Solubility in CO(2) and carbonation studies of epoxidized fatty acid diesters: towards novel precursors for polyurethane synthesis

Aurélie Boyer (1) , Eric Cloutet (1, 2) , Thierry Tassaing (3) , Benoît Gadenne (4) , Carine Alfos (4) , Henri Cramail (1, 5)

1 LCPO - Laboratoire de Chimie des Polymères Organiques
2 Team 4 LCPO : Polymer Materials for Electronic, Energy, Information and Communication Technologies
3 ISM - Institut des Sciences Moléculaires
4 Institut des Corps Gras
5 Team 2 LCPO : Biopolymers & Bio-sourced Polymers

Novel linear polyurethanes were synthesized by bulk polyaddition of diamines with two vegetable-based biscarbonates produced from oleic acid methyl ester. Internal carbonated fatty acid diester (ICFAD) and terminal carbonated fatty acid diester (TCFAD) were obtained by the reaction of their epoxide precursors with CO(2). Terminal epoxy fatty acid diester (TEFAD) was found to be more soluble and more reactive in CO(2) than internal epoxy fatty acid diester (IEFAD). Polyurethanes obtained by polyaddition of TCFAD and ICFAD with diamines exhibit molecular weights up to 13 500 g mol(-1) and glass transitions around -15 degrees C. Amide linkages were not observed when secondary diamine was used as the comonomer.

Mots clés: SOYBEAN OIL; VEGETABLE-OILS; SOY-POLYOLS; DIOXIDE; POLYMERS; ESTERS; NETWORKS; HYDROFORMYLATION; EQUILIBRIA; ROUTE

Domaines: Polymères

Aurélie Boyer, Eric Cloutet, Thierry Tassaing, Benoît Gadenne, Carine Alfos, et al.. Solubility in CO(2) and carbonation studies of epoxidized fatty acid diesters: towards novel precursors for polyurethane synthesis. Green Chemistry, 2010, 12 (12), pp.2205-2213. ⟨10.1039/c0gc00371a⟩. ⟨hal-00679371⟩