Patent GB-976974-A (GB)
Title: Novel phosphine oxides having utility as detergents and detergent supplements
IPC: C07F9/53
Filed: 1961-07-31
Abstract: The invention comprises phosphine oxides of the general formula: <FORM:0976974/C1/1> wherein R is a C10-C16 alkyl radical or an alkylaryl radical in which the alkyl chain has from 8 to 16 carbon atoms and R1 and R2 each represent a C1-C4 alkyl radical or form jointly with the phosphorus atom a cycloaliphatic type phosphorus-containing ring having 4 or 5 carbon atoms. They may be obtained by oxidising the corresponding phosphines with hydrogen peroxide or by heating a quaternary phosphonium hydroxide of the general formula (R)(R1)(R2)(R3)P.OH wherein R, R1 and R2 are as defined above and R3 is phenyl or benzyl. Examples are given for the production of phosphine oxides of the above general formula in which R1 and R2 are each methyl and R is dodecyl or dodecylphenyl, R1 and R2 are each ethyl and R is dodecyl and in which R is dodecyl and R1 and R2 taken together are cyclotetramethylene and cyclopentamethylene radicals respectively. The products have good detergent properties and are useful in stabilizing foams or suds produced from solutions of other known detergents (see Division C5). They also have the property of dispersing water-insoluble soaps produced by dissolving water-soluble soaps in hard water.  The quaternary phosphonium hydroxides may be obtained by heating an aqueous solution of the corresponding phosphonium bromides.  Dimethyldodecylphenyl phosphonium bromide may be obtained by reacting benzene, AlCl3, PCl3 and POCl3 to form C6H5-PCl2 and reacting the latter with MgCH3I to form C6H5(CH3)2P which is then reacted with dodecyl bromide at atmospheric pressure in an atmosphere of carbon dioxide to form the phosphonium bromide. Other phosphonium bromides may be obtained by reacting diethylphenylphosphine, phenylcyclotetramethylene phosphine and phenyl cyclopentamethylene phosphine respectively with dodecyl bromide in an atmosphere of carbon dioxide. Dodecylphenyldichlorophosphine is obtained by reacting n-dodecylbenzene with PCl3, AlCl3 and POCl3 and is converted to dodecylphenyldimethylphosphin by reaction with MgCH3I.ALSO:Phosphine oxides of the general formula <FORM:0976974/C4-C5/1> wherein R is a C10-C16 radical or an alkylaryl radical in which the alkyl chain has from 8 to 16 carbon atoms and R1 and R2 each represent a C1-C4 alkyl radical or form jointly with the phosphorus atom a cycloaliphatic type phosphorus-containing ring (see Division C2) are useful as detergents or detergent supplements and for stabilizing foams or suds formed by agitation of other detergents.  They also have the property of dispersing water-insoluble soaps e.g. calcium or magnesium soaps produced by dissolving water-soluble soaps in hard water.  Specified detergent compositions are mixtures of dimethyldodecyl phosphine oxides with (a) tetrapotassium pyrophosphate, (b) sodium dodecyl sulphate, and (c) an alkylaryl sulphonate and tallow sulphate.  An example is also given which 3.5 parts by weight of various phosphine oxides of the above general formula are added as suds stabilizers to a detergent composition comprising 96.5 parts by weight of a mixture of sodium tetrapropylene benzene sulphonate, sodium toluene sulphonate, tetrasodium pyrophosphate, pentasodium tripolyphosphate, sodium silicate, sodium carboxy methyl cellulose, water and sodium sulphate.ALSO:Phosphine oxides of the general formula: <FORM:0976974/B1-B2/1> in which R is a C10-C16 alkyl radical or an alkylaryl radical in which the alkyl chain has from 8 to 16 carbon atoms and R1 and R2 are each a C1-C4 alkyl radical or form jointly with the phosphorus atom a cycloaliphatic type phosphorus-containing ring having 4 or 5 carbon atoms (see Division C2) are used for dispersing water-insoluble soaps, e.g. calcium or magnesium soaps, formed by the solution of water-soluble soaps in hard water.