US3660290A - Lubricant compositions - Google Patents

Lubricant compositions Download PDF

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Publication number
US3660290A
US3660290A US860035A US3660290DA US3660290A US 3660290 A US3660290 A US 3660290A US 860035 A US860035 A US 860035A US 3660290D A US3660290D A US 3660290DA US 3660290 A US3660290 A US 3660290A
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Prior art keywords
alkylphenyl
naphthylamine
alkyl
naphthylamines
phenyl
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US860035A
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English (en)
Inventor
Roland T Schlobohm
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Shell USA Inc
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Shell Oil Co
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/284—Esters of aromatic monocarboxylic acids
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    • C10M2207/285—Esters of aromatic polycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/064—Di- and triaryl amines
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
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    • C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
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    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/222—Triazines
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/226—Morpholines
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    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/26—Amines
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    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
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    • C10M2219/108—Phenothiazine
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

Definitions

  • This invention relates to a novel class of phenyl-2- befo re described alkylphenyl-alkylnaphthylammes with naphtllylamme denvatlves and to 1ubnant comPosltlons 20 phenyl-2-naphthylamines having alkyl substituents exclucontainlng such compounds.
  • alkyl groups may contain from 2 to 16 carbon lubricating 0115 has led to the development of numerous atoms, but Preferably having 4 to 12 carbon atoms and oxidation inhi it for eXample Phenothiazine, phenyl a tertiary alkyl structure.
  • Certain alkylated phenyl-Z-naphthylamines stituted in the 4 position of the phenyl ring have been have also been Proposed these alkylated compounds found to be particularly elfective when used in combinaing Characterized by having one or more alkyl Substitu' tion with the present additives. Examples of such coments introduced into the phenyl nucleus. With the conpounds include:
  • naphthylamines are efiective in improving the oxidation resistance, cleanliness and bearing performance properties 11 D y aph y mnine of lubricatin oils.
  • the eifectiveness of these com unds g p0 and the like.
  • the alkylphenyl-alkylnaphthylamines of the invention are generally prepared by reacting phenyl-2-naphthyl R1 amine with a 1- or 2-alkene having from 2 to 16, or more, carbon atoms at an elevated temperature in the presence of a Friedel-Crafts catalyst, e.g., aluminum chloride.
  • a Friedel-Crafts catalyst e.g., aluminum chloride.
  • the H reaction conditions largely govern the nature of the alkylated products formed. Conditions conducive to naphthyl wherein R and R are alkyl groups having from 2 to 80, ring substitution are described in Example 1. Employing preferably from 2 to 16, carbon atoms.
  • the alkylphenyl-alkylnaphthylamines of the invention boxylic acids having from 3 to 20, especially 4 to 12 carcan be employed in lubricant compositions either singubon atoms.
  • the ester base may comprise a simple ester larly, in mixtures, or in combination with alkylphenyl-2- (reaction product of a monohydroxyalcohol and a mononaphthylamines which have alkyl substituents exclusively carboxylic acid), a polyester (reaction productof an alon the phenyl nucleus.
  • cohol and an acid one of which has more than one functional group
  • a complex ester reaction product of a polyfunctional acid with more than one alcohol, or of a polyfunctional alcohol with more than one acid.
  • excellent synthetic lubricant may be formulated from mixtures of esters, such as major proportions of complex esters and minor amounts of diesters.
  • ester base oils examples include ethyl palmitate, ethyl laurate, butyl stearate, di(2-ethylhexyl)sebacate, di (2-ethylhexyl)azelate, ethylene glycol diluarate, di-(Z-ethylhexyl)phthalate, di-(3-methylbutyl) adipate, di-(Z-ethylpropyl)azelate, diisopropyloxylate, dicyclohexyl sebacate, glycerol tri-n-heptanoate, di(undecyl)azelate, and tetraethylene glycol di-(2-ethy1 hexanoate), and mixtures thereof.
  • An especially preferred mixture of esters consists of about 50 80% bis(2,2,4 trimethylpentyl)azelate and 20 to 50% 1,1,1'trimethyl propane triheptanoate.
  • esters for use as base stocks in the present invention are esters of monocarboxylic acids having 3 to 12 carbons and polyalcohols such as pentaerythritol, dipentaerythritol, trimethylolpropane and mixtures thereof.
  • esters examples include pentaerythrityl tetrabutyrate, pentaerythrityl tetravalerate, pentaerythrityl tetracaproate, pentaerythrityl dibutyratedicaproate, pentaerythrityl butyratecaproate divalerate, pentaerythrityl butyrate trivaler-ate, .pentaerythrityl butyrate tricaproate, pentaerythrityl tributyratecaproate, mixed C -C saturated fatty acid esters of pentaerythritol, dipentaerythrityl hexavalerate, dipentaerythrityl hexacaproate, dipentaerythrityl hexaheptoate, dipentaerythirtyl hexacaprylate, dipentaerythrityl tributyratetricaproate, dipentaerythrity
  • the additives of this invention may also be incorporated in mineral lubricating oils.
  • the mineral lubricating oil can be obtained from parafiinic, naphthenic, asphaltic or mixed base crudes and/or mixtures thereof, for example neutral oils having viscosities of from 100 to 6500 SSU at 100 F.
  • the alkylpienyl-alkylnaphthylamines of the invention can be incorporated into lubricant compositions in amounts of from 0.01 to 10% by weight of the total composition. Concentrations of 0.5 to 5.0% by weight are generally sufiicient to impart the desired properties to lubricating oils. These concentration ranges are also ap plicable to mixtures of alkylphenyl-alkylnaphthylamines with alkylphenyl-naphthylamines as hereinbefore described.
  • a preferred embodiment of the invention therefore is an ester base lubricating composition containing a total of from 0.01 to 10% by weight of a mixture of one or more 4-a1kylphenyl-1-alkyl-2-naphthylamines with one or more 4-alkylphenyl-Z-naphthylamines, the ratio of the former compounds to the latter being from 1:2 to 10:1.
  • additives recognized in the art to perform a particular function or functions can also be incorporated into the present compositions. These include viscosity improvers, e.g., methacrylate polymers and copolymers, additional antioxidants, corrosion inhibitors, antifoam agents, detergents and the like.
  • EXAMPLE I 5.36 g. (0.04 mole) of aluminum trichloride was added to 87.6 g. (0.4 mole) of phenyl-2-naphthylamine and heated to 120 C. While stirring and under a nitrogen atmosphere, 89.6 g. (0.8 mole) of diisobutylene was added dropwise to the reaction mixture over a period of one hour. After the addition of the diisobutylene, the reaction mixture was heated to 148 C. over a three hour period and the temperature maintained there for an additional two hours.
  • Additive B Mixture of 4-tert-octylphenyl-1-tert-octyl-2- naphthylamine, 4 tert-butylphenyl-l-tert-octy1-2-naphthylamine and 4-tert-octylphenyl-1-tert-butyl-2-naphthylamine with 4 tert-octylphenyl-Z-naphthylamine, Ratio of alkylphenyl-alkylnaphthylamines to 4-tertoctylpheny1-2-naphthylamine is approximately 3 to 1.
  • Base Oils Base Oil W Mixed C acid esters of pentaerythritol and dipentaerythritol containing 0.17% w. of phosphorus extreme pressure agents, 0.1% w. of triazole corrosion inhibitors, 0.25% w. of a copolymeric dispersant, 1.5% W. of an amine antioxidant, 0.02% of a. dibasic acid corrosion inhibitor and 10 ppm. silicone fiuid antifoamant.
  • Base Oil X Base Oil W minus the copolymeric dispersant plus 2.0% w. additional phosphorus extreme pressure agent.
  • Base Oil Y Base Oil X minus the dibasic acid corrosion inhibitor and 1.0% of phosphorus extreme pressure agent plus 0.5% w. of a triazine oxidation inhibitor and an additional 0.5 of the amine antioxidant.
  • Base Oil Z Mixed C acid esters of pentaerythritol and dipentaerythritol containing 0.2% W. phosphorus extreme pressure agent and 0.5 w. of a triazole corrosion inhibitor.
  • compositions V and VI of the invention have outstanding properties in respect to overall cleanliness and viscosity change as compared to Composition IV whech contains an equal molar concentration of a phenyl-Z-naphthylamine having no alkyl substituents on the naphthyl ring. It is indeed surprising that the addition of an alkyl substituent on the naphthyl nucleus (Additive A) would bring about such a significant improvement in the eifectiveness of the inventive compounds.
  • Composition VI which contains a combination of the additives of the invention with the additive employed in Composition IV, has an overall demerit rating superior to that of either Compositions IV or V containing the additives individually, i.e., a total demerit rating of 28.2 as compared to 69 and 38.6 respectively.
  • EXAMPLE IV A further indication of the stability of the compositions of the invention was obtained by subjecting samples of Compositions VII and VIII to the Alcor High Temperature Deposition Test. Basically this test involves circulation of aerated oil over a heated deposition tube. The temperature of the tube is controlled at 525 F. on the inlet side and reaches 650 to 700 F. at the outlet end of the tube. The temperature profile of the tube is measured at the start and shortly before the end of the test. These temperature profiles and the tube deposits per unit length are used to determine the performance of the oil. The critical temperature is that temperature at which deposits begin to significantly affect the heat transfer characteristics of the oil. A temperature of about 600 F. is considered to be very satisfactory.
  • the overall deposit rating is obtained from a combination of the visual deposit rating of the tube, the tube deposit weight and the filter deposit weight. An overall rating of less than 50 is considered very good, a rating of below is considered exceptional. A detailed description of this test is given in Proceedings of the USAF-Southwest Research Institute Turbine Lubrication Conference, September 13-15, 1966, Southwest Research Institute, San Antonio, Texas, page 152. Test results are shown in Table III.
  • composition VIII of the invention has a significantly less tendency to form deposits than Composition V-II which is prepared from the same base oil as Composition VIII but contains an alkylated phenyl-Z-naphthylamine not in accordance with the invention.
  • compositions II and III of the invention have surprisingly less tendency to form sludge than Composition I which contains a molar equivalent of an additive not in accordance with the invention.
  • Composition XI of the invention had a significantly longer oxidation life than either Composition IX containing phenyl-2-naphthylamine, or Composition X containing an equivalent amount of a phenyl-Z-naphthylamine having an alkyl substituent on the phenyl ring alone.
  • a lubricant composition consisting essentially of a major amount of lubricating oil and an oxidation-inhibiting amount of a mixture of at least one 4-alkylphenyl-1- alkyl-2-naphthylamine with at least one 4-alkylphenyl-2- naphthylamine wherein said alkyl substituents have up to 16 carbon atoms and are tertiary alkyl substituents and the ratio of said alkylphenylalkylnaphthylamines to the alkylphenyl-naphthylamines is from 1:2 to 10:1.
  • composition of claim 1 wherein the oxidation inhibiting mixture is present in the amount of from 0.01 to 10% by weight.
  • composition of claim 1 wherein the lubricating oil is an ester of a monocarboxylic acid having 3 to 12 carbon atoms and a polyhydroxy compound selected from the group consisting of pentaerythritol, dipentaerythritol, trimethylolpropane and mixtures thereof.
  • composition of claim 3 wherein all of the alkyl substituents are selected from the group consisting of tertiary-butyl and tertiary-octyl.
  • composition of claim 4 wherein the ester lubricating oil is a mixed C acid ester of pentaerythritol and dipentaerythritol and the oxidation-inhibiting mixture is a mixture of 4-alkylphenyl-l-alkyl-Z-naphthylamines with 4-tert-octylphenyl-Z-napthylamine.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
US860035A 1969-09-22 1969-09-22 Lubricant compositions Expired - Lifetime US3660290A (en)

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JP (1) JPS4910962B1 (enrdf_load_stackoverflow)
BE (1) BE756024A (enrdf_load_stackoverflow)
CA (1) CA924328A (enrdf_load_stackoverflow)
DE (1) DE2005843C3 (enrdf_load_stackoverflow)
FR (1) FR2068867A5 (enrdf_load_stackoverflow)
GB (1) GB1296087A (enrdf_load_stackoverflow)
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3767575A (en) * 1971-11-16 1973-10-23 Mobil Oil Corp Oxidation resistant lubricant compositions
US3944492A (en) * 1966-04-07 1976-03-16 Uniroyal, Inc. Lubricant compositions containing N-substituted naphthylamines as antioxidants
USRE28805E (en) * 1971-11-17 1976-05-11 Mobil Oil Corporation Lubricants containing amine antioxidants
US3990985A (en) * 1973-03-26 1976-11-09 Hoechst Aktiengesellschaft Stable and storable aqueous dispersions of primary aromatic amines, their preparation and use
JPS5316710A (en) * 1976-07-30 1978-02-16 Uniroyal Inc Liquid antioxidant
US4770802A (en) * 1986-02-04 1988-09-13 Nippon Oil Co., Ltd. Lubricating oil compositions
US5283367A (en) * 1989-08-30 1994-02-01 Ciba-Geigy Corporation Substituted 1,4-diamino-2-butene stabilizers
US5489711A (en) * 1994-12-20 1996-02-06 The B. F. Goodrich Company Synthetic lubricant antioxidant from monosubstituted diphenylamines
US6426324B1 (en) 1993-12-15 2002-07-30 Noveon Ip Holdings Corp. Lubricant composition
US20070142243A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine
US20070142246A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions
US20070142245A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions
US20080318815A1 (en) * 2007-06-20 2008-12-25 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a dairylamine
EP2077315A1 (en) 2007-12-20 2009-07-08 Chevron Oronite Company LLC Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant
US20100152079A1 (en) * 2007-12-20 2010-06-17 Chevron Oronite Company Llc Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51111457U (enrdf_load_stackoverflow) * 1975-03-05 1976-09-09
JPS5280751U (enrdf_load_stackoverflow) * 1975-12-15 1977-06-16
JPS52171560U (enrdf_load_stackoverflow) * 1976-06-18 1977-12-27
DE69007214T2 (de) * 1989-08-30 1994-07-14 Ciba Geigy Butenylaromatische Aminstabilisatoren.
GB2294696A (en) * 1994-11-04 1996-05-08 Exxon Research Engineering Co Marine lubricant composition
EP2497796A3 (en) * 2005-10-11 2012-12-26 Chemtura Corporation Diaromatic Amines
US20080287328A1 (en) * 2007-05-16 2008-11-20 Loper John T Lubricating composition

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3944492A (en) * 1966-04-07 1976-03-16 Uniroyal, Inc. Lubricant compositions containing N-substituted naphthylamines as antioxidants
US3767575A (en) * 1971-11-16 1973-10-23 Mobil Oil Corp Oxidation resistant lubricant compositions
USRE28805E (en) * 1971-11-17 1976-05-11 Mobil Oil Corporation Lubricants containing amine antioxidants
US3990985A (en) * 1973-03-26 1976-11-09 Hoechst Aktiengesellschaft Stable and storable aqueous dispersions of primary aromatic amines, their preparation and use
JPS5316710A (en) * 1976-07-30 1978-02-16 Uniroyal Inc Liquid antioxidant
US4770802A (en) * 1986-02-04 1988-09-13 Nippon Oil Co., Ltd. Lubricating oil compositions
US5492954A (en) * 1989-08-30 1996-02-20 Ciba-Geigy Corporation Substituted 1,4-diamino-2-butene stabilizers and stabilized compositions
US5283367A (en) * 1989-08-30 1994-02-01 Ciba-Geigy Corporation Substituted 1,4-diamino-2-butene stabilizers
US5391808A (en) * 1989-08-30 1995-02-21 Ciba-Geigy Corporation Substituted 1,4-diamino-2-butene stabilizers
US6426324B1 (en) 1993-12-15 2002-07-30 Noveon Ip Holdings Corp. Lubricant composition
US5489711A (en) * 1994-12-20 1996-02-06 The B. F. Goodrich Company Synthetic lubricant antioxidant from monosubstituted diphenylamines
US7501386B2 (en) 2005-12-21 2009-03-10 Chevron Oronite Company, Llc Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine
US20070142243A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine
US20070142246A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions
US20070142245A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions
US7285518B2 (en) 2005-12-21 2007-10-23 Chevron Oronite Company Llc Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions
US8003583B2 (en) 2005-12-21 2011-08-23 Chevron Oronite Company Llc Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions
EP2009082A2 (en) 2007-06-20 2008-12-31 Chevron Oronite Company LLC Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a diarylamine
US7683017B2 (en) 2007-06-20 2010-03-23 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a diarylamine
US20080318815A1 (en) * 2007-06-20 2008-12-25 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a dairylamine
EP2077315A1 (en) 2007-12-20 2009-07-08 Chevron Oronite Company LLC Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant
US20100152079A1 (en) * 2007-12-20 2010-06-17 Chevron Oronite Company Llc Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant
US8623798B2 (en) 2007-12-20 2014-01-07 Chevron Oronite Company Llc Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant

Also Published As

Publication number Publication date
BE756024A (nl) 1971-03-11
NL7013904A (enrdf_load_stackoverflow) 1971-03-24
JPS4910962B1 (enrdf_load_stackoverflow) 1974-03-14
GB1296087A (enrdf_load_stackoverflow) 1972-11-15
FR2068867A5 (enrdf_load_stackoverflow) 1971-09-03
DE2005843B2 (de) 1980-07-17
CA924328A (en) 1973-04-10
DE2005843A1 (de) 1971-03-25
DE2005843C3 (de) 1981-05-14

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