Patent GB-787733-A (GB)
Title: Manufacture and use of new condensation products containing nitrogen
IPC: D06M13/467
Filed: 1953-12-10
Abstract: The invention comprises condensation products obtainable from either an alkylene polyamine having at least 2 and at most 6 nitrogen atoms, which polyamine contains directly bound to a nitrogen atom a non-aromatic hydrocarbon radical containing at least 8 carbon atoms, and further contains bound to a nitrogen atom one or more hydroxy alkyl groups containing not less than 2 carbon atoms, or a mono-N-acylation derivative of such an alkylene diamine, the acyl group being that of an aliphatic carboxylic acid containing at least 8 carbon atoms, by condensation of the polyamine or its N-acyl derivative with an N-methylol-amide of an aliphatic or cycloaliphatic carboxylic acid containing at least 8 carbon atoms or an N-methylol derivative of a urethane of an aliphatic or cycloaliphatic alcohol containing at least 8 carbon atoms, and water-soluble or dispersible salts of such condensation products and when the products are tertiary amines, quaternary ammonium compounds thereof.  The condensation which results in etherification of the hydroxy alkyl group of the amino compound by the hydroxy group of the methylol compound, may be effected at for example 90-180 DEG  C., advantageously in the presence of a condensing agent such as boric acid, alkali borates, sodium carbonate or sodium acetate.  The reaction may be effected in an inert gas or under reduced pressure; a solvent may be present. The condensation products may be converted into salts by means of organic and inorganic acids, for example, lactic, formic, acetic, sulphuric or hydrochloric acid.  When the condensation products are tertiary amino compounds they may be quaternized by reaction with alkylating or aralkylating agents such as dimethyl sulphate, ethyl bromide and benzyl chloride; quaternary compounds may also be formed by reacting salts of the amino condensation products with alkylene oxides, e.g. ethylene oxide.  The alkylene polyamines and N-acyl derivatives used as starting materials may be derived from ethylene diamine, trimethylene diamine, diethylene triamine, triethylene tetramine, tetra ethylene pentamine and polyamines obtained by reacting an ethylene dihalide with ammonia or an amine; the non-aromatic hydrocarbon radical of at least 8 carbon atoms present in the amine may be, for example, the 2-ethyl octyl, dodecyl, cetyl, octadecyl, octadecenyl or abietyl radical and the hydroxy alkyl group(s) required may be introduced into the amine by hydroxylalkylation with an alkylene oxide.  The preferred amino reagents are N-hydroxy alkyl diamines in which the nitrogens are joined by an alkylene radical of 2-3 carbon atoms.  Such hydroxy diamines may be obtained by condensing acrylonitrile with an amine containing the required hydrocarbon radical, reducing the nitrile group in the product and then hydroxyalkylating the resulting diamine; appropriate amines are for example dodecylamine, octadecylamine, oleyl amine, mixtures of amines corresponding to coconut nut oil, soya bean oil and tall oil fatty acids and rosin oils such as abietyl amine and hydrogenated abietylamine.  Specified methylol-substituted reagents are the methylol amides of caprylic acid, lauric acid, palmitic acid, stearic acid, oleic acid, linoleic acid, hardened train oil fatty acid, abietic acid and naphthenic acid and the methylol derivative of octadecyl urethane.  The salts and quaternary ammonium salts of the condensation products are textile assistants (see Group IV (c)).  In examples: (1) a mixture of N-alkyl trimethylene diamines in which the alkyl residues correspond to soya bean oil fatty acids is reacted with ethylene oxide (about 3 mols.) and the resulting hydroxy ethylated diamines are condensed with about 1 mol. of commercial stearic acid methylolamide; or (3) with 2 mols. thereof, in the presence of boric acid and sodium carbonate at 108-111 DEG  C. while intermittently reducing the pressure; the product yields salts with acetic and formic acid and is quaternized with benzyl chloride; (2) similarly, N-octadecyl amine is tri-hydroxyethylated and the product condensed with about 1 mol. of commercial stearic acid methylol amide; or (4) about 2 mols. thereof, and the condensate is converted into the acetate salt or is quaternized with benzyl chloride; (5) N-octadecyl trimethylene diamine is mono-acylated with commercial stearic acid, the product is hydroxyethylated with about 1 mol. of ethylene oxide and then condensed with about 1 mol. of stearic acid methylolamide as in (1) yielding a tertiary amino condensate which is converted into its acetate or is quaternized with benzyl chloride; (6) the hydroxyethylated diamine used in (2) is condensed as above described with about 1 mol. or (7) about 2 mols. of the methylol derivative of the urethane of commercial octadecyl alcohol, and the condensate is converted into a quaternary salt with benzyl chloride or into its acetate; (8) the hydroxyethylated amine used in (1) is heated with about 1 mol. of stearic acid methylol amide in toluene under reflux, and then is further heated with the addition of boric acid as catalyst and use of a water-separator; the resulting condensate is converted into its acetate.  Specification 782,974 is referred to.ALSO:As assistants in the treatment of textiles, for example as wetting, foaming, dispersing, levelling or softening agents, use is made of water-soluble or dispersible salts or quaternary ammonium compounds of condensation products obtainable from an alkylene polyamine having 2-6 nitrogen atoms and containing a non-aromatic hydrocarbon radical of at least 8 carbon atoms directly bound to a nitrogen atom and also containing one or more hydroxy alkyl groups, having at least 2 carbon atoms, bound to a nitrogen atom, or from a N-mono acyl derivative of such a polyamine, the acyl group being that of an aliphatic carboxylic acid of 8 or more carbon atoms, by condensing the polyamine or N-acyl derivative thereof with an N-methylolamide of an aliphatic or cycloaliphatic carboxylic acid containing at least 8 carbon atoms or with an N-methylol derivative of a urethane of an aliphatic or cycloaliphatic alcohol containing at least 8 carbon atoms.  In examples: (1) viscose rayon or wool yarn is softened by treatment with an aqueous solution of the acetate of a condensation product from tri-hydroxyethylated N-octadecyl trimethylene diamine and 2 mols. of stearic acid methylol amide; (2) regenerated cellulose staple fibres fabric dyed with the blue-dyeing copper compound of the azo dyestuff from 1 mol. of tetrazotized dianisidine and 2 mols. of 2-oxynaphthalene - 3 : 6 - disulphonic acid is treated with an aqueous bath comprising dimethylol urea, ammonium chloride, ammonia and the acetate described in (1) and the fabric is dried, heated at 130-140 DEG  C. and washed, whereby it is given crease-resistance and a soft feel. Other similar condensation products and their preparation are described (see Group IV (b)). Specification 782,974, is referred to.