Classifications

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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
  • C10M141/06—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 nitrogen-containing compound
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  • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
  • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
  • C10M129/04—Hydroxy compounds
  • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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  • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
  • C10M129/68—Esters
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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
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  • 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
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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
  • C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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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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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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  • 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 invention relates to a phosphite-free lubricating oil composition with high stability against oxidative degradation.
• thermo-oxidative requirement profile of modern engine oils has changed as a result of new engine designs in the field of internal combustion engines with spark ignition.
• nitrogen oxides are increasingly formed, which in turn enter the crankcase as "blow-by" gases.
• the lubricating oil in the upper piston ring and cylinder area takes over the fine sealing to the combustion chamber. This can lead to contamination with high-boiling fuel components. These conditions are exacerbated by the presence of NO x .
• blow-by gases which have increasingly higher NO x contents, now cause the lubricating oil to be more susceptible to oxidation and "sludge germs" are formed, which ultimately lead to undesirable sludge deposits, which have become known as "black sludge”.
• EP-A 0 149 422 describes an antioxidant based on diphenylamines.
• additional additives such as hydroxylated thiophenyl ether, alkylidene bisphenols or thioesters of ⁇ - (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid can be used to further improve the basic properties.
• antioxidant compositions for use with lubricants are known from WO 87/05320. Certain hydroxylated thiomethyl ethers are described which are used in a mixture with diphenylamines.
• EP-A 0 049 133 describes a stabilizer composition which, inter alia, is also suitable for lubricating oils, known, containing diphenylamines, phosphites, thiodipropionic acid esters and optionally one or more polysubstituted phenols.
• Phosphite as a constituent of a stabilizer, which is used in an engine lubricating oil, must be limited or preferably omitted in view of a possible deactivation of the catalyst by phosphorus compounds escaping with the exhaust gas.
• New lubricant compositions and in particular lubricating oil compositions, have now been found which have further improved properties compared to the previously known products, are distinguished by high stability against oxidative degradation and in particular are able to sustainably reduce the negative effects of black sludge in spark ignition internal combustion engines.
• R 1 has the meaning of H, alkyl having 1 to 18 C atoms, allyl, methallyl, benzyl or C 1 -C 11 alkyl-substituted benzyl,
• composition according to the invention relates to phosphite-free lubricating oil compositions containing (a) a mineral oil or a synthetic oil or a mixture thereof and (b) a mixture as mentioned above.
• the composition expediently relates to those of the type described above, in which the lubricating oil is an oil for spark-ignited internal combustion engines.
• compositions represent motor oils for motor vehicles, and essentially for passenger car engines and commercial vehicle engines, which in the API classification (American Petroleum Institute) have the classification with the letters SF and CD or SG and CD, in the CRC classification (coordinating Research Council) the standardized "Caterpillar" test 1-G 1 or 1-G 2 and in the CCMC classification (Committee of Common Market Automobile Constructors) class 1 or 2.
• API classification American Petroleum Institute
• CRC classification coordinating Research Council
• CCMC classification Common Market Automobile Constructors
• compositions with the above-mentioned specifications can be derived analogously from the following description from the compounds of the formulas I and II designated as expedient or preferred.
• the compounds in the mixture are expediently in a mixing ratio of 4 to 5 parts by weight, preferably 4.5 parts by weight, of the aromatic amine (s) of the formula to 1 part by weight the or the phenols of the formula II, or of phenols, at least one of which has the formula II.
• the substituent R 2 in the compounds of the formula has the meaning of phenyl, naphthyl or phenyl, substituted by one or more alkyl groups having a total of 1 to 18 carbon atoms and preferably R 2 has the meaning of phenyl or Phenyl substituted with one or more alkyl groups with a total of 4 to 8 carbon atoms.
• compositions according to the invention is the substituent R 1 in compounds of the formula IH.
• compositions include those in which R 3 in compounds of the formula has the meaning of H, alkyl having 1 to 18 carbon atoms or aralkyl having 7 to 9 carbon atoms, and preference is given to the compounds in which R 3 has the meaning of H or alkyl having 4 to 8 carbon atoms.
• R 3 is in the p- (or 4-) position.
• Compositions are expedient in which R 3 'in compounds of the formula has the meaning of H or alkyl having 4 to 8 C atoms.
• R 3 ' is in the o- (or 2-) position.
• the present compositions comprise at least one compound of the formula II from the series of the phenols.
• R 6 is C 1 to C 18 alkyl, and preferably A has the meaning of CH 2 -SY, where YC 8 -C 12 alkyl or means and R 6 has the meaning of C 8 to C 13 alkyl and in particular iso-C 8 to iso-C 13 alkyl.
• compositions containing compounds of the formula 11 in which R 4 has the meaning of hydrogen or alkyl having 1 to 4 C atoms and preferably the meaning of alkyl having 4 C atoms and in particular tert-butyl are particularly useful.
• compositions which correspond to an expedient embodiment are those in which R 5 in compounds of the formula II is alkyl with 1 to 4 carbon atoms, preferably alkyl with 4 carbon atoms and in particular tert-butyl.
• R 13 iC 8 H 17 to iC 13 H 27 and in particular iC 8 H 17 or iC 13 H 27 .
• R 1 , R 2 and R ' are alkyl having 1 to 18 carbon atoms, where, for example, are methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, pentyl, isopentyl, hexyl, Heptyl, 3-heptyl, octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl, and further isoamyl, 2-ethylbutyl, 1-methylpentyl, 1,3-dimethylbutyl, 1,1,3,3, -Tetramethylbutyl, 1-methylhexyl, isoheptyl, 1-methylh
• alkyl having 1 to 24 carbon atoms is mentioned, eicosyl, hemicosyl and docosyl are also included.
• the meaning of cycloalkyl having 5 to 12 carbon atoms for R 2 , R 4 and R 5 can be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl or cyclododecyl or, in addition, the C 5 -C 12 cycloalkyl group can optionally be by C 1 -C 4 alkyl may be substituted and represent, for example, 2- or 4-methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl or t-butylcyclohexyl.
• R 2 represents substituted phenyl
• the phenyl group can be substituted, for example, with C 1 -C 18 alkoxy, or with one or more alkyl groups with a total of 24 C atoms.
• C 1 to C 8 alkoxy are methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, 2-ethylhexoxy or octoxy.
• C 7 to Cg aralkyl for example, benzyl and a-methylbenzyl can be mentioned.
• Phenyl groups which are substituted by alkyl groups having 1 to 24 carbon atoms can be, for example, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-propylphenyl, 2-, 3- or 4-butylphenyl, 2-, 3- or 4-tert-butylphenyl, 2-, 3- or 4-octylphenyl, 2-, 3- or 4-tert-octylphenyl, 2,4-di-tert-butylphenyl or 2,4-di-tert-octylphenyl.
• C 1 -C 11 alkyl-substituted benzyl examples include 2-, 3- or 4-methylbenzyl, ethylbenzyl, propylbenzyl, n-butylbenzyl, tert-butylbenzyl, n-octylbenzyl, 3,5-di-tert-octylbenzyl or 2,4-di tert-butylbenzyl or 2,4-di-tert-octylbenzyl can be listed.
• R 3 is C 7 to Cg-aralkyl
• benzyl or methylbenzyl can be mentioned, for example.
• R 4 , R 5 and R 6 can be alkyl with 1 to 24 carbon atoms.
• R 4 and R 5 can also be cycloalkyl having 5 to 12 carbon atoms.
• Corresponding examples of such alkyl groups and cycloalkyl groups are given above.
• C 1 to C 8 alkyl for Y or R 10 , R 11 or R 12 can be taken from the above list of alkyl radicals.
• Alkyl radicals with 8 to 13 carbon atoms, as they are called for R 6 can be found in the examples above, iso compounds are 2-ethylhexyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 1,1,3 -Trimethylhexyl and 1-methylundecyl.
• alkyl and cycloalkyl groups mentioned for R 8 and R 9 examples from the above lists can also be assigned in accordance with the C chain length.
• a preferred composition contains a mixture of aromatic amines, the total amount of the amines among them being 100% by weight and a maximum of them a) 5% by weight diphenylamine, 8 to 15% by weight 4-tert-butyl-diphenylamine, 24-32% by weight of amines from the group 4-tert-octyldiphenylamine, 4,4'-di-tert-butyldiphenylamine, 2,4,4'-tris-tert-butyldiphenylamine, 23 to 34% by weight of amines from the group 4-tert-butyl-4'-tert-octyldiphenylamine, o, o ', m, m' or p, p'-di-tert-octyldiphenylamine, 2,4-di-tert-butyl-4'-tert-octyldiphenylamine and 21 to 34% by weight of 2,4-di-tert-oc
• Another preferred composition contains a mixture of an aromatic amine of For mel and a phenol of the formula wherein the weight ratio of amine to phenol is 4 to 5: 1 and preferably 4.5: 1.
• Another preferred composition contains a mixture of 4,4'-di-tert-octyldiphenylamine and one or both phenols of the formulas and or wherein the weight ratio of amine to total phenol is 4 to 5: 1 and preferably 4.5: 1.
• a also preferred composition contains a mixture of aromatic amines, each based on the total amount of amines, a maximum of 5 wt .-% diphenylamine, 8 to 15 wt .-% 4-tert-butyldiphenylamine, 24-32 wt .-% amines the group 4-tert-octyldiphenylamine, 4,4'-di-tert-butyldiphenylamine, 2,4,4'-tris-tert-butyldiphenylamine, 23-34% by weight amines of the group 4-tert-butyl-4 ' -tert-octyldiphenylamine, o, o ', m, m' or p, p'-di-tert-octyldiphenylamine, 2,4-di-tert-butyl-4'-tert-octyldiphenylamine and 21 to 34% by weight 2,4-di-tert
• composition comprising a mixture of 4,4'-di-tert-octyldiphenylamine and a phenol mixture in turn consisting of and wherein the weight ratio of amine to phenols is 4 to 5: 1 and preferably 4.5: 1.
• a group of the diphenylamines as used according to the invention can be prepared, for example, by a process as described in EP-A 149 422 by reacting diphenylamine with diisobutylene in the presence of an active alumina catalyst.
• the phenols are known and can be prepared, for example, by a process according to DE-A 23 64 121 or DE-A 23 64 126.
• the mixture according to the invention can contain an amine and a phenol, but it is also possible that the mixture contains one or more amines and one or more phenols.
• the amines and phenols are premixed with one another in the stated proportions.
• This mixture can then be added, for example, in amounts of 0.01 to 10% by weight, advantageously 0.1 to 5% by weight and preferably 0.2 to 2% by weight, based on the finished lubricating oil .
• the phenols and amines can also be mixed individually one after the other into the lubricating oil, the mixing and concentration ratios mentioned having to be observed.
• oils or partially or fully synthetic oils are used as lubricating oils.
• Such oils and related products are described, for example, in Schewe-Kobek, "The Lubricant Paperback”, Wilsonhig Verlag Heidelberg, 4th edition, 1974, or in Dieter Klamann, "Lubricants and Related Products", Ver was chemistry, Weinheim, 1982 described.
• the lubricating oil can be based on a mineral oil, for example.
• 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-d-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-a-olefins, ester-based lubricants, phosphates, glycols, polyglycols and polyalkylene glycols.
• the invention also relates to a method for preventing or reducing the formation of black sludge in lubricating oils of spark-ignited internal combustion engines, for keeping black sludge particles in the lubricating oil in suspension and for reducing black sludge deposits on the lubrication circuit system of spark-ignited internal combustion engines, which is characterized in that the lubricating oil circuit with a phosphite-free Lubricating oil composition, as described above, is operated.
• the invention also relates to the use of the mixtures of phenols and amines described above as antioxidants in lubricating oils.
• Appropriate and preferred lubricating oil compositions can be derived analogously from the above description, in particular of the compounds of the formula and the formula II and from their preferred compounds and the mixture ratios mentioned with one another.
• the lubricating oil compositions contain phenols of the formula 11 or phenols, at least one of which has the formula II. If phenols, of which at least one has the formula II, are meant, it is a mixture of two or more phenols, of which at least one corresponds to the formula II and examples of one or more further phenols, for example the following list, e.g. under point 1. "Alkylated monophenols” and / or point 7. "Esters of ⁇ - (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid can be removed.
• 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.
• Esters of thiodipropionic acid or thiodiacetic acid, or salts of dithiocarbamide or dithiophosphoric acid are included in 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, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl di- and tri-sulfides, triphenyl phosphorothionates, diethanolaminomethyltolyltriazole, di (2-ethylhexyl) aminol.
• the thermal aging of the formulations is carried out in a differential scanning calorimetry (DSC).
• the DSC cell thermal analysis system 1090 from DuPont
• the DSC cell consists of a heating block made of silver.
• a constantan plate containing the thermocouples Chromel-Alumel
• Sample pans and reference pans are placed on the slightly elevated thermocouples.
• the interior of the DSC cell is covered with a thin gold film (corrosion protection).
• the reference pan remains empty, three drops of the respective formulation are poured into the sample pan.
• the temperature difference between sample and reference pans is determined under isothermal conditions.
• the enthalpy change dH / dt is given in mW. All measurements are carried out in air +400 ppm N0 2 .
• the pressure is 8 bar.
• Aral RL 136 a commercially available "black sludge reference oil", is used as the base oil. To increase the susceptibility to oxidation of the oil, 1% 1-decene is added to this oil.
• the thermal aging of the oils is determined in a further, independent method.
• a DSC pressure cell DuPont 770
• the formulations are aged under the conditions of air + 400 ppm NO 2 , pressure 8 bar.
• the samples aged in the temperature range of 120 ° C - 150 ° C are then examined by means of IR spectroscopy. For this purpose, the spectra are standardized to the same layer thickness.
• two peaks at 1730 cm- 1 and at 1630 cm- 1 are evaluated [1730 cm -1 : 6-membered lactone and 1630 cm -1 : nitrate ester].
• a reduction in these absorption bands is a measure of a lower oxidation.

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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)

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• 1989
  • 1989-06-01 EP EP89810410A patent/EP0346283B1/de not_active Expired - Lifetime
  • 1989-06-01 DE DE8989810410T patent/DE58901932D1/de not_active Expired - Lifetime
  • 1989-06-01 ES ES89810410T patent/ES2043092T3/es not_active Expired - Lifetime
  • 1989-06-01 US US07/360,646 patent/US5091099A/en not_active Expired - Lifetime
  • 1989-06-07 CA CA000601981A patent/CA1335891C/en not_active Expired - Lifetime
  • 1989-06-08 CN CN89103857A patent/CN1019984C/zh not_active Expired - Lifetime
  • 1989-06-08 KR KR1019890007857A patent/KR0125793B1/ko not_active IP Right Cessation
  • 1989-06-09 JP JP01148216A patent/JP3101818B2/ja not_active Expired - Lifetime
• 1995
  • 1995-01-26 HK HK11795A patent/HK11795A/xx not_active IP Right Cessation

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