heat temperature raising, rises to 190 DEG C gradually by outer temperature in 65min, foamable reaction is carried out in 190 ~ 260 DEG C, when being warming up to 190 ~ 260 DEG C in solid phase, insulation 40min, Temperature fall 0.5h, cold water spraying cooling 5h, be cooled to less than 40 DEG C, pulverize, obtain closed loop material.
3) segregation alkali cleaning: under stirring, closed loop material 350kg is added in 2200kg water, then add the sulfuric acid 90kg of 95%, be warming up to 95 DEG C, insulation 1h, the 800kg that then adds water dilutes and is cooled to 40 DEG C, filter, be washed to neutrality, then add the washing lotion of 65 DEG C prepared by water 3500kg at the bottom of concentration 35% liquid caustic soda 350kg and alkali cleaning, alkali cleaning, then be washed to neutrality, dry, obtain vat dyes palm fibre GG, sampling detects, and dark brown powder, purity is 98.2%.
Embodiment 3
1) condensation poach: by 1,5-dichloroanthraquinone 120kg, 1-aminoanthraquinone 180kg, copper powder 7kg and anhydrous sodium carbonate 105kg mix, and 105 DEG C of dehydrations 1h, 2h are warming up to 260 DEG C, carry out solid phase condensation reaction, insulation 8h, Temperature fall 0.5h, cold water cooling 4h, pulverize, generate three anthraquinone imines crude products, three anthraquinone imines crude products are added in 3000kg water, stir, be warming up to 92 DEG C, insulation 1h, adds water and is cooled to less than 60 DEG C, filters, be washed to neutrality, drying, to moisture content≤1%, generates refining three anthraquinone imines.
2) ring-closure reaction: at 50 DEG C, in solid phase reactor, add urea 90kg, Sodium Fluoride 40kg, sodium acetate, anhydrous 4.5kg, aluminum chloride 200kg and add refining three anthraquinone imines 90kg batch mixings, then heat temperature raising, in 50min, outer temperature is risen to 190 DEG C gradually, foamable reaction is carried out in 190 ~ 245 DEG C, when being warming up to 185 ~ 245 DEG C in solid phase, insulation 30min, Temperature fall 0.5h, cold water spraying cooling 4h, be cooled to 45 DEG C, pulverize, obtain closed loop material.
3) segregation alkali cleaning: under stirring, closed loop material 350kg is added in 2200kg water, then add the sulfuric acid 90kg of 95%, be warming up to 92 DEG C, insulation 1h, the 800kg that then adds water dilutes and is cooled to less than 60 DEG C, filter, be washed to neutrality, then add the washing lotion of 65 DEG C prepared by water 3500kg at the bottom of concentration 35% liquid caustic soda 350kg and alkali cleaning, alkali cleaning, then be washed to neutrality, dry, obtain vat dyes palm fibre GG, sampling detects, and dark brown powder, purity is 98.6%.
Comparative example
Formed by Vat Brown 3GR and Vat Olive R blending, its blending ratio is: Vat Brown 3GR 72%, Vat Olive R 28%.
Dyeing application performance prepared by the embodiment of the present invention and comparative example
1, enhancing rate measures, and the results are shown in Table 2
Table 2 K/S value result
2, fastness measures, and result is as shown in table 3:
Colour fixation under table 3 different condition
From table 2 and 3, vat dyes palm fibre GG prepared by the inventive method is compared with comparative example dyestuff, and properties all can reach the requirement of existing blending Vat Brown GG standard, is significantly increased in fixation enhancing rate and colour fixation.
Claims (9)
1. a vat dyes palm fibre GG, it is characterized in that: belong to anthraquinone analog compound, structural formula is,
。
2. a preparation method of vat dyes palm fibre GG described in claim 1, it is characterized in that, step is:
1) condensation poach: 1,5-dichloroanthraquinone, 1-aminoanthraquinone, copper powder and anhydrous sodium carbonate are mixed, 100 ~ 120 DEG C of dehydrations more than 40min, 1.5 ~ 4h are warming up to 260 ~ 265 DEG C, carry out solid phase condensation reaction, insulation 8h, cooling, pulverize, generate three anthraquinone imines crude products, three anthraquinone imines crude products are added to the water, stir, be warming up to 90 ~ 95 DEG C, insulation 1h, add water and be cooled to less than 60 DEG C, filter, be washed to neutrality, drying, to moisture content≤1%, generates refining three anthraquinone imines;
2) ring-closure reaction: in temperature lower than at 50 DEG C, urea, Sodium Fluoride, sodium acetate, anhydrous and aluminum chloride and refining three anthraquinone imines are added in reactor, batch mixing heat temperature raising, outer temperature is risen to 190 ~ 260 DEG C and carries out foamable reaction by 45 ~ 65min gradually, when being warming up to 180 ~ 200 DEG C in solid phase, insulation 10 ~ 40min, is cooled to less than 60 DEG C, pulverize, obtain closed loop material;
3) segregation alkali cleaning: under stirring, closed loop material is added to the water, then adds sulfuric acid, be warming up to 90 ~ 95 DEG C, insulation 1h, then thin up be cooled to less than 60 DEG C, filters, be washed to neutrality, then add the washing lotion of water preparation at the bottom of liquid caustic soda and alkali cleaning, alkali cleaning, then be washed to neutrality, drying, obtains vat dyes palm fibre GG.
3. preparation method according to claim 2, is characterized in that: in step 1), 1,5-described dichloroanthraquinone: 1-aminoanthraquinone: copper powder: anhydrous sodium carbonate: the mass ratio of water is 100 ~ 150:150 ~ 200:100 ~ 120:3 ~ 10:3000.
4. preparation method according to claim 2, is characterized in that: in step 1), and described cool-down method is Temperature fall 0.5h, cold water cooling 4h.
5. preparation method according to claim 2, is characterized in that: step 2) in, described refining three anthraquinone imines: urea: Sodium Fluoride: sodium acetate, anhydrous: aluminum chloride mass ratio is 80 ~ 100:60 ~ 100:20 ~ 50:4.5:200.
6. preparation method according to claim 2, is characterized in that: step 2) in, described cool-down method is: Temperature fall 0.5h, cold water spraying cooling 3 ~ 5h.
7. preparation method according to claim 2, is characterized in that: in step 3), described closed loop material: water: sulfuric acid: liquid caustic soda: the mass ratio of water at the bottom of alkali cleaning is 350:3000:73 ~ 110:300 ~ 400:3500.
8. preparation method according to claim 2, is characterized in that: in step 3), and described washing lotion compound method is: under stirring, be slowly added to the water by liquid caustic soda, and after stirring 15min, be warming up to 60 ~ 70 DEG C, alkali cleaning is for subsequent use, described liquid caustic soda concentration >=30%.
9. preparation method according to claim 2, is characterized in that: in step 3), and described sulfuric acid concentration is >=92.5%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410702950.9A CN104497617B (en) | 2014-11-29 | 2014-11-29 | A kind of reducing dye palm fibre GG and preparation method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410702950.9A CN104497617B (en) | 2014-11-29 | 2014-11-29 | A kind of reducing dye palm fibre GG and preparation method |
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| Publication Number | Publication Date |
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| CN104497617A true CN104497617A (en) | 2015-04-08 |
| CN104497617B CN104497617B (en) | 2016-08-24 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106317955A (en) * | 2016-07-26 | 2017-01-11 | 萧县凯奇化工科技有限公司 | Brown reduction dye and preparation method thereof |
| CN111072658A (en) * | 2019-12-26 | 2020-04-28 | 江苏亚邦染料股份有限公司 | Method for synthesizing vat black 25 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106317955A (en) * | 2016-07-26 | 2017-01-11 | 萧县凯奇化工科技有限公司 | Brown reduction dye and preparation method thereof |
| CN111072658A (en) * | 2019-12-26 | 2020-04-28 | 江苏亚邦染料股份有限公司 | Method for synthesizing vat black 25 |
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| Publication number | Publication date |
|---|---|
| CN104497617B (en) | 2016-08-24 |
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