TWI293966B - Method of polycarbonate preparation - Google Patents
Method of polycarbonate preparation Download PDFInfo
- Publication number
- TWI293966B TWI293966B TW092115108A TW92115108A TWI293966B TW I293966 B TWI293966 B TW I293966B TW 092115108 A TW092115108 A TW 092115108A TW 92115108 A TW92115108 A TW 92115108A TW I293966 B TWI293966 B TW I293966B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- bis
- carbonate
- catalyst
- alkali metal
- Prior art date
Links
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 78
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title claims description 77
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 99
- -1 alkali metal salts Chemical class 0.000 claims abstract description 70
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 59
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 44
- 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 34
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims abstract description 32
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 30
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 239000003426 co-catalyst Substances 0.000 claims abstract description 20
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 11
- 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 10
- 229910001413 alkali metal ion Inorganic materials 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 150000001491 aromatic compounds Chemical class 0.000 claims description 25
- 239000000203 mixture Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000011734 sodium Substances 0.000 claims description 16
- 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 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 229910052708 sodium Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000000155 melt Substances 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 229930185605 Bisphenol Natural products 0.000 claims description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 239000002981 blocking agent Substances 0.000 claims description 7
- 239000006085 branching agent Substances 0.000 claims description 7
- 229910021645 metal ion Inorganic materials 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910001415 sodium ion Inorganic materials 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 238000003723 Smelting Methods 0.000 claims description 4
- 150000001449 anionic compounds Chemical class 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 4
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000002891 organic anions Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 3
- 150000004714 phosphonium salts Chemical group 0.000 claims description 3
- 229910001414 potassium ion Inorganic materials 0.000 claims description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
- 150000003871 sulfonates Chemical class 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 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 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
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 238000010923 batch production Methods 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
- 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
- 238000010924 continuous production Methods 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 claims description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052712 strontium Inorganic materials 0.000 claims 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims 3
- PYOLJOJPIPCRDP-UHFFFAOYSA-N 1,1,3-trimethylcyclohexane Chemical compound CC1CCCC(C)(C)C1 PYOLJOJPIPCRDP-UHFFFAOYSA-N 0.000 claims 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 125000004429 atom Chemical group 0.000 claims 2
- 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 claims 2
- 229910052797 bismuth Inorganic materials 0.000 claims 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- 150000008040 ionic compounds Chemical class 0.000 claims 2
- 150000003254 radicals Chemical group 0.000 claims 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims 1
- NQJCGWSRIVAROT-UHFFFAOYSA-N (4-methylphenyl) hydrogen carbonate Chemical compound CC1=CC=C(OC(O)=O)C=C1 NQJCGWSRIVAROT-UHFFFAOYSA-N 0.000 claims 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- NMGQOXUIQWJLFW-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxyphenyl)propan-2-yl]phenol;4-[2-(4-hydroxy-3-methylphenyl)propan-2-yl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1.C=1C=C(O)C(Cl)=CC=1C(C)(C)C1=CC=C(O)C(Cl)=C1 NMGQOXUIQWJLFW-UHFFFAOYSA-N 0.000 claims 1
- CKNCVRMXCLUOJI-UHFFFAOYSA-N 3,3'-dibromobisphenol A Chemical compound C=1C=C(O)C(Br)=CC=1C(C)(C)C1=CC=C(O)C(Br)=C1 CKNCVRMXCLUOJI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ZUTYZAFDFLLILI-UHFFFAOYSA-N 4-sec-Butylphenol Chemical compound CCC(C)C1=CC=C(O)C=C1 ZUTYZAFDFLLILI-UHFFFAOYSA-N 0.000 claims 1
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims 1
- QQGMMLWLGIWJSP-UHFFFAOYSA-N C(C)(C)C=1C=C(C=CC1O)C1=C(C=CC=C1)C(C)(C)C1=C(C=CC=C1)C1=CC(=C(C=C1)O)C(C)C Chemical compound C(C)(C)C=1C=C(C=CC1O)C1=C(C=CC=C1)C(C)(C)C1=C(C=CC=C1)C1=CC(=C(C=C1)O)C(C)C QQGMMLWLGIWJSP-UHFFFAOYSA-N 0.000 claims 1
- VAMKJHPYGOMHAK-UHFFFAOYSA-N C1CCC(CC1)(C2=CC=CC=C2C3=CC=NC=C3)C4=CC=CC=C4C5=CC=NC=C5 Chemical compound C1CCC(CC1)(C2=CC=CC=C2C3=CC=NC=C3)C4=CC=CC=C4C5=CC=NC=C5 VAMKJHPYGOMHAK-UHFFFAOYSA-N 0.000 claims 1
- APZGLIRQOPUWKW-UHFFFAOYSA-N CC=1C=C(C=CC=1O)C1CC(CCC1)C1=CC(=C(C=C1)O)C Chemical compound CC=1C=C(C=CC=1O)C1CC(CCC1)C1=CC(=C(C=C1)O)C APZGLIRQOPUWKW-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 241001649081 Dina Species 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical class O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 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
- MHFGNKMUCULCRW-UHFFFAOYSA-N bis(4-phenylphenyl) carbonate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1OC(=O)OC(C=C1)=CC=C1C1=CC=CC=C1 MHFGNKMUCULCRW-UHFFFAOYSA-N 0.000 claims 1
- TZSMWSKOPZEMAJ-UHFFFAOYSA-N bis[(2-methoxyphenyl)methyl] carbonate Chemical compound COC1=CC=CC=C1COC(=O)OCC1=CC=CC=C1OC TZSMWSKOPZEMAJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- YWLWJBABFRRMRM-UHFFFAOYSA-N cyclohexene Chemical compound C1C[CH-]C=CC1 YWLWJBABFRRMRM-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 210000004709 eyebrow Anatomy 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 1
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims 1
- 229940032091 stigmasterol Drugs 0.000 claims 1
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 claims 1
- 235000016831 stigmasterol Nutrition 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 88
- 229910000318 alkali metal phosphate Inorganic materials 0.000 abstract description 15
- 238000005259 measurement Methods 0.000 abstract description 3
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 abstract description 2
- NCFMEGVCJUWIRV-UHFFFAOYSA-N bis[4-(2-phenylpropan-2-yl)phenyl] carbonate Chemical compound C=1C=C(OC(=O)OC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 NCFMEGVCJUWIRV-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005618 Fries rearrangement reaction Methods 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 15
- 230000008569 process Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000000356 contaminant Substances 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229960003975 potassium Drugs 0.000 description 5
- 241000894007 species Species 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 235000021419 vinegar Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229960003742 phenol Drugs 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
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- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
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- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
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- 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UVVFKNZCYIIHGM-UHFFFAOYSA-L tetrabutylazanium;carbonate Chemical compound [O-]C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC UVVFKNZCYIIHGM-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JOPDZQBPOWAEHC-UHFFFAOYSA-H tristrontium;diphosphate Chemical compound [Sr+2].[Sr+2].[Sr+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O JOPDZQBPOWAEHC-UHFFFAOYSA-H 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
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- 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 |
|---|---|---|---|
| US10/167,965 US6723823B2 (en) | 2001-07-24 | 2002-06-12 | Method of polycarbonate preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200403279A TW200403279A (en) | 2004-03-01 |
| TWI293966B true TWI293966B (en) | 2008-03-01 |
Family
ID=29732306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092115108A TWI293966B (en) | 2002-06-12 | 2003-06-03 | Method of polycarbonate preparation |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6723823B2 (enExample) |
| EP (1) | EP1519978B1 (enExample) |
| JP (1) | JP2005530001A (enExample) |
| CN (1) | CN1300215C (enExample) |
| AT (1) | ATE369391T1 (enExample) |
| AU (1) | AU2003248552A1 (enExample) |
| DE (1) | DE60315458T2 (enExample) |
| TW (1) | TWI293966B (enExample) |
| WO (1) | WO2003106533A1 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6870025B2 (en) * | 2001-07-24 | 2005-03-22 | General Electric Company | Method of polycarbonate preparation |
| KR100544880B1 (ko) * | 2002-08-19 | 2006-01-24 | 주식회사 엘지화학 | 올레핀 제조용 탄화수소 수증기 열분해 촉매와 이의제조방법 및 이를 이용한 올레핀 제조방법 |
| US7041775B2 (en) * | 2004-04-20 | 2006-05-09 | General Electric Company | Method for preparing a polycarbonate oligomer mixture at low temperature for manufacturing polycarbonate |
| US7148386B2 (en) * | 2004-07-30 | 2006-12-12 | General Electric Company | Processes for preparing benzoquinones and hydroquinones |
| 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 |
| US7793813B2 (en) * | 2006-02-28 | 2010-09-14 | Tyco Healthcare Group Lp | Hub for positioning annular structure on a surgical device |
| 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 |
| US7541420B2 (en) * | 2006-06-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Method for making molded polycarbonate articles with improved color |
| US7482423B2 (en) * | 2006-06-30 | 2009-01-27 | Sabic Innovative Plastics Ip B.V. | Polycarbonates and method of preparing same |
| US7498400B2 (en) * | 2006-06-30 | 2009-03-03 | Sabic Innovative Plastics Ip B.V. | Method of preparing polycarbonate |
| US7645851B2 (en) * | 2006-06-30 | 2010-01-12 | Sabic Innovative Plastics Ip B.V. | Polycarbonate with reduced color |
| US7632913B2 (en) * | 2007-09-28 | 2009-12-15 | Sabic Innovative Plastics Ip B.V. | Method of producing polycarbonate in a flash devolatilization system |
| 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 |
| DE102007052968A1 (de) * | 2007-11-07 | 2009-05-14 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polycarbonat nach dem Schmelzeumesterungsverfahren |
| 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 |
| US20100305010A1 (en) * | 2009-05-28 | 2010-12-02 | Clearwater International, Llc | High density phosphate brines and methods for making and using same |
| US8784963B2 (en) * | 2010-07-08 | 2014-07-22 | Asahi Kasei Chemicals Corporation | Branched polycarbonate |
| US8343608B2 (en) | 2010-08-31 | 2013-01-01 | General Electric Company | Use of appended dyes in optical data storage media |
| KR101346516B1 (ko) * | 2013-01-18 | 2013-12-31 | 아주대학교산학협력단 | 염기 촉매를 이용하여 제조된 고분자량의 지방족 폴리카보네이트 |
| JP6695272B2 (ja) * | 2013-10-08 | 2020-05-20 | 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 | ポリシロキサン−ポリカーボネートブロック共縮合物を調製する方法 |
| EP3274393B1 (en) * | 2015-03-24 | 2019-04-24 | SABIC Global Technologies B.V. | A melt polymerization process and the polycarbonate prepared therefrom |
| KR20180109081A (ko) * | 2016-02-26 | 2018-10-05 | 사빅 글로벌 테크놀러지스 비.브이. | 충격 성능이 개선된 용융 폴리카보네이트 |
| CN108976404B (zh) * | 2018-07-26 | 2020-11-06 | 沈阳建筑大学 | 腰果酚改性的聚-2,6-萘二甲酸乙二醇酯及其制备法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4312390A1 (de) | 1993-04-16 | 1994-10-20 | Bayer Ag | Zweistufen-Verfahren zur Herstellung von thermoplastischem Polycarbonat |
| JP4439737B2 (ja) * | 1998-09-28 | 2010-03-24 | 出光興産株式会社 | ポリカーボネート共重合体の製造法 |
| US6339138B1 (en) * | 1998-11-04 | 2002-01-15 | General Electric Company | Method of manufacturing polycarbonates |
| US6022943A (en) | 1999-04-07 | 2000-02-08 | General Electric Company | Optical quality polycarbonates with reduced static charge and method for making same |
| US6316578B1 (en) | 2000-02-04 | 2001-11-13 | General Electric Company | Salts of non-volatile acids as polymerization catalysts |
| US6300460B1 (en) | 2000-07-06 | 2001-10-09 | General Electric Company | Mixed dialkali metal salts of sulfuric acid containing at least one cesium equivalent as polymerization catalysts |
| US6395862B1 (en) * | 2001-01-12 | 2002-05-28 | General Electric Company | Melt polycarbonate catalyst systems |
-
2002
- 2002-06-12 US US10/167,965 patent/US6723823B2/en not_active Expired - Lifetime
-
2003
- 2003-05-22 EP EP03760221A patent/EP1519978B1/en not_active Expired - Lifetime
- 2003-05-22 DE DE60315458T patent/DE60315458T2/de not_active Expired - Lifetime
- 2003-05-22 JP JP2004513359A patent/JP2005530001A/ja not_active Withdrawn
- 2003-05-22 AT AT03760221T patent/ATE369391T1/de not_active IP Right Cessation
- 2003-05-22 CN CNB038172232A patent/CN1300215C/zh not_active Expired - Fee Related
- 2003-05-22 AU AU2003248552A patent/AU2003248552A1/en not_active Abandoned
- 2003-05-22 WO PCT/US2003/016185 patent/WO2003106533A1/en not_active Ceased
- 2003-06-03 TW TW092115108A patent/TWI293966B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1668672A (zh) | 2005-09-14 |
| JP2005530001A (ja) | 2005-10-06 |
| CN1300215C (zh) | 2007-02-14 |
| WO2003106533A1 (en) | 2003-12-24 |
| US6723823B2 (en) | 2004-04-20 |
| TW200403279A (en) | 2004-03-01 |
| EP1519978A1 (en) | 2005-04-06 |
| AU2003248552A1 (en) | 2003-12-31 |
| DE60315458D1 (de) | 2007-09-20 |
| EP1519978B1 (en) | 2007-08-08 |
| US20030236383A1 (en) | 2003-12-25 |
| ATE369391T1 (de) | 2007-08-15 |
| DE60315458T2 (de) | 2008-04-24 |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |