Phosphorus-free multifunctional additives for lubricants

Details Phosphorus-free multifunctional additives for lubricants Phosphorus-free multifunctional additives for lubricants

2000-02-11

2001-07-03

Gerstl, Robert (Department: 1626)

Solid anti-friction devices, materials therefor, lubricant or se

Lubricants or separants for moving solid surfaces and...

Heterocyclic ring compound; a heterocyclic ring is one...

C548S142000

Reexamination Certificate

active

06255259

ABSTRACT:

The present invention relates to compounds of formula I and II, which are suitable as ash-free antiwear additives and antioxidants, to lubricant compositions comprising said compounds as well as to the use thereof.
For operating combustion engines, it has been found advantageous to use lubricants having a low metal content and, therefore, a low ash content and, in view of exhaust gas catalyst compatibility, also a low phosphorus content. There is therefore a search for metal-free and phosphorus-free additives or additive combinations which approach the good antioxidative and wear protection of the zinc dialkyldithiophosphates. Some experiments are known to intramolecularly combine chemical substructures promising different functions as oil additives.
U.S. Pat. No. 3,676,449 describes 1,3,4-thiadiazole-bridged bis-thiomethylene-phenols of the formula
which are suitable as antioxidants for materials susceptible to oxidation, in particular polyolefins.
U.S. Pat. No. 4,906,393 describes borates as reaction products of
wherein R
1
, R
2
, R
3
and R
4
are hydrogen or C
1
-C
60
hydrocarbon, optionally comprising S, N and/or O; R
5
and R
6
are hydrogen or C
1
-C
20
hydrocarbon, optionally comprising S, N and/or O; R′ is a dimercaptothiadiazole unit; X=0-10, and y+z=3.
U.S. Pat. No. 5,177,212 describes the use of reaction products of 2,5-dimercapto-1,3,4-thiadiazole of type a), b) or c) with aliphatic or aromatic aldehyde and alkylated phenol, at a ratio of 1:1:1 to 2:2:1, as antiwear additives and antioxidants for lubricant compositions:
wherein R=H, the terpene radical, a polymer radical (ex poly-&agr;-olefin or epoxidised poly-&agr;-olefin); R
1
=H, C
1
-C
17
alkyl, phenyl, alkyl-substituted phenyl; R
2
and R
4
=H, OH or alkyl, either R
2
or R
4
being defined as OH; R
3
and R
5
=alkyl, and n=1-2.
This invention relates to compounds of formulae I and II described hereinafter, which are suitable as ash- and phosphorus-free antiwear additives and which additionally have an anti-oxidative effect:
In these formulae:
R
1
=hydrogen or C
1
-C
20
alkyl;
R
2
=hydrogen, C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl, C
7
-C
10
bicycloalkyl, phenyl or C
7
-C
9
phenylalkyl;
R
3
=C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl, phenyl or C
7
-C
9
phenylalkyl;
s=0, 1 or 2;
R
4
=C
5
-C
20
alkyl, C
5
-C
12
cycloalkyl, phenyl, naphthyl, C
7
-C
9
phenylalkyl, which may be interrupted by one or several bivalent radicals from the group consisting of —O—, —NR
5
—, —S—, —C(═O)—O—, —O—C(═O)—, —C(═O)—NR
5
— and —NR
5
—C(═O)— or substituted by one or several radicals from the group consisting of —OH, —NH
2
and —C(═O)—OH, or is —A—[(C
6
H
2
)R
2
(OH)R
3
];
R
5
=H or C
1
-C
18
alkyl;
A=C
1
-C
25
alkylene which may be interrupted by one or several bivalent radicals from the group consisting of —O—, —NR
5
—, —S—, —C(═O)—O—, —O—C(═O)—, —C(═O)—NR
5
— and —NR
5
—C(═O)— or substituted by one or several radicals from the group consisting of —OH, —NH
2
and —C(═O)—OH, at least one unit —C(═O)—O— or —O—C(═O)— being present.
It is preferred that:
R
1
=H;
R
2
=H, C
1
-C
8
alkyl, C
5
-C
6
cycloalkyl, phenyl, benzyl or 2-norbornyl;
R
3
=C
1
-C
8
alkyl, C
5
-C
6
cycloalkyl, phenyl, benzyl or 2-norbornyl;
s=0, 1 or 2;
R
4
=C
5
-C
7
cycloalkyl, phenyl, benzyl, C
1
-C
18
alkyl, which may be interrupted by one or several bivalent radicals from the group consisting of —O—, —NH—, —S—, —C(═O)—O—, —O—C(═O)—, —C(═O)—NR
5
— and —NR
5
—C(═O)— or substituted by one or several radicals from the group consisting of —OH and —C(═O)—OH, or is —A—[(C
6
H
2
)R
2
(OH)R
3
];
R
5
=H or C
1
-C
8
alkyl;
A=C
1
-C
18
alkylene which may be interrupted by one or several bivalent radicals from the group consisting of —O—, —NR
5
—, —S—, —C(═O)—, —O—C(═O)—, —C(═O)—NR
5
— and —NR
5
—C(═O)— or substituted by one or several radicals from the group consisting of —OH, —NH
2
and —C(═O)—OH, at least one unit —C(═O)—O— or —O—C(═O)— being present.
It is particularly preferred that:
R
1
=H; R
2
=methyl or tert-butyl; R
3
=tert-butyl;
s=0, 1 or 2;
R
4
=—A—[(C
6
H
2
)(methyl or tert-butyl)(OH)(tert-butyl)];
A=—CH
2
CH
2
O—(C═O)—CH
2
CH
2
— or —CH
2
CH(CH
3
)—O—(C═O)—CH
2
CH
2
—.
Very particularly preferred compounds are:
These compounds are suitable as multifunctional antiwear additives having additional anti-oxidative activity for base oils of lubricating viscosity as well as for fuels. They are phosphorus-free and substantially ash-free.
In another of its aspects, this invention relates to compositions comprising a compound of formula I or II or mixtures thereof in combination with a base oil of lubricating viscosity or with fuels.
A base oil of lubricating viscosity can be used for the preparation of lubricating greases or lubricants and for metal working, gear or hydraulic fluids.
Such lubricating greases or lubricants, metal working, gear and hydraulic fluids are based, for example, on mineral or synthetic lubricants or oils or on mixtures thereof. The skilled person is familiar with them, and they are described in the relevant literature, for example in
Chemistry and Technology of Lubricants
; Mortier, R. M. and Orszulik, S. T. (Editors); 1992 Blackie and Son Ltd. for GB, VCH-Publishers N.Y for U.S., ISBN 0-216-92921-0, see pages 208 et seq. and 269 et seq.; in
Kirk-Othmer Encyclopedia of Chemical Technology
, fourth Edition 1969, J. Wiley & Sons, New York, Vol. 13, page 533 et seq. (Hydraulic Fluids);
Performance Testing of Hydrauic Fluids
; R. Tourret and E P. Wright, Hyden & Son Ltd. GB, on behalf of The Institute of Petroleum London, ISBN 0 85501 317 6;
Ullmann's Encyclopedia of Ind. Chem
., Fifth Completely revised Edition, Verlag Chemie, DE-Weinheim, VCH-Publishers for U.S., Vol. A 15, page 423 et seq. (lubricants), Vol. A 13, page 165 et seq. (hydraulic fluids).
This invention also relates to a process for improving the performance properties of lubricants or lubricating greases, such as motor oil, turbine oil, gear oil, hydraulic or metal working fluids or liquid fuels (diesel or carburettor fuels), which comprises adding at least one compound of formula I or II to the base oil or fuel to achieve a friction-reducing and/or antioxidative effect. Accordingly, this invention also relates to the use of compounds of formula I or II as additives in motor oils, turbine oils, gear oils, hydraulic fluids, metal working fluids, lubricating greases or diesel or carburettor fuels.
The lubricants are preferably oils and greases, based e.g. on a mineral oil. Oils are preferred.
Another group of lubricants which may be used are vegetable or animal oils, fats, tallows and waxes or their mixtures with each other or their mixtures with the mentioned mineral or synthetic oils. Vegetable and animal oils, fats, tallows and waxes are, for example, palmnut oil, palm oil, olive oil, beet oil, rapeseed oil, linseed oil, groundnut oil, soybean oil, cottonseed oil, sunflower oil, pumpkin seed oil, coconut oil, corn oil, castor oil, walnut oil and mixtures thereof, fish oils, tallows of slaughter animals, such as beef tallow, neat's foot oil and bone fat as well as their modified epoxidised and sulfoxidised forms, for example epoxidised soybean oil.
Examples of synthetic lubricants include lubricants based on aliphatic or aromatic carboxylates, polymeric esters, polyalkylene oxides, poly-&agr;-olefins or silicones, on a diester of divalent acids with a monovalent alcohol, e.g. dioctyl sebacate or dinonyl adipate, on a triester of trimethylolpropane with a monovalent acid or with a mixture of such acids, e.g. trimethylolpropane tripelargonate, trimethylolpropane tricaprylate or mixtures thereof, on a tetraester of pentaerythritol with a monovalent acid or with a mixture of such acids, e.g. pentaerythritol tetracapryl

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