JP2003525959A - 固相重合によるコポリカーボネートの製造 - Google Patents
固相重合によるコポリカーボネートの製造Info
- Publication number
- JP2003525959A JP2003525959A JP2000577219A JP2000577219A JP2003525959A JP 2003525959 A JP2003525959 A JP 2003525959A JP 2000577219 A JP2000577219 A JP 2000577219A JP 2000577219 A JP2000577219 A JP 2000577219A JP 2003525959 A JP2003525959 A JP 2003525959A
- Authority
- JP
- Japan
- Prior art keywords
- component
- copolycarbonate
- polycarbonate
- stage
- precursor
- 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- Withdrawn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
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 239000007787 solid Substances 0.000 title claims description 15
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 43
- 239000004417 polycarbonate Substances 0.000 claims abstract description 43
- 239000002243 precursor Substances 0.000 claims abstract description 27
- 239000000178 monomer Substances 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 238000011067 equilibration Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 39
- 239000003054 catalyst Substances 0.000 claims description 18
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 claims description 9
- -1 diaryl carbonate Chemical compound 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 150000001491 aromatic compounds Chemical class 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 150000004703 alkoxides Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SUOOZFRDMVSBLL-KSBRXOFISA-L (z)-but-2-enedioate;tetramethylazanium Chemical compound C[N+](C)(C)C.C[N+](C)(C)C.[O-]C(=O)\C=C/C([O-])=O SUOOZFRDMVSBLL-KSBRXOFISA-L 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 240000005589 Calophyllum inophyllum Species 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- LYWKAJZTPLXHEM-UHFFFAOYSA-M bis(diethylamino)methylidene-diethylazanium;chloride Chemical compound [Cl-].CCN(CC)C(N(CC)CC)=[N+](CC)CC LYWKAJZTPLXHEM-UHFFFAOYSA-M 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 2
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ADXSSOHCZJOVIJ-UHFFFAOYSA-N 2,2-diphenyldodecanedioic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(CCCCCCCCCC(=O)O)C1=CC=CC=C1 ADXSSOHCZJOVIJ-UHFFFAOYSA-N 0.000 description 1
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-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
- VPIYABOIEBBVSK-UHFFFAOYSA-L CCN(CC)C(=[N+](CC)CC)N(CC)CC.CCN(CC)C(=[N+](CC)CC)N(CC)CC.C1=CC=C(C=C1)[O-].C1=CC=C(C=C1)[O-] Chemical compound CCN(CC)C(=[N+](CC)CC)N(CC)CC.CCN(CC)C(=[N+](CC)CC)N(CC)CC.C1=CC=C(C=C1)[O-].C1=CC=C(C=C1)[O-] VPIYABOIEBBVSK-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-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
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006085 branching agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000000156 glass melt Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical compound C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 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 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005406 washing Methods 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
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1882/CAL/98 | 1998-10-22 | ||
| IN1882CA1998 | 1998-10-22 | ||
| PCT/US1999/022838 WO2000023498A1 (en) | 1998-10-22 | 1999-10-01 | Copolycarbonate preparation by solid state polymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003525959A true JP2003525959A (ja) | 2003-09-02 |
| JP2003525959A5 JP2003525959A5 (enExample) | 2006-11-24 |
Family
ID=11087040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000577219A Withdrawn JP2003525959A (ja) | 1998-10-22 | 1999-10-01 | 固相重合によるコポリカーボネートの製造 |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1123338A1 (enExample) |
| JP (1) | JP2003525959A (enExample) |
| WO (1) | WO2000023498A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6333394B1 (en) * | 1999-08-09 | 2001-12-25 | General Electric Company | Copolycarbonate preparation by solid state polymerization |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2726416A1 (de) * | 1977-06-11 | 1978-12-21 | Bayer Ag | Verfahren zur herstellung von kohlensaeure-bis-diphenol-estern von ueber carbonat-gruppen-verlaengerten polyalkylenoxiddiolen und ihre verwendung zur herstellung von hochmolekularen, segmentierten, thermoplastisch verarbeitbaren polyaether-polycarbonaten |
| US4920200A (en) * | 1988-12-27 | 1990-04-24 | General Electric Company | Hydroquinone-bisphenol cyclic copolycarbonate oligomer |
| US5717056A (en) * | 1996-05-24 | 1998-02-10 | General Electric Company | Method for preparing polycarbonate by solid state polymerization |
-
1999
- 1999-10-01 EP EP99950085A patent/EP1123338A1/en not_active Withdrawn
- 1999-10-01 JP JP2000577219A patent/JP2003525959A/ja not_active Withdrawn
- 1999-10-01 WO PCT/US1999/022838 patent/WO2000023498A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1123338A1 (en) | 2001-08-16 |
| WO2000023498A1 (en) | 2000-04-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH10176047A (ja) | 固相重合によるポリカーボネートの製造方法 | |
| KR100561337B1 (ko) | 고분자량의 폴리카보네이트 수지의 제조방법 | |
| JPS6383130A (ja) | 環状芳香族ポリカ−ボネ−トオリゴマ−からコポリエステルカ−ボネ−トを製造する方法 | |
| JPH0662753B2 (ja) | ハイドロキノン―ビスフエノール環式コポリカーボネート及びその製造法 | |
| JPH08311192A (ja) | 環状ポリカ―ボネ―トオリゴマ―からの樹脂組成物の製造方法 | |
| EP0695511B1 (en) | Preparation of copolyestercarbonates by the bischloroformate process | |
| KR100633974B1 (ko) | 고상 중합에 의한 코폴리카보네이트의 제조방법 | |
| US6031062A (en) | Method for preparing polycarbonates of enhanced crystallinity | |
| US6143859A (en) | Copolycarbonate preparation by solid state polymerization | |
| JP2904914B2 (ja) | 特定のジヒドロキシジフエニルアルカンに基づくポリカーボネートの２段階製造方法 | |
| JP2003525959A (ja) | 固相重合によるコポリカーボネートの製造 | |
| US6034142A (en) | Method for recycling aromatic polycarbonates | |
| KR19990029426A (ko) | 방향족 폴리카보네이트의 재생 방법 | |
| JPH07292095A (ja) | 芳香族ポリカーボネート樹脂の改質法 | |
| KR20010093292A (ko) | 결정화도가 향상된 코폴리카보네이트의 제조방법 | |
| US6433126B1 (en) | Preparation of copolycarbonates via solid state polymerization | |
| JP2006504782A (ja) | １，１−ビス（４′−ヒドロキシ−３′−メチルフェニル）シクロヘキサンの精製方法及びそれからポリカーボネートを製造する方法 | |
| JP4149602B2 (ja) | 芳香族ポリカーボネート共重合体と、その製造方法 | |
| KR19990045077A (ko) | 고상 중합에 의한 폴리카보네이트의 제조 방법 | |
| JPH03152126A (ja) | 反応性に末端停止されたポリカーボネートの製造法 | |
| JP2003521560A (ja) | 固相重合によるポリマーの製造方法 | |
| Varadarajan et al. | Office européen des brevets | |
| EP0949292A1 (en) | Method for recycling aromatic polycarbonates | |
| JP2002069169A (ja) | 溶融流動性芳香族ポリカーボネート | |
| JP2010132842A (ja) | 環状ポリカーボネートオリゴマーおよび環状ポリカーボネートオリゴマーの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20061002 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20061002 |
|
| RD12 | Notification of acceptance of power of sub attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7432 Effective date: 20071030 |
|
| A761 | Written withdrawal of application |
Free format text: JAPANESE INTERMEDIATE CODE: A761 Effective date: 20090115 |