JP2006501347A - ポリカーボネート樹脂の製造方法 - Google Patents
ポリカーボネート樹脂の製造方法 Download PDFInfo
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- JP2006501347A JP2006501347A JP2004541304A JP2004541304A JP2006501347A JP 2006501347 A JP2006501347 A JP 2006501347A JP 2004541304 A JP2004541304 A JP 2004541304A JP 2004541304 A JP2004541304 A JP 2004541304A JP 2006501347 A JP2006501347 A JP 2006501347A
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- Prior art keywords
- polycarbonate resin
- producing
- resin according
- group
- reaction
- Prior art date
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- 229920005668 polycarbonate resin Polymers 0.000 title claims abstract description 81
- 239000004431 polycarbonate resin Substances 0.000 title claims abstract description 81
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 59
- 239000007790 solid phase Substances 0.000 claims abstract description 38
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 16
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 16
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 14
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 14
- 229920000515 polycarbonate Polymers 0.000 claims description 76
- 239000004417 polycarbonate Substances 0.000 claims description 76
- 238000006243 chemical reaction Methods 0.000 claims description 51
- 238000005809 transesterification reaction Methods 0.000 claims description 46
- 150000004650 carbonic acid diesters Chemical class 0.000 claims description 41
- 239000000126 substance Substances 0.000 claims description 39
- 239000007858 starting material Substances 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 21
- 239000002685 polymerization catalyst Substances 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000003963 antioxidant agent Substances 0.000 claims description 10
- 238000002844 melting Methods 0.000 claims description 10
- 230000008018 melting Effects 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- 239000006085 branching agent Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 230000003078 antioxidant effect Effects 0.000 claims description 8
- 150000007514 bases Chemical class 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 239000011261 inert gas Substances 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000012298 atmosphere Substances 0.000 claims description 5
- 230000009477 glass transition Effects 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims description 3
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XDAGXZXKTKRFMT-UHFFFAOYSA-N propan-2-imine Chemical class CC(C)=N XDAGXZXKTKRFMT-UHFFFAOYSA-N 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 6
- 239000000155 melt Substances 0.000 abstract description 2
- 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 52
- 238000000034 method Methods 0.000 description 41
- -1 bisphenol A Chemical compound 0.000 description 32
- 238000002425 crystallisation Methods 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 230000008025 crystallization Effects 0.000 description 15
- 239000007789 gas Substances 0.000 description 10
- 229930185605 Bisphenol Natural products 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 230000009257 reactivity Effects 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- AAOBUKZEIBZRBI-UHFFFAOYSA-M bis(triphenyl-$l^{5}-phosphanylidene)azanium;acetate Chemical compound CC([O-])=O.C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)=[N+]=P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AAOBUKZEIBZRBI-UHFFFAOYSA-M 0.000 description 6
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 5
- 125000005027 hydroxyaryl group Chemical group 0.000 description 5
- 150000002736 metal compounds Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- VVBXKASDRZXWON-UHFFFAOYSA-N N=[PH3] Chemical class N=[PH3] VVBXKASDRZXWON-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229910000765 intermetallic Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- BRRSNXCXLSVPFC-UHFFFAOYSA-N 2,3,4-Trihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1O BRRSNXCXLSVPFC-UHFFFAOYSA-N 0.000 description 2
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- CKNCVRMXCLUOJI-UHFFFAOYSA-N 3,3'-dibromobisphenol A Chemical compound C=1C=C(O)C(Br)=CC=1C(C)(C)C1=CC=C(O)C(Br)=C1 CKNCVRMXCLUOJI-UHFFFAOYSA-N 0.000 description 2
- SQQOWYUPNYZZPI-UHFFFAOYSA-N 3,5-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(O)=CC(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 SQQOWYUPNYZZPI-UHFFFAOYSA-N 0.000 description 2
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 2
- QHJPJZROUNGTRJ-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)octan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCCCCC)C1=CC=C(O)C=C1 QHJPJZROUNGTRJ-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000011324 bead Substances 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
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- LVRCYPYRKNAAMX-UHFFFAOYSA-M bis(triphenylphosphine)iminium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)N=P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LVRCYPYRKNAAMX-UHFFFAOYSA-M 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
- 239000001273 butane Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical compound COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 2
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OKJFKPFBSPZTAH-UHFFFAOYSA-N (2,4-dihydroxyphenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O OKJFKPFBSPZTAH-UHFFFAOYSA-N 0.000 description 1
- NZADFKWJIQWGNZ-UHFFFAOYSA-N (2-ethylphenyl) diphenyl phosphate Chemical compound CCC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 NZADFKWJIQWGNZ-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZKIOSCVVLXTVDG-UHFFFAOYSA-N 1,2,4,6-tetrabromocyclohexa-3,5-diene-1,3-diol Chemical compound OC1=C(Br)C=C(Br)C(O)(Br)C1Br ZKIOSCVVLXTVDG-UHFFFAOYSA-N 0.000 description 1
- SZEZPYPOANXQRS-UHFFFAOYSA-N 1,2,4,6-tetrafluorocyclohexa-3,5-diene-1,3-diol Chemical compound OC1=C(F)C=C(F)C(O)(F)C1F SZEZPYPOANXQRS-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- FQXOOGHQVPKHPG-UHFFFAOYSA-N 1,3-diazinane-2,4,5-trione Chemical compound O=C1NCC(=O)C(=O)N1 FQXOOGHQVPKHPG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GFMYLYZAYMLEMK-UHFFFAOYSA-N 1-(2-phenylpropan-2-yl)cyclohexa-3,5-diene-1,3-diol Chemical compound C1C(O)=CC=CC1(O)C(C)(C)C1=CC=CC=C1 GFMYLYZAYMLEMK-UHFFFAOYSA-N 0.000 description 1
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- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- JZZBTMVTLBHJHL-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphate Chemical compound ClCC(Cl)COP(=O)(OCC(Cl)CCl)OCC(Cl)CCl JZZBTMVTLBHJHL-UHFFFAOYSA-N 0.000 description 1
- FCFIEBVTVHJMQR-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphite Chemical compound ClCC(Cl)COP(OCC(Cl)CCl)OCC(Cl)CCl FCFIEBVTVHJMQR-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-UHFFFAOYSA-N 0.000 description 1
- BRAZJWSWBBLGAH-UHFFFAOYSA-N tris(2-ethylphenyl) phosphite Chemical class CCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CC)OC1=CC=CC=C1CC BRAZJWSWBBLGAH-UHFFFAOYSA-N 0.000 description 1
- XKEHGKBYZJWLQC-UHFFFAOYSA-N tris(2-hydroxyphenyl) phosphite Chemical compound OC1=CC=CC=C1OP(OC=1C(=CC=CC=1)O)OC1=CC=CC=C1O XKEHGKBYZJWLQC-UHFFFAOYSA-N 0.000 description 1
- OOZBTDPWFHJVEK-UHFFFAOYSA-N tris(2-nonylphenyl) phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC OOZBTDPWFHJVEK-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
- 238000001291 vacuum drying Methods 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
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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/307—General preparatory processes using carbonates and phenols
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
R1、R2、R3、及びR4は各々独立的に炭化水素であり、Zは窒素、リンまたは砒素であり、Xはテトラアリールボロヒドリド、ブロマイド、フェノレート、またはジアリールリン酸塩である。その他に非金属化合物触媒系として米国特許第5,168,112号には一次、二次、または三次アミン化合物、ピリジンのような窒素を含む芳香族化合物誘導体、米国特許第5,418,316号はグアニジンとその誘導体、米国特許第5,618,906号はフォスファジン化合物、米国特許第6,262,219号はピペリジンまたはモルホリンのような窒素が含まれた環状化合物について開示している。
本発明者らは溶融重合条件で安定で反応性が優れていて、優れた触媒活性を維持する方法について研究していたところ、ジヒドロキシ化合物及び炭酸ジエステルを含有する出発原料物質をホスフォラニリデンアンモニウム塩単独、またはホスフォラニリデンアンモニウム塩とアルカリ金属またはアルカリ土類金属を含有する化合物の混合物である重合触媒下でエステル交換反応してポリカーボネート樹脂を製造した結果、溶融重合条件で安定で反応性が優れているだけでなく、高分子量のポリカーボネート樹脂を効率的に製造することができることを確認し、これに基づいて本発明を完成した。
R1、R2、及びR3は各々独立的にメチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、オクチル基、またはシクロヘキシル基などの直鎖状または分枝状のアルキル基またはシクロアルキル基;フェニル基、トリル基、ナフチル基、またはビフェニル基である置換基を有するか或いは有しないアリール基;またはベンジル基である置換基を有するか或いは有しないアリールアルキル基であり、この時R1、R2、及びR3のうちのいずれか二つは互いに結合して環を形成することができ、Xはハロゲン原子、ヒドロキシル基、アルキルオキシ基、アリールオキシ基、アルキルカルボニルオキシ基、アリールカルボニルオキシ基、HCO3、CO3、またはBR4 4(ここで、R4は各々独立的に水素原子、アルキル基、またはアリール基である炭化水素である)であり、cはXがCO3であれば2であり、XがCO3でなければ1である。
R5及びR6は各々独立的にフッ素、塩素、臭素、またはヨードなどのハロゲン原子、またはメチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、2級-ブチル基、3級-ブチル基、ペンチル基、ヘキシル基、シクロヘキシル基、ヘプチル基、またはオクチル基などの炭素数1乃至8のアルキル基であり、d、及びeは各々独立的に0乃至4の整数であり、Zは単一結合、炭素数1乃至8のアルキレン基、炭素数2乃至8のアルキリデン基、炭素数5乃至15のシクロアルキレン基、炭素数5乃至15のシクロアルキリデン基、-S、-SO-、-SO2-、-O-、-CO-、下記の化学式3で示される化合物、または下記の化学式4で示される化合物である:
Ar1,及びAr2は各々独立的にアリール基である。
Ar3、及びAr4は各々独立的にアリール基であり、
D1は前述の芳香族ジヒドロキシ化合物から2個のヒドロキシル基を除去して得られた残基である。
R7及びR8は各々独立的に炭素数1乃至6のアルキル基、または炭素数4乃至7のシクロアルキル基である。
R9及びR10は各々独立的に炭素数1乃至6のアルキル基、または炭素数4乃至7のシクロアルキル基であり、
D2は前述の芳香族ジヒドロキシ化合物から2個のヒドロキシル基を除去して得られた残基である。
Ar5はアリール基であり、
R11は炭素数炭素数1乃至6のアルキル基、または炭素数4乃至7のシクロアルキル基である。
Ar6はアリール基であり、
R12は炭素数1乃至6のアルキル基、または炭素数4乃至7のシクロアルキル基であり、
D3は前述の芳香族ジヒドロキシ化合物から2個のヒドロキシル基を除去して得られた残基である。
nは7乃至30の整数である。
R13は各々独立的に炭素数1乃至12のアルキル基であり、
kは1乃至3の整数である。
磁石撹拌機が内在された300mLのガラス反応器にジヒドロキシ化合物としてビスフェノールA(BPA)85.61g(0.375モル)、及び炭酸ジエステルとしてジフェニルカーボネート84.35g(0.394モル)を加え、ここに重合触媒であるホスフォラニリデンアンモニウム塩としてビス(トリフェニルホスフォラニリデン)アンモニウムアセテートをビスフェノールAの1モルに対して2.5×10-4モルの濃度で充填し、次いで反応器内の雰囲気を窒素で5回置換した。前記反応で得られた混合物を170℃まで加熱し、30分間窒素雰囲気で反応させた。次に、混合物を220℃まで加熱し、この温度で30分間真空度を次第に高めて10mbarの真空まで到達した後、90分間反応させて反応を終了して透明なポリカーボネート樹脂を収得した。
重合触媒としてテトラメチルアンモニウムヒドロキシドをビスフェノールAの1モルに対して2.5×10-4モルの濃度で使用したことを除いては、前記実施例1と同様な方法で実施してポリカーボネート樹脂を製造した。
重合触媒としてテトラブチルホスホニウムヒドロキシドをビスフェノールAの1モルに対して2.5×10-4モルの濃度で使用したことを除いては、前記実施例1と同様な方法で実施してポリカーボネート樹脂を製造した。
重合触媒としてビス(トリフェニルホスフォラニリデン)アンモニウムアセテートをビスフェノールAの1モルに対して1.0×10-5モルの濃度で使用したことを除いては、前記実施例1と同様な方法で実施してポリカーボネート樹脂を製造した。
重合触媒としてビス(トリフェニルホスフォラニリデン)アンモニウムアセテートをビスフェノールAの1モルに対して1.0×10-6モルの濃度で使用したことを除いては、前記実施例1と同様な方法で実施してポリカーボネート樹脂を製造した。
重合触媒として酢酸ナトリウム及びビス(トリフェニルホスフォラニリデン)アンモニウムアセテートをビスフェノールAの1モルに対して1.0×10-6モル、及び2.5×10-4モルの濃度で各々使用したことを除いては、前記実施例1と同様な方法で実施してポリカーボネート樹脂を製造した。
重合触媒として酢酸ナトリウムをビスフェノールAの1モルに対して1.0×10-6モルの濃度で使用したことを除いては、前記実施例1と同様な方法で実施してポリカーボネート樹脂を製造した。
磁石撹拌機が内在された300mLのガラス反応器にジヒドロキシ化合物としてビスフェノールA(BPA)85.61g(0.375モル)、及び炭酸ジエステルとしてジフェニルカーボネート84.35g(0.394モル)を加え、ここに重合触媒であるホスフォラニリデンアンモニウム塩としてビス(トリフェニルホスフォラニリデン)アンモニウムアセテートをビスフェノールAの1モルに対して2.5×10-4モルの濃度で充填し、次いで反応器内の雰囲気を窒素で5回置換した。前記反応で得られた混合物を170℃まで加熱して、30分間窒素雰囲気で反応させた。次に、混合物を220℃まで加熱して、この温度で30分間真空度を次第に高めて10mbarの真空まで到達した後、90分間反応させた。
前記実施例5で重合触媒として酢酸ナトリウムをビスフェノールA対比3.0×10-5モルの濃度で使用して重量平均分子量8,548g/モルのポリカーボネートプレポリマーを製造し、これを利用して前記実施例1と同様な方法で固相重合してポリカーボネート樹脂を製造した。
前記実施例5で重合触媒としてテトラメチルアンモニウムヒドロキシドをビスフェノールA対比2.5×10-4モルの濃度で使用して、重合反応時間を4倍長く実施して重量平均分子量9,094g/モルのポリカーボネートプレポリマーを製造し、これを利用して前記実施例1と同様な方法で固相重合してポリカーボネート樹脂を製造した。
前記実施例5で重合触媒としてテトラブチルホスホニウムヒドロキシドをビスフェノールA対比2.5×10-4モルの濃度で使用して重量平均分子量6,740g/モルのポリカーボネートプレポリマーを製造し、これを利用して前記実施例1と同様な方法で固相重合してポリカーボネート樹脂を製造した。
Claims (22)
- ポリカーボネート樹脂の製造方法において、ジヒドロキシ化合物及び炭酸ジエステルを含有する出発原料物質を窒素含有有機塩基性化合物もしくは窒素含有有機塩基性化合物とアルカリ金属またはアルカリ土類金属を含有する化合物との混合物触媒下で重合する段階を含むポリカーボネート樹脂の製造方法。
- 前記窒素含有有機塩基性化合物はホスフォラニリデンアンモニウム塩である、請求項1に記載のポリカーボネート樹脂の製造方法。
- 前記重合はジヒドロキシ化合物及び炭酸ジエステルを含有する出発原料物質を触媒存在下でエステル交換反応させる段階を含む、請求項2に記載のポリカーボネート樹脂の製造方法。
- 前記ホスフォラニリデンアンモニウム塩が下記の化学式1で示される4級アンモニウム塩である、請求項3に記載のポリカーボネート樹脂の製造方法:
R1、R2、及びR3は各々独立的に直鎖状または分枝状のアルキル基またはシクロアルキル基、置換基を有するか或いは有しないアリール基、または置換基を有するか或いは有しないアリールアルキル基であり、この時、R1、R2、及びR3のうちのある2個は互いに結合して環を形成することができ、
Xはハロゲン原子、ヒドロキシル基、アルキルオキシ基、アリールオキシ基、アルキルカルボニルオキシ基、アリールカルボニルオキシ基、HCO3、CO3、またはBR4 4(ここで、R4は各々独立的に水素原子又はアルキル基もしくはアリール基などの炭化水素である)であり、
cはXがCO3であれば2であり、XがCO3でなければ1である。 - 前記ホスフォラニリデンアンモニウム塩が前記出発原料物質であるジヒドロキシ化合物1モルに対して10-1乃至10-6モル含まれる、請求項3に記載のポリカーボネート樹脂の製造方法。
- 前記ホスフォラニリデンアンモニウム塩及びアルカリ金属もしくはアルカリ土類金属を含有する化合物の混合物が出発原料物質であるジヒドロキシ化合物1モルに対して10-1乃至10-8モル含まれる、請求項3に記載のポリカーボネート樹脂の製造方法。
- 前記アルカリ金属またはアルカリ土類金属を含有する化合物が出発原料物質であるジヒドロキシ化合物1モルに対して10-3乃至10-8モル含まれる、請求項3に記載のポリカーボネート樹脂の製造方法。
- 前記炭酸ジエステル及びジヒドロキシ化合物が0.9乃至1.5のモル比で出発原料物質に含まれる、請求項3に記載のポリカーボネート樹脂の製造方法。
- 終結剤、分枝剤、及び酸化防止剤からなる群より1種以上選択される添加剤を追加的に添加する、請求項3に記載のポリカーボネート樹脂の製造方法。
- 前記終結剤が出発原料物質であるジヒドロキシ化合物1モルに対して0.01乃至10モル%含まれる、請求項9に記載のポリカーボネート樹脂の製造方法。
- 前記エステル交換反応は100乃至330℃の反応温度で実施される、請求項3に記載のポリカーボネート樹脂の製造方法。
- 前記エステル交換反応は反応初期に1乃至10気圧の圧力で実施され、反応後期には0.1乃至100mbarの圧力で実施される、請求項3に記載のポリカーボネート樹脂の製造方法。
- 前記エステル交換反応は0.2乃至10時間の反応時間の間に実施される、請求項3に記載のポリカーボネート樹脂の製造方法。
- a)ジヒドロキシ化合物及び炭酸ジエステルを含有する出発原料物質を
i)ホスフォラニリデンアンモニウム塩または
ii)イ)ホスフォラニリデンアンモニウム塩;及び
ロ)アルカリ金属またはアルカリ土類金属を含有する化合物の混合物
を含む重合触媒下でエステル交換反応で予備重合してポリカーボネートプレポリマーを製造する段階と、
b)前記a)段階のポリカーボネートプレポリマーを固相重合する段階とを含むポリカーボネート樹脂の製造方法。 - 前記ホスフォラニリデンアンモニウム塩が出発原料物質であるジヒドロキシ化合物1モルに対して10-2乃至10-8モル含まれる、請求項14に記載のポリカーボネート樹脂の製造方法。
- 前記炭酸ジエステルがジヒドロキシ化合物1モルに対して0.9乃至2.5モル含まれる、請求項14に記載のポリカーボネート樹脂の製造方法。
- 前記エステル交換反応は50乃至350℃の反応温度、0.1mbar乃至100mbarの反応圧力、及び1分乃至10時間の反応時間で実施される、請求項14に記載のポリカーボネート樹脂の製造方法。
- 前記固相重合する段階の前にポリカーボネートプレポリマーを結晶化する段階をさらに含む、請求項14に記載のポリカーボネート樹脂の製造方法。
- 前記結晶化する段階は、
ポリカーボネートプレポリマーを溶媒に溶解する段階と、
溶媒を蒸発させる段階と、
前記ポリカーボネートプレポリマーに貧溶媒を添加して固体のポリカーボネートプレポリマーを析出させる段階とを含む、請求項18に記載のポリカーボネート樹脂の製造方法。 - 前記結晶化する段階はポリカーボネートプレポリマーをそのガラス転移温度より高くて、その溶融温度より低い温度で加熱する段階を含む、請求項18に記載のポリカーボネート樹脂の製造方法。
- 固相重合する段階で終結剤、分枝剤、及び酸化防止剤からなる群より1種以上選択される添加剤を追加的に添加する、請求項14に記載のポリカーボネート樹脂の製造方法。
- 前記固相重合する段階は不活性気体雰囲気で前記ポリカーボネートプレポリマーをそのガラス転移温度より高くて、その溶融温度より低い温度で加熱する段階を含む、請求項14に記載のポリカーボネート樹脂の製造方法。
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KR1020020059757A KR100576223B1 (ko) | 2002-10-01 | 2002-10-01 | 폴리카보네이트 수지의 제조방법 |
PCT/KR2003/000799 WO2004031259A1 (en) | 2002-10-01 | 2003-04-18 | Method for preparing polycarbonate resin |
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JP4125720B2 JP4125720B2 (ja) | 2008-07-30 |
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US (1) | US7339021B2 (ja) |
EP (1) | EP1546233B1 (ja) |
JP (1) | JP4125720B2 (ja) |
KR (1) | KR100576223B1 (ja) |
CN (1) | CN100577711C (ja) |
AT (1) | ATE369392T1 (ja) |
AU (1) | AU2003225388A1 (ja) |
DE (1) | DE60315480T2 (ja) |
ES (1) | ES2287568T3 (ja) |
TW (1) | TWI259191B (ja) |
WO (1) | WO2004031259A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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ES2403122T3 (es) * | 2004-10-21 | 2013-05-14 | Lg Chem, Ltd. | Procedimiento para la preparación de una resina de policarbonato |
KR20070042594A (ko) * | 2005-10-19 | 2007-04-24 | 삼성코닝 주식회사 | 편평한 측면을 갖는 a면 질화물 반도체 단결정 기판 |
US20110201706A1 (en) * | 2008-11-10 | 2011-08-18 | Dow Global Technologies Llc | Isocyanate trimerisation catalyst system, a precursor formulation, a process for trimerising isocyanates, rigid polyisocyanurate/polyurethane foams made therefrom, and a process for making such foams |
ES2788376T3 (es) * | 2013-04-16 | 2020-10-21 | Agc Inc | Método de fabricación de policarbonato y policarbonato |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
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US3153008A (en) * | 1955-07-05 | 1964-10-13 | Gen Electric | Aromatic carbonate resins and preparation thereof |
DE1274578B (de) * | 1965-01-21 | 1968-08-08 | Bayer Ag | Verfahren zur Herstellung von Cycloalkylaminverbindungen |
US4330664A (en) * | 1979-12-26 | 1982-05-18 | General Electric Company | Polycarbonate transesterification with catalyst containing aluminum hydride or borohydride group |
US5025083A (en) * | 1989-02-10 | 1991-06-18 | Daicel Chemical Industries, Ltd. | Process for preparation of polycarbonate |
US5045632A (en) * | 1989-05-25 | 1991-09-03 | The Dow Chemical Company | Novel bis(phosphoranylidene) ammonium salts |
JP3122721B2 (ja) * | 1989-12-28 | 2001-01-09 | 日本ジーイープラスチックス株式会社 | ポリカーボネート組成物およびその製造方法 |
DE4320156A1 (de) * | 1993-06-18 | 1994-12-22 | Bayer Ag | Verfahren zur Herstellung von thermoplastischen Polycarbonaten |
JPH0753705A (ja) | 1993-08-09 | 1995-02-28 | Idemitsu Petrochem Co Ltd | ポリカーボネートの製造法 |
US5401814A (en) * | 1993-10-13 | 1995-03-28 | The Dow Chemical Company | Process for the preparation of thermoplastic poly(hydroxy ethers) |
US5618906A (en) * | 1994-06-01 | 1997-04-08 | Bayer Aktiengesellschaft | Process for the production of thermoplastic polycarbonates |
JPH0841193A (ja) | 1994-07-29 | 1996-02-13 | Idemitsu Kosan Co Ltd | ポリカーボネートの製造法 |
US5922826A (en) | 1995-01-31 | 1999-07-13 | Idemitsu Kosan Co., Ltd. | Process for producing polycarbonate |
JP3354777B2 (ja) | 1995-01-31 | 2002-12-09 | 出光興産株式会社 | ポリカーボネートの製造方法 |
JP3629827B2 (ja) | 1996-07-31 | 2005-03-16 | 出光興産株式会社 | ポリカーボネートの製造方法 |
DE19728805A1 (de) * | 1997-07-05 | 1999-01-07 | Bayer Ag | Verfahren zur Herstellung von Polycarbonat |
JP2000128977A (ja) | 1998-10-28 | 2000-05-09 | Teijin Ltd | 芳香族ポリカーボネートの製造法 |
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2002
- 2002-10-01 KR KR1020020059757A patent/KR100576223B1/ko active IP Right Grant
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2003
- 2003-04-18 US US10/529,699 patent/US7339021B2/en not_active Expired - Lifetime
- 2003-04-18 AU AU2003225388A patent/AU2003225388A1/en not_active Abandoned
- 2003-04-18 CN CN03825174A patent/CN100577711C/zh not_active Expired - Lifetime
- 2003-04-18 JP JP2004541304A patent/JP4125720B2/ja not_active Expired - Lifetime
- 2003-04-18 AT AT03799187T patent/ATE369392T1/de not_active IP Right Cessation
- 2003-04-18 DE DE60315480T patent/DE60315480T2/de not_active Expired - Lifetime
- 2003-04-18 WO PCT/KR2003/000799 patent/WO2004031259A1/en active IP Right Grant
- 2003-04-18 EP EP03799187A patent/EP1546233B1/en not_active Expired - Lifetime
- 2003-04-18 ES ES03799187T patent/ES2287568T3/es not_active Expired - Lifetime
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Also Published As
Publication number | Publication date |
---|---|
AU2003225388A1 (en) | 2004-04-23 |
TW200408661A (en) | 2004-06-01 |
WO2004031259A1 (en) | 2004-04-15 |
KR20040032195A (ko) | 2004-04-17 |
CN100577711C (zh) | 2010-01-06 |
CN1694915A (zh) | 2005-11-09 |
US20060122359A1 (en) | 2006-06-08 |
ATE369392T1 (de) | 2007-08-15 |
DE60315480T2 (de) | 2008-04-30 |
DE60315480D1 (de) | 2007-09-20 |
ES2287568T3 (es) | 2007-12-16 |
TWI259191B (en) | 2006-08-01 |
JP4125720B2 (ja) | 2008-07-30 |
EP1546233B1 (en) | 2007-08-08 |
EP1546233A1 (en) | 2005-06-29 |
US7339021B2 (en) | 2008-03-04 |
KR100576223B1 (ko) | 2006-05-03 |
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