Patent GB-476843-A (GB)
Title: Manufacture of new amino-acid derivatives
Filed: 1936-12-18
Abstract: Amides of aminocarboxylic acids, containing a saturated or unsaturated aliphatic or a saturated hydroaromatic radicle of more than six carbon atoms linked to an amino nitrogen atom, are prepared from halogenated carboxylic amides of the formula XCnH2n CONRR<1>, where X is halogen, n is 1--3, R is hydrogen, an alkyl group of less than six carbon atoms, or an aryl or aralkyl group, and R<1> is an alkyl group of less than six carbon atoms or an aryl or aralkyl group, (1) by reacting the halogenated carboxylic amides with a primary, secondary or tertiary amine containing an aliphatic or hydroaromatic radicle of more than six carbon atoms, or (2) by reacting the halogenated carboxylic amides with ammonia or a primary or secondary amine and treating the products with an alkylating or aralkylating agent, an aliphatic or hydroaromatic radicle of more than six carbon atoms being introduced in one or other of these stages; in either process, such of the products as are not quaternary ammonium compounds may be alkylated or aralkylated to the quaternary stage, or they may be converted into salts with inorganic or organic acids, e.g. into hydrochlorides, sulphates, phosphates, silicofluorides, formates, monochloracetates, oxalates, citrates or tartrates.  The halogenated amides used as starting materials are obtainable from halogenated carboxylic acids containing up to four carbon atoms, or their chlorides, and amines of the type NHRR<1>, where R and R<1> are as above.  The amines used in method (1) or (2) above may be of aliphatic, araliphatic, aromatic or hydroaromatic character, and in the case of secondary or tertiary amines the substituent radicles may be identical or different; if the amine contains alkyl groups, these may be substituted by hydroxyl and/or halogen.  The alkylating or aralkylating agents used in method (2) above, or for after-treating the products of method (1) or (2), may be unsubstituted in the alkyl or aralkyl residue or (in the case of an alkylating agent) may be substituted by hydroxyl and/or halogen or (in the case of an aralkylating agent) may carry any substituents; specified types of alkylating or aralkylating agents are alkyl, aralkyl or alkylene halides, halogenhydrins, dialkyl sulphates, and alkyl or aralkyl sulphonates.  The aliphatic or hydroaromatic residue of more than six carbon atoms in the products may be a residue of an alcohol obtainable by reducing a fat, oil, resin or naphthenic acid. 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 mat 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 combating animal pests, e.g. for protecting plants or for mothproofing, and (g) as bactericides or fungicides.  In the examples: (1) chloracetic acid dimethylamide is condensed with lorylamine, i.e. the amine mixture corresponding to the higher alcohols obtainable from coconut oil; the product may be converted into a salt or a quaternary compound as indicated above and as described more particularly in Specification 471,404; in place of chloracetic acid dimethylamide there may be used the corresponding methylamide, diethylamide, anilide or a substituted anilide such as the methylanilide, methyl-3-chloranilide, benzylanilide, diphenylamide, or a carboxyanilide; in place of lorylamine there may be used cetylamine, cerylamine, stearylamine or oleylamine; (2) dimethylaminoacetic acid monoethylamide is treated with loryl bromide; dimethylaminoacetochlorobenzylphenylamide, diethylaminoacetodiphenylamide, piperidinoacetomonomethylamide, phenylaminoacetodimethylamide, and, in general, N : N<1>-substituted aminoacetamides prepared from diethylamine, mono- or di-ethanolamine, g -chloro-b -oxypropylamine and benzylamine may be similarly treated; a mineral acid ester of oleyl, cetyl or stearyl alcohol may be used in place of loryl bromide, and in place of the chloracetic derivatives used in either of the examples, the corresponding chloropropionic or chlorobutyric acid derivatives may be used.