# US 4,394,279 A · Antioxidant combinations of sulfur containing molybdenum complexes and aromatic amine compounds for lubricating oils > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,394,279 A - Document ID: US4394279A - Status: Granted - Kind: A - Application number: 06/290,914 - Filed: 1981-08-07 - Granted: 1983-07-19 - Earliest claimed: 1981-08-07 - Assignees: Chevron Research Company - Inventors: Louis deVries; John M. King - Web page: https://patentgrep.com/patent/US4394279A ## CPC - C10M 163/00: Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential - C10M 133/12: having amino groups bound to a carbon atom of a six-membered aromatic ring - C10M 133/14: containing hydroxy groups - C10M 135/28: containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring - C10M 2215/04: having amino groups bound to acyclic or cycloaliphatic carbon atoms - C10M 2215/06: having amino groups bound to carbon atoms of six-membered aromatic rings - C10M 2215/062: containing hydroxy groups bound to the aromatic ring - C10M 2215/064: Di- and triaryl amines - C10M 2215/065: Phenyl-Naphthyl amines - C10M 2215/066: Arylene diamines - C10M 2215/067: Polyaryl amine alkanes - C10M 2215/068: having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings - C10M 2215/08: Amides [having hydrocarbon substituents containing less than thirty carbon atoms] - C10M 2215/082: containing hydroxyl groups; Alkoxylated derivatives - C10M 2215/086: Imides [having hydrocarbon substituents containing less than thirty carbon atoms] - C10M 2215/26: Amines - C10M 2215/28: Amides; Imides - C10M 2217/00: Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions - C10M 2217/02: Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds - C10M 2217/04: Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds - C10M 2217/046: Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers - C10M 2217/06: Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound - C10M 2219/086: containing sulfur atoms bound to carbon atoms of six-membered aromatic rings - C10M 2223/065: containing sulfur - C10N 2010/12: Groups 6 or 16 - C10N 2050/10: semi-solid; greasy - C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33) - C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS ## Abstract An antioxidant additive combination for lubricating oils is prepared by combining (a) a sulfur containing molybdenum compound prepared by reacting an acidic molybdenum compound, a basic nitrogen compound, and carbon disulfide, with (b) an aromatic amine compound. ## Claims ### Claim 1 A lubricating oil additive comprising a combination of (a) an oil soluble sulfur containing molybdenum complex prepared by (1) reacting an acidic molybdenum compound and a basic nitrogen compound selected from the group consisting of a succinimide, carboxylic acid amide, Mannich base, phosphonamide, thiophosphonamide, phosphoramide, dispersant viscosity index improvers, or mixtures thereof to form a molybdenum complex wherein from 0.01 to 2 atoms of molybdenum are present per basic nitrogen atom, and (2) reacting said complex with carbon disulfide in an amount to provide 0.1 to 4 atoms of sulfur per atom of molybdenum, and (b) an oil soluble aromatic amine compound or mixtures thereof, wherein the aromatic amine compound of component (b) is present in an amount of from 0.02 to 10 parts by weight per part by weight of the sulfur containing molybdenum complex of component (a). ### Claim 2 (depends on 1) The oil additive of claim 1 wherein the aromatic amine of component (b) is selected from the group consisting of an N-aryl amine and an N,N'-arylene diamine. ### Claim 3 (depends on 2) The oil additive of claim 2, wherein the N-arylamine has the formula ##STR7## wherein R.sub.1 and R.sub.2 are the same or different and each is hydrogen, alkyl of 1 to 18 carbon atoms, aryl of 6 to 14 carbon atoms, alkaryl of 7 to 34 carbon atoms or aralkyl of 7 to 12 carbon atoms; R.sub.3 is aryl of 6 to 14 carbon atoms or alkaryl of 7 to 34 carbon atoms. ### Claim 4 (depends on 2) The oil additive of claim 2 wherein the N,N'-arylene diamine has the formula ##STR8## wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are the same or different and each is hydrogen, alkyl of 1 to 12 carbon atoms, aryl, aralkyl, or alkaryl having from 6 to 22 carbon atoms, and B is selected from the group consisting of arylene containing 6 to 14 carbon atoms and a group of the formula ##STR9## wherein X is a covalent bond, alkylene containing 1 to 8 carbon atoms, --O--, --CO--, --S--, or --SO.sub.2 --. ### Claim 5 (depends on 2) The additive of claim 2 wherein the N-arylamine is selected from the group consisting of N-phenyl-alphanaphthylamine, p,p'-dioctyldiphenylamine and diisobornyldiphenylamine. ### Claim 6 (depends on 1) The oil additive of claim 1 wherein the acidic molybdenum compound is molybdic acid, molybdenum trioxide, and ammonium molybdate. ### Claim 7 (depends on 1) The oil additive of claim 1 wherein the acidic molybdenum compound is molybdic acid, molybdenum trioxide, or ammonium molybdate, and said basic nitrogen compound is a succinimide, carboxylic acid amide, or Mannich base. ### Claim 8 (depends on 7) The oil additive of claim 7 wherein said basic nitrogen compound is a C.sub.24-350 hydrocarbyl succinimide, carboxylic acid amide, or a Mannich base prepared from a C.sub.9-200 alkylphenol, formaldehyde, and an amine. ### Claim 9 (depends on 8) The oil additive of claim 8 wherein said basic nitrogen compound is a polyisobutenyl succinimide prepared from polyisobutenyl succinic anhydride and tetraethylene pentaamine or triethylene tetraamine. ### Claim 10 (depends on 7) The oil additive of claim 7 wherein said basic nitrogen compound is a carboxylic acid amide prepared from one or more carboxylic acids of the formula R.sup.2 COOH, or a derivative thereof which upon reaction with an amine yields a carboxylic acid amide, wherein R.sup.2 is C.sub.12-350 alkyl or C.sub.12-350 alkenyl and a hydrocarbyl polyamine. ### Claim 11 (depends on 10) The oil additive of claim 10 wherein R.sup.2 is C.sub.12-20 alkyl or C.sub.12-20 alkenyl and the hydrocarbyl polyamine is tetraethylene pentaamine or triethylene tetraamine. ### Claim 12 (depends on 7) The oil additive of claim 7 wherein said basic nitrogen compound is a Mannich base prepared from dodecylphenol, formaldehyde, and methylamine. ### Claim 13 (depends on 8) The additive of claim 8 wherein said basic nitrogen compound is a Mannich base prepared from C.sub.80-100 alkylphenol, formaldehyde and triethylene tetraamine, or tetraethylene pentaamine, or mixtures thereof. ### Claim 14 (depends on 1) The oil additive of claim 1 comprising a combination of (a) an oil soluble sulfur containing molybdenum complex prepared by (1) reacting a C.sub.24-350 hydrocarbyl succinimide, and an acidic molybdenum compound selected from the group consisting of molybdic acid, molybdenum trioxide and ammonium molybdate, and (2) reacting said complex with carbon disulfide, and (b) an oil soluble aromatic amine compound selected from the group consisting of N-phenyl-alpha-naphthylamine, p,p'-dioctyldiphenylamine and diisobornyldiphenylamine. ### Claim 15 (depends on 14) The oil additive of claim 14 wherein the hydrocarbyl succinimide is a polyisobutenyl succinimide prepared from polyisobutenyl succinic anhydride and tetraethylene pentaamine or triethylene tetraamine. ### Claim 16 (depends on 1, 2, 3) A lubricating oil composition comprising an oil of lubricating viscosity and from 0.05 to 15 percent by weight of the additive of claims 1, 2 or 3. ### Claim 17 (depends on 1, 2, 3) A lubricating oil concentrate composition comprising an oil of lubricating viscosity and from 15 to 90 percent by weight of the product of claims 1, 2 or 3.