WO2016152871A1 - 光学フィルム - Google Patents
光学フィルム Download PDFInfo
- Publication number
- WO2016152871A1 WO2016152871A1 PCT/JP2016/059034 JP2016059034W WO2016152871A1 WO 2016152871 A1 WO2016152871 A1 WO 2016152871A1 JP 2016059034 W JP2016059034 W JP 2016059034W WO 2016152871 A1 WO2016152871 A1 WO 2016152871A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- block copolymer
- hydride
- optical film
- weight
- polymer
- Prior art date
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- 239000012788 optical film Substances 0.000 title claims abstract description 102
- 229920001400 block copolymer Polymers 0.000 claims abstract description 119
- -1 aromatic vinyl compound Chemical class 0.000 claims abstract description 114
- 229920000642 polymer Polymers 0.000 claims abstract description 106
- 150000004678 hydrides Chemical class 0.000 claims abstract description 84
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims abstract description 49
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 44
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 42
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229920001577 copolymer Polymers 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000010521 absorption reaction Methods 0.000 claims description 15
- 238000007334 copolymerization reaction Methods 0.000 claims description 6
- 239000010410 layer Substances 0.000 description 67
- 229920005989 resin Polymers 0.000 description 65
- 239000011347 resin Substances 0.000 description 65
- 238000000034 method Methods 0.000 description 52
- 238000005984 hydrogenation reaction Methods 0.000 description 49
- 238000006243 chemical reaction Methods 0.000 description 47
- 239000000178 monomer Substances 0.000 description 42
- 239000002952 polymeric resin Substances 0.000 description 35
- 229920003002 synthetic resin Polymers 0.000 description 35
- 239000010408 film Substances 0.000 description 32
- 238000004519 manufacturing process Methods 0.000 description 31
- 238000005452 bending Methods 0.000 description 27
- 125000005370 alkoxysilyl group Chemical group 0.000 description 25
- 238000006116 polymerization reaction Methods 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- 238000009826 distribution Methods 0.000 description 20
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 238000004817 gas chromatography Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- 230000000379 polymerizing effect Effects 0.000 description 10
- 238000001125 extrusion Methods 0.000 description 9
- 238000007142 ring opening reaction Methods 0.000 description 9
- 150000003440 styrenes Chemical class 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000004611 light stabiliser Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000008188 pellet Substances 0.000 description 7
- 150000002978 peroxides Chemical class 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000002834 transmittance Methods 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 150000001934 cyclohexanes Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002685 polymerization catalyst Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000010538 cationic polymerization reaction Methods 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- NOSXUFXBUISMPR-UHFFFAOYSA-N 1-tert-butylperoxyhexane Chemical compound CCCCCCOOC(C)(C)C NOSXUFXBUISMPR-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- YAQDPWONDFRAHF-UHFFFAOYSA-N 2-methyl-2-(2-methylpentan-2-ylperoxy)pentane Chemical compound CCCC(C)(C)OOC(C)(C)CCC YAQDPWONDFRAHF-UHFFFAOYSA-N 0.000 description 2
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002879 Lewis base Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-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
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 2
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000002506 iron compounds Chemical class 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 238000010550 living polymerization reaction Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
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- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
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- 239000007787 solid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 229920000428 triblock copolymer Polymers 0.000 description 2
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 2
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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- 239000004711 α-olefin Substances 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- JBVMSEMQJGGOFR-FNORWQNLSA-N (4e)-4-methylhexa-1,4-diene Chemical compound C\C=C(/C)CC=C JBVMSEMQJGGOFR-FNORWQNLSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
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- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- 229940106006 1-eicosene Drugs 0.000 description 1
- FIKTURVKRGQNQD-UHFFFAOYSA-N 1-eicosene Natural products CCCCCCCCCCCCCCCCCC=CC(O)=O FIKTURVKRGQNQD-UHFFFAOYSA-N 0.000 description 1
- OUSXYCTXXLYBGJ-UHFFFAOYSA-N 1-ethenyl-2,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C=C)C(C(C)C)=C1 OUSXYCTXXLYBGJ-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- JWVTWJNGILGLAT-UHFFFAOYSA-N 1-ethenyl-4-fluorobenzene Chemical compound FC1=CC=C(C=C)C=C1 JWVTWJNGILGLAT-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
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- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
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- B32B25/04—Layered products comprising a layer of natural or synthetic rubber comprising rubber as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B25/08—Layered products comprising a layer of natural or synthetic rubber comprising rubber as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B25/00—Layered products comprising a layer of natural or synthetic rubber
- B32B25/14—Layered products comprising a layer of natural or synthetic rubber comprising synthetic rubber copolymers
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- B32B25/00—Layered products comprising a layer of natural or synthetic rubber
- B32B25/16—Layered products comprising a layer of natural or synthetic rubber comprising polydienes homopolymers or poly-halodienes homopolymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
- B32B27/20—Layered products comprising a layer of synthetic resin characterised by the use of special additives using fillers, pigments, thixotroping agents
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Definitions
- the present invention relates to an optical film.
- a resin film is used as an optical film such as a retardation film, a polarizing plate protective film, and an optical compensation film.
- an optical film such as a retardation film, a polarizing plate protective film, and an optical compensation film.
- One of optical films made of such a resin is a film containing a norbornene-based polymer (see Patent Documents 1 and 2).
- the optical film may be bent during use depending on the application. Therefore, the optical film is required to have excellent bending resistance.
- a conventional film containing a norbornene-based polymer has excellent properties such as tensile elastic modulus and transparency, but has a tendency to be inferior in bending resistance.
- the present invention has been made in view of the above-described problems, and an object thereof is to provide an optical film containing a norbornene-based polymer and having excellent bending resistance.
- the present inventor has found that a first layer containing a hydride of an aromatic vinyl compound / conjugated diene compound block copolymer, a second layer containing a norbornene polymer, and an aromatic An optical film comprising a third layer containing a hydride of an aromatic vinyl compound / conjugated diene compound block copolymer in this order was found to have excellent bending resistance, and the present invention was completed. That is, the present invention is as follows.
- an optical film containing a norbornene polymer and having excellent bending resistance can be provided.
- the present invention will be described in detail with reference to embodiments and examples. However, the present invention is not limited to the following embodiments and exemplifications, and can be implemented with any modifications without departing from the scope of the claims of the present invention and the equivalents thereof.
- the “polarizing plate” includes not only a rigid member but also a flexible member such as a resin film, unless otherwise specified.
- optical film of the present invention is a multilayer film having a first layer, a second layer, and a third layer in this order.
- the first layer includes a hydride of an aromatic vinyl compound / conjugated diene compound block copolymer. Therefore, the first layer is usually a resin layer made of a resin containing a hydride of an aromatic vinyl compound / conjugated diene compound block copolymer.
- the resin containing the hydride of the aromatic vinyl compound / conjugated diene compound block copolymer may be referred to as “hydrogenated polymer resin” as appropriate.
- This hydrogenated polymer resin is usually a thermoplastic resin.
- the aromatic vinyl compound / conjugated diene compound block copolymer is a block copolymer obtained by block copolymerization of an aromatic vinyl compound, a conjugated diene compound, and optionally any monomer.
- the block copolymer may be modified with, for example, alkoxysilane, carboxylic acid, carboxylic anhydride, or the like.
- the aromatic vinyl compound examples include styrene, ⁇ -methylstyrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, 2,4-diisopropylstyrene, 2,4-dimethylstyrene, and 4-t-butyl.
- the aromatic vinyl compound preferably does not contain a polar group.
- styrene is particularly preferable from the viewpoint of industrial availability and impact resistance.
- a chain conjugated diene compound is preferable.
- the chain conjugated diene compound include 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, and the like. One of these may be used alone, or two or more of these may be used in combination at any ratio. Among them, those not containing a polar group are preferable in terms of hygroscopicity, 1,3-butadiene and isoprene are more preferable, and isoprene is particularly preferable.
- the copolymerization ratio of the aromatic vinyl compound / conjugated diene compound is preferably 50/50 or more, more preferably 55/45 or more, particularly preferably 60/40 or more, preferably 90/10 or less, more preferably 85. / 15 or less, particularly preferably 80/20 or less. Therefore, for example, in a styrene / isoprene block copolymer using styrene as the aromatic vinyl compound and isoprene as the conjugated diene compound, the copolymerization ratio of styrene / isoprene is preferably within the above range.
- the copolymerization ratio at least the lower limit of the above range, it is possible to suppress the fusion of the surface of the optical film, and to suppress blocking, and by making it below the upper limit, the bending resistance of the optical film is further improved. Can be improved.
- the block copolymer is a block copolymer of an aromatic vinyl compound and a conjugated diene compound
- the polymer block [A] containing an aromatic vinyl compound unit and a polymer block containing a conjugated diene compound unit are used.
- the aromatic vinyl compound unit refers to a structural unit having a structure formed by polymerizing an aromatic vinyl compound.
- the conjugated diene compound unit refers to a structural unit having a structure formed by polymerizing a conjugated diene compound.
- the polymer block [A] preferably contains an aromatic vinyl compound unit as a main component.
- the ratio of the aromatic vinyl compound unit in the polymer block [A] is preferably 90 to 100% by weight, more preferably 95 to 100% by weight, and 99 to 100% by weight. Particularly preferred.
- the polymer block [A] can contain an arbitrary structural unit in addition to the aromatic vinyl compound unit.
- the arbitrary structural unit include a conjugated diene compound unit and a structural unit having a structure formed by polymerizing a vinyl compound other than an aromatic vinyl compound.
- vinyl compounds other than aromatic vinyl compounds include: chain vinyl compounds; cyclic vinyl compounds; vinyl compounds having a nitrile group, alkoxycarbonyl group, hydroxycarbonyl group, or halogen group; unsaturated cyclic acid anhydrides; Examples thereof include saturated imide compounds.
- chain olefins such as 4,6-dimethyl-1-heptene
- cyclic olefins such as vinylcyclohexane
- the content of any structural unit in the polymer block [A] is preferably 10% by weight or less, more preferably 5% by weight or less, and particularly preferably 1% by weight or less.
- the number of polymer blocks [A] in one molecule of the block copolymer is preferably 2 or more, preferably 5 or less, more preferably 4 or less, and particularly preferably 3 or less.
- the plurality of polymer blocks [A] in one molecule may be the same as or different from each other.
- the weight average molecular weight of the polymer block having the maximum weight average molecular weight in the polymer block [A] is expressed as Mw (A1).
- the weight average molecular weight of the polymer block having the smallest weight average molecular weight is Mw (A2).
- the ratio “Mw (A1) / Mw (A2)” between Mw (A1) and Mw (A2) is preferably 2.0 or less, more preferably 1.5 or less, and particularly preferably 1.2 or less. It is. Thereby, the dispersion
- the polymer block [B] preferably contains a conjugated diene compound unit as a main component.
- the ratio of the conjugated diene compound unit in the polymer block [B] is preferably 90% by weight to 100% by weight, more preferably 95% by weight to 100% by weight, particularly 99% by weight to 100% by weight. preferable.
- the polymer block [B] can contain an arbitrary structural unit in addition to the conjugated diene compound unit.
- the arbitrary structural unit include an aromatic vinyl compound unit and a structural unit having a structure formed by polymerizing a vinyl compound other than the aromatic vinyl compound.
- the content of any structural unit in the polymer block [B] is preferably 10% by weight or less, more preferably 5% by weight or less, and particularly preferably 1% by weight or less.
- the flexibility of the hydrogenated polymer resin at low temperature is improved, and the bending resistance of the optical film at low temperature is improved. It can be improved effectively.
- the number of polymer blocks [B] in one molecule of the block copolymer is usually 1 or more, but may be 2 or more. When the number of polymer blocks [B] in the block copolymer is 2 or more, the polymer blocks [B] may be the same as or different from each other.
- the weight average molecular weight of the polymer block having the largest weight average molecular weight in the polymer block [B] is expressed as Mw (B1).
- Mw (B2) the weight average molecular weight of the polymer block having the smallest weight average molecular weight.
- the ratio “Mw (B1) / Mw (B2)” between Mw (B1) and Mw (B2) is preferably 2.0 or less, more preferably 1.5 or less, and particularly preferably 1.2 or less. It is. Thereby, the dispersion
- the ratio (wA / wB) is preferably 50/50 or more, more preferably 55/45 or more, preferably 90/10 or less, more preferably 85/15 or less.
- the block copolymer block may be a chain block or a radial block.
- a chain type block is preferable because of its excellent mechanical strength.
- both ends thereof are polymer blocks [A]. Thereby, the stickiness of the hydrogenated polymer resin can be suppressed to a low value.
- a particularly preferred block form of the block copolymer is a triblock copolymer having a [A]-[B]-[A] structure in which the polymer block [A] is bonded to both ends of the polymer block [B].
- the polymer block [B] is bonded to both ends of the polymer block [A]
- the polymer block [A] is bonded to the other end of the both polymer blocks [B], [A]-[ B]-[A]-[B]-[A] pentablock copolymer having structure.
- a triblock copolymer is particularly preferable because it is easy to produce and can have physical properties such as viscosity within a desired range.
- the molecular weight of the block copolymer is a weight average molecular weight (Mw) in terms of polystyrene measured by GPC using tetrahydrofuran (THF) as a solvent, preferably 30,000 or more, more preferably 40,000 or more, particularly Preferably it is 50,000 or more, Preferably it is 200,000 or less, More preferably, it is 150,000 or less, Most preferably, it is 100,000 or less. Further, the molecular weight distribution (Mw / Mn) of the block copolymer is preferably 3 or less, more preferably 2 or less, and particularly preferably 1.5 or less.
- the material called “monomer composition” includes not only a mixture of two or more substances but also a material composed of a single substance.
- the monomer composition (a1) and the monomer composition (a2) may be the same or different.
- (Manufacturing method 2) The 1st process of polymerizing the monomer composition (a1) containing an aromatic vinyl compound, and forming polymer block [A], At one end of the polymer block [A], the monomer composition (b1) containing a conjugated diene compound is polymerized to form a polymer block [B], and a diblock polymer of [A]-[B] A second step of forming A third step of obtaining a block copolymer by coupling ends of the diblock polymer on the polymer block [B] side with a coupling agent.
- radical polymerization, anion polymerization, cation polymerization, coordination anion polymerization, coordination cation polymerization and the like can be used.
- radical polymerization, anion polymerization or cationic polymerization is performed by living polymerization is preferable, and a method in which living polymerization is performed by living anion polymerization is particularly preferable.
- the polymerization of the monomer composition is preferably 0 ° C. or higher, more preferably 10 ° C. or higher, particularly preferably 20 ° C. or higher, and preferably 100 ° C. or lower, more preferably 80 ° C. in the presence of a polymerization initiator.
- a polymerization initiator preferably 0 ° C. or higher, more preferably 10 ° C. or higher, particularly preferably 20 ° C. or higher, and preferably 100 ° C. or lower, more preferably 80 ° C. in the presence of a polymerization initiator.
- it can be performed particularly preferably in a temperature range of 70 ° C. or less.
- examples of the polymerization initiator include monoorganolithium such as n-butyllithium, sec-butyllithium, t-butyllithium, hexyllithium; dilithiomethane, 1,4-dilithiobutane, 1,4- And polyfunctional organolithium compounds such as dilithio-2-ethylcyclohexane; One of these may be used alone, or two or more of these may be used in combination at any ratio.
- monoorganolithium such as n-butyllithium, sec-butyllithium, t-butyllithium, hexyllithium
- dilithiomethane 1,4-dilithiobutane
- 1,4- And polyfunctional organolithium compounds such as dilithio-2-ethylcyclohexane
- Examples of the polymerization reaction include solution polymerization and slurry polymerization. In particular, when solution polymerization is used, reaction heat can be easily removed.
- an inert solvent in which the polymer obtained in each step can be dissolved can be used as the solvent.
- the inert solvent include aliphatic hydrocarbon solvents such as n-pentane, isopentane, n-hexane, n-heptane and isooctane; alicyclic carbonization such as cyclopentane, cyclohexane, methylcyclopentane, methylcyclohexane and decalin.
- a hydrogen solvent aromatic hydrocarbon solvents such as benzene and toluene; and the like.
- aromatic hydrocarbon solvents such as benzene and toluene; and the like.
- One of these may be used alone, or two or more of these may be used in combination at any ratio.
- an alicyclic hydrocarbon solvent as a solvent because it can be used as it is as an inert solvent for the hydrogenation reaction and the solubility of the block copolymer is good.
- the amount of the solvent used is preferably 200 to 2000 parts by weight with respect to 100 parts by weight of all the monomers used.
- a randomizer can be used in order to prevent only one component chain from becoming long.
- a Lewis base compound it is preferable to use, for example, a Lewis base compound as a randomizer.
- Lewis base compounds include ether compounds such as dimethyl ether, diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, diphenyl ether, ethylene glycol diethyl ether, and ethylene glycol methyl phenyl ether; and tetramethylethylenediamine, trimethylamine, triethylamine, pyridine, Tertiary amine compounds; alkali metal alkoxide compounds such as potassium-t-amyl oxide and potassium-t-butyl oxide; phosphine compounds such as triphenylphosphine; and the like. One of these may be used alone, or two or more of these may be used in combination at any ratio.
- the hydride of an aromatic vinyl compound / conjugated diene compound block copolymer is a polymer obtained through the above-described process of hydrogenating the aromatic vinyl compound / conjugated diene compound block copolymer.
- This hydride may be modified with, for example, alkoxysilane, carboxylic acid, carboxylic acid anhydride, or the like as necessary.
- alkoxysilane carboxylic acid, carboxylic acid anhydride, or the like as necessary.
- the hydride is obtained by hydrogenating the unsaturated bond of the above-mentioned aromatic vinyl compound / conjugated diene compound block copolymer.
- the unsaturated bond of the block copolymer includes both aromatic and non-aromatic carbon-carbon unsaturated bonds in the main chain and side chain of the block copolymer.
- the hydrogenation rate is preferably 90% or more, more preferably 97% or more, and particularly preferably 99% or more of the total unsaturated bonds of the block copolymer. The higher the hydrogenation rate, the better the heat resistance and light resistance of the hydrogenated polymer resin.
- the hydrogenation rate of the hydride can be determined by measurement by 1 H-NMR.
- the hydrogenation rate of the non-aromatic unsaturated bond is preferably 95% or more, more preferably 99% or more.
- the hydrogenation rate of the aromatic carbon-carbon unsaturated bond is preferably 90% or more, more preferably 93% or more, and particularly preferably 95% or more. Since the glass transition temperature of the polymer block obtained by hydrogenating the polymer block [A] is increased by increasing the hydrogenation rate of the carbon-carbon unsaturated bond of the aromatic ring, the heat resistance of the hydrogenated polymer resin Can be effectively increased.
- the weight average molecular weight (Mw) of the hydride of the block copolymer is a value in terms of polystyrene measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent, preferably 30,000 or more, more preferably Is 40,000 or more, particularly preferably 45,000 or more, preferably 200,000 or less, more preferably 150,000 or less, and particularly preferably 100,000 or less.
- the molecular weight distribution (Mw / Mn) of the hydride of the block copolymer is preferably 3 or less, more preferably 2 or less, and particularly preferably 1.5 or less.
- the weight fraction wA of the whole polymer block [A] in the whole block copolymer, and the weight fraction wB in which the whole polymer block [B] occupies the whole block copolymer is usually the same value as wA / wB in the block copolymer before hydrogenation.
- the hydride of the block copolymer preferably has an alkoxysilyl group in its molecular structure.
- the block copolymer hydride having an alkoxysilyl group can be obtained, for example, by bonding an alkoxysilyl group to a hydride of a block copolymer having no alkoxysilyl group.
- an alkoxysilyl group may be directly bonded to the hydride of the block copolymer, and may be bonded via a divalent organic group such as an alkylene group.
- the hydride of a block copolymer having an alkoxysilyl group is particularly excellent in adhesion to materials such as glass, inorganic substances, and metals. Therefore, when bonding an optical film with arbitrary members, the adhesiveness of an optical film and arbitrary members can be made especially high.
- the introduction amount of the alkoxysilyl group is preferably 0.1 parts by weight or more, more preferably 0.2 parts by weight or more, particularly preferably 100 parts by weight of the hydride of the block copolymer before the introduction of the alkoxysilyl group. It is 0.3 parts by weight or more, preferably 10 parts by weight or less, more preferably 5 parts by weight or less, and particularly preferably 3 parts by weight or less.
- the amount of alkoxysilyl group introduced can be measured by 1 H-NMR spectrum (when the amount introduced is small, the number of integrations is increased).
- the molecular weight of the hydride of the block copolymer having an alkoxysilyl group is usually larger than the molecular weight of the hydride of the block copolymer before introducing the alkoxysilyl group because the amount of the alkoxysilyl group to be introduced is small. It does not change. However, if the hydride of the block copolymer is modified in the presence of a peroxide when introducing an alkoxysilyl group, the crosslinking reaction and cleavage reaction of the hydride proceeds and the molecular weight distribution changes greatly. There is.
- the weight average molecular weight of the hydride of the block copolymer having an alkoxysilyl group is a value in terms of polystyrene measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent, preferably 30,000 or more, More preferably, it is 40,000 or more, Especially preferably, it is 50,000 or more, Preferably it is 200,000 or less, More preferably, it is 150,000 or less, Most preferably, it is 120,000 or less.
- the molecular weight distribution (Mw / Mn) of the hydride of the block copolymer having an alkoxysilyl group is preferably 3.5 or less, more preferably 2.5 or less, and particularly preferably 2.0 or less.
- the weight average molecular weight Mw and molecular weight distribution Mw / Mn of the hydride of the block copolymer having an alkoxysilyl group are within this range, the mechanical strength and tensile elongation of the hydrogenated polymer resin can be improved.
- the method for producing a hydride of a block copolymer as described above usually includes hydrogenating the above-described block copolymer.
- a hydrogenation method that can increase the hydrogenation rate and has less chain-breaking reaction of the block copolymer is preferable.
- Examples of such a preferable hydrogenation method include hydrogenation using a hydrogenation catalyst containing at least one metal selected from the group consisting of nickel, cobalt, iron, titanium, rhodium, palladium, platinum, ruthenium, and rhenium.
- a hydrogenation catalyst may be used individually by 1 type, and may be used combining two or more types by arbitrary ratios.
- the hydrogenation catalyst either a heterogeneous catalyst or a homogeneous catalyst can be used.
- the hydrogenation reaction is preferably performed in an organic solvent.
- the heterogeneous catalyst may be used, for example, in the form of a free metal or metal compound, or may be used by being supported on a suitable carrier.
- suitable carrier include activated carbon, silica, alumina, calcium carbonate, titania, magnesia, zirconia, diatomaceous earth, silicon carbide, calcium fluoride, and the like.
- the supported amount of the catalyst is preferably 0.1% by weight or more, more preferably 1% by weight or more, preferably 60% by weight or less, more preferably 50% by weight or less based on the total amount of the catalyst and the carrier. is there.
- the specific surface area of the supported catalyst is preferably 100 m 2 / g to 500 m 2 / g.
- the average pore diameter of the supported catalyst is preferably 100 mm or more, more preferably 200 mm or more, preferably 1000 mm or less, more preferably 500 mm or less.
- the specific surface area can be obtained by measuring the nitrogen adsorption amount and using the BET equation.
- the average pore diameter can be measured by a mercury intrusion method.
- the homogeneous catalyst for example, a catalyst obtained by combining a nickel, cobalt, titanium or iron compound and an organometallic compound; an organometallic complex catalyst such as rhodium, palladium, platinum, ruthenium or rhenium;
- an organometallic complex catalyst such as rhodium, palladium, platinum, ruthenium or rhenium;
- the nickel, cobalt, titanium, or iron compound include acetylacetonato compounds, carboxylates, and cyclopentadienyl compounds of each metal.
- organometallic compound examples include organoaluminum compounds such as alkylaluminum such as triethylaluminum and triisobutylaluminum, aluminum halide such as diethylaluminum chloride and ethylaluminum dichloride, and alkylaluminum hydride such as diisobutylaluminum hydride; And organic lithium compounds.
- organoaluminum compounds such as alkylaluminum such as triethylaluminum and triisobutylaluminum, aluminum halide such as diethylaluminum chloride and ethylaluminum dichloride, and alkylaluminum hydride such as diisobutylaluminum hydride; And organic lithium compounds.
- organometallic complex catalysts include transition metal complexes such as dihydrido-tetrakis (triphenylphosphine) ruthenium, dihydrido-tetrakis (triphenylphosphine) iron, bis (cyclooctadiene) nickel, and bis (cyclopentadienyl) nickel. Is mentioned.
- the amount of the hydrogenation catalyst is preferably 0.01 parts by weight or more, more preferably 0.05 parts by weight or more, particularly preferably 0.1 parts by weight or more, preferably 100 parts by weight of the block copolymer. Is 100 parts by weight or less, more preferably 50 parts by weight or less, and particularly preferably 30 parts by weight or less.
- the temperature of the hydrogenation reaction is preferably 10 ° C or higher, more preferably 50 ° C or higher, particularly preferably 80 ° C or higher, preferably 250 ° C or lower, more preferably 200 ° C or lower, particularly preferably 180 ° C or lower. .
- the hydrogenation rate can be increased and the molecular cleavage of the block copolymer can be reduced.
- the hydrogen pressure during the hydrogenation reaction is preferably 0.1 MPa or more, more preferably 1 MPa or more, particularly preferably 2 MPa or more, preferably 30 MPa or less, more preferably 20 MPa or less, and particularly preferably 10 MPa or less. .
- the hydrogenation rate can be increased, the molecular chain breakage of the block copolymer can be reduced, and the operability is improved.
- a hydride of the block copolymer is obtained as a product.
- the product after this hydrogenation reaction may be used as it is. Further, the product after the hydrogenation reaction may be further subjected to any treatment as necessary. For example, you may perform the process which introduce
- a method for introducing an alkoxysilyl group into a hydride of a block copolymer for example, a hydride of a block copolymer before introducing an alkoxysilyl group, an ethylenically unsaturated silane compound, a peroxide
- a method of reacting in the presence can be used.
- ethylenically unsaturated silane compound those capable of graft polymerization with a hydride of a block copolymer and capable of introducing an alkoxysilyl group into the hydride of the block copolymer can be used.
- Examples of such ethylenically unsaturated silane compounds include vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, dimethoxymethylvinylsilane, diethoxymethylvinylsilane, p-styryltrimethoxysilane, p-styryltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-acryloxypropyltri Examples include methoxysilane, 3-acryloxypropyltriethoxysilane, and 2-norbornen-5-yltrimethoxysilane.
- vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, dimethoxymethylvinylsilane, diethoxymethylvinylsilane, and p-styryltrimethoxysilane are preferable.
- an ethylenically unsaturated silane compound may be used individually by 1 type, and may be used combining two or more types by arbitrary ratios.
- the amount of the ethylenically unsaturated silane compound is preferably 0.1 parts by weight or more, more preferably 0.2 parts by weight or more with respect to 100 parts by weight of the hydride of the block copolymer before introducing the alkoxysilyl group.
- the amount is particularly preferably 0.3 parts by weight or more, preferably 10 parts by weight or less, more preferably 5 parts by weight or less, and particularly preferably 3 parts by weight or less.
- peroxides examples include dibenzoyl peroxide, t-butyl peroxyacetate, 2,2-di- (t-butylperoxy) butane, t-butylperoxybenzoate, t-butylcumyl peroxide, Milperoxide, di-t-hexyl peroxide, 2,5-dimethyl-2,5-di (t-butylperoxyhexane), di-t-butyl peroxide, 2,5-dimethyl-2,5- Organic peroxides such as di (t-butylperoxy) hexane-3, t-butylhydroperoxide, t-butylperoxyisobutyrate, lauroyl peroxide, dipropionyl peroxide, p-menthane hydroperoxide Can be mentioned.
- t-butyl cumyl peroxide dicumyl peroxide, di-t-hexyl peroxide, 2,5-dimethyl-2,5- Di (t-butylperoxyhexane), di-t-butyl peroxide and the like are preferable.
- a peroxide may be used individually by 1 type and may be used in combination of 2 or more type.
- the amount of the peroxide is preferably 0.01 parts by weight or more, more preferably 0.2 parts by weight or more, particularly preferably 100 parts by weight of the hydride of the block copolymer before introducing the alkoxysilyl group. Is 0.3 parts by weight or more, preferably 5 parts by weight or less, more preferably 3 parts by weight or less, and particularly preferably 2 parts by weight or less.
- the method of reacting the hydride of the block copolymer with the ethylenically unsaturated silane compound in the presence of a peroxide can be performed using, for example, a heating kneader and a reactor.
- a block copolymer hydride, an ethylenically unsaturated silane compound and a peroxide mixture are heated and melted at a temperature equal to or higher than the melting temperature of the block copolymer hydride in a biaxial kneader. Then, by kneading for a desired time, an alkoxysilyl group can be introduced into the hydride of the block copolymer.
- the specific temperature is preferably 180 ° C.
- the heat kneading time is preferably 0.1 minutes or more, more preferably 0.2 minutes or more, particularly preferably 0.3 minutes or more, preferably 15 minutes or less, more preferably 10 minutes or less, particularly preferably. Is less than 5 minutes.
- a continuous kneading facility such as a twin-screw kneader or a single-screw extruder
- kneading and extrusion can be performed continuously with the residence time being in the above range.
- the hydride of the block copolymer obtained by the above-described method is usually obtained as a reaction liquid containing a hydride of the block copolymer, a hydrogenation catalyst, and a polymerization catalyst. Therefore, the hydride of the block copolymer can be recovered from the reaction solution after removing the hydrogenation catalyst and the polymerization catalyst from the reaction solution by a method such as filtration and centrifugation.
- a method of recovering the hydride of the block copolymer from the reaction solution for example, a steam coagulation method in which the solvent is removed from the solution in which the hydride of the block copolymer is dissolved by steam stripping; the solvent is removed under reduced pressure heating. Direct desolvation method; a coagulation method in which a solution is poured into a poor solvent of the block copolymer hydride to precipitate and solidify the hydride of the block copolymer; and the like.
- the hydrogenated polymer resin may contain an arbitrary component in combination with the hydride of the block copolymer described above.
- optional components include a plasticizer for adjusting the glass transition temperature and elastic modulus, a light stabilizer for improving weather resistance and heat resistance, an ultraviolet absorber, an antioxidant, a lubricant, and an inorganic filler. Can be mentioned.
- arbitrary components may be used individually by 1 type, and may be used combining two or more types by arbitrary ratios.
- plasticizer examples include polyisobutene, hydrogenated polyisobutene, hydrogenated polyisoprene, hydrogenated 1,3-pentadiene petroleum resin, hydrogenated cyclopentadiene petroleum resin, hydrogenated styrene / indene petroleum resin, and the like.
- the amount of the plasticizer is preferably 40 parts by weight or less with respect to 100 parts by weight of the hydrogenated polymer resin, and is appropriately selected according to the purpose of adjusting the resin characteristics.
- a hindered amine light stabilizer is preferable, and in the structure, 3,5-di-t-butyl-4-hydroxyphenyl group, 2,2,6,6-tetramethylpiperidyl group, or 1, Particularly preferred are compounds having a 2,2,6,6-pentamethyl-4-piperidyl group.
- Specific examples of the light stabilizer include light stabilizers described in International Publication No. 2014/091941.
- the amount of the light stabilizer is preferably 0.01 parts by weight or more, more preferably 0.02 parts by weight or more, particularly preferably 0.03 parts by weight or more with respect to 100 parts by weight of the hydride of the block copolymer.
- the amount of the light stabilizer preferably 5 parts by weight or less, more preferably 2 parts by weight or less, particularly preferably 1 part by weight or less.
- the ultraviolet absorber examples include benzophenone ultraviolet absorbers, salicylic acid ultraviolet absorbers, and benzotriazole ultraviolet absorbers.
- Specific examples of the ultraviolet stabilizer include ultraviolet absorbers described in International Publication No. 2014/091941.
- the amount of the UV absorber is preferably 0.01 parts by weight or more, more preferably 0.02 parts by weight or more, and particularly preferably 0.04 parts by weight or more with respect to 100 parts by weight of the hydride of the block copolymer. Yes, preferably 1 part by weight or less, more preferably 0.5 part by weight or less, particularly preferably 0.3 part by weight or less.
- the antioxidant examples include phosphorus antioxidants, phenol antioxidants, sulfur antioxidants, and the like, and phosphorus antioxidants with less coloring are preferable.
- Specific examples of the antioxidant include the antioxidants described in International Publication No. 2014/091941.
- the amount of the antioxidant is preferably 0.01 parts by weight or more, more preferably 0.05 parts by weight or more, and particularly preferably 0.1 parts by weight or more with respect to 100 parts by weight of the hydride of the block copolymer. Yes, preferably 1 part by weight or less, more preferably 0.5 part by weight or less, particularly preferably 0.3 part by weight or less.
- the glass transition temperature of the hydrogenated polymer resin is preferably 30 ° C. or higher, more preferably 50 ° C. or higher, particularly preferably 70 ° C. or higher, preferably 200 ° C. or lower, more preferably 180 ° C. or lower, particularly preferably 160 ° C. It is below °C.
- the hydrogenated polymer resin may have a plurality of glass transition temperatures. In this case, it is preferable that the highest glass transition temperature of the resin falls within the above range.
- the hydrogenated polymer resin containing the hydride of the block copolymer is excellent in flexibility. Since the optical film of the present invention includes the flexible hydrogenated polymer resin layers (that is, the first layer and the third layer) on both sides of the second layer containing the norbornene polymer, the norbornene polymer is provided. Bending resistance can be improved without significantly detracting from the excellent characteristics of.
- the thickness of the first layer is preferably 2 ⁇ m or more, more preferably 5 ⁇ m or more, preferably 50 ⁇ m or less, more preferably 30 ⁇ m or less. Bending resistance can be further improved by setting the thickness of the first layer to be equal to or higher than the lower limit value of the range, and the thickness of the entire optical film can be reduced by setting the thickness to be equal to or lower than the upper limit value of the range.
- the ratio between the thickness of the first layer and the thickness of the second layer is preferably 5/95 or more, more preferably 10/90 or more, and preferably 60/40 or less. Preferably it is 40/60 or less. Bending resistance can be further improved by setting the thickness ratio to be equal to or higher than the lower limit value of the range, and maintaining the elastic modulus and heat resistance of the entire optical film by setting the thickness ratio to be equal to or lower than the upper limit value of the range. Can do.
- the second layer contains a norbornene polymer. Therefore, the second layer is usually a resin layer made of a resin containing a norbornene polymer.
- a resin containing a norbornene-based polymer may be referred to as “norbornene-based resin” as appropriate.
- This norbornene-based resin is usually a thermoplastic resin.
- Examples of the norbornene polymer include a ring-opening polymer of a monomer having a norbornene structure and a hydride thereof; an addition polymer of a monomer having a norbornene structure and a hydride thereof.
- Examples of a ring-opening polymer of a monomer having a norbornene structure include a ring-opening homopolymer of one kind of monomer having a norbornene structure and a ring-opening of two or more kinds of monomers having a norbornene structure. Examples thereof include a copolymer and a ring-opening copolymer of a monomer having a norbornene structure and an arbitrary monomer copolymerizable therewith.
- examples of the addition polymer of a monomer having a norbornene structure include an addition homopolymer of one kind of monomer having a norbornene structure and an addition copolymer of two or more kinds of monomers having a norbornene structure. And addition copolymers of a monomer having a norbornene structure and an arbitrary monomer copolymerizable therewith.
- a hydride of a ring-opening polymer of a monomer having a norbornene structure is particularly suitable from the viewpoints of moldability, heat resistance, low moisture absorption, dimensional stability, lightness, and the like.
- Examples of the monomer having a norbornene structure include bicyclo [2.2.1] hept-2-ene (common name: norbornene), tricyclo [4.3.0.1 2,5 ] deca-3,7. -Diene (common name: dicyclopentadiene), 7,8-benzotricyclo [4.3.0.1 2,5 ] dec-3-ene (common name: methanotetrahydrofluorene), tetracyclo [4.4. 0.1 2,5 . 1 7,10 ] dodec-3-ene (common name: tetracyclododecene), and derivatives of these compounds (for example, those having a substituent in the ring).
- examples of the substituent include an alkyl group, an alkylene group, and a polar group. These substituents may be the same or different, and a plurality thereof may be bonded to the ring.
- One type of monomer having a norbornene structure may be used alone, or two or more types may be used in combination at any ratio.
- Examples of the polar group include heteroatoms or atomic groups having heteroatoms.
- Examples of the hetero atom include an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, and a halogen atom.
- Specific examples of the polar group include a carboxyl group, a carbonyloxycarbonyl group, an epoxy group, a hydroxyl group, an oxy group, an ester group, a silanol group, a silyl group, an amino group, a nitrile group, and a sulfonic acid group.
- Examples of the monomer capable of ring-opening copolymerization with a monomer having a norbornene structure include monocyclic olefins such as cyclohexene, cycloheptene, and cyclooctene and derivatives thereof; cyclic conjugated dienes such as cyclohexadiene and cycloheptadiene; Derivatives thereof; and the like.
- monocyclic olefins such as cyclohexene, cycloheptene, and cyclooctene and derivatives thereof
- cyclic conjugated dienes such as cyclohexadiene and cycloheptadiene
- Derivatives thereof and the like.
- the monomer having a norbornene structure and a monomer capable of ring-opening copolymerization one kind may be used alone, or two or more kinds may be used in combination at any ratio.
- a ring-opening polymer of a monomer having a norbornene structure can be produced, for example, by polymerizing or copolymerizing a monomer in the presence of a ring-opening polymerization catalyst.
- Examples of monomers that can be copolymerized with a monomer having a norbornene structure include ⁇ -olefins having 2 to 20 carbon atoms such as ethylene, propylene, and 1-butene, and derivatives thereof; cyclobutene, cyclopentene, and cyclohexene. And non-conjugated dienes such as 1,4-hexadiene, 4-methyl-1,4-hexadiene, 5-methyl-1,4-hexadiene; and the like.
- ⁇ -olefin is preferable, and ethylene is more preferable.
- the monomer which can carry out addition copolymerization with the monomer which has a norbornene structure may be used individually by 1 type, and may be used combining two or more types by arbitrary ratios.
- An addition polymer of a monomer having a norbornene structure can be produced, for example, by polymerizing or copolymerizing a monomer in the presence of an addition polymerization catalyst.
- the hydride of the ring-opening polymer and the addition polymer described above is, for example, carbon-carbon-free in a solution of the ring-opening polymer and the addition polymer in the presence of a hydrogenation catalyst containing a transition metal such as nickel or palladium. Saturated bonds can be produced by hydrogenation, preferably 90% or more.
- X bicyclo [3.3.0] octane-2,4-diyl-ethylene structure and Y: tricyclo [4.3.0.1 2,5 ] decane- Having a 7,9-diyl-ethylene structure, and the amount of these structural units is 90% by weight or more based on the total structural units of the norbornene polymer, and the ratio of X to Y The ratio is preferably 100: 0 to 40:60 by weight ratio of X: Y.
- the norbornene-based polymer preferably has a weight average molecular weight (Mw) of 10,000 or more, more preferably 15,000 or more, particularly preferably 20,000 or more, preferably 100,000 or less, more preferably 80, 000 or less, particularly preferably 50,000 or less.
- Mw weight average molecular weight
- the molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) of the norbornene polymer is preferably 1.2 or more, more preferably 1.5 or more, particularly preferably 1.8 or more, preferably Is 3.5 or less, more preferably 3.0 or less, and particularly preferably 2.7 or less.
- productivity of a norbornene-type polymer can be improved and manufacturing cost can be suppressed.
- the quantity of a low molecular component becomes small by making it into an upper limit or less, relaxation at the time of high temperature exposure can be suppressed and stability of an optical film can be improved.
- the weight average molecular weight (Mw) and number average molecular weight (Mn) were determined by gel permeation chromatography using cyclohexane as a solvent (however, toluene may be used when the sample does not dissolve in cyclohexane). , Polyisoprene or polystyrene as a weight average molecular weight.
- the saturated water absorption of the norbornene polymer is preferably 0.03% by weight or less, more preferably 0.02% by weight or less, and particularly preferably 0.01% by weight or less.
- the saturated water absorption is in the above range, the change with time of optical properties such as retardation of the optical film can be reduced.
- deterioration of members (polarizing plates and the like) and devices (image display devices and the like) including the optical film can be suppressed, and the lifetime of those members and devices can be increased.
- the saturated water absorption is a value obtained by immersing a sample in water at a constant temperature for a certain period of time and representing the mass as a percentage of the mass of the test piece before immersion. Usually, it is measured by immersing in 23 ° C. water for 24 hours.
- the saturated water absorption rate of the polymer can be adjusted to the above range, for example, by reducing the amount of polar groups in the polymer. Therefore, from the viewpoint of lowering the saturated water absorption rate, the norbornene-based polymer preferably has no polar group.
- the amount of the norbornene polymer in the norbornene resin is preferably 50.0 wt% to 100 wt%, more preferably 80.0 wt% to 100 wt%, particularly preferably 90.0 wt% to 100 wt%. is there.
- the optical properties of the norbornene-based polymer can be improved by taking advantage of the properties such as heat resistance, moisture resistance, transparency, mechanical strength, dimensional stability and moldability. A film can be obtained.
- the norbornene-based resin can contain any component in combination with the above-described norbornene-based polymer.
- optional components include colorants such as pigments and dyes; plasticizers; fluorescent brighteners; dispersants; thermal stabilizers; light stabilizers; antistatic agents; ultraviolet absorbers; And the like.
- Arbitrary components may be used individually by 1 type, and may be used combining two or more types by arbitrary ratios.
- the glass transition temperature of the norbornene resin is preferably 100 ° C. or higher, more preferably 110 ° C. or higher, particularly preferably 120 ° C. or higher, preferably 160 ° C. or lower, more preferably 150 ° C. or lower, particularly preferably 140 ° C. or lower. It is.
- the glass transition temperature of the norbornene-based resin higher than the lower limit of the above range, the durability of the optical film in a high temperature environment can be improved, and by making the glass transition temperature lower than the upper limit of the above range, the production of the optical film is easy. Can be done.
- the optical film includes the second layer containing the norbornene-based polymer as described above, the optical film exhibits properties as excellent as those of the conventional film containing the norbornene-based polymer in characteristics such as transparency and tensile elastic modulus. be able to. Furthermore, the optical film can usually exhibit properties as excellent as those of conventional films containing norbornene polymers in properties such as heat resistance, moisture resistance, dimensional stability, and moldability.
- the thickness of the second layer is preferably 5 ⁇ m or more, more preferably 10 ⁇ m or more, preferably 200 ⁇ m or less, more preferably 100 ⁇ m or less.
- the elastic modulus and heat resistance of the entire optical film can be maintained by setting the thickness of the second layer to be equal to or higher than the lower limit value of the range, and the bending resistance is further improved by setting the thickness to be equal to or lower than the upper limit value of the range. be able to.
- the third layer includes a hydride of an aromatic vinyl compound / conjugated diene compound block copolymer. Therefore, the third layer is usually a resin layer made of a hydrogenated polymer resin containing a hydride of an aromatic vinyl compound / conjugated diene compound block copolymer.
- the hydrogenated polymer resin contained in the third layer those in the range described as the hydrogenated polymer resin contained in the first layer can be arbitrarily used.
- the hydrogenated polymer resin contained in the first layer and the hydrogenated polymer resin contained in the third layer may be different, but are the same from the viewpoints of suppressing the manufacturing cost of the optical film and suppressing curling. It is preferable.
- the thickness of the third layer can be arbitrarily set within the range described as the thickness of the first layer.
- the thickness of the first layer and the thickness of the third layer may be different, but are preferably the same from the viewpoint of suppressing curling of the optical film.
- the optical film may be provided with an arbitrary layer in combination with the first layer, the second layer, and the third layer described above as long as the effects of the present invention are not significantly impaired.
- the optical film is preferably a film having a three-layer structure including a first layer, a second layer, and a third layer.
- the optical film described above is excellent in bending resistance. Therefore, the optical film is hardly damaged even when used for an application involving a bending operation.
- the bending resistance of the optical film can be evaluated by the folding resistance.
- the folding resistance of the optical film is usually 500 or more, preferably 1000 or more, more preferably 1500 or more.
- the upper limit of the folding resistance of the optical film is not particularly limited, but may be, for example, 1,000,000 or less.
- the folding resistance of the optical film can be measured by the MIT folding resistance test according to JIS P 8115 “Paper and paperboard—Folding strength test method—MIT testing machine method” according to the following procedure.
- a test piece having a width of 15 mm ⁇ 0.1 mm and a length of about 110 mm is cut out from the optical film as a sample.
- the test piece is prepared so that the direction in which the optical film is most strongly stretched is parallel to the side of about 110 mm of the test piece. Then, using a MIT folding resistance tester (“No.
- the load is 9.8 N
- the curvature of the bent portion is 0.38 ⁇ 0.02 mm
- the bending angle is 135 ° ⁇ 2 °
- the bending speed is Under the condition of 175 times / minute, the test piece is bent so that a fold appears in the width direction of the test piece. This bending is continued, and the number of reciprocal bendings until the test piece breaks is measured.
- Ten test pieces are prepared, and the number of reciprocal bending until the test piece is broken is measured 10 times by the above method. The average of the ten measurement values measured in this way is defined as the folding resistance of the optical film (MIT folding resistance count).
- the above-described optical film has excellent characteristics like a conventional film containing a norbornene polymer.
- the optical film of the present invention has excellent transparency and mechanical strength.
- the total light transmittance of the optical film is preferably 70% to 100%, more preferably 80% to 100%, and particularly preferably 90% to 100%.
- the total light transmittance of the optical film can be measured in the wavelength range of 400 nm to 700 nm using an ultraviolet / visible spectrometer.
- the tensile elastic modulus of the optical film is preferably 1000 MPa or more, more preferably 1400 MPa or more, and particularly preferably 1600 MPa or more.
- the tensile elastic modulus of the optical film can be measured according to JIS K 7161.
- the upper limit of the tensile elasticity modulus of an optical film is not specifically limited, For example, it can be 5000 MPa or less.
- the amount of the volatile component contained in the optical film is preferably 0.1% by weight or less, more preferably 0.05% by weight or less, and further preferably 0.02% by weight or less.
- the amount of the volatile component is a substance having a molecular weight of 200 or less. Examples of volatile components include residual monomers and solvents.
- the amount of volatile components can be quantified by analyzing by gas chromatography as the sum of substances having a molecular weight of 200 or less.
- the optical film is preferably thin. Even if the thickness is thus small, the above-described optical film has high bending resistance.
- the specific thickness of the optical film is preferably 5 ⁇ m or more, more preferably 10 ⁇ m or more, preferably 200 ⁇ m or less, more preferably 100 ⁇ m or less.
- the water absorption of the optical film is preferably 0.1% by weight or less, more preferably 0.05% by weight or less, still more preferably 0.01% by weight or less, and ideally 0% by weight. When the water absorption is within this range, it is possible to extend the life of members (polarizing plates, etc.) and devices (image display devices, etc.) provided with optical films.
- the lower limit of the water absorption rate is not particularly limited, but is ideally 0% by weight.
- the water absorption rate of the optical film is a value measured according to ASTM D570. Specifically, it can be calculated by immersing a 100 mm ⁇ 100 mm film in water at 23 ° C. for 1 hour and measuring the increased weight of the immersion.
- optical film There is no restriction
- the optical film can be manufactured, for example, by a manufacturing method including a step of forming a hydrogenated polymer resin and a norbornene-based resin into a film shape.
- Examples of the resin molding method include a co-extrusion method and a co-casting method.
- the coextrusion method is preferable because it is excellent in production efficiency and hardly causes volatile components to remain in the optical film.
- the coextrusion method includes an extrusion process in which a hydrogenated polymer resin and a norbornene resin are coextruded.
- the hydrogenated polymer resin and the norbornene-based resin are each extruded in layers in a molten state.
- examples of the resin extrusion method include a coextrusion T-die method, a coextrusion inflation method, and a coextrusion lamination method.
- the coextrusion T-die method is preferable.
- the coextrusion T-die method includes a feed block method and a multi-manifold method, and the multi-manifold method is particularly preferable in that variation in thickness can be reduced.
- the melting temperature of the extruded resin is preferably (Tg + 80 ° C.) or higher, more preferably (Tg + 100 ° C.) or higher, preferably (Tg + 180 ° C.) or lower, more preferably (Tg + 170 ° C.) or lower.
- Tg represents the highest temperature among the glass transition temperatures of the hydrogenated polymer resin and the norbornene resin.
- the temperature of the resin in the extruder is preferably Tg to (Tg + 100 ° C.) at the resin inlet, preferably (Tg + 50 ° C.) to (Tg + 170 ° C.) at the extruder outlet, and the die temperature is preferably (Tg + 50 ° C.). To (Tg + 170 ° C.).
- the film-like molten resin extruded from a die is usually brought into close contact with a cooling roll, cooled, and cured.
- examples of the method for bringing the molten resin into close contact with the cooling roll include an air knife method, a vacuum box method, and an electrostatic contact method.
- the number of cooling rolls is not particularly limited, and is usually 2 or more.
- Examples of the arrangement method of the cooling roll include a linear type, a Z type, and an L type.
- the method of passing the molten resin extruded from the die through the cooling roll is not particularly limited.
- the hydrogenated polymer resin and the norbornene resin are formed into a film as described above, the first layer made of the hydrogenated polymer resin, the second layer made of the norbornene resin, and the hydrogenated polymer resin are formed. An optical film provided with the third layer in this order is obtained.
- the method for producing an optical film may further include an optional step in addition to the steps described above.
- the method for producing an optical film may include a step of performing a stretching process on the optical film. By performing the stretching treatment, desired retardation can be expressed in the optical film, and the mechanical properties of the optical film can be improved.
- the method for producing an optical film may include a step of performing a surface treatment on the optical film.
- optical film The use of the optical film is arbitrary. Applications of optical films include, for example, retardation films, polarizing plate protective films, sealing films for optical devices, base films for organic electroluminescence elements, base films for flexible electrodes, base films for touch panels, etc. Is mentioned.
- the folding resistance of the optical film was measured by the MIT folding resistance test according to JIS P 8115 “Paper and paperboard—Folding strength test method—MIT testing machine method” according to the following procedure.
- a test piece having a width of 15 mm ⁇ 0.1 mm and a length of about 110 mm was cut out from the optical film as a sample.
- a MIT folding resistance tester (“No. 307” manufactured by Yasuda Seiki Seisakusho)
- the load is 9.8 N
- the curvature of the bent portion is 0.38 ⁇ 0.02 mm
- the bending angle is 135 ° ⁇ 2 °
- the bending speed is 175 times.
- the test piece was bent so that a crease appeared in the width direction of the test piece under the conditions of / min. This bending was continued, and the number of reciprocal bendings until the test piece broke was measured. Ten test pieces were prepared, and the number of reciprocal bendings until the test pieces were broken by the above method was measured 10 times. The average of the 10 measured values thus measured was defined as the folding resistance of the film (MIT folding resistance count).
- the total light transmittance of the optical film was measured in the wavelength range of 400 nm to 700 nm using an ultraviolet / visible spectrometer.
- the water absorption of the optical film is a value measured according to ASTM D570. Specifically, it was calculated by immersing a 100 mm ⁇ 100 mm film in water at 23 ° C. for 1 hour and measuring the increased weight.
- the obtained block copolymer had a weight average molecular weight (Mw) of 48,300, a molecular weight distribution (Mw / Mn) of 1.03, and the ratio of the styrene block to the isobutylene block was 60:40 by weight.
- the solution was filtered through a Zeta Plus (registered trademark) filter 30H (Cuno, pore size 0.5 ⁇ m to 1 ⁇ m), and further with another metal fiber filter (Nichidai, pore size 0.4 ⁇ m). Sequential filtration removed fine solids. Thereafter, cyclohexane, xylene and other volatile components as solvents were removed from the solution at a temperature of 260 ° C. and a pressure of 0.001 MPa or less using a cylindrical concentration dryer (manufactured by Hitachi, Ltd., Contro).
- the remaining solid content was extruded as a strand in a molten state from a die directly connected to a concentration dryer, cooled, and then cut with a pelletizer to obtain 95 parts of a pellet containing a block copolymer hydride.
- the resulting block copolymer hydride had a weight average molecular weight (Mw) of 50,300, a molecular weight distribution (Mw / Mn) of 1.05, and a hydrogenation rate of almost 100%.
- this pellet resin is referred to as “resin A” as appropriate.
- the obtained block copolymer had a weight average molecular weight (Mw) of 50,400, a molecular weight distribution (Mw / Mn) of 1.03, and the ratio of the styrene block to the isobutylene block was 90:10.
- the hydrogenation reaction of the obtained block copolymer was performed in the same manner as in Production Example 1.
- the weight average molecular weight (Mw) of the block copolymer hydride obtained by the hydrogenation reaction was 53,000, and the molecular weight distribution (Mw / Mn) was 1.04.
- the resulting block polymer hydride was pelletized.
- the resulting block copolymer hydride had a weight average molecular weight (Mw) of 52,200, a molecular weight distribution (Mw / Mn) of 1.05, and a hydrogenation rate of almost 100%.
- this pellet resin is referred to as “resin B” as appropriate.
- the resulting block copolymer had a weight average molecular weight (Mw) of 54000, a molecular weight distribution (Mw / Mn) of 1.04, and the ratio of styrene block to isobutylene block was 75:25 by weight.
- the hydrogenation reaction of the obtained block copolymer was performed in the same manner as in Production Example 1.
- the weight average molecular weight (Mw) of the block copolymer hydride obtained by the hydrogenation reaction was 53100, and the molecular weight distribution (Mw / Mn) was 1.04.
- the resulting block polymer hydride was pelletized.
- the resulting block copolymer hydride had a weight average molecular weight (Mw) of 52,500, a molecular weight distribution (Mw / Mn) of 1.05, and a hydrogenation rate of almost 100%.
- this pellet resin is appropriately referred to as “resin C”.
- the resulting block copolymer had a weight average molecular weight (Mw) of 54000, a molecular weight distribution (Mw / Mn) of 1.04, and the ratio of styrene block to isobutylene block was 95: 5.
- the hydrogenation reaction of the obtained block copolymer was performed in the same manner as in Production Example 1.
- the weight average molecular weight (Mw) of the block copolymer hydride obtained by the hydrogenation reaction was 53000, and the molecular weight distribution (Mw / Mn) was 1.04.
- the resulting block polymer hydride was pelletized.
- the resulting block copolymer hydride had a weight average molecular weight (Mw) of 52200, a molecular weight distribution (Mw / Mn) of 1.05, and a hydrogenation rate of almost 100%.
- this pellet resin is appropriately referred to as “resin D”.
- Example 1 A film forming apparatus for three-layer / three-layer co-extrusion molding having three single-screw extruders a, b and c equipped with a double flight type screw was prepared.
- the three-type three-layer film forming apparatus represents a film forming apparatus capable of producing a film having a three-layer structure using three types of resins.
- the film forming apparatus used in this example is provided with a resin layer charged in the uniaxial extruder a, a resin layer charged in the uniaxial stretching machine b, and a resin layer charged in the uniaxial stretching machine c in this order. It was provided so that a film could be manufactured.
- Resin A pellets were put into a single screw extruder a and a single screw extruder c.
- pellets of norbornene-based resin (“Zeonor 1600” manufactured by Nippon Zeon Co., Ltd.) were charged into the single screw extruder b. Thereafter, the resins charged in the uniaxial stretching machines a, b and c were melted at an extrusion temperature of 260 ° C., respectively.
- the melted resin A and norbornene-based resin were supplied to a multi-manifold die through a leaf disk-shaped polymer filter having an opening of 10 ⁇ m, and extruded from the multi-manifold die at 260 ° C. simultaneously.
- the extruded film-like molten resin is cast on a cooling roll adjusted to a surface temperature of 100 ° C., and then passed between two cooling rolls adjusted to a surface temperature of 50 ° C.
- An optical film having a thickness of 50 ⁇ m was obtained, comprising (thickness 5 ⁇ m) / second layer made of norbornene resin (thickness 40 ⁇ m) / third layer made of resin A (thickness 5 ⁇ m) in this order.
- the obtained optical film was evaluated by the method described above.
- Example 2 An optical film was produced and evaluated in the same manner as in Example 1 except that Resin B was used instead of Resin A.
- Example 3 An optical film was produced and evaluated in the same manner as in Example 1 except that Resin C was used instead of Resin A.
- Example 4 An optical film was produced and evaluated in the same manner as in Example 1 except that Resin D was used instead of Resin A.
- the optical films of Examples 1 to 4 have high folding resistance, low water absorption, and excellent tensile modulus and total light transmittance. Therefore, according to the present invention, it has been confirmed that an optical film excellent in bending resistance can be realized while having characteristics similar to those of a film made of a conventional norbornene resin.
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Abstract
Description
すなわち、本発明は下記の通りである。
ノルボルネン系重合体を含む第二層、及び、
芳香族ビニル化合物/共役ジエン化合物ブロック共重合体の水素化物を含む第三層を、この順に備える、光学フィルム。
〔2〕 前記芳香族ビニル化合物/共役ジエン化合物ブロック共重合体の水素化物が、スチレン/イソプレン共重合体の水素化物である、〔1〕記載の光学フィルム。
〔3〕 前記スチレン/イソプレン共重合体の水素化物におけるスチレン/イソプレンの共重合比が50/50~90/10である、〔2〕記載の光学フィルム。
〔4〕 ASTM D570で測定した吸水率が0.1重量%以下である、〔1〕~〔3〕のいずれか1項に記載の光学フィルム。
以下の説明において、「偏光板」とは、別に断らない限り、剛直な部材だけでなく、例えば樹脂製のフィルムのように可撓性を有する部材も含む。
本発明の光学フィルムは、第一層、第二層及び第三層をこの順に備える複層構造のフィルムである。
第一層は、芳香族ビニル化合物/共役ジエン化合物ブロック共重合体の水素化物を含む。したがって、第一層は、通常、芳香族ビニル化合物/共役ジエン化合物ブロック共重合体の水素化物を含む樹脂からなる樹脂層である。以下、前記の芳香族ビニル化合物/共役ジエン化合物ブロック共重合体の水素化物を含む樹脂を、適宜「水添重合体樹脂」ということがある。この水添重合体樹脂は、通常、熱可塑性樹脂である。
ブロック共重合体が鎖状型ブロックの形態を有する場合、その両端が重合体ブロック[A]であることが好ましい。これにより、水添重合体樹脂のベタツキを低い値に抑えることができる。
また、ブロック共重合体の分子量分布(Mw/Mn)は、好ましくは3以下、より好ましくは2以下、特に好ましくは1.5以下である。
かかる重合体ブロック[A]の一端において、共役ジエン化合物を含有するモノマー組成物(b1)を重合させて重合体ブロック[B]を形成し、[A]-[B]のジブロックの重合体を形成する第二工程と、
かかるジブロックの重合体の、ブロック[B]側の末端において、芳香族ビニル化合物を含有するモノマー組成物(a2)を重合させて、ブロック共重合体を得る第三工程とを有する方法。ただし、モノマー組成物(a1)とモノマー組成物(a2)とは、同一でも異なっていてもよい。
かかる重合体ブロック[A]の一端において、共役ジエン化合物を含有するモノマー組成物(b1)を重合させて重合体ブロック[B]を形成し、[A]-[B]のジブロックの重合体を形成する第二工程と、
かかるジブロックの重合体の、重合体ブロック[B]側の末端同士を、カップリング剤によりカップリングさせて、ブロック共重合体を得る第三工程とを有する方法。
リビングアニオン重合を行う場合は、重合開始剤として、例えば、n-ブチルリチウム、sec-ブチルリチウム、t-ブチルリチウム、ヘキシルリチウム等のモノ有機リチウム;ジリチオメタン、1,4-ジリチオブタン、1,4-ジリチオ-2-エチルシクロヘキサン等の多官能性有機リチウム化合物;などを用いうる。これらは、1種類を単独で用いてもよく、2種類以上を任意の比率で組み合わせて用いてもよい。
溶液重合を行う場合、溶媒としては、各工程で得られる重合体が溶解しうる不活性溶媒を用いうる。不活性溶媒としては、例えば、n-ペンタン、イソペンタン、n-ヘキサン、n-ヘプタン、イソオクタン等の脂肪族炭化水素溶媒;シクロペンタン、シクロヘキサン、メチルシクロペンタン、メチルシクロヘキサン、デカリン等の脂環式炭化水素溶媒;ベンゼン、トルエン等の芳香族炭化水素溶媒;などが挙げられる。これらは、1種類を単独で用いてもよく、2種類以上を任意の比率で組み合わせて用いてもよい。中でも、溶媒として脂環式炭化水素溶媒を用いると、水素化反応に不活性な溶媒としてそのまま使用でき、ブロック共重合体の溶解性も良好であるため、好ましい。溶媒の使用量は、全使用モノマー100重量部に対して、好ましくは200重量部~2000重量部である。
また、芳香族性の炭素-炭素不飽和結合の水素化率は、好ましくは90%以上、より好ましくは93%以上、特に好ましくは95%以上である。芳香環の炭素-炭素不飽和結合の水素化率を高めることにより、重合体ブロック[A]を水素化して得られる重合体ブロックのガラス転移温度が高くなるので、水添重合体樹脂の耐熱性を効果的に高めることができる。
アルコキシシリル基の導入量は、1H-NMRスペクトル(導入量が少ない場合は積算回数を増やす)にて計測しうる。
ニッケル、コバルト、チタン又は鉄の化合物としては、例えば、各金属のアセチルアセトナト化合物、カルボン酸塩、シクロペンタジエニル化合物等が挙げられる。
また、有機金属化合物としては、例えば、トリエチルアルミニウム、トリイソブチルアルミニウム等のアルキルアルミニウム、ジエチルアルミニウムクロリド、エチルアルミニウムジクロリド等のハロゲン化アルミニウム、ジイソブチルアルミニウムハイドライド等の水素化アルキルアルミニウムなどの有機アルミニウム化合物;並びに有機リチウム化合物などが挙げられる。
有機金属錯体触媒としては、例えば、ジヒドリド-テトラキス(トリフェニルホスフィン)ルテニウム、ジヒドリド-テトラキス(トリフェニルホスフィン)鉄、ビス(シクロオクタジエン)ニッケル、ビス(シクロペンタジエニル)ニッケル等の遷移金属錯体が挙げられる。
可塑剤の量は、水添重合体樹脂100重量部に対して、好ましくは40重量部以下で、樹脂特性を調整する目的に合わせて適宜選択される。
光安定剤の量は、ブロック共重合体の水素化物100重量部に対して、好ましくは0.01重量部以上、より好ましくは0.02重量部以上、特に好ましくは0.03重量部以上であり、好ましくは5重量部以下、より好ましくは2重量部以下、特に好ましくは1重量部以下である。光安定剤の量を前記範囲の下限値以上とすることにより、水添重合体樹脂の耐候性を高くできる。また、上限値以下とすることにより、水添重合体樹脂を成形する際に、押出し機のTダイ及び冷却ロールの汚れを防止でき、加工性を高めることができる。
紫外線吸収剤の量は、ブロック共重合体の水素化物100重量部に対して、好ましくは0.01重量部以上、より好ましくは0.02重量部以上、特に好ましくは0.04重量部以上であり、好ましくは1重量部以下、より好ましくは0.5重量部以下、特に好ましくは0.3重量部以下である。紫外線吸収剤を前記範囲の下限値以上用いることにより、水添重合体樹脂の耐光性を改善することができるが、上限を超えて過剰に用いても、更なる改善は得られ難い。
酸化防止剤の量は、ブロック共重合体の水素化物100重量部に対して、好ましくは0.01重量部以上、より好ましくは0.05重量部以上、特に好ましくは0.1重量部以上であり、好ましくは1重量部以下、より好ましくは0.5重量部以下、特に好ましくは0.3重量部以下である。酸化防止剤を前記範囲の下限値以上用いることにより、水添重合体樹脂の熱安定性を改善することができるが、上限を超えて過剰に用いても、更なる改善は得られ難い。
第二層は、ノルボルネン系重合体を含む。したがって、第二層は、通常、ノルボルネン系重合体を含む樹脂からなる樹脂層である。以下、ノルボルネン系重合体を含む樹脂を、適宜「ノルボルネン系樹脂」ということがある。このノルボルネン系樹脂は、通常、熱可塑性樹脂である。
第三層は、芳香族ビニル化合物/共役ジエン化合物ブロック共重合体の水素化物を含む。したがって、第三層は、通常、芳香族ビニル化合物/共役ジエン化合物ブロック共重合体の水素化物を含む水添重合体樹脂からなる樹脂層である。
光学フィルムは、本発明の効果を著しく損なわない限り、上述した第一層、第二層及び第三層に組み合わせて、任意の層を備えうる。ただし、光学フィルムを薄くする観点から、光学フィルムは第一層、第二層及び第三層を備える3層構造のフィルムであることが好ましい。
上述した光学フィルムは、耐折り曲げ性に優れる。そのため、光学フィルムは、屈曲動作を伴う用途に用いても、破損し難い。光学フィルムの耐折り曲げ性は、耐折度によって評価しうる。光学フィルムの耐折度は、通常500以上、好ましくは1000以上、より好ましくは1500以上である。光学フィルムの耐折度の上限は、特に限定されないが、例えば1,000,000以下としうる。
試料としての光学フィルムから、幅15mm±0.1mm、長さ約110mmの試験片を切り出す。この際、光学フィルムが延伸処理を経て製造されたフィルムである場合は、最も強く延伸された方向が試験片の約110mmの辺と平行になるように試験片を作製する。その後、MIT耐折度試験機(安田精機製作所製「No.307」)を用いて、荷重9.8N、屈曲部の曲率0.38±0.02mm、折り曲げ角度135°±2°、折り曲げ速度175回/分の条件で、試験片の幅方向に折れ目が現れるように、前記の試験片を折り曲げる。この折り曲げを継続し、試験片が破断するまでの往復折り曲げ回数を測定する。
10枚の試験片を作製して、前記の方法により、試験片が破断するまでの往復折り曲げ回数を10回測定する。こうして測定された10回の測定値の平均を、当該光学フィルムの耐折度(MIT耐折回数)とする。
光学フィルムの製造方法に制限は無い。光学フィルムは、例えば、水添重合体樹脂及びノルボルネン系樹脂をフィルム状に成形する工程を含む製造方法により、製造し得る。
冷却ロールの数は、特に制限されず、通常は2本以上である。冷却ロールの配置方法としては、例えば、直線型、Z型、L型などが挙げられる。この際、ダイから押出された溶融樹脂の冷却ロールへの通し方は特に制限されない。
例えば、光学フィルムの製造方法は、光学フィルムに延伸処理を施す工程を含んでいてもよい。延伸処理を施すことにより、光学フィルムに所望のレターデーションを発現させたり、光学フィルムの機械的特性を改善したりできる。
また、例えば、光学フィルムの製造方法は、光学フィルムに表面処理を施す工程を含んでいてもよい。
光学フィルムの用途は、任意である。光学フィルムの用途は、例えば、位相差フィルム、偏光板保護フィルム、光学装置用の封止フィルム、有機エレクトロルミネッセンス素子用の基材フィルム、フレキシブル電極用の基材フィルム、タッチパネル用の基材フィルムなどが挙げられる。
以下の説明において、量を表す「%」及び「部」は、別に断らない限り重量基準である。また、以下に説明する操作は、別に断らない限り、常温常圧大気中において行った。
〔引張弾性率の測定方法〕
光学フィルムの引張弾性率は、JIS K 7161に準拠して測定した。
光学フィルムの耐折度は、JIS P 8115「紙及び板紙-耐折強さ試験方法-MIT試験機法」に準拠したMIT耐折試験により、下記の手順で測定した。
試料としての光学フィルムから、幅15mm±0.1mm、長さ約110mmの試験片を切り出した。MIT耐折度試験機(安田精機製作所製「No.307」)を用いて、荷重9.8N、屈曲部の曲率0.38±0.02mm、折り曲げ角度135°±2°、折り曲げ速度175回/分の条件で、試験片の幅方向に折れ目が現れるように、前記の試験片を折り曲げた。この折り曲げを継続し、試験片が破断するまでの往復折り曲げ回数を測定した。
10枚の試験片を作製して、前記の方法により、試験片が破断するまでの往復折り曲げ回数を10回測定した。こうして測定された10回の測定値の平均を、当該フィルムの耐折度(MIT耐折回数)とした。
光学フィルムの全光線透過率は、紫外・可視分光計を用いて、波長400nm~700nmの範囲で測定した。
光学フィルムの吸水率は、ASTM D570に従って測定した値である。具体的には、100mm×100mmのフィルムを23℃の水中で1時間浸漬し、その増加重量を測定することにより算出した。
(ブロック共重合体の製造)
内部が充分に窒素置換された、攪拌装置を備えた反応器に、脱水シクロヘキサン550部、脱水スチレン30.0部、及び、n-ジブチルエーテル0.475部を入れた。全容を60℃で攪拌しながら、n-ブチルリチウム(15%シクロヘキサン溶液)0.83部を加えて重合を開始させ、60℃で攪拌しながら、さらに60分反応させた。反応液をガスクロマトグラフィーにより測定したところ、この時点で重合転化率は99.5%であった。
その後、反応液に脱水イソプレン40.0部を加え、そのまま60℃で30分攪拌を続けた。反応液をガスクロマトグラフィーにより測定したところ、この時点で重合転化率は99%であった。
その後さらに、反応液に脱水スチレンを30.0部加え、全容を60℃で60分攪拌した。反応液をガスクロマトグラフィーにより測定したところ、この時点での重合転化率はほぼ100%であった。
ここでイソプロピルアルコール0.5部を加えて反応を停止させて、ブロック共重合体を含む重合体溶液を得た。得られたブロック共重合体の重量平均分子量(Mw)は48,300、分子量分布(Mw/Mn)は1.03、スチレンブロックとイソブチレンブロックの割合は重量比で60:40であった。
次に、上記重合体溶液を、攪拌装置を備えた耐圧反応器に移送し、水素化触媒として珪藻土担持型ニッケル触媒(日揮触媒化成社製「E22U」、ニッケル担持量60%)4.0部及び脱水シクロヘキサン100部を添加して混合した。反応器内部を水素ガスで置換し、更に溶液を攪拌しながら水素を供給し、温度170℃、圧力4.5MPaにて6時間水素化反応を行った。水素化反応により得られたブロック共重合体水素化物の重量平均分子量(Mw)は51,500、分子量分布(Mw/Mn)は1.04であった。
水素化反応終了後、反応液を濾過して水素化触媒を除去した。その後、濾液にフェノール系酸化防止剤であるペンタエリスリチル・テトラキス[3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート](コーヨ化学研究所社製「Songnox1010」)0.05重量部を溶解したキシレン溶液1.0部を添加して溶解させた。次いで、上記溶液を、ゼータプラス(登録商標)フィルター30H(キュノ社製、孔径0.5μm~1μm)にて濾過し、更に別の金属ファイバー製フィルター(ニチダイ社製、孔径0.4μm)にて順次濾過して、微小な固形分を除去した。その後、円筒型の濃縮乾燥器(日立製作所社製、コントロ)を用いて、温度260℃、圧力0.001MPa以下で、溶液から、溶媒であるシクロヘキサン、キシレン及びその他の揮発成分を除去した。残った固形分を、濃縮乾燥器に直結したダイから溶融状態でストランド状に押し出し、冷却後、ペレタイザーでカットして、ブロック共重合体水素化物を含むペレット95部を得た。得られたペレットのブロック共重合体水素化物の重量平均分子量(Mw)は50,300、分子量分布(Mw/Mn)は1.05、水素化率はほぼ100%であった。以下、このペレットの樹脂を、適宜「樹脂A」と呼ぶ。
内部が充分に窒素置換された、攪拌装置を備えた反応器に、脱水シクロヘキサン550部、脱水スチレン45.0部、及び、n-ジブチルエーテル0.475部を入れた。全容を60℃で攪拌しながら、n-ブチルリチウム(15%シクロヘキサン溶液)0.83部を加えて重合を開始させ、60℃で攪拌しながら、さらに60分反応させた。反応液をガスクロマトグラフィーにより測定したところ、この時点で重合転化率は99.5%であった。
その後、反応液に脱水イソプレン10.0部を加え、そのまま60℃で30分攪拌を続けた。反応液をガスクロマトグラフィーにより測定したところ、この時点で重合転化率は99%であった。
その後さらに、反応液に脱水スチレンを45.0部加え、全容を60℃で60分攪拌した。反応液をガスクロマトグラフィーにより測定したところ、この時点での重合転化率はほぼ100%であった。
ここでイソプロピルアルコール0.5部を加えて反応を停止させて、ブロック共重合体を含む重合体溶液を得た。得られたブロック共重合体の重量平均分子量(Mw)は50,400、分子量分布(Mw/Mn)は1.03、スチレンブロックとイソブチレンブロックの割合は重量比で90:10であった。
内部が充分に窒素置換された、攪拌装置を備えた反応器に、脱水シクロヘキサン550部、脱水スチレン37.5部、及び、n-ジブチルエーテル0.475部を入れた。全容を60℃で攪拌しながら、n-ブチルリチウム(15%シクロヘキサン溶液)0.83部を加えて重合を開始させ、60℃で攪拌しながら、さらに60分反応させた。反応液をガスクロマトグラフィーにより測定したところ、この時点で重合転化率は99.5%であった。
その後、反応液に脱水イソプレン25.0部を加え、そのまま60℃で30分攪拌を続けた。反応液をガスクロマトグラフィーにより測定したところ、この時点で重合転化率は99%であった。
その後さらに、反応液に脱水スチレンを37.5部加え、全容を60℃で60分攪拌した。反応液をガスクロマトグラフィーにより測定したところ、この時点での重合転化率はほぼ100%であった。
ここでイソプロピルアルコール0.5部を加えて反応を停止させて、ブロック共重合体を含む重合体溶液を得た。得られたブロック共重合体の重量平均分子量(Mw)は54000、分子量分布(Mw/Mn)は1.04、スチレンブロックとイソブチレンブロックの割合は重量比で75:25であった。
内部が充分に窒素置換された、攪拌装置を備えた反応器に、脱水シクロヘキサン550部、脱水スチレン47.5部、及び、n-ジブチルエーテル0.475部を入れた。全容を60℃で攪拌しながら、n-ブチルリチウム(15%シクロヘキサン溶液)0.83部を加えて重合を開始させ、60℃で攪拌しながら、さらに60分反応させた。反応液をガスクロマトグラフィーにより測定したところ、この時点で重合転化率は99.5%であった。
その後、反応液に脱水イソプレン5.0部を加え、そのまま60℃で30分攪拌を続けた。反応液をガスクロマトグラフィーにより測定したところ、この時点で重合転化率は99%であった。
その後さらに、反応液に脱水スチレンを47.5部加え、全容を60℃で60分攪拌した。反応液をガスクロマトグラフィーにより測定したところ、この時点での重合転化率はほぼ100%であった。
ここでイソプロピルアルコール0.5部を加えて反応を停止させて、ブロック共重合体を含む重合体溶液を得た。得られたブロック共重合体の重量平均分子量(Mw)は54000、分子量分布(Mw/Mn)は1.04、スチレンブロックとイソブチレンブロックの割合は重量比で95:5であった。
ダブルフライト型のスクリューを備えた3つの一軸押出機a、b及びcを有する3種3層の共押出成形用のフィルム成形装置を準備した。ここで、3種3層のフィルム成形装置とは、3種類の樹脂を用いて3層構造のフィルムを製造しうるフィルム成形装置を表す。本実施例で使用したフィルム成形装置は、一軸押出機aに投入された樹脂の層、一軸延伸機bに投入された樹脂の層及び一軸延伸機cに投入された樹脂の層をこの順に備えるフィルムを製造しうるように設けられていた。
得られた光学フィルムについて、上述した方法により評価を行った。
樹脂Aの代わりに樹脂Bを用いたこと以外は実施例1と同様にして、光学フィルムの製造及び評価を行った。
樹脂Aの代わりに樹脂Cを用いたこと以外は実施例1と同様にして、光学フィルムの製造及び評価を行った。
樹脂Aの代わりに樹脂Dを用いたこと以外は実施例1と同様にして、光学フィルムの製造及び評価を行った。
樹脂Aの代わりにノルボルネン系樹脂を用いたこと以外は実施例1と同様にして、ノルボルネン系樹脂からなる層のみを備えた単層構造の光学フィルムの製造及び評価を行った。
ノルボルネン系樹脂の代わりに樹脂Aを用いたこと以外は実施例1と同様にして、樹脂Aからなる層のみを備えた単層構造の光学フィルムの製造及び評価を行った。
上述した実施例及び比較例の結果を、下記の表1に示す。下記の表1において、略称の意味は、以下の通りである。
St/IP比:芳香族ビニル化合物/共役ジエン化合物ブロック共重合体の水素化物におけるスチレンとイソプレンとの重量比(スチレン/イソプレン)
ZNR:ノルボルネン系樹脂
弾性率:光学フィルムの引張弾性率
透過率:光学フィルムの全光線透過率
表1から分かるように、実施例1~4の光学フィルムは、耐折度が大きく、吸水率が低く、且つ、引張弾性率及び全光線透過率の両方に優れる。したがって、本発明により、従来のノルボルネン系樹脂からなるフィルムと同程度の特性を有しながら、耐折り曲げ性に優れる光学フィルムを実現できることが確認された。
Claims (4)
- 芳香族ビニル化合物/共役ジエン化合物ブロック共重合体の水素化物を含む第一層、
ノルボルネン系重合体を含む第二層、及び、
芳香族ビニル化合物/共役ジエン化合物ブロック共重合体の水素化物を含む第三層を、この順に備える、光学フィルム。 - 前記芳香族ビニル化合物/共役ジエン化合物ブロック共重合体の水素化物が、スチレン/イソプレン共重合体の水素化物である、請求項1記載の光学フィルム。
- 前記スチレン/イソプレン共重合体の水素化物におけるスチレン/イソプレンの共重合比が50/50~90/10である、請求項2記載の光学フィルム。
- ASTM D570で測定した吸水率が0.1重量%以下である、請求項1~3のいずれか1項に記載の光学フィルム。
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WO2019151027A1 (ja) * | 2018-02-02 | 2019-08-08 | 日本ゼオン株式会社 | 積層フィルム及びその製造方法並びに偏光板 |
US11390706B2 (en) * | 2018-02-02 | 2022-07-19 | Zeon Corporation | Laminated film, method for producing same, and polarizing plate |
JP7173053B2 (ja) | 2018-02-02 | 2022-11-16 | 日本ゼオン株式会社 | 積層フィルム及びその製造方法並びに偏光板 |
JPWO2019151027A1 (ja) * | 2018-02-02 | 2021-01-28 | 日本ゼオン株式会社 | 積層フィルム及びその製造方法並びに偏光板 |
KR20210056330A (ko) | 2018-09-07 | 2021-05-18 | 니폰 제온 가부시키가이샤 | 광학 적층 필름 및 도전 필름 |
JPWO2020110673A1 (ja) * | 2018-11-30 | 2021-10-14 | 日本ゼオン株式会社 | 光学フィルム、位相差フィルム、及びそれらの製造方法 |
WO2020110673A1 (ja) * | 2018-11-30 | 2020-06-04 | 日本ゼオン株式会社 | 光学フィルム、位相差フィルム、及びそれらの製造方法 |
JP7338639B2 (ja) | 2018-11-30 | 2023-09-05 | 日本ゼオン株式会社 | 光学フィルム、位相差フィルム、及びそれらの製造方法 |
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TWI700184B (zh) | 2020-08-01 |
US10549514B2 (en) | 2020-02-04 |
TW201641290A (zh) | 2016-12-01 |
JPWO2016152871A1 (ja) | 2018-01-18 |
CN107428137A (zh) | 2017-12-01 |
JP6690635B2 (ja) | 2020-04-28 |
US20180065348A1 (en) | 2018-03-08 |
KR20170130413A (ko) | 2017-11-28 |
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