Patent GB-604351-A (GB)
Title: Manufacture of sulphuric acid esters
Filed: 1944-05-11
Abstract: Compounds obtained by condensing alkylene oxides (2 mols.) with aliphatic substances having the grouping -HN-C(=NH)-N = and at least 12 carbon atoms (1 mol.) are, after sulphonation employed as emulsifying agents and for dissolving lime soaps.  Substituted acylbiguanides, cyanguanidines and guanamines may thus be condensed with ethylene oxide, a -propylene oxide, isobutylene oxide, alkyleneoxide, glycide and epichlorhydrin. Stearoylcyanguanidine, stearylxylylguanamine, o -phenyl-o 1-stearoylbiguanide and coconut-oil acid hydroxyethylbiguanide are used in examples for preparing emulsifying agents.  Reference has been directed by the Comptroller to Specification 546,027.ALSO:A compound which contains at least once the atomic grouping -HN-C(=NH)-N< and an aliphatic residue having at least 12 carbon atoms is condensed with at least twice the amount (molecular proportions) of an alkylene oxide, and the resulting compound is treated with a sulphonating agent. Substituted acylbiguanides, cyanguanidines and guanamines may thus be condensed with ethylene oxide, a -propyleneoxide, isobutylene oxide, alkyl ethyleneoxide, glycide, and epichlorhydrine to give capillary active compounds.  In the examples: (1) stearoyl-cyanguanidine, prepared from stearic acid and dicyandiamide is reacted with sodium ethylate and glycide and the product is sulphonated with chlorsulphonic acid; (2) dicyanamide, coconut oil acid and ethanolamine are condensed together and the product is treated with glycide and then sulphonated with fuming sulphuric acid; (3) stearyl-xylylguanamine is condensed with glycide in the presence of sodium ethylate and the product is sulphonated as in (2); (4) o -phenyl-o 1-stearoyl-biguanide is treated with dimethylsulphate and the product condensed with glycide, which is then sulphonated as above; (5) coconut oil acid hydroxyethyl biguanide is condensed with ethylene oxide and the product is sulphonated.  The products may be used as wetting and emulsifying agents and for stripping vat dyestuffs.  Reference has been directed by the Comptroller to Specification 546,027.ALSO:A compound which contains at least once the atomic grouping-HN-C(=NH)-N<and an aliphatic residue having at least 12 carbon atoms is condensed with at least twice the amount of an alkylene oxide, and the resulting compound is treated with a sulphonating agent.  The products are used for stripping vat dyes p and as wetting agents.  Substituted acylbiguanides, cyanguanidines and guanamines may thus be condensed with ethylene oxide, a -propylene oxide, isobutylene oxide, alkylethylene oxide, glycide, and epichlorhydrin to give capillary active compounds.  In the examples, products obtained as follows are sulphonated.  (1) Stearoylcyanguanidine is reacted with sodium ethylate and glycide; (2) Dicyanamide, cocoanut oil acid and ethanolamine are condensed together and the product is treated with glycide; (3) Stearylxylylguanamine is condensed with glycide; (4) o -phenyl-o 1-stearoylbiguanide is treated with dimethylsulphate and the product condensed with glycide; (5) Cocoanut oil acid hydroxyethylbiguanide is condensed with ethylene oxide.  Reference has been directed by the Comptroller to Specification 546,027.