Carbohydrate‐based poly(ester‐urethane)s: A comparative study regarding cyclic alditols extenders and polymerization procedures

Abstract

Abstract A set of segmented poly(ester‐urethane)s were prepared from diisocyanates HDI or MDI and using 1,4‐butanediol and D ‐glucose‐derived cyclic diols (1,4 : 3,6‐dianhydro‐ D ‐glucitol (isosorbide) or 2,4;3,5‐di‐ O ‐methylidene‐ D ‐glucitol (gludioxol) or mixtures of them) as extenders. Hydroxyl end‐capped polycaprolactone with a molecular weight of 3000 g·mol −1 was used as soft segment. Two polymerization methods, in solution and in bulk, were applied for the synthesis of these poly(ester‐urethane)s. The influence of the preparation procedure and composition in cyclic extender on synthesis results, structure, and properties of the novel poly(ester‐urethane)s was comparatively evaluated and discussed. The effect of replacement of 1,4‐butanediol by isosorbide or gludioxol on hydrodegradability was also assessed; the hydrolysis rate increased noticeably with the presence of glucitol derived units, although degradation of the polymers took place essentially by hydrolysis of the polyester soft segment. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009