CA2306157A1 - Preparation of dihydroxydiphenyl-copolycarbonates by melt re-esterification - Google Patents
Preparation of dihydroxydiphenyl-copolycarbonates by melt re-esterification Download PDFInfo
- Publication number
- CA2306157A1 CA2306157A1 CA002306157A CA2306157A CA2306157A1 CA 2306157 A1 CA2306157 A1 CA 2306157A1 CA 002306157 A CA002306157 A CA 002306157A CA 2306157 A CA2306157 A CA 2306157A CA 2306157 A1 CA2306157 A1 CA 2306157A1
- Authority
- CA
- Canada
- Prior art keywords
- mol
- alkyl
- copolycarbonates
- preparation
- accordance
- 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.)
- Abandoned
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000005886 esterification reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000004417 polycarbonate Substances 0.000 claims abstract description 18
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000000155 melt Substances 0.000 claims abstract description 4
- 150000002780 morpholines Chemical class 0.000 claims abstract description 3
- 150000003053 piperidines Chemical class 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 5
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims description 4
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 230000000295 complement effect Effects 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- 239000004416 thermosoftening plastic Substances 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 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 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- -1 alkyl phosphites Chemical class 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000000463 material Substances 0.000 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 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 230000016507 interphase Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229910000064 phosphane Inorganic materials 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- KXIXHISTUVHOCY-UHFFFAOYSA-N 1-propan-2-ylpiperidine Chemical compound CC(C)N1CCCCC1 KXIXHISTUVHOCY-UHFFFAOYSA-N 0.000 description 1
- VTDIWMPYBAVEDY-UHFFFAOYSA-N 1-propylpiperidine Chemical compound CCCN1CCCCC1 VTDIWMPYBAVEDY-UHFFFAOYSA-N 0.000 description 1
- CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 description 1
- AUNGWUPUJSKFFU-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,5,5-trimethylcyclohex-3-en-1-yl]phenol Chemical compound OC1=CC=C(C=C1)C1(CC(C=C(C1)C)(C)C)C1=CC=C(C=C1)O AUNGWUPUJSKFFU-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- XLZMWNWNBXSZKF-UHFFFAOYSA-N 4-propan-2-ylmorpholine Chemical compound CC(C)N1CCOCC1 XLZMWNWNBXSZKF-UHFFFAOYSA-N 0.000 description 1
- NMILGIZTAZXMTM-UHFFFAOYSA-N 4-propylmorpholine Chemical compound CCCN1CCOCC1 NMILGIZTAZXMTM-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000013500 data storage Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
-
- 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
- C08G64/307—General preparatory processes using carbonates and phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19744693A DE19744693A1 (de) | 1997-10-10 | 1997-10-10 | Verfahren zur Herstellung von speziellen Copolycarbonaten durch Schmelzumesterung |
| DE19744693.0 | 1997-10-10 | ||
| PCT/EP1998/006212 WO1999019380A1 (de) | 1997-10-10 | 1998-09-30 | Herstellung von dihydroxydiphenyl-copolycarbonaten durch schmelzumesterung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2306157A1 true CA2306157A1 (en) | 1999-04-22 |
Family
ID=7845093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002306157A Abandoned CA2306157A1 (en) | 1997-10-10 | 1998-09-30 | Preparation of dihydroxydiphenyl-copolycarbonates by melt re-esterification |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1023357A1 (id) |
| JP (1) | JP2001520242A (id) |
| KR (1) | KR20010031016A (id) |
| CN (1) | CN1266442A (id) |
| AU (1) | AU9541798A (id) |
| BR (1) | BR9812888A (id) |
| CA (1) | CA2306157A1 (id) |
| DE (1) | DE19744693A1 (id) |
| ID (1) | ID24573A (id) |
| IL (1) | IL135003A0 (id) |
| NO (1) | NO20001167L (id) |
| TW (1) | TW426704B (id) |
| WO (1) | WO1999019380A1 (id) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6740714B2 (en) * | 2001-07-20 | 2004-05-25 | Bayer Aktiengesellschaft | Polycarbonate blends |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004510025A (ja) * | 2000-09-26 | 2004-04-02 | バイエル アクチェンゲゼルシャフト | コポリカーボネート組成物、その使用およびそれを含有する成形部品 |
| JP2002114841A (ja) * | 2000-10-06 | 2002-04-16 | Mitsui Chemicals Inc | 光学部品 |
| JP2002114842A (ja) * | 2000-10-06 | 2002-04-16 | Mitsui Chemicals Inc | ポリカーボネート樹脂、及びそれを含んで構成される光学部品 |
| JP4514080B2 (ja) * | 2000-12-28 | 2010-07-28 | 三井化学株式会社 | ポリカーボネート樹脂組成物、及びそれを含んで構成される光学部品 |
| US6608163B2 (en) | 2001-01-17 | 2003-08-19 | General Electric Company | Polycarbonate copolymers having improved hydrolytic stability |
| US7183371B2 (en) * | 2004-11-01 | 2007-02-27 | General Electric Company | Method for making polycarbonate |
| CN102464545A (zh) | 2010-11-11 | 2012-05-23 | 中国石油天然气股份有限公司 | 一种乙烯齐聚制备1-辛烯的方法 |
| TWI693244B (zh) * | 2015-01-20 | 2020-05-11 | 德商科思創德意志股份有限公司 | 藉由轉酯化方法製備高耐熱之[共]聚碳酸酯 |
| WO2023149329A1 (ja) * | 2022-02-07 | 2023-08-10 | 三菱ケミカル株式会社 | ポリカーボネート樹脂組成物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2735775A1 (de) * | 1977-08-09 | 1979-02-22 | Bayer Ag | Verfahren zur herstellung von polycarbonaten |
| JPS61264020A (ja) * | 1985-05-17 | 1986-11-21 | Idemitsu Kosan Co Ltd | 芳香族ポリカ−ボネ−トおよびその製造方法 |
| DE3919046A1 (de) * | 1989-06-10 | 1990-12-20 | Bayer Ag | Neue thermotrope polycarbonate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von formkoerpern, filamenten, fasern und folien |
| JPH05117382A (ja) * | 1991-10-29 | 1993-05-14 | Nippon G Ii Plast Kk | 共重合ポリカーボネート、その製造方法およびそれからなる組成物 |
| US5475079A (en) * | 1993-04-28 | 1995-12-12 | Daicel Chemical Industries, Ltd. | (CO) polycarbonate composition and process for preparing the same |
| JPH08165341A (ja) * | 1994-12-15 | 1996-06-25 | Idemitsu Kosan Co Ltd | ポリカーボネートの製造方法 |
-
1997
- 1997-10-10 DE DE19744693A patent/DE19744693A1/de not_active Withdrawn
-
1998
- 1998-09-21 TW TW087115670A patent/TW426704B/zh not_active IP Right Cessation
- 1998-09-30 EP EP98948996A patent/EP1023357A1/de not_active Withdrawn
- 1998-09-30 KR KR1020007003823A patent/KR20010031016A/ko not_active Withdrawn
- 1998-09-30 WO PCT/EP1998/006212 patent/WO1999019380A1/de not_active Ceased
- 1998-09-30 IL IL13500398A patent/IL135003A0/xx unknown
- 1998-09-30 AU AU95417/98A patent/AU9541798A/en not_active Abandoned
- 1998-09-30 BR BR9812888-4A patent/BR9812888A/pt not_active IP Right Cessation
- 1998-09-30 JP JP2000515948A patent/JP2001520242A/ja active Pending
- 1998-09-30 CN CN98808044A patent/CN1266442A/zh active Pending
- 1998-09-30 CA CA002306157A patent/CA2306157A1/en not_active Abandoned
- 1998-09-30 ID IDW20000622D patent/ID24573A/id unknown
-
2000
- 2000-03-07 NO NO20001167A patent/NO20001167L/no not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6740714B2 (en) * | 2001-07-20 | 2004-05-25 | Bayer Aktiengesellschaft | Polycarbonate blends |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001520242A (ja) | 2001-10-30 |
| ID24573A (id) | 2000-07-27 |
| NO20001167D0 (no) | 2000-03-07 |
| NO20001167L (no) | 2000-03-07 |
| TW426704B (en) | 2001-03-21 |
| IL135003A0 (en) | 2001-05-20 |
| EP1023357A1 (de) | 2000-08-02 |
| WO1999019380A1 (de) | 1999-04-22 |
| DE19744693A1 (de) | 1999-04-15 |
| KR20010031016A (ko) | 2001-04-16 |
| AU9541798A (en) | 1999-05-03 |
| CN1266442A (zh) | 2000-09-13 |
| BR9812888A (pt) | 2000-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |