JP2010256621A - 高屈折率ポリカーボネート共重合体からなる光学レンズ - Google Patents
高屈折率ポリカーボネート共重合体からなる光学レンズ Download PDFInfo
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- JP2010256621A JP2010256621A JP2009106459A JP2009106459A JP2010256621A JP 2010256621 A JP2010256621 A JP 2010256621A JP 2009106459 A JP2009106459 A JP 2009106459A JP 2009106459 A JP2009106459 A JP 2009106459A JP 2010256621 A JP2010256621 A JP 2010256621A
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- Prior art keywords
- bis
- hydroxy
- polycarbonate copolymer
- optical lens
- methylphenyl
- Prior art date
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- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 56
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 56
- 230000003287 optical effect Effects 0.000 title claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- NUDSREQIJYWLRA-UHFFFAOYSA-N 4-[9-(4-hydroxy-3-methylphenyl)fluoren-9-yl]-2-methylphenol Chemical class C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(O)=CC=2)=C1 NUDSREQIJYWLRA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 150000002440 hydroxy compounds Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 15
- 229920005668 polycarbonate resin Polymers 0.000 claims description 13
- 239000004431 polycarbonate resin Substances 0.000 claims description 13
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 12
- IBNFPRMKLZDANU-UHFFFAOYSA-N 4-(4-hydroxy-3-methylphenyl)sulfanyl-2-methylphenol Chemical compound C1=C(O)C(C)=CC(SC=2C=C(C)C(O)=CC=2)=C1 IBNFPRMKLZDANU-UHFFFAOYSA-N 0.000 claims description 7
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 claims description 4
- 230000009477 glass transition Effects 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 24
- -1 carbonyl halide Chemical class 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 19
- 102100038367 Gremlin-1 Human genes 0.000 description 18
- 101001032872 Homo sapiens Gremlin-1 Proteins 0.000 description 18
- 208000016437 hereditary mixed polyposis syndrome Diseases 0.000 description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 150000002989 phenols Chemical class 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000006096 absorbing agent Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000012760 heat stabilizer Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000000465 moulding Methods 0.000 description 8
- SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 238000001746 injection moulding Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- VSVVZZQIUJXYQA-UHFFFAOYSA-N [3-(3-dodecylsulfanylpropanoyloxy)-2,2-bis(3-dodecylsulfanylpropanoyloxymethyl)propyl] 3-dodecylsulfanylpropanoate Chemical compound CCCCCCCCCCCCSCCC(=O)OCC(COC(=O)CCSCCCCCCCCCCCC)(COC(=O)CCSCCCCCCCCCCCC)COC(=O)CCSCCCCCCCCCCCC VSVVZZQIUJXYQA-UHFFFAOYSA-N 0.000 description 4
- 230000004075 alteration Effects 0.000 description 4
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 150000004671 saturated fatty acids Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- BBITXNWQALLODC-UHFFFAOYSA-N 2-[4-(4-oxo-3,1-benzoxazin-2-yl)phenyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C3=CC=C(C=C3)C=3OC(C4=CC=CC=C4N=3)=O)=NC2=C1 BBITXNWQALLODC-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- GWFGDXZQZYMSMJ-UHFFFAOYSA-N Octadecansaeure-heptadecylester Natural products CCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC GWFGDXZQZYMSMJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000006082 mold release agent Substances 0.000 description 3
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 3
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 3
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- UZOYICMDDCNJJG-UHFFFAOYSA-N 2-[[3-(benzotriazol-2-yl)-2-hydroxy-5-methylphenyl]methyl]-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C)=CC(CN2C(C3=C(CCCC3)C2=O)=O)=C1O UZOYICMDDCNJJG-UHFFFAOYSA-N 0.000 description 2
- XHALKWMTKWHQLO-UHFFFAOYSA-N 2-tert-butyl-4-(3-tert-butyl-4-hydroxyphenyl)sulfanylphenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(SC=2C=C(C(O)=CC=2)C(C)(C)C)=C1 XHALKWMTKWHQLO-UHFFFAOYSA-N 0.000 description 2
- DJSYZLHOGGCIPZ-UHFFFAOYSA-N 4-(4-hydroxy-3-phenylphenyl)sulfanyl-2-phenylphenol Chemical compound C1=C(C=2C=CC=CC=2)C(O)=CC=C1SC(C=1)=CC=C(O)C=1C1=CC=CC=C1 DJSYZLHOGGCIPZ-UHFFFAOYSA-N 0.000 description 2
- ICYDRUIZSPKQOH-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)decyl]phenol Chemical compound C=1C=C(O)C=CC=1C(CCCCCCCCC)C1=CC=C(O)C=C1 ICYDRUIZSPKQOH-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- 229920001651 Cyanoacrylate Polymers 0.000 description 2
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- IZMPAOFESFSUKJ-UHFFFAOYSA-N [2,4-bis(2,4-ditert-butylphenyl)-3-phenylphenyl]phosphonous acid Chemical compound CC(C)(C)C1=CC(=C(C=C1)C2=C(C(=C(C=C2)P(O)O)C3=C(C=C(C=C3)C(C)(C)C)C(C)(C)C)C4=CC=CC=C4)C(C)(C)C IZMPAOFESFSUKJ-UHFFFAOYSA-N 0.000 description 2
- OCKWAZCWKSMKNC-UHFFFAOYSA-N [3-octadecanoyloxy-2,2-bis(octadecanoyloxymethyl)propyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC OCKWAZCWKSMKNC-UHFFFAOYSA-N 0.000 description 2
- BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 238000007334 copolymerization reaction Methods 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
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- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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- 239000003960 organic solvent Substances 0.000 description 2
- PXDJXZJSCPSGGI-UHFFFAOYSA-N palmityl palmitate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 2
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- FEODVXCWZVOEIR-UHFFFAOYSA-N (2,4-ditert-butylphenyl) octyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C FEODVXCWZVOEIR-UHFFFAOYSA-N 0.000 description 1
- SXJSETSRWNDWPP-UHFFFAOYSA-N (2-hydroxy-4-phenylmethoxyphenyl)-phenylmethanone Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C(O)=CC=1OCC1=CC=CC=C1 SXJSETSRWNDWPP-UHFFFAOYSA-N 0.000 description 1
- WXENKXQUTQFQIP-PLKIVWSFSA-N (2e,4e)-hexa-2,4-dienoic acid;octadecanoic acid Chemical compound C\C=C\C=C\C(O)=O.CCCCCCCCCCCCCCCCCC(O)=O WXENKXQUTQFQIP-PLKIVWSFSA-N 0.000 description 1
- GPFJHNSSBHPYJK-UHFFFAOYSA-N (3-methylphenyl) hydrogen carbonate Chemical compound CC1=CC=CC(OC(O)=O)=C1 GPFJHNSSBHPYJK-UHFFFAOYSA-N 0.000 description 1
- FUAMQXCTIUGPJK-UHFFFAOYSA-N (5-benzoyl-4-hydroxy-2-methoxyphenyl) hydrogen sulfate Chemical compound C1=C(OS(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 FUAMQXCTIUGPJK-UHFFFAOYSA-N 0.000 description 1
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- 239000008346 aqueous phase Substances 0.000 description 1
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- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
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- AXRSHKZFNKUGQB-UHFFFAOYSA-N octyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC)OC1=CC=CC=C1 AXRSHKZFNKUGQB-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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Abstract
Description
また、他の単官能フェノール類としては、長鎖のアルキル基或いは脂肪族エステル基を置換基として有するフェノール類または安息香酸クロライド類、もしくは長鎖のアルキルカルボン酸クロライド類を使用することができ、これらを用いて芳香族ポリカーボネート共重合体の末端を封鎖すると、これらは末端停止剤または分子量調節剤として機能するのみならず、樹脂の溶融流動性が改良され、成形加工が容易となるばかりでなく、物性も改良される。これらは下記一般式[I−a]〜[I−h]で表される。
Qはハロゲン原子または炭素数1〜10、好ましくは1〜5の一価の脂肪族炭化水素基を示し、pは0〜4の整数を示し、Yは炭素数1〜10、好ましくは1〜5の二価の脂肪族炭化水素基を示し、W1は水素原子、−CO−R17、−CO−O−R18またはR19である、ここでR17、R18およびR19は、それぞれ炭素数1〜10、好ましくは1〜5の一価の脂肪族炭化水素基、炭素数4〜8、好ましくは5〜6の一価の脂環族炭化水素基または炭素数6〜15、好ましくは6〜12の一価の芳香族炭化水素基を示す。
aは4〜20、好ましくは5〜10の整数を示し、mは1〜100、好ましくは3〜60 、特に好ましくは4〜50の整数を示し、Zは単結合または炭素数1〜10、好ましくは1〜5の二価の脂肪族炭化水素基を示し、W2は水素原子、炭素数1〜10、好ましくは1〜5の一価の脂肪族炭化水素基、炭素数4〜8、好ましくは5〜6の一価の脂環族炭化水素基または炭素数6〜15、好ましくは6〜12の一価の芳香族炭化水素基を示す。]
本発明のポリカーボネート共重合体から形成された光学レンズには、本発明の目的を損なわない範囲で各種特性を付与する為に、各種添加剤を使用することができる。添加剤としては離型剤、熱安定剤、紫外線吸収剤、ブルーイング剤、帯電防止剤、難燃剤、熱線遮蔽剤、蛍光染料(蛍光増白剤含む)、顔料、光拡散剤、強化充填剤、他の樹脂やエラストマー等を配合することができる。
ブルーイング剤の配合量は、ポリカーボネート共重合体粉粒体に対して好ましくは0.05〜1.5ppmであり、より好ましくは0.1〜1.2ppmである。
(1)比粘度:ポリマー0.7gを塩化メチレン100mlに溶解し20℃の温度で測定した。
(2)共重合比:ポリマー10mgを重クロロホルム0.6mlに溶解し、日本電子社製JNM−AL400のプロトンNMRを用いて、積算回数128回で測定した。共重合比は9,9−ビス(4−ヒドロキシ−3−メチルフェニル)フルオレンのメチル基に起因するピーク(2.1〜2.ppm)及びビス(4−ヒドロキシ−3−メチルフェニル)スルフィドのメチル基に起因するピーク(2.2〜2.3ppm)の積分比から求めた。
(3)ガラス転移点(Tg):デュポン社製910型DSC により測定した。
(4)屈折率(nd):ATAGO製DR−M2のアッベ屈折計を用いて測定した。
(5)光学歪み:成形したレンズを二枚の偏光板の間に挟み直行ニコル法で後ろからの光漏れを目視することにより評価した。
(6)全光線透過率:1mm厚の成形片を日本電色(株)製MDH−300Aを用いて測定した。
温度計、撹拌機、還流冷却器付き反応器にイオン交換水309.15重量部、25%水酸化ナトリウム水溶液103.05重量部を入れ、9,9−ビス(4−ヒドロキシ−3−メチルフェニル)フルオレン(以下“ビスクレゾールフルオレン”または“BCF”と略称することがある)40.57重量部、ビス(4−ヒドロキシ−3−メチルフェニル)スルフィド(以下“HMPS”と略称することがある)26.41重量部、ハイドロサルファイト0.37重量部を溶解した後、イオン交換水20.64重量部、48%水酸化ナトリウム水溶液14.17重量部、塩化メチレン237.23重量部を加え、撹拌下15〜25℃でホスゲン27.63重量部を60分要して吹き込んだ。ホスゲン吹き込み終了後、p−tert−ブチルフェノール1.13重量部を塩化メチレン3重量部に溶解した溶液および25%水酸化ナトリウム水溶液17.17重量部を加え、乳化後、トリエチルアミン0.12重量部を加えて28〜33℃で1時間撹拌して反応を終了した。反応終了後、生成物を塩化メチレンで希釈して水洗したのち塩酸酸性にして水洗し、水相の導電率がイオン交換水と殆ど同じになったところで、この溶液から溶媒を除去しポリマーを得た。このポリカーボネートはBCFとHMPSとの構成単位の比がモル比で50:50であり、比粘度は0.34、Tgは154℃であった。
EX−PC1のBCFの使用量を34.08重量部、HMPSの使用量を30.63重量部とする以外はEX−PC1と同様にしてポリマーを得た。このポリカーボネートはBCFとHMPSの構成単位の比がモル比で42:58であり、比粘度は0.36、Tgは144℃であった。
EX−PC1のBCFの使用量を40.57重量部、HMPSの使用量を21.13重量部、1,1−ビス(4−ヒドロキシフェニル)デカン(以下、“DED”と省略することがある)の使用量を7.08重量部とする以外はEX−PC1と同様にしてポリマーを得た。このポリカーボネートはBCFとHMPSとDEDの構成単位の比がモル比で50:40:10であり、比粘度は0.34、Tgは151℃であった。
EX−PC1のBCFの使用量を28.40重量部、HMPSをビス(4−ヒドロキシフェニル)スルフィド(以下“TDP”と省略することがある)に変更し、TDPの使用量を30.42重量部とする以外はEX−PC1と同様にしてポリマーを得た。このポリカーボネートはBCFとTDPの構成単位の比がモル比で35:65であり、比粘度は0.27、Tgは143℃であった。
実施例1のBCFの使用量を48.69重量部、HMPSの使用量を36.97重量部とする以外はEX−PC1と同様にしてポリマーを得た。このポリカーボネートはBCFとHMPSの構成単位の比がモル比で60:40であり、比粘度は0.25、Tgは168℃であった。
実施例1のBCFの使用量を16.23重量部、HMPSの使用量を42.25重量部とする以外はEX−PC1と同様にしてポリマーを得た。このポリカーボネートはBCFとHMPSの構成単位の比がモル比で20:80であり、比粘度は0.29、Tgは120℃であった。
EX−PC1のBCFの使用量を56.80重量部、HMPSの使用量を15.84重量部とする以外はEX−PC1と同様にしてポリマーを得た。このポリカーボネートはBCFとHMPSの比がモル比で70:30であり、比粘度は0.28、Tgは181℃であった。
EX−PC1のBCFの使用量を8.11重量部、HMPSの使用量を47.53重量部とする以外はEX−PC1と同様にしてポリマーを得た。このポリカーボネートはBCFとHMPSの比がモル比で10:90であり、比粘度は0.35、Tgは110℃であった。
EX−PC1のBCFの使用量を16.23重量部、HMPSをビスフェノールA(以下“BPA”と省略することがある)に変更し、BPAの使用量を39.16重量部とする以外はEX−PC1と同様にしてポリマーを得た。このポリカーボネートはBCFとBPAの比がモル比で20:80であり、比粘度は0.28、Tgは160℃であった。
EX−PC1のBCFを9,9−ビス(4−ヒドロキシフェニル)フルオレン(以下“ビスフェノールフルオレン”または“BPFL”と略称することがある)の使用量を52.60重量部、HMPSをBPAに変更し、BPAの使用量を14.69重量部とする以外はEX−PC1と同様にしてポリマーを得た。このポリカーボネートはBPFLとBPAの比がモル比で70:30であり、比粘度は0.28、Tgは220℃であった。
作成したポリカーボネート共重合体を100℃で24時間真空乾燥した後、ビス(2,4−ジクミルフェニル)ペンタエリスリトールジホスファイト0.050%、ペンタエリスリトールテトラステアレートを0.10%加えて、ベント付きφ30mm単軸押出機を用いて、ペレット化した後、住友重機械(株)製SE30DU射出成形機を用いて、下記成形条件にて、厚さ0.3mm、凸面曲率半径5mm、凹面曲率半径4mm、φ5mmのレンズを成形した。上記レンズを二枚の偏光板の間に挟み直行ニコル法で後ろからの光漏れを目視することにより評価した。評価は、○:殆ど光漏れがない、×:光漏れが顕著であるとした。また、上記成形片を用いて全光線透過率を測定した。結果を表1に示す。
Claims (7)
- 屈折率が1.61〜1.65、且つガラス転移温度が115℃〜170℃である請求項1に記載のポリカーボネート共重合体からなる光学レンズ。
- 該ポリカーボネート樹脂はそのポリマー0.7gを100mlの塩化メチレンに溶解し、20℃で測定した比粘度が0.12〜0.55である請求項1〜2のいずれか1項に記載のポリカーボネート共重合体からなる光学レンズ。
- 全ヒドロキシ化合物の少なくとも80モル%が9,9−ビス(4−ヒドロキシ−3−メチルフェニル)フルオレン及び式(1)で表されるジヒドロキシ化合物であり、且つ9,9−ビス(4−ヒドロキシ−3−メチルフェニル)フルオレンと及び式(1)で表されるジヒドロキシ化合物の割合がモル比で60:40〜20:80の範囲で構成された請求項1〜3のいずれか1項に記載のポリカーボネート共重合体からなる光学レンズ。
- 全ヒドロキシ化合物の少なくとも80モル%が9,9−ビス(4−ヒドロキシ−3−メチルフェニル)フルオレン及び式(1)で表されるジヒドロキシ化合物であり、且つ9,9−ビス(4−ヒドロキシ−3−メチルフェニル)フルオレンと及び式(1)で表されるジヒドロキシ化合物の割合がモル比で55:45〜25:75の範囲で構成された請求項1〜4のいずれか1項に記載のポリカーボネート共重合体からなる光学レンズ。
- 式(1)で表されるジヒドロキシ化合物がビス(4−ヒドロキシ−3−メチルフェニル)スルフィドである請求項1〜5のいずれか1項に記載のポリカーボネート共重合体からなる光学レンズ。
- 式(1)で表されるジヒドロキシ化合物がビス(4−ヒドロキシフェニル)スルフィドである請求項1〜5のいずれか1項に記載のポリカーボネート共重合体からなる光学レンズ。
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US9127119B2 (en) | 2013-01-11 | 2015-09-08 | Sabic Global Technologies B.V. | Polycarbonate compositions having improved thermal dimensional stability and high refractive index |
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