JP2008519136A - ポリカーボネート樹脂の製造方法 - Google Patents
ポリカーボネート樹脂の製造方法 Download PDFInfo
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- JP2008519136A JP2008519136A JP2007540272A JP2007540272A JP2008519136A JP 2008519136 A JP2008519136 A JP 2008519136A JP 2007540272 A JP2007540272 A JP 2007540272A JP 2007540272 A JP2007540272 A JP 2007540272A JP 2008519136 A JP2008519136 A JP 2008519136A
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- polycarbonate resin
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- polycarbonate
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- 229920005668 polycarbonate resin Polymers 0.000 title claims abstract description 30
- 239000004431 polycarbonate resin Substances 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 20
- 239000004417 polycarbonate Substances 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 238000002844 melting Methods 0.000 claims abstract description 4
- 230000008018 melting Effects 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims 1
- -1 aromatic carbonate compound Chemical class 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 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 5
- 230000006872 improvement Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 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
- 238000002845 discoloration Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
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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
- C08G64/04—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
-
- 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
- C08G64/22—General preparatory processes using carbonyl halides
- C08G64/24—General preparatory processes using carbonyl halides and phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- 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
- C08G64/42—Chemical after-treatment
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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)
- General Chemical & Material Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
下記化学式2を有する末端停止剤を製造するために、ジフェニルカーボネート22.4g及びビスフェノールA18.2gを、ビスフェノールAの濃度に対して0.0001モル%の酢酸ナトリウムと共に100ml容量のガラス反応器に入れて、250℃に昇温し、磁石攪拌器で攪拌しつつ1時間反応させた。このとき、反応器内の圧力は、250mmHgであった。反応後、温度を常温まで下降させ、塩化メチレン100mlを加えて反応物を全て溶かした後、メタノール100mlを添加して沈殿させ、ろ紙でろ過した後に乾燥して、パウダー状の末端停止剤を製造した。NMR分析を通じて下記化学式2の末端停止剤が首尾よく製造されたことを確認した。
本発明者が、溶融重合及び固相重合により製造した数平均分子量15,930g/molであるパウダー状のポリカーボネートと、上記化学式2の構造を有する上記製造例と同じ方法で製造された末端停止剤1.09gとを固体状態で予め混合した後、内部温度が280℃であるモールド型反応器に注入した。
Claims (6)
- 末端反応性ヒドロキシ基を含むポリカーボネートと、末端停止剤として下記化学式1の化合物とを常温常圧下で混合して混合物を形成する工程と、
前記混合物を250℃ないし320℃の温度で減圧下で溶融反応させる工程と、を通じて、ポリカーボネート樹脂の最終末端反応性ヒドロキシ基の濃度を低下させることを特徴とするポリカーボネート樹脂の製造方法:
R1、R2、R3、R4、R5及びR6は、独立的に、水素、ハロゲン原子、または炭素数1ないし18のアルキル基、炭素数1ないし18のアルコキシ基、炭素数6ないし18のアリール基、炭素数7ないし18のアラリール基及び炭素数7ないし18のアラルコキシ基から選択され、a及びbは、0ないし4の整数であり、c及びdは、0ないし5の整数である。 - 前記溶融反応が、5ないし500mmHgの減圧条件で行われることを特徴とする請求項1に記載のポリカーボネート樹脂の製造方法。
- 前記化学式1の化合物の量が、前記ポリカーボネート1.0モルを基準に0.5モルないし20モルであることを特徴とする請求項1に記載のポリカーボネート樹脂の製造方法。
- 前記最終的に製造されたポリカーボネート樹脂の最終末端反応性ヒドロキシ基の濃度が、全末端基の0ないし25.0モル%であることを特徴とする請求項1に記載のポリカーボネート樹脂の製造方法。
- 請求項1ないし請求項4のうちいずれか1項に記載の方法により製造されたポリカーボネート樹脂。
- 前記最終末端反応性ヒドロキシ基の濃度が、ポリカーボネート樹脂の全末端基の0ないし25.0モル%であることを特徴とする、請求項5に記載のポリカーボネート樹脂。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020050018844A KR100713099B1 (ko) | 2005-03-07 | 2005-03-07 | 폴리카보네이트 수지의 제조 방법 |
PCT/KR2006/000756 WO2006095982A1 (en) | 2005-03-07 | 2006-03-06 | Method of preparing polycarbonate resin |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008519136A true JP2008519136A (ja) | 2008-06-05 |
JP4624424B2 JP4624424B2 (ja) | 2011-02-02 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2007540272A Active JP4624424B2 (ja) | 2005-03-07 | 2006-03-06 | ポリカーボネート樹脂の製造方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US7495065B2 (ja) |
EP (1) | EP1856180B1 (ja) |
JP (1) | JP4624424B2 (ja) |
KR (1) | KR100713099B1 (ja) |
CN (1) | CN101061159B (ja) |
ES (1) | ES2373677T3 (ja) |
TW (1) | TWI316949B (ja) |
WO (1) | WO2006095982A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015176662A (ja) * | 2014-03-13 | 2015-10-05 | 国立研究開発法人産業技術総合研究所 | ナトリウムイオン二次電池用正極活物質 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
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KR100713099B1 (ko) | 2005-03-07 | 2007-05-02 | 주식회사 엘지화학 | 폴리카보네이트 수지의 제조 방법 |
JP5359014B2 (ja) * | 2008-04-28 | 2013-12-04 | 三菱瓦斯化学株式会社 | 紫外線吸収能を有するポリカーボネート樹脂 |
CN107207720A (zh) * | 2015-02-17 | 2017-09-26 | 沙特基础工业全球技术有限公司 | 淬灭熔融聚碳酸酯的方法 |
CN108884216B (zh) | 2016-04-28 | 2020-04-07 | 沙特基础工业全球技术有限公司 | 聚(酯-碳酸酯)共聚物、由其形成的制品及制备方法 |
WO2017187428A1 (en) | 2016-04-28 | 2017-11-02 | Sabic Global Technologies B.V. | Laser weldable compositions, articles formed therefrom, and methods of manufacture |
EP3350247B1 (en) | 2016-04-28 | 2019-02-13 | SABIC Global Technologies B.V. | Poly(ester-carbonate) copolymers, articles formed therefrom, and methods of manufacture |
WO2017187427A1 (en) | 2016-04-28 | 2017-11-02 | Sabic Global Technologies B.V. | Poly(ester-carbonate)s, articles formed therefrom, and methods of manufacture |
CN110461904B (zh) * | 2017-03-31 | 2022-06-28 | 出光兴产株式会社 | 热塑性树脂的制造方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH02238020A (ja) * | 1988-12-07 | 1990-09-20 | E I Du Pont De Nemours & Co | 芳香族カーボネートを使用する全芳香族ポリエステルカルボン酸末端の末端遮蔽 |
JP2002322266A (ja) * | 2001-04-27 | 2002-11-08 | Mitsubishi Chemicals Corp | 芳香族ポリカーボネートの製造方法 |
WO2003048230A1 (en) * | 2001-10-10 | 2003-06-12 | General Electric Company | Method for end-capping polycarbonate resins and composition for use in same |
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JPH0727662B2 (ja) * | 1987-08-27 | 1995-03-29 | 出光石油化学株式会社 | 光ディスク基板 |
JPS6456728U (ja) | 1987-10-02 | 1989-04-10 | ||
US4994594A (en) * | 1988-02-29 | 1991-02-19 | General Electric Company | Oligomeric carbonate chainstoppers |
ATE169316T1 (de) * | 1988-09-22 | 1998-08-15 | Ge Plastics Japan Ltd | Verfahren zur herstellung von polycarbonaten |
BR9007196A (pt) * | 1989-12-22 | 1991-12-10 | Gen Electric | Composicao |
JP3218100B2 (ja) * | 1992-10-19 | 2001-10-15 | 三井化学株式会社 | 芳香族ポリカーボネート |
WO1999036458A1 (fr) * | 1998-01-13 | 1999-07-22 | Idemitsu Petrochemical Co., Ltd. | Procede de production de polycarbonate et substrat de disque optique |
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JP4606660B2 (ja) | 2001-07-17 | 2011-01-05 | Sabicイノベーティブプラスチックスジャパン合同会社 | ポリカーボネートの製造方法およびポリカーボネート製造装置 |
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US6706846B2 (en) * | 2001-10-10 | 2004-03-16 | General Electric Company | Method for end-capping polycarbonate resins and composition for use in same |
US6500914B1 (en) * | 2001-10-10 | 2002-12-31 | General Electric Company | Method for end-capping polycarbonate resins and composition for use in same |
KR100713099B1 (ko) | 2005-03-07 | 2007-05-02 | 주식회사 엘지화학 | 폴리카보네이트 수지의 제조 방법 |
-
2005
- 2005-03-07 KR KR1020050018844A patent/KR100713099B1/ko active IP Right Grant
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2006
- 2006-03-06 CN CN2006800012021A patent/CN101061159B/zh active Active
- 2006-03-06 EP EP06716206A patent/EP1856180B1/en active Active
- 2006-03-06 US US11/368,568 patent/US7495065B2/en active Active
- 2006-03-06 JP JP2007540272A patent/JP4624424B2/ja active Active
- 2006-03-06 WO PCT/KR2006/000756 patent/WO2006095982A1/en active Application Filing
- 2006-03-06 ES ES06716206T patent/ES2373677T3/es active Active
- 2006-03-07 TW TW095107561A patent/TWI316949B/zh active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH02238020A (ja) * | 1988-12-07 | 1990-09-20 | E I Du Pont De Nemours & Co | 芳香族カーボネートを使用する全芳香族ポリエステルカルボン酸末端の末端遮蔽 |
JP2002322266A (ja) * | 2001-04-27 | 2002-11-08 | Mitsubishi Chemicals Corp | 芳香族ポリカーボネートの製造方法 |
WO2003048230A1 (en) * | 2001-10-10 | 2003-06-12 | General Electric Company | Method for end-capping polycarbonate resins and composition for use in same |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2015176662A (ja) * | 2014-03-13 | 2015-10-05 | 国立研究開発法人産業技術総合研究所 | ナトリウムイオン二次電池用正極活物質 |
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WO2006095982A1 (en) | 2006-09-14 |
CN101061159A (zh) | 2007-10-24 |
TWI316949B (en) | 2009-11-11 |
CN101061159B (zh) | 2010-09-08 |
EP1856180B1 (en) | 2011-09-14 |
ES2373677T3 (es) | 2012-02-07 |
US20060199940A1 (en) | 2006-09-07 |
TW200631988A (en) | 2006-09-16 |
JP4624424B2 (ja) | 2011-02-02 |
US7495065B2 (en) | 2009-02-24 |
EP1856180A4 (en) | 2009-02-25 |
KR100713099B1 (ko) | 2007-05-02 |
EP1856180A1 (en) | 2007-11-21 |
KR20060097326A (ko) | 2006-09-14 |
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