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Design of original vegetable oil-based cyclic carbonates and amines towards Poly(HydroxyUrethane)s

Abstract : In this thesis, vegetable oils were used as a platform to design original cyclic carbonates and amines with the goal to synthesize fully bio-based poly(hydroxyurethane)s. On the one hand, two routes to fatty acid-based amines were implemented in mild conditions. First, the oxidation of aliphatic alcohols into nitriles was performed under air in the presence of supported TEMPO on silica, followed by hydrogenation of nitrile compounds into corresponding amines. Second, thiol-ene chemistry was performed on unsaturated fatty acid substrates to design original aliphatic bio-based diamines. On the other hand, substituted 5-membered cyclic carbonates were designed from fatty acids and glycerol derivatives to enhance their reactivity towards aminolysis. By inserting ether, thio-ether or ester functionalities in α- or β-position of the cyclic carbonates, their reactivity towards amines could be tuned. Investigations on the selectivity, side reactions and catalysis of the carbonate-amine reaction were carried out to apprehend this route to non-isocyanate polyurethanes. Fully vegetable oil-based PHUs with tunable physico-chemical properties with respect to the monomer structures could be easily achieved.
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Océane Lamarzelle. Design of original vegetable oil-based cyclic carbonates and amines towards Poly(HydroxyUrethane)s. Polymers. Université de Bordeaux, 2016. English. ⟨NNT : 2016BORD0267⟩. ⟨tel-02003488⟩

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