Synthesis of new aromatic perfluorovinyl ether monomers containing phosphonic acid functionality

Souzy, Renaud; Améduri, Bruno; Boutevin, Bernard; Virieux, David

doi:10.1016/j.jfluchem.2004.03.010

Cited by 35 publications

(26 citation statements)

References 42 publications

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“…In fact, in recent decades, fluoropolymers incorporating aromatic monomers with sulfonic acid, like perfluorovinyl aryl ether [13], trifluorostyrene [15,46], or with a phosphonic acid [19,40,41,47,48], have been of growing interest. In the case of trifluorostyrene (functionalised by a phosphonic acid, or by halogenosulfonyl group post hydrolysable into sulfonic acid), polymers are prepared by their (co)polymerisation with trifluorostyrene (TFS).…”

mentioning

confidence: 99%

Proton‐Conducting Polymer Electrolyte Membranes Based on Fluoropolymers Incorporating Perfluorovinyl Ether Sulfonic Acids and Fluoroalkenes: Synthesis and Characterization

et al. 2005

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This paper presents the synthesis of new polymer electrolyte membranes based on fluoropolymers incorporating aromatic perfluorovinyl ether sulfonic acids. A novel synthetic route describing the preparation of perfluorovinyl ether monomer containing sulfonic functionalities, 4‐[(α,β,β‐trifluorovinyl)‐oxy]benzene sulfonic acid (TFVOBSA), is reported. The radical (co) and terpolymerisation of 4‐[(α,β,β‐trifluorovinyl)oxy]benzene sulfonyl chloride (TFVOBSC) with 1,1‐difluoroethylene (or vinylidene fluoride, VDF), hexafluoropropene (HFP), and perfluoromethyl vinyl ether (PMVE) is described. The terpolymers of TFVOBSC with VDF and HFP, or VDF and PMVE, were hydrolysed and also led to new fluorinated terpolymers bearing sulfonic acid aromatic side‐groups. The terpolymers were characterized by 1H and 19F NMR spectroscopies, SEC, DSC, and TGA. Membranes incorporating these functional fluoropolymers were prepared and the electrochemical properties (IEC, proton conductivity, swelling rates) were studied and discussed.

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confidence: 99%

Proton‐Conducting Polymer Electrolyte Membranes Based on Fluoropolymers Incorporating Perfluorovinyl Ether Sulfonic Acids and Fluoroalkenes: Synthesis and Characterization

et al. 2005

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“…These monomers were claimed to be potentially useful for proton exchange membranes for fuel cells [5].…”

Section: Reactions With Phenoxides and Thiophenoxidesmentioning

confidence: 99%

1,2-Dibromotetrafluoroethane (Freon 114B2) as a building block for fluorine compounds

Dmowski

2012

Journal of Fluorine Chemistry

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“…In particular, we have reported the preparation of 4-[(a,h,h-trifluorovinyl)oxy] benzene phosphonic acid [44] (Scheme 4). Using various methods of phosphonation like Michaelis -Arbuzov or Michaelis -Becker reactions, it was shown that the best yield was achieved using a palladium triphenyl phosphine complex as catalyst.…”

Section: Fluoro-copolymers Of Functional Fluorinated Monomers With Flmentioning

confidence: 99%

Functional fluoropolymers for fuel cell membranes

et al. 2005

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International audienceVarious routes to synthesise functional fluoropolymers used in membranes for fuel cell applications are presented. They can be separated into three main families of alternatives. The first concerns the direct radical copolymerisation of fluoroalkenes with fluorinated functional monomers. The latter are either fluorinated vinyl ethers, a,h,h-trifluorostyrenes or trifluorovinyl oxy-aromatic monomers bearing sulfonic or phosphonic acids. The resulting membranes are the well-known Nafion\, Flemion\, Hyflon\, Dow\, Aciplex\ or BAM3G\. The second way deals with the chemical modification of hydrogenated polymers (e.g., polyparaphenylenes) with fluorinated sulfonic acid synthons. The third possibility concerns the synthesis of FP-g-poly(M) graft copolymers (where FP and M stand for fluoropolymer and monomer, respectively) obtained by activation (e.g., by irradiation with electrons, g-rays or ozone) of fluoropolymers, followed by grafting of the monomers. The most used M is styrene, and a further step of sulfonation was achieved onto FP-g-PS, leading to FP-g-PS sulfonic acid graft copolymers

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Synthesis of new aromatic perfluorovinyl ether monomers containing phosphonic acid functionality

Cited by 35 publications

References 42 publications

Proton‐Conducting Polymer Electrolyte Membranes Based on Fluoropolymers Incorporating Perfluorovinyl Ether Sulfonic Acids and Fluoroalkenes: Synthesis and Characterization

Proton‐Conducting Polymer Electrolyte Membranes Based on Fluoropolymers Incorporating Perfluorovinyl Ether Sulfonic Acids and Fluoroalkenes: Synthesis and Characterization

1,2-Dibromotetrafluoroethane (Freon 114B2) as a building block for fluorine compounds

Functional fluoropolymers for fuel cell membranes

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