Non-isocyanate route to biobased polyurethanes and polyureas via AB-type self-polycondensation

Polyurethanes and polyureas from renewable castor oil-derived 10-undecenoic acid were synthesized using the AB-type self-condensation approach. omega-Hydroxy- or omega-amino methyl carbamate ester precursor monomers were prepared under mild conditions from cysteamine methyl carbamate by thiol-ene addition. Synthesis of cysteamine carbamate and the self-condensable monomers derived of 10-unclecenol or 10-undecenylamine was studied by using different synthetic conditions. Two different polymers, a polyurethane and a polyurea, were prepared using conventional catalysts thus following a non-isocyanate route. The proposed synthetic approach constitutes a general route that allows for the easy preparation of methyl carbamate monomers not only from renewable (limonene, myrcene, geraniol, etc.), but also from petroleum-derived unsaturated substrates. (C) 2016 Elsevier Ltd. All rights reserved.