CN113462188B - Pigment yellow 138 easy to disperse in weak solvent and preparation method thereof - Google Patents
Pigment yellow 138 easy to disperse in weak solvent and preparation method thereof Download PDFInfo
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- CN113462188B CN113462188B CN202110663654.2A CN202110663654A CN113462188B CN 113462188 B CN113462188 B CN 113462188B CN 202110663654 A CN202110663654 A CN 202110663654A CN 113462188 B CN113462188 B CN 113462188B
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- 229940067265 pigment yellow 138 Drugs 0.000 title claims abstract description 183
- 238000002360 preparation method Methods 0.000 title claims abstract description 59
- 239000002904 solvent Substances 0.000 title claims abstract description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 72
- 239000000047 product Substances 0.000 claims abstract description 62
- 239000012043 crude product Substances 0.000 claims abstract description 39
- 239000011259 mixed solution Substances 0.000 claims abstract description 34
- 239000000049 pigment Substances 0.000 claims abstract description 30
- 239000012065 filter cake Substances 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 25
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- JHIAOWGCGNMQKA-UHFFFAOYSA-N 2-methyl-8-quinolinamine Chemical compound C1=CC=C(N)C2=NC(C)=CC=C21 JHIAOWGCGNMQKA-UHFFFAOYSA-N 0.000 claims abstract description 12
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 9
- 239000011248 coating agent Substances 0.000 claims abstract description 6
- 238000000576 coating method Methods 0.000 claims abstract description 6
- 238000006482 condensation reaction Methods 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 238000001291 vacuum drying Methods 0.000 claims abstract description 4
- 238000007865 diluting Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 42
- 238000010438 heat treatment Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 14
- 238000010790 dilution Methods 0.000 claims description 13
- 239000012895 dilution Substances 0.000 claims description 13
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 12
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 12
- 239000011343 solid material Substances 0.000 claims description 7
- 239000011592 zinc chloride Substances 0.000 claims description 7
- 235000005074 zinc chloride Nutrition 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- BJSKBZUMYQBSOQ-UHFFFAOYSA-N Jeffamine M-600 Chemical group COCCOCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)OCC(C)N BJSKBZUMYQBSOQ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000583 O-(2-Aminopropyl)-O′-(2-methoxyethyl)polypropylene glycol Polymers 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 238000004090 dissolution Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 210000003298 dental enamel Anatomy 0.000 description 25
- 239000002245 particle Substances 0.000 description 20
- 239000012452 mother liquor Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000002798 polar solvent Substances 0.000 description 9
- 238000009826 distribution Methods 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 239000002736 nonionic surfactant Substances 0.000 description 6
- 239000003973 paint Substances 0.000 description 5
- 238000005086 pumping Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000056 polyoxyethylene ether Chemical group 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C09B25/00—Quinophthalones
-
- 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
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
Abstract
The invention discloses a pigment yellow 138 easy to disperse in a weak solvent and a preparation method thereof. The invention comprises the following steps: 1) Preparation of crude pigment yellow 138: 100kg of o-dichlorobenzene, tetrachlorophthalic anhydride, a catalyst and 8-aminoquinaldine are subjected to condensation reaction under the protection of nitrogen to obtain crude mixed liquor of pigment yellow 138; vacuum drying the pigment yellow 138 crude product mixed solution to obtain a pigment yellow 138 crude product; 2) Preparation of pigment yellow 138 fine product: acid-dissolving the crude pigment yellow 138 product with acetic acid to obtain a refined pigment yellow 138 mixed solution; diluting and filtering the pigment yellow 138 fine mixed solution to obtain pigment yellow 138 fine filter cake; 3) Preparation of the easily dispersible pigment yellow 138 product: coating the pigment surface of the pigment yellow 138 fine filter cake by using water and an auxiliary agent to obtain an easily dispersible pigment yellow 138 material; and drying the materials to obtain a spherical easily-dispersible pigment yellow 138 product.
Description
Technical Field
The invention relates to the technical field of pigments, in particular to pigment yellow 138 easy to disperse in a weak solvent and a preparation method thereof.
Background
The traditional pigment toner is difficult to disperse, common grinding is carried out in resin and polar solvent through pigment addition, resin is used as a carrier and is combined with a coated material or a printed material, and most weak solvents have poor compatibility with the resin due to various types of the resin, so that the phenomena of precipitation and agglomeration can occur in the process of storing paint and ink prepared from the pigment for a long time, the problems of reduced tinting strength and insufficient pigment color development can also exist, and great difficulty is caused for later coating or printing. For this purpose, the applicant has developed an easily dispersible pigment which is easily dispersible in a weak solvent.
Disclosure of Invention
In order to make up for the defects of the prior art, the invention provides an environment-friendly pigment yellow 138 easy to disperse in a weak solvent and a preparation method thereof.
The technical scheme of the invention is as follows:
a preparation method of pigment yellow 138 easy to disperse in an environment-friendly polar solvent comprises the following steps:
1) Preparation of crude pigment yellow 138: 100kg of o-dichlorobenzene, tetrachlorophthalic anhydride, a catalyst and 8-aminoquinaldine are subjected to condensation reaction under the protection of nitrogen to obtain crude mixed liquor of pigment yellow 138; vacuum drying the obtained pigment yellow 138 crude product mixed solution to obtain a pigment yellow 138 crude product;
2) Preparation of pigment yellow 138 fine product: acid-dissolving the crude pigment yellow 138 product with acetic acid to obtain a refined pigment yellow 138 mixed solution; diluting and filtering the pigment yellow 138 fine mixed solution to obtain pigment yellow 138 fine filter cake;
3) Preparation of the easily dispersible pigment yellow 138 product: coating the pigment surface of the pigment yellow 138 fine filter cake by using water and an auxiliary agent to obtain an easily dispersible pigment yellow 138 material; and (3) drying the easily-dispersible pigment yellow 138 material to obtain a spherical solid material, namely an easily-dispersible pigment yellow 138 product.
Preferably, in step 1), the specific process steps of the condensation reaction are: under the condition of low-speed stirring, the o-dichlorobenzene is sequentially added with tetrachlorophthalic anhydride, a catalyst and 8-amino quinaldine, nitrogen is filled for protection, then the temperature is raised to 70-80 ℃ for heat preservation for 1-3 hours, and then the temperature is raised to 180-200 ℃ for heat preservation for 6-10 hours.
Preferably, in the step 1), the temperature is 120-140 ℃ and the vacuum degree is-0.08 MPa to-0.1 MPa in the vacuum drying process to recover the solvent, so as to obtain the crude pigment yellow 138.
Preferably, in the step 1), the mass ratio of the o-dichlorobenzene to the tetrachlorophthalic anhydride, the catalyst and the 8-aminoquinaldine is 10-13:1.65:0.2-0.4:0.4; the catalyst is one of zinc chloride, stannic chloride or anhydrous aluminum trichloride.
Preferably, in the step 2), the specific process steps of the acid dissolution reaction are as follows: mixing the pigment yellow 138 crude product with acetic acid, stirring, heating while stirring, heating to 45-55 ℃, and preserving heat and stirring for 4-8 hours.
Preferably, in step 2), the process steps of dilution are: and (3) dripping the pigment yellow 138 fine product mixture into a mixture of water and ice, controlling the temperature of the mixture below 10 ℃ in the dripping process, and stirring for 1 hour after the dripping is finished.
Preferably, in the step 2), the filter cake is washed to be neutral by ice water with the temperature of 0-5 ℃ in the suction filtration process.
Preferably, in the step 2), the mass ratio of the acetic acid to the crude pigment yellow 138 is 6-12:1; wherein the mass ratio of water, ice and crude pigment yellow 138 is 7.58:15.15:0.9-1.03.
Preferably, in the step 3), the specific process steps of coating the pigment surface of the pigment yellow 138 fine filter cake by using water and an auxiliary agent are as follows: mixing the pigment yellow 138 fine filter cake, water and an auxiliary agent, stirring for 1h at a high speed, heating to 80-90 ℃, and stirring for 2h at a constant temperature to obtain an easily dispersible pigment yellow 138 material.
Preferably, in the step 3), the weight ratio of the auxiliary agent to pigment yellow 138 fine filter cake is 1:0.4-0.6.
Preferably, in step 3), the adjuvant is O- (2-aminopropyl) -O' - (2-methoxyethyl) polypropylene glycol or henckmann polyetheramine surfactant.
Preferably, in step 3), the henckmann polyetheramine is SURFONAMINE ® L-100、SURFONAMINE ® L-200、SURFONAMINE ® L-207 and SURFONAMINE ® One of L-300.
Preferably, in the step 1), the stirring speed of low-speed stirring is 90-130r/min, and in the step 3), the stirring speed of high-speed stirring is 5500-6500r/min.
An easily dispersible pigment yellow 138 product prepared by the method for preparing easily dispersible pigment yellow 138 in a weak polar solvent.
Compared with the prior art, the invention has the following beneficial effects:
the color vividness of the easily dispersible pigment yellow 138 product prepared by the method is higher, and the particle size (D 1 ) More uniform, wherein 80% of the easily dispersible pigment yellow 138 product has a particle size distribution in the range of 0.1-0.3 um.
The method has the advantages that the pigment crude product is fully developed through low shearing force in the preparation process of the pigment yellow 138 crude product, and the vividness and the tinting strength of the crude product are improved;
according to the invention, in the preparation process of the pigment yellow 138 crude product, o-dichlorobenzene is adopted as a solvent for condensation reaction, so that the solvent raw material is easy to obtain and recycle, the recycling rate can be more than 98%, and the problem that the brightness of the pigment is affected due to the fact that the solvent is mixed into the pigment product because of poor recycling can be effectively avoided; in the preparation process of pigment yellow 138 fine product, acetic acid is adopted as solvent, so that pigment yellow 138 crude product has good dissolution effect, pigment formed by acidic body pigment has smaller particle size and larger specific surface area, specifically, because pigment is dispersed in acetic acid to form particles with very fine particle size, commonly called primary particles, the primary particles are influenced by temperature, pressure, an organic solvent system and pH value to form secondary aggregates, the particle size becomes larger, the tinting strength is rapidly reduced, and the larger the aggregated particles are under the conditions of higher general temperature, smaller pressure, more organic phase, higher pH value and the like, therefore, the invention adopts a mode of adding low Wen Di and controlling the mixing temperature to be lower than 10 degrees to dilute, and effectively reduces the formation of the secondary aggregates. In summary, in the preparation process of pigment yellow 138 fine product, the operation is simple and convenient, the procedures are few, the energy is saved, the environment is protected, the tinting strength is better, and the dispersibility is better; in the preparation process of the easily-dispersible pigment yellow 138 product, the invention ensures that the particles form a blocking space between the particles by selecting the effective surfactant to wrap the surfaces of the pigment particles, effectively prevents the particles from agglomerating, ensures that the paint and the ink manufactured by the pigment product are mostly precipitated and agglomerated after long-time storage, effectively improves the storage stability of the easily-dispersible pigment yellow 138 product, and finds that the paint and the ink manufactured by the easily-dispersible pigment yellow 138 product prepared by the invention can be respectively stably stored for 200 days and 180 days through experimental verification; specifically, the nonionic surfactant containing alkyl and polyoxyethylene ether groups is used, so that when the number of ethylene oxide added in the nonionic surfactant is low, the nonionic surfactant is only dissolved in nonpolar mineral oil and is not dissolved in an aqueous medium; when the number of the ethylene oxide added in the nonionic surfactant is increased, the hydrophilic performance of the nonionic surfactant is obviously increased, and the nonionic surfactant can be dissolved in water, the surfactant with a large number of the added ethylene oxide can greatly improve the compatibility with weak solvents (such as alcohols of ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol and the like or ethers of diethylene glycol dimethyl ether, diethylene glycol methyl ether, diethylene glycol diethyl ether and the like); is very suitable for the application in the paint and ink industries.
Detailed Description
Embodiment one:
a preparation method of pigment yellow 138 easy to disperse in an environment-friendly polar solvent comprises the following steps:
1) Preparation of crude pigment yellow 138: adding 3300kg of o-dichlorobenzene into an enamel reaction kettle, sequentially adding 412.5kg of tetrachlorophthalic anhydride, 50kg of zinc chloride and 100kg of 8-amino quinaldine at a rotation speed of 130r/min, charging nitrogen, slowly heating to 80 ℃, preserving heat for 1h, and heating to 180-200 ℃ and preserving heat for 6 h to obtain a pigment yellow 138 crude product mixed solution; putting the obtained pigment yellow 138 crude product mixed solution into a vacuum paddle dryer, and recovering the solvent at the temperature of 120-140 ℃ and the vacuum degree of-0.08 MPa to-0.1 MPa to obtain a pigment yellow 138 crude product, wherein the mass of the pigment yellow 138 crude product is 330kg;
2) Preparation of pigment yellow 138 fine product: adding 3000kg of acetic acid and 330kg of pigment yellow 138 crude product into an acid-soluble enamel reaction tank, stirring, heating to 50 ℃, keeping the temperature, stirring for 4 hours, and dissolving all the pigment yellow 138 crude product into acetic acid to obtain pigment yellow 138 refined mixed solution, wherein the mass concentration of the acetic acid in the step 2) is more than 98%; dropwise adding the pigment yellow 138 fine product mixed solution into an enamel dilution kettle which is pre-added with 2500kg of water and 5000kg of ice cubes, controlling the temperature of the solution in the enamel dilution kettle to be below 10 ℃ in the dropwise adding process of pigment yellow 138 fine product mixed solution, and stirring for 1 hour after the dropwise adding is finished to obtain a diluted solution; pumping the diluted solution into a filter press, washing with 0-5 ℃ ice water to neutrality to obtain pigment yellow 138 fine filter cake, wherein the dry mass of the pigment yellow 138 fine filter cake is 300kg;
3) Preparation of the easily dispersible pigment yellow 138 product: in the step, the auxiliary agent is O- (2-aminopropyl) -O' - (2-methoxyethyl) polypropylene glycol, and is obtained through market purchase. The specific process of the step is as follows: adding 300kg of pigment yellow 138 fine filter cake, 2500kg of water and 180kg of O- (2-aminopropyl) -O' - (2-methoxyethyl) polypropylene glycol into a high-speed dispersion kettle, stirring for 1h at a stirring speed of 6000r/min, heating to 80-90 ℃, preserving heat, stirring for 2h, internally circulating the materials by a pump, and measuring that the quantity distribution of 80% of pigment particle size is 0.1-0.3um by an online particle size analyzer to obtain a qualified easily-dispersible pigment yellow 138 material; and conveying the easily dispersible pigment yellow 138 material to a spray dryer by using a screw pump for drying to obtain a spherical solid material, namely an easily dispersible pigment yellow 138 product.
Embodiment two:
the second embodiment is different from the first embodiment in that: in step 1) of example two, tin tetrachloride was used as the catalyst, and the mass of tin tetrachloride was 50kg. Other preparation process conditions were set as in example one.
Embodiment III:
the third embodiment is different from the first embodiment in that: in step 1) of example three, anhydrous aluminum trichloride was used as the catalyst, and the mass of the anhydrous aluminum trichloride was 50kg. Other preparation process conditions were set as in example one.
Embodiment four:
a preparation method of pigment yellow 138 easy to disperse in an environment-friendly polar solvent comprises the following steps:
1) Preparation of crude pigment yellow 138: 2500kg of o-dichlorobenzene is put into an enamel reaction kettle, 412.5kg of tetrachlorophthalic anhydride, 100kg of zinc chloride and 100kg of 8-amino quinaldine are sequentially put into the enamel reaction kettle at the rotation speed of 130r/min, nitrogen is filled, the temperature is slowly raised to 80 ℃ for 1h, and then the temperature is raised to 180-200 ℃ for 6 h, so as to obtain crude pigment yellow 138 mixed solution; putting the obtained mixed solution into a vacuum paddle dryer, and recovering the solvent at the temperature of 120-140 ℃ and the vacuum degree of-0.08 MPa to-0.1 MPa to obtain a crude pigment yellow 138 product, wherein the mass of the crude pigment yellow 138 product is 328kg;
2) Preparation of pigment yellow 138 fine product: adding 3000kg of acetic acid and 328kg of pigment yellow 138 crude product into an acid-soluble enamel reaction tank, stirring, heating to 50 ℃, preserving heat, stirring for 4 hours, and dissolving all the pigment yellow 138 crude product into acetic acid to obtain pigment yellow 138 refined product mixed solution, wherein the mass concentration of the acetic acid in the step 2) is more than 98%; dropwise adding the pigment yellow 138 fine product mixed solution into an enamel dilution kettle with 2500kg of water and 5000kg of ice blocks in advance, controlling the temperature of the solution in the enamel dilution kettle to be below 10 ℃ in the dropwise adding process of pigment yellow 138 fine product mixed solution, and stirring for 1 hour after the dropwise adding is finished to obtain a diluted solution; pumping the diluted solution into a filter press, washing with 0-5 ℃ ice water to neutrality to obtain pigment yellow 138 fine filter cake, wherein the dry mass of the pigment yellow 138 fine filter cake is 296kg;
3) Preparation of the easily dispersible pigment yellow 138 product: the auxiliary agent in this step is SURFONAMINE ® L-100, wherein the auxiliary agent is obtained through market purchase, and the structural general formula of the auxiliary agent is as follows: CH (CH) 3 -[OCH 2 CH 2 ] x -(OCH 2 CH(CH 3 )] y -NH 2 . The specific process of the step is as follows: adding 296kg of pigment yellow 138 fine filter cake and 2500kg, SURFONAMINE of water into a high-speed dispersing kettle ® L-100 kg, stirring for 1h at a stirring speed of 6000r/min, heating to 80-90 ℃, preserving heat, stirring for 2h, circulating the materials in a pump, and determining that the quantity distribution of 80% of pigment particle size is 0.1-0.3um as qualified by an online particle size analyzer to obtain a pigment yellow 138 material easy to disperse; and then conveying the easily dispersible pigment yellow 138 material to a spray dryer by using a screw pump for drying to obtain a spherical solid material, namely an easily dispersible pigment yellow 138 product.
Fifth embodiment:
the fifth embodiment is different from the fourth embodiment in that: in step 1) of the fifth embodiment, tin tetrachloride was used as the catalyst, and the mass of tin tetrachloride was 100kg. Other preparation process conditions were set in the same manner as in example four.
Example six:
the sixth embodiment is different from the fourth embodiment in that: in step 1) of example six, anhydrous aluminum trichloride was used as the catalyst, and the mass of the anhydrous aluminum trichloride was 100kg. Other preparation process conditions were set in the same manner as in example four.
Embodiment seven:
a preparation method of pigment yellow 138 easy to disperse in an environment-friendly polar solvent comprises the following steps:
1) Preparation of crude pigment yellow 138: 2500kg of o-dichlorobenzene is put into an enamel reaction kettle, 412.5kg of tetrachlorophthalic anhydride, 50kg of zinc chloride and 100kg of 8-amino quinaldine are sequentially put into the enamel reaction kettle at the rotation speed of 130r/min, nitrogen is filled, the temperature is slowly raised to 80 ℃, the temperature is kept for 1h, and the temperature is raised to 180-200 ℃ and the temperature is kept for 4 h, so that a pigment yellow 138 crude product mixed solution is obtained; putting the obtained pigment yellow 138 crude product mixed solution into a vacuum paddle dryer, and recovering the solvent at the temperature of 120-140 ℃ and the vacuum degree of-0.08 MPa to-0.1 MPa to obtain a pigment yellow 138 crude product, wherein the mass of the pigment yellow 138 crude product is 330kg;
2) Preparation of pigment yellow 138 fine product: adding 2000kg of acetic acid and 330kg of pigment yellow 138 crude product into an acid-soluble enamel reaction tank, stirring, heating to 50 ℃, keeping the temperature, stirring for 6 hours, and dissolving all the pigment yellow 138 crude product into acetic acid to obtain pigment yellow 138 refined mixed solution, wherein the mass concentration of the acetic acid in the step 2) is more than 98%; dropwise adding the pigment yellow 138 fine product mixed solution into an enamel dilution kettle which is pre-added with 2500kg of water and 5000kg of ice blocks, controlling the temperature of the solution in the enamel dilution kettle to be below 10 ℃ in the dropwise adding process of pigment yellow 138 fine product mixed solution, and stirring for 1 hour after the dropwise adding is finished to obtain a diluted solution; pumping the diluted solution into a filter press, washing with 0-5 ℃ ice water to neutrality to obtain pigment yellow 138 fine filter cake, wherein the dry mass of the pigment yellow 138 fine filter cake is 300kg;
3) Preparation of the easily dispersible pigment yellow 138 product: the auxiliary agent in this step is SURFONAMINE ® L-200, wherein the auxiliary agent is obtained through market purchase, and the structural general formula of the auxiliary agent is as follows: CH (CH) 3 -[OCH 2 CH 2 ] x -(OCH 2 CH(CH 3 )] y -NH 2 . The specific process of the step is as follows: adding 300kg of pigment yellow 138 fine filter cake and 2500kg, SURFONAMINE of water into a high-speed dispersing kettle ® L-200 180kg, stirring for 1h at 6000r/min, heating to 80-90deg.C, maintaining the temperature, stirring for 2h, circulating the materials with pump, and measuring the distribution of 80% of pigment particle diameter in 0.1-0.3um by online particle size analyzerGet the pigment yellow 138 material of easy dispersion; to obtain a pigment yellow 138 material which is easy to disperse; and then conveying the easily dispersible pigment yellow 138 material to a spray dryer by using a screw pump for drying to obtain a spherical solid material, namely an easily dispersible pigment yellow 138 product.
Example eight:
embodiment eight differs from embodiment seven in that: in step 1) of example eight, tin tetrachloride was used as the catalyst, and the mass of tin tetrachloride was 50kg. Other preparation process conditions were set as in example seven.
Example nine:
embodiment nine differs from embodiment seven in that: in step 1) of example nine, anhydrous aluminum trichloride was used as the catalyst, and the mass of the anhydrous aluminum trichloride was 50kg. Other preparation process conditions were set as in example seven.
Example ten:
a preparation method of pigment yellow 138 easy to disperse in an environment-friendly polar solvent comprises the following steps:
1) Preparation of crude pigment yellow 138: 2500kg of o-dichlorobenzene is put into an enamel reaction kettle, 412.5kg of tetrachlorophthalic anhydride, 50kg of zinc chloride and 100kg of 8-amino quinaldine are sequentially put into the enamel reaction kettle at the rotation speed of 90r/min, nitrogen is filled, the temperature is slowly raised to 80 ℃, the temperature is kept for 1h, and the temperature is raised to 180-200 ℃ and the temperature is kept for 8 h, so that a pigment yellow 138 crude product mixed solution is obtained; putting the obtained pigment yellow 138 crude product mixed solution into a vacuum paddle dryer, and recovering the solvent at the temperature of 120-140 ℃ and the vacuum degree of-0.08 MPa to-0.1 MPa to obtain pigment yellow 138 crude product, wherein the mass of the pigment yellow 138 crude product is 335kg;
2) Preparation of pigment yellow 138 fine product: adding 4000kg of acetic acid and 335kg of pigment yellow 138 crude product into an acid-soluble enamel reaction tank, stirring, heating to 50 ℃, preserving heat, stirring for 8 hours, and dissolving all the pigment yellow 138 crude product into acetic acid to obtain pigment yellow 138 refined product mixed solution, wherein the mass concentration of the acetic acid in the step 2) is more than 98%; dropwise adding the pigment yellow 138 fine product mixed solution into an enamel dilution kettle which is pre-added with 2500kg of water and 5000kg of ice blocks, controlling the temperature of the solution in the enamel dilution kettle to be 2-10 ℃ in the dropwise adding process of pigment yellow 138 fine product mixed solution, and stirring for 1 hour after the dropwise adding is finished to obtain a dilution liquid; pumping the diluted solution into a filter press, washing with 0-5 ℃ ice water to neutrality to obtain pigment yellow 138 fine filter cake, wherein the mass of the pigment yellow 138 fine filter cake is 303kg;
3) Preparation of the easily dispersible pigment yellow 138 product: the auxiliary agent in this step is SURFONAMINE ® L-207, wherein the auxiliary agent is obtained through market purchase, and the structural general formula of the auxiliary agent is as follows: CH (CH) 3 -[OCH 2 CH 2 ] x -(OCH 2 CH(CH 3 )] y -NH 2 . The specific process of the step is as follows: adding 303kg of pigment yellow 138 fine filter cake and 2500kg, SURFONAMINE of water into a high-speed dispersing kettle ® L-207 kg, stirring for 1h at a stirring speed of 6000r/min, heating to 80-90 ℃, preserving heat, stirring for 2h, circulating the materials in a pump, and determining that the quantity distribution of 80% of pigment particle size is 0.1-0.3um as qualified by an online particle size analyzer to obtain a pigment yellow 138 material easy to disperse; and then conveying the easily dispersible pigment yellow 138 material to a spray dryer by using a screw pump for drying to obtain a spherical solid material, namely an easily dispersible pigment yellow 138 product.
Example eleven:
embodiment eleven differs from embodiment eleven in that: in step 1) of example eleven, tin tetrachloride was used as catalyst, and the mass of tin tetrachloride was 50kg. Other preparation process conditions were set in the same manner as in example ten.
Embodiment twelve:
embodiment twelve differs from embodiment ten in that: in step 1) of example twelve, anhydrous aluminum trichloride was used as the catalyst, and the mass of the anhydrous aluminum trichloride was 50kg. Other preparation process conditions were set in the same manner as in example ten.
Embodiment thirteen:
a preparation method of pigment yellow 138 easy to disperse in an environment-friendly polar solvent comprises the following steps:
1) Preparation of crude pigment yellow 138: 2500kg of o-dichlorobenzene is put into an enamel reaction kettle, 412.5kg of tetrachlorophthalic anhydride, 100kg of zinc chloride and 100kg of 8-amino quinaldine are sequentially put into the enamel reaction kettle at the rotation speed of 130r/min, nitrogen is filled into the enamel reaction kettle, the temperature is slowly raised to 80 ℃, the temperature is kept for 1h, and the temperature is raised to 180-200 ℃ and the temperature is kept for 10 h, so that a pigment yellow 138 crude product mixed solution is obtained; and (3) putting the obtained pigment yellow 138 crude product mixed solution into a vacuum paddle dryer, and recovering the solvent at the temperature of 120-140 ℃ and the vacuum degree of-0.08 MPa to-0.1 MPa to obtain the pigment yellow 138 crude product, wherein the quality of the pigment yellow 138 crude product is 340kg.
2) Preparation of pigment yellow 138 fine product: adding 3000kg of acetic acid and 340kg of pigment yellow 138 crude product into an acid-soluble enamel reaction tank, stirring, heating to 45 ℃, keeping the temperature, stirring for 6 hours, and dissolving all the pigment yellow 138 crude product into acetic acid to obtain pigment yellow 138 refined product mixed solution, wherein the mass concentration of the acetic acid in the step 2) is more than 98%; dropwise adding the pigment yellow 138 fine product mixed solution into an enamel dilution kettle with 2500kg of water and 5000kg of ice blocks in advance, controlling the temperature of the solution in the enamel dilution kettle to be below 10 ℃ in the dropwise adding process of pigment yellow 138 fine product mixed solution, and stirring for 1 hour after the dropwise adding is finished to obtain a diluted solution; pumping the diluted solution into a filter press, washing with 0-5 ℃ ice water to neutrality to obtain pigment yellow 138 fine filter cake, wherein the mass of the pigment yellow 138 fine filter cake is 320kg;
3) Preparation of the easily dispersible pigment yellow 138 product: the auxiliary agent in this step is SURFONAMINE ® L-300, wherein the auxiliary agent is obtained through market purchase, and the structural general formula of the auxiliary agent is as follows: CH (CH) 3 -[OCH 2 CH 2 ] x -(OCH 2 CH(CH 3 )] y -NH 2 . The specific process of the step is as follows: adding 320kg of pigment yellow 138 fine filter cake and 2500kg, SURFONAMINE of water into a high-speed dispersing kettle ® L-300 kg, stirring for 1h at a stirring speed of 6000r/min, heating to 80-90 ℃, preserving heat, stirring for 2h, circulating the materials in a pump, and determining that the quantity distribution of 80% of pigment particle size is 0.1-0.3um as qualified by an online particle size analyzer to obtain a pigment yellow 138 material easy to disperse; and then conveying the easily dispersible pigment yellow 138 material to a spray dryer by using a screw pump for drying to obtain a spherical solid material, namely an easily dispersible pigment yellow 138 product and an easily dispersible pigment yellow 138 product.
Fourteen examples:
embodiment fourteen differs from embodiment thirteenth in that: in step 1) of example fourteen, tin tetrachloride was used as the catalyst, and the mass of tin tetrachloride was 100kg. Other preparation process conditions were set in the same manner as in the thirteenth example.
Example fifteen:
the fifteenth embodiment differs from the thirteenth embodiment in that: in step 1) of example fifteen, anhydrous aluminum trichloride was used as the catalyst, and the mass of the anhydrous aluminum trichloride was 100kg. Other preparation process conditions were set in the same manner as in the thirteenth example.
In order to further illustrate the beneficial effects of the present invention, test statistics are specifically performed on the color condition of the crude pigment yellow 138 product, the tinting strength condition of the fine pigment yellow 138 product, the vividness, the easy dispersion degree and the yield of the easily dispersible pigment yellow 138 product in examples one to fifteen, and the statistical results are shown in the following table:
in the invention, the test method of the easy dispersion degree is as follows: adding 10g of sample into 50g of polar solvent, stirring at normal temperature for 10min, filtering out insoluble substances, and drying to obtain insoluble substance number; calculation formula = (sample mass-insoluble matter mass)/sample number x 100%; the judgment result is as follows: and the numerical value is more than 95 percent and is qualified.
The method for expressing the vividness in the invention comprises the following steps: data measured by using a reflected light of a spectrophotometer (color difference meter). Vividness is delta L, and positive value is bright, which is expressed as vivid; negative values are dark and are indicated as not vivid.
The method for expressing the tinting strength in the invention comprises the following steps:
1. examples one to fifteen pigment products and the preparation of the concentrated mother liquor of the standard pigment: the concentrated color mother liquor of examples one to fifteen is the same as the preparation method of the concentrated color mother liquor of the standard sample, and the preparation method is detailed by taking the preparation of the concentrated color mother liquor of the standard sample as an example: weighing 50.000g of standard sample pigment and 60.00g of zirconium beads in a 1000ml sand grinding bottle, grinding, sampling and measuring fineness every 1 hour, controlling for 3 hours, grinding to below 5 micrometers (detecting by a scraper fineness gauge), and filtering out mother liquor for later use;
2. examples one to fifteen pigment products and light color mother liquor preparation of standard pigments: the light-colored mother liquor of examples one to fifteen is the same as the light-colored mother liquor of the standard sample, and the preparation method is detailed by taking the light-colored mother liquor of the standard sample as an example: taking 1g of a concentrated mother liquor color paste of a standard sample and 20g of white emulsion paint, and uniformly stirring in a beaker;
3. the tinting strength identification method comprises the following steps: weighing 0.5g of light color mother liquor of pigment products of one to fifteen examples respectively, placing the light color mother liquor on white board paper, uniformly scraping the light color mother liquor from top to bottom by a wet wax preparation device (or a silk stick), then taking 0.5g of light color mother liquor of fifteen standard samples, wherein one standard sample corresponds to one sample, placing the sample on the white board paper, uniformly scraping the sample from top to bottom by the wet wax preparation device (or the silk stick), keeping the parallel interval between the standard sample and the sample to be about 15 mm, and then measuring data by utilizing reflected light of a spectrophotometer (color difference meter), wherein the ratio of test data of the sample to test data of the standard sample is the tinting strength.
Claims (8)
1. A preparation method of pigment yellow 138 easy to disperse in weak solvent is characterized in that: the method comprises the following steps:
1) Preparation of crude pigment yellow 138: condensation reaction is carried out on o-dichlorobenzene, tetrachlorophthalic anhydride, a catalyst and 8-aminoquinaldine under the protection of nitrogen, so as to obtain crude mixed liquid of pigment yellow 138; vacuum drying the obtained pigment yellow 138 crude product mixed solution to obtain a pigment yellow 138 crude product; the specific process steps of the condensation reaction are as follows: adding tetrachlorophthalic anhydride, a catalyst and 8-amino quinaldine in turn under the condition of low-speed stirring, charging nitrogen for protection, heating to 70-80 ℃, preserving heat for 1-3h, heating to 180-200 ℃ and preserving heat for 6-10 h; the mass ratio of the o-dichlorobenzene to the tetrachlorophthalic anhydride to the catalyst to the 8-aminoquinaldine is 10-13:1.65:0.2-0.4:0.4; the catalyst is one of zinc chloride, stannic chloride or anhydrous aluminum trichloride;
2) Preparation of pigment yellow 138 fine product: acid-dissolving the crude pigment yellow 138 product with acetic acid to obtain a refined pigment yellow 138 mixed solution; diluting and filtering the pigment yellow 138 fine mixed solution to obtain pigment yellow 138 fine filter cake;
3) Preparation of the easily dispersible pigment yellow 138 product: coating the pigment surface of the pigment yellow 138 fine filter cake by using water and an auxiliary agent to obtain an easily dispersible pigment yellow 138 material; and (3) drying the easily-dispersible pigment yellow 138 material to obtain a spherical solid material, namely an easily-dispersible pigment yellow 138 product.
2. The method for preparing the pigment yellow 138 which is easy to disperse in a weak solvent according to claim 1, wherein the method comprises the following steps: in the step 2), the specific process steps of the acid dissolution reaction are as follows: mixing the pigment yellow 138 crude product with acetic acid, stirring, heating to 45-55 ℃, and preserving heat and stirring for 4-8 hours.
3. The method for preparing the pigment yellow 138 which is easy to disperse in a weak solvent according to claim 1, wherein the method comprises the following steps: in the step 2), the mass ratio of the acetic acid to the crude pigment yellow 138 is 6-12:1; in the step 2), the process steps of dilution are as follows: dripping pigment yellow 138 fine product mixture into a mixture of water and ice, controlling the temperature of the mixture below 10 ℃ in the dripping process, and stirring for 1 hour after the dripping is finished; wherein the mass ratio of water, ice and crude pigment yellow 138 is 7.58:15.15:0.9-1.03.
4. The method for preparing the pigment yellow 138 which is easy to disperse in a weak solvent according to claim 1, wherein the method comprises the following steps: in the step 3), the specific process steps of coating the pigment surface of the pigment yellow 138 fine filter cake by using water and an auxiliary agent are as follows: mixing the pigment yellow 138 fine filter cake, water and an auxiliary agent, stirring for 1h at a high speed, heating to 80-90 ℃, and preserving heat and stirring for 2h.
5. The method for preparing the pigment yellow 138 which is easy to disperse in a weak solvent according to claim 1, wherein the method comprises the following steps: in the step 3), the weight ratio of the auxiliary agent to the pigment yellow 138 fine filter cake is 1:0.72-1.5.
6. The method for preparing the pigment yellow 138 which is easy to disperse in a weak solvent according to claim 1, wherein the method comprises the following steps: in the step 3), the auxiliary agent is O- (2-aminopropyl) -O' - (2-methoxyethyl) polypropylene glycol or Hunsman polyether amine surfactant.
7. The method for preparing the pigment yellow 138 which is easy to disperse in a weak solvent according to claim 6, wherein: in step 3), the Hunsman polyetheramine is SURFONAMINE ® L-100、SURFONAMINE ® L-200、SURFONAMINE ® L-207 and SURFONAMINE ® One of L-300.
8. A readily dispersible pigment yellow 138 product prepared by the process for preparing a readily dispersible pigment yellow 138 in a weak solvent according to any one of claims 1 to 6.
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