Patent GB-517339-A (GB)
Title: Improvements in or relating to the production of capillary active substances
IPC: D06M13/463
Filed: 1938-07-23
Abstract: 517,339. Wetting &c. agents. DEUTSCHE HYDRIERWERKE AKT.-GES. July 23, 1938, No. 21956. Convention date, July 23, 1937. [Classes 2 (iii) and 15 (ii)] Wetting, cleansing, emulsifying or dispersing agents are made by reacting organic hydroxyl compounds of the general formula R-Ar-OH, where R represents at least one aliphatic residue containing at least three carbon atoms, and Ar is a residue of the benzene or naphthalene series, or metal compounds thereof, with functional derivatives of nitro-, amino-, or acylamino-aryl sulphonic acids of the benzene or naphthalene series, and treating the products, after reduction of any nitro groups or saponification of any acylamino groups, with agents for introducing water-solubilizing groups at the amino groups, by the methods set out below. R may represent propyl, amyl, octyl, dodecyl, hexadecyl, isopropyl, isohexyl, isodecyl, isotetradecyl, iso-octadecyl, tert. butyl, tert. amyl, di-isobutyl, tri-isobutyl, or tert. ' ethylhexyl groups, or may be a residue derived from the higher aliphatic alcohols obtainable by reduction of fats or waxes, or from alcoholic or olefinic products of wood carbonization etc. The parent hydroxyl compounds may be obtained by condensation of primary, secondary or tertiary aliphatic alcohols or the corresponding olefines, with phenols or naphthols, in the presence of catalysts, e.g., inorganic acids, metal halides, boron fluoride or its addition products. They may also be obtained by esterifying carboxylic acids or derivatives thereof with phenols or naphthols, converting the esters to hydroxyaryl ketones, and if desired, converting the ketone group into a methylene group by reduction. The functional derivatives of nitroaryl sulphonic acids are the anhydrides, esters, hydrides and halides, particularly the latter, the following being specified: 3-nitrobenzene-1-sulphochloride, 5- nitro-2-chlorbenzene-1-sulphochloride, 3 : 5 - dinitrobenzene - 1 - sulphochloride, 2 - nitrotoluene - 4 - sulphochloride, 4 - nitrotoluene - 2- sulphochloride, 5 - nitronaphthalene - 1 - sulphochloride, and 4 - nitronaphthalene - 2 : 5 - disulphochloride. Water solubilizing groups are introduced by reaction with several moles of alkylene oxide, e.g., ethylene oxide or glycide; by reaction with halogen-alkyl sulphuric esters, halogen-alkyl sulphonic or carboxylic acids and halogenalkylaryl sulphonic acids, e.g., 2-chlorethyl sulphuric acid ester, 1-chlorhexyl-6-sulphuric acid ester, mono- or disulphuric acid esters of the chlorhydrins of polyhydric alcohols, e.g., of glycerol, 2-chlorethane sulphonic acid, or benzyl-chloride-4- sulphonic acid ; by forming acyl derivatives with halogen-alkyl carboxylic acids and subsequently replacing the halogen atom by watersolubilizing groups, e.g., -SO3H, -S-SO3M, quaternary ammonium or betine groups, or reacting the compounds directly with betaine ; by acylation with polybasic carboxylic or sulphocarboxylic acids, e.g., sulphoacetic and sulphophthalic acids ; finally, the amino group may be converted by exhaustive alkylation into a water-solubilising quaternary ammonium group. In examples (1) the sodium compound of sec.-octyl-o-cresol (made by condensing 1 : 2-octene with o-cresol)- is condensed with 3-nitro-benzene-1-sulphochloride by heating in xylene, reduced with zinc dust in glacial acetic acid, and treated with sodium #-bromethyl sulphate in alcohol, and (2) the sodium compound of a mixture of iso-alkyl cresols, made by condensation of technical cresol with a synthetic hydrocarbon fraction from carbon monoxide and hydrogen, is condensed with 5- nitronaphthalene - 1 - sulphochloride, reduced, and treated with ethylene oxide under pressure. The Specification as open to inspection under Sect. 91 comprises also the treatment of hydroxyl compounds of the above general formula in which R represents cyclo-aliphatic or hydroaromatic residues, and in which Ar represents any aromatic residue, including residues of phenanthrene, anthracene, diphenyl, diphenylethane, diphenylmethane and phenylnaphthylmethane, which may be substituted by hydrocarbon residues, either directly or through an O or S atom, or may contain substituents such as halogen atoms or hydroxyl groups. The nitroaryl sulphonic acid derivatives may also contain any aromatic residue, including phenanthrene, anthracene, diphenyl or diphenylmethane, which may be substituted ; 4-nitrodiphenyl-4-sulphochloride is specified. This subject-matter does not appear in the Specification as accepted.