CA1339482C - Lubricant or lubricant concentrate - Google Patents

Lubricant or lubricant concentrate

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Publication number
CA1339482C
CA1339482C CA000563060A CA563060A CA1339482C CA 1339482 C CA1339482 C CA 1339482C CA 000563060 A CA000563060 A CA 000563060A CA 563060 A CA563060 A CA 563060A CA 1339482 C CA1339482 C CA 1339482C
Authority
CA
Canada
Prior art keywords
lubricant
weight
concentrate
amount
oil
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 - Fee Related
Application number
CA000563060A
Other languages
French (fr)
Inventor
Erasmus 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.)
Max Grill Gesmbh
Original Assignee
MAX GRILL GES.MBH
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 MAX GRILL GES.MBH filed Critical MAX GRILL GES.MBH
Application granted granted Critical
Publication of CA1339482C publication Critical patent/CA1339482C/en
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Expired - Fee Related 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
    • 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
    • C10M169/044Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
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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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    • 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
    • C10M101/04Fatty oil fractions
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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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    • 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
    • C10M105/40Esters containing free hydroxy or carboxyl groups
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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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    • C10M107/00Lubricating compositions characterised by the base-material being a macromolecular compound
    • 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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    • C10M107/00Lubricating compositions characterised by the base-material being a macromolecular compound
    • 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
    • C10M129/16Ethers
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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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    • C10M129/00Lubricating 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
    • C10M129/76Esters 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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    • 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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    • 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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    • C10M169/06Mixtures of thickeners and additives
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06Well-defined aromatic compounds
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
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    • C10M2203/065Well-defined aromatic compounds used as base material
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  • Lubricants (AREA)

Abstract

Lubricant or lubricant concentrate on mineral oil and/or synthetic oil basis having improved lubricating properties, in particular improved load bearing, sliding and corrosion inhibiting properties, which contains a) one or more mineral oils and/or synthetic oils as base oil and b) at least one compound A containing in its molecule at least one quaternary carbon atom and at least one ester bond and/or ether bond, as well as c) further usual additives.

Description

1339~82 1 D e s c r i p t i o n The present invention refers to a novel lubricant ~luhricating agent) or lubricant concentrate on a mineral oil and/or synthetic oil ~asis having improved lubricating properties, in particular improved load bearing, sliding or gliding as well as corrosi~n preventing properties.

During the last decades nwnerous processes and lubricating systems have been developed in order to reduce the friction and wear of moving machine parts and to lower the costs for energy and replacement parts and to extend the service life of lubricants and of materials. As an ideal lubricant the "lifetime lubricant~ is considered which takes into account the ecological requirements ~ecoming more and more restrictive.

On the way to longlife and hi~hduty lubricants, lubricating systems and lubricating processes in the first step the so-called chemical wear lubrication has been developed. By using it the metal-to-metal contact could be largely prevented by means of the salt formation on the surfaces of the micro-mountains of the moving parts by forming chemically reactive cover coats on the surfaces or by introducing chemically reactive compounds into the base lubricants.
In this manner the seizing of the machine parts could be prevented But simultaneously the wear by shearing of the salt coats between the metal parts moving against one another has been promoted. The service life of the materials therefore remained relatively short. In a further step solid lubricants have been developed which were introduced bet7~7een the moving metal parts such as graphite, MoS2, Tiu2, Ca3(P04)2, teflon etc., which were introduced in the 3~ form of lubricating cover coats, suspensions, pastes or fats. In this way the frictionating parts were better X
2 1339~82 l separated from each other and their loadability was increased.
However, the solid lubricants and base media are separa-ted from each other sooner or later under the influence of centripetal movements of higher circumference speeds and at a higher temperature due to their different specific densities. The longlife lubrication is limited thereby.
In a further step the deposition of suitable metal cations out of chemical complexes dissolved in a lubricant onto the frictionating surfaces in operation has been achieved. There under the pressure and the temperature of the frictionating - parts they for~l eutectica together ~ith th~ metal border layers, which fill up smoothingly the roughness valleys and flatten in part tribochemically in part microplastically the roughness peaks. The anionic part of the organometallic 1~ compounds forms in situ lubricating and adhering reaction layers on the newly rebuilt eutectoid frictional faces.

Besides a starting phase which is too long, a friction coefficient and a wear which are toc high, the control of the reaction proceeding is a problem with these lubri-cating systems. Either ~terial-independent eutectica and reaction layers are achi-eved which do no more function sufficiently as agents for removing the minute unevennesses due to the preparation of the workpieces in narrow fittings 2~ so that at these places overload areas and resulting later metal breaks at the sliding faces occur, or the agcressive component of the organometallic co~pounds is strengthened and this results in the phase of chemical wear lu~rication leading to too high removing rates and to a too short life service.

For example, from DE-PS 941 678 lubricating oils having a content of soluble reaction pro~ucts of phosphorus pentasulfide and liquid or solid aliphatic hydrocarbons or terpene hydrocarbons are known. ~-rom DF-PS 923 984 there -1~39~82 l is known a lubricating oil which contains the metal con-taining alkylphenolsulfide esters in com~ination with zinc sulfonates. ~ro~ DE-AS 1 449 892 there is known a lubricating oil which contains a salt of an aromatic zinc dithiophosphate and a zinc carboxylic acid salt in the presence of water. While both formerly stated products are lubricating oil detergents the latter product is said to prevent the corrosion of silver bearing surfaces.
From DE-AS 1 296 730 there is known a lubricating oil which contains a substituted succinic acid optionally together with a salt of an alkylated or esterified phosphoric acid. This product is an antioxidant functioning as detergent. From D~-AS 1 271 87~ there is known a combi-nation of dithiophosphate and dithiophosphinate salts.
l~ From DE-OS 15 94 ~55 there are known cutting oils which contain free sulfur, a diaIkyldithiophosphate and a chlorinated hydrocarbon. In US-PS 3 462 367 lubricating oils cont~ining a zinc ~r-antimony dithioc~rhRm~te are disclosed. From US-PS 2 758 087 lubricating oils are known, cont~ining a sulfur-phosphorus-compound prepared by reacting phosphorus pentasulfide with an olefin at a higher temperature,and zinc phthalate. However, all these known lubricating oil additives do not fulfill the today's requirements, in particular they lead to heavy 2~ oxidic deposits in the area of the lu~ricating place and caUse a wear which is too high.

From US-PS 2 73~ 86~ it is known to use a lubricating oil additive which is fcrmed of a dithiophosphate of the alkaline earth metal salts in combination with a complex reaction product of phosphorus sulfides, tallow oil fatty acid alcohol esters, zinc chloride and barium hydroxide. The friction coefficients and wear values which can be achieved therewith are too high for today~s requirements and 3~ furthermore the face pressure value is too low. From US-PS

1 2 734 864 lubricating oil additives are known which are formed of a dithiophosphate of the alkaline earth metals in com~ination with a complex reaction product of phosphorus sulfides, wool fat and alcohol esters. The undefined 5 product contains substantial amounts of barium and zinc.
Such a lubricating oil additive is not usable in practice because of its inkearable odor which also jeopardizes the health of the operators getting in contact with it. From DE-PS 1 9~4 452 lubricants on mineral c l and synthetic oil basis are known which contain besides the mineral oil or synthetic oil as additives an ester of an epoxidized fatty acid having 10 to 18 C-atoms and of a monovalent or multivalent alcohol, an alkyl, aralkyl or aryldithiophos-phate of zink, lead, tin, tungsten, molybdenum~ niobium or lanthanum, and optionally a sulfur-phosphorus-compound.
From DE-PS 2 108 780 lubricants on the basis of a mineral oil or synthetic oil and lubricant concentrates, respectively, are known which besides a lead, tungsten, molybdenum and/or vanadium dithiophosphate esterified with alkyl, aryl or aralkyl groups contain in addition at least one zinc dialkyldithiophosphate compound and a sulfur-phosphorus-compound which is free of a metal. Also these latter lubricants which have found a widespread use, do no more fulfill all requirements of modern longlife and highduty lubricants Their friction coefficient and wear are too high, their storage restistance is insufficient, their longlife use leads to a too high reclamation quote in the lubricant field.

The object of the present invention is to provide a novel lubricant (lubricating agent) cr lubricant concentrate on z mineral oil or syr,thetic oil basis having improved lubricating properties, in particular improved friction and wear ~roperties an~ reduces sensibly the need of energy and replacement parts and meets the highest re~uirements.
X

i 1~39482 1 It has no~ been found that this o~ject according to the present invention can be surprisingly reached by adding at least one compound containing in its molecule at least one quaternary car~on aton. and at least one ester ~ond and/or ether ~ond to a mineral oil and/or synthetic oil hesides the usual additives.

The subject of the present invention is a novel lu~ricant or lubricant concentrate on m neral oil and/or synthetic oil ~asis which is characterized in that it contains a) one or more mineral oils and/or-synthetic oils as base oil and b) at least one compound A containing in its molecule at least one quaternary carbon atom and at least one ester lS bond and/or ether bond, as well as c) further usual additives.

The lubricants and lu~ricant concentrates of the invention are superior to the known lubricants and lubricant con-centrates in particular in regard to their friction andwear properties and reduce substantially the need of energy and replacement parts. It is assumed that this is due to the fact that by their use in the friction and slide areas metallic glass surfaces consisting of amorphous solidified metal melts are formed which do not exhi~it any metal crystal lattice structures. The glass-like smooth friction and sliding surfaces which are ~elieved to ~e formed by using the lubricants or lubricant concentrates of the present invention improve substantially the whole lubricating process since the friction coefficient and the ~ear, the oxidation and the corrosion are reduced substantially. Also the so-called fitting-rust is prevented ~y the lu~ricant and lu~ricat concentrate of the invention.
~n addition, the lu~ricants and lu~rican~concentra~es of the 3~ invention are non-polluting since they do not contain any leac, no sulfur containing whale sperm oil and almost no phosphorus. This has been shown in fish tests and bacterial cultivation tests which have been carried out 1 wit~ the lubricant5and lubricant concentratesof the inven-tion Furthermore, it has been shown that they are degra-dable biologically in normal soil within 3 to 4 months to an extent of 60 %
Thus, they can be considered as extremely non-polluting In particular they are suited for the use in homokinetic joints for vehicles, i.e. small joints subject to a high number of revolutions and a hig load, and they are more similar to the ideal lubricant ~lifetime ]u'bricant" tnan all other already known lubricants. Additionally, the compounds having quaternary carbon atoms which are used according to the present invention have a significant thermal stability and enable the utilization o~ high operating temperatures of up to 300~C. They offer the possibility to use them as li~etime lu~rication of high duty engines, turbines, roller bearings, synchronizing joints and other high duty ~achine elements.

The expression~lubricant or lu~ricant concentrate on mineral oil and/or synthetic oil ~asis" used in the present appli-cation is meant to comprise lu~ricating oils as well as lubricating fats on mineral oil and/or synthetic oil basis.

The expression "~uaternary carbon atoms containing compounds"
2~ used here is meant to comprise those compounds wherein the ~ main valences of at leastcne carbon atom per molecule are - -each substituted by ~ carbon atoms Exam~les for such compounds are monomeric, dimeric and trimeric penta-erythritol esters, other polyolesters,pentaerythritol ethoxyesters, pentaerythritol ethers and pentaerythritol ethoxyethers as well as adamentaneester and -ether deri-vatives or telomeric acid diolesters or neopentylpolyclesters and the corresponding ethoxylated esters and ethers.

3~ As can be seen ~rom the examples following below the lubricants und lubricant concentratesof the invention have substantially X~

1 improved properties compared with the known lubricantsand lubricant concentrates.The glass-like smooth friction and sliding faces formed by the lubricant of the inventiOn save driving energy and reduce the friction coefficient per se and also by the formation of a very good adhering boundary lubricating-~ilm which enables an elasto-hydrodynamic lubrication also with a point-like load.
This result5 in a lowering of the friction temperature of the lubricant and of the lubricated pla~e, in an extension of the oxidation resistance of both and the metallic friction partnerS are less subjected to specific change-load ana temperature stresses In summarylthe wear is extremely lowered by these effects and the service life of the friction partners and of the lubricant is extended sensibly. According to the present invention these improvements are achieved within a very broad viscosity range so tha~ now oils having a low viscosity can also be used in those fields where until now the use of oils having high or intermediate viscosity values have been considered as being indispensa~le, for example in gears, differential gears, or gears of turbines.
~ In addition the thermal stability of the lubricant and lubricant concentrate of the invention allows its use in 2~ lubricating places subjectea to high operation temperatures, such as in Diesel engines and aircraft turbines According to a preferred embodiment o~ the invention the lubricant or lubricant concentrate contains as compound A
a compound having 1 to 3 quaternary carbon atoms as well as additionally atleast one free hydroxyl group, wherein compound A preferably has a density d20 of at least 0,900 and an enthalpy ~ of at least 350 kcal/kg.

According to a preferred embodiment o~ the invention the 1339~82 1 lubricant or lubricant concentrate of the invention contains additionally a component having at least one free hydroxyl group.

As component A preferably a tetravalent to octavalent alcohol having at least one quaternary carbon atom and at least one ester bond and/or ether bond in its molecule and having a density d20 of at least 0,900 and an enthalpy H of at least 3~0 kcal/kg is used according to the invention.

The compound A used according to the invention is preferably selected from mono-, di- and tripentaerythritol ester and/or ether derivatives, adamantane ester and/or ether derivatives, telomeric acid diolesters and/or neopentylpolyolesters, especially telomeric acid neopentylglycol , trimethylol-propane and/or pentaerythritol esters and their ethoxylated derivatives.

According to a preferred embodiment of the invention the lubricant or lubricant concentrate contains the compound A
in an amount of from 0,1 to 40 ~ by weight, preferable 0,1 to 20 ~ by weight, in particular 1 to 12 ~ by weight, especially 1,5 to 8 ~ by weight, based on the weight of the mineral oil and/or synthetic oil.

The lubricant or lubricant concentrate of the invention contains as base oil prefera~ly beet oil, natural oil and/or a synthetic oil having a viscosity in the range of from 1,0 mPa.s at 20~C to 2.106 mPa s at 20~C. Particularly pre-ferred is the use of a mineral oil having a viscosity of from 1,0 mPa.s at 20~C to 540 mPa.s at 50~C as natural oil and the use of an aromatic or aliphatic ~icarboxylic acid ester, in particular of a poly-d-olefin-dicarboxylic acid ester, especially -butylester, having a molecular weight in the range of from 1000 to 3000, preferably the use of 9 13~9~8~

1 phthalic acid diisodecylester, trimethyladipic acid ~idecylester and se~acic acid dioctylester, a polyiso~utylene having a molecular weight of from 1000 to 100 000 and a viscosity of from 200 to 43 000 mPa.s at 100~C, of a polymethacryla~ having a viscosity of 1000 mPa.s at 100~C, of a water insoluble polyglycol having a viscosity of from 5 to 60 mPa.s at 100~C, of an isoparaffin oil and/or alkylbenzene having an inflammation point of more than 50~C anda viscosity in-the range of from 1,0 mPa.s at 20~C
to 2 000 000 mPa.s at 20~C and of a telomeric acid ester, preferable a neopentylglycol and/or trimethylolpropane ester of the telomeric acid.

As further additive the lubricant or lubricant concentrate of the invention preferably contains a sulfur containing .
substance, in particular a thiazole, at least one metal-dialkyldithiocarbamate and/or a metaldialkyldithiophosphate and/or a phosphorus cont~;ning substance, in particular an organophosphite, preferably a dialkylarylphosphite, especially didecylphenylphosphite or didodecylphenyl-phosphite and/or a metaldialkyldithiophosphate.

The sulfur cont~;ning substance preferably is contained in the lubricant or lubricant concentrate of the invention in an amount of from 0,5 to 10 % by weight, expecially 1 to 3 % by weight, while it contains the phosphorus containing substance prefera~ly ln an amount of from 0,1 to 5 % by weight, especially 0,5 to 2 ~ by weight.

According to a further preferred embodiment of the invention the lubricant or lubricant concentrate can contain usual antioxidants, metaldeactivators, detergents, dispersants, antifoam agents and/or viscosity index improving agents.

The additives of the invention can be added as single compounds or in the form of a composition asaconcentrate to l the base medium (~ase oil or base fat) in the above stated amounts.

Further features and advantages of the invention can be seen from the following description of the invention.

The compounds A having at least one quaternary carbon atom in the molecule and which are preferably used according to the ~resent invention can comprise the following three groups of compounds:

a) mono-, di- and tripentaerythritol esters and/or ethers and their ethoxylated ester derivatlves and ethoxylated ether derivatives. The basic monG- and dipentaerythritol has the following structure CH2OH , 2 H , 2~~
H2oH ~OH2C-C-CH -O-H C-C-CH OH
CH20H CH2~~ CH20H

monopcntaerythritol dipentaerythritol ~herein the hydroxyl groups are esterified or etherified in part or completely and the ester groups or ether groups thereof preferably contain strainght or branched alkyl, aralkyl or aryl groups having 6 to 18, preferably 8 to 12 carbon atoms.

These compounds can be easily prepared and many represen-tatives of these compounds are commercially available, f.i.
from Ciba-Geigy under the tradename Reolube LP 3600 (a pentaerythritol tetrapelargonate), Reolube LPE 504 (a penta-erythritol tetraoctylester), Reolube LPE 602 (a penta-erythritol tetraheptylester), Irom Akzo under the tradename ~etjenlube*12 (a pentaerythritol tetradecyl/dodecylester *trade-mark X
-- ll 1339482 1 having a statistical C10/C~2-distri~utio~, and from Henkel AG under the tradename Edenor Ke 230 (a pentaerythritol tetraisopalmitic acid ester) and pentaerythritol tetra-isostearic acid ester.
s Examples for suitable pentaerythritol esters are pentaery-thritol monohexylester, pentaerythritol monooctylester, pentaerythritol monononylester, pentaerythrit~l monodecyl-ester, pentaerythritol moncdodecylester,-pentaeryt~~itol-monomyristylester, pentaerythritol monohexadecylester,pentaerythritol monostearylester, pentaerythritol mono-oleylester, pentaerythritol monoisostearyl- and -isopalmitic acid ester; the corresponding dihexyl-, dioctyl-, dinonyl-, didecyl-, didodecyl-, dimyristyl-, dihexadecyl-, distearyl-, dioleyl-, diisostearyl- and diisopalmitic acid esters of the pentaerythritol; the corresponding trihexyl-, trioctyl-, trinonyl-, tridecyl-, tridodecyl-, trimyristyl-, trihexa-decyl-, tristearyl-, trioleyl-, triisostearyl- and triiso-palmitic acid esters of ~entaerythritol as well as the corresponding tetrahexyl-, tetraoctyl-, tetranonyl-, tetradecyl-, tetradodecyl-, tetramyristyl-, tetrahexadexyl-, tetrastearyl-, tetraoleyl-, tetraisostearyl- and tetra-isopalmitic acid esters of pentaerythritol.

Examplesfor suitable pentaerythritol ethers are-pentaery-thritol monohexylether, pentaerythritol monooctylether, pentaerythritol monononylether, pentaerythrltol ~lonodecyl-ether, pentaerythritol monododecylether, pentaerythritol monomyristylether, pentaerythritol monohexadecylether, pentaerythritol monostearylether, pentaerythritol mono-oleylether, pentaerythritol monoisostearyl- and -isopalmitic acid ether; the corrsponding dihexyl-, dioctyl-, dinonyl-, didecyl-, didodecyl-, dimyristyl-, dihexadecyl-, distearyl-, dioleyl-, diisostearyl- and diisopalmitic acid ethers o~ pentaerythritol; the corresponding trihexyl-, trioctyl-, - - *trade-mark - ~.

-- , 1 trinonyl-, tridecyl-, tridodecyl-, trimyristyl-~ ecyl-, tristearyl-, trioleyl-, triisostearyl- und triisopalmitic acid ethers of pentaerythritol as well as the corresponding tetrahexyl-, tetraoctyl-, tetranonyl-, tetradecyl-, tetra-dodecyl-, tetramyristyl-, tetrahexadexyl-, tetrastearyl-, tetraoleyl-, tetraisostearyl- and tetraisopalmitic acid ethers of pentaerythritol.

b) adamantane derivati~s having the adamantane skeleton:

I l C ~ ~,C H
C . CEI, C~
H C cn c H~

adamantane which is substituted in the 1- or 2-position by COOH, Ch2O~
or C2H50H, wherein the OH group of the substituent can ~e esterified oretherified, optionally with one or more ethoxy groups there~etween. The ester groups and ether 2~ groups are prefera~ly straight or branched alkyl grOUDS
having 1 to 10, preferably 2 to 6 carbon atoms or aralkyl or aryl groups having 6 to 18, prefera~ly 8 to 12 carbon atoms.

c) Pentaerythritol telomeric acid derivatives having the following skeleton:
O
C~2-o-c-T
I

~-C-O-~2C-C- Q -O-C-R
O I o CH20-C--~

O

l wherein T is telomer 13 3 9 ~ 8 2 R is T or alkyl.

The telomeric acids are compounds having a relatively high molecular weight and having long-chainea star-like branched structures which can be esterified in the usual manner and the esters thereof are valuable lubricants (commercial product Kortacid T of Akzo Chemistry).

Mineral oils which can be used according to the invention are all usual mineral oils ranging from the isoparaffin oil having a viscosity of 1,0 mPa.s at 20~C over thin spindle oil having a viscosity of 12 mPa.s at 20~C to thehigh viscous brightstock and cylinder oil having a viscosity of 540 mPa.s at SO~C.

Many of the synthetic oils usahle according to the invention are commercially available, f i. from BP Co. under the tra~ena-me "Hyvis~10~ ~a polyisobutylene having a viscosity of 200 mPa.s at 100~C), Hyvis 200" (a polyisobutylene having a viscosity of 4300 mPa.s at 100~C) ana "Hyvis 2000" (a poly-isobutylene having a viscosity of 43 000 mPa.s at 100~C~.
Viscoplex-4-9S of ~ohm Co. (a polymethacrylate1 having a viscosity of 1000 mPa.s at 100~C, Ucolub N9 having a viscosity of 5,7 mPa.s at 100~C, Vcolub N36A having a viscosity of 5,7 mPa s at 100~C, Ucolub N36A having a viscosity of 18 mPa s at 100~C, Ucolub N120A having a viscosity of 55 mPa.s at 100~C
(these all are water insoluble polyglycols) of Union Carbide Co. as well as ~Isopar J" of Esso Co ~an isoparaffin oil) having a viscosity of 1,0 mPa s at 20~C

The organophosphorus which can be used according to the in-vention are compounds of the formula R
~ - P - R

wherein ~ each is a straight or branched or cyclic alkyl group . .
*trad-e-mark X
-1 having 6 to 12 car~on atoms or a phenyl group substituted in o- or p-position by a lower alkyl group having 1 to 6 carbon ato~.s.

Preferred examples of the organophosphorus cGmpounds having the above formula are monodecyl-diphenylphosphite, dide-cylphenylphosphite, triphenylphosphite, dioctyl-phenyl-phosphite, dihexyl-phenyl-phosphite, diisodecyl-phenyl-phosphite, diisooctyl-phen~-'-phosphite, didecyl-o-methyl-phenylphosphite and didecyl-p-methylphenylphosphite.

The metaldialkyldithiocarbamates which can be used according to the invention as sulfur conta~ing s~bstanoe are compounds of the formula /S-Me \ N ~a lkyl ~ alkyl wherein Me is a metal selected from the group copper (Cu), silver (Ag), zinc (Zn), cadmium (Cd), titanium (Ti), boron (B), zirconium (Zr), tin (Sn), lead (Pb), vanadium (V), tantalum (Ta), antimony (Sb), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), cobalt (Co), and nickel (Ni), preferably boron (B~, nickel (Ni), cobalt (Co) or molybdenum (Mo).

The metaldialkyldithiophosphates which can be used accordin~
to the invention as sulfur containing substance as well as phosphorus containing substance are compounds of the formula ~ S-~e S=P ~ O-alkyl ~ o-a lkyl 1 wherein Me is a metal selected from the group copper (Cu), silver (Ag), zinc (Zn), cadmium (Cd), titanium (TiJ, boron (B), zirconium (Zr), tir. (Sn), lead (Pb), vanadium (V), tantalum (Ta), antimony (Sb), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), cobalt (Co), and nickel (Ni), preferably zinc (Zn), nickel (Ni), titanium (Ti), vanadium (V), molybdenum (Mo), tungsten (W) and manganese (Mn).

The aIkyl groups of the above-mentioned metaldialkyldithiocarb-amates and metaldialkyldithiophosphates each preferably contain 4 to 8 carbon atoms, so that the named metal salts are still soluble in the commercially available base oils.
Examples of the particularly advantageous alkyl groups are the n-, i- and tert-~utyl group, the n- and i-amyl groups, the n- and i-hexyl group, the n- and i-heptyl group and the 2-ethylhexyl group. Especially preferred are the i-butyl group, the n- and i-amyl group and the 2-ethylhexyl group.

The invention will be explained in more detail using the following examples, however it is not restricted thereto.

In the following examples commercially available lubricating oils and lubricating fats, respectively, were used having the following composition and they were compared in regard to their lubricating properties~which on the one hand contained the lubricant concentrate of the invention and on the other hand without containing it.

The results obtained in each example are depicted graphi-cally in the diagrams.

~or the carrying-out of the tests a circular plate of refined steel with a diameter of 23 mm and a thickness of 10 mm was used, onto the surface of which a drop of each X

1 lubricant or lu~ricant concentrate to be tested was applied. Onto the area where the drop of the lubricant or lubricant concentrate was located a ~all made of the same refined steel with a diameter of 10 mm was applied, which on account of its load exerted a pressure onto the surface of the metal plate. The metal ~all was moved to and fro on the surface of the metal plate with a frequency of ~0 Hz over an amplitude of 1 mm for 60 to 180 minutes under pressure, whereby during the test the load within the range was varied from ~0 to 300 N and the temperature was ~aried from 50 to 150~C (SRV (swing-friction-wear) apparatus which is sold world-wide by the firm Optimol Gm~.

The wear-profile produced on account of the friction between the loaded ~all and the surface of the metal plate within the testing period diagonal to the oscillation direction of the ball was recorded ~y means of a suita~le recording apparatus, whereby the ~elow given diagrams were obtained, in which on the ordinate, the height of wear is plotted as difference between the highest and lowest point of the surface profile of the metal plate, against the scanning span of the surface of the metal plate on the abscissa.

In the ~elow diagrams a depth of profile on the ordinate of 1 cm corresponàs to a real depth of profile on the surface of the metal plate of 1 ~m, whereas in the diagram B' of example 2 the scanner was so damped that a depth of profile of 1 cm on the diagram corresponds to a real depth of profile on the surface of the plate of 2,~ ~m.

The diagra~.s were recorded under identical conditions (load of the ~all ~0 to 300 ~, friction frequency ~0 Hz, temper~ture ~0 to 1~0~C, friction amplitude 1 mm, testing time 1 to 3 hours).
X

~he friction coefficients indicatea below the diagrams (~ max=
maxlmum friction coef~icient, ~ d = average Iriction coeffi-cient over 9B ~ of the ~riction coefficient curve~ were also determined ~y using the a~ove de5cri~ed S~V apparatuS- In all tests where not statea otherwise ~s lu~ricant concentrate of the invention a product having the following composition was used:

50 ~ C10-C18-compound having a quaternary carbon atom 20 % copolymer ~f ~-olefin esters 9,5 ~ trimethyladipic acid aidecylester 2,5 % dialkylarylphosphite 9 % metaldialkyldithiophosphate/metalaialkylaithiocarbalTlate 7 ~ thiazole aerivative 2 ~ sterically hindered phenol as oxidation inhi~itor ~xample 1 A high viscous lubricating oil having a viscosity of 22~0 mPa s at 50~C and having the following composition was prepared and tested:
trimethyladipic acid didecylester 3 polyiso~utylene 1~3000 mPa s~100~C3 32 1u~rlcant-entraining su~stance 6 lu~ricant concentrate of the invention 28 3~
In the comparative product the lubricant concentrate of the inventlon was omitted Both products were tested for 1 h at a temperature o~ 1~0~C
and a load of 200 N under identical conditions. ~he obtained results are graphically depict~d in the following diagrams A
(according to the invention~ and A' (according to the state -of.art) - - -X

l Diagr~ ~ Diagram A' ~ ~r~ow ~ r~t~ r~

~max = 0,112 ~ max = 0,145 = 0,0~7 ~ d = 0,088 The addition of the lu~ricant concentrate of the invention led to a depth of profile of 0,80 ~m (average of two deter-minations). Without the addition of the lu~ricant concentrate lS of the invention a depth of profile of 1,68~average of two aeterminations) was obtained.

Example 2 An intermediate viscous lubricating oil having a viscosity of 190 to 200 ~Pa.s at 50~C and having the following composition was prepared and tested:
polymeric ~-olefin esters 12 %
25 ~rimethyladipic acid didecylester 36 ~~
~olyiso~utylene (43000 mPa s/100~C~ 18 lu~ricant-entraining substance 6 ~~
lu~ricant concentrate of the invention28 ~

In the com~arative product the lu~ricant ccncentrate of the invention was omitted.

Both products were tested for 1 h at a temPerature of 15~C
and 2 load of 200 N unaer identical con~itions The o~tained re-su-l~s are graphically depicted in the following diagrams B
(according to the invention) and B' (according to the state of art).

Diaaram B Diacram B' . _ _ _ _ _ 1 0 ' ' ~ ' ' -' ' -" '- ' ' -~, mzY. = 0,133 ~ max = 0,128 ~ d = 0,050 ~ d = 0,098 The addition of the lubricant concentrate of the invention led to a depth of profile of o,875 ~m (average of two deter-minations~. Without the addition of the lubricant concentrate of the invention a depth of profile of13,98~m~average of two determinations3 was obtained.

Example 3 An intermediate viscous lubricating oil having a viscosity of 120 to 150 mPa.s at 50~C and having the following composition was prepared and tested:

high viscous ~-olefin ester copolymer 4 intermediate viscous ~-olefin ester polymer 12 30 trimethylaaipic acid didecylester 34 polyisobutylene ~200 mPa.s/100~C) 12 lu~ricant-entraining substance 6 lu~ricant concentrate of the invention 32 l In the comparative product the lu~ricant ccncentrate of the invention was omitted.

Both products were tested for 1 h at a temperature of 150~C
and a load of 200 N under identical conditions. The obtained results are graphically depicted in the following diagrams C
(according to the invention) and C' (according to the state of art).
D~cgr~-C' Diagr~ C

max = 0,112 - -= 0,047 maY. = 0,1~8 ~ 0,135 The additlon of the lubricant concentrate of the invention led to a ~epth of profile of 7,12~m (average of two deter-minations~. Without the addition of the lu~ricant concentrate of the invention a depth of profile of 3,48 ~ average of two 2~ determinations) was o~tained Fxample ~

A high viscous adhering and high temperature lu~ricating oil having a viscosity of 1~ 000 mPa.s at ~0~C and having the following composition was prepared and tested:

trimethyladipic acid didecylester 29 polyisobutylene (~3000 mPa.s/100~C~ ~2 lubricant concentrate of the invention 19 X

1 In the comparative product the lu~ricant concentrate of the invention was omitted.

Both products were tested for 1 h at a temperature of 150~C
and a load of 200 N under identical conditions. The obtained results are graphically depict~d in the following diagrams D
(according to the invention) and D' (according to the state of art).

- Diagram D Diagram D' max = 0,123 ~ maY = 0,121 ~ d = 0,052 ~ d = 0,084 The addition of the lubricant concentrate of the invention led to a depth of profile of 0,80 ~m ~average of three deter-minations). Without the addition of the lubricant concentrateof the invention a depth of profile of 1,57~m(average of two determinations) was obtained.

Example 5 A high duty gear oil SAE 85/90 was tested with and without the additive of the invention consisting of 10 ~ ~y weight of monopentaerythritol tetraester.

Both products were tested for 1 h at a temperature of 90~C
and a load of 200 N under identical conditions. The obtained results are graphically depicted in the following diagrams (according to the in~ention) and E' (according to the state o~ a~t~.
3~

1~9482 Diagram ~ Diaaram E' .
- - - - .. .

. . . . . .. . . . . I ~
_. _ . . _ , _ _ ,_. -- -- ! ___ _ _ .. _ ._ .. _ ~ max = 0,113 ~ max = 0,112 ~ d = 0,076 --~ d = 0,085 The addition of the additive of the invention led to a depth of profile of 0,85 ~m (average of two deter-minations). Without the addition of the additive of the invention a depth of profile of 1,02~m(average of two determinations) was obtained.

Example 6 A lu~ricating fat for multi-purpose lubrication for high duty gears and synchronizing joints having the following composition was prepared and tested:
2~
mineral oil ~ 70 %
consistency improving agent on lithium-stearate basis 9 %
lubricant concentrate of the invention 21 %

In the comparative product t~,e lubricant concentrate of the invention was replaced by 3 % by weight of a molybdenum disulfide/graphite mixture.

B~l. products were tested for 3 h at a temperature of 50~C
and a load of 300 N under identical conditions. The obtained 1~39482 1 results are graphically depicted in the following diagrams (according to the invention) and F' (accor~ing to the state of art).
Diagram F Diaor2m ~' max = 0,176 ~Kmax = 0,177 ~ d = 0,09~ R~d = 0,150 The addition of the lubricant concentrate of the invention led to a depth of profile of 0,95 ~m (average of three deter-minations), . whilè the addition of the comparative additive mixture led a depth of profile of 1,63~average of three determinations) While the invention was explained above in more detail referring to preferred specific emobdiments, it is however obvious that it is not restricted thereto, but that it can be altered and modified in many respects in a manner - obvious to the expert, withcut going beyond the scope 2~ of the present in~-ention.

Claims (23)

1. A lubricant or lubricant concentrate, respectively, on a mineral oil and/or synthetic oil base, comprising at least one base oil selected from the group consisting of mineral oils and synthetic oils and at least one compound having at least one quaternary carbon atom and at least one ester and/or ether bond in its molecule as well as further common additives, characterized in that it contains (a) at least one compound having from 1 to 3 quaternary carbon atoms and at least one free hydroxyl group in its molecule which compound has a density d20 of at least 0,900 and an enthalpy .DELTA.H of at least 350 kcal/kg and is selected from the group consisting of the mono-, di- or tri-pentaery-thritol esters and ethers, the adamantane esters and ethers, the adamantane esters and ethers of adamantane derivatives substituted in 1- or 2-position by -COOH, -CH2OH or -C2H5OH, and the telomeric acid diolesters and neopentylglycol esters and ethoxylated derivates thereof, the ester and ether groups being alkyl, aralkyl or aryl groups having from 6 to 18 carbon atoms, (b) at least one metal dialkyldithiocarbamate of general formula wherein Me is a metal selected from the group consisting of copper, silver, zinc, cadmium, boron, titanium, zirconium, tin, lead, vanadium, tantalum, antimony, chromium, molybdenum, tungsten, manganese, cobalt and nickel and Alkyl is an alkyl group having from 4 to 8 carbon atoms, and (c) further commonly used additives known per se selected from the group consisting of antioxidants, metal deactivators, detergents, dispersants, anti-foam and viscosity index improving agents.
2. The lubricant and lubricant concentrate, respectively, according to claim 1, characterized in that it comprises as a further component (d) at least one metal dialkyldithiophosphate of general formula wherein Me is a metal selected from the group consisting of copper, silver, zinc, cadmium, boron, titanium, zirconium, tin, lead, vanadium, tantalum, antimony, chromium, molybdenum, tungsten, manganese, cobalt and nickel and Alkyl is an alkyl group having from 4 to 8 carbon atoms.
3. The lubricant and lubricant concentrate, respectively, according to claim 1, characterized in that it contains said component (a) in an amount of from 0.1 to 40 % by weight.
4. The lubricant and lubricant concentrate, respectively, according to claim 2, characterized in that it contains said component (a) in an amount of from 0.1 to 40 % by weight.
5. The lubricant and lubricant concentrate, respectively, according to claim 1, characterized in that it contains said component (a) in an amount of from 0.1 to 20 % by weight.
6. The lubricant and lubricant concentrate, respectively, according to claim 2, characterized in that it contains said component (a) in an amount of from 0.1 to 20 % by weight.
7. The lubricant and lubricant concentrate, respectively, according to claim 1, characterized in that it contains said component (a) in an amount of from 1 to 12 % by weight.
8. The lubricant and lubricant concentrate, respectively, according to claim 2, characterized in that it contains said component (a) in an amount of from 1 to 12 % by weight.
9. The lubricant and lubricant concentrate, respectively, according to claim 1, characterized in that it contains said component (a) in an amount of from 1.5 to 8 % by weight, based on the weight of said base oil.
10. The lubricant and lubricant concentrate, respectively, according to claim 2, characterized in that it contains said component (a) in an amount of from 1.5 to 8 % by weight, based on the weight of said base oil.
11. The lubricant and lubricant concentrate, respectively, according any one of claims 1 to 10, characterized in that it contains as said base oil at least one oil selected for the group consisting of a beet oil, a natural oil, a natural oil and a synthetic oil having a viscosity in the range of from 1.0 mPa.s at 20°C to 2.106 mPa.s at 20°C.
12. The lubricant and lubricant concentrate, respectively, according to claim 10, characterized in that it contains as said natural oil, a mineral oil having a viscosity of from 1.0 mPa.s at 20°C at 540 mPa.s at 50°C
13. The lubricant and lubricant concentrate, respectively, according to claim 10, characterized in that it contains as said synthetic oil at least one oil selected from the group consisting of an aromatic or aliphatic dicarboxylic acid ester, in particular a poly-.alpha.-olefin-dicarboxylic acid ester, especially -butylester, having a molecular weight in the range of from 1000 to 3000, preferably phthalic acid diisodecylester, trimethyladipic acid didecylester and sebacic acid dioctylester, a polyisobutylene having a molecular weight of from 1000 to 100,000 and a viscosity of from 200 to 43,000 mPa.s at 100°C, a polymethacrylate having a viscosity of 100 mPa.s at 100°C, a water-insoluble polyglycol having a viscosity of from 5 to 60 mPa.s at 100°C, an isoparaffine oil and an alkyl benzene having an inflammation point of higher than 50°C and a viscosity in the range of from 1.0 mPa.s at 20°C
to 2,000,000 mPa.s at 20°C.
14. The lubricant and lubricant concentrate respectively, according to any one of claims 1, 10, 12 or 13, characterized in that it contains said sulfur containing compound(s) in an amount of from 0.5 to 10% by weight.
15. The lubricant and lubricant concentrate, respectively, according to claim 11, characterized in that it contains said sulfur containing compound(s) in an amount of from 0.5 to 10% by weight.
16. The lubricant and lubricant concentrate, respectively, according to any of claims 1, 10, 12 or 13, characterized in that it contains said sulfur containing compound(s) in an amount of from 1 to 3 % by weight.
17. The lubricant and lubricant concentrate, respectively, according to claim 11, characterized in that it contains said sulfur containing compound(s) in an amount of from 1 to 3 % by weight.
18. The lubricant and lubricant concentrate, respectively, according to any one of claims 2 to 10, 12, 13, 15 or 17, characterized in that it contains said phosphorous containing compound(s) in an amount of from 0.1 to 10% by weight.
19. The lubricant and lubricant concentrate, respectively, according to claim 11, characterized in that it contains said phosphorous containing compound(s) in an amount of from 0.1 to 10 % by weight.
20. The lubricant and lubricant concentrate, respectively, according to claim 14, characterized in that it contains said phosphorous containing compound(s) in an amount of from 0.1 to 10 % by weight.
21. The lubricant and lubricant concentrate, respectively, according to claim 16, characterized in that it contains said phosphorous containing compound(s) in an amount of from 0.1 to 10 % by weight.
22. The lubricant and lubricant concentrate, respectively, according to any one of claims 2 to 10, 12, 13, 15 or 17, characterized in that it contains said phosphorous containing compound(s) in an amount of from 0.1 to 5% by weight.
23. The lubricant and lubricant concentrate, respectively, according to any one of claims 2 to 10, 12, 13, 15 or 17, characterized in that it contains said phosphorous containing compound(s) is an amount of from 0.5 to 2% by weight.
CA000563060A 1987-04-10 1988-04-08 Lubricant or lubricant concentrate Expired - Fee Related CA1339482C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP3712132.4 1987-04-10
DE19873712132 DE3712132A1 (en) 1987-04-10 1987-04-10 LUBRICANTS OR LUBRICANT CONCENTRATE

Publications (1)

Publication Number Publication Date
CA1339482C true CA1339482C (en) 1997-09-30

Family

ID=6325304

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000563060A Expired - Fee Related CA1339482C (en) 1987-04-10 1988-04-08 Lubricant or lubricant concentrate

Country Status (7)

Country Link
EP (1) EP0286141B1 (en)
JP (1) JP2853135B2 (en)
AT (1) ATE111151T1 (en)
CA (1) CA1339482C (en)
DE (2) DE3712132A1 (en)
ES (1) ES2063743T3 (en)
WO (1) WO1988008023A1 (en)

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JPH0816230B2 (en) * 1988-10-20 1996-02-21 日本石油株式会社 Two-cycle engine oil composition
EP0430657A1 (en) * 1989-11-29 1991-06-05 Asahi Denka Kogyo Kabushiki Kaisha Lubricant for refrigerators
DE4214653A1 (en) * 1992-05-02 1993-11-04 Henkel Kgaa ENGINE BASE OIL WITH IMPROVED SEALING COMPATIBILITY
EP0612832B1 (en) * 1992-12-07 1998-07-22 Idemitsu Kosan Company Limited Flame retardant hydraulic oil
FR2986801B1 (en) * 2012-02-15 2014-09-05 Total Raffinage Marketing LUBRICATING COMPOSITIONS FOR TRANSMISSIONS
JP6544953B2 (en) * 2014-05-29 2019-07-17 株式会社リコー Image forming apparatus and grease composition
WO2017222018A1 (en) * 2016-06-23 2017-12-28 Jxtgエネルギー株式会社 Grease composition for constant velocity joints, and constant velocity joint in which same is sealed

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Also Published As

Publication number Publication date
JP2853135B2 (en) 1999-02-03
ATE111151T1 (en) 1994-09-15
WO1988008023A1 (en) 1988-10-20
DE3712132A1 (en) 1988-10-20
EP0286141A1 (en) 1988-10-12
DE3712132C2 (en) 1993-07-08
ES2063743T3 (en) 1995-01-16
JPH01503789A (en) 1989-12-21
EP0286141B1 (en) 1994-09-07
DE3851357D1 (en) 1994-10-13

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