WO2023053819A1 - Microparticules de résine et leur procédé de production - Google Patents
Microparticules de résine et leur procédé de production Download PDFInfo
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- WO2023053819A1 WO2023053819A1 PCT/JP2022/032504 JP2022032504W WO2023053819A1 WO 2023053819 A1 WO2023053819 A1 WO 2023053819A1 JP 2022032504 W JP2022032504 W JP 2022032504W WO 2023053819 A1 WO2023053819 A1 WO 2023053819A1
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- Prior art keywords
- resin
- meth
- resin fine
- fine particles
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- -1 thiol compound Chemical group 0.000 claims abstract description 76
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- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000009483 freeze granulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- ORTRWBYBJVGVQC-UHFFFAOYSA-N hexadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCS ORTRWBYBJVGVQC-UHFFFAOYSA-N 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000012703 microemulsion polymerization Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SKEQOTBKQUCUGK-UHFFFAOYSA-N o-(2-hydroxyethyl) propanethioate Chemical compound CCC(=S)OCCO SKEQOTBKQUCUGK-UHFFFAOYSA-N 0.000 description 1
- XVKLLVZBGMGICC-UHFFFAOYSA-N o-[3-propanethioyloxy-2,2-bis(propanethioyloxymethyl)propyl] propanethioate Chemical compound CCC(=S)OCC(COC(=S)CC)(COC(=S)CC)COC(=S)CC XVKLLVZBGMGICC-UHFFFAOYSA-N 0.000 description 1
- UPHWVVKYDQHTCF-UHFFFAOYSA-N octadecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN UPHWVVKYDQHTCF-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011242 organic-inorganic particle Substances 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QUPCNWFFTANZPX-UHFFFAOYSA-M paramenthane hydroperoxide Chemical compound [O-]O.CC(C)C1CCC(C)CC1 QUPCNWFFTANZPX-UHFFFAOYSA-M 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010333 wet classification Methods 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
-
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (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
- 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
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(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
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- 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
- 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
- C08F230/085—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 the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
Definitions
- the present invention relates to resin fine particles and a method for producing the same. Specifically, (a) a hydrolyzable silicon compound unit having a hydrolyzable silyl group and a radically polymerizable unsaturated group-reactive group, (b) a monofunctional (meth)acrylic monomer unit, (c) a poly
- the present invention relates to a resin fine particle containing a functional (meth)acrylic monomer unit and (d) a thiol compound unit, and a method for producing the resin fine particle.
- Resin films have long been widely used for applications such as packaging materials. In recent years, the applications thereof have been further expanded, and in particular, in applications such as optical members and electronic devices, the characteristics required of resin films are becoming more sophisticated. And it is required to improve productivity while maintaining the high quality. Resin films are often stored in roll form. When stored in a roll form, the resin films may stick to each other at the overlapping portions, resulting in a problem of poor slipperiness and peelability. For this problem, it is known to add various fillers such as organic particles and inorganic particles to the resin film as an anti-sticking agent (anti-blocking agent). Typical fillers include inorganic particles such as silica, and organic particles such as (meth)acrylic resin fine particles.
- the merits include high hardness and the ability to impart sticking prevention properties with the addition of a small amount.
- the material due to the material, there is a demerit that a difference in refractive index occurs with the resin film, which is a factor that impairs transparency.
- organic particles when used as a filler, there is an advantage that sticking prevention can be imparted while maintaining the transparency of the resin film. For this reason, various organic particles have been developed and used in resin films and the like that require high quality.
- Patent Document 1 describes the use of organic polymer particles containing an antioxidant as an anti-blocking agent for films. Heat resistance can be improved by including an antioxidant in the organic polymer particles.
- Patent Document 2 describes core-shell shaped silicone polymer particles that maintain high transparency and hardness.
- Patent Document 3 describes swollen seed polymer particles using polysiloxane particles as seed particles.
- the organic polymer particles described in Patent Document 1 contain an antioxidant. Many antioxidants with high antioxidant functions have a bulky molecular structure, and therefore are difficult to apply to polymerization methods using water as a medium other than suspension polymerization. Therefore, it is difficult to obtain organic polymer particles that have sufficient properties in terms of particle size distribution and particle size and have more precise optical properties.
- the polymer particles described in Patent Document 2 are expected to have better optical properties than inorganic particles, since they are composed of a silicone polymer, there is a difference in refractive index within the film due to the silicone component. There is a possibility that the haze may be increased due to the occurrence of haze. Therefore, it is difficult to obtain highly transparent polymer particles.
- the swelling seed polymer particles described in Patent Document 3 are produced by sol-gel seed polymerization using polysiloxane particles as seed particles, and are expected to have better optical properties.
- the hurdles for required properties such as transparency have been raised, and the effect of polysiloxane seed particles on film haze cannot be ignored, and swelling seed polymer particles with high transparency are used. is difficult.
- the problem to be solved by the present invention is to provide fine resin particles that are excellent in heat resistance and transparency, have a narrow particle size distribution, and have a small particle size.
- the present invention provides the following resin fine particles and a method for producing resin fine particles.
- Item 1 (a) a hydrolyzable silicon compound unit having a hydrolyzable silyl group and a radically polymerizable unsaturated group-reactive group, (b) a monofunctional (meth)acrylic monomer unit, (c) a poly Resin fine particles containing functional (meth)acrylic monomer units and (d) thiol compound units.
- Item 2 The resin fine particles according to Item 1, wherein the content of silicon element in the resin fine particles measured by fluorescent X-ray analysis is 0.03% by mass or more and 1% by mass or less.
- Item 3 The fine resin particles according to Item 1 or 2, further comprising (e) a monofunctional vinyl-based monomer unit having an aromatic ring in the molecular structure.
- Item 4 Any one of Items 1 to 3, wherein the (b) monofunctional (meth)acrylic monomer unit comprises a (meth)acrylic acid alkyl ester unit having an alkyl group having 2 or more carbon atoms. fine resin particles.
- Item 5 The fine resin particles according to any one of Items 1 to 4, which have a heat weight loss rate of 2.5% or less when heat-treated at 280° C. for 1 hour in a nitrogen atmosphere.
- Item 6 The fine resin particles according to any one of Items 1 to 5, having a 3% thermal decomposition temperature of 350° C. or higher in a nitrogen atmosphere.
- Item 7 The fine resin particles according to any one of Items 1 to 6, having a volume average particle diameter of 0.05 ⁇ m or more and 3 ⁇ m or less.
- Item 8 The fine resin particles according to any one of Items 1 to 7, wherein the coefficient of variation of the volume average particle size is 25% or less.
- Item 9 the following measurement range; (Measurement range) Particle size measurement range: 0.5 ⁇ m to 200 ⁇ m, Particle circularity measurement range: 0.97 to 1.00, Item 9.
- Item 10 The resin fine particles according to any one of Items 1 to 9, further comprising (f) a reactive surfactant unit.
- Item 11 A resin fine particle granule formed by aggregating a plurality of the resin fine particles according to any one of Items 1 to 10.
- Item 12 The fine resin particles according to any one of Items 1 to 11, which are used as an anti-sticking agent for resin films.
- Item 13 The resin fine particles according to Item 12, wherein the resin film is a resin film for optical use.
- Item 14 A first step of preparing seed particles by emulsion polymerization or soap-free polymerization of a monomer component containing a monofunctional (meth)acrylic monomer, and A hydrolyzable silicon compound having a group that reacts with a hydrolyzable silyl group and a radically polymerizable unsaturated group, a monofunctional (meth)acrylic monomer, a polyfunctional (meth)acrylic monomer and a thiol compound a second step of polymerizing by absorbing the mixture containing the seed particles;
- a method for producing resin fine particles having Item 15 The method for producing fine resin particles according to Item 14, wherein the mixture used in the second step further contains a monofunctional vinyl-based monomer having an aromatic ring in its molecular structure.
- Item 16 The method for producing resin fine particles according to Item 14 or 15, comprising a step of classifying the obtained resin fine particles with a filter having an absolute filtration accuracy of 5 ⁇ m or less.
- Item 17 A method for producing resin fine particle granules, comprising granulating and drying the resin fine particles obtained by the method for producing resin fine particles according to any one of Items 14 to 16.
- the present invention it is possible to provide fine resin particles having excellent heat resistance and transparency, a narrow particle size distribution, and a small particle size.
- the fine resin particles as an anti-sticking agent for resin films, particularly as an anti-sticking agent for optical-use resin films, it is possible to stably produce highly transparent resin films for optical-use.
- a (meth)acrylic monomer means an acrylic monomer or a methacrylic monomer
- a (meth)acrylate means an acrylate or a methacrylate
- the resin fine particles of the present invention comprise (a) a hydrolyzable silicon compound unit having a hydrolyzable silyl group and a radically polymerizable unsaturated group-reactive group, (b) a monofunctional (meth)acrylic monomer unit, (c) polyfunctional (meth)acrylic monomer units and (d) thiol compound units.
- the resin fine particles of the present invention may further contain (e) a monofunctional vinyl-based monomer unit having an aromatic ring in its molecular structure and/or (f) a reactive surfactant unit.
- the (a) unit in the fine resin particles of the present invention is a unit derived from a hydrolyzable silicon compound having a group that reacts with a hydrolyzable silyl group and a radically polymerizable unsaturated group.
- Hydrolyzable silyl groups possessed by hydrolyzable silicon compounds are those in which 1 to 3 hydrolyzable groups are bonded to a silicon atom. is a silicon-containing group capable of undergoing a condensation reaction to form a siloxane bond and be crosslinked.
- the hydrolyzable group of the hydrolyzable silyl group is not particularly limited. One or more selected from the group consisting of an acid amide group, an aminooxy group, an iminooxy group, a mercapto group, an alkenyloxy group, an oxime group and the like. Among them, an alkoxysilyl group is preferable because the hydrolysis reaction is mild and the handling is easy.
- Alkoxysilyl groups include trialkoxysilyl groups such as trimethoxysilyl group, triethoxysilyl group, triisopropoxysilyl group, and triphenoxysilyl group; propyldimethoxysilyl group, methyldimethoxysilyl group, and methyldiethoxysilyl group; and monoalkoxysilyl groups such as dimethylmethoxysilyl and dimethylethoxysilyl groups.
- a trialkoxysilyl group is preferable, and a trimethoxysilyl group and a triethoxysilyl group are more preferable.
- the group other than the hydrolyzable group bonded to the silicon atom in the hydrolyzable silyl group is not particularly limited.
- alkyl groups having 20 or less carbon atoms such as methyl group, ethyl group, propyl group and isopropyl group, alkenyl groups having 20 or less carbon atoms, aryl groups having 6 to 30 carbon atoms, arylalkyl groups having 7 to 30 carbon atoms, etc.
- alkyl groups having 20 or less carbon atoms such as methyl group, ethyl group, propyl group and isopropyl group
- alkenyl groups having 20 or less carbon atoms such as methyl group, ethyl group, propyl group and isopropyl group
- alkenyl groups having 20 or less carbon atoms such as methyl group, ethyl group, propyl group and isopropyl group
- alkenyl groups having 20 or less carbon atoms such as methyl group,
- the group that the hydrolyzable silicon compound has has a radically polymerizable unsaturated group that reacts with a radically polymerizable unsaturated group such as a (meth)acryloyl group, a (meth)acrylamide group, a vinyl group, and a styryl group. It is not particularly limited as long as it is a group.
- groups that react with radically polymerizable unsaturated groups possessed by the hydrolyzable silicon compound of the present invention include radically polymerizable groups such as (meth)acryloyl groups, (meth)acrylamide groups, vinyl groups, and styryl groups.
- One or more selected from the group consisting of unsaturated groups, mercapto groups, hydroxyl groups, amino groups and the like can be mentioned.
- the hydrolyzable silicon compound having a hydrolyzable silyl group and a radically polymerizable unsaturated group-reactive group includes, for example, vinyltrimethoxysilane, vinyltriethoxysilane, p-styryltrimethoxysilane, 3 -methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-mercaptopropylmethyl One or more selected from the group consisting of dimethoxysilane and 3-mercaptopropyltrimethoxysilane. These may be used individually by 1 type, and may be used in mixture of 2 or more types.
- the (b) unit in the fine resin particles of the present invention is a unit derived from a monofunctional (meth)acrylic monomer.
- the monofunctional (meth)acrylic monomer is not particularly limited as long as it is a compound having only one (meth)acryloyl group in the molecule.
- One or more acid alkyl esters One or
- the (c) unit in the fine resin particles of the present invention is a unit derived from a polyfunctional (meth)acrylic monomer.
- the polyfunctional (meth)acrylic monomer is not particularly limited as long as it is a compound having two or more radically polymerizable unsaturated groups such as (meth)acryloyl groups in the molecule.
- ethylene glycol di(meth)acrylate especially ethylene glycol dimethacrylate
- allyl (meth)acrylate allyl methacrylate
- These polyfunctional (meth)acrylic monomers may be used singly or in combination of two or more.
- the (d) unit in the fine resin particles of the present invention is a unit derived from a thiol compound.
- the thiol-based compound is not particularly limited as long as it is a compound having a thiol group in the molecule, and includes monofunctional thiol-based compounds and polyfunctional thiol-based compounds.
- a thiol-based compound functions as a chain transfer agent and becomes a structural unit of polymer fine particles.
- the thiol compound is a hydrolyzable silicon compound having a hydrolyzable silyl group and a group that reacts with a radically polymerizable unsaturated group, a monofunctional (meth)acrylic monomer and a polyfunctional (meth)acrylic monomer.
- the radical polymerization system in which is polymerized, it receives radicals from the growing polymer chain to terminate the elongation of the polymer chain and generates new radicals to initiate the growth reaction of another polymer chain.
- the molecular weight of the resin fine particles can be made uniform, and the particle size distribution can be made uniform.
- the monofunctional thiol-based compound is not particularly limited as long as it is a compound having one thiol group in the molecule.
- Thiol compounds such as, for example, 1-butanethiol, 1-octanethiol, 1-decanethiol, 1-dodecanethiol, 1-hexadecanethiol, tert-dodecanethiol; thioglycolic acid, 3-mercaptopropionic acid, mercaptosuccinic acid, etc. and one or more selected from the group consisting of acid compounds having a thiol group, esters thereof, and the like.
- These monofunctional thiol compounds may be used singly or in combination of two or more.
- the polyfunctional thiol-based compound is not particularly limited as long as it is a compound having two or more thiol groups in the molecule.
- polyfunctional thiol compounds may be used singly or in combination of two or more.
- ethylene glycol bisthioglycolate (EGTG), 1,4-butanediol bisthiopropionate (BDTP), trimethylolpropane tristhioglycolate (TMTG), pentaerythritol tetrakisthioglycolate (PETG) One or more selected from the group consisting of is preferable.
- the resin fine particles of the present invention may contain the (e) unit in addition to the (a) to (d) units.
- the (e) unit is a unit derived from a monofunctional vinyl-based monomer having an aromatic ring in its molecular structure.
- Monofunctional vinyl-based monomers having an aromatic ring in the molecular structure include those having an aromatic ring in the molecule as well as radically polymerizable non-monomers such as (meth)acryloyl groups, (meth)acrylamide groups, vinyl groups, and styryl groups. It is a monomer having one saturated group. Examples include one or more selected from the group consisting of monofunctional aromatic hydrocarbon-based monomers, polyfunctional aromatic hydrocarbon-based monomers, aromatic ring-containing (meth)acrylic acid ester-based monomers, and the like. . These monofunctional vinyl-based monomer units having an aromatic ring in the molecular structure may be used singly or in combination of two or more.
- monofunctional aromatic hydrocarbon monomers examples include styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene (vinyltoluene), ⁇ -methylstyrene, m-ethylvinylbenzene, p-ethyl
- vinyl benzene vinyl benzoic acid, styrene sulfonic acid, styrene sulfonates such as sodium styrene sulfonate and ammonium styrene sulfonate, vinyl naphthalene, allylbenzene and the like.
- styrene, ⁇ -methylstyrene and sodium styrenesulfonate are preferred.
- These monofunctional aromatic hydrocarbon-based monomers may be used alone or in combination of two or more.
- aromatic ring-containing (meth)acrylic acid ester monomers examples include benzyl (meth)acrylate, phenyl (meth)acrylate and phenoxyethyl (meth)acrylate, 2-(meth)acryloyloxyethyl phthalate, and the like.
- a (meth)acrylic acid ester-based monomer having an aromatic ring in its molecular structure such as benzyl (meth)acrylate
- a monofunctional vinyl-based monomer having an aromatic ring in its molecular structure shall be treated as "body”.
- the fine resin particles of the present invention may contain the (f) unit in addition to the (a) to (d) units.
- the (f) units are units derived from reactive surfactants.
- reactive surfactants include one or more selected from the group consisting of anionic reactive surfactants and nonionic reactive surfactants.
- anionic reactive surfactant include one or more selected from the group consisting of the anionic reactive surfactants exemplified in ⁇ Surfactant> in [Method for producing fine resin particles] below.
- the nonionic reactive surfactant include one or more selected from the group consisting of nonionic reactive surfactants exemplified in ⁇ Surfactant> in [Method for producing fine resin particles] below.
- the resin fine particles of the present invention may contain units other than the units (a) to (f) (hereinafter referred to as "other units").
- Other units include, for example, fatty acid vinyl ester-based monomers, halogenated olefin-based monomers, vinyl cyanide-based monomers, unsaturated carboxylic acid-based monomers, and unsaturated polycarboxylic acid ester-based monomers. isomers, unsaturated carboxylic acid amide-based monomers, unsaturated carboxylic acid amide methylol compound-based monomers, polyfunctional aromatic hydrocarbon-based monomers, polyfunctional allyl-based monomers, etc. Units derived from one or more monomers are included.
- fatty acid vinyl ester monomers examples include vinyl acetate and vinyl propionate. These fatty acid vinyl ester monomers may be used singly or in combination of two or more.
- halogenated olefinic monomers examples include vinyl chloride, vinylidene chloride, tetrafluoroethylene, and vinylidene fluoride. These halogenated olefinic monomers may be used singly or in combination of two or more.
- Vinyl cyanide-based monomers include, for example, (meth)acrylonitrile.
- Unsaturated carboxylic acid-based monomers include unsaturated carboxylic acids, their salts or anhydrides, such as (meth)acrylic acid, crotonic acid, maleic acid, fumaric acid, their ammonium and metal salts. , maleic anhydride, and the like. These unsaturated carboxylic acid-based monomers may be used singly or in combination of two or more.
- the unsaturated polycarboxylic acid ester monomers include unsaturated dicarboxylic acid monoesters, salts thereof, and unsaturated dicarboxylic acid diesters. Examples include monobutyl maleic acid, their ammonium and metal salts, maleic acid dimethyl and the like. These unsaturated polycarboxylic acid ester-based monomers may be used singly or in combination of two or more. Examples of unsaturated carboxylic acid amide-based monomers include (meth)acrylamide and diacetone (meth)acrylamide. These unsaturated carboxylic acid amide-based monomers may be used singly or in combination of two or more.
- unsaturated carboxylic acid amide methylolated monomers examples include N-methylolacrylamide, N-methylolmethacrylamide, methylolated diacetoneacrylamide, and these monomers and alcohols having 1 to 8 carbon atoms. and the like. These unsaturated carboxylic acid amide methylol compound monomers may be used singly or in combination of two or more.
- polyfunctional aromatic hydrocarbon monomers examples include m- or p-divinylbenzene, 1,3-, 1,8-, 1,4-, 1,5-, 2,3-, 2, 6- or 2,7-divinylnaphthalene, 4,4'-, 4,3'-, 2,2'- or 2,4-divinylbiphenyl, 1,2-, 1,3-, 1,4-di At least one selected from the group consisting of isopropenylbenzene, 1,2-divinyl-3,4-dimethylbenzene, derivatives thereof, and the like.
- polyfunctional aromatic hydrocarbon-based monomers may be used singly or in combination of two or more.
- polyfunctional allylic monomers examples include diallyl phthalate and triallyl cyanurate. These polyfunctional allylic monomers may be used singly or in combination of two or more.
- the amount ratio of each unit constituting the resin fine particles can be appropriately determined according to the use of the resin fine particles, desired properties, etc., and is not particularly limited.
- the hydrolyzable silicon compound unit having a hydrolyzable silyl group and a radically polymerizable unsaturated group-reactive group is, for example, 0 when the total of (a) to (d) units is 100% by mass. .1% by mass or more, preferably 0.5% by mass or more, and for example 10% by mass or less, preferably 5% by mass or less.
- the monofunctional (meth)acrylic monomer unit is, for example, 10% by mass or more, preferably 15% by mass or more, when the total of (a) to (d) units is 100% by mass; For example, it is 90% by mass or less, preferably 85% by mass or less.
- the polyfunctional (meth)acrylic monomer unit is, for example, 3% by mass or more, preferably 5% by mass or more, when the total of (a) to (d) units is 100% by mass; For example, it is 50% by mass or less, preferably 40% by mass or less.
- the thiol-based compound unit is, for example, 0.1% by mass or more, preferably 0.3% by mass or more, when the total of (a) to (d) units is 100% by mass, for example 5% by mass % or less, preferably 3 mass % or less.
- the monofunctional vinyl-based monomer unit having an aromatic ring in the molecular structure is 0% by mass or more, for example 5% by mass or more, when the total of units (a) to (e) is taken as 100% by mass. and is, for example, 70% by mass or less, preferably 60% by mass or less.
- the reactive surfactant unit is 0% by mass or more, for example 0.1% by mass or more, preferably 0% by mass when the total of (a) to (d) and (f) units is 100% by mass. .3% by mass or more, for example, 5% by mass or less, preferably 3% by mass or less.
- the content of silicon element in the resin fine particles measured by fluorescent X-ray analysis is preferably 0.03% by mass or more and 1% by mass or less, and preferably 0.05% by mass or more and 0.5% by mass. It is more preferably 0.50% by mass or less.
- the fine resin particles exhibiting such properties are extremely excellent in heat resistance and do not affect haze or the like when formed into a film.
- the silicon element in the resin fine particles in the present invention is defined as "a hydrolyzable silicon compound unit having a group that reacts with a hydrolyzable silyl group and a radically polymerizable unsaturated group, a monofunctional (meth)acrylic unit," which constitutes the resin fine particles. It means a silicon element in a "resin containing a monomer unit, a polyfunctional (meth)acrylic monomer unit, and a thiol compound unit".
- a method for measuring the content of silicon element in the resin microparticles by fluorescent X-ray analysis for example, the method described in Examples below can be used.
- the fine resin particles of the present invention have a heat weight loss rate of 2.5% or less when heat-treated at 280° C. for 1 hour in a nitrogen atmosphere.
- the fine resin particles exhibiting such properties are extremely excellent in heat resistance.
- the method described in Examples below can be used as a method for measuring the weight loss ratio upon heating at 280° C. for 1 hour in a nitrogen atmosphere.
- the resin fine particles of the present invention preferably have a 3% thermal decomposition temperature of 350° C. or higher in a nitrogen atmosphere.
- the 3% thermal decomposition temperature in a nitrogen atmosphere means that the temperature at which the mass of the fine resin particles decreases by 3% when the fine resin particles are heated from around room temperature is 350° C. or higher.
- the fine resin particles exhibiting such properties are extremely excellent in heat resistance.
- the method described in Examples below can be used as a method for measuring the 3% thermal decomposition temperature in a nitrogen atmosphere.
- the volume-average particle size (volume-average primary particle size) of the resin fine particles of the present invention is not particularly limited, and can be appropriately set according to the purpose and application. For example, it is 0.05 ⁇ m or more, preferably 0.07 ⁇ m or more, more preferably 0.1 ⁇ m or more, and for example 3 ⁇ m or less, preferably 2 ⁇ m or less, more preferably 1.5 ⁇ m or less.
- a method for measuring the volume average particle size for example, it can be measured using a laser scattering/diffraction particle size distribution analyzer manufactured by Beckman Coulter.
- the method described in Examples below can be used.
- the variation coefficient of the volume-average particle size of the resin fine particles of the present invention is not particularly limited, and can be appropriately set according to the purpose and application. For example, it is 25% or less, preferably 20% or less, more preferably 17% or less.
- the coefficient of variation of the volume-average particle size of resin fine particles is a numerical value obtained from the following equation (1), and represents the distribution width of data.
- Variation coefficient (%) standard deviation x 100/volume average primary particle size (1)
- the volume average particle size (volume average primary particle size) and its standard deviation of the fine resin particles can be measured using, for example, a laser scattering/diffraction particle size distribution analyzer manufactured by Beckman Coulter.
- the coefficient of variation of the volume average particle size can be obtained, for example, by the method described in Examples below.
- the number of particles having a diameter of 5 ⁇ m or more in 300,000 particles in the following measurement range is preferably 1 or less.
- Classification methods include, but are not particularly limited to, a method of classifying by centrifugal force such as a centrifuge or an air classifier, and a method of classifying by passing through a mesh or filter with a desired opening and absolute filtration accuracy.
- the polymer fine particle slurry obtained by the polymerization reaction is passed through a filter with a desired absolute filtration accuracy to perform wet classification of the resin fine particles, thereby adjusting the number of particles of 5 ⁇ m or more in 300,000 resin fine particles. can do.
- the method described in Examples below can be used.
- the resin fine particle granule of the present invention is formed by aggregating a plurality of resin fine particles.
- the resin fine particle granules can be obtained by spray drying, freeze granulation drying, or the like of the resin fine particle slurry obtained in the polymerization step.
- a spray dryer having an inlet temperature of the fine resin particle slurry of 80° C. or higher and 220° C. or lower and an outlet temperature of the resin fine particle granules of 50° C. or higher and 100° C. or lower may be used. can be done.
- the obtained granules may be superior in handleability to the fine resin particles themselves.
- the resin fine particle granules can be classified as necessary to make the particle size uniform. Classification can be performed by known means.
- the volume average particle size of the resin fine particle granules is not particularly limited. For example, it can be 5 to 200 ⁇ m, preferably 10 to 100 ⁇ m.
- the obtained resin fine particle granules may be pulverized into resin fine particles.
- a wet crushing method using The fine resin particles that are pulverized and dispersed may have good dispersibility in a solvent.
- the resin fine particles of the present invention are excellent in heat resistance and transparency, have a narrow particle size distribution, and have a small particle diameter.
- the fine resin particles of the present invention can be used for various purposes by taking advantage of such characteristics.
- anti-sticking agents for resin molded products (resin films), modifiers for various resin molded products, optical components such as light diffusers, anti-glare, low-reflection, etc., additives for paints, various electronic It can be used as a spacer between minute portions of devices, as a pore-forming agent for various battery members, as a core particle of conductive fine particles responsible for electrical connection, and the like.
- resin fine particles themselves can be mixed with a resin as an anti-sticking agent (anti-blocking agent) for a resin film to form a resin composition, thereby forming a resin molding such as a film.
- the resin fine particles of the present invention are excellent in heat resistance and transparency, have a narrow particle size distribution, and have a small particle diameter. It is possible to suppress the influence on haze and the like. In addition, the occurrence of resin build-up caused by the heat load or the like applied during resin compounding is suppressed, and there is little possibility that the yield will deteriorate.
- the resin fine particles as an anti-sticking agent for resin films, particularly as an anti-sticking agent for resin films for optical applications, highly transparent optical members, for example, optical films such as anti-glare films and light diffusion films, and light It becomes possible to stably produce diffusers and the like.
- the method for producing fine resin particles of the present invention comprises at least a hydrolyzable silicon compound having a group that reacts with a hydrolyzable silyl group and a radically polymerizable unsaturated group, a monofunctional (meth)acrylic monomer, and a polyfunctional (The method is not particularly limited as long as the resin fine particles are formed by reacting the meth)acrylic monomer and the thiol compound.
- seed particles that serve as nuclei are prepared before obtaining the desired resin fine particles.
- the seed particles are generally prepared by emulsion polymerization or soap-free polymerization.
- Seed particles are generally obtained by polymerizing a monomer mixture containing one or more of the aforementioned monofunctional (meth)acrylic monomers and monofunctional vinyl monomers having an aromatic ring in the molecular structure. be able to. At this time, it is preferable to add a monomer having a functional group condensable with the hydrolyzable silicon compound unit to the monomer mixture.
- the monomer having a functional group capable of condensing with the hydrolyzable silicon compound unit is not particularly limited, it may be a vinyl monomer having an epoxy group in the molecular chain or a vinyl monomer having a hydroxyl group in the molecular chain.
- examples include monomers and hydrolyzable silicon compound units having a reactive group copolymerizable with the aforementioned vinyl-based monomers.
- Examples of the vinyl-based monomer having an epoxy group in the molecular chain include one or more selected from the group consisting of glycidyl methacrylate, allyl glycidyl ether, allyl glycidyl phthalate, allyl glycidyl hexahydrophthalate, and the like.
- Vinyl monomers having a hydroxyl group in the molecular chain include, for example, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxybutyl methacrylate, 2- Hydroxybutyl acrylate, 2-hydroxy-3-phenoxypropyl acrylate, glycerin monoallyl ether, neopentyl glycol monoallyl ether, o-allylphenol, glycerin monomethacrylate, polyethylene glycol monomethacrylate, polypropylene glycol monomethacrylate, polyethylene glycol propylene glycol mono One or more selected from the group consisting of methacrylate, polyethylene glycol tetramethylene glycol monomethacrylate, propylene glycol polybutylene glycol monomethacrylate, polyethylene glycol monoacrylate, polypropylene glycol monoacrylate and the like.
- any known polymerization initiator can be used without any particular limitation.
- a thermally decomposable water-soluble polymerization initiator in the case of emulsion polymerization or soap-free polymerization, it is preferable to use a thermally decomposable water-soluble polymerization initiator, and in the case of seed polymerization or suspension polymerization, it is preferable to use a thermally decomposable oil-soluble polymerization initiator.
- a radical polymerization initiator particularly a thermal polymerization initiator.
- water-soluble polymerization initiators include, for example, persulfates (e.g., ammonium persulfate, potassium persulfate, sodium persulfate, etc.), hydrogen peroxide, organic peroxides, nitrile-azo compounds.
- persulfates e.g., ammonium persulfate, potassium persulfate, sodium persulfate, etc.
- hydrogen peroxide e.g., sodium persulfate, etc.
- organic peroxides e.g., nitrile-azo compounds.
- oil-soluble polymerization initiators include, for example, cumene hydroperoxide, di-tert-butyl peroxide, dicumyl peroxide, benzoyl peroxide, lauroyl peroxide, dimethylbis(tert-butyl peroxide, oxy)hexane, dimethylbis(tert-butylperoxy)hexyne-3, bis(tert-butylperoxyisopropyl)benzene, bis(tert-butylperoxy)trimethylcyclohexane, butyl-bis(tert-butylperoxy)valerate , tert-butyl 2-ethylhexaneperoxyate, dibenzoyl peroxide, paramenthane hydroperoxide and organic peroxides such as tert-butyl peroxybenzoate; 2,2′-azobisisobutyronitrile, 2,2 '-
- the polymerization initiator of the above persulfate and organic peroxide, sodium sulfoxylate formaldehyde, sodium hydrogen sulfite, ammonium hydrogen sulfite, sodium thiosulfate, ammonium thiosulfate, hydrogen peroxide, sodium hydroxymethanesulfinate, L - Redox polymerization initiators may be used in combination with reducing agents such as ascorbic acid and its salts, cuprous salts, and ferrous salts.
- 2,2′-azobisisobutyronitrile 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis(2,4-dimethylvaleronitrile)
- 2,2′-azobis isobutyronitrile 2,2′-azobis (2-methylbutyronitrile), 1,1′-azobis (cyclohexane-1-carbonitrile)
- 4,4′-azobis At least one selected from the group consisting of (4-cyanopentanoic acid), cumene hydroperoxide, di-tert-butyl peroxide, dicumyl peroxide, benzoyl peroxide and lauroyl peroxide is preferred.
- These polymerization initiators may be used singly or in combination of two or more.
- the amount of the polymerization initiator used can be appropriately determined according to its type, and is not particularly limited. For example, 0.1 parts by mass or more, preferably 0.3 parts by mass or more, for example 5 parts by mass or less, preferably 3 parts by mass or less, relative to 100 parts by mass of the total amount of all monomers used during polymerization. is within the range of
- the surfactant that may be used in the method for producing resin fine particles of the present invention is not particularly limited, and known surfactants can be used.
- the surfactant is appropriately selected in kind and used in an appropriate amount, taking into account the particle size of the resin fine particles to be obtained, the dispersion stability of the monomer during polymerization, and the like.
- an anionic surfactant such as an anionic non-reactive surfactant or an anionic reactive surfactant can be used. These anionic surfactants may be used singly or in combination of two or more.
- non-reactive anionic surfactants include sodium oleate; fatty acid soaps such as castor oil potash soap; alkyl sulfate ester salts such as sodium lauryl sulfate and ammonium lauryl sulfate; alkyl benzene sulfonates such as sodium dodecylbenzene sulfonate.
- alkylnaphthalenesulfonate alkanesulfonate; dialkylsulfosuccinate; alkyl phosphate; naphthalenesulfonic acid formalin condensate; polyoxyethylene alkylphenyl ether sulfate; One or more selected from the group consisting of polyoxyethylene alkyl sulfate ester salts and the like can be mentioned.
- anionic reactive surfactants examples include JS-20 and RS-3000 of Eleminol (registered trademark) manufactured by Sanyo Kasei Co., Ltd., KH-10 and KH-10 of Aqualon (registered trademark) manufactured by Daiichi Kogyo Seiyaku Co., Ltd.
- nonionic surfactants such as nonionic non-reactive surfactants and nonionic reactive surfactants can be used. These nonionic surfactants may be used singly or in combination of two or more.
- nonionic non-reactive surfactants include polyoxyalkylene branched decyl ether, polyoxyethylene tridecyl ether, polyoxyalkylene alkyl ether, polyoxyalkylene tridecyl ether, polyoxyethylene isodecyl ether, polyoxyalkylene Lauryl ether, polyether polyol, polyoxyethylene styrenated phenyl ether, polyoxyethylene naphthyl ether, polyoxyethylene phenyl ether, polyoxyethylene polyoxypropylene glycol, polyoxyethylene lauryl ether, polyoxyethylene oleyl cetyl ether, isostearic acid Polyoxyethylene glyceryl, polyoxyethylene alkyl ether, polyoxyethylene alkylphen
- nonionic reactive surfactants include, for example, alkyl ether-based surfactants (commercially available products such as ADEKA Corporation, Adekaria Soap ER-10, ER-20, ER-30, ER-40, etc.; Kao Corporation , Latemul PD-420, PD-430, PD-450, etc.); -30, RN-50, AN-10, AN-20, AN-30, AN-5065, etc.; manufactured by ADEKA, Adekaria Soap NE-10, NE-20, NE-30, NE-40, etc.); One or more selected from the group consisting of meth)acrylate sulfate esters (commercially available products include RMA-564, RMA-568, RMA-1114, etc. manufactured by Nippon Nyukazai Co., Ltd.). Among them, those having an oxyalkylene chain in the molecular chain are preferable from the viewpoint of particle dispersion stability.
- alkyl ether-based surfactants commercially available products such as
- a cationic surfactant or an amphoteric surfactant can be used in the method for producing resin fine particles of the present invention.
- These cationic surfactants and amphoteric surfactants may be used singly or in combination of two or more.
- cationic surfactants include one or more selected from the group consisting of alkylamine salts such as laurylamine acetate and stearylamine acetate; quaternary ammonium salts such as lauryltrimethylammonium chloride and the like.
- Amphoteric surfactants include, for example, one or more selected from the group consisting of lauryldimethylamine oxide, betaine laurylaminoacetate, and the like.
- reactive surfactants in particular, one or more selected from the group consisting of anionic reactive surfactants and nonionic reactive surfactants can be used.
- f) Will contain reactive surfactant units.
- the amount of surfactant to be used can be appropriately determined according to its type, and is not particularly limited. For example, 0.1 parts by mass or more, preferably 0.3 parts by mass or more, for example 5 parts by mass or less, preferably 3 parts by mass or less, relative to 100 parts by mass of the total amount of all monomers used during polymerization. is within the range of
- the liquid medium used in the method for producing fine resin particles of the present invention is not particularly limited.
- water, organic solvents, and mixtures thereof can be used.
- an aqueous medium is preferable, and for example, water, lower alcohols having 5 or less carbon atoms such as methyl alcohol and ethyl alcohol, mixtures of water and lower alcohols, and the like can be used.
- a monomer component containing a monofunctional (meth)acrylic monomer is subjected to emulsion polymerization or soap-free polymerization in the first step to prepare seed particles, and then the second step is carried out.
- a hydrolyzable silicon compound unit having a reactive group copolymerizable with a vinyl monomer in the process, a monofunctional (meth)acrylic monomer unit, and a polyfunctional (meth)acrylic monomer unit a method of allowing the seed particles to absorb a monomer mixture containing thiol-based compound units for polymerization.
- the monomer mixture in the second step preferably further contains a monofunctional vinyl-based monomer unit having an aromatic ring in its molecular structure.
- the method for producing fine resin particles of the present invention it is preferable to classify the fine resin particles with a filter having a desired absolute filtration accuracy, for example, an absolute filtration accuracy of 5 ⁇ m or less. Further, in the method for producing resin fine particles of the present invention, the resin fine particles may be granulated and dried to obtain resin fine particle agglomerates.
- the content of silicon element in the fine resin particles was obtained by measuring the peak height of silicon element by fluorescent X-ray spectroscopy, and determining the content of silicon element by the order analysis method (FP bulk method). Specifically, using a fluorescent X-ray analyzer (manufactured by Rigaku Corporation, ZSX Primus IV), the intensity of Si-K ⁇ was measured under the following device conditions and qualitative element conditions, and the resin fine particles were determined by the order analysis method. The content of elemental silicon in the sample was measured.
- a conductive carbon double-sided tape (manufactured by Nissin EM) was pasted on a carbon sample stand (manufactured by Nissin EM). 20 mg of a sample (resin fine particles produced in each example and comparative example) was weighed out on the attached conductive carbon double-sided tape, and the sample was adjusted so as not to expand by 10 mm ⁇ or more. After that, it was covered with a PP film (polypropylene film) and set in a 10 mm diameter sample case attached to the apparatus to obtain a measurement sample. Next, the peak height of silicon element was measured under the following conditions, and the content of silicon element was determined by the order analysis method.
- sample preparation method About 15 mg of fine resin particles (measurement sample) were filled into the bottom of a platinum measurement container so as not to create a gap, thereby preparing a sample.
- Measurement condition A nitrogen gas flow rate of 230 mL/min was used, and alumina was used as a reference substance. The temperature was raised from 40° C.
- the analysis software attached to the apparatus was used to determine the heating weight loss rate at the end of the measurement, and this was defined as the "heating weight loss rate after heat treatment at 280 ° C. for 1 hour in a nitrogen atmosphere.” .
- the "3% thermal decomposition temperature in a nitrogen atmosphere" of the fine resin particles was measured using a simultaneous differential thermogravimetric analyzer (TG/DTA6200, manufactured by SII Nano Technology Co., Ltd.).
- the sample preparation method and measurement conditions are as follows. (Sample preparation method) About 15 mg of fine resin particles (measurement sample) were filled into the bottom of a platinum measurement container so as not to create a gap, thereby preparing a sample. (Measurement condition) A nitrogen gas flow rate of 230 mL/min was used, and alumina was used as a reference material. The temperature is raised from 300°C to 500°C at 10°C/min to obtain a TG/DTA curve. From the obtained TG / DTA curve, using the analysis software attached to the apparatus, the temperature when the mass of the sample decreases by 3% from the start of measurement is obtained, and this is called the "3% thermal decomposition temperature in a nitrogen atmosphere". bottom.
- the measurement conditions of the laser diffraction scattering type particle size distribution analyzer are as follows.
- Refractive index of solid Refractive index of fine resin particles
- the optical model at the time of measurement was adapted to the refractive index of the manufactured resin fine particles.
- the refractive index of a homopolymer of that monomer was used as the refractive index of the resin fine particles.
- the refractive index of the resin fine particles is the average value obtained by weighting and averaging the refractive indices of the homopolymers of each monomer by the amount of each monomer used. was used.
- Variation coefficient of volume average particle size [(standard deviation of volume-based particle size distribution of resin fine particles)/(volume average particle diameter of resin fine particles)] ⁇ 100
- a surfactant aqueous solution was prepared by adding 0.01 part of a surfactant (dodecylbenzenesulfonate) to 4.94 parts of ion-exchanged water. 0.06 parts of resin fine particles are added to the surfactant aqueous solution, and the resin fine particles are dispersed in the surfactant aqueous solution over 10 minutes using a dispersing machine (ultrasonic cleaner (VS-150, manufactured by Vervoclea)). Then, an aqueous dispersion of resin fine particles was obtained.
- a surfactant dodecylbenzenesulfonate
- the obtained resin fine particle aqueous dispersion was subjected to a flow type particle image analyzer (manufactured by Sysmex Corporation, FPIA-3000S; equipped with a standard objective lens (10x), and a particle sheath (manufactured by Sysmex Corporation, PSE-900A) as a sheath liquid. used.) and measured under the following measurement conditions.
- Measurement mode HPF measurement mode
- Particle size measurement range 0.5 to 200 ⁇ m
- Particle circularity measurement range 0.2 to 1.0 Number of particles measured: 100,000
- a suspension of standard polymer particles for example, Thermo Fisher Scientific, 5200A (standard polystyrene particles diluted with ion-exchanged water)
- Thermo Fisher Scientific, 5200A standard polystyrene particles diluted with ion-exchanged water
- the degree of circularity is a value obtained by dividing the perimeter calculated from the diameter of a perfect circle having the same projected area as the image of the fine resin particles by the perimeter of the image of the fine resin particles.
- the number of resin fine particles having a volume average particle diameter of 5 ⁇ m or more was counted.
- a monomer mixture a monomer mixture obtained by mixing monomer components so that the ratio of 120 parts of methyl methacrylate, 1.2 parts of 3-mercaptopropyltrimethoxysilane, and 2.4 parts of 1-octanethiol is used.
- a seed particle B-containing slurry was obtained in the same manner as in Production Example 1, except that The volume average particle diameter of the seed particles B was 177 nm.
- Seed was prepared in the same manner as in Production Example 1, except that the monomer mixture was obtained by mixing the monomer components so that the ratio of 120 parts of methyl methacrylate and 2.4 parts of 1-octanethiol was used as the monomer mixture. A particle C-containing slurry was obtained. The volume average particle diameter of the seed particles C was 175 nm.
- Example/Comparative example ⁇ Example 1> In a polymerization vessel equipped with a stirrer, a thermometer and a cooling mechanism, 280 parts of ion-exchanged water, 20% sodium dodecylbenzenesulfonate solution (manufactured by Daiichi Kogyo Seiyaku Co., Ltd., Neogen S-20D) 2.8 parts, polyoxyethylene 0.7 parts of styrenated phenyl ether (Daiichi Kogyo Seiyaku Co., Ltd., Noigen EA-167) and 0.014 parts of sodium nitrite were mixed to prepare an aqueous phase.
- the oil phase was added to the water phase in the polymerization vessel and stirred at 8000 rpm for 10 minutes using TK Homomixer (manufactured by Primix) to obtain a monomer mixture.
- 33.3 parts of the seed particles A produced in Production Example 1 were added to this monomer mixture and stirred for 3 hours to swell the mixture.
- the temperature was raised to 65° C., and polymerization was carried out by stirring at 65° C. for 6 hours.
- After adding 0.021 part of sulfamic acid the temperature was raised to 100° C., held for 3 hours, and then cooled to prepare a slurry containing fine resin particles.
- the resulting resin fine particle-containing slurry is passed through a 500-mesh SUS mesh, and then through a filter (manufactured by Asahi Kasei Corporation, KDGF-030) with an absolute filtration accuracy of 3 ⁇ m, whereby the resin fine particles are wet-classified and classified. A fine resin particle slurry was obtained.
- the classified resin fine particle slurry was spray-dried using an atomizer take-up type spray dryer (manufactured by Sakamoto Giken, TRS-3WK) under the following spray drying conditions to obtain resin fine particles. . (Spray drying conditions) Slurry supply rate containing fine resin particles: 25 mL/min Atomizer rotation speed: 12000rpm Air volume: 2 m 3 /min Inlet temperature (temperature of inlet into which sprayed slurry containing fine resin particles is introduced): 150°C Outlet temperature (powder outlet temperature at which fine resin particles are discharged): 70°C
- the obtained resin fine particles exhibited the following characteristics. Content of silicon element in resin fine particles measured by fluorescent X-ray analysis: 0.17% by mass Heating weight loss ratio when heat treated for 1 hour at 280°C in a nitrogen atmosphere: 1.8% 3% pyrolysis temperature under nitrogen atmosphere: 356°C Volume average particle size: 350 nm Variation coefficient of volume average particle size: 14.5% Number of particles of 5 ⁇ m or more in 300,000 resin fine particles: 0
- Example 2 to 5 Resin fine particles were obtained in the same manner as in Example 1, except that the monomer composition having the composition shown in Table 1 was used as the monomer composition. Table 1 also shows the properties of the obtained resin fine particles.
- Example 6 As a surfactant component, "20% solution of sodium dodecylbenzenesulfonate (manufactured by Daiichi Kogyo Seiyaku Co., Ltd., Neogen S-20D) 2.8 parts, polyoxyethylene styrenated phenyl ether (manufactured by Daiichi Kogyo Seiyaku Co., Ltd., Neugen EA -167) Resin fine particles were added in the same manner as in Example 4, except that "5 parts of Aqualon KH-1025 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., 25% of the main component)" was used instead of "0.7 parts". Obtained. Table 1 also shows the properties of the obtained resin fine particles.
- Example 1 A slurry containing fine resin particles was obtained in the same manner as in Example 1, except that the monomer composition having the composition shown in Table 1 was used as the monomer composition. The resulting slurry containing fine resin particles was passed through a 500-mesh SUS mesh and then spray-dried in the same manner as in Example 1 to obtain fine resin particles. Table 1 also shows the properties of the obtained resin fine particles.
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Abstract
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JP2013231133A (ja) * | 2012-04-27 | 2013-11-14 | Nippon Shokubai Co Ltd | 重合体粒子および重合体粒子含有組成物 |
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JPS6035353Y2 (ja) | 1978-11-09 | 1985-10-21 | パイオニア株式会社 | 2ケ国語放送受信機 |
JPS5744855Y2 (fr) | 1978-12-30 | 1982-10-04 | ||
JP2009173694A (ja) | 2008-01-21 | 2009-08-06 | Kaneka Corp | シリコーン系重合体粒子および該粒子を含有する硬化性樹脂組成物 |
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- 2022-08-30 JP JP2023550476A patent/JPWO2023053819A1/ja active Pending
- 2022-08-30 KR KR1020247004076A patent/KR20240028518A/ko unknown
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JP2001002716A (ja) * | 1999-04-23 | 2001-01-09 | Tosoh Corp | 粒径単分散粒子、その製造方法及びそれを用いた用途 |
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