Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Organic sulfur compound – wherein the sulfur is single bonded...
Reexamination Certificate
2000-06-02
2002-01-08
McAvoy, Ellen M. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Organic sulfur compound, wherein the sulfur is single bonded...
C585S024000
Reexamination Certificate
active
06337310
ABSTRACT:
BACKGROUND OF THE INVENTION
In the prior art, methods are known for preparing weakly or strongly superalkalinized sulfonates from sulfonic acids obtained by the sulfonation of different alkylaryl hydrocarbons and from an excess of alkaline earth base. The alkylaryl hydrocarbons subjected to the sulfonation reaction are obtained by alkylation via the Friedel-Crafts reaction of different aryl hydrocarbons, particularly aromatic hydrocarbons, with two different types of olefin. The first type of olefins are branched olefins obtained by the oligo-polymerization of propylene to C
15
to C
24
hydrocarbons, particularly the propylene tetrapolymer dimerized to a C
24
olefin. The second type are linear olefins obtained by the oligo-polymerization of ethylene to C
14
to C
40
hydrocarbons.
It is easy to obtain a good dispersion in the medium of the alkaline earth base not fixed in the form of salt if the alkylaryl sulfonic acid is derived from a hydrocarbon obtained by alkylation of an aryl hydrocarbon with a branched olefin. However, dispersion is particularly difficult when a high percentage of the alkylaryl hydrocarbon has the aryl substituent on positions 1 or 2 of a linear alkyl chain, due to the formation of a skin when exposed to open air. This poor dispersion is especially pronounced if the medium also contains a high proportion of sulfonate, that is, if it corresponds to a low Base Number (between 3 and 60), hence to a low content of free lime and the absence of carbon dioxide and carbonate.
In fact, during the alkylation reaction with benzene or another aromatic or aryl hydrocarbon and a linear olefin, 25 mole % of the alkylaryl hydrocarbon has the aryl substituent on positions 1 or 2 of the linear alkyl chain. Traditionally, aromatics attached at the 2-position of the alkyl group give the most absorption of water. When prepared by the method described, for example in French Patent No. 2,564,830, this high proportion of alkylaryl hydrocarbon having an aryl radical on position 1 or 2 of the linear alkyl chain results in a sulfonate that exhibits hygroscopic properties such that a superficial ‘skin’ is formed. This ‘skin’ makes this product unacceptable as an additive for lubricating oil. Furthermore, the formation of this superficial skin is generally accompanied by a very low filtration rate, a high viscosity, a low incorporation of calcium, a deterioration of anti-rust performance, and an undesirable turbid appearance, or even sedimentation, when the sulfonate thus prepared is added at the rate of 10% by weight to a standard lubricating oil and stored for examination.
Chromatographic analysis has been conducted to identify each of the different isomers differing by the position of the aryl radical on the carbon atom of the linear alkyl chain, and their respective influence on the properties of the corresponding alkylaryl sulfonates of alkaline earth obtained from these different isomers has been examined. It was thus discovered that the aforementioned drawbacks could be overcome, inasmuch as the mole % of the aryl hydrocarbon, other than benzene, having the aryl substituent on positions 1 or 2 of the linear alkyl chain was between 0 and 13%, and preferably between 5 and 11%, and more particularly between 7 and 10%. This discovery was the subject of U. S. Pat. No. 5,939,594, issued Aug. 17, 1999 to Le Coent.
However, satisfactory results had not been obtained when the aryl hydrocarbon was benzene. Skin formation occurred with the use of benzene, even if the benzene was alkylated with a very long chain linear mono olefin so that the mole % of the aryl hydrocarbon having the aryl substituent on positions 1 or 2 of the linear alkyl chain was between 0 and 13%, and preferably between 5 and 11%, and more particularly between 7 and 10%.
French Patent Application No. 96/10,833 discloses that the aforementioned drawbacks could be overcome by using a mixture of alkylaryl sulfonates of superalkalinized alkaline earth metals comprising:
(a) from 50% to 85% of a linear mono-alkyl phenyl sulfonate in which the linear alkyl chain contains between 14 and 40 carbon atoms, and between 0 and 13 mole % of the phenyl sulfonate radical of the alkaline earth metal is fixed on position 1 or 2 of the linear alkyl chain, and
(b) from 15% to 50% of a heavy alkylaryl sulfonate selected from:
(i) dialkylaryl sulfonates wherein both alkyl substituents are linear alkyl chains, of which the sum of the carbon atoms is from 16 to 40, or
(ii) mono or polyalkylaryl sulfonates wherein the alkyl substituent or substituents are branched chains, wherein the sum of the carbon atoms is from 15 to 48 carbon atoms.
This mixture of alkylaryl sulfonates has a maximum of 10 mole % of the phenyl sulfonate radical of the alkaline earth metal fixed on position 1 or 2 of the linear alkyl chain. This mixture has no skin formation after three days of storage in an open jar at room temperature. It has good calcium incorporation, a low viscosity, good solubility, and good performance.
European Patent Application No. 98401968.7 discloses a mixture of alkyl phenyl sulfonates of alkaline earth metals having low color and no skin formation even after three days of storage in an open jar at room temperature. That mixture comprises:
(a) from 20% to 70% of a linear mono-alkylphenyl sulfonate in which the linear mono-alkyl substituent contains from 14 to 40 carbon atoms and the mole % of the phenyl sulfonate radical fixed on position 1 or 2 of the linear alkyl chain is between 10% and 25%, and,
(b) from 30% to 80% of a branched mono-alkylphenyl sulfonate in which the branched mono alkyl substituent contains from 14 to 18 carbon atoms.
SUMMARY OF THE INVENTION
The present invention provides an alkylaryl composition wherein the aryl radical is other than phenol and wherein the alkyl radical is derived from an isomerized C
14
to C
40
normal alpha olefin and wherein either (1) the weight percent of the aryl radical fixed at position 1 or 2 of a linear alkyl chain is less than about 23, or (2) at least 28 weight percent of the alkyl radicals are branched chain alkyl radicals, or (3) both.
Further provided in accordance with this invention is an alkaline earth alkylaryl sulfonate having a Base Number of at least 250, where the aryl radical is other than phenol, wherein the alkyl radical is derived from An isomerized C
14
to C
40
normal alpha olefin and wherein either (1) the weight percent of the aryl sulfonate radical fixed at position 1 or 2 of a linear alkyl chain is less than about 23, or (2) at least 28 weight percent of the alkyl radicals are branched chain alkyl radicals, or (3) both.
Also provided in accordance with this invention is an alkaline earth alkylaryl sulfonate having a Base Number of about 2 to about 60, where the aryl radical is other than phenol, wherein the alkyl radical is derived from an isomerized C
14
to C
40
normal alpha olefin and wherein either (1) the weight percent of the aryl sulfonate radical fixed at position 1 or 2 of a linear alkyl chain is less than about 23, or (2) at least 28 weight percent of the alkyl radicals are branched chain alkyl radicals, or (3) both.
The present invention also provides a lubricating oil composition comprising a lubricating oil and an alkaline earth alkylaryl sulfonate having a Base Number of at least 250, where the aryl radical is other than phenol, wherein the alkyl radical is derived from an isomerized C
14
to C
40
normal alpha olefin and wherein either (1) the weight percent of the aryl sulfonate radical fixed at position 1 or 2 of a linear alkyl chain is less than about 23, or (2) at least 28 weight percent of the alkyl radicals are branched chain alkyl radicals, or (3) both.
Further provided in accordance with this invention is a lubricating oil composition comprising a lubricating oil and an alkaline earth alkylaryl sulfonate having a Base Number of about 2 to about 60, where the aryl radical is other than phenol, wherein the alkyl radical is derived from an isomerized C
14
to C
40
normal alpha olefin and wherein either (1) the weight percent of the aryl sulfo
Campbell Curtis B.
Le Coent Jean-Louis Marie
Chevron Oronite Company LLC
McAvoy Ellen M.
Sheridan Richard J.
Stokley Linda A.
Stumpf Walter L.
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