Patent GB-1057292-A (GB)
Title: Water soluble epoxides and coating compositions containing such compounds
Inventor: WONG ROBERT
IPC: C08G59/50
Filed: 1963-07-17
Abstract: Water soluble epoxyamine salts are prepared by reacting in solution an epoxide compound having at least two oxirane rings with a monoamine of the formula: <FORM:1057292/C2/1> wherein R1 is an aliphatic radical having at least one hydroxyl group and R2 is hydrogen, an alkyl radical having up to 6 carbon atoms or an aliphatic radical having at least one hydroxyl group, the ratio of active amine hydrogen atoms to oxirane groups being less than 1:1, separating, if desired, the addition product from the solvent and acid-neutralizing the addition product.  The polyepoxides specified include the monomeric polyglycidyl polyethers of polyhydric phenols. The amines specified are ethanolamine, propanolamine, butanolamine, isopropanolamine, 2-aminobutan-1-ol, methylaminoethanol, ethylaminoethanol, diethanolamine, di-isopropanolamine, 2-aminoethyl 2-hydroxyethyl ether, polyoxyethylene amine, polyoxypropylene amine, 1,2,3,4,5,6-hexahydroxyhexylamine, trishydroxymethylmethylamine, 2-amino-2-methyl-1,3-propanediol. The reaction may be performed in solvents such as toluene, chlorinated hydrocarbons, isopropanol, acetone and diacetone alcohol whilst the salt may be formed using acids such as hydrochloric, sulphuric, phosphoric, acetic and lactic acids.ALSO:Water-soluble acid-neutralized addition products comprising oxirane groups and amine hydrogen are prepared by reacting in solution an epoxide compound having at least two oxirane rings with a monoamine of the formula <FORM:1057292/C3/1> wherein R1 is an aliphatic radical having at least one hydroxyl group and R2 is hydrogen or an aliphatic radical having at least one hydroxyl group or an alkyl radical having up to 6 carbon atoms, the ratio of active amine hydrogen to oxirane groups being less than 1:1, separating, if desired, the addition product from the solvent and acid-neutralizing the addition product.  The polyepoxides specified are glycidyl ethers of polyhydric phenols or of novolac resins, and may be monomeric or polymeric and may be modified with fatty acids.  The amines specified are ethanolamine, propanolamine, butanolamine, isopropanolamine, 2 - aminobutan - 1 - ol, methylaminoethanol, ethylaminoethanol, diethanolamine, di-isopropanolamine, 2 - aminoethyl 2 - hydroxyethyl ether, polyoxyethylene amine, polyoxypropylene amine, 1,2,3,4,5,6-hexahydroxyhexylamine, trishydroxymethyl-methylamine, 2 - amino - 2 - methyl - 1,3-propanediol. Solvents specified as reaction media are toluene, chlorinated hydrocarbons, isopropanol, acetone and diacetone alcohol whilst acids specified for salt formation (water-solubilization) are hydrochloric, sulphuric, phosphoric, acetic and lactic acids.  Forming size compositions for glass fibres comprise aqueous solutions of the amine-epoxide salts to which coupling agents such as g -aminopropyltriethoxsilane, d  - N - ethylaminobutyltriethoxysilane, vinyltrichlorosilane, vinyltris - b - methoxyethoxysilane, diallydiethoxysilane, sodium vinylsiloxanolate and g  - methacryloxypropyltrimethoxysilane and/or lubricants such as animal or vegetable oils or the condensates of stearic or pelargonic acids with tetraethylenepentamine may be added.  The sized glass fibres may be used to reinforce epoxy resins, phenolformaldehyde resins, melamine-formaldehyde resins, polyesters and addition polymers.  The amine-epoxy salts may also be used as adhesives, cast films and coating, casting, laminating and encapsulating compositions, impregnants, in car body and boat repair, solders for metal bonding and as stabilizers for vinyl resins.ALSO:Glass - fibres are coated with forming size-compositions comprising aqueous solutions of salts of acids with the adducts of epoxide compounds having at least two oxirane groups and amines having the formula: <FORM:1057292/D1-D2/1> where R1 is an aliphatic radical having at least one hydroxyl group and R2 is hydrogen, or an aliphatic radical having at least one hydroxyl group or analkyl radical having not more than 6 carbon atoms, the adduct comprising unreacted oxirane groups and amine hydrogen.  The compositions (see Division C3) may also contain coupling agents and'or lubricants.  The size may be applied near the fibre-forming bushing and may be applied by contact, spray or immersion applicators.