JP5734859B2 - 高純度4,4′−ジフルオロベンゾフェノンを使用する、ポリ(アリールエーテルケトン)を製造するための改善された方法 - Google Patents
高純度4,4′−ジフルオロベンゾフェノンを使用する、ポリ(アリールエーテルケトン)を製造するための改善された方法 Download PDFInfo
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- JP5734859B2 JP5734859B2 JP2011532649A JP2011532649A JP5734859B2 JP 5734859 B2 JP5734859 B2 JP 5734859B2 JP 2011532649 A JP2011532649 A JP 2011532649A JP 2011532649 A JP2011532649 A JP 2011532649A JP 5734859 B2 JP5734859 B2 JP 5734859B2
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- difluorobenzophenone
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- paek
- ether ketone
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- 229920006260 polyaryletherketone Polymers 0.000 title claims description 67
- 238000000034 method Methods 0.000 title claims description 52
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 title claims description 30
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- LKFIWRPOVFNPKR-UHFFFAOYSA-N (2-fluorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1F LKFIWRPOVFNPKR-UHFFFAOYSA-N 0.000 claims description 20
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- ADUODNZKKNUWBZ-UHFFFAOYSA-N [4-(4-hydroxybenzoyl)phenyl]-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(C(=O)C=2C=CC(O)=CC=2)C=C1 ADUODNZKKNUWBZ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D7/00—Carbonates of sodium, potassium or alkali metals in general
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4087—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group characterised by the catalyst used
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4093—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group characterised by the process or apparatus used
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/02—Condensation polymers of aldehydes or ketones with phenols only of ketones
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
- C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing heteroatoms
- C08G2261/3444—Polyethersulfones
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
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| PCT/EP2009/064008 WO2010046483A1 (en) | 2008-10-24 | 2009-10-23 | Improved process for preparing a poly(aryl ether ketone) using a high purity 4,4'-difluorobenzophenone |
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| JP2011532649A Active JP5734859B2 (ja) | 2008-10-24 | 2009-10-23 | 高純度4,4′−ジフルオロベンゾフェノンを使用する、ポリ(アリールエーテルケトン)を製造するための改善された方法 |
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| JP2014252460A Active JP5933676B2 (ja) | 2008-10-24 | 2014-12-12 | 高純度ジフェニルスルホン、調製、およびポリ(アリールエーテルケトン)の調製のためのその使用 |
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| JP2014252460A Active JP5933676B2 (ja) | 2008-10-24 | 2014-12-12 | 高純度ジフェニルスルホン、調製、およびポリ(アリールエーテルケトン)の調製のためのその使用 |
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Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102257033B (zh) * | 2008-10-24 | 2014-01-29 | 索维高级聚合物股份有限公司 | 用于制造聚(芳基醚酮)的改进的方法以及用于提供适合于制造聚(芳基醚酮)的碳酸钠的改进的方法 |
| CN101580583B (zh) * | 2009-06-26 | 2011-03-30 | 金发科技股份有限公司 | 采用四元共聚技术制备聚芳醚酮类共聚物的方法 |
| KR20120032014A (ko) | 2009-07-24 | 2012-04-04 | 인비스타 테크놀러지스 에스.에이.알.엘. | 이온성 액체를 사용하는 합성 방법 |
| JP5316727B1 (ja) * | 2011-09-21 | 2013-10-16 | 東レ株式会社 | 環式ポリフェニレンエーテルエーテルケトン組成物の回収方法およびそれを用いたポリフェニレンエーテルエーテルケトンの製造方法 |
| WO2014097564A1 (ja) * | 2012-12-21 | 2014-06-26 | 東レ株式会社 | 環式ポリフェニレンエーテルエーテルケトン組成物および線状ポリフェニレンエーテルエーテルケトンの製造方法、ポリフェニレンエーテルエーテルケトンの製造方法 |
| JP6221311B2 (ja) * | 2013-04-05 | 2017-11-01 | 東レ株式会社 | ポリフェニレンエーテルエーテルケトンの製造方法 |
| US20160075833A1 (en) * | 2013-05-02 | 2016-03-17 | Basf Se | Polyarylethersulfone copolymers |
| JP6169255B2 (ja) * | 2013-05-02 | 2017-07-26 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | ポリアリールエーテルスルホンコポリマー |
| GB201311376D0 (en) | 2013-06-26 | 2013-08-14 | Victrex Mfg Ltd | Polymetric Materials |
| GB2526243B (en) | 2014-02-24 | 2021-07-14 | Victrex Mfg Ltd | Polymeric materials |
| GB201409128D0 (en) * | 2014-05-22 | 2014-07-09 | Ketonex Ltd | Method |
| WO2016028614A1 (en) | 2014-08-21 | 2016-02-25 | Ticona Llc | Composition containing a polyaryletherketone and low naphthenic liquid crystalline polymer |
| EP3183321A1 (en) | 2014-08-21 | 2017-06-28 | Ticona LLC | Polyaryletherketone composition |
| GB201415972D0 (en) | 2014-09-10 | 2014-10-22 | Ketonex Ltd | Process |
| JP6841759B2 (ja) * | 2014-12-19 | 2021-03-10 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | ビメソゲン化合物およびメソゲン性媒体 |
| JP2018502972A (ja) * | 2015-01-23 | 2018-02-01 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 溶融重合法からのポリアリールエーテルの脱塩 |
| EP3247737B1 (de) * | 2015-01-23 | 2018-10-24 | Basf Se | Entsalzung von polyarylethern mittels schmelzeextraktion |
| EP3222651A1 (de) | 2016-03-21 | 2017-09-27 | Basf Se | Entsalzung von polyarylethern mittels schmelzeextraktion |
| GB2569512A (en) * | 2016-09-26 | 2019-06-19 | Victrex Mfg Ltd | Polymers and process for their manufacture |
| WO2018086873A1 (en) | 2016-11-11 | 2018-05-17 | Solvay Specialty Polymers Usa, Llc | Polyarylether ketone copolymer |
| JP7262387B2 (ja) | 2016-11-11 | 2023-04-21 | ソルベイ スペシャルティ ポリマーズ ユーエスエー, エルエルシー | ポリアリールエーテルケトンコポリマー |
| EP3559085B2 (en) * | 2016-12-21 | 2025-08-06 | Solvay Specialty Polymers USA, LLC | Poly(ether ketone ketone) polymers |
| WO2018115035A1 (en) | 2016-12-21 | 2018-06-28 | Solvay Specialty Polymers Usa, Llc | Poly(ether ketone ketone) polymers, corresponding synthesis methods and polymer compositions and articles made therefrom |
| EP3558918B1 (en) * | 2016-12-21 | 2021-11-10 | Solvay Specialty Polymers USA, LLC | Method for decreasing the concentration of a metal in a monomer composition comprising bis(benzoyl)benzene |
| WO2018115033A1 (en) | 2016-12-21 | 2018-06-28 | Solvay Specialty Polymers Usa, Llc | Poly(ether ketone ketone) polymers, corresponding synthesis methods and polymer compositions and articles made therefrom |
| CN110248984B (zh) | 2016-12-21 | 2022-03-04 | 索尔维特殊聚合物美国有限责任公司 | 聚(醚酮酮)聚合物、相应的合成方法和聚合物组合物以及由其制成的制品 |
| CN110809595B (zh) | 2017-06-30 | 2024-03-08 | 索尔维特殊聚合物美国有限责任公司 | 具有低挥发物含量的聚(醚酮酮)聚合物粉末 |
| CN111417670B (zh) | 2017-12-20 | 2024-05-17 | 索尔维特殊聚合物美国有限责任公司 | 制造PEEK-PEmEK共聚物的方法和由该方法获得的共聚物 |
| EP3810678A1 (en) * | 2018-06-21 | 2021-04-28 | Solvay Specialty Polymers USA, LLC. | Poly(ether ketone ketone) (pekk) polymer and composites |
| CN109061026B (zh) * | 2018-09-05 | 2020-12-25 | 九江天赐高新材料有限公司 | 一种对合成的peek样品进行分析检测的方法 |
| US10731001B2 (en) | 2018-11-09 | 2020-08-04 | Arkema France | Method for the recovery of compounds deriving from the synthesis of poly aryl ether ketone polymers |
| EP3650095B1 (en) | 2018-11-09 | 2025-09-03 | Arkema France | Method for the recovery of compounds deriving from the synthesis of aryl ether ketones by evaporation with a rotor |
| WO2020095115A2 (en) | 2018-11-09 | 2020-05-14 | Arkema France | Method for the recovery of compounds deriving from the synthesis of aryl ether ketones |
| CN109725087B (zh) * | 2019-03-16 | 2021-05-14 | 丁立平 | 一种测定纺织品中三种痕量多卤代苯酚的气相色谱-质谱联用法 |
| EP3986971B1 (en) | 2019-06-20 | 2023-08-09 | Solvay Specialty Polymers USA, LLC. | Polymer-metal junction comprising peek-peoek copolymer compositions, in contact with a metal substrate |
| US11845832B2 (en) | 2019-06-20 | 2023-12-19 | Solvay Specialty Polymers Usa, Llc | Method of making a PEEK-PEoEK copolymer and copolymer obtained from the method |
| WO2020254096A1 (en) | 2019-06-20 | 2020-12-24 | Solvay Specialty Polymers Usa, Llc | Peek-peodek copolymer and method of making the copolymer |
| WO2021001132A1 (en) | 2019-07-01 | 2021-01-07 | Solvay Specialty Polymers Usa, Llc | PEEK-PEoEK COPOLYMER POWDER AND METHOD OF PREPARING THE POWDER |
| WO2021008983A1 (en) | 2019-07-12 | 2021-01-21 | Solvay Specialty Polymers Usa, Llc | Fiber reinforced thermoplastic matrix composite material |
| WO2021204718A1 (en) | 2020-04-06 | 2021-10-14 | Solvay Specialty Polymers Usa, Llc | Polyarylether ketone polymers |
| GB2612746B (en) * | 2020-09-02 | 2023-12-06 | Idemitsu Kosan Co | Method for producing aromatic polyether, and potassium carbonate used in same |
| TW202219111A (zh) * | 2020-09-02 | 2022-05-16 | 日商出光興產股份有限公司 | 聚醚醚酮之製造方法 |
| CN116710783A (zh) * | 2020-12-03 | 2023-09-05 | 豪夫迈·罗氏有限公司 | 通过交叉喷雾esi质谱检测目标分析物 |
| CN113563578B (zh) * | 2021-08-16 | 2023-12-26 | 吉林省中研高分子材料股份有限公司 | 一种制备聚(芳基醚酮)的方法及聚(芳基醚酮) |
| CN113912799B (zh) * | 2021-09-16 | 2022-05-10 | 吉林省中研高分子材料股份有限公司 | 聚醚醚酮及其制备方法 |
| CN114230785B (zh) * | 2021-11-17 | 2023-03-03 | 吉林省中研高分子材料股份有限公司 | 一种耐辐射的聚醚醚酮聚合物及其制备方法 |
| EP4286026A1 (en) * | 2022-05-31 | 2023-12-06 | Basf Se | Method for separating an aprotic polar solvent from a mixture comprising water, the aprotic polar solvent and at least one inorganic salt |
| CN116087378A (zh) * | 2022-11-28 | 2023-05-09 | 湖北省宏源药业科技股份有限公司 | 一种气相色谱法测定4,4’-二氟二苯甲酮纯度的方法 |
| CN119264414A (zh) * | 2024-11-15 | 2025-01-07 | 季华实验室 | 一种磺化聚醚醚酮及其制备方法 |
Family Cites Families (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3655331A (en) * | 1969-06-06 | 1972-04-11 | Intermountain Res & Dev Corp | Production of sodium carbonate |
| US3953400A (en) | 1972-01-17 | 1976-04-27 | Raychem Corporation | Polyketones and methods therefor |
| US3928295A (en) | 1973-05-25 | 1975-12-23 | Ici Ltd | Aromatic polymers containing ketone linking groups and process for their preparation |
| US3904733A (en) * | 1973-06-20 | 1975-09-09 | Allied Chem | Prevention of calcium deposition from trona-derived sodium carbonate liquors |
| US3956240A (en) * | 1973-07-12 | 1976-05-11 | Raychem Corporation | Novel polyketones |
| US4151261A (en) * | 1975-06-17 | 1979-04-24 | Allied Chemical Corporation | Method of preparing sodium liquors low in calcium |
| GB1563222A (en) * | 1976-02-10 | 1980-03-19 | Ici Ltd | Aromatic polymer production |
| US4113699A (en) * | 1976-07-08 | 1978-09-12 | Imperial Chemical Industries Limited | Production of aromatic polymers |
| GB1586972A (en) | 1977-02-01 | 1981-03-25 | Ici Ltd | Production of aromatic polyethers |
| USRE34085E (en) | 1977-09-07 | 1992-09-29 | Imperial Chemical Industries | Thermoplastic aromatic polyetherketones |
| EP0001879B2 (en) * | 1977-09-07 | 1989-11-23 | Imperial Chemical Industries Plc | Thermoplastic aromatic polyetherketones, a method for their preparation and their application as electrical insulants |
| US4331798A (en) * | 1979-01-18 | 1982-05-25 | Imperial Chemical Industries Limited | Production of aromatic polyethers with infusible particulate substance |
| DE3342433A1 (de) | 1983-11-24 | 1985-06-05 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von aromatischen polyaethern |
| ES8700647A1 (es) | 1984-10-11 | 1986-11-16 | Raychem Corp | Procedimiento para la preparacion de un compuesto carbonilo aromatico |
| GB8505682D0 (en) | 1985-03-05 | 1985-05-09 | Ici Plc | Polyarylether |
| US4638044A (en) * | 1985-03-20 | 1987-01-20 | Amoco Corporation | Process for preparing poly(aryl ether ketone)s |
| US4954605A (en) * | 1985-05-10 | 1990-09-04 | Hoechst Celanese Corp. | Aromatic polyetherketone fiber product |
| US4731429A (en) * | 1985-06-17 | 1988-03-15 | Amoco Corporation | Novel poly(aryl ether ketones) |
| US5120818A (en) * | 1985-06-21 | 1992-06-09 | Amoco Corporation | Chain-extended poly(aryl ether ketones) |
| US4908425A (en) * | 1985-06-21 | 1990-03-13 | Amoco Corporation | Chain-extended poly(aryl ether ketones) |
| US4774311A (en) * | 1985-08-21 | 1988-09-27 | Amoco Corporation | Preparation of poly(aryl ether ketones) in the presence of an alkali, alkaline earth of lanthanide metal salt |
| EP0211693A1 (en) * | 1985-08-21 | 1987-02-25 | Amoco Corporation | Preparation of poly(aryl ether ketones) |
| GB8601994D0 (en) * | 1986-01-28 | 1986-03-05 | Ici Plc | Aromatic polymer |
| US4767837A (en) * | 1986-01-29 | 1988-08-30 | Raychem Corporation | Method for preparing poly(aryl ether ketones) |
| US4766197A (en) * | 1986-10-28 | 1988-08-23 | Amoco Corporation | Modified poly(aryl ether ketones) derived from biphenol |
| US4906784A (en) * | 1986-11-10 | 1990-03-06 | Amoco Corporation | Thermoplastic polyetherketones |
| DE3700810A1 (de) * | 1987-01-14 | 1988-07-28 | Basf Ag | Hochtemperaturbestaendige polyaryletherketone |
| DE3700808A1 (de) * | 1987-01-14 | 1988-07-28 | Basf Ag | Verfahren zur herstellung von polyaryletherketonen |
| GB8702993D0 (en) * | 1987-02-10 | 1987-03-18 | Ici Plc | Aromatic polymer |
| EP0292211A3 (en) | 1987-05-18 | 1989-06-14 | Imperial Chemical Industries Plc | Production and/or handling of polymers |
| GB8719125D0 (en) | 1987-08-12 | 1987-09-16 | Ici Plc | Aromatic polymer |
| JPS6465129A (en) * | 1987-09-04 | 1989-03-10 | Mitsubishi Gas Chemical Co | Production of aromatic polyether |
| DE3730690A1 (de) * | 1987-09-12 | 1989-03-23 | Bayer Ag | Verfahren zur herstellung von aromatischen polyetherketonen |
| GB8726884D0 (en) * | 1987-11-17 | 1987-12-23 | Raychem Ltd | Poly(arylene ether ketones) |
| GB8730135D0 (en) * | 1987-12-24 | 1988-02-03 | Ici Plc | Polyarylether ketone |
| US4855388A (en) * | 1987-12-29 | 1989-08-08 | Amoco Corporation | Co-reagent stabilization of poly(aryl ether sulfones) using sodium, lithium, alkaline earth or lanthanide metal salts |
| GB8809082D0 (en) | 1988-04-18 | 1988-05-18 | Ici Plc | Aryl ketone monomers |
| DE3840617A1 (de) * | 1988-07-23 | 1990-02-01 | Bayer Ag | Verfahren zur herstellung von aromatischen polyetherketonen |
| DE3829283A1 (de) * | 1988-08-30 | 1990-03-01 | Basf Ag | Polyaryletherketone |
| US5049640A (en) * | 1989-02-23 | 1991-09-17 | Shell Oil Company | Polyetherketones |
| US5017685A (en) * | 1989-02-24 | 1991-05-21 | E. I. Du Pont De Nemours And Company | Process for extracting metal residue from poly(ether ketone ketones) |
| DE3907027A1 (de) * | 1989-03-04 | 1990-09-13 | Basf Ag | Verfahren zur herstellung von polyaryletherketonen durch elektrophile polykondensation |
| DE3907474A1 (de) * | 1989-03-08 | 1990-09-13 | Bayer Ag | Verfahren zur herstellung von aromatischen polyetherketonen |
| EP0388358B1 (de) * | 1989-03-17 | 1996-09-25 | Sumitomo Chemical Company Limited | Neue Polyarylenether |
| WO1990014379A1 (fr) * | 1989-05-23 | 1990-11-29 | Teijin Limited | Poly(arylene-ether-cetone), procede de production et utilisation d'un tel compose |
| DE3926262A1 (de) * | 1989-08-09 | 1991-02-14 | Hoechst Ag | Verfahren zur herstellung eines aromatischen polyethers in gegenwart von feinverteilten kondensationshilfsmitteln |
| DE3926263A1 (de) * | 1989-08-09 | 1991-02-14 | Hoechst Ag | Verfahren zur herstellung eines aromatischen polyethers |
| US5049340A (en) * | 1989-12-18 | 1991-09-17 | E. I. Du Pont De Nemours And Company | Process for making continuous films of ordered poly(ether ketone ketones) |
| US5169923A (en) | 1991-05-23 | 1992-12-08 | Hay Allan S | Bisphenols and poly(imidoarylether ketone)s and poly(imidoarylether sulfone)s produced therefrom |
| DE4121139B4 (de) | 1991-06-26 | 2004-12-09 | Ticona Gmbh | Verfahren zur Herstellung von Polyarylenethern und ihre Verwendung |
| EP0528266A3 (en) * | 1991-08-20 | 1993-05-05 | Basf Aktiengesellschaft | Method for the production of polyarylethers |
| DE4205811A1 (de) * | 1992-02-26 | 1993-11-18 | Hoechst Ag | Polyetherketone und Polyethersulfone auf Basis Phenylindan und ihre Verwendung für optische Systeme |
| TW256843B (OSRAM) * | 1992-06-11 | 1995-09-11 | Hoechst Ag | |
| US5268444A (en) * | 1993-04-02 | 1993-12-07 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Phenylethynyl-terminated poly(arylene ethers) |
| DE4326774A1 (de) * | 1993-08-10 | 1995-02-16 | Basf Ag | Verfahren zur Herstellung von Polyarylenetherketonen |
| EP0759903B1 (en) * | 1994-05-16 | 2001-09-05 | Avecia Limited | Process for the preparation of benzophenthiones and benzophenones |
| GB9409885D0 (en) | 1994-05-18 | 1994-07-06 | Vitrex Manufacturing Limited | Process for making an aromatic polymer |
| US5523384A (en) * | 1995-03-28 | 1996-06-04 | E. I. Du Pont De Nemours And Company | Process for preparing polyether ketones |
| JPH09188757A (ja) * | 1995-11-07 | 1997-07-22 | Alps Electric Co Ltd | 硬化性樹脂組成物、その製造方法および樹脂硬化物 |
| WO2000015691A1 (en) | 1998-09-11 | 2000-03-23 | Victrex Manufacturing Limited | Ion-exchange polymers |
| EP1013629A1 (en) * | 1998-12-22 | 2000-06-28 | Mitsui Chemicals, Inc. | Preparation process of fluorine subsituted aromatic compound |
| WO2001019896A1 (en) * | 1999-09-10 | 2001-03-22 | Victrex Manufacturing Limited | Composite ion-exchange membranes |
| US6593445B2 (en) | 2000-03-03 | 2003-07-15 | Solvay Advanced Polymers, Llc | Low color poly(biphenyl ether sulfone) and improved process for the preparation thereof |
| US7303830B2 (en) * | 2001-03-21 | 2007-12-04 | Victrex Manufacturing Limited | Fuel cell |
| US6939922B2 (en) * | 2001-03-30 | 2005-09-06 | Rohm And Haas Company | Coating and coating composition |
| GB0113053D0 (en) * | 2001-05-30 | 2001-07-18 | Victrex Mfg Ltd | Polyketones |
| WO2003050163A1 (fr) * | 2001-12-11 | 2003-06-19 | Mitsui Chemicals, Inc. | Cetone de polyether et procede de production |
| JP2004315764A (ja) | 2003-04-21 | 2004-11-11 | Sumitomo Chem Co Ltd | 芳香族ポリエーテルの製造法 |
| CN1190451C (zh) * | 2003-07-08 | 2005-02-23 | 吉林大学 | 新型可控交联聚芳醚酮类高性能材料及其制备 |
| GB0322598D0 (en) | 2003-09-26 | 2003-10-29 | Victrex Mfg Ltd | Polymeric material |
| DE102005037337A1 (de) | 2005-08-04 | 2007-02-15 | Inspec Fibres Gmbh | Neues Verfahren zur Herstellung von 4,4'-Difluorbenzophenon |
| WO2007035402A2 (en) * | 2005-09-16 | 2007-03-29 | General Electric Company | Improved poly aryl ether ketone polymer blends |
| US7598337B2 (en) * | 2005-12-20 | 2009-10-06 | General Electric Company | Mixed-sulfonation block copolymers |
| EP1813292A1 (en) * | 2006-01-25 | 2007-08-01 | Inion Oy | Surgical implant and manufacturing method |
| JP2007238890A (ja) | 2006-03-13 | 2007-09-20 | Sumitomo Chemical Co Ltd | 芳香族ポリエーテルを製造する際に使用した反応溶媒の回収方法。 |
| DE102006022442A1 (de) * | 2006-05-13 | 2007-11-15 | Degussa Gmbh | Verfahren zur Herstellung von Polyarylenetherketon |
| GB0611760D0 (en) * | 2006-06-14 | 2006-07-26 | Victrex Mfg Ltd | Polymeric materials |
| GB0611759D0 (en) | 2006-06-14 | 2006-07-26 | Victrex Mfg Ltd | Polymeric material |
| JP2008248013A (ja) * | 2007-03-29 | 2008-10-16 | Sumitomo Chemical Co Ltd | 溶媒の回収方法および芳香族ポリエーテルの製造方法 |
| TWI461458B (zh) * | 2007-08-10 | 2014-11-21 | Solvay Advanced Polymers Llc | 改良之聚(芳基醚酮)類及製造彼等之方法 |
| CN100582133C (zh) | 2008-01-11 | 2010-01-20 | 吉林金正高分子材料研发有限公司 | 一种聚醚醚酮的制备方法 |
| EP2105430B1 (en) * | 2008-03-24 | 2011-11-16 | Gharda Chemicals Limited | Polyether ketone, its monomer and its phenolate |
| CN102257033B (zh) | 2008-10-24 | 2014-01-29 | 索维高级聚合物股份有限公司 | 用于制造聚(芳基醚酮)的改进的方法以及用于提供适合于制造聚(芳基醚酮)的碳酸钠的改进的方法 |
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