Cyclopolymerization of perfluoroisopropenyl vinylacetate

Hirotada Fujiwara, Tadashi Narita, Hiroshi Hamana

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4 Citations (Scopus)

Abstract

To develop the polymerization exploiting the interconversion of fluorinated carbon radical to hydrocarbon radical, the radical cyclopolymerization of perfluoroisopropenyl vinylacetate [CF2=C(CF3)OCOCH 2CH=CH2] (FIA) was investigated to afford a polymer possessing mainly five-membered ring structure with bimodal molecular weight distribution having 1 × 105 as the higher molecular weight. This may be the first example wherein the cyclopolymerization between usual allyl group and fluorinated vinyl group is performed. The degree of cyclization was between 70 and 80% determined by 19F NMR of as-polymerized products. The polymer preparation from perfluoroisopropenyl group, which shows scarce homopolymerization reactivity was accomplished. The mechanism that the addition of hydrocarbon radical to perfluoroisopropenyl group to produce fluorinated carbon radical followed by the intramolecular addition reaction onto allyl group to form five-membered ring is proposed. The hydrolysis of the FIA polymer afforded a polymer possessing hydrophobic fluoroalkyl group with hydrophilic hydroxyl and carboxylic acid groups.

Original languageEnglish
Pages (from-to)3220-3232
Number of pages13
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume44
Issue number10
DOIs
Publication statusPublished - May 15 2006
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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