Patent GB-816044-A (GB)
Title: New derivatives of formaldehyde condensation compounds of melamine and manufacture and use thereof
IPC: C08G12/42
Filed: 1955-05-25
Abstract: Quaternated condensation products containing epoxy-propyl groups are made by reacting under substantially anhydrous conditions more than 1 mol. of epichlorhydrin with 1 mol. of a condensation product of (1) a formaldehyde condensation product of melamine or of ethers thereof with alcohols containing 1 to 4 carbon atoms, and (2) a compound containing at least one basic tertiary nitrogen atom which is a hydroxy ethylated or polyhydroxyethylated aliphatic amine or a hydroxylated polyethylene polyamine containing 3 to 5 nitrogen atoms and acylated at a nitrogen atom by a fatty acid containing 12 to 18 carbon atoms or hydroxyethylated piperazine.  The hydroxyethylated compounds may be prepared by reacting ethylene oxide with aliphatic monoamines and polyamines, polyalkylene polyamines or fatty amines. The products of the invention or salts thereof may be used in the form of solutions, specified solvents being water, formic, acetic or chloracetic acid and diethyl tartrate or triacetin, with or without hardening catalysts, e.g. formic, sulphuric or hydrochloric acid and ammonium chloride, sulphate, nitrate, oxalate or lactate and cross-linking agents, e.g. formaldehyde, di- or poly-hydroxy compounds, diisocyanates, inorganic salts and acids, Friedel-Crafts catalysts, acid anhydrides and polyamines or salts thereof for surface treatment of textile fabrics.  In the examples, epichlorhydrin is used for quaternating condensation products of hexamethylol melamine hexamethyl ether made by reacting hexamethylol melamine with methyl alcohol and (1) and (2) a piperazineethylene oxide reaction product; (3) a triethylene tetramine-ethylene oxide reaction product; (4) dimethyl ethanolamine; (5) the reaction product of ethylene oxide and diethylene triamine previously acylated with stearic acid; (6) a dimethyl ethanolamineethylene oxide reaction product; and (7) and (8) a triethylene tetramine-ethylene oxide reaction product; the quaternated products being (1) used as an anti-electrostatic agent, (2) purified with calcined sodium carbonate, dissolved with methylene tetramine in water and used as an anti-electrostatic agent on artificial silk or nylon fibres; (3) extracted with acetone and used for treating nylon fabrics as in Example (2); (4), (5), (6) and (7) used for treating fabrics as in Example (2); (8) used as in Example (2) for treating polyacrylonitrile fabrics.ALSO:The invention comprises a compound containing at least one quaternary nitrogen atom containing one epoxy propyl group obtained by quaternating a condensation product of a methylolated or C1-4 alkoxymethylated melamine and a compound containing at least one basic tertiary nitrogen atom, which is a hydroxyethylated or polyhydroxyethylated aliphatic amine, a hydroxy ethylated piperazine or a C12-18 fatty acylated hydroxyethylated polyethylene polyamine containing 3 to 5 nitrogen atoms. Quaternization is effected by reaction with one or more moles. of epichlorhydrin under anhydrous conditions.  Specified hydroxyethylated amines are derived from ethylene oxide and mono- and di-alkylamines, alkenylamines, polyalkylene polyamines and mono- and di-alkanolamines.  The melamine derivative may contain 1 to 6 methylol or C1-4 alkoxy methyl groups.  The compounds may be further condensed by treating solutions thereof in organic solvents with acids such as formic, acetic or chloracetic acid or compounds, e.g. diethyl tartrate or triacetin which liberate acid under the action of heat.  In the examples, epichlorhydrin is used for quaternating condensation products of hexa (methoxymethyl) melamine with (1) and (2) dihydroxyethylpiperazine, (3) hydroxyethylated triethylene tetramine, (4) dimethyl ethanolamine, (5) the hydroxyethylation product of stearoylated diethylene triamine, (6) hydroxyethylated dimethyl-ethanolamine and (7) and (8) hydroxyethylated triethylene tetramine.  Hexa (methoxymethyl) melamine is prepared by reacting hexamethylol melamine with methanol in the presence of concentrated hydrochloric acid.  Dihydroxyethyl-piperazine is prepared by treating piperazine with ethylene oxide.  The hydroxy ethylated amines and ethanolamines are made by treating the corresponding amines or ethanolamines with ethylene oxide.  Stearoylated diethylene triamine is made by treating diethylene triamine with stearic acid under nitrogen and is hydroxyethylated with ethylene oxide.ALSO:Textile materials in the form of fibres, yarns or fabrics, e.g cellulose acetate, nylon, polyesters, polyvinyl chloride and polyacrylic derivatives, have their surface conductivity modified by treatment in aqueous or nonaqueous solution with quaternated condensation products (or salts thereof) containing epoxypropyl groups made by reacting under substantially anhydrous conditions more than 1 mol. of epichlorhydrin with 1 mol. of a condensation product of: (1) a formaldehyde condensation product of melamine or of ethers thereof with alcohols containing 1 to 4 carbon atoms; and (2) a compound containing at least one basic tertiary nitrogen atom which is a hydroxyethylated or polyhydroxyethylated aliphatic amine, or a hydroxyethylated polyethylene polyamine containing 3 to 5 nitrogen atoms and acylated at a nitrogen atom by a fatty acid containing 12 to 18 carbon atoms, or hydroxyethylated piperazine.  Specified solvents are formic, acetic and chloracetic acids, diethyl tartrate and triacetin, and the solutions may also contain hardening catalysts, e.g. hydrochloric, sulphuric or formic acid, or ammonium chloride, sulphate, nitrate, oxalate or lactate, and cross-linking agents, e.g. formaldehyde, di-or poly-hydroxy compounds, diisocyanates, inorganic salts and acids, Friedel-Crafts catalysts and anhydrides and polyamines or salts thereof.  In the examples, condensation products of hexamethylol melamine hexamethyl ether and (1) and (2) a piperazine-ethylene oxide reaction product; (3) a triethylene-tetramine-ethyleneoxide reaction product; (4) dimethyl ethanolamine; (5) the reaction product of ethylene oxide and diethylene triamine previously acylated with stearic acid; (6) a dimethylethanolamine-ethylene oxide reaction product; and (7) and (8) a triethylene tetramine ethylene oxide reaction product are quaternated with epichlorohydrin to yield products useful as antistatic agents for textile materials.