CN112654644A - Active energy ray-curable composition and film using same - Google Patents
Active energy ray-curable composition and film using same Download PDFInfo
- Publication number
- CN112654644A CN112654644A CN201980058068.6A CN201980058068A CN112654644A CN 112654644 A CN112654644 A CN 112654644A CN 201980058068 A CN201980058068 A CN 201980058068A CN 112654644 A CN112654644 A CN 112654644A
- Authority
- CN
- China
- Prior art keywords
- meth
- acrylate
- active energy
- energy ray
- curable composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 239000002216 antistatic agent Substances 0.000 claims abstract description 25
- 150000001768 cations Chemical group 0.000 claims abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 139
- 239000011248 coating agent Substances 0.000 claims description 30
- 238000000576 coating method Methods 0.000 claims description 29
- 239000004593 Epoxy Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004437 phosphorous atom Chemical group 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000010408 film Substances 0.000 description 52
- -1 methacryloyl group Chemical group 0.000 description 27
- 150000003077 polyols Chemical class 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- 239000005056 polyisocyanate Substances 0.000 description 13
- 229920001228 polyisocyanate Polymers 0.000 description 13
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- 239000011324 bead Substances 0.000 description 12
- 239000010419 fine particle Substances 0.000 description 12
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
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- 238000011156 evaluation Methods 0.000 description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 9
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 5
- 239000002608 ionic liquid Substances 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003504 photosensitizing agent Substances 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical class C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 3
- 230000005260 alpha ray Effects 0.000 description 3
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 230000005250 beta ray Effects 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000005251 gamma ray Effects 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000005865 ionizing radiation Effects 0.000 description 3
- 239000004973 liquid crystal related substance Substances 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
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
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- 239000003795 chemical substances by application Substances 0.000 description 2
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- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
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- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
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- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
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- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- JZKPKNSYAHAKJY-UHFFFAOYSA-N 1-[4-(4-benzoylphenyl)sulfanylphenyl]-2-methyl-2-(4-methylphenyl)sulfonylpropan-1-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C)(C)C(=O)C(C=C1)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 JZKPKNSYAHAKJY-UHFFFAOYSA-N 0.000 description 1
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- YWEJNVNVJGORIU-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-hydroxy-2-phenylacetate Chemical compound OCCOCCOC(=O)C(O)C1=CC=CC=C1 YWEJNVNVJGORIU-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- 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
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
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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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
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- 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
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
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Abstract
The invention provides an active energy ray-curable composition and a film using the active energy ray-curable composition, wherein the active energy ray-curable composition contains an active energy ray-curable compound (A) and an antistatic agent (B), and the antistatic agent (B) has a cation part represented by formula (1). The active energy ray-curable composition can form a hard coat layer having excellent anti-glare properties and antistatic properties.
Description
Technical Field
The present invention relates to an active energy ray-curable composition capable of forming a hard coat layer and a film using the same.
Background
Resin films are used for various applications such as anti-scratch films for surfaces of Flat Panel Displays (FPDs) such as Liquid Crystal Displays (LCDs), organic EL displays (OLEDs), and Plasma Displays (PDPs), decorative films (sheets) for interior and exterior decoration of automobiles, low reflection films for windows, and heat ray blocking films. However, since the surface of the resin film is soft and has low scratch resistance, the following operation is generally performed in order to compensate for this drawback: a hard coat agent containing an active energy ray-curable composition or the like is applied to the film surface and cured, whereby a hard coat layer is provided on the film surface.
In addition, in these applications, the demand for low cost and high definition has been increasing in recent years, but there are problems as follows: if the hard coating agent is coated at a high speed, peeling electrification is likely to occur, and floating foreign matter in the air is adsorbed to cause coating defects, resulting in a decrease in yield. Therefore, as a measure for suppressing the reduction in the yield, a method of imparting antistatic properties has been widely used, and a quaternary ammonium salt-based antistatic agent which is particularly inexpensive and has high transparency is often used (for example, see patent documents 1 and 2).
On the other hand, as resin films used in the production of FPDs, triacetyl cellulose (TAC) films and cycloolefin polymer (COP) films have been the mainstream so far, but due to the trend toward cost reduction, the use rate of hard coat films using a relatively inexpensive polymethyl methacrylate substrate having low moisture permeability and high dimensional stability as a support substrate has been increasing.
While antiglare hard coat is used for a polarizing plate, antistatic property is further required to be provided in accordance with recent increase in the use of polymethyl methacrylate substrates. However, since the particle aggregation process and the antistatic property development process are mixed during the drying of the coating film of the hard coating composition, it is very difficult to achieve both the low haze and the antistatic property required for the development of the antiglare property.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2004-143303
Patent document 2: japanese laid-open patent publication No. 2004-123924
Disclosure of Invention
Problems to be solved by the invention
An object to be solved by the present invention is to provide an active energy ray-curable composition capable of forming a hard coat layer having excellent anti-glare properties and antistatic properties, and a film using the same.
Means for solving the problems
The invention provides an active energy ray-curable composition and a film using the same, wherein the active energy ray-curable composition contains an active energy ray-curable compound (A) and an antistatic agent (B), and the antistatic agent (B) has a cation portion represented by the following formula (1).
[ solution 1]
(in the formula (1), X represents a phosphorus atom or a nitrogen atom, R1～R4Each independently represents an alkyl group or an alkenyl group having 1 to 20 carbon atoms, and the total number of carbon atoms is 10 or more. )
Effects of the invention
The active energy ray-curable composition of the present invention can form a hard coat layer excellent in coating stability, appearance of a coating film, anti-glare properties, and antistatic properties on various substrates including a polymethyl methacrylate substrate.
Therefore, a film having a hard coat layer comprising a cured coating film of the active energy ray-curable composition of the present invention can be suitably used as an optical film used in a Flat Panel Display (FPD) such as a Liquid Crystal Display (LCD), an organic EL display (OLED), and a Plasma Display (PDP).
Detailed Description
The active energy ray-curable composition of the present invention contains an active energy ray-curable compound (a) and an antistatic agent (B) as essential components.
Examples of the active energy ray-curable compound (a) include urethane (meth) acrylate (a1), epoxy (meth) acrylate (a2), polyfunctional (meth) acrylates other than the urethane (meth) acrylate (a1) and the epoxy (meth) acrylate (a2) (hereinafter, simply referred to as "other polyfunctional (meth) acrylates (A3)"), polyester (meth) acrylates, polyether (meth) acrylates, and styrene. These active energy ray-curable compounds (a) may be used alone, or 2 or more of them may be used in combination. Of these, 1 or more compounds selected from the group consisting of urethane (meth) acrylate (a1), epoxy (meth) acrylate (a2), and other polyfunctional (meth) acrylate (A3) are preferably used from the viewpoint of obtaining still more excellent hard coatability.
In the present invention, "(meth) acrylate" means one or both of acrylate and methacrylate, "(meth) acryloyl group" means one or both of acryloyl group and methacryloyl group, and "(meth) acrylic acid" means one or both of acrylic acid and methacrylic acid.
The urethane (meth) acrylate (a1) is used for the purpose of adjusting scratch resistance and bendability, and includes, for example: a reactant (A1X) of polyisocyanate (A1-1) and (meth) acrylate having a hydroxyl group (A1-2); the reactant (A1Y) of the polyisocyanate (A1-1), the hydroxyl group-containing (meth) acrylate (A1-2) and the polyol (A1-3) may be a urethane (meth) acrylate having 1 or more (meth) acryloyl groups, preferably 2 to 6 (meth) acryloyl groups.
As the polyisocyanate (a1-1), for example, there can be used: aliphatic polyisocyanates such as hexamethylene diisocyanate, lysine diisocyanate, and lysine triisocyanate; alicyclic polyisocyanates such as norbornane diisocyanate, isophorone diisocyanate, methylene bis (4-cyclohexyl isocyanate), 1, 3-bis (isocyanatomethyl) cyclohexane, 2-methyl-1, 3-diisocyanatocyclohexane, and 2-methyl-1, 5-diisocyanatocyclohexane; and aromatic polyisocyanates such as tolylene diisocyanate, xylylene diisocyanate, and diphenylmethane diisocyanate. These polyisocyanates may be used alone, or 2 or more of them may be used in combination.
The polyisocyanate (a1-1) is preferably an aliphatic polyisocyanate and/or an alicyclic polyisocyanate, more preferably 1 or more polyisocyanates selected from the group consisting of hexamethylene diisocyanate, isophorone diisocyanate, and dicyclohexylmethane diisocyanate, and even more preferably hexamethylene diisocyanate and/or isophorone diisocyanate, from the viewpoint of reducing the coloration of the cured coating film of the active energy ray-curable composition.
The (meth) acrylate (a1-2) having a hydroxyl group and a (meth) acryloyl group includes, for example: mono (meth) acrylates of glycols such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 1, 5-pentanediol mono (meth) acrylate, 1, 6-hexanediol mono (meth) acrylate, neopentyl glycol mono (meth) acrylate, hydroxypivalic acid neopentyl glycol mono (meth) acrylate, and the like; mono-or di (meth) acrylates of 3-membered alcohols such as trimethylolpropane di (meth) acrylate, Ethylene Oxide (EO) -modified trimethylolpropane (meth) acrylate, Propylene Oxide (PO) -modified trimethylolpropane di (meth) acrylate, glycerol di (meth) acrylate and bis (2- (meth) acryloyloxyethyl) hydroxyethyl isocyanurate, or mono-and di (meth) acrylates having hydroxyl groups obtained by modifying a part of the alcoholic hydroxyl groups with e-caprolactone; a compound having 1-functional hydroxyl group and 3 or more functional (meth) acryloyl groups such as pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, ditrimethylolpropane tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, or a polyfunctional (meth) acrylate having hydroxyl groups, which is obtained by modifying the compound with e-caprolactone; (meth) acrylates having an oxyalkylene chain such as dipropylene glycol mono (meth) acrylate, diethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, and polyethylene glycol mono (meth) acrylate; (meth) acrylates having an oxyalkylene chain with a block structure such as polyethylene glycol-polypropylene glycol mono (meth) acrylate and polyoxybutylene-polyoxypropylene mono (meth) acrylate; and (meth) acrylates having an oxyalkylene chain of a random structure such as poly (ethylene glycol-tetramethylene glycol) mono (meth) acrylate and poly (propylene glycol-tetramethylene glycol) mono (meth) acrylate. These (meth) acrylic acid esters (a1-2) may be used alone or in combination of 2 or more. Of these, when the type (A1X) in which the polyol (A1-3) is not used is used as the urethane (meth) acrylate (a2), it is preferable to use 1 or more compounds selected from the group consisting of pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, and tripentaerythritol hepta (meth) acrylate from the viewpoint of obtaining still more excellent scratch resistance. When the type (A1Y) in which the polyol (A1-3) is used as the urethane (meth) acrylate (a2), 2-hydroxyethyl (meth) acrylate is preferably used from the viewpoint of obtaining further excellent flexibility.
As the above polyol (a1-3), for example: polyether polyols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol and the like; polyester polyols, polycarbonate polyols, and the like. These polyols may be used alone, or 2 or more kinds may be used in combination. Among these, polyether polyols are preferably used, and polytetramethylene glycol is more preferred, from the viewpoint of obtaining still more excellent bendability.
The reaction of the polyisocyanate (a1-1) with the (meth) acrylate (a1-2) and the reaction of the polyisocyanate (a1-1) with the (meth) acrylate (a1-2) with the polyol (a1-3) can be carried out by a urethanization reaction in a conventional manner. In addition, a urethane-forming catalyst may be used as necessary when the urethane-forming reaction is carried out. As the aforementioned urethane-forming catalyst, for example, there can be used: amine compounds such as pyridine, pyrrole, triethylamine, diethylamine and dibutylamine; phosphorus compounds such as triphenylphosphine and triethylphosphine; and organic tin compounds such as dibutyltin dilaurate, octyltin trilaurate, octyltin diacetate, dibutyltin diacetate, and tin octylate, and organic zinc compounds such as zinc octylate.
The number average molecular weight of the urethane (meth) acrylate in the case where the type (A1Y) of the polyol (A1-3) is used as the urethane (meth) acrylate (A2) is preferably in the range of 800-6,000, more preferably in the range of 1,000 to 4,000, from the viewpoint of obtaining more excellent bendability and scratch resistance. The number average molecular weight of the urethane (meth) acrylate is a value measured by a Gel Permeation Chromatography (GPC) method (eluent: tetrahydrofuran, polystyrene conversion).
When the urethane (meth) acrylate (A1) is used in combination with the urethane (1X) and the urethane (meth) acrylate (A1Y), the mass ratio [ (A1X)/(A1Y) ] is preferably in the range of 10/90 to 90/10, and more preferably in the range of 30/70 to 70/30, from the viewpoint of obtaining further excellent bendability and scratch resistance.
The epoxy (meth) acrylate (a2) is used for the purpose of improving antistatic properties and anti-glare properties, and for example, an addition reaction product of an unsaturated monocarboxylic acid and an epoxy compound can be used.
Examples of the unsaturated monocarboxylic acid include (meth) acrylic acid, crotonic acid, and cinnamic acid. These compounds may be used alone, or 2 or more of them may be used in combination. Among these, (meth) acrylic acid is preferably used from the viewpoint of scratch resistance and antistatic properties.
As the epoxy compound, for example, there can be used: epoxy compounds having a bisphenol a skeleton such as bisphenol a diglycidyl ether, hydrogenated bisphenol a diglycidyl ether, and brominated bisphenol a diglycidyl ether; epoxy compounds having a bisphenol F skeleton such as bisphenol F diglycidyl ether; an epoxy compound having a hydrogenated phthalic acid skeleton; and compounds having an epoxy group and a (meth) acryloyl group such as glycidyl (meth) acrylate, 4-hydroxybutyl acrylate glycidyl ether, and 3, 4-epoxycyclohexylmethyl (meth) acrylate. These compounds may be used alone, or 2 or more of them may be used in combination, or their polymers may be used. Among these, from the viewpoint of scratch resistance and antistatic properties, it is preferable to use an epoxy group and a (meth) acrylic compound, and it is more preferable to use a polymer of glycidyl (meth) acrylate.
When a polymer of the epoxy compound is used as a raw material of the epoxy (meth) acrylate (a2), a solvent may be used in combination from the viewpoint of viscosity adjustment. Examples of the solvent include methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, and butyl acetate. These solvents may be used alone, or 2 or more of them may be used in combination. The content of the solvent is preferably 50 to 150 parts by mass based on 100 parts by mass of the epoxy (meth) acrylate (a 2).
When a polymer of the epoxy compound is used as a raw material of the epoxy (meth) acrylate (a2), the viscosity of the epoxy (meth) acrylate (a2) containing a solvent is preferably in the range of 100 to 3,000mPa · s, and more preferably in the range of 150 to 2,000mPa · s, from the viewpoint of further improving the coating stability when forming a hard coat layer. The viscosity is a value measured by using a B-type viscometer.
The other polyfunctional (meth) acrylate (A3) is used for obtaining a hard coat property, and means a compound having preferably 2 to 8 (meth) acryloyl groups, more preferably 3 to 6 (meth) acryloyl groups in 1 molecule other than the (a1) and (a 2). As the aforementioned other polyfunctional (meth) acrylate (a3), for example, there can be used: di (meth) acrylates of dihydric alcohols such as 1, 4-butanediol di (meth) acrylate, 3-methyl-1, 5-pentanediol di (meth) acrylate, 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, tricyclodecane dimethanol 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; polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, di (meth) acrylate of tris (2-hydroxyethyl) isocyanurate, di (meth) acrylate of diol obtained by adding 4 or more moles of ethylene oxide or propylene oxide to 1 mole of neopentyl glycol; di (meth) acrylate of diol obtained by adding 2 moles of ethylene oxide or propylene oxide to 1 mole of bisphenol a; trimethylolpropane tri (meth) acrylate, ethylene oxide-modified trimethylolpropane tri (meth) acrylate, propylene oxide-modified trimethylolpropane tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tripentaerythritol octa (meth) acrylate, and the like. These compounds may be used alone, or 2 or more of them may be used in combination.
Of the other polyfunctional (meth) acrylates (a3), 1 or more compounds selected from the group consisting of tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, pentaerythritol tetra (meth) acrylate, and pentaerythritol tri (meth) acrylate are more preferably used from the viewpoint of obtaining still more excellent scratch resistance, and pentaerythritol tetra (meth) acrylate and pentaerythritol tri (meth) acrylate are more preferably used.
From the viewpoint of obtaining further excellent antistatic properties, antiglare properties, and scratch resistance, the active energy ray-curable compound (a) is preferably a combination of a urethane (meth) acrylate (a1) and an epoxy (meth) acrylate (a2) with another polyfunctional (meth) acrylate (A3), or a combination of an epoxy (meth) acrylate (a2) with another polyfunctional (meth) acrylate (A3).
When all of (a1) to (A3) are used as the active energy ray-curable compound (a), the amount of the urethane (meth) acrylate (a1) used is preferably in the range of 1 to 50 mass%, more preferably 5 to 30 mass% in the active energy ray-curable compound (a) from the viewpoint of obtaining more excellent scratch resistance, antistatic properties and antiglare properties. The amount of the epoxy (meth) acrylate (a2) used is preferably within a range of 10 to 80 mass%, more preferably within a range of 20 to 60 mass% in the active energy ray-curable compound (a), from the viewpoint of obtaining further excellent scratch resistance, antistatic properties and anti-glare properties.
When a combination of epoxy (meth) acrylate (a2) and another polyfunctional (meth) acrylate (A3) is used as the active energy ray-curable compound (a), the mass ratio [ (a2)/(A3) ] of the polyfunctional (meth) acrylate (a1) to the epoxy (meth) acrylate (A3) is preferably in the range of 20/80 to 90/10, and more preferably in the range of 40/60 to 80/20, from the viewpoint of obtaining further excellent scratch resistance and antistatic properties.
As the active energy ray-curable compound (a), polyester (meth) acrylate, polyether (meth) acrylate, styrene, or the like may be used as needed, in addition to the above (a1) to (A3). These compounds may be used alone, or 2 or more of them may be used in combination. The total mass of the active energy ray-curable compounds (a) of (a1) to (A3) is preferably 50 mass% or more, more preferably 80 mass% or more, and still more preferably 90 mass% or more.
In order to achieve both excellent anti-glare properties and antistatic properties, the antistatic properties (B) must be an ionic liquid having a cation portion represented by the following formula (1).
[ solution 2]
(in the formula (1), X represents a phosphorus atom or a nitrogen atom, R1～R4Each independently represents an alkyl group or an alkenyl group having 1 to 20 carbon atoms, and the total number of carbon atoms is 10 or more. )
It is presumed that the antistatic agent (B) has a long-chain hydrocarbon in the cation portion, and therefore has a larger steric structure and higher hydrophobicity than conventionally used antistatic agents, and thus can achieve both excellent antiglare properties and antistatic properties.
As the antistatic agent (B), for example, there can be used: x in the formula (1) is a phosphorus atom or a nitrogen atom, R1～R4An ionic liquid (B1) which is independently an alkyl group or an alkenyl group having 1 to 20 carbon atoms and has a total of 10 or more and less than 30 carbon atoms; x in the formula (1) is a phosphorus atom or a nitrogen atom, R1～R4And an ionic liquid (B2) which is independently an alkyl group or an alkenyl group having 3 to 20 carbon atoms and has a total of 30 or more carbon atoms.
From the viewpoint of obtaining further excellent antiglare properties and antistatic properties, it is preferable to use R in the formula (1) as the ionic liquid (B1)1～R4Each independently represents an alkyl group having preferably 1 to 16 carbon atoms, more preferably 1 to 14 carbon atoms, and the total number of carbon atoms is preferably in the range of 15 to 28, more preferably in the range of 20 to 26.
From the viewpoint of obtaining further excellent antiglare properties and antistatic properties, the ionic liquid (B2) preferably used is: the foregoing formula (1)Wherein X preferably represents a phosphorus atom, R1～R4Each independently represents an alkyl group having preferably 4 to 18, more preferably 5 to 16 carbon atoms, and the total number of carbon atoms is preferably in the range of 30 to 40, more preferably 31 to 36.
As the anion portion of the antistatic agent (B), Br, for example, can be used-、Cl-、I-、BF4 -、PF6 -、FeCl4 -、AlCl4 -、Al2Cl7 -、NO3 -、ClO4 -、HSO4 -、CH3SO4 -、CH3SO3 -、CF3SO3 -、C6H4CH3SO3 -、C4F7SO3 -、CH3CH2OSO3 -、CH3COO-、CF3COO-、C3F7COO-、(NC)2N-、(CF3SO2)2N-、(C2F5SO2)2N-、(CF3SO2)(CF3CO)N-、Tf2N-、SCN-、(CF3SO2)3C-、AsF6 -、SbF6 -、NbF6 -、TaF6 -、C(CN)3 -And the like.
The content of the antistatic agent (B) is preferably 0.01 to 20% by mass, more preferably 0.05 to 5% by mass in the active energy ray-curable composition, from the viewpoint of obtaining further excellent antiglare properties and antistatic properties.
The active energy ray-curable composition of the present invention preferably contains a solvent (C) for improving coatability.
As the solvent (C), for example, there can be used: methanol, ethanol, propanol, butanol, diacetone alcohol, dimethyl carbitol, methyl acetate, ethyl acetate, methyl ethyl ketone, methyl isobutyl ketone, acetylacetone, propylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether, and the like. These solvents may be used alone, or 2 or more of them may be used in combination. Among these, ethanol is preferably used from the viewpoint of obtaining further excellent antistatic properties.
The amount of the solvent (C) used is preferably in the range of 40 to 80% by mass in the active energy ray-curable composition from the viewpoint of coating properties and the like.
The active energy ray-curable composition of the present invention can form a cured coating film by applying the composition to a substrate and then irradiating the substrate with an active energy ray. The active energy ray is an ionizing radiation such as ultraviolet ray, electron ray, alpha ray, beta ray, or gamma ray. When a cured coating film is formed by irradiation with ultraviolet rays as an active energy ray, it is preferable to add a photopolymerization initiator (D) to the active energy ray-curable composition of the present invention to improve curability. Further, if necessary, a photosensitizer (E) may be further added to improve curability. On the other hand, when ionizing radiation such as electron beam, α -ray, β -ray, γ -ray or the like is used, since curing is rapidly performed without using the photopolymerization initiator (D) or the photosensitizer (E), it is not necessary to add the photopolymerization initiator (D) or the photosensitizer (E) in particular.
As the photopolymerization initiator (D), for example, there can be used: diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, oligo { 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl ] propanone }, benzildimethylketal, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, acetophenone compounds such as 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2-morpholino (4-methylthiophenyl) propan-1-one, and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone; benzoin-based compounds such as benzoin, benzoin methyl ether, benzoin isopropyl ether and the like; acylphosphine oxide-based compounds such as 2,4, 6-trimethylbenzoin diphenylphosphine oxide and bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide; benzil-based compounds such as benzil (dibenzoyl), methylphenylglyoxylic acid ester, oxyphenylacetic acid 2- (2-hydroxyethoxy) ethyl ester, oxyphenylacetic acid 2- (2-oxo-2-phenylacetoxyethoxy) ethyl ester and the like; benzophenone-based compounds such as benzophenone, methyl o-benzoylbenzoate-4-phenylbenzophenone, 4,4 ' -dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4 ' -methyl-diphenyl sulfide, acrylated benzophenone, 3 ', 4,4 ' -tetrakis (t-butylperoxycarbonyl) benzophenone, 3 ' -dimethyl-4-methoxybenzophenone, 2,4, 6-trimethylbenzophenone, and 4-methylbenzophenone; thioxanthone compounds such as 2-isopropylthioxanthone, 2, 4-dimethylthioxanthone, 2, 4-diethylthioxanthone and 2, 4-dichlorothioxanthone; aminobenzophenone-based compounds such as michelson and 4, 4' -diethylaminobenzophenone; 10-butyl-2-chloroacridone, 2-ethylanthraquinone, 9, 10-phenanthrenequinone, camphorquinone, 1- [4- (4-benzoylphenylthio) phenyl ] -2-methyl-2- (4-methylphenylsulfonyl) propan-1-one, and the like. These photopolymerization initiators (D) may be used alone, or 2 or more of them may be used in combination.
Examples of the photosensitizer (E) include tertiary amine compounds such as diethanolamine, N-methyldiethanolamine, and tributylamine, urea compounds such as o-tolylthiourea, and sulfur compounds such as sodium diethyldithiophosphate and s-benzylisothiouronium-p-toluenesulfonate.
The amounts of the photopolymerization initiator (D) and the photosensitizer (E) used are preferably in the range of 0.05 to 20 parts by mass, and more preferably in the range of 0.5 to 10 parts by mass, respectively, per 100 parts by mass of the active energy ray-curable compound (a).
The active energy ray-curable composition of the present invention contains the active energy ray-curable compound (a) and the antistatic agent (B) as essential components, but may contain other additives as necessary.
Examples of the other additives include additives such as a polymerization inhibitor, a surface conditioner, an antistatic agent other than the above (B), an antifoaming agent, a viscosity conditioner, a light stabilizer, a weather stabilizer, a heat stabilizer, an ultraviolet absorber, an antioxidant, a leveling agent, an organic pigment, an inorganic pigment, a pigment dispersant, and fine particles; inorganic fillers such as silica, alumina, titania, zirconia, and antimony pentoxide. These additives may be used alone, or 2 or more of them may be used in combination.
As the fine particles, inorganic fine particles and organic fine particles can be used, and transparent fine particles are preferably used. As the organic fine particles, plastic polymer beads can be used, and for example: styrene beads (refractive index 1.60), melamine beads (refractive index 1.57), acrylic beads (refractive index 1.49 to 1.535), acrylic-styrene beads (refractive index 1.54 to 1.58), benzoguanamine-formaldehyde beads, polycarbonate beads, polyethylene beads, and the like. Examples of the inorganic fine particles include spherical silica and amorphous silica. Among these, organic fine particles are preferably used, and from the viewpoint of having high cohesive force and good compatibility with the antistatic agent (B), and further excellent antistatic property and antiglare property, acrylic beads and/or acrylic-styrene beads are preferably used, and acrylic beads are more preferably used.
The particle diameter of the fine particles is preferably in the range of 0.5 to 5.0. mu.m, more preferably in the range of 0.8 to 3.5. mu.m, and still more preferably in the range of 1.0 to 2.5. mu.m, from the viewpoint of having a high cohesive force and further excellent antistatic property and antiglare property. The particle size of the organic fine particles is a particle size at which the cumulative amount of the particle size distribution in the particle size distribution measurement result in the cumulative particle amount curve is 50%.
The amount of the fine particles used is preferably in the range of 0.5 to 15% by mass, more preferably 1 to 7% by mass, in the active energy ray-curable composition, from the viewpoint of obtaining further excellent antistatic properties and antiglare properties.
The films of the invention were obtained as follows: the active energy ray-curable composition of the present invention is applied to at least 1 surface of a film substrate, and then irradiated with active energy rays to form a cured coating film.
As the material of the film base used in the film of the present invention, a resin having high transparency is preferable, and examples thereof include: polyester resins such as polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate; polyolefin resins such as polypropylene, polyethylene and polymethyl 1-pentene; cellulose resins such as cellulose acetate (e.g., diacetylcellulose and triacetylcellulose), cellulose acetate propionate, cellulose acetate butyrate, cellulose acetate propionate butyrate, cellulose acetate phthalate, and nitrocellulose; acrylic resins such as polymethyl methacrylate; vinyl chloride resins such as polyvinyl chloride and polyvinylidene chloride; polyvinyl alcohol; ethylene-vinyl acetate copolymers; polystyrene; a polyamide; a polycarbonate; polysulfones; polyether sulfone; polyether ether ketone; polyimide resins such as polyimide and polyetherimide; norbornene-based resins (for example, "ZEONOR" manufactured by Zeon corporation, japan), modified norbornene-based resins (for example, "ARTON" manufactured by JSR corporation), cyclic olefin copolymers (for example, "APEL" manufactured by mitsui chemical corporation), and the like. Further, a material obtained by bonding 2 or more substrates containing these resins may be used.
In the present invention, by using the active energy ray-curable composition, a hard coat layer having excellent antiglare properties and antistatic properties can be formed even when polymethyl methacrylate is used as the film base material.
The polymethyl methacrylate substrate (hereinafter, abbreviated as "PMMA") is a substrate formed of a polymer containing polymethyl methacrylate as a main component (preferably 100 mass%), and for example, "technoloys 014G", "technoloys 001G", "technoloys 000" manufactured by sumitomo chemical corporation is available; "ACRYPLEN HBS 006", "ACRYPLEN HBXN 47", "ACRYPLEN HBS 010", manufactured by Mitsubishi chemical corporation; commercially available products such as "Panlite Film PC-2151" manufactured by Dihimurium Kabushiki Kaisha.
The film base material may be in the form of a film or a sheet, and has a thickness of, for example, 20 to 500 μm. When a film-like base film is used, the thickness is preferably in the range of 20 to 200. mu.m, more preferably in the range of 30 to 150. mu.m, and still more preferably in the range of 40 to 130. mu.m. By setting the thickness of the film base material to this range, even when a hard coat layer is provided on one surface of the film by the active energy ray-curable composition of the present invention, curling can be easily suppressed.
Examples of the method for applying the active energy ray-curable composition of the present invention to the film substrate include die coating, microgravure coating, gravure coating, roll coating, comma coating, air knife coating, kiss coating, spray coating, dip coating, spin coating, brush coating, full-size coating using a screen, wire bar coating, and flow coating (flow coat).
After the active energy ray-curable composition is applied to a substrate film, it is preferable to heat or dry the composition at room temperature before the active energy ray irradiation in order to volatilize the solvent (C). The conditions for the heat drying include, for example, heat drying at a temperature of 50 to 100 ℃ for 0.5 to 10 minutes.
The active energy ray for curing the active energy ray-curable composition of the present invention is an ionizing radiation such as an ultraviolet ray, an electron ray, an α ray, a β ray, or a γ ray as described above. When ultraviolet rays are used as the active energy rays, examples of the means for irradiating the ultraviolet rays include a low-pressure mercury lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a metal halide lamp, an electrodeless lamp (fusion lamp), a chemical lamp, a black light lamp, a mercury-xenon lamp, a short arc lamp, a helium-cadmium laser, an argon laser, sunlight, and an LED lamp.
The thickness of the cured coating film when the cured coating film of the active energy ray-curable composition of the present invention is formed on the film base is preferably in the range of 1 to 30 μm, more preferably in the range of 3 to 15 μm, and even more preferably in the range of 4 to 10 μm, from the viewpoint of making the hardness of the cured coating film sufficient and suppressing the curling of the film due to curing shrinkage of the coating film.
As described above, the active energy ray-curable composition of the present invention can form a hard coat layer excellent in coating stability, appearance of a coating film, anti-glare property, and antistatic property on various substrates including a polymethyl methacrylate substrate.
Therefore, a film having a hard coat layer comprising a cured coating film of the active energy ray-curable composition of the present invention can be suitably used as an optical film used in a Flat Panel Display (FPD) such as a Liquid Crystal Display (LCD), an organic EL display (OLED), a Plasma Display (PDP), and the like.
Examples
The present invention will be described more specifically with reference to examples.
[ example 1]
40 parts by mass of a mixture of pentaerythritol tetraacrylate (hereinafter abbreviated as "PETTA") and pentaerythritol triacrylate (hereinafter abbreviated as "PETA"), 20 parts by mass of urethane acrylate (1) (a reaction product of dipentaerythritol pentaacrylate and isophorone diisocyanate, a solid content of 100% by mass, hereinafter abbreviated as "UA (l)"), a reaction product of urethane acrylate (2) (polytetramethylene glycol, isophorone diisocyanate and 2-hydroxyethyl acrylate, a number average molecular weight, 1,600, a solid content of 100% by mass, hereinafter abbreviated as "UA (2)"), epoxy acrylate (1) (a methyl isobutyl ketone solution of a reaction product of polyglycidyl methacrylate and acrylic acid, a solid content of 50% by mass, a viscosity of 1,000 mPas, hereinafter abbreviated as "EA (1)"), 40 parts by mass, 144 parts by mass of ethanol and 5 parts by mass of 1-hydroxycyclohexyl phenyl ketone, and mixing with an antistatic agent (B) (in the formula (1), X represents a phosphorus atom, and R represents1～R3Represents an alkyl group having 6 carbon atoms, R4A C14 alkyl group, a total of 32 carbon atoms, and an anion portion of (CF)3SO2)2N-. )3 parts by mass of organic beads (crosslinked acrylic fine particles manufactured by water-accumulative chemical Co., Ltd., particle diameter of 1.5 μm, refractive index of 1.495)3.5 parts by mass, and the mixture was stirred with a dispersion mixer for 30 minutes to prepare an active energy ray-curable composition.
Examples 2 to 16 and comparative examples 1 to 6
An active energy ray-curable composition was prepared in the same manner as in example 1, except that the kinds and the amounts of the active energy ray-curable compound (a) and the antistatic agent (B) used were changed as shown in tables 1 to 4.
[ preparation of sample for evaluation ]
The active energy ray-curable compositions obtained in examples and comparative examples were coated on a polymethyl methacrylate film having a thickness of 60 μm so as to have a film thickness of 5 μm using a bar coater, dried at 60 ℃ for 1 minute, and then irradiated with an ultraviolet irradiation apparatus (high-pressure mercury lamp, manufactured by EYEGRAPHICS K.) at an irradiation light amount of 75mJ/m under a nitrogen atmosphere2The irradiation was performed 2 times to obtain a polymethyl methacrylate film having a cured coating film as a sample for evaluation.
[ method for evaluating antiglare Property ]
(1) Evaluation of haze
The haze of the obtained sample for evaluation was measured using a haze meter (NDH 4000, manufactured by japan electrical appliances) in accordance with jis k7136: 2000.
(2) Evaluation of Transmission clarity
The obtained evaluation sample was measured for optical comb width using an image clarity measuring instrument ("ICM-IT" manufactured by Suga test machine) according to jis k7374: 2007: the measurement was carried out at 4 points of 0.125, 0.5, 1.0, 2.0 mm. The total value of the measured 4 points was used for evaluation.
From the above, the antiglare property was judged to be excellent when the haze was 4 or less and the transmission clarity was 375% or less.
[ method for evaluating antistatic Property ]
The surface of the cured coating film of the obtained evaluation sample was measured by using a high resistivity meter ("Hiresta-UP MCP-HT 450" manufactured by mitsubishi chemical Analytech) according to JIS test method C2139:2008, to apply a voltage: 500V, measurement time: the surface resistance value was measured for 10 seconds. The surface resistance value (omega/□) is set to 10-13When the order of magnitude is less than or equal to the above range, the antistatic property is judged to be excellent.
[ Table 1]
[ Table 2]
[ Table 3]
[ Table 4]
Abbreviations in table 4 are as follows:
"pyridine-based antistatic agent": 1-butyl-4-methylpyridinium bis (trifluoromethanesulfonyl) imide, manufactured by Tokyo Kasei Kogyo K.K.) "
"imidazole-based antistatic agent": 1-Ethyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide, manufactured by Tokyo Kasei Kogyo K.K.) "
The evaluation results shown in tables 1 to 4 show that: the cured coating films of the active energy ray-curable compositions of examples 1 to 16 of the present invention have excellent antistatic properties and antiglare properties. Further, the more the antistatic agent (B) is added, the less the transmission clarity is reduced, the antiglare property is obtained, and the antistatic property is improved.
In comparative examples 1 to 2 shown in Table 4, the antistatic agent (B) was not contained, and the transmittance was improved and the antistatic property was also poor. In comparative examples 3 to 5, other antistatic agents were used instead of the antistatic agent (B) used in the present application, but the antistatic property was poor.
Claims (9)
1. An active energy ray-curable composition comprising an active energy ray-curable compound (A) and an antistatic agent (B),
the antistatic agent (B) has a cation part represented by the following formula (1),
[ solution 1]
In the formula (1), X represents a phosphorus atom or a nitrogen atom, R1～R4Each independently represents an alkyl group or an alkenyl group having 1 to 20 carbon atoms, and the total number of carbon atoms is 10 or more.
2. The active energy ray-curable composition according to claim 1, wherein the content of the antistatic agent (B) is in the range of 0.01 to 20% by mass.
3. The active energy ray-curable composition according to claim 1, wherein the active energy ray-curable compound (A) is at least 1 compound selected from the group consisting of urethane (meth) acrylate (A1), epoxy (meth) acrylate (A2), and another polyfunctional (meth) acrylate (A3).
4. The active energy ray-curable composition according to claim 1, wherein R in the formula (1)1～R4Each independently represents an alkyl group or an alkenyl group having 1 to 20 carbon atoms, and the total number of carbon atoms is 10 or more and less than 30.
5. The active energy ray-curable composition according to claim 1, wherein R in the formula (1)1～R4Each independently represents an alkyl group or an alkenyl group having 3 to 20 carbon atoms, and the total number of carbon atoms is 30 or more.
6. The active energy ray-curable composition according to claim 1, further comprising a solvent (C).
7. The active energy ray-curable composition according to claim 6, wherein the solvent (C) contains ethanol.
8. A cured product of the active energy ray-curable composition according to any one of claims 1 to 7.
9. A film comprising a cured coating film of the active energy ray-curable composition according to any one of claims 1 to 7.
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| JP2018-168794 | 2018-09-10 | ||
| PCT/JP2019/034546 WO2020054502A1 (en) | 2018-09-10 | 2019-09-03 | Actinic ray curable composition and film using same |
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| CN106459240A (en) * | 2014-06-27 | 2017-02-22 | Dic株式会社 | Active energy ray-curable composition and film using same |
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| JP3963447B2 (en) | 2002-10-03 | 2007-08-22 | 竹本油脂株式会社 | Antistatic agent for polyester film and antistatic method for polyester film |
| JP4229228B2 (en) | 2002-10-25 | 2009-02-25 | 日本合成化学工業株式会社 | Urethane (meth) acrylate compound and active energy ray-curable resin composition using the same |
| JP2015093419A (en) * | 2013-11-12 | 2015-05-18 | 日油株式会社 | Optical laminate |
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| JPH0195105A (en) * | 1987-10-06 | 1989-04-13 | Takemoto Oil & Fat Co Ltd | Photocurable resin composition |
| JP2010085931A (en) * | 2008-10-02 | 2010-04-15 | Dainippon Printing Co Ltd | Method for manufacturing hard coat film and method for manufacturing optical functional member |
| JP2011184490A (en) * | 2010-03-05 | 2011-09-22 | Toyo Ink Sc Holdings Co Ltd | Antistatic agent and use thereof |
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| WO2020054502A1 (en) | 2020-03-19 |
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| TW202030209A (en) | 2020-08-16 |
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