Synthesis and characterization of new poly(ester-amide)s containing oligo(oxyethylene) segments

Segmented poly(ester-amide)s were prepared by polycondensation of a series of monoaminooligo(oxyethylene) pentachlorophenyl succinates, containing 1-3 oxyethylene units. The monomers were prepared by a four-step procedure fro m oligo(oxyethylene) monoamines consisting of: (1) protection of the primar y amine group by di(t-butyl) carbonate, (2) succinoylation of the free hydr oxyl group, (3) esterification of the resulting acid group with pentachloro phenol, and (4) deprotection of the amine group in anhydrous acid condition s. Polycondensation experiments were performed in solution and in bulk at r oom temperature by using triethylamine as a base to restore the active amin e group of the monomer. Only bulk polymerization gave rise to high molecula r weight polymers. Solubility and thermal properties of the materials were found to be related to the length of the oligo(oxyethylene) segment and the presence of strongly interacting amide groups.