Polyurethanes derived from carbohydrates and cystine-based monomers

ABSTRACT Linear [m,n]‐type polyurethanes (PUs) fully based on renewable materials are synthesized by interfacial polycondensation reaction of diamines derived from the amino‐acid cystine with (bis)chloroformates derived from alditols having L‐arabino or xylo configuration. The degradability of the new PUs has been enhanced by the introduction of disulfide linkages into the polymer backbone leading to a new group of stimulus‐responsive sugar‐based polyurethanes able to be degraded by glutathione under physiological conditions. All these polyurethanes are stable up to around 245°C, decomposing at higher temperatures through a one‐stage mechanism. The new materials display high chemical homogeneity and degradability in both hydrolytic and reductive environments, with reductions of above 90% in Mw. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 41304.