JP2006504845A - コポリカーボネート製造方法 - Google Patents
コポリカーボネート製造方法 Download PDFInfo
- Publication number
- JP2006504845A JP2006504845A JP2004550090A JP2004550090A JP2006504845A JP 2006504845 A JP2006504845 A JP 2006504845A JP 2004550090 A JP2004550090 A JP 2004550090A JP 2004550090 A JP2004550090 A JP 2004550090A JP 2006504845 A JP2006504845 A JP 2006504845A
- Authority
- JP
- Japan
- Prior art keywords
- bis
- hydroxyphenyl
- hydroxy
- group
- cyclohexane
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 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 95
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 82
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 76
- 238000000034 method Methods 0.000 claims abstract description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 54
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 34
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000009835 boiling Methods 0.000 claims abstract description 28
- 150000004714 phosphonium salts Chemical group 0.000 claims abstract description 25
- 239000000155 melt Substances 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 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 17
- 239000000203 mixture Substances 0.000 claims abstract description 15
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000005205 dihydroxybenzenes Chemical class 0.000 claims abstract description 4
- -1 diaryl carbonates Chemical class 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 14
- 150000004692 metal hydroxides Chemical class 0.000 claims description 14
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 claims description 14
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002685 polymerization catalyst Substances 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical class COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- SGWZVZZVXOJRAQ-UHFFFAOYSA-N 2,6-Dimethyl-1,4-benzenediol Chemical compound CC1=CC(O)=CC(C)=C1O SGWZVZZVXOJRAQ-UHFFFAOYSA-N 0.000 claims description 6
- VJIDDJAKLVOBSE-UHFFFAOYSA-N 2-ethylbenzene-1,4-diol Chemical compound CCC1=CC(O)=CC=C1O VJIDDJAKLVOBSE-UHFFFAOYSA-N 0.000 claims description 6
- FNYDIAAMUCQQDE-UHFFFAOYSA-N 4-methylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C=C1O FNYDIAAMUCQQDE-UHFFFAOYSA-N 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 6
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 229930185605 Bisphenol Natural products 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 5
- 150000001449 anionic compounds Chemical class 0.000 claims description 5
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 5
- 150000002891 organic anions Chemical class 0.000 claims description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- HLNHDVOODYDVRZ-UHFFFAOYSA-M tetraphenylphosphanium;acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HLNHDVOODYDVRZ-UHFFFAOYSA-M 0.000 claims description 4
- GPASWZHHWPVSRG-UHFFFAOYSA-N 2,5-dimethylbenzene-1,4-diol Chemical compound CC1=CC(O)=C(C)C=C1O GPASWZHHWPVSRG-UHFFFAOYSA-N 0.000 claims description 3
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- CDQXVCNCQFXPSF-UHFFFAOYSA-N 2,3,5,6-tetrabromo-4-[1-(2,3,5,6-tetrabromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound BrC1=C(Br)C(O)=C(Br)C(Br)=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2Br)Br)CCCCC1 CDQXVCNCQFXPSF-UHFFFAOYSA-N 0.000 claims description 2
- VRXQOCASOOBADQ-UHFFFAOYSA-N 2,3,5,6-tetrabromo-4-[2-(2,3,5,6-tetrabromo-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound BrC=1C(Br)=C(O)C(Br)=C(Br)C=1C(C)(C)C1=C(Br)C(Br)=C(O)C(Br)=C1Br VRXQOCASOOBADQ-UHFFFAOYSA-N 0.000 claims description 2
- DNFSJFZWNDZYHA-UHFFFAOYSA-N 2,3,5,6-tetrabromo-4-[3,3,5-trimethyl-1-(2,3,5,6-tetrabromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(Br)C(O)=C(Br)C=1Br)Br)C1=C(Br)C(Br)=C(O)C(Br)=C1Br DNFSJFZWNDZYHA-UHFFFAOYSA-N 0.000 claims description 2
- PBYLGADGYCTQOT-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-[1-(2,3,5,6-tetrachloro-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound ClC1=C(Cl)C(O)=C(Cl)C(Cl)=C1C1(C=2C(=C(Cl)C(O)=C(Cl)C=2Cl)Cl)CCCCC1 PBYLGADGYCTQOT-UHFFFAOYSA-N 0.000 claims description 2
- JRWCWHILGVMUTD-UHFFFAOYSA-N 2,6-dibromo-4-[1-(3,5-dibromo-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Br)C(O)=C(Br)C=1)C1=CC(Br)=C(O)C(Br)=C1 JRWCWHILGVMUTD-UHFFFAOYSA-N 0.000 claims description 2
- XJFNFDUOEIPZNK-UHFFFAOYSA-N 2,6-dibromo-4-[1-(3,5-dibromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)CCCCC1 XJFNFDUOEIPZNK-UHFFFAOYSA-N 0.000 claims description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 2
- RPLUVCHAAFRTMW-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-methylphenyl)-3,3,5-trimethylcyclohexyl]-6-methylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Br)C(O)=C(C)C=1)C1=CC(C)=C(O)C(Br)=C1 RPLUVCHAAFRTMW-UHFFFAOYSA-N 0.000 claims description 2
- LTUNFYAQACHQPQ-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-phenylphenyl)-3,3,5-trimethylcyclohexyl]-6-phenylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(Br)C=1)C=1C=CC=CC=1)C1=CC(Br)=C(O)C(C=2C=CC=CC=2)=C1 LTUNFYAQACHQPQ-UHFFFAOYSA-N 0.000 claims description 2
- MLVSCWXAPGXQPH-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-phenylphenyl)cyclohexyl]-6-phenylphenol Chemical compound OC1=C(Br)C=C(C2(CCCCC2)C=2C=C(C(O)=C(Br)C=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 MLVSCWXAPGXQPH-UHFFFAOYSA-N 0.000 claims description 2
- MDOOVKUOPDTSIM-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-propan-2-ylphenyl)-3,3,5-trimethylcyclohexyl]-6-propan-2-ylphenol Chemical compound BrC1=C(O)C(C(C)C)=CC(C2(CC(C)(C)CC(C)C2)C=2C=C(C(O)=C(Br)C=2)C(C)C)=C1 MDOOVKUOPDTSIM-UHFFFAOYSA-N 0.000 claims description 2
- RGMJRYWGSRIVQU-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Br)C(O)=CC=1)C1=CC=C(O)C(Br)=C1 RGMJRYWGSRIVQU-UHFFFAOYSA-N 0.000 claims description 2
- AOJRBWSWENFQGS-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(Br)C(O)=CC=C1C1(C=2C=C(Br)C(O)=CC=2)CCCCC1 AOJRBWSWENFQGS-UHFFFAOYSA-N 0.000 claims description 2
- MTXHQKMTAGXROL-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-5-tert-butyl-4-hydroxyphenyl)cyclohexyl]-6-tert-butylphenol Chemical compound BrC1=C(O)C(C(C)(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=C(Br)C=2)C(C)(C)C)=C1 MTXHQKMTAGXROL-UHFFFAOYSA-N 0.000 claims description 2
- AKUCXWDJOMIBEH-UHFFFAOYSA-N 2-bromo-4-[2-(3-bromo-4-hydroxy-5-methylphenyl)propan-2-yl]-6-methylphenol Chemical compound BrC1=C(O)C(C)=CC(C(C)(C)C=2C=C(Br)C(O)=C(C)C=2)=C1 AKUCXWDJOMIBEH-UHFFFAOYSA-N 0.000 claims description 2
- HSELEXDWBHMZAV-UHFFFAOYSA-N 2-bromo-4-[2-(3-bromo-4-hydroxy-5-phenylphenyl)propan-2-yl]-6-phenylphenol Chemical compound C=1C(Br)=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=1)=CC(Br)=C(O)C=1C1=CC=CC=C1 HSELEXDWBHMZAV-UHFFFAOYSA-N 0.000 claims description 2
- KCUAYENVADKTFG-UHFFFAOYSA-N 2-bromo-4-[2-(3-bromo-4-hydroxy-5-propan-2-ylphenyl)propan-2-yl]-6-propan-2-ylphenol Chemical compound BrC1=C(O)C(C(C)C)=CC(C(C)(C)C=2C=C(C(O)=C(Br)C=2)C(C)C)=C1 KCUAYENVADKTFG-UHFFFAOYSA-N 0.000 claims description 2
- WBVOKGXUEKNTMN-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxy-5-phenylphenyl)-3,3,5-trimethylcyclohexyl]-6-phenylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(Cl)C=1)C=1C=CC=CC=1)C1=CC(Cl)=C(O)C(C=2C=CC=CC=2)=C1 WBVOKGXUEKNTMN-UHFFFAOYSA-N 0.000 claims description 2
- SJPBRWOPJVJYBC-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxy-5-phenylphenyl)cyclohexyl]-6-phenylphenol Chemical compound OC1=C(Cl)C=C(C2(CCCCC2)C=2C=C(C(O)=C(Cl)C=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 SJPBRWOPJVJYBC-UHFFFAOYSA-N 0.000 claims description 2
- LWRQWMMZXJZIDD-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxy-5-propan-2-ylphenyl)cyclohexyl]-6-propan-2-ylphenol Chemical compound ClC1=C(O)C(C(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=C(Cl)C=2)C(C)C)=C1 LWRQWMMZXJZIDD-UHFFFAOYSA-N 0.000 claims description 2
- HQWMAOQEDASZEY-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxy-5-methylphenyl)propan-2-yl]-6-methylphenol Chemical compound ClC1=C(O)C(C)=CC(C(C)(C)C=2C=C(Cl)C(O)=C(C)C=2)=C1 HQWMAOQEDASZEY-UHFFFAOYSA-N 0.000 claims description 2
- ULUCDUBWKNRXIH-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxy-5-phenylphenyl)propan-2-yl]-6-phenylphenol Chemical compound C=1C(Cl)=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=1)=CC(Cl)=C(O)C=1C1=CC=CC=C1 ULUCDUBWKNRXIH-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- TXYRFLUDJODGTP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(3-tert-butyl-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 TXYRFLUDJODGTP-UHFFFAOYSA-N 0.000 claims description 2
- YOHUHRLGZRQQIM-UHFFFAOYSA-N 2-tert-butyl-4-[1-(3-tert-butyl-5-chloro-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]-6-chlorophenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(Cl)C=1)C(C)(C)C)C1=CC(Cl)=C(O)C(C(C)(C)C)=C1 YOHUHRLGZRQQIM-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 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 claims description 2
- BXNVUESPBYOLFC-UHFFFAOYSA-N 3,5-dibromo-4-[1-(2,6-dibromo-4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexyl]-2,6-dimethylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(C)C(O)=C(C)C=1Br)Br)C1=C(Br)C(C)=C(O)C(C)=C1Br BXNVUESPBYOLFC-UHFFFAOYSA-N 0.000 claims description 2
- BHRBWKGEMXXTGA-UHFFFAOYSA-N 3,5-dibromo-4-[1-(2,6-dibromo-4-hydroxy-3,5-dimethylphenyl)cyclohexyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=C(Br)C(C2(CCCCC2)C=2C(=C(C)C(O)=C(C)C=2Br)Br)=C1Br BHRBWKGEMXXTGA-UHFFFAOYSA-N 0.000 claims description 2
- XHHFWEQKCCPWLK-UHFFFAOYSA-N 3,5-dichloro-4-[1-(2,6-dichloro-4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexyl]-2,6-dimethylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(C)C(O)=C(C)C=1Cl)Cl)C1=C(Cl)C(C)=C(O)C(C)=C1Cl XHHFWEQKCCPWLK-UHFFFAOYSA-N 0.000 claims description 2
- SXXOURCVTACNOD-UHFFFAOYSA-N 3,5-dichloro-4-[1-(2,6-dichloro-4-hydroxy-3,5-dimethylphenyl)cyclohexyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=C(Cl)C(C2(CCCCC2)C=2C(=C(C)C(O)=C(C)C=2Cl)Cl)=C1Cl SXXOURCVTACNOD-UHFFFAOYSA-N 0.000 claims description 2
- HSRPEBYMFQNIEC-UHFFFAOYSA-N 3,5-dichloro-4-[2-(2,6-dichloro-4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=C(Cl)C(C(C)(C)C=2C(=C(C)C(O)=C(C)C=2Cl)Cl)=C1Cl HSRPEBYMFQNIEC-UHFFFAOYSA-N 0.000 claims description 2
- WUGKVYDVIGOPSI-UHFFFAOYSA-N 4-(4-hydroxy-3-methylphenyl)-2-methylphenol Chemical group C1=C(O)C(C)=CC(C=2C=C(C)C(O)=CC=2)=C1 WUGKVYDVIGOPSI-UHFFFAOYSA-N 0.000 claims description 2
- BIOIMCYUMXGFMM-UHFFFAOYSA-N 4-(4-hydroxy-3-octylphenyl)-2-octylphenol Chemical group C1=C(O)C(CCCCCCCC)=CC(C=2C=C(CCCCCCCC)C(O)=CC=2)=C1 BIOIMCYUMXGFMM-UHFFFAOYSA-N 0.000 claims description 2
- UVPFWYYCIQGBKX-UHFFFAOYSA-N 4-[1-(4-hydroxy-2,3,5,6-tetramethylphenyl)cyclohexyl]-2,3,5,6-tetramethylphenol Chemical compound CC1=C(O)C(C)=C(C)C(C2(CCCCC2)C=2C(=C(C)C(O)=C(C)C=2C)C)=C1C UVPFWYYCIQGBKX-UHFFFAOYSA-N 0.000 claims description 2
- XYVIZSMBSJIYLC-UHFFFAOYSA-N 4-[1-(4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexyl]-2,6-dimethylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C)C(O)=C(C)C=1)C1=CC(C)=C(O)C(C)=C1 XYVIZSMBSJIYLC-UHFFFAOYSA-N 0.000 claims description 2
- BWCAVNWKMVHLFW-UHFFFAOYSA-N 4-[1-(4-hydroxy-3,5-dimethylphenyl)cyclohexyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C2(CCCCC2)C=2C=C(C)C(O)=C(C)C=2)=C1 BWCAVNWKMVHLFW-UHFFFAOYSA-N 0.000 claims description 2
- XOZBBYKQVOEIGK-UHFFFAOYSA-N 4-[1-(4-hydroxy-3,5-diphenylphenyl)-3,3,5-trimethylcyclohexyl]-2,6-diphenylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(C=1)C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC(C=2C=CC=CC=2)=C(O)C(C=2C=CC=CC=2)=C1 XOZBBYKQVOEIGK-UHFFFAOYSA-N 0.000 claims description 2
- MOZQWEPHBHLFBF-UHFFFAOYSA-N 4-[1-(4-hydroxy-3,5-diphenylphenyl)cyclohexyl]-2,6-diphenylphenol Chemical compound OC1=C(C=2C=CC=CC=2)C=C(C2(CCCCC2)C=2C=C(C(O)=C(C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 MOZQWEPHBHLFBF-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- HHMYOZSUJUQIRL-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-phenylphenyl)-3,3,5-trimethylcyclohexyl]-2-phenylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=CC=1)C=1C=CC=CC=1)C1=CC=C(O)C(C=2C=CC=CC=2)=C1 HHMYOZSUJUQIRL-UHFFFAOYSA-N 0.000 claims description 2
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- OJTHLNYBRBMCBW-UHFFFAOYSA-N 4,4'-propane-2,2-diylbis(tetrachlorophenol) Chemical compound ClC=1C(Cl)=C(O)C(Cl)=C(Cl)C=1C(C)(C)C1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl OJTHLNYBRBMCBW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AWKDEQSSJOJYMP-UHFFFAOYSA-N 4-[1-(4-hydroxy-2,3,5,6-tetramethylphenyl)-3,3,5-trimethylcyclohexyl]-2,3,5,6-tetramethylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(C)C(O)=C(C)C=1C)C)C1=C(C)C(C)=C(O)C(C)=C1C AWKDEQSSJOJYMP-UHFFFAOYSA-N 0.000 description 1
- XEWPEIOKCHAXBH-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexyl]-2-methylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C)C(O)=CC=1)C1=CC=C(O)C(C)=C1 XEWPEIOKCHAXBH-UHFFFAOYSA-N 0.000 description 1
- BQFWXJYYZILERJ-UHFFFAOYSA-N 4-[1-[4-hydroxy-3,5-di(propan-2-yl)phenyl]-3,3,5-trimethylcyclohexyl]-2,6-di(propan-2-yl)phenol Chemical compound CC(C)C1=C(O)C(C(C)C)=CC(C2(CC(C)(C)CC(C)C2)C=2C=C(C(O)=C(C(C)C)C=2)C(C)C)=C1 BQFWXJYYZILERJ-UHFFFAOYSA-N 0.000 description 1
- WORNSJBXZNNDDJ-UHFFFAOYSA-N 4-[1-[4-hydroxy-3,5-di(propan-2-yl)phenyl]cyclohexyl]-2,6-di(propan-2-yl)phenol Chemical compound CC(C)C1=C(O)C(C(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=C(C(C)C)C=2)C(C)C)=C1 WORNSJBXZNNDDJ-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WFTCMHYQCGRZPR-UHFFFAOYSA-N CC(C=C1Br)=CC(C2(CCCCC2)C(C=C(C)C=C2Br)=C2O)=C1O Chemical compound CC(C=C1Br)=CC(C2(CCCCC2)C(C=C(C)C=C2Br)=C2O)=C1O WFTCMHYQCGRZPR-UHFFFAOYSA-N 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
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000220010 Rhode Species 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
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000004650 carbonic acid diesters Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012937 correction 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
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 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
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- 238000000465 moulding Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006384 oligomerization reaction Methods 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
- 230000000704 physical effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- C08G64/20—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
-
- 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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/284,567 US6657038B1 (en) | 2002-11-01 | 2002-11-01 | Method for making copolycarbonates |
| PCT/US2003/033716 WO2004041907A1 (en) | 2002-11-01 | 2003-10-24 | Method for making copolycarbonates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006504845A true JP2006504845A (ja) | 2006-02-09 |
| JP2006504845A5 JP2006504845A5 (enExample) | 2006-12-21 |
Family
ID=29549769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004550090A Withdrawn JP2006504845A (ja) | 2002-11-01 | 2003-10-24 | コポリカーボネート製造方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6657038B1 (enExample) |
| EP (1) | EP1560871B1 (enExample) |
| JP (1) | JP2006504845A (enExample) |
| KR (2) | KR101192500B1 (enExample) |
| CN (1) | CN100500734C (enExample) |
| AT (1) | ATE342297T1 (enExample) |
| AU (1) | AU2003286649A1 (enExample) |
| DE (1) | DE60309061T2 (enExample) |
| TW (1) | TW200420610A (enExample) |
| WO (1) | WO2004041907A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011500376A (ja) * | 2007-10-31 | 2011-01-06 | ブンデスドルクレイ ゲーエムベーハー | ポリカーボネート多層ポリマー構造体を作製する方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7057004B2 (en) * | 2004-01-29 | 2006-06-06 | General Electric Company | Process for the production of copolycarbonates with reduced color |
| US8916259B2 (en) * | 2008-12-18 | 2014-12-23 | Sabic Global Technologies B.V. | Multilayer films for insert mold decoration, methods for making the same, and articles made therefrom |
| US7834125B2 (en) * | 2008-12-18 | 2010-11-16 | Sabic Innovative Plastics Ip B.V. | Polycarbonates, compositions made therefrom, methods of manufacture thereof, and articles therefrom |
| EP2937372B1 (en) * | 2014-04-25 | 2020-04-22 | SABIC Global Technologies B.V. | A method of melt polymerizing polycarbonate and polycarbonates derived therefrom |
| EP2937371A1 (en) * | 2014-04-25 | 2015-10-28 | SABIC Global Technologies B.V. | A method of melt polymerizing polycarbonate and polycarbonates derived therefrom |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3431927B2 (ja) | 1991-04-09 | 2003-07-28 | 日本ジーイープラスチックス株式会社 | 共重合ポリカーボネート |
| JPH0578466A (ja) | 1991-04-09 | 1993-03-30 | Nippon G Ii Plast Kk | 共重合ポリカーボネートの製造方法 |
| JP2922337B2 (ja) * | 1991-06-28 | 1999-07-19 | 日本ジーイープラスチックス株式会社 | 共重合ポリカーボネートの製造方法 |
| US5510450A (en) | 1992-02-21 | 1996-04-23 | General Electric Company | Method of producing copolymerized polycarbonates |
| US5336751A (en) | 1992-04-06 | 1994-08-09 | General Electric Company | Preparation of copolycarbonate from resorcinol |
| JP3262860B2 (ja) * | 1992-10-22 | 2002-03-04 | 日本ジーイープラスチックス株式会社 | 共重合ポリカーボネートの製造方法 |
| JPH07102164A (ja) | 1993-09-30 | 1995-04-18 | Nippon G Ii Plast Kk | 熱可塑性樹脂組成物 |
| JPH07102162A (ja) | 1993-10-06 | 1995-04-18 | Nippon G Ii Plast Kk | ガラス強化ポリカーボネート系樹脂組成物 |
| JPH07207085A (ja) | 1994-01-12 | 1995-08-08 | Nippon G Ii Plast Kk | 耐衝撃性樹脂組成物 |
| US5412061A (en) * | 1994-03-07 | 1995-05-02 | General Electric Company | Polycarbonate melt condensation synthesis using a tetraorganophosphonium carboxylate salt catalyst |
| DK0788351T3 (da) | 1994-11-10 | 2003-05-26 | Univ Kentucky Res Found | Implanterbar, genopfyldelig anordning til hastighedsreguleret lægemiddeladministration direkte til en indre del af kroppen |
| US5717056A (en) | 1996-05-24 | 1998-02-10 | General Electric Company | Method for preparing polycarbonate by solid state polymerization |
| KR20000022201A (ko) * | 1996-06-26 | 2000-04-25 | 도미나가 가즈토 | 폴리카보네이트의 제조방법 |
| US6228973B1 (en) * | 2000-06-02 | 2001-05-08 | General Electric Company | Method for preparing high molecular weight polycarbonate |
-
2002
- 2002-11-01 US US10/284,567 patent/US6657038B1/en not_active Expired - Lifetime
-
2003
- 2003-10-24 JP JP2004550090A patent/JP2006504845A/ja not_active Withdrawn
- 2003-10-24 AT AT03777856T patent/ATE342297T1/de not_active IP Right Cessation
- 2003-10-24 KR KR1020057008214A patent/KR101192500B1/ko not_active Expired - Fee Related
- 2003-10-24 WO PCT/US2003/033716 patent/WO2004041907A1/en not_active Ceased
- 2003-10-24 DE DE60309061T patent/DE60309061T2/de not_active Expired - Lifetime
- 2003-10-24 AU AU2003286649A patent/AU2003286649A1/en not_active Abandoned
- 2003-10-24 EP EP03777856A patent/EP1560871B1/en not_active Expired - Lifetime
- 2003-10-24 CN CNB2003801074962A patent/CN100500734C/zh not_active Expired - Fee Related
- 2003-10-24 KR KR1020117009031A patent/KR20110069116A/ko not_active Ceased
- 2003-10-31 TW TW092130507A patent/TW200420610A/zh unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011500376A (ja) * | 2007-10-31 | 2011-01-06 | ブンデスドルクレイ ゲーエムベーハー | ポリカーボネート多層ポリマー構造体を作製する方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003286649A1 (en) | 2004-06-07 |
| EP1560871A1 (en) | 2005-08-10 |
| CN1732203A (zh) | 2006-02-08 |
| KR20110069116A (ko) | 2011-06-22 |
| TW200420610A (en) | 2004-10-16 |
| CN100500734C (zh) | 2009-06-17 |
| KR20050086443A (ko) | 2005-08-30 |
| KR101192500B1 (ko) | 2012-10-17 |
| DE60309061D1 (de) | 2006-11-23 |
| US6657038B1 (en) | 2003-12-02 |
| WO2004041907A1 (en) | 2004-05-21 |
| ATE342297T1 (de) | 2006-11-15 |
| DE60309061T2 (de) | 2007-05-10 |
| EP1560871B1 (en) | 2006-10-11 |
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