Patent GB-471404-A (GB)
Title: Manufacture of new amino-acid derivatives
Filed: 1936-12-14
Abstract: Amides of aminocarboxylic acids are obtained by the action of primary, secondary or tertiary amines on halogencarboxylic acid amides of the formula XCnH2nCONRR<1>, where X is halogen, n is 1, 2 or 3, R is a saturated or unsaturated aliphatic or hydroaromatic radicle containing more than six carbon atoms, and R<1> is a cycloalkyl, aralkyl or aryl group.  The amines may be of aliphatic, araliphatic, hydroaromatic or aromatic character, and in the case of secondary or tertiary amines the substituent radicles may be identical or different or may be linked to form, with the nitrogen atom, a heterocyclic ring, as in piperidine, pyridine or nicotine; if the amine contains alkyl groups, these may be substituted by halogen and/or hydroxyl.  The halogenated amides of the formula above are obtainable from halogenated carboxylic acids containing up to 4 carbon atoms, or their chlorides, and amines of the type NHRR<1>, where R and R<1> are as above; in particular, R may be a radicle of a higher alcohol obtainable by reducing a fat, oil, resin or naphthenic acid.  When the aminocarboxylic amides obtained as described above contain secondary or tertiary amino groups, they may be after-treated with alkylating or aralkylating agents, which may contain hydroxyl and/or halogen in the alkyl or aralkyl group; specified types of alkylating or aralkylating agents are mineral-acid esters of saturated or unsaturated alcohols, such as alkyl, aralkyl or alkylene halides, halogenhydrins, and dialkyl sulphates, and also alkyl or aralkyl sulphonates; the products containing secondary or tertiary amino groups may also be converted into salts with inorganic or organic acids, e.g. into hydrochlorides, sulphates, phosphates, silicofluorides, formates, monochloracetates, oxalates, citrates or tartrates.  The products are useful (a) as wetting agents, (b) for improving the fastness of direct dyeings to water, (c) for stripping Naphthol AS dyeings, (d) for imparting a matt appearance to regenerated cellulose, e.g. by impregnating the material with an aqueous emulsion containing lithopone, an emulsifying agent, and a product of the invention, (e) as softening agents for textiles, (f) as agents for combatting animal pests, e.g. for protecting plants or for moth-proofing, and (g) as bactericides or fungicides.  In the examples, (1) dimethylaminoacetic acid N - lorylanilide ("loryl" meaning the radicle of the mixture of higher alcohols obtainable from coconut oil) is prepared from dimethylamine and chloracetic acid N-lorylanilide, obtainable by chloracetylating lorylaniline; the conversion of the product into salts with oxalic, sulphuric, hydrochloric, phosphoric, formic and chloracetic acids, and also the after-treatment of the product with allyl bromide, butyl bromide, glycol chlorhydrin, glycerol a -chlorhydrin, o-chlorobenzyl chloride, p-toluenesulphonic acid amyl ester, and chloromethylsalicylic acid are described; in place of lorylaniline the corresponding cetyl, ceryl, stearyl or oleyl compounds may be used, as well as benzyldodecylamine or a naphthenaniline; (2) chloracetolorylanilide is treated with diamylamine; the product may be converted into salts or after-treated as described in example 1; its after-treatment with dimethyl sulphate is also described; (3) chloracetolorylanilide is treated with piperidine; the after-treatment of the product with benzyl chloride is described; the dimethylamine, diamylamine and piperidine used in examples 1--3 may be replaced by mono- or di-ethylamine, mono- or di-ethanolamine, g -chloro-b -oxypropylamine, cyclohexylaniline or benzylamine; (4) chloracetolorylanilide (or another of the starting materials specified in example 1) is treated with trimethylamine, triethylamine, triethanolamine, pyridine or nicotine; the chloracetic acid derivatives used in examples 1--4 may be replaced by the corresponding chloropropionic or chlorobutyric acid derivatives.  Specification 428,153 is referred to.