Patent GB-1016082-A (GB)
Title: Phosphorus containing surface active products
IPC: C07F9/08
Filed: 1963-05-16
Abstract: Phosphorus containing surface active agents are prepared by reacting an hydroxylic, nonionic surface active agent obtainable by reaction of at least one alkylene oxide with at least one organic compound having a reactive hydrogen atom, with a polyphosphoric acid having a P2O5 constant of 73 to 85% by weight, using 0.6 to 2.0 moles of the acid per each hydroxyl group in each mole of surface active agent. The preferred alkylene oxide is ethylene oxide, which may be reacted with alcohols, phenols, thiols, primary and secondary amines, and sulphonic and carboxylic acids and their amides, to give products containing 20 to 85% by weight of combined alkylene oxide. Particularly suitable non-ionic surfactants are the reaction products of ethylene oxide, and polyglycols of molecular weight about 300 to 3000, prepared by polymerizing 1:2 alkylene oxides, which may be substituted, in the presence of alkali, at at elevated temperature and pressure, to give a water-insoluble polyglycol, which is then reacted with ethylene oxide to give the required nonionic surfactant. The surfactants for phosphorylation should have a molecular weight of about 1200 to 15,000, preferably about 2000 to 10,000.  The reaction is suitably performed by addition of the phosphoric acid to the surfactant at about ambient temperature, and then heating to 80 DEG to 100 DEG  C. 1 to 1.3 moles of the acid may be employed for each hydroxy-group in each mole of surfactant but less than 1 mole is preferred for lower molecular weight surfactants, and up to 2.0 moles for those of high molecular weight.  Colour preventing agents, such as hydrazine hydrate or H2O2, may be added before the reaction. Examples describe the preparation of phosphorylated ethylene oxide adducts of I p-t-octyl phenol; II a C11-C14 t-alkyl primary amine; III a mixture of cetyl and stearyl alcohols.ALSO:Phosphorus-containing surface-active agents are prepared by reacting a hydroxylic, non-ionic surface-active agent, obtainable by reaction of at least one alkylene oxide with at least one organic compound having a reactive hydrogen atom, with a polyphosphoric acid having a P2O5 content of 73 to 85% by weight, using 0.6 to 2 moles of the acid for each hydroxyl group in each mole of surface-active agent.  The preferred alkylene oxide is ethylene oxide, which may be reacted with phenols, alcohols, thiols, amines, or sulphonic or carboxylic acids or their amides.  The reaction with polyphosphoric acid is suitably performed by adding the acid to the surfactant at about ambient temperature, and heating to 80 DEG  to 100 DEG  C. Colour-preventing agents, e.g. hydrazine hydrate or H2O2, may be added.  Particularly suitable non-ionic surfactants are the reaction products of ethylene oxide and polyglycols of molecular weight of about 300 to 3000, prepared by polymerizing 1.2-alkylene oxides, which may be substituted, in the presence of alkali at elevated temperature and pressure; suitable alkylene oxides are: butylene oxide, arylene oxide, styrene oxide, cyclohexene oxide, cyclo-octene oxide and propylene oxide.  Examples describe the preparation of phosphorylated ethylene oxide adducts of: (I) p-t-octylphenol; (II) a C11-C14 t-alkyl primary amine; and (III) a mixture of cetyl and stearyl alcohols.  The compounds are useful as surface-active agents, anti-static agents, emulsifiers, and hydrotropic agents for stabilizing non-ionic surfactants.