TW583219B - Process for the production of polycarbonate - Google Patents
Process for the production of polycarbonate Download PDFInfo
- Publication number
- TW583219B TW583219B TW091119263A TW91119263A TW583219B TW 583219 B TW583219 B TW 583219B TW 091119263 A TW091119263 A TW 091119263A TW 91119263 A TW91119263 A TW 91119263A TW 583219 B TW583219 B TW 583219B
- Authority
- TW
- Taiwan
- Prior art keywords
- polycarbonate
- group
- phenoxycarbonyl
- phenyl
- carbonate
- Prior art date
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- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 85
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 85
- 238000000034 method Methods 0.000 title claims description 52
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 83
- -1 phenoxy, benzyl Chemical group 0.000 claims abstract description 80
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 238000011049 filling Methods 0.000 claims description 20
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 15
- 150000002989 phenols Chemical class 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 238000002844 melting Methods 0.000 claims description 13
- 230000008018 melting Effects 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 230000002079 cooperative effect Effects 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 238000005809 transesterification reaction Methods 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 7
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- 239000007822 coupling agent Substances 0.000 claims description 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 239000002981 blocking agent Substances 0.000 claims description 4
- 150000004650 carbonic acid diesters Chemical class 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 4
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
- YREGHLXGICXCQA-UHFFFAOYSA-N (2-phenylmethoxyphenyl)methyl hydrogen carbonate Chemical compound OC(=O)OCC1=CC=CC=C1OCC1=CC=CC=C1 YREGHLXGICXCQA-UHFFFAOYSA-N 0.000 claims 1
- RMTZJDQQUXFDOJ-UHFFFAOYSA-N 2-hydroxy-3,4-diphenylbenzoic acid Chemical compound C=1C=CC=CC=1C1=C(O)C(C(=O)O)=CC=C1C1=CC=CC=C1 RMTZJDQQUXFDOJ-UHFFFAOYSA-N 0.000 claims 1
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 22
- 239000006227 byproduct Substances 0.000 description 15
- 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 13
- 230000000052 comparative effect Effects 0.000 description 12
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical class OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 6
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 229960000969 phenyl salicylate Drugs 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000006085 branching agent Substances 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- VGHVJQXWDXRTRJ-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-2-phenylethanone Chemical compound OC1=CC=CC=C1C(=O)CC1=CC=CC=C1 VGHVJQXWDXRTRJ-UHFFFAOYSA-N 0.000 description 2
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-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
- 150000001639 boron compounds Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000005027 hydroxyaryl group Chemical group 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- GPFJHNSSBHPYJK-UHFFFAOYSA-N (3-methylphenyl) hydrogen carbonate Chemical compound CC1=CC=CC(OC(O)=O)=C1 GPFJHNSSBHPYJK-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
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 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 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- RSSGMIIGVQRGDS-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-phenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=CC=C1 RSSGMIIGVQRGDS-UHFFFAOYSA-N 0.000 description 1
- YTRKBSVUOQIJOR-UHFFFAOYSA-N 4-[2-(4-hydroxy-1-methylcyclohexa-2,4-dien-1-yl)propan-2-yl]-4-methylcyclohexa-1,5-dien-1-ol Chemical compound C1C=C(O)C=CC1(C)C(C)(C)C1(C)CC=C(O)C=C1 YTRKBSVUOQIJOR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DHGXBGYCISZSMU-UHFFFAOYSA-N C(OC)(OC1=C(C=CC=C1)CC=1C(O)=CC=CC1)=O Chemical compound C(OC)(OC1=C(C=CC=C1)CC=1C(O)=CC=CC1)=O DHGXBGYCISZSMU-UHFFFAOYSA-N 0.000 description 1
- WKXLBMSIZWFZMI-UHFFFAOYSA-N C1=CC=C(C=C1)C2=C(C(=CC=C2)OC(=O)O)CC3=CC=CC=C3O Chemical compound C1=CC=C(C=C1)C2=C(C(=CC=C2)OC(=O)O)CC3=CC=CC=C3O WKXLBMSIZWFZMI-UHFFFAOYSA-N 0.000 description 1
- IVSJLKUMBSPGHB-UHFFFAOYSA-N C=1C=CC=C(CC=2C=CC=CC=2)C=1OC(=O)OC1=CC=CC=C1CC1=CC=CC=C1 Chemical compound C=1C=CC=C(CC=2C=CC=CC=2)C=1OC(=O)OC1=CC=CC=C1CC1=CC=CC=C1 IVSJLKUMBSPGHB-UHFFFAOYSA-N 0.000 description 1
- QFMNKBLKCMHBCR-UHFFFAOYSA-N CCC1=CC=CC=C1C2=CC=CC=C2OC(=O)O Chemical compound CCC1=CC=CC=C1C2=CC=CC=C2OC(=O)O QFMNKBLKCMHBCR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YBYPIHIBEKCZHL-UHFFFAOYSA-N [O].C1(=CC=CC=C1)C(C)(C)C1=CC=CC=C1 Chemical compound [O].C1(=CC=CC=C1)C(C)(C)C1=CC=CC=C1 YBYPIHIBEKCZHL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 229910001038 basic metal oxide Inorganic materials 0.000 description 1
- CJPIDIRJSIUWRJ-UHFFFAOYSA-N benzene-1,2,4-tricarbonyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C(C(Cl)=O)=C1 CJPIDIRJSIUWRJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- MUCRFDZUHPMASM-UHFFFAOYSA-N bis(2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=CC=CC=C1Cl MUCRFDZUHPMASM-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- VYBMHUHRNNELCP-UHFFFAOYSA-N chloroarsinic acid Chemical compound O[AsH](Cl)=O VYBMHUHRNNELCP-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000110 cooling liquid Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- BJCPQBMZYYGEPJ-UHFFFAOYSA-M dimethyl(diphenyl)azanium;hydroxide Chemical compound [OH-].C=1C=CC=CC=1[N+](C)(C)C1=CC=CC=C1 BJCPQBMZYYGEPJ-UHFFFAOYSA-M 0.000 description 1
- FHESUNXRPBHDQM-UHFFFAOYSA-N diphenyl benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OC=2C=CC=CC=2)=CC=1C(=O)OC1=CC=CC=C1 FHESUNXRPBHDQM-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- ZIRIVHVGOAIFRG-UHFFFAOYSA-N methyl 2-(2-carboxyoxyphenyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC=CC=C1OC(O)=O ZIRIVHVGOAIFRG-UHFFFAOYSA-N 0.000 description 1
- MOVBJUGHBJJKOW-UHFFFAOYSA-N methyl 2-amino-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1N MOVBJUGHBJJKOW-UHFFFAOYSA-N 0.000 description 1
- ZTHFCQCESXOLMQ-UHFFFAOYSA-N methyl 2-hydroxybenzoate;phenyl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1.COC(=O)C1=CC=CC=C1O ZTHFCQCESXOLMQ-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- SJDACOMXKWHBOW-UHFFFAOYSA-N oxyphenisatine Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2NC1=O SJDACOMXKWHBOW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 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
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
-
- 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
-
- 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
-
- 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
- C08G64/42—Chemical after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/948,253 US6525163B1 (en) | 2001-09-07 | 2001-09-07 | Process for the production of polycarbonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW583219B true TW583219B (en) | 2004-04-11 |
Family
ID=25487545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091119263A TW583219B (en) | 2001-09-07 | 2002-08-26 | Process for the production of polycarbonate |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6525163B1 (enExample) |
| EP (1) | EP1427770B1 (enExample) |
| JP (1) | JP4237619B2 (enExample) |
| KR (1) | KR100900112B1 (enExample) |
| CN (1) | CN100349952C (enExample) |
| DE (1) | DE60202691T2 (enExample) |
| TW (1) | TW583219B (enExample) |
| WO (1) | WO2003022905A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60126431T2 (de) * | 2000-12-28 | 2007-08-23 | General Electric Co. | Verfahren zur herstellung von polycarbonat |
| US6870025B2 (en) * | 2001-07-24 | 2005-03-22 | General Electric Company | Method of polycarbonate preparation |
| US20030120025A1 (en) * | 2001-09-07 | 2003-06-26 | Brack Hans Peter | Process for the production of polycarbonate |
| US6706846B2 (en) * | 2001-10-10 | 2004-03-16 | General Electric Company | Method for end-capping polycarbonate resins and composition for use in same |
| US6747119B2 (en) * | 2002-03-28 | 2004-06-08 | General Electric Company | Method and system for preparing a polycarbonate, copolymerization reagent and polycarbonate |
| US7041775B2 (en) * | 2004-04-20 | 2006-05-09 | General Electric Company | Method for preparing a polycarbonate oligomer mixture at low temperature for manufacturing polycarbonate |
| US7312352B2 (en) * | 2004-08-02 | 2007-12-25 | Paul William Buckley | Method of preparing ester-substituted diaryl carbonates |
| KR100614586B1 (ko) * | 2004-08-13 | 2006-08-25 | 주식회사 삼양사 | 내스크래치성이 우수한 폴리카보네이트 수지 조성물, 이를이용한 폴리카보네이트 글레이징 및 그의 제조방법 |
| US7105626B2 (en) * | 2004-09-10 | 2006-09-12 | General Electric Company | Method for incorporating alkyl ester endgroups to improve the release properties of melt polycarbonate |
| US7132498B2 (en) * | 2004-09-27 | 2006-11-07 | General Electric Company | Process to make polycarbonate from bismethylsalicylcarbonate (BMSC) |
| US7230066B2 (en) * | 2004-12-16 | 2007-06-12 | General Electric Company | Polycarbonate—ultem block copolymers |
| KR100868238B1 (ko) * | 2005-08-31 | 2008-11-12 | 주식회사 삼양사 | 표면경도 및 내스크래치성이 우수한 폴리카보네이트글레이징 |
| KR100889829B1 (ko) * | 2005-12-01 | 2009-03-20 | 주식회사 삼양사 | 내스크래치성 및 가공성이 우수한 폴리카보네이트 글레이징 |
| US7365149B2 (en) * | 2005-12-12 | 2008-04-29 | Hans-Peter Brack | Equipment cleaning in the manufacture of polycarbonates |
| US7485695B2 (en) * | 2005-12-21 | 2009-02-03 | Sabic Innovative Plastics Ip B.V | Polycarbonates containing low levels of methyl salicylate prepared by a melt polymerization in a reactive extruder |
| US7485694B2 (en) * | 2005-12-21 | 2009-02-03 | Sabic Innovative Plastics Ip B.V. | Polycarbonates containing low levels of methyl salicylate prepared by a melt polymerization in a reactive extruder |
| US7498399B2 (en) * | 2006-05-31 | 2009-03-03 | Sabic Innovative Plastics Ip B.V. | Method of preparing ester-substituted diaryl carbonates |
| US7495064B2 (en) * | 2006-06-26 | 2009-02-24 | Sabic Innovative Plastics Ip Bv | Manufacture of polycarbonates |
| US7498400B2 (en) * | 2006-06-30 | 2009-03-03 | Sabic Innovative Plastics Ip B.V. | Method of preparing polycarbonate |
| US7482423B2 (en) * | 2006-06-30 | 2009-01-27 | Sabic Innovative Plastics Ip B.V. | Polycarbonates and method of preparing same |
| US7541420B2 (en) * | 2006-06-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Method for making molded polycarbonate articles with improved color |
| US7645851B2 (en) * | 2006-06-30 | 2010-01-12 | Sabic Innovative Plastics Ip B.V. | Polycarbonate with reduced color |
| DE102007022130B4 (de) * | 2007-05-11 | 2015-02-19 | Bayer Intellectual Property Gmbh | Verfahren zur Herstellung von Polycarbonat nach dem Schmelzeumesterungsverfahren |
| US7619053B2 (en) * | 2007-09-28 | 2009-11-17 | Sabic Innovative Plastics Ip B.V. | Monomer solution for producing polycarbonate |
| US7601794B2 (en) * | 2007-09-28 | 2009-10-13 | Sabic Innovative Plastics Ip B.V. | Monomer solution for producing polycarbonate |
| US7632913B2 (en) * | 2007-09-28 | 2009-12-15 | Sabic Innovative Plastics Ip B.V. | Method of producing polycarbonate in a flash devolatilization system |
| US7615605B2 (en) * | 2008-03-26 | 2009-11-10 | Sabic Innovative Plastics Ip B.V. | Monomer solution for producing polycarbonate |
| US7671165B2 (en) * | 2008-05-16 | 2010-03-02 | Sabic Innovative Plastics Ip B.V. | Method of forming polycarbonate |
| US7674872B2 (en) * | 2008-06-17 | 2010-03-09 | Sabic Innovative Plastics Ip B.V. | Method of producing high molecular weight polymer |
| US7547799B1 (en) | 2008-06-20 | 2009-06-16 | Sabic Innovative Plastics Ip B.V. | Method for producing phenolic compound |
| JP6245097B2 (ja) * | 2014-07-14 | 2017-12-13 | 三菱ケミカル株式会社 | 炭酸ジフェニルの製造方法およびポリカーボネートの製造方法 |
| US20190010279A1 (en) * | 2015-09-18 | 2019-01-10 | Mitsubishi Gas Chemical Company, Inc. | Polycarbonate resin, method for producing same, molded article, sheet, and film formed using same, and method for producing same |
| JP2024501410A (ja) * | 2020-12-02 | 2024-01-12 | コベストロ、ドイチュラント、アクチエンゲゼルシャフト | ハロゲン化ジアリールカーボネートを用いたポリカーボネートを製造する方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4520074A (en) | 1984-07-20 | 1985-05-28 | General Electric Company | Polymerizable 3-aroyloxyphenyl carbamates and methods for their preparation and use |
| JPH06145516A (ja) | 1992-05-13 | 1994-05-24 | Mitsui Toatsu Chem Inc | ポリイミド樹脂組成物 |
| JP3253029B2 (ja) | 1992-11-19 | 2002-02-04 | 日本ジーイープラスチックス株式会社 | 芳香族ポリカーボネートの製造法 |
| JPH0790074A (ja) | 1993-09-24 | 1995-04-04 | Idemitsu Kosan Co Ltd | ポリカーボネートの製造方法 |
| EP0764673B1 (en) | 1995-09-19 | 1999-11-17 | Teijin Limited | Process for the production of polycarbonate |
| US5759689A (en) | 1996-06-13 | 1998-06-02 | General Electric Company | Coextruded polycarbonate sheet with improved weathering |
| US6410777B1 (en) | 1997-04-04 | 2002-06-25 | Teijin Limited | Salicylic acid ester derivative and its production |
| DE69824569D1 (de) * | 1997-04-18 | 2004-07-22 | Teijin Ltd | Verfahren zur herstellung von polycarbonatharz |
| US6303734B1 (en) | 1998-03-27 | 2001-10-16 | Teijin Limited | Stabilized aromatic polycarbonate |
-
2001
- 2001-09-07 US US09/948,253 patent/US6525163B1/en not_active Expired - Lifetime
-
2002
- 2002-08-13 KR KR1020047003376A patent/KR100900112B1/ko not_active Expired - Fee Related
- 2002-08-13 CN CNB028219155A patent/CN100349952C/zh not_active Expired - Fee Related
- 2002-08-13 DE DE60202691T patent/DE60202691T2/de not_active Expired - Lifetime
- 2002-08-13 WO PCT/US2002/025688 patent/WO2003022905A1/en not_active Ceased
- 2002-08-13 JP JP2003526976A patent/JP4237619B2/ja not_active Expired - Fee Related
- 2002-08-13 EP EP02768525A patent/EP1427770B1/en not_active Expired - Lifetime
- 2002-08-26 TW TW091119263A patent/TW583219B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60202691D1 (de) | 2005-02-24 |
| JP4237619B2 (ja) | 2009-03-11 |
| EP1427770A1 (en) | 2004-06-16 |
| CN1610715A (zh) | 2005-04-27 |
| JP2005518460A (ja) | 2005-06-23 |
| KR100900112B1 (ko) | 2009-06-01 |
| CN100349952C (zh) | 2007-11-21 |
| KR20040033023A (ko) | 2004-04-17 |
| DE60202691T2 (de) | 2005-12-01 |
| US6525163B1 (en) | 2003-02-25 |
| EP1427770B1 (en) | 2005-01-19 |
| WO2003022905A1 (en) | 2003-03-20 |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |