CN101679562B - 具有长支链的可熔融加工的含氟聚合物及其制备方法和应用 - Google Patents
具有长支链的可熔融加工的含氟聚合物及其制备方法和应用 Download PDFInfo
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- CN101679562B CN101679562B CN200880015518.5A CN200880015518A CN101679562B CN 101679562 B CN101679562 B CN 101679562B CN 200880015518 A CN200880015518 A CN 200880015518A CN 101679562 B CN101679562 B CN 101679562B
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| GB0709033.5 | 2007-05-11 | ||
| GB0709033A GB0709033D0 (en) | 2007-05-11 | 2007-05-11 | Melt-Processible fluoropolymers having long-chain branches, Methods of preparing them and uses thereof |
| PCT/US2008/061424 WO2008140914A1 (en) | 2007-05-11 | 2008-04-24 | Melt-processible fluoropolymers having long-chain branches, methods of preparing them and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101679562A CN101679562A (zh) | 2010-03-24 |
| CN101679562B true CN101679562B (zh) | 2012-03-14 |
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Country Status (6)
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| US (1) | US8969500B2 (enExample) |
| EP (2) | EP2147028B1 (enExample) |
| JP (2) | JP5726519B2 (enExample) |
| CN (1) | CN101679562B (enExample) |
| GB (1) | GB0709033D0 (enExample) |
| WO (1) | WO2008140914A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
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| ATE485316T1 (de) * | 2006-08-24 | 2010-11-15 | 3M Innovative Properties Co | Verfahren zur herstellung von fluorpolymeren |
| GB0709033D0 (en) * | 2007-05-11 | 2007-06-20 | 3M Innovative Properties Co | Melt-Processible fluoropolymers having long-chain branches, Methods of preparing them and uses thereof |
| GB0801194D0 (en) * | 2008-01-23 | 2008-02-27 | 3M Innovative Properties Co | Processing aid compositions comprising fluoropolymers having long-chain branches |
| JP5582877B2 (ja) * | 2010-06-07 | 2014-09-03 | 信越ポリマー株式会社 | フィルムキャパシタ用フィルムの製造方法及びフィルムキャパシタ用フィルム |
| EP2409998B1 (en) * | 2010-07-23 | 2015-11-25 | 3M Innovative Properties Company | High melting PTFE polymers suitable for melt-processing into shaped articles |
| GB201012944D0 (en) * | 2010-08-02 | 2010-09-15 | 3M Innovative Properties Co | Peroxide curable fluoroelastomers containing modifiers and iodine or bromine endgroups |
| JP6017550B2 (ja) * | 2011-06-09 | 2016-11-02 | ソルベイ スペシャルティ ポリマーズ イタリー エス.ピー.エー. | 超分岐フルオロエラストマー添加剤 |
| WO2014023611A1 (en) | 2012-08-10 | 2014-02-13 | Solvay Specialty Polymers Italy S.P.A. | Allyl-bearing fluorinated ionomers |
| US20160083489A1 (en) * | 2013-06-14 | 2016-03-24 | 3M Innovative Properties Company | Fluoropolymers comprising monomeric units derived from a vinyl perfluoroalkyl or vinyl perfluoroalkylenoxide perfluorovinyl ether |
| EP3114167B1 (en) | 2014-03-06 | 2020-05-27 | 3M Innovative Properties Company | Highly fluorinated elastomers |
| CN108350244B (zh) | 2015-10-23 | 2021-01-29 | 3M创新有限公司 | 包含无定形含氟聚合物和氟塑料粒子的组合物及其制备方法 |
| CN108495877B (zh) | 2016-01-21 | 2021-06-08 | 3M创新有限公司 | 含氟聚合物的增材加工 |
| JP7160035B2 (ja) * | 2017-07-05 | 2022-10-25 | Agc株式会社 | 含フッ素弾性共重合体、その組成物および架橋ゴム物品 |
| TW201908426A (zh) | 2017-07-19 | 2019-03-01 | 美商3M新設資產公司 | 藉由加成性加工製造聚合物物品及聚合物複合物之方法以及聚合物及複合物品 |
| CA3070323A1 (en) | 2017-07-19 | 2019-01-24 | 3M Innovative Properties Company | Additive processing of fluoropolymers |
| JP6959885B2 (ja) * | 2018-03-14 | 2021-11-05 | 株式会社クレハ | 非水電解質二次電池用のポリマーゲル電解質および非水電解質二次電池 |
| EP3807344B1 (en) | 2018-06-12 | 2023-12-27 | 3M Innovative Properties Company | Fluoropolymer coating compositions comprising aminosilane curing agents, coated substrates and related methods |
| EP3807369B1 (en) | 2018-06-12 | 2024-07-24 | 3M Innovative Properties Company | Fluoropolymer compositions comprising fluorinated additives, coated substrates and methods |
| EP3825336A4 (en) * | 2018-07-20 | 2021-06-16 | Kureha Corporation | PARTICULATE POLYMER BASED ON VINYLIDEN FLUORIDE AND A PROCESS FOR PRODUCING A PARTICULATE POLYMER BASED ON VINYLIDEN FLUORIDE |
| WO2020132309A1 (en) | 2018-12-21 | 2020-06-25 | Honeywell International Inc. | Solvent compositions containing 1,2,2-trifluoro-1-trifluoromethylcyclobutane (tfmcb) |
| WO2021088198A1 (en) | 2019-11-04 | 2021-05-14 | 3M Innovative Properties Company | Electronic telecommunications articles comprising crosslinked fluoropolymers and methods |
| CN114630874B (zh) * | 2019-11-04 | 2023-12-05 | 3M创新有限公司 | 包含具有烯键式不饱和基团和电子供体基团的固化剂的含氟聚合物组合物及用其涂覆的基底 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1155554A (zh) * | 1995-08-21 | 1997-07-30 | 拜尔公司 | 新的反应性和可加工性含氟弹性体的制备和用途 |
| US20050182199A1 (en) * | 2000-12-06 | 2005-08-18 | Naiyong Jing | Fluoropolymer coating compositions with multifunctional fluoroalkyl crosslinkers for anti-reflective polymer films |
| CN1764678A (zh) * | 2003-03-25 | 2006-04-26 | 3M创新有限公司 | 加工特性改善的可熔融加工的热塑性含氟聚合物及其制造方法 |
| CN1802393A (zh) * | 2003-06-09 | 2006-07-12 | 3M创新有限公司 | 一种包含具有长支链的含氟聚合物的可熔融加工的聚合物组合物 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2409274A (en) * | 1943-04-23 | 1946-10-15 | Du Pont | Polyfluoro organic ethers and their preparation |
| US4349650A (en) * | 1979-03-14 | 1982-09-14 | E. I. Du Pont De Nemours And Company | Polyfluoroallyloxy compounds, their preparation and copolymers therefrom |
| US4612357A (en) | 1985-07-09 | 1986-09-16 | E. I. Du Pont De Nemours And Company | Melt-processible tetrafluoroethylene copolymers and process for preparing them |
| JPS6323907A (ja) * | 1986-07-16 | 1988-02-01 | Nippon Mektron Ltd | パ−オキサイド加硫可能な含フツ素エラストマ−の製造方法 |
| JP2524123B2 (ja) * | 1986-08-18 | 1996-08-14 | 日本メクトロン株式会社 | 含フッ素共重合体の製法 |
| JPS63238115A (ja) | 1987-03-27 | 1988-10-04 | Asahi Glass Co Ltd | 環状構造を有する含フツ素共重合体の製造法 |
| US4897457A (en) * | 1987-08-14 | 1990-01-30 | Asahi Glass Company Ltd. | Novel fluorine-containing cyclic polymer |
| AU648048B2 (en) | 1989-10-06 | 1994-04-14 | E.I. Du Pont De Nemours And Company | Fluoropolymer process aids containing functional groups |
| JP3169187B2 (ja) * | 1992-01-21 | 2001-05-21 | 出光興産株式会社 | オレフィン系共重合体及びその製造法 |
| WO1995014719A1 (en) | 1992-08-28 | 1995-06-01 | E.I. Du Pont De Nemours And Company | Low-melting tetrafluoroethylene copolymer and its uses |
| JPH06324512A (ja) * | 1993-05-12 | 1994-11-25 | Konica Corp | 現像剤と画像形成方法 |
| US5312882A (en) * | 1993-07-30 | 1994-05-17 | The University Of North Carolina At Chapel Hill | Heterogeneous polymerization in carbon dioxide |
| IT1265461B1 (it) * | 1993-12-29 | 1996-11-22 | Ausimont Spa | Fluoroelastomeri comprendenti unita' monomeriche derivanti da una bis-olefina |
| IT1265460B1 (it) * | 1993-12-29 | 1996-11-22 | Ausimont Spa | Elastomeri termoplastici fluorurati dotati di migliorate proprieta' meccaniche ed elastiche, e relativo processo di preparazione |
| DE19530636A1 (de) * | 1995-08-21 | 1997-02-27 | Bayer Ag | Reaktive und verarbeitbare Fluorkautschuke, ein Verfahren zu deren Herstellung, ein Verfahren zur Herstellung von vernetzten, bepfropften oder modifizierten Fluorelastomeren unter Einsatz der reaktiven und verarbeitbaren Fluorkautschuke und deren Verwendung |
| US5859171A (en) | 1997-05-21 | 1999-01-12 | Dupont Toray | Polyimide copolymer, polyimide copolymer resin molded products and their preparation |
| US6270901B1 (en) * | 1997-12-19 | 2001-08-07 | Dyneon Llc | Compositions for bonding fluoroplastics |
| US6023002A (en) | 1998-01-26 | 2000-02-08 | 3M Innovative Properties Company | Process for preparing hydrofluoroethers |
| US6046368A (en) * | 1998-03-17 | 2000-04-04 | 3M Innovative Properties Company | Catalytic process for making hydrofluoroethers |
| US6221987B1 (en) * | 1998-04-17 | 2001-04-24 | Asahi Glass Company Ltd. | Method for producing a fluorine-containing polymer |
| US6429258B1 (en) | 1999-05-20 | 2002-08-06 | E. I. Du Pont De Nemours & Company | Polymerization of fluoromonomers |
| DE60019747T2 (de) | 1999-06-04 | 2006-05-11 | E.I. Du Pont De Nemours And Co., Wilmington | Verfahren zur herstellung von fluorolefinen |
| TW552435B (en) * | 2000-06-12 | 2003-09-11 | Asahi Glass Co Ltd | Plastic optical fiber |
| JP4415458B2 (ja) * | 2000-06-30 | 2010-02-17 | 旭硝子株式会社 | 含フッ素共重合体及び成形体 |
| DE60135080D1 (de) * | 2000-12-26 | 2008-09-11 | Asahi Glass Co Ltd | Festpolymer-Elektrolyt Material, flüssige Zusammensetzung, Festpolymer Brennstoffzelle und Fluorpolymer |
| DE60201386T8 (de) * | 2001-07-18 | 2006-08-24 | Asahi Glass Co., Ltd. | Optische Kunststofffaser und Verfahren zu deren Herstellung |
| US6861489B2 (en) * | 2001-12-06 | 2005-03-01 | Gore Enterprise Holdings, Inc. | Low equivalent weight ionomer |
| ATE413418T1 (de) | 2004-09-09 | 2008-11-15 | 3M Innovative Properties Co | Fluoropolymer zur herstellung von einem fluoroelastomer |
| JP2006236837A (ja) * | 2005-02-25 | 2006-09-07 | Fuji Photo Film Co Ltd | 固体電解質およびその製造方法、電極膜接合体、ならびに、燃料電池 |
| US7795332B2 (en) * | 2005-07-15 | 2010-09-14 | 3M Innovative Properties Company | Method of removing fluorinated carboxylic acid from aqueous liquid |
| GB0709033D0 (en) * | 2007-05-11 | 2007-06-20 | 3M Innovative Properties Co | Melt-Processible fluoropolymers having long-chain branches, Methods of preparing them and uses thereof |
| US11274172B2 (en) | 2009-08-27 | 2022-03-15 | Daikin Industries, Ltd. | Processing additive, molding composition masterbatch of processing additive and molding article |
-
2007
- 2007-05-11 GB GB0709033A patent/GB0709033D0/en not_active Ceased
-
2008
- 2008-04-24 CN CN200880015518.5A patent/CN101679562B/zh not_active Expired - Fee Related
- 2008-04-24 WO PCT/US2008/061424 patent/WO2008140914A1/en not_active Ceased
- 2008-04-24 US US12/597,022 patent/US8969500B2/en not_active Expired - Fee Related
- 2008-04-24 JP JP2010507519A patent/JP5726519B2/ja not_active Expired - Fee Related
- 2008-04-24 EP EP08746785.8A patent/EP2147028B1/en not_active Not-in-force
- 2008-04-24 EP EP12163339.0A patent/EP2474564B1/en not_active Not-in-force
-
2013
- 2013-11-05 JP JP2013229394A patent/JP2014065911A/ja not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1155554A (zh) * | 1995-08-21 | 1997-07-30 | 拜尔公司 | 新的反应性和可加工性含氟弹性体的制备和用途 |
| US20050182199A1 (en) * | 2000-12-06 | 2005-08-18 | Naiyong Jing | Fluoropolymer coating compositions with multifunctional fluoroalkyl crosslinkers for anti-reflective polymer films |
| CN1764678A (zh) * | 2003-03-25 | 2006-04-26 | 3M创新有限公司 | 加工特性改善的可熔融加工的热塑性含氟聚合物及其制造方法 |
| CN1802393A (zh) * | 2003-06-09 | 2006-07-12 | 3M创新有限公司 | 一种包含具有长支链的含氟聚合物的可熔融加工的聚合物组合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US8969500B2 (en) | 2015-03-03 |
| EP2474564A3 (en) | 2012-10-31 |
| JP2010526908A (ja) | 2010-08-05 |
| EP2147028A4 (en) | 2011-10-12 |
| CN101679562A (zh) | 2010-03-24 |
| JP2014065911A (ja) | 2014-04-17 |
| WO2008140914A1 (en) | 2008-11-20 |
| GB0709033D0 (en) | 2007-06-20 |
| US20100121012A1 (en) | 2010-05-13 |
| EP2474564A2 (en) | 2012-07-11 |
| JP5726519B2 (ja) | 2015-06-03 |
| EP2147028A1 (en) | 2010-01-27 |
| EP2147028B1 (en) | 2013-09-04 |
| EP2474564B1 (en) | 2014-01-22 |
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