JP2019073617A - Active energy ray-curable composition and film using the same - Google Patents
Active energy ray-curable composition and film using the same Download PDFInfo
- Publication number
- JP2019073617A JP2019073617A JP2017200263A JP2017200263A JP2019073617A JP 2019073617 A JP2019073617 A JP 2019073617A JP 2017200263 A JP2017200263 A JP 2017200263A JP 2017200263 A JP2017200263 A JP 2017200263A JP 2019073617 A JP2019073617 A JP 2019073617A
- Authority
- JP
- Japan
- Prior art keywords
- active energy
- energy ray
- meth
- acrylate
- curable composition
- Prior art date
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- Granted
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- 239000011347 resin Substances 0.000 claims abstract description 42
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 21
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 20
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 239000011248 coating agent Substances 0.000 claims description 37
- 238000000576 coating method Methods 0.000 claims description 36
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 230000005865 ionizing radiation Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
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- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 3
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- 229920008347 Cellulose acetate propionate Polymers 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
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- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 2
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- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 2
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- 239000012860 organic pigment Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- ZKDDJTYSFCWVGS-UHFFFAOYSA-M sodium;diethoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].CCOP([S-])(=S)OCC ZKDDJTYSFCWVGS-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- IWDANOJGJIFBEL-UHFFFAOYSA-N spiro[3.4]octane Chemical group C1CCC21CCCC2 IWDANOJGJIFBEL-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- MVQLEZWPIWKLBY-UHFFFAOYSA-N tert-butyl 2-benzoylbenzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 MVQLEZWPIWKLBY-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- FCGQIZKUTMUWDC-UHFFFAOYSA-M trimethyl(propyl)azanium;bromide Chemical compound [Br-].CCC[N+](C)(C)C FCGQIZKUTMUWDC-UHFFFAOYSA-M 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- FEPMHVLSLDOMQC-UHFFFAOYSA-N virginiamycin-S1 Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC=CC=2)N(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O FEPMHVLSLDOMQC-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
-
- 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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- 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
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- 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
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- 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
- C08F222/106—Esters of polycondensation macromers
- C08F222/1065—Esters of polycondensation macromers of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- 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
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09D201/025—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
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- 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
- C08J2400/00—Characterised by the use of unspecified polymers
- C08J2400/10—Polymers characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C08J2400/106—Polymers characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
Abstract
Description
本発明は、活性エネルギー線硬化性組成物及びそれを用いたフィルムに関する。 The present invention relates to an active energy ray curable composition and a film using the same.
各種樹脂フィルムは、液晶ディスプレイ（ＬＣＤ）、有機ＥＬディスプレイ（ＯＬＥＤ）、プラズマディスプレイ（ＰＤＰ）等のフラットパネルディスプレイ（ＦＰＤ）表面の傷付き防止用フィルム、自動車の内外装用加飾フィルム（シート）、窓向けの低反射フィルムや熱線カットフィルムなど各種用途に用いられている。しかしながら、樹脂フィルム表面は柔らかく耐擦傷性が低いため、これを補う目的で、ＵＶ硬化性組成物等からなるハードコート剤をフィルム表面に塗工、硬化させハードコート層をフィルム表面に設けることが一般的に行われている。ハードコート層を設ける工程を概略すると、ロール状に巻いてあるフィルム原反から塗工機へ送り出され、ハードコート剤が塗工され、紫外線照射により硬化してハードコート層を形成した後、再度ロール状に巻き取られる。 Various resin films are used to prevent scratching of flat panel displays (FPDs) such as liquid crystal displays (LCDs), organic EL displays (OLEDs), plasma displays (PDPs), etc., decorative films (sheets) for interior and exterior of automobiles, It is used in various applications such as low reflection films for windows and heat ray cut films. However, since the resin film surface is soft and has low abrasion resistance, a hard coat agent composed of a UV curable composition or the like is coated on the film surface and cured to provide a hard coat layer on the film surface for the purpose of compensating for this. It is commonly done. If the process of providing a hard coat layer is outlined, it is sent out to a coating machine from a film original roll wound in a roll, a hard coat agent is applied, and after curing by ultraviolet irradiation to form a hard coat layer, Rolled up in a roll.
この巻き取り工程でフィルム同士の摩擦によりフィルム表面に静電気が発生するため、再加工時にフィルムをロールから繰り出した際にフィルム同士が張り付いてしまう問題や静電気によりフィルム表面に埃等が付着しやすくなる問題があった。また、このフィルムを液晶ディスプレイ等に用いた場合、発生した静電気によりディスプレイが誤動作する問題もあった。 Since static electricity is generated on the film surface due to the friction between the films in this winding process, the films stick to each other when the film is drawn out from the roll during reprocessing, and dust and the like are easily attached to the film surface due to static electricity. Was a problem. Moreover, when this film is used for a liquid crystal display etc., there also existed a problem which a display malfunctions by the static electricity which generate | occur | produced.
このフィルム表面での静電気の発生を抑制するため、ハードコート剤に帯電防止剤を配合する手法が一般的に行われている。例えば、ポリオキシエチレン鎖と４級アンモニウム塩とを有する化合物を帯電防止剤としてハードコート剤に配合する方法が提案されている（例えば、特許文献１参照。）。 In order to suppress the generation of static electricity on the film surface, a method of blending an antistatic agent with a hard coating agent is generally performed. For example, a method has been proposed in which a compound having a polyoxyethylene chain and a quaternary ammonium salt is blended in a hard coat agent as an antistatic agent (see, for example, Patent Document 1).
また、４級アンモニウム塩を有する重合性単量体を原料とした２種の共重合体を帯電防止剤としてハードコート剤に配合する方法が提案されている（例えば、特許文献２参照。）。 In addition, there has been proposed a method in which two types of copolymers using a polymerizable monomer having a quaternary ammonium salt as a raw material are blended in a hard coating agent as an antistatic agent (see, for example, Patent Document 2).
しかしながら、これらの帯電防止剤を配合したハードコート剤は、帯電防止性能が十分ではなかった。さらに、帯電防止剤を多量に配合した場合には、帯電防止性能が向上するが、湿熱条件下での使用後に帯電防止剤のブリードが発生してしまう問題があった。 However, hard coat agents containing these antistatic agents do not have sufficient antistatic performance. Furthermore, when a large amount of the antistatic agent is blended, the antistatic performance is improved, but there is a problem that bleeding of the antistatic agent occurs after use under wet heat conditions.
本発明が解決しようとする課題は、優れた帯電防止性、及び、耐ブリード性を両立したハードコート層を形成できる活性エネルギー線硬化性組成物及びそれを用いたフィルムを提供することである。 The problem to be solved by the present invention is to provide an active energy ray-curable composition capable of forming a hard coat layer compatible with excellent antistatic property and bleed resistance, and a film using the same.
本発明は、活性エネルギー線硬化性化合物（Ａ）と、脂環構造及び４級アンモニウム塩を有する樹脂（Ｂ）と、４級アンモニウム塩を有し、かつ脂環構造を有しない化合物（Ｃ）と、有機溶剤（Ｄ）とを含有することを特徴とする活性エネルギー線硬化性組成物、及び、それを用いたフィルムを提供するものである。 The present invention provides an active energy ray-curable compound (A), a resin (B) having an alicyclic structure and a quaternary ammonium salt, and a compound (C) having a quaternary ammonium salt and not having an alicyclic structure And an organic solvent (D), and provides an active energy ray-curable composition, and a film using the same.
本発明の活性エネルギー線硬化性組成物は、フィルム表面に塗工、硬化することで、優れた帯電防止性、及び、鉛筆硬度を有するハードコート層を形成することができる。したがって、本発明の活性エネルギー線硬化性組成物の硬化塗膜は、フィルム表面に静電気を発生することを抑制できる。よって、各種フィルムに、張り付き防止、静電気による埃等の付着防止等の機能を付与できる。したがって、本発明の活性エネルギー線硬化性組成物の硬化塗膜を有するフィルムは、ロール状に巻き取る際、ロールから繰り出す際にも、張り付き、埃等の付着などのトラブルも回避できるため、その後のハンドリングに優れたフィルムを提供することができる。更に、本発明の活性エネルギー線硬化性組成物の硬化塗膜は、優れた耐ブリード性を有するものであり、湿熱条件下での使用後においても、帯電防止剤のブリードが発生せず、帯電防止性の変化も少ないものである。 The active energy ray-curable composition of the present invention can form a hard coat layer having excellent antistatic properties and pencil hardness by coating and curing on the film surface. Therefore, the cured coating film of the active energy ray curable composition of the present invention can suppress generation of static electricity on the film surface. Therefore, functions such as sticking prevention and adhesion prevention of dust due to static electricity can be provided to various films. Therefore, the film having the cured coating film of the active energy ray-curable composition of the present invention can also avoid problems such as sticking and adhesion of dust, etc. when winding it out from a roll when wound up in a roll. Can provide a film excellent in the handling of Furthermore, the cured coating film of the active energy ray-curable composition of the present invention has excellent bleed resistance, and no bleeding of the antistatic agent occurs even after use under moist heat conditions, and charging is not performed. The change in prevention is also small.
また、本発明の活性エネルギー線硬化性組成物の硬化塗膜からなるハードコート層を有するフィルムは、液晶ディスプレイ（ＬＣＤ）、有機ＥＬディスプレイ（ＯＬＥＤ）、プラズマディスプレイ（ＰＤＰ）等のフラットパネルディスプレイ（ＦＰＤ）に用いる光学フィルムとして好適に用いることができる。さらに、これらの用途に用いる際にも優れた帯電防止性があることから、埃等の付着を抑制できる。さらに、このフィルムを液晶ディスプレイ等に用いた場合、発生した静電気によるディスプレイの誤動作も防止できる。 In addition, a film having a hard coat layer comprising a cured coating film of the active energy ray curable composition of the present invention is a flat panel display such as a liquid crystal display (LCD), an organic EL display (OLED) or a plasma display (PDP) It can be suitably used as an optical film used for FPD. Furthermore, since it has the antistatic property excellent also when using for these uses, adhesion of dust etc. can be suppressed. Furthermore, when this film is used for a liquid crystal display etc., the malfunction of the display by the static electricity which generate | occur | produced can also be prevented.
本発明の活性エネルギー線硬化性組成物は、活性エネルギー線硬化性化合物（Ａ）と、脂環構造及び４級アンモニウム塩を有する樹脂（Ｂ）と、４級アンモニウム塩を有し、かつ脂環構造を有しない化合物（Ｃ）と、有機溶剤（Ｄ）とを含有するものである。 The active energy ray-curable composition of the present invention comprises an active energy ray-curable compound (A), a resin (B) having an alicyclic structure and a quaternary ammonium salt, and a quaternary ammonium salt, and an alicyclic It contains a compound (C) having no structure and an organic solvent (D).
前記活性エネルギー線硬化性化合物（Ａ）としては、例えば、多官能（メタ）アクリレート、ウレタン（メタ）アクリレート等を用いることができる。 As said active energy ray curable compound (A), polyfunctional (meth) acrylate, urethane (meth) acrylate etc. can be used, for example.
前記多官能（メタ）アクリレートとしては、例えば、１，４−ブタンジオールジ（メタ）アクリレート、３−メチル−１，５−ペンタンジオールジ（メタ）アクリレート、１，６−ヘキサンジオールジ（メタ）アクリレート、ネオペンチルグリコールジ（メタ）アクリレート、２−メチル−１，８−オクタンジオールジ（メタ）アクリレート、２−ブチル−２−エチル−１，３−プロパンジオールジ（メタ）アクリレート、トリシクロデカンジメタノールジ（メタ）アクリレート、エチレングリコールジ（メタ）アクリレート、ジエチレングリコールジ（メタ）アクリレート、トリエチレングリコールジ（メタ）アクリレート、ジプロピレングリコールジ（メタ）アクリレート、トリプロピレングリコールジ（メタ）アクリレート等の２価アルコールのジ（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、ポリプロピレングリコールジ（メタ）アクリレート、トリス（２−ヒドロキシエチル）イソシアヌレートのジ（メタ）アクリレート、ネオペンチルグリコール１モルに４モル以上のエチレンオキサイドもしくはプロピレンオキサイドを付加して得たジオールのジ（メタ）アクリレート、ビスフェノールＡ１モルに２モルのエチレンオキサイドもしくはプロピレンオキサイドを付加して得たジオールのジ（メタ）アクリレート、トリメチロールプロパントリ（メタ）アクリレート、エチレンオキサイド変性トリメチロールプロパントリ（メタ）アクリレート、プロピレンオキサイド変性トリメチロールプロパントリ（メタ）アクリレート、ジトリメチロールプロパントリ（メタ）アクリレート、ジトリメチロールプロパンテトラ（メタ）アクリレート、トリス（２−（メタ）アクリロイルオキシエチル）イソシアヌレート、グリセリントリ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート、ジペンタエリスリトールトリ（メタ）アクリレート、ジペンタエリスリトールテトラ（メタ）アクリレート、ジペンタエリスリトールペンタ（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレート、トリペンタエリスリトールヘプタ（メタ）アクリレート、トリペンタエリスリトールオクタ（メタ）アクリレート、ポリペンタエリスリトールポリ（メタ）アクリレート等が挙げられる。これらの化合物は単独で用いても２種以上を併用してもよい。 Examples of the polyfunctional (meth) acrylates include 1,4-butanediol di (meth) acrylate, 3-methyl-1,5-pentanediol di (meth) acrylate, and 1,6-hexanediol di (meth) Acrylate, neopentyl glycol di (meth) acrylate, 2-methyl-1,8-octanediol di (meth) acrylate, 2-butyl-2-ethyl-1,3-propanediol di (meth) acrylate, tricyclode Candimethanol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, etc. Divalent a Cole di (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, tri (2 hydroxyethyl) isocyanurate di (meth) acrylate, neopentyl glycol at least 4 moles per mole Di (meth) acrylate of diol obtained by addition of ethylene oxide or propylene oxide, di (meth) acrylate of diol obtained by addition of 2 mol of ethylene oxide or propylene oxide to 1 mol of bisphenol A, trimethylolpropane tri ( Meta) acrylate, ethylene oxide modified trimethylolpropane tri (meth) acrylate, propylene oxide modified trimethylolpropane tri (meth) acrylate, ditrimethylo Propane tri (meth) acrylate, ditrimethylol propane tetra (meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, glycerin tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate ) Acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tripenta Examples include erythritol octa (meth) acrylate, polypentaerythritol poly (meth) acrylate and the like. These compounds may be used alone or in combination of two or more.
前記ウレタン（メタ）アクリレートは、ポリイソシアネートと水酸基を有する（メタ）アクリレートとの反応物を用いることができる。 As the urethane (meth) acrylate, a reaction product of polyisocyanate and (meth) acrylate having a hydroxyl group can be used.
前記ポリイソシアネートとしては、脂肪族ポリイソシアネートと芳香族ポリイソシアネートとが挙げられるが、本発明の活性エネルギー線硬化性組成物の硬化塗膜の着色を低減できることから、脂肪族ポリイソシアネートが好ましい。 Although the aliphatic polyisocyanate and aromatic polyisocyanate are mentioned as said polyisocyanate, Since the coloring of the cured coating film of the active energy ray curable composition of this invention can be reduced, aliphatic polyisocyanate is preferable.
前記脂肪族ポリイソシアネートは、イソシアネート基を除く部位が脂肪族炭化水素から構成される化合物である。この脂肪族ポリイソシアネートの具体例としては、ヘキサメチレンジイソシアネート、リジンジイソシアネート、リジントリイソシアネート等の脂肪族ポリイソシアネート；ノルボルナンジイソシアネート、イソホロンジイソシアネート、メチレンビス（４−シクロヘキシルイソシアネート）、１，３−ビス（イソシアナトメチル）シクロヘキサン、２−メチル−１，３−ジイソシアナトシクロヘキサン、２−メチル−１，５−ジイソシアナトシクロヘキサン等の脂環式ポリイソシアネートなどが挙げられる。また、前記脂肪族ポリイソシアネート又は脂環式ポリイソシアネートを３量化した３量化物も前記脂肪族ポリイソシアネートとして用いることができる。また、これらの脂肪族ポリイソシアネートは、１種で用いることも２種以上併用することもできる。 The said aliphatic polyisocyanate is a compound in which the site | part except an isocyanate group is comprised from an aliphatic hydrocarbon. Specific examples of the aliphatic polyisocyanate include aliphatic polyisocyanates such as hexamethylene diisocyanate, lysine diisocyanate and lysine triisocyanate; norbornane diisocyanate, isophorone diisocyanate, methylene bis (4-cyclohexyl isocyanate) and 1,3-bis (isocyanate) Alicyclic polyisocyanates such as methyl) cyclohexane, 2-methyl-1,3-diisocyanatocyclohexane, 2-methyl-1,5-diisocyanatocyclohexane and the like can be mentioned. In addition, a trimerized trimerized aliphatic polyisocyanate or alicyclic polyisocyanate can also be used as the aliphatic polyisocyanate. Moreover, these aliphatic polyisocyanates can be used alone or in combination of two or more.
前記脂肪族ポリイソシアネートの中でも塗膜の耐擦傷性を向上させるには、脂肪族ポリイソシアネートの中でも、直鎖脂肪族炭化水素のジイソシアネートであるヘキサメチレンジイソシアネート、脂環式ジイソシアネートであるノルボルナンジイソシアネート、イソホロンジイソシアネートが好ましい。 Among the aliphatic polyisocyanates, hexamethylene diisocyanate, which is a linear aliphatic hydrocarbon diisocyanate, norbornane diisocyanate, which is a cycloaliphatic diisocyanate, isophorone, among aliphatic polyisocyanates, among aliphatic polyisocyanates. Diisocyanate is preferred.
前記（メタ）アクリレートは、水酸基と（メタ）アクリロイル基とを有する化合物である。この（メタ）アクリレートの具体例としては、２−ヒドロキシエチル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、２−ヒドロキシブチル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレート、１，５−ペンタンジオールモノ（メタ）アクリレート、１，６−ヘキサンジオールモノ（メタ）アクリレート、ネオペンチルグリコールモノ（メタ）アクリレート、ヒドロキシピバリン酸ネオペンチルグリコールモノ（メタ）アクリレート等の２価アルコールのモノ（メタ）アクリレート；トリメチロールプロパンジ（メタ）アクリレート、エチレンオキサイド（ＥＯ）変性トリメチロールプロパン（メタ）アクリレート、プロピレンオキサイド（ＰＯ）変性トリメチロールプロパンジ（メタ）アクリレート、グリセリンジ（メタ）アクリレート、ビス（２−（メタ）アクリロイルオキシエチル）ヒドロキシエチルイソシアヌレート等の３価のアルコールのモノ又はジ（メタ）アクリレート、あるいは、これらのアルコール性水酸基の一部をε−カプロラクトンで変性した水酸基を有するモノ及びジ（メタ）アクリレート；ペンタエリスリトールトリ（メタ）アクリレート、ジトリメチロールプロパントリ（メタ）アクリレート、ジペンタエリスリトールペンタ（メタ）アクリレート等の１官能の水酸基と３官能以上の（メタ）アクリロイル基を有する化合物、あるいは、該化合物をさらにε−カプロラクトンで変性した水酸基を有する多官能（メタ）アクリレート；ジプロピレングリコールモノ（メタ）アクリレート、ジエチレングリコールモノ（メタ）アクリレート、ポリプロピレングリコールモノ（メタ）アクリレート、ポリエチレングリコールモノ（メタ）アクリレート等のオキシアルキレン鎖を有する（メタ）アクリレート；ポリエチレングリコール−ポリプロピレングリコールモノ（メタ）アクリレート、ポリオキシブチレン−ポリオキシプロピレンモノ（メタ）アクリレート等のブロック構造のオキシアルキレン鎖を有する（メタ）アクリレート；ポリ（エチレングリコール−テトラメチレングリコール）モノ（メタ）アクリレート、ポリ（プロピレングリコール−テトラメチレングリコール）モノ（メタ）アクリレート等のランダム構造のオキシアルキレン鎖を有する（メタ）アクリレートなどが挙げられる。これらの（メタ）アクリレートは、１種で用いることも２種以上併用することもできる。 The (meth) acrylate is a compound having a hydroxyl group and a (meth) acryloyl group. Specific examples of this (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 1,5 Mono (meta) of a dihydric alcohol such as pentanediol mono (meth) acrylate, 1,6-hexanediol mono (meth) acrylate, neopentyl glycol mono (meth) acrylate, hydroxypivalate neopentyl glycol mono (meth) acrylate ) Acrylate; trimethylolpropane di (meth) acrylate, ethylene oxide (EO) modified trimethylolpropane (meth) acrylate, propylene oxide (PO) modified trimethylolpropane di (meth) acrylate Mono- or di (meth) acrylates of trihydric alcohols such as glycerine di (meth) acrylate and bis (2- (meth) acryloyloxyethyl) hydroxyethyl isocyanurate, or some of these alcoholic hydroxyl groups Mono- and di (meth) acrylates having hydroxyl groups modified with caprolactone; monofunctional hydroxyl groups and trifunctional groups such as pentaerythritol tri (meth) acrylate, ditrimethylolpropane tri (meth) acrylate, dipentaerythritol penta (meth) acrylate The compound having the above (meth) acryloyl group, or the polyfunctional (meth) acrylate having a hydroxyl group obtained by further modifying the compound with ε-caprolactone; dipropylene glycol mono (meth) acrylate, diethylene glycol mono (Meth) acrylates having an oxyalkylene chain such as meta) acrylates, polypropylene glycol mono (meth) acrylates, polyethylene glycol mono (meth) acrylates; polyethylene glycol-polypropylene glycol mono (meth) acrylates, polyoxybutylene-polyoxypropylene mono (Meth) acrylates having an oxyalkylene chain of a block structure such as (meth) acrylates; poly (ethylene glycol-tetramethylene glycol) mono (meth) acrylates, poly (propylene glycol-tetramethylene glycol) mono (meth) acrylates, etc. The (meth) acrylate etc. which have the oxyalkylene chain | strand of a random structure are mentioned. These (meth) acrylates can be used alone or in combination of two or more.
前記ポリイソシアネートと前記（メタ）アクリレートとの反応は、常法のウレタン化反応により行うことができる。また、ウレタン化反応の進行を促進するために、ウレタン化触媒の存在下でウレタン化反応を行うことが好ましい。前記ウレタン化触媒としては、例えば、ピリジン、ピロール、トリエチルアミン、ジエチルアミン、ジブチルアミン等のアミン化合物；トリフェニルホスフィン、トリエチルホスフィン等のリン化合物；ジブチル錫ジラウレート、オクチル錫トリラウレート、オクチル錫ジアセテート、ジブチル錫ジアセテート、オクチル酸錫等の有機錫化合物、オクチル酸亜鉛等の有機亜鉛化合物などが挙げられる。 The reaction of the polyisocyanate and the (meth) acrylate can be carried out by a conventional urethanation reaction. Moreover, in order to accelerate | stimulate advancing of a urethanization reaction, it is preferable to perform a urethanation reaction in presence of a urethanization catalyst. Examples of the urethanization catalyst include amine compounds such as pyridine, pyrrole, triethylamine, diethylamine and dibutylamine; phosphorus compounds such as triphenylphosphine and triethylphosphine; dibutyltin dilaurate, octyltin trilaurate, octyltin diacetate, dibutyltin Examples include organotin compounds such as diacetate and tin octylate, and organozinc compounds such as zinc octylate.
なお、本発明において、「（メタ）アクリレート」とは、アクリレートとメタクリレートの一方又は両方をいい、「（メタ）アクリロイル」とは、アクリロイルとメタクリロイルの一方又は両方をいう。 In the present invention, “(meth) acrylate” refers to one or both of acrylate and methacrylate, and “(meth) acryloyl” refers to one or both of acryloyl and methacryloyl.
前記活性エネルギー線硬化性化合物（Ａ）としては、前記した中でも、より一層優れた帯電防止性、及び、高硬度性が得られることから、水酸基価が４０ｍｇＫＯＨ／ｇ以下のものを用いることが好ましく、ジペンタエリスリトールヘキサアクリレート、及び／又は、ペンタエリスリトールテトラアクリレートを用いることがより好ましい。 Among the above-mentioned active energy ray-curable compounds (A), those having a hydroxyl value of 40 mg KOH / g or less are preferably used because even more excellent antistatic properties and high hardness can be obtained among them. More preferably, dipentaerythritol hexaacrylate and / or pentaerythritol tetraacrylate is used.
前記樹脂（Ｂ）は、優れた帯電防止性を得るうえで、４級アンモニウム塩を有するものであることが必須である。 The resin (B) is essential to have a quaternary ammonium salt in order to obtain excellent antistatic properties.
前記樹脂（Ｂ）は、優れた帯電防止性を得るうえで、脂環構造及び４級アンモニウム塩を有することが必須である。 The resin (B) must have an alicyclic structure and a quaternary ammonium salt in order to obtain excellent antistatic properties.
前記樹脂（Ｂ）としては、具体的には、例えば、脂環構造を有する重合性単量体（ｂ１）と、４級アンモニウム塩を有する重合性単量体（ｂ２）と、及び、前記（ｂ１）及び（ｂ２）と共重合可能なその他の重合性単量体（ｂ３）との共重合体が挙げられる。 Specifically as the resin (B), for example, a polymerizable monomer (b1) having an alicyclic structure, a polymerizable monomer (b2) having a quaternary ammonium salt, and Copolymers with other polymerizable monomers (b3) copolymerizable with b1) and (b2) can be mentioned.
前記重合性単量体（ｂ１）は、脂環構造を有するものである。前記脂環構造としては、例えば、シクロプロパン環、シクロブタン環、シクロペンタン環、シクロヘキサン環、シクロヘプタン環、シクロオクタン環、シクロノナン環、シクロデカン環等の単環脂環構造；ビシクロウンデカン環、デカヒドロナフタレン（デカリン）環、トリシクロ［５．２．１．０２，６］デカン環、ビシクロ［４．３．０］ノナン環、トリシクロ［５．３．１．１］ドデカン環、トリシクロ［５．３．１．１］ドデカン環、スピロ［３．４］オクタン環等の多環脂環構造などが挙げられる。また、前記重合性単量体（ｂ１）の具体例としては、シクロヘキシル（メタ）アクリレート、１，４−シクロヘキサンジメタノールモノ（メタ）アクリレート、イソボルニル（メタ）アクリレート、ジシクロペンテニル（メタ）アクリレート、ジシクロペンテニルオキシエチル（メタ）アクリレート、ジシクロペンタニル（メタ）アクリレート等が挙げられる。これらの重合性単量体（ｂ１）は、１種で用いることも２種以上併用することもできる。 The polymerizable monomer (b1) has an alicyclic structure. Examples of the alicyclic structure include monocyclic alicyclic structures such as cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring, cyclononane ring, cyclodecane ring and the like; bicycloundecane ring, decahydro Naphthalene (decalin) ring, tricyclo [5.2.1.0 2,6 ] decane ring, bicyclo [4.3.0] nonane ring, tricyclo [5.3.1.1] dodecane ring, tricyclo [5. 3.1.1] Polycyclic alicyclic structures such as dodecane ring, spiro [3.4] octane ring and the like can be mentioned. Further, specific examples of the polymerizable monomer (b1) include cyclohexyl (meth) acrylate, 1,4-cyclohexanedimethanol mono (meth) acrylate, isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, Dicyclopentenyl oxyethyl (meth) acrylate, dicyclopentanyl (meth) acrylate, etc. are mentioned. These polymerizable monomers (b1) can be used alone or in combination of two or more.
前記４級アンモニウム塩を有する重合性単量体（ｂ２）としては、例えば、２−［（メタ）アクリロイルオキシ］エチルトリメチルアンモニウムクロライド、３−［（メタ）アクリロイルオキシ］プロピルトリメチルアンモニウムクロライド等のカウンターアニオンがクロライドのもの；２−［（メタ）アクリロイルオキシ］エチルトリメチルアンモニウムブロマイド、３−［（メタ）アクリロイルオキシ］プロピルトリメチルアンモニウムブロマイド等のカウンターアニオンがブロマイドのもの；２−［（メタ）アクリロイルオキシ］エチルトリメチルアンモニウムメチルフェニルスルホネート、２−［（メタ）アクリロイルオキシ］エチルトリメチルアンモニウムメチルスルホネート、３−［（メタ）アクリロイルオキシ］プロピルトリメチルアンモニウムメチルフェニルスルホネート、３−［（メタ）アクリロイルオキシ］プロピルトリメチルアンモニウムメチルスルホネート、２−［（メタ）アクリロイルオキシ］エチルトリメチルアンモニウムメチルスルフェート、３−［（メタ）アクリロイルオキシ］プロピルトリメチルアンモニウムメチルスルフェート等のカウンターアニオンが非ハロゲン系のもの；ジメチルアミノエチル（メタ）アクリルアミド塩化メチル４級塩、ジメチルアミノプロピル（メタ）アクリルアミド塩化メチル４級塩などが挙げられる。これらの重合性単量体（ｂ２）は、１種で用いることも２種以上併用することもできる。 Examples of the polymerizable monomer (b2) having a quaternary ammonium salt include, for example, a counter such as 2-[(meth) acryloyloxy] ethyltrimethylammonium chloride, 3-[(meth) acryloyloxy] propyltrimethylammonium chloride, etc. Whose anion is chloride; counter anions such as 2-[(meth) acryloyloxy] ethyltrimethylammonium bromide, 3-[(meth) acryloyloxy] propyltrimethylammonium bromide are bromide; 2-[(meth) acryloyloxy Ethyltrimethylammonium methylphenylsulfonate, 2-[(meth) acryloyloxy] ethyltrimethylammonium methylsulfonate, 3-[(meth) acryloyloxy] propyl tri Ethylammonium methylphenylsulfonate, 3-[(meth) acryloyloxy] propyltrimethylammonium methylsulfonate, 2-[(meth) acryloyloxy] ethyltrimethylammonium methyl sulfate, 3-[(meth) acryloyloxy] propyltrimethylammonium methyl When the counter anion such as sulfate is non-halogen, dimethylaminoethyl (meth) acrylamido methyl chloride quaternary salt, dimethylaminopropyl (meth) acrylamido methyl chloride quaternary salt and the like can be mentioned. These polymerizable monomers (b2) can be used alone or in combination of two or more.
前記その他の重合性単量体（ｂ３）としては、例えば、メチル（メタ）アクリレート、エチル（メタ）アクリレート、ｎ−プロピル（メタ）アクリレート、ｎ−ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、ｎ−ペンチル（メタ）アクリレート、ｎ−ヘキシル（メタ）アクリレート、ｎ−ヘプチル（メタ）アクリレート、ｎ−オクチル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、ノニル（メタ）アクリレート、デシル（メタ）アクリレート、ドデシル（メタ）アクリレート等のアルキル（メタ）アクリレート；メトキシポリエチレングリコールモノ（メタ）アクリレート、オクトキシポリエチレングリコール・ポリプロピレングリコールモノ（メタ）アクリレート、ラウロキシポリエチレングリコールモノ（メタ）アクリレート、ステアロキシポリエチレングリコールモノ（メタ）アクリレート、フェノキシポリエチレングリコールモノ（メタ）アクリレート、フェノキシポリエチレングリコール・ポリプロピレングリコールモノ（メタ）アクリレート、ノニルフェノキシポリプロピレングリコールモノ（メタ）アクリレート、ノニルフェノキシポリ（エチレングリコール・プロピレングリコール）モノ（メタ）アクリレート等のポリアルキレングリコールのモノ（メタ）アクリレート；２−パーフルオロヘキシルエチル（メタ）アクリレート等のフッ素化アルキル基を有する（メタ）アクリレートなどが挙げられる。これらの重合性単量体（ｂ３）は、１種で用いることも２種以上併用することもできる。 Examples of the other polymerizable monomer (b3) include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-butyl (meth) acrylate and isobutyl (meth) acrylate, n-Pentyl (meth) acrylate, n-hexyl (meth) acrylate, n-heptyl (meth) acrylate, n-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) Acrylate, alkyl (meth) acrylates such as dodecyl (meth) acrylate; methoxypolyethylene glycol mono (meth) acrylate, octoxy polyethylene glycol / polypropylene glycol mono (meth) acrylate, lauroxy polyethylene glycol (Mono) (meth) acrylate, stearoxy polyethylene glycol mono (meth) acrylate, phenoxy polyethylene glycol mono (meth) acrylate, phenoxy polyethylene glycol polypropylene glycol mono (meth) acrylate, nonyl phenoxy polypropylene glycol mono (meth) acrylate, nonyl phenoxy poly (Ethylene glycol, propylene glycol) mono (meth) acrylates of polyalkylene glycols such as mono (meth) acrylate; (meth) acrylates having a fluorinated alkyl group such as 2-perfluorohexylethyl (meth) acrylate . These polymerizable monomers (b3) can be used alone or in combination of two or more.
前記重合性単量体（ｂ３）としては、より一層優れた帯電防止性が得られる点から、フッ素化アルキル基を有する（メタ）アクリレート、及び／又は、ポリアルキレングリコールのモノ（メタ）アクリレートを用いることが好ましく、また前記ポリアルキレングリコールのモノ（メタ）アクリレートとしてはメトキシポリエチレングリコールモノ（メタ）アクリレートがより好ましい。 As the polymerizable monomer (b3), a (meth) acrylate having a fluorinated alkyl group and / or a mono (meth) acrylate of a polyalkylene glycol, from the viewpoint that a further excellent antistatic property is obtained It is preferable to use, and as the mono (meth) acrylate of the polyalkylene glycol, methoxy polyethylene glycol mono (meth) acrylate is more preferable.
前記ポリアルキレングリコールのモノ（メタ）アクリレートの中でも、より一層優れた帯電防止性が得られる点から、前記ポリアルキレングリコールのモノ（メタ）アクリレートの原料となるポリアルキレングリコールの数平均分子量が２００〜８，０００の範囲のものが好ましく、３００〜６，０００の範囲のものがより好ましく、４００〜４，０００の範囲のものがさらに好ましく、４００〜２，０００の範囲のものが特に好ましい。 Among the mono (meth) acrylates of the polyalkylene glycols, the number average molecular weight of the polyalkylene glycol as a raw material of the mono (meth) acrylates of the polyalkylene glycols is 200 or more, from the viewpoint that much more excellent antistatic properties can be obtained. The range of 8,000 is preferable, the range of 300 to 6,000 is more preferable, the range of 400 to 4,000 is more preferable, and the range of 400 to 2,000 is particularly preferable.
前記樹脂（Ｂ）の原料全量中の前記重合性単量体（ｂ１）の比率は、本発明の活性エネルギー線硬化性組成物の硬化塗膜の帯電防止性をより向上できることから、５〜５５質量％の範囲が好ましく、１０〜５０質量％の範囲がより好ましく、１２〜４５質量％の範囲がさらに好ましい。 The ratio of the polymerizable monomer (b1) to the total amount of the raw material of the resin (B) can improve the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention, so 5 to 55 The range of mass% is preferable, the range of 10 to 50 mass% is more preferable, and the range of 12 to 45 mass% is more preferable.
また、前記樹脂（Ｂ）の原料全量中の前記重合性単量体（ｂ２）の比率は、本発明の活性エネルギー線硬化性組成物の硬化塗膜の帯電防止性をより向上できることから、３０〜９０質量％の範囲が好ましく、４０〜８０質量％の範囲がより好ましく、４５〜７０質量％の範囲がより好ましい。 Further, the ratio of the polymerizable monomer (b2) to the total amount of the raw material of the resin (B) can improve the antistatic property of the cured coating film of the active energy ray curable composition of the present invention, The range of -90 mass% is preferable, the range of 40-80 mass% is more preferable, and the range of 45-70 mass% is more preferable.
前記重合性単量体（ｂ３）として前記ポリアルキレングリコールのモノ（メタ）アクリレートを用いる場合は、本発明の活性エネルギー線硬化性組成物の硬化塗膜の帯電防止性をより向上できることから、前記樹脂（Ｂ）の原料全量中のポリアルキレングリコールのモノ（メタ）アクリレートの比率は、５〜６０質量％の範囲が好ましく、１０〜５０質量％の範囲がより好ましく、２０〜４０質量％の範囲がさらに好ましい。 When using the mono (meth) acrylate of the said polyalkylene glycol as said polymerizable monomer (b3), since the antistatic property of the cured coating film of the active energy ray curable composition of this invention can be improved more, The range of 5-60 mass% of the ratio of the polyalkylene glycol mono (meth) acrylate in the raw material whole quantity of resin (B) is preferable, The range of 10-50 mass% is more preferable, The range of 20-40 mass% Is more preferred.
また、前記重合性単量体（ｂ３）として前記フッ素化アルキル基を有する（メタ）アクリレートを用いる場合は、本発明の活性エネルギー線硬化性組成物の硬化塗膜の帯電防止性をより向上できることから、前記樹脂（Ｂ）の原料全量中のフッ素化アルキル基を有する（メタ）アクリレートの比率は、０．１〜２０質量％の範囲が好ましく、０．５〜１０質量％の範囲がより好ましく、１〜５質量％の範囲がさらに好ましい。 Moreover, when using the (meth) acrylate which has the said fluorinated alkyl group as said polymerizable monomer (b3), the antistatic property of the cured coating film of the active energy ray curable composition of this invention can be improved more. From the above, the ratio of the (meth) acrylate having a fluorinated alkyl group in the total amount of the raw material of the resin (B) is preferably in the range of 0.1 to 20% by mass, and more preferably in the range of 0.5 to 10% by mass The range of 1 to 5% by mass is more preferable.
前記樹脂（Ｂ）の重量平均分子量は、本発明の活性エネルギー線硬化性組成物の硬化塗膜の帯電防止性をより向上できることから、１，０００〜１００，０００の範囲が好ましく、２，０００〜５０，０００の範囲がより好ましく、３，０００〜３０，０００の範囲がさらに好ましい。なお、本発明における重量平均分子量は、ゲル・パーミエーション・クロマトグラフィー（ＧＰＣ）法により測定したポリスチレン換算での値である。 The weight average molecular weight of the resin (B) is preferably in the range of 1,000 to 100,000 because the antistatic property of the cured coating film of the active energy ray curable composition of the present invention can be further improved, and 2,000 The range of-50,000 is more preferable, and the range of 3,000 to 30,000 is more preferable. The weight average molecular weight in the present invention is a value in terms of polystyrene measured by gel permeation chromatography (GPC).
前記樹脂（Ｂ）の配合量は、本発明の活性エネルギー線硬化性組成物の硬化塗膜の帯電防止性及び耐ブリード性をより向上できることから、前記活性エネルギー線硬化性組成物（Ａ）１００質量部に対して、０．１〜１０質量部の範囲が好ましく、１．３〜５質量部の範囲がより好ましく、１．５〜２質量部の範囲が更に好ましい。 The compounding amount of the resin (B) can further improve the antistatic property and the bleeding resistance of the cured coating film of the active energy ray curable composition of the present invention, so the active energy ray curable composition (A) 100 The range of 0.1-10 mass parts is preferable with respect to a mass part, the range of 1.3-5 mass parts is more preferable, and the range of 1.5-2 mass parts is still more preferable.
前記化合物（Ｃ）は、４級アンモニウム塩を有し、かつ脂環構造を有しないものである。前記化合物（Ｃ）と前記樹脂（Ｂ）とを併用することにより、帯電防止剤（前記樹脂（Ｂ）及び化合物（Ｃ））の使用量を低減した場合であっても、硬化塗膜の優れた帯電防止性を発現することができ、ブリードも抑制することができる。 The compound (C) has a quaternary ammonium salt and does not have an alicyclic structure. Even when the usage of the antistatic agent (the resin (B) and the compound (C)) is reduced by using the compound (C) and the resin (B) in combination, the cured coating film is excellent. Antistatic properties can be exhibited, and bleeding can also be suppressed.
前記化合物（Ｃ）としては、例えば、前記樹脂（Ｂ）の原料として用いることができる前記４級アンモニウム塩を有する重合性単量体（ｂ２）、前記４級アンモニウム塩を有する重合性単量体（ｂ２）と前記その他の重合性単量体（ｂ３）との共重合体を用いることができる。 As said compound (C), the polymerizable monomer (b2) which has the said quaternary ammonium salt which can be used as a raw material of the said resin (B), the polymerizable monomer which has the said quaternary ammonium salt, for example A copolymer of (b2) and the other polymerizable monomer (b3) can be used.
前記化合物（Ｃ）の重量平均分子量としては、より一層優れた帯電防止性及び耐ブリード性が得られる点から、１００〜１，０００の範囲であることが好ましく、１３０〜５００の範囲がより好ましく、１５０〜３００の範囲が更に好ましい。 The weight average molecular weight of the compound (C) is preferably in the range of 100 to 1,000, and more preferably in the range of 130 to 500, from the viewpoint of obtaining further excellent antistatic property and bleed resistance. The range of 150 to 300 is more preferable.
前記化合物（Ｃ）には、耐ブリード性を高める点から、活性エネルギー線硬化性官能基を有することが更に好ましい。 The compound (C) more preferably has an active energy ray-curable functional group from the viewpoint of enhancing the bleed resistance.
前記化合物（Ｃ）としては、前記した中でも、より一層優れた帯電防止性及び耐ブリード性が得られる点から、２−［（メタ）アクリロイルオキシ］エチルトリメチルアンモニウムクロライド、３−［（メタ）アクリロイルオキシ］プロピルトリメチルアンモニウムクロライド、ジメチルアミノエチル（メタ）アクリルアミド塩化メチル４級塩、及び、ジメチルアミノプロピル（メタ）アクリルアミド塩化メチル４級塩からなる群より選ばれる１種以上の化合物を用いることが好ましい。 Among the compounds (C) described above, 2-[(meth) acryloyloxy] ethyltrimethylammonium chloride, 3-[(meth) acryloylyl, from the viewpoint that even more excellent antistatic property and bleed resistance can be obtained among the above-mentioned compounds. It is preferable to use one or more compounds selected from the group consisting of oxy] propyltrimethylammonium chloride, dimethylaminoethyl (meth) acrylamide methyl chloride quaternary salt, and dimethylaminopropyl (meth) acrylamide methyl chloride quaternary salt .
前記化合物（Ｃ）の配合量は、本発明の活性エネルギー線硬化性組成物の硬化塗膜の帯電防止性及び耐ブリード性をより向上できることから、前記活性エネルギー線硬化性組成物（Ａ）１００質量部に対して、０．１〜１５質量部の範囲が好ましく、１〜１０質量部の範囲がより好ましく、３〜８質量部の範囲が更に好ましい。 The compounding amount of the compound (C) can further improve the antistatic property and the bleeding resistance of the cured coating film of the active energy ray-curable composition of the present invention, so the active energy ray-curable composition (A) 100 The range of 0.1-15 mass parts is preferable with respect to a mass part, the range of 1-10 mass parts is more preferable, and the range of 3-8 mass parts is still more preferable.
前記樹脂（Ｂ）と前記化合物（Ｃ）との合計配合量としては、帯電防止性と耐ブリード性のバランスをより一層向上でき、湿熱条件下での使用後においても帯電防止性の変化も少ない点から、前記活性エネルギー線硬化性化合物（Ａ）１００質量部に対して、１〜１０質量部の範囲であることが好ましく、３〜８質量部の範囲がより好ましい。 With respect to the total blending amount of the resin (B) and the compound (C), the balance between the antistatic property and the bleed resistance can be further improved, and the change in the antistatic property is small even after use under moist heat conditions From the point of view, the amount is preferably in the range of 1 to 10 parts by mass, and more preferably 3 to 8 parts by mass with respect to 100 parts by mass of the active energy ray curable compound (A).
前記樹脂（Ｂ）と前記化合物（Ｃ）との質量比［（Ｂ）／（Ｃ）］としては、帯電防止性と耐ブリード性のバランスをより一層向上でき、かつ湿熱条件下での使用後においても帯電防止性の変化も少ない点から、５／９５〜４０／６０の範囲であることが好ましく、１０／９０〜３０／７０の範囲がより好ましく、１３／８７〜２０／８０の範囲が更に好ましい。 As a mass ratio [(B) / (C)] between the resin (B) and the compound (C), the balance between the antistatic property and the bleeding resistance can be further improved, and after use under wet heat conditions Even in the above, the range of 5/95 to 40/60 is preferable, the range of 10/90 to 30/70 is more preferable, and the range of 13/87 to 20/80 is also preferable because the change in the antistatic property is also small. More preferable.
前記有機溶剤（Ｄ）は、本発明の活性エネルギー線硬化性組成物中の他の成分を溶解できるものであれば特に制限なく用いることができる。前記有機溶剤（Ｄ）としては、例えば、トルエン、キシレン等の芳香族炭化水素；メタノール、エタノール、イソプロパノール、ｔ−ブタノール等のアルコール類；酢酸エチル、酢酸ブチル、プロピレングリコールモノメチルエーテルアセテート等のエステル類；アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン類などが挙げられる。これらの有機溶剤は単独で用いても２種以上を併用してもよい。 The organic solvent (D) can be used without particular limitation as long as it can dissolve other components in the active energy ray curable composition of the present invention. Examples of the organic solvent (D) include aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, isopropanol and t-butanol; and esters such as ethyl acetate, butyl acetate and propylene glycol monomethyl ether acetate And ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone. These organic solvents may be used alone or in combination of two or more.
本発明の活性エネルギー線硬化性組成物中の前記有機溶剤（Ｄ）の配合量は、後述する塗工方法に適した粘度になる量とすることが好ましい。 It is preferable that the compounding quantity of the said organic solvent (D) in the active energy ray curable composition of this invention sets it as the quantity used as the viscosity suitable for the coating method mentioned later.
また、本発明の活性エネルギー線硬化性組成物は、基材に塗工後、活性エネルギー線を照射することで硬化塗膜とすることができる。この活性エネルギー線とは、紫外線、電子線、α線、β線、γ線等の電離放射線をいう。活性エネルギー線として紫外線を照射して硬化塗膜とする場合には、本発明の活性エネルギー線硬化性組成物中に光重合開始剤（Ｅ）を添加し、硬化性を向上することが好ましい。また、必要であればさらに光増感剤を添加して、硬化性を向上することもできる。一方、電子線、α線、β線、γ線等の電離放射線を用いる場合には、光重合開始剤（Ｅ）や光増感剤を用いなくても速やかに硬化するので、特に光重合開始剤（Ｅ）や光増感剤を添加する必要はない。 Moreover, the active energy ray curable composition of this invention can be made into a cured coating film by irradiating an active energy ray after coating on a base material. The active energy ray refers to ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays. When ultraviolet rays are irradiated as active energy rays to form a cured coating film, it is preferable to add a photopolymerization initiator (E) to the active energy ray-curable composition of the present invention to improve the curability. Further, if necessary, a photosensitizer can be further added to improve the curability. On the other hand, in the case of using ionizing radiation such as electron beam, α ray, β ray, γ ray, etc., the photopolymerization initiator (E) and the photosensitizer are rapidly cured even without using the photopolymerization initiator, in particular There is no need to add an agent (E) or a photosensitizer.
前記光重合開始剤（Ｅ）としては、例えば、ジエトキシアセトフェノン、２−ヒドロキシ−２−メチル−１−フェニルプロパン−１−オン、オリゴ｛２−ヒドロキシ−２−メチル−１−［４−（１−メチルビニル）フェニル］プロパノン｝、ベンジルジメチルケタール、１−（４−イソプロピルフェニル）−２−ヒドロキシ−２−メチルプロパン−１−オン、４−（２−ヒドロキシエトキシ）フェニル−（２−ヒドロキシ−２−プロピル）ケトン、１−ヒドロキシシクロヘキシルフェニルケトン、２−メチル−２−モルホリノ（４−チオメチルフェニル）プロパン−１−オン、２−ベンジル−２−ジメチルアミノ−１−（４−モルホリノフェニル）−ブタノン等のアセトフェノン系化合物；ベンゾイン、ベンゾインメチルエーテル、ベンゾインイソプロピルエーテル等のベンゾイン系化合物；２，４，６−トリメチルベンゾインジフェニルホスフィンオキシド、ビス（２，４，６−トリメチルベンゾイル）−フェニルホスフィンオキシド等のアシルホスフィンオキシド系化合物；ベンジル（ジベンゾイル）、メチルフェニルグリオキシエステル、オキシフェニル酢酸２−（２−ヒドロキシエトキシ）エチルエステル、オキシフェニル酢酸２−（２−オキソ−２−フェニルアセトキシエトキシ）エチルエステル等のベンジル系化合物；ベンゾフェノン、ｏ−ベンゾイル安息香酸メチル−４−フェニルベンゾフェノン、４，４’−ジクロロベンゾフェノン、ヒドロキシベンゾフェノン、４−ベンゾイル−４’−メチル−ジフェニルサルファイド、アクリル化ベンゾフェノン、３，３’，４，４’−テトラ（ｔ−ブチルペルオキシカルボニル）ベンゾフェノン、３，３’−ジメチル−４−メトキシベンゾフェノン、２，４，６−トリメチルベンゾフェノン、４−メチルベンゾフェノン等のベンゾフェノン系化合物；２−イソプロピルチオキサントン、２，４−ジメチルチオキサントン、２，４−ジエチルチオキサントン、２，４−ジクロロチオキサントン等のチオキサントン系化合物；ミヒラ−ケトン、４，４’−ジエチルアミノベンゾフェノン等のアミノベンゾフェノン系化合物；１０−ブチル−２−クロロアクリドン、２−エチルアンスラキノン、９，１０−フェナンスレンキノン、カンファーキノン、１−［４−（４−ベンゾイルフェニルサルファニル）フェニル］−２−メチル−２−（４−メチルフェニルサルフォニル）プロパン−１−オン等が挙げられる。これらの光重合開始剤（Ｅ）は、１種で用いることも、２種以上併用することもできる。 Examples of the photopolymerization initiator (E) include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, oligo {2-hydroxy-2-methyl-1- [4- (4) 1-Methylvinyl) phenyl] propanone}, benzyl dimethyl ketal, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy) 2-Propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) Acetophenone compounds such as butanone; benzoin, benzoin methyl ether, benzoi Benzoin compounds such as isopropyl ether; Acyl phosphine oxide compounds such as 2,4,6-trimethylbenzoin diphenyl phosphine oxide, bis (2,4,6-trimethyl benzoyl) -phenyl phosphine oxide; benzyl (dibenzoyl), methyl phenyl Benzyl compounds such as glyoxy ester, oxyphenylacetic acid 2- (2-hydroxyethoxy) ethyl ester, oxyphenylacetic acid 2- (2-oxo-2-phenylacetoxyethoxy) ethyl ester; benzophenone, methyl o-benzoylbenzoate -4-phenylbenzophenone, 4,4'-dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, acrylated benzophenone, 3,3 ', Benzophenone compounds such as 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, 3,3′-dimethyl-4-methoxybenzophenone, 2,4,6-trimethylbenzophenone, 4-methylbenzophenone and the like; 2-isopropylthioxanthone, Thioxanthone compounds such as 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone; aminobenzophenone compounds such as Michael-ketone, 4,4'-diethylaminobenzophenone; 10-butyl-2- Chloroacridone, 2-ethylanthraquinone, 9,10-phenanthrenequinone, camphorquinone, 1- [4- (4-benzoylphenylsulfanyl) phenyl] -2-methyl-2- (4-methylphenylsal) Phonil) Propan-1-one and the like can be mentioned. These photopolymerization initiators (E) can be used alone or in combination of two or more.
また、前記光増感剤としては、例えば、ジエタノールアミン、Ｎ−メチルジエタノールアミン、トリブチルアミン等の３級アミン化合物、ｏ−トリルチオ尿素等の尿素化合物、ナトリウムジエチルジチオホスフェート、ｓ−ベンジルイソチウロニウム−ｐ−トルエンスルホネート等の硫黄化合物などが挙げられる。 Also, as the photosensitizer, for example, tertiary amine compounds such as diethanolamine, N-methyldiethanolamine, tributylamine, urea compounds such as o-tolylthiourea, sodium diethyl dithiophosphate, s-benzylisothironium-p -Sulfur compounds such as toluene sulfonate and the like can be mentioned.
上記の光重合開始剤（Ｅ）及び光増感剤の使用量は、本発明の活性エネルギー線硬化性組成物中の前記活性エネルギー線硬化性（Ａ）１００質量部に対し、各々０．０５〜２０質量部が好ましく、０．５〜１０質量％がより好ましい。 The amount of the photopolymerization initiator (E) and the photosensitizer used is 0.05 for each 100 parts by mass of the active energy ray curable (A) in the active energy ray curable composition of the present invention. -20 mass parts are preferable, and 0.5-10 mass% is more preferable.
本発明の活性エネルギー線硬化性組成物には、上記の成分（Ａ）〜（Ｅ）以外のその他の配合物として、用途、要求特性に応じて、重合禁止剤、表面調整剤、消泡剤、粘度調整剤、耐光安定剤、耐候安定剤、耐熱安定剤、紫外線吸収剤、酸化防止剤、レベリング剤、有機顔料、無機顔料、顔料分散剤、シリカビーズ、有機ビーズ等の添加剤；酸化ケイ素、酸化アルミニウム、酸化チタン、ジルコニア、五酸化アンチモン等の無機充填剤などを配合することができる。これらその他の配合物は、１種で用いることも２種以上併用することもできる。 In the active energy ray-curable composition of the present invention, as other compounds other than the above components (A) to (E), a polymerization inhibitor, a surface control agent, an antifoamer according to the application and the required characteristics. Additives such as viscosity modifiers, light stabilizers, weather stabilizers, heat stabilizers, UV absorbers, antioxidants, leveling agents, organic pigments, inorganic pigments, pigment dispersants, silica beads, organic beads, etc .; silicon oxide Inorganic fillers such as aluminum oxide, titanium oxide, zirconia, and antimony pentoxide can be blended. These other compounds may be used alone or in combination of two or more.
本発明のフィルムは、フィルム基材の少なくとも１面に、本発明の活性エネルギー線硬化性組成物を塗工し、その後活性エネルギー線を照射して硬化塗膜とすることで得られたものである。 The film of the present invention is obtained by applying the active energy ray-curable composition of the present invention on at least one surface of a film substrate and then irradiating the active energy ray to form a cured coating film. is there.
本発明のフィルムで用いる前記フィルム基材の材質としては、透明性の高い樹脂が好ましく、例えば、ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリエチレンナフタレート等のポリエステル系樹脂；ポリプロピレン、ポリエチレン、ポリメチルペンテン−１等のポリオレフィン系樹脂；セルロースアセテート（ジアセチルセルロース、トリアセチルセルロース等）、セルロースアセテートプロピオネート、セルロースアセテートブチレート、セルロースアセテートプロピオネートブチレート、セルロースアセテートフタレート、硝酸セルロース等のセルロース系樹脂；ポリメチルメタクリレート等のアクリル系樹脂；ポリ塩化ビニル、ポリ塩化ビニリデン等の塩化ビニル系樹脂；ポリビニルアルコール；エチレン−酢酸ビニル共重合体；ポリスチレン；ポリアミド；ポリカーボネート；ポリスルホン；ポリエーテルスルホン；ポリエーテルエーテルケトン；ポリイミド、ポリエーテルイミド等のポリイミド系樹脂；ノルボルネン系樹脂（例えば、日本ゼオン株式会社製「ゼオノア」）、変性ノルボルネン系樹脂（例えば、ＪＳＲ株式会社製「アートン」）、環状オレフィン共重合体（例えば、三井化学株式会社製「アペル」）などが挙げられる。さらに、これらの樹脂からなる基材を２種以上貼り合わせたものを用いても構わない。 The material of the film substrate used in the film of the present invention is preferably a highly transparent resin, for example, polyester resins such as polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, etc .; polypropylene, polyethylene, polymethylpentene-1 And polyolefin resins such as cellulose acetate (diacetyl cellulose, triacetyl cellulose etc.), cellulose acetate propionate, cellulose acetate butyrate, cellulose acetate propionate butyrate, cellulose acetate phthalate, cellulose nitrate such as cellulose nitrate; Acrylic resins such as methyl methacrylate; vinyl chloride resins such as polyvinyl chloride and polyvinylidene chloride; polyvinyl alcohol; ethylene-vinyl acetate Copolymer; polystyrene; polyamide; polycarbonate; polysulfone; polyethersulfone; polyetheretherketone; polyimide, polyimide resin such as polyimide, polyetherimide; norbornene resin (for example, "Zeonor" manufactured by Nippon Zeon Co., Ltd.), modified Norbornene-based resins (for example, "Arton" manufactured by JSR Corporation), cyclic olefin copolymers (for example, "Aper" manufactured by Mitsui Chemicals, Inc.), and the like. Furthermore, you may use what bonded the base material which consists of these resin in 2 or more types.
また、前記フィルム基材は、フィルム状でもシート状でもよく、その厚さは、２０〜５００μｍの範囲が好ましい。また、フィルム状の基材フィルムを用いる場合には、その厚さは、２０〜２００μｍの範囲が好ましく、３０〜１５０μｍの範囲がより好ましく、４０〜１３０μｍの範囲がさらに好ましい。フィルム基材の厚さを当該範囲とすることで、フィルムの片面に、本発明の活性エネルギー線硬化性組成物によりハードコート層を設けた場合にもカールを抑制しやすくなる。 The film substrate may be in the form of film or sheet, and the thickness thereof is preferably in the range of 20 to 500 μm. Moreover, when using a film-like base film, the range of 20-200 micrometers is preferable, as for the thickness, the range of 30-150 micrometers is more preferable, and the range of 40-130 micrometers is further more preferable. By setting the thickness of the film substrate to the above range, curling can be easily suppressed even when a hard coat layer is provided on one side of the film by the active energy ray curable composition of the present invention.
前記フィルム基材に本発明の活性エネルギー線硬化性組成物を塗工する方法としては、例えば、ダイコート、マイクログラビアコート、グラビアコート、ロールコート、コンマコート、エアナイフコート、キスコート、スプレーコート、ディップコート、スピンナーコート、刷毛塗り、シルクスクリーンによるベタコート、ワイヤーバーコート、フローコート等が挙げられる。 As a method of applying the active energy ray-curable composition of the present invention to the film substrate, for example, die coating, microgravure coating, gravure coating, roll coating, comma coating, air knife coating, kiss coating, spray coating, dip coating , Spinner coat, brush coating, silk screen beta coat, wire bar coat, flow coat and the like.
本発明の活性エネルギー線硬化性組成物中に含む有機溶媒は、活性エネルギー線硬化性組成物を基材フィルムへの塗工した後、活性エネルギー線を照射する前に揮発させ、また、前記樹脂（Ｂ）及び化合物（Ｃ）を塗膜表面に偏析させるために、加熱又は室温乾燥することが好ましい。加熱乾燥の条件としては、有機溶剤が揮発する条件であれば、特に限定しないが、通常は、温度５０〜１００℃の範囲で、時間は０．５〜１０分の範囲で加熱乾燥することが好ましい。 The organic solvent contained in the active energy ray-curable composition of the present invention volatilizes the active energy ray-curable composition before the active energy ray is irradiated after being applied to the substrate film, and the resin In order to cause (B) and the compound (C) to segregate on the coating film surface, it is preferable to heat or dry at room temperature. The heating and drying conditions are not particularly limited as long as the organic solvent is volatilized, but the heating and drying may be usually performed at a temperature of 50 to 100 ° C. and for a time of 0.5 to 10 minutes. preferable.
本発明の活性エネルギー線硬化性組成物を硬化させる活性エネルギー線としては、上記の通り、紫外線、電子線、α線、β線、γ線等の電離放射線である。ここで、活性エネルギー線として紫外線を用いる場合、その紫外線を照射する装置としては、例えば、低圧水銀ランプ、高圧水銀ランプ、超高圧水銀ランプ、メタルハライドランプ、無電極ランプ（フュージョンランプ）、ケミカルランプ、ブラックライトランプ、水銀−キセノンランプ、ショートアーク灯、ヘリウム・カドミニウムレーザー、アルゴンレーザー、太陽光、ＬＥＤランプ等が挙げられる。 The active energy ray for curing the active energy ray-curable composition of the present invention is, as described above, ionizing radiation such as ultraviolet light, electron beam, α-ray, β-ray and γ-ray. Here, when using an ultraviolet ray as an active energy ray, as an apparatus which irradiates the ultraviolet ray, for example, a low pressure mercury lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, a metal halide lamp, an electrodeless lamp (fusion lamp), a chemical lamp, Black light lamps, mercury-xenon lamps, short arc lamps, helium / cadmium lasers, argon lasers, sunlight, LED lamps and the like can be mentioned.
前記フィルム基材上に本発明の活性エネルギー線硬化性組成物の硬化塗膜を形成する際の硬化塗膜の膜厚は、硬化塗膜の硬さを充分なものとし、かつ塗膜の硬化収縮によるフィルムのカールを抑制できることから、１〜３０μｍの範囲が好ましいが、３〜１５μｍの範囲がより好ましく、４〜１０μｍの範囲がさらに好ましい。 The film thickness of the cured coating film at the time of forming the cured coating film of the active energy ray curable composition of the present invention on the film substrate makes the hardness of the cured coating film sufficient and cures the coating film The range of 1 to 30 μm is preferable because curling of the film due to shrinkage can be suppressed, but the range of 3 to 15 μm is more preferable, and the range of 4 to 10 μm is more preferable.
以上、本発明の活性エネルギー線硬化性組成物は、優れた帯電防止性、及び、耐ブリード性を有するハードコート層を形成できるものである。前記活性エネルギー線硬化性組成物の硬化塗膜の表面抵抗値としては、１×１０７〜９．９９×１０９Ω／□の範囲であることが好ましく、１×１０８〜９．９９×１０８Ω／□の範囲がより好ましい。なお、前記硬化塗膜の表面抵抗値の測定方法は、実施例にて記載する。 As described above, the active energy ray curable composition of the present invention can form a hard coat layer having excellent antistatic property and bleed resistance. The surface resistance value of the cured coating film of the active energy ray-curable composition is preferably in the range of 1 × 10 7 to 9.99 × 10 9 Ω / □, and 1 × 10 8 to 9.99 × The range of 10 8 Ω / □ is more preferable. In addition, the measuring method of the surface resistance value of the said cured coating film is described in an Example.
以下、実施例により本発明をより具体的に説明する。 Hereinafter, the present invention will be more specifically described by way of examples.
（製造例１：脂環構造及び４級アンモニウム塩を有する樹脂（Ｂ−１）の製造）
攪拌装置、還流冷却管及び窒素導入管を備えたフラスコ中に、窒素ガスを導入して、フラスコ内の空気を窒素ガスで置換した。その後、フラスコに２−（メタクリロイルオキシ）エチルトリメチルアンモニウムクロライド５４．７質量部、シクロヘキシルメタクリレート１９．９質量部、メトキシポリエチレングリコールメタクリレート（日油株式会社製「ブレンマー ＰＭＥ−１０００」；繰り返し単位数ｎ≒２３、分子量１，０００）２４．９質量部、メタクリル酸０．５質量部、メタノール５０質量部及びＰＧＭＥ１０質量部を加えた。次いで、重合開始剤（アゾビスイソブチロニトリル）０．１質量部をＰＧＭＥ２．４質量部で溶解した溶液を３０分かけて滴下した後、６５℃で３時間反応させた。次いで、メタノールを加えて希釈し、脂環構造及び４級アンモニウム塩を有する樹脂（Ｂ−２）の４５質量％溶液を得た。得られた樹脂（Ｂ−１）の重量平均分子量は１万であった。
Production Example 1 Production of Resin (B-1) Having Alicyclic Structure and Quaternary Ammonium Salt
Nitrogen gas was introduced into a flask equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, and the air in the flask was replaced with nitrogen gas. Thereafter, 54.7 parts by mass of 2- (methacryloyloxy) ethyl trimethyl ammonium chloride, 19.9 parts by mass of cyclohexyl methacrylate, methoxy polyethylene glycol methacrylate ("Blenmer PME-1000" manufactured by NOF Corporation) in a flask; the number of repeating units n ≒ 23, 24.9 parts by mass of molecular weight 1,000), 0.5 parts by mass of methacrylic acid, 50 parts by mass of methanol and 10 parts by mass of PGME were added. Next, a solution in which 0.1 part by mass of a polymerization initiator (azobisisobutyro nitrile) was dissolved in 2.4 parts by mass of PGME was added dropwise over 30 minutes, and then reacted at 65 ° C. for 3 hours. Subsequently, methanol was added for dilution to obtain a 45% by mass solution of resin (B-2) having an alicyclic structure and a quaternary ammonium salt. The weight average molecular weight of the obtained resin (B-1) was 10,000.
（製造例２：脂環構造及び４級アンモニウム塩を有する樹脂（Ｂ−２）の製造）
攪拌装置、還流冷却管及び窒素導入管を備えたフラスコ中に、窒素ガスを導入して、フラスコ内の空気を窒素ガスで置換した。その後、フラスコに２−（メタクリロイルオキシ）エチルトリメチルアンモニウムクロライド５３．７質量部、シクロヘキシルメタクリレート２９．３質量部、メトキシポリエチレングリコールメタクリレート（日油株式会社製「ブレンマー ＰＭＥ−１０００」；繰り返し単位数ｎ≒２３、分子量１，０００）１４.６質量部、２−パーフルオロヘキシルエチルアクリレート１．９質量部、メタクリル酸０．５質量部、メタノール５０質量部及びプロピレングリコールモノメチルエーテル１０質量部を加えた。次いで、重合開始剤（アゾビスイソブチロニトリル）０．１質量部をプロピレングリコールモノメチルエーテル２．４質量部で溶解した溶液を３０分かけて滴下した後、６５℃で３時間反応させた。次いで、メタノールを加えて希釈し、脂環構造及び４級アンモニウム塩を有する樹脂（Ｂ−２）の４５質量％溶液を得た。得られた樹脂（Ｂ−１）の重量平均分子量は１万であった。
Production Example 2: Production of Resin (B-2) Having Alicyclic Structure and Quaternary Ammonium Salt
Nitrogen gas was introduced into a flask equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, and the air in the flask was replaced with nitrogen gas. Thereafter, 53.7 parts by mass of 2- (methacryloyloxy) ethyl trimethyl ammonium chloride, 29.3 parts by mass of cyclohexyl methacrylate, methoxypolyethylene glycol methacrylate ("Blenmer PME-1000" manufactured by NOF Corporation) in a flask; the number of repeating units n ≒ 23, 14.6 parts by mass of molecular weight 1,000), 1.9 parts by mass of 2-perfluorohexylethyl acrylate, 0.5 parts by mass of methacrylic acid, 50 parts by mass of methanol and 10 parts by mass of propylene glycol monomethyl ether were added. Next, a solution of 0.1 parts by mass of a polymerization initiator (azobisisobutyro nitrile) dissolved in 2.4 parts by mass of propylene glycol monomethyl ether was dropped over 30 minutes, and then reacted at 65 ° C. for 3 hours. Subsequently, methanol was added for dilution to obtain a 45% by mass solution of resin (B-2) having an alicyclic structure and a quaternary ammonium salt. The weight average molecular weight of the obtained resin (B-1) was 10,000.
上記で得られた樹脂（Ｂ−１）、及び、（Ｂ−２）の重量平均分子量は、ゲル・パーミエーション・クロマトグラフィー（ＧＰＣ）法により、下記の条件で測定した。 The weight average molecular weights of the resins (B-1) and (B-2) obtained above were measured by gel permeation chromatography (GPC) under the following conditions.
測定装置：高速ＧＰＣ装置（東ソー株式会社製「ＨＬＣ−８２２０ＧＰＣ」）
カラム：東ソー株式会社製の下記のカラムを直列に接続して使用した。
「ＴＳＫｇｅｌ Ｇ５０００」（７．８ｍｍＩ．Ｄ．×３０ｃｍ）×１本
「ＴＳＫｇｅｌ Ｇ４０００」（７．８ｍｍＩ．Ｄ．×３０ｃｍ）×１本
「ＴＳＫｇｅｌ Ｇ３０００」（７．８ｍｍＩ．Ｄ．×３０ｃｍ）×１本
「ＴＳＫｇｅｌ Ｇ２０００」（７．８ｍｍＩ．Ｄ．×３０ｃｍ）×１本
検出器：ＲＩ（示差屈折計）
カラム温度：４０℃
溶離液：テトラヒドロフラン（ＴＨＦ）
流速：１．０ｍＬ／分
注入量：１００μＬ（試料濃度０．４質量％のテトラヒドロフラン溶液）
標準試料：下記の標準ポリスチレンを用いて検量線を作成した。
Measuring device: High-speed GPC device ("HLC-8220GPC" manufactured by Tosoh Corporation)
Column: The following columns manufactured by Tosoh Corporation were used in series connection.
"TSKgel G5000" (7.8 mm ID × 30 cm) × 1 "TSK gel G 4000" (7.8 mm ID × 30 cm) × 1 "TSK gel G 3000" (7.8 mm ID × 30 cm) × 1 This "TSKgel G2000" (7.8 mm ID × 30 cm) × 1 detector: RI (differential refractometer)
Column temperature: 40 ° C
Eluent: Tetrahydrofuran (THF)
Flow rate: 1.0 mL / min Injection volume: 100 μL (tetrahydrofuran solution with a sample concentration of 0.4% by mass)
Standard sample: A calibration curve was prepared using the following standard polystyrene.
（標準ポリスチレン）
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ａ−５００」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ａ−１０００」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ａ−２５００」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ａ−５０００」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−１」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−２」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−４」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−１０」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−２０」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−４０」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−８０」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−１２８」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−２８８」
東ソー株式会社製「ＴＳＫｇｅｌ 標準ポリスチレン Ｆ−５５０」
(Standard polystyrene)
Tosoh Corporation "TSKgel standard polystyrene A-500"
Tosoh Corporation "TSKgel standard polystyrene A-1000"
Tosoh Corporation "TSKgel standard polystyrene A-2500"
Tosoh Corporation "TSKgel standard polystyrene A-5000"
Tosoh Corporation "TSKgel standard polystyrene F-1"
Tosoh Corporation "TSKgel standard polystyrene F-2"
Tosoh Corporation "TSKgel standard polystyrene F-4"
Tosoh Corporation "TSKgel standard polystyrene F-10"
Tosoh Corporation "TSKgel standard polystyrene F-20"
Tosoh Corporation "TSKgel standard polystyrene F-40"
Tosoh Corporation "TSKgel standard polystyrene F-80"
Tosoh Corporation "TSKgel standard polystyrene F-128"
Tosoh Corporation "TSKgel standard polystyrene F-288"
Tosoh Corporation "TSKgel standard polystyrene F-550"
［水酸基価の測定方法］
活性エネルギー線硬化性化合物の水酸基価はＪＩＳ−Ｋ００７０に記載の水酸基価測定方法を用いて、以下のように測定した。
無水酢酸２５ｇを全量フラスコ１００ｍｌに取り、ピリジンを加えて全量を１００ｍｌにして混合均一にした混合液を５ｍｌ秤量し、これに活性エネルギー線硬化性化合物を溶解させた後、１００℃で１時間、無水酢酸と活性エネルギー線硬化性化合物中の水酸基とを反応させる。放冷後、水１ｍｌを加えて攪拌混合し、更に１００℃で１０分間撹拌して、過剰の無水酢酸を分解し、放冷後エタノール５ｍｌでフラスコ等の壁を洗う。フェノールフタレイン溶液数滴を指示薬として加え、０．５ｍｏｌ／Ｌ水酸化カリウムエタノール溶液で滴定する（滴定量βｍｌ）。活性エネルギー線硬化性化合物を用いないブランク測定を同様に行い滴定する（滴定量β0ｍｌ）。水酸基価は下記式（１）から求められる。
水酸基価（ｍｇＫＯＨ／ｇ）＝（β0−β）×ｆ×２８．０５／Ｓ＋Ｄ （１）
但し ｆ：０．５ｍｏｌ／Ｌ水酸化カリウムエタノール溶液のファクター
Ｓ：活性エネルギー線硬化性化合物の実採取重量（単位：ｇ）
Ｄ：酸価（ｍｇＫＯＨ／ｇ）
[Method of measuring hydroxyl value]
The hydroxyl value of the active energy ray curable compound was measured as follows using the hydroxyl value measurement method described in JIS-K0070.
Take 25 g of acetic anhydride in a 100 ml volumetric flask, add pyridine to make the total volume 100 ml, and mix and homogenize 5 ml of the mixed liquid. Weigh the active energy ray-curable compound in this, and then at 100 ° C for 1 hour Acetic anhydride and a hydroxyl group in the active energy ray curable compound are reacted. After allowing to cool, 1 ml of water is added and mixed with stirring, and the mixture is further stirred at 100 ° C. for 10 minutes to decompose excess acetic anhydride, and after allowing to cool, the wall etc. Add a few drops of phenolphthalein solution as an indicator and titrate with 0.5 mol / L potassium hydroxide ethanol solution (titer β ml). A blank measurement without active energy ray-curable compound is likewise carried out and titrated (titrated β 0 ml). A hydroxyl value is calculated | required from following formula (1).
Hydroxyl value (mg KOH / g) = (β 0 -β) × f × 28.05 / S + D (1)
However, f: Factor S of 0.5 mol / L potassium hydroxide ethanol solution: Actual collected weight of active energy ray-curable compound (unit: g)
D: Acid value (mg KOH / g)
（実施例１）
ジペンタエリスリトールヘキサアクリレート（以下、「ＤＰＨＡ」と略記する。）１００質量部、製造例１で得られた樹脂（Ｂ−１）溶液２．２２質量部（樹脂（Ｂ−１）として１質量部）、ジメチルアミノプロピルアクリルアミド塩化メチル４級塩（以下、（Ｃ−１）と略記する。）５質量部、光重合開始剤（１−ヒドロキシシクロヘキシルフェニルケトン）５質量部、溶剤（エタノール／ｎ−プロピルアルコール／メタノール＝８５．５／９．６／４．９（質量比））１００質量部を均一に混合して活性エネルギー線硬化性組成物（１）を得た。
Example 1
100 parts by mass of dipentaerythritol hexaacrylate (hereinafter abbreviated as "DPHA"), 2.22 parts by mass of the resin (B-1) solution obtained in Production Example 1 (1 part by mass as resin (B-1) 5 parts by mass of dimethylaminopropyl acrylamide methyl chloride quaternary salt (hereinafter abbreviated as (C-1)), 5 parts by mass of a photopolymerization initiator (1-hydroxycyclohexyl phenyl ketone), a solvent (ethanol / n-) 100 parts by mass of propyl alcohol / methanol = 85.5 / 9.6 / 4.9 (mass ratio) were uniformly mixed to obtain an active energy ray-curable composition (1).
（実施例２、比較例１〜３）
表１に示した組成に変更した以外は実施例１と同様に行い、活性エネルギー線硬化性組成物（２）、（Ｒ１）〜（Ｒ３）を得た。
(Example 2, Comparative Examples 1 to 3)
It carried out like Example 1 except having changed into the composition shown in Table 1, and obtained active energy ray hardening composition (2), (R1)-(R3).
［評価用サンプルの作製］
活性エネルギー線硬化性組成物を、厚さ６０μｍのトリアセチルセルロース（ＴＡＣ）フィルム（富士フイルム株式会社製）に、バーコーターで膜厚５μｍとなるように塗工し、６０℃で１．５分間乾燥した後、空気雰囲気下で紫外線照射装置（アイグラフィックス株式会社製、高圧水銀ランプ）を用いて照射光量３ｋＪ／ｍ２で照射し、硬化塗膜を有するＴＡＣフィルムを評価用サンプルとして得た。
また、この評価用サンプルを、温度：６５℃、湿度：９５％の条件下で３００時間放置し、これを耐湿熱試験後の評価用サンプルとした。
[Preparation of sample for evaluation]
The active energy ray-curable composition is coated on a 60 μm thick triacetyl cellulose (TAC) film (Fuji Film Co., Ltd.) with a bar coater to a film thickness of 5 μm, and at 60 ° C. for 1.5 minutes After drying, it was irradiated at an irradiation light quantity of 3 kJ / m 2 using an ultraviolet irradiation apparatus (high pressure mercury lamp manufactured by Eye Graphics Co., Ltd.) in an air atmosphere to obtain a TAC film having a cured coating film as a sample for evaluation. .
Moreover, this sample for evaluation was left to stand for 300 hours under the conditions of temperature: 65 ° C. and humidity: 95%, and this was used as the sample for evaluation after the heat and humidity resistance test.
［表面抵抗値の測定（帯電防止性の評価）］
上記で得られた評価用サンプル、及び、耐久性試験後の評価用サンプルの硬化塗膜の表面について、ＪＩＳ試験方法Ｋ６９１１−１９９５に準拠して、高抵抗率計（株式会社三菱化学アナリテック製「ハイレスタ−ＵＰ ＭＣＰ−ＨＴ４５０」）を用いて、印加電圧５００Ｖ、測定時間１０秒で表面抵抗値を測定した。
[Measurement of surface resistance (evaluation of antistatic property)]
A high resistivity meter (Mitsubishi Chemical Analytech Co., Ltd.) was applied to the surface of the cured sample of the evaluation sample obtained above and the evaluation sample after the durability test according to JIS test method K6911-1995. The surface resistance value was measured at an applied voltage of 500 V and a measurement time of 10 seconds using “Hiresta-UP MCP-HT450”.
［耐ブリード性の評価方法］
上記で得られた評価用サンプル、及び、耐久性試験後の評価用サンプルの硬化塗膜の表面について、目視観察により以下のように評価した。
「○」：ブリード物が確認されない。
「×」：ブリード物が確認される。
[Method of evaluating resistance to bleeding]
About the surface of the cured coating film of the sample for evaluation obtained above, and the sample for evaluation after a durability test, it evaluated as follows by visual observation.
"○": Bleed material is not confirmed.
"X": A bleed thing is confirmed.
［鉛筆硬さの評価方法］
上記で得られた評価用サンプル、及び、耐久性試験後の評価用サンプルの硬化塗膜の表面について、ＪＩＳ試験方法Ｋ５６００−５−４：１９９９に準拠して、鉛筆硬さを測定した。
[Evaluation method of pencil hardness]
The pencil hardness was measured based on JIS test method K5600-5-4: 1999 about the surface of the cured coating film of the sample for evaluation obtained above, and the sample for evaluation after a durability test.
表１に示す略語は下記の化合物を示す。
「ＰＥＴＡ」：ペンタエリスリトールテトラアクリレート
「（Ｃ−２）」：２−［メタアクリロイルオキシ］エチルトリメチルアンモニウムクロライド
The abbreviations shown in Table 1 indicate the following compounds.
"PETA": pentaerythritol tetraacrylate "(C-2)": 2- [methacryloyloxy] ethyl trimethyl ammonium chloride
本発明の活性エネルギー線硬化性組成物の硬化塗膜は、優れた鉛筆硬度を有し、表面抵抗値が１０の８乗〜９乗オーダーで帯電防止性も高いことが確認できた。また、耐湿熱試験後においても、表面抵抗値の変化が少なく、ブリード物も確認されなかった。 The cured coating film of the active energy ray-curable composition of the present invention has excellent pencil hardness, and it has been confirmed that the surface resistance value is high on the order of 10 to 9 of 10, and the antistatic property is also high. In addition, even after the heat and humidity resistance test, the change in the surface resistance was small, and no bleeding was observed.
一方、比較例１は、樹脂（Ｂ）を配合しない態様であるが、表面抵抗値が１０の１３乗オーダーであり、帯電防止性が不良であった。 On the other hand, Comparative Example 1 is an embodiment in which the resin (B) is not blended, but the surface resistance value is on the order of 10 to the 13th power, and the antistatic property is poor.
比較例２は、化合物（Ｃ）を配合しない態様であるが、表面抵抗値が１０の１１乗オーダーであり、帯電防止性が不良であった。 Comparative Example 2 is an embodiment in which the compound (C) is not blended, but the surface resistance value is on the order of 10 11 and the antistatic property is poor.
比較例３も化合物（Ｃ）を配合しない態様であり、表面抵抗値は良好なものの、耐湿熱試験後のブリード物が顕著に確認された。 The comparative example 3 is also an aspect which does not mix | blend a compound (C), Although the surface resistance value is favorable, the bleed thing after a moist heat resistance test was confirmed notably.
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| JP2006342213A (en) * | 2005-06-07 | 2006-12-21 | Mitsubishi Rayon Co Ltd | Photocurable resin composition, resin laminate, and method for producing the resin laminate |
| JP2012177050A (en) * | 2011-02-28 | 2012-09-13 | Nippon Kasei Chem Co Ltd | Antistatic resin composition, and film or molded product having antistatic layer |
| WO2015198959A1 (en) * | 2014-06-27 | 2015-12-30 | Dic株式会社 | Active energy ray-curable composition and film using same |
| JP2017039891A (en) * | 2015-08-21 | 2017-02-23 | Dic株式会社 | Active energy ray-curable composition and film prepared therewith |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI796371B (en) | 2023-03-21 |
| TW201917179A (en) | 2019-05-01 |
| CN109666361A (en) | 2019-04-23 |
| JP7114874B2 (en) | 2022-08-09 |
| KR102625535B1 (en) | 2024-01-17 |
| KR20190042451A (en) | 2019-04-24 |
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