LUBRIFIANT OU CONCENTRE DE LUBRIFIANT

LUBRICANT OR LUBRICANT CONCENTRATE

Abrégé anglais

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.

Revendications

- 24 -
THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
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
<IMG>
wherein
Me is a metal selected from the group consisting of
copper, silver, zinc, cadmium, boron, titanium,
zirconium, tin, lead, vanadium, tantalum, antimony,

- 25 -
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
<IMG>
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.

- 26 -
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,

- 27 -
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

- 28 -
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

- 29 -
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.

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

1339482
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

6 1339482
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~

1339482
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

1339482
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
-

- 1339482
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

1339-482
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

1339482
16
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

1339482
~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

18 1339482
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).

1339 182
19
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

1339482
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

21 - 1339482
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
22
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

23
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.