Classifications

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  • 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
  • C10M141/08—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
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  • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
  • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
  • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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  • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
  • C10M135/20—Thiols; Sulfides; Polysulfides
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  • 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
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  • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
  • C10M135/20—Thiols; Sulfides; Polysulfides
  • C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
  • C10M135/30—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups; Derivatives thereof
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  • 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
  • C10M135/34—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon only
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  • 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
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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
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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
  • C10M2215/066—Arylene diamines
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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
  • C10M2215/067—Polyaryl amine alkanes
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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
  • C10M2215/068—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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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
  • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
  • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
  • C10M2219/088—Neutral salts
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
  • C10M2219/106—Thiadiazoles
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
  • C10M2219/108—Phenothiazine
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  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

• the present invention relates to new lubricant and hydraulic fluid compositions with high stability against oxidative degradation.
• additives from the series of diphenylamines as described in EP-A-0 149 422, are added to the lubricating oils, for example.
• New lubricant compositions have now been found which have further improved properties compared to the previously known products and are distinguished by high stability against oxidative degradation.
• the present invention relates to a composition
• a composition comprising at least one lubricant, in particular based on mineral oil, synthetic oils or mixtures thereof, or a hydraulic fluid, and a mixture of one or more compounds from the series A) and one or more compounds from the series B.
• the compounds of series A) having the general formula have in which R1 and R1 'are the same or different and -H, alkyl having 1 to 24 carbon atoms, cycloalkyl having 5 to 12 carbon atoms or phenyl- (C1-C4) alkyl and n is a number from 0 , 1 or 2 means and the compounds of series B) the general formula have in which R2 -H, alkyl having 1 to 24 carbon atoms, phenyl, substituted with NO2, Cl, Br, F, C1-C12-alkyl and / or C1-C12-alkoxy phenyl, phenyl- (C1-C4 ) alkyl, phenyl of the general formula wherein R6 -H, alkyl having 1 to 20 C atoms or phenyl- (C1-C4) alkyl and x is 1 or 2, or R2 means furyl, tetrahydrofuryl, 2-methylfuryl, 2-methylte
• substituents R1, R1 ′, R2, R3 or R5 are alkyl having 1 to 24 carbon atoms, these are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, 2-butyl, t-butyl, pentyl, 1- Methylphenyl, isopentyl, hexyl, 1,3-dimethylbutyl, heptyl, 1,1,3,3-tetramethylbutyl, 1-methylhexyl, 3-heptyl, octyl, 2-ethylhexyl, 1-methylheptyl, nonyl, 1,1,3- Trimethylhexyl, decyl, undecyl, dodecyl, 1-methylundecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octa
• R1 or R1 'cycloalkyl having 5 to 12 carbon atoms it is about a group of the formula where a is a number from 3 to 9.
• This cycloalkyl group can optionally be substituted by C1-C4-alkyl. Examples are cyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, t-butylcyclohexyl, cyclooctyl and cyclododecyl.
• the substituent phenyl- (C1-C4) alkyl is preferably benzyl.
• R2 or R3 can represent a phenyl substituted by C1-C12-alkyl.
• C1-C12 alkyl can be taken from the above list. Examples are methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, t-butylphenyl, isopropylphenyl, di-t-butylphenyl or 2,6-di-t-butyl-4-methylphenyl.
• R4 'in formula (IIa) can mean unsubstituted or C1-C18 alkyl substituted alkylene.
• Examples include methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, decamethylene or dodecamethylene, furthermore di-1,1-dimethyl-2,2-dimethyldimethylene, 1,1,2-trimethyl-2- n-propyltrimethylene, 2-ethyl-2-n-butyltrimethylene, 1-iso-propyl-2,2-dimethyltrimethylene, 1-methyltrimethylene, 2,2-dimethyltrimethylene, 1,1,3-trimethylene or 2,2,4- or 2,4,4-trimethylhexamethylene.
• R4 ' represents dimethylene or trimethylene.
• R1 and R1 ' are the same or different in the compounds of the formula I and are -H, alkyl having 4 to 12 carbon atoms, cycloalkyl and preferably cyclohexyl, or phenyl- (C1-C4) alkyl.
• R1 and R1 ' represent -H or alkyl having 4 to 8 carbon atoms.
• reaction products can be used as compounds of series A) obtainable by the method according to EP-A-0 149 422 can be used.
• the reaction product produced by the process mentioned is preferably used as such.
• diphenylamine is reacted with diisobutylene in the presence of a catalyst to form a liquid antioxidant composition such that the reaction of diphenylamine with an excess of diisobutylene is carried out in the presence of an active alumina catalyst such that the concentration of diisobutylene over the reaction period in the It is kept essentially constant that the reaction temperature is at least 160 ° C., that 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 10% by weight, preferably below 5% by weight, that the catalyst and unreacted diisobutylene are removed and that the resulting liquid product is isolated.
• This process results in a liquid reaction mixture containing 4,4'-di-tert-ocytyldiphenylamine.
• This reaction mixture comprising the compounds from the series A), is preferably used for the mixture together with the compounds from the series B), as mentioned.
• This mixture can be obtained in particular by the process mentioned.
• R4 denotes alkyl having 4 to 12 carbon atoms, phenyl or - (CH2) -OR5, where R5 is alkyl with 1 to 18 carbon atoms and preferably for alkyl with 8-13 carbon atoms and s is 1 or 2.
• the very particularly preferred compounds of the formula II include those in which R2 is -H, alkyl having 1 to 8 C atoms, furyl or phenyl, then compounds in which R3 -H, alkyl having 1 to 8 C atoms or where R4 has the meaning given above.
• R4 preferably has the meaning of alkyl having 8 to 12 carbon atoms or -CH2- -OR5, wherein R5 is branched alkyl having 8 to 13 carbon atoms and in particular tert-butyl or 2-ethylhexyl.
• Compounds from series B) can be used as individual compounds or as a mixture of different compounds from series B) with one another in each case in a mixture with a compound from series A) or a mixture of compounds from series A).
• the lubricant composition accordingly contains a mixture of at least one compound from the series A) with the formula I and at least one compound from the series B) with the formula II.
• Mixtures of 1 to 9 parts by weight of the compound or compounds of series A) with 9 to 1 parts by weight of the compound or compounds of series B), and preferably of 2 to 8 parts by weight of the compound or compounds of series A) and 8, are expedient up to 2 parts by weight of the compound or the compounds of series B) applied.
• Mixtures are preferably also used, comprising as compounds of series A) a reaction mixture containing 4,4'-di-tert-octyldiphenylamine and as compounds of series B), a compound of the formula where i-C8H17 is a mixture of branched isomers each having 8 carbon atoms, in a mixing ratio of A) to B) from 9: 1 to 1: 1 parts by weight.
• the mixing ratio of A) to B) is 9: 1 or 7: 3 or 1: 1 parts by weight.
• a preferred mixture contains as compounds of series A) a reaction mixture containing 4,4'-di-tert-octyldiphenylamine and, as a compound of series B), a compound of the formula where i-C8H17 is a mixture of branched isomers each having 8 carbon atoms, in a mixing ratio of A) to B) from 9: 1 to 1: 9 parts by weight.
• the mixing ratio of A) to B) is 9: 1 or 3: 7 or 1: 9 parts by weight.
• the compounds of formula II are for example from Reid, "Organic Chemistry of Bivalent Sulfur", vol. 3, pp. 320-341, Chemical Publishing Company, New York, 1960, and can be synthesized in a manner known per se.
• the following reaction routes are available, for example: this method can be carried out without a solvent or in a solvent, for example in cyclohexane, toluene, xylene or nitro or chlorobenzene.
• the process can be carried out either without the presence of a solvent or e.g. perform in methanol, ethanol, hexane or toluene as the solvent.
• the mixture according to the invention is suitable for adding lubricants, in particular those based on mineral oils, synthetic oils or semi-synthetic lubricating oils and hydraulic fluids.
• the lubricant can thus be, for example, an oil based on a mineral oil or a synthetic oil, or a fat.
• mineral oil includes all mineral oils for lubrication purposes, such as hydrocarbon-based mineral oils.
• Synthetic oils can be, for example, aliphatic or aromatic carboxyl esters, polymeric esters, polyalkylene oxides, phosphoric acid esters, poly- ⁇ -olefins, silicones, glycols, polyglycols or polyalkylene glycols.
• the lubricants can additionally contain other additives which are added in order to further improve the basic properties of lubricants; these include: other antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents, thickeners, biocides, anti-foaming agents, demulsifiers and emulsifiers, as well as high-pressure additives and friction reducers.
• additives which are added in order to further improve the basic properties of lubricants; these include: other antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents, thickeners, biocides, anti-foaming agents, demulsifiers and emulsifiers, as well as high-pressure additives and friction reducers.
• 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-cyclopentyl4-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.
• esters of ⁇ - (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols e.g.
• Methanol diethylene glycol, octadecanol, triethylene glycol, 1,6-hexanediol, pentaerythritol, neopentyl glycol, tris-hydroxyethyl isocyanurate, thiodiethylene glycol, bis-hydroxyethyl oxalic acid diamide.
• esters of ⁇ - (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid with mono- or polyhydric alcohols e.g.
• 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 passivators examples are:
• Triazoles for copper, for example: Triazoles, benzotriazoles and their derivatives, 2-mercaptobenzothiazole, 5,5'-methylenebisbenztriazole, 4,5,6,7-tetrahydrobenzetriazole, 2,5-di-mercaptothiadiazole, salicylidene-propylenediamine, salts of salicylaminoguanidine.
• 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 low mixers are:
• dispersants / surfactants examples are:
• Polybutenylsuccinic acid imides polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulfonates and phenolates.
• wear protection additives are:
• Compounds containing sulfur and / or phosphorus and / or halogen such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl disulfides, triphenylphosphorothionates, diethanolaminomethyltolyltriazole and di (2-isooctyl) aminomethyltolyl.
• the invention also encompasses the use of mixtures of compounds of series B) as an antioxidant in lubricants and hydraulic fluids.
• the additives according to the invention are also effective in lubrication systems of the type described above, but which additionally have a co-lubrication system which contains customary amounts of solid lubricants, such as graphite, boron nitride, molybdenum disulfide or polytetrafluoroethylene.
• solid lubricants such as graphite, boron nitride, molybdenum disulfide or polytetrafluoroethylene.
• the compounds of the series A) and the compounds of the series B) can be mixed with one another in the proportions indicated and the mixture can then be mixed in with the lubricant or the hydraulic fluid in the quantities mentioned. It is also expedient to mix the compounds of the series A) and the compounds of the series B) separately with the lubricant or the hydraulic fluid, the quantitative proportions given also having to be adhered to in this case. The production of so-called masterbatches is also possible.
• the reaction mass is cooled to 60 ° C. and the catalyst is removed by vacuum filtration.
• the filtrate is transferred to a distillation apparatus and the pressure is reduced to 26 mbar with heating and stirring.
• the liquid has the approximate composition of 3.2% by weight diphenylamine, 13.2% by weight 4-tert-butyldiphenylamine, 25.3% by weight of compounds from the 4-tert-octyldiphenylamine series, 4.4 '-Di-tert-butylamine and 2,4,4'-tris-tert-butylamine, 24.2% by weight of compounds from the series 4-tert-butyl-4'-tert-octyldiphenylamine, 2.2' - or 2,4'-di-tert-octyldiphenylamine and 2,4-di-tert-butyl-4'tert-octyldiphenylamine and 18.2% by weight of 4,4'-di-tert-octyldiphenylamine and 6.0 Wt .-% 2,4-di-tert-octyl-4'-tert-butyldiphenylamine, as well as further shares in other higher alkyl
• the thioketal compound according to a) and the reaction mixture according to b) are mixed with one another in the amounts evident from example 4. These latter mixtures are mixed in an amount of 0.25% by weight, based on the oil, of a mineral oil of the Mobil 15 SS4 type.
• the thioketal compound according to a) and the reaction mixture according to b) are mixed with one another in the amounts evident from example 4. These latter mixtures are mixed in an amount of 0.25% by weight, based on the oil, of a mineral oil of the Mobil 15 SS4 type.
• the compounds according to a) and the reaction mixture according to b) are combined in the proportions from a) to b) of 9: 1, 7: 3, 1: 1, 3: 7 and 1: 9 parts by weight and processed into corresponding mixtures.
• the oil to be tested (Mobil 15 SS4) is heated to 95 ° C. in the presence of water, oxygen, an iron-copper catalyst and the stabilizer for 1000 hours.
• the TAN acid value (in mg KOH consumption per g test oil) and the sludge (SLUDGE) (in mg residue per batch) are then determined.
• the results are summarized in Table 1.
• the concentration of the stabilizer mixtures is 0.25% by weight, based on the oil.
• Table 2 below shows the measured values from the TOST test for various mixtures of compounds according to Example 3. The test procedure and conditions are given above, except for the test duration which is 500 hours and the oil (mineral oil BB).
• Table 2 Example 4 Stabilizer (total 0.25% by weight) mixture of 500 hours TOST % By weight according to the example % By weight according to the example TAN (mg KOH / g oil) SLUDGE (mg) G) 10 3a) 90 3b) 0.24 58 H) 30 3a) 70 3b) 0.25 38 i) 50 3a) 50 3b) 0.11 14 k) 70 3a) 30 3b) 0.08 27th l) 90 3a) 10 3b) 0.08 87

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