CN111704808A - A pigment Red 57:1 preparation method - Google Patents
A pigment Red 57:1 preparation method Download PDFInfo
- Publication number
- CN111704808A CN111704808A CN202010721498.6A CN202010721498A CN111704808A CN 111704808 A CN111704808 A CN 111704808A CN 202010721498 A CN202010721498 A CN 202010721498A CN 111704808 A CN111704808 A CN 111704808A
- Authority
- CN
- China
- Prior art keywords
- acid
- sulfonic acid
- pigment red
- amino
- preparation
- 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
- 239000000049 pigment Substances 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 238000010168 coupling process Methods 0.000 claims abstract description 20
- 238000005859 coupling reaction Methods 0.000 claims abstract description 19
- 230000008878 coupling Effects 0.000 claims abstract description 18
- 238000001035 drying Methods 0.000 claims abstract description 15
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 claims abstract description 13
- FLIOATBXVNLPLK-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1N FLIOATBXVNLPLK-UHFFFAOYSA-N 0.000 claims abstract description 13
- RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- BTMZHHCFEOXAAN-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;2-dodecylbenzenesulfonic acid Chemical compound OCCN(CCO)CCO.CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O BTMZHHCFEOXAAN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000227 grinding Methods 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 8
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 48
- 238000003756 stirring Methods 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 14
- 239000012295 chemical reaction liquid Substances 0.000 claims description 12
- 239000011259 mixed solution Substances 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 8
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 claims description 7
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 7
- 235000010288 sodium nitrite Nutrition 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000004321 preservation Methods 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 5
- 229940105956 tea-dodecylbenzenesulfonate Drugs 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 2
- 238000012986 modification Methods 0.000 claims 2
- 239000012467 final product Substances 0.000 claims 1
- 239000002245 particle Substances 0.000 abstract description 14
- 239000013078 crystal Substances 0.000 abstract description 7
- 235000010187 litholrubine BK Nutrition 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 4
- 239000002270 dispersing agent Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 abstract 1
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 230000003313 weakening effect Effects 0.000 abstract 1
- 238000004040 coloring Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- FZOHYRVMPWJCPV-UHFFFAOYSA-N NN.OCCCC(=O)O Chemical compound NN.OCCCC(=O)O FZOHYRVMPWJCPV-UHFFFAOYSA-N 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VPWFPZBFBFHIIL-UHFFFAOYSA-L Lithol Rubine Chemical compound OC=1C(=CC2=CC=CC=C2C1N=NC1=C(C=C(C=C1)C)S(=O)(=O)[O-])C(=O)[O-].[Na+].[Na+] VPWFPZBFBFHIIL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
- C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
- C09B29/0834—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -O-
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/26—Amino phenols
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
Abstract
A method of preparing c.i. pigment red 57: the process 1 comprises the steps of improving the process, adding 2-aminophenol-4-sulfonic acid, 1-amino-2-naphthol-4-sulfonic acid or 3-amino-4-methoxybenzenesulfonic acid as a second coupling component, weakening the acting force among particles, changing the particle size and the color light, simultaneously selecting dodecylbenzene sulfonic acid triethanolamine, 4-hydroxy hydrazine butyrate and 4-hydroxy butyl acrylate as modifying substances and dispersing agents, enhancing the tinting strength, effectively controlling the growth of pigment crystals, increasing the fluidity, adopting microwave drying, improving the drying efficiency, avoiding the water loss conversion of crystal forms, reducing the average particle size of the pigment by pneumatic grinding drying, and increasing the tinting strength.
Description
Technical Field
The invention belongs to the technical field of organic raw material preparation, and particularly relates to a C.I. pigment red 57: 1. A process for producing the same.
Background
Organic pigments are an important class of colored substances used for coloring objects. Compared with inorganic pigment, the said pigment has wide variety, complete color spectrum, bright color and high coloring strength, and may be used widely in coloring ink, paint, plastic, rubber, synthetic fiber, daily chemical product, etc. and printing fabric. The c.i. pigment red 57 is the most important pigment for high quality printing red ink, and its lake salts include calcium, strontium, barium, manganese, among which calcium salt is the most widely used, and is c.i. pigment red 57:1, which accounts for about one fourth of the yield of red pigment.
C.i. pigment red 57:1 is also called lithol rubine, and the prior art is mainly to diazotize 4-aminotoluene-3-sulfonic acid (4B) at pH < 2 and temperature < 5 ℃, then couple with 2, 3-acid, use calcium ion suspension prepared by using calcium chloride as raw material as coupling lake raw material and adjust pH alkaline condition, and prepare pigment red 57 by coupling salting out: 1. however, the pigment prepared by the method has the defects of low dispersibility, low coloring strength and the like. With the pigment red 57 in domestic and foreign markets: 1, and the quality is required to be improved, and therefore, improvement of pigment red 57:1, improving the product quality.
Disclosure of Invention
The invention aims to overcome the defects of the prior pigment red 57:1, the production process and the product quality are insufficient, and the preparation of the pigment red 57:1, by adding coupling components and modified additives and the like, the interaction force among particles and the surface polarity state of pigment particles are adjusted, the particle size is improved, and the performances of the product such as flowability, dispersibility, tinting strength and the like are improved.
In order to achieve the purpose, the invention adopts the following technical scheme:
a process for preparing pigment Red 57:1, the specific steps are as follows:
(1) adding 4-aminotoluene-3-sulfonic acid and 50% by mass of sodium hydroxide solution into a reaction bottle with a stirring device, cooling after 4B acid is completely dissolved, adding 36% by mass of hydrochloric acid solution at 0-10 ℃, stirring for 5-10min, adding 30% by mass of sodium nitrite aqueous solution, stirring for reaction for 35-39min, adding 40% by mass of calcium hydroxide solution, and stirring for 5-10 min;
(2) adding 2, 3-acid, 50% sodium hydroxide solution and the second coupling component into another reaction bottle with a stirring device, stirring for dissolving at 25-30 ℃, continuing to react for 20-30min, adding the modified component, and continuing to stir for 10-20 min;
(3) dropwise adding the mixed solution obtained in the step (2) into the mixed solution obtained in the step (1), adjusting the pH of the system to 8.0-9.5 by using alkali liquor, and carrying out heat preservation and stirring reaction at 70-85 ℃ for 40-60 min;
the step is mainly coupling and color precipitation, and the coupling component (2) is added into the diazonium salt (1) for trans-coupling, so that the fluidity and the transparency are better.
(4) Filtering and rinsing the reaction liquid obtained in the step (3), drying the reaction liquid for 1.5 to 2.5 hours at the temperature of between 60 and 70 ℃, and carrying out ultrafine grinding by adopting an airflow mill.
In the step (1), the molar ratio of the 4B acid to the sodium hydroxide to the hydrochloric acid is 1: 1.5-2.0: 2.8-3.5.
In the step (1), the molar ratio of the 4B acid to the sodium nitrite is 1: 1.03-1.06.
In the step (1), the molar ratio of the 4B acid to the calcium hydroxide is 1: 1.05-1.12.
In the step (2), the molar ratio of the 2, 3-acid to the 4B acid is 1: 1.03-1.05.
In the step (2), the molar ratio of the 2, 3-acid to the sodium hydroxide is 1: 1.3-1.5. The sodium hydroxide is mainly used for adjusting the coupling pH, because the pigment shows different characteristics under different pH values, for example, the pigment is brighter in color and has high fluidity and more stable crystal form when the pH value is 8.0-9.5, but when the pH value is increased again, the transparency is good, but the fluidity is lower.
The second coupling component in the step (2) is two or three of 2-aminophenol-4-sulfonic acid, 1-amino-2-naphthol-4-sulfonic acid or 3-amino-4-methoxybenzenesulfonic acid which are mixed in any proportion. The total dosage of the compound is 1.5 to 2.5 percent of the total mass dosage of the 2, 3-acid.
Preferably, the second coupling component is a combination of 2-aminophenol-4-sulfonic acid and 1-amino-2-naphthol-4-sulfonic acid in a mass ratio of 1: 1;
preferably, the mass ratio of the 1-amino-2-naphthol-4-sulfonic acid to the 3-amino-4-methoxybenzenesulfonic acid is 1: 2;
preferably, the mass ratio of the 2-aminophenol-4-sulfonic acid to the 3-amino-4-methoxybenzenesulfonic acid is 2: 1;
preferably, the mass ratio of the 2-aminophenol-4-sulfonic acid to the 1-amino-2-naphthol-4-sulfonic acid to the 3-amino-4-methoxybenzenesulfonic acid is 1: 1: 1.
the modified components in the step (2) are dodecyl benzene sulfonic acid triethanolamine, 4-hydroxy butyric acid hydrazine and 4-hydroxy butyl acrylate, and the mass of the modified components is 5-7% of the theoretical yield of the pigment.
The alkali liquor adopted in the step (3) is ammonia water or sodium carbonate aqueous solution.
The pigment red described herein is c.i. pigment red.
The invention has the beneficial effects that:
aiming at the problems of poor fluidity, low coloring strength and the like of the pigment prepared by the prior art, the invention adds 2-aminophenol-4-sulfonic acid, 1-amino-2-naphthol-4-sulfonic acid or 3-amino-4-methoxybenzenesulfonic acid as a second coupling component, the selected second coupling component contains an electron-withdrawing group sulfonic group, the induction and conjugation effects of the second coupling component can effectively reduce the electron cloud density, and electron-donating groups such as hydroxyl, amino and the like can increase the electron cloud density of a conjugation system, so that the maximum absorption wavelength is in red shift. The co-coupling process of the second coupling component weakens the acting force among particles, changes the particle size and the color light and improves the transparency.
On the other hand, the triethanolamine dodecylbenzene sulfonate is selected as a modifying substance and can also play a role of a dispersing agent, one end of the triethanolamine dodecylbenzene sulfonate has long chain hydrocarbon, ester group or double bond with hydrophobicity and is used as a lipophilic group, the wetting angle is very large, the tinting strength is strong, the other end of the triethanolamine dodecylbenzene sulfonate contains hydrophilic groups such as sulfonic group and hydroxyl group, and the hydrophilic groups can be well adsorbed or covered on the surface of particles.
Adopt microwave drying, the object of being heated itself is the heat-generating body, does not need hot conductive process, and the heat penetrates inside and outside the object from all sides and makes the object reach even heating in the very short time simultaneously, and non-traditional by outside and in dry, has shortened drying time greatly, accomplishes even heating and even drying simultaneously. Use microwave drying, can avoid using high temperature can reach fine drying effect, avoided pigment red 57 in the high temperature drying: the alpha and gamma crystal forms in 1 are dehydrated and transformed into beta and crystal forms respectively, thereby causing the change of chromatic light.
The average particle size of the pigment is reduced to increase the coloring strength, namely, the coloring power depends on the dispersion level of the pigment to a great extent, the pigment is crushed by an air flow mill, the collision frequency between particles is far higher than that between the particles and the wall of the container, the pigment can achieve a better crushing effect, the surface morphology of the pigment is damaged while the particle size of the pigment is reduced, active sites are increased, the activity of pigment seed crystals is improved, meanwhile, the agglomeration of the pigment can be avoided by the air flow mill grinding, the agglomeration degree of the pigment seed crystals is reduced, and the pigment has better dispersity and coloring degree.
Detailed Description
The present invention will be further illustrated by the following examples, which are intended to be merely illustrative and not limitative.
Example 1: (1) 187.2g (1mol) of 4-aminotoluene-3-sulfonic acid and 120g (1.5mol) of 50% sodium hydroxide solution are added into a reaction bottle with a stirring device, 4B acid is completely dissolved, the temperature is reduced, 283.9g (2.8mol) of 36% hydrochloric acid solution is added at 0 ℃, after 5min of stirring, 236.9g (1.03mol) of 30% sodium nitrite aqueous solution is added, the stirring reaction is carried out for 35min, 194.3g (1.05mol) of 40% calcium hydroxide solution is added, and the stirring is carried out for 5 min.
(2) 178.8g (0.95mol) of 2, 3-acid, 98.8g (1.235mol) of 50 percent sodium hydroxide solution, 1.35g of 2-aminophenol-4-sulfonic acid and 1.35g of 1-amino-2-naphthol-4-sulfonic acid are added into another reaction bottle with a stirring device, the mixture is stirred and dissolved at 25 ℃ and then continuously reacted for 20min, then 21.2g of triethanolamine dodecylbenzene sulfonate is added, and the mixture is continuously stirred for 10 min.
(3) And (3) dropwise adding the mixed solution obtained in the step (2) into the mixed solution obtained in the step (1), then adjusting the pH of the system to 8.0 by adopting ammonia water, and carrying out heat preservation and stirring reaction at 70 ℃ for 40 min.
(4) And (4) filtering and rinsing the reaction liquid obtained in the step (3), drying the reaction liquid for 1.5 hours at the temperature of 60 ℃, and performing superfine grinding by adopting an airflow mill.
Example 2: (1) 187.2g (1mol) of 4-aminotoluene-3-sulfonic acid and 160g (2mol) of 50% sodium hydroxide solution are added into a reaction bottle with a stirring device, 4B acid is completely dissolved, the temperature is reduced, 354.9g (3.5mol) of 36% hydrochloric acid solution is added at 10 ℃, after 10min of stirring, 241.5g (1.05mol) of 30% sodium nitrite aqueous solution is added, 39min of stirring reaction is carried out, 207.2g (1.12mol) of 40% calcium hydroxide solution is added, and the mixture is stirred for 10 min.
(2) 182.6g (0.97mol) of 2, 3-acid, 116.4g (1.455mol) of 50 percent sodium hydroxide solution, 1.52g of 1-amino-2-naphthol-4-sulfonic acid and 3.04g of 3-amino-4-methoxybenzenesulfonic acid are added into another reaction bottle with a stirring device, the mixture is stirred and dissolved at 30 ℃ and then continuously reacted for 30min, then 29.7g of hydrazine 4-hydroxybutyrate is added, and the mixture is continuously stirred for 20 min.
(3) And (3) dropwise adding the mixed solution obtained in the step (2) into the mixed solution obtained in the step (1), then adjusting the pH of the system to 9.5 by adopting sodium carbonate, and carrying out heat preservation and stirring reaction for 60min at 85 ℃.
(4) And (4) filtering and rinsing the reaction liquid obtained in the step (3), drying the reaction liquid for 2.5 hours at 70 ℃, and performing superfine grinding by using an airflow mill.
Example 3: (1) 187.2g (1mol) of 4-aminotoluene-3-sulfonic acid and 140g (1.75mol) of 50% sodium hydroxide solution are added into a reaction bottle with a stirring device, after 4B acid is completely dissolved, the temperature is reduced, 304.2g (3.0mol) of 36% hydrochloric acid solution is added at 5 ℃, after 5min of stirring, 243.8g (1.06mol) of 30% sodium nitrite aqueous solution is added, the reaction is carried out for 37min of stirring, and then 194.3g (1.05mol) of 40% calcium hydroxide solution is added, and the reaction is carried out for 5min of stirring.
(2) Adding 180.7g (0.96mol) of 2, 3 acid, 105.6g (1.32mol) of 50 percent sodium hydroxide solution, 1.2g of 2-aminophenol-4-sulfonic acid, 1.2g of 1-amino-2-naphthol-4-sulfonic acid and 1.2g of 3-amino-4-methoxybenzenesulfonic acid into another reaction bottle with a stirring device, stirring and dissolving at 25 ℃, continuing to react for 20min, then adding 25.4g of 4-hydroxybutyl acrylate, and continuing to stir for 18 min.
(3) And (3) dropwise adding the mixed solution obtained in the step (2) into the mixed solution obtained in the step (1), then adjusting the pH of the system to 9.0 by adopting ammonia water, and carrying out heat preservation and stirring reaction for 45min at the temperature of 80 ℃.
(4) And (4) filtering and rinsing the reaction liquid obtained in the step (3), drying the reaction liquid for 2.5 hours at the temperature of 60 ℃, and performing superfine grinding by adopting an airflow mill.
Example 4:
(1) 187.2g (1mol) of 4-aminotoluene-3-sulfonic acid and 150g (1.875mol) of 50% sodium hydroxide solution are added into a reaction bottle with a stirring device, 4B acid is completely dissolved, the temperature is reduced, 324.4g (3.2mol) of 36% hydrochloric acid solution is added at 8 ℃, after 5min of stirring, 236.9g (1.03mol) of 30% sodium nitrite aqueous solution is added, the stirring reaction is carried out for 35min, 203.8g (1.1mol) of 40% calcium hydroxide solution is added, and the stirring is carried out for 7 min.
(2) 178.8g (0.95mol) of 2, 3 acid, 99.2g (1.24mol) of 50 percent sodium hydroxide solution, 2.62g of 2-aminophenol-4-sulfonic acid and 1.31g of 3-amino-4-methoxybenzenesulfonic acid are added into another reaction bottle with a stirring device, the mixture is stirred and dissolved at 25 ℃ and then continuously reacted for 20min, and then 25.4g of triethanolamine dodecylbenzenesulfonic acid is added and the mixture is continuously stirred for 15 min.
(3) And (3) dropwise adding the mixed solution obtained in the step (2) into the mixed solution obtained in the step (1), then adjusting the pH of the system to 8.0 by adopting ammonia water, and carrying out heat preservation and stirring reaction for 50min at 85 ℃.
(4) And (4) filtering and rinsing the reaction liquid obtained in the step (3), drying the reaction liquid for 2 hours at 65 ℃, and performing superfine grinding by using an airflow mill.
Performance testing
(1) The pigment prepared by the invention and similar products sold in the market are added with water to prepare color paste, the fineness of the pigment is measured by a scraper blade fineness meter, and the test result is as follows
| Pigment numbering | Example 1 | Example 2 | Example 3 | Example 4 | Commercially available product |
| Fineness/. mu.m | 2.8 | 2.2 | 2.6 | 2.5 | 8.7 |
The pigment particles prepared by the invention are loose in aggregation and better in dispersibility.
(2) After the pigment prepared by the invention and color paste prepared by similar products sold in the market are placed for 24 hours, a DV-I Prime type viscometer is used for measuring the viscosity of the color paste, and under the condition of 100r/min, the measurement result is as follows:
the pigment of the invention has better rheological property compared with the similar products.
(3) Pigment red 57 prepared by the present invention: 1 compared with the common similar products, the visual method specified in GB/T5211.19 is used for comparison detection. The relative tinting strength results were as follows:
the pigment of the invention has better tinting strength compared with similar products.
Claims (10)
1. A process for preparing pigment Red 57: the process of 1 is characterized by comprising the following specific steps:
(1) adding 4-aminotoluene-3-sulfonic acid and 50% by mass of sodium hydroxide solution into a reaction bottle with a stirring device, cooling after 4B acid is completely dissolved, adding 36% by mass of hydrochloric acid solution at 0-10 ℃, stirring for 5-10min, adding 30% by mass of sodium nitrite aqueous solution, stirring for reaction for 35-39min, adding 40% by mass of calcium hydroxide solution, and stirring for 5-10 min;
(2) adding 2, 3-acid, 50% sodium hydroxide solution and the second coupling component into another reaction bottle with a stirring device, stirring for dissolving at 25-30 ℃, continuing to react for 20-30min, adding the modified component, and continuing to stir for 10-20 min;
(3) dropwise adding the mixed solution obtained in the step (2) into the mixed solution obtained in the step (1), adjusting the pH of the system to 8.0-9.5 by using alkali liquor, and carrying out heat preservation and stirring reaction at 70-85 ℃ for 40-60 min;
(4) and (4) filtering and rinsing the reaction liquid obtained in the step (3), drying the reaction liquid at 60-70 ℃ for 1.5-2.5h by microwave, and performing ultrafine grinding by using an airflow mill to obtain a final product.
2. Preparation of pigment red 57 according to claim 1: 1, characterized in that the molar ratio of 2, 3-acid to 4B acid in step (2) is 1: 1.03-1.05.
3. Preparation of pigment red 57 according to claim 1: 1, characterized in that in step (2) the molar ratio of 2, 3-acid to sodium hydroxide is 1: 1.3-1.5.
4. Preparation of pigment red 57 according to claim 1: the process of 1 is characterized in that the second coupling component in the step (2) is two or three of 2-aminophenol-4-sulfonic acid, 1-amino-2-naphthol-4-sulfonic acid or 3-amino-4-methoxybenzenesulfonic acid which are mixed in any proportion, and the total amount of the second coupling component is 1.5-2.5% of the total mass amount of the 2, 3-acid.
5. Preparation of pigment Red 57 according to claim 4: 1, characterized in that the second coupling component is a combination of 2-aminophenol-4-sulfonic acid and 1-amino-2-naphthol-4-sulfonic acid, the mass ratio of which is 1: 1.
6. preparation of pigment Red 57 according to claim 4: 1, characterized by the combination of 1-amino-2-naphthol-4-sulfonic acid and 3-amino-4-methoxybenzenesulfonic acid in a mass ratio of 1: 2.
7. preparation of pigment Red 57 according to claim 4: 1, characterized by the combination of 2-aminophenol-4-sulfonic acid and 3-amino-4-methoxybenzenesulfonic acid, in a mass ratio of 2: 1.
8. preparation of pigment Red 57 according to claim 4: 1, the process is characterized in that the mass ratio of the 2-aminophenol-4-sulfonic acid, the 1-amino-2-naphthol-4-sulfonic acid and the 3-amino-4-methoxybenzenesulfonic acid is 1: 1: 1.
9. preparation of pigment red 57 according to claim 1: the process of 1 is characterized in that the modification components in the step (2) are triethanolamine dodecylbenzene sulfonate, 4-hydroxy hydrazine butyrate and 4-hydroxy butyl acrylate, and the mass of the modification components is 5-7% of the theoretical yield of the pigment.
10. Preparation of pigment red 57 according to claim 1: the process of 1 is characterized in that the alkali liquor adopted in the step (3) is ammonia water or sodium carbonate aqueous solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010721498.6A CN111704808B (en) | 2020-07-24 | 2020-07-24 | A pigment Red 57:1 preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010721498.6A CN111704808B (en) | 2020-07-24 | 2020-07-24 | A pigment Red 57:1 preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111704808A true CN111704808A (en) | 2020-09-25 |
| CN111704808B CN111704808B (en) | 2022-06-17 |
Family
ID=72547711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010721498.6A Active CN111704808B (en) | 2020-07-24 | 2020-07-24 | A pigment Red 57:1 preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111704808B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114231103A (en) * | 2022-02-10 | 2022-03-25 | 洪嵩(上海)科技有限公司 | Super-hydrophobic pigment, paint, coating and preparation method thereof |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101983992A (en) * | 2010-11-29 | 2011-03-09 | 苏州林通化工科技股份有限公司 | Synthetic method of paratonere 57:1 |
| CN202254744U (en) * | 2011-09-29 | 2012-05-30 | 湖南巨发科技有限公司 | Microwave drying device for environmental-friendly inorganic pigment production |
| CN102620544A (en) * | 2012-03-12 | 2012-08-01 | 吕晓萍 | Microwave drying device for chemical pigment production |
| CN103483863A (en) * | 2013-09-30 | 2014-01-01 | 苏州思睿屹新材料股份有限公司 | Method for preparing CI pigment red 57:1 |
| CN106189358A (en) * | 2016-07-26 | 2016-12-07 | 萧县凯奇化工科技有限公司 | A kind of black vat dye of high fastness and preparation method thereof |
| CN106221278A (en) * | 2016-07-26 | 2016-12-14 | 萧县凯奇化工科技有限公司 | A kind of preparation method of reducing dye Vat Yellow 1 |
| CN108864752A (en) * | 2018-08-10 | 2018-11-23 | 天津城建大学 | A kind of water-dispersion type paratonere 57:1 modified pigment and preparation method thereof |
| CN110093047A (en) * | 2018-01-31 | 2019-08-06 | 上海汇友精密化学品有限公司 | A kind of ultra fine technology of dyestuff |
| CN110734651A (en) * | 2019-10-23 | 2020-01-31 | 广东丰霖新材料科技有限公司 | brownish red pigment, and preparation method and application thereof |
| CN111040470A (en) * | 2019-12-17 | 2020-04-21 | 佛山科学技术学院 | Blue inorganic pigment and preparation method thereof |
| CN111363384A (en) * | 2020-03-31 | 2020-07-03 | 正太新材料科技有限责任公司 | Visible light catalytic pigment, preparation method and application thereof |
-
2020
- 2020-07-24 CN CN202010721498.6A patent/CN111704808B/en active Active
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101983992A (en) * | 2010-11-29 | 2011-03-09 | 苏州林通化工科技股份有限公司 | Synthetic method of paratonere 57:1 |
| CN202254744U (en) * | 2011-09-29 | 2012-05-30 | 湖南巨发科技有限公司 | Microwave drying device for environmental-friendly inorganic pigment production |
| CN102620544A (en) * | 2012-03-12 | 2012-08-01 | 吕晓萍 | Microwave drying device for chemical pigment production |
| CN103483863A (en) * | 2013-09-30 | 2014-01-01 | 苏州思睿屹新材料股份有限公司 | Method for preparing CI pigment red 57:1 |
| CN106189358A (en) * | 2016-07-26 | 2016-12-07 | 萧县凯奇化工科技有限公司 | A kind of black vat dye of high fastness and preparation method thereof |
| CN106221278A (en) * | 2016-07-26 | 2016-12-14 | 萧县凯奇化工科技有限公司 | A kind of preparation method of reducing dye Vat Yellow 1 |
| CN110093047A (en) * | 2018-01-31 | 2019-08-06 | 上海汇友精密化学品有限公司 | A kind of ultra fine technology of dyestuff |
| CN108864752A (en) * | 2018-08-10 | 2018-11-23 | 天津城建大学 | A kind of water-dispersion type paratonere 57:1 modified pigment and preparation method thereof |
| CN110734651A (en) * | 2019-10-23 | 2020-01-31 | 广东丰霖新材料科技有限公司 | brownish red pigment, and preparation method and application thereof |
| CN111040470A (en) * | 2019-12-17 | 2020-04-21 | 佛山科学技术学院 | Blue inorganic pigment and preparation method thereof |
| CN111363384A (en) * | 2020-03-31 | 2020-07-03 | 正太新材料科技有限责任公司 | Visible light catalytic pigment, preparation method and application thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114231103A (en) * | 2022-02-10 | 2022-03-25 | 洪嵩(上海)科技有限公司 | Super-hydrophobic pigment, paint, coating and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111704808B (en) | 2022-06-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4158572A (en) | Process of producing a phthalocyanine pigment | |
| CN111704808B (en) | A pigment Red 57:1 preparation method | |
| WO2023088293A1 (en) | Use of quaternary ammonium salt derivative in preparation of red pigment, red pigment, and preparation method | |
| CN111875984B (en) | Preparation method of high-temperature-resistant iron oxide yellow pigment | |
| CN102585546A (en) | Preparation method for C.I. pigment red 53:1 | |
| CN102399453A (en) | Preparation method of lightfast organic pigment red 48: 1 | |
| CN108864752B (en) | Water-dispersible pigment red 57:1 modified pigment and preparation method thereof | |
| TW202012550A (en) | Lake pigment preparation method, lake pigment and application thereof | |
| JP4068681B2 (en) | Aqueous coating system containing phthalocyanine | |
| CN110591413B (en) | Preparation method of photodegradation-resistant, dust-free and easy-to-disperse organic pigment solid color paste | |
| US5256772A (en) | Monoazo lake pigment and uses thereof | |
| CN115584143B (en) | Preparation method of fast alkaline lake pigment | |
| CN116751463A (en) | Composite pigment coated with nano aluminum hydroxide and preparation method thereof | |
| CN114685810A (en) | Preparation method and application of carboxyl lignin derivative for dispersing phthalocyanine pigment | |
| US5286287A (en) | Monoazo lake pigment suitable for use in printing ink and process for the production thereof | |
| US3748162A (en) | Light stable quinacridonequinone yellow pigment | |
| CA1169604A (en) | Soft textured high strength alkali blue pigment | |
| JP2629067B2 (en) | Monoazo lake pigment and printing ink composition | |
| CN114752073B (en) | Preparation method and application of disperse phthalocyanine pigment plant derivative | |
| CN110283475B (en) | Preparation method of pigment red 146 | |
| Lv et al. | Modification of CI Pigment Red 146 with surfactants and graphene oxide | |
| CN103421356B (en) | Preparation method of rare earth modified iron oxide black | |
| CN115785697B (en) | Method for improving low temperature resistance stability of phthalocyanine blue pigment dispersion liquid | |
| US2305088A (en) | Pigment | |
| US2087866A (en) | Vat dyestuff preparations |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A Preparation Method of Pigment Red 57:1 Effective date of registration: 20230322 Granted publication date: 20220617 Pledgee: Shandong Penglai Rural Commercial Bank Co.,Ltd. Pledgor: PENGLAI XINGUANG PIGMENT CHEMICAL Co.,Ltd. Registration number: Y2023980035839 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20220617 Pledgee: Shandong Penglai Rural Commercial Bank Co.,Ltd. Pledgor: PENGLAI XINGUANG PIGMENT CHEMICAL Co.,Ltd. Registration number: Y2023980035839 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right |