JP6591858B2 - Thermoplastic resin and optical member - Google Patents
Thermoplastic resin and optical member Download PDFInfo
- Publication number
- JP6591858B2 JP6591858B2 JP2015209020A JP2015209020A JP6591858B2 JP 6591858 B2 JP6591858 B2 JP 6591858B2 JP 2015209020 A JP2015209020 A JP 2015209020A JP 2015209020 A JP2015209020 A JP 2015209020A JP 6591858 B2 JP6591858 B2 JP 6591858B2
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- Prior art keywords
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- carbon atoms
- thermoplastic resin
- formula
- resin according
- Prior art date
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- 229920005992 thermoplastic resin Polymers 0.000 title claims description 75
- 230000003287 optical effect Effects 0.000 title claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 61
- 238000005452 bending Methods 0.000 claims description 26
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 125000005587 carbonate group Chemical group 0.000 claims description 5
- 229920000515 polycarbonate Polymers 0.000 claims description 5
- 239000004417 polycarbonate Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000010408 film Substances 0.000 description 26
- 229920005668 polycarbonate resin Polymers 0.000 description 26
- 239000004431 polycarbonate resin Substances 0.000 description 26
- 239000008188 pellet Substances 0.000 description 22
- 238000000034 method Methods 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000007334 copolymerization reaction Methods 0.000 description 13
- 238000000465 moulding Methods 0.000 description 13
- -1 spiroglycol Chemical compound 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 7
- 238000005809 transesterification reaction Methods 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001746 injection moulding Methods 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 5
- 150000004650 carbonic acid diesters Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 239000002685 polymerization catalyst Substances 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 4
- 230000004075 alteration Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000000748 compression moulding Methods 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000005453 pelletization Methods 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000012788 optical film Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- UTNSTOOXQPHXJQ-UHFFFAOYSA-N 2-[4-[4-(2-hydroxyethoxy)phenyl]sulfonylphenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1S(=O)(=O)C1=CC=C(OCCO)C=C1 UTNSTOOXQPHXJQ-UHFFFAOYSA-N 0.000 description 2
- NQXNYVAALXGLQT-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1(C=2C=CC(OCCO)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 NQXNYVAALXGLQT-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- NUDSREQIJYWLRA-UHFFFAOYSA-N 4-[9-(4-hydroxy-3-methylphenyl)fluoren-9-yl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(O)=CC=2)=C1 NUDSREQIJYWLRA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- UCVMQZHZWWEPRC-UHFFFAOYSA-L barium(2+);hydrogen carbonate Chemical compound [Ba+2].OC([O-])=O.OC([O-])=O UCVMQZHZWWEPRC-UHFFFAOYSA-L 0.000 description 2
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 2
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 2
- 229940031993 lithium benzoate Drugs 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 description 2
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 2
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 2
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 2
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 2
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 2
- 239000002370 magnesium bicarbonate Substances 0.000 description 2
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 239000004300 potassium benzoate Substances 0.000 description 2
- 235000010235 potassium benzoate Nutrition 0.000 description 2
- 229940103091 potassium benzoate Drugs 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 229940114930 potassium stearate Drugs 0.000 description 2
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 229960003885 sodium benzoate Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910000018 strontium carbonate Inorganic materials 0.000 description 2
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 2
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 2
- RXSHXLOMRZJCLB-UHFFFAOYSA-L strontium;diacetate Chemical compound [Sr+2].CC([O-])=O.CC([O-])=O RXSHXLOMRZJCLB-UHFFFAOYSA-L 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- VLCQYXZALXDPEV-UHFFFAOYSA-N (2,3,4-triethylphenyl)boron Chemical compound [B]C1=CC=C(CC)C(CC)=C1CC VLCQYXZALXDPEV-UHFFFAOYSA-N 0.000 description 1
- PJAWEFMLSSLAIM-UHFFFAOYSA-N (2,3,4-trimethylphenyl)boron Chemical compound [B]C1=CC=C(C)C(C)=C1C PJAWEFMLSSLAIM-UHFFFAOYSA-N 0.000 description 1
- IHPFDBSMYWRYHQ-UHFFFAOYSA-N (2-benzylphenyl)-diphenylborane Chemical compound C=1C=CC=C(B(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1CC1=CC=CC=C1 IHPFDBSMYWRYHQ-UHFFFAOYSA-N 0.000 description 1
- GCLVVFYKIZYIIL-UHFFFAOYSA-N (2-butylphenyl)-diphenylborane Chemical compound CCCCC1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 GCLVVFYKIZYIIL-UHFFFAOYSA-N 0.000 description 1
- KBIWOGUYLGWUTF-UHFFFAOYSA-N (2-methylphenyl)-diphenylborane Chemical compound CC1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 KBIWOGUYLGWUTF-UHFFFAOYSA-N 0.000 description 1
- GPFJHNSSBHPYJK-UHFFFAOYSA-N (3-methylphenyl) hydrogen carbonate Chemical compound CC1=CC=CC(OC(O)=O)=C1 GPFJHNSSBHPYJK-UHFFFAOYSA-N 0.000 description 1
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 1
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- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- KDQQMEAEIKFPLQ-UHFFFAOYSA-N n-(1-cyanocyclohexyl)-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC1(C#N)CCCCC1 KDQQMEAEIKFPLQ-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
- QIXYEYFEDNMCCE-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid;naphthalene-2,7-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21.C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 QIXYEYFEDNMCCE-UHFFFAOYSA-N 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- GVMDZMPQYYHMSV-UHFFFAOYSA-N octyl benzenesulfonate Chemical compound CCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVMDZMPQYYHMSV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- LYTNHSCLZRMKON-UHFFFAOYSA-L oxygen(2-);zirconium(4+);diacetate Chemical compound [O-2].[Zr+4].CC([O-])=O.CC([O-])=O LYTNHSCLZRMKON-UHFFFAOYSA-L 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- AJDJKHROQJQURF-UHFFFAOYSA-N phenanthrene-1,2-dicarboxylic acid Chemical compound C1=CC=C2C3=CC=C(C(=O)O)C(C(O)=O)=C3C=CC2=C1 AJDJKHROQJQURF-UHFFFAOYSA-N 0.000 description 1
- RKHQZMOCQHXUBC-UHFFFAOYSA-N phenol;potassium Chemical compound [K].OC1=CC=CC=C1 RKHQZMOCQHXUBC-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- KZQFPRKQBWRRHQ-UHFFFAOYSA-N phenyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=CC=C1 KZQFPRKQBWRRHQ-UHFFFAOYSA-N 0.000 description 1
- CGEXUOTXYSGBLV-UHFFFAOYSA-N phenyl benzenesulfonate Chemical compound C=1C=CC=CC=1S(=O)(=O)OC1=CC=CC=C1 CGEXUOTXYSGBLV-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 159000000008 strontium salts Chemical class 0.000 description 1
- WJMMDJOFTZAHHS-UHFFFAOYSA-L strontium;carbonic acid;carbonate Chemical compound [Sr+2].OC([O-])=O.OC([O-])=O WJMMDJOFTZAHHS-UHFFFAOYSA-L 0.000 description 1
- FRKHZXHEZFADLA-UHFFFAOYSA-L strontium;octadecanoate Chemical compound [Sr+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O FRKHZXHEZFADLA-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical class CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
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- Manufacture Of Macromolecular Shaped Articles (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
本発明は、高屈折率、高アッベ数であり、かつ、耐折り曲げ性に優れた熱可塑性樹脂に関する。また、該熱可塑性樹脂からなる光学部材に関する。 The present invention relates to a thermoplastic resin having a high refractive index, a high Abbe number, and excellent bending resistance. The present invention also relates to an optical member made of the thermoplastic resin.
２，２−ビス（４−ヒドロキシフェニル）プロパン（通称ビスフェノールＡ）とホスゲンあるいは炭酸ジフェニルなどの炭酸エステル形成性化合物と反応させて製造される従来のポリカーボネート樹脂は、透明性が高く、耐熱性や耐衝撃性に優れるため、光ディスク等の光学部材に使用されてきた。しかしながら、屈折率が低く、複屈折が大きく、表面が傷つきやすいといった欠点があり、使用用途が限られていた。高屈折化、低複屈折化する方法として、側鎖にフルオレン構造を有するビスフェノール類の共重合が報告されている。（特許文献１，２，３）。しかしながら、特許文献１のポリカーボネート樹脂は、溶融時の粘度が極めて高く、光学レンズや光ディスクなどを成形するのは困難である。また、特許文献２や特許文献３のポリカーボネート樹脂は、成形上の問題のない溶融粘度を有するポリカーボネートであり、光ディスクに好適との記載があるが、光学レンズに使用するには屈折率が不十分であった。
A conventional polycarbonate resin produced by reacting 2,2-bis (4-hydroxyphenyl) propane (commonly called bisphenol A) with a carbonate ester-forming compound such as phosgene or diphenyl carbonate has high transparency, heat resistance, Since it has excellent impact resistance, it has been used for optical members such as optical disks. However, the refractive index is low, the birefringence is large, and the surface is easily damaged. Copolymerization of bisphenols having a fluorene structure in the side chain has been reported as a method for increasing the refractive index and reducing the birefringence. (
そこで、さらに高屈折率であるポリカーボネート樹脂が提案されている（特許文献４，５）。しかしながら、特許文献４，５に記載のポリカーボネート樹脂は脆いため、射出成形時に成形片やスプルーが折れやすいという問題があった。また、光学フィルムとして使用する際に、耐折り曲げ性が不十分であるといった問題もあった。 Therefore, a polycarbonate resin having a higher refractive index has been proposed (Patent Documents 4 and 5). However, since the polycarbonate resins described in Patent Documents 4 and 5 are brittle, there is a problem that the molded piece and the sprue are easily broken during injection molding. Moreover, when using as an optical film, there also existed a problem that bending resistance was inadequate.
そこで本発明の目的は、高屈折率、高アッベ数であり、かつ、耐折り曲げ性に優れた熱可塑性樹脂を提供することにある。また、該熱可塑性樹脂からなる光学部材を提供することにある。 Therefore, an object of the present invention is to provide a thermoplastic resin having a high refractive index, a high Abbe number, and excellent bending resistance. Moreover, it is providing the optical member which consists of this thermoplastic resin.
本発明者らはこの目的を達成せんとして鋭意研究を重ねた結果、下記熱可塑性樹脂及び光学部材によって、上記課題を解決することができることを見出し本発明に到達した。 The inventors of the present invention have intensively studied to achieve this object, and as a result, have found that the above problems can be solved by the following thermoplastic resin and optical member, and have reached the present invention.
すなわち、本発明は、
１．式（１）と式（２）で表される構成単位を含み、式（１）と式（２）との割合がモル比で７５：２５〜１０：９０の範囲で構成されたポリカーボネートまたはポリエステルカーボネートである熱可塑性樹脂。
２．式（１）で表される単位と式（２）で表される単位との割合がモル比で５０：５０〜１０：９０の範囲で構成された前記１に記載の熱可塑性樹脂。
３．式（１）で表される単位において、Ｒ１、Ｒ２が水素原子、Ｘがエチレン基、ｍ、ｎが１である上記１〜２のいずれかに記載の熱可塑性樹脂。
４．式（２）で表される単位において、Ｒ３、Ｒ４がフェニル基、Ｙがエチレン基、ｏ、ｐが１である前記１〜３のいずれかに記載の熱可塑性樹脂。
５．式（２）で表される単位において、Ｒ３、Ｒ４が水素原子、Ｙがエチレン基、ｏ、ｐが１である前記１〜３のいずれかに記載の熱可塑性樹脂。
６．熱可塑性樹脂中のエステル基のモル量がエステル基とカーボネート基の合計モル量の０〜５０モル％である前記１〜５のいずれかに記載の熱可塑性樹脂。
７．比粘度が０．１２〜０．４０である前記１〜６のいずれかに記載の熱可塑性樹脂。
８．アッベ数が２３〜２６である前記１〜７のいずれかに記載の熱可塑性樹脂。
９．屈折率が１．６３５〜１．６６０である前記１〜８のいずれかに記載の熱可塑性樹脂。
１０．配向複屈折の絶対値が６×１０−３以下である前記１〜９のいずれかに記載の熱可塑性樹脂。
１１．耐折り曲げ性が２０ｍｍ以下である前記１〜１０のいずれかに記載の熱可塑性樹脂。
１２．前記１〜１１のいずれかに記載の熱可塑性樹脂からなる光学部材。
１３．前記１〜１１のいずれかに記載の熱可塑性樹脂からなる光学レンズ。
１４．前記１〜１１のいずれかに記載の熱可塑性樹脂からなる透明フィルム。
That is, the present invention
1. Polycarbonate or polyester comprising structural units represented by formula (1) and formula (2), wherein the ratio of formula (1) and formula (2) is in a molar ratio of 75:25 to 10:90 A thermoplastic resin that is carbonate .
2 . 2. The thermoplastic resin according to 1 above, wherein the ratio of the unit represented by the formula (1) and the unit represented by the formula (2) is 50:50 to 10:90 in a molar ratio.
3 . The thermoplastic resin according to any one of 1 to 2 above, wherein in the unit represented by the formula (1), R 1 and R 2 are hydrogen atoms, X is an ethylene group, and m and n are 1.
4 . The thermoplastic resin according to any one of 1 to 3 , wherein in the unit represented by the formula (2), R 3 and R 4 are a phenyl group, Y is an ethylene group, o and p are 1.
5 . The thermoplastic resin according to any one of 1 to 3 , wherein in the unit represented by the formula (2), R 3 and R 4 are hydrogen atoms, Y is an ethylene group, o and p are 1.
6 . The thermoplastic resin according to any one of 1 to 5 , wherein the molar amount of the ester group in the thermoplastic resin is 0 to 50 mol% of the total molar amount of the ester group and the carbonate group.
7 . The thermoplastic resin according to any one of 1 to 6 , which has a specific viscosity of 0.12 to 0.40.
8 . The thermoplastic resin according to any one of 1 to 7 above, wherein the Abbe number is 23 to 26.
9 . The thermoplastic resin according to any one of 1 to 8 above, which has a refractive index of 1.635 to 1.660.
10 . The thermoplastic resin according to any one of 1 to 9 above, wherein the absolute value of orientation birefringence is 6 × 10 −3 or less.
11 . The thermoplastic resin according to any one of 1 to 10 above, which has a bending resistance of 20 mm or less.
12 . An optical member made of a thermoplastic resin according to any one of 1-11.
13 . An optical lens made of the thermoplastic resin according to any one of 1 to 11 above.
14 . A transparent film made of a thermoplastic resin according to any one of 1-11.
本発明の熱可塑性樹脂及び光学部材は、高屈折率、高アッベ数であり、かつ、耐折り曲げ性に優れるため、その奏する産業上の効果は、格別である。 Since the thermoplastic resin and the optical member of the present invention have a high refractive index, a high Abbe number, and excellent bending resistance, the industrial effects produced by the thermoplastic resin and optical member are exceptional.
以下、本発明の実施形態について具体的に説明する。
〈熱可塑性樹脂〉
本発明の熱可塑性樹脂は、式（１）で表される単位と式（２）で表される単位との割合がモル比で、１００：０〜５：９５であり、７５：２５〜１０：９０であると好ましく、５０：５０〜１０：９０であるとより好ましい。式（１）と式（２）の割合が上記範囲内であると、高屈折率、高アッベ数であり、耐折り曲げ性に優れるため好ましい。
Hereinafter, embodiments of the present invention will be specifically described.
<Thermoplastic resin>
In the thermoplastic resin of the present invention, the ratio of the unit represented by the formula (1) and the unit represented by the formula (2) is 100: 0 to 5:95 in terms of molar ratio, and 75:25 to 10 : 90 is preferable, and 50:50 to 10:90 is more preferable. It is preferable that the ratio of the formula (1) and the formula (2) is within the above range because it has a high refractive index and a high Abbe number and is excellent in bending resistance.
（式（１）中、Ｒ１、Ｒ２はそれぞれ独立に、水素原子、炭素数１〜２０のアルキル基、炭素数１〜２０のアルコキシル基、炭素数５〜２０のシクロアルキル基、炭素数５〜２０のシクロアルコキシル基、炭素数６〜２０のアリール基または炭素数６〜２０のアリールオキシ基である。Ｘは炭素数２〜８のアルキレン基、炭素数５〜１２のシクロアルキレン基または炭素数６〜２０のアリーレン基である。ｍおよびｎはそれぞれ独立に１〜１０の整数である。）
(In the formula (1), each
（式（２）中のＲ３〜Ｒ４は、それぞれ独立に、水素原子、炭素数１〜２０のアルキル基、炭素数１〜２０のアルコキシル基、炭素数５〜２０のシクロアルキル基、炭素数５〜２０のシクロアルコキシル基、炭素数６〜２０のアリール基または炭素数６〜２０のアリールオキシ基である。Ｙは炭素数２〜８のアルキレン基、炭素数５〜１２のシクロアルキレン基または炭素数６〜２０のアリーレン基である。ｏおよびｐはそれぞれ独立に１〜１０の整数である。） (R 3 to R 4 in Formula (2) are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxyl group having 1 to 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, or a carbon atom. A cycloalkoxyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aryloxy group having 6 to 20 carbon atoms, where Y is an alkylene group having 2 to 8 carbon atoms, and a cycloalkylene group having 5 to 12 carbon atoms. Or an arylene group having 6 to 20 carbon atoms, and o and p are each independently an integer of 1 to 10.)
本発明の熱可塑性樹脂の式（１）で表される単位において、Ｒ１、Ｒ２はそれぞれ独立に水素原子またはフェニル基であることが好ましい。
本発明の熱可塑性樹脂の式（１）で表される単位において、Ｘはエチレン基であることが好ましい。
本発明の熱可塑性樹脂の式（１）で表される単位において、ｍ、ｎはそれぞれ独立に１〜２であることが好ましい。
本発明の熱可塑性樹脂の式（２）で表される単位において、Ｒ３、Ｒ４はそれぞれ独立に水素原子またはフェニル基であることが好ましい。
本発明の熱可塑性樹脂の式（２）で表される単位において、Ｙはエチレン基であることが好ましい。
本発明の熱可塑性樹脂の式（２）で表される単位において、ｏ、ｐはそれぞれ独立に１〜２であることが好ましい。
In the unit represented by the formula (1) of the thermoplastic resin of the present invention, R 1 and R 2 are preferably each independently a hydrogen atom or a phenyl group.
In the unit represented by the formula (1) of the thermoplastic resin of the present invention, X is preferably an ethylene group.
In the unit represented by the formula (1) of the thermoplastic resin of the present invention, it is preferable that m and n are each independently 1-2.
In the unit represented by the formula (2) of the thermoplastic resin of the present invention, R 3 and R 4 are preferably each independently a hydrogen atom or a phenyl group.
In the unit represented by the formula (2) of the thermoplastic resin of the present invention, Y is preferably an ethylene group.
In the unit represented by the formula (2) of the thermoplastic resin of the present invention, it is preferable that o and p are each independently 1-2.
本発明の熱可塑性樹脂は、式（１）および／または、式（２）で表される構成単位を含むが、本発明の特性を損なわい程度に他のジオール成分を共重合してもよい。他のジオール成分は、全繰り返し単位中１０ｍｏｌ％以下が好ましい。その他のジオール成分として、エチレングリコール、プロパンジオール、ブタンジオール、ペンタンジオール、ヘキサンジオール、ヘプタンジオール、オクタンジオール、ノナンジオール、トリシクロ［５．２．１．０２，６］デカンジメタノール、シクロヘキサン−１，４−ジメタノール、デカリン−２，６−ジメタノール、ノルボルナンジメタノール、ペンタシクロペンタデカンジメタノール、シクロペンタン−１，３−ジメタノール、スピログリコール、イソソルビド、ヒドロキノン、レゾルシノール、２，２−ビス（４−ヒドロキシフェニル）プロパン、２，２−ビス（３−メチル−４−ヒドロキシフェニル）プロパン、１，１−ビス（４−ヒドロキシフェニル）−１−フェニルエタン、ビス（４−ヒドロキシフェニル）ジフェニルメタン、１，３−ビス（２−（４−ヒドロキシフェニル）−２−プロピル）ベンゼン、ビス（４−ヒドロキシフェニル）スルホン、ビス（４−（２−ヒドロキシエトキシ）フェニル）スルホン、ビス（４−ヒドロキシフェニル）スルフィド、１，１−ビス（４−ヒドロキシフェニル）−３，３，５−トリメチルシクロヘキサン、１，１−ビス（４−ヒドロキシフェニル）シクロヘキサン、ビフェノール、ビスフェノールフルオレン、ビスクレゾールフルオレン、１，１−ビ（２−（２−ヒドロキシエトキシ）ナフタレン）、１，１−ビ−２−ナフトール、ジヒドロキシナフタレン、ビス（２−ヒドロキシエトキシ）ナフタレン、１０，１０−ビス（４−ヒドロキシフェニル）アントロン等が挙げられる。 The thermoplastic resin of the present invention contains the structural unit represented by the formula (1) and / or the formula (2), but other diol components may be copolymerized to such an extent that the characteristics of the present invention are not impaired. . The other diol component is preferably 10 mol% or less in all repeating units. Other diol components include ethylene glycol, propanediol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, tricyclo [5.2.1.02,6] decandimethanol, cyclohexane-1, 4-dimethanol, decalin-2,6-dimethanol, norbornane dimethanol, pentacyclopentadecanedimethanol, cyclopentane-1,3-dimethanol, spiroglycol, isosorbide, hydroquinone, resorcinol, 2,2-bis (4 -Hydroxyphenyl) propane, 2,2-bis (3-methyl-4-hydroxyphenyl) propane, 1,1-bis (4-hydroxyphenyl) -1-phenylethane, bis (4-hydroxyphenyl) diphenyl Tan, 1,3-bis (2- (4-hydroxyphenyl) -2-propyl) benzene, bis (4-hydroxyphenyl) sulfone, bis (4- (2-hydroxyethoxy) phenyl) sulfone, bis (4- Hydroxyphenyl) sulfide, 1,1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane, 1,1-bis (4-hydroxyphenyl) cyclohexane, biphenol, bisphenol fluorene, biscresol fluorene, 1, 1-bi (2- (2-hydroxyethoxy) naphthalene), 1,1-bi-2-naphthol, dihydroxynaphthalene, bis (2-hydroxyethoxy) naphthalene, 10,10-bis (4-hydroxyphenyl) anthrone, etc. Is mentioned.
本発明の熱可塑性樹脂は、式（１）および／または、式（２）で表されるカーボネート単位を含むが、エステル単位も含むポリエステルカーボネート樹脂であっても良い。
本発明の熱可塑性樹脂中のエステル基のモル量は、エステル基とカーボネート基の合計モル量の０〜５０モル％であると好ましく、０〜２５モル％であるとより好ましい。
The thermoplastic resin of the present invention includes a carbonate unit represented by the formula (1) and / or the formula (2), but may be a polyester carbonate resin including an ester unit.
The molar amount of the ester group in the thermoplastic resin of the present invention is preferably 0 to 50 mol% and more preferably 0 to 25 mol% of the total molar amount of the ester group and the carbonate group.
本発明の熱可塑性樹脂中のエステル基を構成するジカルボン酸成分として、マロン酸、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、メチルマロン酸、エチルマロン酸等の脂肪族ジカルボン酸が挙げられる。また、フタル酸、テレフタル酸、イソフタル酸等の単環式芳香族ジカルボン酸や、２，６−ナフタレンジカルボン２，７−ナフタレンジカルボン酸、２，３−ナフタレンジカルボン酸、１，４−ナフタレンジカルボン酸、１，８−ナフタレンジカルボン酸、アントラセンジカルボン酸、フェナントレンジカルボン酸等の多環式芳香族ジカルボン酸が挙げられる。また、２，２’−ビフェニルジカルボン酸等のビフェニルジカルボン酸や、１，４−シクロジカルボン酸、２，６−デカリンジカルボン酸等の脂還族ジカルボン酸が挙げられる。これらは単独または二種以上組み合わせて用いてもよい。また、これらの誘導体としては酸クロライドやエステル類が用いられる。
As dicarboxylic acid components constituting the ester group in the thermoplastic resin of the present invention, aliphatic acids such as malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, methylmalonic acid, ethylmalonic acid, etc. Dicarboxylic acid is mentioned. In addition, monocyclic aromatic dicarboxylic acids such as phthalic acid, terephthalic acid, isophthalic acid, 2,6-
本発明の熱可塑性樹脂の比粘度は、０．１２〜０．４０が好ましく、０．１５〜０．３５であるとさらに好ましく、０．１８〜０．３０であるとよりいっそう好ましい。比粘度が上記範囲内であると成形性と機械強度のバランスに優れるため好ましい。
本発明の熱可塑性樹脂の屈折率は、１．６３５〜１．６６０であると好ましく、１．６４０〜１．６６０であるとさらに好ましく、１．６４３〜１．６６０であるとよりいっそう好ましい。屈折率は２５℃、波長５８９ｎｍにおいて測定する。屈折率が１．６３５以上の場合、レンズの球面収差を低減でき、さらにレンズの焦点距離を短くする事ができるため好ましい。
The specific viscosity of the thermoplastic resin of the present invention is preferably from 0.12 to 0.40, more preferably from 0.15 to 0.35, and even more preferably from 0.18 to 0.30. It is preferable for the specific viscosity to be in the above range since the balance between moldability and mechanical strength is excellent.
The refractive index of the thermoplastic resin of the present invention is preferably 1.635 to 1.660, more preferably 1.640 to 1.660, and even more preferably 1.643 to 1.660. The refractive index is measured at 25 ° C. and wavelength 589 nm. A refractive index of 1.635 or more is preferable because the spherical aberration of the lens can be reduced and the focal length of the lens can be shortened.
本発明の熱可塑性樹脂のアッベ数（ν）は、２３〜２６であると好ましい。アッベ数は２５℃、波長４８６ｎｍ、５８９ｎｍ、６５６ｎｍの屈折率から下記式を用いて算出する。また、小数点以下は四捨五入して算出する。
ν＝（ｎＤ−１）／（ｎＦ−ｎＣ）
ｎＤ：波長５８９ｎｍでの屈折率
ｎＣ：波長６５６ｎｍでの屈折率
ｎＦ：波長４８６ｎｍでの屈折率
The Abbe number (ν) of the thermoplastic resin of the present invention is preferably 23 to 26. The Abbe number is calculated from the refractive index at 25 ° C., wavelengths 486 nm, 589 nm, and 656 nm using the following formula. The figures after the decimal point are rounded off.
v = (nD-1) / (nF-nC)
nD: Refractive index at a wavelength of 589 nm nC: Refractive index at a wavelength of 656 nm nF: Refractive index at a wavelength of 486 nm
本発明の熱可塑性樹脂は、配向複屈折（Δｎ）の絶対値が、好ましくは０〜６×１０−３、より好ましくは０〜４×１０−３、さらに好ましくは０〜２×１０−３の範囲である。配向複屈折（Δｎ）は、該ポリカーボネート樹脂より得られる厚さ１００μｍのキャストフィルムをＴｇ＋１０℃で２倍延伸した時、波長５８９ｎｍにおいて測定する。配向複屈折が上記範囲内であると、レンズの光学歪が小さくなるため好ましい。
本発明の熱可塑性樹脂は、１ｍｍ厚の全光線透過率が、好ましくは８０％以上、より好ましくは８５％以上、さらに好ましくは８８％以上である。全光線透過率が上記範囲内であると、光学部材として適している。
In the thermoplastic resin of the present invention, the absolute value of orientation birefringence (Δn) is preferably 0 to 6 × 10 −3 , more preferably 0 to 4 × 10 −3 , and still more preferably 0 to 2 × 10 −3. Range. The orientation birefringence (Δn) is measured at a wavelength of 589 nm when a cast film having a thickness of 100 μm obtained from the polycarbonate resin is stretched twice at Tg + 10 ° C. It is preferable that the orientation birefringence is within the above range because the optical distortion of the lens becomes small.
The thermoplastic resin of the present invention has a total light transmittance of 1 mm thickness, preferably 80% or more, more preferably 85% or more, and still more preferably 88% or more. When the total light transmittance is within the above range, it is suitable as an optical member.
本発明の熱可塑性樹脂は、２３℃、２４時間浸漬後の吸水率が０．２５％以下であると好ましく、０．２０％以下であるとより好ましい。吸水率が上記範囲内であると、吸水による光学特性の変化が小さいため好ましい。
本発明の熱可塑性樹脂は、ガラス転移点（Ｔｇ）が１２０〜１６０℃であると好ましく、１３０〜１６０℃であるとより好ましい。ガラス転移点が上記範囲内であると、耐熱性と成形性のバランスに優れるため好ましい。
The thermoplastic resin of the present invention preferably has a water absorption rate of 0.25% or less after being immersed at 23 ° C. for 24 hours, and more preferably 0.20% or less. It is preferable for the water absorption rate to be within the above range since the change in optical properties due to water absorption is small.
The thermoplastic resin of the present invention preferably has a glass transition point (Tg) of 120 to 160 ° C, more preferably 130 to 160 ° C. It is preferable for the glass transition point to be in the above-mentioned range because of excellent balance between heat resistance and moldability.
本発明の熱可塑性樹脂は、耐折り曲げ性が２０ｍｍ以下であると好ましく、１５ｍｍ以下であるとより好ましく、１０ｍｍ以下であるとよりいっそう好ましい。耐折り曲げ性とは、長さ４０ｍｍ、幅１０ｍｍ、厚さ１００μｍのフィルムを用いて、万力の左右の接合面の間隔を４０ｍｍに開き、前記試験片の両端を接合面内に固定した。次に左右の接合面の間隔を２ｍｍ／秒以下の速度で狭めていき、折れ曲がった試験片全体を該接合面内で圧縮した。そして、接合面間が完全に密着する迄に試験片が折れ曲がり部で２片（又は３片以上の破片）に割れた際、万力の接合面の移動を停止し、接合面の間隔を測定した。耐折り曲げ性の数値が大きいほど、フィルムが割れやすいことを示す。耐折り曲げ性が上記範囲内であると、光学部材として十分な機械強度があるため好ましい。
本発明の熱可塑性樹脂は、用途や必要に応じて熱安定剤、可塑剤、光安定剤、重合金属不活性化剤、難燃剤、滑剤、帯電防止剤、界面活性剤、抗菌剤、紫外線吸収剤、離型剤等の添加剤を配合することができる。
The thermoplastic resin of the present invention preferably has a bending resistance of 20 mm or less, more preferably 15 mm or less, and even more preferably 10 mm or less. With bending resistance, using a film having a length of 40 mm, a width of 10 mm, and a thickness of 100 μm, the space between the left and right joint surfaces of the vise was opened to 40 mm, and both ends of the test piece were fixed in the joint surface. Next, the interval between the left and right joint surfaces was narrowed at a speed of 2 mm / second or less, and the entire bent test piece was compressed in the joint surface. And when the test piece is bent into two pieces (or more than three pieces) at the bent part until the joint surfaces are completely in close contact, the movement of the joint surface of the vise is stopped and the distance between the joint surfaces is measured. did. It shows that a film is easily broken, so that a numerical value of bending resistance is large. It is preferable for the bending resistance to be within the above range since there is sufficient mechanical strength as an optical member.
The thermoplastic resin of the present invention can be used as a heat stabilizer, a plasticizer, a light stabilizer, a polymerized metal deactivator, a flame retardant, a lubricant, an antistatic agent, a surfactant, an antibacterial agent, and an ultraviolet absorber. Additives such as agents and mold release agents can be blended.
〈ポリカーボネートの製造方法〉
本発明のポリカーボネート樹脂は、通常のポリカーボネート樹脂を製造するそれ自体公知の反応手段、例えばジオール成分に炭酸ジエステルなどのカーボネート前駆物質を反応させる方法により製造される。次にこれらの製造方法について基本的な手段を簡単に説明する。
<Production method of polycarbonate>
The polycarbonate resin of the present invention is produced by a reaction means known per se for producing an ordinary polycarbonate resin, for example, a method of reacting a diol component with a carbonate precursor such as a carbonic acid diester. Next, basic means for these manufacturing methods will be briefly described.
カーボネート前駆物質として炭酸ジエステルを用いるエステル交換反応は、不活性ガス雰囲気下所定割合の芳香族ジヒドロキシ成分を炭酸ジエステルと加熱しながら撹拌して、生成するアルコールまたはフェノール類を留出させる方法により行われる。反応温度は生成するアルコールまたはフェノール類の沸点などにより異なるが、通常１２０〜３００℃の範囲である。反応はその初期から減圧にして生成するアルコールまたはフェノール類を留出させながら反応を完結させる。また、必要に応じて末端停止剤、酸化防止剤等を加えてもよい。 The transesterification reaction using a carbonic acid diester as a carbonate precursor is performed by a method in which an aromatic dihydroxy component in a predetermined ratio is stirred with a carbonic acid diester while heating with an inert gas atmosphere to distill the generated alcohol or phenols. . The reaction temperature varies depending on the boiling point of the alcohol or phenol produced, but is usually in the range of 120 to 300 ° C. The reaction is completed while distilling off the alcohol or phenol produced under reduced pressure from the beginning. Moreover, you may add a terminal terminator, antioxidant, etc. as needed.
前記エステル交換反応に使用される炭酸ジエステルとしては、置換されてもよい炭素数６〜１２のアリール基、アラルキル基等のエステルが挙げられる。具体的には、ジフェニルカーボネート、ジトリールカーボネート、ビス（クロロフェニル）カーボネートおよびｍ−クレジルカーボネート等が例示される。なかでもジフェニルカーボネートが特に好ましい。ジフェニルカーボネートの使用量は、ジヒドロキシ化合物の合計１モルに対して、好ましくは０．９０〜１．０２モル、より好ましは０．９５〜１．００モルである。 Examples of the carbonic acid diester used in the transesterification include esters such as an aryl group having 6 to 12 carbon atoms and an aralkyl group which may be substituted. Specific examples include diphenyl carbonate, ditolyl carbonate, bis (chlorophenyl) carbonate and m-cresyl carbonate. Of these, diphenyl carbonate is particularly preferred. The amount of diphenyl carbonate to be used is preferably 0.90 to 1.02 mol, more preferably 0.95 to 1.00 mol, based on 1 mol of the total of dihydroxy compounds.
また溶融重合法においては重合速度を速めるために、重合触媒を用いることができ、かかる重合触媒としては、アルカリ金属化合物、アルカリ土類金属化合物、塩基性リン化合物、含窒素化合物、金属化合物等が挙げられる。このような化合物としては、アルカリ金属やアルカリ土類金属の、有機酸塩、無機塩、酸化物、水酸化物、水素化物、アルコキシド、４級アンモニウムヒドロキシド等が好ましく用いられ、これらの化合物は単独もしくは組み合わせて用いることができる。 In the melt polymerization method, a polymerization catalyst can be used to increase the polymerization rate. Examples of the polymerization catalyst include alkali metal compounds, alkaline earth metal compounds, basic phosphorus compounds, nitrogen-containing compounds, and metal compounds. Can be mentioned. As such compounds, organic acid salts, inorganic salts, oxides, hydroxides, hydrides, alkoxides, quaternary ammonium hydroxides, and the like of alkali metals and alkaline earth metals are preferably used. It can be used alone or in combination.
アルカリ金属化合物としては、水酸化ナトリウム、水酸化カリウム、水酸化セシウム、水酸化リチウム、炭酸水素ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、炭酸リチウム、酢酸ナトリウム、酢酸カリウム、酢酸セシウム、酢酸リチウム、ステアリン酸ナトリウム、ステアリン酸カリウム、ステアリン酸セシウム、ステアリン酸リチウム、水素化ホウ素ナトリウム、安息香酸ナトリウム、安息香酸カリウム、安息香酸セシウム、安息香酸リチウム、リン酸水素２ナトリウム、リン酸水素２カリウム、リン酸水素２リチウム、フェニルリン酸２ナトリウム、ビスフェノールＡの２ナトリウム塩、２カリウム塩、２セシウム塩、２リチウム塩、フェノールのナトリウム塩、カリウム塩、セシウム塩、リチウム塩等が例示される。 Examples of the alkali metal compound include sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium acetate, potassium acetate, cesium acetate, lithium acetate, Sodium stearate, potassium stearate, cesium stearate, lithium stearate, sodium borohydride, sodium benzoate, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, phosphorus Examples include dilithium oxyhydrogen, disodium phenylphosphate, disodium salt of bisphenol A, 2 potassium salt, 2 cesium salt, 2 lithium salt, sodium salt of phenol, potassium salt, cesium salt, lithium salt and the like.
アルカリ土類金属化合物としては、水酸化マグネシウム、水酸化カルシウム、水酸化ストロンチウム、水酸化バリウム、炭酸マグネシウム、炭酸カルシウム、炭酸ストロンチウム、炭酸バリウム、炭酸水素カルシウム、炭酸水素バリウム、炭酸水素マグネシウム、炭酸水素ストロンチウム、二酢酸マグネシウム、二酢酸カルシウム、二酢酸ストロンチウム、二酢酸バリウム等が例示される。塩基性ホウ素化合物としては、例えば、テトラメチルホウ素、テトラエチルホウ素、テトラプロピルホウ素、テトラブチルホウ素、トリメチルエチルホウ素、トリメチルベンジルホウ素、トリメチルフェニルホウ素、トリエチルメチルホウ素、トリエチルベンジルホウ素、トリエチルフェニルホウ素、トリブチルベンジルホウ素、トリブチルフェニルホウ素、テトラフェニルホウ素、ベンジルトリフェニルホウ素、メチルトリフェニルホウ素、ブチルトリフェニルホウ素等のナトリウム塩、カリウム塩、リチウム塩、カルシウム塩、バリウム塩、マグネシウム塩、あるいはストロンチウム塩等が挙げられる。 Alkaline earth metal compounds include magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, magnesium carbonate, calcium carbonate, strontium carbonate, barium carbonate, calcium bicarbonate, barium bicarbonate, magnesium bicarbonate, bicarbonate Examples include strontium, magnesium diacetate, calcium diacetate, strontium diacetate, and barium diacetate. Examples of the basic boron compound include tetramethyl boron, tetraethyl boron, tetrapropyl boron, tetrabutyl boron, trimethylethyl boron, trimethylbenzyl boron, trimethylphenyl boron, triethylmethyl boron, triethylbenzyl boron, triethylphenyl boron, tributylbenzyl. Examples include sodium, potassium, lithium, calcium, barium, magnesium, or strontium salts such as boron, tributylphenylboron, tetraphenylboron, benzyltriphenylboron, methyltriphenylboron, and butyltriphenylboron. It is done.
塩基性リン化合物としては、例えば、トリエチルホスフィン、トリ−ｎ−プロピルホスフィン、トリイソプロピルホスフィン、トリ−ｎ−ブチルホスフィン、トリフェニルホスフィン、トリブチルホスフィン、あるいは四級ホスホニウム塩等が挙げられる。 Examples of the basic phosphorus compound include triethylphosphine, tri-n-propylphosphine, triisopropylphosphine, tri-n-butylphosphine, triphenylphosphine, tributylphosphine, and quaternary phosphonium salts.
含窒素化合物としては、テトラメチルアンモニウムヒドロキシド、テトラエチルアンモニウムヒドロキシド、テトラプロピルアンモニウムヒドロキシド、テトラブチルアンモニウムヒドロキシド、トリメチルベンジルアンモニウムヒドロキシド等のアルキル、アリール基等を有する４級アンモニウムヒドロキシド類が挙げられる。また、トリエチルアミン、ジメチルベンジルアミン、トリフェニルアミン等の３級アミン類、２−メチルイミダゾール、２−フェニルイミダゾール、ベンゾイミダゾール等のイミダゾール類が挙げられる。また、アンモニア、テトラメチルアンモニウムボロハイドライド、テトラブチルアンモニウムボロハイドライド、テトラブチルアンモニウムテトラフェニルボレート、テトラフェニルアンモニウムテトラフェニルボレート等の塩基あるいは塩基性塩等が例示される。 Examples of nitrogen-containing compounds include quaternary ammonium hydroxides having alkyl, aryl groups, etc., such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, and trimethylbenzylammonium hydroxide. Can be mentioned. Further, tertiary amines such as triethylamine, dimethylbenzylamine, and triphenylamine, and imidazoles such as 2-methylimidazole, 2-phenylimidazole, and benzimidazole can be used. Moreover, bases or basic salts such as ammonia, tetramethylammonium borohydride, tetrabutylammonium borohydride, tetrabutylammonium tetraphenylborate, tetraphenylammonium tetraphenylborate and the like are exemplified.
金属化合物としては亜鉛アルミニウム化合物、ゲルマニウム化合物、有機スズ化合物、アンチモン化合物、マンガン化合物、チタン化合物、ジルコニウム化合物等が例示される。これらの化合物は１種または２種以上併用してもよい。
これらの重合触媒の使用量は、ジオール成分１モルに対し好ましくは１×１０−９〜１×１０−２当量、好ましくは１×１０−８〜１×１０−３当量、より好ましくは１×１０−７〜１×１０−５当量の範囲で選ばれる。
Examples of metal compounds include zinc aluminum compounds, germanium compounds, organotin compounds, antimony compounds, manganese compounds, titanium compounds, zirconium compounds, and the like. These compounds may be used alone or in combination of two or more.
The amount of these polymerization catalysts used is preferably 1 × 10 −9 to 1 × 10 −2 equivalent, preferably 1 × 10 −8 to 1 × 10 −3 equivalent, more preferably 1 ×, relative to 1 mol of the diol component. It is selected in the range of 10 −7 to 1 × 10 −5 equivalents.
また、必要によって反応後期に触媒失活剤を添加してもよい。使用する触媒失活剤としては、公知の触媒失活剤が有効に使用されるが、この中でもスルホン酸のアンモニウム塩、ホスホニウム塩が好ましい。更にドデシルベンゼンスルホン酸テトラブチルホスホニウム塩等のドデシルベンゼンスルホン酸の塩類、パラトルエンスルホン酸テトラブチルアンモニウム塩等のパラトルエンスルホン酸の塩類が好ましい。 Further, if necessary, a catalyst deactivator may be added at a later stage of the reaction. As the catalyst deactivator to be used, a known catalyst deactivator is effectively used. Among them, sulfonic acid ammonium salt and phosphonium salt are preferable. Furthermore, salts of dodecylbenzenesulfonic acid such as tetrabutylphosphonium salt of dodecylbenzenesulfonic acid and salts of paratoluenesulfonic acid such as tetrabutylammonium salt of paratoluenesulfonic acid are preferable.
また、スルホン酸のエステルとして、ベンゼンスルホン酸メチル、ベンゼンスルホン酸エチル、ベンゼンスルホン酸ブチル、ベンゼンスルホン酸オクチル、ベンゼンスルホン酸フェニル、パラトルエンスルホン酸メチル、パラトルエンスルホン酸エチル、パラトルエンスルホン酸ブチル、パラトルエンスルホン酸オクチル、パラトルエンスルホン酸フェニル等が好ましく用いられる。なかでも、ドデシルベンゼンスルホン酸テトラブチルホスホニウム塩が最も好ましく使用される。 Also, as esters of sulfonic acid, methyl benzenesulfonate, ethyl benzenesulfonate, butyl benzenesulfonate, octyl benzenesulfonate, phenyl benzenesulfonate, methyl paratoluenesulfonate, ethyl paratoluenesulfonate, butyl paratoluenesulfonate In addition, octyl paratoluenesulfonate, phenyl paratoluenesulfonate, and the like are preferably used. Among these, dodecylbenzenesulfonic acid tetrabutylphosphonium salt is most preferably used.
これらの触媒失活剤の使用量はアルカリ金属化合物および／またはアルカリ土類金属化合物より選ばれた少なくとも１種の重合触媒を用いた場合、その触媒１モル当たり好ましくは０．５〜５０モルの割合で、より好ましくは０．５〜１０モルの割合で、更に好ましくは０．８〜５モルの割合で使用することができる。 The amount of the catalyst deactivator used is preferably 0.5 to 50 mol per mol of the catalyst when at least one polymerization catalyst selected from alkali metal compounds and / or alkaline earth metal compounds is used. It can be used in a proportion, more preferably in a proportion of 0.5 to 10 mol, still more preferably in a proportion of 0.8 to 5 mol.
〈ポリエステルカーボネートの製造方法〉
本発明のポリエステルカーボネート樹脂は、ジオール成分とジカルボン酸成分またはそのエステル形成性誘導体と炭酸ジエステルとを、触媒の存在下、溶融重縮合法により好適に得ることができる。
本発明のポリエステルカーボネート樹脂に使用する触媒として使用する塩基性化合物としては水酸化ナトリウム、水酸化カリウム、水酸化リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素リチウム、炭酸ナトリウム、炭酸カリウム、炭酸リチウム、酢酸ナトリウム、酢酸カリウム、酢酸リチウム、ステアリン酸ナトリウム、ステアリン酸カリウム、ステアリン酸リチウム、ビスフェノールＡのナトリウム塩、カリウム塩、リチウム塩、安息香酸ナトリウム、安息香酸カリウム、安息香酸リチウム等が挙げられる。アルカリ土類金属化合物としては水酸化カルシウム、水酸化バリウム、水酸化マグネシウム、水酸化ストロンチウム、炭酸水素カルシウム、炭酸水素バリウム、炭酸水素マグネシウム、炭酸水素ストロンチウム、炭酸カルシウム、炭酸バリウム、炭酸マグネシウム、炭酸ストロンチウム、酢酸カルシウム、酢酸バリウム、酢酸マグネシウム、酢酸ストロンチウム、ステアリン酸カルシウム、ステアリン酸バリウム、ステアリン酸マグネシウム、ステアリン酸ストロンチウム等が挙げられる。
<Method for producing polyester carbonate>
The polyester carbonate resin of the present invention can be suitably obtained by a melt polycondensation method in the presence of a diol component and a dicarboxylic acid component or an ester-forming derivative thereof and a carbonic acid diester.
The basic compound used as the catalyst used in the polyester carbonate resin of the present invention is sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium hydrogen carbonate, potassium hydrogen carbonate, lithium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium carbonate. Sodium acetate, potassium acetate, lithium acetate, sodium stearate, potassium stearate, lithium stearate, sodium salt of bisphenol A, potassium salt, lithium salt, sodium benzoate, potassium benzoate, lithium benzoate and the like. Alkaline earth metal compounds include calcium hydroxide, barium hydroxide, magnesium hydroxide, strontium hydroxide, calcium bicarbonate, barium bicarbonate, magnesium bicarbonate, strontium bicarbonate, calcium carbonate, barium carbonate, magnesium carbonate, strontium carbonate , Calcium acetate, barium acetate, magnesium acetate, strontium acetate, calcium stearate, barium stearate, magnesium stearate, strontium stearate and the like.
本発明のポリエステルカーボネート樹脂に使用する助触媒として使用する含窒素塩基性化合物としてはテトラメチルアンモニウムヒドロキシド、テトラエチルアンモニウムヒドロキシド、テトラブチルアンモニウムヒドロキシド、トリメチルベンジルアンモニウムヒドロキシド、トリメチルアミン、トリエチルアミン、ジメチルベンジルアミン、トリフェニルアミン、ジメチルアミノピリジン等が挙げられる。 Nitrogen-containing basic compounds used as a co-catalyst for use in the polyester carbonate resin of the present invention include tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrabutylammonium hydroxide, trimethylbenzylammonium hydroxide, trimethylamine, triethylamine, dimethylbenzyl Examples include amine, triphenylamine, dimethylaminopyridine and the like.
本発明のポリエステルカーボネート樹脂に使用するエステル交換触媒としては亜鉛、スズ、ジルコニウム、鉛、チタン、ゲルマニウム、アンチモン、オスミウム、アルミニウムの塩が挙げられ、例えば、酢酸亜鉛、安息香酸亜鉛、２−エチルヘキサン酸亜鉛、塩化スズ（ＩＩ）、塩化スズ（ＩＶ）、酢酸スズ（ＩＩ）、酢酸スズ（ＩＶ）、ジブチルスズジラウレート、ジブチルスズオキサイド、ジブチルスズジメトキシド、ジルコニウムアセチルアセトナート、オキシ酢酸ジルコニウム、ジルコニウムテトラブトキシド、酢酸鉛（ＩＩ）、酢酸鉛（ＩＶ）、チタンテトラブトキシド（ＩＶ）、チタンテトライソプロポキシド、チタン（ＩＶ）＝テトラキス（２−エチル−１−ヘキサノラート）、酸化チタン、トリス（２，４−ペンタジオネート）アルミニウム（ＩＩＩ）等が用いられる。
本発明のポリエステルカーボネート樹脂に使用する触媒は単独で用いても、二種以上併用してもよく、これらの重合触媒の使用量はジオール成分とジカルボン酸成分の合計１モルに対して、１０−９〜１０−３モルの比率で用いられる。また、必要によって反応後期に触媒失活剤を添加してもよい。
Examples of the transesterification catalyst used in the polyester carbonate resin of the present invention include zinc, tin, zirconium, lead, titanium, germanium, antimony, osmium, and aluminum salts, such as zinc acetate, zinc benzoate, and 2-ethylhexane. Zinc acid, tin chloride (II), tin chloride (IV), tin acetate (II), tin acetate (IV), dibutyltin dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, Lead (II) acetate, lead (IV) acetate, titanium tetrabutoxide (IV), titanium tetraisopropoxide, titanium (IV) = tetrakis (2-ethyl-1-hexanolate), titanium oxide, tris (2,4- Pentazone ) Aluminum (III) or the like is used.
The catalyst used for the polyester carbonate resin of the present invention may be used alone or in combination of two or more. The amount of these polymerization catalysts used is 10 − based on a total of 1 mol of the diol component and the dicarboxylic acid component. It is used in a ratio of 9 to 10 −3 mol. Further, if necessary, a catalyst deactivator may be added at a later stage of the reaction.
〈光学部材〉
本発明の熱可塑性樹脂からなる光学部材は、射出成形、圧縮成形、射出圧縮成形、溶融押出成形、溶融押出製膜、キャスティング製膜等の任意の方法により成形、加工することができる。
本発明の熱可塑性樹脂からなる光学部材とは、光ディスク、透明導電性基板、光カード、シート、フィルム、光ファイバー、レンズ、プリズム、光学膜、基盤、光学フィルター、ハードコート膜等である。
<Optical member>
The optical member made of the thermoplastic resin of the present invention can be molded and processed by any method such as injection molding, compression molding, injection compression molding, melt extrusion molding, melt extrusion film formation, casting film formation and the like.
The optical member made of the thermoplastic resin of the present invention includes an optical disk, a transparent conductive substrate, an optical card, a sheet, a film, an optical fiber, a lens, a prism, an optical film, a substrate, an optical filter, a hard coat film, and the like.
〈光学レンズ〉
本発明の熱可塑性樹脂からなる光学レンズは、射出成形、圧縮成形、射出圧縮成形、溶融押出成形、キャスティング等の任意の方法により成形、加工することができるが、射出成形が特に好適である。射出成形の成形条件は特に限定されないが、成形機のシリンダ温度は１８０〜３２０℃が好ましく、２２０〜３００℃がより好ましく、２６０〜２９０℃がよりいっそう好ましい。また、金型温度は７０〜１５０℃が好ましく、８０〜１４０℃がより好ましく、９０〜１３０℃がよりいっそう好ましい。射出圧力は１００〜２，０００ｋｇｆ／ｃｍ２が好ましく、５００〜１，７００ｋｇｆ／ｃｍ２が好ましく、７００〜１，５００ｋｇｆ／ｃｍ２がよりいっそう好ましい。また、成形加工前に、本発明のポリカーボネート樹脂を１００〜１３０℃で１〜１２時間事前乾燥することが好ましい。
<Optical lens>
The optical lens made of the thermoplastic resin of the present invention can be molded and processed by any method such as injection molding, compression molding, injection compression molding, melt extrusion molding, and casting, but injection molding is particularly suitable. The molding conditions for injection molding are not particularly limited, but the cylinder temperature of the molding machine is preferably 180 to 320 ° C, more preferably 220 to 300 ° C, and even more preferably 260 to 290 ° C. The mold temperature is preferably 70 to 150 ° C, more preferably 80 to 140 ° C, and still more preferably 90 to 130 ° C. Injection pressure is preferably 100~2,000kgf / cm 2, preferably 500~1,700kgf / cm 2, and still more preferably, 700~1,500kgf / cm 2. Moreover, it is preferable to pre-dry the polycarbonate resin of this invention at 100-130 degreeC for 1 to 12 hours before a shaping | molding process.
本発明のポリカーボネート樹脂からなる光学レンズは、屈折率が高いことを特徴とする。一般的に、屈折率が高いと、同一屈折率を有するレンズエレメントをより曲率の小さい面で実現できるため、この面で発生する収差量を小さくできる。その結果、レンズの枚数を減らしたり、レンズの偏心感度を低減したり、レンズ厚みを薄くして軽量化することが可能になる。 The optical lens made of the polycarbonate resin of the present invention has a high refractive index. In general, when the refractive index is high, a lens element having the same refractive index can be realized on a surface with a smaller curvature, so that the amount of aberration generated on this surface can be reduced. As a result, it is possible to reduce the number of lenses, reduce the decentration sensitivity of the lenses, or reduce the lens thickness to reduce the weight.
本発明の熱可塑性樹脂からなる光学レンズは、光学歪みが小さいことを特徴とする。一般的なビスフェノールＡタイプのポリカーボネートからなる光学レンズは光学歪みが大きい。成形条件によりその値を低減することも不可能ではないが、その条件幅は非常に小さく成形が非常に困難となる。本発明の樹脂は、樹脂の配向により生じる光学歪みが極めて小さく、また成形歪みも小さいため、成形条件を厳密に設定しなくても良好な光学レンズを得ることができる。 The optical lens made of the thermoplastic resin of the present invention is characterized by small optical distortion. An optical lens made of a general bisphenol A type polycarbonate has a large optical distortion. Although it is not impossible to reduce the value depending on molding conditions, the condition width is very small and molding becomes very difficult. Since the resin of the present invention has a very small optical strain caused by the orientation of the resin and a small molding strain, a good optical lens can be obtained without strictly setting molding conditions.
本発明の熱可塑性樹脂からなる光学レンズは、必要に応じて非球面レンズの形で用いることが好適に実施される。非球面レンズは、１枚のレンズで球面収差を実質的にゼロとすることが可能であるため、複数の球面レンズの組み合わせで球面収差を取り除く必要がなく、軽量化および生産コストの低減化が可能になる。従って、非球面レンズは、光学レンズの中でも特にカメラレンズとして有用である。 The optical lens made of the thermoplastic resin of the present invention is preferably used in the form of an aspheric lens as necessary. Since an aspheric lens can substantially eliminate spherical aberration with a single lens, there is no need to remove spherical aberration with a combination of a plurality of spherical lenses, thus reducing weight and reducing production costs. It becomes possible. Therefore, the aspherical lens is particularly useful as a camera lens among optical lenses.
また、本発明の熱可塑性樹脂は、流動性が高いため、薄肉小型で複雑な形状である光学レンズの材料として特に有用である。具体的なレンズサイズとして、中心部の厚みが０．０５〜３．０ｍｍ、より好ましくは０．０５〜２．０ｍｍ、さらに好ましくは０．１〜１．０ｍｍである。また、直径が１．０ｍｍ〜２０．０ｍｍ、より好ましくは１．０〜１０．０ｍｍ、さらに好ましくは３．０〜１０．０ｍｍである。また、その形状として片面が凸、片面が凹であるメニスカスレンズであることが好ましい。 Further, since the thermoplastic resin of the present invention has high fluidity, it is particularly useful as a material for an optical lens having a thin and small size and a complicated shape. As a specific lens size, the thickness of the central portion is 0.05 to 3.0 mm, more preferably 0.05 to 2.0 mm, and still more preferably 0.1 to 1.0 mm. Moreover, a diameter is 1.0 mm-20.0 mm, More preferably, it is 1.0-10.0 mm, More preferably, it is 3.0-10.0 mm. In addition, it is preferably a meniscus lens having a convex surface on one side and a concave surface on the other side.
本発明の熱可塑性樹脂からなる光学レンズの表面には、必要に応じ、反射防止層あるいはハードコート層といったコート層が設けられていても良い。反射防止層は、単層であっても多層であっても良く、有機物であっても無機物であっても構わないが、無機物であることが好ましい。具体的には、酸化ケイ素、酸化アルミニウム、酸化ジルコニウム、酸化チタニウム、酸化セリウム、酸化マグネシウム、フッ化マグネシウム等の酸化物あるいはフッ化物が例示される。
また、本発明の熱可塑性樹脂からなる光学レンズは、金型成形、切削、研磨、レーザー加工、放電加工、エッジングなど任意の方法により成形されてもよい。さらには、金型成形がより好ましい。
On the surface of the optical lens made of the thermoplastic resin of the present invention, a coating layer such as an antireflection layer or a hard coating layer may be provided as necessary. The antireflection layer may be a single layer or a multilayer, and may be organic or inorganic, but is preferably inorganic. Specific examples include oxides or fluorides such as silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, cerium oxide, magnesium oxide, and magnesium fluoride.
Further, the optical lens made of the thermoplastic resin of the present invention may be molded by any method such as mold molding, cutting, polishing, laser processing, electric discharge machining, edging. Furthermore, mold molding is more preferable.
〈透明フィルム〉
本発明の熱可塑性樹脂からなる透明フィルムは、溶融押出製膜、キャスト製膜等の任意の方法により成形、加工することができる。
本発明の熱可塑性樹脂からなる透明フィルムとは、ディスプレイ用フィルム、延伸フィルム、加飾フィルム等である。
溶融押出製膜においては、Ｔダイを用いて樹脂を押し出し冷却ロールに送る方法が好ましく用いられる。押出機のシリンダ温度は、１８０〜３２０℃が好ましく、２００℃〜３００℃の範囲がより好ましい。また、成形加工前に、本発明の熱可塑性樹脂を１００〜１３０℃で１〜１２時間事前乾燥することが好ましい。
<Transparent film>
The transparent film made of the thermoplastic resin of the present invention can be molded and processed by any method such as melt extrusion film formation or cast film formation.
The transparent film made of the thermoplastic resin of the present invention includes a display film, a stretched film, a decorative film, and the like.
In melt extrusion film formation, a method in which a resin is extruded using a T die and sent to a cooling roll is preferably used. The cylinder temperature of the extruder is preferably 180 to 320 ° C, and more preferably 200 to 300 ° C. Moreover, it is preferable to pre-dry the thermoplastic resin of this invention at 100-130 degreeC for 1 to 12 hours before a shaping | molding process.
本発明で用いる熱可塑性樹脂は、有機溶媒に対する溶解性が良好なので、溶液キャスト製膜も適用することが出来る。溶媒としては塩化メチレン、１，２−ジクロロエタン、１，１，２，２−テトラクロロエタン、ジオキソラン、ジオキサン等が好適に用いられる。
本発明の熱可塑性樹脂からなる透明フィルムの厚みは、３０〜５００μｍの範囲が好ましく、より好ましくは４０〜４００μｍの範囲である。
Since the thermoplastic resin used in the present invention has good solubility in organic solvents, solution cast film formation can also be applied. As the solvent, methylene chloride, 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, dioxolane, dioxane and the like are preferably used.
The thickness of the transparent film made of the thermoplastic resin of the present invention is preferably in the range of 30 to 500 μm, more preferably in the range of 40 to 400 μm.
以下に実施例を挙げて本発明をさらに説明する。
各実施例および比較例の評価用サンプルは以下の（ａ）の方法で調製した。
（ａ）フィルム
得られた樹脂３ｇを塩化メチレン５０ｍｌに溶解させ、ガラスシャーレ上にキャストする。室温にて十分に乾燥させた後、該樹脂のＴｇから１２０℃以下の温度にて８時間乾燥して、厚さ約１００μｍのキャストフィルムを作成した。
The following examples further illustrate the present invention.
Samples for evaluation of the examples and comparative examples were prepared by the following method (a).
(A) Film 3 g of the obtained resin is dissolved in 50 ml of methylene chloride and cast on a glass petri dish. After sufficiently drying at room temperature, the resin was dried at a temperature of 120 ° C. or lower from the Tg of the resin for 8 hours to prepare a cast film having a thickness of about 100 μm.
評価は下記の方法によった。
（１）比粘度：重合終了後に得られた樹脂を十分に乾燥し、該樹脂０．７ｇを塩化メチレン１００ｍｌに溶解した溶液から、その溶液の２０℃における比粘度（ηｓｐ）を測定した。
（２）共重合比：重合終了後に得られた樹脂を日本電子社製ＪＮＭ−ＡＬ４００のプロトンＮＭＲを用いて測定した。
（３）屈折率（ｎｄ）、アッベ数（ν）：（ａ）の手法により作成したフィルムをＡＴＡＧＯ製ＤＲ−Ｍ２のアッベ屈折計を用いて、２５℃における屈折率（波長：５８９ｎｍ）及びアッベ数を測定した。
（４）配向複屈折：（ａ）の手法により作成したフィルムを長さ７ｃｍ、幅１．５ｃｍにカットした後、長手方向の両端をチャックに挟み（チャック間４．５ｃｍ）、樹脂のＴｇ＋１０℃で２倍延伸し、日本分光（株）製エリプソメーターＭ−２２０を用いて５８９ｎｍにおける位相差（Ｒｅ）を測定し、下記式より配向複屈折（Δｎ）を求めた。
Δｎ＝Ｒｅ／ｄ
Δｎ：配向複屈折
Ｒｅ：位相差
ｄ：厚さ
（５）耐折り曲げ性：（ａ）の手法により作成したフィルムから長さ４０ｍｍ、幅１０ｍｍの長方形の試験片を切り出した。万力の左右の接合面の間隔を４０ｍｍに開き、前記試験片の両端を接合面内に固定した。次に左右の接合面の間隔を２ｍｍ／秒以下の速度で狭めていき、折れ曲がった試験片全体を該接合面内で圧縮した。そして、接合面間が完全に密着する迄に試験片が折れ曲がり部で２片（又は３片以上の破片）に割れた際、万力の接合面の移動を停止し、接合面の間隔を測定した。
Evaluation was based on the following method.
(1) Specific viscosity: The resin obtained after the completion of the polymerization was sufficiently dried, and the specific viscosity (η sp ) at 20 ° C. of the solution was measured from a solution obtained by dissolving 0.7 g of the resin in 100 ml of methylene chloride.
(2) Copolymerization ratio: The resin obtained after polymerization was measured using proton NMR of JNM-AL400 manufactured by JEOL Ltd.
(3) Refractive index (nd), Abbe number (ν): A film prepared by the method of (a) was measured with a refractive index (wavelength: 589 nm) and Abbe at 25 ° C. using an Abbe refractometer manufactured by ATAGO DR-M2. Number was measured.
(4) Oriented birefringence: after the film prepared by the method (a) is cut into a length of 7 cm and a width of 1.5 cm, both ends in the longitudinal direction are sandwiched between chucks (4.5 cm between chucks), and the resin Tg + 10 ° C. The phase difference (Re) at 589 nm was measured using an ellipsometer M-220 manufactured by JASCO Corporation, and the orientation birefringence (Δn) was determined from the following formula.
Δn = Re / d
Δn: orientation birefringence Re: retardation d: thickness (5) Bending resistance: A rectangular test piece having a length of 40 mm and a width of 10 mm was cut out from the film prepared by the method of (a). The space between the left and right joint surfaces of the vise was opened to 40 mm, and both ends of the test piece were fixed in the joint surface. Next, the interval between the left and right joint surfaces was narrowed at a speed of 2 mm / second or less, and the entire bent test piece was compressed in the joint surface. And when the test piece is bent into two pieces (or more than three pieces) at the bent part until the joint surfaces are completely in close contact, the movement of the joint surface of the vise is stopped and the distance between the joint surfaces is measured. did.
（光学レンズの成形）
作成したポリカーボネート樹脂１００重量部に、ＢＡＳＦ製ＩＲＧＡＦＯＳ１６８を０．０５重量部、理研ビタミン（株）製リケマールＳ−１００Ａを０．１重量部加えて、ベント付きφ１５ｍｍ単軸押出機を用いてペレット化した。その後、１２０℃で８時間乾燥した後、住友重機械（株）製ＳＥ３０ＤＵ射出成形機を用いて、厚さ０．３ｍｍ、凸面曲率半径５ｍｍ、凹面曲率半径４ｍｍ、φ５ｍｍの光学レンズを射出成形した。評価は、５００ショット成形した際に、成形片、スプルー、ランナーが折れ、金型に樹脂が残ってしまう等で連続成形を止めた回数を評価し、結果を表１に記載した。
(Molding optical lenses)
Add 0.05 parts by weight of BASF IRGAFOS168 and 0.1 parts by weight of Rikenmar S-100A from Riken Vitamin Co. to 100 parts by weight of the prepared polycarbonate resin, and pelletize using a 15 mm single screw extruder with a vent. did. Then, after drying at 120 ° C. for 8 hours, an optical lens having a thickness of 0.3 mm, a convex curvature radius of 5 mm, a concave curvature radius of 4 mm, and φ5 mm was injection molded using a SE30DU injection molding machine manufactured by Sumitomo Heavy Industries, Ltd. . The evaluation was carried out by evaluating the number of times that continuous molding was stopped because the molded piece, sprue, and runner were broken when 500 shots were molded and the resin remained in the mold, and the results are shown in Table 1.
実施例１
ビス（４−（２−ヒドロキシエトキシ）フェニル）スルホン（以下“ＢＰＳ−２ＥＯ”と省略することがある）１０１．５１部、ジフェニルカーボネート（以下“ＤＰＣ”と省略することがある）６３．６２部、及び水酸化ナトリウム０．０１２×１０−３部を攪拌機および留出装置付きの反応釜に入れ、窒素置換を３度行った後、ジャケットを１８０℃に加熱し、原料を溶融させた。完全溶解後、２０分かけて２０ｋＰａまで減圧すると同時に、６０℃／ｈｒの速度でジャケットを２６０℃まで昇温し、エステル交換反応を行った。その後、ジャケットを２６０℃に保持したまま、８０分かけて０．１３ｋＰａまで減圧し、２６０℃、０．１３ｋＰａ以下の条件下で５〜３０分重合反応を行った。反応終了後、生成したポリカーボネート樹脂をペレタイズしながら抜き出し、ポリカーボネート樹脂ペレットを得た。該ペレットを用いて、比粘度、共重合比、屈折率、配向複屈折、耐折り曲げ性を測定し、結果を表１に記載した。
Example 1
101.51 parts of bis (4- (2-hydroxyethoxy) phenyl) sulfone (hereinafter sometimes abbreviated as “BPS-2EO”), 63.62 parts of diphenyl carbonate (hereinafter sometimes abbreviated as “DPC”) , And 0.012 × 10 −3 parts of sodium hydroxide were placed in a reaction kettle equipped with a stirrer and a distillation apparatus, and after nitrogen substitution three times, the jacket was heated to 180 ° C. to melt the raw material. After complete dissolution, the pressure was reduced to 20 kPa over 20 minutes, and at the same time, the jacket was heated to 260 ° C. at a rate of 60 ° C./hr to conduct a transesterification reaction. Thereafter, the pressure was reduced to 0.13 kPa over 80 minutes while maintaining the jacket at 260 ° C., and a polymerization reaction was performed for 5 to 30 minutes under the conditions of 260 ° C. and 0.13 kPa or less. After completion of the reaction, the produced polycarbonate resin was extracted while pelletizing to obtain polycarbonate resin pellets. Using the pellets, specific viscosity, copolymerization ratio, refractive index, orientation birefringence, and bending resistance were measured, and the results are shown in Table 1.
実施例２
ＢＰＳ−２ＥＯを７６．１４部、９，９−ビス［４−（２−ヒドロキシエトキシ）−３−フェニルフェニル］フルオレン（以下“ＯＰＢＰＥＦ”と省略することがある）４４．３０部、ＤＰＣを６３．６２部、及び水酸化ナトリウム０．０１２×１０−３部を攪拌機および留出装置付きの反応釜に入れ、窒素置換を３度行った後、ジャケットを１８０℃に加熱し、原料を溶融させた。完全溶解後、２０分かけて２０ｋＰａまで減圧すると同時に、６０℃／ｈｒの速度でジャケットを２６０℃まで昇温し、エステル交換反応を行った。その後、ジャケットを２６０℃に保持したまま、８０分かけて０．１３ｋＰａまで減圧し、２６０℃、０．１３ｋＰａ以下の条件下で５〜３０分重合反応を行った。反応終了後、生成したポリカーボネート樹脂をペレタイズしながら抜き出し、ポリカーボネート樹脂ペレットを得た。該ペレットを用いて、比粘度、共重合比、屈折率、配向複屈折、耐折り曲げ性を測定し、結果を表１に記載した。
Example 2
76.14 parts of BPS-2EO, 44.30 parts of 9,9-bis [4- (2-hydroxyethoxy) -3-phenylphenyl] fluorene (hereinafter sometimes abbreviated as “OPBPEF”), 63 DPC .62 parts and 0.012 × 10 −3 parts of sodium hydroxide were placed in a reaction kettle equipped with a stirrer and a distillation apparatus, and after replacing with nitrogen three times, the jacket was heated to 180 ° C. to melt the raw material. It was. After complete dissolution, the pressure was reduced to 20 kPa over 20 minutes, and at the same time, the jacket was heated to 260 ° C. at a rate of 60 ° C./hr to conduct a transesterification reaction. Thereafter, the pressure was reduced to 0.13 kPa over 80 minutes while maintaining the jacket at 260 ° C., and a polymerization reaction was performed for 5 to 30 minutes under the conditions of 260 ° C. and 0.13 kPa or less. After completion of the reaction, the produced polycarbonate resin was extracted while pelletizing to obtain polycarbonate resin pellets. Using the pellets, specific viscosity, copolymerization ratio, refractive index, orientation birefringence, and bending resistance were measured, and the results are shown in Table 1.
実施例３
ＢＰＳ−２ＥＯを５０．７６部、ＯＰＢＰＥＦを８８．６１部とする以外は、実施例２と同様の方法でポリカーボネート樹脂ペレットを得た。該ペレットを用いて、比粘度、共重合比、屈折率、配向複屈折、耐折り曲げ性を測定し、結果を表１に記載した。
Example 3
Polycarbonate resin pellets were obtained in the same manner as in Example 2, except that 50.76 parts of BPS-2EO and 88.61 parts of OPBPEF were used. Using the pellets, specific viscosity, copolymerization ratio, refractive index, orientation birefringence, and bending resistance were measured, and the results are shown in Table 1.
実施例４
ＢＰＳ−２ＥＯを２５．３８部、ＯＰＢＰＥＦを１３２．９１部とする以外は、実施例２と同様の方法でポリカーボネート樹脂ペレットを得た。該ペレットを用いて、比粘度、共重合比、屈折率、配向複屈折、耐折り曲げ性を測定し、結果を表１に記載した。
Example 4
Polycarbonate resin pellets were obtained in the same manner as in Example 2 except that 25.38 parts of BPS-2EO and 132.91 parts of OPBPEF were used. Using the pellets, specific viscosity, copolymerization ratio, refractive index, orientation birefringence, and bending resistance were measured, and the results are shown in Table 1.
実施例５
ＢＰＳ−２ＥＯを１５．２３部、ＯＰＢＰＥＦを１５０．６３部とする以外は、実施例２と同様の方法でポリカーボネート樹脂ペレットを得た。該ペレットを用いて、比粘度、共重合比、屈折率、配向複屈折、耐折り曲げ性を測定し、結果を表１に記載した。
Example 5
A polycarbonate resin pellet was obtained in the same manner as in Example 2 except that 15.23 parts of BPS-2EO and 150.63 parts of OPBPEF were used. Using the pellets, specific viscosity, copolymerization ratio, refractive index, orientation birefringence, and bending resistance were measured, and the results are shown in Table 1.
実施例６
ＢＰＳ−２ＥＯを１０．１５部、ＯＰＢＰＥＦを１５９．４９部とする以外は、実施例２と同様の方法でポリカーボネート樹脂ペレットを得た。該ペレットを用いて、比粘度、共重合比、屈折率、配向複屈折、耐折り曲げ性を測定し、結果を表１に記載した。
Example 6
Polycarbonate resin pellets were obtained in the same manner as in Example 2 except that 10.15 parts of BPS-2EO and 159.49 parts of OPBPEF were used. Using the pellets, specific viscosity, copolymerization ratio, refractive index, orientation birefringence, and bending resistance were measured, and the results are shown in Table 1.
実施例７
ＢＰＳ−２ＥＯを１５．２３部、ＯＰＢＰＥＦを９，９−ビス（４−（２−ヒドロキシエトキシ）フェニル）フルオレン（以下“ＢＰＥＦ”と省略することがある）に変更し、１１１．８２部とする以外は、実施例２と同様の方法でポリカーボネート樹脂ペレットを得た。該ペレットを用いて、比粘度、共重合比、屈折率、配向複屈折、耐折り曲げ性を測定し、結果を表１に記載した。
Example 7
Change BPS-2EO to 15.23 parts and OPBPEF to 9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene (hereinafter sometimes abbreviated as “BPEF”) to 111.82 parts. Except for the above, polycarbonate resin pellets were obtained in the same manner as in Example 2. Using the pellets, specific viscosity, copolymerization ratio, refractive index, orientation birefringence, and bending resistance were measured, and the results are shown in Table 1.
実施例８
ＢＰＳ−２ＥＯを１０．１５部、ＯＰＢＰＥＦを１５０．６３部、テレフタル酸ジメチル（以下、“ＤＭＴ”と省略することがある）を２．９１部、ＤＰＣを６０．４１部、及びチタンテトラブトキシド１５．３×１０−３部を攪拌機および留出装置付きの反応釜に入れ、窒素置換を３度行った後、ジャケットを１８０℃に加熱し、原料を溶融させた。完全溶解後、２０分かけて４０ｋＰａまで減圧すると同時に、６０℃／ｈｒの速度でジャケットを２６０℃まで昇温し、エステル交換反応を行った。その後、ジャケットを２６０℃に保持したまま、８０分かけて０．１３ｋＰａまで減圧し、２６０℃、０．１３ｋＰａ以下の条件下で５〜３０分重合反応を行った。反応終了後、生成したポリカーボネート樹脂をペレタイズしながら抜き出し、ポリカーボネート樹脂ペレットを得た。該ペレットを用いて、比粘度、共重合比、屈折率、配向複屈折、耐折り曲げ性を測定し、結果を表１に記載した。
Example 8
10.15 parts of BPS-2EO, 150.63 parts of OPBPEF, 2.91 parts of dimethyl terephthalate (hereinafter may be abbreviated as “DMT”), 60.41 parts of DPC, and titanium tetrabutoxide 15 .3 × 10 −3 parts were put into a reaction kettle equipped with a stirrer and a distillation apparatus, and after nitrogen substitution three times, the jacket was heated to 180 ° C. to melt the raw material. After complete dissolution, the pressure was reduced to 40 kPa over 20 minutes, and at the same time, the jacket was heated to 260 ° C. at a rate of 60 ° C./hr to conduct a transesterification reaction. Thereafter, the pressure was reduced to 0.13 kPa over 80 minutes while maintaining the jacket at 260 ° C., and a polymerization reaction was performed for 5 to 30 minutes under the conditions of 260 ° C. and 0.13 kPa or less. After completion of the reaction, the produced polycarbonate resin was extracted while pelletizing to obtain polycarbonate resin pellets. Using the pellets, specific viscosity, copolymerization ratio, refractive index, orientation birefringence, and bending resistance were measured, and the results are shown in Table 1.
比較例１
ＢＰＳ−２ＥＯを０部、ＯＰＢＰＥＦを１７７．２１部とする以外は、実施例１と同様の方法で、ＷＯ２０１４／０７３４９６号公報の実施例１２相当のポリカーボネート樹脂ペレットを得た。該ペレットを用いて、比粘度、共重合比、屈折率、配向複屈折、耐折り曲げ性を測定し、結果を表１に記載した。
Comparative Example 1
A polycarbonate resin pellet corresponding to Example 12 of WO2014 / 073496 was obtained in the same manner as in Example 1 except that 0 part of BPS-2EO and 177.21 part of OPBPEF were used. Using the pellets, specific viscosity, copolymerization ratio, refractive index, orientation birefringence, and bending resistance were measured, and the results are shown in Table 1.
比較例２
ＯＰＢＰＥＦを１５９．４９部、９，９−ビス（４−ヒドロキシ−３−メチルフェニル）フルオレン（以下、“ＢＣＦ”と省略すること事がある）１１．３６部、ＤＰＣを６４．９１部、及び水酸化ナトリウム０．０１２×１０−３部を攪拌機および留出装置付きの反応釜に入れ、窒素置換を３度行った後、ジャケットを１８０℃に加熱し、原料を溶融させた。完全溶解後、２０分かけて２０ｋＰａまで減圧すると同時に、６０℃／ｈｒの速度でジャケットを２６０℃まで昇温し、エステル交換反応を行った。その後、ジャケットを２６０℃に保持したまま、８０分かけて０．１３ｋＰａまで減圧し、２６０℃、０．１３ｋＰａ以下の条件下で５〜３０分重合反応を行った。反応終了後、生成したポリカーボネート樹脂をペレタイズしながら抜き出し、特開２０１５−８６２６５号公報の実施例４相当のポリカーボネート樹脂ペレットを得た。該ペレットを用いて、比粘度、共重合比、屈折率、配向複屈折、耐折り曲げ性を測定し、結果を表１に記載した。
Comparative Example 2
159.49 parts of OPBPEF, 11.36 parts of 9,9-bis (4-hydroxy-3-methylphenyl) fluorene (hereinafter sometimes abbreviated as “BCF”), 64.91 parts of DPC, and After placing 0.012 × 10 −3 parts of sodium hydroxide in a reaction kettle equipped with a stirrer and a distiller and performing nitrogen substitution three times, the jacket was heated to 180 ° C. to melt the raw material. After complete dissolution, the pressure was reduced to 20 kPa over 20 minutes, and at the same time, the jacket was heated to 260 ° C. at a rate of 60 ° C./hr to conduct a transesterification reaction. Thereafter, the pressure was reduced to 0.13 kPa over 80 minutes while maintaining the jacket at 260 ° C., and a polymerization reaction was performed for 5 to 30 minutes under the conditions of 260 ° C. and 0.13 kPa or less. After completion of the reaction, the produced polycarbonate resin was extracted while pelletizing to obtain polycarbonate resin pellets corresponding to Example 4 of JP-A-2015-86265. Using the pellets, specific viscosity, copolymerization ratio, refractive index, orientation birefringence, and bending resistance were measured, and the results are shown in Table 1.
比較例３
ＢＣＦをビス（４−ヒドロキシフェニル）スルホン（以下、ＢＰＳと省略することがある）に変更し、７．５１部とする以外は、比較例２と同様の方法でポリカーボネート樹脂ペレットを得た。該ペレットを用いて、比粘度、共重合比、屈折率、配向複屈折、耐折り曲げ性を測定し、結果を表１に記載した。
Comparative Example 3
A polycarbonate resin pellet was obtained in the same manner as in Comparative Example 2 except that BCF was changed to bis (4-hydroxyphenyl) sulfone (hereinafter sometimes abbreviated as BPS) to 7.51 parts. Using the pellets, specific viscosity, copolymerization ratio, refractive index, orientation birefringence, and bending resistance were measured, and the results are shown in Table 1.
実施例１〜８で得られた熱可塑性樹脂は、高屈折率、高アッベ数であり、かつ、耐折り曲げ性に優れる。また、連続成形性も良い。これに対して、比較例１〜３で得られた熱可塑性樹脂は、脆いため、耐折り曲げ性及び連続成形性に劣る。 The thermoplastic resins obtained in Examples 1 to 8 have a high refractive index, a high Abbe number, and excellent bending resistance. Moreover, continuous moldability is also good. On the other hand, since the thermoplastic resins obtained in Comparative Examples 1 to 3 are brittle, they are inferior in bending resistance and continuous moldability.
本発明の熱可塑性樹脂は、光ディスク、透明導電性基板、光カード、シート、フィルム、光ファイバー、レンズ、プリズム、光学膜、基盤、光学フィルター、ハードコート膜等の光学部材に用いることができ極めて有用である。 The thermoplastic resin of the present invention can be used for optical members such as optical disks, transparent conductive substrates, optical cards, sheets, films, optical fibers, lenses, prisms, optical films, substrates, optical filters, and hard coat films, and is extremely useful. It is.
１．作業台
２．万力
２１．取付基部
２２．上取付部
２３．下取付部
２３１．取付雌ネジ
２３２．取付ネジ軸
２３３．ハンドル
２３４．挟持板
２４．固定口金
２４１．試験片設置用治具
２４２．挟持雌ネジ
２４３．接合面
２５．可動口金
２５１．試験片設置用治具
２５２．シャフト
２５３．ハンドル
２５４．接合面
３．試験片
1. Working table 2.
Claims (14)
A transparent film of a thermoplastic resin according to any one of claims 1 to 11.
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