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
  • C10M133/38—Heterocyclic nitrogen compounds
  • C10M133/40—Six-membered ring containing nitrogen and carbon only
• • 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
  • C10M2215/22—Heterocyclic nitrogen compounds
• • 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
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/221—Six-membered rings containing nitrogen and carbon only
• • 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
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
• • 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
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
  • C10M2215/226—Morpholines
• • 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
  • C10M2215/30—Heterocyclic compounds
• • 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
• • 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
  • C10N2040/251—Alcohol fueled 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

Definitions

• the present invention relates to lubricant compositions that are stabilized against oxidative degradation. Stabilization is achieved by adding a sterically hindered amine with a specific structure.
• Organic antioxidants for lubricants are primarily organic sulfur and phosphorus compounds, but also aromatic amines and phenols, especially sterically hindered phenols (see, for example, Ullmanns Encyklopadie der Technische Chemie, 4th edition, Verlag Chemie, Volume 20 (1981); page 541- 43). Sterically hindered amines for stabilizing lubricating oils have also been proposed, e.g. in US-A-4 069 199 or JP-A-85/28496.
• EP-A-356 677 proposes mixtures of aromatic amines and sterically hindered amines as antioxidants for lubricants, it also being possible to add phenolic antioxidants to these mixtures.
• R1, R3, R4, R5 or R6 are C1-C12-alkyl, this can be linear or branched alkyl, e.g. Methyl, ethyl, propyl, isopropyl, butyl, isoamyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl.
• R3 as C1-C18 alkyl can also e.g. Tetradecyl, hexadecyl or octadecyl.
• R1, R4, R5 and R6 as alkyl are preferably unbranched C1-C4 alkyl.
• R2, R3 or R5 are C5-C12-cycloalkyl, this can e.g. Cyclopentyl, cyclohexyl, methylcyclohexyl, cyclooctyl or cyclododecyl, but preferably cyclohexyl.
• R2 or R3 are C2-C5-hydroxyalkyl, this can e.g. 2-Hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl or 2-hydroxybutyl, but preferably 2-hydroxyethyl.
• R3 as C3-C18 alkoxyalkyl can e.g. 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 3-isopropoxypropyl, 3-butoxypropyl or 3-dodecyloxypropyl.
• R3 as C4-C20 dialkylaminoalkyl can e.g. 2-Dimethylaminoethyl, 3-dimethylaminopropyl, 3-di (isopropyl) aminopropyl or 3-di (octyl) aminopropyl.
• R6 as C1-C12 alkoxy is preferably C1-C4 alkoxy, especially methoxy or ethoxy.
• Preferred as component (B) is a compound of the formula I in which n is 1 or 2, R is hydrogen, R1 is hydrogen, C1-C4-alkyl, allyl, benzyl, acetyl or -OR5, R2 is hydrogen, C1-C4- Is alkyl or a group of the formula II, R3 if n is 1, is hydrogen, C1-C8-alkyl or C3-C1 Alk-alkoxyalkyl and if n is 2, is C2-C8-alkylene, and R5 C6-C10- Means alkyl, cyclohexyl or benzyl.
• a particularly preferred component (B) is a compound of the formula I in which n is 1 or 2, R is hydrogen, R1 is hydrogen, methyl or acetyl, R2 is hydrogen and R3, if n is 1, is hydrogen or C3-C8- Alkoxyalkyl means, and when n is 2, means C2-C6 alkylene.
• component (B) are the compounds of the formula I in which n is 2 and R3 is C2-C6alkylene.
• the compounds of formula I are known compounds which e.g. in U.S. Patents 3,684,765, 3,904,581 and 4,104,248. They are used as light stabilizers for organic polymers.
• Examples of individual compounds of the formula I are: 2,2,6,6-tetramethyl-4-butylaminopiperidine 2,2,6,6-tetramethyl-4-octylaminopiperidine 2,2,6,6-tetramethyl-4-cyclohexylaminopiperidine 2,2,6,6-tetramethyl-4- (N-hydroxyethylbutylamino) piperidine 2,2,6,6-tetramethyl-4- (3-methoxypropylamino) piperidine 2,2,6,6-tetramethyl-4- (3-dimethylaminopropylamino) piperidine Bis (2,2,6,6-tetramethylpiperidin-4-yl) amine 2,3,6-trimethyl-2,6-diethyl-4-isopropylaminopiperidine 1,2,2,6,6-pentamethyl-4-dodecylaminopiperidine 1,2,2,6,6-pentamethyl-4- (N-methyldodecylamino) piperidine 1-acetyl-2,2,
• Component (A) is a mineral or synthetic base oil, as is common for the preparation of lubricants.
• Synthetic oils can e.g. Esters of polycarboxylic acids or of polyols, they can be aliphatic polyesters or poly- ⁇ -olefins, silicones, phosphoric acid esters or polyalkylene glycols.
• the lubricant can also be a grease based on an oil and a thickener. Such lubricants are e.g. described in D. Klamann "Lubricants and related products", Verlag Chemie, Weinheim 1982.
• Component (B) is preferably added to the base oil in an amount of 0.05 to 5, in particular 0.1 to 2% by weight, based on the base oil.
• the addition can take place directly or a concentrated solution of (B) in the oil or in another solvent is first prepared and this solution is added to the oil.
• the lubricant composition may additionally contain other additives such as e.g. Phosphorus III esters, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, surfactants or wear protection additives.
• additives e.g. Phosphorus III esters, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, surfactants or wear protection additives.
• Examples of phosphorus III esters are: Triphenyl phosphite, decyl diphenyl phosphite, phenyl didecyl phosphite, tris- (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl-pentaerythritol diphosphite, tris- (2,4-di-tert.butylphenyl) -phosphite, diisodechritol , 4-di-tert.butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert.butylphenyl) -4,4′-biphenylene diphosphonite, bis- (2,6-di- tert-butyl-4
• metal deactivators for example for copper
• Triazoles 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.
• viscosity index improvers are: Polyacrylates, polymethacrylates, vinyl pyrrolidone / methacrylate copolymers, polyvinyl pyrrolidones, polybutenes, olefin copolymers, styrene / acrylate copolymers, polyethers.
• pour point depressants are: Polymethacrylate, alkylated naphthalene derivatives.
• dispersants / surfactants are: Polybutenylsuccinic acid amides or 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 di- and tri-sulfides, triphenyl phosphorothionates, diethanolaminomethyltolyltriazole, di (2-ethyltylylolyl) aminol.
• sulfurized vegetable oils such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl di- and tri-sulfides, triphenyl phosphorothionates, diethanolaminomethyltolyltriazole, di (2-ethyltylylolyl) aminol.
• the lubricant can also contain solid lubricants, such as graphite or molybdenum sulfide.
• Table 1 shows the induction times. The longer the induction time, the higher the antioxidant effect of the tested stabilizer.

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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)

Applications Claiming Priority (2)

Publications (2)

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• 1990
  • 1990-07-04 EP EP90112761A patent/EP0406825B1/de not_active Expired - Lifetime
  • 1990-07-04 DE DE9090112761T patent/DE59000955D1/de not_active Expired - Fee Related
  • 1990-07-05 CA CA002020552A patent/CA2020552A1/en not_active Abandoned
  • 1990-07-06 JP JP2179384A patent/JPH0345695A/ja active Pending

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