Role of cyclic dithiocarbonate as a promoter in the reaction of epoxide and imine in the presence of water

It was demonstrated that the reaction of epoxide and imine as a latent initiator under highly humid conditions was accelerated by addition of 5‐phenoxymethyl‐1,3‐oxathiolane‐2‐thione (1). When 1 was added to a mixture of glycidyl phenyl ether and an imine, the reaction of the epoxide with an amine released from the imine became faster than was the case without 1, that is, 1 worked as a promoter of the reaction. The curing rate and initial adhesive strength of epoxy resin increased compared with that without 1. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 4276–4283, 2004 The reaction of epoxide and amine released from imine was promoted by five‐membered cyclic dithiocarbonate (DTC) in one‐component epoxy resin with imine as a latent initiator. At first, DTC reacted with the amine, which hydrolyzed from imine, to convert into a thiol‐containing thiourethane. The thiol group interacted with the epoxide by hydrogen bonding to enhance the reactivity with the amine.