Effect of structure on the properties of polyurethanes based on aromatic cardanol-based polyols prepared by thiol-ene coupling

Industrial-grade cardanol and 2-mercaptoethanol were reacted to generate hydroxyl-functionalized cardanol by UV, free-radical-initiated thiol-ene coupling between the double bond moieties of the cardanol long carbon side chain and thiol functional groups. The average hydroxyl number of the hydroxyl-functionalized cardanol was controlled by reaction time, with the hydroxyl values of this ranging within 168-201 mg KOH g(-1). This cardanol was then used as a polyol to prepare cardanol-based polyurethane with hexamethylene diisocyanate and a NCO/OH ratio of 1. To compare the effect of cardanol-based polyols with the properties of cardanol-based polyurethane, cardanol modified with 10-undecylenate was used as a raw material to prepare cardanol-based polyols, including the long carbon chain of 10-undecylenate. All properties were examined, and data revealed that cardanol-based polyols including this long carbon chain can improve the hydrophobic and mechanic properties of the cardanol-based polyurethane. (C) 2015 Elsevier B.V. All rights reserved.