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



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