GB1034197A - Sulphonic acid derivatives of fluorocarbon vinyl ethers, and polymers thereof - Google Patents

Sulphonic acid derivatives of fluorocarbon vinyl ethers, and polymers thereof

Info

Publication number
GB1034197A
GB1034197A GB35711/64A GB3571164A GB1034197A GB 1034197 A GB1034197 A GB 1034197A GB 35711/64 A GB35711/64 A GB 35711/64A GB 3571164 A GB3571164 A GB 3571164A GB 1034197 A GB1034197 A GB 1034197A
Authority
GB
United Kingdom
Prior art keywords
compounds
radical
fluorine
polymers
alkali metal
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.)
Expired
Application number
GB35711/64A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US384545A external-priority patent/US3282875A/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1034197A publication Critical patent/GB1034197A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
    • C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/78—Halides of sulfonic acids
    • C07C309/79—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms
    • C07C309/82—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms of a carbon skeleton substituted by singly-bound oxygen atoms
    • 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
    • C08F16/00—Homopolymers and 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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F16/12—Homopolymers and 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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
    • C08F16/14—Monomers containing only one unsaturated aliphatic radical
    • 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
    • C08F216/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F216/12—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
    • C08F216/14—Monomers containing only one unsaturated aliphatic radical
    • C08F216/1466—Monomers containing sulfur
    • C08F216/1475—Monomers containing sulfur and oxygen
    • 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
    • C08F28/00—Homopolymers and 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 bond to sulfur or by a heterocyclic ring containing sulfur

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:1034197/C2/1> wherein RF is fluorine or a C1-10 perfluoralkyl radical, Y is -F or -CF3, n is 1, 2 or 3, and M is fluorine, a hydroxyl radical, an amino radical or a radical of the formula -OMet where Met is an alkali metal or a substituted or unsubstituted ammonium radical. The compounds in which M is fluorine can be prepared by pyrolysis of compounds having the formulae <FORM:1034197/C2/2> and <FORM:1034197/C2/3> where RF, Y and n are as defined above and X is an alkali metal. The compounds in which M is fluorine can be converted into compounds in which M is -OH by hydrolysis with water and into compounds in which M is -NH2 by treatment with aqueous ammonia. Compounds in which M is -OMet are obtained by salifying compounds in which M is -OH with an alkali metal compound or an ammonium or substituted ammonium compound. Examples are given.ALSO:The invention comprises polymeric material containing the structure <FORM:1034197/C3/1> wherein RF is fluorine or a C1- 10 perfluoroalkyl radical, Y is -F or -CF3, n is 1, 2 or 3, and M is fluorine, a hydroxyl radical, an amino radical or a radical of the formula -OMet where Met is an alkali metal or a substituted or unsubstituted ammonium radical. The material may be prepared by homopolymerization of compounds of the formula CF2=CF-(-O-CF2-CFY-)n -O-CF2-CFRF-SO2-M RF, Y, M and n being as defined above, or by the copolymerization of such compounds with any ethylenically unsaturated monomer capable of homopolymerization. Comonomers exemplified are perfluoro(alkyl vinyl ethers) and perfluoro alpha-olefins. The sulphonyl groups in the polymer may be subjected to known reactions of sulphonyl groups. Copolymers of the invention may be vulcanized using the -SO2M group by heating in the presence of metal oxides or by reaction with polyfunctional reagents such as diamines. The polymers are useful as ion exchange resins. The polymers may be moulded or extruded and, when M is -ONa, may be used as aqueous dispersions to coat surfaces such as metals. In the preparation of elastomeric products, various fillers may be compounded into the polymers by milling, the mixture then being moulded under heat and pressure. Examples are given.ALSO:Aqueous dispersions of polymers containing the group <FORM:1034197/B1-B2/1> SO2-ONa <FORM:1034197/B1-B2/2> in which RF is fluorine or a C1-10 perfluoralkyl radial, Y is -F or -CF3 and n is 1, 2 or 3 (see Division C3), may be employed to coat metals and other surfaces, and form coherent and continuous coatings without the requirement of sintering or melting the polymer.
GB35711/64A 1963-09-13 1964-09-01 Sulphonic acid derivatives of fluorocarbon vinyl ethers, and polymers thereof Expired GB1034197A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30865063A 1963-09-13 1963-09-13
US384545A US3282875A (en) 1964-07-22 1964-07-22 Fluorocarbon vinyl ether polymers

Publications (1)

Publication Number Publication Date
GB1034197A true GB1034197A (en) 1966-06-29

Family

ID=26976360

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35711/64A Expired GB1034197A (en) 1963-09-13 1964-09-01 Sulphonic acid derivatives of fluorocarbon vinyl ethers, and polymers thereof

Country Status (3)

Country Link
JP (1) JPS417949B1 (en)
DE (1) DE1595071B2 (en)
GB (1) GB1034197A (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996023010A2 (en) * 1995-01-24 1996-08-01 E.I. Du Pont De Nemours And Company α-OLEFINS AND OLEFIN POLYMERS AND PROCESSES THEREFOR
US5595676A (en) * 1992-07-30 1997-01-21 Imperial Chemical Industries Plc Fluorinated polymers
US5866663A (en) * 1995-01-24 1999-02-02 E. I. Du Pont De Nemours And Company Processes of polymerizing olefins
WO1999052954A1 (en) * 1998-04-16 1999-10-21 E.I. Du Pont De Nemours And Company Ionomers and ionically conductive compositions
US6897272B1 (en) 1995-01-24 2005-05-24 E.I. Du Pont De Nemours And Company α-olefins and olefin polymers and processes therefor
US7005545B2 (en) 2002-06-14 2006-02-28 Daikin Industries, Ltd. Process for producing fluorinated fluorosulfonylalkyl vinyl ether
WO2006038928A1 (en) * 2004-07-19 2006-04-13 3M Innovative Properties Company Method of hydrolyzing a dispersion of ionic fluoropolymer
US7304101B2 (en) 2004-07-19 2007-12-04 3M Innovative Properties Company Method of purifying a dispersion of ionic fluoropolymer
US7348386B2 (en) * 2002-06-14 2008-03-25 Daikin Industries, Ltd. Process for producing fluorocopolymer, fluorocopolymer, and molded object
WO2011069281A1 (en) 2009-12-11 2011-06-16 山东东岳神舟新材料有限公司 Perfluorinated ion exchange resin, preparation method and use thereof
WO2011072418A1 (en) 2009-12-15 2011-06-23 山东东岳神舟新材料有限公司 High exchange capacity perfluorinated ion exchange resin, preparation method and use thereof
US8071702B2 (en) * 2001-12-06 2011-12-06 Gore Enterprise Holdings, Inc. Low equivalent weight ionomer
CN103840178A (en) * 2012-11-23 2014-06-04 中国科学院大连化学物理研究所 Application of fluorine-containing sulfonate ion exchange membrane in flow energy storage battery
US9109053B2 (en) 2002-06-17 2015-08-18 Daikin Industries, Ltd. Fluoropolymer dispersion and process for producing fluoropolymer dispersion

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS551351B2 (en) * 1974-03-07 1980-01-12
US4329434A (en) * 1979-05-31 1982-05-11 Asahi Kasei Kogyo Kabushiki Kaisha Novel fluorinated cation exchange membrane and process for producing the same
AU3097084A (en) * 1983-08-12 1985-02-14 Dionex Corporation Coated cation exchange resin
US5281680A (en) * 1993-01-14 1994-01-25 E. I. Du Pont De Nemours And Company Polymerization of fluorinated copolymers
WO1999045048A1 (en) * 1998-03-03 1999-09-10 E.I. Du Pont De Nemours And Company Substantially fluorinated ionomers
JP4815672B2 (en) * 2001-01-22 2011-11-16 旭硝子株式会社 Method for producing fluorine-containing sulfonimide polymer
JP4817542B2 (en) * 2001-06-29 2011-11-16 旭化成ケミカルズ株式会社 Production method of fluorinated vinyl ether
CN100338013C (en) * 2001-06-29 2007-09-19 旭化成株式会社 Process for producing fluorinated vinyl ether
JP4817541B2 (en) * 2001-06-29 2011-11-16 旭化成ケミカルズ株式会社 Method for producing fluorinated vinyl ether
US20070141425A1 (en) * 2003-12-01 2007-06-21 Takuya Arase Liquid fluoropolymer composition and process for producing crosslinked fluorochemical
JP4916144B2 (en) * 2005-08-05 2012-04-11 旭化成株式会社 Aromatic sulfide and / or sulfone derivatives
JP7136569B2 (en) * 2018-03-14 2022-09-13 旭化成株式会社 Method for producing sulfonate
JPWO2022244785A1 (en) * 2021-05-19 2022-11-24

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5595676A (en) * 1992-07-30 1997-01-21 Imperial Chemical Industries Plc Fluorinated polymers
US6670297B1 (en) 1995-01-24 2003-12-30 E. I. Du Pont De Nemours And Company Late transition metal diimine catalyst
US6140439A (en) * 1995-01-24 2000-10-31 E. I. Du Pont De Nemours And Company Polymers of cyclopentene
US6573353B1 (en) 1995-01-24 2003-06-03 E. I. Du Pont De Nemours And Company α-olefins and olefin polymers and processes therefor
US5880241A (en) * 1995-01-24 1999-03-09 E. I. Du Pont De Nemours And Company Olefin polymers
US5880323A (en) * 1995-01-24 1999-03-09 E. I. Du Pont De Nemours And Company Processes for making α-olefins
US5886224A (en) * 1995-01-24 1999-03-23 E. I. Du Pont De Nemours And Company α-diimines for polymerization catalysts
US5891963A (en) * 1995-01-24 1999-04-06 E. I. Du Pont De Nemours And Company α-olefins and olefin polymers and processes therefor
US5916989A (en) * 1995-01-24 1999-06-29 E. I. Du Pont De Nemours And Company Polymers of C4 and higher α-olefins
US7271231B2 (en) 1995-01-24 2007-09-18 E. I. Du Pont De Nemours And Company Polymerization of olefins
US6034259A (en) * 1995-01-24 2000-03-07 E. I. Du Pont De Nemours And Company α-olefins and olefin polymers and processes therefor
US6107422A (en) * 1995-01-24 2000-08-22 E.I. Du Pont De Nemours And Company Copolymer of an olefin and an unsaturated partially fluorinated functionalized monomer
US6894134B2 (en) 1995-01-24 2005-05-17 E. I. Dupont De Nemours And Company α-olefins and olefin polymers and processes therefor
US6218493B1 (en) 1995-01-24 2001-04-17 E. I. Du Pont De Nemours And Company α-olefins and olefin polymers and processes therefor
US6310163B1 (en) 1995-01-24 2001-10-30 E. I. Du Pont De Nemours And Company α-olefins and olefin polymers and processes therefor
US5866663A (en) * 1995-01-24 1999-02-02 E. I. Du Pont De Nemours And Company Processes of polymerizing olefins
WO1996023010A2 (en) * 1995-01-24 1996-08-01 E.I. Du Pont De Nemours And Company α-OLEFINS AND OLEFIN POLYMERS AND PROCESSES THEREFOR
WO1996023010A3 (en) * 1995-01-24 1996-12-05 Du Pont α-OLEFINS AND OLEFIN POLYMERS AND PROCESSES THEREFOR
US6897272B1 (en) 1995-01-24 2005-05-24 E.I. Du Pont De Nemours And Company α-olefins and olefin polymers and processes therefor
WO1999052954A1 (en) * 1998-04-16 1999-10-21 E.I. Du Pont De Nemours And Company Ionomers and ionically conductive compositions
US20120046371A1 (en) * 2001-12-06 2012-02-23 Huey Shen Wu Low Equivalent Weight Ionomer
US8071702B2 (en) * 2001-12-06 2011-12-06 Gore Enterprise Holdings, Inc. Low equivalent weight ionomer
US7348386B2 (en) * 2002-06-14 2008-03-25 Daikin Industries, Ltd. Process for producing fluorocopolymer, fluorocopolymer, and molded object
US7005545B2 (en) 2002-06-14 2006-02-28 Daikin Industries, Ltd. Process for producing fluorinated fluorosulfonylalkyl vinyl ether
US9109053B2 (en) 2002-06-17 2015-08-18 Daikin Industries, Ltd. Fluoropolymer dispersion and process for producing fluoropolymer dispersion
US7304101B2 (en) 2004-07-19 2007-12-04 3M Innovative Properties Company Method of purifying a dispersion of ionic fluoropolymer
WO2006038928A1 (en) * 2004-07-19 2006-04-13 3M Innovative Properties Company Method of hydrolyzing a dispersion of ionic fluoropolymer
WO2011069281A1 (en) 2009-12-11 2011-06-16 山东东岳神舟新材料有限公司 Perfluorinated ion exchange resin, preparation method and use thereof
US9023554B2 (en) 2009-12-11 2015-05-05 Shandong Huaxia Shenzhou New Material Co., Ltd. Perfluorinated ion exchange resin, preparation method and use thereof
WO2011072418A1 (en) 2009-12-15 2011-06-23 山东东岳神舟新材料有限公司 High exchange capacity perfluorinated ion exchange resin, preparation method and use thereof
US9090723B2 (en) 2009-12-15 2015-07-28 Shandong Huaxia Shenzou New Material Co., Ltd. High exchange capacity perfluorinated ion exchange resin, preparation method and use thereof
CN103840178A (en) * 2012-11-23 2014-06-04 中国科学院大连化学物理研究所 Application of fluorine-containing sulfonate ion exchange membrane in flow energy storage battery

Also Published As

Publication number Publication date
DE1595071B2 (en) 1971-09-09
DE1595071A1 (en) 1970-04-16
JPS417949B1 (en) 1966-04-26

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