2,3-Epoxy carbamates

This invention is novel compounds containing one or more 2,3-epoxyalkyl carbamate moieties wherein the carbamate nitrogen is tertiary; prepared by a process which comprises (A) contacting an epihalohydrin carbonate with a secondary amine-containing compound wherein the secondary amine has a pKa of between 6 and 12, in a polar organic solvent under conditions such that a 3-halo-2-hydroxyalkyl carbamate wherein the carbamate nitrogen is tertiary is prepared; and (B) contacting the 3-halo-2-hydroxyalkyl carbamate with an alkali metal hydroxide, alkaline earth metal hydroxide, a secondary amine with a pH of 8 or grater, or an ion-exchange resin with pendant moieties containing hydroxide moieties or a secondary amine moiety with a pH of 8 or greater, in a lower alkanol solvent under conditions such that the 3-halo-2-hydroxy moieties are converted to 2,3-epoxyalkyl moieties so as to prepare a 2,3-epoxyalkyl carbamate. Another aspect of this invention is a polyepoxide which comprises the reaction product of (a) a 2,3-epoxyalkyl carbamate or poly-(2,3-epoxyalkyl) polycarbamate, wherein the carbamate nitrogen atom is a tertiary nitrogen atom, and (b) an active hydrogen-containing compound. A further aspect of this invention is a cured epoxy resin which comprises the reaction product of (a) a 2,3-epoxyalkyl carbamate or poly-(2,3-epoxyalkyl) polycarbamate, wherein the carbamate nitrogen atom is a tertiary nitrogen atom; (b) an active hydrogen-containing compound; and (c) an epoxy resin curing agent.