TW202208500A - 化合物、樹脂、聚碳酸酯樹脂及光學成形體 - Google Patents
化合物、樹脂、聚碳酸酯樹脂及光學成形體 Download PDFInfo
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- TW202208500A TW202208500A TW110127768A TW110127768A TW202208500A TW 202208500 A TW202208500 A TW 202208500A TW 110127768 A TW110127768 A TW 110127768A TW 110127768 A TW110127768 A TW 110127768A TW 202208500 A TW202208500 A TW 202208500A
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- fluorene
- polycarbonate resin
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 67
- 239000004431 polycarbonate resin Substances 0.000 title claims description 88
- 229920005668 polycarbonate resin Polymers 0.000 title claims description 88
- 230000003287 optical effect Effects 0.000 title claims description 45
- 229920005989 resin Polymers 0.000 title claims description 35
- 239000011347 resin Substances 0.000 title claims description 35
- 238000000465 moulding Methods 0.000 title description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000005647 linker group Chemical group 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 18
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 239000012788 optical film Substances 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- -1 9,9-bis(1'- Hydroxymethyl)-2,7-bis[4-(naphthalen-2-yl)phenyl]-9H-fluorene Chemical compound 0.000 description 30
- 238000000034 method Methods 0.000 description 27
- 239000012153 distilled water Substances 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- 150000002430 hydrocarbons Chemical group 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 238000004128 high performance liquid chromatography Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000006096 absorbing agent Substances 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 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 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
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- 230000006837 decompression Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000006068 polycondensation reaction Methods 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000001746 injection moulding Methods 0.000 description 7
- 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 7
- 150000003839 salts Chemical class 0.000 description 7
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
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- 239000000463 material Substances 0.000 description 6
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- 239000013076 target substance Substances 0.000 description 6
- NQXNYVAALXGLQT-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1(C=2C=CC(OCCO)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 NQXNYVAALXGLQT-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000004650 carbonic acid diesters Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000006082 mold release agent Substances 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 150000004671 saturated fatty acids Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
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- 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 4
- AVXFJPFSWLMKSG-UHFFFAOYSA-N 2,7-dibromo-9h-fluorene Chemical compound BrC1=CC=C2C3=CC=C(Br)C=C3CC2=C1 AVXFJPFSWLMKSG-UHFFFAOYSA-N 0.000 description 3
- GCUOLJOTJRUDIZ-UHFFFAOYSA-N 2-(2-bromoethoxy)oxane Chemical compound BrCCOC1CCCCO1 GCUOLJOTJRUDIZ-UHFFFAOYSA-N 0.000 description 3
- BYVYQBCQUOLMSE-UHFFFAOYSA-N 2-[9-(2-hydroxyethyl)-2,7-bis(3-naphthalen-2-ylphenyl)fluoren-9-yl]ethanol Chemical compound OCCC(CCO)(C1=C2)C(C=C(C=C3)C4=CC(C5=CC6=CC=CC=C6C=C5)=CC=C4)=C3C1=CC=C2C1=CC(C2=CC3=CC=CC=C3C=C2)=CC=C1 BYVYQBCQUOLMSE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 230000004075 alteration Effects 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
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- 229920002223 polystyrene Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 2
- LXSAALCCSMKXOE-UHFFFAOYSA-N 2-[2,7-dibromo-9-(2-hydroxyethyl)fluoren-9-yl]ethanol Chemical compound C1=C(Br)C=C2C(CCO)(CCO)C3=CC(Br)=CC=C3C2=C1 LXSAALCCSMKXOE-UHFFFAOYSA-N 0.000 description 2
- YEUSOKGOVHMKHM-UHFFFAOYSA-N 2-[9-(2-hydroxyethyl)-2,7-bis(4-naphthalen-2-ylphenyl)fluoren-9-yl]ethanol Chemical compound OCCC(CCO)(C1=C2)C(C=C(C=C3)C(C=C4)=CC=C4C4=CC5=CC=CC=C5C=C4)=C3C1=CC=C2C(C=C1)=CC=C1C1=CC2=CC=CC=C2C=C1 YEUSOKGOVHMKHM-UHFFFAOYSA-N 0.000 description 2
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920001651 Cyanoacrylate Polymers 0.000 description 2
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 229910052775 Thulium Inorganic materials 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 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 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 235000010338 boric acid Nutrition 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
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- 238000005266 casting Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- VZEGPPPCKHRYGO-UHFFFAOYSA-N diethoxyphosphorylbenzene Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1 VZEGPPPCKHRYGO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 239000012467 final product Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
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- 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
- KCRLWVVFAVLSAP-UHFFFAOYSA-N octyl dihydrogen phosphite Chemical compound CCCCCCCCOP(O)O KCRLWVVFAVLSAP-UHFFFAOYSA-N 0.000 description 2
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- ULBTUVJTXULMLP-UHFFFAOYSA-N butyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCC ULBTUVJTXULMLP-UHFFFAOYSA-N 0.000 description 1
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- 125000005587 carbonate group Chemical group 0.000 description 1
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- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- BLUMOBPWAAOPOY-UHFFFAOYSA-M cesium;benzoate Chemical compound [Cs+].[O-]C(=O)C1=CC=CC=C1 BLUMOBPWAAOPOY-UHFFFAOYSA-M 0.000 description 1
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- NFJPGAKRJKLOJK-UHFFFAOYSA-N chembl1901631 Chemical compound CCCCOP(=O)OCCCC NFJPGAKRJKLOJK-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 239000011247 coating layer Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
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- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
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- TWLCPLJMACDPFF-UHFFFAOYSA-N cyclohexane;1,2-diisocyanatoethane Chemical compound C1CCCCC1.O=C=NCCN=C=O TWLCPLJMACDPFF-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
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- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- GLOQRSIADGSLRX-UHFFFAOYSA-N decyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCC)OC1=CC=CC=C1 GLOQRSIADGSLRX-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- OSPSWZSRKYCQPF-UHFFFAOYSA-N dibutoxy(oxo)phosphanium Chemical compound CCCCO[P+](=O)OCCCC OSPSWZSRKYCQPF-UHFFFAOYSA-N 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 1
- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- XFUSKHPBJXJFRA-UHFFFAOYSA-N dihexyl hydrogen phosphite Chemical compound CCCCCCOP(O)OCCCCCC XFUSKHPBJXJFRA-UHFFFAOYSA-N 0.000 description 1
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- REKWWOFUJAJBCL-UHFFFAOYSA-L dilithium;hydrogen phosphate Chemical compound [Li+].[Li+].OP([O-])([O-])=O REKWWOFUJAJBCL-UHFFFAOYSA-L 0.000 description 1
- OXDOANYFRLHSML-UHFFFAOYSA-N dimethoxyphosphorylbenzene Chemical compound COP(=O)(OC)C1=CC=CC=C1 OXDOANYFRLHSML-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- XMQYIPNJVLNWOE-UHFFFAOYSA-N dioctyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OCCCCCCCC XMQYIPNJVLNWOE-UHFFFAOYSA-N 0.000 description 1
- MKZVQIIAAIPNGH-UHFFFAOYSA-N dioctyl phenyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OC1=CC=CC=C1 MKZVQIIAAIPNGH-UHFFFAOYSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- PXGLYSITKOROKV-UHFFFAOYSA-N dipropoxyphosphorylbenzene Chemical compound CCCOP(=O)(OCCC)C1=CC=CC=C1 PXGLYSITKOROKV-UHFFFAOYSA-N 0.000 description 1
- CSVGEMRSDNSWRF-UHFFFAOYSA-L disodium;dihydrogen phosphate Chemical compound [Na+].[Na+].OP(O)([O-])=O.OP(O)([O-])=O CSVGEMRSDNSWRF-UHFFFAOYSA-L 0.000 description 1
- TYJOJLOWRIQYQM-UHFFFAOYSA-L disodium;phenyl phosphate Chemical compound [Na+].[Na+].[O-]P([O-])(=O)OC1=CC=CC=C1 TYJOJLOWRIQYQM-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- ANCBHJKEYPZCTE-UHFFFAOYSA-N ethyl 5-carbamoyl-4-methyl-2-[(2,3,4,5,6-pentafluorobenzoyl)amino]thiophene-3-carboxylate Chemical compound CC1=C(C(N)=O)SC(NC(=O)C=2C(=C(F)C(F)=C(F)C=2F)F)=C1C(=O)OCC ANCBHJKEYPZCTE-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
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- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- KYYWBEYKBLQSFW-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCC(O)=O KYYWBEYKBLQSFW-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- IVQOVYWBHRSGJI-UHFFFAOYSA-N hexyl 4-methylbenzenesulfonate Chemical compound CCCCCCOS(=O)(=O)C1=CC=C(C)C=C1 IVQOVYWBHRSGJI-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000005027 hydroxyaryl group Chemical group 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
- 230000000415 inactivating effect Effects 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 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
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- 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
- 239000000314 lubricant Substances 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
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- 239000011654 magnesium acetate Substances 0.000 description 1
- 229940069446 magnesium acetate Drugs 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
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 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
- 239000008204 material by function Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-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
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-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
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 1
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- CHJUOCDSZWMLRU-UHFFFAOYSA-N oxo(dipropoxy)phosphanium Chemical compound CCCO[P+](=O)OCCC CHJUOCDSZWMLRU-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- LYTNHSCLZRMKON-UHFFFAOYSA-L oxygen(2-);zirconium(4+);diacetate Chemical compound [O-2].[Zr+4].CC([O-])=O.CC([O-])=O LYTNHSCLZRMKON-UHFFFAOYSA-L 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- VCAFTIGPOYBOIC-UHFFFAOYSA-N phenyl dihydrogen phosphite Chemical compound OP(O)OC1=CC=CC=C1 VCAFTIGPOYBOIC-UHFFFAOYSA-N 0.000 description 1
- SMIZARYCGYRDGF-UHFFFAOYSA-N phenyl dipropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC1=CC=CC=C1 SMIZARYCGYRDGF-UHFFFAOYSA-N 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 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
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 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
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 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
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 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
- 229940093625 propylene glycol monostearate Drugs 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000005728 strengthening Methods 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
- 239000001384 succinic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical class CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-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
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 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
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- AJHKJOCIGPIJFZ-UHFFFAOYSA-N tris(2,6-ditert-butylphenyl) phosphite Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1OP(OC=1C(=CC=CC=1C(C)(C)C)C(C)(C)C)OC1=C(C(C)(C)C)C=CC=C1C(C)(C)C AJHKJOCIGPIJFZ-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 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
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C33/36—Polyhydroxylic alcohols containing six-membered aromatic rings and other rings
-
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- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
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- C08G64/307—General preparatory processes using carbonates and phenols
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
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Abstract
Description
本發明是有關於一種化合物、由該化合物獲得的樹脂及聚碳酸酯樹脂、以及包含該樹脂及聚碳酸酯樹脂的光學成形體。
作為照相機、膜一體型照相機、攝像機等各種照相機的光學系統中所使用的光學透鏡的材料,使用光學玻璃或光學用樹脂。光學玻璃的耐熱性、透明性、尺寸穩定性、耐化學品性等優異,存在具有各種折射率或阿貝數的多種材料。但是,具有材料成本高、成形加工性差、生產性低的問題點。
另一方面,包含光學用樹脂的光學透鏡具有可藉由射出成形進行大量生產的優點。例如於照相機用透鏡中,使用聚碳酸酯樹脂等。然而,近年來由於製品的輕薄短小化,要求開發折射率高的樹脂。一般而言,若光學材料的折射率高,則可以曲率更小的面實現具有相同折射率的透鏡元件,因此可減小於該面上產生的像差量。結果,可減少透鏡的枚數、降低透鏡的離心感度、使透鏡厚度變薄來實現輕量化。
作為與光學用樹脂相關的技術,例如可列舉專利文獻1及專利文獻2中記載者。
專利文獻1(日本專利特開2005-241962號公報)中記載一種包含具有芴結構的聚碳酸酯樹脂的光學透鏡。
專利文獻2(日本專利特開2005-187661號公報)中記載一種藉由向含芴聚酯中摻合(混合、添加)含硫化合物來簡便地提高折射率的方法。
[現有技術文獻]
[專利文獻]
[專利文獻1]日本專利特開2005-241962號公報
[專利文獻2]日本專利特開2005-187661號公報
[發明所欲解決之課題]
但是,如專利文獻1所記載般的聚碳酸酯樹脂的折射率低,並不充分滿足。
另外,如專利文獻2記載般,向含芴聚酯中摻合含硫化合物時折射率提高,但由於添加低分子量成分,因此熱穩定性降低,於摻合的二成分的相容性差的情況下,透明性降低。
本發明是鑒於所述情況而成者,提供一種可實現高折射率且透明性優異的光學成形體的樹脂及聚碳酸酯樹脂。
[解決課題之手段]
本發明者等人為了提供可實現高折射率且透明性優異的光學成形體的聚碳酸酯樹脂而進行了努力研究。結果發現,將下述式(1)所表示的化合物聚合而獲得的樹脂可實現高折射率且透明性優異的光學成形體,從而完成了本發明。
根據本發明,提供以下的通式(1)所表示的化合物、由該化合物獲得的樹脂、自該化合物衍生的聚碳酸酯樹脂、及光學成形體。
[1]一種化合物,其由通式(1)表示。
[化1]
(通式(1)中,Ar1
及Ar2
獨立地表示選自
[化2]
中的基,R1
~R6
表示氫原子、烴基或含雜原子的烴基,A1
~A5
及B1
~B5
表示氫原子、烴基或含雜原子的烴基,A1
~A5
中的至少一個為-Y1
-Ar3
基,B1
~B5
中的至少一個為-Y2
-Ar4
基,Y1
及Y2
表示單鍵或連結基,Ar3
及Ar4
表示芳香族基,X1
~X4
為-O-、-S-、-NR'-、或-C(Me)2
-,Z1
~Z4
表示氫原子、烴基或含雜原子的烴基,R'表示氫原子、烴基或含雜原子的烴基,o及p表示1~4的整數)。
[2]如所述[1]所述的化合物,其中所述通式(1)中的o及p為2。
[3]如所述[1]或[2]所述的化合物,其中所述通式(1)中的Ar1
及Ar2
獨立地表示選自
[化3]
中的基,R1
~R6
表示氫原子、烴基或含雜原子的烴基,o及p表示1~4的整數。
[4]一種樹脂,其是將如所述[1]至[3]中任一項所述的通式(1)所表示的化合物聚合而成。
[5]一種聚碳酸酯樹脂,其是自如所述[1]至[3]中任一項所述的通式(1)所表示的化合物衍生。
[6]一種光學成形體,其包含如所述[4]或[5]所述的樹脂。
[7]如所述[6]所述的光學成形體,其為光學透鏡。
[8]如所述[6]所述的光學成形體,其為光學膜。
[發明的效果]
根據本發明,可提供可實現高折射率且透明性優異的光學成形體的樹脂及聚碳酸酯樹脂。
以下,對本發明的實施形態進行說明。再者,文中的位於數字之間的「~」只要無特別說明,則表示以上至以下。
[化5]
中的基,
R1
~R6
表示氫原子、烴基或含雜原子的烴基,
A1
~A5
及B1
~B5
表示氫原子、烴基或含雜原子的烴基,A1
~A5
中的至少一個為-Y1
-Ar3
基,
B1
~B5
中的至少一個為-Y2
-Ar4
基,
Y1
及Y2
表示單鍵或連結基,Ar3
及Ar4
表示芳香族基,X1
~X4
為-O-、-S-、-NR'-、或-C(Me)2
-,
Z1
~Z4
表示氫原子、烴基或含雜原子的烴基,
R'表示氫原子、烴基或含雜原子的烴基,
o及p表示1~4的整數。
通式(1)中,R1
~R6
較佳為分別獨立地選自氫原子及碳數1~3的烷基或碳數6~20的芳基中,R1
~R6
更佳為分別獨立地選自氫原子、甲基、苯基、聯苯基、萘基中,R1
~R6
進而佳為氫原子。
通式(1)中,o及p為1~4的整數,較佳為1或2,更佳為2。藉由o及p為所述範圍,由通式(1)的化合物獲得的聚碳酸酯樹脂具有優異的耐熱性。
作為通式(1)中的Ar1
及Ar2
的較佳的態樣,可列舉以下。
作為所述通式(1)所表示的化合物,例如可列舉:9,9-雙(1'-羥基甲基)-2,7-二萘-2''-基-9H-芴、9,9-雙(1'-羥基甲基)-2,7-二萘-1''-基-9H-芴、9,9-雙(1'-羥基甲基)-3,6-二萘-2''-基-9H-芴、9,9-雙(1'-羥基甲基)-3,6-二萘-1''-基-9H-芴、9,9-雙(1'-羥基甲基)-2,7-二-對聯苯-9H-芴、9,9-雙(1'-羥基甲基)-2,7-二-間聯苯-9H-芴、9,9-雙(1'-羥基甲基)-2,7-雙(3'',5''-二苯基苯基)-9H-芴、9,9-雙(1'-羥基甲基)-2,7-雙〔二苯並[b,d]呋喃-4''-基〕-9H-芴、9,9-雙(1'-羥基甲基)-2,7-雙〔二苯並[b,d]噻吩-4''-基〕-9H-芴、9,9-雙(1'-羥基甲基)-2,7-雙(4''-苯氧基苯基)-9H-芴、9,9-雙(1'-羥基甲基)-2,7-雙(4''-苯基萘-1''-基)-9H-芴、9,9-雙(1'-羥基甲基)-2,7-雙〔4-(萘-2-基)苯基〕-9H-芴、9,9-雙(1'-羥基甲基)-2,7-雙〔3-(萘-2-基)苯基〕-9H-芴、9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴、9,9-雙(2'-羥基乙基)-2,7-二萘-1''-基-9H-芴、9,9-雙(2'-羥基乙基)-3,6-二萘-2''-基-9H-芴、9,9-雙(2'-羥基乙基)-3,6-二萘-1''-基-9H-萘、9,9-雙(2'-羥基乙基)-2,7-二-對聯苯-9H-芴、9,9-雙(2'-羥基乙基)-2,7-二-間聯苯-9H-芴、9,9-雙(2'-羥基乙基)-2,7-二-鄰聯苯-9H-芴、9,9-雙(2'-羥基乙基)-2,7-雙(3'',5''-二苯基苯基)-9H-芴、9,9-雙(2'-羥基乙基)-2,7-雙〔二苯並[b,d]呋喃-4''-基〕-9H-芴、9,9-雙(2'-羥基乙基)-2,7-雙〔二苯並[b,d]噻吩-4''-基〕-9H-芴、9,9-雙(2'-羥基乙基)-2,7-雙(4''-苯氧基苯基)-9H-芴、9,9-雙(2'-羥基乙基)-2,7-雙(3'',5''-二苯氧基苯基)-9H-芴、9,9-雙(2'-羥基乙基)-2,7-雙(4''-苯基萘-1''-基)-9H-芴、9,9-雙(2'-羥基乙基)-2,7-雙〔4-(萘-2-基)苯基〕-9H-芴、9,9-雙(2'-羥基乙基)-2,7-雙〔3-(萘-2-基)苯基〕-9H-芴、9,9-雙(2'-羥基乙基)-2,7-雙〔3-(萘-1-基)苯基〕-9H-芴、9,9-雙(2'-羥基乙基)-2,7-雙〔4-(萘-1-基)苯基〕-9H-芴、9,9-雙(2'-羥基乙基)-2,7-二菲基-9''-基-9H-芴、9,9-雙(2'-羥基乙基)-2,7-雙〔9'',9''-二甲基-9''-芴-2''-基〕-9H-芴、9,9-雙(3'-羥基丙基)-2,7-二萘-2''-基-9H-芴、9,9-雙(3'-羥基丙基)-2,7-二萘-1''-基-9H-芴、9,9-雙(3'-羥基丙基)-3,6-二萘-2''-基-9H-芴、9,9-雙(3'-羥基丙基)-3,6-二萘-1''-基-9H-萘、9,9-雙(4'-羥基丁基)-2,7-二萘-2''-基-9H-芴、9,9-雙(4'-羥基丁基)-2,7-二萘-1''-基-9H-芴、9,9-雙(4'-羥基丁基)-3,6-二萘-2''-基-9H-芴、9,9-雙(4'-羥基丁基)-3,6-二萘-1''-基-9H-萘、9,9-雙(4'-羥基丁基)-3,6-雙〔4-(萘-2-基)苯基〕-9H-芴等。
該些中,較佳為可列舉9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴、9,9-雙(2'-羥基乙基)-2,7-二萘-1''-基-9H-芴。該些可單獨使用,或者亦可將兩種以上組合而使用。
[通式(1)所表示的化合物的製造方法]
本實施形態的通式(1)所表示的化合物可藉由以下的步驟(i)及步驟(ii)合成。
步驟(i):於溶媒(例如,四氫呋喃、1,4-二噁烷、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、二甲基亞碸、環丁碸)中,利用鹼(例如,氫氧化鈉、氫氧化鉀、碳酸鈉、碳酸鉀、氫化鈉、氫化鉀、甲氧基鈉、乙氧基鈉、第三丁氧基鈉、第三丁氧基鉀、正丁基鋰)對2,7-二溴-9H-芴或3,6-二溴-9H-芴等二鹵代-9H-芴進行處理,藉此抽出二鹵代-9H-芴的9位的氫,之後使具有脫離基的羥基烷基(此處作為脫離基,可列舉:氯、溴、碘等鹵素、對甲苯磺醯氧基、甲基磺醯氧基、三氟甲基磺醯氧基等)發揮作用,從而製造9,9-雙(羥基烷基)-2,7-二溴-9H-芴或9,9-雙(羥基烷基)-3,6-9H-芴等9,9-雙(羥基烷基)-二鹵代-9H-芴。
步驟(ii):於步驟(i)中獲得的9,9-雙(羥基烷基)-2,7-二溴-9H-芴或9,9-雙(羥基烷基)-3,6-9H-芴等9,9-雙(羥基烷基)-二鹵代-9H-芴中,於溶媒(例如,甲苯及水、四氫呋喃及水、二甲基亞碸及水)中、鹼(例如,碳酸鈉、碳酸鉀、乙酸鈉、乙酸鉀、磷酸鈉、磷酸鉀)及四(三苯基膦)鈀等鈀系觸媒的存在下,使萘基硼酸發生作用,根據所謂的鈴木-宮浦偶合的條件來製造目標通式(1)的化合物。
此處,步驟(i)的反應可藉由-78℃至溶媒的沸點之間的任意溫度實施。另外,反應條件可適用一般的烷基化反應的條件。根據需要,亦可利用任意的保護基(例如,乙醯基等酯基、四氫吡喃基等醚基、第三丁氧基羰基等碳酸酯基)保護具有脫離基的羥基烷基的羥基,最後進行脫保護。
步驟(ii)的反應可藉由室溫至溶媒的沸點為止的任意溫度實施。反應條件可適用所謂的鈴木-宮浦偶合中一般所使用的反應條件。
[樹脂]
本發明的一態樣為將通式(1)所表示的化合物聚合而成的樹脂。
此處,作為將通式(1)所表示的化合物聚合而獲得的樹脂,可列舉:聚酯樹脂、聚胺基甲酸酯樹脂、聚碳酸酯樹脂、聚醚樹脂等。
聚酯樹脂藉由使通式(1)所表示的化合物、與芳香族二羧酸(例如,對苯二甲酸、間苯二甲酸、2,6-萘二羧酸)、或脂肪族二羧酸(例如,乙二酸、丙二酸、丁二酸)發生反應來獲得。
聚胺基甲酸酯樹脂藉由使通式(1)所表示的化合物、與芳香族二異氰酸酯(例如,二苯乙烯二異氰酸酯、二甲苯二異氰酸酯)、或脂肪族二異氰酸酯(例如,五亞甲基二異氰酸酯、六亞甲基二異氰酸酯、環己烷二亞甲基二異氰酸酯)發生反應來獲得。
聚碳酸酯樹脂如後述般,藉由使通式(1)所表示的化合物與碳酸二酯等碳酸酯前驅物質發生反應來獲得。
聚醚樹脂藉由在鹼的存在下使通式(1)所表示的化合物與脂肪族二鹵素化合物(例如,二溴乙烷、二溴丙烷)發生反應來獲得。
於該些樹脂中,本申請案的通式(1)所表示的化合物以外的反應物可單獨使用,亦可併用多個。另外,亦可併用本申請案的通式(1)所表示的化合物以外的二羥基化合物使樹脂進行聚合。
於併用本申請案的通式(1)所表示的化合物以外的二羥基化合物的情況下,相對於本申請案的通式(1)所表示的化合物與通式(1)所表示的化合物以外的二羥基化合物的合計,通式(1)所表示的化合物的比例較佳為5莫耳%以上且99莫耳%以下,更佳為10莫耳%以上且99莫耳%以下,進而佳為15莫耳%以上且99莫耳%以下。
此處,作為通式(1)所表示的化合物以外的二羥基化合物,例如可列舉:9,9-雙〔4-(2-羥基乙氧基)苯基〕芴、9,9-雙〔4-(2-羥基乙氧基)-3-甲基苯基〕芴、9,9-雙〔4-(2-羥基乙氧基)-3-乙基苯基〕芴、9,9-雙〔4-(2-羥基乙氧基)-3-正丙基苯基〕芴、9,9-雙〔4-(2-羥基乙氧基)-3-異丙基苯基〕芴、9,9-雙〔4-(2-羥基乙氧基)-3-正丁基苯基〕芴、9,9-雙〔4-(2-羥基乙氧基)-3-第二丁基苯基〕芴、9,9-雙〔4-(2-羥基乙氧基)-3-第三丁基苯基〕芴、9,9-雙〔4-(2-羥基乙氧基)-3-環己基苯基〕芴、9,9-雙〔4-(2-羥基乙氧基)-2-苯基苯基〕芴、9,9-雙〔4-(2-羥基乙氧基)-3-苯基苯基〕芴、9,9-雙〔4-(2-羥基乙氧基)-3-(3-甲基苯基)苯基〕芴、雙〔4-(2'-羥基乙氧基)苯基〕硫醚、雙〔4-(2'-羥基乙氧基)-3-甲基苯基〕硫醚、雙〔4-(2'-羥基乙氧基)苯基〕碸、雙〔4-(2'-羥基乙氧基)-3-甲基苯基〕碸、雙〔4-(2'-羥基乙氧基)苯基〕亞碸、雙〔4-(2'-羥基乙氧基)苯基〕亞碸、雙(4-羥基苯基)甲烷、2,2-雙(4-羥基苯基)丙烷、1,1-雙(4-羥基苯基)乙烷、1,1-雙(4-羥基苯基)苯基乙烷、2,2-雙(4-羥基-3-甲基苯基)丙烷、2,2-雙(4-羥基苯基)庚烷、2,2-雙(4-羥基-3,5-二氯苯基)丙烷、2,2-雙(4-羥基-3,5-二溴苯基)丙烷、4,4-二羥基苯基-1,1-間二異丙基苯等雙(4-羥基芳基)烷烴類;1,1-雙(4-羥基苯基)環戊烷、1,1-雙(4-羥基苯基)環己烷、1,1-雙(4-羥基苯基)-3,3,5-三甲基環己烷、2,2,2,2-四氫-3,3,3,3-四甲基-1,1-螺雙〔1H茚〕-6,6-二醇等雙(羥基芳基)環烷烴類;雙(4-羥基苯基)醚、雙(4-羥基-3,5-二氯苯基)醚等二羥基芳基醚類;9,9-雙(4-羥基苯基)芴、9,9-雙(4-羥基-3-甲基苯基)芴、9,9-雙(4-羥基-3-第三丁基苯基)芴、9,9-雙(4-羥基-3-異丙基苯基)芴、9,9-雙(4-羥基-3-環己基苯基)芴、9,9-雙(4-羥基-3-苯基苯基)芴;乙二醇、1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,4-環己烷二甲醇、2,2-二甲基-1,3-丙二醇、1,10-癸二醇、二乙二醇、四乙二醇、降冰片烷二甲醇、十氫萘二甲醇、三環[5.2.1.02.6
]癸烷二甲醇、五環十五烷二甲醇、環戊烷-1,3-二甲醇、螺甘油等。
[聚碳酸酯樹脂]
本實施形態的聚碳酸酯樹脂是使用本實施形態的通式(1)所表示的化合物來製造。本實施形態的聚碳酸酯樹脂具有式(1p)所表示的源自通式(1)所表示的化合物的結構單元。此種聚碳酸酯樹脂可實現高折射率且透明性優異的光學成形體。結果,可較佳地用作光學透鏡的材料。
式(1p)中,Ar1
及Ar2
、R1
及R2
、以及o及p與式(1)中者含義相同。較佳的態樣亦相同。
本實施形態的聚碳酸酯樹脂的聚苯乙烯換算的重量平均分子量(Mw)較佳為1.5×103
以上且2.0×105
以下,更佳為2.0×103
以上且1.2×105
以下。
若Mw為所述下限值以上,則可進一步抑制所獲得的成形體變脆,因此較佳。若Mw為所述上限值以下,則熔融黏度變得更適度,因此製造後的樹脂的取出變得更容易,流動性進一步變得更良好,容易於熔融狀態下射出成形,因此較佳。
本實施形態的聚碳酸酯樹脂於23℃、波長633 nm下的折射率(nD)較佳為1.70以上且1.85以下,更佳為1.70以上且1.82以下,進而佳為1.71以上且1.81以下,特佳為1.72以上且1.81以下。
可於本實施形態的聚碳酸酯樹脂中摻合其他樹脂,供於成形體的製造。作為其他樹脂,例如可列舉:聚醯胺、聚縮醛、聚碳酸酯、改質聚苯醚、聚對苯二甲酸乙二酯、聚對苯二甲酸丁二酯等。
進而可於本實施形態的聚碳酸酯樹脂中添加抗氧化劑、脫模劑、紫外線吸收劑、流動性改質劑、結晶成核劑、強化劑、染料、抗靜電劑、抗菌劑等。
作為成形方法,除可例示射出成形以外,亦可例示壓縮成形、澆注、輥加工、擠出成形、延伸等,但並不限於該些。
於將本實施形態的聚碳酸酯樹脂用於射出成形的情況下,較佳的玻璃轉移溫度(Tg)為80℃以上且190℃以下,更佳為85℃以上且180℃以下,進而佳為90℃以上且170℃以下。若Tg為所述下限值以上,則使用溫度範圍變得更寬,因此較佳。另外若Tg為所述上限值以下,則樹脂的熔融溫度更低,更不易發生樹脂的分解或著色,因此較佳。另外若Tg為所述上限值以下,則即便利用通用的模具溫度調整機亦可減小模具溫度與樹脂玻璃轉移溫度的差。因此,容易於對製品要求嚴格的表面精度的用途中使用而較佳。
使用本實施形態的聚碳酸酯樹脂獲得的光學成形體依據JIS K-7361-1(1997)而測定的總光線透過率較佳為82%以上,更佳為85%以上,與雙酚A型聚碳酸酯樹脂等相比亦不遜色。
[聚碳酸酯樹脂的製造方法]
實施形態的聚碳酸酯樹脂可使用所述通式(1)所表示的化合物作為原料來製造。具體而言,可於鹼性化合物觸媒或酯交換觸媒或包含該兩者的混合觸媒的存在下、或者於無觸媒下,藉由熔融縮聚法使通式(1)所表示的化合物及碳酸二酯等碳酸酯前驅物質反應來製造。
作為本實施形態的聚碳酸酯樹脂的製造中所使用的碳酸二酯,可列舉:碳酸二苯酯、碳酸二對甲苯酯、碳酸二間甲苯酯、碳酸二鄰甲苯酯、雙(對氯苯基)碳酸酯、雙(間氯苯基)碳酸酯、雙(鄰氯苯基)碳酸酯、碳酸間甲苯酚基酯、碳酸二甲酯、碳酸二乙酯、碳酸二正丁酯、碳酸二環己酯等。該些中,較佳為碳酸二苯酯。碳酸二苯酯較佳為相對於通式(1)所表示的化合物1莫耳而以0.97莫耳~1.20莫耳的比率使用,更佳為0.98莫耳~1.10莫耳的比率。
作為本實施形態的聚碳酸酯樹脂的製造中所使用的鹼性化合物觸媒,可列舉:鹼金屬化合物、鹼土金屬化合物、及含氮化合物等。作為此種化合物,可較佳地使用鹼金屬化合物及鹼土金屬化合物等的有機酸鹽、無機鹽、氧化物、氫氧化物、氫化物或醇鹽、或者氫氧化四級銨及該些的鹽、胺類等,該些化合物可單獨使用或組合而使用。
作為鹼金屬化合物,例如可列舉:鹼金屬的有機酸鹽、無機鹽、氧化物、氫氧化物、氫化物或醇鹽等。具體而言,可使用氫氧化鈉、氫氧化鉀、氫氧化銫、氫氧化鋰、碳酸氫鈉、碳酸鈉、碳酸氫鉀、碳酸鉀、碳酸銫、碳酸鋰、乙酸鈉、乙酸鉀、乙酸銫、乙酸鋰、硬脂酸鈉、硬脂酸鉀、硬脂酸銫、硬脂酸鋰、氫化硼鈉、苯基化硼鈉、苯甲酸鈉、苯甲酸鉀、苯甲酸銫、苯甲酸鋰、磷酸氫二鈉、磷酸氫二鉀、磷酸氫二鋰、磷酸苯基二鈉、雙酚A的二鈉鹽、二鉀鹽、二銫鹽或二鋰鹽、苯酚的鈉鹽、鉀鹽、銫鹽或鋰鹽等。
作為鹼土金屬化合物,例如可列舉:鹼土金屬化合物的有機酸鹽、無機鹽、氧化物、氫氧化物、氫化物或醇鹽等。具體而言,可使用氫氧化鎂、氫氧化鈣、氫氧化鍶、氫氧化鋇、碳酸氫鎂、碳酸氫鈣、碳酸氫鍶、碳酸氫鋇、碳酸鎂、碳酸鈣、碳酸鍶、碳酸鋇、乙酸鎂、乙酸鈣、乙酸鍶、乙酸鋇、硬脂酸鎂、硬脂酸鈣、苯甲酸鈣、苯基磷酸鎂等。
作為含氮化合物,例如可列舉氫氧化四級銨及該些的鹽、胺類等。具體而言,可使用氫氧化四甲基銨、氫氧化四乙基銨、氫氧化四正丙基銨、氫氧化四正丁基銨、氫氧化三甲基苄基銨等具有烷基、芳基等的氫氧化四級銨類;三乙胺、二甲基苄基胺、三苯基胺等三級胺類;二乙胺、二丁胺等二級胺類;正丙胺、正丁胺等一級胺類;2-甲基咪唑、2-苯基咪唑、苯並咪唑等咪唑類;或者氨、四甲基硼氫化銨、四正丁基硼氫化銨、四正丁基四苯基硼酸銨、四苯基四苯基硼酸銨等鹼或鹼性鹽等。
作為酯交換觸媒,可較佳地使用鋅、錫、鋯、鉛等的鹽,該些可單獨使用或組合使用。作為酯交換觸媒,具體而言,可使用乙酸鋅、苯甲酸鋅、2-乙基己酸鋅、氯化錫(II)、氯化錫(IV)、乙酸錫(II)、乙酸錫(IV)、二月桂酸二丁基錫、二丁基氧化錫、二丁基二甲氧基錫、乙醯丙酮鋯、羥乙酸鋯(zirconium oxyacetate)、四丁氧基鋯、乙酸鉛(II)、乙酸鉛(IV)等。
相對於通式(1)所表示的化合物的合計1莫耳,該些觸媒以10-9
莫耳~10-3
莫耳的比率使用,較佳為以10-7
莫耳~10-4
莫耳的比率使用。
熔融縮聚法是使用所述原料及觸媒,於加熱下、常壓或減壓下,藉由酯交換反應去除副產物的同時進行熔融縮聚。
本實施形態的熔融縮聚法理想的是將所述通式(1)所表示的化合物、及碳酸二酯於反應容器中熔融後,於使副產生的單羥基化合物滯留的狀態下進行反應。
為了滯留,可封閉反應裝置、或進行減壓或進行加壓等來控制壓力。該步驟的反應時間較佳為20分鐘以上且240分鐘以下,更佳為40分鐘以上且180分鐘以下,特佳為60分鐘以上且150分鐘以下。此時,若生成副產生的單羥基化合物後立即餾去,則最終獲得的聚碳酸酯樹脂中高分子量體的含量少。但是,若使副產生的單羥基化合物於反應容器中滯留一定時間,則關於最終獲得的聚碳酸酯樹脂,可獲得高分子量體的含量多的樹脂。
一般而言,熔融縮聚反應可藉由兩階段以上的多階段步驟實施。具體而言,使第一階段的反應於較佳為120℃~260℃、更佳為180℃~240℃的溫度下、在常壓或加壓下反應較佳為0.1小時~5小時、更佳為0.5小時~3小時。繼而,較佳為於提高反應體系的減壓度的同時提高反應溫度,使通式(1)所表示的化合物與碳酸二酯進行反應,最終於133 Pa(1 mmHg)以下的減壓度、200℃~350℃的溫度下進行0.05小時~2小時的縮聚反應。
熔融縮聚反應可以連續式進行,亦可以分批式進行。
進行反應時所使用的反應裝置可為配備錨型攪拌葉片、馬克斯摻合(Maxblend)攪拌葉片、螺帶(helical ribbon)型攪拌葉片等的立式,亦可為配備槳式葉片、格子葉片、眼鏡葉片等的臥式,抑或可為配備螺桿的擠出機型。另外,考慮到聚合物的黏度而較佳地實施使用將該些反應裝置適宜組合後的反應裝置。
本實施形態的聚碳酸酯樹脂於縮聚反應結束後,為了保持熱穩定性及水解穩定性,可去除觸媒或使觸媒失活。一般而言,可較佳地實施藉由添加公知的酸性物質來進行觸媒的失活的方法。作為酸性物質,具體而言,可較佳地使用苯甲酸丁酯等酯類;對甲苯磺酸等芳香族磺酸類;對甲苯磺酸丁酯、對甲苯磺酸己酯等芳香族磺酸酯類;亞磷酸、磷酸、膦酸等磷酸類;亞磷酸三苯酯、亞磷酸單苯酯、亞磷酸二苯酯、亞磷酸二乙酯、亞磷酸二正丙酯、亞磷酸二正丁酯、亞磷酸二正己酯、亞磷酸二正辛酯、亞磷酸單正辛酯等亞磷酸酯類;磷酸三苯酯、磷酸二苯酯、磷酸單苯酯、磷酸二正丁酯、磷酸二正辛酯、磷酸單正辛酯等磷酸酯類;二苯基膦酸、二正辛基膦酸、二正丁基膦酸等膦酸類;苯基膦酸二乙酯等膦酸酯類;三苯基膦、雙(二苯基膦基)乙烷等膦類;硼酸、苯基硼酸等硼酸類;正十二烷基苯磺酸四正丁基鏻鹽等芳香族磺酸鹽類;硬脂酸氯化物、苯甲醯氯、對甲苯磺酸氯化物等有機鹵化物;二甲基硫酸等烷基硫酸;氯化苄基等有機鹵化物等。該些失活劑相對於觸媒量而言,較佳為使用0.01倍莫耳~50倍莫耳,更佳為使用0.3倍莫耳~20倍莫耳。若相對於觸媒量而言少於0.01倍莫耳,則失活效果不充分而欠佳。另外,若相對於觸媒量而言多於50倍莫耳,則樹脂的耐熱性降低,成形體容易著色,因此欠佳。
亦可設置於觸媒失活後於13 Pa~133 Pa(0.1 mmHg~1 mmHg)的壓力、200℃~350℃的溫度下將聚合物中的低沸點化合物脫揮去除的步驟。於該步驟中可較佳地使用包括槳式葉片、格子葉片、眼鏡葉片等表面更新能力優異的攪拌葉片的臥式裝置、或薄膜蒸發器。
本實施形態的聚碳酸酯樹脂期望異物含量盡可能少,可較佳地實施熔融原料的過濾、觸媒液的過濾等。過濾器的網眼較佳為5 μm以下,更佳為1 μm以下。進而,可較佳地實施利用聚合物過濾器對生成的樹脂進行過濾。聚合物過濾器的網眼較佳為100 μm以下,更佳為30 μm以下。另外,採取樹脂顆粒的步驟較佳為當然低塵環境,更佳為等級1000以下的清潔度。
[光學成形體]
本實施形態的光學成形體包含本實施形態的聚碳酸酯樹脂,可使用本實施形態的聚碳酸酯樹脂來製造光學成形體。
例如可藉由射出成形法、壓縮成形法、射出壓縮成形法、擠出成形法、溶液澆鑄法等任意方法進行成形。
本實施形態的聚碳酸酯樹脂由於成形性及耐熱性優異,因此可於需要射出成形的光學透鏡中特別有利地使用。於成形時可將本實施形態的聚碳酸酯樹脂與其他聚碳酸酯樹脂或聚酯樹脂等其他樹脂混合而使用。
另外,為了於不損害本實施形態的目的的範圍內賦予各種特性,可使用各種添加劑。作為添加劑,可列舉:抗氧化劑、加工穩定劑、脫模劑、紫外線吸收劑、上藍劑(blueing agent)、聚合金屬鈍化劑、阻燃劑、潤滑劑、抗靜電劑、熱射線遮蔽劑、螢光染料(包含螢光增白劑)、顏料、光散射劑、強化填充劑、界面活性劑、抗菌劑、塑化劑、相容化劑、其他樹脂或彈性體等。
作為抗氧化劑,例如可列舉:三乙二醇-雙[3-(3-第三丁基-5-甲基-4-羥基苯基)丙酸酯]、1,6-己二醇-雙[3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯]、季戊四醇-四[3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯]、十八烷基-3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯、1,3,5-三甲基-2,4,6-三(3,5-二-第三丁基-4-羥基苄基)苯、N,N-六亞甲基雙(3,5-二-第三丁基-4-羥基-氫化肉桂醯胺)、3,5-二-第三丁基-4-羥基-苄基磷酸酯-二乙基酯、三(3,5-二-第三丁基-4-羥基苄基)異三聚氰酸酯及3,9-雙{1,1-二甲基-2-[β-(3-第三丁基-4-羥基-5-甲基苯基)丙醯氧基]乙基}-2,4,8,10-四氧雜螺(5,5)十一烷等。
相對於聚碳酸酯樹脂100質量份,聚碳酸酯樹脂中的抗氧化劑的含量較佳為0.001質量份~0.3質量份。
作為加工穩定劑,例如可列舉磷系加工熱穩定劑、硫系加工熱穩定劑等。
作為磷系加工熱穩定劑,例如可列舉:亞磷酸、磷酸、亞膦酸、膦酸及該些的酯等。具體而言,可列舉:三苯基亞磷酸鹽、三(壬基苯基)亞磷酸鹽、三(2,4-二-第三丁基苯基)亞磷酸鹽、三(2,6-二-第三丁基苯基)亞磷酸鹽、三正癸基亞磷酸鹽、三正辛基亞磷酸鹽、三正十八烷基亞磷酸鹽、二正癸基單苯基亞磷酸鹽、二正辛基單苯基亞磷酸鹽、二異丙基單苯基亞磷酸鹽、單正丁基二苯基亞磷酸鹽、單癸基二苯基亞磷酸鹽、單正辛基二苯基亞磷酸鹽、雙(2,6-二-第三丁基-4-甲基苯基)季戊四醇二亞磷酸鹽、2,2-亞甲基雙(4,6-二-第三丁基苯基)辛基亞磷酸鹽、雙(正壬基苯基)季戊四醇二亞磷酸鹽、雙(2,4-二戊基苯基)季戊四醇二亞磷酸鹽、雙(2,4-二-第三丁基苯基)季戊四醇二亞磷酸鹽、二硬脂基季戊四醇二亞磷酸鹽、磷酸三正丁酯、磷酸三乙酯、磷酸三甲酯、磷酸三苯酯、二苯基單鄰聯苯基磷酸酯(diphenyl monoorthoxenyl phosphate)、磷酸二正丁酯、磷酸二正辛酯、磷酸二異丙酯、苯膦酸二甲酯、苯膦酸二乙酯、苯膦酸二丙酯、四(2,4-二-第三丁基苯基)-4,4'-伸聯苯二膦酸酯、四(2,4-二-第三丁基苯基)-4,3'-伸聯苯二膦酸酯、四(2,4-二-第三丁基苯基)-3,3'-伸聯苯二膦酸酯、雙(2,4-二-第三丁基苯基)-4-苯基-苯基膦酸酯及雙(2,4-二-第三丁基苯基)-3-苯基-苯基膦酸酯等。
相對於聚碳酸酯樹脂100質量份,聚碳酸酯樹脂中的磷系加工熱穩定劑的含量較佳為0.001質量份~0.2質量份。
作為硫系加工熱穩定劑,例如可列舉:季戊四醇-四(3-月桂基硫代丙酸酯)、季戊四醇-四(3-肉豆蔻基硫代丙酸酯)、季戊四醇-四(3-硬脂基硫代丙酸酯)、二月桂基-3,3'-硫代二丙酸酯、二肉豆蔻基-3,3'-硫代二丙酸酯、二硬脂基-3,3'-硫代二丙酸酯等。
相對於聚碳酸酯樹脂100質量份,聚碳酸酯樹脂中的硫系加工熱穩定劑的含量較佳為0.001質量份~0.2質量份。
作為脫模劑,較佳為其90質量%以上包含醇與脂肪酸的酯。作為醇與脂肪酸的酯,具體可列舉一元醇與脂肪酸的酯、或多元醇與脂肪酸的部分酯或全部酯。作為所述一元醇與脂肪酸的酯,較佳為碳原子數1~20的一元醇與碳原子數10~30的飽和脂肪酸的酯。另外,作為所述多元醇與脂肪酸的部分酯或全部酯,較佳為碳原子數1~25的多元醇與碳原子數10~30的飽和脂肪酸的部分酯或全部酯。
作為一元醇與飽和脂肪酸的酯,例如可列舉:硬脂酸硬脂酯、棕櫚酸棕櫚酯、硬脂酸正丁酯、月桂酸甲酯、棕櫚酸異丙酯等。作為多元醇與飽和脂肪酸的部分酯或全部酯,例如可列舉:硬脂酸單甘油酯、硬脂酸二甘油酯、硬脂酸三甘油酯、硬脂酸單山梨酸酯、山萮酸單甘油酯、癸酸單甘油酯、月桂酸單甘油酯、季戊四醇單硬脂酸酯、季戊四醇四硬脂酸酯、季戊四醇四壬酸酯、丙二醇單硬脂酸酯、聯苯酸聯苯酯、山梨糖醇單硬脂酸酯、硬脂酸2-乙基己酯、二季戊四醇六硬脂酸酯等二季戊四醇的全部酯或部分酯等。
相對於聚碳酸酯樹脂100質量份,該些脫模劑的含量較佳為0.005質量份~2.0質量份的範圍,更佳為0.01質量份~0.6質量份的範圍,進而佳為0.02質量份~0.5質量份的範圍。
作為紫外線吸收劑,較佳為選自由苯並三唑系紫外線吸收劑、二苯甲酮系紫外線吸收劑、三嗪系紫外線吸收劑、環狀亞胺基酯系紫外線吸收劑及丙烯酸氰基酯系紫外線吸收劑所組成的群組中的至少一種紫外線吸收劑。以下列舉的紫外線吸收劑可單獨使用任一種,亦可將兩種以上組合而使用。
作為苯並三唑系紫外線吸收劑,例如可列舉:2-(2-羥基-5-甲基苯基)苯並三唑、2-(2-羥基-5-第三辛基苯基)苯並三唑、2-(2-羥基-3,5-二戊基苯基)苯基苯並三唑、2-(2-羥基-3-第三丁基-5-甲基苯基)-5-氯苯並三唑、2,2'-亞甲基雙[4-(1,1,3,3-四甲基丁基)-6-(2N-苯並三唑-2-基)苯酚]、2-(2-羥基-3,5-二-第三丁基苯基)苯並三唑、2-(2-羥基-3,5-二-第三丁基苯基)-5-氯苯並三唑、2-(2-羥基-3,5-二-第三戊基苯基)苯並三唑、2-(2-羥基-5-第三丁基苯基)苯並三唑、2-(2-羥基-4-正辛氧基苯基)苯並三唑、2,2'-亞甲基雙(4-戊基-6-苯並三唑苯基)、2,2'-對伸苯基雙(1,3-苯並噁嗪-4-酮)、2-[2-羥基-3-(3,4,5,6-四氫鄰苯二甲醯亞胺甲基)-5-甲基苯基]苯並三唑等。
作為二苯甲酮系紫外線吸收劑,例如可列舉:2,4-二羥基二苯甲酮、2-羥基-4-甲氧基二苯甲酮、2-羥基-4-正辛氧基二苯甲酮、2-羥基-4-苄氧基二苯甲酮、2-羥基-4-甲氧基-5-磺酸氧基二苯甲酮、2-羥基-4-甲氧基-5-磺酸氧基三氫化物レイト二苯甲酮、2,2'-二羥基-4-甲氧基二苯甲酮、2,2',4,4'-四羥基二苯甲酮、2,2'-二羥基-4,4'-二甲氧基二苯甲酮、2,2'-二羥基-4,4'-二甲氧基-5-鈉磺酸氧基二苯甲酮、雙(5-苯甲醯基-4-羥基-2-甲氧基苯基)甲烷、2-羥基-4-正十二烷氧基二苯甲酮、2-羥基-4-甲氧基-2'-羧基二苯甲酮等。
作為三嗪系紫外線吸收劑,例如可列舉2-(4,6-二苯基-1,3,5-三嗪-2-基)-5-[(正己基)氧基]-苯酚、2-(4,6-雙(2,4-二甲基苯基)-1,3,5-三嗪-2-基)-5-[(正辛基)氧基]-苯酚等。
作為環狀亞胺基酯系紫外線吸收劑,例如可列舉:2,2'-雙(3,1-苯並噁嗪-4-酮)、2,2'-對伸苯基雙(3,1-苯並噁嗪-4-酮)、2,2'-間伸苯基雙(3,1-苯並噁嗪-4-酮)、2,2'-(4,4'-二伸苯基)雙(3,1-苯並噁嗪-4-酮)、2,2'-(2,6-伸萘基)雙(3,1-苯並噁嗪-4-酮)、2,2'-(1,5-伸萘基)雙(3,1-苯並噁嗪-4-酮)、2,2'-(2-甲基-對伸苯基)雙(3,1-苯並噁嗪-4-酮)、2,2'-(2-硝基-對伸苯基)雙(3,1-苯並噁嗪-4-酮)及2,2'-(2-氯-對伸苯基)雙(3,1-苯並噁嗪-4-酮)等。
作為丙烯酸氰基酯系紫外線吸收劑,例如可列舉:1,3-雙-[(2'-氰基-3',3'-二苯基丙烯醯基)氧基]、2,2-雙[(2-氰基-3,3-二苯基丙烯醯基)氧基]甲基丙烷、及1,3-雙-[(2-氰基-3,3-二苯基丙烯醯基)氧基]苯等。
相對於聚碳酸酯樹脂100質量份,紫外線吸收劑的含量較佳為0.01質量份~3.0質量份,更佳為0.02質量份~1.0質量份,進而佳為0.05質量份~0.8質量份。若為所述調配量的範圍,則可根據用途對聚碳酸酯樹脂賦予充分的耐候性。
作為上藍劑,例如可列舉拜耳公司的馬高列斯紫(Macrolex Violet)B及馬高列斯藍(Macrolex Blue)RR以及科萊恩(Clariant)公司的珀利辛思倫藍(Polysynthren Blue)RLS等。
為了消除聚碳酸酯樹脂的黃色調,有效的是上藍劑。特別是於賦予耐候性的聚碳酸酯樹脂的情況下,由於調配有一定量的紫外線吸收劑,因此存在因「紫外線吸收劑的作用或顏色」而導致聚碳酸酯樹脂成形品容易帶有黃色調的傾向,特別是為了對片或透鏡賦予自然的透明感,有效的是調配上藍劑。
相對於聚碳酸酯樹脂,上藍劑的調配量例如較佳為0.05 ppm~1.5 ppm,更佳為0.1 ppm~1.2 ppm。
本實施形態的聚碳酸酯樹脂顯示出高折射率與優異的耐熱性,而且具有適於成形的流動性。進而,由於雙折射低且難以發生光學應變,因此除了可有利地用作光學透鏡以外,亦可有利地用作適於液晶顯示器、有機EL顯示器、太陽能電池等中所使用的透明導電性基板、光碟、液晶面板、光卡、片、膜、光纖、連接器、蒸鍍塑膠反射鏡、顯示器等光學零件的結構材料或功能材料用途的光學用成形體。
視需要亦可於光學成形體的表面設置防反射層或硬塗層等塗佈層。防反射層可為單層亦可為多層,可為有機物亦可為無機物,但較佳為無機物。具體而言,可例示:氧化矽、氧化鋁、氧化鋯、氧化鈦、氧化鈰、氧化鎂、氟化鎂等氧化物或氟化物。
(光學透鏡)
使用本實施形態的聚碳酸酯樹脂而製造的光學透鏡為高折射率,且耐熱性優異,因此可用於望遠鏡、雙目鏡、電視投影儀等先前使用高價的高折射率玻璃透鏡的領域,極其有用。視需要,較佳為以非球面透鏡的形式使用。非球面透鏡中可利用一枚透鏡使球面像差實質上為零,因此不需要藉由多個球面透鏡的組合來去除球面像差,從而可實現輕量化及生產成本的降低化。因此,非球面透鏡於光學透鏡中特別是作為照相機透鏡而言有用。
本實施形態的光學透鏡例如可利用射出成形法、壓縮成形法、射出壓縮成形法等任意方法來成形。根據本實施形態,可更簡便地獲得利用玻璃透鏡於技術上難以加工的高折射率低雙折射非球面透鏡。
(光學膜)
使用本實施形態的聚碳酸酯樹脂而製造的光學膜由於透明性及耐熱性優異,因此可較佳地用於液晶基板用膜、光學記憶卡等。
以上,對本發明的實施形態進行了敘述,但該些為本發明的例示,亦可採用所述以外的各種結構。
[實施例]
以下,參照實施例、比較例對本實施形態進行詳細說明。再者,本實施形態並不受該些實施例的記載的任何限定。
1.測定、評價方法
於以下的實施例、比較例中,各物性的測定及評價是利用以下的方法進行。
1)聚苯乙烯換算的重量平均分子量(Mw):使用凝膠滲透層析儀(GPC:沃特世(Waters)公司製造的1515、2414及2489),將氯仿作為溶析液,使用已知的分子量(分子量分佈=1)的標準聚苯乙烯製成校準曲線。基於該校準曲線,由GPC的滯留時間(retention time)算出Mw。
2)折射率(n633):使用旋塗機以200 rpm且20秒、1000 rpm且5秒將8.5 wt%濃度的樹脂的氯仿溶液塗佈於矽晶圓上,於120℃下烘烤5分鐘,於200℃下烘烤2分鐘來調整樣品,使用分光橢圓儀GES5E(瑟米萊伯[SEMILAB]公司製造),對波長200 nm-1000 nm下的光學測定資料擬合以下所示的光學模型,藉此進行膜的折射率及膜厚的算出。
(光學模型)
積層結構:膜/SiO2
(2 nm厚)/Si基板(500 μm厚)
膜的色散公式:柯西+洛倫茲振子模型
3)玻璃轉移溫度(Tg):利用示差熱掃描量熱分析計(DSC:島津製作所製造的DSC-60)進行測定。
1.式(1)所表示的化合物的製備
(實施例1)
9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴的合成
步驟(i):9,9-雙(2'-羥基乙基)-2,7-二溴-9H-芴的合成
於500 ml的燒瓶中裝入2,7-二溴-9H-芴66.5 g(0.2 mol)、氫氧化鉀(粉末狀)56 g(0.998 mol)、碘化鉀3.4 g(0.02 mol)、二甲基亞碸150 ml,利用冰水冷卻至10℃。之後,花費45分鐘滴加2-溴乙醇58.4 g(0.467 mol),之後於室溫下攪拌一晚。之後,將反應液加熱至50℃並加熱攪拌40小時。將反應混合物排出至蒸餾水2升中,利用濃鹽酸將pH值調合為6。過濾分離所獲得的固體並利用水3升加以清洗。將所獲得的固體溶解於乙酸乙酯1升中,利用蒸餾水500 ml清洗後,利用蒸發器加以濃縮,並添加氯仿,藉此以34.8 g的無色結晶的形式獲得9,9-雙(2'-羥基乙基)-2,7-二溴-9H-芴。
步驟(ii):9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴的製備
於1升的燒瓶中裝入9,9-雙(2'-羥基乙基)-2,7-二溴-9H-芴20.75 g(50 mmol)、萘-2-硼酸19.17 g(0.11 mol)、碳酸鉀15.3 g(0.11 mol)、蒸餾水250 g及二甲基亞碸400 g。於該反應混合物中添加四(三苯基膦)鈀3.0 g,加熱至100℃並加熱攪拌5小時。冷卻後過濾分離所生成的固體,並利用水500 g加以清洗,於50℃下進行真空乾燥。乾燥後利用氯仿對固體進行懸浮清洗,從而以無色結晶的形式獲得9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴20.87 g。利用DSC測定的熔點為236℃。
(實施例2)
9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴的合成
步驟(i):2-(2'-溴乙氧基)四氫吡喃的合成
於包括攪拌機、溫度計及滴加漏斗的2升的圓底燒瓶中裝入2-溴乙醇150 g(1.20 mol)及二氯甲烷800 ml,利用冰水進行冷卻。之後,於內溫達到5℃的時刻,於10℃以下滴加3,4-二氫-2H-吡喃130 g(1.56 mol)。滴加結束後,添加對甲苯磺酸吡啶鎓30 g(0.12 mol),於室溫下攪拌一晚。之後,添加碳酸氫鈉飽和水,並對二氯甲烷層進行水洗。利用蒸發器對所獲得的二氯甲烷層進行濃縮,從而以淡黃色的油狀物的形式獲得2-(2'-溴乙氧基)四氫吡喃255 g。
步驟(ii):9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二溴-9H-芴的合成
於包括攪拌機、溫度計及回流管的2升圓底燒瓶中投入2-(2'-溴乙氧基)四氫吡喃255 g、甲苯270 ml及2,7-二溴-9H-芴164 g(0.506 mol),向其中添加50%氫氧化鈉水溶液270 ml。之後,添加溴化四丁基銨8.5 g(26.2 mmol),加熱至100℃並加熱攪拌11.5小時。之後,將反應混合物冷卻至室溫為止,對水層進行分液後,添加乙酸乙酯700 ml及蒸餾水700 ml來進行水洗。進而重覆水洗後,將包含乙酸乙酯及甲苯的層分離,利用蒸發器加以濃縮。向濃縮後獲得的黏稠的液體中添加少量的9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二溴-9H-芴的籽晶,進行添加了甲醇的結晶化。對所獲得的結晶進行過濾,並利用少量的甲醇清洗後,自甲醇500 ml進行加熱再結晶,從而以淡黃色結晶的形式獲得目標9,9-雙〔2-(2'-四氫吡喃基)乙氧基〕-2,7-二溴-9H-芴246 g。
m.p.98.5℃1
H-NMR(CDCl3
)δ 1.30-1.53 (m, 12H), 2.34-2.38 (t, 4H), 2.70-3.5 (m, 8H), 4.1 (t, 2H), 7.43-7.55 (m, 6H)
步驟(iii):9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-2''-基-9H-芴的合成
於包括攪拌機、溫度計及回流管的1升圓底燒瓶中投入9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二溴-9H-芴72.55 g(125 mmol)、甲苯475 ml、碳酸鉀61 g(442 mmol)、2-萘硼酸47.29 g(275 mmol)及蒸餾水211 ml並攪拌,同時向該反應混合物中添加四(三苯基膦)鈀1.4 g,升溫至80℃為止。於80℃下進行12小時的加熱攪拌,之後冷卻至室溫為止。對水層進行分液後,利用蒸餾水清洗甲苯層,之後利用蒸發器對甲苯層進行濃縮。於濃縮殘渣中添加甲醇730 ml,過濾分離所產生的固體,利用甲醇加以清洗。之後,藉由矽膠管柱層析法(溶析液甲苯~甲苯/乙酸乙酯=9/1)進行精製,之後自甲基賽珞蘇進行再結晶,從而獲得121.01 g的目標物。收率72%、HPLC純度99.3%、m.p.148℃、1
H-NMR(CDCl3
)δ 1.20-1.70 (m, 12H), 2,55 (t, 4H), 2.8-3.5 (m, 8H), 4.16 (m, 2H), 7.40-7.65 (m, 4H), 7.70-8.05 (m, 14H), 8.1 (s, 2H)
步驟(iv):9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴的合成
於包括攪拌機、溫度計及回流管的1升圓底燒瓶中投入9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-2''-基‐9H-芴60.00 g(88.9 mmol)、甲基賽珞蘇600 ml、蒸餾水25 ml及濃鹽酸7 ml,於攪拌的同時升溫至115℃,於該溫度下加熱攪拌4小時。之後,冷卻至室溫為止,添加水180 ml,並過濾分離所產生的結晶。利用蒸餾水清洗所獲得的結晶後,於50℃下減壓乾燥,之後利用熱甲基賽珞蘇進行懸浮清洗,從而獲得目標物38.73 g。收率85%、m.p.249.5℃、1
H-NMR(DMSO-d6
)δ 2.43 (t, 4H), 2.80 (t, 4H), 4.16 (t, 2H), 7.50-7.60 (m, 4H), 7.8-8.1 (m, 12H), 8.35 (s, 2H)
(實施例3)
9,9-雙(2'-羥基乙基)-2,7-雙〔二苯並[b,d]呋喃-4''-基〕-9H-芴的合成
於實施例2的步驟(iii)中,使用二苯並[b,d]呋喃-4-基硼酸58.85 g(275 mmol)代替使用2-萘硼酸47.29 g(275 mmol),除此以外按照實施例2的步驟(iii)中記載的操作,獲得9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔二苯並[b,d]呋喃-4''-基〕-9H-芴66.05 g。收率70%、HPLC純度97.5%、m.p.176.7℃、1
H-NMR(CDCl3
)δ 1.29-1.45 (10H, m), 1.58 (2H, m), 2.58 (4H, t), 2.98 (2H, q), 3.24 (2H, dt), 3.40 (2H, q), 3.55 (2H, dt), 4.23 (2H, s), 7.39 (2H, t), 7.48 (4H, q), 7.64 (2H, d), 7.68-7.71 (2H, m), 7.90-8.03 (10H, m)
於實施例2的步驟(iv)中,使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔二苯並[b,d]呋喃-4''-基〕-9H-芴60.00 g(79.4 mmol)、甲基賽珞蘇540 ml、蒸餾水22 ml及濃鹽酸6.2 ml代替使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-2''-基-9H-芴60.00 g(88.9 mmol)、甲基賽珞蘇600 ml、蒸餾水25 ml及濃鹽酸7 ml,除此以外按照實施例2的步驟(iv)中記載的操作,獲得目標物41.03 g。收率88%、HPLC純度99.4%、m.p.247.4℃、1
H-NMR(DMSO-d6
)δ 2.40 (4H, t), 2.98 (4H, m), 4.24 (2H, t), 7.46 (2H, t), 7.58 (4H, dt), 7.82 (4H, dd), 8.03-8.10 (6H, m), 8.22 (4H, dd)
(實施例4)
9,9-雙(2'-羥基乙基)-2,7-雙〔4-(萘-2-基)苯基〕-9H-芴的合成
於實施例2的步驟(iii)中,使用4-(萘-2-基)苯基硼酸68.22 g(275 mmol)代替使用2-萘硼酸47.29 g(275 mmol),除此以外按照實施例2的步驟(iii)中記載的操作,獲得9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔4-(萘-2-基)苯基〕-9H-芴68.23 g。收率66%、HPLC純度99.2%、m.p.209.4℃、1
H-NMR(CDCl3
)δ 1.26-1.61 (12H, m), 2.55 (4H, t), 2.86 (2H, q), 3.22-3.32 (4H, m), 3.51-3.56 (2H, m), 4.17 (2H, t), 7.49-7.55 (4H, m), 7.67 (2H, d), 7.75 (2H, d), 7.78-7.82 (6H, m), 7.84-7.90 (8H, m), 7.95 (4H, t), 8.13 (2H, s)
於實施例2的步驟(iv)中,使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔4-(萘-2-基)苯基〕-9H-芴60.00 g、甲基賽珞蘇500 ml、蒸餾水20 ml及濃鹽酸6 ml代替使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-2''-基-9H-芴60.00 g(88.9 mmol)、甲基賽珞蘇600 ml、蒸餾水25 ml及濃鹽酸7 ml,除此以外按照實施例2的步驟(iv)中記載的操作,獲得目標物41.10 g。收率86%、HPLC純度99.6%、m.p.341.3℃、1
H-NMR(DMSO-d6
)δ 2.41 (4H, t), 2.83 (4H, q), 4.20 (2H, t), 7.53-7.60 (4H, m), 7.83 (2H, d), 7.94-8.00 (16H, m), 8.06 (4H, d), 8.33 (2H, s)
(實施例5)
9,9-雙(2'-羥基乙基)-2,7-雙〔3-(萘-2-基)苯基〕-9H-芴的合成
於實施例2的步驟(iii)中,使用3-(萘-2-基)苯基硼酸68.22 g(275 mmol)代替使用2-萘硼酸47.29 g(275 mmol),除此以外按照實施例2的步驟(iii)中記載的操作,獲得9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔3-(萘-2-基)苯基〕-9H-芴70.30 g。收率68%、HPLC純度98.9%、m.p.171.6℃、1
H-NMR(CDCl3
)δ 1.26-1.58 (12H, m), 2.54 (4H, t), 2.86 (2H, q), 3.22-3.30 (4H, m), 3.49-3.54 (2H, m), 4.16 (2H, t), 7.51-7.61 (6H, m), 7.66-7.74 (8H, m), 7.81 (2H, d), 7.84 (2H, dd), 7.90 (2H, d), 7.94-7.99 (6H, m), 8.14 (2H, s)
於實施例2的步驟(iv)中,使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔3-(萘-2-基)苯基〕-9H-芴60.00 g(72.5 mmol)、甲基賽珞蘇500 ml、蒸餾水20 ml及濃鹽酸5.7 g代替使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-2''-基-9H-芴60.00 g(88.9 mmol)、甲基賽珞蘇600 ml、蒸餾水25 ml及濃鹽酸7 ml,除此以外按照實施例2的步驟(iv)中記載的操作,獲得目標物41.58 g。收率87%。再者,最終品的精製是藉由管柱層析法(溶析液:乙酸乙酯/氯仿=1/8→1/4)來實施。HPLC純度99.7%、m.p.143.1℃、1
H-NMR(DMSO-d6
)δ:2.52 (4H, t), 3.17 (4H, q), 7.51-7.54 (4H, m), 7.60 (2H, t), 7.67-7.69 (2H, m), 7.74 (2H, dd), 7.76 (2H, s), 7.82-7.91 (6H, m), 7.94-7.99 (6H, m), 8.14 (2H, s)
(實施例6)
9,9-雙(2'-羥基乙基)-2,7-二菲-9''-基-9H-芴的合成
於實施例2的步驟(iii)中,使用菲-9-基硼酸61.06 g(275 mmol)代替使用2-萘硼酸47.29 g(275 mmol),除此以外按照實施例2的步驟(iii)中記載的操作,獲得9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二菲-9''-基-9H-芴73.62 g。收率76%、HPLC純度95.9%、黏稠固體、1
H-NMR(CDCl3
)δ 1.36-1.64 (12H, m), 2.50 (4H, t), 2.99 (2H, q), 3.30-3.43 (4H, m), 3.58 (2H, dt), 4.29 (2H, s), 7.57 (4H, d), 7.63-7.72 (8H, m), 7.77 (2H, s), 7.90 (2H, d), 7.93-7.95 (2H, m), 8.03 (2H, d), 8.79 (4H, dd)
於實施例2的步驟(iv)中,使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二菲-9''-基-9H-芴70.00 g(90.3 mmol)、甲基賽珞蘇610 ml、蒸餾水25 ml及濃鹽酸7 ml代替使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-2''-基-9H-芴60.00 g(88.9 mmol)、甲基賽珞蘇600 ml、蒸餾水25 ml及濃鹽酸7 ml,除此以外按照實施例2的步驟(iv)中記載的操作,獲得目標物48.22 g。收率88%。再者,最終品的精製是藉由管柱層析法(溶析液:乙酸乙酯/氯仿=1/6→1/4)來實施。HPLC純度99.3%、m.p.226.9℃、1
H-NMR(DMSO-d6
)δ 2.48 (4H, t), 3.31 (4H, q), 7.57-7.73 (12H, m), 7.77 (2H, s), 7.95 (6H, dd), 8.79 (4H, dd)
(實施例7)
9,9-雙(2'-羥基乙基)-2,7-雙〔二苯並[b,d]噻吩-4''-基〕-9H-芴的合成
於實施例2的步驟(iii)中,使用二苯並[b,d]噻吩-4-基硼酸62.72 g(275 mmol)代替使用2-萘硼酸47.29 g(275 mmol),除此以外按照實施例2的步驟(iii)中記載的操作,獲得9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔二苯並[b,d]噻吩-4''-基〕-9H-芴68.87 g。收率70%、HPLC純度99.1%、黏稠固體、1
H-NMR(CDCl3
)δ 1.28-1.43 (10H, m), 1.55 (2H, m), 2.56 (4H, t), 2.95 (2H, q), 3.22 (2H, dt), 3.37 (2H, q), 3.52 (2H, dt), 4.20 (2H, s), 7.51 (2H, t), 7.68 (4H, q), 7.85 (2H, d), 7.82-7.89 (2H, m), 8.11-8.24 (10H, m)
於實施例2的步驟(iv)中,使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔二苯並[b,d]噻吩-4''-基〕-9H-芴60.00 g(76.4 mmol)、甲基賽珞蘇500 ml、蒸餾水20 ml及濃鹽酸6.0 ml代替使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-2''-基-9H-芴60.00 g(88.9 mmol)、甲基賽珞蘇600 ml、蒸餾水25 ml及濃鹽酸7 ml,除此以外按照實施例2的步驟(iv)中記載的操作,獲得目標物40.10 g。收率85%、HPLC純度98.9%、m.p.223.6℃、1
H-NMR(DMSO-d6
)δ 2.38 (4H, t), 2.93 (4H, dt), 4.26 (2H, t), 7.57 (4H, dd), 7.69-7.71 (4H, m), 7.79 (2H, d), 7.97 (2H, s), 8.04 (2H, dd), 8.10 (2H, d), 8.43-8.47 (4H, dd)
(實施例8)
9,9-雙(2'-羥基乙基)-2,7-雙〔4''-苯氧基苯基〕-9H-芴的合成
於實施例2的步驟(iii)中,使用4-苯氧基苯基硼酸58.86 g(275 mmol)代替使用2-萘硼酸47.29 g(275 mmol),除此以外按照實施例2的步驟(iii)中記載的操作,獲得9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔4-苯氧基苯基〕-9H-芴68.31 g。收率72%、HPLC純度98.8%、黏稠固體、1
H-NMR(CDCl3
)δ 1.24-1.59 (12H, m), 2.48 (4H, t), 2.81 (2H, q), 3.20-3.27 (4H, m), 3.48-3.54 (2H, m), 4.14 (2H, t), 7.07-7.15 (10H, m), 7.37 (4H, dt), 7.55 (2H, d), 7.60-7.63 (6H, m), 7.74 (2H, d)
於實施例2的步驟(iv)中,使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔4''-苯氧基苯基〕-9H-芴60.00 g(79.1 mmol)、甲基賽珞蘇530 ml、蒸餾水22 ml及濃鹽酸6.2 ml代替使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-2''-基-9H-芴60.00 g(88.9 mmol)、甲基賽珞蘇600 ml、蒸餾水25 ml及濃鹽酸7 ml,除此以外按照實施例2的步驟(iv)中記載的操作,獲得目標物38.29 g。收率82%、HPLC純度99.7%、m.p.134.1℃、1
H-NMR(DMSO-d6
)δ 2.34 (4H, t), 2.76 (4H, q), 4.14 (2H, t), 7.07-7.20 (10H, m), 7.43 (4H, t), 7.67 (2H, dd), 7.81 (6H, t), 7.90 (2H, d)
(實施例9)
9,9-雙(2'-羥基乙基)-2,7-雙〔4''-苯基萘-1''-基〕-9H-芴的合成
於實施例2的步驟(iii)中,使用4-苯基萘-1-基硼酸68.22 g(275 mmol)代替使用2-萘硼酸47.29 g(275 mmol),除此以外按照實施例2的步驟(iii)中記載的操作,獲得9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔4''-苯基萘-1''-基〕-9H-芴73.4 g。收率71%、HPLC純度99.8%、m.p.230.3℃、1
H-NMR(CDCl3
)δ 1.36-1.61 (12H, m), 2.50 (4H, t), 2.97 (2H, q), 3.30 (2H, dt), 3.38 (2H, q), 3.57 (2H, dt), 4.27 (2H, s), 7.45-7.58 (20H, m), 7.66 (2H, s), 7.89 (2H, d), 7.98-8.00 (2H, m), 8.05-8.10 (2H, m)
於實施例2的步驟(iv)中,使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔4''-苯基萘-1''-基〕-9H-芴70.00 g(84.6 mmol)、甲基賽珞蘇570 ml、蒸餾水24 ml及濃鹽酸7.0 ml代替使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-2''-基-9H-芴60.00 g(88.9 mmol)、甲基賽珞蘇600 ml、蒸餾水25 ml及濃鹽酸7 ml,除此以外按照實施例2的步驟(iv)中記載的操作,獲得目標物47.95 g。收率86%、HPLC純度99.0%、m.p.271.4℃、1
H-NMR(DMSO-d6
)δ 2.34 (4H, t), 2.95 (4H, dt), 4.24 (2H, t), 7.51-7.63 (20H, m), 7.72 (2H, s), 7.90-7.93 (2H, m), 7.99-8.01 (2H, m), 8.08 (2H, d)
(實施例10)
9,9-雙(2'-羥基乙基)-2,7-雙〔9'',9''-二甲基-9''H-芴-2''-基〕-9H-芴的合成
於實施例2的步驟(iii)中,使用9,9-二甲基-9H-芴-2-基硼酸65.47 g(275 mmol)代替使用2-萘硼酸47.29 g(275 mmol),除此以外按照實施例2的步驟(iii)中記載的操作,獲得9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔9'',9''-二甲基-9''H-芴-2''-基〕-9H-芴76.67 g。收率76%、HPLC純度91.0%、黏稠固體、1
H-NMR(CDCl3
)δ 1.25-1.50 (12H, m), 1.58 (12H, s), 2.56 (4H, t), 2.87 (2H, q), 3.23-3.32 (4H, m), 3.51-3.57 (2H, m), 4.16 (2H, t), 7.32-7.39 (4H, m), 7.47 (2H, dd), 7.62-7.67 (4H, m), 7.69-7.72 (4H, m), 7.76-7.82 (6H, m)
於實施例2的步驟(iv)中,使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-雙〔9'',9''-二甲基-9''H-芴-2''-基〕-9H-芴70.00 g(89.7 mmol)、甲基賽珞蘇590 ml、蒸餾水24 ml及濃鹽酸6.8 ml代替使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-2''-基-9H-芴60.00 g(88.9 mmol)、甲基賽珞蘇600 ml、蒸餾水25 ml及濃鹽酸7 ml,除此以外按照實施例2的步驟(iv)中記載的操作,獲得目標物48.21 g。收率87%、HPLC純度96.9%、m.p.272.3℃、1
H-NMR(DMSO-d6
)δ 1.55 (12H, s), 2.42 (4H, t), 2.79 (4H, m), 4.18 (2H, t), 7.33-7.40 (4H, m), 7.59 (2H, dd), 7.76-7.79 (4H, m), 7.88 (2H, d), 7.95 (8H, dd)
(實施例11)
9,9-雙(2'-羥基乙基)-2,7-二萘-1''-基-9H-芴的合成
於實施例2的步驟(iii)中,使用1-萘硼酸47.29 g(275 mmol)代替使用2-萘硼酸47.29 g(275 mmol),除此以外按照實施例2的步驟(iii)中記載的操作,獲得9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘基-1''-基-9H-芴65.80 g。收率78%、HPLC純度91.0%、黏稠固體1
H-NMR(CDCl3
)δ 1.14-1.46 (m, 12H), 2.47 (t, 4H), 2.9-3.6 (m, 8H), 4.2 (s, 2H), 7.5-8.1 (m, 20H)
於實施例2的步驟(iv)中,使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-1''-基-9H-芴60.00 g(88.9 mmol)代替使用9,9-雙〔2-(2'-四氫吡喃氧基)乙基〕-2,7-二萘-2''-基-9H-芴60.00 g(88.9 mmol),除此以外按照實施例2的步驟(iv)中記載的操作,獲得目標物35.13 g。收率78%、HPLC純度95.4%、黏稠固體、1
H-NMR(DMSO-d6
)δ 2.3 (t, 4H), 2.9 (t, 4H), 4.2 (2, 2H), 7.5-8.2 (m, 20H)
(比較合成例1)
於實施例1中,使用苯基硼酸13.41 g(0.11 mol)代替使用19.17 g(0.11 mol)的萘-2-硼酸,除此以外按照實施例1中記載的操作,以無色結晶的形式獲得9,9-雙(2'-羥基乙基)-2,7-二苯基-9H-芴19.9 g。
2.聚碳酸酯樹脂的製造
(實施例12)
將實施例1中獲得的9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴20.26 g(40 mmol)、碳酸二苯酯(以下,有時簡稱為「DPC」)8.56 g(40 mmol)及0.02M-碳酸氫鈉水溶液15 μL(3×10-6
莫耳)裝入至帶餾出裝置的反應器中,於240℃、100 kPa下反應1小時。之後,將減壓度調整為19 kPa並使其反應20分鐘後,於該溫度該壓力下反應70分鐘。其次將減壓度調整為16 kPa,並使其反應20分鐘,進而將減壓度調整為13 kPa並使其反應20分鐘後,花費40分鐘將減壓度設為130 Pa,於該壓力下反應30分鐘而達到規定的轉矩,結果利用氮氣將真空放壓,從而將聚碳酸酯樹脂抽出。
所獲得的聚碳酸酯樹脂的重量平均分子量(Mw)為32300,Tg為135℃。
該聚碳酸酯樹脂的折射率(n633)為1.7608。
(比較例2)
於實施例12中,使用9,9-雙(2'-羥基乙基)-2,7-二苯基-9H-芴16.26 g(40 mmol)代替使用實施例1中獲得的9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴20.26 g(40 mmol),除此以外設為實施例12中記載的操作,獲得聚碳酸酯樹脂。
所獲得的聚碳酸酯樹脂的重量平均分子量(Mw)為28300,Tg為112℃。
該聚碳酸酯樹脂的折射率(n633)為1.6959。
(實施例13)
將實施例2中獲得的9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴20.26 g(40 mmol)、碳酸二苯酯8.56 g(40 mmol)及0.02M-碳酸氫鈉水溶液15 μL(3×10-6
莫耳)裝入至帶餾出裝置的反應器中,於260℃、100 kPa下反應20分鐘,於270℃、100 kPa下反應30分鐘。之後,將減壓度調整為22 kPa並使其反應20分鐘後,於該溫度該壓力下反應60分鐘。其次將減壓度調整為16 kPa,並使其反應20分鐘,進而將減壓度調整為13 kPa並使其反應20分鐘後,花費40分鐘將減壓度設為130 Pa,於該壓力下反應30分鐘而達到規定的轉矩,結果利用氮氣將真空放壓,從而將聚碳酸酯樹脂抽出。
所獲得的聚碳酸酯樹脂是重量平均分子量(Mw)為4250、Tg為115℃、Tm為172℃(熱量:1.87 J/g)的結晶性聚合物。
該聚碳酸酯樹脂的折射率(n633)為1.7708。
(實施例14)
將實施例3中獲得的9,9-雙(2'-羥基乙基)-2,7-雙〔二苯並[b,d]呋喃-4''-基〕-9H-芴23.46 g(40 mmol)、DPC 8.56 g(40 mmol)及0.02M-碳酸氫鈉水溶液15 μL(3×10-6
莫耳)裝入至帶餾出裝置的反應器中,於240℃、100 kPa下反應1小時。之後,將減壓度調整為22 kPa,並使其反應20分鐘,進而將減壓度調整為13 kPa並使其反應20分鐘後,花費40分鐘將減壓度設為130 Pa,於該壓力下反應30分鐘而達到規定的轉矩,結果利用氮氣將真空放壓,從而將聚碳酸酯樹脂抽出。
所獲得的聚碳酸酯樹脂的重量平均分子量(Mw)為8430,Tg為118℃。
該聚碳酸酯樹脂的折射率(n633)為1.730。
(實施例15)
於實施例14中,使用實施例5中獲得的9,9-雙(2'-羥基乙基)-2,7-雙〔3-(萘-2-基)苯基〕-9H-芴26.35 g(40 mmol)代替使用實施例3中獲得的9,9-雙(2'-羥基乙基)-2,7-雙〔二苯並[b,d]呋喃-4''-基〕-9H-芴23.46 g(40 mmol),除此以外按照實施例14中記載的操作製造聚碳酸酯樹脂。
所獲得的聚碳酸酯樹脂的重量平均分子量(Mw)為5240,Tg為105℃。
該聚碳酸酯樹脂的折射率(n633)為1.735。
(實施例16)
於實施例14中,使用實施例6中獲得的9,9-雙(2'-羥基乙基)-2,7-二菲-9''-基-9H-芴24.27 g(40 mmol)代替使用實施例3中獲得的9,9-雙(2'-羥基乙基)-2,7-雙〔二苯並[b,d]呋喃-4''-基〕-9H-芴23.46 g(40 mmol),除此以外按照實施例14中記載的操作製造聚碳酸酯樹脂。
所獲得的聚碳酸酯樹脂的重量平均分子量(Mw)為5550,Tg為126℃。
該聚碳酸酯樹脂的折射率(n633)為1.718。
(實施例17)
於實施例14中,使用實施例8中獲得的9,9-雙(2'-羥基乙基)-2,7-雙(4''-苯氧基苯基)-9H-芴23.63 g(40 mmol)代替使用實施例3中獲得的9,9-雙(2'-羥基乙基)-2,7-雙〔二苯並[b,d]呋喃-4''-基〕-9H-芴23.46 g(40 mmol),除此以外按照實施例14中記載的操作製造聚碳酸酯樹脂。
所獲得的聚碳酸酯樹脂的重量平均分子量(Mw)為4870,Tg為67℃。
該聚碳酸酯樹脂的折射率(n633)為1.715。
(實施例18)
於實施例14中,使用實施例9中獲得的9,9-雙(2'-羥基乙基)-2,7-雙(4''-苯基萘-1''-基)-9H-芴26.35 g(40 mmol)代替使用實施例3中獲得的9,9-雙(2'-羥基乙基)-2,7-雙〔二苯並[b,d]呋喃-4''-基〕-9H-芴23.46 g(40 mmol),除此以外按照實施例14中記載的操作製造聚碳酸酯樹脂。
所獲得的聚碳酸酯樹脂是重量平均分子量(Mw)為6170、Tg為122℃、Tm為273℃(熱量:8.82 J/g)的結晶性聚合物。
該聚碳酸酯樹脂的折射率(n633)為1.796。
(實施例19)
將實施例2中獲得的9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴4.04 g(8 mmol)、9,9-雙〔4'-(2''-羥基乙氧基)苯基〕-9H-芴10.52 g(24 mmol)、雙酚A 1.32 g(8 mmol)、DPC 8.57 g(40 mmol)及0.02M-碳酸氫鈉水溶液15 μL(3×10-6
莫耳)裝入至帶餾出裝置的反應器中,於240℃、100 kPa下反應1小時。之後,將減壓度調整為22 kPa,並使其反應20分鐘,進而將減壓度調整為13 kPa並使其反應20分鐘後,花費40分鐘將減壓度設為130 Pa,於該壓力下反應30分鐘而達到規定的轉矩,結果利用氮氣將真空放壓,從而將聚碳酸酯樹脂抽出。
所獲得的聚碳酸酯樹脂的重量平均分子量(Mw)為32500,Tg為139℃。
該聚碳酸酯樹脂的折射率(n633)為1.713。
另外,於250℃下進行了熱壓的聚碳酸酯樹脂的500 μm厚的片的總光線透過率為82%。
(實施例20)
將實施例4中獲得的9,9-雙(2'-羥基乙基)-2,7-雙〔4-(萘-2-基)苯基〕-9H-芴4.00 g(6 mmol)、9,9-雙〔4'-(2''-羥基乙氧基)苯基〕-9H-芴7.98 g(18 mmol)、雙酚A 1.39 g(6 mmol)、DPC 6.55 g(30 mmol)及0.02M-碳酸氫鈉水溶液10 μL(2×10-6
mol)裝入至帶餾出裝置的反應器中,於270℃、100 kPa下反應1小時。之後,將減壓度調整為22 kPa,並使其反應20分鐘,進而將減壓度調整為13 kPa並使其反應20分鐘後,花費40分鐘將減壓度設為130 Pa,於該壓力下反應70分鐘而達到規定的轉矩,結果利用氮氣將真空放壓,從而將聚碳酸酯樹脂抽出。
所獲得的聚碳酸酯樹脂的重量平均分子量(Mw)為27800,Tg為157℃。聚碳酸酯樹脂的外觀為無色透明。
(實施例21)
將包含實施例2中獲得的9,9-雙(2'-羥基乙基)-2,7-二萘-2''-基-9H-芴3.0375 g(6 mmol)、9,9-雙〔4'-(2''-羥基乙氧基)苯基〕-9H-芴6.1380 g(14 mmol)、2,6-萘二甲酸二甲酯4.8850 g(8 mmol)及四異丙醇鈦3.7 μl(以Ti計為50 ppm)的混合物裝入至帶餾出裝置的反應器中,於280℃、100 kPa下反應1小時。之後,將減壓度調整為20 kPa,並使其反應20分鐘,進而將減壓度調整為13 kPa,並使其反應20分鐘後,花費30分鐘將減壓度設為130 Pa,於該壓力下反應30分鐘而達到規定的轉矩,結果利用氮氣將真空放壓,從而將聚酯樹脂抽出。
所獲得的聚酯樹脂的重量平均分子量(Mw)為6300,Tg為118℃。
根據以上可理解,由本實施形態的通式(1)所表示的化合物獲得的聚碳酸酯樹脂具有高折射率。
本申請案主張以2020年7月28日申請的日本專利申請案特願2020-127221號為基礎的優先權,將其揭示的全部內容併入本申請案中。
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Claims (8)
- 如請求項1所述的化合物,其中所述通式(1)中的o及p為2。
- 一種樹脂,其是將如請求項1至請求項3中任一項所述的通式(1)所表示的化合物聚合而成。
- 一種聚碳酸酯樹脂,其是自如請求項1至請求項3中任一項所述的通式(1)所表示的化合物衍生。
- 一種光學成形體,其包含如請求項4或請求項5所述的樹脂。
- 如請求項6所述的光學成形體,其為光學透鏡。
- 如請求項6所述的光學成形體,其為光學膜。
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