Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Organic phosphorus compound – wherein the phosphorus is...
Reexamination Certificate
1995-05-26
2002-04-30
McAvoy, Ellen M. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Organic phosphorus compound, wherein the phosphorus is...
C252S078500, C558S160000
Reexamination Certificate
active
06380139
ABSTRACT:
The present invention relates to novel bisdithiophosphoric acid derivatives, to the use thereof as additives in lubricants, machining fluids and hydraulic fluids, and to compositions containing said derivatives.
Mixed oxothiophosphoric acids are disclosed as, lubricant additives in U.S. Pat. No. 4,544,492.
Methyl esters of formula
R′
2
are hydrocarbon radicals and R′
3
is hydrogen or lower alkyl, are disclosed for the same utility in GB 1 347 845.
Dithiophosphoric acid derivatives which contain —C═C— double bonds or —C(OH)— groups are disclosed in U.S. Pat. No. 4,081.387.
Adducts of dithiophosphoric acids and acrylates are disclosed in U.S. Pat. No. 3,784,588. These adducts are esters of monohydric to hexahydric alcohols. The use of such compounds in hydraulic oils is disclosed in EP 465 156.
Surprisingly, it has been found that some esters of dihydric alcohols have particularly good properties as lubricant additives.
Specifically, the invention relates to compounds of formula
wherein
R
1
and R
2
are each independently of the other C
3
-C
18
alkyl, C
5
-C
12
cycloalkyl,
C
5
-C
6
cycloalkylmethyl, C
9
-C
10
bicycloalkylmethyl, C
9
-C
10
tricycloalkylmethyl, phenyl,
C
7
-C
24
alkylphenyl or, taken together, are
R
3
is &Parenopenst;CH
2
&Parenclosest;
b
, C
4
-C
40
alkylene which is interrupted by —O—, —S—, or —NR
4
—, or is a group of formula
R
4
is hydrogen, C
1
-C
18
alkyl, phenyl-C
1
-C
4
alkyl, phenyl or C
1
-C
6
alkyl-substituted phenyl,
R
5
is hydrogen or methyl, and
b is an integer from 3 to 18.
Preferred compounds of formula I are those wherein R
1
and R
2
are each independently of the other C
3
-C
10
alkyl, C
5
-C
6
cycloalkyl, C
5
-C
6
cycloalkylmethyl, C
9
-C
10
bicycloalkylmethyl, C
9
-C
10
tricycloalkylmethyl, phenyl, C
7
-C
18
alkylphenyl or, taken together, are
R
3
is &Parenopenst;CH
2
&Parenclosest;
b
, C
4
-C
20
alkylene which is interrupted by —O— or NR
4
, or is a group of formula
R
4
is hydrogen or C
1
-C
4
alkyl, and b is an integer from 3 to 10, and compounds wherein R
5
is hydrogen.
Also preferred are compounds wherein R
3
is &Parenopenst;CH
2
&Parenclosest;
b
, C
4
-C
12
alkylene which is interrupted by —O— or NR
4
, or is
R
4
is C
1
-C
4
alkyl and b is an integer from 3 to 6.
Further preferred compounds are those wherein R
1
and R
2
are C
3
-C
6
alkyl.
b is preferably 4 to 6 and, most preferably, 4.
R
4
is preferably hydrogen or C
1
-C
4
alkyl.
R
1
and R
2
defined in the above formulae as C
3
-C
18
alkyl are branched or unbranched radicals. Illustrative examples are propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, 3-heptyl, octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, 2-ethylbutyl, 1-methylpentyl, 1,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylhexyl, isoheptyl, 1-methylheptyl, 1,1,3-trimethylhexyl or 1-methylundecyl.
R
1
and R
2
defined as C
5
-C
12
cycloalkyl may typically be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl or cyclododecyl. Cyclopentyl and cyclohexyl are preferred. Cyclohexyl is most preferred.
R
1
and R
2
defined as C
5
-C
6
cycloalkylmethyl will be taken to mean cyclopentylmethyl and, preferably, cyclohexylmethyl.
R
1
and R
2
defined as C
9
-C
10
bicycloalkylmethyl are typically decalinylmethyl. R
1
and R
2
defined as C
9
-C
10
tricycloalkylmethyl are preferably a group of formula
R
1
and R
2
defined as C
9
-C
24
alkylphenyl are phenyl groups which are substituted by one or more than one alkyl group, preferably by 1 to 3, most preferably 1 or 2, alkyl groups together containing 3 to 18 carbon atoms. Typical examples of such alkyl groups are methyl and ethyl and those cited above.
R
1
and R
2
are preferably identical.
Interrupted C
4
-C
40
alkylene R
3
is preferably straight-chain and preferably contains ethylene units with alternating O, S or NR
4
. The interruption is preferably by oxygen, resulting in polyethylene glycol groups.
The invention further relates to compositions comprising
a) a lubricant, a machining fluid or hydraulic fluid, and
b) at least one compound of formula I as described above.
Preferred compositions are those wherein R
1
and R
2
are each independently of the other C
3
-C
10
alkyl, C
5
-C
6
-Cycloalkyl, C
5
-C
6
cycloalkylmethyl, C
9
-C
10
bicycloalkylmethyl, C
9
-C
10
tricycloalkylmethyl, phenyl, C
7
-C
18
alkylphenyl or, taken together, are
R
3
is &Parenopenst;CH
2
&Parenclosest;
b
, C
4
-C
20
alkylene which is interrupted by —O— or NR
4
, or is a group of formula
R
4
is hydrogen or C
1
-C
4
alkyl and b is an integer from 3 to 10.
Particularly preferred compositions are those wherein
R
3
is &Parenopenst;CH
2
&Parenclosest;
b
, C
4
-C
12
alkylene which is interrupted by —O— or NR
4
, or is
R
4
is C
1
-C
4
alkyl and b is an integer from 3 to 6, and also compositions wherein R
5
is hydrogen.
Compositions meriting special interest are those wherein R
1
and R
2
are C
3
-C
6
alkyl.
The lubricants, machining fluids or hydraulic fluids contained in the inventive compositions can decompose readily to a greater or lesser degree under the action of heat, mechanical stress (especially induced by shear forces) and chemical reagents (especially atmospheric oxygen).
The compounds of formula I afford protection against such influences and will conveniently be present in the novel compositions in amounts of 0.01 to 10% by weight, typically 0.05 to 5% by weight, preferably 0.05 to 3% by weight and, most preferably, 0.1 to 2% by weight. The novel compositions may contain one or more than one of these compounds, and the percentages by weight are based on the total amount of said compounds. The basis of calculation is the total weight of the lubricant, machining fluid or hydraulic fluid without the compounds of formula I.
The invention thus also relates to the use of compounds of formula I as additives for lubricants, hydraulic fluids and machining fluids, especially as extreme-pressure and antiwear additives as well as friction modifiers.
Such a utility also entails a process for enhancing the performance properties of lubricants, hydraulic fluids and machining fluids. The novel utility also encompasses the protection of the metal parts to be lubricated against mechanical wear (antiwear protection).
The suitable lubricants, hydraulic fluids and machining fluids are typically based on mineral or synthetic oils or mixtures thereof. The lubricants are known to the skilled person and are described in the relevant literature, inter alia in Dieter Klamann, “Schmier-stoffe and verwandte Produkte” (Lubricants and Related Products) (Verlag Chemie, Weinheim, 1982), in Schewe-Kobek, “Das Schmiermittel-Taschenbuch” (Handbook of Lubricants) (Dr. Alfred Hüthig-Verlag, Heidelberg, 1974), and in “Ullmanns Enzyklopädie der technischen Chemie” (Ullmann's Encyclopedia of Industrial Chemistry), Vol. 13, pages 85-94 (Verlag Chemie, Weinheim, 1977).
The lubricants are preferably oils and fats are typically derived from a mineral oil. Oils are preferred.
A further group of lubricants suitable for use in the practice of this invention comprises vegetable or animal oils, fats, tallows and waxes or mixtures with one another or with the mineral or synthetic oils referred to above. Vegetable and animal oils, fats, tallows and waxes are typically palm nut oil, palm oil, olive oil, beet oil, rapeseed oil, linseed oil, ground nut oil, soybean oil, cottonseed oil, sunflower seed oil, pumpkin seed oil, coconut oil, corn oil, castor oil, walnut oil and mixtures thereof, fish oils, the tallows of slaughter animals, e.g. beef tallow, neat's foot and bone oil, as well as the modified, epoxidised and sulfoxidised forms thereof, typically epoxidised soybean oil.
The mineral oils are based in particular on hydrocarbon compounds.
Synthetic lubricants typically comprise lubricants based on aliphatic or aromatic carboxylates, polymeric esters, polyalkylene oxides, phosphates, poly-&agr;-olefins or silicones, on a diester of a divalent acid with a monohydric alcohol, typically di
Schumacher Rolf
Zinke Horst
Ciba Specialty Chemicals Corporation
Mansfield Kevin T.
McAvoy Ellen M.
LandOfFree
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