US3011976A - Stabilization of lubricants - Google Patents

Stabilization of lubricants Download PDF

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Publication number
US3011976A
US3011976A US826441A US82644159A US3011976A US 3011976 A US3011976 A US 3011976A US 826441 A US826441 A US 826441A US 82644159 A US82644159 A US 82644159A US 3011976 A US3011976 A US 3011976A
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United States
Prior art keywords
methane
sec
tetra
inhibitor
diaminodiphenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US826441A
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English (en)
Inventor
Henry A Cyba
Robert H Rosenwald
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Universal Oil Products Co
Original Assignee
Universal Oil Products Co
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Filing date
Publication date
Priority to NL123811D priority Critical patent/NL123811C/xx
Priority to NL253735D priority patent/NL253735A/xx
Application filed by Universal Oil Products Co filed Critical Universal Oil Products Co
Priority to US826441A priority patent/US3011976A/en
Priority to GB24219/60A priority patent/GB905548A/en
Priority to ES0259601A priority patent/ES259601A1/es
Priority to DEU7315A priority patent/DE1150170B/de
Priority to FR832957A priority patent/FR1262418A/fr
Application granted granted Critical
Publication of US3011976A publication Critical patent/US3011976A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04—Elements
    • C10M2201/041—Carbon; Graphite; Carbon black
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06—Metal compounds
    • C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/102—Silicates
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/102—Silicates
    • C10M2201/103—Clays; Mica; Zeolites
    • C—CHEMISTRY; METALLURGY
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    • C10M2201/14—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • 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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    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • 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
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    • 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
    • C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
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    • 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
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    • 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
    • C10M2229/046—Siloxanes with specific structure containing silicon-oxygen-carbon bonds
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    • 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
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    • 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
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    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
    • C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2290/00—Mixtures of base materials or thickeners or additives
    • C10M2290/02—Mineral base oils; Mixtures of fractions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/06—Groups 3 or 13
    • 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
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
    • 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
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention relates to the stabilization of lubricants and more particularly to the use of improved inhibitors for efiecting the stabilization of lubricants.
  • Petroleum lubricants are unsatisfactory at high altitudes or in the Winter season for use in machine guns and automatic cannons which frequently could not be made to fire because of congealed lubricants. Because they are used under such stringent conditions, the synthetic lubricants undergo undesirable deterioration including, for example, formation of deposits, discoloration, change of viscosity, etc. While the features of the present invention are particularly applicable to the stabilization of synthetic lubricants, it is understood that they also may be used for the stabilization of petroleum lubricants.
  • the synthetic lubricants are of varied types including aliphatic esters, polyalkylene oxides, silicones, esters of phosphoric and silicic acids, highly fluorine-substituted hydrocarbons, etc.
  • aliphatic esters di-(Z-ethylhexyl) sebacate is being used on a comparatively large commercial scale.
  • Other aliphatic esters include dialkyl azelates, dialkyl suberates, dialkyl pimelates, diallcyl adipates, dialkyl glutarates, etc.
  • esters include clihexyl azelate, di-(Z-ethylhexyl) azelate, bis-(l-methyl cyclohexylmethyl) sebaca-te, di-3,5,5-trimethylhexyl glutarate, di-3,5,S-trimethylpentyl glutarate, di-(Z-ethylhexyl) pimelate, di-(Z-ethylhexl) adipate, triamyl tricarballylate, pentaerythiitol tetracaproate, dipropylene glycol dipelargonate, 1,5-pentanediol-di-(2- ethylhexanonate), etc.
  • the polyalkylene oxides include polyisopropylene oxide, polyisopropylene oxide diether, polyisopropylene oxide diester, etc.
  • the silicones include methyl silicone, methyl-phenyl silicone, chlorophenylsilicone, methylchlorophenylsilicone, etc, and the silicates include, for example, tetraisooctyl silicate, tetrakis-n-dodecyl silane, didodecyldioctyl silane, diphenyl-di-n-dodecyl silane, octadecyltridecyl silane, hexa-Z-ethylhexoxydisiloxane, etc.
  • phosphates as tricresyl phos phate, trioctyl phosphate, tris-(chlorophenyl) phosphate, chlorophenylphenyl phosphate also are being used.
  • the highly fluorinated hydrocarbons include fiuorinated oil, perfiuorohydrocarbons, etc.
  • Other synthetic lubricants proposed for use in high temperature service as, for example, jet fuel lubrication, etc. include pentaerythritol esters and trimethylolpropane esters.
  • the present invention also is applicable to the stabilization of greases made by compositing metallic soaps with the synthetic lubricating oils described above and are referred to herein as synthetic greases.
  • These metal base synthetic greases may be further classified as lithium base synthetic grease, sodium base synthetic grease, calcium base synthetic grease, barium base synthetic grease, strontium base synthetic grease, aluminum basesynthetic grease, etc.
  • These greases are solid or semi-solid gels and, in general, are prepared by the addition to the synthetic lubricating oil of hydrocarbon-soluble metal soaps or salts of higher fatty acids as, for example, lithium stearate, calcium stearate, aluminum naphthenate, etc.
  • the grease also may contain thickening agents such as silica, carbon black, metal oxides, phthalocyanines, polyacrylates, talc, bentone and organo-treated clays, etc. Alkylureas, arylureas, p-tolyl and p-chlorophenylurea derivatives of bitolylendi-isocyanate, pteridines, N-n-octadecylterephthalornate and other organic thickencrs are used.
  • the inhibitors also may be used in petroleum base grease.
  • the inhibitor in many applications it is important that the inhibitor also serves to retard and/or prevent corrosion of the metal surfaces with which the lubricant comes into contact.
  • the metal surfaces with which the lubricant comes into contact Generally at least a small amount of Water is present, either being formed during combustion and/or entrained in the fuel supplied to the engine. The combination of water and corrosive constituents cause corrosion of the metal. Accordingly, the inhibitor serves an important function in also retarding and/ or preventing such corrosion.
  • the inhibitor In addition tomeeting the chemical and physical requirements hereinbefore described, the inhibitor must be of sutficiently low cost to be economically acceptable. In other words, regardless of how effective an inhibitor is, if it cannot be marketed at a reasonable price, it will not be accepted in the industry because of economic reasons.
  • Applicants have made a detailed research inyestigation of extensive. classes of chemical compounds which might meet inhibitor requirements and still be marketed at a reasonable cost.
  • dianu'nodiphenyl methane compounds meet these requirements provided that the diaminodiphenyl methanes themselves are selected with certain important requirements.
  • diamino-diphenyl methane compounds meeting the important requirements to be hereinafter set forth in detail, appear to be particularly desirable for use in the stabilization of lubricants.
  • the use of diaminodiphenyl compounds has been proposed heretofore for use as an additive in lubricating oil and other substrates.
  • diaminodiphenyl compounds will meet these requirements, provided that they, in turn, meet other important requirements.
  • the diarninodiphenyl compounds having metallic constituents are undesired because of the possible adverse effect on engine performance as hereinbefore set forth.
  • Applicants have ruled out the diaminodiphenyl sulfides because of the possible undesirable corrosion effect due to the use of inhibitors containing sulfur.
  • the inhibitor compound is sufiiciently low in cost to be economically acceptable and this in turn has ruled out the diaminodiphenyl ethers because they are more expensive to manufacture.
  • diaminodiphenyl methanes appear to best meet the requirements hereinbefore set forth and furthermore that only those having the amino groups in the 4,4 positions should be used.
  • 4,4'-diaminodiphenyl methane may be prepared at a lower cost than other diaminodiphenyl methanes in which the amino groups are arranged in different positions on the phenyl nuclei, and accordingly offers a less expensive source for preparing the desired inhibitors.
  • the diaminodiphenyl methane must contain one or two alkyl groups substituted on each nitrogen atom.
  • both of the alkyl groups must be of secondary configuration.
  • the alkyl groups must be either of secondary configuration or comprise ethyl groups.
  • the phenyl nuclei When bearing corrosion inhibition is important, the phenyl nuclei must not contain an alkyl substituent in a position ortho to the nitrogen atoms.
  • each of the specific requirements enumerated above are essential, as will be shown by the examples appended to the present specifications.
  • the inhibitor compounds meeting these requirements are efiective inhibitors and may be manufactured at a reasonable cost, thereby offering to the industry an improved inhibitor which may be incorporated into lubricants for use under the severe conditions of modern technology.
  • the present invention relates to a method of stabilizing a lubricant which comprises incorporating therein a stabilizing concentration of an inhibitor selected from the group consisting of 4,4'-di-(secalkylamino) diphenyl methane, N,N,N',N'-tetra(secalkyl)-4,4-diaminodiphenyl methane and N,N,N,N'- tetra-ethyl-4,4-di-aminodiphenyl methane.
  • an inhibitor selected from the group consisting of 4,4'-di-(secalkylamino) diphenyl methane, N,N,N',N'-tetra(secalkyl)-4,4-diaminodiphenyl methane and N,N,N,N'- tetra-ethyl-4,4-di-aminodiphenyl methane.
  • the present invention relates to a method of stabilizing lubricating oil and preventing corrosion of metal surfaces contacting said lubricating oil which comprises incorporating in said lubricating oil an inhibitor having antioxidant and corrosion inhibiting properties, said inhibitor being selected from the group consisting of 4,4'-di-(secalkylamino)-diphenyl methane, N,N,N,N'-tetra-(sec-alkyl)-4,4'-diaminodiphenyl methane, and N,N,N,Ntetra-ethyl-4,4-diaminodiphenyl methane, said inhibitor being devoid of alkyl substituents in the positions ortho to the nitrogen atoms.
  • the present invention relates to a method of stabilizing a lubricant which comprises incorporating therein a stabilizing concentration of 4,4'-di-(sec-'butylamino)-diphenyl methane.
  • the present invention relates to a lubricant containing the inhibitor as herein set forth.
  • inhibitor compounds meeting the requirements hereinbefore set forth include 4,4-di-(secamylamino)-diphenyl methane, 4,4-di-(sec-hexylamino)- diphenyl methane, 4,4'-di-(sec-heptylamino)-diphenyl methane, 4,4'-di(sec-octylamino)-diphenyl methane, 4,4'-di-(sec-nonylamino)-diphenyl methane, 4,4-di-(secdecylamino)-diphenyl methane, 4,4-di-(sec-undecylamino)- diphenyl methane, 4,4'-di-(sec-dodecylamino)-diphenyl methane, etc., N,N,N',N'-tetra-(sec-amyl)-4,4- diamino-diphenyl methan
  • the alkyl substituents are the same and contain from 3 to about 12 carbon atoms each in the di-alkyl substituted compounds and from 2 to about 12 carbon atoms each in the tetra-alkyl substituted compounds. In some cases, these alkyl groups each may contain a larger number of carbon atoms, although in general should not exceed about 20 carbon atoms each. In still other cases, the substituents attached to the nitrogen atoms, particularly in the tetra-alkyl substituted compounds, may be ditferent but at least one each of the substituents attached to the nitrogen atoms must contain the secondary alkyl group with the exception of the tetraethyl amino substituted compound. While all of these compounds are elfective for the purpose, it must be pointed out that they will not necessarily be equivalent in the same or different substrates.
  • alkyl substituents in the 2,2 positions on the phenyl nuclei do not reduce the potency of the inhibitor but do not appear to increase the potency. Accordingly, there is no objection to the inhibitor compounds containing alkyl substituents in the 2,2 positions.
  • Illustrative compounds in this category include 2,2'-dimethy1-4,4'-di-(sec-butylamino)-diphenyl methane, 2,2- di-ethyl-4,4-di-(sec-butylamino)-diphenyl methane, 2,2- di-propyl-4,4'-di-(sec-butylamino)diphenyl methane, 2,2-
  • the inhibitor compound in lubricating oil for use in automobile engines, diesel engines, stationary engines, etc., the inhibitor compound must be devoid of alkyl substituents in the 3,3 positions. This will be illustrated further in the examples appended to the present specifications.
  • the inhibitor for use in the present invention may be prepared in any suitable manner.
  • Diaminodiphenyl methane is available commercially or may be prepared in any suitable manner as, for example, by the reaction of aniline with formaldehyde in the presence of an acid.
  • Diaminodiphenyl methane then is reductively alkylated with the esired ketone in the presence of a suitable catalyst to produce either the dior tetra-substituted derivative.
  • Any suitable catalyst may be used in the reductive alkylation including those containing platinum, palladium, cobalt, nickel, molybdenum, etc.
  • Another catalyst used for this reaction is a mixture of the oxides of chromium, copper and barium.
  • reaction is effected at an elevated temperature of from about 200 to about 500 F. and a hydrogen pressure of from about 50 to about 2000 pounds per square inch or more.
  • 4,4-di(sec-butylamino)-diphenyl methane is prepared by the reductive alkylation of 4,4"-diaminodiph'enyl methane with methylethyl ketone.
  • acetone is used as the alkylating agent.
  • 4,4.'-di-(l-methylheptylamino)-diphenyl methane is pre pared by the reductive alkylation of 4,4'-diarninodiphenyl methane with methyl he-xyl ketone.
  • 4,4'-di-(1-ethyl- 3-rnethylpentylamino)-diphenyl methane is prepared by the reductive alkylation of 4,4'-diaminodiphenyl methane with ethylisoamyl ketone.
  • the ketone is reacted in the inhibitor may be added to one or more the components of the grease before final compositing thereof.
  • the inhibitor may be prepared as a solution in a suitable solvent including, for example, aromatic hydrocarbons such as benzene, toluene, xylene, ethyl benzene, cumene, decalin, etc., or mixtures such as naphtha, kerosene, lube oil, etc.
  • the inhibitor may be used along with other additives incorporated in the lubricant.
  • a metal deactivator, dye, viscosity index improver, pour point depressant, anti-foaming additive, lubricity and extreme pressure additive, anti-scufiing additive, detergent, etc may be incorporated in the lubricant.
  • the inhibitor of the present inven tion may be prepared as a mixture with one or more of these other additives and incorporated in this manner in the lubricant.
  • the diaminodiphenyl methane must contain at least one or two alkyl groups attached to each nitrogen atom.
  • the alkyl substituents must be of secondary configuration. This is shown in the following table which compares the results of tests conducted with ditferent samples of the lubricant containing diferent additives. Each of the additives was employed in a concentration of 0.5% by weight of the lubricating Run No. Additive Noneoil before testing Noneoil after testing 4,4'-dlaminodiphenyl methane.
  • 2,2-di-met11yl-4,4-diaruino-diphenyl urethane 3,3-di-lsopr0py1-4,4-diamino-diphenyl methane 3,3-di-sec-butyl-4,4-diamino-diphenyl methane 4,4-di-(meth ylamino)diphonyl methane.
  • the inhibitor will be used in the substrate in an amount sufiicient to obtain the desired stabilization and, when desired, bearing corrosion inhibition. In general this concentration will be within the range of from about 0.01% to about 5% and preferably of from about 0.1% to about 3% by weight of the lubricant.
  • the inhibitor is added to the lubricant in any suitable manner and prefer: ably with intimate mixing in order to obtain uniform distribution of the inhibitor in the lubricant.
  • the inhibitor may be added to the lubricant during the manufacture thereof as, for example, when used in grease
  • the lubricating oil after evaluation in the Lauson engine underwent a bearing weight loss of almost three grams, an increase in neutralization number to above ten, anincrease in pentane insoluble material to over 5 percent,'and almost double increase in viscosity (compare run number 2 with run number 1).
  • the diaminodiphenyl methane must contain certain alkyl substituents attached to the nitrogen atoms.
  • diaminodiphenyl methane (run number 3) was not soluble in the oil and accordingly is of no use for the purpose and obviously could be evaluated in the Lauson engine.
  • di-methyl groups attached to the phenyl nuclei (run number 4) or methyl groups attached to the nitrogen atoms (run number 7), the compounds were not soluble in the oil.
  • the alkyl substituents must be attached to the nitrogen atoms and must be of secondary configuration in the dialkylated derivatives. This is clearly illustrated by comparing run number 9 with the oil containing 4,4'-di (sec-butylamino) diphenyl methane (run number 12) induced very small bearing weight loss of only 0.0018 gram, a low neutralization number and pentane insolubles, and also resulted in an oil of substantially the same viscosity as the original oil.
  • Run number 13 illustrates an additional dialkylated compound in which the alkyl substituents are of secondary configuration and are attached to the nitrogen atoms.
  • the normal .propyl derivative was of comparatively small benefit in that the bearing weight loss was still above 0.8 gram and the viscosities were 491 and 62 seconds.
  • run number 10 using 4,4'-d.i(isopropylamino) diphenyl methane, the bearing weight loss induced by the lubricating oil containing this additive was only 0.0092 and the neutralization number 0.1 2, the pentane insolubles only 0.1% and the viscosity substantially the same as the original oil (run number 1).
  • this compound was extremely effective, both in inhibiting bearing corrosion and in stabilizing the oil, so that the used oil retained substantially the same properties as the original oil.
  • run number 12 In run number 11, in which the alkyl substituent is of normal configuration, the oil containing this inhibitor induced considerable bearing corrosion (2.726 grams loss) and also resulted in considerable deterioration of the oil as evidenced by the neutralization number and high viscosity. In contrast,
  • the lubricating oil used in this example was a syn-v thetic oil, more particularly dioctyl sebacate, marketed under the trade name of Plexol 201.
  • the oil was evaluated in accordance with an Oxygen Stability Test in which a 100 cc. sample of the lubricating oil is placed in a bath maintained at 400 F.
  • the data are reported in the following table and include results obtained with a sample of the lubricating oil without additive and samples containing dilferent additives, including those comprised within the present invention an dthose outside of the scope of the present invention.
  • the additive in all cases was used in a concentration of 0.0033 mole per 100 cc. of lubricating oil. This is approximately 1% by weight thereof.
  • run members 22 and 25 in which the secondary alkyl groups are attached to the phenyl nuclei and run numbers 23 and 26 in which the alkyl groups attached to the nitrogen atoms are of normal configuration, all resulted in stabilities of about one-half of those obtained in run numbers 24, 27 and 28 in which the alkyl substituents are of secondary configuration and are attached to the nitrogen atoms.
  • the inhibitor also may contain alkyl substituents in the 3,3 positions. Also, as hereinbefore set forth, such substitutions in the 2,2 positions are of minor effect. This is illustrated by the data in the following table. For ready reference run numbers 24 and 27 of Table IV are repeated in the following table. The data reported in this table were obtained in the same manner as described in Table IV.
  • EXAMPLE VI A similar series of runs were conducted in the same manner as Examples IV and V for the purpose of evaluating the tetra-alkylated derivatives.
  • the substrate was Plexol 201 and the concentration of additives and other conditions of evaluation were the same as described in Example IV. These results are reported in the following table.
  • a lubricant consisting essentially of an oil of lubri cating viscosity and a stabilizing concentration of an inhibitor selectedfrom the group consisting of 4,4'-di-(secalkylamino) diphenyl methane, N,N,N,N-tetra-(sec- 6.
  • a lubricant consisting essentially of an oil of lubricating viscosity and a stabilizing concentration of N,N,N,N'-tetra-(sec-butyl)-4,4-diaminodiphenyl methane.
  • a lubricant consisting essentially of an oil of lubricating viscosity and a stabilizing concentration of N,N,N',N'-tetra-ethy1-4,4'-diaminodiphenyl methane.
  • a lubricant consisting essentially of an oil of lubricating viscosity and a stabilizing concentration of an inhibitor having both antioxidant and corrosion bearing inhibiting properties, said inhibitor being selected from the group consisting of 4,4'-di-(sec-alkylamino)-diphenyl methane, N,N,N',N'-tetra-(sec-alkyl) 4,4 diaminodiphenyl methane and N,N,N',N-tetra-ethyl-4,4-diamino- 1 1 diphenyl methane, said inhibitor being devoid of alkyl substituents in positions ortho to the nitrogen atoms.
  • a lubricant consisting essentially of a lubricating component selected from the group consisting of greases and oils of lubricating viscosity, and a stabilizing concentration of an inhibitor selected from the group consisting of 4,4-di-(sec-alkylamino) -diphenyl methane, N,N,N,N- tetra-(sec-alkyl) 4,4 diaminodiphenyl methane and N,N,N',N-tetra-ethyl-4,4'-diaminodiphenyl methane.
  • the lubricant of claim '9 further characterized in that the lubricating component thereof is a grease comprising a lubricating oil and a metal soap of a higher fatty acid.
  • a lubricant consisting essentially of a lubricating component selected from the group consisting of greases and oils of lubricating viscosity, and a stabilizing concentration of 4,4'-di-(isopropylamino)-diphenyl methane.
  • a lubricant consisting essentially of a lubricating component selected from the group consisting of greases and oils of lubricating viscosity, and a stabilizing concentration of 4,4'-di-(sec-butylamino)-diphenyl methane.
  • a lubricant consisting essentially of a lubricating component selected from the group consisting of greases and oils of lubricating viscosity, and a stabilizing concentration of N,N,N,N-tetra-(isopropyl)-4,4'-diaminodi- 25 phenyl methane.
  • a lubricant consisting essentially of a lubricating 12 component selected from the group consisting of greases and oils of lubricating viscosity, and a stabilizing concentration of N,N,N',N'-tetra- (sec-butyl)-4,4'-diaminodiphenyl methane.
  • a lubricant consisting essentially of a lubricating component selected from the group consisting of greases and oils of lubricating viscosity, and a stabilizing concentration of N,N,N,N'-tetra-ethyl-4,4'-diaminodiphenyl methane.
  • a lubricant consisting essentially of a lubricating component selected from the group consisting of greases and oils of lubricating viscosity, and a stabilizing concentration of an inhibitor having both antioxidant and corrosion bearing inhibiting properties, said inhibitor being selected from the group consisting of 4,4-di-(sec-alkylamino) -diphenyl methane, N,N,N',Ntetra-( sec-alkyl 4,4-diaminodiphenyl methane and N,N,N',N'-tetra-ethyl- 4,4-diaminodiphenyl methane, said inhibitor being devoid of alkyl substituents in positions ortho to the nitro gen atoms.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US826441A 1959-07-13 1959-07-13 Stabilization of lubricants Expired - Lifetime US3011976A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
NL123811D NL123811C (de) 1959-07-13
NL253735D NL253735A (de) 1959-07-13
US826441A US3011976A (en) 1959-07-13 1959-07-13 Stabilization of lubricants
GB24219/60A GB905548A (en) 1959-07-13 1960-07-12 Stabilisation of lubricants
ES0259601A ES259601A1 (es) 1959-07-13 1960-07-12 Un procedimiento para estabilizar un lubricante
DEU7315A DE1150170B (de) 1959-07-13 1960-07-13 Schmiermittel
FR832957A FR1262418A (fr) 1959-07-13 1960-07-13 Procédé de stabilisation des lubrifiants et produits en résultant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US826441A US3011976A (en) 1959-07-13 1959-07-13 Stabilization of lubricants

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US3011976A true US3011976A (en) 1961-12-05

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US826441A Expired - Lifetime US3011976A (en) 1959-07-13 1959-07-13 Stabilization of lubricants

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US (1) US3011976A (de)
DE (1) DE1150170B (de)
ES (1) ES259601A1 (de)
FR (1) FR1262418A (de)
GB (1) GB905548A (de)
NL (2) NL123811C (de)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3110671A (en) * 1960-07-05 1963-11-12 Universal Oil Prod Co Stabilized lubricants
US3179620A (en) * 1961-01-12 1965-04-20 Universal Oil Prod Co Stabilization of polyolefin plastics with substituted diamino diphenyl alkanes
US3182633A (en) * 1961-05-16 1965-05-11 Lodige Wilhelm Method and apparatus for enveloping granular and/or short fibred substances in coatings of other substances, preferably in thin films of synthetic plastic substances
US3201350A (en) * 1963-04-08 1965-08-17 Monsanto Res Corp Lubricants containing a schiff base
US3216939A (en) * 1962-06-18 1965-11-09 Universal Oil Prod Co Stabilization of lubricants
US3696851A (en) * 1964-02-11 1972-10-10 Geigy Chem Corp Chemical compounds and compositions
US3977987A (en) * 1973-03-09 1976-08-31 Universal Oil Products Company Fuel and lubricant compositions containing novel pyrrolidinyl or piperidinyl-substituted diphenyl alkane antioxidants
US4885150A (en) * 1986-02-28 1989-12-05 The Dow Chemical Company Stable thiocyanogen composition
US5560848A (en) * 1995-05-26 1996-10-01 Exxon Research And Engineering Company Combination diphenyl amine-phenothiazine additive for improved oxidation stability in polyol ester based greases (Law236)
WO2018125569A1 (en) * 2016-12-27 2018-07-05 The Lubrizol Corporation Lubricating composition including n-alkylated dianiline
US11162048B2 (en) 2016-12-27 2021-11-02 The Lubrizol Corporation Lubricating composition with alkylated naphthylamine

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4370246A (en) * 1981-04-27 1983-01-25 Chevron Research Company Antioxidant combinations of molybdenum complexes and aromatic amine compounds

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2000045A (en) * 1933-05-26 1935-05-07 Goodrich Co B F Antioxidant
US2452320A (en) * 1944-12-02 1948-10-26 Texas Co Oxidation-inhibited lubricating compositions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2000045A (en) * 1933-05-26 1935-05-07 Goodrich Co B F Antioxidant
US2452320A (en) * 1944-12-02 1948-10-26 Texas Co Oxidation-inhibited lubricating compositions

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3110671A (en) * 1960-07-05 1963-11-12 Universal Oil Prod Co Stabilized lubricants
US3179620A (en) * 1961-01-12 1965-04-20 Universal Oil Prod Co Stabilization of polyolefin plastics with substituted diamino diphenyl alkanes
US3182633A (en) * 1961-05-16 1965-05-11 Lodige Wilhelm Method and apparatus for enveloping granular and/or short fibred substances in coatings of other substances, preferably in thin films of synthetic plastic substances
US3216939A (en) * 1962-06-18 1965-11-09 Universal Oil Prod Co Stabilization of lubricants
US3201350A (en) * 1963-04-08 1965-08-17 Monsanto Res Corp Lubricants containing a schiff base
US3696851A (en) * 1964-02-11 1972-10-10 Geigy Chem Corp Chemical compounds and compositions
US3977987A (en) * 1973-03-09 1976-08-31 Universal Oil Products Company Fuel and lubricant compositions containing novel pyrrolidinyl or piperidinyl-substituted diphenyl alkane antioxidants
US4885150A (en) * 1986-02-28 1989-12-05 The Dow Chemical Company Stable thiocyanogen composition
US5560848A (en) * 1995-05-26 1996-10-01 Exxon Research And Engineering Company Combination diphenyl amine-phenothiazine additive for improved oxidation stability in polyol ester based greases (Law236)
WO2018125569A1 (en) * 2016-12-27 2018-07-05 The Lubrizol Corporation Lubricating composition including n-alkylated dianiline
US11162048B2 (en) 2016-12-27 2021-11-02 The Lubrizol Corporation Lubricating composition with alkylated naphthylamine

Also Published As

Publication number Publication date
NL253735A (de)
DE1150170B (de) 1963-06-12
FR1262418A (fr) 1961-05-26
GB905548A (en) 1962-09-12
NL123811C (de)
ES259601A1 (es) 1961-01-16

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