Patent GB-498090-A (GB)
Title: Process for the production of water-soluble, nitrogenous compounds
Filed: 1937-11-08
Abstract: Amidines having the formula RC(NR2R3): NR1 wherein R is an alkyl, aralkyl, aryl or hydroaryl radicle, R1 the same radicles as R and also a heterocyclic radicle, the alkyl and aralkyl radicles possibly containing a hetero atom, e.g. S,O or NH and R2 and R3 are hydrogen or an alkyl, aralkyl, aryl or hydroaryl radicle, R1 and R3 possibly belonging to the same hydroaromatic ring, are treated with alkylating or aralkylating agents to convert them into water soluble form.  In examples: (1) dimethylphenylbenzamidine is treated with dimethylsulphate, benzylchloride dodecylbromide, pentadecylbromide and octodecyl bromide; (2) ethylphenylbenzamidine is treated with dimethylsulphate; (3) benzoylchloride is condensed with pentadecylamine and dimethyl pentadecylbenzamidine is formed by treating with dimethylamine the imide chloride obtained by reacting the condensation product with thionylchloride; the amidine is alkylated with dimethyl or diethylsulphate; benzoylchloride may be replaced by campholic or fencholic acid chlorides; (4) phenylpiperidylbenzamidine or a derivative thereof halogenated in the acid or amide residue is treated with dimethylsulphate; (5) cetyl or dodecylbromide is used to alkylate dimethyl cyclohexylbenzamidine; (6) dimethylsulphate is used to alkylate a  : a -dichlorpalmitic acid dimethylphenyl amidine which is prepared by reacting dimethyl amine with the chloride obtained by treating palmitic acid anilide with phosphoruspentachloride; (7) palmitic acid o-toluyldimethylamidine is alkylated with dimethylsulphate; (8) benzanilide is converted into the imide-chloride and the latter reacted with diethylethylenediamine; the resulting amidine or the corresponding amidine derived from the imide chloride from campholic acid butylamide is treated with dodecyl or octadecylbromide; (9) dodecylbromide is reacted with the amidine from dimethylamine and ethylbenzimide chloride; (10) ethylpiperidylbenzamidine is treated with dodecylbromide.  The amidines besides being made from the imide halides and ammonia or any primary or secondary amine, may be made by decomposing the corresponding cyanides or thioamides with ammonia or primary or secondary amines. Carboxylic acid amides of secondary amines may also be transformed into the ketochlorides and then reacted with primary amines. Specified components for producing the amidines include: a -chlorisobutyric acid, hexahydrobenzoic acid, dichloracetic acid, amines derived by Hofmann's reaction from amides of fatty acids, e.g. cod liver oil acid, amines derived from ammonia by reaction with alcohols such as those obtained by hydrogenation of fats, resins and naphthenic acids or benzylphenols, unsym: diethyl-p-phenylenediamine, 4-chlor or 3 : 4-dichloraniline, cyclohexylaniline and 2-aminobenzthiazole.  For the alkylation and aralkylation are specified: methylchloride, laurylchloride, nuclear halogenated benzyl chlorides, glycerinechlorhydrin and chloracetic ester.  The phosphates, silicofluorides, formates and oxalates of the amidines are mentioned.  The products are stated to be textile assistants and may be used for wetting, improving the fastness of direct dyeings, stripping naphthol AS dyeings, imparting a mat appearance to regenerated cellulose, softening textiles and combating animal pests, e.g. mothproofing.  They also have bactericidal and fungicidal properties.