Patent GB-679463-A (GB)
Title: Improvements in lubricant improving agent and lubricant containing same
IPC: C10M159/12
Filed: 1947-05-07
Abstract: Products obtained by treating, with a phosphorus- and sulphur-containing reagent, a sulphurized ester of an unsaturated monocarboxylic acid and an organic compound containing one or two -OH or -SH groups, are employed as additives in lubricants (see Group III).  Unsaturated monocarboxylic acids which may be employed in preparing the esters are acrylic, crotonic, isocrotonic, methacrylic, methyl-2-buten-2-oic, heptenoic, octenoic, propiolic, decen-9-oic, undecen-9-oic, dodecen-9-oic, myristoleic, oleic, ricinoleic, petroselinic, vaccenic, erucic, selacholeic, stearolic, tariric, laurolenic, chaulmoogric, hydnocarpic, tetrahydrobenzoic, tetrahydrotoluic, methyl cyclohexylidene acetic, abietic, cyclohexyl propenoic, cinnamic, benzal lactic, phenyl butenoic, phenyl decenoic and phenyl oleic acids.  Alcohols from which the esters may be prepared are methyl, ethyl, amyl, heptyl, octyl, decyl, lauryl, cetyl, stearyl, oleyl, cyclopropyl, cyclohexyl, propyl cyclohexyl, butyl cyclohexyl, cyclohexyl cyclohexyl, cycloheptyl furfuryl and tetrahydrofurfuryl alcohols, also mixtures of cyclohexanol and its homologues, mixtures of homologues of cyclohexanol, decahydro - b  - naphthol, tetrahydro - a  - naphthol, tetrahydrophenol, borneol, isoborneol, 3-hydroxyl-p-menthone, cholesterol, terpineols, cyclobutyl carbinol, hydrogenated benzophenone, hydrogenated acetophenone, ethylene glycol, diethylene glycol, propandiols, tetramethylene glycol, hexandiols, octandiols, decandiols, hexahydro-hydroquinone and hexahydro-resorcinol. Specific esters which may be employed as starting materials are (i) one of the following oleates: methyl, ethyl, capryl, lauryl, tetradecyl, oleyl, stearyl, phenyl, capryl phenyl, lauryl phenyl, naphthyl or methyl naphthyl; or (ii) butyl ricinoleate, butyl palmitoleate, ethylene glycol di-oleate, hexamethylene glycol dioleate, soyabean oil or sperm oil.  The esters are sulphurized by treatment with sulphur or other sulphur-imparting reagent and then treated with phosphorus sulphide or other reagent containing phosphorus and sulphur. Suitable sulphur-imparting and phosphorus-and sulphur-containing reagents are listed.  The preparation of P4S3-treated sulphurized methyl oleate is given in detail.  Specifications 679,461, 679,462, 679,464, 679,465 and 679,466 are referred to.  The Specification as open to inspection under Sect. 91 gives lists of other acids and alcohols which may be used in preparing esters and also specifies further esters which may be sulphurized and phosphor-sulphurized. This subject-matter does not appear in the Specification as accepted.ALSO:A lubricating composition especially suitable as a gear lubricant comprises a major proportion of lubricating oil and from about 8 per cent to about 20 per cent of the product obtained by treating, with a phosphorus- and sulphur-containing re-agent, a sulphurized ester derived from an unsaturated monocarboxylic acid and an organic compond containing one or two -OH or -SH groups. The lubricating oil may be of mineral, animal, vegetable or synthetic origin.  The composition may also contain other ingredients such as pour point depressors, solubilizing agents, thickeners and viscosity improvers.  Unsaturated monocarboxylic acids which may be employed in preparing the esters are acrylic, crotonic, isocrotonic, methacrylic, methyl-2-buten-2-oic, heptenoic, octenoic, propiolic, decen-9- oic, undecen-9-oic, dodecen-9-oic, myristoleic, oleic, ricinoleic, petroselinic, vaccenic, erucic, selacholeic, stearolic, tariric, laurolenic, chaulmoogric, hydrocarpic, tetrahydrobenzoic, tetrahydrotoluic, methyl cyclohexylidene acetic, abietic, cyclohexyl propenoic cinnamic, benzal lactic, phenyl butenoic, phenyl decenoic and phenyl oleic acids.  Alcohols from which the esters may be prepared are methyl, ethyl, amyl, heptyl, octyl, decyl, lauryl, cetyl, stearyl, oleyl, cyclopropyl, cyclohexyl, propyl cyclohexyl, butyl cyclohexyl, cyclohexyl cyclohexyl, cycloheptyl furfuryl and tetrahydrofurfuryl alcohols, also mixtures of cyclohexanol and its homologues, mixtures of homologues of cyclohexanol, decahydro-b -naphthol, tetrahydro-a -naphthol, tetrahydro-phenol, borneol, isoborneol, 3-hydroxyl-p-mehane, chorlesterol, terpineols, cyclobutyl carbinol, hydrogenated benzophenone, hydrogenated acetophenone, ethylene glycol, diethyleneglycol, propandiols, tetramethylene glycol, hexandiols, octandiols, decandiols, hexahydro-hydroquinone and hexahydro-resorcinol. Specific esters which may be employed as starting material are (i) one of the following oleates:-methyl, ethyl, capryl, lauryl, tetradecyl, oleyl, stearyl, phenyl, capryl phenyl, lauryl phenyl, naphthyl or methyl naphthyl; or (ii) butyl ricinoleate, butyl palmitoleate, ethylene glycol di-oleate, hexamethylene glycol dioleate, soyabean oil or sperm oil.  The esters are sulphurized by treatment with sulphur or other sulphur-imparting reagent and then treated with phosphorus sulphide or other reagent containing phosphorus and sulphur.  Suitable sulphur-imparting and phosphorus- and sulphur-containing reagents are listed.  An example of a sutable additive is P4S3-treated sulphurized methyl oleate. Specifications 679,461, 679,462, 679,464, 679,465 and 679,466, and U.S.A.  Specification 2,042,880 are referred to.