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

Abstract

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

Metal‐free ring‐opening polymerization of glycidyl phenyl ether initiated by tetra‐n‐butylammonium acetate and its application to the hydroxyl‐terminated telechelic polymer

“…The ring‐opening polymerization of glycidyl phenyl ether (GPE), a common epoxide widely used as a monofunctional diluent in epoxy resins and as a modifier for dyes and fibers, has been investigated by many researchers as a polymerization technique for developing effective curing systems 8–12. The presence of metal initiators during curing often results in polymers that have low insulation and that tend to rust out.…”

“…[8][9][10][11][12] The presence of metal initiators during curing often results in polymers that have low insulation and that tend to rust out. It should also be noted that the polymerization of GPE is accompanied by frequent side reactions (i.e., chain transfer and termination reactions) that limit the increase in the molecular weights of poly(GPE).…”

Control of reactions and network structures of epoxy thermosets

“…Thanks to their fast hydrolysis rate, these imines are used as hardeners for adhesives [184]. Endo and coworkers also show that it is possible to increase the curing rate of epoxy-imine mixtures by adding five-membered cyclic dithiocarbonates [186,187]. Its reaction with an amine released from the imine results in the formation of a thiol group able to catalyse the amine-epoxide reaction.…”

One‐component epoxy resin with imine as water‐initiated latent hardener: Improvement of the mechanical and adhesive properties by the addition of methacrylate copolymer

“…We previously elucidated the curing of one‐component epoxy resin containing a bifunctional five‐membered cyclic dithiocarbonate (DTC) 5. DTC reacts with an amine to give the corresponding thiourethane compound with a thiol group 6. DTC‐containing epoxy resin is tough compared with common epoxy resin because, presumably, the thiourethane moieties effectively provide flexibility for the amine–epoxy networked polymer.…”