Patent GB-782974-A (GB)
Title: New quaternary ammonium compounds and processes for their manufacture and application
IPC: D06M13/322
Filed: 1953-11-25
Abstract: Quaternary ammonium compounds obtainable from an aliphatic or cycloaliphatic tertiary amine which contains at least 2 aliphatic or cycloaliphatic residues each containing at least 8 carbon atoms, the amine being a condensation product of an N-methylol derivative of an aliphatic or cycloaliphatic acid amide or urethane containing at least 8 carbon atoms with an Nhydroxyalkyl aliphatic or cycloaliphatic tertiary amine, the hydroxyalkyl group or groups of which contain at least 2 carbon atoms, by quaternation with an aralkyl halide or with an alkyl halide containing an epoxy or carboxylic acid amide group until the product is soluble in hot water (see Group IV (b)) may be used as wetting, foaming, dispersing or especially softening agents in the treatment of textiles, in particular, cellulose, wool and polyacrylonitrile fibres.  Numerous quaternary compounds are described characterized by having the quaternated nitrogen atom connected to the nitrogen atom of the above specified amide or urethane by the group -alkylene-O-CH2-; at least one such configuration must be present and two are required when the hydroxy alkyl tertiary amine does not have an aliphatic or cycloaliphatic hydrocarbon radical of at least 8 carbon atoms directly bound to the nitrogen.  In examples: (10) upon or wool yarn is softened by treatment with an aqueous solution of a quaternary compound obtained by condensing triethanolamine in two stages with about 2 mols. of commercial stearic acid methylolamide and quaternating the product with benzyl chloride; (11) staple fibre fabric is treated with an aqueous solution comprising dimethylol urea, ammonia, ammonium chloride and the quaternary compound of (10) and the material is then dried, heated at 130-140 DEG  C. and washed, being thereby provided with a crease-proof finish and soft handle. Specification 600,707 is referred to.ALSO:The invention comprises quaternary ammonium compounds obtainable from an aliphatic or cycloaliphatic tertiary amine which contains at least 2 aliphatic or cycloaliphatic residues, each residue containing at least 8 carbon atoms, the amine being a condensation product of an N-methylol derivative of an aliphatic or cyclo aliphatic amide or urethane containing at least 8 carbon atoms with an N-hydroxy alkyl aliphatic or cycloaliphatic tertiary amine, the hydroxy alkyl group or groups of which contain at least 2 carbon atoms, by quaternation of the amine condensation product, with the aid of heat, with an aralkyl halide or with an alkyl halide containing an epoxy or carboxylic acid amide group until the reaction product is soluble in hot water.  The tertiary amine condensation products have the tertiary nitrogen atom connected to the amido nitrogen atom of the above specified amide or urethane by the grouping -alkylene-O-CH2-; at least one such configuration must be present and two are required when the N-hydroxy tertiary amine does not have an aliphatic or cycloaliphatic hydrocarbon radical of at least 8 carbon atoms directly bound to the tertiary nitrogen atom, such as the dodecyl, cetyl, octadecyl, octadecenyl, abietyl or 2-ethyloctyl radical.  Numerous amido compounds are specified for use in the form of their methylol derivatives in the condensation, including the amides of caprylic acid, palmitic acid, oleic acid, hardened train oil fatty acid, abietic acid and of naphthenic acids, N-ethyl, hydroxy ethyl or dihydroxypropyl lauric acid amide and octadecyl urethane.  The quaternation is suitably effected at 90-120 DEG  C. with, for example, benzyl chloride, p-chlorobenzyl chloride, chloracetamide or epichlorhydrin.  The products are textile assistants (see Group IV (c)).  In typical examples: (1) and (3) commercial stearic acid methylolamide is condensed with about 1 mol. of triethanol amine in the presence of sodium carbonate by heating under reduced pressure; the product is then similarly reacted with additional amounts of stearic acid methylol amide yielding products containing two or three stearamido-methylene oxy residues respectively and the products are quaternated with benzyl chloride; (4) triethanolamine is similarly condensed with about 2 mols. of coconut oil fatty acid methylolamide and the product quaternated as in (1); (5) a mixture of octadecenylamine, octadecylamine and hexadecylamine is reacted with about 2 mols. of ethylene oxide and the product is condensed with about 1 or 2 mols. of stearic acid methylamide and then quaternated with benzyl chloride; in this experiment, the methylolamide may be replaced by N-methylol octadecyl urethane and the benzyl chloride by chloracetamide or epichlorhydrin; (6) the methylol compound used in the second step of (1) is replaced by N-methylol octadecyl urethane; (10) diethylene triamine is condensed with 5 mols. of ethylene oxide and the hydroxyethylated product is condensed with about 2 mols. of stearic acid methylolamide and then quaternated with benzyl chloride. Specification 600,707 is referred to.