Radical polyaddition reaction of bis(α-trifluoromethyl-β,β-difluorovinyl) terephthalate with ethylamine compounds

In order to develop the radical polyaddition of bis(α-trifluoromethyl-β,β-difluorovinyl) terephthalate [CF2C(CF3)OCOC6H4COOC(CF3)CF2] (BFP) with 1,4-dioxane, the polyaddition of BFP with ethylamine derivatives was investigated. Prior to preparation of polymers, the model reactions, 2-benzoxypentafluoropropene [CF2C(CF3)OCOC6H5] (BPFP) with several ethylamine compounds, were examined to discover the proper polyaddition reaction condition. A 3:1 addition product was yielded by the reaction of BPFP with triethylamine in the presence of benzoyl peroxide or 2,2′-azobisisobutyronitrile at 60 °C for 24 h. The reaction of BPFP with diethylaniline afforded no addition products. Polyaddition of BFP with triethylamine was investigated to afford soluble polymers possessing triethylamine moiety in main chain. The highest molecular weight obtained was Mn=6.3×103. The reaction turned out to take place mainly at methylene groups of triethylamine.