GB950084A - Improvements in or relating to fluorine containing copolymers, their production and cured products obtained therefrom - Google Patents

Improvements in or relating to fluorine containing copolymers, their production and cured products obtained therefrom

Info

Publication number
GB950084A
GB950084A GB2037160A GB2037160A GB950084A GB 950084 A GB950084 A GB 950084A GB 2037160 A GB2037160 A GB 2037160A GB 2037160 A GB2037160 A GB 2037160A GB 950084 A GB950084 A GB 950084A
Authority
GB
United Kingdom
Prior art keywords
copolymer
transfer agent
weight
cured
curing
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
GB2037160A
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 US10095A external-priority patent/US3069401A/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB950084A publication Critical patent/GB950084A/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
    • C08F214/00Copolymers 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
    • C08F214/18Monomers containing fluorine
    • C08F214/28Hexyfluoropropene
    • 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
    • C08F214/00Copolymers 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
    • C08F214/18Monomers containing fluorine
    • C08F214/22Vinylidene fluoride
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00Compositions of homopolymers or 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; Compositions of derivatives of such polymers
    • C08L27/02Compositions of homopolymers or 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; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/12Compositions of homopolymers or 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; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08L27/16Homopolymers or copolymers or vinylidene fluoride

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Vinylidene fluoride and hexafluoropropylene are copolymerized by heating in the presence of a chain transfer agent, which is a C8 or lower aliphatic alcohol, ketone or carboxylic acid ester, and in contact with a polymerization initiator, the proportions of monomers and transfer agent being such that in the copolymer the weight ratio of -CH2-CF2- to -C3F6- units is from 70:30 to 45:55 with the radicals of the transfer agent present on average about once per molecule of copolymer, and the copolymer has an inherent viscosity from 0.025 to 0.25 at 30 DEG C. in 0.1% by weight solution in a mixture of 86.1% by weight tetrahydrofuran and 13.9% by weight dimethylformamide. The copolymers are stated to range from viscous oils to semi-solid greases at room temperature and to be capable of being cured to plastic or elastomeric products. Chain transfer agents specified are methanol, ethanol, isopropanol, 2-ethylhexanol-1, acetone, methyl ethyl or propyl ketone, ethyl acetate and hexanoate, butyl formate and amyl acetate. Copolymerization may be effected in the presence or absence of a solvent with a peroxy catalyst, e.g. acetyl, chloroacetyl, benzoyl, dicumyl or di-t-butyl peroxide or cumene hydroperoxide, with or without a reducing agent, or in aqueous emulsion with a redox catalyst e.g. ammonium persulphate and sodium bisulphate, and may be on a batch or continuous basis. The products may be cured by the conventional procedures for fluorocarbon elastomers. Specification 789,786 is referred to.ALSO:Vinylidene fluoride and hexafluoropropylene are copolymerized by heating in the presence of a chain transfer agent, which is a C8 or lower aliphatic alcohol, ketone or carboxylic acid ester, and in contact with a polymerization initiator, the proportions of monomers and transfer agent being such that in the copolymer the weight ratio of -CH2-CF2- to -C3F6- units is from 70:30 to 45:55 with the radicals of the transfer agent present on average about once per molecule of copolymer, and the copolymer has an inherent viscosity from 0.025 to 0.25 at 30 DEG C. in 0.1% by weight solution in a mixture of 86.1% by weight tetrahydrofuran and 13.9% by weight dimethylformamide. The copolymers are stated to range from viscous oils to semisolid greases at room temperature and to be capable of being cured to plastic or elastomeric products. Chain transfer agents specified are methanol, ethanol, isopropanol, 2-ethylhexanol-1, acetone, methyl ethyl or propyl ketone, ethyl acetate and hexanoate, butyl formate and amyl acetate. Copolymerization may be effected in the presence or absence of a solvent with a peroxy catalyst, e.g. acetyl, chloroacetyl, benzoyl, dicumyl or di-t-butyl peroxide or cumene hydroperoxide, with or without a reducing agent, or in aqueous emulsion with a redox catalyst e.g. ammonium persulphate and sodium bisulphate, and may be on a batch or continuous basis. Curing. The products may be cured by the conventional procedures for fluorocarbon elastomers. They may be compounded with an acid acceptor, e.g. magnesium oxide, followed by a curing agent. Examples are given of the following types of curing agents:-organic or inorganic peroxides; alkylene diamine carbamates, polythiols combined with a tertiary amine; and N,N1-diarylidene diamine. Curing is preferably effected in two temperature stages. Fillers such as carbon black may be introduced with the curing agents. Specification 789,986 is referred to.
GB2037160A 1959-06-24 1960-06-09 Improvements in or relating to fluorine containing copolymers, their production and cured products obtained therefrom Expired GB950084A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US82244759A 1959-06-24 1959-06-24
US10095A US3069401A (en) 1960-02-23 1960-02-23 Copolymers of hexafluoropropylene vinylidene fluoride and aliphatic, chain transfer agents

Publications (1)

Publication Number Publication Date
GB950084A true GB950084A (en) 1964-02-19

Family

ID=26680772

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2037160A Expired GB950084A (en) 1959-06-24 1960-06-09 Improvements in or relating to fluorine containing copolymers, their production and cured products obtained therefrom

Country Status (1)

Country Link
GB (1) GB950084A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4985520A (en) * 1988-07-29 1991-01-15 Asahi Kasei Kogyo Kabushiki Kaisha Fluoroelastomer having excellent processability
CN104870552A (en) * 2012-11-05 2015-08-26 3M创新有限公司 Peroxide-curable fluoropolymer composition including solvent and method of using the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4985520A (en) * 1988-07-29 1991-01-15 Asahi Kasei Kogyo Kabushiki Kaisha Fluoroelastomer having excellent processability
CN104870552A (en) * 2012-11-05 2015-08-26 3M创新有限公司 Peroxide-curable fluoropolymer composition including solvent and method of using the same
US11130829B2 (en) 2012-11-05 2021-09-28 3M Innovative Properties Company Peroxide-curable fluoropolymer composition including solvent and method of using the same

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