JP5773099B2 - 環状オレフィン樹脂フィルム - Google Patents
環状オレフィン樹脂フィルム Download PDFInfo
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- JP5773099B2 JP5773099B2 JP2015505435A JP2015505435A JP5773099B2 JP 5773099 B2 JP5773099 B2 JP 5773099B2 JP 2015505435 A JP2015505435 A JP 2015505435A JP 2015505435 A JP2015505435 A JP 2015505435A JP 5773099 B2 JP5773099 B2 JP 5773099B2
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- JP
- Japan
- Prior art keywords
- meth
- acrylate
- cyclic olefin
- olefin resin
- mass
- 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.)
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- 229920005672 polyolefin resin Polymers 0.000 title claims description 58
- 125000004122 cyclic group Chemical group 0.000 title claims description 57
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 139
- 239000000203 mixture Substances 0.000 claims description 79
- 239000011248 coating agent Substances 0.000 claims description 54
- 238000000576 coating method Methods 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000003999 initiator Substances 0.000 claims description 33
- -1 2- (2-oxo-2-phenylacetoxyethoxy) ethyl Chemical group 0.000 claims description 27
- 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 claims description 11
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 9
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- 239000011256 inorganic filler Substances 0.000 claims description 4
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 239000010408 film Substances 0.000 description 88
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 47
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 29
- 239000010419 fine particle Substances 0.000 description 20
- 239000000377 silicon dioxide Substances 0.000 description 20
- 239000005056 polyisocyanate Substances 0.000 description 17
- 229920001228 polyisocyanate Polymers 0.000 description 17
- 238000011156 evaluation Methods 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- WVSFUMAHZBOQGJ-UHFFFAOYSA-N phosphono 2-methylprop-2-eneperoxoate Chemical compound CC(=C)C(=O)OOP(O)(O)=O WVSFUMAHZBOQGJ-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process 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
- 239000012788 optical film Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 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 3
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 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
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 239000003504 photosensitizing agent Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 2
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 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
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 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
- 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
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000003851 corona treatment Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- ZMHZSHHZIKJFIR-UHFFFAOYSA-N octyltin Chemical compound CCCCCCCC[Sn] ZMHZSHHZIKJFIR-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical group O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- MLKGHQNOKUCQBA-UHFFFAOYSA-N (2-methyl-4-phenylphenyl)-phenylmethanone Chemical compound CC1=CC(C=2C=CC=CC=2)=CC=C1C(=O)C1=CC=CC=C1 MLKGHQNOKUCQBA-UHFFFAOYSA-N 0.000 description 1
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-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
- 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
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-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
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- VYMSWGOFSKMMCE-UHFFFAOYSA-N 10-butyl-2-chloroacridin-9-one Chemical compound ClC1=CC=C2N(CCCC)C3=CC=CC=C3C(=O)C2=C1 VYMSWGOFSKMMCE-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- CZZVAVMGKRNEAT-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)CO.OCC(C)(C)C(O)=O CZZVAVMGKRNEAT-UHFFFAOYSA-N 0.000 description 1
- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-UHFFFAOYSA-N 0.000 description 1
- LZHUBCULTHIFNO-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCO)C=C1 LZHUBCULTHIFNO-UHFFFAOYSA-N 0.000 description 1
- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- GNDOBZLRZOCGAS-JTQLQIEISA-N 2-isocyanatoethyl (2s)-2,6-diisocyanatohexanoate Chemical compound O=C=NCCCC[C@H](N=C=O)C(=O)OCCN=C=O GNDOBZLRZOCGAS-JTQLQIEISA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-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
- 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
-
- 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
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- 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
- C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
-
- 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
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
-
- 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
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
- C08J2323/04—Homopolymers or copolymers of ethene
- C08J2323/08—Copolymers of ethene
-
- 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
- C08J2423/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2423/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
- C08J2423/04—Homopolymers or copolymers of ethene
- C08J2423/08—Copolymers of ethene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Polymerisation Methods In General (AREA)
- Materials Engineering (AREA)
- Laminated Bodies (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Description
攪拌機、ガス導入管、冷却管及び温度計を備えたフラスコに、酢酸ブチル254質量部、イソホロンジイソシアネート222質量部、p−メトキシフェノール0.5質量部及びジブチル錫ジアセテート0.5質量部を仕込み、空気を吹き込みながら、70℃に昇温した後、ペンタエリスリトールトリアクリレート(以下、「PE3A」と略記する。)及びペンタエリスリトールテトラアクリレート(以下、「PE4A」と略記する。)の混合物(PE3A/PE4A=75/25(質量比))400質量部とイソシアヌル酸エチレンオキシド変性ジアクリレート497質量部を1時間かけて滴下した。滴下終了後、70℃で3時間反応させ、さらにイソシアネート基を示す2250cm−1の赤外線吸収スペクトルが消失するまで反応を行い、1分子中に6つのアクリロイル基を有するウレタンアクリレート(A2−1)を含む不揮発分80質量%溶液を得た。なお、この溶液には、不揮発分中にウレタンアクリレート(A2−1)の他にPE4Aが19.5質量%含まれる。
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。)及びジペンタエリスリトールペンタアクリレート(以下、「DPPA」と略記する。)の混合物(DPHA/DPPA=65/35(質量比))35質量部、ポリエステルアクリレート(4官能、分子量1,800)65質量部、シリカ微粒子(日産化学工業株式会社製「MEK−ST」、平均粒子径10〜20nm、オルガノシリカゾルの30質量%メチルエチルケトン分散液;以下、「シリカ微粒子分散液(1)」と略記する。)25質量部(シリカ微粒子として7.5質量部)、及び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(以下、「光重合開始剤(B1−1)」と略記する。)3質量部を均一に攪拌した後、メチルエチルケトンで希釈して、不揮発分25質量%の紫外線硬化性組成物(1)を調製した。
上記で得られた紫外線硬化性組成物(1)を、予めその表面を電気的処理(コロナ放電処理;出力100W、速度1.0m/分)した環状オレフィン樹脂フィルム(日本ゼオン株式会社製「ゼオノアフィルムZF16−100」、厚さ100μm)上に、ワイヤーバーを用いて塗布し、60℃で90秒間加熱後、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「MIDN−042−C1」、ランプ:120W/cm、高圧水銀灯)を用いて、照射光量0.3J/cm2で紫外線を照射して、厚さ4μmの硬化塗膜を有する評価用フィルムを得た。
上記で得られた評価用フィルムの硬化塗膜の表面について、クロックメーター形摩擦試験器(直径1.0cm円形摩擦子、スチールウール#0000、荷重300g、10往復)を用いて試験を行い、試験後の硬化塗膜表面を目視で観察し、下記の基準により耐擦傷性を評価した。
A:傷の数が9本以下である。
B:傷の数が10本以上である。
上記で得られた評価用フィルムに、フィルムの硬化被膜表面に1mm間隔で縦、横11本の切れ目を入れて100個のマス目を作製した。次いで、市販のセロハンテープをその表面に密着させた後、一気に剥がす操作を2回繰り返した。剥離せずに残ったマス目の数を数え、下記の基準により密着性を評価した。
A:残ったマス目の数が100個である。
B:残ったマス目の数が80個以上99個以下である。
C:残ったマス目の数が60個以上80個以下である。
D:残ったマス目の数が59個以下である。
紫外線硬化性組成物(1)塗布量を変更した以外は上記の評価用フィルムの作製と同様に行い、厚さ6μmの硬化塗膜を有する厚膜密着性評価用フィルムを得た。得られたフィルムについて、上記の密着性の評価と同様に行い、厚膜密着性を評価した。
上記で得られた評価用フィルムを50mm×80mmの大きさにカットし、外径8mmのロッドにフィルムを巻き付け、セロハンテープで固定した。次いで、ロッドを引き抜いた後、ロール状の評価用フィルムの色味を目視で観察し、下記の基準により塗膜着色を評価した。
A:無色である。
B:黄味の着色がある。
光重合開始剤(B1−1)の配合量を3質量部から6質量部に変更した以外は実施例1と同様に行い、紫外線硬化性組成物(2)を調製した。
光重合開始剤(B1−1)の配合量を3質量部から9質量部に変更した以外は実施例1と同様に行い、不揮発分25質量%の紫外線硬化性組成物(3)を調製した。
合成例1で得られた多官能ウレタンアクリレート(A2−1)(不揮発分80質量%)125質量部(多官能アクリレートとして100質量部)、シリカ微粒子分散液(1)25質量部(シリカ微粒子として7.5質量部)及び光重合開始剤(B1−1)3質量部を均一に攪拌した後、メチルエチルケトンで希釈して、不揮発分25質量%の紫外線硬化性組成物(4)を調製した。
光重合開始剤(B1−1)の配合量を3質量部から6質量部に変更した以外は実施例4と同様に行い、不揮発分25質量%の紫外線硬化性組成物(5)を調製した。
光重合開始剤(B1−1)の配合量を3質量部から9質量部に変更した以外は実施例4と同様に行い、不揮発分25質量%の紫外線硬化性組成物(6)を調製した。
合成例1で得られた多官能ウレタンアクリレート(A2−1)(不揮発分80質量%)125質量部(多官能アクリレートとして100質量部)、シリカ微粒子(日産化学工業株式会社製「MEK−ST40」、平均粒子径10〜20nm、オルガノシリカゾルの40質量%メチルエチルケトン分散液;以下、「シリカ微粒子分散液(2)」と略記する。)62.5質量部(シリカ微粒子として25質量部)、及び光重合開始剤(B1−1)6質量部を均一に攪拌した後、メチルエチルケトンで希釈して、不揮発分25質量%の紫外線硬化性組成物(7)を調製した。
多官能ウレタンアクリレート(A2−1)(不揮発分80質量%)123.75質量部(多官能アクリレートとして99質量部)、リン酸基を有するメタクリレート(MIWON社製「ミラマー SC1400」;以下、「リン酸メタクリレート(1)」と略記する。)1質量部、シリカ微粒子分散液(2)62.5質量部(シリカ微粒子として25質量部)、及び光重合開始剤(B1−1)6質量部を均一に攪拌した後、メチルエチルケトンで希釈して、不揮発分25質量%の紫外線硬化性組成物(8)を調製した。
多官能ウレタンアクリレート(A2−1)(不揮発分80質量%)118.75質量部(多官能アクリレートとして95質量部)、リン酸メタクリレート(1)5質量部、シリカ微粒子分散液(2)62.5質量部(シリカ微粒子として25質量部)、及び光重合開始剤(B1−1)6質量部を均一に攪拌した後、メチルエチルケトンで希釈して、不揮発分25質量%の紫外線硬化性組成物(9)を調製した。
多官能ウレタンアクリレート(A2−1)(不揮発分80質量%)113.75質量部(多官能アクリレートとして91質量部)、リン酸メタクリレート(1)9質量部、シリカ微粒子分散液(2)62.5質量部(シリカ微粒子として25質量部)、及び光重合開始剤(B1−1)6質量部を均一に攪拌した後、メチルエチルケトンで希釈して、不揮発分25質量%の紫外線硬化性組成物(10)を調製した。
シリカ微粒子分散液(2)を配合しなかった以外は実施例7と同様に行い、不揮発分25質量%の紫外線硬化性組成物(11)を調製した。
シリカ微粒子分散液(2)を配合しなかった以外は実施例9と同様に行い、不揮発分25質量%の紫外線硬化性組成物(12)を調製した。
実施例1で用いた光重合開始剤(B1−1)に代えて、4−(4−メチルフェニルチオ)ベンゾフェノン(以下、「光重合開始剤(R1)」と略記する。)を用いた以外は実施例1と同様に行い、紫外線硬化性組成物(R1)を調製した。
実施例1で用いた光重合開始剤(B1−1)3質量部に代えて、光重合開始剤(R1)9質量部を用いた以外は実施例1と同様に行い、紫外線硬化性組成物(R2)を調製した。
実施例1で用いた光重合開始剤(B1−1)3質量部に代えて、1−ヒドロキシシクロヘキシルフェニルケトン(以下、「光重合開始剤(R2)」と略記する。)6質量部を用いた以外は実施例1と同様に行い、紫外線硬化性組成物(R3)を調製した。
実施例1で用いた光重合開始剤(B1−1)3質量部に代えて、2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)−1−ブタノン(以下、「光重合開始剤(R3)」と略記する。)6質量部を用いた以外は実施例1と同様に行い、紫外線硬化性組成物(R4)を調製した。
実施例1で用いた光重合開始剤(B1−1)3質量部に代えて、2−メチル−1−(4−メチルチオフェニル)−2−モルホリノプロパン−1−オン(以下、「光重合開始剤(R4)」と略記する。)6質量部を用いた以外は実施例1と同様に行い、紫外線硬化性組成物(R5)を調製した。
実施例1で用いた光重合開始剤(B1−1)3質量部に代えて、2−ヒドロキシ−1−[4−(2−ヒドロキシエトキシ)−フェニル]−2−メチル−1−プロパン−1−オン(以下、「光重合開始剤(R5)」と略記する。)6質量部を用いた以外は実施例1と同様に行い、紫外線硬化性組成物(R6)を調製した。
実施例1で用いた光重合開始剤(B1−1)3質量部に代えて、ジフェニル(2,4,6−トリメチルベンゾイル)ホスフィンオキサイド(以下、「光重合開始剤(R6)」と略記する。)6質量部を用いた以外は実施例1と同様に行い、紫外線硬化性組成物(R7)を調製した。
実施例1で用いた光重合開始剤(B1−1)3質量部に代えて、2−ヒドロキシ−2−メチル−1−フェニル−1−プロパノン(以下、「光重合開始剤(R7)」と略記する。)6質量部を用いた以外は実施例1と同様に行い、紫外線硬化性組成物(R8)を調製した。
実施例1で用いた光重合開始剤(B1−1)3質量部に代えて、2−ヒロドキシ−1−{4−[4−(2−ヒドロキシ−2−メチル−プロピオニル)−ベンジル]フェニル}−2−メチル−1−プロパノン(以下、「光重合開始剤(R8)」と略記する。)6質量部を用いた以外は実施例1と同様に行い、紫外線硬化性組成物(R9)を調製した。
実施例1で用いた光重合開始剤(B1−1)3質量部に代えて、2,4−ジエチルチオキサントン(以下、「光重合開始剤(R9)」と略記する。)6質量部を用いた以外は実施例1と同様に行い、紫外線硬化性組成物(R10)を調製した。
Claims (7)
- 前記化合物(B1)が、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)エチルエステルである請求項1記載の環状オレフィン樹脂フィルム。
- 前記紫外線硬化性化合物(A)が、多官能(メタ)アクリレート(A1)を含むものである請求項1又は2記載の環状オレフィン樹脂フィルム。
- 前記多官能(メタ)アクリレート(A1)が、ジペンタエリスリトールヘキサ(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、ペンタエリスリトールテトラ(メタ)アクリレート及びペンタエリスリトールトリ(メタ)アクリレートからなる群から選ばれる1種以上のものである請求項3記載の環状オレフィン樹脂フィルム。
- 前記紫外線硬化性組成物が、さらにリン酸基を有する(メタ)アクリレート(A4)を含有する請求項1〜4のいずれか1項記載の環状オレフィン樹脂フィルム。
- 前記紫外線硬化性組成物が、さらに無機充填剤を含有する請求項1〜5のいずれか1項記載の環状オレフィン樹脂フィルム。
- 環状オレフィン樹脂フィルムの少なくとも1面が予め電気的処理を施されており、該処理面に前記紫外線硬化性組成物を塗工し、その後紫外線を照射して硬化塗膜とすることで得られる請求項1記載の環状オレフィン樹脂フィルム。
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