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

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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.

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