WO2015170691A1 - 重縮合で製造された樹脂および樹脂組成物 - Google Patents
重縮合で製造された樹脂および樹脂組成物 Download PDFInfo
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- WO2015170691A1 WO2015170691A1 PCT/JP2015/063143 JP2015063143W WO2015170691A1 WO 2015170691 A1 WO2015170691 A1 WO 2015170691A1 JP 2015063143 W JP2015063143 W JP 2015063143W WO 2015170691 A1 WO2015170691 A1 WO 2015170691A1
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- resin
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- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 1
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- OXDOANYFRLHSML-UHFFFAOYSA-N dimethoxyphosphorylbenzene Chemical compound COP(=O)(OC)C1=CC=CC=C1 OXDOANYFRLHSML-UHFFFAOYSA-N 0.000 description 1
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
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- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- XMQYIPNJVLNWOE-UHFFFAOYSA-N dioctyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OCCCCCCCC XMQYIPNJVLNWOE-UHFFFAOYSA-N 0.000 description 1
- MKZVQIIAAIPNGH-UHFFFAOYSA-N dioctyl phenyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OC1=CC=CC=C1 MKZVQIIAAIPNGH-UHFFFAOYSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
- PXGLYSITKOROKV-UHFFFAOYSA-N dipropoxyphosphorylbenzene Chemical compound CCCOP(=O)(OCCC)C1=CC=CC=C1 PXGLYSITKOROKV-UHFFFAOYSA-N 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- VBVCYAZECWLFHP-UHFFFAOYSA-N dodecyl benzenesulfonate;tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC.CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 VBVCYAZECWLFHP-UHFFFAOYSA-N 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
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- 238000002523 gelfiltration Methods 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 238000003384 imaging method Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QJXZDBOIVBLYSJ-UHFFFAOYSA-N o-[3-heptadecanethioyloxy-2,2-bis(heptadecanethioyloxymethyl)propyl] heptadecanethioate Chemical compound CCCCCCCCCCCCCCCCC(=S)OCC(COC(=S)CCCCCCCCCCCCCCCC)(COC(=S)CCCCCCCCCCCCCCCC)COC(=S)CCCCCCCCCCCCCCCC QJXZDBOIVBLYSJ-UHFFFAOYSA-N 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
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- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
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- 125000000962 organic group Chemical group 0.000 description 1
- CHJUOCDSZWMLRU-UHFFFAOYSA-N oxo(dipropoxy)phosphanium Chemical compound CCCO[P+](=O)OCCC CHJUOCDSZWMLRU-UHFFFAOYSA-N 0.000 description 1
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- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 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
- 238000005453 pelletization Methods 0.000 description 1
- VCAFTIGPOYBOIC-UHFFFAOYSA-N phenyl dihydrogen phosphite Chemical compound OP(O)OC1=CC=CC=C1 VCAFTIGPOYBOIC-UHFFFAOYSA-N 0.000 description 1
- SMIZARYCGYRDGF-UHFFFAOYSA-N phenyl dipropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC1=CC=CC=C1 SMIZARYCGYRDGF-UHFFFAOYSA-N 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
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- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- QVLTXCYWHPZMCA-UHFFFAOYSA-N po4-po4 Chemical class OP(O)(O)=O.OP(O)(O)=O QVLTXCYWHPZMCA-UHFFFAOYSA-N 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 229940093625 propylene glycol monostearate Drugs 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
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- 235000011008 sodium phosphates Nutrition 0.000 description 1
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- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
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- 239000012086 standard solution Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 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 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AJHKJOCIGPIJFZ-UHFFFAOYSA-N tris(2,6-ditert-butylphenyl) phosphite Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1OP(OC=1C(=CC=CC=1C(C)(C)C)C(C)(C)C)OC1=C(C(C)(C)C)C=CC=C1C(C)(C)C AJHKJOCIGPIJFZ-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 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
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/19—Hydroxy compounds containing aromatic rings
- C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/19—Hydroxy compounds containing aromatic rings
- C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
- C08G63/197—Hydroxy compounds containing aromatic rings containing two or more aromatic rings containing condensed aromatic rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/005—Stabilisers against oxidation, heat, light, ozone
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/02—Halogenated hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/91—Photovoltaic applications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the present invention relates to a resin and a resin composition
- a resin and a resin composition comprising a structural unit having a specific binaphthyl skeleton and a structural unit having a specific fluorene structure and produced by polycondensation.
- Optical glass or optical transparent resin is used as a material for optical elements used in the optical systems of various cameras such as cameras, film-integrated cameras, and video cameras.
- Optical glass is excellent in heat resistance, transparency, dimensional stability, chemical resistance, etc., and there are many types of optical glass with various refractive indexes and Abbe numbers, but the material cost is high and the molding process The problem is that the productivity is poor and the productivity is low.
- processing to an aspheric lens used for aberration correction is a serious obstacle to practical use because it requires extremely high technology and high cost.
- optical lenses made of optical transparent resins can be mass-produced by injection molding, and have the advantage of being easy to manufacture aspherical lenses, Currently used as a camera lens.
- the optical transparent resin include polycarbonate made of bisphenol A, polymethyl methacrylate, and amorphous polyolefin.
- aberration correction is performed by combining a plurality of concave lenses and convex lenses.
- the chromatic aberration produced by the convex lens is combined with a concave lens having a chromatic aberration with the opposite sign to that of the convex lens, thereby canceling the chromatic aberration synthetically.
- the concave lens is required to have high dispersion (that is, low Abbe number).
- Patent Document 1 discloses a polyester resin composition obtained by copolymerizing a fluorene-based dihydroxy compound having a refractive index of about 1.66 and an Abbe number of about 20 as a resin used for a concave lens for aberration correction.
- Polycarbonate resin made of bisphenol A is widely used for optical lens applications, but has limitations in application because it has a weak point that birefringence is large.
- a resin material having high imaging performance and low birefringence has been demanded as the resolution is increased by increasing the number of pixels.
- Patent Document 5 As a method for realizing low birefringence of a resin material, there is a method of canceling birefringence between compositions having positive and negative birefringences having different signs (Patent Document 5).
- the sign of birefringence is determined by the difference between the polarizability in the polymer main chain direction and the polarizability in the polymer side chain direction.
- a polycarbonate resin made of bisphenol A whose polarizability in the polymer main chain direction is larger than the polarizability in the polymer side chain direction has a positive birefringence, and the fluorene structure has a higher polarizability in the polymer side chain direction.
- Polycarbonate resin made of bisphenol having a negative birefringence For this reason, the composition ratio of materials having birefringence with different signs is very important. By using a resin having a small birefringence, the optical distortion is reduced.
- Patent Document 6 describes that use of a dicarboxylic acid having a fluorene structure as a raw material in a polyester resin is effective in reducing birefringence.
- Carboxylic acid is a kind of compound having a hydroxyl group (Non-patent Document 1).
- Patent Documents 2, 3 and 4 polymers having a 1,1′-binaphthalene structure are described in Patent Documents 2, 3 and 4.
- Patent Document 2 and Patent Document 3 do not disclose a resin having a structural unit derived from the compound represented by the general formula (1).
- Patent Document 4 describes a polymer containing a structural unit represented by the general formula (A), but is not a polymer containing a structural unit having a fluorene structure.
- sign of birefringence of the polymer including the structural unit represented by the general formula (A) is positive or negative.
- X is an alkylene group having 1 to 10 carbon atoms.
- A represents an alkylene group having 2 to 4 carbon atoms.
- the naphthalene ring may be substituted with a substituent, or the substituted substituents may be condensed.
- M and l are each 0. ⁇ m ⁇ 50, 0 ⁇ l ⁇ 50 represents an integer.
- an object of the present invention is to provide a resin having excellent optical properties such as a high refractive index and a low Abbe number.
- the present inventors have found that a resin using a specific monomer exhibits optically superior performance such as a high refractive index and a low Abbe number. That is, the present invention is as follows, for example.
- a structural unit derived from a compound represented by the following general formula (1), a structural unit derived from a compound represented by the following general formula (2), and a structural unit derived from a dicarboxylic acid or a derivative thereof Polyester resin containing: [In Formula (1), X is an alkylene group having 1 to 10 carbon atoms] [In Formula (2), R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- each Y independently represents a single bond, 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 5 to 20 carbon atoms.
- the proportion of the structural unit derived from the compound represented by the general formula (1) among the structural units derived from the dihydroxy compound is 5 to 95 mol%, and the general formula (2)
- the proportion of the structural unit derived from the compound represented by is from 2.5 to 47.5 mol%.
- the proportion of the structural unit derived from glycol in the structural unit derived from the dihydroxy compound in the polyester resin is 5 to 70 mol% [1] to [4]
- the polyester resin in any one of.
- X is an alkylene group having 1 to 10 carbon atoms
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- An optical member comprising the polyester resin according to any one of [1] to [5-1].
- the optical member is a single-lens reflex camera, a digital still camera, a video camera, a mobile phone with a camera, a film with a lens, a telescope, binoculars, a microscope, or a projector.
- X is an alkylene group having 1 to 10 carbon atoms
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- polyester carbonate resin according to [8] or [9], wherein the dicarboxylic acid or a derivative thereof is naphthalenedicarboxylic acid, terephthalic acid, isophthalic acid, dicarboxylic acid having a fluorene group, or an ester thereof.
- each Y independently represents a single bond, 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 5 to 20 carbon atoms.
- the carbonic acid diester is selected from the group consisting of diphenyl carbonate, ditolyl carbonate, bis (chlorophenyl) carbonate, m-cresyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, and dicyclohexyl carbonate [8] -Polyester carbonate resin according to any one of [10-1].
- polyester carbonate resin the proportion of the structural unit derived from the compound represented by the general formula (1) among the structural units derived from the dihydroxy compound is 5 to 95 mol%, and the general formula (2
- X is an alkylene group having 1 to 10 carbon atoms
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- a group, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms, R is a hydrogen atom or a hydroxyalkyl group having 1 to 20 carbon atoms).
- An optical member comprising the polyester carbonate resin according to any one of [8] to [13].
- the optical member according to [14], wherein the optical member is a single-lens reflex camera, a digital still camera, a video camera, a camera-equipped mobile phone, a lensed film, a telescope, binoculars, a microscope, or an optical lens of a projector.
- Polycarbonate resin [In Formula (1), X is an alkylene group having 1 to 10 carbon atoms]
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- X is an alkylene group having 1 to 10 carbon atoms
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- the release agent is an ester of an alcohol and a fatty acid.
- the resin composition according to [20] wherein the ester of alcohol and fatty acid is stearic acid monoglyceride or lauric acid monoglyceride.
- a phenol resin comprising a polycarbonate resin containing a structural unit derived from the compound represented by the following general formula (1) and a polycarbonate resin containing a structural unit derived from the compound represented by the following general formula (2)
- Polycarbonate resin composition having a content of 0.1 to 3000 ppm:
- X is an alkylene group having 1 to 10 carbon atoms.
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- a group, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms, R is a hydrogen atom or a hydroxyalkyl group having 1 to 20 carbon atoms.
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- a group, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms, R is a hydrogen atom or a hydroxyalkyl group having 1 to 20 carbon atoms.
- a compound having a binaphthyl skeleton represented by general formula (1) and a compound having a fluorene skeleton represented by general formula (4) are: (A) a compound having two or more functional groups of one or more selected from a hydroxyl group, a hydroxycarbonyl group, an alkoxycarbonyl group, an acyloxycarbonyl group, or a halogenated carbonyl group, or in combination, and , (B) with or without carbonic acid diester, Resin produced by polycondensation.
- X is an alkylene group having 1 to 10 carbon atoms.
- Y is an organic group having 1 to 40 carbon atoms and 1 to 4 oxygen atoms having one or more functional groups selected from a hydroxyl group, a hydroxycarbonyl group, an alkoxycarbonyl group, an acyloxycarbonyl group, or a halogenated carbonyl group.
- a compound having a binaphthyl skeleton represented by general formula (1) A compound having two or more functional groups selected from a hydroxyl group, a hydroxycarbonyl group, an alkoxycarbonyl group, an acyloxycarbonyl group, or a halogenated carbonyl group, with or without a combination thereof; and With or without carbonic acid diester, Resin produced by polycondensation, and, (B) a compound having a fluorene skeleton represented by the general formula (4), A compound having two or more functional groups of one or more selected from a hydroxyl group, a hydroxycarbonyl group, an alkoxycarbonyl group, an acyloxycarbonyl group, or a halogenated carbonyl group, or in combination, and With or without carbonic acid diester, A resin composition obtained by mixing resins produced by polycondensation.
- R 1 and R 2 each independently represent 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 number of 5 A cycloalkoxyl group having 20 carbon atoms, an aryl group having 6-20 carbon atoms, or an aryloxy group having 6-20 carbon atoms.
- R 1 and R 2 each independently represent 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 number of 5 A cycloalkoxyl group having 20 carbon atoms, an aryl group having 6-20 carbon atoms, or an aryloxy group having 6-20 carbon atoms.
- R 1 and R 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.
- Y is independently a single bond, 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 cycloalkoxyl group having 5 to 20 carbon atoms. And represents an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms.
- a resin excellent in optical properties such as a high refractive index and a low Abbe number can be obtained.
- the resin according to the embodiment of the present invention is a resin produced by polycondensation using at least a compound represented by the general formula (1) and a compound represented by the general formula (2) as raw materials.
- the resin produced by polycondensation is preferably polyester, polyester carbonate, or polycarbonate.
- the structural unit derived from the compound represented by the general formula (1) contributes to a high refractive index and contributes to the reduction of the Abbe number as compared with the structural unit derived from the compound represented by the general formula (2).
- the structural unit derived from the compound represented by the general formula (2) contributes to a high refractive index and a low Abbe number, and reduces the birefringence value derived from the compound represented by the general formula (1).
- Optical characteristics such as refractive index, Abbe number, and birefringence value are greatly affected by the chemical structure of the structural units, and the influence of whether the chemical bond between the structural units is an ester bond or a carbonate bond is relatively small.
- the functional group contributing to polycondensation is an alcoholic hydroxyl group.
- a representative example of a functional group contributing to polycondensation is a hydroxyl group, and examples thereof include an alcoholic hydroxyl group, a phenolic hydroxyl group, and a hydroxyl group of a carboxylic acid.
- the resin according to the embodiment has a structural unit derived from a dihydroxy compound (excluding dicarboxylic acid) and a structural unit derived from dicarboxylic acid, but the raw material of this resin is limited to a dihydroxy compound or dicarboxylic acid. I don't mean. For example, not only dicarboxylic acids but also dicarboxylic acid esters, acid anhydrides, and acid halides can be used as raw materials.
- a component derived from a dihydroxy compound in a resin may be referred to as a dihydroxy component or a dihydroxy structural unit
- a component derived from a dicarboxylic acid may be referred to as a dicarboxylic acid component or a dicarboxylic acid structural unit.
- carboxylic acid is a kind of hydroxy compound
- dicarboxylic acid is a kind of dihydroxy compound.
- a resin composition obtained by mixing a resin obtained by polycondensation of a compound represented by general formula (1) and a resin obtained by polycondensation of a compound represented by at least general formula (2).
- a resin composition contains the structural unit derived from the compound represented by General formula (1), and the structural unit derived from the compound represented by General formula (2).
- Optical properties such as refractive index, Abbe number, and birefringence value are greatly influenced by the structure of these structural units, and the structural units exist in one molecule as in a copolymer, or the structural units as in a mixture. The effect of existing across multiple molecules is relatively small.
- Examples of the dihydroxy compound represented by the general formula (1) include 2,2′-bis (hydroxymethoxy) -1,1′-binaphthalene, 2,2′-bis (2-hydroxyethoxy) -1,1. Examples thereof include '-binaphthalene, 2,2'-bis (3-hydroxypropyloxy) -1,1'-binaphthalene, 2,2'-bis (4-hydroxybutoxy) -1,1'-binaphthalene and the like. Among these, 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene is preferably used.
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- a group, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms, R is a hydrogen atom or a hydroxyalkyl group having 1 to 20 carbon atoms.
- compounds having a fluorene structure represented by the general formula (2a) or (2b) are preferably used. These may be used alone or in combination of two or more.
- R 1 and R 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, carbon 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.
- a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms is preferable, and a hydrogen atom, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group Group, sec-butyl group, tert-butyl group, cyclohepta group, cyclopropyl group, or phenyl group are more preferable, and a hydrogen atom, methyl group, or phenyl group is particularly preferable.
- Examples of the dihydroxy compound represented by the formula (2a) include 9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene, 9,9-bis (4- (2-hydroxyethoxy) -3- Methylphenyl) fluorene, 9,9-bis (4- (2-hydroxyethoxy) -3,5-dimethylphenyl) fluorene, 9,9-bis (4- (2-hydroxyethoxy) -3-tert-butylphenyl ) Fluorene, 9,9-bis (4- (2-hydroxyethoxy) -3-isopropylphenyl) fluorene, 9,9-bis (4- (2-hydroxyethoxy) -3-cyclohexylphenyl) fluorene, 9,9 -Bis (4- (2-hydroxyethoxy) -3-phenylphenyl) fluorene is exemplified. Of these, 9,9-bis (4- (2-hydroxyethoxy) phenyl) fluorene is preferably used
- R 1 and R 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.
- R 1 and R 2 are preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and include a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, An isobutyl group, a sec-butyl group, a tert-butyl group, a cyclohepta group, a cyclopropyl group, or a phenyl group is more preferable, and a hydrogen atom or a methyl group is particularly preferable.
- Examples of the dihydroxy compound represented by the formula (2b) include 9,9-bis (4-hydroxyphenyl) fluorene, 9,9-bis (4-hydroxy-3-methylphenyl) fluorene, 9,9-bis (4 -Hydroxy-3-ethylphenyl) fluorene, 9,9-bis (4-hydroxy-3-n-propylphenyl) fluorene, 9,9-bis (4-hydroxy-3-isopropylphenyl) fluorene, 9,9- Bis (4-hydroxy-3-n-butylphenyl) fluorene, 9,9-bis (4-hydroxy-3-sec-butylphenyl) fluorene, 9,9-bis (4-hydroxy-3-tert-butylphenyl) ) Fluorene, 9,9-bis (4-hydroxy-3-cyclohexylphenyl) fluorene, 9,9-bis (4-hydro) Ci-2-phenylphenyl) fluorene, 9,9-bis (4-hydroxy-3-phenyl
- the resin of the present invention is preferably polyester, polyester carbonate, or polycarbonate.
- polyester polyester carbonate
- polycarbonate a resin that is a resin that is a resin that is a resin that is a resin that is a resin that is a resin that is a resin that is a resin that is a resin that is a resin that is a resin that is a resin that is a resin that is a resin that is a resin that is preferably polyester, polyester carbonate, or polycarbonate.
- polyester polyester carbonate
- polycarbonate polycarbonate
- Polycarbonate resin The polycarbonate resin according to the embodiment is represented by the structural unit derived from the compound represented by the general formula (1) (hereinafter, sometimes referred to as the structural unit (A)) and the general formula (2). It is a polycarbonate resin having a structural unit derived from a compound (excluding carboxylic acid) (hereinafter sometimes referred to as the structural unit (B)). In the polycarbonate resin, each structural unit is bonded through a carbonate bond.
- X is an alkylene group having 1 to 10 carbon atoms
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- a group, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms, R is a hydrogen atom or a hydroxyalkyl group having 1 to 20 carbon atoms.
- a compound represented by the general formula (2a) and a compound represented by the general formula (2b) can be suitably used.
- R 1 and R 2 are as defined in Formula (2) above).
- R 1 and R 2 are as defined in Formula (2) above).
- the details of the compound represented by the general formula (2a) or (2b) are as described above.
- an aromatic dihydroxy compound or an aliphatic dihydroxy compound can be used in combination with the compound of the general formula (1) or general formula (2) (excluding carboxylic acid).
- polycarbonate resin containing a structural unit derived from the compound represented by the general formula (2a) comprises a structural unit (A) derived from the compound represented by the general formula (1) and And a structural unit derived from the compound represented by the general formula (2a) (hereinafter sometimes referred to as the structural unit (C)).
- the total proportion of the carbonate units derived from the structural unit (A) and the carbonate units derived from the structural unit (C) is preferably 50 mol% or more, more preferably 80 mol%, based on the total carbonate units constituting the polycarbonate resin.
- the above is preferable, 90 mol% or more is particularly preferable, and 100 mol% is most preferable.
- This polycarbonate resin may contain structural units other than the structural units (A) and (C).
- the molar ratio (A / C) between the structural unit (A) and the structural unit (C) is preferably 20/80 to 99/1, more preferably 30/70 to 95/5, and 40/60 to 90/10. Particularly preferred.
- the proportion of the carbonate unit derived from the structural unit (A) is preferably 1 to 99 mol% with respect to all the carbonate units constituting the polycarbonate resin. More preferably, the proportion of carbonate units derived from the structural unit (A) is 30 to 90 mol%, more preferably 40 to 80 mol%, based on the total carbonate units constituting the polycarbonate resin.
- Preferred polystyrene-reduced weight average molecular weight (Mw) of this polycarbonate resin ) Is 20,000 to 200,000. More preferably, the polystyrene-equivalent weight average molecular weight (Mw) is 25,000 to 120,000, more preferably 25,000 to 60,000, particularly preferably 40,000 to 60,000. When Mw is smaller than 20000, the molded product becomes brittle, which is not preferable. If Mw is larger than 200,000, the melt viscosity becomes high, so that it is difficult to take out the resin from the mold at the time of molding.
- the polycarbonate resin may have any structure of random, block and alternating copolymer.
- the refractive index (nD) of this polycarbonate resin at 23 ° C. and a wavelength of 589 nm is preferably 1.640 to 1.680, more preferably 1.645 to 1.675, and further preferably 1.650 to 1.670. .
- the polycarbonate resin has a high refractive index (nD) and is suitable for optical lens materials.
- the refractive index can be measured by a method of JIS-K-7142 using an Abbe refractometer for a film having a thickness of 0.1 mm.
- the Abbe number ( ⁇ ) of this polycarbonate resin is preferably 24 or less, more preferably 23 or less, and still more preferably 22 or less.
- the Abbe number can be calculated from the refractive indexes of wavelengths 486 nm, 589 nm, and 656 nm at 23 ° C. using the following formula.
- ⁇ (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
- a preferable glass transition temperature is 95 to 180 ° C., more preferably 110 to 170 ° C., further preferably 115 to 160 ° C., and particularly preferably 125 to 145 ° C.
- Tg is lower than 95 ° C.
- the melting temperature of the resin becomes high, and the resin is likely to be decomposed or colored, which is not preferable.
- the glass transition temperature of resin is too high, in a general-purpose mold temperature controller, the difference between the mold temperature and the resin glass transition temperature becomes large. Therefore, in applications where strict surface accuracy is required for products, it is difficult and undesirable to use a resin having a glass transition temperature that is too high.
- This polycarbonate resin preferably has a 5% weight loss temperature (Td) of 350 ° C. or higher measured at a temperature rising rate of 10 ° C./min as an index of thermal stability to withstand heating during injection molding.
- Td 5% weight loss temperature
- the thermal decomposition during the molding is severe and it becomes difficult to obtain a good molded product, which is not preferable.
- This polycarbonate resin has an orientation birefringence ( ⁇ n), which is a measure of the birefringence, preferably 1.0 ⁇ 10 ⁇ 3 or less, more preferably 0.8 ⁇ 10 ⁇ 3 or less, and further preferably 0.3 ⁇ . 10 ⁇ 3 or less, particularly preferably 0.2 ⁇ 10 ⁇ 3 or less.
- ⁇ n is obtained by cutting a cast film having a thickness of 0.1 mm into a square of 5.0 cm square, sandwiching both ends of the film between chucks (3.0 cm between chucks), and stretching the polycarbonate resin by 1.5 times at Tg + 5 ° C.
- ⁇ n The sign of birefringence ( ⁇ n) is expressed by the following equation using the refractive index (n //) in the film stretching direction and the refractive index (n ⁇ ) in the direction perpendicular to the stretching direction, and ⁇ n is positive.
- the case of positive birefringence or negative is called negative birefringence.
- the phenol content in the polycarbonate resin is preferably 0.1 to 3000 ppm, more preferably 0.1 to 2000 ppm, and 1 to 1000 ppm, 1 to 800 ppm, 1 to 500 ppm, or 1 to 300 ppm. Is particularly preferred.
- the carbonic acid diester content in the polycarbonate resin is preferably from 0.1 to 1000 ppm, more preferably from 0.1 to 500 ppm, and particularly preferably from 1 to 100 ppm.
- the optical molded body obtained using this polycarbonate resin has a total light transmittance of preferably 85% or more, more preferably 88% or more, and is comparable to bisphenol A type polycarbonate resin.
- an antioxidant a release agent, an ultraviolet absorber, a fluidity modifier, a crystal nucleating agent, a reinforcing agent, a dye, an antistatic agent, an antibacterial agent, or the like may be added to the polycarbonate resin.
- Examples of the carbonic acid diester used in this reaction include diphenyl carbonate, ditolyl carbonate, bis (chlorophenyl) carbonate, m-cresyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, and dicyclohexyl carbonate. Of these, diphenyl carbonate is particularly preferred.
- the carbonic acid diester is preferably used in a ratio of 0.97 to 1.20 mol, more preferably 0 mol. The ratio is 98 to 1.10 mol. When the amount of the carbonic acid diester is outside these ranges, problems such as the resin not reaching the desired molecular weight, unreacted raw materials remaining in the resin, and optical properties may be deteriorated.
- Examples of basic compound catalysts include alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds.
- alkali metal compound examples include organic acid salts, inorganic salts, oxides, hydroxides, hydrides, and alkoxides of alkali metals.
- alkaline earth metal compound examples include organic acid salts, inorganic salts, oxides, hydroxides, hydrides or alkoxides of alkaline earth metal compounds.
- magnesium hydroxide, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenyl phosphate and the like are used.
- nitrogen-containing compound examples include quaternary ammonium hydroxide and salts thereof, amines and the like.
- quaternary ammonium hydroxides having an alkyl group, an aryl group, and the like such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, and trimethylbenzylammonium hydroxide;
- Tertiary amines such as triethylamine, dimethylbenzylamine and triphenylamine; secondary amines such as diethylamine and dibutylamine; primary amines such as propylamine and butylamine; 2-methylimidazole, 2-phenylimidazole and benzimidazole Imidazoles such as ammonia, tetramethylammonium borohydride, tetrabutylammonium borohydride, te
- salts of zinc, tin, zirconium, lead, etc. are preferably used, and these can be used alone or in combination.
- transesterification catalyst examples include zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin (II) chloride, tin (IV) chloride, tin (II) acetate, tin (IV) acetate, and dibutyltin.
- Dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead (II) acetate, lead (IV) acetate and the like are used.
- catalysts are used in a ratio of 1 ⁇ 10 ⁇ 9 to 1 ⁇ 10 ⁇ 3 mol, preferably 1 ⁇ 10 ⁇ 7 to 1 ⁇ 10 ⁇ 4 mol, relative to a total of 1 mol of the dihydroxy compound. .
- Two or more types of catalysts may be used in combination.
- the catalyst itself may be added as it is, or it may be added after being dissolved in a solvent such as water or phenol.
- the melt polycondensation method is a method in which melt polycondensation is carried out using the above-mentioned raw materials and catalysts under heating and further under normal pressure or reduced pressure while removing by-products by transesterification.
- the catalyst may be present together with the raw materials from the beginning of the reaction, or may be added during the reaction.
- the compound represented by the general formula (1) and the general formula (2a) and the carbonic acid diester are melted in a reaction vessel, and then the by-product monohydroxy compound is not distilled off. You may perform reaction in the state made to stay.
- the reaction time is from 20 minutes to 240 minutes, preferably from 40 minutes to 180 minutes, particularly preferably from 60 minutes to 150 minutes. It is as follows. At this time, if the by-product monohydroxy compound is distilled off immediately after production, the polycarbonate resin finally obtained has a low content of high molecular weight.
- the preferred reaction time can vary depending on the reaction scale.
- the melt polycondensation reaction may be carried out continuously or batchwise.
- the reaction equipment used for the reaction is a horizontal type equipped with paddle blades, lattice blades, glasses blades, etc., even if it is a vertical type equipped with vertical stirring blades, Max blend stirring blades, helical ribbon type stirring blades, etc. Or an extruder type equipped with a screw. In view of the viscosity of the polymer, it is preferable to use these reactors in appropriate combination.
- the catalyst may be removed or deactivated after the polymerization reaction in order to maintain thermal stability and hydrolysis stability, but it is not always necessary to deactivate.
- a method for deactivation of the catalyst by adding a known acidic substance can be preferably carried out.
- the acidic substance include esters such as butyl benzoate; aromatic sulfonic acids such as p-toluenesulfonic acid; aromatic sulfonic acid esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate.
- Phosphoric acids such as phosphorous acid, phosphoric acid, phosphonic acid; triphenyl phosphite, monophenyl phosphite, diphenyl phosphite, diethyl phosphite, di-n-propyl phosphite, diphosphorous acid Phosphorous esters such as n-butyl, di-n-hexyl phosphite, dioctyl phosphite, monooctyl phosphite; triphenyl phosphate, diphenyl phosphate, monophenyl phosphate, dibutyl phosphate, phosphoric acid Phosphate esters such as dioctyl and monooctyl phosphate; Phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid and dibutylphosphonic acid Phosphonates such as diethyl phenylphosphonate; pho
- p-toluene or butyl sulfonate is particularly preferable.
- These deactivators are used in an amount of 0.01 to 50 times mol, preferably 0.3 to 20 times mol for the amount of catalyst. When the amount is less than 0.01 times the amount of the catalyst, the deactivation effect is insufficient, which is not preferable. Moreover, when it is more than 50 times mole with respect to the amount of catalyst, since the heat resistance of resin falls and it becomes easy to color a molded object, it is unpreferable.
- the addition of the deactivator can be carried out by kneading and may be either a continuous type or a batch type.
- the temperature at the time of kneading is preferably 200 to 350 ° C, more preferably 230 to 300 ° C, and particularly preferably 250 to 270 ° C.
- the kneader is preferably an extruder if it is a continuous type, and a lab plast mill and a kneader are preferably used if it is a batch type. Examples of the extruder include a single screw extruder, a twin screw extruder, and a multi-screw extruder.
- the extruder can be appropriately provided with a gear pump for stably quantifying the resin discharge amount.
- the atmospheric pressure for melt kneading of the resin composition is not particularly limited, and normal pressure or reduced pressure, for example, pressure of normal pressure (760 mmHg) to 0.1 mmHg is used to prevent oxidation, decomposition products, removal of low-boiling components such as phenol. It is preferable from the viewpoint.
- the extruder may be a vent type or a no vent type, but is preferably a vent type extruder from the viewpoint of improving the quality of the extruded product.
- the pressure at the vent port may be normal pressure or reduced pressure, but may be, for example, normal pressure (760 mmHg) to 0.1 mmHg, preferably 100 to 0.1 mmHg.
- the pressure is about 50 to 0.1 mmHg from the viewpoint of prevention of oxidation, decomposition products, decomposition products, and removal of low-boiling components such as phenol.
- hydrogen devolatilization may be performed for the purpose of more efficiently reducing low-boiling components such as phenol.
- the kneading of the deactivator may be performed immediately after the completion of the polymerization reaction, or may be performed after pelletizing the polymerized resin.
- other additives antioxidants, mold release agents, UV absorbers, fluidity modifiers, crystal nucleating agents, reinforcing agents, dyes, antistatic agents, antibacterial agents, etc. It can be added in a similar manner.
- the temperature during devolatilization is preferably 230 to 300 ° C, more preferably 250 to 270 ° C.
- a horizontal apparatus equipped with a stirring blade having excellent surface renewability, such as a paddle blade, a lattice blade, or a glasses blade, or a thin film evaporator is preferably used.
- This polycarbonate resin is desired to have as little foreign matter content as possible, and filtration of the molten raw material, filtration of the catalyst solution, and the like are suitably performed.
- the filter mesh is preferably 5 ⁇ m or less, more preferably 1 ⁇ m or less.
- generate is implemented suitably.
- the mesh of the polymer filter is preferably 100 ⁇ m or less, more preferably 30 ⁇ m or less.
- the step of collecting the resin pellets must be a low dust environment, and is preferably class 6 or less, more preferably class 5 or less.
- An optical molded body can be manufactured using the polycarbonate resin.
- it is molded by an arbitrary method such as an injection molding method, a compression molding method, an extrusion molding method, or a solution casting method.
- the polycarbonate resin according to the embodiment is excellent in moldability and heat resistance, and thus can be used particularly advantageously in an optical lens that requires injection molding.
- the polycarbonate resin according to the embodiment can be used by mixing with other resins such as other polycarbonate resins and polyester resins.
- antioxidants processing stabilizers, light stabilizers, polymerized metal deactivators, flame retardants, lubricants, antistatic agents, surfactants, antibacterial agents, mold release agents, UV absorbers, plasticizers, compatibilizing You may mix additives, such as an agent.
- Antioxidants include triethylene glycol-bis [3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate], 1,6-hexanediol-bis [3- (3,5-di- -Tert-butyl-4-hydroxyphenyl) propionate], pentaerythritol-tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5-di- tert-butyl-4-hydroxyphenyl) propionate, 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, N, N-hexamethylene Bis (3,5-di-tert-butyl-4-hydroxy-hydrocinnamide), 3,5-di-te t-butyl-4-hydroxy-benzylphosphonate-diethy
- processing stabilizers include phosphorus processing heat stabilizers and sulfur processing heat stabilizers.
- the phosphorus processing heat stabilizer include phosphorous acid, phosphoric acid, phosphonous acid, phosphonic acid, and esters thereof.
- triphenyl phosphite tris (nonylphenyl) phosphite, tris (2,4-di-tert-butylphenyl) phosphite, tris (2,6-di-tert-butylphenyl) phosphite, Tridecyl phosphite, trioctyl phosphite, trioctadecyl phosphite, didecyl monophenyl phosphite, dioctyl monophenyl phosphite, diisopropyl monophenyl phosphite, monobutyl diphenyl phosphite, monodecyl dipheny
- Sulfur-based processing heat stabilizers include pentaerythritol-tetrakis (3-laurylthiopropionate), pentaerythritol-tetrakis (3-myristylthiopropionate), pentaerythritol-tetrakis (3-stearylthiopropionate) Dilauryl-3,3′-thiodipropionate, dimyristyl-3,3′-thiodipropionate, distearyl-3,3′-thiodipropionate, and the like.
- the content of the sulfur-based processing heat stabilizer in the polycarbonate resin is preferably 0.001 to 0.2 parts by weight with respect to 100 parts by weight of the polycarbonate resin.
- esters of alcohol and fatty acid include esters of monohydric alcohol and fatty acid, partial esters or total esters of polyhydric alcohol and fatty acid.
- the ester of the monohydric alcohol and the fatty acid is preferably an ester of a monohydric alcohol having 1 to 20 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms.
- the partial ester or total ester of a polyhydric alcohol and a fatty acid is preferably a partial ester or total ester of a polyhydric alcohol having 1 to 25 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms.
- examples of the ester of a monohydric alcohol and a saturated fatty acid include stearyl stearate, palmityl palmitate, butyl stearate, methyl laurate, isopropyl palmitate and the like.
- Examples of partial esters or total esters of polyhydric alcohols and saturated fatty acids include stearic acid monoglyceride, stearic acid diglyceride, stearic acid triglyceride, stearic acid monosorbate, behenic acid monoglyceride, capric acid monoglyceride, lauric acid monoglyceride, pentaerythritol monostearate.
- Dipentaerythritol such as rate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, biphenyl biphenate, sorbitan monostearate, 2-ethylhexyl stearate, dipentaerythritol hexastearate And all esters or partial esters.
- stearic acid monoglyceride and lauric acid monoglyceride are particularly preferred.
- the content of these release agents is preferably in the range of 0.005 to 2.0 parts by weight, more preferably in the range of 0.01 to 0.6 parts by weight, with respect to 100 parts by weight of the polycarbonate resin.
- the range of 0.5 part by weight is more preferable.
- the ultraviolet absorber at least one ultraviolet ray selected from the group consisting of a benzotriazole ultraviolet absorber, a benzophenone ultraviolet absorber, a triazine ultraviolet absorber, a cyclic imino ester ultraviolet absorber, and a cyanoacrylate ultraviolet absorber.
- Absorbents are preferred. That is, any of the ultraviolet absorbers listed below may be used alone or in combination of two or more.
- benzotriazole ultraviolet absorber examples include 2- (2-hydroxy-5-methylphenyl) benzotriazole, 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, 2- (2-hydroxy- 3,5-dicumylphenyl) phenylbenzotriazole, 2- (2-hydroxy-3-tert-butyl-5-methylphenyl) -5-chlorobenzotriazole, 2,2′-methylenebis [4- (1,1 , 3,3-tetramethylbutyl) -6- (2N-benzotriazol-2-yl) phenol], 2- (2-hydroxy-3,5-di-tert-butylphenyl) benzotriazole, 2- ( 2-hydroxy-3,5-di-tert-butylphenyl) -5-chlorobenzotriazole, 2- (2-hydroxy -3,5-di-tert-amylphenyl) benzotriazole, 2- (2-hydroxy-5-tert-octyl
- benzophenone ultraviolet absorbers examples include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-benzyloxybenzophenone, 2-hydroxy-4- Methoxy-5-sulfoxybenzophenone, 2-hydroxy-4-methoxy-5-sulfoxytrihydridolate benzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy-5-sodiumsulfoxybenzophenone, bis (5-benzoyl-4-hydroxy-2- Methoxyphenyl) Down, 2-hydroxy -4-n-dodecyloxy benzophenone, 2-hydroxy-4-methoxy-2'-carboxy benzophenone.
- triazine ultraviolet absorbers examples include 2- (4,6-diphenyl-1,3,5-triazin-2-yl) -5-[(hexyl) oxy] -phenol, 2- (4,6-bis ( 2,4-Dimethylphenyl) -1,3,5-triazin-2-yl) -5-[(octyl) oxy] -phenol, 2,4,6-tris (2-hydroxy-4-hexyloxy-3) -Methylphenyl) -1,3,5-triazine and the like.
- Cyclic imino ester UV absorbers include 2,2′-bis (3,1-benzoxazin-4-one), 2,2′-p-phenylenebis (3,1-benzoxazin-4-one) 2,2′-m-phenylenebis (3,1-benzoxazin-4-one), 2,2 ′-(4,4′-diphenylene) bis (3,1-benzoxazin-4-one), 2,2 '-(2,6-naphthalene) bis (3,1-benzoxazin-4-one), 2,2'-(1,5-naphthalene) bis (3,1-benzoxazin-4-one) ), 2,2 ′-(2-methyl-p-phenylene) bis (3,1-benzoxazin-4-one), 2,2 ′-(2-nitro-p-phenylene) bis (3,1- Benzoxazin-4-one) and 2,2 '-(2-chloro-p- Eniren) bis (3,1-benzoxazin-4-one
- Cyanoacrylate-based ultraviolet absorbers include 1,3-bis-[(2′-cyano-3 ′, 3′-diphenylacryloyl) oxy] -2,2-bis [(2-cyano-3,3-diphenyl). And acryloyl) oxy] methyl) propane and 1,3-bis-[(2-cyano-3,3-diphenylacryloyl) oxy] benzene.
- the content of the ultraviolet absorber is preferably 0.01 to 3.0 parts by weight, more preferably 0.02 to 1.0 parts by weight, and still more preferably 0 to 100 parts by weight of the polycarbonate resin. .05 to 0.8 parts by weight. If it is the range of this compounding quantity, it is possible to provide sufficient weather resistance to polycarbonate resin according to a use.
- the polycarbonate resin according to the embodiment exhibits a high refractive index and excellent heat resistance, and has fluidity suitable for molding. Furthermore, because of low birefringence and optical distortion hardly occur, in addition to optical lenses, transparent conductive substrates, optical disks, liquid crystal panels, optical cards, sheets, films used for liquid crystal displays, organic EL displays, solar cells, etc. It can be advantageously used as an optical molded body suitable for structural material or functional material use of optical components such as optical fibers, connectors, vapor-deposited plastic reflectors, and displays.
- a coating layer such as an antireflection layer or a hard coating layer may be provided on the surface of the optical molded body, if 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.
- An optical lens manufactured using the polycarbonate resin according to the embodiment has a high refractive index and excellent heat resistance, and thus, conventionally, an expensive high refractive index glass lens such as a telescope, binoculars, and a TV projector has been used. It can be used in the field and is extremely useful. If necessary, it is preferably used in the form of an aspheric lens. Since an aspherical lens can substantially eliminate spherical aberration with a single lens, there is no need to remove spherical aberration by combining a plurality of spherical lenses, which reduces weight and reduces production costs. It becomes possible. Therefore, the aspherical lens is particularly useful as a camera lens among optical lenses.
- the optical lens is molded by an arbitrary method such as an injection molding method, a compression molding method, or an injection compression molding method.
- an injection molding method such as an injection molding method, a compression molding method, or an injection compression molding method.
- the molding environment In order to avoid the contamination of foreign matter into the optical lens as much as possible, the molding environment must naturally be a low dust environment, preferably class 6 or less, more preferably class 5 or less.
- optical film Since the optical film manufactured using the polycarbonate resin according to the embodiment is excellent in transparency and heat resistance, it is suitably used for a film for a liquid crystal substrate, an optical memory card, and the like.
- the molding environment In order to avoid contamination of foreign matter to the optical film as much as possible, the molding environment must naturally be a low dust environment, preferably class 6 or less, more preferably class 5 or less.
- the said polycarbonate resin may be the form of the resin composition containing multiple types of resin. That is, the polycarbonate resin composition comprises a polycarbonate resin (E) having a structural unit (A) derived from a compound represented by the general formula (1), and a compound represented by the general formula (2) (however, dicarboxylic acid A polycarbonate resin (F) having a structural unit (B) derived from
- the polycarbonate resin composition is derived from the polycarbonate resin (E) having the structural unit (A) derived from the compound represented by the general formula (1) and the compound represented by the general formula (2). At least a polycarbonate resin (F) having a structural unit (B).
- the compounds represented by the general formula (2) those containing a structural unit derived from the compound represented by the general formula (2a) or the general formula (2b) are preferable, and the compound represented by the general formula (2a) What contains the structural unit derived from is further more preferable.
- the polycarbonate resin composition may contain other resins in addition to the polycarbonate resin (E) and the polycarbonate resin (F) as long as the characteristics of the present invention are not impaired.
- other resins that may be included in the polycarbonate resin composition include the following: Polyethylene, polypropylene, polyvinyl chloride, polystyrene, (meth) acrylic resin, ABS resin, polyamide, polyacetal, polycarbonate (but not polycarbonate resin (E) or polycarbonate resin (F)), polyphenylene ether, polyester, polyphenylene sulfide, polyimide , Polyethersulfone, polyetheretherketone, fluororesin, cycloolefin polymer, ethylene / vinyl acetate copolymer, epoxy resin, silicone resin, phenol resin, unsaturated polyester resin, polyurethane.
- the content of other resins that may be contained in the polycarbonate resin composition is preferably 20 parts by mass or less, and more preferably 10 parts by mass or less, with respect to the total mass of the polycarbonate resin (E) and the polycarbonate resin (F).
- compatibility will worsen and the transparency of a resin composition may fall.
- the polycarbonate resin (E) is preferably composed of a carbonate unit derived from the structural unit (A), and the polycarbonate resin (F) is a carbonate derived from the structural unit (B). It preferably consists of units.
- the resin composition which consists only of polycarbonate resin (E) and polycarbonate resin (F) is especially preferable.
- the polycarbonate resin composition contains, as impurities, phenol produced when each resin constituting the composition is produced and carbonic diester remaining without reacting.
- the phenol content in the polycarbonate resin composition is preferably 0.1 to 3000 ppm, more preferably 0.1 to 2000 ppm, 1 to 1000 ppm, 1 to 800 ppm, 1 to 500 ppm, or 1 to 300 ppm. It is particularly preferred.
- the carbonic acid diester content in the polycarbonate resin composition is preferably from 0.1 to 1000 ppm, more preferably from 0.1 to 500 ppm, and particularly preferably from 1 to 100 ppm.
- Polycarbonate resin (E) contains the structural unit derived from the compound represented by General formula (1).
- a structural unit derived from a compound other than the general formula (1) may be included, but the amount is 20 mol% with respect to 100 mol% of the structural unit (A). The following is desirable, and 10 mol% or less is more desirable. Within this range, a high refractive index is maintained.
- the polystyrene-converted average molecular weight Mw of the polycarbonate resin (E) is preferably 20000 to 200000, more preferably 25000 to 120,000, and particularly preferably 25000 to 50000. When Mw is smaller than 20000, the resin becomes brittle, which is not preferable. If Mw is larger than 200,000, the melt viscosity becomes high, so that it becomes difficult to remove the resin from the mold at the time of molding.
- the manufacturing method of polycarbonate resin (E) is not specifically limited.
- the dihydroxy compound represented by the general formula (1) can be produced by a melt polycondensation method in the presence of a carbonic acid diester and a catalyst.
- a catalyst a basic compound catalyst, a transesterification catalyst, or a mixed catalyst composed of both can be used.
- Polycarbonate resin (E) may contain the structural unit derived from other dihydroxy compounds other than the dihydroxy compound of General formula (1).
- Other dihydroxy compounds include ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 1,5-heptane Aliphatic dihydroxy compounds such as diol and 1,6-hexanediol; 1,2-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,4-cyclohexanedimethanol, tricyclodecane dimethanol, pentacyclopentadecanedi Methanol, 2,6-decalin dimethanol, 1,5-decalin dimethanol, 2,3-decalin dimethanol, 2,3-norbornane dimethanol, 2,5-norbornane dimethanol, 1,3-adamantane dimethanol, etc.
- the other dihydroxy compound is preferably added in an amount of 20 mol% or less, more preferably 10 mol% or less, relative to 100 mol% of the structural unit derived from the dihydroxy compound of the general formula (1). Within this range, a high refractive index is maintained.
- the specific production method, the compound to be used, etc. are structural units derived from the compound represented by the above “(2) general formula (2a)” except that the compound represented by the general formula (2a) is not used. It is the same as described in “Production Method of Polycarbonate Resin”.
- the method for producing the polycarbonate resin (F) is the same as the method for producing the polycarbonate resin (E) except that the compound represented by the general formula (1) is changed to the compound represented by the general formula (2). is there.
- the production method of the polycarbonate resin composition is not particularly limited.
- the kneading may be either a continuous type or a batch type.
- the kneader is preferably an extruder if it is a continuous type, and a lab plast mill and a kneader are preferably used if it is a batch type.
- the polycarbonate resin composition may contain 2 or more types of polycarbonate resin (E) and polycarbonate resin (F), respectively. In that case, (E) and (F) in the formula (100 ⁇ (E)) / ((E) + (F)) are respectively two or more types of polycarbonate resins (E) and (F). It means the total weight.
- the polystyrene equivalent weight average molecular weight difference ( ⁇ Mw) between the polycarbonate resin (E) and the polycarbonate resin (F) is preferably 0 to 120,000, more preferably 0 to 80,000, and particularly preferably 0. ⁇ 20,000. If it is this range, since compatibility is good without the viscosity difference of polycarbonate resin (E) and polycarbonate resin (F) being too large, and transparency of a blend resin composition becomes high, it is preferable.
- an antioxidant is added to the polycarbonate resin composition as necessary. May be.
- These additives may be added in advance to each or either of the polycarbonate resin (E) and the polycarbonate resin (F) before kneading, or may be added and kneaded at the same time during kneading. It may be kneaded after mixing.
- the polycarbonate resin composition may contain polycarbonate resins other than polycarbonate resin (E) and polycarbonate resin (F), it is more preferable not to contain substantially.
- antioxidant processing stabilizer, mold release agent, and ultraviolet absorber contained in the resin composition
- those similar to those described in the above-mentioned “(5) Optical molded article using polycarbonate resin” are used. The same applies to the amount added.
- Optical molded body using polycarbonate resin composition By using the above polycarbonate resin composition, the same method as described in “(5) Optical molded body using polycarbonate resin”, an optical lens or An optical molded body such as an optical film can be produced. Since the polycarbonate resin composition according to the embodiment is excellent in moldability and heat resistance, it can be used particularly advantageously in an optical lens that requires injection molding.
- the molecular weight (polystyrene equivalent weight average molecular weight (Mw)) of the polycarbonate resin composition (after mixing) according to the embodiment is preferably 20000 to 200000, more preferably 25000 to 120,000, and particularly preferably 25000 to 50000.
- the glass transition temperature of the polycarbonate resin composition according to the embodiment is preferably 95 ° C. to 180 ° C., more preferably 115 ° C. to 160 ° C.
- the refractive index (23 ° C., wavelength 589 nm) of the molded body produced from the polycarbonate resin composition according to the embodiment is preferably 1.640 to 1.680, and more preferably 1.650 to 1.670.
- the Abbe number of the molded body produced from the polycarbonate resin composition according to the embodiment is preferably 24 or less, and more preferably 23 or less.
- the optical distortion of the polycarbonate resin composition according to the embodiment when the molded piece of the polycarbonate resin composition is sandwiched between two polarizing plates and light leakage from behind is visually observed by the orthogonal Nicol method, the light leakage is remarkable. There is not, and it is preferable that there are few.
- the molded body produced from the polycarbonate resin composition according to the embodiment has low birefringence, it is suitable as a structural material for optical parts such as lenses, optical films, and optical sheets. Particularly, it is suitable for optical parts such as lenses because of low birefringence and high transparency.
- a coating layer such as an antireflection layer or a hard coating layer may be provided on the surface of the optical molded body, if 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.
- polyester resin is represented by a structural unit derived from the dihydroxy compound represented by the general formula (1) (hereinafter sometimes referred to as a structural unit (G)) and a general formula (2).
- a structural unit derived from a dihydroxy compound hereinafter sometimes referred to as a structural unit (H)).
- each structural unit is bonded through an ester bond. This ester bond is also referred to as “structural unit derived from dicarboxylic acid or a derivative thereof” or “dicarboxylic acid structural unit”.
- X is an alkylene group having 1 to 10 carbon atoms
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- a group, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms, R is a hydrogen atom or a hydroxyalkyl group having 1 to 20 carbon atoms.
- a compound represented by the general formula (2a) and a compound represented by the general formula (2b) can be suitably used.
- R 1 and R 2 are as defined in Formula (2) above).
- R 1 and R 2 are as defined in Formula (2) above).
- the details of the compound represented by the general formula (2a) or (2b) are as described above.
- structural unit (I) the structural unit derived from the compound represented by the general formula (2a) may be referred to as “structural unit (I)”.
- the total ratio of the dihydroxy structural unit and the dicarboxylic acid structural unit in all the structural units of the polyester resin is preferably 80 mol% or more, more preferably 90 mol% or more, and particularly preferably 100 mol%.
- the polyester resin according to the embodiment may include a structural unit derived from a dihydroxy compound, and as a dihydroxy compound (however, excluding dicarboxylic acid and derivatives thereof), an alkylene glycol (For example, ethylene glycol, propylene glycol, trimethylene glycol, 1,3-butanediol, tetramethylene glycol (1,4-butanediol), hexanediol, neopentyl glycol, octanediol, decanediol, Examples thereof include branched C2-12 alkylene glycol and (poly) oxyalkylene glycol (for example, diethylene glycol, triethylene glycol, dipropylene glycol).
- the structural units derived from these dihydroxy compounds one kind may be contained alone, or two or more kinds may be contained in combination.
- the proportion of the structural unit derived from ethylene glycol in the total dihydroxy structural unit is preferably 5 to 70 mol%, more preferably 5 to 40 mol%.
- the proportion of the structural unit (G) in all the dihydroxy structural units is preferably from 5 to 95 mol%, more preferably from 60 to 95%.
- the content of the structural unit (H) is preferably from 95 to 5 mol%, more preferably from 40 to 5 mol%, based on all dihydroxy structural units (excluding structural units derived from dicarboxylic acids). The same applies when the structural unit (H) is the structural unit (I).
- the molar ratio (G / H) of the structural unit (G) to the structural unit (H) is preferably 40/60 to 99/1, more preferably 60/40 to 95/5, and 70/30 to 90/10. Particularly preferred. The same applies when the structural unit (H) is the structural unit (I).
- the dicarboxylic acid structural unit contained in the polyester resin according to the embodiment is not particularly limited, but aromatic such as naphthalene dicarboxylic acid, terephthalic acid, isophthalic acid, phthalic acid, 2-methyl terephthalic acid, biphenyl dicarboxylic acid, tetralin dicarboxylic acid Dicarboxylic acid, oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, dodecanedicarboxylic acid, cyclohexanedicarboxylic acid, decalin dicarboxylic acid Acid, norbornane dicarboxylic acid, tricyclodecanedicarboxylic acid, pentacyclododecanedicarboxylic acid, 3,9-bis (1,1-dimethyl-2-
- Undecane 5 Carboxy-5-ethyl-2- (1,1-dimethyl-2-carboxyethyl) -1,3-dioxane, a structural unit derived from an aliphatic dicarboxylic acid and their derivatives such as dimer acid.
- dicarboxylic acid derivatives include esters, acid anhydrides, and acid halides.
- the structural unit derived from dicarboxylic acid shown by General formula (3) and its derivative (s) is also preferable.
- Y is independently a single bond, 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 cycloalkoxyl group having 5 to 20 carbon atoms. And represents an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms.
- the dicarboxylic acid structural unit constituting the polyester resin according to the embodiment may be composed of one type of the exemplified structural units, or may be composed of two or more types.
- the polyester resin may have any structure of random, block and alternating copolymer.
- the polyester resin includes a compound that generates a dicarboxylic acid structural unit (in addition to dicarboxylic acid, its ester, acid anhydride, and acid halide are exemplified) and a compound that generates a dihydroxy structural unit (however, derived from dicarboxylic acid) It can be produced by reacting a dihydroxy compound with the exception of the structural unit. Specifically, a compound represented by the general formula (1), a compound represented by the general formula (2) (preferably a compound represented by the general formula (2a) or (2b)), and a dicarboxylic acid or The derivative is reacted.
- reaction method examples include various methods such as a transesterification method, a melt polymerization method such as a direct polymerization method, a solution polymerization method, and an interfacial polymerization method. Among them, a melt polymerization method that does not use a reaction solvent is preferable.
- the dicarboxylic acid or a derivative thereof is preferably used in a ratio of 0.90 to 1.01 mol with respect to 1 mol of the total dihydroxy compound.
- the transesterification method which is one of the melt polymerization methods, involves reacting a dicarboxylic acid ester with a dihydroxy compound (excluding the dicarboxylic acid) in the presence of a catalyst, and transesterifying it while distilling off the resulting alcohol. Is generally used for the synthesis of polyester resins.
- a dicarboxylic acid and a dihydroxy compound are dehydrated to form an ester compound, and then an ester exchange reaction is performed while distilling off the excess dihydroxy compound under reduced pressure. It is a method of obtaining a polyester resin by performing.
- the direct polymerization method has an advantage that an alcohol is not distilled as in the transesterification method, and an inexpensive dicarboxylic acid can be used as a raw material.
- catalyst amount polymerization conditions such as temperature
- additives such as thermal stabilizers, etherification inhibitors and catalyst deactivators when carrying out these melt polymerization methods. Can do.
- the reaction may be performed in the presence of a catalyst.
- a metal catalyst for example, various catalysts used for producing a polyester resin, for example, a metal catalyst can be used.
- a metal catalyst for example, a metal compound containing an alkali metal, an alkaline earth metal, a transition metal, a periodic table group 13 metal, a periodic table group 14 metal, a periodic table group 15 metal, or the like is used.
- the metal compound include alkoxide, organic acid salt (acetate, propionate, etc.), inorganic acid salt (borate, carbonate, etc.), metal oxide and the like. These catalysts can be used alone or in combination of two or more.
- the amount of the catalyst used is, for example, about 0.01 ⁇ 10 ⁇ 4 to 100 ⁇ 10 ⁇ 4 mol, preferably about 0.1 ⁇ 10 ⁇ 4 to 40 ⁇ 10 ⁇ 4 mol with respect to 1 mol of the dicarboxylic acid. Also good.
- alkali metal compound examples include sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium acetate, potassium acetate, acetic acid.
- Cesium lithium acetate, sodium stearate, potassium stearate, cesium stearate, stearium, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, dilithium hydrogen phosphate, phenyl Disodium phosphate, disodium salt of bisphenol A, dipotassium salt, cesium salt, dilithium salt, phenol sodium salt, potassium salt, cesium salt, lithium salt and the like are used.
- alkaline earth metal compound examples include magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, magnesium hydrogen carbonate, calcium hydrogen carbonate, strontium hydrogen carbonate, barium hydrogen carbonate, magnesium carbonate, calcium carbonate.
- Strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenyl phosphate, and the like are used.
- zinc, tin, zirconium and lead salts are preferably used, and these can be used alone or in combination.
- These catalysts are generally used in a ratio of about 1 ⁇ 10 ⁇ 9 to 1 ⁇ 10 ⁇ 3 moles with respect to a total of 1 mole of dihydroxy compounds (excluding dicarboxylic acids), preferably 1 ⁇ It is used at a ratio of about 10 ⁇ 7 to 1 ⁇ 10 ⁇ 4 mol.
- Polyester resins include other resins, antioxidants, mold release agents, light stabilizers, UV absorbers, plasticizers, extenders, matting agents, drying regulators, antistatic agents, antisettling agents, and surfactants.
- Various additives such as fluidity modifiers, drying oils, waxes, fillers, colorants, reinforcing agents, surface smoothing agents, leveling agents, curing reaction accelerators, thickeners, and molding aids may be added. it can. Specific examples and addition amounts of these additives are as described in “1. Polycarbonate resin”.
- a fluidity modifier or mold release agent an ester of a polyfunctional alcohol and a fatty acid, particularly a stearic acid ester of glycerin, is 0.005 to 2.0 parts by weight, preferably 0.8. Addition in the range of 01 to 0.6 parts by weight, more preferably 0.02 to 0.5 parts by weight is preferable because troubles due to defective mold release can be reduced.
- the catalyst can be deactivated by adding a known acidic substance.
- the acidic substance used for deactivation of the catalyst include aromatic sulfonic acids such as p-toluenesulfonic acid; aromatic sulfonic acid esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate; Aromatic sulfonates such as tetrabutylphosphonium salt of dodecylbenzene sulfonate; Organic halides such as stearic acid chloride, benzoyl chloride, p-toluenesulfonic acid chloride; Alkyl sulfuric acid such as dimethyl sulfate; Organic halides such as benzyl chloride Are preferably used.
- the polyester resin according to the embodiment is desired to have as little foreign matter content as possible, and it is preferable to perform filtration of the molten raw material, filtration of the catalyst solution, and filtration of the molten oligomer.
- the filter mesh is preferably 7 ⁇ m or less, more preferably 5 ⁇ m or less.
- the mesh of the polymer filter is preferably 100 ⁇ m or less, more preferably 30 ⁇ m or less.
- the step of collecting the resin pellets must be a low dust environment, and is preferably class 6 or less, more preferably class 5 or less.
- the refractive index and Abbe number can be measured by the following methods.
- a cast film is prepared by dissolving a polyester resin in methylene chloride, and the refractive index is measured with a refractometer.
- the refractive index is a value measured at 25 ° C. and 589 nm (d-line)
- the Abbe number is a value calculated from refractive indices measured at 656 nm (C-line), 486 nm (F-line), and d-line.
- the refractive index measured in this way is preferably 1.60 or more, and more preferably 1.645 to 1.70.
- the Abbe number is preferably 21 or less, more preferably 20 or less, for example, 17 to 21.
- the glass transition temperature is measured with a differential scanning calorimeter and is not particularly limited, but is usually 110 ° C. or higher, preferably 115 ° C. or higher, more preferably 120 ° C. or higher.
- the glass transition temperature of the polyester resin and the polyester carbonate resin is easily 110 by appropriately selecting a conventionally known diol or dicarboxylic acid such as a diol having a cyclic acetal skeleton or an aromatic hydrocarbon group or a dicarboxylic acid having a naphthalene skeleton. It can be over °C.
- the glass transition temperature is preferably less than 150 ° C.
- the polyester resin can be used for various applications.
- it can be used for injection molded articles, sheets, films, extruded molded articles such as pipes, bottles, foams, adhesives, adhesives, paints and the like.
- the sheet may be a single layer or a multilayer
- the film may be a single layer or a multilayer.
- the sheet may be unstretched, or may be stretched in one direction or in two directions. May be.
- the bottle may be a direct blow bottle, an injection blow bottle, or an injection molded bottle.
- the foam may be a bead foam or an extruded foam.
- Applications that require high heat resistance and water vapor barrier, such as products used in automobiles, packaging materials for import / export, electronic materials such as solar cell backsheets, food packaging materials for retort processing and microwave heating Can be suitably used.
- An excellent optical lens can be obtained by injection-molding the polyester resin according to the embodiment into a lens shape by an injection molding machine or an injection compression molding machine.
- the molding environment must naturally be a low dust environment, and is preferably class 6 or less, more preferably class 5 or less.
- An optical lens obtained by molding a polyester resin is preferably used in the form of an aspheric lens as necessary. Since an aspherical lens can substantially eliminate spherical aberration with a single lens, there is no need to remove spherical aberration by combining a plurality of spherical lenses, which reduces weight and reduces production costs. It becomes possible. Therefore, the aspherical lens is particularly useful as a camera lens among optical lenses.
- the astigmatism of the aspheric lens is preferably 0 to 15 m ⁇ , more preferably 0 to 10 m ⁇ .
- a coating layer such as an antireflection layer or a hard coating layer may be provided on the surface of the optical lens obtained by molding the polyester resin.
- 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.
- Optical lenses obtained by molding polyester resin can be used for various lenses such as pickup lenses, f- ⁇ lenses, and eyeglass lenses. However, because of their high refractive index and low Abbe number, they are used for chromatic aberration correction. It can be particularly suitably used as a lens. Specifically, it is suitably used as a lens for a single-lens reflex camera, a digital still camera, a video camera, a camera-equipped mobile phone, a lens-equipped film, a telescope, a binocular, a microscope, a projector, or the like.
- the optical lens using the polyester resin according to the embodiment is a concave lens, it can be used as an optical lens system with little chromatic aberration in combination with another convex lens having a high Abbe number.
- the Abbe number of the convex lens to be combined is preferably 40 to 60, and more preferably 50 to 60.
- polyester carbonate resin which concerns on embodiment is the structural unit (L) derived from the dihydroxy compound represented by General formula (1), and the structural unit (L) derived from the dihydroxy compound represented by General formula (2) ( M).
- each structural unit is bonded through a carbonate bond and an ester bond.
- This carbonate bond is also referred to as “structural unit derived from carbonic acid diester”, and the ester bond is also referred to as “structural unit derived from dicarboxylic acid or a derivative thereof” or “dicarboxylic acid structural unit”.
- X is an alkylene group having 1 to 10 carbon atoms
- R 1 and R 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 cycloalkoxyl having 5 to 20 carbon atoms.
- a group, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms, R is a hydrogen atom or a hydroxyalkyl group having 1 to 20 carbon atoms.
- a compound represented by the general formula (2a) and a compound represented by the general formula (2b) can be suitably used.
- R 1 and R 2 are as defined in Formula (2) above).
- R 1 and R 2 are as defined in Formula (2) above).
- the details of the compound represented by the general formula (2a) or (2b) are as described above.
- a structural unit derived from the compound represented by the general formula (2a) may be referred to as a structural unit (N).
- the total proportion of dihydroxy structural units (excluding structural units derived from dicarboxylic acid), carbonic acid diester structural units and dicarboxylic acid structural units in all structural units of the polyester carbonate resin is preferably 80 mol% or more, more preferably. Is 90 mol% or more, particularly preferably 100 mol%.
- the proportion of structural unit (L) in all dihydroxy structural units (excluding dicarboxylic acid structural units) is preferably 5 to 95 mol%.
- the content of the structural unit (M) is preferably 2.5 to 47.5 mol%, more preferably 5 to 45 mol%, based on all dihydroxy structural units (including dicarboxylic acid structural units). The same applies when the structural unit (M) is the structural unit (N).
- the molar ratio (L / M) of the structural unit (L) to the structural unit (M) is preferably 1/99 to 99/1, more preferably 20/80 to 95/5, and 40/60 to 90/10. Particularly preferred. The same applies when the structural unit (M) is the structural unit (N).
- the polyester carbonate resin may have any structure of random, block and alternating copolymer.
- the polyester carbonate resin according to the embodiment may include structural units derived from other dihydroxy compounds, and as dihydroxy compounds (those other than dicarboxylic acids and derivatives thereof).
- Alkylene glycol for example, ethylene glycol, propylene glycol, trimethylene glycol, 1,3-butanediol, tetramethylene glycol (1,4-butanediol), hexanediol, neopentyl glycol, octanediol, decanediol, etc.
- Examples thereof include chain or branched C2-12 alkylene glycol and (poly) oxyalkylene glycol (for example, diethylene glycol, triethylene glycol, dipropylene glycol).
- chain or branched C2-12 alkylene glycol and (poly) oxyalkylene glycol for example, diethylene glycol, triethylene glycol, dipropylene glycol.
- structural units derived from these dihydroxy compounds one kind may be contained alone, or two or more kinds may be contained in combination.
- Carbonic acid diester which is a carbonate bond precursor examples include diphenyl carbonate, ditolyl carbonate, bis (chlorophenyl) carbonate, m-cresyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, and dicyclohexyl carbonate.
- diphenyl carbonate is particularly preferred.
- Diphenyl carbonate is preferably used in a ratio of 0.97 to 1.10 mol, more preferably 0.98 to 1.05 mol, based on 1 mol of the total of dihydroxy compounds.
- the structural unit derived from the dicarboxylic acid contained in the polyester carbonate resin according to the embodiment is not particularly limited, but naphthalene dicarboxylic acid, terephthalic acid, isophthalic acid, phthalic acid, 2-methyl terephthalic acid, biphenyl dicarboxylic acid, tetralin dicarboxylic acid Aromatic dicarboxylic acid, oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, dodecanedicarboxylic acid, cyclohexanedicarboxylic acid Acid, decalin dicarboxylic acid, norbornane dicarboxylic acid, tricyclodecane dicarboxylic acid, pentacyclododecane
- dicarboxylic acid derivatives examples include esters, acid anhydrides, and acid halides.
- the structural unit derived from dicarboxylic acid represented by General formula (3) and its derivative (s) is also preferable.
- Y is independently a single bond, 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 cycloalkoxyl group having 5 to 20 carbon atoms.
- the dicarboxylic acid structural unit may be composed of one type of the exemplified structural units, or may be composed of two or more types.
- the polyester carbonate resin is obtained by transesterifying a compound that generates a carbonic acid diester structural unit, a compound that generates a dicarboxylic acid structural unit, and a compound that generates a dihydroxy structural unit in a molten state in the presence of a catalyst.
- a compound represented by the general formula (1), a compound represented by the general formula (2) (preferably a compound represented by the general formula (2a) or (2b)), a dicarboxylic acid or its The derivative and the carbonic acid diester are reacted.
- reaction method examples include various methods such as a transesterification method, a melt polymerization method such as a direct polymerization method, a solution polymerization method, and an interfacial polymerization method. Among them, a melt polymerization method that does not use a reaction solvent is preferable.
- the carbonic acid diester is preferably used in a ratio of 0.97 to 1.10 mol, more preferably 0.98 to 1.05 mol, based on 1 mol of the total of dihydroxy compounds. Further, the dicarboxylic acid or derivative thereof is preferably used in a ratio of 0.01 to 0.20 mol, more preferably 0.05 to 0, per 1 mol of the total of dihydroxy compounds (excluding dicarboxylic acid). .15 mole ratio.
- the transesterification method which is one of the melt polymerization methods, involves reacting a dicarboxylic acid ester with a dihydroxy compound (excluding the dicarboxylic acid) in the presence of a catalyst, and transesterifying it while distilling off the resulting alcohol. Is generally used for the synthesis of polyester resins.
- a dicarboxylic acid and a dihydroxy compound are dehydrated to form an ester compound, and then an ester exchange reaction is performed while distilling off the excess dihydroxy compound under reduced pressure. It is a method of obtaining a polyester resin by performing.
- the direct polymerization method has the advantage that no distillate of alcohol is used unlike the transesterification method, and an inexpensive dicarboxylic acid can be used as a raw material.
- catalyst amount polymerization conditions such as temperature
- additives such as thermal stabilizers, etherification inhibitors and catalyst deactivators when carrying out these melt polymerization methods. Can do.
- the reaction may be performed in the presence of a catalyst.
- a catalyst various catalysts used for the production of a polyester carbonate resin, such as a metal catalyst, can be used.
- a metal catalyst for example, a metal compound containing an alkali metal, an alkaline earth metal, a transition metal, a periodic table group 13 metal, a periodic table group 14 metal, a periodic table group 15 metal, or the like is used.
- the metal compound include alkoxide, organic acid salt (acetate, propionate, etc.), inorganic acid salt (borate, carbonate, etc.), metal oxide and the like. These catalysts can be used alone or in combination of two or more.
- the amount of the catalyst used is, for example, about 0.01 ⁇ 10 ⁇ 4 to 100 ⁇ 10 ⁇ 4 mol, preferably about 0.1 ⁇ 10 ⁇ 4 to 40 ⁇ 10 ⁇ 4 mol, relative to 1 mol of the dicarboxylic acid component. May be.
- alkali metal compound examples include sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium carbonate, sodium acetate, potassium acetate, acetic acid.
- Cesium lithium acetate, sodium stearate, potassium stearate, cesium stearate, stearium, potassium benzoate, cesium benzoate, lithium benzoate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, dilithium hydrogen phosphate, phenyl Disodium phosphate, disodium salt of bisphenol A, dipotassium salt, cesium salt, dilithium salt, phenol sodium salt, potassium salt, cesium salt, lithium salt and the like are used.
- alkaline earth metal compound examples include magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, magnesium hydrogen carbonate, calcium hydrogen carbonate, strontium hydrogen carbonate, barium hydrogen carbonate, magnesium carbonate, calcium carbonate.
- Strontium carbonate, barium carbonate, magnesium acetate, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenyl phosphate, and the like are used.
- zinc, tin, zirconium and lead salts are preferably used, and these can be used alone or in combination.
- These catalysts are generally used in a ratio of 1 ⁇ 10 ⁇ 9 to 1 ⁇ 10 ⁇ 3 moles with respect to a total of 1 mole of dihydroxy compounds (excluding dicarboxylic acids), preferably 10 ⁇ 7. Used in a ratio of ⁇ 10 ⁇ 4 mol.
- Polyester carbonate resins include other resins, antioxidants, mold release agents, light stabilizers, UV absorbers, plasticizers, extenders, matting agents, drying regulators, antistatic agents, antisettling agents, and surfactants. Add various additives such as additives, fluidity modifiers, drying oils, waxes, fillers, colorants, reinforcing agents, surface smoothing agents, leveling agents, curing reaction accelerators, thickeners, and molding aids. You can also. Specific examples and addition amounts of these additives are the same as those in the above-mentioned “1. Polycarbonate resin”.
- an ester of a polyfunctional alcohol and a fatty acid, particularly a stearic acid ester of glycerin is 0.005 to 2.0 parts by weight, preferably 0.8. Addition in the range of 01 to 0.6 parts by weight, more preferably 0.02 to 0.5 parts by weight is preferable because troubles due to defective mold release can be reduced.
- the catalyst can be deactivated by adding a known acidic substance.
- the acidic substance used for deactivation of the catalyst include aromatic sulfonic acids such as p-toluenesulfonic acid; aromatic sulfonic acid esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate; Aromatic sulfonates such as tetrabutylphosphonium salt of dodecylbenzene sulfonate; Organic halides such as stearic acid chloride, benzoyl chloride, p-toluenesulfonic acid chloride; Alkyl sulfuric acid such as dimethyl sulfate; Organic halides such as benzyl chloride Are preferably used
- the polyester carbonate resin according to the embodiment is desired to have as little foreign matter content as possible, and it is preferable to perform filtration of the molten raw material, filtration of the catalyst solution, and filtration of the molten oligomer.
- the filter mesh is preferably 7 ⁇ m or less, more preferably 5 ⁇ m or less.
- the mesh of the polymer filter is preferably 100 ⁇ m or less, more preferably 30 ⁇ m or less.
- the step of collecting the resin pellets must be a low dust environment, and is preferably class 6 or less, more preferably class 5 or less.
- the refractive index and Abbe number can be measured by the following measuring method.
- a polyester carbonate resin is dissolved in methylene chloride to prepare a cast film, and the refractive index is measured with a refractometer.
- the refractive index is a value measured at 25 ° C. and 589 nm (d line)
- the Abbe number is a value calculated from the refractive indices measured at 656 nm (C line), 486 nm (F line), and d line.
- the refractive index measured in this way is preferably 1.60 or more, and more preferably 1.645 to 1.665.
- the Abbe number is preferably 24 or less, more preferably 21 or less, for example, 18 to 24.
- the glass transition temperature is measured with a differential scanning calorimeter and is not particularly limited, but is usually 110 ° C. or higher, preferably 115 ° C. or higher, more preferably 120 ° C. or higher.
- the glass transition temperature of the polyester resin and the polyester carbonate resin can be easily adjusted to 110 ° C. by appropriately selecting a conventionally known diol or dicarboxylic acid such as a diol having a cyclic acetal skeleton or an aromatic hydrocarbon group or a dicarboxylic acid having a naphthalene skeleton. This can be done.
- the glass transition temperature is if the glass transition temperature is too high, it is necessary to increase the temperature at which the resin is molded, and the resin itself may unexpectedly undergo thermal decomposition. Therefore, the glass transition temperature is preferably less than 150 ° C.
- the weight average molecular weight (Mw) in terms of polystyrene is preferably 10,000 to 100,000, more preferably 20,000 to 50,000. If Mw is less than 10,000, the resulting resin molded product tends to become brittle, which is not preferable. If Mw is larger than 100,000, the melt viscosity becomes high, so that it becomes difficult to take out the resin from the mold at the time of molding, and further, the fluidity becomes worse and it becomes difficult to perform injection molding in the molten state.
- the solution hue (lightness; L value) is measured by the method shown in Examples, but is preferably 88 or more, more preferably 95 to 99.
- L value is measured by the method shown in Examples, but is preferably 88 or more, more preferably 95 to 99.
- the L value is less than 88, the resin is strongly colored and is difficult to use as an optical material.
- polyester carbonate resin The intrinsic viscosity and semi-crystallization time of the polyester carbonate resin according to the embodiment are the same as those described in “2. Polyester resin” above.
- the resin according to the embodiment preferably satisfies the following physical properties (1) and (2).
- the polyester carbonate resin can be used for various applications.
- it can be used for injection molded articles, sheets, films, extruded molded articles such as pipes, bottles, foams, adhesives, adhesives, paints and the like.
- the sheet may be a single layer or a multilayer
- the film may be a single layer or a multilayer.
- the sheet may be unstretched, or may be stretched in one direction or in two directions. May be.
- the bottle may be a direct blow bottle, an injection blow bottle, or an injection molded bottle.
- the foam may be a bead foam or an extruded foam.
- Applications that require high heat resistance and water vapor barrier, such as products used in automobiles, packaging materials for import / export, electronic materials such as solar cell backsheets, food packaging materials for retort processing and microwave heating Can be suitably used.
- An excellent optical lens can be obtained by injection-molding the polyester carbonate resin according to the embodiment into a lens shape particularly by an injection molding machine or an injection compression molding machine.
- the molding environment must naturally be a low dust environment, and is preferably class 6 or less, more preferably class 5 or less.
- the optical lens obtained by molding the polyester carbonate resin is preferably used in the form of an aspherical lens as necessary. Since an aspherical lens can substantially eliminate spherical aberration with a single lens, there is no need to remove spherical aberration by combining a plurality of spherical lenses, which reduces weight and reduces production costs. It becomes possible. Therefore, the aspherical lens is particularly useful as a camera lens among optical lenses.
- the astigmatism of the aspheric lens is preferably 0 to 15 m ⁇ , more preferably 0 to 10 m ⁇ .
- a coating layer such as an antireflection layer or a hard coating layer may be provided on the surface of the optical lens obtained by molding the polyester carbonate resin.
- 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.
- Optical lenses obtained by molding polyester carbonate resin can be used for various lenses such as pickup lenses, f- ⁇ lenses, and spectacle lenses, but because of their high refractive index and low Abbe number, they are used for chromatic aberration correction. It can be particularly suitably used as a lens. Specifically, it is suitably used as a lens for a single-lens reflex camera, a digital still camera, a video camera, a camera-equipped mobile phone, a lens-equipped film, a telescope, a binocular, a microscope, a projector, or the like.
- the optical lens using the polyester carbonate resin according to the embodiment is a concave lens, it can be used as an optical lens system with little chromatic aberration in combination with another convex lens having a high Abbe number.
- the Abbe number of the convex lens to be combined is preferably 40 to 60, and more preferably 50 to 60.
- Mw Weight average molecular weight in terms of polystyrene
- Refractive index (nD) Using a Abbe refractometer, a 0.1 mm thick film made of the polycarbonate resin produced in the example was measured by the method of JIS-K-7142 (23 ° C., wavelength 589 nm).
- ⁇ (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
- Tg Glass transition temperature
- DSC differential thermal scanning calorimeter
- Td Thermal decomposition start temperature
- Oriented birefringence ( ⁇ n) After cutting a cast film having a thickness of 0.1 mm into a square of 5.0 cm square, both ends of the film are sandwiched between chucks (3.0 cm between chucks), and the polycarbonate resin Tg + 5 ° C. Stretched 1.5 times. The phase difference (Re) at 589 nm was measured using an ellipsometer M-220 manufactured by JASCO Corporation, and the orientation birefringence ( ⁇ n) was determined from the following formula.
- the birefringence code is obtained by using an ellipsometer M-220 manufactured by JASCO Corporation to determine the direction in which the refractive index is maximum in the plane of the stretched film, Judging from the relationship with the stretching direction.
- the stretching direction is the direction in which the refractive index is maximum in the film plane.
- the stretching direction is a direction orthogonal to the direction in which the refractive index is maximum in the film plane.
- Total light transmittance Measured by a method of JIS-K-7361-1 using a turbidimeter NDH2000 manufactured by Nippon Denshoku Industries Co., Ltd. for a 0.1 mm thick film made of polycarbonate resin produced in the examples. did.
- Residual phenol and residual diphenyl carbonate amount 1.0 g of the weighed polycarbonate resin was precisely weighed, dissolved in 10 ml of dichloromethane, and gradually added to 100 ml of methanol with stirring to reprecipitate the resin. After sufficiently stirring, the precipitate was filtered off, and 1.0 g of a standard substance solution was precisely weighed and added to the solid obtained by concentrating the filtrate with an evaporator. Further, a solution diluted by adding 1 g of chloroform was quantified by GC-MS.
- Standard solution Chloroform solution of 200 ppm trimethylolphenol Measuring device (GC-MS): Agilent HP6890 / 5973MSD
- Column Capillary column DB-5MS, 30m ⁇ 0.25mm ID, film thickness 0.5 ⁇ m
- Temperature rise conditions 50 °C (5min hold) to 300 °C (15min hold), 10 °C / min
- Ionization method EI method
- Carrier gas He, 1.0 ml / min Aux temperature: 300 °C Mass scan range: 33-700
- Example 1 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene (hereinafter sometimes abbreviated as “BHEBN”) 13.4 g (0.035 mol), 9,9-bis (4- ( 2-hydroxyethoxy) phenyl) fluorene (hereinafter abbreviated as “BPEF”) 35.6 g (0.081 mol), diphenyl carbonate (hereinafter abbreviated as “DPC”) 25.0 g (0.
- BHEBN 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene
- BPEF 9,9-bis (4- ( 2-hydroxyethoxy) phenyl) fluorene
- DPC diphenyl carbonate
- the reaction was carried out while maintaining the temperature for 20 minutes. Further, the temperature was raised to 230 ° C. at a rate of 75 ° C./hr, and 10 minutes after the completion of the temperature raising, the degree of vacuum was reduced to 1 mmHg or less over 1 hour while maintaining the temperature. Thereafter, the temperature was raised to 240 ° C. at a rate of 60 ° C./hr, and the reaction was further performed with stirring for 30 minutes. After completion of the reaction, nitrogen was blown into the reactor to return to normal pressure, and the produced polycarbonate resin was taken out. The amount of residual phenol in the polycarbonate resin was 150 ppm, and the amount of residual DPC was 120 ppm.
- Example 2 The amount of BHEBN, BPEF, DPC and sodium bicarbonate was adjusted to 17.1 g (0.046 mol) BHEBN, 30.1 g (0.069 mol) BPEF, 25.0 g (0.117 mol) DPC and 8.7 ⁇ sodium bicarbonate. Except for changing to 10 ⁇ 5 g (1.0 ⁇ 10 ⁇ 6 mol), the same operation as in Example 1 was performed, and the produced polycarbonate resin was taken out. The amount of residual phenol in the polycarbonate resin was 60 ppm, and the amount of residual DPC was 250 ppm.
- Example 3 The amount of BHEBN, BPEF, DPC and sodium bicarbonate was adjusted to 30.0 g (0.080 mol) BHEBN, 15.1 g (0.034 mol) BPEF, 25.0 g (0.117 mol) DPC, and 8.7 sodium bicarbonate. Except for changing to x10 -5 g (1.0 x 10 -6 mol), the same operation as in Example 1 was performed, and the produced polycarbonate resin was taken out. The amount of residual phenol in the polycarbonate resin was 120 ppm.
- Example 4 The amount of BHEBN, BPEF, DPC and sodium bicarbonate was adjusted to 38.9 g (0.104 mol) BHEBN, 5.07 g (0.012 mol), BPEF 25.0 g (0.117 mol), and sodium bicarbonate 1.1.
- the produced polycarbonate resin was taken out in the same manner as in Example 1 except that it was changed to ⁇ 10 ⁇ 4 g (1.3 ⁇ 10 ⁇ 6 mol).
- the amount of residual phenol in the polycarbonate resin was 100 ppm.
- Example of production of optical film (1) The polycarbonate resins obtained in Examples 1 to 4, Reference Example 1 and Comparative Example 1 were dissolved in methylene chloride to prepare a resin solution having a solid content concentration of 5.3% by weight. This resin solution was poured into a cast film making mold, peeled off after methylene chloride volatilization, and dried to prepare a cast film having a thickness of 0.1 mm. The cast film was evaluated for refractive index (nD), Abbe number ( ⁇ ), and total light transmittance. Moreover, the obtained cast film was extended
- polystyrene conversion weight average molecular weight (Mw), glass transition temperature (Tg), and thermal decomposition start temperature (Td) of the resins obtained in the above-described Examples, Reference Examples and Comparative Examples were measured. These values are shown in Table 1.
- Table 2 shows the birefringence.
- Table 3 shows the evaluation criteria for the orientation birefringence ( ⁇ n) in Table 2.
- Example 7 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene (hereinafter sometimes abbreviated as “BHEBN”) 3.44 g (0.009 mol), 9,9-bis (4- ( 2-hydroxyethoxy) -3-phenylphenyl) fluorene (hereinafter abbreviated as “BEPF”) 48.9 g (0.083 mol), diphenyl carbonate (hereinafter abbreviated as “DPC”) 20.
- BHEBN 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene
- BEPF 9,9-bis (4- ( 2-hydroxyethoxy) -3-phenylphenyl) fluorene
- DPC diphenyl carbonate
- the reaction was carried out while maintaining the temperature for 20 minutes. Further, the temperature was raised to 230 ° C. at a rate of 75 ° C./hr, and 10 minutes after the completion of the temperature raising, the degree of vacuum was reduced to 1 mmHg or less over 1 hour while maintaining the temperature. Thereafter, the temperature was raised to 240 ° C. at a rate of 60 ° C./hr, and the reaction was further performed with stirring for 30 minutes. After completion of the reaction, nitrogen was blown into the reactor to return to normal pressure, and the produced polycarbonate resin was taken out.
- Example 8 The amount of BHEBN, BEPF, DPC and sodium bicarbonate was adjusted to 5.17 g (0.014 mol) of BHEBN, 19.0 g (0.032 mol) of BEPF, 10.0 g (0.047 mol) of DPC, 9.7 ⁇ sodium bicarbonate. Except for changing to 10 ⁇ 5 g (1.2 ⁇ 10 ⁇ 6 mol), the same operation as in Example 7 was performed, and the produced polycarbonate resin was taken out.
- Example 9 The amounts of BHEBN, BEPF, DPC and sodium bicarbonate were adjusted to 13.8 g (0.037 mol) of BHEBN, 32.6 g (0.055 mol) of BEPF, 20.0 g (0.093 mol) of DPC, 1.5 ⁇ sodium bicarbonate. Except for changing to 10 ⁇ 4 g (1.8 ⁇ 10 ⁇ 6 mol), the same operation as in Example 7 was performed, and the produced polycarbonate resin was taken out.
- Example 10 The amount of BHEBN, BEPF, DPC and sodium bicarbonate was determined by adding 24.4 g (0.065 mol) of BHEBN, 16.5 g (0.028 mol) of BEPF, 20.2 g (0.094 mol) of DPC, 1.6 ⁇ sodium bicarbonate. Except for changing to 10 ⁇ 4 g (1.9 ⁇ 10 ⁇ 6 mol), the same operation as in Example 7 was performed, and the produced polycarbonate resin was taken out.
- Example 11 The amount of BHEBN, BEPF, DPC and sodium bicarbonate was adjusted to 31.0 g (0.083 mol) of BHEBN, 5.4 g (0.009 mol) of BEPF, 20.0 g (0.093 mol) of DPC, 1.5 ⁇ sodium bicarbonate. Except for changing to 10 ⁇ 4 g (1.8 ⁇ 10 ⁇ 6 mol), the same operation as in Example 7 was performed, and the produced polycarbonate resin was taken out.
- Example of polycarbonate resin composition The measured value in the Example of polycarbonate resin composition was measured using the following method or apparatus.
- Refractive index (nD) A molded product obtained by press-molding a polycarbonate resin composition into a 3 mm thick ⁇ 8 mm ⁇ 8 mm rectangular parallelepiped was measured with a refractometer (KPR-200) manufactured by Shimadzu Corporation (23 ° C., wavelength 589 nm).
- Abbe number ( ⁇ ) A molded product obtained by press-molding a polycarbonate resin composition into a 3 mm thick ⁇ 8 mm ⁇ 8 mm rectangular parallelepiped was measured at a wavelength of 486 nm, 589 nm, and 656 nm using a refractometer (KPR-200) manufactured by Shimadzu Corporation.
- ⁇ (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
- Optical distortion Evaluation was performed by sandwiching a molded piece made of polycarbonate resin composition having a thickness of 3 mm between two polarizing plates and visually observing light leakage from behind by a crossed Nicols method. More specifically, the polycarbonate resin compositions obtained in Examples 13 to 17 and Comparative Examples 3 to 5 were used, and the diameter was 50 mm and the thickness was 3 mm using a FANUC ROBOSHOT S-2000i30A injection molding machine. The molded piece was injection molded. This molded piece was sandwiched between two polarizing plates and evaluated by visually observing light leakage from behind using a crossed Nicols method. In the evaluation, A: slight light leakage was observed, B: light leakage was present, and C: light leakage was significant.
- the temperature was raised to 230 ° C. at a rate of 45 ° C./hr, and maintained at 230 ° C. and 200 mmHg for 10 minutes.
- the pressure reduction degree was adjusted to 150 mmHg over 20 minutes, and it hold
- it adjusted to 120 mmHg over 10 minutes, and hold
- the polymerization reaction was carried out while stirring for 30 minutes under conditions of 230 ° C.
- the temperature was raised to 240 ° C. at a rate of 37.5 ° C./hr, and held at 240 ° C. and 150 mmHg for 10 minutes. Then, it adjusted to 120 mmHg over 10 minutes, and hold
- Example 13 0.44 kg of the polycarbonate resin (A1) pellets produced in Synthesis Example 1, 4.57 kg of the polycarbonate resin (B1) pellets produced in Synthesis Example 2, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4 -Hydroxyphenyl) propionate] and 7.5 g of stearic acid monoglyceride were shaken well, kneaded by an extruder at 260 ° C. and pelletized to obtain 3.3 kg of blended pellets.
- the Tg of the pellet was 142 ° C. and no inflection point was found.
- the phenol content in the pellets was 450 ppm.
- Mw of this pellet was 25,000.
- the pellet was injection-molded to obtain a disc having a diameter of 50 mm and a thickness of 3 mm. The disc was transparent. Table 7 shows the evaluation results.
- Example 14 1.34 kg of the polycarbonate resin (A1) pellets prepared in Synthesis Example 1, 3.66 kg of the polycarbonate resin (B1) pellets manufactured in Synthesis Example 2, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4 -Hydroxyphenyl) propionate] and 7.5 g of stearic acid monoglyceride were shaken well, kneaded by an extruder at 260 ° C., and pelletized to obtain 3.2 kg of blended pellets. The pellet had a Tg of 136 ° C. and no inflection point was found. Moreover, Mw of this pellet was 26,000. The phenol content in the pellets was 350 ppm. The pellet was injection-molded to obtain a disc having a diameter of 50 mm and a thickness of 3 mm. The disc was transparent. Table 7 shows the evaluation results.
- Example 15 2.30 kg of the polycarbonate resin (A1) pellets produced in Synthesis Example 1, 2.70 kg of the polycarbonate resin (B1) pellets produced in Synthesis Example 2, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4 -Hydroxyphenyl) propionate] and 7.5 g of stearic acid monoglyceride were shaken well, kneaded by an extruder at 260 ° C., and pelletized to obtain 3.2 kg of blended pellets.
- the Tg of the pellet was 128 ° C., and no inflection point was found.
- Mw of this pellet was 27,000.
- the phenol content in the pellets was 370 ppm.
- the pellet was injection-molded to obtain a disc having a diameter of 50 mm and a thickness of 3 mm. The disc was transparent. Table 7 shows the evaluation results.
- Example 16 3.33 kg of the polycarbonate resin (A1) pellets prepared in Synthesis Example 1, 1.67 kg of the polycarbonate resin (B1) pellets manufactured in Synthesis Example 2, and pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4 -Hydroxyphenyl) propionate] and 7.5 g of stearic acid monoglyceride were shaken well, kneaded by an extruder at 260 ° C. and pelletized to obtain 3.3 kg of blended pellets. The Tg of the pellet was 123 ° C., and no inflection point was found. Moreover, Mw of this pellet was 29,000. The phenol content in the pellets was 450 ppm. The pellet was injection-molded to obtain a disc having a diameter of 50 mm and a thickness of 3 mm. The disc was transparent. Table 7 shows the evaluation results.
- Example 17 4.43 kg of the polycarbonate resin (A1) pellets produced in Synthesis Example 1, 0.58 kg of the polycarbonate resin (B1) pellets produced in Synthesis Example 2, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4 -Hydroxyphenyl) propionate] and 7.5 g of lauric acid monoglyceride were shaken well, kneaded by an extruder at 260 ° C. and pelletized to obtain 3.3 kg of blended pellets. The pellet had a Tg of 117 ° C. and no inflection point was found. Moreover, Mw of this pellet was 31,000. The phenol content in the pellets was 380 ppm. The pellet was injection-molded to obtain a disc having a diameter of 50 mm and a thickness of 3 mm. The disc was transparent. Table 7 shows the evaluation results.
- Mw Weight average molecular weight in terms of polystyrene
- ⁇ (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 wavelength 486 nm
- Example 18 In a glass flask equipped with a heating device, a stirring blade, a condenser, a trap, a thermometer, and a nitrogen gas introduction tube, 1.00 mol of dimethyl terephthalate (hereinafter referred to as DMT), 2.20 mol of ethylene glycol, 9, 9-bis [4- (2-hydroxyethoxy) phenyl] fluorene (hereinafter referred to as BPEF) 0.10 mol, 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene (hereinafter referred to as BHEBN) ) 0.81 mol was added.
- DMT dimethyl terephthalate
- BPEF 9, 9-bis [4- (2-hydroxyethoxy) phenyl] fluorene
- BHEBN 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene
- the mixture was gradually heated and melted under stirring in a nitrogen atmosphere to carry out an esterification reaction. After the reaction conversion rate of the dicarboxylic acid component reached 90% or more, 0.14 mol% germanium oxide and 0.12 mol% triethyl phosphate were added to 100 mol% of the dicarboxylic acid component. The temperature was gradually increased and the pressure was reduced, ethylene glycol was removed while the pressure was reduced, and finally polycondensation was performed at 250 to 280 ° C. and 0.1 kPa or less.
- the obtained polyester resin had a polystyrene-reduced weight average molecular weight of 42,000.
- Table 8 shows the physical property evaluation.
- Example 19 The same operation as in Example 1 was carried out except that BPEF was changed to 0.27 mol, BHEBN was changed to 0.63 mol, and DMT was changed to dimethyl 2,6-naphthalenedicarboxylate (hereinafter abbreviated as NDCM). As a result, a polyester copolymer having a weight average molecular weight of 40,500 was obtained. Table 8 shows the physical property evaluation.
- Polyester carbonate resin ⁇ Evaluation method of polyester carbonate resin> The measured value in the Example of polyester carbonate resin was measured using the following method or apparatus.
- 1) Average molecular weight: Created a calibration curve using standard polystyrene with known molecular weight (molecular weight distribution 1) using tetrahydrofuran permeation solvent as gel permeation chromatograph (GPC) Shodex GPC-101 manufactured by Showa Denko K.K. did. Based on this calibration curve, the number average molecular weight (Mn) and the weight average molecular weight (Mw) were calculated from the retention time of GPC.
- Mn number average molecular weight
- Mw weight average molecular weight
- BHEBN 2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene
- BPEF 9,9-bis (4- ( 2-hydroxyethoxy) phenyl) fluorene
- DPC diphenyl carbonate
- DMT dimethyl terephthalate
- the rotational speed was increased to 200 rpm
- the pressure was reduced to 200 mmHg at a speed of 28 mmHg / min
- the temperature was increased to 260 ° C at a speed of 60 ° C / hr.
- the start of distillation of by-produced phenol was confirmed.
- the pressure was reduced at 10 mmHg / min, and the reaction was completed in 20 minutes after the pressure reached 0 mmHg.
- nitrogen was blown into the reactor to return to normal pressure, and the produced polyester carbonate resin was taken out.
- Example 21 17.3 g (0.046 mol) of BHEBN, 25.27 g (0.058 mol) of BPEF, 19.94 g (0.093 mol) of DPC, and 2.239 g (0.012 mol) of DMT were added to a 300 ml solution equipped with a stirrer and a distiller. Placed in a neck flask. Depressurization and nitrogen filling were repeated 5 times, and then heated at 180 ° C. in a nitrogen atmosphere of 760 mmHg. After 10 minutes from the start of heating, complete dissolution of the raw materials was confirmed, and then stirring was performed for 10 minutes under the same conditions.
- the rotational speed was increased to 200 rpm
- the pressure was reduced to 200 mmHg at a speed of 28 mmHg / min
- the temperature was increased to 240 ° C at a speed of 60 ° C / hr.
- the start of distillation of by-produced phenol was confirmed.
- the pressure was reduced at 10 mmHg / min, and the reaction was completed in 40 minutes after the pressure reached 0.8 mmHg.
- nitrogen was blown into the reactor to return to normal pressure, and the produced polyester carbonate resin was taken out.
- Example 22 35.64 g (0.095 mol) of BHEBN, 4.615 g (0.011 mol) of BPEF, 20.00 g (0.093 mol) of DPC, and 2.557 g (0.013 mol) of DMT Placed in a neck flask. Depressurization and nitrogen filling were repeated 5 times, and then heated at 180 ° C. in a nitrogen atmosphere of 760 mmHg. After 10 minutes from the start of heating, complete dissolution of the raw materials was confirmed, and then stirring was performed for 10 minutes under the same conditions. Thereafter, the pressure was reduced to 200 mmHg at 28 mmHg / min, and the temperature was raised to 250 ° C at a rate of 60 ° C / hr. At this time, the start of distillation of by-produced phenol was confirmed. Finally, nitrogen was blown into the reactor to return to normal pressure, and the produced polyester carbonate resin was taken out.
- Example 23 3.928 g (0.011 mol) of BHEBN, 41.95 g (0.096 mol) of BPEF, 20.34 g (0.095 mol) of DPC, and 2.287 g (0.012 mol) of DMT were added to a 300 ml flask equipped with a stirrer and a distiller. Placed in a neck flask. Depressurization and nitrogen filling were repeated 5 times, and then heated at 180 ° C. in a nitrogen atmosphere of 760 mmHg. After 10 minutes from the start of heating, complete dissolution of the raw materials was confirmed, and then stirring was performed for 10 minutes under the same conditions.
- the rotational speed was increased to 200 rpm
- the pressure was reduced to 200 mmHg at a speed of 28 mmHg / min
- the temperature was increased to 260 ° C at a speed of 60 ° C / hr.
- the start of distillation of by-produced phenol was confirmed.
- the pressure was reduced at 1.6 mmHg / min.
- the reaction was completed in 20 minutes after the pressure reached 0.8 mmHg. Nitrogen was blown into the reactor to return to normal pressure, and the produced polyester carbonate resin was taken out.
- BHEBN 10.92 g (0.029 mol), BPEF 33.41 g (0.076 mol), DPC 20.10 g (0.093 mol), and DMT 2.289 g (0.0118 mol) were added to a 300 ml flask with stirrer and distiller. Placed in a neck flask. Depressurization and nitrogen filling were repeated 5 times, and then heated at 180 ° C. in a nitrogen atmosphere of 760 mmHg. After 10 minutes from the start of heating, complete dissolution of the raw materials was confirmed, and then stirring was performed for 10 minutes under the same conditions.
- the rotational speed was increased to 200 rpm
- the pressure was reduced to 200 mmHg at a speed of 4.6 mmHg / min
- the temperature was increased to 260 ° C at a speed of 60 ° C / hr.
- the start of distillation of by-produced phenol was confirmed.
- the pressure was reduced at 3.3 mmHg / min, and the reaction was completed in 60 minutes after the pressure reached 0.8 mmHg.
- nitrogen was blown into the reactor to return to normal pressure, and the produced polyester carbonate resin was taken out.
- the rotational speed was increased to 200 rpm
- the pressure was reduced to 200 mmHg at a speed of 28 mmHg / min
- the temperature was increased to 260 ° C at a speed of 60 ° C / hr.
- the start of distillation of by-produced phenol was confirmed.
- the pressure was reduced at 3.3 mmHg / min, and the reaction was completed in 30 minutes after the pressure reached 0.8 mmHg.
- nitrogen was blown into the reactor to return to normal pressure, and the produced polyester carbonate resin was taken out.
- the rotational speed was increased to 200 rpm
- the pressure was reduced to 200 mmHg at a speed of 28 mmHg / min
- the temperature was increased to 260 ° C at a speed of 60 ° C / hr.
- the start of distillation of by-produced phenol was confirmed.
- the pressure was reduced at 10 mmHg / min, and the reaction was terminated after the pressure reached 0.8 mmHg. Nitrogen was blown into the reactor to return to normal pressure, and the produced polyester carbonate resin was taken out.
- the rotational speed was increased to 200 rpm, the pressure was reduced to 200 mmHg at a speed of 28 mmHg / min, and the temperature was raised to 260 ° C at a speed of 60 ° C / hr. At this time, the start of distillation of by-produced phenol was confirmed. After reaching a pressure of 200 mmHg and a temperature of 260 ° C., the pressure was reduced at 10 mmHg / min, and the reaction was terminated after the pressure reached 0.8 mmHg. Nitrogen was blown into the reactor to return to normal pressure, and the produced polyester carbonate resin was taken out.
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Abstract
Description
[式(1)において、Xは炭素数1~10のアルキレン基である]
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。
[2] 前記一般式(2)で表される化合物は、下記一般式(2a)または(2b)で表される化合物である[1]に記載のポリエステル樹脂:
[式(2a)において、R1およびR2は[1]で定義した通りである]
[式(2b)において、R1およびR2は[1]で定義した通りである]。
[3] 前記ジカルボン酸またはその誘導体は、ナフタレンジカルボン酸、テレフタル酸、イソフタル酸、フルオレン基を有するジカルボン酸、またはこれらのエステルである[1]または[2]に記載のポリエステル樹脂。
[3-1] 前記フルオレン基を有するジカルボン酸は、以下の一般式(3)で表されるジカルボン酸である[3]に記載のポリエステル樹脂:
(式(3)において、Yは、それぞれ独立に、単結合、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を示す)。
[4] 前記ポリエステル樹脂において、ジヒドロキシ化合物に由来する構成単位のうち前記一般式(1)で表される化合物に由来する構成単位の割合は5~95モル%であり、前記一般式(2)で表される化合物に由来する構成単位の割合は2.5~47.5モル%である、[1]~[3-1]のいずれかに記載のポリエステル樹脂。
[5] さらにグリコールに由来する構成単位を含み、前記ポリエステル樹脂におけるジヒドロキシ化合物に由来する構成単位のうちグリコールに由来する構成単位の割合は、5~70モル%である[1]~[4]のいずれかに記載のポリエステル樹脂。
[5-1] 下記一般式(1)で表される化合物と、下記一般式(2)で表される化合物と、ジカルボン酸またはその誘導体とを共重合させて得られるポリエステル樹脂:
(式(1)において、Xは炭素数1~10のアルキレン基である)
(式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である)。
[6] [1]~[5-1]のいずれかに記載のポリエステル樹脂を含む光学部材。
[7] 前記光学部材が、一眼レフカメラ、デジタルスチルカメラ、ビデオカメラ、カメラ付携帯電話、レンズ付フィルム、望遠鏡、双眼鏡、顕微鏡、またはプロジェクターの光学レンズである[6]に記載の光学部材。
[式(1)において、Xは炭素数1~10のアルキレン基である]
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。
[9] 前記一般式(2)で表される化合物は、下記一般式(2a)または(2b)で表される化合物である[8]に記載のポリエステルカーボネート樹脂:
[式(2a)において、R1およびR2は[8]で定義した通りである]
[式(2b)において、R1およびR2は[8]で定義した通りである]。
[10] 前記ジカルボン酸またはその誘導体は、ナフタレンジカルボン酸、テレフタル酸、イソフタル酸、フルオレン基を有するジカルボン酸、またはこれらのエステルである[8]または[9]に記載のポリエステルカーボネート樹脂。
[10-1] 前記フルオレン基を有するジカルボン酸は、以下の一般式(3)で表されるジカルボン酸である[10]に記載のポリエステルカーボネート樹脂:
(式(3)において、Yは、それぞれ独立に、単結合、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を示す)。
[10-2] 前記炭酸ジエステルは、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、m-クレジルカーボネート、ジメチルカーボネート、ジエチルカーボネート、ジブチルカーボネートおよびジシクロヘキシルカーボネートからなる群より選択される[8]~[10-1]のいずれかに記載のポリエステルカーボネート樹脂。
[11] 前記ポリエステルカーボネート樹脂において、ジヒドロキシ化合物に由来する構成単位のうち前記一般式(1)で表される化合物に由来する構成単位の割合は5~95モル%であり、前記一般式(2)で表される化合物に由来する構成単位の割合は2.5~47.5モル%である、[8]~[10-2]のいずれかに記載のポリエステルカーボネート樹脂。
[11-1] 下記一般式(1)で表される化合物と、下記一般式(2)で表される化合物と、炭酸ジエステルと、ジカルボン酸またはその誘導体とを共重合させて得られるポリエステルカーボネート樹脂:
(式(1)において、Xは炭素数1~10のアルキレン基である)
(式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である)。
[12] 屈折率が1.645~1.660である、[8]~[11-1]のいずれかに記載のポリエステルカーボネート樹脂。
[13] ポリスチレン換算重量平均分子量(Mw)が14,000~100,000である、[8]~[12]のいずれかに記載のポリエステルカーボネート樹脂。
[14] [8]~[13]のいずれかに記載のポリエステルカーボネート樹脂を含む光学部材。
[15] 前記光学部材が、一眼レフカメラ、デジタルスチルカメラ、ビデオカメラ、カメラ付携帯電話、レンズ付フィルム、望遠鏡、双眼鏡、顕微鏡、またはプロジェクターの光学レンズである[14]に記載の光学部材。
ポリカーボネート樹脂:
[式(1)において、Xは炭素数1~10のアルキレン基である]
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。
[17] 下記一般式(1)で表される化合物に由来する構成単位と、下記一般式(2)で表される化合物に由来する構成単位とを含み、炭酸ジエステル含有量が0.1~1000ppmであるポリカーボネート樹脂:
[式(1)において、Xは炭素数1~10のアルキレン基である]
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。
[18] 下記一般式(1)で表される化合物に由来する構成単位と、下記一般式(2)で表される化合物に由来する構成単位とを含むポリカーボネート樹脂、ならびに酸化防止剤および/または離型剤を含む樹脂組成物:
[式(1)において、Xは炭素数1~10のアルキレン基である]
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。
[19] 前記酸化防止剤が、ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート]である[18]に記載の樹脂組成物。
[20] 前記離型剤が、アルコールと脂肪酸とのエステルである[18]または[19]に記載の樹脂組成物。
[20-1] 前記アルコールと脂肪酸とのエステルが、ステアリン酸モノグリセリドまたはラウリン酸モノグリセリドである[20]に記載の樹脂組成物。
[式(1)において、Xは炭素数1~10のアルキレン基である]。
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。
[22] 下記一般式(1)で表される化合物に由来する構成単位を含むポリカーボネート樹脂と、下記一般式(2)で表される化合物に由来する構成単位を含むポリカーボネート樹脂とを含み、炭酸ジエステル含有量が0.1~1000ppmであるポリカーボネート樹脂組成物:
[式(1)において、Xは炭素数1~10のアルキレン基である]。
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。
[23] さらに、酸化防止剤および/または離型剤を含む、[20]または[21]に記載の樹脂組成物。
[24] 前記酸化防止剤が、ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート]である[23]に記載の樹脂組成物。
[25] 前記離型剤が、アルコールと脂肪酸とのエステルである[22]または[23]に記載の樹脂組成物。
[25-1] 前記アルコールと脂肪酸とのエステルが、ステアリン酸モノグリセリドまたはラウリン酸モノグリセリドである[25]に記載の樹脂組成物。
一般式(1)に示すビナフチル骨格を有する化合物、および、一般式(4)に示すフルオレン骨格を有する化合物を、
(a)ヒドロキシル基、ヒドロキシカルボニル基、アルコキシカルボニル基、アシルオキシカルボニル基、または、ハロゲン化カルボニル基から選ばれる1種以上の官能基を、2個以上有する化合物を併用してあるいは併用せず、かつ、
(b)炭酸ジエステルを使用してあるいは使用せずに、
重縮合して製造した樹脂。
(Xは炭素数1~10のアルキレン基である。)
(Yは、ヒドロキシル基、ヒドロキシカルボニル基、アルコキシカルボニル基、アシルオキシカルボニル基、もしくはハロゲン化カルボニル基から選ばれる1種以上の官能基を有する、炭素数1~40かつ酸素数1~4の有機基である。)
<2>
(a)一般式(1)に示すビナフチル骨格を有する化合物を、
ヒドロキシル基、ヒドロキシカルボニル基、アルコキシカルボニル基、アシルオキシカルボニル基、またはハロゲン化カルボニル基から選ばれる1種以上の官能基を、2個以上有する化合物を併用してあるいは併用せず、かつ、
炭酸ジエステルを使用してあるいは使用せずに、
重縮合して製造した樹脂、
および、
(b)一般式(4)に示すフルオレン骨格を有する化合物を、
ヒドロキシル基、ヒドロキシカルボニル基、アルコキシカルボニル基、アシルオキシカルボニル基、または、ハロゲン化カルボニル基から選ばれる1種以上の官能基を、2個以上有する化合物を併用してあるいは併用せず、かつ、
炭酸ジエステルを使用してあるいは使用せずに、
重縮合して製造した樹脂を、混合した樹脂組成物。
<3>
一般式(4)で表される化合物が、一般式(2a)で表される化合物である<1>記載の樹脂または<2>記載の樹脂組成物。
(式(2a)中、R1および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。)
<4>
一般式(4)で表される化合物が、一般式(2b)で表される化合物である<1>記載の樹脂または<2>記載の樹脂組成物。
(式(2b)中、R1および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。)
<5>
一般式(4)で表される化合物が、一般式(3)で表される化合物である<1>記載の樹脂または<2>記載の樹脂組成物。
(式中、Yはそれぞれ独立に、単結合、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を示す。)
重縮合して製造される樹脂は、ポリエステル、ポリエステルカーボネート、ポリカーボネートが好ましい。
屈折率、アッベ数、複屈折値などの光学特性は、構成単位の化学構造による影響が大きく、構成単位間の化学結合がエステル結合であるか、カーボネート結合であるかによる影響は比較的小さい。
一般式(2)で表される化合物において、重縮合に寄与する官能基の代表例はヒドロキシル基であり、アルコール性のヒドロキシル基、フェノール性のヒドロキシル基、カルボン酸のヒドロキシル基が例示される。
屈折率、アッベ数、複屈折値などの光学特性は、これら構成単位の構造によって大きく影響され、共重合体のように構成単位が一つの分子中に存在するか、混合物のように構成単位が複数の分子にまたがって存在するかの影響は比較的小さい。
(Xは炭素数1~10のアルキレン基である。)
一般式(1)で表されるジヒドロキシ化合物の例としては、2,2´-ビス(ヒドロキシメトキシ)-1,1´-ビナフタレン、2,2´-ビス(2-ヒドロキシエトキシ)-1,1´-ビナフタレン、2,2´-ビス(3-ヒドロキシプロピルオキシ)-1,1´-ビナフタレン、2,2´-ビス(4-ヒドロキシブトキシ)-1,1´-ビナフタレン等が例示される。中でも、2,2´-ビス(2-ヒドロキシエトキシ)-1,1´-ビナフタレンが好適に使用される。
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。
(式(2a)中、R1および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。)
(式(2b)中、R1および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。)
実施形態に係るポリカーボネート樹脂は、一般式(1)で表される化合物に由来する構成単位(以下、構成単位(A)と記載することがある)と、一般式(2)で表される化合物(ただしカルボン酸を除く)に由来する構成単位(以下構成単位(B)と記載することがある)を有するポリカーボネート樹脂である。ポリカーボネート樹脂において、各構成単位は、カーボネート結合を介して結合される。
[式(1)において、Xは炭素数1~10のアルキレン基である]
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。
(式(2a)中、R1およびR2は、上記式(2)において定義した通りである)。
(式(2b)中、R1およびR2は、上記式(2)において定義した通りである)。
なお、一般式(2a)または(2b)で表される化合物の詳細は、上述した通りである。
好ましい実施形態において、ポリカーボネート樹脂は、一般式(1)で表される化合物に由来する構成単位(A)と、一般式(2a)で表される化合物に由来する構成単位(以下、構成単位(C)と記載することがある)とを含む。
構成単位(A)と構成単位(C)のモル比(A/C)は、20/80~99/1が好ましく、30/70~95/5がより好ましく、40/60~90/10が特に好ましい。
より好ましくは、上記構成単位(A)から誘導されるカーボネート単位の割合は、ポリカーボネート樹脂を構成する全カーボネート単位に対して30~90mol%であり、さらに好ましくは40~80mol%である。
)は、20000~200000である。より好ましくは、ポリスチレン換算重量平均分子量(Mw)は25000~120000であり、さらに好ましくは25000~60000、特に好ましくは40000~60000である。
Mwが20000より小さいと、成形体が脆くなるため好ましくない。Mwが200000より大きいと、溶融粘度が高くなるため成形時に金型からの樹脂の取り出しが困難になり、更には流動性が悪くなり溶融状態で射出成形しにくくなるため好ましくない。
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
Δnは、厚さ0.1mmのキャストフィルムを5.0cm角の正方形に切出した後、フィルムの両端をチャックに挟み(チャック間3.0cm)、ポリカーボネート樹脂のTg+5℃で1.5倍に延伸し、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)を測定した後、下記式より求めることができる。
Δn=Re/d
Δn:配向複屈折
Re:位相差
d:厚さ
一般式(2a)で表される化合物に由来する構成単位を有するポリカーボネート樹脂は、一般式(1)で表される化合物、一般式(2a)で表される化合物、および炭酸ジエステルなどのカーボネート前駆物質を、塩基性化合物触媒もしくはエステル交換触媒またはその双方からなる混合触媒の存在下、あるいは無触媒下において、溶融重縮合法により製造することができる。
触媒は、2種類以上を併用してもよい。また、触媒自体をそのまま添加してもよく、あるいは、水やフェノール等の溶媒に溶解してから添加してもよい。
上記ポリカーボネート樹脂を用いて光学成形体を製造できる。例えば射出成形法、圧縮成形法、押出成形法、溶液キャスティング法など任意の方法により成形される。実施形態に係るポリカーボネート樹脂は、成形性および耐熱性に優れているので、射出成形が必要となる光学レンズにおいて特に有利に使用することができる。成形の際には、実施形態に係るポリカーボネート樹脂を他のポリカーボネート樹脂やポリエステル樹脂などの他の樹脂と混合して使用することが出来る。また、酸化防止剤、加工安定剤、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、離型剤、紫外線吸収剤、可塑剤、相溶化剤等の添加剤を混合しても構わない。
実施形態に係るポリカーボネート樹脂を用いて製造される光学レンズは、高屈折率であり、耐熱性に優れるため、望遠鏡、双眼鏡、テレビプロジェクター等、従来、高価な高屈折率ガラスレンズが用いられていた分野に用いることができ、極めて有用である。必要に応じて、非球面レンズの形で用いることが好ましい。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によって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。
光学レンズは、例えば射出成形法、圧縮成形法、射出圧縮成形法など任意の方法により成形される。実施形態に係るポリカーボネート樹脂を使用することにより、ガラスレンズでは技術的に加工の困難な高屈折率低複屈折非球面レンズをより簡便に得ることができる。
実施形態に係るポリカーボネート樹脂を用いて製造される光学フィルムは、透明性および耐熱性に優れるため、液晶基板用フィルム、光メモリーカード等に好適に使用される。
上記ポリカーボネート樹脂は、複数種の樹脂を含む樹脂組成物の形態であってもよい。すなわち、ポリカーボネート樹脂組成物は、一般式(1)で表される化合物に由来する構成単位(A)を有するポリカーボネート樹脂(E)、および一般式(2)で表される化合物(ただしジカルボン酸を除く)に由来する構成単位(B)を有するポリカーボネート樹脂(F)を含む。
ポリカーボネート樹脂組成物に含まれても良い他の樹脂として、以下のものが例示される:
ポリエチレン、ポリプロピレン、ポリ塩化ビニル、ポリスチレン、(メタ)クリル樹脂、ABS樹脂、ポリアミド、ポリアセタール、ポリカーボネート(ただしポリカーボネート樹脂(E)及びポリカーボネート樹脂(F)でないもの)、ポリフェニレンエーテル、ポリエステル、ポリフェニレンサルファイド、ポリイミド、ポリエーテルサルホン、ポリエーテルエーテルケトン、フッ素樹脂、シクロオレフィンポリマー、エチレン・酢酸ビニル共重合体、エポキシ樹脂、シリコーン樹脂、フェノール樹脂、不飽和ポリエステル樹脂、ポリウレタン。
他の樹脂の含量が多すぎると、相溶性が悪くなり、樹脂組成物の透明性が低下する場合がある。
<ポリカーボネート樹脂(E)>
ポリカーボネート樹脂(E)は一般式(1)で表される化合物に由来する構成単位を含む。
ポリカーボネート樹脂(E)の繰り返し構成単位として、一般式(1)以外の化合物に由来する構成単位が含まれても良いが、その量は、構成単位(A)100モル%に対して20モル%以下が望ましく、10モル%以下がさらに望ましい。この範囲内であれば、高屈折率が保持される。
ポリカーボネート樹脂(E)のポリスチレン換算平均分子量Mwは、20000~200000が好ましく、25000~120000がさらに好ましく、25000~50000が特に好ましい。
Mwが20000より小さいと、樹脂が脆くなるため好ましくない。Mwが200000より大きいと、溶融粘度が高くなるため、成形時に金型からの樹脂の抜き取りが困難になり、更には流動性が悪くなり溶融状態で扱い難くなるため好ましくない。
ポリカーボネート樹脂(E)の製造方法について記載する。
ポリカーボネート樹脂(E)の製造方法は特に限定されない。例えば、一般式(1)で表されるジヒドロキシ化合物を、炭酸ジエステル及び触媒の存在下、溶融重縮合法により製造することができる。触媒としては、塩基性化合物触媒、エステル交換触媒またはその双方からなる混合触媒を用いることができる。
等の芳香族ビスフェノール類が挙げられる。
ポリカーボネート樹脂(F)の製造方法は、一般式(1)で表される化合物を一般式(2)で表される化合物に変更することを除き、上記ポリカーボネート樹脂(E)の製造方法と同様である。
ポリカーボネート樹脂組成物の製造方法は、特に制限はなく、例えば、
〔1〕ポリカーボネート樹脂(E)とポリカーボネート樹脂(F)のそれぞれの固体を混合し、混練機により混練する方法、
〔2〕溶融状態のポリカーボネート樹脂(E)に、固体のポリカーボネート樹脂(F)を添加して混練する方法、
〔3〕溶融状態のポリカーボネート樹脂(F)に、固体のポリカーボネート樹脂(E)を添加して混練する方法、
〔4〕溶融状態のポリカーボネート樹脂(E)とポリカーボネート樹脂(F)の樹脂を混合して混練する方法、
のいずれの方法によっても製造することができる。混練は、連続式、バッチ式のどちらでもよい。混練機は、連続式ならば押出し機が好適であり、バッチ式ならばラボプラストミル、ニーダーが好適に使用される。
なお、ポリカーボネート樹脂組成物は、ポリカーボネート樹脂(E)及びポリカーボネート樹脂(F)をそれぞれ2種類以上含有していてもよい。その場合は、式(100×(E))/((E)+(F))中の(E)及び(F)はそれぞれ、2種類以上のポリカーボネート樹脂(E)及び(F)のそれぞれの合計の重量を意味する。
また、ポリカーボネート樹脂組成物は、ポリカーボネート樹脂(E)及びポリカーボネート樹脂(F)以外のポリカーボネート樹脂を含有してもよいが、実質的に含有しないのがさらに好ましい。
上記ポリカーボネート樹脂組成物を使用して、上記「(5)ポリカーボネート樹脂を使用した光学成形体」に記載したのと同様の方法により、光学レンズや光学フィルム等の光学成形体を製造することができる。実施形態に係るポリカーボネート樹脂組成物は、成形性および耐熱性に優れているので、射出成形が必要となる光学レンズにおいて特に有利に使用することができる。
実施形態に係るポリカーボネート樹脂組成物(混合後)の分子量(ポリスチレン換算重量平均分子量(Mw))は、20000~200000が好ましく、25000~120000がさらに好ましく、25000~50000が特に好ましい。
実施形態に係るポリカーボネート樹脂組成物のガラス転移温度は、95℃~180℃が好ましく、115℃~160℃がさらに好ましい。
実施形態に係るポリカーボネート樹脂組成物から作製された成形体の屈折率(23℃、波長589nm)は、1.640~1.680が好ましく、1.650~1.670がさらに好ましい。
実施形態に係るポリカーボネート樹脂組成物から作製された成形体のアッベ数は、24以下が好ましく、23以下がさらに好ましい。
実施形態に係るポリカーボネート樹脂組成物の光学歪みについては、ポリカーボネート樹脂組成物の成形片を二枚の偏光板の間に挟み、直交ニコル法で後ろからの光漏れを目視したときに、光漏れが顕著であることはなく、僅かであることが好ましい。
実施形態に係るポリエステル樹脂は、一般式(1)で表されるジヒドロキシ化合物に由来する構成単位(以下、構成単位(G)と記載することがある)と、一般式(2)で表されるジヒドロキシ化合物に由来する構成単位(以下、構成単位(H)と記載することがある)を有する。ポリエステル樹脂において、各構成単位は、エステル結合を介して結合される。このエステル結合は、「ジカルボン酸またはその誘導体に由来する構成単位」または「ジカルボン酸構成単位」とも称する。
[式(1)において、Xは炭素数1~10のアルキレン基である]
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。
(式(2a)中、R1およびR2は、上記式(2)において定義した通りである)。
(式(2b)中、R1およびR2は、上記式(2)において定義した通りである)。
なお、一般式(2a)または(2b)で表される化合物の詳細は、上述した通りである。
これらのジヒドロキシ化合物に由来する構成単位は、1種が単独で又は2種以上が組み合わされて含まれてもよい。
(式中、Yはそれぞれ独立に、単結合、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を示す。)
上記ポリエステル樹脂は、ジカルボン酸構成単位を生成する化合物(ジカルボン酸の他、そのエステル、酸無水物および酸ハロゲン化物が例示される)と、ジヒドロキシ構成単位を生成する化合物(ただしジカルボン酸に由来する構成単位を除き、ジヒドロキシ化合物が例示される)とを反応させて製造することができる。具体的には、一般式(1)で表される化合物、一般式(2)で表される化合物(好ましくは、一般式(2a)または(2b)で表される化合物)、およびジカルボン酸またはその誘導体を反応させる。反応方法としては、エステル交換法、直接重合法などの溶融重合法、溶液重合法、界面重合法等の種々の方法が挙げられるが、中でも、反応溶媒を用いない溶融重合法が好ましい。
屈折率およびアッベ数は、以下の方法により測定できる。
ポリエステル樹脂を塩化メチレンに溶解してキャストフィルムを作成し、屈折率計により屈折率を測定する。屈折率は、25℃、589nm(d線)で測定した値であり、アッベ数は、656nm(C線)、486nm(F線)、及びd線で測定した屈折率から算出した値である。
実施形態に係るポリエステル樹脂においては、このように測定した屈折率が1.60以上であることが好ましく、1.645~1.70であることがより好ましい。また、アッベ数は、21以下であることが好ましく、20以下であることがより好ましく、例えば17~21である。
上記ポリエステル樹脂は、種々の用途に用いることができる。例えば、射出成形体、シート、フィルム、パイプ等の押し出し成形体、ボトル、発泡体、粘着材、接着剤、塗料等に用いることができる。更に詳しく述べるとすれば、シートは単層でも多層でもよく、フィルムも単層でも多層でもよく、また未延伸のものでも、一方向、又は二方向に延伸されたものでもよく、鋼板などに積層してもよい。ボトルは、ダイレクトブローボトルでもインジェクションブローボトルでもよく、射出成形されたものでもよい。発泡体は、ビーズ発泡体でも押し出し発泡体でもよい。特に自動車内で使用する製品、輸出入用の包装材、太陽電池のバックシートなどの電子材料、レトルト処理や電子レンジ加熱を行う食品包装材等、高い耐熱性や水蒸気バリヤ性が要求される用途に好適に用いることができる。
実施形態に係るポリエステルカーボネート樹脂は、一般式(1)で表されるジヒドロキシ化合物に由来する構成単位(L)と、一般式(2)で表されるジヒドロキシ化合物に由来する構成単位(M)とを有する。ポリエステルカーボネート樹脂において、各構成単位は、カーボネート結合およびエステル結合を介して結合される。このカーボネート結合は、「炭酸ジエステルに由来する構成単位」とも称し、エステル結合は、「ジカルボン酸またはその誘導体に由来する構成単位」または「ジカルボン酸構成単位」とも称する。
[式(1)において、Xは炭素数1~10のアルキレン基である]
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。
(式(2a)中、R1およびR2は、上記式(2)において定義した通りである)。
(式(2b)中、R1およびR2は、上記式(2)において定義した通りである)。
なお、一般式(2a)または(2b)で表される化合物の詳細は、上述した通りである。
実施形態に係るポリエステルカーボネート樹脂には、構成単位(L)~(N)以外にもその他のジヒドロキシ化合物に由来する構成単位が含まれて良く、ジヒドロキシ化合物(ジカルボン酸およびその誘導体以外のもの)として、アルキレングリコール(例えば、エチレングリコール、プロピレングリコール、トリメチレングリコール、1,3-ブタンジオール、テトラメチレングリコール(1,4-ブタンジオール) 、ヘキサンジオール、ネオペンチルグリコール、オクタンジオール、デカンジオールなどの直鎖状又は分岐鎖状のC2-12のアルキレングリコール、(ポリ)オキシアルキレングリコール(例えば、ジエチレングリコール、トリエチレングリコール、ジプロピレングリコール)が例示される。
これらのジヒドロキシ化合物に由来する構成単位は、1種が単独で又は2種以上が組み合わされて含まれても良い。
カーボネート結合の前駆体である炭酸ジエステルとしては、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、m-クレジルカーボネート、ジメチルカーボネート、ジエチルカーボネート、ジブチルカーボネート、ジシクロヘキシルカーボネート等が挙げられる。これらの中でも特に、ジフェニルカーボネートが好ましい。ジフェニルカーボネートは、ジヒドロキシ化合物の合計1モルに対して0.97~1.10モルの比率で用いられることが好ましく、更に好ましくは0.98~1.05モルの比率である。
実施形態に係るポリエステルカーボネート樹脂に含まれるジカルボン酸に由来する構成単位は、特に限定されないが、ナフタレンジカルボン酸、テレフタル酸、イソフタル酸、フタル酸、2-メチルテレフタル酸、ビフェニルジカルボン酸、テトラリンジカルボン酸などの芳香族ジカルボン酸、シュウ酸、マロン酸、コハク酸、マレイン酸、フマル酸、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、セバシン酸、デカンジカルボン酸、ドデカンジカルボン酸、シクロヘキサンジカルボン酸、デカリンジカルボン酸、ノルボルナンジカルボン酸、トリシクロデカンジカルボン酸、ペンタシクロドデカンジカルボン酸、3,9-ビス(1,1-ジメチル-2-カルボキシエチル)-2,4,8,10-テトラオキサスピロ〔5.5〕ウンデカン、5-カルボキシ-5-エチル-2-(1,1-ジメチル-2-カルボキシエチル)-1,3-ジオキサン、ダイマー酸等の脂肪族ジカルボン酸およびそれらの誘導体に由来する構成単位が好ましい。ジカルボン酸の誘導体としては、エステル、酸無水物、酸ハロゲン化物が例示される。また、一般式(3)で表されるジカルボン酸およびその誘導体に由来する構成単位も好ましい。
(式中、Yはそれぞれ独立に、単結合、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を示す。)
ジカルボン酸構成単位は、例示した構成単位の1種類から構成されても、2種類以上から構成されてもよい。
上記ポリエステルカーボネート樹脂は、炭酸ジエステル構成単位を生成する化合物と、ジカルボン酸構成単位を生成する化合物と、ジヒドロキシ構成単位を生成する化合物とを、触媒の存在下、溶融状態でエステル交換反応させることによって製造される。具体的には、一般式(1)で表される化合物、一般式(2)で表される化合物(好ましくは、一般式(2a)または(2b)で表される化合物)、ジカルボン酸またはその誘導体、および炭酸ジエステルを反応させる。反応方法としては、エステル交換法、直接重合法などの溶融重合法、溶液重合法、界面重合法等の種々の方法が挙げられるが、中でも、反応溶媒を用いない溶融重合法が好ましい。
アルカリ土類金属化合物としては、具体的には、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、炭酸水素マグネシウム、炭酸水素カルシウム、炭酸水素ストロンチウム、炭酸水素バリウム、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、酢酸マグネシウム、酢酸カルシウム、酢酸ストロンチウム、酢酸バリウム、ステアリン酸マグネシウム、ステアリン酸カルシウム、安息香酸カルシウム、フェニルリン酸マグネシウム等が用いられる。
屈折率およびアッベ数は、以下の測定方法により測定できる。
ポリエステルカーボネート樹脂を塩化メチレンに溶解して、キャストフィルムを作成し、屈折率計により屈折率を測定する。屈折率は、25℃、589nm(d線)で測定した値であり、アッベ数は656nm(C線)、486nm(F線)、及びd線で測定した屈折率から算出した値である。
実施形態に係るポリエステルカーボネート樹脂においては、このように測定した屈折率が1.60以上であることが好ましく、1.645~1.665であることがより好ましい。また、アッベ数は、24以下であることが好ましく、21以下であることがより好ましく、例えば18~24である。
Mwが10000より小さいと、得られる樹脂成形体が脆くなる傾向があるため好ましくない。Mwが100000より大きいと、溶融粘度が高くなるため成形時に金型からの樹脂の取り出しが困難になり、更には流動性が悪くなり溶融状態で射出成形しにくくなるため好ましくない。
(1)JIS規格K7121にあるプラスチックの転移温度測定方法において、中間点ガラス転移温度の測定値が120℃以上を示す。
(2)フェノールと1,1,2,2-テトラクロロエタンとの質量比6:4の混合溶媒を用いた25℃での極限粘度の測定値が、0.2~1.0dl/gを示す。
上記ポリエステルカーボネート樹脂は、種々の用途に用いることができる。例えば、射出成形体、シート、フィルム、パイプ等の押し出し成形体、ボトル、発泡体、粘着材、接着剤、塗料等に用いることができる。更に詳しく述べるとすれば、シートは単層でも多層でもよく、フィルムも単層でも多層でもよく、また未延伸のものでも、一方向、又は二方向に延伸されたものでもよく、鋼板などに積層してもよい。ボトルは、ダイレクトブローボトルでもインジェクションブローボトルでもよく、射出成形されたものでもよい。発泡体は、ビーズ発泡体でも押し出し発泡体でもよい。特に自動車内で使用する製品、輸出入用の包装材、太陽電池のバックシートなどの電子材料、レトルト処理や電子レンジ加熱を行う食品包装材等、高い耐熱性や水蒸気バリヤ性が要求される用途に好適に用いることができる。
(A)ポリカーボネート樹脂の実施例
ポリカーボネート樹脂の実施例中の測定値は、以下の方法あるいは装置を用いて測定した。
1)ポリスチレン換算重量平均分子量(Mw):ゲル浸透クロマトグラフ(GPC)を用い、テトラヒドロフランを展開溶媒として、既知の分子量(分子量分布=1)の標準ポリスチレンを用いて検量線を作成した。この検量線に基づいて、GPCのリテンションタイムからMwを算出した。
[測定条件]
装置;東ソー株式会社製、HLC-8320GPC
カラム;ガードカラム:TSKguardcolumn SuperMPHZ-M×1本
分析カラム:TSKgel SuperMultiporeHZ-M×3本
溶媒;テトラヒドロフラン
注入量;10μL
試料濃度;0.2w/v% テトラヒドロフラン溶液
溶媒流速;0.35ml/min
測定温度;40℃
検出器;RI
3)アッベ数(ν):実施例で製造したポリカーボネート樹脂からなる厚さ0.1mmフィルムについて、アッベ屈折計を用い、23℃下での波長486nm、589nmおよび656nmの屈折率を測定し、さらに下記式を用いてアッベ数を算出した。
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
5)熱分解開始温度(Td):示差熱天秤(TG-DTA)を使用し、空気気流下、重量が5%減少した温度を測定した。昇温速度は10℃/minである(測定機器:日立ハイテクサイエンス示差熱熱重量同時測定装置STA7000)。
Δn=Re/d
Δn:配向複屈折
Re:位相差
d:厚さ
また複屈折符号は、日本分光(株)製エリプソメーターM-220を用い、上記延伸フィルムの面内で屈折率が最大となる方向を求め、延伸方向との関係から判断した。
複屈折符号が正の場合:延伸方向は、フィルム面内で屈折率が最大となる方向。
複屈折符号が負の場合:延伸方向は、フィルム面内で屈折率が最大となる方向と直交する方向。
標準物質溶液:200ppmトリメチロールフェノールのクロロホルム溶液
測定装置(GC-MS):Agilent HP6890/5973MSD
カラム:キャピラリーカラム DB-5MS, 30m×0.25mm I.D.,膜厚0.5μm
昇温条件:50℃(5min hold)~300℃(15min hold),10℃/min
注入口温度:300℃、打ち込み量:1.0μl(スプリット比25)
イオン化法:EI法
キャリアーガス:He,1.0ml/min
Aux温度:300℃
質量スキャン範囲:33-700
(実施例1)
2,2´-ビス(2-ヒドロキシエトキシ)-1,1´-ビナフタレン(以下“BHEBN”と省略することがある)13.4g(0.035モル)、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)35.6g(0.081モル)、ジフェニルカーボネート(以下“DPC”と省略することがある)25.0g(0.117モル)、および炭酸水素ナトリウム8.8×10-5g(1.0×10-6モル)を攪拌機および留出装置付きの300ml四口フラスコに入れ、窒素雰囲気760mmHgの下、180℃に加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で110分間攪拌を行った。その後、減圧度を200mmHgに調整すると同時に、60℃/hrの速度で200℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。その後、20分間その温度に保持して反応を行った。さらに、75℃/hrの速度で230℃まで昇温し、昇温終了10分後、その温度で保持しながら、1時間かけて減圧度を1mmHg以下とした。その後、60℃/hrの速度で240℃まで昇温し、さらに30分間攪拌下で反応を行った。反応終了後、反応器内に窒素を吹き込んで常圧に戻し、生成したポリカーボネート樹脂を取り出した。ポリカーボネート樹脂における残存フェノール量は150ppm、残存DPC量は120ppmであった。
BHEBN、BPEF、DPCおよび炭酸水素ナトリウムの量を、BHEBN17.1g(0.046モル)、BPEF30.1g(0.069モル)、DPC25.0g(0.117モル)および炭酸水素ナトリウム8.7×10-5g(1.0×10-6モル)に変更した以外は実施例1と同様の操作を行い、生成したポリカーボネート樹脂を取り出した。ポリカーボネート樹脂における残存フェノール量は60ppm、残存DPC量は250ppmであった。
BHEBN、BPEF、DPCおよび炭酸水素ナトリウムの量を、BHEBN30.0g(0.080モル)、BPEF15.1g(0.034モル)、DPC25.0g(0.117モル)、および炭酸水素ナトリウム8.7×10-5g(1.0×10-6モル)に変更した以外は実施例1と同様の操作を行い、生成したポリカーボネート樹脂を取り出した。ポリカーボネート樹脂における残存フェノール量は120ppmであった。
BHEBN、BPEF、DPCおよび炭酸水素ナトリウムの量を、BHEBN38.9g(0.104モル)、BPEF5.07g(0.012モル)、DPC25.0g(0.117モル)、および炭酸水素ナトリウム1.1×10-4g(1.3×10-6モル)に変更した以外は実施例1と同様の操作を行い、生成したポリカーボネート樹脂を取り出した。ポリカーボネート樹脂における残存フェノール量は100ppmであった。
窒素雰囲気760mmHgの下で180℃に加熱し、原料の完全溶解を確認後、同条件で110分間攪拌を行う操作を、30分間に短縮し、最終減圧度を50mmHgにした以外は実施例1と同様に行い、生成したポリカーボネート樹脂を取り出した。ポリカーボネート樹脂における残存フェノール量は3500ppm、残存DPC量は1200ppmであった。
ビスフェノールA(以下“BPA”と省略することがある)からなるポリカーボネート樹脂として、商品名「ユーピロンH-4000」(三菱エンジニアリングプラスチックス(株)製;Mw=33,000、Tg=148℃)を用いた。
実施例1~4、参考例1および比較例1で得られたポリカーボネート樹脂を塩化メチレンに溶解させ、固形分濃度5.3重量%の樹脂溶液を調製した。この樹脂溶液をキャストフィルム作成型に流し込み、塩化メチレン揮発後に剥離、乾燥して、厚み0.1mmのキャストフィルムを作製した。そのキャストフィルムについて、屈折率(nD)、アッベ数(ν)および全光線透過率を評価した。また、得られたキャストフィルムをTg+5℃で1.5倍に延伸し、配向複屈折(Δn)を評価した。
なお、参考例1で得られたポリカーボネート樹脂は、分子量が低いため脆くキャストフィルム化できなかった。
(実施例7)
2,2´-ビス(2-ヒドロキシエトキシ)-1,1´-ビナフタレン(以下“BHEBN”と省略することがある)3.44g(0.009モル)、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“BEPF”と省略することがある)48.9g(0.083モル)、ジフェニルカーボネート(以下“DPC”と省略することがある)20.3g(0.095モル)、および炭酸水素ナトリウム1.5×10-4g(1.8×10-6モル)を攪拌機および留出装置付きの300ml四口フラスコに入れ、窒素雰囲気760mmHgの下、180℃に加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で110分間攪拌を行った。その後、減圧度を200mmHgに調整すると同時に、60℃/hrの速度で200℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。その後、20分間その温度に保持して反応を行った。さらに、75℃/hrの速度で230℃まで昇温し、昇温終了10分後、その温度で保持しながら、1時間かけて減圧度を1mmHg以下とした。その後、60℃/hrの速度で240℃まで昇温し、さらに30分間攪拌下で反応を行った。反応終了後、反応器内に窒素を吹き込んで常圧に戻し、生成したポリカーボネート樹脂を取り出した。
BHEBN、BEPF、DPCおよび炭酸水素ナトリウムの量を、BHEBN5.17g(0.014モル)、BEPF19.0g(0.032モル)、DPC10.0g(0.047モル)、炭酸水素ナトリウム9.7×10-5g(1.2×10-6モル)に変更した以外は実施例7と同様の操作を行い、生成したポリカーボネート樹脂を取り出した。
BHEBN、BEPF、DPCおよび炭酸水素ナトリウムの量を、BHEBN13.8g(0.037モル)、BEPF32.6g(0.055モル)、DPC20.0g(0.093モル)、炭酸水素ナトリウム1.5×10-4g(1.8×10-6モル)に変更した以外は実施例7と同様の操作を行い、生成したポリカーボネート樹脂を取り出した。
BHEBN、BEPF、DPCおよび炭酸水素ナトリウムの量を、BHEBN24.4g(0.065モル)、BEPF16.5g(0.028モル)、DPC20.2g(0.094モル)、炭酸水素ナトリウム1.6×10-4g(1.9×10-6モル)に変更した以外は実施例7と同様の操作を行い、生成したポリカーボネート樹脂を取り出した。
BHEBN、BEPF、DPCおよび炭酸水素ナトリウムの量を、BHEBN31.0g(0.083モル)、BEPF5.4g(0.009モル)、DPC20.0g(0.093モル)、炭酸水素ナトリウム1.5×10-4g(1.8×10-6モル)に変更した以外は実施例7と同様の操作を行い、生成したポリカーボネート樹脂を取り出した。
ビスフェノールA(以下“BPA”と省略することがある)からなるポリカーボネート樹脂として、商品名「ユーピロンH-4000」(三菱エンジニアリングプラスチックス(株)製;Mw=33,000、Tg=148℃)を用いた。
BHEBN24.4g(0.065モル)、BPEF16.5g(0.028モル)、DPC20.2g(0.094モル)、および炭酸水素ナトリウム1.6×10-4g(1.9×10-6モル)を攪拌機および留出装置付きの300ml四口フラスコに入れ、窒素雰囲気760mmHgの下、180℃に加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で20分間攪拌を行った。その後、減圧度を200mmHgに調整すると同時に、60℃/hrの速度で200℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。その後、20分間その温度に保持して反応を行った。さらに、75℃ /hrの速度で230℃まで昇温し、昇温終了10分後、その温度で保持しながら、1時間かけて減圧度を1mmHg以下とした。その後、60℃/hrの速度で240℃まで昇温し、さらに30分間攪拌下で反応を行った。反応終了後、反応器内に窒素を吹き込んで常圧に戻し、生成したポリカーボネート樹脂を取り出した。
実施例7~11、比較例2および参考例2で得られたポリカーボネート樹脂を塩化メチレンに溶解させ、固形分濃度5.3重量%の樹脂溶液を調製した。この樹脂溶液をキャストフィルム作成型に流し込み、塩化メチレン揮発後に剥離、乾燥して、厚み0.1mmのキャストフィルムを作製した。そのキャストフィルムについて、屈折率(nD)、アッベ数(ν)および全光線透過率を評価した。また、得られたキャストフィルムをTg+5℃で1.5倍に延伸し、配向複屈折(Δn)を評価した。
なお、参考例2で得られたポリカーボネート樹脂は、分子量が低いため脆くキャストフィルム化できなかった。
ポリカーボネート樹脂組成物の実施例中の測定値は、以下の方法あるいは装置を用いて測定した。
1)ポリスチレン換算重量平均分子量(Mw):ゲル浸透クロマトグラフ(GPC)を用い、テトラヒドロフランを展開溶媒として、既知の分子量(分子量分布=1)の標準ポリスチレンを用いて検量線を作成した。この検量線に基づいて、GPCのリテンションタイムから算出した。
[測定条件]
装置;東ソー株式会社製、HLC-8320GPC
カラム;ガードカラム:TSKguardcolumn SuperMPHZ-M×1本
分析カラム:TSKgel SuperMultiporeHZ-M×3本
溶媒;テトラヒドロフラン
注入量;10μL
試料濃度;0.2w/v% テトラヒドロフラン溶液
溶媒流速;0.35ml/min
測定温度;40℃
検出器;RI
2)ガラス転移温度(Tg):示差熱走査熱量分析計(DSC)により測定した(測定機器:株式会社日立ハイテクサイエンスDSC7000X)。
4)アッベ数(ν):ポリカーボネート樹脂組成物を3mm厚×8mm×8mmの直方体にプレス成形した成形体について、株式会社島津製作所製屈折率計(KPR-200)により波長486nm、589nm、656nmの屈折率を測定し、さらに下記式を用いてアッベ数を算出した。
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
2,2´-ビス(2-ヒドロキシエトキシ)-1,1´-ビナフタレン20.0kg(53.4モル)、ジフェニルカーボネート11.7kg(54.5モル)、および炭酸水素ナトリウム6.7×10-2g(8.0×10-4モル)を攪拌機および留出装置付きの50リットル反応器に入れ、窒素雰囲気760mmHgの下で、1時間かけて200℃に加熱して撹拌した。その後、同条件で110分間攪拌を行った。その後、20分かけて減圧度を200mmHgに調整し、200℃、200mmHgの条件下で40分間保持してエステル交換反応を行った。さらに、45℃/hrの速度で230℃まで昇温し、230℃、200mmHgで10分間保持した。その後、20分かけて減圧度を150mmHgに調整し、230℃、150mmHgで10分間保持した。その後、10分かけて120mmHgに調整し、230℃、120mmHgで70分間保持した。その後、10分かけて100mmHgに調整し、230℃、100mmHgで10分間保持した。更に40分かけて1mmHg以下とし、230℃、1mmHg以下の条件下で30分間撹拌しながら重合反応を行った。反応終了後、反応器内に窒素を吹き込んで加圧し、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た。得られたポリカーボネート樹脂(A1)のMwは33000、Tgは115℃、残存フェノールは300ppm、残存DPCは250ppmであった。
9,9-ビス(4-(2-ヒドロキシエトキシ)フェニル)フルオレン19.5kg(44.5モル)、ジフェニルカーボネート9.93kg(46.3モル)、および炭酸水素ナトリウム2.2×10-2g(2.7×10-4モル)を攪拌機および留出装置付きの50リットル反応器に入れ、窒素雰囲気760mmHgの下で、1時間かけて215℃に加熱して撹拌した。その後、15分かけて減圧度を150mmHgに調整し、215℃、15mmHgの条件下で20分間保持し、エステル交換反応を行った。さらに37.5℃/hrの速度で240℃まで昇温し、240℃、150mmHgで10分間保持した。その後、10分かけて120mmHgに調整し、240℃、120mmHgで70分間保持した。その後、10分かけて100mmHgに調整し、240℃、100mmHgで10分間保持した。更に40分かけて1mmHg以下とし、240℃、1mmHg以下の条件下で10分間撹拌しながら重合反応を行った。反応終了後、反応器内に窒素を吹き込んで加圧し、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た。得られたポリカーボネート樹脂(B1)のMwは25000、Tgは146℃、残存フェノールは250ppm、残存DPCは230ppmであった。
合成例1で製造したポリカーボネート樹脂(A1)ペレット0.44kg、合成例2で製造したポリカーボネート樹脂(B1)ペレット4.57kg、ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート]7.5g、およびステアリン酸モノグリセリド7.5gをよく振り混ぜ、押出し機により260℃で混練してペレタイズし、ブレンドペレット3.3kgを得た。該ペレットのTgは142℃であり、変曲点は発見されなかった。ペレット中のフェノール含有量は450ppmであった。また、該ペレットのMwは25,000であった。該ペレットを射出成形して、直径50mm及び厚さ3mmの円板を得た。円板は透明であった。評価結果を表7に示す。
合成例1で製造したポリカーボネート樹脂(A1)ペレット1.34kg、合成例2で製造したポリカーボネート樹脂(B1)ペレット3.66kg、ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート]7.5g、およびステアリン酸モノグリセリド7.5gをよく振り混ぜ、押出し機により260℃で混練してペレタイズし、ブレンドペレット3.2kgを得た。該ペレットのTgは136℃であり、変曲点は発見されなかった。また、該ペレットのMwは26,000であった。ペレット中のフェノール含有量は350ppmであった。該ペレットを射出成形して、直径50mm及び厚さ3mmの円板を得た。円板は透明であった。評価結果を表7に示す。
合成例1で製造したポリカーボネート樹脂(A1)ペレット2.30kg、合成例2で製造したポリカーボネート樹脂(B1)ペレット2.70kg、ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート]7.5g、およびステアリン酸モノグリセリド7.5gをよく振り混ぜ、押出し機により260℃で混練してペレタイズし、ブレンドペレット3.2kgを得た。該ペレットのTgは128℃であり、変曲点は発見されなかった。また、該ペレットのMwは27,000であった。ペレット中のフェノール含有量は、370ppmであった。該ペレットを射出成形して、直径50mm及び厚さ3mmの円板を得た。円板は透明であった。評価結果を表7に示す。
合成例1で製造したポリカーボネート樹脂(A1)ペレット3.33kg、合成例2で製造したポリカーボネート樹脂(B1)ペレット1.67kg、ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート]7.5g、およびステアリン酸モノグリセリド7.5gをよく振り混ぜ、押出し機により260℃で混練してペレタイズし、ブレンドペレット3.3kgを得た。該ペレットのTgは123℃であり、変曲点は発見されなかった。また、該ペレットのMwは29,000であった。ペレット中のフェノール含有量は450ppmであった。該ペレットを射出成形して、直径50mm及び厚さ3mmの円板を得た。円板は透明であった。評価結果を表7に示す。
合成例1で製造したポリカーボネート樹脂(A1)ペレット4.43kg、合成例2で製造したポリカーボネート樹脂(B1)ペレット0.58kg、ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート]7.5g、およびラウリン酸モノグリセリド7.5gをよく振り混ぜ、押出し機により260℃で混練してペレタイズし、ブレンドペレット3.3kgを得た。該ペレットのTgは117℃であり、変曲点は発見されなかった。また、該ペレットのMwは31,000であった。ペレット中のフェノール含有量は380ppmであった。該ペレットを射出成形して、直径50mm及び厚さ3mmの円板を得た。円板は透明であった。評価結果を表7に示す。
ビスフェノールA型ポリカーボネート樹脂からなるポリカーボネート樹脂“ユーピロンH-4000”(商品名:三菱エンジニアリングプラスチックス社製、MW:33000)のペレットを射出成形して、直径50mm厚さ3mmの円板を得た。円板は透明であった。評価結果を表7に示す。
合成例1で製造したペレットを射出成形して、直径50mm厚さ3mmの円板を得た。円板は透明であった。評価結果を表7に示す。
<ポリエステル樹脂の評価方法>
本実施例で使用したポリエステル樹脂の評価方法は以下の通りである。
(1)ポリスチレン換算重量平均分子量(Mw):ゲル濾過クロマトグラフ(GPC)を用い、クロロホルムを展開溶媒として、既知の分子量(分子量分布=1)の標準ポリスチレンを用いて検量線を作成した。この検量線に基づいて、GPCのリテンションタイムからMwを算出した。
[測定条件]
装置;東ソー株式会社製、HLC-8320GPC
カラム;ガードカラム:TSKguardcolumn SuperMPHZ-M×1本
分析カラム:TSKgel SuperMultiporeHZ-M×3本
溶媒;テトラヒドロフラン
注入量;10μL
試料濃度;0.2w/v% テトラヒドロフラン溶液
溶媒流速;0.35ml/min
測定温度;40℃
検出器;RI
ポリエステル樹脂を塩化メチレンに溶解させ、固形分濃度5.3重量%の樹脂溶液を調製した。この樹脂溶液をキャストフィルム作成型に流し込み、塩化メチレン揮発後に剥離、乾燥して、厚み0.1mmのキャストフィルムを作製した。そのキャストフィルムについて、屈折率(nD)およびアッベ数(ν)を評価した。
屈折率については、ATAGO(株)製屈折率計を用い、JIS-K-7142の方法で測定した(25℃、波長589nm)。 アッベ数については、ATAGO(株)製屈折率計を用い、25℃下での波長486nm、589nmおよび656nmの屈折率を測定し、さらに下記式を用いてアッベ数を算出した。
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
(3)ガラス転移温度(Tg):示差熱走査熱量分析計(DSC)により測定した(測定機器:株式会社日立ハイテクサイエンスDSC7000X)。
加熱装置、撹拌翼、分縮器、トラップ、温度計及び窒素ガス導入管を備えたガラス製フラスコに、テレフタル酸ジメチル(以下、DMTという)1.00モル、エチレングリコール2.20モル、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という)0.10モル、2,2´-ビス(2-ヒドロキシエトキシ)-1,1´-ビナフタレン(以下、BHEBNという)0.81モルを加えた。ジカルボン酸成分に対して酢酸亜鉛二水和物0.023モル%の存在下、窒素雰囲気下で攪拌しながら徐々に加熱溶融し、エステル化反応を行った。ジカルボン酸成分の反応転化率が90%以上になった後、ジカルボン酸成分100モル%に対して、酸化ゲルマニウム0.14モル%及びリン酸トリエチル0.12モル%を加えた。昇温と減圧を徐々に行い、減圧しながらエチレングリコールを除去し、最終的に250~280℃、0.1kPa以下で重縮合を行った。この後、内容物を反応器から取り出し、フルオレン骨格を有する共重合ポリエステル樹脂を得た。
得られたポリエステル樹脂のポリスチレン換算重量平均分子量は42,000であった。物性評価については表8に示す。
BPEFを0.27モル、BHEBNを0.63モル、DMTを2,6-ナフタレンジカルボン酸ジメチル(以下、NDCMと略)に変更した以外は、実施例1と同様の操作を行った。その結果、重量平均分子量40,500のポリエステル共重合体が得られた。物性評価については表8に示す。
表8に記載の原料及び仕込み量に変更した以外は、上記実施例18と同一の装置及び反応条件でエステル交換反応及び重縮合反応を実施し、共重合ポリエステル樹脂を得た。得られた樹脂の物性評価結果は表8に示す。
<ポリエステルカーボネート樹脂の評価方法>
ポリエステルカーボネート樹脂の実施例中の測定値は、以下の方法あるいは装置を用いて測定した。
1)平均分子量:昭和電工(株)製ゲル浸透クロマトグラフ(GPC)Shodex GPC-101を用い、テトラヒドロフランを展開溶媒として、既知の分子量(分子量分布=1)の標準ポリスチレンを用いて検量線を作成した。この検量線に基づいて、GPCのリテンションタイムから数平均分子量(Mn)及び重量平均分子量(Mw)を算出した。
[測定条件]
装置;東ソー株式会社製、HLC-8320GPC
カラム;ガードカラム:TSKguardcolumn SuperMPHZ-M×1本
分析カラム:TSKgel SuperMultiporeHZ-M×3本
溶媒;テトラヒドロフラン
注入量;10μL
試料濃度;0.2w/v% テトラヒドロフラン溶液
溶媒流速;0.35ml/min
測定温度;40℃
検出器;RI
3)屈折率(nD):ポリエステルカーボネート樹脂を直径40mm、3mm厚の円盤にプレス成形し、株式会社島津デバイス製造製屈折率計(KPR-200)により、25℃における屈折率(波長:589nm)を測定した。
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
2,2´-ビス(2-ヒドロキシエトキシ)-1,1´-ビナフタレン(以下“BHEBN”と省略することがある)17.3g(0.046モル)、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)25.27g(0.058モル)、ジフェニルカーボネート(以下“DPC”と省略することがある)19.94g(0.093モル)、およびテレフタル酸ジメチル(以下”DMT”と省略することがある)2.239g(0.012モル)を攪拌機および留出装置付きの300ml四口フラスコに入れた。減圧と窒素封入を5回繰り返した後、760mmHgの窒素雰囲気下、180℃にて加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で10分間攪拌を行った。その後、回転速度を200rpm迄上昇させ、28mmHg/minの速度で200mmHgまで減圧し、さらに、60℃/hrの速度で260℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。圧力200mmHg、温度260℃に到達後、10mmHg/minで減圧し、圧力が0mmHgに到達した後20分間で反応終了とした。最後に反応器内に窒素を吹き込んで常圧に戻し、生成したポリエステルカーボネート樹脂を取り出した。
BHEBN17.3g(0.046モル)、BPEF25.27g(0.058モル)、DPC19.94g(0.093モル)、およびDMT2.239g(0.012モル)を攪拌機および留出装置付きの300ml四口フラスコに入れた。減圧と窒素封入を5回繰り返した後、760mmHgの窒素雰囲気下、180℃にて加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で10分間攪拌を行った。その後、回転速度を200rpm迄上昇させ、28mmHg/minの速度で200mmHgまで減圧し、さらに、60℃/hrの速度で240℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。圧力200mmHg、温度240℃に到達後、10mmHg/minで減圧し、圧力が0.8mmHgに到達した後40分間で反応終了とした。最後に反応器内に窒素を吹き込んで常圧に戻し、生成したポリエステルカーボネート樹脂を取り出した。
BHEBN35.64g(0.095モル)、BPEF4.615g(0.011モル)、DPC20.00g(0.093モル)、およびDMT2.557g(0.013モル)を攪拌機および留出装置付きの300ml四口フラスコに入れた。減圧と窒素封入を5回繰り返した後、760mmHgの窒素雰囲気下、180℃にて加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で10分間攪拌を行った。その後、28mmHg/minで200mmHgまで減圧し、60℃/hrの速度で250℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。最後に反応器内に窒素を吹き込んで常圧に戻し、生成したポリエステルカーボネート樹脂を取り出した。
BHEBN3.928g(0.011モル)、BPEF41.95g(0.096モル)、DPC20.34g(0.095モル)、およびDMT2.287g(0.012モル)を攪拌機および留出装置付きの300ml四口フラスコに入れた。減圧と窒素封入を5回繰り返した後、760mmHgの窒素雰囲気下、180℃にて加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で10分間攪拌を行った。その後、回転速度を200rpm迄上昇させ、28mmHg/minの速度で200mmHgまで減圧し、さらに、60℃/hrの速度で260℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。圧力200mmHg、温度260℃に到達後、1.6mmHg/minで減圧した。最後に圧力が0.8mmHgに到達した後20分間で反応終了とした。反応器内に窒素を吹き込んで常圧に戻し、生成したポリエステルカーボネート樹脂を取り出した。
BHEBN10.92g(0.029モル)、BPEF33.41g(0.076モル)、DPC20.10g(0.093モル)、およびDMT2.289g(0.0118モル)を攪拌機および留出装置付きの300ml四口フラスコに入れた。減圧と窒素封入を5回繰り返した後、760mmHgの窒素雰囲気下、180℃にて加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で10分間攪拌を行った。その後、回転速度を200rpm迄上昇させ、4.6mmHg/minの速度で200mmHgまで減圧し、さらに、60℃/hrの速度で260℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。圧力200mmHg、温度260℃に到達後、3.3mmHg/minで減圧し、圧力が0.8mmHgに到達した後60分間で反応終了とした。最後に反応器内に窒素を吹き込んで常圧に戻し、生成したポリエステルカーボネート樹脂を取り出した。
BHEBN23.96g(0.064モル)、BPEF17.61g(0.040モル)、DPC19.84g(0.093モル)、およびDMT2.289g(0.012モル)を攪拌機および留出装置付きの300ml四口フラスコに入れた。減圧と窒素封入を5回繰り返した後、760mmHgの窒素雰囲気下、180℃にて加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で10分間攪拌を行った。その後、回転速度を200rpm迄上昇させ、28mmHg/minの速度で200mmHgまで減圧し、さらに、60℃/hrの速度で260℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。圧力200mmHg、温度260℃に到達後、3.3mmHg/minで減圧し、圧力が0.8mmHgに到達した後30分間で反応終了とした。最後に反応器内に窒素を吹き込んで常圧に戻し、生成したポリエステルカーボネート樹脂を取り出した。
BHBN12.94g(0.035モル)、BPEF24.77g(0.057モル)、DPC20.09g(0.094モル)、およびDMT2.187g(0.0113モル)を攪拌機および留出装置付きの300ml四口フラスコに入れた。減圧と窒素封入を5回繰り返した後、760mmHgの窒素雰囲気下、180℃にて加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で10分間攪拌を行った。その後、回転速度を200rpm迄上昇させ、28mmHg/minの速度で200mmHgまで減圧し、さらに、60℃/hrの速度で260℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。圧力200mmHg、温度260℃に到達後、10mmHg/minで減圧し、圧力が0.8mmHgに到達した後反応を終了した。反応器内に窒素を吹き込んで常圧に戻し、生成したポリエステルカーボネート樹脂を取り出した。
BHBN26.80g(0.072モル)、BPEF4.544g(0.0104モル)、DPC19.98g(0.093モル)、およびDMT2.236g(0.0115モル)を攪拌機および留出装置付きの300ml四口フラスコに入れた。減圧と窒素封入を5回繰り返した後、760mmHgの窒素雰囲気下、180℃にて加熱した。加熱開始10分後に原料の完全溶解を確認し、その後同条件で10分間攪拌を行った。回転速度を200rpm迄上昇させ、28mmHg/minの速度で200mmHgまで減圧し、さらに、60℃/hrの速度で260℃まで昇温を行った。この際、副生したフェノールの留出開始を確認した。圧力200mmHg、温度260℃に到達後、10mmHg/minで減圧し、圧力が0.8mmHgに到達した後反応を終了した。反応器内に窒素を吹き込んで常圧に戻し、生成したポリエステルカーボネート樹脂を取り出した。
Claims (21)
- 前記ジカルボン酸またはその誘導体は、ナフタレンジカルボン酸、テレフタル酸、イソフタル酸、フルオレン基を有するジカルボン酸、またはこれらのエステルである請求項1または2に記載のポリエステル樹脂。
- 前記ポリエステル樹脂において、ジヒドロキシ化合物に由来する構成単位のうち前記一般式(1)で表される化合物に由来する構成単位の割合は5~95モル%であり、前記一般式(2)で表される化合物に由来する構成単位の割合は2.5~47.5モル%である、請求項1~3のいずれか1項に記載のポリエステル樹脂。
- さらにグリコールに由来する構成単位を含み、前記ポリエステル樹脂におけるジヒドロキシ化合物に由来する構成単位のうちグリコールに由来する構成単位の割合は、5~70モル%である請求項1~4のいずれか1項に記載のポリエステル樹脂。
- 請求項1~5のいずれか1項に記載のポリエステル樹脂を含む光学部材。
- 前記光学部材が、一眼レフカメラ、デジタルスチルカメラ、ビデオカメラ、カメラ付携帯電話、レンズ付フィルム、望遠鏡、双眼鏡、顕微鏡、またはプロジェクターの光学レンズである請求項6に記載の光学部材。
- 下記一般式(1)で表される化合物に由来する構成単位と、下記一般式(2)で表される化合物に由来する構成単位と、ジカルボン酸またはその誘導体に由来する構成単位と、炭酸ジエステルに由来する構成単位とを含むポリエステルカーボネート樹脂:
[式(1)において、Xは炭素数1~10のアルキレン基である]
[式(2)において、
R1および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り、
Rは、水素原子または炭素数1~20のヒドロキシアルキル基である]。 - 前記ジカルボン酸またはその誘導体は、ナフタレンジカルボン酸、テレフタル酸、イソフタル酸、フルオレン基を有するジカルボン酸、またはこれらのエステルである請求項8または9に記載のポリエステルカーボネート樹脂。
- 前記ポリエステルカーボネート樹脂において、ジヒドロキシ化合物に由来する構成単位のうち前記一般式(1)で表される化合物に由来する構成単位の割合は5~95モル%であり、前記一般式(2)で表される化合物に由来する構成単位の割合は2.5~47.5モル%である、請求項8~10のいずれか1項に記載のポリエステルカーボネート樹脂。
- 屈折率が1.645~1.660である、請求項8~11のいずれか1項に記載のポリエステルカーボネート樹脂。
- ポリスチレン換算重量平均分子量(Mw)が14,000~100,000である、請求項8~12のいずれか1項に記載のポリエステルカーボネート樹脂。
- 請求項8~13のいずれか1項に記載のポリエステルカーボネート樹脂を含む光学部材。
- 前記光学部材が、一眼レフカメラ、デジタルスチルカメラ、ビデオカメラ、カメラ付携帯電話、レンズ付フィルム、望遠鏡、双眼鏡、顕微鏡、またはプロジェクターの光学レンズである請求項14に記載の光学部材。
- 前記酸化防止剤が、ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート]である請求項18に記載の樹脂組成物。
- 前記離型剤が、アルコールと脂肪酸とのエステルである請求項18または19に記載の樹脂組成物。
- 前記アルコールと脂肪酸とのエステルが、ステアリン酸モノグリセリドまたはラウリン酸モノグリセリドである請求項20に記載の樹脂組成物。
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WO2017146023A1 (ja) * | 2016-02-24 | 2017-08-31 | 富士フイルム株式会社 | ポリカーボネート樹脂、成形体、光学部材及びレンズ |
JP2018035228A (ja) * | 2016-08-30 | 2018-03-08 | 帝人株式会社 | ポリエステル樹脂 |
JPWO2017078071A1 (ja) * | 2015-11-04 | 2018-08-30 | 三菱瓦斯化学株式会社 | 樹脂組成物の製造方法 |
WO2018181157A1 (ja) * | 2017-03-31 | 2018-10-04 | 三菱瓦斯化学株式会社 | ポリカーボネート樹脂組成物及びそれを用いた光学レンズ |
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Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10816699B2 (en) * | 2014-12-04 | 2020-10-27 | Mitsubishi Gas Chemical Company, Inc. | Functional sheet including polyester resin, and lens using functional sheet |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000302857A (ja) * | 1999-04-21 | 2000-10-31 | Mitsubishi Gas Chem Co Inc | 光記録媒体用成形材料 |
WO2007142149A1 (ja) * | 2006-06-05 | 2007-12-13 | Mitsubishi Gas Chemical Company, Inc. | 光学レンズ |
JP2009067681A (ja) * | 2007-09-10 | 2009-04-02 | Mitsubishi Chemicals Corp | ビスフェニルフルオレンジカルボン酸ジエステルの製造方法、並びにこれを重合してなるポリマー |
JP2010100770A (ja) * | 2008-10-27 | 2010-05-06 | Mitsubishi Gas Chemical Co Inc | 熱可塑性樹脂の製造方法、ポリエステル樹脂及びポリカーボネート樹脂、ならびにそれらの用途 |
JP2010248445A (ja) * | 2009-04-20 | 2010-11-04 | Mitsubishi Gas Chemical Co Inc | ポリカーボネート樹脂組成物 |
JP2011168722A (ja) * | 2010-02-19 | 2011-09-01 | Osaka Gas Chem Kk | フルオレン骨格を有するポリエステル樹脂 |
WO2014073496A1 (ja) * | 2012-11-07 | 2014-05-15 | 三菱瓦斯化学株式会社 | ポリカーボネート樹脂、その製造方法および光学成形体 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5043237A (en) * | 1990-01-12 | 1991-08-27 | E. I. Du Pont De Nemours And Company | Inhibitor-containing photohardenable electrostatic master compositions having improved resolution |
EP0653451B1 (en) * | 1992-07-30 | 1999-02-17 | Kanebo, Ltd. | Polyester |
IL115803A (en) * | 1994-11-03 | 2000-02-17 | Ppg Industries Inc | Indeno-naphthopyran derivatives useful for photochromic articles |
JP3331121B2 (ja) | 1996-05-17 | 2002-10-07 | カネボウ株式会社 | ポリエステル重合体およびその成形体 |
US5955520A (en) * | 1996-06-17 | 1999-09-21 | Ppg Industries, Inc. | Photochromic indeno-fused naphthopyrans |
US5723072A (en) * | 1996-06-17 | 1998-03-03 | Ppg Industries, Inc. | Photochromic heterocyclic fused indenonaphthopyrans |
JPH1087800A (ja) * | 1996-09-10 | 1998-04-07 | Teijin Chem Ltd | ポリエステルカーボネート樹脂 |
CN1234796A (zh) * | 1996-10-02 | 1999-11-10 | Ppg工业公司 | 新的取代萘并吡喃化合物 |
JP2001072872A (ja) | 1999-07-02 | 2001-03-21 | Konica Corp | 樹脂組成物および光学用レンズ |
JP2002332345A (ja) * | 2001-05-08 | 2002-11-22 | Konica Corp | 樹脂組成物及び光学用レンズ |
US6946227B2 (en) * | 2002-11-20 | 2005-09-20 | Xerox Corporation | Imaging members |
JP4281998B2 (ja) * | 2003-06-06 | 2009-06-17 | 三菱瓦斯化学株式会社 | ポリカーボネート樹脂組成物 |
JP4908781B2 (ja) | 2005-06-06 | 2012-04-04 | 大阪瓦斯株式会社 | ポリエステル樹脂組成物および光学部品 |
JP2007057916A (ja) | 2005-08-25 | 2007-03-08 | Mitsubishi Gas Chem Co Inc | 光学レンズ |
JP5005949B2 (ja) * | 2006-05-01 | 2012-08-22 | 出光興産株式会社 | ポリカーボネート系樹脂組成物、光学成形品及び照明ユニット |
EP2308928B1 (en) * | 2008-07-25 | 2014-03-05 | Mitsubishi Gas Chemical Company, Inc. | Polycarbonate resin composition and optical material using the same |
JP5526579B2 (ja) * | 2009-04-06 | 2014-06-18 | 三菱瓦斯化学株式会社 | ポリカーボネート樹脂組成物、並びにそれを用いた成形品の製造方法及び成形品 |
JP6087490B2 (ja) | 2010-10-06 | 2017-03-01 | 帝人株式会社 | フルオレン誘導体からなる熱可塑性樹脂およびその溶融重合方法 |
JP5719854B2 (ja) | 2011-01-19 | 2015-05-20 | 帝人株式会社 | ポリエステルカーボネート共重合体およびその製造方法 |
JP5914261B2 (ja) | 2011-08-29 | 2016-05-11 | 大阪ガスケミカル株式会社 | フルオレン骨格を有するポリエステル樹脂 |
JP5914259B2 (ja) | 2011-08-29 | 2016-05-11 | 大阪ガスケミカル株式会社 | フルオレン骨格を有するポリエステル樹脂 |
JP6154337B2 (ja) * | 2013-02-20 | 2017-06-28 | 帝人株式会社 | ポリカーボネート共重合体 |
JP6139258B2 (ja) * | 2013-05-13 | 2017-05-31 | 帝人株式会社 | ポリエステルカーボネート共重合体 |
US9982129B2 (en) * | 2014-05-02 | 2018-05-29 | Mitsubishi Gas Chemical Company, Inc. | Polycarbonate resin composition, and optical material and optical lens each manufactured using same |
-
2015
- 2015-05-01 JP JP2016517907A patent/JP6631514B2/ja active Active
- 2015-05-01 KR KR1020167023960A patent/KR102289075B1/ko active Active
- 2015-05-01 US US15/306,638 patent/US10689486B2/en active Active
- 2015-05-01 WO PCT/JP2015/063143 patent/WO2015170691A1/ja active Application Filing
- 2015-05-01 CN CN201580022948.XA patent/CN106255712B/zh active Active
- 2015-05-01 CN CN201811501106.4A patent/CN109593196B/zh active Active
- 2015-05-01 EP EP15789371.0A patent/EP3141570B1/en active Active
- 2015-05-01 EP EP18201503.2A patent/EP3483197A1/en not_active Withdrawn
- 2015-05-04 TW TW104114090A patent/TWI662059B/zh active
-
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- 2019-11-18 JP JP2019207891A patent/JP6908092B2/ja active Active
-
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- 2020-02-25 US US16/800,130 patent/US11370882B2/en active Active
-
2022
- 2022-05-16 US US17/745,289 patent/US20220282038A1/en active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000302857A (ja) * | 1999-04-21 | 2000-10-31 | Mitsubishi Gas Chem Co Inc | 光記録媒体用成形材料 |
WO2007142149A1 (ja) * | 2006-06-05 | 2007-12-13 | Mitsubishi Gas Chemical Company, Inc. | 光学レンズ |
JP2009067681A (ja) * | 2007-09-10 | 2009-04-02 | Mitsubishi Chemicals Corp | ビスフェニルフルオレンジカルボン酸ジエステルの製造方法、並びにこれを重合してなるポリマー |
JP2010100770A (ja) * | 2008-10-27 | 2010-05-06 | Mitsubishi Gas Chemical Co Inc | 熱可塑性樹脂の製造方法、ポリエステル樹脂及びポリカーボネート樹脂、ならびにそれらの用途 |
JP2010248445A (ja) * | 2009-04-20 | 2010-11-04 | Mitsubishi Gas Chemical Co Inc | ポリカーボネート樹脂組成物 |
JP2011168722A (ja) * | 2010-02-19 | 2011-09-01 | Osaka Gas Chem Kk | フルオレン骨格を有するポリエステル樹脂 |
WO2014073496A1 (ja) * | 2012-11-07 | 2014-05-15 | 三菱瓦斯化学株式会社 | ポリカーボネート樹脂、その製造方法および光学成形体 |
Non-Patent Citations (1)
Title |
---|
See also references of EP3141570A4 * |
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US10689486B2 (en) | 2020-06-23 |
EP3141570A4 (en) | 2018-01-10 |
JP6631514B2 (ja) | 2020-01-15 |
KR102289075B1 (ko) | 2021-08-11 |
CN106255712A (zh) | 2016-12-21 |
CN109593196B (zh) | 2021-08-13 |
EP3141570A1 (en) | 2017-03-15 |
CN109593196A (zh) | 2019-04-09 |
JP6908092B2 (ja) | 2021-07-21 |
EP3483197A1 (en) | 2019-05-15 |
JPWO2015170691A1 (ja) | 2017-04-20 |
CN106255712B (zh) | 2018-12-18 |
TWI662059B (zh) | 2019-06-11 |
EP3141570B1 (en) | 2018-12-05 |
US20220282038A1 (en) | 2022-09-08 |
US11370882B2 (en) | 2022-06-28 |
JP2020045492A (ja) | 2020-03-26 |
KR20170005792A (ko) | 2017-01-16 |
US20170044312A1 (en) | 2017-02-16 |
TW201546110A (zh) | 2015-12-16 |
US20200190259A1 (en) | 2020-06-18 |
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