Glycolipids as a source of polyols for the design of original linear and cross-linked polyurethanes

Abstract

Two novel sugar-based fatty ester polyols were synthesized by selective transesterification of epoxidized methyl or ethyl oleate with unprotected methyl α-D-glucopyranoside and sucrose respectively, followed by hydrolysis of the epoxide moiety. The so-formed polyols were then used as polyurethane (PU) precursors in the polyaddition with isophorone diisocyanate (IPDI) in the presence of dibutyl tin dilaurate (DBTDL) as a catalyst. Interestingly, the reactivity of the hydroxyl functions attached to the sugar and to the fatty ester chain moieties respectively could be discriminated with respect to the solvent used, enabling the synthesis of either linear or cross-linked PUs. The linear PUs were studied by means of FTIR, 1H NMR spectroscopy and size exclusion chromatography, SEC. The thermo-mechanical properties of these original PUs bearing pendant or intramolecular sugar units were also analyzed by differential scanning calorimetry, DSC.