Activated lipidic cyclic carbonates for non-isocyanate polyurethane synthesis

Activated 5-membered cyclic carbonates were prepared from glycerol and fatty acid derivatives. Ester and ether moieties were introduced in the beta position to the cyclic carbonate, in order to enhance its reactivity towards amines. H-1 NMR kinetic investigation of the aminolysis of these cyclic carbonates demonstrated a higher reactivity compared to the one of alkyl substituted cyclic carbonates. In the case of ester-activated carbonates, a reactivity similar to the one of 6-membered ring cyclic carbonates was observed. Moreover, these carbonates exhibited amidation side-reactions with amines that could be however prevented by decreasing the temperature to room temperature. Poly(hydroxyurethane) s (PHUs) were then synthesized from these activated 5-membered ring cyclic carbonates at 70 degrees C in DMF (1 mol L-1) and exhibited molar masses up to 13 700 g mol(-1) with T-g in the range -26 to -10 degrees C.