Bio-based aliphatic polyurethanes through ADMET polymerization in bulk and green solvent

Abstract

A new route to α,ω-diene urethane monomer is proposed by converting 10-undecenoic acid into the corresponding acyl azide, followed by urethanization with 10-undecenol. ADMET polymerizations of this α,ω-diene urethane monomer as well as other bio-based α,ω-dienes bearing various organic functions (ester, carbonate, ether, amide) were carried out in bulk and solution conditions. A screening of the most commonly used metathesis catalysts allows to evaluate their tolerance toward the urethane function as well as toward Polarclean, a "green" and nontoxic high boiling point solvent. The influence of the nature of the central organic function in these α,ω-diene monomers on the thermomechanical properties is investigated.

Keywords: ADMET; Curtius rearrangement; fatty acids; polyurethane; solution.