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EP0398215A1 - Compositions lubrifiantes - Google Patents

Compositions lubrifiantes Download PDF

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Publication number
EP0398215A1
EP0398215A1 EP90109025A EP90109025A EP0398215A1 EP 0398215 A1 EP0398215 A1 EP 0398215A1 EP 90109025 A EP90109025 A EP 90109025A EP 90109025 A EP90109025 A EP 90109025A EP 0398215 A1 EP0398215 A1 EP 0398215A1
Authority
EP
European Patent Office
Prior art keywords
tert
compounds
diphenylamine
octyldiphenylamine
compound
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.)
Withdrawn
Application number
EP90109025A
Other languages
German (de)
English (en)
Inventor
Miles Dr. Hutchings
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0398215A1 publication Critical patent/EP0398215A1/fr
Withdrawn legal-status Critical Current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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • 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
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/20—Thiols; Sulfides; Polysulfides
    • C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M135/24—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/20—Thiols; Sulfides; Polysulfides
    • C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M135/26—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
    • C—CHEMISTRY; METALLURGY
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
    • 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
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
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    • 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
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    • 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
    • C10M2215/064—Di- and triaryl amines
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    • 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
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/066—Arylene diamines
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/067—Polyaryl amine alkanes
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    • C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • 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
    • C10M2215/30—Heterocyclic compounds
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol-fuelled engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines
    • 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
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • 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
    • C10N2040/32—Wires, ropes or cables lubricants
    • 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
    • C10N2040/34—Lubricating-sealants
    • 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
    • C10N2040/36—Release agents or mold release agents
    • 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
    • C10N2040/38—Conveyors or chain belts
    • 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
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • 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
    • C10N2040/42—Flashing oils or marking oils
    • 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
    • C10N2040/44—Super vacuum or supercritical use
    • 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
    • C10N2040/50—Medical uses

Definitions

  • the invention relates to new lubricant compositions with high stability against oxidative degradation.
  • additives are generally added to lubricants to improve their performance properties. Since lubricants require a high load-bearing capacity to transmit larger forces, so-called high-pressure and anti-wear additives are added to them, which greatly reduces the signs of wear that would otherwise occur. On the other hand, e.g. If oxygen and moisture act on a metal surface at the same time, corrosion can occur, which is why corrosion inhibitors are added with the aim of preventing such substances from entering the metal surface. The oxidation reactions in a lubricant that occur, for example, at elevated temperature due to atmospheric oxygen can be prevented by adding antioxidants. It is known that certain substances as additives for lubricants can combine a number of such properties; they are referred to as so-called multi-purpose additives. Such materials are of course in high demand for economic and practical reasons.
  • additives which prevent the oxidative degradation of the lubricants and ensure high storage and effectiveness stability.
  • additives from the series of diphenylamines as described in EP-A-0 149 422, are added to the lubricating oils, for example.
  • thio group ether-containing compounds are known which likewise prevent the oxidative degradation of the lubricants and also combine other properties of a multipurpose additive.
  • Stabilized organic materials are known from US Pat. No. 4,829,115, containing a phenolic and / or amine stabilizer and a synergist with a molecular weight above 400 and a structural element where R z. B. means alkyl in the molecule.
  • compositions containing lubricants have now been found which have very outstanding properties and which clearly differ in their action behavior from the compositions described above.
  • the compositions according to the invention in particular have improved properties with regard to oxidative degradation and consequently ensure high stability in storage and effectiveness.
  • the lubricating oils for internal combustion engines are described as the lubricating oils that serve the lubricating circuit of an internal combustion engine from the crankcase or dry sump.
  • Internal combustion engines mean, for example, reciprocating or rotary piston engines with internal or external ignition (diesel or petrol principle).
  • component B) contained in the composition itself is liquid even at room temperature and is therefore particularly suitable for incorporation into lubricants, such as industrial oils and lubricating oils for internal combustion engines.
  • the composition of the diphenylamine mixture B1) is determined by its production (reaction of diphenylamine with diisobutylene), which is described below.
  • fractions c), d) and e) the compounds denoted by i) are the main components.
  • the preferred content of fraction e) is 15 to 29% by weight.
  • the mixture of diphenylamine compounds B1) can be obtained, for example, by reacting diphenylamine with diisobutylene, the reaction of diphenylamine being carried out with an excess of diisobutylene in the presence of an active alumina catalyst, the concentration of diisobutylene is kept substantially constant over the reaction period, the reaction temperature is at least 160 ° C., the reaction is carried out until the 4,4′-di-tert-octyldiphenylamine content, based on the reaction mass without catalyst, is below 30% by weight, preferably below 25% by weight, and the diphenylamine content below 5% by weight, the catalyst and unreacted diisobutylene are removed and the resulting liquid product is isolated.
  • the most important process steps are characterized, for example, by the fact that the reaction is expediently carried out by pouring the diphenylamine and the catalyst into the reaction vessel and by heating the mixture to at least 160 ° C., preferably to at least 165 ° C., and preferably with stirring. Diisobutylene can then be metered into the hot mixture of diphenylamine and catalyst in such a way that the temperature of the mixture does not drop below 160 ° C., preferably not below 165 ° C.
  • the temperature is kept at at least 160 ° C. with frequent sampling until the product, without catalyst, less than 30% by weight of 4,4′-di-tert-octyldiphenylamine and less than 10% by weight contains diphenylamine.
  • the temperature at which the process according to the invention is carried out is at least 160 ° C, but can be considerably higher, e.g. up to 250 ° C.
  • the usual maximum temperature is around 190 ° C.
  • the time over which the diisobutylene can be added to the hot mixture of diphenylamine and catalyst can vary within a wide range depending on the reaction temperature, but is usually within 3-30 hours.
  • the molar ratio of diphenylamine to diisobutylene can vary over a wide range, but is preferably kept in the range from 1: 1.11 to 1: 2.5, particularly preferably 1: 1.3 to 1: 1.75, in order to reduce the cost of To reduce the starting material and to keep the addition time of diisobutylene as short as possible.
  • the catalyst is expediently recovered by vacuum filtration of the hot reaction mixture. Excess diisobutylene can easily be recovered by vacuum distillation of the reaction mixture.
  • the active alumina catalyst used in the process according to the invention preferably has a free moisture content of less than 10% by weight, particularly preferably one of less than 5% by weight.
  • Fulcat® 14 Fulmont® 700C
  • Fulmont® 237 catalyst K-10 (Süd-Chemie)
  • Fulcat® 22B an alumina activated with sulfuric acid
  • the Fulcat and Fulmont catalysts are commercially available from Laporte Industries.
  • a particularly preferred diphenylamine mixture B1) contains 3.2% diphenylamine, 13.2% mono-t-butyldiphenylamine, 25.3% mono-t-octyldiphenylamine and di-t-butyldiphenylamine, 24.2% t-butyl-t -octyldiphenylamine, 24.3% di-t-octyldiphenylamine and other higher alkylated diphenylamines, the content of 4,4'-di-t-octyldiphenylamine being 18.2%, and other smaller amounts of diphenylamines with partially modified side chains and polymers to 100%.
  • compositions according to the invention contain C) at least one compound of the general formula I, as described above.
  • R.sup.1 and R.sup.2 in formula I independently of one another, represent an alkyl group having 3 to 9 carbon atoms and can be, for example, propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2 -Ethylhexyl, 2-ethylbutyl, 1-methylpentyl, 1,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylhexyl, isoheptyl, 1-methylheptyl, 1,1,3-trimethylhexyl, nonyl or tert.- Act nonyl.
  • R1 and R2 in formula I independently of one another, represent a C5-C10 cycloalkyl, examples of which are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl or cyclodecyl. Cyclohexyl is preferred. Another preferred group is the pinan-10-yl of the formula
  • Preferred compounds of formula I for R1 and R2 have tert-C4-tert-C7-alkyl groups or C5- or C6-cycloalkyl.
  • the compounds of the formula I are prepared in a manner known per se. They are e.g. also described in European Patent Application No. 0349 483.
  • alkyl thiaglycidyl ethers serving as an intermediate for the compounds of the formula I are prepared in the following manner: wherein the substituent R has the meaning already given for R1 or R2.
  • a phase transfer catalyst such as, for example, tetrabutylammonium chloride, is particularly advantageous for this reaction.
  • the preparation of alkyl thiaglycidyl ethers is also described in US-A-2 965 652, US-A-2 731 437 and BE-A-609 375.
  • alkyl-thiaglycidyl ethers of the formula Y can then be reacted, for example, with sodium hydrogen sulfide to give compounds of the type of the formula Ia or Ic.
  • Compounds of the type of the formula Ib can be obtained, for example, by reacting compounds of the formula Y with 1,2-dimercaptoethane.
  • compositions according to the invention containing components B) and C) are preferred in a mutual weight ratio of B) to c) of 1 to 0.6 to 1 to 3, in particular 1 to 1.8 to 1 to 2.2 .
  • compositions according to the invention contain as lubricant A) an industrial oil or a lubricating oil for internal combustion engines.
  • compositions according to the invention contain A) an industrial oil and at least one component B) selected from components B1) to B10), as described above, and C) at least one compound of the general formula I, as described above.
  • compositions are particularly suitable for use in turbines, in hydraulic systems or for compressors.
  • compositions according to the invention contain A) a lubricating oil for internal combustion engines, at least one component B) selected from components B1) to B10) as described above, C) at least one compound of the general formula I as described above, and D) at least a compound of formula II as mentioned below.
  • R11 is C1-C12 alkyl, it is straight-chain or branched alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, straight-chain or branched Pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl.
  • alkyl radicals such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, straight-chain or branched Pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl.
  • R11 is C2-C12-alkyl which is interrupted by -O-, -S- or -C (O) O-
  • the hetero atom or the C (O) O group can be in any possible position, and the C2-C12 alkyl radical can be single or multiple be interrupted, the interruption can take place both by the same or different heteroatoms and by C (O) O groups. An interruption is preferred.
  • R11 represents phenyl or naphthyl substituted by C1-C12-alkyl, the phenyl or naphthyl radical can be substituted one or more times, but preferably mono- or disubstituted;
  • C1-C12-alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, straight-chain or branched nonyl or dodecyl.
  • R11 is C5-C12 cycloalkyl, it is for example cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl or cyclododecyl, preferably cyclohexyl.
  • R11 is C--C12-cycloalkyl substituted by C1-C4, it can be a single or multiple substitution, but is preferably a simple substitution; such as methylcyclohexyl, trimethylcyclohexyl, butylcyclohexyl or propylcyclopentyl.
  • R11 is C7-C13 aralkyl, it is, for example, benzyl, 1- or 2-phenethyl, 3-phenylpropyl, ⁇ , ⁇ -dimethylbenzyl, 2-phenylisopropyl, 2-phenylhexyl, benzhydryl or naphthylmethyl, but preferably benzyl .
  • M represents a k-valent metal cation
  • k in the case of k equals 1, it is, for example, Li ⁇ , Na ⁇ , K ⁇ and, in the case of k equals 2, eg Mg 2 ⁇ , Ca 2 ⁇ , Ba 2 ⁇ , Zn 2 ⁇ .
  • Preferred metal cation M is Zn 2 ⁇ .
  • a further preferred embodiment is represented by compositions in which in the compounds of the formula II R11 is C1-C12-alkyl, which is optionally interrupted by -O-, -S- or -C (O) O-, or unsubstituted or by C1- C12-alkyl, especially C8-C12-alkyl, substituted phenyl or naphthyl; Cyclohexyl or benzyl, where R11 is preferably C3-C12 alkyl, which is optionally interrupted by -C (O) O-, or phenyl or nonylphenyl.
  • compositions in which X in the compounds of the formula II is oxygen, furthermore those in which in the compounds of the formula II X1 and X2 are oxygen or those in which in the compounds of the formula II X and X2 are sulfur and X1 are oxygen mean.
  • compositions in which M in the compounds of the formula II denotes Zn2+.
  • compositions in which in the compounds of the formula II X and X2 are sulfur, X1 is oxygen, R11 is C3-C8-alkyl, n * 2 and M is Zn2+.
  • compositions in which X in the compounds of formula II is sulfur, further in those in which in the compounds of formula II X is sulfur and X 1 and X 2 are oxygen; or those in which, in the compounds of the formula II, X is oxygen and X1 and X2 are sulfur.
  • the compounds of formula II according to the present invention can advantageously be added to a lubricating oil for internal combustion engines, as mentioned above.
  • the use of the compounds of the formula II in lubricants in general and in industrial oils in particular is readily possible, but very often is not necessary because of a different type of load on such oils.
  • Components B), accordingly the compounds or mixtures designated B1) to B10), alone or in a mixture with one another, C) compounds of the formula I and, if appropriate, D), compounds of the formula II, are added to the respective lubricant A) for example in total in an amount of 0.01 to 10% by weight, advantageously in an amount of 0.03 to 5% by weight, preferably in an amount of 0.05 to 3% by weight and very particularly preferably of 0.5 to 1.5 wt .-%, based on the finished Lubricant composition added.
  • An amount of 0.5 to 0.75% by weight of compounds B) and C) together, based on the finished lubricant composition is very particularly preferred.
  • An amount of 1.25 to 1.5% by weight of compounds B), C) and D), based on the finished lubricant composition is also very particularly preferred.
  • the quantitative ratios between B) and C) are mentioned above. If D), a compound of the formula II, is used, the quantitative ratio [B) + C)] to D) is, for example, 10 to 1 to 0.5 to 1, preferably 2 to 1 to 0.6 to 1.
  • An amount of 0.5 to 0.75% by weight of compounds B) and C) together is very particularly preferred, with a content of compound D) of the formula II of 0.75% by weight, based on the finished lubricant composition.
  • the additives B), C) and D) can be added to the lubricant in a manner known per se.
  • the compounds are readily soluble in oil, for example. It is also possible to produce a so-called masterbatch, which can be diluted to the appropriate concentration with the appropriate lubricant depending on the consumption.
  • the lubricants in question are based, for example, on mineral or synthetic oils or mixtures thereof.
  • the lubricants are familiar to the person skilled in the art and are found in the relevant specialist literature, for example in Dieter Klamann, "Lubricants and Related Products” (Verlag Chemie, Weinheim, 1982), in Schewe-Kobek, "The Lubricant Pocket Book” (Dr. Alfred Hüthig- Verlag, Heidelberg, 1974) and in "Ullmann's Encyclopedia of Technical Chemistry", Vol. 13, pages 85-94 (Verlag Chemie, Weinheim, 1977).
  • the lubricants are especially oils. Fats, for example based on a mineral oil, can also be included.
  • the mineral oils are based in particular on hydrocarbon compounds.
  • Examples of synthetic lubricants include lubricants based on the aliphatic or aromatic carboxylic esters, the polymeric esters, the polyalkylene oxides, the phosphoric acid esters, the poly- ⁇ -olefins or the silicones, a diester of a dibasic acid with a monohydric alcohol, e.g. Dioctyl sebacate or dinonyl adipate, a triester of trimethylolpropane with a monohydric acid or with a mixture of such acids, e.g.
  • mineral oils e.g. Poly- ⁇ -olefins, ester-based lubricants, phosphates, glycols, polyglycols and polyalkylene glycols, and mixtures thereof with water.
  • the lubricants can additionally contain other additives which are added in order to further improve the basic properties thereof. These include other antioxidants, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents and other wear protection additives.
  • 2,6-di-tert-butyl-4-methylphenol 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-iso-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2- ( ⁇ -methylcyclohexyl ) -4,6-dimethylphenol, 2,6-di-octadecyl-4-methylphenol, 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol.
  • mono- or polyhydric alcohols e.g. with methanol, diethylene glycol, octadecanol, triethylene glycol, 1,6-hexanediol, pentaerythritol, neopentyl glycol, tris-hydroxyethyl isocyanurate, thiodiethylene glycol, bis-hydroxyethyl oxalic acid diamide.
  • mono- or polyhydric alcohols e.g. with methanol, diethylene glycol, octadecanol, triethylene glycol, 1,6-hexanediol, pentaerythritol, neopentyl glycol, tris-hydroxyethyl isocyanurate, thiodiethylene glycol, di-hydroxyethyl oxalic acid diamide.
  • Aliphatic or aromatic phosphites esters of thiodipropionic acid or thiodiacetic acid, or salts of dithiocarbamide or dithiophosphoric acid.
  • metal deactivators e.g. for copper
  • metal deactivators e.g. for copper
  • Triazoles benzotriazoles and their derivatives, tolutriazoles and their derivatives, 2-mercaptobenzthiazole, 2-mercaptobenztriazole, 2,5-dimercaptobenztriazole, 2,5-dimercaptobenzthiadiazole, 5,5'-methylenebisbenzotriazole, 4,5,6,7-tetrahydrobenztriazole, salicylides -propylenediamine, salicylaminoguanidine and its salts.
  • rust inhibitors are:
  • viscosity index improvers examples are:
  • Polyacrylates polymethacrylates, vinyl pyrrolidone / methacrylate copolymers, polyvinyl pyrrolidones, polybutenes, olefin copolymers, styrene / acrylate copolymers, polyethers.
  • pour point depressants examples are:
  • dispersants / surfactants examples are:
  • wear protection additives are:
  • Compounds containing sulfur and / or phosphorus and / or halogen such as sulfurized vegetable oils, tritolyl phosphate, chlorinated paraffins, alkyl and aryldi and tri sulfides, triphenylphosphorothionates, diethanolaminomethyltolyltriazole, di (2-ethylhexyl) aminomethyltolyltriazole.
  • the present invention also relates to the use of the above-mentioned mixture of at least one component B) and at least one compound of the general formula I as an antioxidant in lubricants.
  • compositions containing A) a base oil of the type AARG 51 [formulated 15W-50 motor oil with a concentration of zinc dialkyldithiophosphate of 0.75%, phosphorus content 0.06%], certain concentrations (B1) of the components of the mixture of diphenylamine Prepared compounds and (C) a compound of formula I.
  • the diphenylamine mixture (B1) for all three examples contains 3.2% diphenylamine, 13.2% mono-t-butyldiphenylamine, 25.3% mono-t-octyldiphenylamine and di-t-butyldiphenylamine, 24.2% t- Butyl-t-octyldiphenylamine, 24.3% di-t-octyldiphenylamine and other higher alkylated diphenylamines, the content of 4,4'-di-t-octyldiphenylamine being 18.2%, and other smaller amounts of diphenylamines with partially modified ones Side chains and polymers to 100%.
  • TFOUT test ASTM D 4742 Thin-Film Oxygen Uptake Test, National Bureau of Standards (NBS), Washington DC USA
  • RBOT Ritary Bomb Oxidation Test for Mineral Oils
  • the oil to be tested (1.5 g) is in a glass, which is in a steel container (bomb), in the presence of 2% water, a liquid oxidized, nitrated fraction of petrol as a catalyst (4% concentration ) and a liquid metal naphtenate as a further catalyst (4% usage con concentration) (the water and the two liquid catalyst substances are available from the National Bureau of Standards (NBS) with analysis certificate under No. Standard Reference Material 1817) at an oxygen pressure of 6.3 bar (90 psi) (oxygen volume 65 ml ).
  • NBS National Bureau of Standards
  • the bomb rotates in an inclined position at 100 rpm. in a liquid bath at 160 ° C. The inclined position and the rotation cause a film-like distribution of the oil on the outer surface of the glass container.
  • the oil After a certain induction time, the oil begins to oxidize under these conditions.
  • the oxidation causes oxygen consumption, which is visible in a significant drop in pressure.
  • the time until the start of the oxidation in minutes, the so-called induction time, is taken as a measure of the oxidation stability.
  • compositions containing an oil of the type XE9 [an ISO VG32 mineral oil from EXXON, sold under the name EXXON 1243, containing 4.5% CA, 60.5% CP, 35% CN and 0.19% S], containing one mixture of additives known per se from 0.075% (% by weight, based on the composition in each case) of 2,6-di-tert-butylphenol as an antioxidant, 0.025% of an alkenylsuccinic acid partial ester as a corrosion inhibitor and 0.025% of a benzotriazole as a copper metal deactivator, will once with 0.025% diphenylamine mixture (B1) according to example 1 and once with 0.025% diphenylamine mixture (B1) according to example 1 and 0.015% of a compound (C) of formula I [i) according to example 1] manufactured and subjected to the TOST-LIFE test.
  • an oil of the type XE9 an ISO VG32 mineral oil from EXXON, sold under the name EXX
  • composition to be tested is heated to 95 ° C. in the presence of water, oxygen, an iron-copper catalyst and the stabilizer. If the acid value TAN (in mg KOH consumption per g test oil) is 2 mg KOH / g, the test is stopped and the time in hours from the start of the test to the stated TAN value is determined.
  • acid value TAN in mg KOH consumption per g test oil
  • a base oil of the type AARG 51 formulated motor oil with a concentration of zinc dialkyldithiophosphate of 0.75%, phosphorus content 0.06%
  • the result is a TFOUT value of 207 min.
  • compositions containing (A) an oil of the type AARG 51 [formulated motor oil with 0.75% by weight zinc dialkylkdithiophosphate (phosphorus content 0.06% by weight)], in each case 0.25% by weight of different compounds of the series ( B) and 0.5 wt .-% (C), a compound of the formula are subjected to the TFOUT test ASTM D 4742.

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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)
EP90109025A 1989-05-17 1990-05-14 Compositions lubrifiantes Withdrawn EP0398215A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH184389 1989-05-17
CH1843/89 1989-05-17

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CA (1) CA2016838A1 (fr)
DD (1) DD299654A5 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0480875A1 (fr) * 1990-10-08 1992-04-15 Ciba-Geigy Ag Composition de lubrifiant
CN114634835A (zh) * 2022-01-26 2022-06-17 中国科学院兰州化学物理研究所 一种高导电、强润滑镓基液态金属润滑剂的制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8466096B2 (en) 2007-04-26 2013-06-18 Afton Chemical Corporation 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2367059A1 (fr) * 1976-10-06 1978-05-05 Ciba Geigy Ag Additifs pour lubrifiants
EP0149422A2 (fr) * 1983-12-08 1985-07-24 Ciba-Geigy Ag Préparation d'antioxidant
EP0166696A2 (fr) * 1984-06-29 1986-01-02 Ciba-Geigy Ag Additifs pour lubrifiants
EP0349483A2 (fr) * 1988-06-13 1990-01-03 Ciba-Geigy Ag Des additifs pour fluides fonctionnels

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2367059A1 (fr) * 1976-10-06 1978-05-05 Ciba Geigy Ag Additifs pour lubrifiants
EP0149422A2 (fr) * 1983-12-08 1985-07-24 Ciba-Geigy Ag Préparation d'antioxidant
EP0166696A2 (fr) * 1984-06-29 1986-01-02 Ciba-Geigy Ag Additifs pour lubrifiants
EP0349483A2 (fr) * 1988-06-13 1990-01-03 Ciba-Geigy Ag Des additifs pour fluides fonctionnels

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0480875A1 (fr) * 1990-10-08 1992-04-15 Ciba-Geigy Ag Composition de lubrifiant
CN114634835A (zh) * 2022-01-26 2022-06-17 中国科学院兰州化学物理研究所 一种高导电、强润滑镓基液态金属润滑剂的制备方法

Also Published As

Publication number Publication date
DD299654A5 (de) 1992-04-30
CA2016838A1 (fr) 1990-11-17
JPH03215596A (ja) 1991-09-20

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