Patent GB-861959-A (GB)
Title: Hydroxyalkylated polyamines and a process for their preparation
IPC: C08G59/64
Filed: 1957-07-26
Abstract: Compositions containing polyepoxy compounds having per average molecule an epoxy equivalency of more than one, contain as hardening agent a hydroxylated polyamine of the general formula R1.NH.R11.(NH.R)x.NH2 wherein R and R11 are divalent alkylene radicals -CnH2n-, n being an integer from 2 to 6, R1 is a phenyl-substituted hydroxyalkyl radical, and X is an integer from 1 to 3.  Specified hydroxylated polyamines are unsymmetrical N - (b  - phenyl - b  - hydroxyethyl) diethylenetriamine and the corresponding dipropylenetriamine derivative.  Specified polyepoxy compounds are polyglycidyl polyethers of dihydric phenols such as diglycidyl ethers of resorcinol or of dihydric bisphenols, e.g. diglycidyl ethers of 2,2 - bis - (p - hydroxyphenyl) - propane.  Polyepoxy aromatic amines and polyamines such as diglycidyl aniline and tetraglycidyl phenylene diamine, polyglycidyl thioethers of polythiols, and products made by epoxidizing diphenol reaction products of phenol and formaldehyde, or by epoxidizing phenol-formaldehyde novolaks, glycerine, glycols, or bis-cyclopentenyl ether, are also mentioned as compounds which may be hardened by means of the hydroxylated polyamines.  The compositions preferably contain equivalent proportions of polyamine and polyepoxy compound although proportions ranging from 0.25 to 2.0 equivalents of hardener per equivalent weight of polyepoxy resin may be used. Examples describe compositions containing a resinous diglycidyl ether, having an epoxy equivalent of 195 and made by reacting epichlorohydrin with 2.2-bis-(p-hydroxyphenyl) propane in the presence of sodium hydroxide as catalyst and ethyl alcohol as solvent, and containing as hardening agent unsymmetrical N - (b  - phenyl - b  - hydroxyethyl) diethylene triamine.  The hardening properties of these compositions and the physical properties of the hardened compositions are compared with similar compositions containing other hardening agents.  Curing may be initiated or accelerated by moderate heating, e.g. by infra-red lamps. Uses.-Casting tools, dies, jigs and fixtures; encapsulating, potting, laminating and bonding.ALSO:The invention comprises hydroxylated polyamines of the general formula R1.NH.R11.(NH.R)x.NH2 wherein R and R11 are divalent alkylene radicals -CnH2n-, n being an integer from 2 to 6, R1 is a phenyl substituted hydroxyalkyl radical, and X is an integer from 1 to 3.  Such compounds may be obtained by reacting an olefine oxide containing an aromatic ring in its structure with an appropriate aliphatic polyamine.  Specified hydroxyalkylated polyamines are unsymmetrical N-(b -phenyl-b -hydroxyethyl) diethylenetriamine and the corresponding dipropylenetriamine derivative.  Styrene oxide may be used as the olefine oxide reactant. The reaction may be carried out either in the absence of solvents or in presence of water or an aliphatic alcohol at temperatures of from 20 DEG  C. to the boiling-point.  Preferably a stoichiometric excess of polyamine is employed and on completion of the reaction the unreacted polyamine is removed.  In an example, diethylene triamine and water are mixed together in a reaction vessel, styrene oxide is added slowly, and agitation is continued for 1 day at room temperature, after which the mixture is heated to 100 DEG  C. for several hours.  The unreacted diethylene triamine is removed by flash distillation under reduced pressure and the residue is fractionally distilled to obtain unsymmetrical N - (b  - phenyl - b  - hydroxy - ethyl) diethylene triamine.  The corresponding dipropylene triamine is made in a similar manner. The hydroxyalkylated polyamines of the stated general formula may be used as hardeners for polyepoxy resins (see Group IV (a)).