Patent GB-377258-A (GB)
Title: Manufacture of products useful as wetting agents, dispersing agents, emulsifying agents and washing agents
Filed: 1931-04-15
Abstract: Ethereal products, stated to be dispersing, and emulsifying agents, are obtained by condensing (a) an aliphatic or aliphatic-aromatic compound containing at least four carbon atoms and a hydroxyl but no carboxyl group, or a derivative thereof, with an aliphatic or aliphatic-aromatic sulphonic acid containing a hydroxyl group, which in the case of the aliphatic-aromatic sulphonic acids is in the aliphatic residue, but no carboxylic group or a derivative thereof, (b) an alkali compound of an aliphatic or aliphatic-aromatic hydroxy compound containing at least four carbon atoms but no carboxyl group or a derivative thereof, with an aliphatic, hydroaromatic or aliphatic-aromatic sulphonic acid containing halogen which in the case of the aliphatic-aromatic sulphonic acids is in the aliphatic residue, but no carboxylic group or a derivative thereof or (c) an aliphatic compound containing at least six carbon atoms and a halogen but no carboxyl group or a derivative thereof, with a salt of an aliphatic, hydroaromatic or aliphatic-aromatic sulphonic acid containing a hydroxyl group, which in the case of the aliphatic-aromatic sulphonic acids is in the aliphatic residue, no carboxyl group or a derivative thereof.  Gaseous hydrochloric acid may be used to facilitate the production of the ethers by the first method, and ethionic acid or carbylsulphate, which liberate sulphuric acid in the course of the reaction may be used in preference to hydroxyethanesulphonic acid.  Similarly, homologues of ethionic acid, e.g. the compound prepared from butyalcohol or butylene and sulphur trioxide in the presence of liquid sulphur dioxide may be employed. In examples: (1) ethionic acid is condensed with stearyl alcohol, cotton, Japanese wax and with spermaceti: the product from Japanese wax may be used in the preparation of paraffin emulsions; (2) isethionic acid is condensed with the mixture of alcohols obtained by the hydrogenation of coco nut oil, and with n-butyl alcohol; (3) the sodium compound produced by treating a solution of sodium hydroxyethanesulphonate in xylene with sodium is condensed with stearyl chloride: (4) carbylsulphate is condensed with beeswax. The condensation of hydroxybutanesulphonic acid with the mixture of alcohols obtained by the hydrogenation of coco nut oil is referred to.  Products are also obtained by condensing sodium hexylalcoholate with sodium-1-chlorcyclohexane-2-sulphonate, sodium benzylchloride-sulphonate with the sodium compounds of the mixture of alcohols obtained from coco nut oil, and hexylchloride with the sodium compound of sodium-1-cyclohexanol-2-sulphonate. The following compounds containing one or more hydroxy groups are mentioned: cetyl and olein alcohols, sterols, e.g. phytosterol, mixtures containing sterine, e.g. wool wax, starch, cellulose, polyvinyl-alcohol, polyglycerine and the partial saponification products of polyvinyl acetate, and the following derivatives of aliphatic hydroxy compounds: waxes, such as carnauba, montan, and fossil waxes and the wax-like compounds obtained by the oxidation of paraffin and by the esterification of aliphatic or hydroaromatic carboxylic acids containing at least four carbon atoms with aliphatic alcohols containing at least four carbon atoms.  For the condensation of the aliphatic compounds containing at least six carbon atoms and at least one halogen atom, with aliphatic, hydroaromatic or aliphatic-aromatic hydroxysulphonic acids the followng compounds may be used: stearyldichloride and chlorinated paraffins, and 1 : 3-hydroxypropanesulphonic acid, 1 : 2-cyclohexanolsulphonic acid, 1 : 2 : 3-methylcyclohexanolsulphonic acid and p-benzylalcoholsulphonic acid.ALSO:Ethereal products, stated to be wetting, dispersing, washing, and emulsifying agents, are obtained by condensing (a) an aliphatic or aliphatic-aromatic compound containing at least four p carbon atoms and a hydroxyl but no carboxyl group, or a derivative thereof, with an aliphatic or aliphatic-aromatic sulphonic acid containing a hydroxyl group, which in the case of the aliphatic-aromatic sulphonic acids is in the aliphatic residue, but no carboxylic group or a derivative thereof, (b) an alkali compound of an aliphatic or aliphatic-aromatic hydroxy compound containing at least four carbon atoms but no carboxyl group or a derivative thereof, with an aliphatic, hydroaromatic or aliphatic-aromatic sulphonic acid containing halogen, which in the case of the aliphatic-aromatic sulphonic acids is in the aliphatic residue, but no carboxylic group or a derivative thereof or (c) an aliphatic compound containing at least six carbon atoms and a halogen but no carboxyl group or a derivative thereof, with a salt of an alphatic, hydroaromatic or aliphaticaromatic sulphonic acid containing a hydroxyl group, which in the case of the aliphatic-aromatic sulphonic acid is in the aliphatic residue, but no carboxyl group or a derivative thereof.  Gaseous hydrochloric acid may be used to facilitate the production of the ethers by the first method, and ethionic acid or carbyl sulphate, which liberate sulphuric acid in the course of the reaction may be used in preference to hydroxyethanesulphonic acid.  Similarly, homologues of ethionic acid, e.g. the compound prepared from butylalcohol or butylene and sulphur trioxide in the presence of liquid sulphur dioxide may be employed. The products may be used in mercerizing, carbonizing, and other processes in the textile industry.  In examples (1) ethionic acid is condensed with stearyl alcohol, cotton, Japan wax, and with spermaceti; (2) isethionic acid is condensed with the mixture of alcohols obtained by the hydrogenation of coconut oil, and with n-butyl alcohol; (3) the sodium compound produced by treating a solution of sodium hydroxyethanesulphonate in xylene with sodium is condensed with stearyl chloride; (4) carbylsulphate is condensed with beeswax. The condensation of hydroxybutanesulphonic acid with the mixture of alcohols obtained by the hydrogenation of coconut oil is referred to.  Products are also obtained by condensing sodium hexylalcoholate with sodium-1-chlorcyclohexane-2-sulphonate, (obtained from phosphorus pentachloride and sodium 1-cyclohexanol-2-sulphonate), sodium benzylchloride-sulphonate with the sodium compounds of the mixture of alcohols obtained from coconut oil, and hexylchloride with the sodium compound of sodium 1-cyclohexanol-2-sulphonate.  The following compounds containing one or more hydroxy groups are mentioned : cetyl and olein alcohols, sterols, e.g. phytosterol, mixtures containing stearine, e.g. wool wax, starch, cellulose, polyvinylalcohol, polyglycerine and the partial saponification products of polyvinyl acetate, and the following derivatives of aliphatic hydroxy compounds : waxes, such as carnauba, montan, and fossil waxes and the wax-like compounds obtained by the oxidation of paraffin and by the esterification of aliphatic or hydroaromatic carboxylic acids containing at least four carbon atoms with aliphatic alcohols containing at least four carbon atoms.  For the condensation of the aliphatic compounds containing at least six carbon atoms and at least one halogen atom, with aliphatic, hydroaromatic or aliphatic-aromatic hydroxy sulphonic acids the following compounds may be used : stearyldichloride and chlorinated paraffins, and 1 : 3-hydroxypropanesulphonic acid 1 : 2-cyclohexanolsulphonic acid, 1 : 2 : 3-methylcyclohexanolsulphonic acid and p-benzyl-alcoholsulphonic acid.  The latter may be prepared by heating p-brombenzylalcohol with sodium sulphite in an autoclave.