Undecylenic acid: A tunable bio-based synthon for materials applications

An undecylenic acid-based monoglyceride prepared from glycidol and undecylenic acid is used as suitable and tunable synthon for polymerization applications. Epoxidation and acrylation reactions lead to photopolymerizable monomers while transesterification with dimethyl carbonate, metathesis and aminolysis reactions provide access to polyhydroxyurethane-based Materials. The successive intermediates were synthesized according to a green chemistry approach implicating solvent-less and catalyzed reactions, and were at each step fully characterized by infrared, H-1 and C-13{H-1} NMR spectroscopy, elemental analysis and mass spectrometry. Analyses of the resulting polymer materials were performed by infrared, H-1 and C-13{H-1} NMR, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and gel permeation chromatography (GPC). (C) 2015 Elsevier Ltd. All rights reserved.