Patent GB-439261-A (GB)
Title: Manufacture of alkylated imidazoles of high molecular weight
Filed: 1934-12-11
Abstract: Alkylated imidazoles of high molecular weight are prepared by treating on imidazole which contains the atomic grouping <FORM:0439261/IV/1> wherein R stands for an aromatic nucleus, other than a benzimidazole or naphthimidazole substituted at the m -carbon atom by an aliphatic residue having at least three carbon atoms or by a hydroaromatic residue, with an alkylating agent containing at least 7 carbon atoms and if desired treating the product with a sulphonating agent or an alkylating agent or with both agents in either order.  A modification of this process comprises treating an N-oxyalkyl derivative of an imidazole containing the above group, other than a benzimidazole or naphthimidazole substituted at the m -carbon atom by an aliphatic residue having at least three carbon atoms or by a hydroaromatic residue, with an acylating agent whose acyl group contains a number of carbon atoms such that the acylated oxyalkyl group attached to nitrogen in the product contains at least 7 carbon atoms.  R in the foregoing formula may be a residue of the benzene, naphthalene, anthracene, phenanthrene or diphenyl series which may be substituted, for example, by alkyl, hydroxyl, alkoxy-, carboxyl or sulphonic acid groups; parent materials specified are benzimidazole and m -substituted derivatives such as m -methyl, -oxymethyl, -ethyl, -vinyl, -methoxy, -ethoxy, -amino, -alkylamino, -mercapto, and -thioalkyl derivatives of benzimidazole or naphthimidazoles. Specified alkylating agents are chloracetic acid amyl ester, b -chlorlactic acid butyl ester, chloracetic acid dodecyl ester, dodecyl - b  - chlorethyl ether, octadecylchlormethyl ether, octadecylchlormethyl-thioether, cetyl-b -chlorethyl-thioether, chloracetyl-decylamide, heptylchloride, octylbromide, dodecyliodide, octadecyl chloride, alkylene-oxides containing more than 7 carbon atoms and sulphuric acid esters of alcohols of high molecular weight. The products are of use as auxiliary agents in emulsifying, dispersing, softening, washing and wetting processes, and their capillary activity is enhanced by the subsequent alkylation and/or sulphonation.  In examples: (1) m -methylbenzimidazole is condensed with lauryl chloride (or cetyl-, stearyl-, or oleyl-chlorides) at 160 DEG  C.; the product is a softening agent for viscose artificial silk; (2) benzimidazole is condensed with cetyl chloride at 160 DEG C.; (3) N-cetyl-m -methylbenzimidazole (prepared as in (1)) is treated with soda lye and the resulting base treated with ethylchloride at 150--155 DEG  C.; the product has pronounced dispersing action and enhances the fastness to water of dyeings obtained with direct dyestuffs; (4) m -methylbenzimidazole is condensed with chloracetic acid dodecylester at 170--175 DEG  C.; the product improves the fastness of dyed fabrics to water and softens them; (5) m -oxymethylbenzimidazole is condensed with dodecylchloride; the product is an acid equalizing agent in dyeing; a similar product is obtained using m -methoxymethylbenzimidazole; (6) m  - methyl - N - oxyethylbenzimidazole is condensed with stearic acid chloride at 105--110 DEG  C.; the product is an equalizing agent in dyeing and a softening agent; (7) m -ethylbenzimidazole is condensed with octylbromide; (8) N - cetyl - m  - methylbenzimidazole is treated with sulphuric acid monohydrate; the product is a washing and equalizing agent.  Samples have been furnished under Sect. 2 (5) of the following: (I) hydrochloride of m -methylbenzimidazole N-acetic acid methyl - laurylamide prepared by reacting chloracetylchloride with methyllaurylamine and condensing the product with m -methylbenzimidazole; (II) hydrochloride of m -ethylbenzimidazole-N-acetic acid-laurylamide prepared by reacting laurylamine with chloracetyl chloride and the product with m -ethylbenzimidazole; (III) hydrochloride of m -methylbenzimidazole-N-octodecyl-thioethylether prepared by first treating ethylenechlorhydrin with sodium hydrosulphide, the product with octodecyl bromide and the resulting octadecylchlorethylthioether with thionylchloride; the product is condensed with m -methylbenzimidazole; (IV) hydrochloride of m  - phenyl - N - laurylbenzimidazole prepared by condensing m  - phenylbenzimidazole with dodecylchloride; (V) hydrochloride of m -oxymethyl-N-laurylbenzimidazole prepared by reacting m -oxymethylbenzimidazole with dodecylchloride; (VI) hydrochloride of m - methoxymethyl - N - laurylbenzimidazole prepared by reacting m -methoxymethylbenzimidazole with dodecyl chloride; (VII) sulphonic acid of m -thioethylether of N-laurylbenzimidazole prepared by reacting m -mercaptobenzimidazole with ethyl chloride, the product with dodecyl chloride, and finally sulphonating.  Specifications 403,977 and 419,010 are referred to.ALSO:Alkylated imidazoles are prepared by treating an imidazole containing the atomic grouping <FORM:0439261/III/1> wherein R represents an aromatic nucleus other than a benzimidazole or naphthimidazole substituted at the m -carbon atom by an aliphatic residue having at least three carbon atoms or by a hydroaromatic residue, with an alkylating agent containing at least 7 carbon atoms, and if desired the products are treated with a sulphonating agent or alkylating agent or with both such agents in either order.  The products are capillary active and applicable as auxiliary agents in emulsifying, dispersing, softening, washing, and wetting processes.