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Synthesis and Polymerization of Maleimides Containing Perfluoroalkyl Groups

Novel types of N-(perfluoro-n-octylethoxycarbonylmethyl)maleimide (PFOM) and N-(perfluoro-n-hexylethoxycarbonylmethyl)maleimide (PFHM) were synthesized from maleic anhydride, glycine and the corresponding perfluoroalkylethyl alcohols. PFOM and PFHM were polymerized with radical initiators in bulk and in several solvents at 60°C to 130°C. The resulting polymers were soluble only in trifluoroacetic acid (TFAA). The highest yield and highest reduced viscosity (ηsp/c) for the polymers were 96% in bulk and 0.53 dl g−1 (in TFAA at 30°C), respectively. The monomer reactivity ratios (r1, r2) in the copolymerizations of PFOM (or PFHM) with styrene or methyl methacrylate, and Alfrey–Price Q, e values for PFOM and PFHM were determined.