Patent GB-448469-A (GB)
Title: Manufacture of water-soluble salts of imidoethers, imidothioethers or amidines
Filed: 1934-12-13
Abstract: Water soluble salts of imidoethers, imidothioethers and amidines are obtained by causing a mixture of at least two aliphatic or cycloaliphatic nitriles, at least one of which contains more than eight carbon atoms, to react in the presence of an acid with a compound of the general formula R.X in which R is an alkyl, aryl or hydroaryl radicle and R is OH, SH, NH2 or NHAlkyl.  Water soluble salts of amidines are also obtained by causing a salt of an imidoether to react with ammonia or a primary or secondary amine.  In examples: (1) a nitrile mixture prepared catalytically from commercial stearic acid and ammonia is reacted with hydrochloric acid and (a) butylalcohol to give an imidobutylether hydrochloride, (b) ethylmercaptan to give an imidothioether hydrochloride and (c) butylamine to give an amidine hydrochloride; (2) a nitrile mixture prepared from coconut fatty acid is reacted with ethylalcohol and hydrochloric acid; (3) the imidoethylether hydrochloride prepared according to example 2, is treated with ammonia to give an amidine hydrochloride.  The products are stated to be finishing agents for textiles.  Samples have been furnished under Sect. 2 (5) as follows: (1) the imidobutyletherhydrochloride of example 1; (2) the product obtained by reacting a fraction of a nitrile mixture derived from palm nut oil fatty acid with the reaction product of ethylenechlorhydrin and hydrogen chloride; (3) the imidomethylether hydrochloride derived from a palm oil fatty acid nitrile mixture; (4) an amidine hydrochloride derived from an imidoethyletherhydrochloride obtained from commercial stearic acid nitrile by reaction with a polyethylenepolyamine; (5) the amidinehydrochloride obtained by reacting with ammonia the imidomethyletherhydrochloride derived from a coconut oil fatty acid nitrile mixture; (6) the amidine hydrochloride obtained by reacting with ammonia the imidomethyletherhydrochloride derived from a mixture of nitriles obtained from carboxylicacids resulting from the oxidation of paraffin; (7) the formate derived from the amidine hydrochloride of sample 4; (8) the amidine hydrochloride obtained from the imidobutyletherhydrochloride of example 1 and ethylenediamine; (9) the oxalate derived from the amidine hydrochloride of sample 6; (10) the amidine hydrochloride obtained by reacting the imidobutyletherhydrochloride of example 1 with diethylamine; (11) the diethylaminoethylamidinehydrochloride derived from the imidomethylether hydrochloride obtained from a mixture of commercial stearic acid nitriles and diethylethylenediamine; (12) the imidoethylthioetherhydrochloride derived from palm oil fatty acid nitriles; (13) the amidine hydrochloride prepared by reacting aniline with the imidoethyletherhydrochloride derived from nitriles corresponding to the carboxylicacids obtained by oxidizing paraffin; (14) the imidocyclohexylether hydrochloride derived from palm oil fatty acid nitriles.  The Specification as open to inspection under Sect. 91 comprises also the use of compounds RX in which R is a heterocyclic radicle and X is as above defined.  Tetrahydrofurfuryl alcohol, octadecylalcohol, glycol, glycerol, phenol, benzylalcohol, cresol, dibutylamine, dodecylamine, glucamine, mono- and di-ethanolamines, phenylenediamine, urea, amides and urethanes are further examples of suitable components which may be used.  In additional detailed examples: (1) an imidomethylether hydrochloride is prepared from a nitrile mixture derived from palm oil fatty acid; (2) an imidopropyletherhydrochloride is prepared from a fraction of a nitrile mixture derived from palm oil fatty acid; (3) an imidoethyletherhydrobromide is prepared from a mixture of palmitic nitrile with a -ethylhexylcyanide; (4) an amidine hydrochloride is obtained by treating with diethylenetriamine an imidomethyletherhydrochloride prepared from coconut fatty acid nitrile.  This subject-matter does not appear in the Specification as accepted.