Radical polyaddition reaction of bis(α-trifluoromethyl-β,β-difluorovinyl) terephthalate onto diformylalkane

Radical polyaddition of bis(α-trifluoromethyl-β,β-difluorovinyl) terephthalate [CF2C(CF3)OCOC6H4COOC(CF3)CF2] (BFP) with diformylalkanes to produce fluorinated polymer bearing ketone-carbonyl groups in main chain is described. The radical additions of hexanal, pentanal and benzaldehyde with 2-benzoxypentafluoropropene [CF2C(CF3)OCOC6H5] were examined as model reactions to yield the corresponding addition product with hexanal and pentanal in high yields, and no product with benzaldehyde. The addition of acyl and hydrogen was found to take place to perfluoroisopropenyl group. The results of the model reactions suggested that the reaction might be applicable to polyaddition to produce polymers with diformylalkanes. The results of polyaddition of BFP with glutaraldehyde under the emulsion polymerization condition showed that the polymer of Mn=4.8×103 was obtained in fairly high yields. This might be a novel preparation method of polymers bearing fluorinated polyketone structure.