GB560897A - Process for the manufacture of new hydroxamic acid derivatives - Google Patents

Abstract

A hydroxamic acid which contains a basic group or at least 8 carbon atoms in an aliphatic or cycloaliphatic residue is treated with an acylating agent capable of introducing the residue of a carboxylic or sulphonic acid. The latter may contain halogen, which may be exchanged for a quaternary ammonium group, an isothiourea resudue in salt form or a neutralised thiosulphuric acid residue so as to render the product soluble in water. Groups which render the products soluble may be already present in the acylating agents. In a modification, a hydroxamic acid containing halogen may be used as starting material. It is first acylated and then the halogen is exchanged for a basic group. For the acylation, carboxylic or sulphonic acids or their functional derivatives are employed. Examples of such agents are: maleic anhydride, succinic anhydride, phthalic anhydride, sulphoacetic acid, sulphochloracetic acid, sulphosuccinic acid, sulphophthalic anhydride, 3 : 5-disulphophthalic anhydride, benzoylchloride-3 : 5-disulphonic acid and chloracetic acid. The products may be used as wetting, levelling, emulsifying and washing agents in the textile and leather industries. The high molecular products, when applied to cellulose, regenerated cellulose, wool or silk fabrics and subjected to a heat treatment render them water repellent. Products containing a basic group improve the fastness of cellulose dyed with acid dyes, and may be used for animalising cellulose. Salts of weak acids, alkali hydroxides, paraffin wax, methylol compounds of higher fatty acid amides, thioureas, aminothiazines and synthetic resins may be used in conjunction with the products for the treatment of textiles so as to increase the hydrophobic and anticrease properties of the latter. In examples: (1) lauric or stearic hydroxamic acid is acylated with acetic anhydride; (2) stearichydroxamic acid is treated with benzoic acid meta-sulphochloride or para - chlormethylbenzoylchloride in the presence of pyridine; (3) 4-chlormethylbenzoyl-chloride is condensed with hydroxylamine-hydrochloride and the resulting 4-chlormethylbenzhydroxamic acid first reacted with trimethylamine and then acylated with acetic anhydride; (4) a mixture of palmitic and stearic hydroxamic acids is treated with chloracetylchloride in dioxane and the product made soluble by treating with sodium thiosulphate in methanol or with thiourea in acetone; (5) cotton fabric is treated with a solution containing acetone, caustic soda and the acetylated stearic hydroxamic acid of example (1); (6) cotton material is treated with products obtained as in examples (2) and (3). The hydroxamic acids may be derived from aliphatic, aliphatic aromatic, aromatic and cycloaliphatic carboxylic acids and may be prepared by known methods. Thus, stearic acid methyl ester may be reacted with hydroxylaminic hydrochloride to give stearic hydroxamic acid and parastearylaminobenzoylchloride may be reacted with hydroxylamine to give the corresponding hydroxamic acid.