DE3712133C2 - - Google Patents

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Publication number
DE3712133C2
DE3712133C2 DE3712133A DE3712133A DE3712133C2 DE 3712133 C2 DE3712133 C2 DE 3712133C2 DE 3712133 A DE3712133 A DE 3712133A DE 3712133 A DE3712133 A DE 3712133A DE 3712133 C2 DE3712133 C2 DE 3712133C2
Authority
DE
Germany
Prior art keywords
lubricant
mpa
oil
viscosity
ester
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.)
Expired - Lifetime
Application number
DE3712133A
Other languages
German (de)
Other versions
DE3712133A1 (en
Inventor
Erasmus Dr Froeschmann
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.)
Bremer and Leguil GmbH
Original Assignee
SIWA GmbH
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 SIWA GmbH filed Critical SIWA GmbH
Priority to DE19873712133 priority Critical patent/DE3712133A1/en
Priority to CA000563732A priority patent/CA1340272C/en
Priority to EP88105725A priority patent/EP0286139B1/en
Priority to JP63503324A priority patent/JP2843584B2/en
Priority to ES88105725T priority patent/ES2064326T3/en
Priority to KR1019880701563A priority patent/KR960014936B1/en
Priority to AT88105725T priority patent/ATE111149T1/en
Priority to PCT/EP1988/000300 priority patent/WO1988008021A1/en
Priority to DE3851355T priority patent/DE3851355D1/en
Publication of DE3712133A1 publication Critical patent/DE3712133A1/en
Application granted granted Critical
Publication of DE3712133C2 publication Critical patent/DE3712133C2/de
Priority to US08/147,014 priority patent/US5665683A/en
Granted legal-status Critical Current

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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M161/00Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M101/00Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02Petroleum fractions
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    • C10M101/00Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/04Fatty oil fractions
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    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02Well-defined hydrocarbons
    • C10M105/06Well-defined hydrocarbons aromatic
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    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/18Ethers, e.g. epoxides
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    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32Esters
    • C10M105/36Esters of polycarboxylic acids
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    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32Esters
    • C10M105/38Esters of polyhydroxy compounds
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    • C10M107/00Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C10M107/08Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing butene
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    • C10M107/20Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/22Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/28Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
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    • C10M107/20Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34Polyoxyalkylenes
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    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68Esters
    • C10M129/74Esters of polyhydroxy compounds
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    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68Esters
    • C10M129/76Esters containing free hydroxy or carboxyl groups
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    • C10M135/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/18Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
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    • C10M135/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/36Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
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    • C10M137/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
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    • C10M137/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04Phosphate esters
    • C10M137/10Thio derivatives
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    • C10M141/00Lubricating 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
    • C10M141/10Lubricating 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
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    • C10M169/00Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04Mixtures of base-materials and additives
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    • C10M169/04Mixtures of base-materials and additives
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  • Lubricants (AREA)

Abstract

A lubricant or lubricant concentrate derived from mineral and/or synthetic oils possessing improved lubricating properties, in particular improved load-bearing, sliding and anti-corrosion properties, contains a) one or more mineral and/or synthetic oils as the basic oil, b) at least one (OH)4 to (OH)8 alcohol with at least one quaternary carbon atom and at least one ester bond in the molecule, and having a density d20 of at least 0.900 and an enthalpy H of at least 350 kcal/kg, c) at least one asymmetrical organo-metallic compound, d) at least one phosphorus carrier, e) at least one sulphur carrier, and f) other usual additives.

Description

Die Erfindung betrifft ein Schmiermittel bzw. Schmiermit­ telkonzentrat mit verbesserten Schmiereigenschaften, ins­ besondere verbesserten Lasttrage-, Gleit- und Korrosions­ schutzeigenschaften auf der Basis von Mineral- und/oder Syntheseöl, das eine Verbindung mit mindestens einem quar­ tären Kohlenstoffatom und mindestens einer Esterbindung im Molekül sowie weitere übliche Zusätze enthält.The invention relates to a lubricant or Schmiermit telkonzentrat with improved lubricating properties, ins special improved load carrying, sliding and corrosion protective properties on the basis of mineral and / or Synthetic oil which is a compound having at least one quar tary carbon atom and at least one ester bond in the Molecule and other common additives.

Während der letzten Jahrzehnte wurden zahlreiche Verfahren und Schmierstoffsysteme entwickelt, um bei bewegten Maschinen­ teilen die Reibung und den Verschleiß zu mindern, somit Energie und Er­ satzteilkosten zu senken und die Lebensdauer der Schmierstoffe und Werkstoffe zu verlängern. Als idealer Schmierstoff gilt dabei der "Lifetime Lubricant", der auch den immer drängender werdenden ökologischen Forderungen entgegenkommt.During the last decades numerous procedures have been carried out and lubricant systems designed to work on moving machines Sharing reduces friction and wear, thus reducing energy and he lower part costs and the life of the lubricants and extend materials. An ideal lubricant The "Lifetime Lubricant", which is also the more urgent accommodating ecological demands.

Auf dem Wege zu Langzeit- und Hochleistungs-Schmierstoffen, -Schmiersystemen und -Schmierverfahren wurde in der ersten Stufe die sogenannte chemische Verschleißschmierung ent­ wickelt. Mit ihrer Hilfe konnte durch Aufbringung chemisch reaktiver Deckschichten auf Oberflächen oder durch Einbrin­ gung chemisch reaktiver Verbindungen in Grundschmiermittel der Metall-Metall-Kontakt durch Salzbildung an den Ober­ flächen der Mikrogebirge bewegter Teile weitgehend unter­ bunden werden. Auf diese Weise konnte das Festfressen der Maschinenteile verhindert werden. Gleichzeitig wurde aber der laufende Verschleiß durch Abscherung der Salzschichten bei der Bewegung der Metallteile gegeneinander gefördert. Die Lebensdauer der Werkstoffe blieb daher verhältnismäßig kurz. In einer weiteren Stufe wurden Festschmierstoffe entwickelt, die zwischen die bewegten Metallteile einge­ bracht wurden, wie z. B. Graphit, MoS₂, TiO₂, Ca₃(PO₄)₂, Teflon und dgl., die als schmierfähige Deckschichten, Sus­ pensionen, Pasten oder Fette eingebracht wurden. Dadurch wurden die Reibpartner besser voneinander getrennt und ihre Belastbarkeit erhöht. Bei zentripetalen Bewegungen höherer Umfangsgeschwindigkeit und bei höherer Temperatur trennen sich jedoch die Festschmierstoffe und Trägermedien über kurz oder lang voneinander aufgrund ihrer unterschiedli­ chen spezifischen Dichten. Der Langzeitschmierung waren dadurch Grenzen gesetzt. In einem weiteren Schritt gelang es, aus in einem Schmierstoff gelösten chemischen Komplexen heraus geeignete Metallkationen auf reibende Oberflächen während des Betriebs aufzubringen. Sie bilden dort unter Druck und Temperatur der Reibpartner Eutektikas mit den Metallrandschichten, welche die Rauheitstäler glättend auffüllen und die Rauheitsspritzen zum Teil tribochemisch, zum Teil mikroplastisch abflachen. Der anionische Teil der metallorganischen Verbindungen bildet in situ schmier- und haftfähige Reaktionsschichten auf den frisch umgeformten eutektoiden Reibflächen.Towards long-term and high-performance lubricants, Lubricating systems and lubrication was in the first Stage the so-called chemical wear lubrication ent wraps. With their help, by applying chemical reactive surface layers on surfaces or by Einbrin supply of chemically reactive compounds in base lubricants the metal-to-metal contact by salt formation at the upper surfaces of the micro mountains of moving parts largely under to be bound. In this way, the seizing of the Machine parts are prevented. At the same time but was the ongoing wear by shearing the salt layers promoted against each other during the movement of the metal parts. The life of the materials therefore remained relatively short. In a further stage were solid lubricants developed, which inserted between the moving metal parts were brought, such. As graphite, MoS₂, TiO₂, Ca₃ (PO₄) ₂, Teflon and the like, which are used as lubricious topcoats, Sus pensions, pastes or fats were introduced. Thereby  the friction partners were better separated from each other and increased their capacity. In centripetal movements higher peripheral speed and at higher temperature However, the solid lubricants and carrier media separate sooner or later from each other due to their differences specific densities. The long-term lubrication were this limits. In a further step succeeded it, from chemical complexes dissolved in a lubricant out suitable metal cations on rubbing surfaces during operation. They form under there Pressure and temperature of the friction partners Eutektikas with the Metal edge layers smoothing the roughness valleys fill up and the roughness splash partly tribochemical, partially flattened microplastically. The anionic part of organometallic compounds forms lubricating and in situ Adhesive reaction layers on the freshly formed eutectoid friction surfaces.

Neben einer noch zu langen Einlaufphase, einem zu hohen Reibungskoeffizienten und Abrieb hat sich bei diesen Schmiersystemen die Steuerung des Reaktionsablaufes als problematisch erwiesen.In addition to a too long run-in phase, too high Friction coefficient and abrasion has increased in these Lubricating systems controlling the reaction process as proved problematic.

Entweder gelangte man zu werkstoffunabhängigen Eutektikas und Reaktionsschichten, die eine Feinabtragung herstellungs­ bedingter Werkstoffunebenheiten in engen Passungen nicht mehr ausreichend vornahmen, so daß an diesen Stellen Über­ lastungsbereiche entstanden, die zu späteren Metallausbrüchen an den Gleitflächen führten, oder es wurde die aggressive Kom­ ponente der metallorganischen Verbindungen verstärkt und damit geriet man wieder in die Phase chemischer Verschleiß­ schmierung mit einer zu hohen Abtragungsrate und somit zu kurzer Lebensdauer. Either you came to material-independent eutectic and reaction layers producing a fine abrasion conditional material unevenness in tight fits not made more sufficient, so that in these places About Lastungsbereiche emerged, leading to later metal outbreaks led to the sliding surfaces, or it was the aggressive Kom reinforced component of organometallic compounds and With that you got back into the phase of chemical wear lubrication with too high erosion rate and thus too short life.  

Aus der DE-PS 9 41 678 sind beispielsweise Schmieröle mit einem Gehalt an löslichen Umsetzungsprodukten von Phosphor­ pentasulfid mit flüssigen oder festen aliphatischen Kohlen­ wasserstoffen oder Terpenkohlenwasserstoffen bekannt. Aus der DE-PS 9 23 984 ist ein Schmieröl bekannt, das metallhal­ tige Alkylphenolsulfidester in Kombination mit Zinksulfo­ naten enthält. Aus der DE-AS 14 44 892 ist ein Schmieröl bekannt, das ein Salz aus einem aromatischen Zinkdithio­ phosphat und einem Zinkcarbonsäuresalz in Gegenwart von Wasser enthält. Während die beiden erstgenannten Produkte Schmieröldetergentien darstellen, soll das letztgenannte Produkt die Korrosion von Silberlagerflächen verhindern. Aus der DE-AS 12 96 730 ist ein Schmieröl bekannt, das ein Salz einer substituierten Bernsteinsäure enthält, gegebenen­ falls zusammen mit einem Salz einer alkylierten oder ver­ esterten Phosphorsäure. Dabei handelt es sich um ein Anti­ oxidationsmittel mit Detergenswirkung. Aus der DE-AS 12 71 878 ist eine Kombination von Dithiophosphat und Dithiophosphinatsalzen bekannt. Aus der DE-OS 15 94 555 sind Schneidöle mit einem Gehalt an freiem Schwefel, einem Dialkyldithiophosphat und einem chlorierten Kohlenwasser­ stoff bekannt. Aus der US-PS 34 62 367 sind Schmieröle mit einem Gehalt an Zink- oder Antimondithiocarbamat be­ kannt. Aus der US-PS 27 58 087 sind Schmieröle bekannt, die eine Schwefel-Phosphor-Verbindung enthalten, die durch Umsetzung von Phosphorpentasulfid mit einem Olefin bei höherer Temperatur erhalten wird und die Zinkphthalat enthält. Alle diese bekannten Schmierölzusätze genügen den heutigen Anforderungen nicht mehr, insbesondere führen sie zu starken oxidischen Ablagerungen im Bereich der Schmier­ stelle und verursachen einen zu hohen Abrieb. Aus der US-PS 27 34 865 ist es bekannt, ein Schmieröladditiv zu verwenden, das aus einem Dithiophosphat der Erdalkalisalze in Kombination mit einem komplexen Um­ setzungsprodukt aus Phosphorsulfiden, Tallölfettsäureal­ koholestern, Zinkchlorid und Bariumhydroxid gebildet wird. Die damit erzielbaren Reibbeiwerte und Abriebswerte sind jedoch für die heutigen Anforderungen zu hoch, darüber hinaus ist ihr Flächenpressungswert zu niedrig. Aus der US-PS 27 34 864 sind ferner Schmieröladditive bekannt, die aus einem Dithiophosphat der Erdalkalisalze in Kombination mit einem komplexen Umsetzungsprodukt aus Phosphorsulfiden, Wollfett und Alkoholestern gebildet werden. Das undefinierte Produkt enthält beträchtliche Mengen an Barium und Zink. Ein solches Schmieröladditiv ist schon wegen seines uner­ träglichen Geruches, der auch die damit in Kontakt kommenden Personen gesundheitlich gefährdet, in der Praxis nicht verwendbar. Aus der DE-PS 19 54 452 sind Schmiermittel auf der Basis von Mineralöl- oder Syntheseöl bekannt, die neben dem Mineral- oder Syntheseöl als Zusätze einen Ester einer epoxidierten Fettsäure mit 10 bis 18 C-Atomen mit ein- oder mehrwertigen Alkoholen, ein Alkyl-, Aralkyl- oder Aryldi­ thiophosphat von Zink, Blei, Zinn, Wolfram, Molybdän, Niob oder Lanthan und gegebenenfalls eine Schwefelphosphorver­ bindung enthalten. Aus der DE-PS 21 08 780 sind Schmiermittel auf der Basis von Mineral- oder Syntheseöl bzw. Schmiermittel­ konzentrate bekannt, die neben einem mit Alkyl-, Aryl- oder Aralkylgruppen veresterten Blei-, Wolfram-, Molybdän und/oder Vanadindithiophosphat noch mindestens eine Zinkdialkyldithio­ phosphat- und eine metallfreie Schwefel-Phosphor-Verbindung enthalten. Auch diese zuletzt genannten Schmiermittel, die eine weit verbreitete Anwendung gefunden haben, genügen den Anfor­ derungen, die an moderne Langzeit- und Hochleistungsschmierstof­ fe gestellt werden, nicht mehr in allen Belangen. Ihr Reibungs­ koeffizient und Abrieb liegen zu hoch, ihre Lagerbeständigkeit ist unzureichend, im Langzeiteinsatz zeigt sich eine zu hohe Re­ klamationsquote im schmiertechnischen Bereich. From DE-PS 9 41 678, for example, lubricating oils with a content of soluble reaction products of phosphorus pentasulfide with liquid or solid aliphatic carbons hydrogen or terpene hydrocarbons. Out DE-PS 9 23 984 a lubricating oil is known, the metallhal tiger Alkylphenolsulfidester in combination with zinc sulfo contains data. From DE-AS 14 44 892 is a lubricating oil known to be a salt of an aromatic zinc dithio phosphate and a zinc carboxylic acid salt in the presence of Contains water. While the first two products Represent the latter Product to prevent corrosion of silver bearing surfaces. From DE-AS 12 96 730 a lubricating oil is known, the one Salt of a substituted succinic acid, given if together with a salt of an alkylated or ver esterified phosphoric acid. It is an anti detergent oxidant. From DE-AS 12 71 878 is a combination of dithiophosphate and Dithiophosphinatsalzen known. From DE-OS 15 94 555 are cutting oils containing free sulfur, a Dialkyl dithiophosphate and a chlorinated hydrocarbon substance known. From US-PS 34 62 367 are lubricating oils Containing zinc or antimony thiocarbamate be known. From the US-PS 27 58 087 lubricating oils are known, which contain a sulfur-phosphorus compound by Implementation of phosphorus pentasulfide with an olefin at higher temperature is obtained and the zinc phthalate contains. All these known lubricating oil additives satisfy the  no longer meet today's requirements, in particular they lead too strong oxidic deposits in the area of the lubricants cause and cause excessive abrasion. From US-PS 27 34 865 it is known a To use lubricating oil additive, which consists of a dithiophosphate the alkaline earth salts in combination with a complex Um Substitution product of phosphorus sulfides, Tallölfettsäureal koester, zinc chloride and barium hydroxide is formed. The achievable friction coefficients and abrasion values are however, for today's requirements too high, beyond is their surface pressure too low. From the US PS 27 34 864 lubricating oil additives are also known, the a dithiophosphate of alkaline earth salts in combination with a complex reaction product of phosphorus sulfides, Wool fat and alcohol esters are formed. The undefined Product contains significant amounts of barium and zinc. Such a lubricating oil additive is already because of its uner odor, which also comes into contact with it Persons at risk, not in practice usable. From DE-PS 19 54 452 are lubricants the basis of mineral oil or synthetic oil known in addition to the mineral or synthetic oil as additives an ester of a epoxidized fatty acid having 10 to 18 C atoms with or without polyhydric alcohols, an alkyl, aralkyl or aryldi thiophosphate of zinc, lead, tin, tungsten, molybdenum, niobium or lanthanum and optionally a Schwefelphosphorver binding included. DE-PS 21 08 780 are lubricants based on mineral or synthetic oil or lubricant Concentrates known in addition to one with alkyl, aryl or Aralkyl groups esterified lead, tungsten, molybdenum and / or Vanadium dithiophosphate still at least one Zinkdialkyldithio phosphate and a metal-free sulfur-phosphorus compound contain. Also these last mentioned lubricants, the one have found widespread application, meet the requirements modifications to modern long-term and high-performance lubricants no longer in all respects. Your friction Coefficient and abrasion are too high, their storage life is insufficient, in long-term use shows too high Re Clearing rate in the lubrication sector.  

Aus der DE-OS 25 20 459 ist es bereits bekannt, Pentaery­ thrit- und/oder Dipentaerythritester von linearen gesät­ tigten Fettsäuren mit 7 bis 18 Kohlenstoffatomen als Schmiermittel oder Schmiermittelzusatz zu verwenden. In der GB-PS 21 34 538 sind Schmierölzusammensetzungen be­ schrieben, die zu 5 bis 70 Gew.-% aus einem Mineralöl und/oder Syntheseöl und zum Rest aus einem Ester eines sterisch gehinderten Alkohols und einer ungesättigten Fettsäure mit 18 Kohlenstoffatomen bestehen. Auch aus der DE-OS 20 34 383 ist es bereits bekannt, Gemische von syn­ thetischen Estern als Zusätze in Schmiermitteln zu verwen­ den. Die darin beschriebenen spezifischen Gemische beste­ hen aus veresterten Trimethylolpropanestern von aliphati­ schen C₄-C₁₂-Monocarbonsäuren und veresterten Dipentaery­ thritestern von aliphatischen C₄-C₁₀-Monocarbonsäuren. Al­ len diesen bekannten Schmiermittelzusätzen ist gemeinsam, daß sie hinsichtlich ihrer Schmiereigenschaften, insbeson­ dere ihrer Verschleißschutzeigenschaften, den heutigen ge­ stiegenen Anforderungen nicht mehr genügen.From DE-OS 25 20 459 it is already known, pentaery thritic and / or dipentaerythritol esters of linear sown saturated fatty acids having 7 to 18 carbon atoms Use lubricant or lubricant additive. In GB-PS 21 34 538 are lubricating oil compositions be from 5 to 70% by weight of a mineral oil and / or synthetic oil and the remainder of an ester of a sterically hindered alcohol and an unsaturated one Consist of fatty acid with 18 carbon atoms. Also from the DE-OS 20 34 383 it is already known mixtures of syn thetic esters as additives in lubricants verwen the. The specific mixtures described therein best esterified trimethylolpropane esters of aliphati rule C₄-C₁₂ monocarboxylic acids and esterified dipentaery thritestern of aliphatic C₄-C₁₀ monocarboxylic acids. al len these known lubricant additives is common, that with regard to their lubricating properties, in particular their anti-wear properties, today's ge Increasing requirements are no longer sufficient.

Aufgabe der Erfindung war es daher, ein Schmiermittel bzw. Schmiermittelkonzentrat auf der Basis von Mineral- und/oder Syntheseöl zu schaffen, das hinsichtlich seiner Schmiereigenschaften, insbesondere seiner Reib- und Ver­ schleißschutzeigenschaften, den Stand der Technik über­ trifft und somit den Energie- und Ersatzteilbedarf spür­ bar verringert und damit auch den höchsten gestellten An­ forderungen gerecht wird.The object of the invention was therefore to provide a lubricant or Lubricant concentrate based on mineral and / or To create synthetic oil, which in terms of its Lubricating properties, especially its friction and Ver Wear protection properties, the state of the art over meets and thus feels the need for energy and spare parts bar and thus also the highest level requirements.

Es wurde nun gefunden, daß diese Aufgabe erfindungsgemäß dadurch gelöst werden kann, daß einem Mineral- und/oder Syntheseöl neben den üblichen Zusätzen mindestens ein 4- bis 8wertiger Alkohol mit mindestens einem quartären Koh­ lenstoffatom sowie mindestens einer Esterbindung im Mole­ kül und mit einer kritischen Dichte und einer kritischen Enthalpie, eine zusätzliche Komponente mit mindestens ei­ ner freien Hydroxylgruppe im Molekül, mindestens eine spe­ zifische Metalldialkyldithiocarbamatverbindung der nach­ stehend angegebenen allgemeinen Formel, mindestens ein spezifisches Organophosphit und ein Thiazol zugesetzt wer­ den.It has now been found that this object according to the invention can be solved by a mineral and / or Synthetic oil in addition to the usual additives at least 4- to 8wertiger alcohol with at least one quaternary Koh and at least one ester bond in the mole and with a critical density and a critical one Enthalpy, an additional component with at least ei ner free hydroxyl group in the molecule, at least one spe  zifische Metalldialkyldithiocarbamatverbindung of standing specified general formula, at least one specific organophosphite and a thiazole added the.

Gegenstand der Erfindung ist ein Schmiermittel bzw. Schmiermittelkonzentrat auf der Basis von Mineral- und/oder Syntheseöl, das eine Verbindung mit min­ destens einem quartären Kohlenstoffatom und mindestens einer Esterbindung im Molekül sowie weitere übliche Zusätze enthält, dadurch gekennzeichnet, daß es enthältThe invention is a Lubricant or lubricant concentrate on the basis of mineral and / or synthetic oil which is a compound with min at least one quaternary carbon atom and at least one Contains ester bond in the molecule and other conventional additives, characterized in that it contains

  • (a) mindestens einen 4- bis 8wertigen Alkohol mit mindestens einem quartären Kohlenstoffatom im Molekül mit einer Dichte d₂₀ von mindestens 0,900 und einer Enthalpie H von mindestens 350 kcal/kg, ausgewählt aus der Gruppe der Mono-, Di- und Tripentaerythrite, deren alko­ holische Hydroxylgruppe(n) durch eine Säure mit unverzweigter oder verzweig­ ter Alkyl-, Aralkyl- oder Arylgruppe mit 6 bis 18 Kohlenstoff­ atomen verestert oder ethoxyverestert ist (sind),(a) at least one 4- to 8-valent alcohol having at least a quaternary carbon atom in the molecule with a density d₂₀ of at least 0.900 and an enthalpy H of at least 350 kcal / kg, selected from the group of mono-, di- and tripentaerythrits whose alko holische hydroxyl group (s) by an acid with unbranched or branched the alkyl, aralkyl or aryl group having 6 to 18 carbon is esterified or ethoxyesterified (are),
  • (b) eine zusätzliche Komponente mit mindestens einer freien Hydroxylgruppe im Molekül,(b) an additional component with at least one free one Hydroxyl group in the molecule,
  • (c) mindestens ein Metalldialkyldithiocarbamat der Formel worin bedeuten:
    Me ein Metall aus der Gruppe Kupfer, Silber, Zink, Cad­ mium, Bor, Titan, Zirkonium, Zinn, Blei, Vanadin, Tan­ tal, Antimon, Chrom, Molybdän, Wolfram, Mangan, Ko­ balt und Nickel und
    Alkyl eine Alkylgruppe mit 4 bis 8 Kohlenstoffatomen,
    (C) at least one Metalldialkyldithiocarbamat of the formula in which mean:
    Me is a metal from the group consisting of copper, silver, zinc, cadmium, boron, titanium, zirconium, tin, lead, vanadium, talc, antimony, chromium, molybdenum, tungsten, manganese, cobalt and nickel and
    Alkyl is an alkyl group having 4 to 8 carbon atoms,
  • (d) mindestens ein Dialkylaryl-, Monoalkyldiaryl-, Trialkyl- oder Triarylphosphit, in dem die Alkylgruppe unverzweigt, ver­ zweigt oder zyklisch ist und 8 bis 12 Kohlenstoffatome auf­ weist(d) at least one dialkylaryl, monoalkyldiaryl, trialkyl or triaryl phosphite in which the alkyl group is unbranched, ver is branched or cyclic and has 8 to 12 carbon atoms has
  • (e) ein Thiazol und(e) a thiazole and
  • (f) als weitere übliche Zusätze an sich bekannte Antioxida­ tionsmittel, Metalldesaktivatoren, Detergentien, Dispergier­ mittel, Antischaummittel und/oder Viskositätsindexverbesse­ rungsmittel.(f) as further customary additives per se known antioxidant tion agents, metal deactivators, detergents, dispersants medium, antifoam and / or viscosity index insurance agent.

Vorzugsweise enthält das erfindungsgemäße Schmiermittel bzw. Schmiermittelkonzentrat als weitere KomponentePreferably, the lubricant according to the invention contains or lubricant concentrate as another component

  • (g) mindestens ein Metalldialkyldithiophosphat der allgemei­ nen Formel worin bedeuten:
    Me ein Metall aus der Gruppe Kupfer, Silber, Zink, Cadmium, Bor, Titan, Zirkonium, Zinn, Blei, Vanadin, Tantal, An­ timon, Chrom, Molybdän, Wolfram, Mangan, Cobalt und Nickel und
    Alkyl eine Alkylgruppe mit 4 bis 8 Kohlenstoffatomen.
    (g) at least one metal dialkyldithiophosphate of the general formula in which mean:
    Me is a metal from the group of copper, silver, zinc, cadmium, boron, titanium, zirconium, tin, lead, vanadium, tantalum, antonone, chromium, molybdenum, tungsten, manganese, cobalt and nickel and
    Alkyl is an alkyl group having 4 to 8 carbon atoms.

Die Menge, in der die Komponenten (c) und (g) verwendet werden können, beträgt vorzugsweise 0,1 bis 10 Gew.-%, insbesondere 0,1 bis 5 Gew.-%, speziell 1 bis 3 Gew.-%.The amount in which components (c) and (g) are used is preferably 0.1 to 10 wt .-%, in particular 0.1 to 5 wt .-%, especially 1 to 3 wt .-%.

Weitere bevorzugte Ausgestaltungen des erfindungsgemäßen Schmiermittels bzw. Schmiermittelkonzentrats ergeben sich aus den Unteransprüchen 3 bis 9. Further preferred embodiments of the invention Lubricant or lubricant concentrate result from the dependent claims 3 to 9.  

Die erfindungsgemäßen Schmiermittel bzw. Schmiermittelkon­ zentrate weisen gegenüber den bekannten Schmiermitteln bzw. Schmiermittelkonzentraten wesentlich verbesserte Schmiereigen­ schaften, insbesondere in bezug auf Reibung und Verschleiß, und somit einen erniedrigten Energie- und Ersatzteilbe­ darf auf. Es wird angenommen, daß dies darauf zurückzu­ führen ist, daß bei ihrer Verwendung im Reib- und Gleitbe­ reich metallische Glasflächen aus amorph erstarrten Metall­ schmelzen, die keine Metallkristallgitterstrukturen mehr aufweisen, entstehen. Die glasartigen glatten Reib- und Gleitflächen, die mit dem erfindungsgemäßen Schmiermittel bzw. Schmiermittelkonzentrat vermutlich erzeugt werden, verbessern deutlich den gesamten Schmiervorgang, da der Reibkoeffizient und mit ihm der Abrieb, die Oxidation und die Korrosion erheblich gesenkt werden. Auch der sogenannte Passungsrost wird durch das erfindungsgemäße Schmiermittel bzw. Schmiermittelkonzentrat verhindert. Hinzu kommt, daß die erfindungsgemäßen Schmiermittel bzw. Schmiermittelkon­ zentrate außerordentlich umweltfreundlich sind, da sie kaum Blei, kein geschwefeltes Walspermöl und kaum Phosphor enthalten. Dies haben Fischtests, Rattentests und Bakterienwachstumstests, die mit den erfindungsgemäßen Schmiermitteln bzw. Schmiermittelkonzentraten durchgeführt wurden, gezeigt. Außerdem wurde festgestellt, daß sie schon innerhalb von 3 bis 4 Monaten in normaler Erde zu mindestens 60% biologisch abbaubar sind, so daß sie auch als außerordentlich umweltverträglich bezeichnet werden können. Sie sind besonders gut geeignet für die Verwendung in homokinetischen Gelenken für Fahrzeuge, d. h. kleinen Gelenken mit einer hohen Drehzahl und einer hohen Belastung, und sie kommen dem als idealen Schmierstoff ange­ sehenen "Lifetime Lubricant" wesentlich näher als alle bisher bekannten Schmiermittel. Hinzu kommt, daß die erfindungsge­ mäß eingesetzten, quartäre Kohlenstoffatome enthaltenden Polyolester- Verbindungen thermisch sehr stabil sind und daher hohe Be­ triebstemperaturen von bis zu 300°C erlauben. Sie eröffnen daher die Möglichkeit zur Lebensdauerschmierung höchstbe­ lasteter Motoren, Turbinen, Wälzlager, Gleichlaufgelenke und anderer Hochleistungsmaschinenelemente. The lubricant or lubricant con centrate wise over the known lubricants or lubricant concentrates significantly improved greasiness in particular with regard to friction and wear, and thus a reduced energy and spare parts may open. It is believed that this is back to it lead is that when used in friction and Gleitbe rich metallic glass surfaces of amorphous solidified metal Melt that no metal crystal lattice structures more have arise. The glassy smooth friction and Sliding surfaces with the lubricant of the invention or lubricant concentrate are presumed to be produced, significantly improve the overall lubrication process, since the Friction coefficient and with it the abrasion, the oxidation and the corrosion can be lowered considerably. Also the so-called Fretting corrosion is caused by the lubricant according to the invention or lubricant concentrate prevented. In addition, that the lubricant or lubricant con Centrates are extremely environmentally friendly as they barely Lead, no sulfurized whale oil and hardly any phosphorus contain. These have fish tests, rat tests and Bacterial growth tests with the inventive Lubricants or lubricant concentrates performed were shown. It was also found that they already within 3 to 4 months in normal soil too at least 60% biodegradable so that they are also extremely environmentally friendly can be designated. They are particularly well suited for use in homokinetic joints for vehicles, d. H. small joints with a high speed and a high Load, and they are considered as an ideal lubricant "Lifetime Lubricant" is much closer than any known lubricant. In addition, the erfindungsge according to used, quaternary carbon atoms containing polyolester Compounds are thermally very stable and therefore high Be allow operating temperatures of up to 300 ° C. They open therefore the possibility for lifetime lubrication hochbe lastet engines, turbines, bearings, constant velocity joints and other high performance machine elements.  

Unter dem hier verwendeten Ausdruck "Schmiermittel bzw. Schmiermittelkonzentrat auf der Basis von Mineral- und/oder Syntheseöl" sind sowohl Schmieröle als auch Schmierfette auf Mineral- und/oder Syntheseölbasis zu verstehen.As used herein, the term "lubricant or Lubricant concentrate based on mineral and / or Synthetic oil "are both lubricating oils and greases on a mineral and / or synthetic oil basis to understand.

Unter quartäre Kohlenstoffatome enthaltenden Verbindungen sind hier solche Verbindungen zu verstehen, in denen die vier Hauptvalenzen mindestens eines Kohlenstoffatoms je Molekül mit vier Kohlenstoffatomen besetzt sind. Beispiele für solche Verbindungen sind mono-, di- und trimere Pentaerythritester, Pentaerythritethoxy­ ester sowie Telomersäurepentaerythritester und die ent­ sprechenden ethoxylierten Ester.Among quaternary carbon-containing compounds Here are those compounds in which the four major valences of at least one carbon atom each Molecule occupied by four carbon atoms. Examples for such compounds are mono-, di- and trimer Pentaerythritol ester, pentaerythritolethoxy ester and telomeric acid pentaerythritol ester and the ent speaking ethoxylated ester.

Die erfindungsgemäßen Schmiermittel bzw. Schmiermittelkonzen­ trate weisen gegenüber den bekannten Schmiermitteln bzw. Schmiermittelkonzentraten deutlich verbesserte Eigenschaften auf, wie die weiter unten folgenden Beispiele zeigen. Die durch den erfindungsgemäßen Schmierstoff erzeugten glasartigen glat­ ten Reib- und Gleitflächen ersparen Antriebsenergie und erniedrigen den Reibungs­ koefffizienten per se und durch Aufbau eines sehr haftfesten Grenzschmierfilms, der eine elastohydrodynamische Schmierung auch bei punktförmiger Belastung ermöglicht. Hierdurch wird die Reibtemperatur von Schmierstoff und Schmierstelle herabge­ setzt, die Oxidationsbeständigkeit beider verlängert und die metallischen Reibungspartner weniger spezifisch wechsellast- und temperaturbeansprucht.The lubricants or lubricant concentrates according to the invention have trate towards the known lubricants or Lubricant concentrates significantly improved properties on, as the examples below below show. The produced by the lubricant according to the invention glassy glat The friction and sliding surfaces save energy and reduce friction coefficient of coefficient per se and by building a very adherent Grenzschmierfilms, the one Elastohydrodynamische lubrication even with punctiform load allows. This will the friction temperature of lubricant and lubrication point herabge sets, the oxidation resistance of both extended and the metallic friction partner less specific alternating load and temperature-stressed.

Insgesamt werden durch diese Effekte der Verschleiß außeror­ dentlich erniedrigt und die Lebensdauer der Reibpartner und des Schmierstoffs deutlich erhöht. Erfindungsgemäß werden diese Verbesserungen innerhalb eines sehr breiten Viskosi­ tätsbereiches erzielt, so daß nunmehr auch Öle mit niedriger Viskosität dort verwendet werden können, wo bisher hohe oder mittlere Viskositätsgrade als unbedingt erforderlich an­ gesehen wurden, beispielsweise bei Getrieben, Differential­ getrieben oder Turbinenuntersetzungsgetrieben. Auch erlaubt die thermische Beständigkeit des erfindungsgemäßen Schmier­ mittels bzw. Schmiermittelkonzentrats seine Verwendung an Schmierstellen hoher Betriebstemperatur, beispielsweise in Dieselmotoren und Flugturbinen. Overall, the effects of wear are extraordinary dienst humbled and the life of the friction partners and of the lubricant significantly increased. According to the invention these improvements within a very broad viscous scored so that now also oils with lower Viscosity can be used where previously high or medium viscosity levels as absolutely necessary have been seen, for example in transmissions, differential driven or turbine reduction gears. Also allowed the thermal stability of the lubricant according to the invention by means of or lubricant concentrate its use Lubrication points high operating temperature, for example in diesel engines and aircraft turbines.  

Gemäß der obengenannten Definition der Erfindung enthält das Schmiermittel bzw. Schmiermittelkonzentrat als Kompo­ nente (a) Mono-, Di- oder Tripentaerythrit, dessen alkoholische Hydroxylgruppe(n) durch eine Säure mit unverzweigter oder verzweigter Alkyl-, Aralkyl- oder Arylgruppe mit 6 bis 18 Kohlenstoff­ atomen, vorzugsweise 6 bis 12 Kohlenstoffatomen, insbeson­ dere 8 bis 12 Kohlenstoffatomen, verestert oder ethoxyver­ estert ist (sind).According to the above definition of the invention the lubricant or lubricant concentrate as a compo (a) mono-, di- or tripentaerythritol, the alcoholic Hydroxyl group (s) by an acid with unbranched or branched Alkyl, aralkyl or aryl group of 6 to 18 carbon atoms, preferably 6 to 12 carbon atoms, in particular from 8 to 12 carbon atoms, esterified or ethoxyver estert is (are).

Gemäß der obengenannten Definition der Erfindung enthält das Schmiermittel bzw. Schmiermittelkonzentrat zusätzlich eine Komponente (b) mit mindestens einer freien Hydroxylgruppe.According to the above definition of the invention the lubricant or lubricant concentrate in addition a component (b) with at least one free one Hydroxyl group.

Das erfindungsgemäße Schmiermittel bzw. Schmiermittelkonzen­ trat enthält die Komponente (a) gemäß einer weiteren bevor­ zugten Ausgestaltung der Erfindung in einer Menge von 0,1 bis 40 Gew.-%, vorzugsweise von 0,1 bis 20 Gew.-%, insbe­ sondere von 1 bis 12 Gew.-%, speziell von 2 bis 6 Gew.-%, bezogen auf das Gewicht des Mineral- und/oder Syntheseöls.The lubricant or lubricant concentrate according to the invention Step 2 contains component (a) according to another zugten embodiment of the invention in an amount of 0.1 to 40 wt .-%, preferably from 0.1 to 20 wt .-%, in particular especially from 1 to 12% by weight, especially from 2 to 6% by weight, based on the weight of the mineral and / or synthetic oil.

Gemäß einer weiteren bevorzugten Ausgestaltung der Erfindung enthält das erfindungsgemäße Schmiermittel bzw. Schmiermit­ telkonzentrat als Komponente (a) ein Ester- und/oder ethoxyliertes Esterderivat von Mono-, Di- oder Tripenta­ erythrit und/oder einen Telomersäurepentaerythritester oder ein ethoxyliertes Derivat davon.According to a further preferred embodiment of the invention Contains the lubricant or lubricant according to the invention telkonzentrat as component (a) an ester and / or ethoxylated ester derivative of mono-, di- or tripenta erythritol and / or a telomeric acid pentaerythritol ester or an ethoxylated derivative thereof.

Als Grundöl enthält das erfindungsgemäße Schmiermittel bzw. Schmiermittelkonzentrat vorzugsweise Rüböl, Naturöl und/oder ein Syntheseöl mit einer Viskosität in dem Bereich von 1,0 mPa · s bei 20°C bis 2 · 10⁶ mPa · s bei 20°C. Besonders bevor­ zugt ist die Verwendung eines Mineralöls mit einer Visko­ sität von 1,0 mPa · s bei 20°C bis 540 mPa · s bei 50°C als Naturöl sowie die Verwendung eines aromatischen oder alipha­ tischen Dicarbonsäureesters, insbesondre Poly-α-olefin­ dicarbonsäureesters, speziell -butylesters, mit einem Molekulargewicht im Bereich von 1000 bis 3000, vorzugs­ weise von Phthalsäurediisodecylester, Trimethyladipinsäure­ didecylester und Sebacinsäuredioctylester, eines Polyiso­ butylens mit einem Molekulargewicht von 1000 bis 100 000 und einer Viskosität von 200 bis 43 000 mPa · s bei 100°C, eines Polymethacrylats mit einer Viskosi­ tät von 1000 mPa · s bei 100°C, eines nicht wasserlöslichen Polyglykols mit einer Viskosität von 5 bis 60 mPa · s bei 100°C, eines Isoparaffinöls und/oder Alkylbenzols mit einem Flamm­ punkt von über 50°C und einer Viskosität im Bereich von 1,0 mPa · s bei 20°C bei 2 000 000 mPa · s bei 20°c und eines Telo­ mersäureesters, vorzugsweise eines Neopentylglykol- oder Trimmethylolpropanesters der Telomersäure.As a base oil contains the lubricant according to the invention or Lubricant concentrate preferably rapeseed oil, natural oil and / or a synthetic oil having a viscosity in the range of 1.0 mPa · s at 20 ° C to 2 x 10⁶ mPa · s at 20 ° C. Especially before zugt is the use of a mineral oil with a Visko  of 1.0 mPa · s at 20 ° C to 540 mPa · s at 50 ° C as Natural oil as well as the use of an aromatic or alipha dicarboxylic acid esters, in particular poly-α-olefin dicarboxylic acid ester, especially butyl ester, with one Molecular weight in the range of 1000 to 3000, preferably example of diisodecyl phthalate, trimethyladipic acid didecyl ester and sebacic acid dioctyl ester, a polyiso Butylene with a molecular weight of 1000 to 100,000 and a viscosity of 200 to 43,000 mPa · s at 100 ° C, a polymethacrylate with a Viskosi of 1000 mPa · s at 100 ° C, a non-water soluble Polyglycol having a viscosity of 5 to 60 mPa · s at 100 ° C, an isoparaffin oil and / or alkylbenzene with a flame point above 50 ° C and a viscosity in the range of 1.0 mPa · s at 20 ° C at 2,000,000 mPa · s at 20 ° c and a telo mersäureesters, preferably a Neopentylglykol- or Trimethylolpropane ester of the telomeric acid.

Als weiteren Zusatz enthält das erfindungsgemäße Schmier­ mittel bzw. Schmiermittelkonzentrat ein Thiazol, mindestens ein Metalldialkyldithiocarbamat und ein Organophosphit, vorzugsweise ein Dialkylarylphosphit, speziell Didecylphenylphosphit oder Didodecylphenylphosphit sowie gegebenenfalls mindestens ein Metalldialkyldithiophosphat.As a further additive, the lubricant according to the invention contains medium or lubricant concentrate Thiazole, at least one Metalldialkyldithiocarbamat and an organophosphite, preferably a dialkylaryl phosphite, especially didecylphenyl phosphite or didodecylphenyl phosphite as well optionally at least one Metalldialkyldithiophosphat.

Das Thiazol ist vorzugsweise in einer Menge von 0,5 bis 10 Gew.-%, insbesondere von 1 bis 3 Gew.-%, in dem Schmiermittel bzw. Schmiermittelkonzentrat enthalten, wäh­ rend es das Phosphit vorzugsweise in einer Menge von 0,1 bis 5 Gew.-% insbesondere von 0,5 bis 2 Gew.-%, enthält.The thiazole is preferably in an amount of 0.5 to 10 wt .-%, in particular from 1 to 3 wt .-%, in the Contain lubricant or lubricant concentrate, wäh it preferably contains the phosphite in an amount of 0.1 to 5 wt .-% in particular from 0.5 to 2% by weight.

Als weitere übliche Zusätze enthält das erfindungsgemäße Schmiermittel bzw. Schmiermittelkonzentrat übliche Anti­ oxidantien, Metalldesaktivatoren, Detergentien, Dispergiermittel, Antischaummittel und/oder Viskositäts­ indexverbesserer. As further customary additives, the inventive Lubricant or lubricant concentrate usual anti oxidants, metal deactivators, detergents, Dispersant, antifoam and / or viscosity index improvers.  

Weitere Merkmale und Vorteile der Erfindung ergeben sich aus der nachfolgenden Beschreibung.Other features and advantages of the invention will become apparent from the description below.

Zu den erfindungsgemäß verwendeten 4- bis 8wertigen Al­ koholen mit mindestens einem quartären Kohlenstoffatom im Molekül gehören die folgenden Verbindungen:To the 4- to 8-valent Al used in the invention koholen with at least one quaternary carbon atom in Molecule include the following compounds:

a) Ester und ethoxylierte Ester von Mono-, Di- und Tripentaerythrita) Esters and ethoxylated esters of mono-, di- and tripentaerythritol

Der ihnen zugrunde liegende Mono- und Dipentaerythrit hat die Struktur:The underlying mono- and dipentaerythritol has the structure:

in denen die Hydroxylgruppe(n) durch eine Säure mit geraden oder verzweigten Alkyl-, Aralkyl- oder Arylgruppen mit 6 bis 18 vorzugsweise 8 bis 12, Kohlenstoffatomen verestert ist (sind).in which the hydroxyl group (s) by an acid with straight or branched alkyl, aralkyl or aryl groups of 6 to 18 preferably 8 to 12, carbon atoms is (are) esterified.

Diese Verbindungen lassen sich leicht herstellen und zahl­ reiche Vertreter dieser Verbindungen sind im Handel er­ hältlich, beispielsweise von der Firma Ciba-Geigy unter den Handelsbezeichnungen Reolube LP 3600® (Pentaerythrit­ tetrapelargonat), Reolube, LPE 504® (Pentaerythrittetraoctyl­ ester), Reolube LPE 602® (Pentaerythrittetraheptylester), von der Firma Akzo unter der Handelsbezeichnung Ketjenlube 12® (Pentaerythrittetradecyl/dodecylester mit statistischer C₁₀/C₁₂-Verteilung), und von der Firma Henkel AG unter der Handelsbezeichnung Edenor Ke 230® (Pentaerythrittetraisopalmitinsäure­ ester) und Pentaerythrittetraisostearylsäure­ ester.These compounds are easy to manufacture and pay rich representatives of these compounds are in commerce festlich, for example, by the company Ciba-Geigy the trade names Reolube LP 3600® (pentaerythritol tetrapelargonat), Reolube, LPE 504® (pentaerythritol tetraoctyl ester), Reolube LPE 602® (pentaerythritol tetraheptyl ester), from Akzo under the trade name Ketjenlube 12® (pentaerythritol tetradecyl / dodecyl ester with statistical  C₁₀ / C₁₂ distribution), and from the company Henkel AG under the Trade name Edenor Ke 230® (pentaerythritol tetraisopalmitic acid ester) and pentaerythritol tetraisostearic acid ester.

Beispiele für geeignete Pentaerythritester sind die Tetrahexyl-, Tetraoctyl-, Tetranonyl-, Tetradecyl-, Tetradodecyl-, Tetramyristyl-, Tetrahexadecyl-, Tetra­ stearyl-, Tetraoleyl-, Tetraisostearyl- und Tetraisopalmitin­ säureester des Pentaerythrits.Examples of suitable pentaerythritol esters are the tetrahexyl, tetraoctyl, tetranonyl, tetradecyl, Tetradodecyl, tetramyristyl, tetrahexadecyl, tetra stearyl, tetraoleyl, tetraisostearyl and tetraisopalmitin acid ester of pentaerythritol.

b) Pentaerythrittelomersäurederivate mit der folgenden Grundstrukturb) Pentaerythrittelomeric acid derivatives having the following basic structure

worin bedeuten:
T=Telomer
R=T oder Alkyl
in which mean:
T = telomere
R = T or alkyl

Bei Telomersäuren handelt es sich bekanntlich um Verbin­ dungen mit verhältnismäßig hohen Molekulargewichten und langkettigen, sternartig verzweigten Strukturen, die auf übliche Weise verestert werden können und deren Ester wert­ volle Schmierstoffe darstellen (Handelsprodukt Kortacid T der Firma Akzo Chemie).Telomeric acids are known to be verbin with relatively high molecular weights and  long-chain, star-like branched structures on usual way can be esterified and their esters worth represent full lubricants (commercial product Kortacid T the company Akzo Chemie).

Erfindungsgemäß verwendbare Mineralöle sind alle üblichen Mineralöle vom Isoparaffinöl mit einer Viskosität von 1,0 mPa · s bei 20°C über dünnes Spindelöl mit einer Viskosität von 12 mPa · s bei 20°C bis zu hochviskosem Brightstock und Zylin­ deröl mit einer Viskosität von 540 mPa · s bei 50°C.Mineral oils which can be used according to the invention are all customary Mineral oils of isoparaffin oil with a viscosity of 1.0 mPa · s at 20 ° C over thin spindle oil with a viscosity of 12 mPa · s at 20 ° C to high viscosity brightstock and cylin oil with a viscosity of 540 mPa · s at 50 ° C.

Viele der erfindungsgemäß verwendbaren Syntheseöle sind im Handel erhältlich, beispielsweise von der Firma BP unter den Warenzeichen "Hyvis 10" (ein Polyisobutylen mit einer Viskosität bei 100°C von 200 mPa · s), "Hyvis 200" (ein Polyisobutylen mit einer Viskosität bei 100°C von 4300 mPa · s) und "Hyvis 2000" (ein Polyisobutylen mit einer Viskosität bei 100°C von 43 000 mPa · s), "Viscoplex 4-95" der Firma Röhm (ein Polymethacrylat) mit ei­ ner Viskosität von 1000 mPa · s bei 100°C, "Ucolub N9" mit ei­ ner Viskosität von 5,7 mPa · s bei 100°C, "Ucolub N36A" mit ei­ ner Viskosität von 18 mPa · s bei 100°C, "Ucolub N 120A" mit ei­ ner Viskosität von 55 mPa · s bei 100°C (alles nicht-wasserlös­ liche Polyglykole) der Firma Union Carbide, sowie "Isopar J" der Firma Esso (ein Isoparaffinöl) mit einer Viskosität bei 20°C von 1,0 mPa · s.Many of the synthetic oils useful in this invention are commercially available, for example from the company BP under the trademark "Hyvis 10" (a polyisobutylene with a viscosity at 100 ° C of 200 mPa · s), "Hyvis 200" (a polyisobutylene having a viscosity at 100 ° C of 4300 mPa · s) and "Hyvis 2000" (a polyisobutylene with a viscosity at 100 ° C of 43,000 mPa · s), "Viscoplex 4-95" from Röhm (a polymethacrylate) with egg ner viscosity of 1000 mPa · s at 100 ° C, "Ucolub N9" with egg ner viscosity of 5.7 mPa · s at 100 ° C, "Ucolub N36A" with egg ner viscosity of 18 mPa · s at 100 ° C, "Ucolub N 120A" with egg ner viscosity of 55 mPa · s at 100 ° C (all non-aqueous polyglycols) of Union Carbide, as well as "Isopar J" from the company Esso (an isoparaffin oil) with a Viscosity at 20 ° C of 1.0 mPa · s.

Bei den erfindungsgemäß als Phosphorträger verwendbaren Organophosphorverbindungen handelt es sich um Verbindungen der FormelIn the invention usable as a phosphorus carrier Organophosphorus compounds are compounds the formula

worin R jeweils eine geradkettige, verzweigte oder cyclische Alkylgruppe mit 6 bis 12 Kohlenstoffatomen oder Arylgruppe bedeuten.wherein each R is a straight-chain, branched or cyclic alkyl group having 6 to 12 carbon atoms or aryl group mean.

Bevorzugte Beispiele für Organophosphorverbindungen der oben­ genannten Formel sind Monodecyl-diphenylphosphit, Dide­ cylphenylphosphit, Triphenylphosphit, Dioctyl-phenylphosphit, Dihexyl-phenyl-phosphit, Diisodecyl-phenylphosphit, Diisooctyl-phenyl-phosphit, Didecyl-o-methylphenyl­ phosphit und Didecyl-p-methylphenylphosphit.Preferred examples of organophosphorus compounds of the above mentioned formula are monodecyl-diphenyl phosphite, dide  cylphenyl phosphite, triphenyl phosphite, dioctyl phenyl phosphite, Dihexyl phenyl phosphite, diisodecyl phenyl phosphite, Diisooctyl-phenyl-phosphite, didecyl-o-methylphenyl phosphite and didecyl-p-methylphenyl phosphite.

Bei den erfindungsgemäß verwendbaren Metall­ dialkyldithiocarbamaten handelt es sich um Verbindungen der FormelIn the metal used in the invention Dialkyldithiocarbamaten are compounds of formula

worin Me ein Metall aus der Gruppe Kupfer, Silber, Zink, Cadmium, Bor, Titan, Zirkonium, Zinn, Blei, Vanadin, Tan­ tal, Antimon, Chrom, Molybdän, Wolfram, Mangan, Kolbalt und Nickel, vorzugsweise Bor, Nickel, Kobalt oder Molybdän bedeutet.where Me is a metal from the group consisting of copper, silver, zinc, Cadmium, boron, titanium, zirconium, tin, lead, vanadium, tan tal, antimony, chromium, molybdenum, tungsten, manganese, and Kolbalt Nickel, preferably boron, nickel, cobalt or molybdenum means.

Bei den erfindungsgemäß verwendbaren Metalldialkyldithiophos­ phaten handelt es sich um Verbindungen der FormelIn the invention usable metal dialkyl dithiophos phaten are compounds of the formula

worin Me für ein Metall aus der Gruppe Kupfer, Silber, Zink, Cadmium, Bor, Titan, Zirkonium, Zinn, Blei, Vanadin, Tantal, Antimon, Chrom, Molybdän, Wolfram, Mangan, Kobalt und Nickel, vorzugsweise für Zink, Nickel, Titan, Vanadin, Molybdän, Wolfram und Mangan, steht.where Me is a metal from the group copper, silver, Zinc, cadmium, boron, titanium, zirconium, tin, lead, vanadium, Tantalum, antimony, chromium, molybdenum, tungsten, manganese, cobalt and nickel, preferably for zinc, nickel, titanium, vanadium, Molybdenum, tungsten and manganese, stands.

Die Alkylgruppe in den obengenannten Metalldialkyldithio­ carbamaten und Metalldialkyldithiophosphaten enthält jeweils 4 bis 8 Kohlenstoffatome, so daß die genannten Metallsalze in den handelsüblichen Grundölen noch löslich sind. Zu Beispielen für besonders vorteilhafte Alkylgruppen gehören die n-, i- und tert-Butylgruppe, die n- und i-Amyl­ gruppe, die n- und i-Hexylgruppe, die n- und i-Heptylgruppe und die 2-Ethylhexylgruppe. Ganz besonders bevorzugt sind die i-Butylgruppe, die n- und i-Amylgruppe und die 2- Ethylhexylgruppe.The alkyl group in the above-mentioned Metalldialkyldithio  carbamates and Metalldialkyldithiophosphaten contains each 4 to 8 carbon atoms, so that said Metal salts in the commercial base oils still soluble are. Examples of particularly advantageous alkyl groups include the n-, i- and tert-butyl group, the n- and i-amyl group, the n- and i-hexyl group, the n- and i-heptyl group and the 2-ethylhexyl group. Very particularly preferred are the i-butyl group, the n- and i-amyl groups and the 2- Ethylhexyl.

Beispiele für erfindungsgemäß mit besonderem Vorteil ver­ wendbare Metalldialkyldithiocarbamate sind folgende: Kupferdialkyldithiocarbamate und Kupferbisdialkyldithio­ carbammate; Silberdialkyldithiocarbamate; Zink- und Cadmium­ bisdialkyldithiocarbamate; Bortrisdialkyldithiocarbamate; Titan-, Zirkonium-, Zinn- und Bleitetrakisdialkyldithio­ carbamate sowie Zinn- und Bleibisdialkyldithiocarbamate; Antimon-, Vanadin- und Tantaltrisdialkyldithiocarbamate, -tetrakis- und -pentakisdialkyldithiocarbamate sowie die Dialkyldithiocarbamate, in denen diese Metalle in gemisch­ ten Oxidationsstufen vorliegen; Chrombis-, Chromtris-, Chromtetrakis- und Chromhexakisdialkyldithiocarbamate, Molybdän- und Wolframtetrakis-, -hexakis- und -oxybis- und -oxy­ tetrakisdialkyl-dithiocarbamate; Manganbis-, -tris- und -hexakisdialkyldithiocarbamate; und Kobalt- und Nickel­ bis- und -tis-dialkyldithiocarbamate.Examples of inventive ver with particular advantage reversible metal dialkyldithiocarbamates are the following: Kupferdialkyldithiocarbamate and Kupferbisdialkyldithio carbammate; Silberdialkyldithiocarbamate; Zinc and cadmium bisdialkyldithiocarbamate; Bortrisdialkyldithiocarbamate; Titanium, zirconium, tin and lead tetrakisdialkyldithio carbamates, and tin and bis-bis-dialkyl dithiocarbamates; Antimony, vanadium and tantalum trialkyldithiocarbamates, tetrakis and pentakisdialkyldithiocarbamates and the Dialkyldithiocarbamates in which these metals in mixture th oxidation states are present; Chromium Bomb, Chromium Tris, Chromium tetrakis and chromium hexakisdialkyldithiocarbamates, Molybdenum and tungsten tetrakis, hexakis and oxybis and oxy tetrakisdialkyl dithiocarbamates; Manganis, tris and -hexakisdialkyldithiocarbamate; and cobalt and nickel bis- and -tis-dialkyldithiocarbamates.

Unter diesen Verbindungen besonders bevorzugt sind die Bortrisdialkyldithiocarbamate, die Nickeltrisdialkyl­ dithiocarbamate und die Molybdäntetrakis- und Molybdänoxy­ tetrakisdialkyldithiocarbamate.Among these compounds, particularly preferred are the Bortrisdialkyldithiocarbamate, the Nickeltrisdialkyl dithiocarbamate and the molybdenum tetrakis and molybdenoxy tetrakisdialkyldithiocarbamate.

Metalldialkyldithiophophate, die erfindungsgemäß mit besonderem Vorteil verwendet werden können, sind die Dialkyldithiophosphate der gleichen Metalle in den glei­ chen Oxidationsstufen wie sie oben für die Metalldialkyldi­ thiocarbamate aufgezählt worden sind.Metalldialkyldithiophophate according to the invention with can be used to particular advantage are the Dialkyldithiophosphate of the same metals in the same chen oxidation states as above for the Metalldialkyldi  thiocarbamate have been enumerated.

Ganz besonders vorteilhaft sind Zinkbisdialkyldithiophos­ phate, Nickelbis- und -trisdialkyldithiophosphate, Titan- und Vanadintetrakisdialkyldithiophosphate, Molybdän- und Wolframtetrakisdialkyldithiophosphate und Molybdän- und Wolframoxytetrakisdialkyldithiophosphate.Very particularly advantageous are zinc bisdialkyldithiophos phate, nickel bis- and tris-dialkyl dithiophosphates, titanium and vanadium tetrakisdialkyldithiophosphates, molybdenum and Tungsten tetrakisdialkyldithiophosphate and molybdenum and Wolframoxytetrakisdialkyldithiophosphate.

Besonders bevorzugte Vertreter der erfindungsgemäß verwen­ deten Metalldialkyldithiocarbamate sind:Particularly preferred representatives of the invention verwen The metal dialkyldithiocarbamates are:

Bortrisdiisobutyldithiocarbamat, Bortrisdiamyldi­ thiocarbamat, Bortrisdi-2-ethylhexyl­ dithiocarbamat, Nickeltrisdiisobutyldithiocarbamat, Nickeltrisdiamyldithiocarbamat, Nickeltrisdi-2-ethylhexyl­ dithiocarbamat, Molybdäntetrakisdi-2-ethylhexyldithio­ carbamat, Molybdänoxytetrakisdi-2-ethylhexyldithiocarb­ amat und Kobaltbisdiisobutyldithiocarbamat.Boron trisdiisobutyl dithiocarbamate, boron triadiyldi thiocarbamate, boron trisdi-2-ethylhexyl dithiocarbamate, nickeltrisdiisobutyldithiocarbamate, Nickel trisdiamyl dithiocarbamate, nickel trisdi-2-ethylhexyl dithiocarbamate, molybdenum tetrakisdi-2-ethylhexyldithio carbamate, molybdenum oxytetrakisdi-2-ethylhexyldithiocarb amate and cobalt bisdiisobutyldithiocarbamate.

Besonders bevorzugte Vertreter der erfindungsgemäß verwen­ deten Metalldialkyldithiophosphate sind Zinkbisdi-2-ethyl­ hexyldithiophosphat, Nickelbis- und -trisdi-2-ethylhexyldi­ thiophosphat, Titan- und Vanadintetrakisdi-2-ethylhexyl­ dithiophosphat sowie Molybdän- und Wolframtetrakis- und Molybdänoxy- und Wolframoxytetrakisdi-2-ethylhexyldi­ thiophosphat.Particularly preferred representatives of the invention verwen The metal dialkyldithiophosphates are zinc bisdi-2-ethyl hexyldithiophosphate, nickel bis- and trisdi-2-ethylhexyldi thiophosphate, titanium and vanadium tetrakis-2-ethylhexyl dithiophosphate and molybdenum and tungsten tetrakis and Molybdenoxy and tungsten oxytetrakis-2-ethylhexyldi thiophosphate.

Die Erfindung wird durch die folgenden Beispiele näher erläu­ tert.The invention will be explained in more detail by the following examples tert.

In den nachstehend beschriebenen Beispielen wurden jeweils handelsübliche Schmieröle bzw. Fette mit den angegebenen Zusammensetzungen einmal mit und einmal ohne das erfindungs­ gemäße Schmiermittelkonzentrat auf ihre Schmiereigenschaften hin untersucht und die dabei erzielten Ergebnisse miteinander verglichen.In the examples described below, respectively Commercially available lubricating oils or greases with the specified Compositions once with and once without the invention appropriate lubricant concentrate on their lubricating properties investigated and the results achieved compared to each other.

Die erzielten Ergebnisse sind in den beigefügten Diagrammen graphisch dargestellt. The results obtained are included in the attached Diagrams graphed.  

Zur Durchführung der Versuche wurde eine kreisrunde Scheibe aus Edelstahl mit einem Durchmesser von 23 mm und einer Dicke von 10 mm verwendet, auf deren Oberfläche ein Tropfen des jeweils zu untersuchenden Schmieröls bzw. Schmierfettes aufgebracht wurde. Auf die Stelle, auf der sich das Schmier­ öl bzw. Schmierfett befand, wurde eine Kugel aus dem gleichen Edelstahl mit einem Durchmesser von 10 mm aufgebracht, die aufgrund ihrer Belastung einen Druck auf die Oberfläche der Metallscheibe ausübte. Die Metallkugel wurde mit einer Frequenz von 50 Hz über eine Amplitude von 1 mm 60-180 min lang unter Belastung auf der Oberfläche der Metallscheibe hin- und herbewegt, wobei während des Versuchs die Belastung innerhalb des Bereiches von 50 bis 300 N und die Tempera­ tur innerhalb des Bereiches von 50 bis 150°C variiert wurden (SRV=Schwing-Reib-Verschleiß-Gerät der Firma Optimol GmbH).To carry out the experiments was a circular disc made of stainless steel with a diameter of 23 mm and a Thickness of 10 mm used, on the surface of which a drop of the respective lubricating oil or grease to be examined was applied. In the place where the smear oil or grease, was a ball of the same Stainless steel with a diameter of 10 mm applied, because of their stress a pressure on the surface the metal disc exerted. The metal ball was with a Frequency of 50 Hz over an amplitude of 1 mm for 60-180 min under load on the surface of the metal disc and moved, with the load during the experiment within the range of 50 to 300 N and the tempera were varied within the range of 50 to 150 ° C. (SRV = vibration-friction-wear device of Optimol GmbH).

Da aufgrund der Reibung zwischen der belasteten Kugel und der Oberfläche der Metallscheibe innerhalb des Versuchs­ zeitraums erzeugte Verschleißprofil quer zur Oszillations­ richtung der Kugel wurde mittels eines geeigneten Aufzeich­ nungsgerätes aufgezeichnet, wobei die beiliegen­ den Diagramme erhalten wurden, in denen auf der Ordinate die Verschleißhöhe als Differenz zwischen dem höchsten und dem tiefsten Punkt des Oberflächenprofils der Metallscheibe in Abhängigkeit von der Abtaststrecke der Oberfläche der Metallscheibe auf der Abszisse dargestellt ist.Because of the friction between the loaded ball and the surface of the metal disk within the experiment Periodically generated wear profile across the oscillation Direction of the ball was by means of a suitable Aufzeich recorded, with the enclosed The diagrams were obtained in which on the ordinate the wear height as the difference between the highest and the lowest point of the surface profile of the metal disk depending on the scanning distance of the surface of Metal disc is shown on the abscissa.

In den beiliegenden Diagrammen entspricht eine Profiltiefe auf der Ordinate von 1 cm einer realen Profiltiefe in der Oberfläche der Metallscheibe von 1 µm mit Ausnahme des Diagramms B′ des Beispiels 2. Darin entspricht eine Profil­ tiefe von 1 cm einer realen Profiltiefe von 2,5 µm. In the accompanying diagrams corresponds to a tread depth on the ordinate of 1 cm of a real tread depth in the Surface of the metal disc of 1 micron with the exception of Diagram B 'of Example 2. This corresponds to a profile depth of 1 cm of a real tread depth of 2.5 microns.  

Die Diagramme wurden unter im übrigen identischen Bedingun­ gen aufgezeichnet (Belastung der Kugel 50 bis 300 N, Reibfrequenz 50 Hz, Temperatur 50 bis 150°C, Reibamplitude 1 mm, Versuchsdauer 1 bis 3 h). Die unterhalb der Diagramme an­ gegebenen Reibkoeffizienten (RKmax=maximaler Reibkoeffizient; RKd=durchschnittlicher Reibkoeffizient über 80% der Reibko­ effizientenkurve) wurden ebenfalls mit dem o. g. SRV-Gerät gemessen. In allen Versuchen wurde, sofern nicht anders angegeben, als er­ findungsgemäßes Schmiermittelkonzentrat ein Produkt mit der folgenden Zusammensetzung verwendet: The diagrams were recorded under otherwise identical conditions (load on the ball 50 to 300 N, friction frequency 50 Hz, temperature 50 to 150 ° C., friction amplitude 1 mm, test duration 1 to 3 h). The friction coefficients given below the diagrams (R K max = maximum friction coefficient, R K d = average coefficient of friction over 80% of the friction coefficient curve) were likewise measured with the above-mentioned SRV device. In all experiments, unless otherwise stated, the product of the following composition was used as the lubricant concentrate according to the invention:

50%50% Pentaerythrittetraoctylester (Ciba 602® der Firma Ciba AG)Pentaerythritol tetraoctyl ester (Ciba 602® from Ciba AG) 20%20% Copolymer von α-Olefindicarbonsäurebutanolester (Ketjenlube 135® der Firma Akzo)Copolymer of α-olefinic acid carboxylic acid butanol ester (Ketjenlube 135® from Akzo) 3%3% Polyalkylenglycol (EMKAROX VG 380® der Firma ICI, Hamburg)Polyalkylene glycol (EMKAROX VG 380® from ICI, Hamburg) 6,5%6.5% TrimethyladipinsäuredidecylesterTrimethyladipinsäuredidecylester 2,5%2.5% Didecylphenylphosphitdidecylphenylphosphite 9%9% Molybdän-di-(2-ethylhexyldithiophosphat)/Molybdän-di-(2-ethylhexyldi-thiocarbamat) (1 : 4)Molybdenum di (2-ethylhexyl dithiophosphate) / molybdenum di (2-ethylhexyl di-thiocarbamate) (1: 4) 7%7% Ethylhexylthiadiazol (Amoco 158® der Firma Amoco)Ethyl hexyl thiadiazole (Amoco 158® from Amoco) 2%2% Bis-2,6-di-tert-butylphenolBis-2,6-di-tert-butyl phenol

Beispiel 1Example 1

Es wurde ein hochviskoses Schmieröl mit einer Viskosität von 2200 mPa · s bei 50°C der folgenden Zusammensetzung hergestellt und getestet:It became a highly viscous lubricating oil with a viscosity of 2200 mPa · s at 50 ° C of the following composition manufactured and tested:

Trimethyladipinsäuredidecylester|34%Trimethyladipinsäuredidecylester | 34% Polyisobutylen 43 000 mPa · s/100°CPolyisobutylene 43,000 mPa · s / 100 ° C 32%32% Schmiermittel-SchleppsubstanzLubricant drag substance 6%6% erfindungsgemäßes SchmiermittelkonzentratInventive lubricant concentrate 28%28%

In dem Vergleichsprodukt wurde das erfindungsgemäße Schmier­ mittelkonzentrat weggelassen.In the comparative product was the inventive lubricating medium concentrate omitted.

Beide Produkte wurden 1 h lang bei einer Temperatur von 150°C und einer Belastung von 200 N unter identischen Be­ dingungen getestet. Die erzielten Ergebnisse sind in den bei­ gefügten Diagrammen A (erfindungsgemäß) und A′ (gemäß Stand der Technik) graphisch dargestellt.Both products were kept at a temperature of 1 h for 1 h 150 ° C and a load of 200 N under identical loading conditions tested. The results obtained are in the joined diagrams A (according to the invention) and A '(according to Stand the technique) graphically.

Mit dem erfindungsgemäßen Schmiermittelzusatz ergab sich eine Profiltiefe von 0,80 µm (Mittelwert aus zwei Messungen). Ohne den erfindungsgemäßen Schmiermittelzusatz ergab sich eine Profiltiefe von 1,68 (Mittelwert aus zwei Messungen).With the lubricant additive of the invention resulted a profile depth of 0.80 μm (mean of two measurements). Without the lubricant additive of the invention resulted a tread depth of 1.68 (mean of two measurements).

Beispiel 2example 2

Es wurde ein mittelviskoses Schmieröl mit einer Viskosität von 190 bis 200 mPa · s bei 50°C der folgenden Zusammensetzung hergestellt:It became a medium viscosity lubricating oil with a viscosity from 190 to 200 mPa · s at 50 ° C of the following composition manufactured:

polymere α-Olefinester (Ketjenlube 135®)|12%polymeric α-olefin esters (Ketjenlube 135®) | 12% TrimethyladipinsäuredidecylesterTrimethyladipinsäuredidecylester 36%36% Polyisobutylen 4300 mPa · s/100°CPolyisobutylene 4300 mPa · s / 100 ° C 18%18% Schmiermittel-SchleppsubstanzLubricant drag substance 6%6% erfindungsgemäßes SchmiermittelkonzentratInventive lubricant concentrate 28%28%

Bei dem Vergleichsprodukt wurde das erfindungsgemäße Schmier­ mittelkonzentrat weggelassen.The comparative product was the inventive lubricating medium concentrate omitted.

Die Versuche wurden unter identischen Bedingungen 1 h lang bei einer Temperatur von 150°C und einer Belastung von 200 N durchgeführt. Dabei wurden die in den beigefügten Dia­ grammen B und B′ graphisch dargestellten Ergebnisse erzielt. Während bei Verwendung des erfindungsgemäßen Schmiermittels die Profiltiefe bei 0,875 µm (Durchschnitt aus zwei Mes­ sungen) lag, betrug die Profiltiefe bei Verwendung des Vergleichsprodukts 13,98 µm.The experiments were carried out under identical conditions for 1 h at a temperature of 150 ° C and a load of 200 N performed. In doing so, the attached dia B and B 'graphically presented results achieved. While using the lubricant of the invention the profile depth at 0.875 μm (average of two mes the tread depth when using the Comparative product 13.98 microns.

Beispiel 3example 3

Es wurde ein Schmieröl mittlerer Viskosität von 120 bis 150 mPa · s bei 50°C mit der nachstehend angegebenen Zusam­ mensetzung hergestellt:It became a lubricating oil medium viscosity of 120 to 150 mPa.s at 50 ° C with the following composition Composition:

hochviskoses α-olefinester-Copolymeres (Ketjenlube 165)|4%high viscosity α-olefin ester copolymer (Ketjenlube 165) | 4% mittelviskoses α-Olefinesterpolymeres (Ketjenlube 135®medium-viscosity α-olefin ester polymer (Ketjenlube 135® 12%12% TrimethyladipinsäuredidecylesterTrimethyladipinsäuredidecylester 34%34% Polyisobutylen 200 mPa · s/100°CPolyisobutylene 200 mPa · s / 100 ° C 12%12% Schmiermittel-SchleppsubstanzLubricant drag substance 6%6% erfindungsgemäßes KonzentratInventive concentrate 32%32%

In dem Vergleichsprodukt wurde das erfindungsgemäße Schmier­ mittelkonzentrat weggelassen.In the comparative product was the inventive lubricating medium concentrate omitted.

Die Versuche wurden unter identischen Bedingungen 1 h lang bei einer Temperatur von 150°C und einer Belastung von 200 N durchgeführt. Die dabei erzielten Ergebnisse sind in den beigefügten Diagrammen C (erfindungsgemäß) und C′ (Vergleichsprodukt) graphisch dargestellt. The experiments were carried out under identical conditions for 1 h at a temperature of 150 ° C and a load of 200 N performed. The results obtained are in the attached diagrams C (according to the invention) and C ' (Comparative product) shown graphically.  

Die Profiltiefe bei Verwendung des erfindungsgemäßen Schmier­ öls betrug 1,12 µm (Durchschnitt aus drei Messungen). Die Profiltiefe bei Verwendung des Vergleichsprodukts betrug 3,48 µm.The tread depth when using the lubricating invention oil was 1.12 μm (average of three measurements). The Profile depth when using the comparison product was 3.48 μm.

Beispiel 4example 4

Es wurde ein hochviskoses Haft- und Hochtemperaturschmier­ öl mit einer Viskosität von 15 000 mPa · s bei 50°C mit der nachstehend angegebenen Zusammensetzung hergestellt:It became a highly viscous adhesive and high temperature lubricant Oil with a viscosity of 15 000 mPa · s at 50 ° C with the prepared according to the following composition:

Trimethyladipinsäuredidecylester|29%Trimethyladipinsäuredidecylester | 29% Polyisobutylen 43 000 mPa · s/100°CPolyisobutylene 43,000 mPa · s / 100 ° C 52%52% erfindungsgemäßes SchmiermittelkonzentratInventive lubricant concentrate 19%19%

Als Vergleichsprodukt wurde das gleiche Schmieröl ohne das erfindungsgemäße Schmiermittelkonzentrat verwendet.As a comparative product, the same lubricating oil without the used lubricant concentrate according to the invention.

Die Versuche wurden 1 h lang bei einer Temperatur von 150°C und einer Belastung von 200 N unter identischen Bedingungen durchgeführt.The experiments were carried out at a temperature of 150 ° C for 1 h and a load of 200 N under identical conditions carried out.

Bei Verwendung des erfindungsgemäßen Schmieröls betrug die Profiltiefe 0,80 µm, (Durchschnittswert aus drei Messungen), während die Profiltiefe bei Verwendung des Vergleichsprodukts 1,57 µm betrug, wie die beigefügten Diagramme D (erfindungsge­ mäß) und D′ (Vergleichsprodukt) zeigen.When using the lubricating oil according to the invention was Tread depth 0.80 μm, (average of three measurements), while the tread depth when using the reference product 1.57 microns, as the accompanying diagrams D (erfindungsge and D '(comparative product).

Beispiel 5example 5

Es wurde ein Schmierfett für die Mehrzweckschmierung höchst­ belasteter Getriebe und Gleichlaufgelenke der folgenden Zusammensetzung hergestellt:It was a grease for multi-purpose lubrication highest loaded gearbox and constant velocity joints of the following Composition produced:

Mineralöl SAE 80 (Solvent Raffinat HR80)|70%Mineral oil SAE 80 (solvent raffinate HR80) | 70% Konsistenzgeber auf LithiumstearatbasisBodying agent based on lithium stearate 9%9% erfindungsgemäßes SchmiermittelkonzentratInventive lubricant concentrate 21%21%

Als Vergleichsprodukt wurde das gleiche Schmierfett ohne das erfindungsgemäße Schmiermittelkonzentrat, jedoch mit 3 Gew.-% Molybdändisulfid/Graphit-Gemisch als Zusatz, verwendet. Die Versuche wurden 3 h lang bei einer Temperatur von 50°C und einer Belastung von 300 N durchgeführt bei ansonsten identischen Bedingungen.As a comparative product, the same grease was without the lubricant concentrate according to the invention, but with 3 wt .-% molybdenum disulfide / graphite mixture as an additive used. The experiments were carried out at a temperature of 50 ° C for 3 hours and a load of 300 N carried out at otherwise identical conditions.

Bei Verwendung des erfindungsgemäßen Schmierfettes betrug die Profiltiefe 0,95 µm (Durchschnittswert aus drei Messungen), während die Profiltiefe bei Verwendung des Vergleichsprodukts 1,63 µm (Durchschnitt aus drei Messungen) betrug, wie die beigefügten Diagramme E (erfindungsgemäß) und E′ (Ver­ gleichsprodukt) zeigen. When using the lubricating grease according to the invention the profile depth 0.95 μm (average of three measurements), while the tread depth when using the reference product 1.63 μm (average of three measurements) was, like the attached diagrams E (according to the invention) and E '(Ver same product).  

VergleichsversuchComparative test

Es wurden weitere Vergleichstests durchgeführt auf die gleiche Weise wie in den vorstehenden Beispielen beschrieben, jedoch unter Einhaltung der folgenden identischen Testbedingungen (falls nichts anderes angegeben ist): Belastung 200 N; Temperatur 125°C; Versuchsdauer 2 Stunden.Further comparative tests were carried out on the same way as in the previous examples described, but in compliance with the following identical test conditions (if nothing else specified): load 200 N; Temperature 125 ° C; Duration of the test 2 hours.

Die Zusammensetzungen der bei diesen Versuchen verwendeten Schmiermittel-Testproben (a) bis (h) gemäß der Erfindung und (i) gemäß Stand der Technik, wie er durch die DE-OS 20 34 383 repräsentiert wird, sowie die dabei erzielten Ergebnisse sind in der folgenden Tabelle zusammengefaßt.The compositions used in these experiments Lubricant test samples (a) to (h) according to the invention and (i) according to the prior art, as described by DE-OS 20 34 383 is represented as well as the achieved Results are summarized in the following table.

Die Probe (a) entspricht einer erfindungsgemäßen Probe, die ohne Verwendung eines Metalldialkyldithiophosphats und unter alleiniger Verwendung von Metalldialkyldithiocarbamaten als Additiv hergestellt wurde.The sample (a) corresponds to a sample according to the invention, those without the use of a Metalldialkyldithiophosphats and using only Metalldialkyldithiocarbamaten prepared as an additive has been.

Die Proben (b) bis (h) stellen ebenfalls erfindungsgemäße Proben dar, wobei die Proben (e), (f) und (g), die eine identische Zusammensetzung aufweisen, sich nur dadurch unterschieden, daß sie bei unterschiedlichen Temperaturen (100°C/1 h bzw. 130°C/1 h bzw. 150°C/1 h in der genannten Reihenfolge getestet wurden.The samples (b) to (h) are also inventive Samples, wherein the samples (e), (f) and (g), the one have identical composition, only by it distinguished that they are at different temperatures (100 ° C / 1 h or 130 ° C / 1 h or 150 ° C / 1 h in said Order were tested.

Die Probe (i) ist eine Probe gemäß Stand der Technik, repräsentiert durch DE-OS 20 34 383, die als Additiv neben dem Pentaerythritester noch Zink-di-(2-ethylhexyl­ dithiophosphat enthielt. Diese Vergleichsprobe wurde bei 200 N/150°C/1 h getestet.The sample (i) is a sample according to the prior art, represented by DE-OS 20 34 383, as an additive next the pentaerythritol still zinc di- (2-ethylhexyl dithiophosphate contained. This comparative sample was included 200 N / 150 ° C / 1 h tested.

Wie aus den in der folgenden Tabelle zusammengefaßten SRV- Verschleiß-Testergebnissen ersichtlich, waren die erfindungsgemäßen Schmiermittelproben durchweg etwa um den Faktor 10 (unter Berücksichtigung der Testdauer) besser in bezug auf die Verschleißschutzwirkung (bessere Schmierwirkung) als das Produkt gemäß Stand der Technik, wobei die erfindungsgemäßen Proben auch bei unterschiedlichen Temperaturen deutlich verbessert waren (Proben (e) bis (h)). As can be seen from the SRVs summarized in the following table: Wear test results, were the Lubricant samples according to the invention throughout about the  Factor 10 (considering the test duration) better in regarding the wear protection effect (better Lubricating action) as the product according to the prior art, wherein the samples of the invention also in different temperatures were significantly improved (Samples (e) to (h)).  

Tabelle table

Claims (9)

1. Schmiermittel bzw. Schmiermittelkonzentrat auf der Basis von Mineral- und/oder Syntheseöl, das eine Verbin­ dung mit mindestens einem quartären Kohlenstoffatom und mindestens einer Esterbindung im Molekül sowie weitere üb­ liche Zusätze enthält, dadurch gekennzeich­ net, daß es enthält
  • a) mindestens einen 4- bis 8wertigen Alkohol mit mindestens einem quartären Kohlenstoffatom im Molekül mit einer Dichte d₂₀ von mindestens 0,900 und einer Enthalpie H von mindestens 350 kcal/kg, ausgewählt aus der Gruppe der Mono-, Di- und Tripentaerythrite, deren alkoholische Hydroxylgruppe(n) durch eine Säure mit unverzweigter oder verzweigter Alkyl-, Aralkyl- oder Arylgruppe mit 6 bis 18 Kohlenstoffatomen verestert oder ethoxyverestert ist (sind)
  • b) eine zusätzliche Komponente mit mindestens einer freien Hydroxylgruppe im Molekül,
  • (c) mindestens ein Metalldialkyldithiocarbamat der Formel worin bedeuten:
    Me ein Metall aus der Gruppe Kupfer, Silber, Zink, Cad­ mium, Bor, Titan, Zirkonium, Zinn, Blei, Vanadin, Tan­ tal, Antimon, Chrom, Molybdän, Wolfram, Mangan, Ko­ balt und Nickel und
    Alkyl eine Alkylgruppe mit 4 bis 8 Kohlenstoffatomen,
  • d) mindestens ein Dialkylaryl-, Monoalkyldiaryl-, Trialkyl- oder Triarylphosphit, in dem die Alkylgruppe unverzweigt, ver­ zweigt oder zyklisch ist und 8 bis 12 Kohlenstoffatome auf­ weist,
  • e) ein Thiazol und
  • f) als weitere übliche Zusätze an sich bekannte Antioxida­ tionsmittel, Metalldesaktivatoren, Detergentien, Dispergier­ mittel, Antischaummittel und/oder Viskositätsindexverbesse­ rungsmittel.
1. lubricant or lubricant concentrate based on mineral and / or synthetic oil containing a connec tion with at least one quaternary carbon atom and at least one ester bond in the molecule and other üb Liche additives, characterized in that it contains
  • a) at least one 4- to 8-valent alcohol having at least one quaternary carbon atom in the molecule with a density d₂₀ of at least 0.900 and an enthalpy H of at least 350 kcal / kg, selected from the group of mono-, di- and Tripentaerythrite whose alcoholic hydroxyl group (n) is esterified or ethoxylated by an acid of unbranched or branched alkyl, aralkyl or aryl group of 6 to 18 carbon atoms
  • b) an additional component having at least one free hydroxyl group in the molecule,
  • (C) at least one Metalldialkyldithiocarbamat of the formula in which mean:
    Me is a metal from the group consisting of copper, silver, zinc, cadmium, boron, titanium, zirconium, tin, lead, vanadium, talc, antimony, chromium, molybdenum, tungsten, manganese, cobalt and nickel and
    Alkyl is an alkyl group having 4 to 8 carbon atoms,
  • d) at least one dialkylaryl, monoalkyldiaryl, trialkyl or triaryl phosphite, in which the alkyl group is unbranched, branched or cyclic and has from 8 to 12 carbon atoms,
  • e) a thiazole and
  • f) as further customary additives per se known antioxidant tion agents, metal deactivators, detergents, dispersants, antifoams and / or Viskositätsindexverbesse medium.
2. Schmiermittel bzw. Schmiermittelkonzentrat nach Anspruch 1, dadurch gekennzeichnet, daß es als weitere Komponente ent­ hält
  • (g) mindestens ein Metalldialkyldithiophosphat der allgemei­ nen Formel worin bedeuten:
    Me ein Metall aus der Gruppe Kupfer, Silber, Zink, Cadmium, Bor, Titan, Zirkonium, Zinn, Blei, Vanadin, Tantal, An­ timon, Chrom, Molybdän, Wolfram, Mangan, Cobalt und Nickel und
    Alkyl eine Alkylgruppe mit 4 bis 8 Kohlenstoffatomen.
2. lubricant or lubricant concentrate according to claim 1, characterized in that it holds ent as a further component
  • (g) at least one metal dialkyldithiophosphate of the general formula in which mean:
    Me is a metal from the group of copper, silver, zinc, cadmium, boron, titanium, zirconium, tin, lead, vanadium, tantalum, antonone, chromium, molybdenum, tungsten, manganese, cobalt and nickel and
    Alkyl is an alkyl group having 4 to 8 carbon atoms.
3. Schmiermittel bzw. Schmiermittelkonzentrat nach Anspruch 2, dadurch gekennzeichnet, daß es Bortrisdiisobutyldithiocar­ bamat und/oder Bortrisdi-2-ethylhexyldithiocarbamat in Kombi­ nation mit Nickeltrisdiisobutyldithiocarbamat, Nickeltrisdi­ amyldithiocarbamat und/oder Nickeltrisdi-2-ethylhexyldithio­ carbamat sowie Zinkbisdi-2-ethylhexyldithiophosphat, Nickel­ trisdi-2-ethylhexyldithiophosphat, Titantetrakisdi-2-ethyl­ hexyldithiophosphat, Vanadintetrakisdi-2-ethylhexyldithio­ phosphat, Molybdäntetrakis- oder Molybdänoxytetrakisdi-2- ethylhexyldithiophosphat, Wolframtetrakis- und/oder Wolfram­ oxytetrakisdi-2-ethylhexyldithiophosphat enthält.3. lubricant or lubricant concentrate according to claim 2, characterized in that it is boron tris diisobutyl dithiocar bamate and / or boron trisdi-2-ethylhexyldithiocarbamate in combi nation with nickel trisdiisobutyl dithiocarbamate, nickel trisdi amyldithiocarbamate and / or nickeltrisdi-2-ethylhexyldithio carbamate and zinc bisdi-2-ethylhexyl dithiophosphate, nickel tris-di-2-ethylhexyl dithiophosphate, titanium tetrakisdi-2-ethyl hexyl dithiophosphate, vanadium tetrakisdi-2-ethylhexyl dithio phosphate, molybdenum tetrakis or molybdenum oxytetrakisdi-2 ethylhexyl dithiophosphate, tungsten tetrakis and / or tungsten oxytetrakisdi-2-ethylhexyl dithiophosphate contains. 4. Schmiermittel bzw. Schmiermittelkonzentrat nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß es die Komponente (a) in einer Menge von 0,1 bis 40 Gew.-%, vorzugs­ weise 0,1 bis 20 Gew.-%, insbesondere 1 bis 12 Gew.-%, spe­ ziell 2 bis 6 Gew.-%, bezogen auf das Gewicht des Mineral- und/oder Syntheseöls, enthält. 4. Lubricant or lubricant concentrate after a of claims 1 to 3, characterized in that it is the Component (a) in an amount of 0.1 to 40 wt .-%, preferably from 0.1 to 20 wt .-%, in particular 1 to 12 wt .-%, spe 2 to 6% by weight, based on the weight of the mineral and / or synthetic oil.   5. Schmiermittel bzw. Schmiermittelkonzentrat nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß es als Grundöl Rüböl, Naturöl und/oder ein Syntheseöl mit einer Viskosität im Bereich von 1,0 bis 2×10⁶ mPa · s bei 20°C enthält.5. lubricant or lubricant concentrate according to one of Claims 1 to 4, characterized in that it as a base oil Rapeseed oil, natural oil and / or a synthetic oil with a viscosity in Range of 1.0 to 2 × 10⁶ mPa · s at 20 ° C. 6. Schmiermittel bzw. Schmiermittelkonzentrat nach Anspruch 5, dadurch gekennzeichnet, daß es als Naturöl ein Mineralöl mit einer Viskosität von 1,0 mPa · s bei 20°C bis 540 mPa · s bei 50°C und/oder als Syntheseöl einen aromatischen oder alipha­ tischen Dicarbonsäureester, insbesondere Poly-α-olefin-dicar­ bonsäureester, speziell -butylester, mit einem Molekularge­ wicht im Bereich von 1000 bis 3000, vorzugsweise Phthalsäu­ rediisodecylester, Trimethyladipinsäuredidecylester und Se­ bacinsäuredioctylester, ein Polyisobutylen mit einem Moleku­ largewicht von 1000 bis 100 000 und einer Viskosität von 200 bis 43 000 mPa · s bei 100°C, ein Polymethacrylat mit ei­ ner Viskosität von 1000 mPa · s bei 100°C, ein nicht-wasser­ lösliches Polyglycol mit einer Viskosität von 5 bis 60 mPa · s bei 100°C, ein Isoparaffinöl und/oder Alkylbenzol mit einem Flammpunkt von über 50°C und einer Viskosität im Bereich von 1,0 bis 2 000 000 mPa · s bei 20°C und/oder einen Telomersäure­ ester, vorzugsweise einen Neopentylglycol- oder Trimethylol­ propanester der Telomersäure, enthält.6. lubricant or lubricant concentrate according to claim 5, characterized in that it is a mineral oil as natural oil with a viscosity of 1.0 mPa · s at 20 ° C to 540 mPa · s at 50 ° C and / or as a synthetic oil an aromatic or alipha dicarboxylic acid esters, in particular poly-α-olefin dicar Bicester, especially butyl ester, with a Molekularge in the range of 1000 to 3000, preferably phthalic acid redisodecyl ester, trimethyl adipic acid dicylate and Se bacic acid dioctyl ester, a polyisobutylene with a molecule largeweight of 1000 to 100 000 and a viscosity of 200 to 43,000 mPa · s at 100 ° C, a polymethacrylate with egg ner viscosity of 1000 mPa · s at 100 ° C, a non-water soluble polyglycol having a viscosity of 5 to 60 mPa · s at 100 ° C, an isoparaffin oil and / or alkylbenzene with a Flash point of over 50 ° C and a viscosity in the range of 1.0 to 2,000,000 mPa · s at 20 ° C and / or a telomeric acid ester, preferably a neopentyl glycol or trimethylol propane ester of the telomeric acid. 7. Schmiermittel bzw. Schmiermittelkonzentrat nach einem der An­ sprüche 1 bis 6, dadurch gekennzeichnet, daß es die Komponente(n) (c) und ggf. (g) in einer Menge von 0,1 bis 10 Gew.-%, vorzugsweise von 0,1 bis 5 Gew.-%, insbesondere von 0,1 bis 3 Gew.-%, enthält.7. Lubricant or lubricant concentrate according to one of the An Claims 1 to 6, characterized in that it contains the component (s) (c) and optionally (g) in an amount of 0.1 to 10 wt .-%, preferably from 0.1 to 5 wt .-%, in particular from 0.1 to 3 wt .-%, contains. 8. Schmiermittel bzw. Schmiermittelkonzentrat nach einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, daß es das Thiazol in einer Menge von 0,5 bis 10 Gew.-%, vorzugsweise 1 bis 3 Gew.-%, enthält.8. Lubricant or lubricant concentrate after a of claims 1 to 7, characterized in that it the thiazole in an amount of 0.5 to 10 wt .-%, preferably 1 to 3 wt .-%, contains. 9. Schmiermittel bzw. Schmiermittelkonzentrat nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, daß es das Phosphit in einer Menge von 0,1 bis 5 Gew.-%, vorzugsweise 0,5 bis 2 Gew.-%, enthält.9. Lubricant or lubricant concentrate after a of claims 1 to 8, characterized in that it the phosphite in an amount of 0.1 to 5 wt .-%, preferably 0.5 to 2 wt .-%, contains.
DE19873712133 1987-04-10 1987-04-10 LUBRICANTS OR LUBRICANT CONCENTRATE Granted DE3712133A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DE19873712133 DE3712133A1 (en) 1987-04-10 1987-04-10 LUBRICANTS OR LUBRICANT CONCENTRATE
CA000563732A CA1340272C (en) 1987-04-10 1988-04-08 Lubricant or lubricant concentrate
JP63503324A JP2843584B2 (en) 1987-04-10 1988-04-11 Lubricant or lubricant concentrate
ES88105725T ES2064326T3 (en) 1987-04-10 1988-04-11 LUBRICATING AGENT OR LUBRICATING AGENT CONCENTRATE.
EP88105725A EP0286139B1 (en) 1987-04-10 1988-04-11 Lubricant or lubricant concentrate
KR1019880701563A KR960014936B1 (en) 1987-04-10 1988-04-11 Lubricant or lubricant concentrate
AT88105725T ATE111149T1 (en) 1987-04-10 1988-04-11 LUBRICANTS RESPECTIVELY. LUBRICANT CONCENTRATE.
PCT/EP1988/000300 WO1988008021A1 (en) 1987-04-10 1988-04-11 Lubricant or lubricant concentrate
DE3851355T DE3851355D1 (en) 1987-04-10 1988-04-11 Lubricant or lubricant concentrate.
US08/147,014 US5665683A (en) 1987-04-10 1993-11-03 Lubricant and lubricant concentrate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19873712133 DE3712133A1 (en) 1987-04-10 1987-04-10 LUBRICANTS OR LUBRICANT CONCENTRATE

Publications (2)

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DE3712133A1 DE3712133A1 (en) 1988-10-20
DE3712133C2 true DE3712133C2 (en) 1993-07-15

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DE19873712133 Granted DE3712133A1 (en) 1987-04-10 1987-04-10 LUBRICANTS OR LUBRICANT CONCENTRATE
DE3851355T Expired - Lifetime DE3851355D1 (en) 1987-04-10 1988-04-11 Lubricant or lubricant concentrate.

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Application Number Title Priority Date Filing Date
DE3851355T Expired - Lifetime DE3851355D1 (en) 1987-04-10 1988-04-11 Lubricant or lubricant concentrate.

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EP (1) EP0286139B1 (en)
JP (1) JP2843584B2 (en)
KR (1) KR960014936B1 (en)
AT (1) ATE111149T1 (en)
CA (1) CA1340272C (en)
DE (2) DE3712133A1 (en)
ES (1) ES2064326T3 (en)
WO (1) WO1988008021A1 (en)

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DE4128647A1 (en) * 1991-08-29 1993-03-11 Henkel Kgaa USE OF ISOPALMITINE ACID ESTERS AS LUBRICANTS FOR SECONDARY MOTORS
DE4128646A1 (en) * 1991-08-29 1993-03-04 Henkel Kgaa ESTER MIXTURES OF STRONG BRANCHED CARBONIC ACIDS
FR2684108B1 (en) * 1991-11-27 1994-10-28 Mobil Oil France NEW GREASE, ESPECIALLY FOR USE IN HOMOCINETIC JOINTS.
JP4098513B2 (en) * 2001-02-02 2008-06-11 新日本石油株式会社 Lubricating oil composition
JP4801574B2 (en) * 2006-12-11 2011-10-26 株式会社リコー Protective agent for image carrier, protective layer forming apparatus, image forming method, image forming apparatus, and process cartridge
JP2008297501A (en) * 2007-06-01 2008-12-11 New Japan Chem Co Ltd Lubricating oil for use in bearing

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Also Published As

Publication number Publication date
ATE111149T1 (en) 1994-09-15
KR890701717A (en) 1989-12-21
WO1988008021A1 (en) 1988-10-20
ES2064326T3 (en) 1995-02-01
EP0286139A1 (en) 1988-10-12
JPH01503543A (en) 1989-11-30
JP2843584B2 (en) 1999-01-06
EP0286139B1 (en) 1994-09-07
DE3712133A1 (en) 1988-10-20
DE3851355D1 (en) 1994-10-13
KR960014936B1 (en) 1996-10-21
CA1340272C (en) 1998-12-15

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Owner name: BREMER & LEGUIL GMBH, 47051 DUISBURG, DE