Patent GB-513663-A (GB)
Title: Manufacture of amino fatty acid derivatives
Filed: 1938-04-04
Abstract: 513,663. Quaternary ammonium compounds; proofing permeable materials. GEIGY AKT.-GES., J. R. April 4, 1938, No. 10320. Addition to 471,404. [Class 2 (iii)] [Also in Group VIII] A mono- or poly-amine of the formula HNRR<1> or RNHR<11>NHR, where R is a mononuclear aryl radicle which may contain substituents other than a nitro or a hydroxy group, R<1> is hydrogen, an alkyl group containing not more than six carbon atoms, or an aralkyl group, and R" is an alkylene group containing not more than six carbon atoms, is acylated by reaction with a halogenated aliphatic acid of the formula XCnH2nCOOH, where X is halogen and n is 1, 2 or 3 or an ester, chloride or other suitable derivative of such an acid, the proportion of the acid or its derivative being sufficient to acylate all the acylatable amino groups of the amine. The halogenated aliphatic acid amides so obtained are then converted into amino acid amides by reaction with ammonia or a primary, secondary or tertiary aliphatic, aliphatic-araliphatic, aliphatic - hydroaromatic, aliphatic - aromatic, hydroaromatic or aromatic amine containing neither a nuclear nitrogen atom nor an aliphatic or hydroaromatic group of more than six carbon atoms, the reagents being so selected that the products contain at least one halogen atom linked to a nucleus. Finally, if the products are not quaternary ammonium compounds, they are converted into the quaternary form by reaction with an aralkylating agent or an alkylating agent containing not more than six carbon atoms in the alkyl group(s). The secondary or tertiary amines which may be used for reaction with the halogenated acid amides may contain identical or different 'radicles linked to the nitrogen atom, and the alkyl groups which may be present in the reagents may be substituted by hydroxyl and (or) halogen. The alkylating or aralkylating agents may be alkyl, aralkyl or alkylene halides, halogenhydrins, halogenated fatty acids or their esters or amides, dialkyl sulphates, or sulphonic acid alkyl or aralkyl esters. The products are useful for protecting wool, furs, feathers, hair, leather, paper and other natural or artificial fibres against moths and other pests. Examples and a table are given, according to which (1) 3:4-dichloraniline is acylated by reaction with chloracetyl chloride, and the chlorine atom in the chloracetyl residue is then eliminated by reaction with dimethylamine ; finally, the product is converted into the quaternary form by reaction with chloracetyl- 3:4-dichloraniline, benzyl chloride, p-chlorobenzyl chloride, 3:4-dichloro-#-chloroacetophenone, chloracetyl-4-chloraniline, or chloracetyl-4-chlorothiophenol; (2) chloracetylated 4-chloromethylaniline or 41-chlorobenzyl-4- chloraniline is treated with dimethylamine, and the product is treated with 3:4-dichlorobenzyl chloride ; (3) chloracetylated 41-chlorobenzyl-4-chloraniline is treated with dimethylamine and the product is treated with chloracetyl-3:4-dichloraniline ; (4) chloracetyl- 3:4-dichloro-N-ethylaniline is treated with dimethylamine and the product is' treated with 3:4-dichlorobenzyl chloride ; (5) chloracetyl- 3:4-dichloraniline is treated with diethanolamine, and the product is treated with pchlorobenzyl chloride ; (6) chloracetyl-3:5- dichloraniline is' treated with dimethylamine and the product is treated with 3:5-dichlorobenzyl chloride ; (7) chloracetyl-3:4:5-trichloraniline is treated with dimethylamine and the product is treated with benzyl chloride; (8) di(chloracetyl)-di-(4-chlorophenyl) ethylene diamine is treated with two mols. of dimethylamine and the product is treated with two mols. of 3:4-dichlorobenzyl chloride or chloracetyl-3:4-dichloraniline. Other amines from which the halogenated aliphatic acid amides may be made are o-chloraniline, p-chloro-N-ethylaniline, 2:4- and 2:5-dichloraniline, 2:4:6- trichloraniline 2:4-dichloro-N-methylaniline, 3- chloro-2-methylaniline, 1:3-diamino-4-chlorobenzene, and 3:4-dichloro-N-(4<1>-chlorobenzyl) aniline. Specifications 120,383 [Class 2 (iii)], 476,843 and 503,694 also are referred to.