Radical polyaddition reaction of bis(α-trifluoromethyl-β,β-difluorovinyl) 2,3,5,6-tetrafluoroterephthalate

Hirotada Fujiwara, Tadashi Narita, Hiroshi Hamana, Ryo Kurata

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1 Citation (Scopus)

Abstract

To develop the radical polyaddition of bisperfluoroisopropenyl esters to preparation of polymers bearing higher fluorine content, the polyaddition reactivity of bis(α-trifluoromethyl-β,β-difluorovinyl) 2,3,5,6-tetrafluoroterephthalate [CF2=C(CF3) OCOC6F4COOC(CF3)=CF2] (TFT) with 1,4-dioxane (DOX) and diethoxydimethylsilane (DEOMS) were described. The results of the model reactions of 2-pentafluorobenzoxypentafluoropropene [CF2=C(CF3)OCOC6F5] (PFBP) with THF, DOX and DEOMS showed that the reactions took place almost quantitatively and the main products were mono-addition compound for THF and di-addition compounds for DOX and DEOMS, respectively. The polyaddition of TFT with DOX or DEOMS yielded corresponding polymers of about 1×104 as a molecular weight bearing unimodal molecular weight distribution by the initiation of peroxides such as benzoyl peroxide and di-tert-butyl peroxide. TFT showed the slightly higher reactivity compared to that of non-fluorinated analogue, bis(α-trifluoromethyl-β,β-difluorovinyl) terephthalate (BFP), by the results of ternary polyaddition of TFT/BFP/DOX system. Polymers bearing TFT moiety showed the higher thermostability and contact angle.

Original languageEnglish
Pages (from-to)381-389
Number of pages9
JournalJournal of Fluorine Chemistry
Volume125
Issue number3
DOIs
Publication statusPublished - Mar 1 2004
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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