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Telomerisation Reactions of fluorinated alkenes

  • Bruno Améduri
  • Bernard Boutevin
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 192)

Abstract

The synthesis of fluorinated oligomers by radical telomerisation of fluoroalkenes is discussed. After a brief presentation of the various parameters which direct this reaction and the kinetic laws, this review outlines the traditional telogens efficient in telomerisation and also considers other transfer agents which undergo less known cleavages. Telomerisation involving main fluorinated alkenes (vinylidene fluoride, tetrafluoroethylene, chlorotrifluoroethylene, trifluoroethylene and hexafluoropropene) and less used agents is then reviewed, considering either the method of initiation including new activation systems, or specific cleavage of the telogens used. Some examples of cotelomerisation are given constituting interesting models of copolymerisation. General concepts of reactivity regarding the orientation of addition of free radicals to unsymmetrical fluorinated alkenes and also comparison of the reactivity of various fluorinated alkenes with the telogens are discussed and several examples given. Beside the traditional process of telomerisation, the living telomerisation methods are also described. In these methods, the living character is mentioned and well chosen transfer agents with specific cleavable bonds described. The living behaviour of the iodine transfer polymerisation or stepwise cotelomerisation occurs in the presence of perfluoroalkyl iodides or α, ω-diiodoperfluoroalkanes as the telogens and shows high interest in the synthesis of structurally well defined telomers. Finally, the application of fluoropolymers synthesised from these telomers is presented showing the high added value of these materials.

Keywords

Telomerisation fluoroalkene telogen free radical livingness 

List of Symbols and Abbreviations

AIBN

azobisisobutyronitrile

BEPH

butyl ethyl peroxyhexanoate

BDE

bond dissociation energy

Bu

n-butyl

tBu

tertio-butyl

CR

counter radical

CT

transfer constant

CTFE

chlorotrifluoroethylene

d

day

DBP

dibenzoyl peroxide

DIPC

diisopropyl peroxydicarbonate

DPn

average degree of polymerisation in number

DTBP

ditertio-butyl peroxide

F113

1,1,2-trifluorotrichloroethane

HFPO

hexafluoropropylene oxide

iPr

isopropyl

IRFI

α, ω-diiodoperfluoroalkane

ITP

iodine transfer polymerisation

M

monomer

[M]

concentration of monomer

Mn

average molecular weight in number

Mω

average molecular weight in weight

NMR

nuclear magnetic resonance

PCTFE

poly(chlorotrifluoroethylene)

PHFP

poly(hexafluoropropene)

PTFE

poly(tetrafluoroethylene)

PVDF

poly(vinylidene fluoride)

PVF

poly(vinyl fluoride)

R

alkyl radical

R

alkyl group

RF

perfluorinated group

RF,Cl

chlorofluorinated group

RFBr

perfluoroalkyl bromide

RFI

perfluoroalkyl iodide

RT

room temperature

sc

supercritical

Tempo

2,2,6,6-tetramethyl piperidinyl-1-oxyl

TFE

tetrafluoroethylene

Tg

glass transition temperature

THF

tetrahydrofuran

UV

ultra violet

VDF

vinylidene fluoride

VF

vinyl fluoride

Δ

heating

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Copyright information

© Springer Verlag Berlin Heidelberg 1997

Authors and Affiliations

  • Bruno Améduri
    • 1
  • Bernard Boutevin
    • 1
  1. 1.ESA 5076 (CNRS) Ecole Nationale Supérieure de Chimie de Montpellier 8Montpellier Cedex 5France

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