Undecylenic acid: A tunable bio-based synthon for materials applications. (January 2016)

• Record Type: Journal Article
• Authors: Bigot, Sandra; Daghrir, Mohamed; Mhanna, Ali; Boni, Gilles; Pourchet, Sylvie; Lecamp, Laurence; Plasseraud, Laurent
• Is Part Of: European polymer journal. Volume 74(2016:Jan.)
• Page Start: 26
• Page End: 37
• Publication Date: 2016-01
• Subjects: Renewable resources -- Fatty acid -- Glycidol -- Organic carbonate -- Polyhydroxyurethanes (PHUs) -- Photopolymerization; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; Polymerization; Polymers; Periodicals; Electronic journals; 547.705
• DOI: 10.1016/j.eurpolymj.2015.11.008
• Languages: English
• ISSNs: 0014-3057

Abstract

Graphical abstract: Highlights: An undecylenic acid-based monoglyceride is made from glycidol and undecylenic acid. New bio-based non isocyanate polyhydroxyurethanes were prepared. Monoglyceride epoxidation and acrylation lead to a photopolymerizable monomer. Some green chemistry principles were applied for monomers syntheses. The resulting polymers were chemically and thermally investigated. Abstract: 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, 1 H and 13 C{ 1 H} NMR spectroscopy, elemental analysis and mass spectrometry. Analyses of the resulting polymer materials were performed by infrared, 1 H and 13 C{ 1 H} NMR, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and gel permeation chromatography (GPC).