Concept and Synthesis of Poly(ester amide)s with One Isolated, Two or Three Consecutive Amide Bonds Randomly Distributed Along the Polyester Backbone

Poly(ester amide)s (PEAs) were prepared from diols, amino alcohols and diamines with an in-built amide group via polycondensation with 1,4-butanediol and dimethyl adipate. The tailor-made monomers were synthesized by ring opening of e-caprolactone and E-caprolactam using 1,4-diaminobutane, 4-aminobutanol and 2-aminoethanol. PEAs having an isolated amide bond or two or three consecutive amide bonds in the poly(butylene adipate) (PBA) backbone, respectively, were obtained via melt polycondensation. The concentration of the amide groups in the PEAs was varied by the amount of preformed alpha,omega-diamines, amino alcohols or diols introduced in the feed. A simple synthetic route to these preformed monomers and the corresponding PEAs is described. The products were obtained in high purity and high yields. (C) Koninklijke Brill NV, Leiden, 2009