CN114773914A - Pigment dispersion liquid and preparation method and application thereof - Google Patents
Pigment dispersion liquid and preparation method and application thereof Download PDFInfo
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- CN114773914A CN114773914A CN202210542117.7A CN202210542117A CN114773914A CN 114773914 A CN114773914 A CN 114773914A CN 202210542117 A CN202210542117 A CN 202210542117A CN 114773914 A CN114773914 A CN 114773914A
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- pigment
- pigment dispersion
- dispersion liquid
- parts
- binder resin
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- 239000000049 pigment Substances 0.000 title claims abstract description 136
- 239000006185 dispersion Substances 0.000 title claims abstract description 101
- 239000007788 liquid Substances 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title abstract description 20
- 239000000178 monomer Substances 0.000 claims abstract description 57
- 229920005989 resin Polymers 0.000 claims abstract description 50
- 239000011347 resin Substances 0.000 claims abstract description 50
- 239000011230 binding agent Substances 0.000 claims abstract description 49
- 239000002270 dispersing agent Substances 0.000 claims abstract description 30
- 239000003960 organic solvent Substances 0.000 claims abstract description 20
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 10
- 150000003949 imides Chemical class 0.000 claims abstract description 10
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 9
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 9
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 27
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 13
- -1 glycidyl alpha-n-propyl acrylate Chemical compound 0.000 claims description 12
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 238000000227 grinding Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 claims description 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 claims description 5
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 claims description 4
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 claims description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000002245 particle Substances 0.000 abstract description 35
- 238000009826 distribution Methods 0.000 abstract description 15
- 238000005054 agglomeration Methods 0.000 abstract description 6
- 230000002776 aggregation Effects 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 25
- 238000003756 stirring Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 8
- 238000000498 ball milling Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000011259 mixed solution Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000012860 organic pigment Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000001055 blue pigment Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000005626 carbonium group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007561 laser diffraction method Methods 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002159 nanocrystal Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 229940067265 pigment yellow 138 Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/002—Pigment pastes, e.g. for mixing in paints in organic medium
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
The invention discloses a pigment dispersion liquid and a preparation method and application thereof, wherein the pigment dispersion liquid comprises a pigment, a dispersing agent, a binder resin solution and an organic solvent, wherein the binder resin is obtained by copolymerizing an unsaturated carboxylic acid monomer, an unsaturated carboxylic ester monomer containing an epoxy group, an unsaturated imide monomer and an aromatic vinyl monomer which can be selectively added. The pigment dispersion liquid can realize that the particle size of the pigment reaches a nanometer level and narrower particle size distribution, and simultaneously, the stability of the pigment dispersion liquid is improved, and the problem of particle agglomeration is not easy to occur.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a pigment dispersion liquid, a preparation method thereof and application of the pigment dispersion liquid in manufacturing a color filter of a display.
Background
With the continuous development of the technology, the requirements of color filters for Liquid Crystal Displays (LCDs) are higher, such as higher transmittance, higher contrast, etc. To achieve these characteristics more efficiently, it is often necessary to treat the pigment to make the pigment particle size smaller. Chinese patent CN101081943A discloses an organic pigment nano dispersion and a preparation method thereof, wherein, the preparation of the organic pigment nano particles is that organic pigment is dissolved in good solvent to form solution, and then mixed with poor solvent to precipitate organic pigment with nano size. Chinese patent CN101302354A discloses a method for preparing pigment particle aggregates and dispersions, wherein the organic pigment nanoparticles are also prepared by the above-mentioned "good solvent" dissolution and "poor solvent" precipitation methods. Chinese patent CN101622315A discloses surface-modified nanoparticles comprising cationic colorants for use in color filters, formed by covalent attachment of the cationic colorant (di (tri) -aryl (hetero) -dye or tri-aryl (hetero) carbonium pigment) to an organophilic modified natural or synthetic phyllosilicate. According to the preparation method of the blue pigment with the nanometer particle size, the photosensitive resin and the color filter disclosed in the Chinese patent CN110294945B, the self-made first or second or third or fourth synergist is mixed with the blue pigment, and then the mixture is subjected to ball milling in a PGMEA medium, so that nanometer blue pigment particles with the particle size of less than 50nm are obtained. Although the above method can effectively obtain the pigment with smaller particle size, the specific surface area of the pigment particles is increased with the continuous reduction of the particle size of the pigment particles, and the tendency of pigment particle agglomeration is very strong, so that the use amount of the dispersing agent is increased, or a more efficient dispersing agent is developed to avoid or slow down the secondary agglomeration phenomenon of the small particle pigment in the solvent, so that the pigment can exist in the solvent with more stable particle size distribution. U.S. Pat. No. 4,8465553 discloses a method for preparing a pigment dispersion liquid for a photoresist from an azo pigment, an azo pigment derivative, a dispersant, etc., the pigment derivative contributing to the improvement of the dispersion effect of the pigment dispersion liquid. Chinese patent CN101405310B discloses a polymer compound and a method for producing the same, which is used for preparing a pigment dispersion liquid for a color filter. Chinese patent CN110088650B discloses a dispersion, and an ink composition for ink jet, a light conversion layer and a liquid crystal display element using the dispersion, wherein a polymer dispersant with an amine value of more than or equal to 5mgKOH/g, an acid value of less than or equal to 50mgKOH/g and a weight average molecular weight of more than 1000 is selected to improve the dispersibility of nanocrystals. In addition, chinese patent CN102081305B discloses a blue coloring composition for color filters, a color filter, and a color display, in which a salt-formed product of a xanthene acid dye and a compound having a cationic group is added to a colorant, and a binder resin is added to a color filter composition formed from the colorant, so that the resulting pigment dispersion has higher dispersion stability.
Although the micronization of the pigment and the dispersion stability of the pigment in a solvent can be improved by the method, the phenomena of thickening and precipitation caused by re-agglomeration of pigment particles due to long-term storage cannot be effectively avoided, so that the problems of reduced contrast ratio of the optical filter, reduced product performance and the like appear in practical application.
Disclosure of Invention
In order to solve the above technical problems, the present invention aims to provide a pigment dispersion, a preparation method and an application thereof; the pigment dispersion liquid can realize the particle size distribution of the pigment reaching the nanometer level and being narrower, simultaneously improves the stability of the pigment dispersion liquid, and is not easy to cause the problem of particle agglomeration.
In order to achieve the technical purpose and achieve the technical effect, the invention is realized by the following technical scheme:
a pigment dispersing liquid is prepared from pigment, disperser, adhesive resin solution and organic solvent through copolymerizing unsaturated carboxylic acid monomer, unsaturated carboxylate monomer containing epoxy group, unsaturated imide monomer and optional aromatic vinyl monomer.
Further, the pigment dispersion liquid comprises the following components in percentage by mass: 5 to 30 percent of pigment, 3 to 25 percent of dispersant, 0.5 to 45 percent of binder resin solution and 37.5 to 91.5 percent of organic solvent.
Further, the unsaturated carboxylic acid monomer is selected from one or more of (methyl) acrylic acid, vinyl benzoic acid, maleic acid, fumaric acid, itaconic acid and crotonic acid; the unsaturated carboxylic ester monomer containing epoxy group is one or more of glycidyl (meth) acrylate, glycidyl alpha-ethacrylate, glycidyl alpha-n-propyl acrylate and glycidyl alpha-n-butyl acrylate; the unsaturated imide monomer is selected from one or more of N-phenyl maleimide, N-benzyl maleimide and N-cyclohexyl maleimide; the aromatic vinyl monomer is selected from one or more of styrene, alpha-methyl styrene, p-methyl styrene, m-methyl styrene and p-methoxy styrene.
Further, the binder resin has a structure represented by formula (I):
in the formula (I), a, b, c and d are integers, a is more than or equal to 35 and less than or equal to 45, b is more than or equal to 55 and less than or equal to 70, c is more than or equal to 50 and less than or equal to 65, and d is more than or equal to 40 and less than or equal to 55; r is1-R4Each independently selected from H, CH3、COOH、CH2COOH、C6H5COOH；R5Selected from phenyl, benzyl, cyclohexyl; r6Selected from hydrogen, methyl, ethyl, n-propyl, n-butyl; r7Selected from H, CH 3; r is8Selected from m-methylphenyl, p-methylphenyl and p-methoxyphenyl.
Further, the dispersant is at least one selected from acrylate dispersant, polyester dispersant and polyurethane dispersant, such as BYK2000, BYK163, SOLSPERSE 24000 and SOLSPERSE 32000.
Further, the organic solvent is at least one selected from propylene glycol methyl ether acetate, propylene glycol methyl ether, cyclohexanone, ethyl acetate, butyl acetate and propylene glycol.
Further, the solvent used for the binder resin solution is the same as the organic solvent used for the pigment dispersion liquid.
The invention further provides a preparation method of the pigment dispersion liquid, which comprises the following steps: mixing, dispersing and grinding the whole amount of the pigment, the dispersing agent, the binder resin solution and a part amount of the organic solvent according to the mass percentage to obtain a pigment pre-dispersion liquid, and mixing, dispersing and grinding the obtained pigment pre-dispersion liquid and the rest organic solvent to obtain a pigment dispersion liquid.
The invention also provides the application of the pigment dispersion liquid in manufacturing a color filter of a display.
The beneficial effects of the invention are:
the binder resin used in the present invention can be blended with a dispersant, and the microparticulated pigment can be effectively dispersed without increasing the amount of the dispersant added, and the dispersion stability of the pigment dispersion can be improved and the particle size distribution can be narrowed.
The binder resin is obtained by copolymerization reaction of unsaturated double bonds of an acrylic monomer containing unsaturated double bonds, an unsaturated carboxylic ester monomer containing epoxy groups, an unsaturated imide monomer and an aromatic vinyl monomer which is selectively added. Wherein the unsaturated carboxylic ester containing epoxy group can provide crosslinking functional group, which is convenient to form crosslinking structure after being applied in color filter composition (composition containing pigment dispersion liquid, initiator, catalyst, etc.), thereby improving curing sensitivity of the color filter composition; the aromatic vinyl compound, the unsaturated imide and the organic solvent have good compatibility, the dispersion stability of the pigment dispersion liquid is improved, and the intensity of a coloring cured film can be improved after the pigment dispersion liquid is applied to the color filter composition; wherein the acid group at the end of the unsaturated carboxylic acid can serve as an anchor at the time of dispersion, thereby improving the dispersion stability of the pigment dispersion.
The binder resin can act synergistically with a dispersant on the premise of not influencing the strength and the developability of a colored cured film, improve the dispersion stability of a pigment dispersion liquid, prevent the problem of re-agglomeration of pigment particles caused by long-time storage of the pigment dispersion liquid, effectively disperse micronized pigment without increasing the addition amount of the dispersant, and realize the particle size distribution of the pigment to be nanoscale and narrower.
Drawings
FIG. 1 is an infrared spectrum of a binder resin of Synthesis example 1 of the present invention.
FIG. 2 is a graph showing the distribution of the average particle diameter of the pigment in 24 hours and 30 days after the preparation of the pigment dispersion liquid of example 1 of the present invention.
FIG. 3 is a graph showing the distribution of the average particle diameter of the pigment in 24 hours and 30 days after the preparation of the pigment dispersion liquid of example 2 of the present invention.
FIG. 4 is a graph showing the distribution of the average particle diameter of the pigment in 24 hours and 30 days after the preparation of the pigment dispersion liquid of example 3 of the present invention.
FIG. 5 is a graph showing the distribution of the average particle diameter of the pigment in 24 hours and 30 days after the preparation of the pigment dispersion liquid of example 4 of the present invention.
FIG. 6 is a graph showing the average particle diameter distribution of the pigment of 24 hours and 30 days after the preparation of the pigment dispersion liquid of example 5 of the present invention
FIG. 7 is a graph showing the average particle diameter distribution of the pigment 24 hours and 30 days after the preparation of the pigment dispersion liquid of example 6 of the present invention
FIG. 8 is a graph showing the average particle size distribution of the pigment dispersion liquid of example 7 of the present invention at 24 hours and 30 days after the preparation.
Fig. 9 is a graph showing the average particle diameter distribution of the pigment at 24 hours and 30 days after the preparation of the pigment dispersion liquid of the comparative example.
Detailed Description
The technical solutions in the present invention will be described clearly and completely with reference to specific embodiments, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments in the present invention, belong to the protection scope of the present invention.
The invention provides a pigment dispersion liquid which comprises a pigment, a dispersing agent, a binder resin solution and an organic solvent, wherein the binder resin is obtained by copolymerizing an unsaturated carboxylic acid monomer, an unsaturated carboxylic ester monomer containing an epoxy group, an unsaturated imide monomer and an aromatic vinyl monomer which can be selectively added.
Further, the pigment dispersion liquid comprises the following components in percentage by mass: 5 to 30 percent of pigment, 3 to 25 percent of dispersant, 0.5 to 45 percent of binder resin solution and 37.5 to 91.5 percent of organic solvent.
Wherein the unsaturated carboxylic acid monomer is selected from one or more of (methyl) acrylic acid, vinyl benzoic acid, maleic acid, fumaric acid, itaconic acid and butenoic acid; the unsaturated carboxylic ester monomer containing epoxy group is one or more of glycidyl (meth) acrylate, glycidyl alpha-ethacrylate, glycidyl alpha-n-propyl acrylate and glycidyl alpha-n-butyl acrylate; the unsaturated imide monomer is selected from one or more of N-phenyl maleimide, N-benzyl maleimide and N-cyclohexyl maleimide; the aromatic vinyl monomer is selected from one or more of styrene, alpha-methyl styrene, p-methyl styrene, m-methyl styrene and p-methoxy styrene.
The binder resin has a structure represented by formula (I):
in the formula (I), a, b, c and d are integers, a is more than or equal to 35 and less than or equal to 45, b is more than or equal to 55 and less than or equal to 70, c is more than or equal to 50 and less than or equal to 65, and d is more than or equal to 40 and less than or equal to 55; r is1-R4Each independently selected from H, CH3、COOH、CH2COOH、C6H5COOH；R5Selected from phenyl, benzyl, cyclohexyl; r6Selected from hydrogen, methyl, ethyl, n-propyl, n-butyl; r7Selected from H, CH 3; r is8Selected from m-methylphenyl, p-methylphenyl and p-methoxyphenyl.
The preparation process of the binder resin solution comprises the following steps: adding 10-30 parts of unsaturated carboxylic acid (monomer), 10-30 parts of unsaturated imide (monomer), 20-50 parts of unsaturated carboxylic ester (monomer) containing epoxy groups, 0-20 parts of aromatic vinyl monomer and 0.5-15 parts of chain transfer agent into a reactor, stirring and mixing the materials uniformly in an inert atmosphere (such as nitrogen), gradually heating the mixed solution to 80 ℃, and then adding 50-500 parts of propylene glycol methyl ether acetate solution containing 0.5-12 parts of initiator. Keeping the reaction temperature unchanged at 80 ℃, continuously stirring for reaction for 2h, continuously heating the reaction solution to 100 ℃, reacting for 2h, cooling, and taking materials to obtain a binder resin solution;
the dispersant is at least one selected from acrylate dispersant, polyester dispersant and polyurethane dispersant, such as BYK2000, BYK163, SOLSPERSE 24000, SOLSPERSE32000, etc.
The organic solvent in the pigment dispersion liquid is preferably at least one of propylene glycol methyl ether acetate, propylene glycol methyl ether, cyclohexanone, ethyl acetate, butyl acetate, and propylene glycol. The organic solvent used for the pigment dispersion may be the same as that used for the binder resin solution to improve component compatibility.
The invention further provides a preparation method of the pigment dispersion liquid, which comprises the following steps: mixing, dispersing and grinding the whole amount of the pigment, the dispersing agent, the binder resin solution and part amount of the organic solvent according to the mass percent to obtain a pigment pre-dispersion liquid, and mixing, dispersing and grinding the obtained pigment pre-dispersion liquid and the rest organic solvent to obtain the pigment dispersion liquid.
The invention also provides application of the pigment dispersion liquid in manufacturing a color filter of a display, and particularly, the pigment dispersion liquid, an initiator, a catalyst and the like can be prepared into a color filter composition for manufacturing the color filter of the display.
The present invention will be further described with reference to the following specific examples. In the following examples and comparative examples, "parts" means parts by weight.
Synthesis example of binder resin solution:
synthesis example 1
Adding 20 parts of methacrylic acid (monomer), 30 parts of N-phenylmaleimide (monomer), 30 parts of glycidyl methacrylate (monomer), 20 parts of styrene and 2.5 parts of alpha-methylstyrene dimer into a reactor, stirring and mixing the above materials uniformly in an inert atmosphere (such as nitrogen), gradually heating the mixed solution to 80 ℃, and then adding 200 parts of propylene glycol methyl ether acetate solution containing 5 parts of azobisisobutyronitrile. Keeping the reaction temperature unchanged at 80 ℃, continuously stirring for reaction for 2 hours, continuously heating the reaction solution to 100 ℃, reacting for 2 hours, cooling, and taking materials to obtain a binder resin solution 1; wherein the percentage content of the binder resin is 37%, and Mw is 7800; the infrared spectrum of the binder resin in synthetic example 1 is shown in FIG. 1; the analytical explanation of the infrared spectrogram is shown in Table 1.
TABLE 1
Synthesis example 2
Adding 20 parts of methacrylic acid (monomer), 30 parts of N-benzyl maleimide (monomer), 30 parts of glycidyl methacrylate (monomer), 20 parts of styrene and 2.5 parts of alpha-methyl styrene dimer into a reactor, stirring and uniformly mixing the above substances in an inert atmosphere (such as nitrogen), gradually heating the mixed solution to 80 ℃, and adding 200 parts of propylene glycol methyl ether acetate solution containing 5 parts of azobisisobutyronitrile. Keeping the reaction temperature unchanged at 80 ℃, continuously stirring for reaction for 2 hours, continuously heating the reaction solution to 100 ℃, reacting for 2 hours, cooling, and taking materials to obtain a binder resin solution 2; wherein the percentage content of the binder resin is 37%, and Mw is 8100.
Synthesis example 3
20 parts of methacrylic acid (monomer), 30 parts of N-phenylmaleimide (monomer), 30 parts of alpha-ethyl glycidyl acrylate (monomer), 20 parts of styrene and 2.5 parts of alpha-methyl styrene dimer are added into a reactor, the materials are stirred and mixed uniformly under the inert atmosphere (such as nitrogen), the temperature of the mixed solution is gradually increased to 80 ℃, and 200 parts of propylene glycol methyl ether acetate solution containing 5 parts of azodiisobutyronitrile is added. Keeping the reaction temperature unchanged at 80 ℃, continuously stirring for reaction for 2h, continuously heating the reaction solution to 100 ℃, reacting for 2h, cooling, and taking materials to obtain a binder resin solution 3; wherein, the percentage content of the binder resin is 37%, and Mw is 8000.
Synthesis example 4
Adding 25 parts of acrylic acid (monomer), 25 parts of N-phenylmaleimide (monomer), 30 parts of glycidyl methacrylate (monomer), 20 parts of styrene and 2.5 parts of alpha-methyl styrene dimer into a reactor, stirring and mixing the above materials uniformly in an inert atmosphere (such as nitrogen), gradually heating the mixed solution to 80 ℃, and then adding 200 parts of propylene glycol methyl ether acetate solution containing 5 parts of azodiisobutyronitrile. Keeping the reaction temperature unchanged at 80 ℃, continuously stirring for reaction for 2 hours, continuously heating the reaction solution to 100 ℃, reacting for 2 hours, cooling, and taking materials to obtain a binder resin solution 4; wherein the percentage content of the binder resin is 37%, and Mw is 7200.
Synthesis example 5
Adding 25 parts of acrylic acid (monomer), 25 parts of N-phenylmaleimide (monomer), 30 parts of glycidyl methacrylate (monomer), 20 parts of alpha-methyl styrene and 2.5 parts of alpha-methyl styrene dimer into a reactor, stirring and mixing the above substances uniformly in an inert atmosphere (such as nitrogen), gradually heating the mixed solution to 80 ℃, and adding 200 parts of propylene glycol methyl ether acetate solution containing 5 parts of azodiisobutyronitrile. Keeping the reaction temperature unchanged at 80 ℃, continuously stirring for reaction for 2 hours, continuously heating the reaction solution to 100 ℃, reacting for 2 hours, cooling, and taking materials to obtain a binder resin solution 5; wherein the percentage content of the binder resin is 37%, and Mw is 7400.
Synthesis example 6
Adding 20 parts of methacrylic acid (monomer), 30 parts of N-cyclohexylmaleimide (monomer), 30 parts of glycidyl methacrylate (monomer), 20 parts of styrene and 2.5 parts of alpha-methylstyrene dimer into a reactor, stirring and mixing the above materials uniformly in an inert atmosphere (such as nitrogen), gradually heating the mixed solution to 80 ℃, and then adding 200 parts of propylene glycol methyl ether acetate solution containing 5 parts of azobisisobutyronitrile. Keeping the reaction temperature unchanged at 80 ℃, continuously stirring for reaction for 2h, continuously heating the reaction solution to 100 ℃, reacting for 2h, cooling, and taking materials to obtain a binder resin solution 6; wherein the percentage content of the binder resin is 37%, and Mw is 7900.
Synthesis example 7
20 parts of methacrylic acid (monomer), 30 parts of N-cyclohexylmaleimide (monomer), 30 parts of alpha-N-propylglycidyl acrylate (monomer), 20 parts of styrene and 2.5 parts of alpha-methylstyrene dimer are added into a reactor, and the mixture is stirred and mixed uniformly under an inert atmosphere (such as nitrogen), and then the temperature of the mixed solution is gradually increased to 80 ℃, and 200 parts of propylene glycol methyl ether acetate solution containing 5 parts of azobisisobutyronitrile is added. Keeping the reaction temperature unchanged at 80 ℃, continuously stirring for reaction for 2h, continuously heating the reaction solution to 100 ℃, reacting for 2h, cooling, and taking materials to obtain a binder resin solution 7; wherein the percentage content of the binder resin is 37%, and Mw is 8600.
Preparation of pigment Dispersion
Example 1
Fully stirring 30 parts of C.I. pigment red 254 fine powder, 28 parts of binder resin solution 1, 24 parts of BYK2000 and 58 parts of propylene glycol methyl ether acetate, and then carrying out ball milling for 2 hours at the rotating speed of 800r/min to obtain a pigment pre-dispersion liquid; 60 parts of propylene glycol methyl ether acetate is added into the obtained pigment pre-dispersion liquid, and the mixture is ground for 4 hours at the rotating speed of 2500r/min to obtain the pigment dispersion liquid.
Example 2
Fully stirring 30 parts of C.I. pigment red 254 fine powder, 28 parts of binder resin solution 2, 24 parts of BYK2000 and 58 parts of propylene glycol methyl ether acetate, and then ball-milling at the rotating speed of 800r/min for 2 hours to obtain a pigment pre-dispersion liquid; 60 parts of propylene glycol methyl ether acetate was further added to the obtained pigment pre-dispersion liquid, and the mixture was ground at a rotation speed of 2500r/min for 4 hours to obtain a pigment dispersion liquid.
Example 3
Fully stirring 30 parts of C.I. pigment red 254 fine powder, 28 parts of binder resin solution 1, 24 parts of BYK163 and 58 parts of propylene glycol methyl ether acetate, and then carrying out ball milling for 2 hours at the rotating speed of 800r/min to obtain a pigment pre-dispersion liquid; 60 parts of propylene glycol methyl ether acetate solvent is added into the obtained pigment pre-dispersion liquid, and the mixture is ground for 4 hours at the rotating speed of 2500r/min to obtain the pigment dispersion liquid.
Example 4
Fully stirring 30 parts of C.I. pigment red 254 fine powder, 28 parts of binder resin solution 2, 12 parts of SOLSPERSE32000 and 70 parts of propylene glycol methyl ether acetate, and then carrying out ball milling at the rotating speed of 800r/min for 2 hours to obtain a pigment pre-dispersion liquid; 60 parts of propylene glycol methyl ether acetate was further added to the obtained pigment pre-dispersion liquid, and the mixture was ground at a rotation speed of 2500r/min for 4 hours to obtain a pigment dispersion liquid.
Example 5
Fully stirring 30 parts of C.I. pigment red 177 fine powder, 28 parts of binder resin solution 3, 24 parts of EFKA4330 and 65 parts of propylene glycol methyl ether acetate, and then performing ball milling at the rotating speed of 800r/min for 2 hours to obtain a pigment pre-dispersion liquid; 60 parts of propylene glycol methyl ether acetate is added into the obtained pigment pre-dispersion liquid, and the mixture is ground for 4 hours at the rotating speed of 2500r/min to obtain the pigment dispersion liquid.
Example 6
Fully stirring 30 parts of C.I. pigment yellow 138 fine powder, 28 parts of binder resin solution 4, 24 parts of BYK2000 and 58 parts of propylene glycol methyl ether acetate, and then carrying out ball milling for 2 hours at the rotating speed of 800r/min to obtain a pigment pre-dispersion liquid; 60 parts of propylene glycol methyl ether acetate was further added to the obtained pigment pre-dispersion liquid, and the mixture was ground at a rotation speed of 2500r/min for 4 hours to obtain a pigment dispersion liquid.
Example 7
Fully stirring 30 parts of fine powder of 15:6 parts of C.I. pigment blue, 28 parts of binder resin solution 5, 24 parts of BYK2000 and 58 parts of propylene glycol methyl ether acetate, and then ball-milling at the rotating speed of 800r/min for 2 hours to obtain a pigment pre-dispersion liquid; 60 parts of propylene glycol methyl ether acetate is added into the obtained pigment pre-dispersion liquid, and the mixture is ground for 4 hours at the rotating speed of 2500r/min to obtain the pigment dispersion liquid.
Comparative example
Fully stirring and uniformly mixing 30 parts of C.I. pigment red 254 fine powder, 45 parts of BYK2000 and 125 parts of propylene glycol methyl ether acetate in a high-speed dispersion machine to obtain a pigment pre-dispersion liquid; and grinding the obtained pigment pre-dispersion liquid for 4 hours at the rotating speed of 2500r/min to obtain the pigment dispersion liquid.
Evaluation method and evaluation result
The average particle size and polydispersity PDI 24 hours after the pigment dispersion was prepared, the average particle size and polydispersity PDI of the pigment dispersion after 30 days of standing, and the rate of change in the average particle size before and after standing were measured according to the national standard GB/T19077-2016 particle size distribution laser diffraction method, and the results are shown in Table 2 below.
TABLE 2
As is apparent from the test results in table 2, the pigment particles can be effectively dispersed in the embodiment of the present invention through the effective combination of the binder resin and the dispersant, and the embodiment of the present invention can maintain good dispersion stability and narrow pigment particle size distribution.
The above description is only an embodiment of the present invention, and is not intended to limit the scope of the present invention, and all modifications, equivalent changes, direct or indirect applications made by using the contents of the present specification and the attached drawings, or other related fields are included in the scope of the present invention.
Claims (9)
1. A pigment dispersion liquid is characterized by comprising a pigment, a dispersing agent, a binder resin solution and an organic solvent, wherein the binder resin is obtained by copolymerizing an unsaturated carboxylic acid monomer, an unsaturated carboxylic ester monomer containing an epoxy group, an unsaturated imide monomer and an aromatic vinyl monomer which can be selectively added.
2. The pigment dispersion according to claim 1, comprising 5 to 30% of a pigment, 3 to 25% of a dispersant, 0.5 to 45% of a binder resin solution, and 37.5 to 91.5% of an organic solvent.
3. The pigment dispersion according to claim 1, wherein the unsaturated carboxylic acid monomer is selected from one or more of (meth) acrylic acid, vinylbenzoic acid, maleic acid, fumaric acid, itaconic acid, crotonic acid; the unsaturated carboxylic ester monomer containing epoxy group is one or more of glycidyl (meth) acrylate, glycidyl alpha-ethacrylate, glycidyl alpha-n-propyl acrylate and glycidyl alpha-n-butyl acrylate; the unsaturated imide monomer is selected from one or more of N-phenyl maleimide, N-benzyl maleimide and N-cyclohexyl maleimide; the aromatic vinyl monomer is selected from one or more of styrene, alpha-methyl styrene, p-methyl styrene, m-methyl styrene and p-methoxy styrene.
4. The pigment dispersion according to claim 1 or 3, wherein the binder resin has a structure represented by formula (I):
in the formula (I), a, b, c and d are integers, a is more than or equal to 35 and less than or equal to 45, b is more than or equal to 55 and less than or equal to 70, c is more than or equal to 50 and less than or equal to 65, and d is more than or equal to 40 and less than or equal to 55; r1-R4Each independently selected from H, CH3、COOH、CH2COOH、C6H5COOH；R5Selected from phenyl, benzyl, cyclohexyl; r6Selected from hydrogen, methyl, ethyl, n-propyl, n-butyl; r7Selected from H, CH 3; r is8Selected from m-methylphenyl, p-methylphenyl and p-methoxyphenyl.
5. The pigment dispersion liquid according to claim 1, wherein the dispersant is at least one of an acrylate dispersant, a polyester dispersant and a polyurethane dispersant.
6. The pigment dispersion according to claim 1, wherein the organic solvent is at least one selected from the group consisting of propylene glycol methyl ether acetate, propylene glycol methyl ether, cyclohexanone, ethyl acetate, butyl acetate, and propylene glycol.
7. The pigment dispersion according to claim 1, wherein the solvent used for the binder resin solution is the same as the organic solvent used for the pigment dispersion.
8. A process for preparing a pigment dispersion according to any one of claims 1 to 7, characterized by comprising the steps of: mixing, dispersing and grinding the pigment, the dispersing agent, the binder resin solution and a part of organic solvent to obtain a pigment pre-dispersion liquid, and mixing, dispersing and grinding the obtained pigment pre-dispersion liquid and the rest organic solvent to obtain the pigment dispersion liquid.
9. Use of the pigment dispersion according to any one of claims 1 to 7 for the manufacture of color filters for displays.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109696801A (en) * | 2017-10-20 | 2019-04-30 | 东友精细化工有限公司 | Color dispersion liquid, photosensitive composition, pattern layer, colour filter and display device |
| CN111032720A (en) * | 2017-10-10 | 2020-04-17 | 昭和电工株式会社 | Resin, photosensitive resin composition, resin cured film, and image display device |
| CN113004458A (en) * | 2021-03-03 | 2021-06-22 | 传美讯电子科技（珠海）有限公司 | Three-component acrylate dispersant and preparation method thereof, and organic pigment color paste and preparation method thereof |
| WO2021200540A1 (en) * | 2020-04-01 | 2021-10-07 | 株式会社日本触媒 | N-substituted maleimide polymer and method for producing same |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111032720A (en) * | 2017-10-10 | 2020-04-17 | 昭和电工株式会社 | Resin, photosensitive resin composition, resin cured film, and image display device |
| CN109696801A (en) * | 2017-10-20 | 2019-04-30 | 东友精细化工有限公司 | Color dispersion liquid, photosensitive composition, pattern layer, colour filter and display device |
| WO2021200540A1 (en) * | 2020-04-01 | 2021-10-07 | 株式会社日本触媒 | N-substituted maleimide polymer and method for producing same |
| CN113004458A (en) * | 2021-03-03 | 2021-06-22 | 传美讯电子科技（珠海）有限公司 | Three-component acrylate dispersant and preparation method thereof, and organic pigment color paste and preparation method thereof |
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