Patent GB-415718-A (GB)
Title: Process for the manufacture of acid amide derivatives
IPC: C09K23/00
Filed: 1933-02-28
Abstract: Carboxylic and sulphonic acid amides stated to be useful as emulsifying agents in the textile industry are prepared by treating one molecular proportion of an acid amide having the formula RCON <R>1H or RSO2N <R>1H in which R is an organic residue containing at least eight carbon atoms directly connected together and R1 is hydrogen or alkyl, aralkyl, aryl or cycloalkyl groups which must be free from hydroxyalkyl and oxyalkyloxy groups, with not more than three molecular proportions of alkylene oxide for each reactive hydrogen atom in the amide group.  In order to improve their solubility, the products may be treated with polybasic mineral acids containing oxygen, e.g. phosphoric or sulphuric acid.  The acid amides used as starting material may be prepared by condensing the carboxylic or sulphonic acids with ammonia, or mono or diamines. Fatty acids obtained by oxidation of paraffins, undecylenic acid, lauric acid, stearic acid, oleic acid, dihydroxystearic acid, resin and montan wax acids, naphthenic acids, phthalic acid, phthalamic acid, 1 : 8-naphthalenedicarboxylic acid and cyclohexylpropionic acid may serve as the parent acids for the amides as well as the fatty acids of palm oil, coco nut oil, poppy seed oil, rape oil, linseed oil, soya bean oil, train oil, chinawood oil and castor oil. Palmitic sulphonamide, cetylsulphonamide, 1-hydroxynaphthalene-2-sulphonamide and dichlorstearylethylamide are mentioned as starting materials. Aniline, aminonaphthols and phenols, phenylenediamine and methyl, butyl, benzyl, undecyl, cyclohexyl, heptadecyl and heptadecylene amines are bases which are specified.  The more soluble products may be used for emulsifying oils, fats and hydrocarbons.  The lipoid soluble products may be used in the production of salves, cosmetics, pharmaceutical preparations, greasing and stuffing agents and cutting and boring oils.  Soaps, turkey red oils, mineral oils, fatty alcohol sulphonates, alkylated-naphthalenesulphonic acids, glue, gelatine, sulphite cellulose liquor, gums, mucilages, alcohols, ketones, hydrocarbons and halogenated hydrocarbons may be used with the products.  In examples: (1) ethylene oxide is introduced into a product derived from partially hydrogenated train oil and ammonia (cf. Specification 384,665, [Group IV]) whereby a product is obtained which may be used for emulsifying mineral oils: (2) dibutylnaphthalenesulphonamide is treated with ethylene oxide.  The Specification as open to inspection under Sect. 91 comprises also the treatment with ethylene oxide of crude acid amides derived from glycerides, to obtain similar products.  The use of the products together with condensation products of fatty acids with hydroxy and aminoalkylsulphonic acids, albumin degradation products and enzymes is referred to.  The following components are also mentioned: dodecylsulphuric ester amide (obtainable by treating with ammonia the acid chloride prepared by reacting dodecylsulphuric ester with phosphorus pentachloride) and 4-hydroxyphenylethyl-amine.  This subject-matter does not appear in the Specification as accepted.ALSO:Carboxylic and sulphonic acid amides stated to be useful as wetting, cleaning, emulsifying and levelling agents in the textile industry are prepared by treating one molecular proportion of an acid amide having the formula, <FORM:0415718/IV/1> organic residue containing at least eight carbon atoms directly connected together and R1 is hydrogen or an alkyl, aralkyl, aryl or cycloalkyl group which must be free from hydrooxyalkyl and oxyalkyloxy groups, with not more than three molecular proportions of alkylene oxide for each reactive hydrogen atom in the amide group.  Alkaline substances may be used to assist the reaction and water is preferably excluded as far as possible.  In order to improve their solubility, the products may be treated with polybasic mineral acids containing oxygen, e.g., phosphoric or sulphuric acid.  The acid amides used as starting material may be prepared by condensing the carboxylic or sulphonic acids with ammonia, or mono or diamines.  Fatty acids obtained by oxidation of paraffins, undecylenic acid, lauric acid, stearic acid, oleic acid, dihydroxystearic acid, resin and montan wax acids, naphthenic acids, phthalic acid, phthalamic acid, 1 : 8-naphthalenedicarboxylic acid and cyclohexylpropionic acid may serve as the parent acids for the amides as well as the fatty acids of palm oil, coconut oil, poppyseed oil, rape oil, linseed oil, soya bean oil, train oil, chinawood oil and castor oil. Palmitic sulphonamide, cetyl-sulphonamide, 1-hydroxynaphthalene-2-sulphonamide and dichlorstearylethylamide are mentioned as starting materials. Aniline, aminonaphthols and phenols, phenylenediamine and methyl, butyl, benzyl, undecyl, cyclohexyl, heptadecyl, and heptadecylene amines are bases which are specified.  The more soluble products may be added to dyeing, mercerizing, carbonizing and fulling baths and may be used for improving the fastness of dyeings to rubbing, preparing dyepastes and emulsifying oils, fats and hydrocarbons.  The lipoid soluble products may be used in preparations for oiling, sizing and softening textiles and in the production of salves, cosmetics, pharmaceutical preparations, greasing and stuffing agents, cutting and boring oils, polishes, protecting preparations for metals, lacquers, varnishes and caoutchouc.  Soaps, turkey red oils, mineral oils, fatty alcohol sulphonates, alkylated naphthalenesulphonic acids, glue, gelatine, sulphite cellulose liquor, gums, mucilages, alcohols, ketones, hydrocarbons and halogenated hydrocarbons may be used with the products.  In examples: (1) ethylene oxide is introduced into a product derived from partially hydrogenated train oil and ammonia (cf. Specification 384,665), whereby a product is obtained which may be used for emulsifying mineral oils: (2) dibutyl naphthalenesulphonamide (obtained by treating dibutylnaphthalene sulphonic acid with phosphorus pentachloride and condensing the acid-chloride with ammonia) is treated with ethylene oxide.  Dichlorstearylethylamide may be obtained by chlorinating stearic acid chloride to form dichlorstearylchloride and condensing the latter with ethylamine. The Specification as open to inspection under Sect. 91 comprises also the treatment with ethylene oxide of crude acid amides derived from glycerides, the clarification of the products by treating with peroxides, hypochlorites, decolorizing carbon or Fuller's earth and their use for stabilizing diazo solutions.  The use of the products together with condensation products of fatty acids with hydroxy and aminoalkylsulphonic acids, albumin degradation products and enzymes is referred to.  The following components are also mentioned; dodecylsulphuric ester amide (obtainable by treating with ammonia the acid chloride prepared by reacting dodecylsulphuric ester with phosphorus pentachloride) and 4-hydroxyphenylethylamine.  This subject-matter does not appear in the Specification as accepted.