Utilization of cyclocarbonated lignin as a bio-based cross-linker for the preparation of poly(hydroxy urethane)s

Abstract

In this work, cyclocarbonated modified lignin, the most abundant reservoir of aromatic moieties in nature, was used as a green bio-based cross-linker on polyhydroxy urethane formulations. As a preliminary study, a complete 13C NMR characterization of the aminolysis products of cyclocarbonated lignin with 1,12-diaminododecane was provided. The best reaction conditions found for the aminolysis reaction were applied for the preparation of thermoset resins. Cyclocarbonated lignin was then reacted with 1,12-diaminododecane, acting as a chain extender, in the presence of poly(ethylene glycol) bis cyclic carbonate, a soft segment used to tune the resin properties. Different (total cyclocarbonates)/(total amines) equivalent ratios and diverse poly(ethylene glycol)/lignin stoichiometry were tested. The evolution in time of the molecular weight distribution of a selected composition was followed by gel permeation chromatography until the solubility in THF was appreciable. Moreover, some significant resin samples were subjected to DSC analysis to evaluate favourable changes in the glass transition temperature and compared to blank experiments that did not include lignin in the composition.