Patent GB-744845-A (GB)
Title: New and improved ester-salts of phosphoric acid
Inventor: ZENFTMAN HENRYK
IPC: C09K23/00
Filed: 1953-04-24
Abstract: The invention comprises amine salts of an orthophosphoric acid wherein one hydroxyl hydrogen atom is replaced by an alkyl group containing not more than three carbon atoms and one other hydroxyl hydrogen atom is replaced by the p-tertiary-octyl-phenyl group of a p-tertiary octyl-phenol derived from isobutylene and phenol, the salt-forming amine having the formula NR2R3R4 where R2 and R3 are each hydrogen, or an alkyl or hydroxy-alkyl group having not more than two carbon atoms, and R4 is an alkyl or cycloaliphatic group having not more than six carbon atoms.  The amine salts are produced by reacting in a fluid state a p-tertiary-octyl-phenyl alkyl hydrogen phosphate wherein the p-tertiary-octyl-phenyl group is that corresponding to a p-tertiary-octyl-phenol prepared from isobutylene and phenol and the alkyl group is one containing not more than three carbon atoms with the amine having the hereinbefore specified constitution.  The amine radical may be derived from monoethanol amine, mono-butylamine, mono-cyclohexylamine, monoethanolamine, trimethylamine, diethylmonoethanolamine or triethanolamine.  The reaction may be carried out in an aqueous reaction medium or the amine may be added to the molten alkyl p-tertiary-octylphenyl hydrogen phosphate.  In examples cyclohexylammonium methyl p-tertiary-octylphenyl phosphate is obtained by reacting methyl p-tertiary-octyl-phenyl hydrogen phosphate with cyclohexylamine in lignoin (1); butylammonium (2); diethylmonoethanol ammonium (3); and methylammonium (4).  Methyl p-tertiary octyl-phenyl phosphates are similarly prepared using butylamine, diethyl monoethanolamine and gaseous monomethylamine instead of cyclohexylamine and the cyclohexyl ammonium salt is obtained by reacting methyl p-tertiary-octyl-phenyl-hydrogen phosphate and cyclohexylamine in water.  The products of the invention are employed as emulsifying agents, e.g. in the preparation of emulsions of mineral oil in water (see Group III) and in preventing corrosion of ferrous metals by water (see Group XVIII).  Reference has been directed by the Comptroller to Specification 699,080, [Group III].ALSO:In the preparation of emulsions of mineral oil in water for use as lubricants, e.g. as cutting oils or in the drawing or cold working of copper, amine salts of an orthophosphoric acid wherein one hydroxyl hydrogen atom is replaced by an alkyl group containing not more than three carbon atoms and one other hydroxyl hydrogen atom is replaced by the p-tertiary-octyl-phenyl group of a p-tertiary-octyl phenol derived from isobutylene and phenol the salt-forming amine having the formula NR2R3R4 where R2 and R3 are each hydrogen, or an alkyl or hydroxy-alkyl group having not more than two carbon atoms, and R4 is an alkyl or cycloaliphatic group having not more than six carbon atoms (see Group IV(b)) are employed as emulsifying agents.  A self-emulsifying composition comprises a mineral oil and in solution therein a cyclohexylammonium methyl p-tertiaryoctyl phenyl phosphate of the kind defined above.  In examples: An emulsion is formed by dissolving cyclohexylammonium methyl p-tertiary-octyl-phenyl phosphate in mineral oil and stirring the solution with water to obtain a cutting oil (1), a mineral oil in water emulsion is similarly obtained using butyl ammonium methyl p-tertiary-octyl-phenyl phosphate as emulsifying agent (2); cyclohexylammonium methyl p-tertiary-octyl-phenyl phosphate is mixed with cresol, amyl alcohol, oleyl sulphate and water and this solution is dissolved in mineral oil to obtain an oil which emulsifies with water (5).  The ester-salts also inhibit corrosion of ferrous metals by aqueous mineral oil emulsions (see Group XVIII).  Reference has been directed by the Comptroller to Specification 699,080.