Original diols from sunflower and ricin oils: Synthesis,characterization, and use as polyurethane building blocks

A series of novel fatty acid‐based diols were designed and synthesized from sunflower and ricin oils using optimized chemical reactions and purifications. These diols were categorized in two different types: (i) fatty acid‐based monoester containing diols (FAmE‐1 to FAmE‐6) and (ii) fatty acid‐based diester containing diols (FAdE‐1 to FAdE‐8). Their synthesis involved a series of reactions such as transesterification, epoxidation, ring opening of epoxide, and thiol‐ene additions. Analyses of these new fatty acid‐based diols were performed by HPLC/GC and NMR spectroscopy. The latter were then demonstrated as polyurethane (PU) precursors in the bulk polymerization with isophorone diisocyanate in the presence of dibutyl tin dilaurate as a catalyst. The effects of the diol nature and purity on the PU synthesis and properties were investigated. The structural characterization of the different PUs was carried out by means of FTIR, ¹H NMR, and ¹H DOSY NMR spectroscopy. The thermomechanical and rheological properties of these new PUs were found dependent on the chemical structure and purity of the diol building block. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012