CN103387754A - Method for producing pigment red 48:2 with excellent heat resistance and migration resistance - Google Patents
Method for producing pigment red 48:2 with excellent heat resistance and migration resistance Download PDFInfo
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- CN103387754A CN103387754A CN2013103457781A CN201310345778A CN103387754A CN 103387754 A CN103387754 A CN 103387754A CN 2013103457781 A CN2013103457781 A CN 2013103457781A CN 201310345778 A CN201310345778 A CN 201310345778A CN 103387754 A CN103387754 A CN 103387754A
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- 238000013508 migration Methods 0.000 title claims abstract description 22
- 230000005012 migration Effects 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 229940099800 pigment red 48 Drugs 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- 239000000049 pigment Substances 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000003756 stirring Methods 0.000 claims abstract description 26
- 239000007788 liquid Substances 0.000 claims abstract description 25
- 239000000243 solution Substances 0.000 claims abstract description 17
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 16
- 238000005859 coupling reaction Methods 0.000 claims abstract description 15
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims abstract description 14
- 239000001110 calcium chloride Substances 0.000 claims abstract description 13
- 229910001628 calcium chloride Inorganic materials 0.000 claims abstract description 13
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 238000006193 diazotization reaction Methods 0.000 claims abstract description 8
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- 239000012670 alkaline solution Substances 0.000 claims abstract description 3
- 230000004048 modification Effects 0.000 claims abstract description 3
- 238000012986 modification Methods 0.000 claims abstract description 3
- ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 claims description 18
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 15
- 238000010792 warming Methods 0.000 claims description 10
- 239000002270 dispersing agent Substances 0.000 claims description 9
- KMIGBVSYNVXBEI-UHFFFAOYSA-M sodium;2-amino-4-chloro-5-methylbenzenesulfonate Chemical compound [Na+].CC1=CC(S([O-])(=O)=O)=C(N)C=C1Cl KMIGBVSYNVXBEI-UHFFFAOYSA-M 0.000 claims description 7
- 238000009413 insulation Methods 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 2
- 239000001054 red pigment Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 8
- 238000001914 filtration Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 4
- 239000011734 sodium Substances 0.000 abstract description 3
- 229910052708 sodium Inorganic materials 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000004743 Polypropylene Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 5
- 238000001514 detection method Methods 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 230000008569 process Effects 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- VRLPHBSFRWMMPW-UHFFFAOYSA-N 2-amino-4-chloro-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1Cl VRLPHBSFRWMMPW-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- 239000004707 linear low-density polyethylene Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Landscapes
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
The invention relates to a method for producing a pigment red 48:2 with excellent heat resistance and migration resistance and belongs to the technical field of fine chemical industries. The method comprises the following process steps of: under an acidic condition, carrying out stirring diazotization reaction on 6-chloro-4-aminotoluene-3-sodium sulfonate and sodium nitrite for 1 hour, then, adding calcium chloride aqueous solution, and continuously carrying out stirring reaction; after the reaction is ended, adding material liquid into a clear alkaline solution of 2-hydroxy-3-naphthoic acid, so as to carry out coupling reaction; and after the reaction is ended, adjusting the pH value of a reaction solution to 7.0, then, adding a mixed assistant aqueous solution into the reaction solution so as to carry out surface modification, then, heating the reaction solution to 95-100 DEG C, carrying out heat-preserved reaction, then, adding water for cooling to below 60 DEG C, filtering, washing with water and drying, thus obtaining the pigment red 48:2. The method has the advantages that the dispersity, heat resistance, solvent resistance and fluidity of the pigment can be improved remarkably, and the coloring effect of the pigment can be improved effectively.
Description
Technical field
The invention belongs to the fine chemical technology field, be specifically related to the production method of a kind of pigment red 4 8:2 of superior heat resistance resistance to migration energy.
Background technology
6-chloro-4-aminotoluene-3-sulfonic acid sodium salt (being called for short 2B acid sodium) is a kind of important pigment dyestuff intermediate.It is the blue light redness as synthetic C.I.P.R.48:2 (everbright fast red BBC) toner of diazo component, is widely used in hard or flexible PVC, LLDPE, LDPE, HDPE, PP plastic cement system, and also applicable in rubber and PU.
The industrialized preparing process that C.I.P.R.48:2 is traditional is: after 2B acid sodium, water high temperatureization is clear, with hydrochloric acid acid out salify, add sodium nitrite in aqueous solution diazotization, coupled reaction is carried out in its diazonium salt and coupling component 2,3 acid, again with the calcium chloride effect, be transformed into the calcium salt color lake, with rosined soap, process before filtration, finally by Overheating Treatment, filtration, washing, drying.The pigmenting power of its preparation is lower, and owing to having introduced rosin, descend to some extent on resistance toheat, heat-resisting 210 ℃ of * 5min in PP, in transport property on PU below 3 grades.
Summary of the invention
Problem for the prior art existence, the object of the invention is to design the technical scheme of the production method of the pigment red 4 8:2 that a kind of superior heat resistance resistance to migration energy is provided, the method can improve dispersiveness, thermotolerance, solvent resistance and the mobility of pigment significantly, and the coloring effect that effectively improves pigment.
The production method of the pigment red 4 8:2 of described a kind of superior heat resistance resistance to migration energy is characterized in that comprising following processing step:
1) under acidic conditions, temperature-10 ℃～5 ℃, after 6-chloro-4-aminotoluene-3-sulfonic acid sodium salt and Sodium Nitrite generation diazotization stirring reaction 1h, add calcium chloride water to proceed stirring reaction;
2) after reaction finishes, at 12～15 ℃ of temperature, the feed liquid that step 1) is obtained is added in the alkaline solution of the 2-hydroxyl of clarification-3-naphthoic acid carries out coupled reaction;
3) after reaction finishes, with step 2) the pH value of the reaction solution that obtains adjusts to 7.0, add the mixed aid aqueous solution to carry out surface modification in this reaction solution again, then this reaction solution is warming up to 95～100 ℃ and carries out insulation reaction, then add below water for cooling to 60 ℃, filter, washing, oven dry, obtain red pigment 48:2.
The production method of the pigment red 4 8:2 of described a kind of superior heat resistance resistance to migration energy, the weight ratio that feeds intake that it is characterized in that the 6-chloro-4-aminotoluene-3-sulfonic acid sodium salt described in described step 1) and calcium chloride is 100:120～250, and the mass concentration of described calcium chloride water is 30%.
The production method of the pigment red 4 8:2 of described a kind of superior heat resistance resistance to migration energy, it is characterized in that mixed aid in described step 3) by the good hyper-dispersant of thermotolerance and Soxylat A 25-7 is composite forms, the weight proportion of described hyper-dispersant and Soxylat A 25-7 is 100:20～200.
The production method of the pigment red 4 8:2 of described a kind of superior heat resistance resistance to migration energy, it is characterized in that in described step 3), hyper-dispersant is super dispersed system CH-M8, CH-3A or CH-2C, described Soxylat A 25-7 is Soxylat A 25-7 O-15, Soxylat A 25-7 O-9 or Soxylat A 25-7 MOA-3.
Described a kind of superior heat resistance resistance to migration can the production method of pigment red 4 8:2, it is characterized in that in described step 3), the weight ratio that feeds intake of 6-chloro-4-aminotoluene-3-sulfonic acid sodium salt and hyper-dispersant is 100:1～15.
Concrete reaction equation of the present invention is as follows:
Chemical reagent involved in the present invention is currently available products, all can buy on market.
The production method of the pigment red 4 8:2 of above-mentioned a kind of superior heat resistance resistance to migration energy, reasonable in design, compared with prior art, have following beneficial effect:
1) the present invention is added to calcium chloride water in diazo liquid, the color lake reaction is advanceed to coupled reaction to be carried out simultaneously, the pigment molecule that makes solubility when just starting to form immediately color lake change into insoluble calcium precipitation, transparency and tinting strength improve greatly, and the partially blue phase of form and aspect;
2) the invention provides the using method of the compound auxiliary of the hyper-dispersant of fine heat-resisting performance and Soxylat A 25-7, change the surface polarity of granules of pigments by the synergy of compound auxiliary, substantially exceeded the covered effect sum of independent auxiliary agent, thereby improve pigment thermotolerance, dispersiveness, solvent resistance and mobility, obviously improve simultaneously the resistance to migration application performance of this blue light Pigment red in the PU application, increase economic efficiency;
3) the present invention has removed the use rosined soap process for treating surface of Traditional Industrialization production method, make its resistance toheat in PP reach 230 ℃ of * 5min, more common P.R.48:2 resistance toheat is high 20 ℃, make pigment be more suitable for the application of PU system owing to having removed the rosined soap processing, resistance to migration in the PU system rises to 5 grades, promote application performance, improved economic benefit.
Embodiment
The present invention will be further described below in conjunction with specific embodiment, but embodiment does not limit the scope of the invention.
Embodiment 1:
1) 200Kg6-chloro-4-aminotoluene-3-sulfonic acid sodium salt is added reactor, add 1800Kg water, be warming up to 90～95 ℃, stirring reaction 10～20min; Add concentrated hydrochloric acid in 5min, more than stirring reaction 30min; Then slowly adding 30% sodium nitrite in aqueous solution 250Kg to carry out diazotization reaction at 0 ℃ stirred 1 hour; Again 30% calcium chloride water 800Kg is joined in above diazo liquid;
2) add 2000Kg water in the coupled reaction still, 285Kg liquid caustic soda and 160Kg2,3 acid, stir at 40～50 ℃ of temperature, obtain clear liquor;
3) diazo liquid is injected this coupled reaction still under 12～15 ℃ and carry out coupled reaction, diazo liquid adds rear stirring 3 hours; After this reacting liquid pH value is adjusted to 7.0, with 2Kg CH-M8,4Kg O-15 add in 400Kg water be warming up to more than 90 ℃ molten clear after, slowly be added drop-wise in above reaction solution, after stirring 10～20min, again this reaction solution is warmed up to 95～100 ℃, insulation 30min, then add below water for cooling to 60 ℃, press filtration, washing, oven dry, obtain pigment red 4 8:2 under 80～100 ℃.Output: 385Kg, productive rate: 101.58%, the pigment outward appearance is bright-coloured, easy grinding disperses, and the tinting strength in the PVC medium, up to 110%, can reach 230 ℃ of * 5min on the PP resistance toheat, the PU transport property detection display class 5 of anti-migration level.
Embodiment 2
1) 200Kg6-chloro-4-aminotoluene-3-sulfonic acid sodium salt is added reactor, add 1800Kg water, be warming up to 90～95 ℃, stirring reaction 10～20min; Add concentrated hydrochloric acid in 5min, more than stirring reaction 30min; Then slowly adding 30% sodium nitrite in aqueous solution 250Kg to carry out diazotization reaction at 5 ℃ stirred 1 hour; Again 30% calcium chloride water 1000Kg is joined in above diazo liquid;
2) add 2000Kg water in reactor, 285Kg liquid caustic soda and 180Kg2,3 acid, stir at 40～50 ℃ of temperature, obtain clear liquor;
3) diazo liquid is injected this coupled reaction still under 12～15 ℃ and carry out coupled reaction, diazo liquid adds rear stirring 3 hours; After this reacting liquid pH value is adjusted to 7.0, with 10Kg CH-3A, 10Kg O-9 add in 400Kg water be warming up to more than 90 ℃ molten clear after, slowly be added drop-wise in above reaction solution, after stirring 10-20min, again this reaction solution is warmed up to 95～100 ℃, insulation 30min, cooling, press filtration, washing, oven dry, obtain pigment red 4 8:2 under 80～100 ℃.Output: 403Kg, productive rate: 102.54%, the pigment outward appearance is bright-coloured, easy grinding disperses, and the tinting strength in the PVC medium, up to 105%, can reach 230 ℃ of * 5min on the PP resistance toheat, the PU transport property detection display class 5 of anti-migration level.
Embodiment 3
1) 200Kg6-chloro-4-aminotoluene-3-sulfonic acid sodium salt is added reactor, add 1800Kg water, be warming up to 90～95 ℃, stirring reaction 10～20min; Add concentrated hydrochloric acid in 5min, more than stirring reaction 30min; Then slowly adding 30% sodium nitrite in aqueous solution 250Kg to carry out diazotization reaction at 0 ℃ stirred 1 hour; Again 30% calcium chloride water 1200Kg is joined in above diazo liquid;
2) add 2000Kg water in reactor, 285Kg liquid caustic soda and 200Kg2,3 acid, stir at 40～50 ℃ of temperature, obtain clear liquor;
3) diazo liquid is injected this coupled reaction still under 12～15 ℃ and carry out coupled reaction, diazo liquid adds rear stirring 3 hours; After this reacting liquid pH value is adjusted to 7.0, with 12Kg CH-2C, 18Kg MOA-3 add in 400Kg water be warming up to more than 90 ℃ molten clear after, slowly be added drop-wise in above reaction solution, after stirring 10～20min, again this reaction solution is warmed up to 95～100 ℃, insulation 30min, cooling, press filtration, washing, oven dry, obtain pigment red 4 8:2 under 80～100 ℃.Output: 418Kg, productive rate: 103.72%, the pigment outward appearance is bright-coloured, easy grinding disperses, and the tinting strength in the PVC medium, up to 108%, can reach 230 ℃ of * 5min on the PP resistance toheat, the PU transport property detection display class 5 of anti-migration level.
Embodiment 4
1) 200Kg6-chloro-4-aminotoluene-3-sulfonic acid sodium salt is added reactor, add 1800Kg water, be warming up to 90～95 ℃, stirring reaction 10～20min; Add concentrated hydrochloric acid in 5min, more than stirring reaction 30min; Then slowly adding 30% sodium nitrite in aqueous solution 250Kg to carry out diazotization reaction at 0 ℃ stirred 1 hour; Again 30% calcium chloride water 1650Kg is joined in above diazo liquid;
2) add 2000Kg water in reactor, 285Kg liquid caustic soda and 200Kg2,3 acid, stir at 40～50 ℃ of temperature, obtain clear liquor;
3) diazo liquid is injected this coupled reaction still under 12～15 ℃ and carry out coupled reaction, diazo liquid adds rear stirring 3 hours; After this reacting liquid pH value is adjusted to 7.0, with 20Kg CH-M8,4Kg MOA-3 add in 400Kg water be warming up to more than 90 ℃ molten clear after, slowly be added drop-wise in above reaction solution, after stirring 10～20min, again this reaction solution is warmed up to 95～100 ℃, insulation 30min, cooling, press filtration, washing, oven dry, obtain pigment red 4 8:2 under 80～100 ℃.Output: 411Kg, productive rate: 103.53%, the pigment outward appearance is bright-coloured, easy grinding disperses, and the tinting strength in the PVC medium, up to 108%, can reach 230 ℃ of * 5min on the PP resistance toheat, the PU transport property detection display class 5 of anti-migration level.
Claims (5)
- A superior heat resistance resistance to migration can the production method of pigment red 4 8:2, it is characterized in that comprising following processing step:1) under acidic conditions, temperature-10 ℃～5 ℃, after 6-chloro-4-aminotoluene-3-sulfonic acid sodium salt and Sodium Nitrite generation diazotization stirring reaction 1h, add calcium chloride water to proceed stirring reaction;2) after reaction finishes, at 12～15 ℃ of temperature, the feed liquid that step 1) is obtained is added in the alkaline solution of the 2-hydroxyl of clarification-3-naphthoic acid carries out coupled reaction;3) after reaction finishes, with step 2) the pH value of the reaction solution that obtains adjusts to 7.0, add the mixed aid aqueous solution to carry out surface modification in this reaction solution again, then this reaction solution is warming up to 95～100 ℃ and carries out insulation reaction, then add below water for cooling to 60 ℃, filter, washing, oven dry, obtain red pigment 48:2.
- A kind of superior heat resistance resistance to migration as claimed in claim 1 can the production method of pigment red 4 8:2, it is characterized in that the calcium chloride solution described in described step 1) joins in diazo liquid, the weight ratio that feeds intake of 6-chloro-4-aminotoluene-3-sulfonic acid sodium salt and calcium chloride is 100:120～250, and the mass concentration of described calcium chloride water is 30%.
- A kind of superior heat resistance resistance to migration as claimed in claim 1 can the production method of pigment red 4 8:2, it is characterized in that mixed aid in described step 3) by the good hyper-dispersant of thermotolerance and Soxylat A 25-7 is composite forms, the weight proportion of described hyper-dispersant and Soxylat A 25-7 is 100:20～200.
- As claim 1,3 described a kind of superior heat resistance resistances to migration can the production method of pigment red 4 8:2, it is characterized in that in described step 3), hyper-dispersant is CH-M8, CH-3A or CH-2C, described Soxylat A 25-7 is Soxylat A 25-7 O-15, Soxylat A 25-7 O-9 or Soxylat A 25-7 MOA-3.
- A kind of superior heat resistance resistance to migration as claimed in claim 1 can the production method of pigment red 4 8:2, it is characterized in that in described step 3), the weight ratio that feeds intake of 6-chloro-4-aminotoluene-3-sulfonic acid sodium salt and hyper-dispersant is 100:1～15.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104962101A (en) * | 2015-06-26 | 2015-10-07 | 嘉兴科隆化工有限公司 | Industrial production method for safe and environment-friendly red-light yellow pigment PY191:1 for food plastic packaging |
| CN106084882A (en) * | 2016-06-23 | 2016-11-09 | 嘉兴科隆化工有限公司 | A kind of plastic cement industrialized preparing process of low PAHs content safety and environmental protection C lake red CAN'T pigment 53:1 |
| CN106084875A (en) * | 2016-06-13 | 2016-11-09 | 嘉兴科隆化工有限公司 | The industrialized production of the paratonere PR 48:2 of a kind of excellence resistance to migration heat resistance and detection method |
| CN106634040A (en) * | 2016-08-30 | 2017-05-10 | 上虞市东海化工有限公司 | Preparation method of red pigment |
| CN111675922A (en) * | 2020-06-22 | 2020-09-18 | 浙江东海新材料科技有限公司 | Environment-friendly organic pigment applied to agricultural seed coating and preparation process thereof |
| CN113429805A (en) * | 2021-06-24 | 2021-09-24 | 鞍山市五色石新材料科技有限公司 | Production method of high-performance mixed crystal pigment taking C.I. pigment red 168 as main body |
| CN113462189A (en) * | 2021-06-25 | 2021-10-01 | 杭州映山花颜料化工有限公司 | Preparation method of azo pigment |
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| CN106084875A (en) * | 2016-06-13 | 2016-11-09 | 嘉兴科隆化工有限公司 | The industrialized production of the paratonere PR 48:2 of a kind of excellence resistance to migration heat resistance and detection method |
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