ALTERNATING COPOLYMERIZATION OF 3,4-EPOXY-1-BUTENE AND DERIVATIVES WITH MALEIC-ANHYDRIDE

3,4-Epoxy-1-butene (I<under bar>), prepared by the selective oxidation of butadiene, is an unusual difunctional monomer containing polymeriz able vinyl and epoxy groups. As expected, free radical homopolymerizat ion of I<under bar> and its cyclic ketal derivatives was found to be v ery sluggish, as expected, for the allylic monomer structures. However , I<under bar> was found to form alternating copolymers with maleic an hydride with both 1,2- and 1,5-enchainment observed. The structures of the alternating copolymers were observed to be solvent dependent with the in situ formation of cyclic ketals and their incorporation into t he copolymers in polymerizations done in ketone solvents. Various cycl ic ketal monomers derived from I readily formed alternating copoymers with maleic anhydride. Thermally activated self-crosslinking of these resins was observed.