Synthesis and characterization of ammonium containing cyclocarbonates and polyurethanes there from

Abstract

Using a three steps procedure a water soluble cationic bis-cyclocarbonate was prepared. Aminolysis was attempted in water but was not successful because of rapid hydrolysis of the starting cyclocarbonate in these basic conditions. Non-isocyanate polyurethanes (linear and crosslinked) were then prepared in acetonitrile with high yields. The resulting materials exhibited good thermal properties (Tdeg > 230 °C) and Tg > 60 °C. The presence of the cationic moiety led to hydrophilic materials with swelling rate of 45% and a plastification effect was observed with Tg decreasing down to −28 °C. Further, considering ammonium characteristics, antibacterial properties were assessed. Surface adhesion test showed a 99,9% inhibition towards gram-positive and gram-negative bacteria for the polyurethane thermoset. Acute toxicity was evaluated on the bis-cyclocarbonate oligomer confirming its innocuity in the studied concentration range.