Patent GB-490774-A (GB)
Title: Improvements relating to textile assistants
IPC: D06M15/423
Filed: 1937-03-18
Abstract: Imidazoles containing at the m  carbon atom an alkyl chain of at least two carbon atoms in which the hydrogen atoms attached to the a carbon are unsubstituted are treated with aldehydes.  The alkyl chain may be interrupted by oxygen, sulphur or nitrogen and the products may be sulphonated, reduced, alkylated or aralkylated.  The products, which may be cation active or anion active, are stated to have emulsifying and dispersing properties. The following aldehydes may be employed: benzaldehyde, chlor and nitrobenzaldehyde, anisicaldehyde, cinnamic aldehyde, phenylacetaldehyde, formaldehyde, acetaldehyde, valerylaldehyde, oenanthol, lauric aldehyde and heterocyclic aldehydes, e.g. furfural.  In an example, m -heptadecylbenzimidazole is heated in an atmosphere of carbon dioxide with benzaldehyde and boric acid as a condensing agent; the benzal-m -heptadecylbenzimidazole may be treated with sulphuric monohydrate, benzyl-chloride or ethylchloride.  Samples have been furnished under Sect. 2 (5) of products prepared by treating with benzaldehyde (a) dodecyl-m -methylenebenzimidazolthioether, (b) p-tolyl-m -methylenebenzimidazol, ether, (c) the octadecyl amide of benzimidazole-m -propionic acid.  The Specification as open to inspection under Sect. 91 comprises also the treatment with an aldehyde of any cyclic amidine which at the m -carbon atom contains an alkyl chain of at least two carbon atoms, in which the hydrogen atoms of the a  carbon are unsubstituted.  The products may also be arylated.  The following additional components are mentioned, dialkylaminobenzaldehyde, paraformaldehyde, ethylbromide and iodide, m -heptadecenylbenzimidazole and tridecyl-, pentadecyl- and undecyl-benzimidazoles.  The propylation of the products is referred to.  This subject-matter does not appear in the Specification as accepted.ALSO:Imidazoles containing at the m  carbon atom an alkyl chain of at least two carbon atoms in which the hydrogen atoms attached to the a  carbon are unsubstituted are treated with aldehydes.  The alkyl chain may be interrupted by oxygen, sulphur or nitrogen and the products may be sulphonated, reduced, alkylated or aralkylated.  By suitably selecting the final treatment, textile assistants which are cation active or anion active may be obtained. The products precipitate dyestuffs containing sulpho groups from their solutions and are stated to have wetting, emulsifying, dispersing, washing, softening and foaming properties.  The following aldehydes may be employed; benzaldehyde, chlor and nitrobenzaldehyde, anisicaldehyde, cinnamic aldehyde, phenylacetaldehyde, formaldehyde, acetaldehyde, valerylaldehyde, oenanthol, lauric aldehyde and heterocyclic aldehydes, e.g. furfurol.  In examples, (1) m -heptadecyl benzimidazole is heated in an atmosphere of carbon dioxide with benzaldehyde, and boric acid as a condensing agent; the benzal-m -heptadecylbenzimidazole is purified by precipitating it as hydrochloride; the treatment with sulphuric monohydrate, benzyl chloride and ethylchloride is described; (2) the sulphonated product is used for washing raw wool; (3) the product obtained by treating with ethylchloride is used in dyeing cotton yarn with Direct sky blue green shade; (4) benzylheptadecylbenzimidazole, obtained as described in example 1, is treated with fuming sulphuric acid; (5) benzalheptadecylbenzimidazole is treated with hydrogen under pressure in the presence of nickel catalyst.  Samples have been furnished under Sect. 2 (5) of products prepared by treating with benzaldehyde: (a) dodecylmethylenebenzimidazolthioether, (b) p-tolylmethylenebenzimidazolether, and (c) the octadecyl-amide of benzimidazolepropionic acid. Dodecylmethylenebenzimidazolthioether is prepared by condensing thioglycollic acid with a mixture of olefines having 10-12 carbon atoms and heating the product with o-phenylenediamine. p-Tolylmethylenebenzimidazole ether is prepared from o-phenylenediamine and p-methylphenoxyacetic acid.  The octadecylamide of benzimidazole propionic acid is prepared by heating together octadecylamine and benzimidazol-m -propionic acid ethylester.  The Specification as open to inspection under Sect. 91 comprises also the treatment with an aldehyde of any cyclic amidine which, at the m  carbon atom contains an alkyl chain of at least two carbon atoms, in which the hydrogen atoms of the a  carbon are unsubstituted.  The products may also be arylated.  The following p additional components are mentioned: dialkylaminobenzaldehyde, paraformaldehyde, ethylbromide and iodide, m -heptadecenylbenzimidazole and tridecyl-, pentadecyl- and undecyl-benzimidazoles.  The propylation of the products is referred to.  This subject-matter does not appear in the Specification as accepted.