Abstract
A series of multi-functional thiols having thiourethane moieties were successfully obtained by the reactions of 5-membered dithiocarbonates (DTC) with amines and the obtained thiols were reacted with epoxides to examine those reaction behaviors. The polyaddition reactions of the DTC-derived bifunctional thiols with bisphenol A diglycidyl ether were performed in bulk with studying the time-dependence of the viscosity to reveal that those thiols exhibited much higher reactivity than simple alkane dithiols such as 1, 10-decanedithiol. The difference in the reactivities between the DTC-derived thiols and the alkane dithiol suggested that the thiourethane moiety in the former ones played an important role for the promotion of the reaction, which would involve 1) intra-molecular hydrogen bonding between the thiol and the thiourethane groups that promoted deprotonation from the thiol to enhance its nucleophilicity and 2) inter-molecular hydrogen bonding between the thiourethane group and the oxygen atom of the epoxide to enhance its electrophilicity.
