GB534129A - Manufacture of new amino fatty acid derivatives - Google Patents

Abstract

534,129. Amino fatty acid derivatives. GEIGY AKT.-GES., J. R. Dec. 29, 1939, No. 33042. Convention date, Dec. 30, 1938. Addition to 471,404. [Class 2 (iii)] The process described in the parent Specification in which compounds of the general formula where R is alkyl or a hydroaromatic residue of high molecular weight and R<SP>1</SP> is a cyclo-alkyl, aralkyl, or aryl group are reacted with certain amines is modified in that R in the formula above stands for hydrogen, alkyl or aralkyl, and R<SP>1</SP> for a radical of the formula which may be attached by either the alkyl or the aryl end. The amines which are used to react with these compounds include all the basic compounds referred to in Specifications 471,404, 476,843 and 503,694, and include ammonia, a primary, secondary or tertiary aliphatic, aliphatic-araliphatic, aliphatic-hydroaromatic, aliphatic-aromatic hydro-aromatic, aromatic or heterocyclic amines. The amines may also contain the same or different substituents on the nitrogen, which substituents may themselves be substituted particularly by hydroxyl and halogen atoms. The reaction of the halogen fatty acid amides with amine is carried out according to known general methods, and where primary, secondary, or tertiary amino fatty acid amides are so prepared, they can be further alkylated up to the quarternary state. For this purpose there may be used alkylating agents such as alkyl, aralkyl, or alkylene halids, halogen hydrins, halogen fatty acids halogen fatty acid esters and amides and dialkyl sulphones. Sulphonic acid esters may also be used. The compounds so produced with the exception of the quarternary compounds, insoluble in water in the form of their bases, but form water soluble salts, such as hydrochlorides, sulphates, phosphates, fluosilicates, formates, chloracetates, oxalates, citrates, tartarates. The compounds are useful as preserving agents against moths in the case of wool, fur, feathers, hair, leather, paper, natural or synthetic fibres or fabrics. In examples (1) lauroylbenzene is treated with ammonium formate to give the formyl compound of α-undecyl benzylamine, which is then treated with chloracetyl chloride to form α-undecyl-benzyl-dimethylamino acetamide; This may then be converted into its quarternary compound by treatment with dimethyl sulphate. (2) The formation of the quarternary compound in example (1) may be effected with diethyl sulphate, benzyl chloride, allyl bromide, glycol-chlorhydrin, or glycerine-α-chlorhydrin. (3) Para-lauryl amiline, prepared as described in Specification 468,226 is treated with chloracetyl chloride, and then with dimethylamine to give dimethylamino-acetic acid-laurylanilide. This is converted into a quaternary compound by means of dimethyl sulphate. (4) The compound of example (3) is treated with the quarternary forming compounds of example (2).