TWI289574B - Method of preparing polyestercarbonates - Google Patents
Method of preparing polyestercarbonates Download PDFInfo
- Publication number
- TWI289574B TWI289574B TW092107283A TW92107283A TWI289574B TW I289574 B TWI289574 B TW I289574B TW 092107283 A TW092107283 A TW 092107283A TW 92107283 A TW92107283 A TW 92107283A TW I289574 B TWI289574 B TW I289574B
- Authority
- TW
- Taiwan
- Prior art keywords
- carbonate
- bis
- group
- acid
- catalyst
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 58
- -1 activated diaryl carbonate Chemical compound 0.000 claims abstract description 57
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 39
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 27
- 229920000728 polyester Polymers 0.000 claims description 22
- 239000002685 polymerization catalyst Substances 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000000155 melt Substances 0.000 claims description 17
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 229930185605 Bisphenol Natural products 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052784 alkaline earth metal Chemical class 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- NKOPSNSLUIFZFO-UHFFFAOYSA-N carbonic acid;2-methoxybenzoic acid Chemical compound OC(O)=O.COC1=CC=CC=C1C(O)=O.COC1=CC=CC=C1C(O)=O NKOPSNSLUIFZFO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- 239000003426 co-catalyst Substances 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 150000001491 aromatic compounds Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 150000001449 anionic compounds Chemical class 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 150000004679 hydroxides Chemical class 0.000 claims description 3
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 claims description 3
- 150000002891 organic anions Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- XIVVYHYWAJAJJH-UHFFFAOYSA-N 2-butoxybenzoic acid;carbonic acid Chemical compound OC(O)=O.CCCCOC1=CC=CC=C1C(O)=O.CCCCOC1=CC=CC=C1C(O)=O XIVVYHYWAJAJJH-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
- 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 claims description 2
- 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 2
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- HBLSZXRYFSCREB-UHFFFAOYSA-N bis(2,4-dichlorophenyl) carbonate Chemical compound ClC1=CC(Cl)=CC=C1OC(=O)OC1=CC=C(Cl)C=C1Cl HBLSZXRYFSCREB-UHFFFAOYSA-N 0.000 claims description 2
- DEVXPGMBRTYKHS-UHFFFAOYSA-N bis(2-cyanophenyl) carbonate Chemical compound C=1C=CC=C(C#N)C=1OC(=O)OC1=CC=CC=C1C#N DEVXPGMBRTYKHS-UHFFFAOYSA-N 0.000 claims description 2
- PQFHDQYJJVVZLN-UHFFFAOYSA-N bis(2-fluorophenyl) carbonate Chemical compound FC1=CC=CC=C1OC(=O)OC1=CC=CC=C1F PQFHDQYJJVVZLN-UHFFFAOYSA-N 0.000 claims description 2
- POSZYPCJRYUXEU-UHFFFAOYSA-N bis(4-cyanophenyl) carbonate Chemical compound C=1C=C(C#N)C=CC=1OC(=O)OC1=CC=C(C#N)C=C1 POSZYPCJRYUXEU-UHFFFAOYSA-N 0.000 claims description 2
- HZCHHQPBFVITLD-UHFFFAOYSA-N bis(4-ethylphenyl) carbonate Chemical compound C1=CC(CC)=CC=C1OC(=O)OC1=CC=C(CC)C=C1 HZCHHQPBFVITLD-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
- JFQUVGSOOYKCAH-UHFFFAOYSA-N bis[4-(trifluoromethyl)phenyl] carbonate Chemical compound C1=CC(C(F)(F)F)=CC=C1OC(=O)OC1=CC=C(C(F)(F)F)C=C1 JFQUVGSOOYKCAH-UHFFFAOYSA-N 0.000 claims description 2
- GYDIUBRZHJFDFW-UHFFFAOYSA-N carbonic acid;2-ethoxybenzoic acid Chemical compound OC(O)=O.CCOC1=CC=CC=C1C(O)=O.CCOC1=CC=CC=C1C(O)=O GYDIUBRZHJFDFW-UHFFFAOYSA-N 0.000 claims description 2
- ITTYRUSZRZUFKR-UHFFFAOYSA-N carbonic acid;2-phenylmethoxybenzoic acid Chemical compound OC(O)=O.OC(=O)C1=CC=CC=C1OCC1=CC=CC=C1.OC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 ITTYRUSZRZUFKR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical class [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 239000010931 gold Chemical class 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910000342 sodium bisulfate Inorganic materials 0.000 claims description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims 10
- 150000001450 anions Chemical class 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 claims 2
- FNYDIAAMUCQQDE-UHFFFAOYSA-N 4-methylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C=C1O FNYDIAAMUCQQDE-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 claims 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims 2
- BNJOQKFENDDGSC-UHFFFAOYSA-N octadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)=O BNJOQKFENDDGSC-UHFFFAOYSA-N 0.000 claims 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 claims 2
- ZNVZNEACQAUNGE-UHFFFAOYSA-N 1,2-diphenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1C1=CC=CC=C1 ZNVZNEACQAUNGE-UHFFFAOYSA-N 0.000 claims 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 claims 1
- GMDZOEQOTJOQIL-UHFFFAOYSA-N 2,4-bis[4-(dibutylamino)-2-hydroxyphenyl]cyclobutane-1,3-dione Chemical compound OC1=CC(N(CCCC)CCCC)=CC=C1C1C(=O)C(C=2C(=CC(=CC=2)N(CCCC)CCCC)O)C1=O GMDZOEQOTJOQIL-UHFFFAOYSA-N 0.000 claims 1
- LYXCJGJSIWFKHZ-UHFFFAOYSA-N 4-phenylbenzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=CC=C1 LYXCJGJSIWFKHZ-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 claims 1
- LWENJPFDNGZPHJ-UHFFFAOYSA-L O(C1=CC=CC=C1)[Mo]OC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)[Mo]OC1=CC=CC=C1 LWENJPFDNGZPHJ-UHFFFAOYSA-L 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- MUCRFDZUHPMASM-UHFFFAOYSA-N bis(2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=CC=CC=C1Cl MUCRFDZUHPMASM-UHFFFAOYSA-N 0.000 claims 1
- YAPBIDJHZIYQSK-UHFFFAOYSA-N bis(2-ethylphenyl) carbonate Chemical compound CCC1=CC=CC=C1OC(=O)OC1=CC=CC=C1CC YAPBIDJHZIYQSK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- KNBQQUUTGVXWSV-UHFFFAOYSA-N bis[2-(trifluoromethyl)phenyl] carbonate Chemical compound FC(F)(F)C1=CC=CC=C1OC(=O)OC1=CC=CC=C1C(F)(F)F KNBQQUUTGVXWSV-UHFFFAOYSA-N 0.000 claims 1
- GOFURTAJNOZTTO-UHFFFAOYSA-N bis[2-chloro-4-(trifluoromethyl)phenyl] carbonate Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OC(=O)OC1=CC=C(C(F)(F)F)C=C1Cl GOFURTAJNOZTTO-UHFFFAOYSA-N 0.000 claims 1
- 229910052797 bismuth Inorganic materials 0.000 claims 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 1
- XTUQWEXQGVCYCU-UHFFFAOYSA-N carbonic acid 2-propoxybenzoic acid Chemical compound C(O)(O)=O.C(CC)OC=1C(C(=O)O)=CC=CC1 XTUQWEXQGVCYCU-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims 1
- 239000000539 dimer Substances 0.000 claims 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims 1
- ZJTLZYDQJHKRMQ-UHFFFAOYSA-N menadiol Chemical compound C1=CC=CC2=C(O)C(C)=CC(O)=C21 ZJTLZYDQJHKRMQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 claims 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 150000003871 sulfonates Chemical class 0.000 claims 1
- WVRJUMZHKISIJD-UHFFFAOYSA-N tetraazanium;disulfate Chemical class [NH4+].[NH4+].[NH4+].[NH4+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O WVRJUMZHKISIJD-UHFFFAOYSA-N 0.000 claims 1
- 125000004360 trifluorophenyl group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 6
- 238000010348 incorporation Methods 0.000 abstract description 2
- 125000001142 dicarboxylic acid group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920000515 polycarbonate Polymers 0.000 description 9
- 239000004417 polycarbonate Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000004679 31P NMR spectroscopy Methods 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
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 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
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010309 melting process Methods 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Chemical group 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- JPNBVWIRDQVGAC-UHFFFAOYSA-N (2-nitrophenyl) hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1[N+]([O-])=O JPNBVWIRDQVGAC-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- OXOWWPXTTOCKKU-UHFFFAOYSA-N 2-propoxybenzoic acid Chemical compound CCCOC1=CC=CC=C1C(O)=O OXOWWPXTTOCKKU-UHFFFAOYSA-N 0.000 description 1
- COEDEXNNGUYSOV-UHFFFAOYSA-N 3-chlorodioxaphospholane Chemical compound ClP1CCOO1 COEDEXNNGUYSOV-UHFFFAOYSA-N 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 1
- GPNLQCFFHCXCFG-UHFFFAOYSA-N CC(=O)NC1=CC=CC=C1OC(=O)OC1=CC=CC=C1NC(C)=O Chemical compound CC(=O)NC1=CC=CC=C1OC(=O)OC1=CC=CC=C1NC(C)=O GPNLQCFFHCXCFG-UHFFFAOYSA-N 0.000 description 1
- 229910005831 GeO3 Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
- DJUMOTUYTWSRJH-UHFFFAOYSA-J [Na+].[Na+].[Mg+2].[O-]C(=O)N(C([O-])=O)CCN(C([O-])=O)C([O-])=O Chemical compound [Na+].[Na+].[Mg+2].[O-]C(=O)N(C([O-])=O)CCN(C([O-])=O)C([O-])=O DJUMOTUYTWSRJH-UHFFFAOYSA-J 0.000 description 1
- PZAGQUOSOTUKEC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.OS(O)(=O)=O PZAGQUOSOTUKEC-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 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
- 125000006267 biphenyl group Chemical group 0.000 description 1
- JOJNCSKBTSMKKW-UHFFFAOYSA-N bis(2,4,6-trichlorophenyl) carbonate Chemical compound ClC1=CC(Cl)=CC(Cl)=C1OC(=O)OC1=C(Cl)C=C(Cl)C=C1Cl JOJNCSKBTSMKKW-UHFFFAOYSA-N 0.000 description 1
- QHPJQGFYPDCWTG-UHFFFAOYSA-N bis(2,4,6-trifluorophenyl) carbonate Chemical compound FC1=CC(F)=CC(F)=C1OC(=O)OC1=C(F)C=C(F)C=C1F QHPJQGFYPDCWTG-UHFFFAOYSA-N 0.000 description 1
- URZKFDMKDWGAGV-UHFFFAOYSA-N bis(2,4-difluorophenyl) carbonate Chemical compound FC1=CC(F)=CC=C1OC(=O)OC1=CC=C(F)C=C1F URZKFDMKDWGAGV-UHFFFAOYSA-N 0.000 description 1
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Chemical compound [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 description 1
- 235000010237 calcium benzoate Nutrition 0.000 description 1
- 239000004301 calcium benzoate 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
- HZQXCUSDXIKLGS-UHFFFAOYSA-L calcium;dibenzoate;trihydrate Chemical compound O.O.O.[Ca+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HZQXCUSDXIKLGS-UHFFFAOYSA-L 0.000 description 1
- KTAAUBVMSAZOLC-UHFFFAOYSA-L calcium;hexanedioate Chemical compound [Ca+2].[O-]C(=O)CCCCC([O-])=O KTAAUBVMSAZOLC-UHFFFAOYSA-L 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- VGBWDOLBWVJTRZ-UHFFFAOYSA-K cerium(3+);triacetate Chemical compound [Ce+3].CC([O-])=O.CC([O-])=O.CC([O-])=O VGBWDOLBWVJTRZ-UHFFFAOYSA-K 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- KZNDOLITVANVRE-UHFFFAOYSA-L dipotassium;dodecanedioate Chemical compound [K+].[K+].[O-]C(=O)CCCCCCCCCCC([O-])=O KZNDOLITVANVRE-UHFFFAOYSA-L 0.000 description 1
- KVJXEJFFQNSORF-UHFFFAOYSA-L disodium acetic acid diacetate Chemical compound [Na+].[Na+].CC(O)=O.CC(O)=O.CC([O-])=O.CC([O-])=O KVJXEJFFQNSORF-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass 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
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- DHQYGULKBJTHIW-UHFFFAOYSA-J tetrasodium N-carboxylato-N-[2-(dicarboxylatoamino)ethyl]carbamate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)N(C([O-])=O)CCN(C([O-])=O)C([O-])=O DHQYGULKBJTHIW-UHFFFAOYSA-J 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- 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
-
- 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
-
- 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
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/118,634 US6600004B1 (en) | 2002-04-10 | 2002-04-10 | Method of preparing polyestercarbonates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200307704A TW200307704A (en) | 2003-12-16 |
| TWI289574B true TWI289574B (en) | 2007-11-11 |
Family
ID=27610681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092107283A TWI289574B (en) | 2002-04-10 | 2003-03-31 | Method of preparing polyestercarbonates |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6600004B1 (https=) |
| EP (1) | EP1504048B1 (https=) |
| JP (1) | JP2005522545A (https=) |
| KR (1) | KR20040107502A (https=) |
| CN (1) | CN100500728C (https=) |
| AU (1) | AU2003220407A1 (https=) |
| DE (1) | DE60317660T2 (https=) |
| TW (1) | TWI289574B (https=) |
| WO (1) | WO2003087190A1 (https=) |
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| US6870025B2 (en) * | 2001-07-24 | 2005-03-22 | General Electric Company | Method of polycarbonate preparation |
| US20050135706A1 (en) * | 2003-12-19 | 2005-06-23 | General Electric Company | System and method for shadow imaging |
| US7041775B2 (en) * | 2004-04-20 | 2006-05-09 | General Electric Company | Method for preparing a polycarbonate oligomer mixture at low temperature for manufacturing polycarbonate |
| ATE538778T1 (de) | 2004-05-28 | 2012-01-15 | Unigen Inc | 1-(3-methyl-2,4-dimethoxyphenyl)-3-(2',4'- dihydroxyphenyl)-propan als hochwirksamer tyrosinase-inhibitor |
| US7312352B2 (en) * | 2004-08-02 | 2007-12-25 | Paul William Buckley | Method of preparing ester-substituted diaryl carbonates |
| 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 |
| US7365149B2 (en) * | 2005-12-12 | 2008-04-29 | Hans-Peter Brack | Equipment cleaning in the manufacture of polycarbonates |
| 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 |
| 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 |
| US20070208159A1 (en) * | 2006-03-02 | 2007-09-06 | General Electric Company | Poly(arylene ether) block copolymer compositions, methods, and articles |
| 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 |
| US7645851B2 (en) * | 2006-06-30 | 2010-01-12 | Sabic Innovative Plastics Ip B.V. | Polycarbonate with reduced color |
| 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 |
| 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 |
| 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 |
| US7666972B2 (en) * | 2007-10-18 | 2010-02-23 | SABIC Innovative Plastics IP B., V. | Isosorbide-based polycarbonates, method of making, and articles formed therefrom |
| US7718755B2 (en) * | 2007-10-18 | 2010-05-18 | Sabic Innovative Plastics Ip B.V. | Aliphatic diol-based polycarbonates, method of making, and articles formed therefrom |
| 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 |
| CA2730265C (en) * | 2008-07-21 | 2016-06-28 | Unigen, Inc. | Series of skin-whitening (lightening) compounds |
| CN102648388B (zh) * | 2009-10-19 | 2015-04-15 | 贝邓肯电子公司 | 多转动传感器 |
| US8273849B2 (en) * | 2009-12-30 | 2012-09-25 | Sabic Innovative Plastics Ip B.V. | Isosorbide-based polycarbonates, method of making, and articles formed therefrom |
| US8343608B2 (en) | 2010-08-31 | 2013-01-01 | General Electric Company | Use of appended dyes in optical data storage media |
| AU2012231008B2 (en) | 2011-03-24 | 2017-05-11 | Unigen, Inc. | Compounds and methods for preparation of diarylpropanes |
| JP2015193674A (ja) * | 2012-08-15 | 2015-11-05 | 旭硝子株式会社 | ポリエステルカーボネートの製造方法 |
| US10265608B2 (en) | 2015-07-17 | 2019-04-23 | Albert S. Abraham | Assembly and method for frame side matching game play |
| WO2018002828A1 (en) * | 2016-06-28 | 2018-01-04 | Sabic Global Technologies B.V. | Polyestercarbonate compositions, articles formed therefrom, and methods of manufacture |
| KR20220117226A (ko) * | 2019-12-16 | 2022-08-23 | 코베스트로 인텔렉쳐 프로퍼티 게엠베하 운트 콤파니 카게 | 지방족 이산 및 지방족 디올로부터의 폴리에스테르 카르보네이트, 및 그의 제조 방법 |
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| US4323668A (en) | 1980-12-03 | 1982-04-06 | General Electric Company | (Ortho-alkoxycarbonyaryl)-carbonate transesterification |
| US5278279A (en) * | 1992-03-11 | 1994-01-11 | Daicel Chemical Industries, Ltd. | Process for producing (co)polycarbonate with transesterification catalyst and compound |
| JPH08183852A (ja) * | 1994-12-28 | 1996-07-16 | Nippon G Ii Plast Kk | コポリカーボネート、コポリカーボネート組成物およびこれらの製造方法 |
| DE69605167T2 (de) | 1995-09-19 | 2000-09-14 | Teijin Ltd., Osaka | Verfahren zur Herstellung von Polycarbonat |
| US6300459B1 (en) | 1998-03-17 | 2001-10-09 | Teijin Limited | Process for producing aromatic polycarbonate |
| JP2002528614A (ja) * | 1998-10-29 | 2002-09-03 | ゼネラル・エレクトリック・カンパニイ | 耐候性ブロックコポリエステルカーボネートおよびそれを含むブレンド |
| EP1114841B1 (en) | 1999-04-20 | 2003-10-08 | Teijin Limited | Process for producing polyarylate |
| US6232429B1 (en) | 1999-11-01 | 2001-05-15 | General Electric Company | Method for making polyester carbonates |
| JP2001200037A (ja) * | 2000-01-19 | 2001-07-24 | Teijin Ltd | 全芳香族ポリエステルの製造方法 |
| CN1187390C (zh) * | 2000-06-01 | 2005-02-02 | 帝人株式会社 | 全芳香族聚酯碳酸酯及其制造法 |
| JP2002069164A (ja) * | 2000-08-30 | 2002-03-08 | Teijin Ltd | 全芳香族ポリエステルカーボネートおよびその製造方法 |
| US6228973B1 (en) * | 2000-06-02 | 2001-05-08 | General Electric Company | Method for preparing high molecular weight polycarbonate |
| US6255438B1 (en) * | 2000-07-20 | 2001-07-03 | General Electric Company | Phenolic compounds, polymers derived therefrom, and method |
| US6482977B1 (en) * | 2000-07-28 | 2002-11-19 | General Electric Company | Melt process for the synthesis of diaryl esters of aliphatic diacids |
| US6414106B1 (en) * | 2001-03-02 | 2002-07-02 | General Electric Company | Process for the neutralization of residual acid species in crude dihydric phenols |
| US6365702B1 (en) * | 2001-05-31 | 2002-04-02 | General Electric Company | Polyestercarbonates and methods for the direct incorporation of acids into polycarbonate chains by SSP |
-
2002
- 2002-04-10 US US10/118,634 patent/US6600004B1/en not_active Expired - Lifetime
-
2003
- 2003-03-20 DE DE60317660T patent/DE60317660T2/de not_active Expired - Lifetime
- 2003-03-20 EP EP03716711A patent/EP1504048B1/en not_active Expired - Lifetime
- 2003-03-20 JP JP2003584144A patent/JP2005522545A/ja active Pending
- 2003-03-20 CN CNB038133156A patent/CN100500728C/zh not_active Expired - Fee Related
- 2003-03-20 WO PCT/US2003/008494 patent/WO2003087190A1/en not_active Ceased
- 2003-03-20 KR KR10-2004-7016226A patent/KR20040107502A/ko not_active Ceased
- 2003-03-20 AU AU2003220407A patent/AU2003220407A1/en not_active Abandoned
- 2003-03-31 TW TW092107283A patent/TWI289574B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005522545A (ja) | 2005-07-28 |
| KR20040107502A (ko) | 2004-12-20 |
| EP1504048B1 (en) | 2007-11-21 |
| DE60317660D1 (de) | 2008-01-03 |
| TW200307704A (en) | 2003-12-16 |
| CN1659207A (zh) | 2005-08-24 |
| EP1504048A1 (en) | 2005-02-09 |
| CN100500728C (zh) | 2009-06-17 |
| WO2003087190A1 (en) | 2003-10-23 |
| US6600004B1 (en) | 2003-07-29 |
| DE60317660T2 (de) | 2008-10-30 |
| AU2003220407A1 (en) | 2003-10-27 |
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