Patent GB-1042208-A (GB)
Title: Carbamoyl and thiocarbamoyl phosphorus compounds, the preparation thereof and lubricating compositions containing them
IPC: C07F9/40
Filed: 1964-10-13
Abstract: A lubricant composition comprises a major proportion of a hydrocarbon lubricant and a minor proportion of an oil-soluble carbamoyl or thio-carbamoyl phosphorus compound of the formula Y-C(X)-NH-R wherein Y represents [R1(O)n]2P-or [R1(O)n]2P(X)-, n being 0 or 1, each X independently represents O or S, each R1 independently represents hydrocarbon group or a substituted hydrocarbon group or the two groups R1 form together with the P atom a saturated or unsaturated, unsubstituted or alkyl-substituted heterocyclic 5- or 6-membered ring and R has the same significance as the individual R1 group or is an acyl group (see Division C2). The oil may be derived from a highly paraffinic crude oil or a highly aromatic crude oil containing paraffinic hydrocarbons which is then refined by distillation and solvent extraction.  The hydrocarbon oils may be mixtures of various mineral oil distillates and of bright stocks. Mixtures of mineral oils and fatty oils, such as castor oil and lard oil, and/or synthetic lubricants such as polymerized olefins may be used. The phosphorus compounds may also be incorporated in greases.  Minor proportions of phenolic anti-oxidants, such as alkyl phenols, aryl amines or dialkyl sulphides may be incorporated. Other additives are organic phosphites, phosphates, phosphonates or the thio derivatives thereof, P2S5-terpene reaction products or alkali metal salts thereof.  The lubricating compositions may also contain minor amounts of other conventional additives, such as silicone anti-foaming agents, polyacrylate esters as viscosity index improvers and oiliness-improvers.ALSO:Compounds of the formula Y-C(X)-NH-R where Y represents an [R1(O)n]2P- or [R1(O)n]2 P(X)-group, in which n is 0 or 1, each X independently represents 0 or 5, each R1 independently represents a hydrocarbon or a substituted hydrocarbon group or the two groups R1 form together with the P atom a saturated or unsaturated, unsubstituted or alkyl-substituted heterocyclic 5- or 6-membered ring and R has the same significance as the individual R1 group or is an acyl group are obtained by reacting an isocyanate or thioisocyanate of the formula X = C = N-R with a compound HY. The reaction is preferably carried out in an organic solvent at temperatures below 100 DEG  C. in the absence of oxygen.  The invention also comprises compounds in which R is an acyl group and X and Y are as above, and compounds of the formula (R1)2P(S)-C(X)-NH-R where R, R1 and X are as defined above with respect to the general formula.  The phosphine sulphides are preferably prepared by first reacting the isocyanate or thioisocyanate of the above formula with a phosphine of the formula (R1)2PH.  The resulting carbamoyl or thiocarbamoyl phosphine is then reacted in a second stage with sulphur or a sulphur-containing compound such as thiourea or an episulphide. The R1 groups may be substituted by amino groups or halogen atoms.  Specified R1 groups are ethyl, butyl, isooctyl, phenyl, tolyl, xylyl, octyl phenyl, naphthyl, benzyl, p-dimethyl aminophenyl and p-trifluoromethyl phenyl. Specified acyl groups representing R are benzoyl, acetyl, chloro- and trichloro-acetyl, butyryl, isooctanoyl, lauroyl or stearoyl groups. The products are useful as lubricant additives (see Division C5).