CN116333221A - Color pigment dispersion liquid, color photoresist and preparation method thereof - Google Patents
Color pigment dispersion liquid, color photoresist and preparation method thereof Download PDFInfo
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- CN116333221A CN116333221A CN202310151874.6A CN202310151874A CN116333221A CN 116333221 A CN116333221 A CN 116333221A CN 202310151874 A CN202310151874 A CN 202310151874A CN 116333221 A CN116333221 A CN 116333221A
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- pigment dispersion
- dispersion liquid
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- photoresist
- color pigment
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- 239000000049 pigment Substances 0.000 title claims abstract description 104
- 239000006185 dispersion Substances 0.000 title claims abstract description 103
- 239000007788 liquid Substances 0.000 title claims abstract description 72
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 40
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 40
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 36
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000002245 particle Substances 0.000 claims abstract description 26
- 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 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims abstract description 13
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 12
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims abstract description 12
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 claims abstract description 11
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000011347 resin Substances 0.000 claims abstract description 10
- 229920005989 resin Polymers 0.000 claims abstract description 10
- 239000000654 additive Substances 0.000 claims abstract description 9
- 230000000996 additive effect Effects 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011259 mixed solution Substances 0.000 claims description 45
- 238000000227 grinding Methods 0.000 claims description 39
- 239000002202 Polyethylene glycol Substances 0.000 claims description 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
- 229920001223 polyethylene glycol Polymers 0.000 claims description 29
- 238000003756 stirring Methods 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011324 bead Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 239000004576 sand Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 239000004925 Acrylic resin Substances 0.000 claims description 5
- 229920000178 Acrylic resin Polymers 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000005303 weighing Methods 0.000 claims description 5
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 4
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 claims description 3
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000007822 coupling agent Substances 0.000 claims description 3
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 claims description 3
- 229940116423 propylene glycol diacetate Drugs 0.000 claims description 3
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 claims description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 2
- 239000013530 defoamer Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000009736 wetting Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 5
- 229910052777 Praseodymium Inorganic materials 0.000 description 4
- 238000005054 agglomeration Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- 239000001052 yellow pigment Substances 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000003020 moisturizing effect Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 230000003381 solubilizing effect Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Classifications
-
- 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
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- 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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- 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
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
-
- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
-
- 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
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
The invention relates to a color pigment dispersion liquid, a color photoresist and a preparation method thereof, belonging to the technical field of color pigment dispersion liquid and photoresist. The color pigment dispersion liquid comprises the following raw materials: styrene, maleic anhydride, vinyltrimethoxysilane, methoxypolyethylene glycol methacrylate mixtures, isooctyl acrylate, azobisisobutyronitrile, diethylene glycol, ethyl butyrate, n-butanol and isopropanol. The color photoresist includes the color pigment dispersion liquid as described above, and further includes a photoresist resin, a photoinitiator, a solvent, and an additive. In the preparation of the color pigment dispersion liquid, styrene, maleic anhydride and vinyl trimethoxy silane are added to perform synergistic action, so that the prepared dispersion liquid has excellent dispersion performance; the azodiisobutyronitrile and the diglycol are added, so that the surfaces of pigment particles can be quickly wetted, and the fluidity of dispersion liquid can be improved; the addition of the methoxypolyethylene glycol methacrylate mixture improves the stability of the dispersion on the pigment surface.
Description
Technical Field
The invention belongs to the technical field of color pigment dispersion liquid and photoresist, and particularly relates to a color pigment dispersion liquid, a color photoresist and a preparation method thereof.
Background
The organic pigment has complete color spectrum, high coloring strength, bright color and wide pigment application range, and is an indispensable part for industrial raw materials and colorful life of people in the fields of paint, ink, rubber, synthetic fiber, plastics and the like. The dispersion process of the pigment comprises three steps of wetting, dispersing and stabilizing, wherein in the wetting process, air and water vapor on the surface of the pigment are replaced by a resin solution, and a solid/gas phase is converted into a solid/liquid phase; in the dispersing process, the agglomeration state of the pigment is broken into smaller particles mainly under the action of mechanical energy to become a dispersing state; in the stabilizing process, the dispersing agent is used for keeping the dispersion state of the pigment stable, preventing uncontrolled flocculation and re-agglomeration of particles, so that the suspension liquid obtains a stable state.
In addition, the pigment dispersion is also one of important raw materials for preparing pigment photoresist, and the prepared pigment photoresist is commonly used for preparing a plurality of structures of a color filter, and particularly can comprise a black shading layer, a color filter pixel, a supporting protrusion, a surface protection layer and the like, so the pigment dispersion serving as a product preparation base is particularly important. However, many enterprises find that the dispersibility of the color pigment dispersion liquid to pigment particles is not as strong as imagination in the process of purchasing and using the existing commercial color pigment dispersion liquid, and even if the color pigment dispersion liquid with good dispersibility is purchased, the stability of the color pigment dispersion liquid on the surface of the pigment is weak, which causes great confusion to users.
Disclosure of Invention
The invention aims to provide a color pigment dispersion liquid, a color photoresist and a preparation method thereof, styrene and maleic anhydride are added to form a stable transition state of positive and negative polarity phase absorption, and vinyl trimethoxy silane is mixed on the basis to perform synergistic action, so that the dispersion performance of the color pigment dispersion liquid is enhanced; the azodiisobutyronitrile and the diglycol are added, and after the azodiisobutyronitrile is decomposed for a period of time, more free radicals can be generated, so that the growth of the polymer chain is promoted to be completed in a shorter time; the diethylene glycol can play roles in regulating the viscosity of the system and solubilizing and moisturizing, effectively regulate and control electrostatic repulsive force among pigment particles, and prevent small particles from agglomerating in the system to further generate large particles; the mixture of methoxy polyethylene glycol methacrylate is added, and the mixture is formed by mixing 2 methoxy polyethylene glycol methacrylate with different molecular weights according to the mass ratio of the proper substances, so that the stability of the dispersion liquid on the surface of the pigment is improved. In addition, the color pigment dispersion liquid is also applied to the color photoresist, and has good developing performance and high color saturation. Solves the problems of weak dispersibility and poor stability on the surface of pigment existing in the color pigment dispersion liquid in the prior art.
The aim of the invention can be achieved by the following technical scheme:
a color pigment dispersion liquid comprising the following raw materials in parts by weight:
further, the methoxy polyethylene glycol methacrylate mixture comprises methoxy polyethylene glycol methacrylate with the molecular weight of 1100 and methoxy polyethylene glycol methacrylate with the molecular weight of 550 which are mixed according to the mass ratio of 0.9-1.1:0.3-0.4.
Further, the preparation method of the color pigment dispersion liquid comprises the following steps:
(1) Preparation of a mixed solution A: weighing ethyl butyrate and azodiisobutyronitrile, placing the ethyl butyrate and azodiisobutyronitrile into a reactor, sequentially adding styrene, maleic anhydride and vinyltrimethoxysilane into the reactor, starting the reactor, stirring under the protection of nitrogen, heating, keeping the temperature after the heating is finished, and reacting for 2.5-3h to obtain a mixed solution A after the reaction is finished;
(2) Preparation of a mixed solution B: dropwise adding n-butanol into the mixed solution A prepared in the step (1), and then adding methoxy polyethylene glycol methacrylate mixture, isooctyl acrylate and diethylene glycol after the dropwise adding is finished, and carrying out reflux reaction to obtain a mixed solution B;
(3) Preparation of color pigment dispersion: adding isopropanol into the mixed solution B obtained in the step (2), stirring uniformly to obtain mixed solution C, transferring the mixed solution C into a grinding tank, grinding at a controlled speed by adopting a ball mill, filtering by qualitative filter paper after finishing grinding to obtain a pre-dispersion liquid, and transferring the pre-dispersion liquid into a sand mill for grinding and dispersing to obtain the color pigment dispersion liquid.
Further, the reactor in the step (1) is a four-neck flask provided with a thermometer, a stirring device, a constant pressure dropping funnel and a condensing tube, and the temperature is raised to 75-85 ℃ while stirring.
Further, the speed of dropwise adding the n-butanol in the step (2) is 4-5s/d, and the reflux reaction time is 3-4.5h.
Further, the grinding medium of the grinding tank in the step (3) is zirconium dioxide beads with the particle size of 0.4-0.6mm, the mass of the zirconium dioxide beads is 2 times that of the mixed solution C, the speed of speed-controlled grinding is 580-610r/min, and the grinding dispersion is specifically that a sand mill is firstly used for grinding 5-10min at the speed of 2.5-4.5m/s, and then is used for grinding for 2-5h at the speed of 8.5-13.5 m/s.
As a preferred embodiment of the present invention, a color photoresist includes any one of the above color pigment dispersions, and the color photoresist further includes a photoresist resin, a photoinitiator, a solvent, and an additive.
Further, the photoresist resin is acrylic resin, the photoinitiator comprises one of a photoinitiator OXE-01 and isopropyl thioxanthone, the solvent comprises one or more of propylene glycol methyl ether acetate, propylene glycol diacetate, cyclopentanone, cyclohexanone, diethylene glycol methyl ethyl ether and diethylene glycol dibutyl ether, and the additive comprises one or more of a leveling agent, a coupling agent, a defoaming agent and an ultraviolet absorber.
Further, the weight ratio of the color pigment dispersion liquid to the photoresist resin to the photoinitiator to the solvent to the additive is 26.3-68.5:10.1-18.6:2.1-2.8:18-56:1-1.9.
Further, the preparation method of the color photoresist comprises the steps of mixing and stirring the dispersion liquid, the photoresist resin, the photoinitiator, the solvent and the additive for 6-8 hours to obtain the color photoresist.
The invention has the beneficial effects that:
(1) The invention adds the synergistic effect of the styrene, the maleic anhydride and the vinyl trimethoxy silane, so that the prepared color pigment dispersion liquid has excellent dispersion performance. In detail, maleic anhydride has strong electron withdrawing group with positive polarity, although steric hindrance is larger, it is difficult to self-polymerize, but because styrene has benzene ring conjugation effect, electrons can be given out to become negative polarity, so that styrene and maleic anhydride can form stable transition state of positive and negative polarity attraction, vinyl trimethoxy silane is mixed on the basis, and the synthesized polymer molecular chain contains more silanol groups with reactivity.
(2) According to the invention, the azodiisobutyronitrile is used as an initiator, the diglycol is used as a cosolvent, the effects of rapidly wetting the surfaces of pigment particles and improving the fluidity of the color pigment dispersion liquid are achieved, the grinding time of the pigment in the grinding equipment is shortened, the grinding efficiency is improved, the energy consumption of the equipment is reduced, and meanwhile, the fluidity of the dispersion liquid is improved, and the phenomena of agglomeration, sedimentation, flooding, and the like of pigment particles can be effectively prevented. This is because azobisisobutyronitrile, after a period of time of decomposition, can generate more radicals, causing the polymer chain growth to be completed in a shorter time; the diethylene glycol can play roles in regulating the viscosity of the system and solubilizing and moisturizing, effectively regulate and control electrostatic repulsive force among pigment particles, and prevent small particles from agglomerating in the system to further generate large particles.
(3) The methoxy polyethylene glycol methacrylate mixture added in the invention is formed by mixing methoxy polyethylene glycol methacrylate with the molecular weight of 1100 and methoxy polyethylene glycol methacrylate with the molecular weight of 550, so that the prepared color pigment dispersion liquid has excellent stabilizing effect. The invention reasonably prepares the mass ratio of 2 methoxy polyethylene glycol methacrylates with different molecular weights, is favorable for the methoxy polyethylene glycol methacrylate with the long-chain branch to be uniformly distributed on the main molecular chain of the polymer, and simultaneously, improves the stability of the color pigment dispersion liquid on the surface of the pigment.
(4) The preparation method of the color pigment dispersion liquid developed by the invention is simple, and the added raw materials ensure the excellent dispersibility of the prepared dispersion liquid and the stability of the dispersion liquid on the surface of the pigment, thereby producing obvious beneficial and practical effects. In addition, the color pigment dispersion liquid can be used as one of the preparation raw materials of the color photoresist, and the use method is simple and the finished product has wide application.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
A color pigment dispersion liquid comprising the following raw materials in parts by weight:
the methoxy polyethylene glycol methacrylate mixture comprises methoxy polyethylene glycol methacrylate with the molecular weight of 1100 and methoxy polyethylene glycol methacrylate with the molecular weight of 550 which are mixed according to the mass ratio of 1:0.3.
The preparation method of the color pigment dispersion liquid comprises the following steps:
(1) Preparation of a mixed solution A: weighing ethyl butyrate and azodiisobutyronitrile, placing the ethyl butyrate and azodiisobutyronitrile in a four-neck flask provided with a thermometer, a stirring device, a constant pressure dropping funnel and a condensing tube, sequentially adding styrene, maleic anhydride and vinyl trimethoxysilane into the four-neck flask, heating to 75 ℃ under the protection of nitrogen while stirring, keeping the temperature after the heating is finished, reacting for 3 hours, and obtaining a mixed solution A after the reaction is finished;
(2) Preparation of a mixed solution B: dropwise adding n-butanol into the mixed solution A prepared in the step (1) at the speed of 5s/d, and then adding methoxy polyethylene glycol methacrylate mixture, isooctyl acrylate and diethylene glycol after the dropwise adding is finished, and carrying out reflux reaction for 4h to obtain mixed solution B;
(3) Preparation of color pigment dispersion: adding isopropanol into the mixed solution B obtained in the step (2), stirring uniformly to obtain mixed solution C, transferring the mixed solution C into a zirconium dioxide bead grinding tank with the particle size of 0.5mm, grinding by adopting a ball mill at a speed of 580r/min, filtering by qualitative filter paper after grinding to obtain a pre-dispersion liquid, transferring the pre-dispersion liquid into a sand mill, grinding at a speed of 3.5m/s for 8 min, grinding at a speed of 13.5m/s for 4h, and obtaining the color pigment dispersion liquid after grinding.
Wherein the mass of the zirconium dioxide beads is 2 times of that of the mixed solution C.
Example 2
A color pigment dispersion liquid comprising the following raw materials in parts by weight:
the methoxy polyethylene glycol methacrylate mixture comprises methoxy polyethylene glycol methacrylate with the molecular weight of 1100 and methoxy polyethylene glycol methacrylate with the molecular weight of 550 which are mixed according to the mass ratio of 0, 9:0.4.
The preparation method of the color pigment dispersion liquid comprises the following steps:
(1) Preparation of a mixed solution A: weighing ethyl butyrate and azodiisobutyronitrile, placing the ethyl butyrate and azodiisobutyronitrile in a four-neck flask provided with a thermometer, a stirring device, a constant pressure dropping funnel and a condenser pipe, sequentially adding styrene, maleic anhydride and vinyl trimethoxysilane into the four-neck flask, heating to 85 ℃ under the protection of nitrogen while stirring, keeping the temperature after the temperature is increased, reacting for 2.5 hours, and obtaining a mixed solution A after the reaction is finished;
(2) Preparation of a mixed solution B: dropwise adding n-butanol into the mixed solution A prepared in the step (1) at the speed of 5s/d, and then adding methoxy polyethylene glycol methacrylate mixture, isooctyl acrylate and diethylene glycol after the dropwise adding is finished, and carrying out reflux reaction for 3h to obtain mixed solution B;
(3) Preparation of color pigment dispersion: adding isopropanol into the mixed solution B obtained in the step (2), stirring uniformly to obtain mixed solution C, transferring the mixed solution C into a zirconium dioxide bead grinding tank with the particle size of 0.6mm, grinding by adopting a ball mill at a speed of 610r/min, filtering by qualitative filter paper after grinding to obtain a pre-dispersion liquid, transferring the pre-dispersion liquid into a sand mill, grinding at a speed of 2.5m/s for 10min, grinding at a speed of 8.5m/s for 2h, and obtaining the color pigment dispersion liquid after grinding.
Wherein the mass of the zirconium dioxide beads is 2 times of that of the mixed solution C.
Example 3
A color pigment dispersion liquid comprising the following raw materials in parts by weight:
the methoxy polyethylene glycol methacrylate mixture comprises methoxy polyethylene glycol methacrylate with the molecular weight of 1100 and methoxy polyethylene glycol methacrylate with the molecular weight of 550 which are mixed according to the mass ratio of 1.1:0.3.
The preparation method of the color pigment dispersion liquid comprises the following steps:
(1) Preparation of a mixed solution A: weighing ethyl butyrate and azodiisobutyronitrile, placing the ethyl butyrate and azodiisobutyronitrile in a four-neck flask provided with a thermometer, a stirring device, a constant pressure dropping funnel and a condenser pipe, sequentially adding styrene, maleic anhydride and vinyl trimethoxysilane into the four-neck flask, heating to 80 ℃ under the protection of nitrogen while stirring, keeping the temperature after the heating is finished, reacting for 3 hours, and obtaining a mixed solution A after the reaction is finished;
(2) Preparation of a mixed solution B: dropwise adding n-butanol into the mixed solution A prepared in the step (1) at the speed of 4s/d, and adding methoxy polyethylene glycol methacrylate mixture, isooctyl acrylate and diethylene glycol after the dropwise adding is finished, and carrying out reflux reaction for 4.5h to obtain a mixed solution B;
(3) Preparation of color pigment dispersion: adding isopropanol into the mixed solution B obtained in the step (2), stirring uniformly to obtain mixed solution C, transferring the mixed solution C into a zirconium dioxide bead grinding tank with the particle size of 0.4mm, grinding by adopting a ball mill at a speed of 595 r/min, filtering by qualitative filter paper after grinding to obtain a pre-dispersion liquid, transferring the pre-dispersion liquid into a sand mill, grinding at a speed of 4.5m/s for 5 min, grinding at a speed of 11m/s for 5h, and obtaining the color pigment dispersion liquid after grinding.
Wherein the mass of the zirconium dioxide beads is 2 times of that of the mixed solution C.
Comparative examples 1 to 3
In comparison with example 1, the parts by weight of styrene, maleic anhydride and vinyltrimethoxysilane in comparative examples 1 to 3 are shown in Table 1, and the remaining preparation steps and parameters are the same.
TABLE 1
Comparative example 4
In comparison with example 1, azobisisobutyronitrile was 3 parts by weight, and the remaining preparation steps and parameters were the same.
Comparative example 5
In comparison with example 1, azobisisobutyronitrile was 10 parts by weight, and the remaining preparation steps and parameters were the same.
Comparative example 6
In comparison with example 1, diethylene glycol was 45 parts by weight, and the remaining preparation steps and parameters were the same.
Comparative example 7
In comparison with example 1, diethylene glycol was 78 parts by weight, the remaining preparation steps and parameters being identical.
Comparative example 8
In comparison with example 1, the methoxypolyethylene glycol methacrylate having a molecular weight of 1100 in the methoxypolyethylene glycol methacrylate mixture was replaced with methoxypolyethylene glycol methacrylate having a molecular weight of 2000, and the remaining preparation steps and parameters were identical.
Comparative example 9
In comparison with example 1, the methoxypolyethylene glycol methacrylate having a molecular weight of 550 in the methoxypolyethylene glycol methacrylate mixture was replaced with methoxypolyethylene glycol methacrylate having a molecular weight of 350, and the remaining preparation steps and parameters were identical.
Comparative examples 10 to 13
In comparison with example 1, the amounts of the methoxypolyethylene glycol methacrylate having a molecular weight of 1100 and methoxypolyethylene glycol methacrylate having a molecular weight of 550 in comparative examples 10 to 13 are shown in Table 2, and the remaining preparation steps and parameters are the same.
TABLE 2
Example 4
The color photoresist comprises the following raw materials in parts by weight:
the preparation method of the color photoresist comprises the following steps: the color pigment dispersion liquid prepared in example 1, acrylic resin, isopropyl thioxanthone, cyclohexanone and ultraviolet absorbent were mixed and stirred for 6 hours to obtain a color photoresist.
The color photoresist prepared based on the pigment dispersion prepared in example 1 was tested for good development and high color saturation.
Example 5
The color photoresist comprises the following raw materials in parts by weight:
the preparation method of the color photoresist comprises the following steps: the color pigment dispersion liquid prepared in example 2, acrylic resin, a photoinitiator OXE-01, diethylene glycol methyl ethyl ether and a coupling agent are mixed and stirred for 7 hours, and then the color photoresist is obtained.
The color photoresist prepared based on the pigment dispersion prepared in example 2 was tested for good development and high color saturation.
Example 6
The color photoresist comprises the following raw materials in parts by weight:
the preparation method of the color photoresist comprises the following steps: the color pigment dispersion liquid prepared in example 3, acrylic resin, a photoinitiator OXE-01, propylene glycol diacetate and a leveling agent are mixed and stirred for 8 hours, and then the color photoresist is obtained.
The color photoresist prepared based on the pigment dispersion prepared in example 3 was tested for good development and high color saturation.
Test example 1
The color pigment dispersion liquid and pigment (praseodymium yellow pigment is selected in the test example) prepared in the examples 1-3 and the comparative examples 1-3 are respectively taken to prepare praseodymium yellow pigment suspension liquid with the mass fraction of 5%, after the suspension liquid is fully mixed and ultrasonically oscillated for 30 min, 10mL of the suspension liquid is measured and placed in a 10mL colorimetric tube, the suspension liquid is vertically placed on a test tube rack for standing, and meanwhile, the time for counting is started, and the time required for the pigment to completely settle is recorded.
The longer the time to complete sedimentation, the better the pigment dispersion, and the results are shown in Table 3.
TABLE 3 Table 3
As is clear from Table 3, the color pigment dispersion liquid obtained by the present invention has excellent dispersion properties. Styrene and maleic anhydride are added to form a stable transition state of positive and negative polarity attraction, vinyl trimethoxy silane is mixed on the basis to act synergistically, and the synthesized polymer molecular chain contains more silanol groups with reactivity.
Test example 2
The color pigment dispersions prepared in examples 1-3 and comparative examples 4-7 were respectively taken, pigments (praseodymium yellow pigments were used in this test example) were added, stirring was carried out by a stirrer for 30 min, the wetting speed of the pigment particles on the surfaces and the fluidity of the pigment dispersion among the pigment particles during observation were recorded according to the evaluation results, and after completion of stirring, whether pigment particle agglomeration phenomenon occurred in the system was observed and recorded;
evaluation results:
pigment particle surface wetting speed: fast, faster, medium, slower, slow;
fluidity of pigment dispersion among pigment particles: good, better, medium, weaker, weak.
The results are shown in Table 4.
TABLE 4 Table 4
As is clear from Table 4, the color pigment dispersion liquid prepared by the present invention has the effect of rapidly wetting the surfaces of pigment particles and improving the fluidity of the color pigment dispersion liquid. This is because azobisisobutyronitrile, after a period of time of decomposition, can generate more radicals, causing the polymer chain growth to be completed in a shorter time; the diethylene glycol can play roles in regulating the viscosity of the system and solubilizing and moisturizing, effectively regulate and control electrostatic repulsive force among pigment particles, and prevent small particles from agglomerating in the system to further generate large particles.
Test example 3
The color pigment dispersions prepared in examples 1-3 and comparative examples 8-13 were each prepared by adding a pigment (praseodymium yellow pigment was used in this test example), stirring and pulverizing uniformly with a stirrer, a disperser, and a sand mill to obtain a pigment dispersion, centrifuging the pigment dispersion in a centrifuge tube at 3000 r/min for 30 min, collecting 1 drop of the upper dispersion after centrifugation, diluting with deionized water by a certain multiple, and measuring its absorbance A at 550nm with a 722-type spectrophotometer 1 In addition, the color pigment dispersion liquid which is not centrifuged is diluted by the same multiple, the absorbance A is measured, and the stability of the dispersion system is characterized by the ratio R of the absorbance of the system before and after centrifugation:
the larger the R value, the better the dispersion stability, and the results are shown in Table 5.
TABLE 5
As is clear from Table 5, the color pigment dispersion liquid obtained by the present invention has excellent stabilizing effect. The methoxy polyethylene glycol methacrylate mixture added in the invention is formed by mixing methoxy polyethylene glycol methacrylate with longer branched chain and 1100 molecular weight and methoxy polyethylene glycol methacrylate with shorter branched chain and 550 molecular weight, and the mass ratio of 2 methoxy polyethylene glycol methacrylates with different molecular weights is prepared, so that the methoxy polyethylene glycol methacrylate with long branched chain is uniformly distributed on the main molecular chain of the polymer, and meanwhile, the stability of the dispersion liquid on the surface of the pigment is further improved.
In the description of the present specification, the descriptions of the terms "one embodiment," "example," "specific example," and the like, mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the present invention. In this specification, schematic representations of the above terms do not necessarily refer to the same embodiments or examples. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is merely illustrative and explanatory of the invention, as various modifications and additions may be made to the particular embodiments described, or in a similar manner, by those skilled in the art, without departing from the scope of the invention or exceeding the scope of the invention as defined in the claims.
Claims (10)
1. The color pigment dispersion liquid is characterized by comprising the following raw materials in parts by weight:
2. the color pigment dispersion according to claim 1, wherein the methoxypolyethylene glycol methacrylate mixture comprises methoxypolyethylene glycol methacrylate having a molecular weight of 1100 and methoxypolyethylene glycol methacrylate having a molecular weight of 550 in a mass ratio of 0.9 to 1.1:0.3 to 0.4.
3. A method of preparing a color pigment dispersion according to any one of claims 1 to 2, comprising the steps of:
(1) Preparation of a mixed solution A: weighing ethyl butyrate and azodiisobutyronitrile, placing the ethyl butyrate and azodiisobutyronitrile into a reactor, sequentially adding styrene, maleic anhydride and vinyltrimethoxysilane into the reactor, starting the reactor, stirring under the protection of nitrogen, heating, keeping the temperature after the heating is finished, and reacting for 2.5-3h to obtain a mixed solution A after the reaction is finished;
(2) Preparation of a mixed solution B: dropwise adding n-butanol into the mixed solution A prepared in the step (1), and then adding methoxy polyethylene glycol methacrylate mixture, isooctyl acrylate and diethylene glycol after the dropwise adding is finished, and carrying out reflux reaction to obtain a mixed solution B;
(3) Preparation of color pigment dispersion: adding isopropanol into the mixed solution B obtained in the step (2), stirring uniformly to obtain mixed solution C, transferring the mixed solution C into a grinding tank, grinding at a controlled speed by adopting a ball mill, filtering by qualitative filter paper after finishing grinding to obtain a pre-dispersion liquid, and transferring the pre-dispersion liquid into a sand mill for grinding and dispersing to obtain the color pigment dispersion liquid.
4. The method for producing a color pigment dispersion liquid according to claim 3, wherein the reactor in the step (1) is a four-necked flask equipped with a thermometer, a stirring device, a constant pressure dropping funnel and a condenser tube, and the temperature is raised to 75 to 85℃while stirring.
5. A method for preparing a color pigment dispersion according to claim 3, wherein the rate of dropping n-butanol in step (2) is 4-5s/d, and the reflux reaction time is 3-4.5h.
6. The method for preparing a color pigment dispersion according to claim 3, wherein the grinding medium in the grinding tank in the step (3) is zirconium dioxide beads with a particle size of 0.4-0.6mm, the mass of the zirconium dioxide beads is 2 times that of the mixed solution C, the speed of the grinding is 580-610r/min, and the grinding dispersion is specifically that a sand mill is firstly ground for 5-10min at a speed of 2.5-4.5m/s, and then ground for 2-5h at a speed of 8.5-13.5 m/s.
7. A color photoresist comprising the color pigment dispersion of any one of claims 1-2, the color photoresist further comprising a photoresist resin, a photoinitiator, a solvent, and an additive.
8. The color photoresist according to claim 7, wherein the photoresist resin is acrylic resin, the photoinitiator comprises one of photoinitiator OXE-01 and isopropyl thioxanthone, the solvent comprises one or more of propylene glycol methyl ether acetate, propylene glycol diacetate, cyclopentanone, cyclohexanone, diethylene glycol methyl ethyl ether and diethylene glycol dibutyl ether, and the additive comprises one or more of leveling agent, coupling agent, defoamer and ultraviolet absorber.
9. The colored photoresist according to claim 7, wherein the weight ratio of the colored pigment dispersion, the photoresist resin, the photoinitiator, the solvent and the additive is 26.3-68.5:10.1-18.6:2.1-2.8:18-56:1-1.9.
10. The method for preparing the color photoresist according to claim 7, wherein the method comprises the step of mixing and stirring the dispersion liquid, the photoresist resin, the photoinitiator, the solvent and the additive for 6-8 hours to obtain the color photoresist.
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