Patent GB-516879-A (GB)
Abstract: 516,879. Wetting &c. agents. DEUTSCHE HYDRIERWERKE AKT.-GES. July 11, 1938, No. 20529. Convention date, July 10, 1937.. [Classes 2 (iii) and 15 (ii)] Capillary active agents are made by'condensing compounds of the general formulaR-Ar- OH, or metal compounds thereof (R =an aliphatic residue containing at least three carbon atoms, and Ar=a benzene or substituted benzene residue) with aliphatic halogenoketones containing at least one exchangeable hydrogen atom, reducing the ketone group of the condensation product, preferably by catalytic hydrogenation, to a secondary alcohol group, and converting the latter, by sulphonation or treatment with alkylene oxides, into a watersolubilizing group. The compounds of the general formula R-Ar-OH are made by condensation of primary, secondary or tertiary alcohols, or mixtures thereof, or the corresponding olefines, with phenols. As starting materials for the preparation of these compounds may be used aliphatic alcohols obtained by reduction of fats or waxes, also pentylmethylcarbinol, #- ethylbutyl alcohol, #-ethylhexyl alcohol, #-butyl octyl alcohol, methylisobutylcarbinol, alcoholic and olefinic products of wood condensation, etc. The compounds of the general formula may also be obtained by esterifying carboxylic acids with aromatic hydroxy compounds, converting the esters into the corresponding oxyaryl ketones, and if desired converting the ketone group into a methylene group by reduction. The aliphatic halogehoketones may be made by simple halogenation of the ketones ; specified halogenoketones are chloracetone, bromacetone, brommethylethylketone. The products may be used as wetting, washing, cleansing, emulsifying and dispersing agents. In an example, the sodium compound of sec.-octyl-o-cresol (made from 1:2-octene and o-cresol) is condensed with chloracetone, the sec-octyl-cresoxyacetone obtained is hydrogenated in the presence of a copper catalyst, and the resulting alcohol is sulphonated with chlorsulphonic acid, or is converted into a water-soluble compound by heating with caustic soda and ethylene oxide under pressure. Instead of sec-octyl-o-cresol, 1:4-(##gammagamma-tetramethyl)-n-butyl phenol, or the condensation product from o-cresol and a synthetic hydrocarbon fraction obtained from carbon monoxide and hydrogen may be used. The Specification as open to inspection under Sect. 91 comprises also the use of starting materials of the general formula in which Ar represents any aromatic residue, the residues of naphthalene, phenanthrene, anthracene, diphenyl, diphenylmethane, ,diphenylethane, and phenylnaphthylmethane being specified. The symbol R also includes cycloaliphatic and fatty aromatic residues, e.g. cyclohexyl, tetrahydro- and decahydro-naphthyl, benzyl, etc. The residues represented by R may. also contain other atoms or atom groups, e.g. halogen, oxygen, sulphur or nitrogen. Naphthenic and resin alcohols are also specified as parent materials for the preparation of compounds of the general formula. Other solubilizing groups, e.g., phosphoric ester and thiosulphuric ester groups may also be introduced into the secondary alcohols. This subject-matter does not appear in the Specification as accepted.