Vegetable‐based building‐blocks for the synthesis of thermoplastic renewable polyurethanes and polyesters

Abstract

Abstract Fatty acid derivatives, viz, methyl oleate and methyl 10‐undecenoate were systematically explored to obtain a set of monomers with defined functionality. More specifically, AB‐type self‐condensable monomers containing hydroxyl‐acyl azide functionality and diols with pre‐formed ester linkage were synthesized. A series of polyurethanes was prepared using two methods: (i) AB‐type self‐polycondensation reaction of hydroxyl‐acyl azide moiety, and (ii) polymerization of diols with isophorone diisocyanate and methylene diphenyl diisocyanate. The diols were also reacted with a bio‐sourced diester using organocatalyst to obtain a set of polyesters. The obtained polyurethanes and polyesters were thoroughly analyzed with fourier‐transformed infrared, nuclear magnetic resonance, size exclusion chromatography, differential scanning calorimetry and thermogravimetric analysis experiments. The polymers displayed amorphous to semi‐crystalline behaviors with regard to the structure of the monomers. Both, polyurethanes and polyesters displayed a good thermal stability with no significant weight loss below 200°C.