A Green Approach Toward Oleic- and Undecylenic Acid-Derived Polyurethanes

Naturally occurring oleic and undecylenic acids were used as raw materials for the synthesis of novel polyurethanes (PUs). The application of environmentally friendly thiol-ene additions to 10-undecenoate and oleate derivatives was studied with the goal of obtaining renewable diols. The resulting monomers were then polymerized with 4,4'-methylenebis (phenylisocyanate), in N, N-dimethylformamide solution using tin (II) 2-ethylhexanoate as catalyst, to produce the corresponding thermoplastic PUs (TPUs). Also, ultrasound irradiation has been tested to improve the synthesis of PU. Under these conditions, TPUs were obtained in high yields (80-99%) with weight-average molecular weights in the 36-83 kDa range. The chemical structures of PUs were assessed by FTIR and NMR spectroscopy. The thermal and mechanical properties of the synthesized TPUs have been studied and they showed a clear dependence on the structure of the parent diol. MTT test was carried out to asses the potential cytotoxicity of the prepared PUs, indicating no cytotoxic response. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 2407-2416, 2011