TWI606080B - 聚碳酸酯之製造方法 - Google Patents
聚碳酸酯之製造方法 Download PDFInfo
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- TWI606080B TWI606080B TW105104060A TW105104060A TWI606080B TW I606080 B TWI606080 B TW I606080B TW 105104060 A TW105104060 A TW 105104060A TW 105104060 A TW105104060 A TW 105104060A TW I606080 B TWI606080 B TW I606080B
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- Prior art keywords
- polycarbonate
- reactor
- temperature
- reaction
- dihydroxy compound
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- 229920000515 polycarbonate Polymers 0.000 title claims description 191
- 239000004417 polycarbonate Substances 0.000 title claims description 191
- 238000004519 manufacturing process Methods 0.000 title description 36
- 150000001875 compounds Chemical class 0.000 claims description 164
- 230000000052 comparative effect Effects 0.000 claims description 64
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 54
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 39
- 150000004650 carbonic acid diesters Chemical class 0.000 claims description 31
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 27
- 235000019253 formic acid Nutrition 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 239000000470 constituent Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 15
- 238000003756 stirring Methods 0.000 description 169
- 238000006068 polycondensation reaction Methods 0.000 description 97
- 239000002994 raw material Substances 0.000 description 80
- 238000006243 chemical reaction Methods 0.000 description 76
- 238000000034 method Methods 0.000 description 61
- -1 alkylene glycol Chemical compound 0.000 description 57
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 53
- 239000000600 sorbitol Substances 0.000 description 53
- 238000006116 polymerization reaction Methods 0.000 description 50
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 49
- 125000002723 alicyclic group Chemical group 0.000 description 36
- 229920000642 polymer Polymers 0.000 description 35
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- 239000000155 melt Substances 0.000 description 29
- 239000000463 material Substances 0.000 description 28
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 27
- 230000003287 optical effect Effects 0.000 description 27
- 239000003054 catalyst Substances 0.000 description 24
- 238000004821 distillation Methods 0.000 description 24
- 238000002156 mixing Methods 0.000 description 23
- 230000009477 glass transition Effects 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 239000006227 byproduct Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 15
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- 238000004040 coloring Methods 0.000 description 12
- 125000005647 linker group Chemical group 0.000 description 11
- 238000000465 moulding Methods 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 11
- 238000005809 transesterification reaction Methods 0.000 description 11
- 239000000178 monomer Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229910000147 aluminium phosphate Inorganic materials 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
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
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- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 150000004292 cyclic ethers Chemical group 0.000 description 7
- 230000006866 deterioration Effects 0.000 description 7
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- 238000004898 kneading Methods 0.000 description 7
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229920005668 polycarbonate resin Polymers 0.000 description 6
- 239000004431 polycarbonate resin Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 238000001746 injection moulding Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 238000009792 diffusion process Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
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- 229910052759 nickel Inorganic materials 0.000 description 4
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- 238000007086 side reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
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- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
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- 125000004429 atom Chemical group 0.000 description 3
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 3
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 3
- 229910001863 barium hydroxide Inorganic materials 0.000 description 3
- UCVMQZHZWWEPRC-UHFFFAOYSA-L barium(2+);hydrogen carbonate Chemical compound [Ba+2].OC([O-])=O.OC([O-])=O UCVMQZHZWWEPRC-UHFFFAOYSA-L 0.000 description 3
- AGXUVMPSUKZYDT-UHFFFAOYSA-L barium(2+);octadecanoate Chemical compound [Ba+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AGXUVMPSUKZYDT-UHFFFAOYSA-L 0.000 description 3
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 3
- 239000002585 base Substances 0.000 description 3
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- 238000006297 dehydration reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
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- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- NNJPAMQRBHASEV-UHFFFAOYSA-N (2-phosphonophenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1P(O)(O)=O NNJPAMQRBHASEV-UHFFFAOYSA-N 0.000 description 2
- CYOQTWZWFHXPDM-UHFFFAOYSA-N (2-tridecylphenyl) dihydrogen phosphate Chemical compound CCCCCCCCCCCCCc1ccccc1OP(O)(O)=O CYOQTWZWFHXPDM-UHFFFAOYSA-N 0.000 description 2
- KLDXJTOLSGUMSJ-UNTFVMJOSA-N (3s,3ar,6s,6ar)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-UNTFVMJOSA-N 0.000 description 2
- TYCLKLCKLGCVEZ-UHFFFAOYSA-N 1,1-bis(2,6-ditert-butyl-4-methylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol phosphono dihydrogen phosphate Chemical compound OP(O)(=O)OP(=O)(O)O.C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1C(C)(C)C)C)C(C)(C)C TYCLKLCKLGCVEZ-UHFFFAOYSA-N 0.000 description 2
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- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
- NCMRSHZOFGKWRG-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)phenyl]-10h-anthracen-9-yl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1(C=2C=CC(OCCO)=CC=2)C2=CC=CC=C2CC2=CC=CC=C21 NCMRSHZOFGKWRG-UHFFFAOYSA-N 0.000 description 2
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- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
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- 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
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- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
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- 238000007599 discharging Methods 0.000 description 2
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- 125000000623 heterocyclic group Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
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- NVTNQIBQPLGHGE-UHFFFAOYSA-N n,n-dibutylbutan-1-amine;hydrate Chemical compound [OH-].CCCC[NH+](CCCC)CCCC NVTNQIBQPLGHGE-UHFFFAOYSA-N 0.000 description 1
- JEUXZUSUYIHGNL-UHFFFAOYSA-N n,n-diethylethanamine;hydrate Chemical compound O.CCN(CC)CC JEUXZUSUYIHGNL-UHFFFAOYSA-N 0.000 description 1
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- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 description 1
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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 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WKJXXIJJVMOWCA-UHFFFAOYSA-N phenyl dipropan-2-yl phosphate Chemical compound CC(C)OP(=O)(OC(C)C)OC1=CC=CC=C1 WKJXXIJJVMOWCA-UHFFFAOYSA-N 0.000 description 1
- KEWQEYWDKQFKLA-UHFFFAOYSA-N phenyl tridecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCOP(O)(=O)OC1=CC=CC=C1 KEWQEYWDKQFKLA-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002961 polybutylene succinate Polymers 0.000 description 1
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- 229920000728 polyester Polymers 0.000 description 1
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- 229920001228 polyisocyanate Polymers 0.000 description 1
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- 239000004626 polylactic acid Substances 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- 229940103091 potassium benzoate Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
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- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 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
- 230000008569 process Effects 0.000 description 1
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- 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
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- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
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- 125000006850 spacer group Chemical group 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-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
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- GAJQCIFYLSXSEZ-UHFFFAOYSA-L tridecyl phosphate Chemical compound CCCCCCCCCCCCCOP([O-])([O-])=O GAJQCIFYLSXSEZ-UHFFFAOYSA-L 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- GPHXJBZAVNFMKX-UHFFFAOYSA-M triethyl(phenyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)C1=CC=CC=C1 GPHXJBZAVNFMKX-UHFFFAOYSA-M 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- FDGZUBKNYGBWHI-UHFFFAOYSA-N trioctadecyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC FDGZUBKNYGBWHI-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical class [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Liquid Crystal (AREA)
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| JP2007322490 | 2007-12-13 | ||
| JP2007322491 | 2007-12-13 |
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| TW201617382A TW201617382A (zh) | 2016-05-16 |
| TWI606080B true TWI606080B (zh) | 2017-11-21 |
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| TW105104060A TWI606080B (zh) | 2007-12-13 | 2008-12-12 | 聚碳酸酯之製造方法 |
| TW097148425A TWI428369B (zh) | 2007-12-13 | 2008-12-12 | 聚碳酸酯之製造方法 |
| TW102140657A TWI554546B (zh) | 2007-12-13 | 2008-12-12 | 聚碳酸酯之製造方法 |
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| Application Number | Title | Priority Date | Filing Date |
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| TW097148425A TWI428369B (zh) | 2007-12-13 | 2008-12-12 | 聚碳酸酯之製造方法 |
| TW102140657A TWI554546B (zh) | 2007-12-13 | 2008-12-12 | 聚碳酸酯之製造方法 |
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| US (1) | US8445624B2 (enExample) |
| EP (3) | EP3061782A1 (enExample) |
| JP (3) | JP4697295B2 (enExample) |
| KR (1) | KR101285525B1 (enExample) |
| CN (3) | CN101896535B (enExample) |
| TW (3) | TWI606080B (enExample) |
| WO (1) | WO2009075305A1 (enExample) |
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| JP5001110B2 (ja) * | 2007-10-04 | 2012-08-15 | 帝人株式会社 | ポリカーボネート樹脂およびその製造方法 |
| KR101285525B1 (ko) * | 2007-12-13 | 2013-07-17 | 미쓰비시 가가꾸 가부시키가이샤 | 폴리카보네이트의 제조 방법 |
| WO2010061927A1 (ja) * | 2008-11-28 | 2010-06-03 | 三菱化学株式会社 | ポリカーボネート樹脂、ポリカーボネート樹脂組成物、光学フィルム及びポリカーボネート樹脂成形品 |
| WO2010061929A1 (ja) * | 2008-11-28 | 2010-06-03 | 三菱化学株式会社 | ポリカーボネート樹脂、ポリカーボネート樹脂組成物、光学フィルム及びポリカーボネート樹脂成形品 |
| US8399598B2 (en) * | 2009-04-16 | 2013-03-19 | Teijin Limited | Copolycarbonate and process for producing the same |
| EP3520981B1 (en) * | 2009-11-30 | 2022-06-15 | Mitsubishi Chemical Corporation | Polycarbonate resins and processes for producing the same |
| JP5895339B2 (ja) * | 2009-12-11 | 2016-03-30 | 三菱化学株式会社 | ポリカーボネート樹脂 |
| JP5978554B2 (ja) * | 2009-12-22 | 2016-08-24 | 三菱化学株式会社 | ポリカーボネート樹脂組成物及び成形品 |
| JP5978555B2 (ja) * | 2010-01-07 | 2016-08-24 | 三菱化学株式会社 | ポリカーボネート樹脂組成物及びその成形品 |
| JP5966251B2 (ja) | 2010-03-26 | 2016-08-10 | 三菱化学株式会社 | ポリカーボネート樹脂組成物及び成形品 |
| JP5502556B2 (ja) * | 2010-03-30 | 2014-05-28 | 大王製紙株式会社 | シリカ複合粒子の製造方法 |
| JP5486377B2 (ja) * | 2010-03-31 | 2014-05-07 | 大王製紙株式会社 | シリカ複合混合無機粒子の製造方法及びシリカ複合混合無機粒子 |
| WO2011129940A1 (en) | 2010-04-14 | 2011-10-20 | Dow Global Technologies Llc | Polycarbonate polyols and polyurethanes made therefrom |
| CN102844353B (zh) | 2010-04-14 | 2016-02-17 | 三菱化学株式会社 | 聚碳酸酯二醇及其制备方法，以及使用了其的聚氨酯和活性能量射线固化性聚合物组合物 |
| WO2011149073A1 (ja) | 2010-05-27 | 2011-12-01 | 三菱化学株式会社 | ポリカーボネート樹脂およびそれよりなる透明フィルム |
| JP2012067294A (ja) * | 2010-08-25 | 2012-04-05 | Mitsubishi Chemicals Corp | ポリカーボネート樹脂組成物及び成形品 |
| JP2012067287A (ja) * | 2010-08-26 | 2012-04-05 | Mitsubishi Chemicals Corp | 樹脂成形品 |
| JP5786556B2 (ja) * | 2010-08-26 | 2015-09-30 | 三菱化学株式会社 | 樹脂成形品の製造方法 |
| JP6044058B2 (ja) * | 2010-08-31 | 2016-12-14 | 三菱化学株式会社 | ポリカーボネート樹脂組成物及び成形品 |
| EP2662396B1 (en) | 2011-01-07 | 2023-06-07 | Mitsubishi Chemical Corporation | Production method of polycarbonate |
| WO2012111718A1 (ja) * | 2011-02-16 | 2012-08-23 | 三菱化学株式会社 | ポリカーボネート樹脂組成物及び成形品 |
| JP5895581B2 (ja) * | 2011-02-16 | 2016-03-30 | 三菱化学株式会社 | ポリカーボネート樹脂組成物及び成形品 |
| KR101898306B1 (ko) | 2011-03-30 | 2018-09-12 | 미쯔비시 케미컬 주식회사 | 폴리카보네이트 수지의 제조 방법 |
| JP5987406B2 (ja) * | 2011-03-30 | 2016-09-07 | 三菱化学株式会社 | ポリカーボネート樹脂の製造方法 |
| JP5906887B2 (ja) * | 2011-03-30 | 2016-04-20 | 三菱化学株式会社 | ポリカーボネート樹脂の製造方法 |
| KR101898308B1 (ko) | 2011-03-30 | 2018-09-12 | 미쯔비시 케미컬 주식회사 | 폴리카보네이트 수지의 제조 방법 |
| KR20130122980A (ko) * | 2011-03-31 | 2013-11-11 | 미쓰비시 가가꾸 가부시키가이샤 | 폴리카보네이트 수지의 제조 방법, 폴리카보네이트 수지, 폴리카보네이트 수지 필름, 그리고 폴리카보네이트 수지 펠릿 및 폴리카보네이트 수지 필름의 제조 방법 |
| JP5857852B2 (ja) * | 2011-03-31 | 2016-02-10 | 三菱化学株式会社 | ポリカーボネートの製造方法、ポリカーボネートペレットおよび透明フィルム |
| CN103459463B (zh) * | 2011-03-31 | 2015-09-30 | 三菱化学株式会社 | 聚碳酸酯的制造方法以及透明薄膜 |
| WO2012133853A1 (ja) * | 2011-03-31 | 2012-10-04 | 三菱化学株式会社 | ポリカーボネートの製造方法およびポリカーボネートペレット |
| KR101944129B1 (ko) * | 2011-03-31 | 2019-01-30 | 미쯔비시 케미컬 주식회사 | 폴리카보네이트 수지의 제조 방법, 폴리카보네이트 수지, 폴리카보네이트 수지제 필름 및 폴리카보네이트 수지 펠릿의 제조 방법 |
| WO2012133855A1 (ja) * | 2011-03-31 | 2012-10-04 | 三菱化学株式会社 | ポリカーボネート樹脂の製造方法 |
| EP2692498B1 (en) * | 2011-03-31 | 2019-10-02 | Mitsubishi Chemical Corporation | Method for manufacturing polycarbonate resin |
| CN103562264B (zh) | 2011-05-30 | 2016-08-17 | 三菱化学株式会社 | 聚碳酸酯多元醇的制造方法及使用该聚碳酸酯多元醇的聚氨酯 |
| JP2013084584A (ja) * | 2011-09-30 | 2013-05-09 | Mitsubishi Chemicals Corp | Ｌｅｄ照明用部材 |
| JP2013103977A (ja) * | 2011-11-11 | 2013-05-30 | Mitsubishi Rayon Co Ltd | 重合体または重合体溶液の製造方法、重合体、重合体溶液 |
| TW201341424A (zh) | 2011-12-28 | 2013-10-16 | Mitsubishi Gas Chemical Co | 高分子量聚碳酸酯樹脂之連續製造方法 |
| KR102136974B1 (ko) | 2012-02-20 | 2020-07-23 | 미쯔비시 케미컬 주식회사 | 수지 조성물 및 그 성형체 |
| JP6167570B2 (ja) * | 2012-03-30 | 2017-07-26 | 三菱ケミカル株式会社 | 芳香族ポリカーボネートの製造方法及び製造設備 |
| JP2013209581A (ja) * | 2012-03-30 | 2013-10-10 | Mitsubishi Chemicals Corp | 成形体 |
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| EP2952536A3 (en) | 2016-03-23 |
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| JP5857406B2 (ja) | 2016-02-10 |
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| EP2952536A2 (en) | 2015-12-09 |
| JP2011080091A (ja) | 2011-04-21 |
| TWI554546B (zh) | 2016-10-21 |
| EP2952536B1 (en) | 2021-02-24 |
| US20110034646A1 (en) | 2011-02-10 |
| TW201617382A (zh) | 2016-05-16 |
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