Synthesis of pseudo-telechelic diols by transesterification and thiol-ene coupling

Myriam Desroches (1) , Sylvain Caillol (1) , Rémi Auvergne (1) , Bernard Boutevin (1)

1 ICGM ICMMM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier

Transesterification of methyl esters of rapeseed oil with ethylene glycol in excess led to a v-hydroxy fatty ester with a yield of 90%. 2-Mercaptoethanol was grafted onto the double bonds of this v-hydroxy fatty ester by UV initiated thiol-ene coupling under mild conditions. Double bond conversion was found to be quantitative and yielded a polyol with average of two primary hydroxyl functions. This pseudo-diol was characterized by means of NMR spectroscopy, titration and mass spectroscopy (MS) and was used to synthesize polyurethane (PU) by step growth polyaddition with methylene diphenyl-4,40-diisocyanate. The polymer, analyzed by thermogravimetric analysis (TGA) and DSC, showed a glass transition temperature of -3°C, close to the one measured (8°C) on a PU based on a commercial polyol, Desmophen 1150.

Mots clés: Polyurethane; Renewable resources; Synthesis; Thiol-ene coupling; Transesterification

Domaines: Polymères

Myriam Desroches, Sylvain Caillol, Rémi Auvergne, Bernard Boutevin. Synthesis of pseudo-telechelic diols by transesterification and thiol-ene coupling. European Journal of Lipid Science and Technology, 2012, 114, pp.84. ⟨10.1002/ejlt.201100132⟩. ⟨hal-00668984⟩