GB1108128A - Perfluoro (polyethylene glycol divinyl ethers) and polymers thereof - Google Patents

Perfluoro (polyethylene glycol divinyl ethers) and polymers thereof

Info

Publication number
GB1108128A
GB1108128A GB2458666A GB2458666A GB1108128A GB 1108128 A GB1108128 A GB 1108128A GB 2458666 A GB2458666 A GB 2458666A GB 2458666 A GB2458666 A GB 2458666A GB 1108128 A GB1108128 A GB 1108128A
Authority
GB
United Kingdom
Prior art keywords
formula
alkali metal
compounds
prepared
fluoride
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
GB2458666A
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
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1108128A publication Critical patent/GB1108128A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F16/00Homopolymers 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
    • C08F16/12Homopolymers 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
    • C08F16/14Monomers containing only one unsaturated aliphatic radical
    • C08F16/24Monomers containing halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:1108128/C3/1> wherein n is an integer from 2 to 20. The compounds are prepared by reacting hexafluoropropylene with a compound of the formula <FORM:1108128/C3/2> under anhydrous conditions in the presence of an inert polar solvent and of an alkali metal, silver or quaternary ammonium fluoride to give a compound of the formula <FORM:1108128/C3/3> which is converted to the desired product by (i) pyrolysis in the presence of an alkali metal carbonate or zinc oxide, or (ii) by reaction with an aqueous alkali metal hydroxide to give the corresponding carboxylic acid salt which is then dried and pyrolysed. The diacyl fluoride starting material is prepared by reacting tetrafluoroethylene epoxide with oxalyl fluoride in an inert solvent and in the presence of a quaternary ammonium fluoride formed in situ by adding the corresponding cyanide to the reaction system. The compounds of the invention may be converted to thermoset resins consisting essentially of recurring units of the formula <FORM:1108128/C3/4> wherein the unsatisfied valency bonds are linked to other of the same units, by polymerization at 20-250 DEG C. at atmospheric or under autogenous pressure and in the presence of a free radical polymerization initiator. Reference has been directed by the Comptroller to Specifications 952,281 and 1,033,919.ALSO:The invention comprises compounds of the general formula <FORM:1108128/C2/1> wherein n is an integer from 2 to 20. The compounds are prepared by reacting hexafluoroproylene with a compound of the formula <FORM:1108128/C2/2> under anhydrous conditions in the presence of an inert polar sovent and of an alkali metal, silver or quaternary ammonium fluoride to give a compound of the formula <FORM:1108128/C2/3> <FORM:1108128/C2/4> which is converted to the desired product by (i) pyrolysis in the presence of an alkali metal carbonate or zinc oxide; or (ii) by reaction with an aqueous alkali metal hydroxide to give the corresponding carboxylic acid salt which is then dried and pyrolysed. The diaryl fluoride starting material is prepared by reacting tetrafluoroethylene epoxide with oxalyl fluoride in an inert solvent and in the presence of a quaternary ammonium fluoride formed in situ by adding the corresponding cyanide to the reaction system. Compounds of the formula <FORM:1108128/C2/5> where R is -CF3 or -C4F9, used as free-radical polymerization initiators, are prepared by reaction of CF3-C­C-R with N2F4. Reference has been directed by the Comptroller to Specifications 1,033,919 and 952,281.
GB2458666A 1965-06-02 1966-06-02 Perfluoro (polyethylene glycol divinyl ethers) and polymers thereof Expired GB1108128A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US46161065A 1965-06-02 1965-06-02

Publications (1)

Publication Number Publication Date
GB1108128A true GB1108128A (en) 1968-04-03

Family

ID=23833262

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2458666A Expired GB1108128A (en) 1965-06-02 1966-06-02 Perfluoro (polyethylene glycol divinyl ethers) and polymers thereof

Country Status (3)

Country Link
DE (1) DE1645142A1 (en)
GB (1) GB1108128A (en)
NL (1) NL6607678A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7737307B2 (en) 2007-08-06 2010-06-15 E. I. Du Pont De Nemours And Company Fluorinated nonionic surfactants
WO2022138510A1 (en) * 2020-12-25 2022-06-30 Agc株式会社 Fluorine-containing polyether compound production method, fluorine-containing divinyl polyether compound production method, and fluorine-containing divinyl polyether compound
WO2022138511A1 (en) * 2020-12-25 2022-06-30 Agc株式会社 Production method of fluorine-containing polyether compound

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7737307B2 (en) 2007-08-06 2010-06-15 E. I. Du Pont De Nemours And Company Fluorinated nonionic surfactants
WO2022138510A1 (en) * 2020-12-25 2022-06-30 Agc株式会社 Fluorine-containing polyether compound production method, fluorine-containing divinyl polyether compound production method, and fluorine-containing divinyl polyether compound
WO2022138511A1 (en) * 2020-12-25 2022-06-30 Agc株式会社 Production method of fluorine-containing polyether compound

Also Published As

Publication number Publication date
NL6607678A (en) 1966-12-05
DE1645142A1 (en) 1970-10-22

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