Résumé : |
Within the general context of depleting fossil feed stocks, current efforts aim at developing polymers from bio-renouvelable resources within green and sustainable chemistry. The actual challenge in polyurethane industry is to establish a synthetic procedure exempt of isocyanate. To tackle this issue, we propose a simple isocyanate-free method to synthesize (poly(trimethylene carbonate hydroxy-urethane)s, using trimethylene carbonate (TMC) derived from glycerol, a by-product of biofuels made from plant oils, as a key starting material. The strategy first involves the synthesis of an α,ω-dihydroxy telechelic polycarbonate upon immortal ring-opening polymerization (iROP) of TMC using a diol as a chain transfer agent. This macrodiol is subsequently chemically modified into the corresponding α,ω-di(cyclo carbonate) telechelic polycarbonate upon reaction with succinic anhydride followed by coupling to glycerol carbonate. Alternatively, an α,ω--hydroxy-cyclo carbonate telechelic (poly(trimethylene carbonate) (PTMC), prepared from the iROP of TMC using glycerol carbonate as chain transfer agent, can be similarly tailored into the corresponding di(cyclo carbonate) functionalized PTMC. Ultimately, ring-opening polyaddition of the terminal cyclic carbonate of the α,ω-di(cyclo carbonate) telechelic PTMC with a diamine generates the non-isocyanate polyurethane (NIPUs) upon creating bonds between carbon and nitrogen. |