GB797241A - N:n-bis [(1-aminocycloalkyl)methyl] alkylene diamines - Google Patents

Abstract

N,N1 - bis[(1 - aminocycloalkyl) - methyl] - alkylene diamines are prepared by catalytic hydrogenation of N,N1-bis[(1-nitrocycloalkyl)-methyl]-alkylene diamines preferably in the presence of a solvent such as methanol, ethanol, isopropanol, dioxane, benzene, cyclohexane, petroleum ether or mixtures of an alkanol having 1-3 carbon atoms and water such as a 50/50 mixture of ethanol and water. Suitable catalysts are Raney nickel, nickel oxides, finely-divided metals of Group VIII of the Periodic Table, e.g. nickel, iron, cobalt, platinum, palladium or rhodium, Group VIII metals or copper supported on pumice, asbestos, kieselguhr, alumina, silica gel or charcoal, finely-divided copper, palladium or platinum black, colloidal palladium or platinum or platinum sponge. Quantities of catalyst of from one part per million of nitro compound may be used. The temperature of the reaction is preferably between the freezing and boiling point of the mixture under reaction conditions. Pressures from 1-1000 atmospheres may be used. The tetramines are separated from the reaction mixtures by filtering off the catalyst and insoluble material, distilling off the solvent, and thereafter distilling the residue at reduced pressure. The process may also be carried out continuously or in combination with the process of Specification 793,425 for producing N,N1-bis-[(1-nitrocycloalkyl)-methyl]-alkylene diamines. Th N,N1-bis[(1-aminocycloalkyl)-methyl]-alkylene diamines may be used in a process for the chelation of a heavy metal, e.g. copper, cobalt, or nickel, and also for curing epoxy resins. Examples are given of the preparation of N,N1-bis[(1 - aminocyclohexyl) - methyl] - ethylenediamine, and N,N1 - bis[(1 - nitrocyclohexyl) - methyl]-hexamethylenediamine.ALSO:N,N1 - bis - [(1 - aminocycloalkyl)methyl]alkylene diamines are used as curing agents for epoxy resins. Examples are given of compositions of an epoxy resin with (1) N,N1-bis-[(1-aminocyclohexyl)methyl]ethylene diamine; (2) N,N1 - bis - [(1 - aminocyclohexyl)methyl] hexamethylene diamine; (3) m-phenylenediamine; (4) methylenedianiline. Specification 793,425, [Group IV (b)], is referred to.