Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Sulfurized compound of indeterminate structure – which is a...
Reexamination Certificate
2001-03-05
2003-04-01
Howard, Jacqueline V. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Sulfurized compound of indeterminate structure, which is a...
C508S433000, C558S183000, C558S186000
Reexamination Certificate
active
06541428
ABSTRACT:
This application is a 371 of PCT/FR98/00974 May 15, 1998.
A subject-matter of the present invention is a composition formed of orthophosphates of alkoxylated sulphurized alcohols, a preparation process and their use as multifunctional additives in aqueous lubricating or detergent formulations.
Additives for lubricating formulations employed under very harsh conditions (shear, temperature) and comprising phosphorus and sulphur have been developed for some years. Such compounds make it possible to improve the antiwear and corrosion-inhibiting performances of the lubricating formulations proper. Mention may be made, among the compounds of this type of those disclosed in Patent FR 2 342 983. These compounds are sulphurized monoesters of monophosphoric acid.
These compounds, the advantage of which is not challenged here, nevertheless exhibit the disadvantage of not being water-soluble. Consequently, while their use does not present any difficulty for applications in oil-based lubricating compositions, it is necessary, in the case of use in aqueous formulations, as are, for example, metal cutting fluids, to combine them with appropriate surfactants. In this way, the operation is carried out in the presence of an emulsion. However, environmental restrictions are instead tending to limit the use of such compounds.
One of the objects of the present invention is thus to provide a composition which is both water-soluble or water-dispersible and which exhibits properties compatible in particular with use in aqueous lubricating fluids, without it being necessary to add surfactants.
Thus, a first subject-matter of the invention is alkoxylated sulphurized orthophosphate compositions (SOPC):
(i) comprising at least one compound of formula (I)
(R
1
−O)
3
—P═O
or a salt of this compound,
in which formula the R
1
radicals, which are identical or different, represent:
at least one of them, the R
1
—(O—X)
n
—radical:
in which
R
1
is a hydrogen atom or a saturated or unsaturated, linear, branched or cyclic, hydrocarbonaceous radical comprising 1 to 30 carbon atoms,
X is a linear or branched alkylene radical comprising 2 to 4 carbon atoms,
n having a mean value of between 1 and 100, preferably 2 to 50.
a hydrogen atom,
a saturated or unsaturated, linear, branched or cyclic, hydrocarbonaceous radical comprising 1 to 30 carbon atoms,
at least one of the R
1
radicals of a molecule of compound of formula (I) being connected to another R
1
radical of another molecule of compound of formula (I) via one or more mono- or polysulphide bridges using S—C bonds;
(ii) and exhibiting a level of sulphur ranging from 1 to 50% by weight.
Another subject-matter of the invention is a process for the preparation of such compositions in which a sulphurization is carried out of an orthophosphate composition (OPC) comprising:
at least one orthophosphoric compound of formula (II):
(R
2
—O)
3
—P═O
or a salt of this compound,
in which formula the R
2
radicals, which are identical or different, represent:
at least one of them, the R
2
—(O—X)
n
—radical:
in which
R
2
is a hydrogen atom or a saturated or unsaturated, linear, branched or cyclic, hydrocarbonaceous radical comprising 1 to 30 carbon atoms,
X is a linear or branched alkylene radical comprising 2 to 4 carbon atoms,
n having a mean value of between 1 and 100, preferably 2 to 50,
a hydrogen atom,
a saturated or unsaturated, linear, branched or cyclic, hydrocarbonaceous radical comprising 1 to 30 carbon atoms,
at least one alcohol of formula R
2
—(O—X)
n
—OH, in which R
2
, X and n correspond to the above definition;
optionally at least one alcohol of formula R
2
—OH, in which R
2
has the same definition as above;
and in which the iodine number of the R
2
radicals, measured on the alcohol of formula R
2
—OH, is between 10 and 300, preferably between 50 and 120.
Finally, a subject-matter of the present invention is of use of these compounds as additives in aqueous formulations.
The composition according to the invention exhibits the advantage of introducing both phosphorus and sulphur and of being water-soluble or water-dispersable, without it being necessary to introduce a surfactant.
However, other advantages and objectives of the present invention will become more clearly apparent on reading the description and the example which will follow.
As was indicated previously, the composition according to the invention comprises orthophosphates of formula (I)(R
1
—O)
3
—P═O.
According to a more specific embodiment of invention, the R
1
radicals, which can be identical or different, are preferably linear or branched alkyl or mono- or polyunsaturated alkenyl radicals comprising 8 to 22 carbon atoms. Mention may in particular be made, as example of such radicals, of the stearyl, oleyl, linoleyl and linolenyl radicals.
The (SOPC) compositions according to the invention are particularly composed of molecules of orthophosphoric mono- or diesters, in the acid or salified form, or optionally of orthophosphoric triesters. It should be noted that they can be composed of a mixture of these species. And the (SOPC) compositions preferably comprise a mixture of orthophosphoric mono- and diesters. The (SOPC) compositions according to the invention can additionally comprise free phosphoric add. When it is present, the content of phosphoric acid, in the acid or salified form, can represent up to 10% by weight of the composition.
Mention may be made, among the salts of orthophosphoric compounds of formula (I), of those of the metals which appear from the columns IA, IIA, IB and VIII of the table of the Periodic Classification of the Elements. According to a particularly advantageous alternative form of the present invention, the salt of orthophosphoric compounds is a sodium, potassium, calcium, magnesium, iron, copper or zinc salt.
Mention may likewise be made, among the salts capable of being suitable, of salts of ammonium of formula —NR
4
+, in which the R radicals, which are or are not identical, represent a hydrogen atom or an alkyl radical, optionally substituted by one or more hydroxyl groups, comprising 1 to 30, more particularly from 1 to 10, carbon atoms. Mention may be made, for example, of the ammonium deriving from ammonia, methylamine, ethylamine, propylamine, isopropylamine, monoethanolamine, diethanolamine, triethanolamine, monoethylethanolamine, from aminoethylethanolamine, diethylethanolamine or from aminomethylpropanolamine.
Up to 50% by weight of at least one alcohol of formula R
1
—(O—X)
n
—OH and optionally of at least one alcohol of formula R
1
—OH, in which formulae R
1
, X and n are defined as above, can also be present in said (SOPC) compositions.
In addition, it should be noted that the R
1
radicals can optionally be connected to other R
1
radicals present in the abovementioned alcohols or alternatively to R
1
radicals present in the orthophosphoric compounds of formula (I) via one or more mono- or polysulphide bridges using S—C bonds.
A second subject-matter of the invention is a process which makes it possible to prepare the sulphurized orthophosphate compositions (SOPC).
Said process consists in carrying, out a sulphurization of an orthophosphate composition (OPC) comprising:
at least one orthophosphoric compound of formula (II):
(R
2
—O)
3
—P═O
or a salt of this compound,
in which formula the R
2
radicals, which are identical or different, represent:
at least one of them, the R
2
—(O—X)
n—
radical:
in which
R
2
is a hydrogen atom or a saturated or unsaturated, linear, branched or cyclic, hydrocarbonaceous radical comprising 1 to 30 carbon atoms,
X is a linear or branched alkylene radical comprising 2 to 4 carbon atoms,
n having a mean value of between 1 and 100, preferably 2 to 50,
a hydrogen atom,
a saturated or unsaturated, linear, branched or cyclic, hydrocarbonaceous radical comprising 1 to 30 carbon atoms,
at least one alcohol of formula R
2
—(O—X)
n
—OH, in which R
2
, X and n correspond to the above definition;
optionally at least one alcohol of formula R
2
—OH, in which R
2
Burns Doane Swecker & Mathis L.L.P.
Howard Jacqueline V.
Rhodia Chimie
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