EP0022281B1 - Amino compounds and use of amino compounds as antioxydant in lubricating oils - Google Patents

Amino compounds and use of amino compounds as antioxydant in lubricating oils Download PDF

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Publication number
EP0022281B1
EP0022281B1 EP19800200511 EP80200511A EP0022281B1 EP 0022281 B1 EP0022281 B1 EP 0022281B1 EP 19800200511 EP19800200511 EP 19800200511 EP 80200511 A EP80200511 A EP 80200511A EP 0022281 B1 EP0022281 B1 EP 0022281B1
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EP
European Patent Office
Prior art keywords
alpha
aniline
methyl
antioxidant
hydrogen
Prior art date
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Expired
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EP19800200511
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German (de)
English (en)
French (fr)
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EP0022281A1 (en
Inventor
Baldev Kumar Bandlish
Frederick C. Loveless
Walter Nudenberg
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Uniroyal Inc
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Uniroyal Inc
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Publication of EP0022281A1 publication Critical patent/EP0022281A1/en
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Classifications

    • 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
    • C10M133/14—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups
    • 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
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/16—Naphthenic acids
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • 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
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • 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

Definitions

  • lubricating oils that are effective at elevated temperatures.
  • Polyesters, polyolefins, polyglycols, polyphenyl ethers, phosphates, silicones, etc. have been used as suitable lubricating oils. These lubricating oils undergo oxidative degradation at elevated temperatures. Loss of lubricating properties due to oxidative breakdown of these oils may cause failure of a part, or parts, in contact with the oils.
  • the prior art discloses the stabilization of lubricating oils using various amines including diphenyl- and substituted diphenylamines, p-phenylenediamine and substituted naphthylamine. There appears to be no recognition of the use of secondary amines wherein one of the groups attached the amino nitrogen is an aromatic or substituted aromatic ring and the other group is an aliphatic carbon which in turn is attached to an aromatic or substituted aromatic ring.
  • U.S.-A-1,469,245 discloses N-(o-Hydroxybenzyl)-N'-phenyl-p-phenylene diamine as an anti- degradant for rubber.
  • This compound belongs to the class of phenylene diamines which are known antioxidants. Furthermore, its use as a stabilizer for lubricating oils is neither disclosed in that patent, nor elsewhere.
  • U.S.-A-2,108,147 teaches a method for preparing secondary and tertiary amines including 1-anilino-1-phenylethane.
  • Hickenbottom teaches a phenylamine compound designated as alpha- phenylethyl-p-toluidine; see Journal of the Chemical Society (1934) pages 319-322.
  • Beilstein discloses a phenyl amine compound of the general formula wherein R can be phenyl; see Handbuch Der Organischen Chemie 4th Ed., Vol XII Pat. IV pages 2403-4. None of the aforegoing compounds are taught to be antioxidants.
  • Y is: When Y is the moiety of formula (II), Z is H or C 1 to C 3 alkyl; and X and R 2 are each independently selected from the group consisting of hydrogen, C,-C 12 alkyl, C 1 -C 12 alkoxy; C 1 -C 18 carbalkoxy, halogen, or nitro and R 1 is hydrogen, C 1 C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 18 carbalkoxy, halogen, amino or nitro.
  • R 1 and R 3 are each independently selected from the group of moieties set forth as R, above and R 2 is as previously defined; provided, however, R, and R 2 may not be simultaneously hydrogen when Z is hydrogen.
  • the antioxidants of this invention are used in conjunction with a metal deactivator and a metal or metal salt.
  • the preferred metal salts are oil soluble organic salts, e.g., metal napthenates.
  • This invention relates to a compound for the stabilizing lubricating oils against oxidation and sludge formation.
  • this invention relates to stabilizing such oils utilizing phenylated benzylamines or phenylated tetrahydro naphthylamines, which may be substituted or unsubstituted, either alone or in conjunction with a metal deactivator and a metal compound.
  • This stabilizer system provides a surprisingly high degree of resistance to oxidative breakdown of lubricating oils as well as resulting in dramatic reductions in sludge formation.
  • Certain of the phenylated benzylamines and phenylated tetrahydro naphthylamines used in the practice of this invention are novel compounds.
  • antioxidants which are amino compounds having the general formula wherein Y is:
  • Z and X are each independently selected from the group consisting of H or C, to C 3 alkyl; provided that both X and Z are not simultaneously H;
  • R 2 is selected from the group consisting of hydrogen, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 18 carbalkoxy, p-acetyl, alpha-anilinoethyl, halogen, or nitro; and
  • R 1 is hydrogen, C 1 -C2 alkyl, C 1 -C 12 alkoxy, C 2 C 18 carbalkoxy, halogen or nitro;
  • R 1 and R 3 are each independently selected from the group consisting of hydrogen, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 18 carbalkoxy, halogen, amino or nitro
  • the compounds of the invention as defined above are novel compounds, provided that when Y is the moiety of formula (II), X is methyl and both Z and R 2 are hydrogen, R 1 is not p-methoxy.
  • the compound N-(a/pha-methyl benzyl)-p-methoxyaniline has been disclosed in Chemical Abstracts, Vol. 63, 63, No. 4, August 16, 1965, abstract 4191 C, but no use as an antioxidant in lubricating oils is indicated in this reference.
  • the preferred antioxidants of this invention are:
  • the amines of this invention are useful in stabilizing a wide range of lubricating oils including polyester oils, mineral oils and synthetic hydrocarbon oils.
  • the stabilizer system of this invention is particularly effective for use in polyolester lubricating oils.
  • the polylolester lubricating oils for which the stabilizer systems of this invention are suitable are synthetic lubricants based upon one or more organic carboxylic acid esters.
  • Illustrative examples of such oils are diesters such as dioctyl sebacate or dinonyl adipate prepared by the reaction of a dibasic acid and a monohydric alcohol; triesters such as trimethylolpropane tripelogonate or trimethylolpropane tricaprilate prepared by the reaction of trimethylol propane and a monobasic acid; tetraesters such as pentaerythritol tetracaprilate prepared by the reaction of pentaerythritol and a monobasic acid; esters of trimethylolpropane or pentaerythritol prepared by reaction with mixtures of monobasic acids; or complex esters prepared by reacting mixtures of monobasic acids, dibasic acids and polyhdyric alcohols.
  • the synthetic hydrocarbon oils to which the stabilizer system of this system of this invention may be added are oligomers of alpha olefins.
  • the preferred alpha olefins are C l -C, 4 alpha-olefins.
  • these hydrocarbon oils have a number of average molecular weight of about 280 to about 2,000; preferably about 350 to about 1,500.
  • These lubricating oils have low unsaturation preferably having an iodine number of less than 3.
  • antioxidant when used in the specification and claims means the substituted phenylated amines and substituted tetrahydronaphthyiamines of this invention.
  • stabilizer system as used in the specification means the aforegoing antioxidants in conjunction with a metal compound and a metal deactivator.
  • the metal may be present either as the free metal or a salt of a metal.
  • the salt must be soluble in the lubricating oil and is preferably an organometallic salt.
  • the preferred salts include naphthenates, stearates, acetylacetonates, octoates, decanoates etc.
  • the metal deactivators useful in the practice of this invention are benzotriazole and benzotriazole derivatives.
  • the benzotriazole derivative can be alkyl substituted or dialkyl amino alkyl substituted; preferably dialkyl amino alkyl substituted. Substitution is on the seconday nitrogen of the triangle.
  • the alkyl group can be a C 1 to C 20 alkyl and each alkyl may be the same or different than the others.
  • the alkyl groups are selected to give the benzotriazole derivative sufficient oil solubility to be incorporated into the lubricant in an effective amount e.g. C 6 -C 12 alkyl. Typical of such compounds is Reomet 38 marketed by Ciba Geigy Co.
  • the term "metal deactivator" as used in the specification and claims means a compound which when added to a lubricant will neutralize the catalytic effect of metals e.g. copper in promoting oxidation.
  • the various components of the antioxidant system which may be added in any order are used in the following amounts.
  • the antioxidant of this invention is used in amounts varying from about 0.5 to about 5.0 parts by weight per 100 parts of the oil, preferably, about 1.0 to about 4.0 parts; more preferably 2.0 to 2.5 parts.
  • the metal deactivators can be used in amounts of about 0.05 to about 1.0 part by weight per 100 parts of the oil, preferably, 0.1 to 0.3 part.
  • Metal or metal salts are used in the amounts of about 1 to about 25 parts of metal by weight per million parts of the oil; preferably 2 to 10 parts.
  • the preferred metal is copper.
  • polyester as used in the specification and claims means a polyester prepared from a polyol by reacting the polyol with a stoichiometric equivalent of mono basic acids.
  • This example shows the unexpected ability of the antioxidant of the present invention to protect polyester based lubricating oils against oxidative degradation.
  • the oil used was a commercially available polyolester fluid, Hercolube A (marketed by Hercules Inc.) and believed to be one prepared from pentaerythritol and a mixture of monocarboxylic acids, e.g., valeric acid and pelargonic acid.
  • the neutralization number was determined by the color-indicator titration method according to ASTM Procedure D974-55T.
  • the Kinematic Viscosity was determined according to ASTM Procedure D445-53T.
  • the metal washers which were weighed initially, were then carefully washed and weighed again to determine the weight change in grams.
  • Sample C wherein the test was conducted in the presence of copper, was slightly more deteroriated than Sample B, where no copper was present.
  • This example demonstrates the effect of the addition of and changes in the levels of a metal deactivator such as Reomet-38, a benzotriazole derivative marketed by Ciba Geigy Co., on the stabilization of a polyolester based lubricating oil while the level of N-(alpha-methylbenzyl)aniline and copper are maintained constant.
  • a metal deactivator such as Reomet-38, a benzotriazole derivative marketed by Ciba Geigy Co.
  • Table III shows that a stabilizer system containing N-(alpha-methylbenzyl)aniline and Reomet-38 is ineffective in the absence of copper (Sample A, Table III) in decreasing the amounts of sludge, maintaining low viscosity, low neutralization number, and protecting the metal washers from oxidation. In the absence of copper, Reomet 38 functions as a pro-degradant.
  • the data in Table III further shows that increasing amounts of copper above 10 ppm causes the stabilizer system to exhibit a decrease in its efficiency in controlling oxidative breakdown.
  • Sample II-D illustrates that when the amine, a metal deactivator and copper are present, the greatest protection is afforded to the oil.
  • Sample I-B amine but no copper
  • Sample I-C amine and copper
  • Sample III-A amine and metal deactivator but no copper
  • This example demonstrates how the stabilization of a polyolester based lubricating oil is affected by changes in the level of N-(a/pha-methylbenzyl)aniline while maintaining constant Reomet-38 level in the presence of a constant amount of copper metal.
  • the samples were prepared as in EXAMPLE I, using the amounts of ingredients shown in Table V.
  • This example demonstrates how various substituted N-benzylanilines effect the stabilization of a polyolester based oil while maintaining a constant Reomet-38 level in the presence of a constant amount of copper metal.
  • N-benzylanilines were prepared by catalytic hydrogenation of the corresponding Schiffs bases. Five percent Pd/C was used as the catalyst and ethanol was used as the solvent for hydrogenating the Schiff's bases.
  • Schiff's bases were prepared by the reaction of the appropriate ketones and anilines in the presence of molecular sieves. About 40 grams of molecular sieves (Linde 5A) were added to 1.0 mole of ketone and 1.0 to 1.2 moles of aromatic amine in 200 ml. of benzene; see Kazuo Taguchi and F. H. Westheimer, J. ORG. CHEM. 36, 1570 (1971).
  • the reaction mixture was refluxed with continuous removal of water until almost no free ketone could be detected in the reaction mixture by I.R. spectroscopy.
  • the mixture was then filtered and the molecular sieves washed with benzene. The filtrate and washings were combined and evaporated to dryness under reduced pressure.
  • the crude product was purified by either crystallization or by vacuum distillation.
  • a preferred embodiment of this invention involves alkylation in the benzyl ring and/or the aniline ring of the parent alpha-methyl benzyl aniline. This is beneficial in that it results in decreased volatility of the parent compound.
  • R 2 can be H, or a C 1 to C 12 alkyl group and R 1 can be H or a C 4 to C 12 alkyl group; provided that R 1 and R 2 are not simultaneously both hydrogen.
  • R 2 can be a C 1 to C 12 alkyl group which may or may not be branched.
  • R 1 can be an alkyl group, preferably in the para-position or a tertiary alkyl group such as those derived from isobutylene, isobutylene dimer, isobutylene trimer, propylene trimer, alpha-methyl styrene and the like.
  • This example shows how phenylated-alpha-tetralylamine affects the stabilization of a polyolester based lubricating oil.
  • Table VIII shows that the addition of phenylated-alpha-tetralylamine, a metal deactivator and copper or a copper salt to a polyloester lubricating oil such as Hercolube A stabilizes the said oil against oxidative breakdown.
  • Example II.E To 100 parts of polydecene synthetic hydrocarbon oil is added 2.0 parts of N-(alpha- methylbenzyl)aniline and 0.5 parts Reomet 38 as in Example II.E.
  • the resulting blend exhibits excellent anitoxidant properties when aging is performed at elevated temperatures.
  • N-alpha-methyl-p-nonyl benzylidene) aniline (40g) prepared by the procedure described in Example XVI A was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent.
  • N-(alpha-methyl-p-nonyl benzyl) aniline (XXXI) was obtained by fractional distillation. XXXI had a boiling point of 183°C at 20 Pa (0.15 millimeter).
  • the desired product II had a boiling point of 173 to 178°C at 3.3 Pa (0.025 millimeter).
  • Nonyl benzene was prepared by alkylating benzene with mixed propylene trimer using Friedel Crafts reaction. Nonyl benzene was nitrated and reduced to give p-nonyl aniline. A solution of p-nonyl aniline (30g), acetophenone (60g), toluene (200ml) and pyridine (20mi) was refluxed with continuous removal of water. N-(a-methyl benzylidene)-p-nonyl aniline (III) was obtained by fractional distillation. III had a boiling point of 194°C at 6.6 Pa (0.05 millimeter).
  • N-( ⁇ -methyl benzylidene)-p-nonyl aniline (III) (16.5g) prepared by the procedure described in Example IIA was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent.
  • N-(a-methyl benzyl)-p-nonyl aniline (IV) was obtained by fractional distillation. IV had a boiling point of 180-184°C at 3.3 Pa (0.025 millimeter).
  • N-(a-methyl benzylidene)-p-anisidine (VII) prepared by the procedure described in example IVA was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent to give N-(a-methyl benzyl)-p-anisidine (VIII). VIII had a melting point of 64°C.
  • N-( ⁇ -methyl benzylidene)-p-carbethoxyaniline (XI) prepared by the procedure described in example XXIIA was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent to give N-(a-methyl benzyl)-p-carbethoxy aniline (XII).
  • XII had a m.p. of 88°C.
  • N-( ⁇ -methyl benzylidene)-m-carbethoxyaniline (27g) prepared by the procedure described in example VIIA was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent.
  • N-(a-methyl benzyl m-carbethoxy aniline (XIV) was obtained by fractional distillation. XIV had a boiling point of 156°C at 13 Pa (0.1 millimeter).
  • N-(a-methyl benzylidene)-o-carbethoxyaniline (13g) prepared by the procedure described in example XXVA was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent.
  • N-( ⁇ -methyl benzyl)-o-carbethoxyaniline (XVI) (12g) was obtained by fractional distillation. XVI had a boiling point of 168°C at 185 Pa (1.4 millimeter).
  • XIX m-Chloro-N-( ⁇ -methyl benzylidene) aniline (XIX) (24g) prepared by the procedure described in example XXVIIA was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent. m-Chloro-N-(a-methyl benzyl) aniline (XX) was obtained by fractional distillation. XX had a boiling point of 133°C at 20 Pa (0.15 millimeter).
  • o-Chloro-N-(a-methyl benzylidene) aniline (XXI) (15g) prepared by the procedure described in example XXVIIIA was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent.
  • o-Chloro-N-(a-methyl benzyl) aniline (XXII) was obtained by fractional distillation.
  • XXII had a boiling point of 134°C at 160 Pa (1.2 millimeter).
  • XXIII p-Acetyl-N-(a-methylbenzylidene) aniline (30g) prepared by the procedure described in Example XXIXA was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent.
  • p-Acetal-N-( ⁇ -methyl benzyl) aniline (XXIV) was obtained by fractional distillation. XXIV had a boiling point of 165°C at 13 Pa (0.1 millimeter).
  • XXIII p-acetyl-N-( ⁇ -methyl benzylidene) aniline (XXIII) (40g) prepared by the procedure described in example XXIXA and aniline (20ml) was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent. The crude product was crystallized from ethanol to give 1,4-Bis-(1-anilinoethyl) benzene (XXV). XXV had a melting point of 169-170°C.
  • XXVII N-(1,2,3,4-tetrahydronaphthylidene) aniline (38g) prepared as described in example XXXIA was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent. The crude product was crystallized from ethanol to give 1-(p-dodecylanilino)-1,2,3,4-tetrahydronaphthalene (XXVII). XXVII had a melting point of 34°C.
  • N-(1,2,3,4-Tetrahydronaphthylidene)-p-carbethoxyaniline (XXVIII) (30g) prepared by the procedure described in example XXXIIA was hydrogenated using 5% Pd/C as the catalyst and 95% ethanol to give 1-(p-carbethoxy-anilino)-1,2,3,4-tetahydronaphthalene (XXIX).
  • XXIX had a melting point of 34°C.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP19800200511 1979-05-31 1980-05-30 Amino compounds and use of amino compounds as antioxydant in lubricating oils Expired EP0022281B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US4399679A 1979-05-31 1979-05-31
US43996 1979-05-31

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EP0022281A1 EP0022281A1 (en) 1981-01-14
EP0022281B1 true EP0022281B1 (en) 1983-09-14

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EP19800200511 Expired EP0022281B1 (en) 1979-05-31 1980-05-30 Amino compounds and use of amino compounds as antioxydant in lubricating oils

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EP (1) EP0022281B1 (2)
JP (1) JPS55161894A (2)
BR (1) BR8003141A (2)
CA (1) CA1138472A (2)
DE (1) DE3064808D1 (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9920285D0 (en) 1999-08-27 1999-10-27 Johnson Matthey Plc Improved catalytic process

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH312721A (de) * 1952-02-07 1956-02-29 Yair Dr Sprinzak Verfahren zur Herstellung sekundärer cyclischer Benzylamine
US3366683A (en) * 1963-10-23 1968-01-30 Gen Aniline & Film Corp Method for the production of benzyl anilines
US3579582A (en) * 1967-02-16 1971-05-18 Universal Oil Prod Co Hydroxy and/or hydrocarbyloxy and amino substituted tetrahydronaphthalenes
US3822284A (en) * 1970-07-16 1974-07-02 Shell Oil Co 1-and 3-substituted (3,5-di-t-butyl-4-hydroxybenzyl)carbazole

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

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EP0022281A1 (en) 1981-01-14
JPS55161894A (en) 1980-12-16
BR8003141A (pt) 1980-12-23
JPH0144276B2 (2) 1989-09-26
DE3064808D1 (en) 1983-10-20
CA1138472A (en) 1982-12-28

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