RenewableBeta-Elemene based Cyclic Carbonates for the Preparation of Oligo(hydroxyurethane)s

We report on the conversion of β-elemene into new β-elemene dicarbonatesvia epoxidation and halide salt-catalyzed CO2cycloaddition reactions. Step-growth polyaddition of this dicarbonatetofive different,commercial diamines was investigatedunder neat conditions at 150 ºC yielding non-isocyanate-based low molecular weight oligo(hydroxyurethane)swith 1.3 ≤ Mn≤ 6.3 kDaand1.3 ≤ Ð≤ 2.1, and with glass transitiontemperaturesranging from −59 to84 ºC. The preparation of one selected polyhydroxyurethanematerial, obtained in the presence ofJeffamine®D-2010 wasscaled-up to 43 g. The latter, when combined in a formulation usingIrgacure®2100 and Laromer®LR 9000 allowedthe preparation of coatings that were analyzed with several techniques showing the potential of these biobased oligourethanestowards the preparation of commercially relevant materials.