WO2023085339A1 - 熱可塑性樹脂及びそれを含む光学レンズ - Google Patents
熱可塑性樹脂及びそれを含む光学レンズ Download PDFInfo
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- WO2023085339A1 WO2023085339A1 PCT/JP2022/041824 JP2022041824W WO2023085339A1 WO 2023085339 A1 WO2023085339 A1 WO 2023085339A1 JP 2022041824 W JP2022041824 W JP 2022041824W WO 2023085339 A1 WO2023085339 A1 WO 2023085339A1
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- SODJJEXAWOSSON-UHFFFAOYSA-N bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O SODJJEXAWOSSON-UHFFFAOYSA-N 0.000 description 1
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- HJJZFSVYWJHHFE-UHFFFAOYSA-N docosanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCCCCCCCCCCCCCCCC(O)=O HJJZFSVYWJHHFE-UHFFFAOYSA-N 0.000 description 1
- UWLPCYBIJSLGQO-UHFFFAOYSA-N dodecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCC(O)=O UWLPCYBIJSLGQO-UHFFFAOYSA-N 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 229960002479 isosorbide Drugs 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 229940031993 lithium benzoate Drugs 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 1
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- JGIZKLDQCIOYLH-UHFFFAOYSA-L magnesium;phenyl phosphate Chemical compound [Mg+2].[O-]P([O-])(=O)OC1=CC=CC=C1 JGIZKLDQCIOYLH-UHFFFAOYSA-L 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- ADFPJHOAARPYLP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;styrene Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1 ADFPJHOAARPYLP-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- YJFCFSVVFTZXBL-UHFFFAOYSA-N o-[3-henicosanethioyloxy-2,2-bis(henicosanethioyloxymethyl)propyl] henicosanethioate Chemical compound CCCCCCCCCCCCCCCCCCCCC(=S)OCC(COC(=S)CCCCCCCCCCCCCCCCCCCC)(COC(=S)CCCCCCCCCCCCCCCCCCCC)COC(=S)CCCCCCCCCCCCCCCCCCCC YJFCFSVVFTZXBL-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
- 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
- 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 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
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- LYTNHSCLZRMKON-UHFFFAOYSA-L oxygen(2-);zirconium(4+);diacetate Chemical compound [O-2].[Zr+4].CC([O-])=O.CC([O-])=O LYTNHSCLZRMKON-UHFFFAOYSA-L 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229940026235 propylene glycol monolaurate Drugs 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940100515 sorbitan Drugs 0.000 description 1
- 229950006451 sorbitan laurate Drugs 0.000 description 1
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 229950004959 sorbitan oleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- WJMMDJOFTZAHHS-UHFFFAOYSA-L strontium;carbonic acid;carbonate Chemical compound [Sr+2].OC([O-])=O.OC([O-])=O WJMMDJOFTZAHHS-UHFFFAOYSA-L 0.000 description 1
- RXSHXLOMRZJCLB-UHFFFAOYSA-L strontium;diacetate Chemical compound [Sr+2].CC([O-])=O.CC([O-])=O RXSHXLOMRZJCLB-UHFFFAOYSA-L 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 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
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-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
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- 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
- 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
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/305—General preparatory processes using carbonates and alcohols
-
- 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
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/307—General preparatory processes using carbonates and phenols
-
- 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
Definitions
- the present invention relates to a thermoplastic resin and an optical lens containing the same. More particularly, the present invention relates to polycarbonate resins and optical lenses containing the same.
- Optical glass or optical resin is used as the material for the optical lenses 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., but has problems of high material cost, poor moldability, and low productivity.
- optical lenses made of optical resins have the advantage that they can be mass-produced by injection molding, and polycarbonate, polyester carbonate, polyester resin, etc. are used as high refractive index materials for camera lenses.
- Patent Documents 1 to 5 When optical resins are used as optical lenses, heat resistance, transparency, low water absorption, chemical resistance, low birefringence, resistance to moist heat, etc. are required in addition to optical properties such as refractive index and Abbe number. Especially in recent years, there has been a demand for optical lenses having a high refractive index and high heat resistance, and various resins have been developed (Patent Documents 1 to 5).
- thermoplastic resins made from 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene have excellent optical properties and are useful as various optical materials (Patent Document 6. ).
- Patent Document 6. thermoplastic resins made from 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene have excellent optical properties and are useful as various optical materials.
- aberration correction is performed by combining multiple concave and convex lenses. That is, the chromatic aberration caused by the convex lens is synthetically canceled by combining the concave lens having the opposite sign of the chromatic aberration to that of the convex lens. At this time, the concave lens is required to have high dispersion (that is, low Abbe number).
- Patent Document 7 discloses that a copolymer of a bisphenol A-type polycarbonate structural unit and a structural unit represented by the following formula (E) has an improved refractive index.
- Examples of Patent Document 7 describe that a refractive index of 1.62 to 1.64 and an Abbe number of 23 to 26 were achieved. It is considered that the reason why the refractive index is improved in this way is due to the constitutional unit represented by the formula (E).
- Patent Document 8 discloses a copolymer of polycarbonate resin and bisphenol A containing structural units having a fluorene structure. Examples in this document describe achieving refractive indices of 1.616 to 1.636. Note that the structural unit disclosed in this document is different from the formula (E).
- An object of the present invention is to provide a thermoplastic resin that is excellent in optical properties such as refractive index, Abbe number, and haze, and is also excellent in in-plane birefringence, and an optical lens using the same.
- Another object of the present invention is to provide a polycarbonate resin having a high refractive index and a low Abbe number, a small absolute value of birefringence intensity, and a small in-plane birefringence, and an optical lens using the same.
- the present inventors have found that by blending a specific amount of a diol compound having a specific structure, optical properties such as refractive index, Abbe number and haze are excellent, and , and found that a thermoplastic resin having excellent in-plane birefringence can be obtained, and completed the present invention. Furthermore, the inventors have found that the above problems can be solved by the following polycarbonate resin and optical lens, and have completed the present invention.
- the present invention includes the following aspects. ⁇ 1> With respect to the total amount (100 mol%) of the structural units in the resin, 22 to 49 mol% of the structural unit (A) derived from the diol represented by the following general formula (1A) and the following general formula ( 40 to 75 mol% of the structural unit (B) derived from the diol represented by 2A), and 0 to 15 mol% of the structural unit (C) derived from the diol represented by the following general formula (3A), It is a thermoplastic resin containing (In general formula (1A), R a , R b , R aa and R bb are each independently a hydrogen atom, a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, a substituent an alkoxy group having 1 to 20 carbon atoms which may have a cycloalkyl group having 5 to 20 carbon atoms which may have a substituent; , an aryl group having 6 to 20 carbon atoms
- thermoplastic resin according to ⁇ 1> above is 0 to 8 mol % of the thermoplastic resin according to ⁇ 1> above.
- ⁇ 3> The thermoplastic resin according to ⁇ 1> or ⁇ 2> above, wherein the diol represented by the general formula (1) contains a diol represented by the following structural formula.
- ⁇ 4> The thermoplastic resin according to any one of ⁇ 1> to ⁇ 3> above, wherein the diol represented by the general formula (2A) contains at least one of the diols represented by the following structural formulas.
- ⁇ 5> The thermoplastic resin according to any one of ⁇ 1> to ⁇ 4> above, wherein the diol represented by the general formula (3A) contains a diol represented by the following structural formula.
- thermoplastic resin according to any one of ⁇ 1> to ⁇ 5> which is a polycarbonate resin.
- thermoplastic resin according to any one of ⁇ 1> to ⁇ 6> further comprising a structural unit derived from at least one monomer selected from the following monomer group. .
- nD refractive index
- MVR melt volume flow rate
- An optical member comprising the thermoplastic resin according to any one of ⁇ 1> to ⁇ 14> above.
- An optical lens comprising the thermoplastic resin according to any one of ⁇ 1> to ⁇ 14>.
- An optical film comprising the thermoplastic resin according to any one of ⁇ 1> to ⁇ 14> above.
- the ratio of the structural unit represented by the following general formula (1B) is 1 mol% or more and less than 10 mol%
- the ratio of the structural unit represented by the following general formula (2B) is 10 to 60 mol%
- the above polycarbonate resin, wherein the ratio of structural units represented by the following general formula (3B) is 5 to 80 mol%.
- X represents an alkylene group having 1 to 4 carbon atoms, and a and b each independently represents an integer of 1 to 10.
- Y represents an alkylene group having 1 to 4 carbon atoms, and c and d each independently represents an integer of 1 to 10.
- Z represents an alkylene group having 1 to 4 carbon atoms
- R 1 to R 6 each independently represents 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 group having 5 to 20 carbon atoms.
- thermoplastic resin excellent in optical properties such as refractive index, Abbe number, and haze, as well as excellent in-plane birefringence
- an optical lens containing the same Furthermore, according to the present invention, it is possible to provide a polycarbonate resin having a high refractive index and a low Abbe number, a small absolute value of birefringence intensity, and a small in-plane birefringence, and an optical lens containing the same. can.
- thermoplastic resin 22 to 49 mol% of a structural unit (A) derived from a diol represented by the following general formula (1A) with respect to the total amount (100 mol%) of structural units in the resin. and 40 to 75 mol% of the structural unit (B) derived from the diol represented by the following general formula (2A), and 0 of the structural unit (C) derived from the diol represented by the following general formula (3A). ⁇ 15 mol% of the thermoplastic resin.
- R a , R b , R aa and R bb each independently have a hydrogen atom, a halogen atom (fluorine atom, chlorine atom, bromine atom or iodine atom), a substituent Alkyl groups having 1 to 20 carbon atoms (preferably alkyl groups having 1 to 6 carbon atoms), optionally substituted alkoxy groups having 1 to 20 carbon atoms (preferably having 1 to 6 carbon atoms) alkoxy group), an optionally substituted C5-20 cycloalkyl group (preferably a C5-10 cycloalkyl group), an optionally substituted C5-20 a cycloalkoxy group (preferably a cycloalkoxy group having 5 to 10 carbon atoms), an optionally substituted aryl group having 6 to 20 carbon atoms (preferably an aryl group having 6 to 12 carbon atoms
- R a and R b each independently represent a hydrogen atom, a methyl group, an ethyl group, or a phenyl group
- R aa and R bb each independently represent a hydrogen atom or a phenyl group.
- R h in -C ⁇ C-R h is an optionally substituted aryl group having 6 to 20 carbon atoms (preferably an aryl group having 6 to 12 carbon atoms), or O, N and S It represents an optionally substituted heteroaryl group having 6 to 20 carbon atoms (preferably a heteroaryl group having 6 to 12 carbon atoms) containing one or more hetero ring atoms selected from .
- Each X independently represents an optionally substituted alkylene group having 1 to 5 carbon atoms (preferably an alkylene group having 1 to 3 carbon atoms, more preferably an ethylene group).
- a and b each independently represent an integer of 0 to 10, preferably an integer of 1 to 3, more preferably 1;
- substituents in the case of "optionally having a substituent" include halogen, a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms. be done.
- the structural unit (A) derived from the diol represented by the general formula (1A) is is preferable because the refractive index and the Abbe number are well balanced when used as an optical lens.
- BPEF 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene
- OPPFL 9,9-bis[ 4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene
- R c and R d are each independently a hydrogen atom, a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted carbon an alkoxy group having 1 to 20 carbon atoms, an optionally substituted cycloalkyl group having 5 to 20 carbon atoms, an optionally substituted cycloalkoxy group having 5 to 20 carbon atoms, and having a substituent an aryl group having 6 to 30 carbon atoms which may be substituted, a heteroaryl group having 6 to 30 carbon atoms which may be substituted, which contains one or more hetero ring atoms selected from O, N and S, a substituent selected from the group consisting of an aryloxy group having 6 to 20 carbon atoms which may have R h is an optionally substituted aryl group having 6 to 20 carbon atoms, or an optionally
- R c and R d in the general formula (2A) are each independently preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an aryl group having 6 to 30 carbon atoms. group, more preferably an aryl group having 6 to 20 carbon atoms, still more preferably an aryl group having 6 to 14 carbon atoms. At least one of R c and R d in general formula (2A) is preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 14 carbon atoms, particularly More preferably, two of R c and R d are aryl groups having 6 to 14 carbon atoms or 6 to 12 carbon atoms.
- R c and R d may be the same or different and are monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, or monocyclic or polycyclic aryl groups having 5 to 5 ring atoms. may be selected from 36 heteroaryl groups wherein 1, 2, 3 or 4 of the ring atoms are selected from nitrogen, sulfur and oxygen and the other ring atoms are carbon .
- the monocyclic or polycyclic aryl group and the monocyclic or polycyclic heteroaryl group may be unsubstituted.
- R c and R d may each be selected from the following group. i.e. azulenyl, which may be unsubstituted, phenyl and bonded to each other by a single bond, may be directly fused together, and/or saturated or unsaturated 4-10 membered monocyclic or bicyclic 2, 3, 4 or indenyl optionally substituted by 5 substituents, unsubstituted phenyl, phenyl substituted by one or two CN groups, phenyl and a 4- to 10-membered monocyclic or bicyclic hydrocarbon ring which may be bonded to each other by a single bond or may be directly fused together and/or saturated or unsaturated; substituted by 2, 3, 4 or 5 substituents selected from polycyclic aryl having 2, 3 or 4 phenyl rings optionally fused to Phenyl, which is may be directly fused to each other and/or may be fused to saturated or unsaturated 4- to 10-membered monocyclic or bicyclic hydro
- each of R c and R d may be selected from the following group. i.e. phenyl, which is unsubstituted or optionally substituted by 1, 2, 3, 4 or 5 phenyl groups, phenyl substituted by one or two CN groups, phenyl substituted by one or two polycyclic aryl groups selected from biphenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl and pyrenyl, and optionally further substituted by one phenyl group; unsubstituted or naphthyl substituted by one or two substituents selected from CN, phenyl and polycyclic aryl selected from biphenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl and pyrenyl; biphenylenyl, triphenylenyl, tetraphenylenyl, phenanthryl, pyrenyl, 9H-
- R c and R d are selected from the group consisting of phenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 2-naphthyl, 1-naphthyl and 9-naphthyl; preferable.
- each of R c and R d may be selected from the following group. i.e. a heteroaromatic monocyclic group having 5 or 6 ring atoms and having 1, 2, 3 or 4 nitrogen atoms or 1 oxygen atom and 0, 1 or 2 , or a heteroaromatic monocyclic group having 3 nitrogen atoms, or 1 sulfur atom and 0, 1, 2, or 3 nitrogen atoms, the other ring atoms being carbon atoms , a heteroaromatic polycyclic group comprising said monocyclic heteroaromatic ring and 1, 2, 3, 4 or 5 further aromatic rings selected from phenyl and monocyclic heteroaromatic rings; and the (hetero)aromatic rings of the polycyclic heteroaryl may be attached to each other by covalent bonds or may be directly fused to each other and/or saturated or unsaturated 4- to 10-membered rings a heteroaromatic polycyclic group optionally fused to a monocyclic or bicyclic hydrocarbon ring of at least one saturated or partially unsaturated 5- or
- each of R c and R d may be selected from the following group. i.e. furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, benzofuryl, dibenzofuranyl, benzothienyl, dibenzothienyl, thianthrenyl, naphthofuryl, furo[3,2-b]furanyl, furo[2,3-b]furanyl, furo[3, 4-b]furanyl, oxanthrenyl, indolyl, isoindolyl, carbazolyl, indoli
- Each X in the general formula (2A) is independently preferably an alkylene group having 2 to 4 carbon atoms, more preferably an alkylene group having 2 or 3 carbon atoms, and particularly preferably an ethylene group.
- c and d in the general formula (2A) are each independently preferably an integer of 1 to 6, more preferably an integer of 1 to 4, and particularly preferably 2 or 3.
- the diol represented by the general formula (2A) preferably contains at least one of the diols represented by the following structural formulas.
- R e and R f are each independently a hydrogen atom, a halogen atom (fluorine atom, chlorine atom, bromine atom, or iodine atom), optionally having substituent(s) 1 to 20 alkyl group (preferably C1-C6 alkyl group), optionally substituted C1-C20 alkoxy group (preferably C1-C6 alkoxy group), substituent A cycloalkyl group having 5 to 20 carbon atoms (preferably a cycloalkyl group having 5 to 10 carbon atoms) which may have a cycloalkoxy group having 5 to 20 carbon atoms which may have a substituent (preferably , a cycloalkoxy group having 5 to 10 carbon atoms), an optionally substituted aryl group having 6 to 20 carbon atoms (preferably an aryl group having 6 to 12 carbon atoms), O
- R e and R f each independently represent a hydrogen atom or a phenyl group.
- R h in -C ⁇ C-R h is an optionally substituted aryl group having 6 to 20 carbon atoms (preferably an aryl group having 6 to 12 carbon atoms), or O, N and S It represents an optionally substituted heteroaryl group having 6 to 20 carbon atoms (preferably a heteroaryl group having 6 to 12 carbon atoms) containing one or more hetero ring atoms selected from .
- Each X independently represents an optionally substituted alkylene group having 1 to 5 carbon atoms (preferably an alkylene group having 1 to 3 carbon atoms, more preferably an ethylene group).
- e and f each independently represent an integer of 0 to 10, preferably an integer of 1 to 3, more preferably 1;
- the diol represented by the general formula (3A) is NOLE (9,9-bis[6-(2-hydroxyethoxy)-2-naphthyl]fluorene represented by the following structural formula ) is particularly preferable, and in the present invention, a commercially available product or a synthesized product may be used.
- thermoplastic resin of one embodiment of the present invention is polyester resin, polycarbonate resin, polyester carbonate resin, epoxy resin, polyurethane resin, polyacrylic acid ester resin, polymethacrylic acid ester resin, etc., but is not particularly limited.
- a polyester resin or a polyester carbonate resin is preferable, and a polycarbonate resin is more preferable.
- the total ratio of structural units (A), (B) and (C) to all structural units is preferably 80 to 100 mol% of all structural units. , more preferably 90 to 100 mol %, particularly preferably 100 mol %. That is, the thermoplastic resin of one embodiment of the present invention, in addition to the structural units (A) to (C), is generally used as a structural unit of a polycarbonate resin or a polyester carbonate resin within a range that does not impair the effects of the present invention. Structural units derived from the aliphatic dihydroxy compound used and structural units derived from the aromatic dihydroxy compound can be included.
- various aliphatic dihydroxy compounds can be mentioned, and in particular, 1,4-cyclohexanedimethanol, tricyclodecanedimethanol, 1,3-adamantanedimethanol, 2,2-bis( 4-hydroxycyclohexyl)-propane, 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, 2-(5-ethyl -5-hydroxymethyl-1,3-dioxan-2-yl)-2-methylpropan-1-ol, isosorbide, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, etc.
- aromatic dihydroxy compounds can be mentioned, but in particular 2,2-bis(4-hydroxyphenyl)propane [bisphenol A], bis(4-hydroxyphenyl)methane, 1,1-bis( 4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 4,4'-dihydroxydiphenyl, bis(4-hydroxyphenyl)cycloalkane, bis(4-hydroxyphenyl) ) oxide, bis(4-hydroxyphenyl) sulfide, bis(4-hydroxyphenyl) sulfone, bis(4-hydroxyphenyl) sulfoxide, and bis(4-hydroxyphenyl) ketone, bisphenoxyethanol fluorene, and the like.
- bisphenol A 2,2-bis(4-hydroxyphenyl)propane
- 1,1-bis( 4-hydroxyphenyl)ethane 1,1-bis( 4-hydroxyphenyl)ethane
- the thermoplastic resin of one embodiment of the present invention also preferably contains structural units derived from at least one monomer selected from the following monomer group.
- R 1 and R 2 each independently represent a hydrogen atom, a methyl group or an ethyl group
- R 3 and R 4 each independently represent a hydrogen atom, a methyl group, an ethyl group or a represents an alkylene glycol of ⁇ 5.
- the polycarbonate resin of a preferred embodiment of the present invention contains alcohol-based compounds such as phenol-based compounds that may be produced as by-products during production, and diol components or carbonic acid diesters that remain unreacted as impurities.
- Alcoholic compounds such as phenolic compounds and carbonic acid diesters, which are impurities, can cause a decrease in strength and generation of odor when formed into a molded article.
- the content of the remaining phenolic compound is preferably 3000 mass ppm or less, more preferably 1000 mass ppm or less, and particularly preferably 300 mass ppm or less based on 100 mass% of the polycarbonate resin.
- the content of the remaining diol component is preferably 1000 mass ppm or less, more preferably 100 mass ppm or less, and particularly preferably 10 mass ppm or less based on 100 mass% of the polycarbonate resin.
- the content of the remaining carbonic acid diester is preferably 1000 mass ppm or less, more preferably 100 mass ppm or less, and particularly preferably 10 mass ppm or less based on 100 mass% of the polycarbonate resin.
- it is preferable that the content of compounds such as phenol and t-butylphenol is small, and that the content of these compounds is within the above range.
- the content of the phenolic compound remaining in the polycarbonate resin can be measured by a method of analyzing the phenolic compound extracted from the polycarbonate resin using gas chromatography.
- the content of the alcohol-based compound remaining in the polycarbonate resin can also be measured by a method of analyzing the alcohol-based compound extracted from the polycarbonate resin using gas chromatography.
- the contents of diol components and carbonic acid diesters remaining in the polycarbonate resin can also be measured by extracting these compounds from the polycarbonate resin and analyzing them using gas chromatography.
- by-product alcoholic compounds such as phenolic compounds, diol components, and carbonic acid diesters may be reduced to the extent that they are not detected. good too. Moreover, if the amount is very small, the plasticity can be improved when the resin is melted.
- each of the remaining phenolic compound, diol component, or diester carbonate is, for example, 0.01 mass ppm or more, 0.1 mass ppm or more, or 1 mass ppm or more with respect to 100 mass% of the polycarbonate resin.
- the content of the remaining alcohol compound may be, for example, 0.01 mass ppm or more, 0.1 mass ppm or more, or 1 mass ppm or more with respect to 100 mass% of the polycarbonate resin.
- by-product alcohol compounds such as phenolic compounds, diol components, and carbonic acid diesters in the polycarbonate resin are adjusted so as to fall within the above ranges by appropriately adjusting the polycondensation conditions and equipment settings. It is possible. It can also be adjusted by the conditions of the extrusion process after polycondensation.
- the residual amount of by-product alcoholic compounds such as phenolic compounds is related to the type of diester carbonate used in the polymerization of the polycarbonate resin, the polymerization reaction temperature, the polymerization pressure, and the like. By adjusting these, the residual amount of by-product alcoholic compounds such as phenolic compounds can be reduced.
- the content of the remaining by-product alcohol compound in the obtained polycarbonate resin is preferably 3000 mass ppm or less with respect to the polycarbonate resin (100 mass %).
- the content of the remaining alcohol-based compound is preferably 3000 mass ppm or less, more preferably 1000 mass ppm or less, and particularly preferably 300 mass ppm or less based on 100 mass% of the polycarbonate resin.
- thermoplastic resin ⁇ Physical properties of thermoplastic resin> (1) Refractive index (nD)
- one of the characteristics of the thermoplastic resin is that it has a high refractive index. is more preferable, and 1.662 to 1.689 is particularly preferable.
- the refractive index can be measured by the method described in Examples below.
- the Abbe number of the thermoplastic resin is preferably 16.0 to 21.0, more preferably 16.3 to 20.5, and 16.6 to 20.2. is particularly preferred. In the present invention, the Abbe number can be measured by the method described in Examples below.
- one of the characteristics of the thermoplastic resin is high heat resistance, and the glass transition temperature (Tg) is preferably 130 to 190 ° C., and at 135 to 180 ° C. 140 to 165°C is particularly preferred.
- the glass transition temperature can be measured by the method described in Examples below.
- the polystyrene equivalent weight average molecular weight of the thermoplastic resin is preferably 10,000 to 100,000, more preferably 20,000 to 70,000, 30,000 to 60,000 is particularly preferred.
- melt volume flow rate (MVR) of the thermoplastic resin is preferably 20-55, more preferably 25-50, particularly preferably 30-45.
- the melt volume flow rate (MVR) in the present invention can be measured by the method described in Examples below.
- the haze of the thermoplastic resin is preferably 0.01 to 1.00, more preferably 0.05 to 0.50, and 0.10 to 0.30 is particularly preferred. In the present invention, haze can be measured by the method described in Examples below.
- the in-plane birefringence of the thermoplastic resin is preferably 1 to 21, more preferably 2 to 15, and 2 to 13. It is particularly preferred to have In the present invention, the in-plane birefringence of the lens can be measured by the method described in Examples below.
- thermoplastic resin composition Another embodiment of the invention is a thermoplastic resin composition comprising the thermoplastic resin described above and an additive.
- the thermoplastic resin composition of the present embodiment is a thermoplastic resin other than the thermoplastic resin of the present invention containing the above-described structural units (A), (B) and (C) within a range that does not impair the desired effects of the present embodiment.
- a resin can be used in combination.
- Such resins include, but are not limited to, polycarbonate resins, polyester resins, polyester carbonate resins, (meth)acrylic resins, polyamide resins, polystyrene resins, cycloolefin resins, acrylonitrile-butadiene-styrene copolymer resins, chloride At least one resin selected from the group consisting of vinyl resins, polyphenylene ether resins, polysulfone resins, polyacetal resins and methyl methacrylate-styrene copolymer resins can be used. Various known ones can be used as these, and they can be added to the thermoplastic resin composition singly or in combination of two or more.
- the thermoplastic resin composition preferably contains an antioxidant as the additive.
- an antioxidant it is preferable to contain at least one of a phenolic antioxidant and a phosphite antioxidant.
- phenolic antioxidants 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene, 1,3,5-tris(3 ,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine e-2,4,6(1H,3H,5H)-trione, 4,4′,4′′-(1 -methylpropanyl-3-ylidene)tris(6-tert-butyl-m-cresol), 6,6'-di-tert-butyl-4,4'-butylidenedi-m-cresol, ocladecyl 3-(3, 5-di-tert-butyl-4-hydroxyphenyl)propionate, pentaery
- Phosphite antioxidants such as 2-ethylhexyldiphenylphosphite, isodecyldiphenylphosphite, triisodecylphosphite, triphenylphosphite, 3,9-bis(octadecyloxy)-2,4,8,10- Tetraoxy-3,9-diphosphaspiro[5.5]undecane, 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa- 3,9-diphosphaspiro[5.5]undecane, 2,2′-methylenebis(4,6-di-tert-butylphenyl) 2-ethylhexylphosphite, tris(2,4-ditert-butylphenyl ) phosphite, tris(nonylphenyl)phosphite, tetra-C12-15-alky
- any one of the above may be used alone, or a mixture of two or more may be used. Further, in the present invention, 5,7-di-tert-butyl-3-(3,4-dimethylphenyl)-3H-benzofuran- 2-ones may also be used.
- the antioxidant is preferably contained in an amount of 1 ppm to 3000 ppm by weight based on the total weight of the resin composition.
- the content of the antioxidant in the thermoplastic resin composition is more preferably 50 ppm to 2500 ppm by weight, more preferably 100 ppm to 2000 ppm by weight, and particularly preferably 150 ppm to 1500 ppm by weight. and more preferably 200 ppm to 1500 ppm by weight.
- the thermoplastic resin composition preferably contains a release agent as the additive.
- release agents include ester compounds such as glycerin fatty acid esters such as mono- and diglycerides of glycerin fatty acid, glycol fatty acid esters such as propylene glycol fatty acid esters and sorbitan fatty acid esters, higher alcohol fatty acid esters, aliphatic polyhydric alcohols and aliphatic carboxylic acids. Full esters with acids, mono fatty acid esters, and the like can be mentioned.
- ester of an aliphatic polyhydric alcohol and an aliphatic carboxylic acid is used as the release agent, either a monoester, a full ester, or the like can be used.
- release agents include the following. Namely, sorbitan fatty acid esters such as sorbitan stearate, sorbitan laurate, sorbitan oleate, sorbitan trioleate, sorbitan tribehenate, sorbitan stearate, sorbitan tristearate, sorbitan caprylate; Propylene glycol fatty acid esters such as propylene glycol monostearate, propylene glycol monooleate, propylene glycol monobehenate, propylene glycol monolaurate, and propylene glycol monopalmitate; Higher alcohol fatty acid esters such as stearyl stearate; Glycerin monostearate, glycerin mono-12-hydroxystearate, etc.
- sorbitan fatty acid esters such as sorbitan stearate, sorbitan laurate, sorbitan oleate, sorbitan trioleate, sorbitan tribehenate, sorbitan stea
- the release agent is preferably contained in an amount of 1 ppm to 5000 ppm by weight based on the total weight of the resin composition.
- the content of the release agent in the thermoplastic resin composition is more preferably 50 wt ppm to 4000 wt ppm, still more preferably 100 wt ppm to 3500 wt ppm, and particularly preferably 500 wt ppm to 13000 wt ppm. and more preferably 1000 ppm to 2500 ppm by weight.
- additives may be added to the thermoplastic resin composition in addition to the antioxidant and release agent described above.
- additives that may be contained in the thermoplastic resin composition include compounding agents, catalyst deactivators, heat stabilizers, plasticizers, fillers, ultraviolet absorbers, rust inhibitors, dispersants, antifoaming agents, leveling agents, Examples include flame retardants, lubricants, dyes, pigments, bluing agents, nucleating agents, and clarifying agents.
- the content of additives other than antioxidants and release agents in the thermoplastic resin composition is preferably 10 wt ppm to 5.0 wt %, more preferably 100 wt ppm to 2.0 wt %. and more preferably 1000 ppm by weight to 1.0% by weight, but not limited thereto.
- the above additives may adversely affect the transmittance and should not be added in excess, eg the total amount added is within the above range.
- the catalyst may be removed or deactivated in order to maintain thermal stability and hydrolytic stability after the completion of the polymerization reaction, but it is not always necessary to deactivate it. do not have.
- the known method for deactivating the catalyst by adding an acidic substance can be suitably carried out.
- acidic substances include esters such as butyl benzoate; aromatic sulfonic acids such as p-toluenesulfonic acid; aromatic sulfonate esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate.
- Phosphoric acid phosphoric acid, phosphoric acid such as phosphonic acid
- triphenyl phosphite monophenyl phosphite, diphenyl phosphite, diethyl phosphite, di-n-propyl phosphite, di Phosphites such as n-butyl, di-n-hexyl phosphite, dioctyl phosphite, monooctyl phosphite
- Phosphonic acid esters such as dioctyl and monooctyl phosphate
- Phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid and dibutylphosphonic acid
- Phosphonic acid esters such as diethyl phenylphosphonate
- deactivator From the viewpoint of the effect of the deactivator, the stability to the resin, and the like, p-toluene, butyl sulfonate, or tetrabutyl phosphonium dodecylbenzenesulfonate is particularly preferred.
- These deactivators are used in an amount of 0.01 to 50 times mol, preferably 0.3 to 20 times mol, relative to the catalyst amount. If it is less than 0.01 times the molar amount of the catalyst, the deactivation effect becomes insufficient, which is not preferable. On the other hand, when the amount is more than 50 times the molar amount of the catalyst, the heat resistance of the resin is lowered, and the molded article tends to be colored, which is not preferable.
- the deactivator may be kneaded immediately after completion of the polymerization reaction, or may be kneaded after pelletizing the polymerized resin. In addition to the deactivator, other additives can also be added by the same method.
- thermoplastic resin or thermoplastic resin composition (hereinafter simply referred to as "resin composition") of the present invention can be suitably used for optical members.
- An embodiment of the present invention provides an optical member containing the resin composition of the present invention.
- optical members include optical discs, transparent conductive substrates, optical cards, sheets, films, optical fibers, lenses, prisms, optical films, substrates, optical filters, hard coat films, etc. It is not limited to these.
- the resin composition of the present invention has a high fluidity and can be molded by a casting method, so it is particularly suitable for manufacturing thin optical members.
- the optical member produced using the resin composition of the present invention may be an optical lens.
- the optical member produced using the resin composition of the present invention may be an optical film.
- an optical member containing the resin composition of the present invention is produced by injection molding, it is preferable to perform molding under the conditions of a cylinder temperature of 260 to 350°C and a mold temperature of 90 to 170°C. More preferably, molding is carried out under conditions of a cylinder temperature of 270 to 320°C and a mold temperature of 100 to 160°C. If the cylinder temperature is higher than 350°C, the resin composition will decompose and color, and if it is lower than 260°C, the melt viscosity will be high and molding will be difficult. Moreover, when the mold temperature is higher than 170° C., it tends to be difficult to remove the molded piece made of the resin composition from the mold.
- the mold temperature is less than 90° C.
- the resin will harden too quickly in the mold during molding, making it difficult to control the shape of the molded piece, or the mold applied to the mold will not be sufficiently transferred. It is easy to become difficult.
- the resin composition can be suitably used for optical lenses.
- Optical lenses manufactured using the resin composition of the present invention have a high refractive index and excellent heat resistance, so conventionally, expensive high refractive index glass lenses have been used for telescopes, binoculars, television projectors, and the like. It can be used in various fields and is extremely useful.
- a lens molded from a resin containing a structural unit derived from any of the monomers of the above formulas can be superimposed and used as a lens unit.
- the optical lens of the present invention is preferably implemented in the form of an aspherical lens if necessary.
- Aspherical lenses can eliminate spherical aberration with a single lens, so there is no need to combine multiple spherical lenses to remove spherical aberration, which helps reduce weight and molding costs. be possible. Therefore, aspherical lenses are particularly useful as camera lenses among optical lenses.
- the optical lens of the present invention is particularly useful as a material for thin, compact, and complicated-shaped optical lenses because of its high molding fluidity.
- the thickness of the central portion is preferably 0.05 to 3.0 mm, more preferably 0.05 to 2.0 mm, still more preferably 0.1 to 2.0 mm.
- the diameter is preferably 1.0 mm to 20.0 mm, more preferably 1.0 to 10.0 mm, still more preferably 3.0 to 10.0 mm.
- the lens is a meniscus lens having a convex surface on one side and a concave surface on the other side.
- the optical lens of the present invention can be molded by any method such as mold molding, cutting, polishing, laser processing, electrical discharge machining, and etching. Among these, mold molding is more preferable from the viewpoint of manufacturing cost.
- the resin composition can be suitably used for optical films.
- the optical film produced using the polycarbonate resin of the present invention is excellent in transparency and heat resistance, and thus is suitably used for films for liquid crystal substrates, optical memory cards, and the like.
- the molding environment must naturally be a low-dust environment, preferably class 6 or less, more preferably class 5 or less.
- a second embodiment of the present invention comprises a structural unit represented by the following general formula (1B), a binaphthol derivative unit represented by the following general formula (2B), and a fluorene derivative represented by the following general formula (3B).
- X represents an alkylene group having 1 to 4 carbon atoms, and a and b each independently represents an integer of 1 to 10.
- Y represents an alkylene group having 1 to 4 carbon atoms, and c and d each independently represent an integer of 1 to 10.
- Z represents an alkylene group having 1 to 4 carbon atoms
- R 1 to R 6 each independently represents 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 group having 5 to 20 carbon atoms. group, an aryl group having 6 to 20 carbon atoms or an aryloxy group having 6 to 20 carbon atoms, e and f each independently represent an integer of 0 to 5; )
- the polycarbonate resin of the present invention preferably consists essentially of structural units represented by general formulas (1B) to (3B).
- "consisting essentially of” means that the polycarbonate resin of the present invention may contain other structural units within a range that does not impair the effects of the invention.
- the constituent units of the polycarbonate resin of the present invention preferably 90% or more, more preferably 95% or more, and still more preferably 98% or more are composed of structural units represented by general formulas (1B) to (3B). .
- the proportion of the structural unit represented by the general formula (1B) is 1 mol% or more and less than 10 mol%, and the proportion of the structural unit represented by the general formula (2B) is 10 to 60 mol. %, and the proportion of the structural unit represented by the general formula (3B) is 5 to 80 mol %.
- the ratio of the structural unit represented by general formula (1B) is 2 to 9 mol%, and the general formula ( The ratio of the structural unit represented by 2B) is 20 to 60 mol%, and the ratio of the structural unit represented by general formula (3B) is preferably 30 to 70 mol%.
- the proportion of the structural unit represented by the general formula (2B) is 3 to 8 mol%, the proportion of the structural unit represented by the general formula (2B) is 30 to 60 mol%, and the proportion of the structural unit represented by the general formula (3B) A proportion of 40 to 60 mol % is particularly preferred.
- the polycarbonate resin of the present invention is not particularly limited in how the structural units represented by general formulas (1B) to (3B) are included in the resin.
- the polycarbonate resin may contain a copolymer containing structural units represented by general formulas (1B) to (3B), and a ternary containing a homopolymer consisting of each structural unit It may be a system resin. Alternatively, it may be a blend of a copolymer containing structural units represented by general formulas (1B) and (2B) and a homopolymer containing structural units represented by general formula (3B). A copolymer containing structural units represented by formulas (1B) and (2B) and a copolymer containing structural units represented by general formulas (1B) and (3B) may be blended. .
- the polycarbonate resin of the present invention may contain any of random, block and alternating copolymer structures.
- the preferred polystyrene equivalent weight average molecular weight (Mw) of the polycarbonate resin of the present invention is 20,000 to 200,000. More preferably, the polystyrene equivalent weight average molecular weight (Mw) is 25,000 to 120,000, still more preferably 28,000 to 55,000, and particularly preferably 30,000 to 45,000.
- Mw is less than 20,000, the compact becomes brittle, which is not preferable. If Mw is more than 200,000, the melt viscosity becomes high, making it difficult to take out the resin after production.
- the refractive index (nD) of the polycarbonate resin of the present invention at 23° C. and a wavelength of 589 nm is preferably 1.635 to 1.695, more preferably 1.640 to 1.690, and still more preferably 1.645 to 1.685. and particularly preferably 1.650 to 1.680.
- the polycarbonate resin of the present invention has a high refractive index (nD) and is suitable for optical lens materials.
- the refractive index can be measured by the method of JIS B 7071-2:2018 using an Abbe refractometer for a film having a thickness of 0.1 mm.
- the Abbe number ( ⁇ ) of the polycarbonate resin of the present invention is preferably 24 or less, more preferably 22 or less, still more preferably 21 or less.
- the melt volume flow rate (MVR) of the polycarbonate resin of the present invention is preferably 10-100, more preferably 30-100, and particularly preferably 30-50.
- MVR can be measured by the method described in Examples below.
- the birefringence intensity of the polycarbonate resin of the present invention is preferably ⁇ 0.6 to +0.7, more preferably ⁇ 0.5 to +0.5, and particularly preferably ⁇ 0.3 to +0.3. be.
- the birefringence intensity can be measured by the method described in Examples below.
- the in-plane birefringence of the polycarbonate resin of the present invention is preferably 0.1-15, more preferably 1-10, and particularly preferably 2-7.
- the in-plane birefringence of the lens can be measured by the method described in Examples below.
- the haze of the polycarbonate resin of the present invention is preferably 0.05 to 3.00, more preferably 0.10 to 2.00.
- haze can be measured by the method described in Examples below.
- the polycarbonate resin of the present invention can be blended with other resins and used for the production of molded articles.
- other resins include polyamide, polyacetal, polycarbonate, modified polyphenylene ether, polyethylene terephthalate, polybutylene terephthalate and the like.
- antioxidants can be added to the polycarbonate resin of the present invention.
- molding methods include, but are not limited to, injection molding, compression molding, cast molding, roll processing, extrusion molding, and stretching.
- the glass transition temperature (Tg) is preferably 90 to 180°C, more preferably 95 to 175°C, still more preferably 100 to 170°C, still more preferably 130 to 170°C, particularly preferably 135 to 150°C. If the Tg is lower than 90°C, the usable temperature range becomes narrow, which is not preferable. On the other hand, if it exceeds 180° C., the melting temperature of the resin becomes high, and the resin tends to be decomposed or colored, which is not preferable. If the glass transition temperature of the resin is too high, the difference between the mold temperature and the glass transition temperature of the resin becomes large with a general-purpose mold temperature controller.
- the lower limit of Tg is preferably 130°C, more preferably 135°C, and the upper limit of Tg is preferably 160°C, more preferably 150°C.
- the amount of residual phenol contained in the polycarbonate resin of the present invention is preferably 500 ppm or less, more preferably 300 ppm or less, and even more preferably 50 ppm or less.
- the amount of residual diphenyl carbonate (DPC) contained in the polycarbonate resin of the present invention is preferably 200 ppm or less, more preferably 100 ppm or less, and even more preferably 50 ppm or less.
- Polycarbonate resins having structural units represented by general formulas (1B) to (3B) according to the present invention are represented by general formulas (4B) to (6B) below.
- X represents an alkylene group having 1 to 4 carbon atoms
- a and b each independently represents an integer of 1 to 10.
- Y represents an alkylene group having 1 to 4 carbon atoms
- c and d each independently represent an integer of 1 to 10.
- Z represents an alkylene group having 1 to 4 carbon atoms
- R 1 to R 6 each independently represents 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 group having 5 to 20 carbon atoms.
- a compound represented by as the dihydroxy component can be prepared by using a compound represented by as the dihydroxy component and reacting it with a carbonate precursor such as a carbonate diester.
- a carbonate precursor such as a carbonate diester.
- the compound represented by the general formulas (4B) to (6B) and a carbonate precursor such as a diester carbonate are mixed in the presence or absence of a mixed catalyst consisting of a basic compound catalyst or an ester exchange catalyst or both. It can be produced by a melt polycondensation method in the presence of a catalyst.
- Compounds of general formula (4B) include 9,9-bis(hydroxy(poly)alkoxynaphthyl)fluorenes.
- compounds of general formula (4) include 9,9-bis[6-(1-hydroxymethoxy)naphthalen-2-yl]fluorene, 9,9-bis[6-(2-hydroxyethoxy)naphthalene-2 -yl]fluorene, 9,9-bis[6-(3-hydroxypropoxy)naphthalen-2-yl]fluorene, and 9,9-bis[6-(4-hydroxybutoxy)naphthalen-2-yl]fluorene, etc. is mentioned. Among them, 9,9-bis[6-(2-hydroxyethoxy)naphthalen-2-yl]fluorene is preferred. These may be used alone or in combination of two or more.
- a compound in which either a or b is 0 may be produced as an impurity by-product.
- the total content of such impurities in the monomer containing the compound of general formula (4B) as a main component is preferably 1000 ppm or less, more preferably 500 ppm or less, and 200 ppm or less. More preferably, it is particularly preferably 100 ppm or less.
- fluorenone which is one of the raw materials, may also be included as an impurity.
- the content of fluorenone is preferably 1000 ppm or less, more preferably 100 ppm or less, even more preferably 50 ppm or less, and 10 ppm or less in the monomer containing the compound of general formula (4B) as a main component. is particularly preferred. Fluorenone contained in the monomer containing the compound of general formula (4B) as a main component may remain in the resin after polymerization. The smaller the content of fluoronolene, the better the hue of the resin, which is preferable.
- the total amount of compounds in which a and b in general formula (4B) are not the same is 50 ppm or less in the monomer containing the compound of general formula (4B) as a main component. is preferred, and 20 ppm or less is more preferred.
- the compound of general formula (4B) can be produced by various synthetic methods. For example, as described in Japanese Patent No. 5442800, (a) a method of reacting fluorenones and hydroxynaphthalenes in the presence of hydrogen chloride gas and mercaptocarboxylic acid, (b) acid catalyst (and alkyl mercaptan) (c) a method of reacting a fluorenone with a hydroxynaphthalene in the presence of hydrochloric acid and a thiol (mercaptocarboxylic acid, etc.); (d) a method of reacting a fluorenone with a hydroxynaphthalene in the presence of sulfuric acid and A method of producing bisnaphtholfluorene by reacting fluorenones and hydroxynaphthalenes in the presence of thiols (mercaptocarboxylic acids, etc.) and crystallizing them with a crystallization solvent composed of hydrocarbons and a polar solvent, etc
- 9,9-bis(hydroxynaphthyl)fluorenes which are then reacted with compounds corresponding to [XO]a and [XO]b groups (such as alkylene oxides and haloalkanols).
- compounds corresponding to [XO]a and [XO]b groups such as alkylene oxides and haloalkanols.
- 9,9-bis[6-(2-hydroxyethoxy)naphthyl]fluorene is obtained by reacting 9,9-bis[6-hydroxynaphthyl]fluorene with 2-chloroethanol under alkaline conditions.
- dihydroxy compounds represented by general formula (5B) examples include 2,2′-bis(1-hydroxymethoxy)-1,1′-binaphthalene, 2,2′-bis(2-hydroxyethoxy)-1, 1'-binaphthalene, 2,2'-bis(3-hydroxypropyloxy)-1,1'-binaphthalene, 2,2'-bis(4-hydroxybutoxy)-1,1'-binaphthalene and the like.
- BHEBN 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene
- BHEBN 2,2'-bis(2-hydroxyethoxy)-1,1'-binaphthalene
- a compound in which either c or d is 0 may be produced as an impurity by-product.
- the total content of such impurities in the monomer containing the compound of general formula (5B) as a main component is preferably 1000 ppm or less, more preferably 500 ppm or less, and 200 ppm or less. More preferably, it is particularly preferably 100 ppm or less.
- the total amount of compounds in the general formula (5B) where c and d are not the same (i.e., c ⁇ d) is 50 ppm or less in the monomer containing the compound of the general formula (5B) as a main component. is preferred, and 20 ppm or less is more preferred.
- Examples of dihydroxy compounds represented by general formula (6B) include 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene (hereinafter sometimes abbreviated as “BPEF”), 9,9-bis [4-(2-hydroxyethoxy)-3-methylphenyl]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 (hereinafter sometimes abbreviated as “BPPEF”) and the like.
- BPEF 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene
- BPPEF 9,9-bis[4-(
- 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene and 9,9-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]fluorene are preferred. These may be used alone or in combination of two or more.
- a compound in which either e or f is 0 may be produced as an impurity by-product.
- the total content of such impurities in the monomer containing the compound of general formula (6B) as a main component is preferably 1000 ppm or less, more preferably 500 ppm or less, and 200 ppm or less. More preferably, it is particularly preferably 100 ppm or less.
- the total amount of compounds in which e and f in general formula (6B) are not the same that is, e ⁇ f) is 50 ppm or less in the monomer containing the compound of general formula (6B) as a main component. is preferred, and 20 ppm or less is more preferred.
- aromatic dihydroxy compounds examples include bisphenol A, bisphenol AP, bisphenol AF, bisphenol B, bisphenol BP, bisphenol C, bisphenol E, bisphenol F, bisphenol G, bisphenol M, bisphenol S, and bisphenol.
- P, bisphenol PH, bisphenol TMC, bisphenol Z and the like are exemplified.
- Carbonic acid diesters used in the present invention include diphenyl carbonate, ditolyl carbonate, bis(chlorophenyl) carbonate, m-cresyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate and the like.
- diphenyl carbonate is particularly preferred.
- Diphenyl carbonate is preferably used in a ratio of 0.97 to 1.20 mol, more preferably in a ratio of 0.98 to 1.10 mol, per 1 mol of the total dihydroxy compound.
- examples of basic compound catalysts include alkali metal compounds, alkaline earth metal compounds, and nitrogen-containing compounds.
- alkali metal compounds used in the present invention include organic acid salts, inorganic salts, oxides, hydroxides, hydrides and alkoxides of alkali metals.
- alkaline earth metal compounds include organic acid salts, inorganic salts, oxides, hydroxides, hydrides and alkoxides of alkaline earth metal compounds.
- magnesium hydroxide, calcium acetate, strontium acetate, barium acetate, magnesium stearate, calcium stearate, calcium benzoate, magnesium phenylphosphate and the like are used.
- nitrogen-containing compounds include quaternary ammonium hydroxides and salts thereof, amines, and the like.
- quaternary ammonium hydroxides having an alkyl group, an aryl group such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylbenzylammonium hydroxide; tertiary amines such as triethylamine, dimethylbenzylamine, triphenylamine; secondary amines such as diethylamine and dibutylamine; primary amines such as propylamine and butylamine; 2-methylimidazole, 2-phenylimidazole, benzimidazole or imidazoles such as ammonia, tetramethylammonium borohydride, tetrabutylammonium borohydride, tetrabut
- Salts of zinc, tin, zirconium, lead, etc. are preferably used as transesterification catalysts, and these can be used alone or in combination.
- transesterification catalysts include zinc acetate, zinc benzoate, zinc 2-ethylhexanoate, tin (II) chloride, tin (IV) chloride, tin acetate (II), tin acetate (IV), and dibutyltin.
- Dilaurate, dibutyltin oxide, dibutyltin dimethoxide, zirconium acetylacetonate, zirconium oxyacetate, zirconium tetrabutoxide, lead acetate (II), lead acetate (IV) and the like are used.
- These catalysts are used in a ratio of 1 ⁇ 10 ⁇ 9 to 1 ⁇ 10 ⁇ 3 mol, preferably in a ratio of 1 ⁇ 10 ⁇ 7 to 1 ⁇ 10 ⁇ 4 mol, per 1 mol of the total dihydroxy compound. .
- melt polycondensation is performed under heat and under normal or reduced pressure while removing by-products through transesterification.
- Melt polycondensation in this composition system is performed by melting the compounds represented by the general formulas (4B) to (6B) and the diester carbonate in a reaction vessel, and then allowing the by-product monohydroxy compound to stay in the reaction vessel. It is desirable to The pressure can be controlled by closing the reaction apparatus, depressurizing or pressurizing the reaction apparatus for retention.
- the reaction time for this step is 20 minutes or more and 240 minutes or less, preferably 40 minutes or more and 180 minutes or less, and particularly preferably 60 minutes or more and 150 minutes or less.
- the by-produced monohydroxy compound is distilled off immediately after its formation, the finally obtained polycarbonate resin has a low content of high molecular weight substances.
- the finally obtained polycarbonate resin has a large content of high molecular weight substances.
- the melt polycondensation reaction may be performed continuously or batchwise.
- the reactor used for the reaction may be of a vertical type equipped with anchor-type stirring blades, MAXBLEND stirring blades, helical ribbon-type stirring blades, etc., or a horizontal type equipped with paddle blades, lattice blades, spectacle blades, etc. It may be of the extruder type equipped with a screw.
- the catalyst may be removed or deactivated after completion of the polymerization reaction in order to maintain thermal stability and hydrolytic stability.
- a method of deactivating the catalyst by adding a known acidic substance can be preferably carried out.
- acidic substances include esters such as butyl benzoate, aromatic sulfonic acids such as p-toluenesulfonic acid, and aromatic sulfonate esters such as butyl p-toluenesulfonate and hexyl p-toluenesulfonate.
- Phosphoric acid phosphoric acid, phosphoric acid such as phosphonic acid
- triphenyl phosphite monophenyl phosphite, diphenyl phosphite, diethyl phosphite, di-n-propyl phosphite, di Phosphites such as n-butyl, di-n-hexyl phosphite, dioctyl phosphite, monooctyl phosphite
- Phosphonic acid esters such as dioctyl and monooctyl phosphate
- Phosphonic acids such as diphenylphosphonic acid, dioctylphosphonic acid and dibutylphosphonic acid
- Phosphonic acid esters such as diethyl phenylphosphonate
- butyl p-toluenesulfonate and tetrabutylphosphonium dodecylbenzenesulfonate are particularly preferably used.
- These deactivators are used in an amount of 0.01 to 50 times mol, preferably 0.3 to 20 times mol, relative to the catalyst amount. If it is less than 0.01 times the molar amount of the catalyst, the deactivation effect becomes insufficient, which is not preferable. On the other hand, when the amount is more than 50 times the molar amount of the catalyst, the heat resistance of the resin is lowered, and the molded article tends to be colored, which is not preferable.
- a step of devolatilizing and removing low boiling point compounds in the polymer at a pressure of 0.1 to 1 mmHg and a temperature of 200 to 350°C may be provided.
- a horizontal apparatus equipped with stirring blades with excellent surface renewal performance such as paddle blades, lattice blades, or spectacle blades, or a thin film evaporator is preferably used.
- the polycarbonate resin of the present invention is desired to contain as little foreign matter as possible, and filtration of the molten raw material, filtration of the catalyst solution, etc. are preferably carried out.
- the mesh of the filter is preferably 5 ⁇ m or less, more preferably 1 ⁇ m or less.
- filtration of the resulting resin through a polymer filter is preferably carried out.
- the mesh of the polymer filter is preferably 100 ⁇ m or less, more preferably 30 ⁇ m or less.
- the step of collecting resin pellets must naturally be in a low dust environment, preferably class 6 or less, more preferably class 5 or less.
- a copolymer containing structural units represented by the general formulas (1B) to (3B) may be produced, and the compounds represented by the general formulas (4B) to (6B) are separately polymerized to obtain each It may be produced as a ternary resin containing a homopolymer consisting of constitutional units.
- a copolymer containing structural units represented by general formulas (1B) and (2B) and a homopolymer containing structural units represented by general formula (3B) may be blended after polymerization.
- a copolymer containing structural units represented by (1B) and (2B) and a copolymer containing structural units represented by general formulas (1B) and (3B) may be polymerized and then blended.
- An optical molded article can be produced using the polycarbonate resin of the present invention.
- it is molded by any method such as injection molding, compression molding, extrusion molding, or solution casting. Since the polycarbonate resin of the present invention is excellent in moldability and heat resistance, it can be used particularly advantageously in optical lenses that require injection molding.
- the polycarbonate resin of the present invention can be used by mixing with other resins such as other polycarbonate resins and polyester resins.
- 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-tert-butyl-4-hydroxy-benzylphosphonate-diethyl ester,
- processing stabilizers include phosphorus-based processing heat stabilizers and sulfur-based processing heat stabilizers.
- Phosphorous processing heat stabilizers include phosphorous acid, phosphoric acid, phosphonous acid, phosphonic acid and esters thereof.
- triphenylphosphite tris(nonylphenyl)phosphite, tris(2,4-di-tert-butylphenyl)phosphite, tris(2,6-di-tert-butylphenyl)phosphite, tridecylphosphite, trioctylphosphite, trioctadecylphosphite, didecylmonophenylphosphite, dioctylmonophenylphosphite, diisopropylmonophenylphosphite, monobutyldiphenylphosphite, monodecyldiphenylphosphite
- Sulfur-based processing heat stabilizers include pentaerythritol-tetrakis (3-laurylthiopropionate), pentaerythritol-tetrakis (3-myristylthiopropionate), and 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 per 100 parts by weight of the polycarbonate resin.
- esters of alcohols and fatty acids include esters of monohydric alcohols and fatty acids, and partial or full esters of polyhydric alcohols and fatty acids.
- ester of monohydric alcohol and fatty acid an ester of monohydric alcohol having 1 to 20 carbon atoms and saturated fatty acid having 10 to 30 carbon atoms is preferable.
- Partial or full esters of a polyhydric alcohol and a fatty acid are preferably partial or full esters of a polyhydric alcohol having 1 to 25 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms.
- esters of monohydric alcohols and saturated fatty acids include stearyl stearate, palmityl palmitate, butyl stearate, methyl laurate, and isopropyl palmitate.
- Partial or full esters of polyhydric alcohols with saturated fatty acids include stearic acid monoglyceride, stearic acid monoglyceride, stearic acid diglyceride, stearic acid triglyceride, stearic acid monosorbitate, behenic acid monoglyceride, capric acid monoglyceride, lauric acid monoglyceride, Pentaerythritol monostearate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, biphenyl biphenate, sorbitan monostearate, 2-ethylhexyl stearate, dipentaerythritol
- Full esters or partial esters of pentaerythritol and the like can be mentioned.
- the content of these releasing 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, and 0.02 to 0.02 parts by weight, based on 100 parts by weight of the polycarbonate resin. A range of 0.5 parts by weight is more preferred.
- At least one ultraviolet absorber selected from the group consisting of benzotriazole-based ultraviolet absorbers, benzophenone-based ultraviolet absorbers, triazine-based ultraviolet absorbers, cyclic iminoester-based ultraviolet absorbers, and cyanoacrylate-based ultraviolet absorbers.
- Absorbents are preferred. That is, any of the ultraviolet absorbers listed below may be used alone, or two or more thereof may be used in combination.
- Benzotriazole-based UV absorbers 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-octylpheny
- Benzophenone UV absorbers 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-sulfoxytrihydrate benzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone , 2,2′-dihydroxy-4,4′-dimethoxybenzophenone, 2,2′-dihydroxy-4,4′-dimethoxy-5-sodium sulfoxybenzophenone, bis(5-benzoyl-4-hydroxy-2- methoxyphenyl)methane, 2-hydroxy-4-n-dodecyloxybenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone and the like.
- Triazine-based UV absorbers 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 and the like.
- Cyclic imino ester UV absorbers include 2,2′-bis(3,1-benzoxazin-4-one) and 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-phenylene)bis(3,1-benzoxazin-4-one).
- cyanoacrylate ultraviolet absorber 1,3-bis-[(2'-cyano-3',3'-diphenylacryloyl)oxy]-2,2-bis[(2-cyano-3,3-diphenyl acryloyl)oxy]methyl)propane, 1,3-bis-[(2-cyano-3,3-diphenylacryloyl)oxy]benzene and the like.
- 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 parts by weight with respect to 100 parts by weight of the polycarbonate resin. 0.05 to 0.8 parts by weight. Within such a blending amount range, it is possible to impart sufficient weather resistance to the polycarbonate resin depending on the application.
- the polycarbonate resin of the present invention has a high refractive index and a low Abbe number.
- a coat layer such as an antireflection layer or a hard coat layer may be provided on the surface of the optical molded body, if necessary.
- the antireflection layer may be a single layer or multiple layers, and may be organic or inorganic, but is preferably inorganic. Specifically, oxides or fluorides such as silicon oxide, aluminum oxide, zirconium oxide, titanium oxide, cerium oxide, magnesium oxide and magnesium fluoride are exemplified.
- the optical lens manufactured using the polycarbonate resin of the present invention has a high refractive index, a low Abbe number, a small absolute value of birefringence intensity, and a small in-plane birefringence. It can be used in fields such as projectors where expensive high-refractive-index glass lenses have conventionally been used, and is extremely useful. If necessary, it is preferably used in the form of an aspherical lens. Since aspherical lenses can eliminate spherical aberration with a single lens, there is no need to remove spherical aberration by combining multiple spherical lenses, which helps reduce weight and production costs. be possible. Therefore, aspherical lenses are particularly useful as camera lenses among optical lenses.
- the optical lens is molded by any method such as injection molding, compression molding, injection compression molding, and the like. According to the present invention, it is possible to easily obtain a high-refractive-index, low-birefringence aspherical lens, which is technically difficult to process with a glass lens.
- the molding environment In order to avoid foreign matter from entering 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 films produced using the polycarbonate resin of the present invention are excellent in transparency and heat resistance, and are therefore suitably used for films for liquid crystal substrates, optical memory cards, and the like.
- the molding environment In order to avoid foreign matter from entering 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.
- refractive index (nD) Based on JIS B 7071-2: 2018, polycarbonate resin was molded to obtain a V block and used as a test piece. The refractive index was measured at 23° C. using a refractometer (KPR-3000 manufactured by Shimadzu Corporation).
- Tg Glass transition temperature Measurement was performed with a differential thermal scanning calorimeter in accordance with JIS K7121-1987 with a heating program of 10°C/min. Differential scanning calorimeter: X-DSC7000 manufactured by Hitachi High-Tech Science Co., Ltd.
- Example 2A-4A Comparative Examples 1A-8A
- a polycarbonate resin was obtained in the same manner as in Example 1A, except that the raw materials shown in Table 1 were used.
- Table 2 shows the physical properties of the obtained resin.
- Example 2B Comparative Examples 1B to 3B
- a polycarbonate resin was obtained in the same manner as in Example 1B, except that the raw materials shown in Table 4 were used.
- Table 3 shows the physical properties of the obtained resin.
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Abstract
Description
さらに近年では、複屈折強度の絶対値が小さく、レンズ面内複屈折も小さいポリカーボネート樹脂及び光学レンズが求められている。
<1> 樹脂中の構成単位の全量(100モル%)に対して、下記一般式(1A)で表されるジオールに由来する構成単位(A)を22~49モル%と、下記一般式(2A)で表されるジオールに由来する構成単位(B)を40~75モル%と、下記一般式(3A)で表されるジオールに由来する構成単位(C)を0~15モル%と、を含む熱可塑性樹脂である。
Rhは置換基を有してもよい炭素数6~20のアリール基、又は、O、N及びSから選択される1つ以上のヘテロ環原子を含む、置換基を有してもよい炭素数6~20のヘテロアリール基を表し、
Xは、それぞれ独立に、置換基を有してもよい炭素数1~5のアルキレン基を表し、
a及びbは、それぞれ独立に、0~10の整数を表す。)
Rhは置換基を有してもよい炭素数6~20のアリール基、又は、O、N及びSから選択される1つ以上のヘテロ環原子を含む、置換基を有してもよい炭素数6~20のヘテロアリール基を表し、
Xは、それぞれ独立に、置換基を有してもよい炭素数1~5のアルキレン基を表し、
c及びdは、それぞれ独立に、0~10の整数を表す。)
Rhは置換基を有してもよい炭素数6~20のアリール基、又は、O、N及びSから選択される1つ以上のヘテロ環原子を含む、置換基を有してもよい炭素数6~20のヘテロアリール基を表し、
Xは、それぞれ独立に、置換基を有してもよい炭素数1~5のアルキレン基を表し、
e及びfは、それぞれ独立に、0~10の整数を表す。)
<2> 樹脂中の構成単位の全量(100モル%)に対する、前記一般式(1A)で表されるジオールに由来する構成単位(A)の割合が、24~47モル%であり、前記一般式(2A)で表されるジオールに由来する構成単位(B)の割合が、45~70モル%であり、前記一般式(3A)で表されるジオールに由来する構成単位(C)の割合が、0~8モル%である、上記<1>に記載の熱可塑性樹脂である。
<3> 前記一般式(1)で表されるジオールが、下記構造式で表されるジオールを含む、上記<1>または<2>に記載の熱可塑性樹脂である。
<7> 前記熱可塑性樹脂が、更に、下記のモノマー群から選択される少なくとも一つのモノマーに由来する構成単位を含む、上記<1>から<6>のいずれかに記載の熱可塑性樹脂である。
<8> 前記熱可塑性樹脂のレンズ面内複屈折が1~21である、上記<1>から<7>のいずれかに記載の熱可塑性樹脂である。
<9> 前記熱可塑性樹脂のポリスチレン換算の重量平均分子量(Mw)が、10,000~100,000である、上記<1>から<8>のいずれかに記載の熱可塑性樹脂である。
<10> 前記熱可塑性樹脂の屈折率(nD)が、1.650~1.695である、上記<1>から<9>のいずれかに記載の熱可塑性樹脂である。
<11> 前記熱可塑性樹脂のアッベ数(ν)が、16.0~21.0である、上記<1>から<10>のいずれかに記載の熱可塑性樹脂である。
<12> 前記熱可塑性樹脂のガラス転移温度が、130~190℃である、上記<1>から<11>のいずれかに記載の熱可塑性樹脂である。
<13> 前記熱可塑性樹脂のメルトボリュームフローレイト(MVR)が、20~55である、上記<1>から<12>のいずれかに記載の熱可塑性樹脂である。
<14> 前記熱可塑性樹脂のヘーズが、0.01~1.00である、上記<1>から<13>のいずれかに記載の熱可塑性樹脂である。
<15> 上記<1>から<14>のいずれかに記載の熱可塑性樹脂を含む、光学部材である。
<16> 上記<1>から<14>のいずれかに記載の熱可塑性樹脂を含む、光学レンズである。
<17> 上記<1>から<14>のいずれかに記載の熱可塑性樹脂を含む、光学フィルムである。
<18>
下記一般式(1B)で表される構成単位と、下記一般式(2B)で表される構成単位と、下記一般式(3B)で表される構成単位と、を含むポリカーボネート樹脂であって、
下記一般式(1B)で表される構成単位の割合が1モル%以上10モル%未満であり、
下記一般式(2B)で表される構成単位の割合が10~60モル%であり、
下記一般式(3B)で表される構成単位の割合が5~80モル%である、前記ポリカーボネート樹脂である。
Zは炭素数1~4のアルキレン基を表し、
R1~R6は、各々独立に、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のアリール基又は炭素数6~20のアリールオキシ基を表し、
e及びfは、各々独立に、0~5の整数を表す。)
<19>
前記一般式(1B)で表される構成単位の割合が2~9モル%であり、
前記一般式(2B)で表される構成単位の割合が20~60モル%であり、
前記一般式(3B)で表される構成単位の割合が30~70モル%である、上記<18>に記載のポリカーボネート樹脂である。
<20>
上記<18>または<19>に記載のポリカーボネート樹脂を含む、光学レンズである。
<熱可塑性樹脂>
本発明の第1実施形態は、樹脂中の構成単位の全量(100モル%)に対して、下記一般式(1A)で表されるジオールに由来する構成単位(A)を22~49モル%と、下記一般式(2A)で表されるジオールに由来する構成単位(B)を40~75モル%と、下記一般式(3A)で表されるジオールに由来する構成単位(C)を0~15モル%と、を含む熱可塑性樹脂である。
好ましくは、Ra及びRbは、それぞれ独立して、水素原子、メチル基、エチル基、又はフェニル基を表し、Raa及びRbbは、それぞれ独立して、水素原子、又はフェニル基を表す。
上記-C≡C-RhにおけるRhは、置換基を有してもよい炭素数6~20のアリール基(好ましくは、炭素数6~12のアリール基)、又は、O、N及びSから選択される1つ以上のヘテロ環原子を含む、置換基を有してもよい炭素数6~20のヘテロアリール基(好ましくは、炭素数6~12のヘテリアリール基)を表す。
Xは、それぞれ独立に、置換基を有してもよい炭素数1~5のアルキレン基(好ましくは炭素数1~3のアルキレン基、より好ましくはエチレン基)を表す。
a及びbは、それぞれ独立に、0~10の整数を表し、好ましくは1~3の整数を表し、より好ましくは1を表す。
なお、本明細書において、「置換基を有してもよい」という場合の置換基としては、ハロゲン、シアノ基、炭素数1~20のアルキル基、または炭素数6~12のアリール基が挙げられる。
Rhは置換基を有してもよい炭素数6~20のアリール基、又は、O、N及びSから選択される1つ以上のヘテロ環原子を含む、置換基を有してもよい炭素数6~20のヘテロアリール基を表し、
Xは、それぞれ独立に、置換基を有してもよい炭素数1~5のアルキレン基を表し、
c及びdは、それぞれ独立に、0~10の整数を表す。
アズレニル、
置換されていないか、フェニル、及び、単結合によって互いに結合されていてもよく、互いに直接縮合されていてもよく、及び/又は、飽和あるいは不飽和の4~10員環の単環式あるいは二環式の炭化水素環に縮合されていてもよい、2個、3個、あるいは4個のフェニル環を有する多環式アリールからなる群から選択される、2個、3個、4個、あるいは5個の置換基によって置換されていてもよい、インデ二ル、
置換されていないフェニル、
1個あるいは2個のCN基によって置換されているフェニル、
フェニル、及び、単結合によって互いに結合されていてもよく、互いに直接縮合されていてもよく、及び/又は、飽和あるいは不飽和の4~10員環の単環式あるいは二環式の炭化水素環に縮合されていてもよい、2個、3個、あるいは4個のフェニル環を有する多環式アリールから選択される、2個、3個、4個、あるいは5個の置換基によって置換されているフェニル、
互いに直接縮合されていてもよく、及び/又は、飽和あるいは不飽和の4~10員環の単環式あるいは二環式の炭化水素環に縮合されていてもよい、2個、3個、あるいは4個のフェニル環を有する多環式アリールであって、前記多環式アリールは、置換されていないか、あるいは、フェニル、及び、2個あるいは3個のフェニル環を有する多環式アリールから選択される1個あるいは2個の置換基によって置換されていてもよく、2個あるいは3個の前記フェニル環は、単結合によって互いに結合されていてもよく、互いに直接縮合されていてもよく、及び/又は、飽和の4~10員環の単環式あるいは二環式の炭化水素環に縮合されていてもよく、多環式アリールの前記フェニル環は、置換されていないか、あるいは、1個あるいは2個の置換基Raを有する、多環式アリール、からなる群である。
置換されていないか、1個、2個、3個、4個、あるいは5個のフェニル基によって置換されていてもよい、フェニル、
1個あるいは2個のCN基によって置換されているフェニル、
ビフェニル、ナフチル、フルオレニル、アントラセニル、フェナントリル、及び、ピレニルから選択される1個あるいは2個の多環式アリール基によって置換され、及び、1個のフェニル基によってさらに置換されていてもよいフェニル、
置換されていないか、CN、フェニル、及び、ビフェニル、ナフチル、フルオレニル、アントラセニル、フェナントリル及びピレニルから選択される多環式アリールから選択される1個あるいは2個の置換基によって置換されるナフチル、
ビフェニレニル、
トリフェニレニル、
テトラフェニレニル、
フェナントリル、
ピレニル、
9H-フルオレニル、
ジベンゾ[a,e][8] アヌレニル、
ペリレニル、及び、
9,9’-スピロビ[9H-フルオレン]イルからなる群である。
ここで、Rc及びRdとは、フェニル、2-シアノフェニル、3-シアノフェニル、4-シアノフェニル、2-ナフチル、1-ナフチル、及び、9-ナフチルからなる群から選択されることが好ましい。
5あるいは6個の環原子を有するヘテロ芳香族単環基であって、1個、2個、3個、あるいは4個の窒素原子、または1個の酸素原子及び0個、1個、2個、あるいは3個の窒素原子、または1個の硫黄原子及び0個、1個、2個、あるいは3個の窒素原子を有し、他の環原子は炭素原子である、ヘテロ芳香族単環基、
ヘテロ芳香族多環基であって、前記のヘテロ芳香族単環と、フェニル及びヘテロ芳香族単環から選択される1個、2個、3個、4個、あるいは5個のさらなる芳香環を有し、多環式ヘテロアリールの(ヘテロ)芳香環は、共有結合によって互いに結合されていてもよく、互いに直接縮合されていてもよく、及び/又は、飽和あるいは不飽和の4~10員環の単環式あるいは二環式の炭化水素環に縮合されていてもよい、ヘテロ芳香族多環基、及び、
ヘテロ芳香族多環基であって、還原子として酸素、硫黄、及び、窒素から選択される1個あるいは2個のヘテロ原子を有する少なくとも1個の飽和あるいは部分的に不飽和の5あるいは6員環のヘテロ環と、フェニル及び前記のヘテロ芳香族単環から選択される1個、2個、3個、4個、あるいは5個のさらなる芳香環を有し、少なくとも1個のさらなる前記芳香環は、飽和あるいは部分的に不飽和の5あるいは6員環のヘテロ環状基に直接縮合されていて、多環ヘテロアリール芳香環の他のさらなる芳香環は、共有結合によって互いに結合されていてもよく、互いに直接縮合されていてもよく、及び/又は、飽和あるいは不飽和の4~10員環の単環式あるいは二環式の炭化水素環に縮合されていてもよい、ヘテロ芳香族多環基、からなる群である。
また、上記一般式(2A)におけるc及びdは、それぞれ独立に、好ましくは1~6の整数であり、より好ましくは1~4の整数であり、特に好ましくは2または3である。
好ましくは、Re及びRfは、それぞれ独立して、水素原子、又はフェニル基を表す。
上記-C≡C-RhにおけるRhは、置換基を有してもよい炭素数6~20のアリール基(好ましくは、炭素数6~12のアリール基)、又は、O、N及びSから選択される1つ以上のヘテロ環原子を含む、置換基を有してもよい炭素数6~20のヘテロアリール基(好ましくは、炭素数6~12のヘテリアリール基)を表す。
Xは、それぞれ独立に、置換基を有してもよい炭素数1~5のアルキレン基(好ましくは炭素数1~3のアルキレン基、より好ましくはエチレン基)を表す。
e及びfは、それぞれ独立に、0~10の整数を表し、好ましくは1~3の整数を表し、より好ましくは1を表す。
つまり、本発明の一実施形態の熱可塑性樹脂は、構成単位(A)~(C)以外にも、本発明の効果を損なわない範囲で、一般的にポリカーボネート樹脂やポリエステルカーボネート樹脂の構成単位として用いられる脂肪族ジヒドロキシ化合物から誘導される構成単位や芳香族ジヒドロキシ化合物から誘導される構成単位を含むことができる。
具体的には、脂肪族ジヒドロキシ化合物としては、様々なものが挙げられるが、特に、1,4-シクロヘキサンジメタノール、トリシクロデカンジメタノール、1,3-アダマンタンジメタノール、2,2-ビス(4-ヒドロキシシクロヘキシル)-プロパン、3,9-ビス(2-ヒドロキシ-1,1-ジメチルエチル)-2,4,8,10-テトラオキサスピロ[5.5]ウンデカン、2-(5-エチル-5-ヒドロキシメチル-1,3-ジオキサン-2-イル)-2-メチルプロパン-1-オール、イソソルビド、1,3-プロパンジオール、1,4-ブタンジオール、1,6-ヘキサンジオール等が挙げられる。
芳香族ジヒドロキシ化合物としては、様々なものを挙げることができるが、特に2,2-ビス(4-ヒドロキシフェニル)プロパン〔ビスフェノールA〕、ビス(4-ヒドロキシフェニル)メタン、1,1-ビス(4-ヒドロキシフェニル)エタン、2,2-ビス(4-ヒドロキシ-3,5-ジメチルフェニル)プロパン、4,4’-ジヒドロキシジフェニル、ビス(4-ヒドロキシフェニル)シクロアルカン、ビス(4-ヒドロキシフェニル)オキシド、ビス(4-ヒドロキシフェニル)スルフィド、ビス(4-ヒドロキシフェニル)スルホン、ビス(4-ヒドロキシフェニル)スルホキシド、及びビス(4-ヒドロキシフェニル)ケトン、ビスフェノキシエタノールフルオレン等を挙げることができる。
不純物であるフェノール系化合物などのアルコール系化合物や炭酸ジエステルは、成形体としたときの強度低下や、臭気発生の原因ともなり得るため、これらの含有量は極力少ない程好ましい。
残存するジオール成分の含有量は、ポリカーボネート樹脂100質量%に対して、好ましくは1000質量ppm以下、より好ましくは100質量ppm以下、特に好ましくは10質量ppm以下である。
残存する炭酸ジエステルの含有量は、ポリカーボネート樹脂100質量%に対して、好ましくは1000質量ppm以下、より好ましくは100質量ppm以下、特に好ましくは10質量ppm以下である。
特に、フェノール、t-ブチルフェノールなどの化合物の含有量が、少ないことが好ましく、これらの化合物が上記範囲内であることが好ましい。
ポリカーボネート樹脂中に残存するアルコール系化合物の含有量についても、ポリカーボネート樹脂から抽出したアルコール系化合物を、ガスクロマトグラフィーを用いて分析する手法により測定することができる。
ポリカーボネート樹脂中に残存するジオール成分、炭酸ジエステルの含有量も、ポリカーボネート樹脂からこれらの化合物を抽出し、ガスクロマトグラフィーを用いて分析する手法により測定することができる。
残存するアルコール系化合物の含有量は、ポリカーボネート樹脂100質量%に対して、例えば、0.01質量ppm以上、0.1質量ppm以上、又は1質量ppm以上であってもよい。
(1)屈折率(nD)
本発明の一実施形態において、熱可塑性樹脂は高屈折率であることが特徴の一つであり、屈折率は、1.650~1.695であることが好ましく、1.660~1.690であることがより好ましく、1.662~1.689であることが特に好ましい。本発明において屈折率は、後述する実施例に記載の方法で測定することができる。
本発明の一実施形態において、熱可塑性樹脂のアッベ数は、16.0~21.0であることが好ましく、16.3~20.5であることがより好ましく、16.6~20.2であることが特に好ましい。本発明においてアッベ数は、後述する実施例に記載の方法で測定することができる。
本発明の一実施形態において、熱可塑性樹脂は、高耐熱性であることが特徴の一つであり、ガラス転移温度(Tg)は、130~190℃であることが好ましく、135~180℃であることがより好ましく、140~165℃であることが特に好ましい。本発明においてガラス転移温度は、後述する実施例に記載の方法で測定することができる。
本発明の一実施形態において、熱可塑性樹脂のポリスチレン換算重量平均分子量は、10,000~100,000であることが好ましく、20,000~70,000であることがより好ましく、30,000~60,000であることが特に好ましい。
本発明の一実施形態において、熱可塑性樹脂のメルトボリュームフローレイト(MVR)は、20~55であることが好ましく、25~50であることがより好ましく、30~45であることが特に好ましい。本発明においてメルトボリュームフローレイト(MVR)は、後述する実施例に記載の方法で測定することができる。
本発明の一実施形態において、熱可塑性樹脂のヘーズは、0.01~1.00であることが好ましく、0.05~0.50であることがより好ましく、0.10~0.30であることが特に好ましい。本発明においてヘーズは、後述する実施例に記載の方法で測定することができる。
本発明の一実施形態において、熱可塑性樹脂のレンズ面内複屈折は、1~21であることが好ましく、2~15であることがより好ましく、2~13であることが特に好ましい。本発明においてレンズ面内複屈折は、後述する実施例に記載の方法で測定することができる。
本発明の別の実施形態は、上述した熱可塑性樹脂と添加剤とを含む熱可塑性樹脂組成物である。本実施形態の熱可塑性樹脂組成物は、本実施形態の所望とする効果を損なわない範囲で、上述した構成単位(A)、(B)及び(C)を含む本発明の熱可塑性樹脂以外の樹脂を併用することができる。そのような樹脂としては、特に限定されないが、例えば、ポリカーボネート樹脂、ポリエステル樹脂、ポリエステルカーボネート樹脂、(メタ)アクリル樹脂、ポリアミド樹脂、ポリスチレン樹脂、シクロオレフィン樹脂、アクリロニトリル-ブタジエン-スチレン共重合樹脂、塩化ビニル樹脂、ポリフェニレンエーテル樹脂、ポリスルホン樹脂、ポリアセタール樹脂及びメチルメタクリレート-スチレン共重合樹脂からなる群より選択される少なくとも1つの樹脂が挙げられる。これらは種々既知のものを用いることができ、1種を単独で又は2種以上を併用して熱可塑性樹脂組成物に加えることができる。
熱可塑性樹脂組成物は、上記添加剤として酸化防止剤を含むことが好ましい。
酸化防止剤として、フェノール系酸化防止剤及びホスファイト系酸化防止剤の少なくとも一方を含むことが好ましい。
フェノール系酸化防止剤として、1,3,5-トリス(3,5-ジ-tert-ブチル-4-ヒドロキシフェニルメチル)-2,4,6-トリメチルベンゼン、1,3,5-トリス(3,5-ジ-tert-ブチル-4-ヒドロキシベンジル)-1,3,5-トリアジンe-2,4,6(1H,3H,5H)-トリオン、4,4’,4’’-(1-メチルプロパニル-3-イリデン)トリス(6-tert-ブチル-m-クレゾール)、6,6’-ジ-tert-ブチル-4,4’-ブチリデンジ-m-クレゾール、オクラデシル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、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]、3,9-ビス{2-[3-(3-tert-ブチル-4-ヒドロキシ-5-メチルフェニル)プロピオニルオキシ]-1,1-ジメチルエチル}-2,4,8,10-テトラオキソスピロ[5.5]ウンデカン、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]等が挙げられ、好ましくは、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。
ホスファイト系酸化防止剤として、2-エチルヘキシルジフェニルフォスファイト、イソデシルジフェニルフォスファイト、トリイソデシルフォスファイト、トリフェニルフォスファイト、3,9-ビス(オクタデシルオキシ)-2,4,8,10-テトラオキシ-3,9-ジフォスファスピロ[5.5]ウンデカン、3,9-ビス(2,6-ジ-tert-ブチル-4-メチルフェノキシ)-2,4,8,10-テトラオキサ-3,9-ジフォスファスピロ[5.5]ウンデカン、2,2’-メチルエンビス(4,6-ジ-tert-ブチルフェニル)2-エチルヘキシルフォスファイト、トリス(2,4-ジtert-ブチルフェニル)フォスファイト、トリス(ノニルフェニル)フォスファイト、テトラ-C12-15-アルキル(プロパン-2,2-ジイルビス(4,1-フェニルエン))ビス(フォスファイト)等が挙げられ、好ましくは、3,9-ビス(2,6-ジ-tert-ブチル-4-メチルフェノキシ)-2,4,8,10-テトラオキサ-3,9-ジフォスファスピロ[5.5]ウンデカンである。
酸化防止剤として、上述のいずれか1種類のみを用いても、2種類以上の混合物を用いてもよい。
また、本発明において、フェノール系酸化防止剤及びホスファイト系酸化防止剤以外の酸化防止剤として、5,7-ジ-tert-ブチル-3-(3,4-ジメチルフェニル)-3H-ベンゾフラン-2-オンを用いてもよい。
熱可塑性樹脂組成物は、上記添加剤として離型剤を含むことが好ましい。
離型剤として、エステル化合物、例えば、グリセリン脂肪酸のモノ・ジグリセリド等のグリセリン脂肪酸エステル、プロピレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル等のグリコール脂肪酸エステル、高級アルコール脂肪酸エステル、脂肪族多価アルコールと脂肪族カルボン酸とのフルエステルあるいはモノ脂肪酸エステル等が挙げられる。離型剤として、脂肪族多価アルコールと脂肪族カルボン酸とのエステルを用いる場合、モノエステル、フルエステル等、いずれも採用できるが、例えばモノエステル等のフルエステル以外であってもよい。
離型剤の具体例として、以下のものが挙げられる。
すなわち、ソルビタン ステアレート、ソルビタン ラウレート、ソルビタン オレート、ソルビタン トリオレート、ソルビタン トリベヘネート、ソルビタン ステアレート、ソルビタン トリステアレート、ソルビタン カプリレート等のソルビタン脂肪酸エステル;
プロピレングリコール モノステアレート、プロピレングリコール モノオレート、プロピレングリコール モノベヘネート、プロピレングリコール モノラウレート、プロピレングリコール モノパルミテート等のプロピレングリコール脂肪酸エステル;
ステアリル ステアレート等の高級アルコール脂肪酸エステル;
グリセリン モノステアレート、グリセリン モノ12-ヒドロキシステアレート等のグリセリン モノヒドロキシステアレート、グリセリン モノオレート、グリセリン モノベヘネート、グリセリン モノカプリレート、グリセリン モノカプレート、グリセリン モノラウレート等のモノグリセライド:グリセリンモノ・ジステアレート、グリセリンモノ・ジステアレート、グリセリンモノ・ジベヘネート、グリセリンモノ・ジオレート等のモノ・ジグリセライド:を含む、グリセリン脂肪酸エステルモノグリセライド;
グリセリン ジアセトモノ ラウレート等のグリセリン脂肪酸エステルアセチル化モノグリセライド;
クエン酸脂肪酸 モノグリセライド、コハク酸脂肪酸 モノグリセライド、ジアセチル酒石酸脂肪酸 モノグリセライド等のグリセリン脂肪酸エステル有機酸モノグリセライド;
ジグリセリン ステアレート、ジグリセリン ラウレート、ジグリセリン オレート、ジグリセリン モノステアレート、ジグリセリン モノラウレート、ジグリセリン モノミリステート、ジグリセリン モノオレート、テトラグリセリン ステアレート、デカグリセリン ラウレート、デカグリセリン オレート、ポリグリセリン ポリリシノレート等のポリグリセリン脂肪酸エステル等が挙げられる。
これらの中でも、離型剤として、グリセリン モノステアレートが好ましい。
熱可塑性樹脂組成物には、上述の酸化防止剤及び離型剤以外にも、その他の添加剤を加えてもよい。例えば、熱可塑性樹脂組成物が含み得る添加剤として、配合剤、触媒失活剤、熱安定剤、可塑剤、充填剤、紫外線吸収剤、防錆剤、分散剤、消泡剤、レベリング剤、難燃剤、滑剤、染料、顔料、ブルーイング剤、核剤、透明化剤等が挙げられる。
熱可塑性樹脂組成物における酸化防止剤及び離型剤以外のその他の添加剤の含有量は、好ましくは10重量ppm~5.0重量%であり、より好ましくは100重量ppm~2.0重量%であり、さらに好ましくは1000重量ppm~1.0重量%であるが、これには限定されない。
上述の添加剤は、透過率に悪影響を与える可能性があり、過剰に添加しないことが好ましく、例えば、合計の添加量は上述の範囲内である。
失活剤の混練は、重合反応終了後すぐに行ってもよく、あるいは、重合後の樹脂をペレット化してから行ってもよい。また、失活剤の他、その他の添加剤も、同様の方法で添加することができる。
本発明の熱可塑性樹脂又は熱可塑性樹脂組成物(以下、単に「樹脂組成物」と略す)は、光学部材に好適に用いることができる。本発明の一実施形態において、本発明の樹脂組成物を含む光学部材が提供される。本発明の一実施形態において、光学部材には、光ディスク、透明導電性基板、光カード、シート、フィルム、光ファイバー、レンズ、プリズム、光学膜、基盤、光学フィルター、ハードコート膜等が含まれるが、これらに限定されない。本発明の樹脂組成物は、高流動でキャスト法による成形が可能であるため、特に薄型の光学部材の製造に好適である。本発明の好ましい実施形態において、本発明の樹脂組成物を用いて製造される光学部材は、光学レンズであってよい。本発明の別の好ましい実施形態において、本発明の樹脂組成物を用いて製造される光学部材は、光学フィルムであってよい。
本発明の一実施形態において、樹脂組成物は、光学レンズに好適に用いることができる。本発明の樹脂組成物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。
例えばスマートフォンのレンズでは、構成単位(A)、(B)及び(C)を含む熱可塑性樹脂から成形されたレンズと、あるいは、
上記式のいずれかのモノマーに由来する構成単位を含む樹脂から成形されたレンズとを、重ね合わせてレンズユニットとして用いることができる。
本発明の光学レンズは、金型成形、切削、研磨、レーザー加工、放電加工、エッチングなど任意の方法により成形される。この中でも、製造コストの面から金型成形がより好ましい。
本発明の一実施形態において、樹脂組成物は、光学フィルムに好適に用いることができる。特に、本発明の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、透明性及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。
光学フィルムへの異物の混入を極力避けるため、成形環境も当然低ダスト環境でなければならず、クラス6以下であることが好ましく、より好ましくはクラス5以下である。
<ポリカーボネート樹脂>
本発明の第2実施形態は、下記一般式(1B)で表される構成単位と、下記一般式(2B)で表されるビナフトール誘導体単位と、下記一般式(3B)で表されるフルオレン誘導体単位と、を含むポリカーボネート樹脂である。
Zは炭素数1~4のアルキレン基を表し、
R1~R6は、各々独立に、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のアリール基又は炭素数6~20のアリールオキシ基を表し、
e及びfは、各々独立に、0~5の整数を表す。)
本発明のポリカーボネート樹脂は、一般式(1B)で表される構成単位の割合が1モル%以上10モル%未満であり、一般式(2B)で表される構成単位の割合が10~60モル%であり、一般式(3B)で表される構成単位の割合が5~80モル%である。また、複屈折強度の絶対値が小さく、レンズ面内複屈折も小さい樹脂が得られることから、一般式(1B)で表される構成単位の割合が2~9モル%であり、一般式(2B)で表される構成単位の割合が20~60モル%であり、一般式(3B)で表される構成単位の割合が30~70モル%であることが好ましく、一般式(1B)で表される構成単位の割合が3~8モル%であり、一般式(2B)で表される構成単位の割合が30~60モル%であり、一般式(3B)で表される構成単位の割合が40~60モル%であることが特に好ましい。
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
本発明による一般式(1B)~(3B)で表される構成単位を有するポリカーボネート樹脂は、下記一般式(4B)~(6B)
Zは炭素数1~4のアルキレン基を表し、
R1~R6は、各々独立に、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のアリール基又は炭素数6~20のアリールオキシ基を表し、
e及びfは、各々独立に、0~5の整数を表す。)
で表される化合物をジヒドロキシ成分として使用し、炭酸ジエステルなどのカーボネート前駆物質と反応させて製造することができる。具体的には、一般式(4B)~(6B)で表される化合物及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もしくはその双方からなる混合触媒の存在下、又は無触媒下において、溶融重縮合法により反応させて製造することができる。
本発明の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。本発明のポリカーボネート樹脂は、成形性及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、本発明の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。
本発明の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、低アッベ数であり、複屈折強度の絶対値が小さく、レンズ面内複屈折も小さいため、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、軽量化及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。本発明により、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。
本発明の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、透明性及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。
JIS B 7071-2:2018に基づき、ポリカーボネート樹脂を成形してVブロックを得て試験片とした。23℃にて屈折率計(島津製作所製KPR-3000)を用いて屈折率を測定した。
屈折率測定で用いたものと同様の試験片(Vブロック)を用い、屈折率計を用い、23℃下での波長486nm、589nm、656nmの屈折率を測定し、下記式を用いてアッベ数を算出した。
屈折率計:島津製作所製KPR-3000
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
・試験片の成形
得られた樹脂を押し出し成形して、厚さ100μmのフィルム試験片を得た。
成形機:PULAENG-EXTRUDER
成形条件:シリンダー温度 260℃ ロール温度 Tg+10℃
・複屈折の測定:
上述のフィルム試験片を延伸して、450nmに於ける複屈折を測定した。
測定装置:JASCO Spectroellipsometer M-220
測定条件:1.5倍延伸したフィルムを用いて測定
複屈折強度は、得らえた樹脂の450nmに於ける複屈折とBPEFに由来するポリカーボネート(ホモ体)の450nmに於ける複屈折との比である。
JIS K7121-1987に基づき示差熱走査熱量分析計により、10℃/分の昇温プログラムにて測定した。
示差熱走査熱量分析計:株式会社日立ハイテクサイエンス製 X-DSC7000
得られた樹脂の重量平均分子量は、ゲル浸透クロマトグラフィー(GPC)法によって測定し、標準ポリスチレン換算で算出した。使用装置、カラム、及び測定条件は以下の通りである。
・GPC装置:東ソー(株)製、HLC-8420GPC
・カラム:東ソー(株)製、TSKgel SuperHM-M ×3本
東ソー(株)製、TSKgel guardcolumn SuperH-H ×1本
東ソー(株)製、TSKgel SuperH-RC ×1本
・検出器:RI検出器
・標準ポリスチレン:東ソー(株)製、標準ポリスチレンキット PStQuick C
・試料溶液:0.2質量%テトラヒドロフラン溶液
・溶離液:テトラヒドロフラン
・溶離液流速:0.6mL/min
・カラム温度:40℃
得られた樹脂を120℃で4時間真空乾燥し、JIS K7210に準拠して測定した。
測定装置:株式会社東洋精機製作所製 メルトインデクサーT-111
測定条件:温度260℃、荷重2160gにて測定した。
操作:シリンダー底部に設置された標準ダイから10分間あたり押し出される樹脂量からMVR(単位:cm3/10min)を算出した。
・試験片の成形
得らえた樹脂を射出成形して、直径4.5mm、中心厚0.2mmの凹型レンズ試験片を得た。
成形機:SUMITOMO SHI DEMAG SE50EV
成形条件:シリンダー温度 280℃、金型温度 Tg-15 ℃、射出速度40mm/s、VP圧70MPa(位置2.3mm), 保圧65MPax1s+55MPax1.5s
・レンズ面内復屈折の測定
上述より得られた凹型レンズ試験片のレタデーションを測定した。
測定装置:株式会社フォトニックラティス WPA-100
データ処理方法:株式会社フォトニックラティス製ソフトウェア「PA/WPA View」を用い、レタデーション平均値よりレンズ面内複屈折の値を求めた。
得られた樹脂を3mm厚に成形し、JIS K-7136に準拠して測定した。
測定機器:日本電色工業株式会社製分光ヘーズメーター SH7000
原料として、下記構造式で表される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”OPPFL”と省略する事がある)を9391.9g(15.9モル)、下記構造式で表される9,9-ビス[6-(2-ヒドロキシエトキシ)-2-ナフチル]フルオレン(以下”NOLE”と省略する事がある)を1457.7g(2.7モル)、下記構造式で表される2,2’-ビス(2-ヒドロキシエトキシ)-1,1’ -ビナフチル(以下”BNE”と省略する事がある)を5700.0g(15.2モル)、ジフェニルカーボネート(以下”DPC”と省略する事がある)を7450g(34.8モル)、及び2.5×10-2モル/リットルの炭酸水素ナトリウム水溶液12ミリリットル(3.0×10-4モル、即ち、ジヒドロキシ化合物の合計1モルに対して、10×10-6モル)を攪拌機及び留出装置付きの50リットル反応器に入れ、窒素置換を行った後、窒素雰囲気700Torrの下、1時間かけて200℃に加熱し攪拌した。加熱開始20分後に原料の完全溶解を確認し、その後同条件で80分間攪拌した。その後、20分かけて減圧度を200Torrに調整し、200℃、200Torrの条件で10分保持し、エステル交換反応を行った。さらに30分間で215℃まで昇温、180Torrまで減圧した。その後、40分かけて230℃、150Torrに調整した。その後、10分かけて120Torrに調整した。さらに10分かけて100Torr、240℃とした。その後50分かけて1Torrとし、240℃、1Torrで30分間重合を行った。反応終了後、反応器内に窒素を反応系に導入して加圧し、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、ポリカーボネート樹脂を得た。得られた樹脂の物性を表2に示す。
表1に記載の原料を用いる以外は、実施例1Aと同様にしてポリカーボネート樹脂を得た。
得られた樹脂の物性を表2に示す。
原料として、9,9-ビス(6-(2-ヒドロキシエトキシ)ナフタレン-2-イル)フルオレン(BNEF)1690g(3.14mol)、2,2’-ビス(2-ヒドロキシエトキシ)-1,1’-ビナフタレン(BNE)、6170g(16.5mol)、9,9-ビス(4-(2-ヒドロキシエトキシ)フェニル)フルオレン(BPEF)4760g(10.9mol)、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(BPPEF)8390g(14.2mol)、ジフェニルカーボネート(DPC)10000g(46.7mol)、及び2.5×10-2モル/リットルの炭酸水素ナトリウム水溶液16ml(4.0×10-4モル、即ち、ジヒドロキシ化合物の合計1モルに対して、8.9×10-6モル)を攪拌機及び留出装置付きの50Lの反応器に入れ、窒素雰囲気760mmHgの下、180℃に加熱した。加熱開始30分後に原料の完全溶解を確認し、その後、同条件で120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200℃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、2時間かけて減圧度を1mmHg以下とした。その後、60℃/hrの速度で245℃まで昇温し、さらに30分間攪拌を行った。反応終了後、反応器内に窒素を反応系に導入して加圧し、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、ポリカーボネート樹脂を得た。得られた樹脂の物性値を表3に示す。
表4に示した原料を用いる以外は、実施例1Bと同様にしてポリカーボネート樹脂を得た。得られた樹脂の物性値を表3に示す。
Claims (20)
- 樹脂中の構成単位の全量(100モル%)に対して、下記一般式(1A)で表されるジオールに由来する構成単位(A)を22~49モル%と、下記一般式(2A)で表されるジオールに由来する構成単位(B)を40~75モル%と、下記一般式(3A)で表されるジオールに由来する構成単位(C)を0~15モル%と、を含む熱可塑性樹脂。
Rhは置換基を有してもよい炭素数6~20のアリール基、又は、O、N及びSから選択される1つ以上のヘテロ環原子を含む、置換基を有してもよい炭素数6~20のヘテロアリール基を表し、
Xは、それぞれ独立に、置換基を有してもよい炭素数1~5のアルキレン基を表し、
a及びbは、それぞれ独立に、0~10の整数を表す。)
Rhは置換基を有してもよい炭素数6~20のアリール基、又は、O、N及びSから選択される1つ以上のヘテロ環原子を含む、置換基を有してもよい炭素数6~20のヘテロアリール基を表し、
Xは、それぞれ独立に、置換基を有してもよい炭素数1~5のアルキレン基を表し、
c及びdは、それぞれ独立に、0~10の整数を表す。)
Rhは置換基を有してもよい炭素数6~20のアリール基、又は、O、N及びSから選択される1つ以上のヘテロ環原子を含む、置換基を有してもよい炭素数6~20のヘテロアリール基を表し、
Xは、それぞれ独立に、置換基を有してもよい炭素数1~5のアルキレン基を表し、
e及びfは、それぞれ独立に、0~10の整数を表す。) - 樹脂中の構成単位の全量(100モル%)に対する、前記一般式(1A)で表されるジオールに由来する構成単位(A)の割合が、24~47モル%であり、前記一般式(2A)で表されるジオールに由来する構成単位(B)の割合が、45~70モル%であり、前記一般式(3A)で表されるジオールに由来する構成単位(C)の割合が、0~8モル%である、請求項1に記載の熱可塑性樹脂。
- ポリカーボネート樹脂である、請求項1から5のいずれかに記載の熱可塑性樹脂。
- 前記熱可塑性樹脂のレンズ面内複屈折が1~21である、請求項1から7のいずれかに記載の熱可塑性樹脂。
- 前記熱可塑性樹脂のポリスチレン換算の重量平均分子量(Mw)が、10,000~100,000である、請求項1から8のいずれかに記載の熱可塑性樹脂。
- 前記熱可塑性樹脂の屈折率(nD)が、1.650~1.695である、請求項1から9のいずれかに記載の熱可塑性樹脂。
- 前記熱可塑性樹脂のアッベ数(ν)が、16.0~21.0である、請求項1から10のいずれかに記載の熱可塑性樹脂。
- 前記熱可塑性樹脂のガラス転移温度が、130~190℃である、請求項1から11のいずれかに記載の熱可塑性樹脂。
- 前記熱可塑性樹脂のメルトボリュームフローレイト(MVR)が、20~55である、請求項1から12のいずれかに記載の熱可塑性樹脂。
- 前記熱可塑性樹脂のヘーズが、0.01~1.00である、請求項1から13のいずれかに記載の熱可塑性樹脂。
- 請求項1から14のいずれかに記載の熱可塑性樹脂を含む、光学部材。
- 請求項1から14のいずれかに記載の熱可塑性樹脂を含む、光学レンズ。
- 請求項1から14のいずれかに記載の熱可塑性樹脂を含む、光学フィルム。
- 下記一般式(1B)で表される構成単位と、下記一般式(2B)で表される構成単位と、下記一般式(3B)で表される構成単位と、を含むポリカーボネート樹脂であって、
下記一般式(1B)で表される構成単位の割合が1モル%以上10モル%未満であり、
下記一般式(2B)で表される構成単位の割合が10~60モル%であり、
下記一般式(3B)で表される構成単位の割合が5~80モル%である、前記ポリカーボネート樹脂。
Zは炭素数1~4のアルキレン基を表し、
R1~R6は、各々独立に、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のアリール基又は炭素数6~20のアリールオキシ基を表し、
e及びfは、各々独立に、0~5の整数を表す。) - 前記一般式(1B)で表される構成単位の割合が2~9モル%であり、
前記一般式(2B)で表される構成単位の割合が20~60モル%であり、
前記一般式(3B)で表される構成単位の割合が30~70モル%である、請求項18に記載のポリカーボネート樹脂。 - 請求項18または19に記載のポリカーボネート樹脂を含む、光学レンズ。
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