JP5684707B2 - パーフルオロモノマーと、官能基および重合可能な炭素−炭素二重結合を有するモノマーとから生じる繰り返し単位を含むフルオロポリマーを製造する水性重合方法 - Google Patents
パーフルオロモノマーと、官能基および重合可能な炭素−炭素二重結合を有するモノマーとから生じる繰り返し単位を含むフルオロポリマーを製造する水性重合方法 Download PDFInfo
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- JP5684707B2 JP5684707B2 JP2011522264A JP2011522264A JP5684707B2 JP 5684707 B2 JP5684707 B2 JP 5684707B2 JP 2011522264 A JP2011522264 A JP 2011522264A JP 2011522264 A JP2011522264 A JP 2011522264A JP 5684707 B2 JP5684707 B2 JP 5684707B2
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- 239000012286 potassium permanganate Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/26—Tetrafluoroethene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/26—Tetrafluoroethene
- C08F214/262—Tetrafluoroethene with fluorinated vinyl ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/26—Tetrafluoroethene
- C08F214/265—Tetrafluoroethene with non-fluorinated comonomers
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- Polymers & Plastics (AREA)
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- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8740108P | 2008-08-08 | 2008-08-08 | |
| US61/087,401 | 2008-08-08 | ||
| PCT/US2009/053106 WO2010017450A1 (en) | 2008-08-08 | 2009-08-07 | Aqueous polymerization process for the manufacture of fluoropolymer comprising repeating units arising from a perfluoromonomer and a monomer having a functional group and a polymerizable carbon-carbon double bond |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011530628A JP2011530628A (ja) | 2011-12-22 |
| JP2011530628A5 JP2011530628A5 (enExample) | 2012-08-30 |
| JP5684707B2 true JP5684707B2 (ja) | 2015-03-18 |
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| JP2011522264A Expired - Fee Related JP5684707B2 (ja) | 2008-08-08 | 2009-08-07 | パーフルオロモノマーと、官能基および重合可能な炭素−炭素二重結合を有するモノマーとから生じる繰り返し単位を含むフルオロポリマーを製造する水性重合方法 |
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| EP (1) | EP2310428A1 (enExample) |
| JP (1) | JP5684707B2 (enExample) |
| CN (1) | CN102112501B (enExample) |
| WO (1) | WO2010017450A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100034504A1 (en) * | 2008-08-08 | 2010-02-11 | E.I. Du Pont De Nemours And Company | Melt Processible Semicrystalline Fluoropolymer Comprising Repeating Units Arising from Tetrafluoroethylene and a Hydrocarbon Monomer Having a Functional Group and a Polymerizable Carbon-Carbon Double Bond, and Multilayer Articles Therefrom |
| EP2310427A1 (en) * | 2008-08-08 | 2011-04-20 | E. I. du Pont de Nemours and Company | Melt processible semicrystalline fluoropolymer having repeating units arising from tetrafluoroethylene, hexafluoropropylene, and hydrocarbon monomer having a carboxyl group and a polymerizable carbon-carbon double bond and multi-layer articles comprising a layer of the melt processible semicrystalline fluoropolymer |
| JP4858628B2 (ja) * | 2010-05-25 | 2012-01-18 | ユニマテック株式会社 | 含フッ素ポリマー水性分散液 |
| WO2012030784A1 (en) * | 2010-09-01 | 2012-03-08 | Arkema Inc. | Method of producing fluoropolymers using acid-functionalized monomers |
| CN106574055B (zh) * | 2014-08-01 | 2019-09-20 | Agc株式会社 | 树脂粉末、其制造方法、复合体、成形体、陶瓷成形体的制造方法、金属层叠板、印刷基板以及预浸料 |
| US11643484B2 (en) | 2015-03-16 | 2023-05-09 | Arkema Inc. | Modified fluoropolymers |
| WO2019076901A1 (en) * | 2017-10-17 | 2019-04-25 | Solvay Specialty Polymers Italy S.P.A. | PROCESS FOR SYNTHESIZING FLUOROPOLYMERS |
| US11441051B2 (en) | 2018-01-26 | 2022-09-13 | Uwm Research Foundation, Inc. | 3D hybrid composite coating |
| US12252596B2 (en) | 2018-07-23 | 2025-03-18 | Agc Chemicals Americas, Inc. | Glass-reinforced fluoropolymer compositions |
| EP4662061A1 (en) | 2023-02-07 | 2025-12-17 | Syensqo Specialty Polymers USA, LLC | Composite films for mobile electronic device components |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2468664A (en) * | 1945-08-28 | 1949-04-26 | Du Pont | Tetrafluoroethylene copolymers |
| US3250806A (en) * | 1962-04-05 | 1966-05-10 | Du Pont | Fluorocarbon ethers of tetrafluoroethylene epoxide |
| US3445434A (en) * | 1964-10-30 | 1969-05-20 | Du Pont | Copolymers of tetrafluoroethylene,ethylene and an olefinic acid |
| FR1437472A (fr) * | 1965-02-24 | 1966-05-06 | Aquitaine Petrole | Perfectionnement à la polymérisation de diènes conjugués |
| US3933773A (en) * | 1972-06-08 | 1976-01-20 | Thiokol Corporation | Thermoplastic elastomeric copolymers and terpolymers of tetrafluoroethylene and propylene and method of making the same |
| JPS5679110A (en) * | 1979-11-30 | 1981-06-29 | Asahi Glass Co Ltd | Preparation of modified polytetrafluoroethylene |
| US4837267A (en) * | 1988-03-21 | 1989-06-06 | E. I. Du Pont De Nemours And Company | Tetrafluoroethylene copolymers |
| KR960003930B1 (ko) * | 1988-05-13 | 1996-03-23 | 아사히가라스 가부시끼가이샤 | 수성 분산액의 제조방법, 수성 분산액 및 수성 도포 조성물 |
| US5349003A (en) * | 1988-09-20 | 1994-09-20 | Japan Synthetic Rubber Co., Ltd. | Aqueous fluorine-containing polymer dispersion and aqueous dispersion containing fluorine-containing polymer and water-soluble resin and/or water dispersible resin |
| US5064594A (en) * | 1989-10-06 | 1991-11-12 | E. I. Du Pont De Nemours And Company | Extrusion process for difficultly-melt-processible polymers |
| IT1271422B (it) * | 1993-10-15 | 1997-05-28 | Ausimont Spa | Procedimento per la preparazione di copolimeri del tetrafluoroetilene con altri monomeri perfluorurati |
| DE69835649T2 (de) * | 1997-10-15 | 2007-09-13 | E.I. Dupont De Nemours And Co., Wilmington | Copolymere aus Maleinsäure oder dessen Anhydrid und fluorierten Olefinen |
| US6300446B1 (en) * | 1998-03-31 | 2001-10-09 | Asahi Glass Company, Limited | Fluorine-containing copolymer and composition thereof |
| JP2000129193A (ja) * | 1998-08-20 | 2000-05-09 | Asahi Glass Co Ltd | フッ素系共重合体の水性分散液 |
| US6680357B1 (en) * | 1999-07-14 | 2004-01-20 | Atofina Chemicals, Inc. | Crosslinkable aqueous fluoropolymer based dispersions |
| JPWO2002010237A1 (ja) * | 2000-07-27 | 2004-01-08 | 旭硝子株式会社 | フッ素系共重合体の水性分散液 |
| JP4240201B2 (ja) * | 2002-02-22 | 2009-03-18 | 旭硝子株式会社 | 含フッ素共重合体 |
| US6822059B2 (en) * | 2002-04-05 | 2004-11-23 | 3M Innovative Properties Company | Dispersions containing bicomponent fluoropolymer particles and use thereof |
| JP4123272B2 (ja) * | 2002-06-17 | 2008-07-23 | ダイキン工業株式会社 | 含フッ素ポリマー分散体及び含フッ素ポリマー分散体製造方法 |
| EP1531164B1 (en) * | 2002-06-27 | 2006-09-27 | Asahi Glass Company Ltd. | Fluorocopolymer |
| JP4619650B2 (ja) * | 2002-06-27 | 2011-01-26 | 旭硝子株式会社 | 積層ホース |
| EP1576020B1 (en) * | 2002-12-23 | 2011-01-26 | 3M Innovative Properties Company | Fluoroplastic polymers having nitrogen-containing cure sites |
| JP4206968B2 (ja) * | 2004-03-24 | 2009-01-14 | Jsr株式会社 | 光導波路形成用樹脂組成物、その硬化物及び光導波路 |
| JP4424246B2 (ja) * | 2004-10-28 | 2010-03-03 | 旭硝子株式会社 | 含フッ素共重合体及びその用途 |
| US20060178472A1 (en) * | 2005-02-10 | 2006-08-10 | Johnson David W | Process for producing low fluorosurfactant-containing aqueous fluoropolymer dispersions with controlled pH |
| US7803867B2 (en) * | 2005-05-19 | 2010-09-28 | Arkema Inc. | Highly weatherable roof coatings containing aqueous fluoropolymer dispersions |
| TW200740913A (en) * | 2006-02-02 | 2007-11-01 | Jsr Corp | Polymer composition, paste for secondary battery electrode, and secondary battery electrode |
| TWI437009B (zh) * | 2007-04-24 | 2014-05-11 | Solvay Solexis Spa | 1,1-二氟乙烯共聚物類 |
| US20110092644A1 (en) * | 2008-07-10 | 2011-04-21 | E.I. Du Pont De Nemours And Company | Aqueous dispersion polymerization process for ethylene/tetrafluoroethylene copolymer |
| US8058376B2 (en) * | 2008-12-23 | 2011-11-15 | E. I. Du Pont De Nemours And Company | Fluoropolymer produced by aqueous polymerization using dispersed particulate of fluorinated lonomer produced in situ |
-
2009
- 2009-07-29 US US12/511,295 patent/US20100036053A1/en not_active Abandoned
- 2009-08-07 CN CN200980129795.3A patent/CN102112501B/zh not_active Expired - Fee Related
- 2009-08-07 EP EP09791272A patent/EP2310428A1/en not_active Withdrawn
- 2009-08-07 WO PCT/US2009/053106 patent/WO2010017450A1/en not_active Ceased
- 2009-08-07 JP JP2011522264A patent/JP5684707B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010017450A1 (en) | 2010-02-11 |
| JP2011530628A (ja) | 2011-12-22 |
| CN102112501A (zh) | 2011-06-29 |
| US20100036053A1 (en) | 2010-02-11 |
| EP2310428A1 (en) | 2011-04-20 |
| CN102112501B (zh) | 2014-11-19 |
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