KR20040030938A - 폴리카보네이트의 제조 방법 - Google Patents
폴리카보네이트의 제조 방법 Download PDFInfo
- Publication number
- KR20040030938A KR20040030938A KR10-2004-7001819A KR20047001819A KR20040030938A KR 20040030938 A KR20040030938 A KR 20040030938A KR 20047001819 A KR20047001819 A KR 20047001819A KR 20040030938 A KR20040030938 A KR 20040030938A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- bisphenol
- polycarbonate
- bis
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 72
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 72
- 238000000034 method Methods 0.000 title claims abstract description 65
- -1 tetraalkyl phosphonium carboxylate Chemical class 0.000 claims abstract description 74
- 238000006243 chemical reaction Methods 0.000 claims abstract description 68
- 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 claims abstract description 55
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 25
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000047 product Substances 0.000 claims description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 46
- 238000005809 transesterification reaction Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 claims description 15
- 239000006227 byproduct Substances 0.000 claims description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229930185605 Bisphenol Natural products 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical group CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- XBQRPFBBTWXIFI-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C)(C)C1=CC=C(O)C(Cl)=C1 XBQRPFBBTWXIFI-UHFFFAOYSA-N 0.000 claims description 3
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- SVOBELCYOCEECO-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-methylphenyl)cyclohexyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(CCCCC2)C=2C=C(C)C(O)=CC=2)=C1 SVOBELCYOCEECO-UHFFFAOYSA-N 0.000 claims description 3
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 claims description 3
- IJWIRZQYWANBMP-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-propan-2-ylphenyl)propan-2-yl]-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)C)=C1 IJWIRZQYWANBMP-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007942 carboxylates Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000002891 organic anions Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- MUCRFDZUHPMASM-UHFFFAOYSA-N bis(2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=CC=CC=C1Cl MUCRFDZUHPMASM-UHFFFAOYSA-N 0.000 claims description 2
- DQPSUGZZTADITQ-UHFFFAOYSA-N bis(2-nitrophenyl) carbonate Chemical compound [O-][N+](=O)C1=CC=CC=C1OC(=O)OC1=CC=CC=C1[N+]([O-])=O DQPSUGZZTADITQ-UHFFFAOYSA-N 0.000 claims description 2
- FSTRGOSTJXVFGV-UHFFFAOYSA-N bis(4-chlorophenyl) carbonate Chemical compound C1=CC(Cl)=CC=C1OC(=O)OC1=CC=C(Cl)C=C1 FSTRGOSTJXVFGV-UHFFFAOYSA-N 0.000 claims description 2
- VSNGLBILYXOLGD-UHFFFAOYSA-N bis(4-fluorophenyl) carbonate Chemical compound C1=CC(F)=CC=C1OC(=O)OC1=CC=C(F)C=C1 VSNGLBILYXOLGD-UHFFFAOYSA-N 0.000 claims description 2
- IZJIAOFBVVYSMA-UHFFFAOYSA-N bis(4-methylphenyl) carbonate Chemical compound C1=CC(C)=CC=C1OC(=O)OC1=CC=C(C)C=C1 IZJIAOFBVVYSMA-UHFFFAOYSA-N 0.000 claims description 2
- ACBQROXDOHKANW-UHFFFAOYSA-N bis(4-nitrophenyl) carbonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)OC1=CC=C([N+]([O-])=O)C=C1 ACBQROXDOHKANW-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 abstract description 13
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000000376 reactant Substances 0.000 abstract description 2
- 230000003606 oligomerizing effect Effects 0.000 abstract 1
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- 102100029290 Transthyretin Human genes 0.000 description 3
- 108050000089 Transthyretin Proteins 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 3
- PMMUFDGWDXRPRQ-UHFFFAOYSA-N 2-hydroxy-5-[2-(4-hydroxyphenyl)propan-2-yl]benzoic acid Chemical compound C=1C=C(O)C(C(O)=O)=CC=1C(C)(C)C1=CC=C(O)C=C1 PMMUFDGWDXRPRQ-UHFFFAOYSA-N 0.000 description 2
- XILNKQWGKMTFFA-UHFFFAOYSA-N 4-[2-(4-hydroxy-2-methylphenyl)propan-2-yl]-3-methylphenol Chemical compound CC1=CC(O)=CC=C1C(C)(C)C1=CC=C(O)C=C1C XILNKQWGKMTFFA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052760 oxygen Chemical group 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- WHDWTYUVZOXXKX-UHFFFAOYSA-M tetrabutylphosphanium;formate Chemical compound [O-]C=O.CCCC[P+](CCCC)(CCCC)CCCC WHDWTYUVZOXXKX-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RHXYELSOROSQRL-UHFFFAOYSA-N 2-hydroxy-5-[2-(4-hydroxy-2-methylphenyl)propan-2-yl]-4-methylbenzoic acid Chemical compound CC1=CC(O)=CC=C1C(C)(C)C1=CC(C(O)=O)=C(O)C=C1C RHXYELSOROSQRL-UHFFFAOYSA-N 0.000 description 1
- ODOOTSAYZCWANC-UHFFFAOYSA-N 2-hydroxy-5-[2-(4-hydroxy-3-methylphenyl)propan-2-yl]-3-methylbenzoic acid Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C(O)=C(C)C=2)C(O)=O)=C1 ODOOTSAYZCWANC-UHFFFAOYSA-N 0.000 description 1
- 241000408939 Atalopedes campestris Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000005618 Fries rearrangement reaction Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- PQFHDQYJJVVZLN-UHFFFAOYSA-N bis(2-fluorophenyl) carbonate Chemical compound FC1=CC=CC=C1OC(=O)OC1=CC=CC=C1F PQFHDQYJJVVZLN-UHFFFAOYSA-N 0.000 description 1
- BKMGMIWOLYYOCK-UHFFFAOYSA-L butanedioate;tetrabutylphosphanium Chemical compound [O-]C(=O)CCC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC.CCCC[P+](CCCC)(CCCC)CCCC BKMGMIWOLYYOCK-UHFFFAOYSA-L 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000006066 glass batch Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 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 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- UOWATYKFBJJASJ-UHFFFAOYSA-L oxalate;tetrabutylphosphanium Chemical compound [O-]C(=O)C([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC.CCCC[P+](CCCC)(CCCC)CCCC UOWATYKFBJJASJ-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WQTXZYHEQMEIDJ-UHFFFAOYSA-L propanedioate;tetrabutylphosphanium Chemical compound [O-]C(=O)CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC.CCCC[P+](CCCC)(CCCC)CCCC WQTXZYHEQMEIDJ-UHFFFAOYSA-L 0.000 description 1
- FJDDUGDZOMECHA-UHFFFAOYSA-M propanoate;tetrabutylphosphanium Chemical compound CCC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC FJDDUGDZOMECHA-UHFFFAOYSA-M 0.000 description 1
- OYNYQOJNEQMVMJ-UHFFFAOYSA-M propanoate;tetramethylphosphanium Chemical compound CCC([O-])=O.C[P+](C)(C)C OYNYQOJNEQMVMJ-UHFFFAOYSA-M 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- PVGBHEUCHKGFQP-UHFFFAOYSA-N sodium;n-[5-amino-2-(4-aminophenyl)sulfonylphenyl]sulfonylacetamide Chemical compound [Na+].CC(=O)NS(=O)(=O)C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 PVGBHEUCHKGFQP-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- PCOLIQZVEZUFAA-UHFFFAOYSA-L terephthalate;tetrabutylphosphanium Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1.CCCC[P+](CCCC)(CCCC)CCCC.CCCC[P+](CCCC)(CCCC)CCCC PCOLIQZVEZUFAA-UHFFFAOYSA-L 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- ZMENDZUPTXLTAG-UHFFFAOYSA-M tetrabutylphosphanium;benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.CCCC[P+](CCCC)(CCCC)CCCC ZMENDZUPTXLTAG-UHFFFAOYSA-M 0.000 description 1
- JRQMGUGXUVNKFF-UHFFFAOYSA-M tetraethylphosphanium;acetate Chemical compound CC([O-])=O.CC[P+](CC)(CC)CC JRQMGUGXUVNKFF-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- HYVDRSVZYMKTKG-UHFFFAOYSA-M tetramethylphosphanium;acetate Chemical compound CC([O-])=O.C[P+](C)(C)C HYVDRSVZYMKTKG-UHFFFAOYSA-M 0.000 description 1
- LEAIJASTTLNZRQ-UHFFFAOYSA-M tetrapropylphosphanium;acetate Chemical compound CC([O-])=O.CCC[P+](CCC)(CCC)CCC LEAIJASTTLNZRQ-UHFFFAOYSA-M 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- VLYYMDKODYFUEQ-UHFFFAOYSA-M tributyl(pentyl)phosphanium;acetate Chemical compound CC([O-])=O.CCCCC[P+](CCCC)(CCCC)CCCC VLYYMDKODYFUEQ-UHFFFAOYSA-M 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
-
- 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
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/924,137 US6569985B2 (en) | 2001-08-08 | 2001-08-08 | Method for making polycarbonate |
| US09/924,137 | 2001-08-08 | ||
| PCT/US2002/023175 WO2003014188A1 (en) | 2001-08-08 | 2002-07-19 | Method for making polycarbonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040030938A true KR20040030938A (ko) | 2004-04-09 |
Family
ID=25449762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2004-7001819A Ceased KR20040030938A (ko) | 2001-08-08 | 2002-07-19 | 폴리카보네이트의 제조 방법 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6569985B2 (https=) |
| EP (1) | EP1417248A1 (https=) |
| JP (1) | JP2004537623A (https=) |
| KR (1) | KR20040030938A (https=) |
| CN (1) | CN1289568C (https=) |
| WO (1) | WO2003014188A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170115559A (ko) * | 2015-02-26 | 2017-10-17 | 사빅 글로벌 테크놀러지스 비.브이. | 폴리카보네이트 합성에서 유기 불순물의 조절 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6797802B2 (en) * | 2002-10-07 | 2004-09-28 | General Electric Company | Method of polycarbonate preparation |
| US20070208159A1 (en) * | 2006-03-02 | 2007-09-06 | General Electric Company | Poly(arylene ether) block copolymer compositions, methods, and articles |
| 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 |
| US7875217B2 (en) * | 2006-09-29 | 2011-01-25 | Johnson & Johnson Vision Care, Inc. | Excess polymer ring removal during ophthalmic lens manufacture |
| US7666977B2 (en) * | 2007-05-03 | 2010-02-23 | Sabic Innovative Plastics Ip B.V. | Poly(carbonate-co-urea) copolymers and melt transesterification method of preparing these copolymers |
| US7557175B2 (en) * | 2007-05-03 | 2009-07-07 | Sabic Innovative Plastics Ip B.V. | Poly(carbonate-co-urea) copolymers and melt transesterification method of preparing these copolymers |
| US20110224372A1 (en) * | 2008-11-24 | 2011-09-15 | Guenter Jueptner | Process for preparing linear polycarbonate with improved impact properties |
| WO2010065805A2 (en) * | 2008-12-05 | 2010-06-10 | E. I. Du Pont De Nemours And Company | Method for reducing vibrations from a motor vehicle exhaust system |
| US8051947B2 (en) * | 2009-03-12 | 2011-11-08 | E.I. Du Pont De Nemours And Company | Energy absorbing thermoplastic elastomer |
| US8343608B2 (en) | 2010-08-31 | 2013-01-01 | General Electric Company | Use of appended dyes in optical data storage media |
| EP2730618B1 (en) * | 2012-11-07 | 2016-10-12 | SABIC Global Technologies B.V. | Process for producing polycarbonate compositions |
| US20140179855A1 (en) * | 2012-12-20 | 2014-06-26 | Sabic Innovative Plastics Ip B.V. | Thermoplastic compositions, methods of manufacture, and articles thereof |
| US10370533B2 (en) | 2014-06-05 | 2019-08-06 | Sabic Global Technologies B.V. | Thermoplastic composition and laser-welded article |
| JP2017524051A (ja) * | 2014-08-01 | 2017-08-24 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | 分岐構造および環状オリゴマーならびに改善したレオロジー特性を有するコポリカーボネート組成物 |
| CN110982054B (zh) * | 2019-12-28 | 2021-03-12 | 中国科学院过程工程研究所 | 一种用于催化合成聚碳酸酯的复合催化剂及催化合成聚碳酸酯的方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG73354A1 (en) | 1988-07-11 | 2000-06-20 | Ge Plastics Japan Ltd | Process for preparing polycarbonates |
| DE4238123C2 (de) | 1992-11-12 | 2000-03-09 | Bayer Ag | Verfahren zur Herstellung von thermoplastischen Polycarbonaten |
| DE4312390A1 (de) | 1993-04-16 | 1994-10-20 | Bayer Ag | Zweistufen-Verfahren zur Herstellung von thermoplastischem Polycarbonat |
| US5412061A (en) | 1994-03-07 | 1995-05-02 | General Electric Company | Polycarbonate melt condensation synthesis using a tetraorganophosphonium carboxylate salt catalyst |
| DE19504622A1 (de) | 1995-02-13 | 1996-08-14 | Bayer Ag | Zweistufen-Verfahren zur Herstellung von thermoplastischem Polycarbonat |
| DE19612139A1 (de) | 1996-03-27 | 1997-10-02 | Bayer Ag | Zweistufenverfahren zur Herstellung von thermoplastischem Polycarbonat |
| US5717056A (en) * | 1996-05-24 | 1998-02-10 | General Electric Company | Method for preparing polycarbonate by solid state polymerization |
| ATE395373T1 (de) * | 1998-12-18 | 2008-05-15 | Gen Electric | Optischer datenträger enthaltend polycarbonat mit verringertem fries gehalt |
| DE19933128A1 (de) * | 1999-07-19 | 2001-01-25 | Bayer Ag | Polycarbonat und dessen Formkörper |
| US6184335B1 (en) * | 2000-04-10 | 2001-02-06 | General Electric Company | Salts of aryl sulfonic acids as polymerization catalysts |
| US6228973B1 (en) | 2000-06-02 | 2001-05-08 | General Electric Company | Method for preparing high molecular weight polycarbonate |
| US6414106B1 (en) * | 2001-03-02 | 2002-07-02 | General Electric Company | Process for the neutralization of residual acid species in crude dihydric phenols |
-
2001
- 2001-08-08 US US09/924,137 patent/US6569985B2/en not_active Expired - Lifetime
-
2002
- 2002-07-19 WO PCT/US2002/023175 patent/WO2003014188A1/en not_active Ceased
- 2002-07-19 JP JP2003519133A patent/JP2004537623A/ja active Pending
- 2002-07-19 KR KR10-2004-7001819A patent/KR20040030938A/ko not_active Ceased
- 2002-07-19 CN CNB028197321A patent/CN1289568C/zh not_active Expired - Fee Related
- 2002-07-19 EP EP02761147A patent/EP1417248A1/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170115559A (ko) * | 2015-02-26 | 2017-10-17 | 사빅 글로벌 테크놀러지스 비.브이. | 폴리카보네이트 합성에서 유기 불순물의 조절 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1564838A (zh) | 2005-01-12 |
| JP2004537623A (ja) | 2004-12-16 |
| CN1289568C (zh) | 2006-12-13 |
| US6569985B2 (en) | 2003-05-27 |
| WO2003014188A1 (en) | 2003-02-20 |
| EP1417248A1 (en) | 2004-05-12 |
| US20030065129A1 (en) | 2003-04-03 |
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