METHOD FOR IMPROVING THE COKING RESISTANCE OF A LUBRICATING COMPOSITION

Abstract

Disclosed is a method of lubrication including a step of lubricating a machine with a lubricating composition, the lubricating composition including 20-100% ionic liquid or of a mixture of several ionic liquids. The ionic liquid or the mixture is selected from at least: an anion A.sup.− chosen from sulfonylimides, the substituent(s) of which is (are) independently chosen from a fluoroalkyl, fluoroether, perfluorinated alkyl or perfluoroether group; and a cation C.sup.+ including a nitrogen-containing heterocycle or a quaternary ammonium, the substituent(s) of which is (are) independently chosen from: a hydrogen atom or alkyl, alkoxy, fluorinated alkyl, perfluorinated alkyl, alkylsilane, alkyl alcohol, vinyl, alkyl allyl, ether or polyether groups having a linear or branched chain having 1-3 carbon atoms. The deposition start temperature in thin film of the ionic liquid or of the mixture of ionic liquids is at least equal to 330° C. The lubricating composition reduces deposits formed in the machine.

Claims

1-14. (canceled)

15. Method of lubrication which comprises a step of lubricating a machine with a lubricating composition, the lubricating composition comprising, in mass with respect to the total mass of said lubricating composition, from 20% to 100% of an ionic liquid or of a mixture of several ionic liquids, wherein said ionic liquid or said mixture of ionic liquids is selected from an ionic liquid or a mixture of ionic liquids comprising at least: an anion A.sup.− chosen from sulfonylimides, the substituent(s) of which is (are) independently chosen from a fluoroalkyl, fluoroether, perfluorinated alkyl or perfluoroether group, and a cation C.sup.+ comprising a nitrogen-containing heterocycle or a quaternary ammonium, the substituent(s) of which is (are) independently chosen from: a hydrogen atom or alkyl, alkoxy, fluorinated alkyl, perfluorinated alkyl, alkylsilane, alkyl alcohol, vinyl, alkyl allyl, ether or polyether groups having a linear or branched chain having from 1 to 3 carbon atoms, on condition that when the cation is a quaternary ammonium, at least two of these substituents are a methyl group, the deposition start temperature (TDD) in thin film, determined by the MCT method according to the standard GFC Lu-27 A-13, of the ionic liquid or of the mixture of ionic liquids being at least equal to 330° C., said lubricating composition being suitable to reduce the deposits formed in said machine.

16. Method according to claim 15, in which the lubricating step is carried out at high temperatures of between 200 and 500° C.

17. Method according to claim 15, in which said cation C.sup.+ comprising a nitrogen-containing heterocycle is selected among: imidazolium, pyrazolium, quinolium, pyridinium, piperidinium, oxazolium, thiazolium, benzothiazolium or morpholinium.

18. Method according to claim 15, in which the cation C.sup.+ comprising a nitrogen-containing heterocycle is selected among: imidazolium, pyridinium, or pyrazolium.

19. Method according to claim 15, in which the deposition start temperature (TDD) in thin film, determined by the method MCT according to the standard GFC Lu-27 A-13, of said ionic liquid or of said mixture of ionic liquids is at least equal to 350° C.

20. Method according to claim 17, in which the cation C.sup.+ is imidazolium comprising at least two methyl groups at position 1 and 2 or at position 2 and 3, or a pyridinium comprising at least one methyl group.

21. Method according to claim 20, in which the cation C.sup.+ is a pyridinium comprising at least one methyl group at position 3, 4 or 5.

22. Method according to claim 20, in which the imidazolium comprising a methyl group at position 1 and 2 or at position 2 and 3 comprises a hydrogen atom at position 4 and 5.

23. Method according to claim 22, in which the imidazolium cation C.sup.+ is 1-ethyl-2,3-dimethylimidazolium or 1,2-dimethyl-3-((trimethylsilyl)methyl)imidazolium.

24. Method according to claim 22, in which the imidazolium, whose substituents in position 1 and 2 are methyls, the substituents in position 4 and 5 are hydrogen atoms, comprises a substituent in position 3 independently selected among the alkyl, fluorinated alkyl, perfluorinated alkyl, alkyl silane, alkyl alcohol or vinyl groups having a linear chain or a branched chain with 1 to 3 carbon atoms.

25. Method according to claim 15, in which said ##STR00061## sulfonylimide corresponds to the following general formula: in which R.sub.1 and R.sub.2 are identical or different and independently selected among a fluoroalkyl, fluoroether, perfluorinated alkyl or perfluoroether group, such as [(CF.sub.3SO.sub.2).sub.2N].sup.−, [(CF.sub.3CF.sub.2SO.sub.2).sub.2N].sup.−, [(CF.sub.3CF.sub.2CF.sub.2CF.sub.2SO.sub.2).sub.2N].sup.− or [(CF.sub.3CF.sub.2CF.sub.2SO.sub.2).sub.2N].sup.−.

26. Method according to claim 25, in which said sulfonylimide corresponds to [(CF.sub.3SO.sub.2).sub.2N].sup.−, [(CF.sub.3CF.sub.2SO.sub.2).sub.2N].sup.−, [(CF.sub.3CF.sub.2CF.sub.2CF.sub.2SO.sub.2).sub.2N].sup.− or [(CF.sub.3CF.sub.2CF.sub.2SO.sub.2).sub.2N].sup.−.

27. Method according to claim 15, in which the ionic liquid or at least one of the ionic liquids of the mixture is selected among: 3-(2-hydroxyethyl)-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide; 3-(2-hydroxypropyl)-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide; 1-ethyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide; 1-ethyl-2,3-dimethylimidazolium bis(pentafluoroethylsulfony)imide; 3-allyl-1,2-dimethylimidazolium bis(trifluoromethylsulfonyl)imide; 1,2-dimethyl-3-(trimethylsilyl)methyl)imidazolium bis(pentafluoroethylsulfony)imide; 1,2-dimethyl-3-((trimethylsilyl)methyl)imidazolium bis(trifluoromethylsulfonyl)imide; 1,2-dimethyl-3-((trimethylsilyl)propyl)imidazolium bis(trifluoromethylsulfonyl)imide; 2,3-dimethyl-1-propylimidazolium bis(pentafluoroethylsulfony)imide 2,3-dimethyl-1-propylimidazolium bis(trifluoromethylsulfonyl)imide; 2,3-dimethyl-1-propylimidazolium 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonylimide; 3-(2-methoxyethyl)-1,2-dimethylimidazolium bis(pentafluoroethylsulfony)imide; 3-(2-methoxyethyl)-1,2-dimethylimidazolium bis(trifluoromethylsulfonyl)imide; 2,3-dimethyl-1-propanolimidazolium bis(trifluoromethylsulfonyl)imide; 1,2 dimethyl-3-allylimidazolium bis(trifluoroethylsulfonyl)imide; 1-propyl-3,5-dimethylpyridinium bis(trifluoromethyl)sulfonyl)imide; 1-(2-hydroxyethyl)-3,5-dimethylpyridinium bis(trifluoromethyl)sulfonyl)imide; ethyldimethylpropylammonium bis(trifluoromethylsulfonyl)imide; N-ethyl-2-hydroxy-N,N-dimethylethaneammonium bis(trifluoromethylsulfonyl)imide; N-ethyl-2-hydroxy-N,N-dimethylethaneammonium bis(pentafluoroethylsulfonyl) imide; N-(2-hydroxyethyl)-N,N-dimethylpropaneammonium bis(trifluoromethylsulfonyl) imide; 1-propyl-4-methylpyridin-1-ium bis(trifluoromethylsulfonyl)imide; 1-ethyl-3-methylpyridin-1-ium bis(trifluoromethylsulfonyl)imide; 1-propyl-3,5-dimethylpyridinium bis(trifluoromethylsulfonyl)imide; 1-(2-hydroxyethyl)-3,5-dimethylpyridinium bis(trifluoromethylsulfonyl)imide; or a mixture thereof.

28. Method according to claim 15, in which the lubricating composition comprises at least 50% to 100% of said ionic liquid with respect to the total mass of the lubricating composition.

29. Method according to claim 28, in which the lubricating composition comprises at 75 mass-% to 100 of said ionic liquids with respect to the total mass of the lubricating composition.

30. Method according to claim 15, in which the lubricating composition comprises from 0 mass-% to 25 mass-% of one or of several additives with respect to the total mass of the lubricating composition.

31. Method according to claim 30, in which the additive or the additives are selected from: anti-wear agents, anti-corrosion agents, antioxidants, and a mixture of two or more of these additives.

32. Method for reducing the deposits formed in a machine by using a lubricating composition, in which said lubricating composition comprises, by mass with respect to its total mass, from 20% to 100% of an ionic liquid or of a mixture of several ionic liquids, said ionic liquid or said mixture of ionic liquids being selected from an ionic liquid or a mixture of ionic liquids comprising at least: an anion A− chosen from sulfonylimides, the substituent(s) of which is (are) independently chosen from a fluoroalkyl, fluoroether, perfluorinated alkyl, perfluoroether or perfluorosulfonyl group, and a cation C+ comprising a nitrogen-containing heterocycle or a quaternary ammonium, the substituent(s) of which is (are) independently chosen from: a hydrogen atom or alkyl, alkoxy, fluorinated alkyl, perfluorinated alkyl, alkylsilane, alkyl alcohol, vinyl, alkyl allyl, ether or polyether groups having a linear or branched chain having from 1 to 3 carbon atoms, on condition that when the cation is a quaternary ammonium, at least two of these substituents are a methyl group, the deposition start temperature (TDD) in thin film, determined by the MCT method according to the standard GFC Lu-27 A-13, of the ionic liquid or of the mixture of ionic liquids is at least equal to 330° C.

33. Method according to claim 32, wherein the deposition start temperature (TDD) in thin film, determined by the MCT method according to the standard GFC Lu-27 A-13, of the ionic liquid or of the mixture of ionic liquids is higher than or equal to 350° C.

34. The method of claim 20, wherein the cation C.sup.+ is a pyridinium comprising at least one methyl group at position 3, 4 or 5.

Description

DESCRIPTION OF THE INVENTION

[0056] The applicant strived to develop new compounds having an excellent resistance to thin-film coking at very high temperature (for example between 200° C. and 500° C.), suitable for a use in lubricating compositions, especially for turbines for aviation or for conveyor chains.

[0057] The applicant has further shown that a specific selection of cations and of anions forming an ionic liquid makes it possible to form a lubricating base for lubricating compositions used, for example, in turbine engines of aircraft.

[0058] Although it is known that ionic liquids have a good thermal stability (up to 500° C., determined by a thermogravimetric analysis, TGA), the applicant has surprisingly found that a particular combination of anions and of cations form ionic liquids having a very high resistance to thin-film coking, especially determined by the MCT method (standard GFC Lu-27 A-13, version 2) and that this surprising effect was not at all related to their thermal stability determined by the thermogravimetric analysis (TGA). In other words, even when an ionic liquid is known for having a good thermal stability by TGA, this does not mean that it also has a good resistance to thin-film coking at high temperature, and especially when this is determined by a MicroCoking Test (MCT).

[0059] The applicant has thus further shown that the selected combination has improved properties (i.e. an improved resistance to thin-film coking) with respect to other ionic liquids and with respect to lubricating bases conventionally used especially for aircraft turbines or conveyor chains.

[0060] The applicant has shown that thermal stability as well as resistance to thin-film coking of an ionic liquid depends on the nature of the anion, on the nature of the cation and on their substituents.

[0061] Different publications describe that alkyl chains having more than six atoms of carbon on the cationic part of the ionic liquid make it possible to increase the lubricating performance of the ionic liquids.

[0062] The applicant has however surprisingly discovered that cations having substituents with short chains, such as an alkyl chain, alkyl silane, alcohol, or a C1-C3 alkoxy chain, make it possible to improve the resistance to thin-film coking and to obtain a TDD of at least 330° C. and preferably of at least 350° C., while having a good lubricating power.

[0063] The applicant has also discovered that the choice of the anion is not arbitrary and that only some anions selected among sulfonylimides make it possible to form, together with the appropriate cations, an ionic liquid having an excellent resistance to coking. That effect can be further improved by a particular selection of the substituents of the anion, which are preferably substituents selected among: fluoroalkyl, fluoroether, perfluorinated alkyl or perfluoroethers.

[0064] The present invention therefore aims at a method of lubrication which comprises a step of lubricating a machine, such as an engine or a turbine, with a lubricating composition, the lubricating composition comprising, in mass with respect to the total mass of said lubricating composition, from 20% to 100% of an ionic liquid or of a mixture of several ionic liquids,

[0065] characterized in that said ionic liquid or said mixture of ionic liquids is selected from an ionic liquid or a mixture of ionic liquids comprising at least: [0066] an anion A.sup.− chosen from sulfonylimides, the substituent(s) of which is (are) independently chosen from a fluoroalkyl, fluoroether, perfluorinated alkyl or perfluoroether group, and [0067] a cation C.sup.+ comprising a nitrogen-containing heterocycle or a quaternary ammonium, the substituent(s) of which is (are) independently chosen from: a hydrogen atom or alkyl, alkoxy, fluorinated alkyl, perfluorinated alkyl, alkylsilane, alkyl alcohol, vinyl, alkyl allyl, ether or polyether groups having a linear or branched chain having from 1 to 3 carbon atoms, on condition that when the cation is a quaternary ammonium, at least two of these substituents are a methyl group,

[0068] the deposition start temperature (TDD) in thin film, determined by the MCT method according to the standard GFC Lu-27 A-13, of the ionic liquid or of the mixture of ionic liquids being at least equal to 330° C.,

[0069] said lubricating composition being suitable to reduce the deposits, such as carbonaceous residues, formed in said machine.

[0070] Another subject of the present invention is the use of a lubricating composition for reducing the deposits, such as carbonaceous residues, formed in a machine (for example during a lubricating step), in which said lubricating composition comprises, by mass with respect to its total mass, from 20% to 100% of an ionic liquid or of a mixture of several ionic liquids, said ionic liquid or said mixture of ionic liquids being selected from an ionic liquid or a mixture of ionic liquids comprising at least: [0071] an anion A.sup.− chosen from sulfonylimides, the substituent(s) of which is (are) independently chosen from a fluoroalkyl, fluoroether, perfluorinated alkyl or perfluoroether group, and [0072] a cation C.sup.+ comprising a nitrogen-containing heterocycle or a quaternary ammonium, the substituent(s) of which is (are) independently chosen from: a hydrogen atom or alkyl, alkoxy, fluorinated alkyl, perfluorinated alkyl, alkylsilane, alkyl alcohol, vinyl, alkyl allyl, ether or polyether groups having a linear or branched chain having from 1 to 3 carbon atoms, on condition that when the cation is a quaternary ammonium, at least two of these substituents are a methyl group,

[0073] the deposition start temperature (TDD) in thin film, determined by the MCT method according to the standard GFC Lu-27 A-13, of the ionic liquid or of the mixture of ionic liquids is at least equal to 330° C., preferably higher than or equal to 350° C.

[0074] For the remainder of the description below, the features are valid both for the lubricating process and for the use, described above.

[0075] Especially, the deposition start temperature TDD in thin film of said ionic liquid or of said mixture of ionic liquids, as determined by the MCT method, is higher than or equal to 330° C., preferably higher than or equal to 340° C., especially higher than 350° C.

[0076] According to the invention, a temperature TDD of at least 330° C. comprises especially the following values: 330, 331, 332, 333, 334, 335, 336, 337, 338, 339, 340, 341, 342, 343, 344, 345, 346, 347, 348, 349, 350, 351, 352, 353, 354, 355, 356, 357, 358, 359, 360, 365, 370, 380, 385, 390, 395, 400, 405, 410, 415, 420, 425, 430, 435, 440, 445, 450, 455, 460, 465, 470, 475, 480, 485, 490, 495, 500, etc., or any interval situated between these values.

[0077] Thus, the ionic liquid or liquids selected according to the invention have an excellent thermal stability such that the lubricating step can be carried out under high temperatures of between 200° C. and 500° C., preferably between 280° C. and 500° C.

[0078] Thus, within the present invention, at least one cation C.sup.+ may be selected among the following ones, provided that it forms with the anion an ionic liquid having a TDD higher than or equal to 330° C.: a nitrogen-containing heterocycle or a quaternary ammonium.

[0079] Generally, the nitrogen-containing heterocycle according to the invention is selected among: imidazolium, pyrazolium, quinolium, pyridinium, piperidinium, oxazolium, thiazolium, benzothiazolium, morpholinium or one of the derivatives thereof. The term “derivatives” designates the derivatives of said cations according to the position of their hetero-atoms and the saturation of their cycle.

[0080] Generally, the nitrogen-containing heterocycle forming the cation C+ of the ionic liquid or of the mixture of ionic liquids according to the invention can be selected among: imidazolium, pyrazolium, quinolium, pyridinium, piperidinium, oxazolium, thiazolium, benzothiazolium or morpholinium or one of the derivatives thereof,

[0081] the substituent or substituents thereof being selected independently among: the hydrogen atom or the alkyl, aryl, aryloxy, alkylthioether, fluorinated alkyl, perfluorinated alkyl, alkyl silane, alkyl alcohol, allyl, vinyl, ether, arylether, arylthioether or polyether groups, having a linear or branched chain having from 1 to 3 carbon atoms according to the nature of the cation.

[0082] Within the present invention, it is understood that a linear chain or a branched chain having from 1 to 3 carbon atoms is a chain having a number of carbon atom(s) equal to 1, 2 or 3; these numbers comprising thus the intervals of 1 to 3, of 1 to 2 or of 2 to 3 carbon atoms.

[0083] The cation C.sup.+ according to the invention is particularly represented hereafter:

TABLE-US-00001 [00001]   imidazolium [00002]   pyridinium [00003]   piperidinium [00004]   oxazolium [00005]   benzothiazolium [00006]   thiazolium [00007]   pyrazolium [00008]   morpholinium [00009]   quinolium [00010]   quatemary ammonium

[0084] whose substituents R.sub.1 to R.sub.12, such as indicated hereabove are identical or different and are selected independently among: [0085] hydrogen atom and/or [0086] alkyl, aryl, alkylthioether, arylether, arylthioether, aryloxy, fluorinated alkyl, perfluorinated alkyl, alkyl silane, alkyl alcohol, allyl, ether, arylether, arylthioether, or polyether group with a linear chain or a branched chain having 1 to 3 carbon atoms.

[0087] Preferably, the nitrogen-containing heterocycle is selected among imidazolium, pyridinium, or pyrazolium.

[0088] As an example, the cation C.sup.+ can be an imidazolium cation having the above represented formula, i.e. :

##STR00011##

[0089] where

[0090] R.sub.4 and R.sub.5 are identical or different, preferably hydrogen atoms;

[0091] R.sub.1 and R.sub.2 can be: a hydrogen atom, a methyl, ethyl, propyl, vinyl, allyl, cyano group, preferably a methyl group;

[0092] R.sub.3 is independently selected among the following group: alkyl, alkyl silane, a fluorinated alkyl, a perfluorinated alkyl, an alkyl alcohol, an allyl, ether or polyether, said group being linear or branched having from 1 to 3 carbon atoms.

[0093] In particular, the imidazolium comprises at least two methyl groups at position 1 and 2 or at position 2 and 3.

[0094] Preferably, the imidazolium comprising a methyl group at position 1 and 2 or at position 2 and 3 comprises a hydrogen atom at position 4 and 5 and is preferably 1-ethyl-2,3-dimethyl-imidazolium or 1,2-dimethyl-3-((trimethylsilyl)methyl)imidazolium.

[0095] Even more preferably, when the substituents in position 1 and 2 of the imidazolium are methyls, the substituents in position 4 and 5 are hydrogen atoms and the substituent in position 3 is independently selected among the alkyl, fluorinated alkyl, perfluorinated alkyl, alkyl silane, alkyl alcohol or vinyl groups, having a linear chain or a branched chain with 1 to 3 carbon atoms.

[0096] According to a particular embodiment, the cation according to the invention is not 1-ethyl-3-methyl-imidazolium. According to this mode, the following ionic liquid can be excluded from the ionic liquids according to the invention: 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide.

[0097] According to another embodiment, the cation can be a thiazolidinium with the formula represented above, i.e.:

##STR00012##

[0098] where

[0099] R.sub.3 and R.sub.4 are identical or different, preferably hydrogen atoms,

[0100] R.sub.1 may be a hydrogen, a methyl, ethyl, propyl, vinyl, allyl, cyano group; preferably a methyl group,

[0101] R.sub.2 is independently selected among the following group: an alkyl, a fluorinated alkyl, a perfluorinated alkyl, an alkyl alcohol, an allyl, a vinyl, an ether or a polyether, said group being linear or branched with 1 to 3 carbon atoms.

[0102] As well, the cation C+ can be a pyridinium cation having the formula represented above, i.e.:

##STR00013##

[0103] where

[0104] R.sub.1 is independently selected among: an alkyl, fluorinated alkyl, perfluorinated alkyl, alkyl silane, alkyl alcohol, allyl, vinyl, ether or polyether group, preferably among an alkyl, alkyl silane, ether, fluorinated alkyl, perfluorinated alkyl group, said group being linear or branched and having 1 to 3 carbon atoms;

[0105] R.sub.2 to R.sub.6 are identical or different, selected among: hydrogen atom, methyl group, ethyl group, a halogenated derivative, a dimethyl amino group, preferably hydrogen atoms.

[0106] In particular, the pyridinium comprises at least one methyl group, or even two, preferably at position 3, 4 or 5.

[0107] Preferably, the pyridinium comprises at least two methyl groups at position 3 and 5.

[0108] The cation C.sup.+ can be a morpholinium cation with the formula represented above, i.e.:

##STR00014##

[0109] where

[0110] R.sub.1 to R.sub.8 are identical or different, selected among: hydrogen atom, a methyl or ethyl group, preferably hydrogen atoms;

[0111] R.sub.9 and R.sub.10 are independently selected among an alkyl, fluorinated alkyl, perfluorinated alkyl, alkyl silane, alkyl alcohol, allyl, vinyl, ether or polyether group, preferably among an alkyl, alkyl silane, ether, alkyl alcohol, fluorinated alkyl, perfluorinated alkyl group, said group being linear or branched with 1 to 3 carbon atoms; R.sub.9 is preferably a methyl.

[0112] The cation C.sup.+ can be a piperidinium cation having the formula represented above, i.e.:

##STR00015##

[0113] where

[0114] R.sub.1 to R.sub.10 are identical or different, selected among: hydrogen atom, a methyl or ethyl group, preferably a hydrogen atom;

[0115] R.sub.11 and R.sub.12 are independently selected among an alkyl, fluorinated alkyl, perfluorinated alkyl, alkyl silane, alkyl alcohol, allyl, vinyl, ether or polyether group; preferably among an alkyl, alkyl silane, ether, fluorinated alkyl, perfluorinated alkyl group, said group being linear or branched with 1 to 3 carbon atoms; R.sub.11 is preferably a methyl group.

[0116] Equally, the cation C.sup.+ can be a quaternary ammonium cation having the formula represented above, i.e.:

##STR00016##

[0117] where

[0118] R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are identical or different, are selected among an alkyl, fluorinated alkyl, perfluorinated alkyl, alkyl silane, alkyl alcohol, ether or polyether group with a linear chain or a branched chain with 1 to 3, on condition that at least two among the radicals R.sub.1 to R.sub.4 are methyl groups.

[0119] As an example, the cation C.sup.+ can be a quinolium cation having the formula such as represented further up, i.e.:

##STR00017##

[0120] where

[0121] R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are identical or different, selected among: hydrogen atom, a methyl, ethyl, propyl, butyl, dimethylamine group, preferably hydrogen atoms;

[0122] R.sub.1 is independently selected among: an alkyl, fluorinated alkyl, perfluorinated alkyl, an alkyl alcohol, an ether or a polyether, said group being linear or branched with 1 to 3 carbon atoms.

[0123] As an example, the cation C.sup.+ can be a pyrazolium cation with the formula such as represented further up, i.e.:

##STR00018##

[0124] where

[0125] R.sub.2 and R.sub.3 are identical or different, preferably hydrogen atoms;

[0126] R.sub.1 and R.sub.5 may be: hydrogen atom, a methyl, ethyl, propyl, vinyl, cyano group, preferably a methyl group;

[0127] R.sub.4 is independently selected among: an alkyl, alkyl silane, fluorinated alkyl, perfluorinated alkyl, alkyl alcohol, an ether or a polyether group, said group being linear or branched with 1 to 3 carbon atoms.

[0128] As a further but not limiting example, the substituents R.sub.1 to R.sub.12 of the cations according to the invention are groups or linear or branched chains which can be selected among the following ones, provided the conditions listed further up are fulfilled:

[0129] the alkyls: methyl, ethyl, propyl, butyl;

[0130] the fluorinated alkyls: trifluoromethyl, trifluoroethyl, trifluoropropyl, etc;

[0131] the perfluorinated alkyls: perfluoromethyl, perfluoroethyl, perfluoropropyl, etc;

[0132] the alkyl silanes: trimethylsilylmethyl; triethylsilylmethyl; trimethylsilylethyl; trimethylsilylpropyl; etc;

[0133] the alkyl alcohols: hydroxymethyl, hydroxyethyl, hydroxypropyl, etc

[0134] the alkenes: vinyl, allyl, etc;

[0135] the ethers: methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethyl, etc;

[0136] the polyethers: polymethylene, polyethylene, polypropylene, etc.

[0137] Generally, all of the radicals R.sub.1 to R.sub.12 have short chains and comprise no more than 3 carbon atoms.

[0138] The applicant has further discovered that the selection of the anion and its substituents is important for forming an ionic liquid having a good resistance to coking for thin films.

[0139] As mentioned above, the anion A.sup.− according to the invention is selected among sulfonylimide, whose substituent or substituents are independently selected among the following: a fluoroalkyl, fluoroether, perfluorinated alkyl or perfluoroether group.

[0140] In particular, the sulfonylimide compound according to the invention corresponds to the following general formula:

##STR00019##

[0141] where R.sub.1 and R.sub.2 are identical or different, independently selected among a fluoroalkyl, fluoroether, perfluorinated alkyl or perfluoroether group.

[0142] As an example, the following compounds are suitable as sulfonylimide according to the invention: [(CF.sub.3SO.sub.2).sub.2N].sup.−, [(CF.sub.3CF.sub.2SO.sub.2).sub.2N].sup.−, [(CF.sub.3CF.sub.2CF.sub.2CF.sub.2SO.sub.2).sub.2N].sup.− or [(CF.sub.3CF.sub.2CF.sub.2SO.sub.2).sub.2N].sup.−.

[0143] Generally, the ionic liquids or at least one of the ionic liquids of the mixture being suitable within the terms of the present invention can be selected among: [0144] 3-(2-hydroxyethyl)-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide; [0145] 3-(2-hydroxypropyl)-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide; [0146] 1-ethyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide; [0147] 1-ethyl-2,3-dimethylimidazolium bis(pentafluoroethylsulfonyl)imide; [0148] 3-allyl-1,2-dimethylimidazolium bis(trifluoromethylsulfonyl)imide; [0149] 1,2-dimethyl-3-(trimethylsilyl)methyl)imidazolium bis(pentafluoroethylsulfonyl)-imide; [0150] 1,2-dimethyl-3-((trimethylsilyl)methyl)imidazolium bis(trifluoromethylsulfonyl)-imide; [0151] 1,2-dimethyl-3-((trimethylsilyl)propyl)imidazolium bis(trifluoromethylsulfonyl)-imide; [0152] 2,3-dimethyl-1-propylimidazolium bis(pentafluoroethylsulfonyl)imide; [0153] 2,3-dimethyl-1-propylimidazolium bis(trifluoromethylsulfonyl)imide; [0154] 2,3-dimethyl-1-propylimidazolium 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonyl-imide; [0155] 3-(2-methoxyethyl)-1,2-dimethylimidazolium bis(pentafluoroethylsulfonyl)imide; [0156] 3-(2-methoxyethyl)-1,2-dimethylimidazolium bis(trifluoromethylsulfonyl)imide; [0157] 2,3-dimethyl-1-propanolimidazolium bis(trifluoromethylsulfonyl)imide; [0158] 1,2 dimethyl-3-allylimidazolium bis(trifluoroethylsulfonyl)imide; [0159] 1-propyl-3,5-dimethylpyridinium bis(trifluoromethyl)sulfonyl)imide; [0160] 1-(2-hydroxyethyl)-3,5-dimethylpyridinium bis(trifluoromethyl)sulfonyl)imide; [0161] ethyldimethylpropylammonium bis(trifluoromethylsulfonyl)imide; [0162] N-ethyl-2-hydroxy-N,N-dimethylethaneammonium bis(trifluoromethylsulfonyl)-imide; [0163] N-ethyl-2-hydroxy-N,N-dimethylethaneammonium bis(pentafluoroethylsulfonyl)-imide; [0164] N-(2-hydroxyethyl)-N,N-dimethylpropaneammonium bis(trifluoromethylsulfonyl)-imide; [0165] 1-propyl-4-methylpyridin-1-ium bis(trifluoromethylsulfonyl)imide; [0166] 1-ethyl-3-methylpyridin-1-ium bis(trifluoromethylsulfonyl)imide; [0167] 1-propyl-3,5-dimethylpyridinium bis(trifluoromethylsulfonyl)imide; [0168] 1-(2-hydroxyethyl)-3,5-dimethylpyridinium bis(trifluoromethylsulfonyl)imide; [0169] or a mixture thereof.

[0170] As an example, the mixtures of the following ionic liquids are suitable within the present invention and make it possible to have a TDD≧330° C.: [0171] 80% 1-propyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide and 20% 1,2-dimethyl-3-(trimethylsilyl)imidazolium bis(pentafluoromethylsulfonyl); [0172] 80% 1-propyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide and 20% 1,2-dimethyl-3-(trimethylsilyl)imidazolium bis(trifluoromethylsulfonyl)imide; [0173] 80% 1-propyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide and 20% 1,2-dimethyl-3-ethylimidazolium bis(trifluoromethylsulfonyl)imide.

[0174] Preferably, the ionic liquid or the mixture of ionic liquids is chosen from: [0175] 1-ethyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide; [0176] 1,2-dimethyl-3-((trimethylsilyl)methyl)imidazolium bis(trifluoromethylsulfonyl)-imide; [0177] 1,2-dimethyl-3-((trimethylsilyl)methyl)imidazolium bis(pentafluoromethyl-sulfonyl)imide.

[0178] As indicated here above, the lubricating composition comprises in mass, with respect to its total mass, from 20% to 100% ionic liquid or ionic liquids, preferably from 50% to 100% and ideally from 75% to 100%.

[0179] Within the present invention, the term “at least 20 mass-%” comprises at least 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 92%, 95%, 97%, 98%, 99%, 99.5%, 99.9%.

[0180] Generally, the ionic liquid(s) constitute(s) the lubricating base of the lubricating composition.

[0181] According to one feature of the invention, that lubricating base can also comprise conventional oils known to the person skilled in the art, such as one or more long-chain esters.

[0182] Advantageously, the ester(s) with long chains is/are selected among the group formed by the reaction products of one or more polyols with one or more carboxylic acid(s) having 4 to 12 carbon atoms, the carbon chains of said carboxylic acids being either linear or branched. For a non limitative illustration purpose only, polyols appropriate for obtaining esters suitable for use in lubricating compositions for aircraft turbines include trimethylol propane, pentaerythritol, dipentaerythritol, neopentylglycol, tripentaerythritol, ditrimethylol propane, and their mixtures. For a non limitative illustration purpose only, carboxylic acids appropriate for obtaining esters suitable for use in lubricating compositions for aircraft turbines include: valeric acid, isovaleric acid, heptanoic acid, caprylic acid, nonanoic acid, isononanoic acid and capric acid. Thus, the long-chain ester(s) of said lubricating composition may be selected from products resulting from the reaction of pentaerythritol and of dipentaerythritol with one or more carboxylic acid(s) selected from the group consisting of valeric acid, isovaleric acid, heptanoic acid, caprylic acid, nonanoic acid, isononanoic acid and capric acid.

[0183] For a non limitative illustration purpose only, long-chain esters may be prepared by reacting a commercially available technical pentaerythritol with a mixture of carboxylic acids having 4 to 12 carbon atoms under standard esterification conditions that are well known to the person skilled in the art. Technical pentaerythritol is a mixture comprising from about 85% to 92% by weight of monopentaerythritol and from 8% to 15% by weight of dipentaerythritol. It may further comprise some amount of tri- and tetra-pentaerythritol which are traditionally formed as by-products during the preparation of technical pentaerythritol. As an example of a mixture of esters appropriate for the lubricating composition according to the invention, mention may be made of the composition of synthetic esters marketed by NYCO under the reference Nycobase 5750.

[0184] The lubricating composition comprises generally from 0 mass-% to 25 mass-% of one or more additives not belonging to the family of ionic liquids.

[0185] These additives are for example anti-wear agent(s), anti-corrosion agent(s) and/or yellow metal deactivating additive(s), antioxidant(s), or mixtures of two or more of these additives.

[0186] The anti-wear additives are known to the person skilled in the art and comprise among others the family of triarylphosphates (tricresyl phosphate, tri(butylphenyl) phosphate, tri(isopropylphenyl) phosphate, trixylylphosphate).

[0187] The anti-corrosion additive or additives and/or yellow metal deactivating additive(s) are selected from agents well known to the person skilled in the art, especially from derivatives of benzotriazole. For a non limitative illustration purpose only, particularly preferred additives include benzotriazole and methyl benzotriazole.

[0188] The antioxidant(s) in the lubricating composition of the invention may be selected from compounds well known to the person skilled in the art such as aromatic amines, aromatic amine oligomers, and their mixtures, that list being not limitative. In a preferred embodiment, the antioxidant agent(s) is or are selected from aromatic amines and, especially, from diaryl amines, N-arylnaphthyl amines, homo- and hetero-oligomers thereof and their mixtures. Aromatic rings of diaryl amines, N-arylnaphthyl amines and oligomers thereof may be optionally substituted with one or more alkyl group(s) comprising 2 to 10 carbon atoms. The person skilled in the art could for example refer to the international application WO95/16765, which discloses the preparation of an anti-oxidizing composition comprising diaryl amine oligomers as well as diaryl amine/N-aryl naphthyl amine heterodimers, or to the U.S. Pat. No. 5,489,711 which discloses the preparation of diaryl amine oligomers possessing anti-oxidizing properties.

[0189] For a non limitative illustration purpose only, particularly preferred antioxidants include di(octylphenyl)amines, octylphenyl-α-naphthyl amines and their oligomers.

[0190] The lubricating composition may comprise other additives known to the person skilled in the art, such as polymers which improve viscosity, dispersants, additives which lower the pour-point, etc.

[0191] The ionic liquids having a deterioration start temperature, as determined by MCT, of higher than or equal to 294° C. are preferably used for reducing the deposits formed in the machine when it is lubricated with the lubricating composition described above.

[0192] The lubricating composition as defined above may thus be used in machines for reducing the deposits of coke for thin films.

[0193] The examples hereinafter, which are not limiting, illustrate the present invention.

EXAMPLES

[0194] The applicant has shown by the following experimental testings that a precise combination of anions and cations as well as of their substituents make it possible to form an ionic liquid or a mixture of ionic liquids having an excellent resistance to coking for thin films.

[0195] The applicant has also tested the ionic liquids disclosed in the prior art cited further up. In a surprising manner, it has been stated that most of the ionic liquids as thin films degrade very quickly as the tables hereinafter show, notwithstanding their remarkable thermal stability which goes along with their very good results in TGA.

[0196] A. Experimental Protocol

[0197] The conditions of the experimental testing are as follows: [0198] 0.6 ml of oil without anti-foam [0199] duration: 90 min [0200] plate made of an aluminum alloy tilted by 1.5%+/−0.05% toward the hot point which is situated at the lower point comprising a trough [0201] temperature gradient here generally from 250° C. to 300° C. (or more, for example 280° C. to 350° C.).

[0202] When the temperature conditions are fulfilled, 0.6 ml of a lubricating composition to be tested is placed in the trough of a plate made of an aluminum alloy and is exposed to a temperature gradient of 250° C. to 330° C. (or more).

[0203] After 90 minutes of heating, the excess oil which is still liquid is withdrawn, drained and rinsed with a mineral oil. Then the plate is left to cool before being degreased. Then, the place and the aspect of the deposits are evaluated for determining the deposition start temperature.

[0204] For doing this, the color of the deposits obtained on the trough is compared to that of standard varnishes according to the CRC scale of varnishes—scale C. The deposition start temperature corresponds to an AMF of 9 (mean coefficient of merit obtained for a plate of essentially intrinsic color to slightly colored). By assimilating the gradient to a thermal straight line, that temperature is determined by (cf. FIG. 1 which represents diagrammatically a plate of that experimental testing):

TDD=θ1−[(θ1−θ2)×L/81]

with: [0205] TDD=deposition start temperature of size AMF 9 (° C.), [0206] θ1=adjustment temperature of the hot point (° C.), [0207] θ2=adjustment temperature of the cold point (° C.), [0208] L=distance between the adjusting hole and the beginning of deposits of size AMF 9 (mm), [0209] 81=distance (mm) between the two holes for thermal probes.

[0210] Thus, with MCT, the higher the value of the deposition start temperature (TDD), the better is the thermal stability of the lubricating composition.

[0211] The TGA measurement was carried out with a temperature ramp of 10° C./min under an inert atmosphere (N.sub.2 gas).

[0212] B. Influence of the Nature of the Anion on the Thermal Stability Determined by TGA and MCT of the Ionic Liquids (Table 1)

[0213] Table 1 shows that the nature of the anion is very important for the thermal stability of the ionic liquid.

[0214] These tests thus show that the anions A− chosen from sulfates, bis(fluorosulfonyl)imide, phosphates, dicyanamides, borates, sulfonates, thiolates or else acetates did not make it possible to obtain a deposition start temperature of at least 330° C., even if these compounds have a very good thermal stability according to the TGA test under N.sub.2.

[0215] On the other hand, generally, whatever the nature of the cation as defined according to the invention, the perfluorosulfonylimide anions make it possible to have a deterioration start temperature as determined by MCT which is higher than or equal to 330° C. or even higher than or equal to 350° C.

[0216] C. Influence of the Nature of the Cation and of Its Substituents on the Thermal Stability Determined by TGA (N.sub.2) and MCT of the Ionic Liquids (Table 2)

[0217] Consequently, the experimental testings show that particular cations according to the invention make it possible to obtain, combined with the appropriate anion, an ionic liquid having an excellent resistance to thin-film coking.

[0218] Further, as shown by examples 25 to 31, it is essential that the cations comprise the substituents according to the invention, i.e. hydrogen atom or alkyl, fluorinated alkyl, perfluorinated alkyl, alkyl silane, alkyl alcohol, allyl, ether or polyether group having a linear chain or a branched chain with 1 to 3 carbon atoms. In particular, when the cation is a quarternary ammonium, it is important that at least two of its substituents are a methyl as shown by examples 24 to 26 above.

[0219] D. Examples of Ionic Liquids Having a Degradation Start Temperature Determined by MCT Higher Than or Equal to 330° C. (Table 3).

TABLE-US-00002 TABLE 3 TGA MCT Ex Nomenclature Cation Anion (10° C./mn) (250-300° C.) 32 3-(2-hydroxyethyl)-2,3-dimethyl- imidazolium bis(trifluoromethylsulfonyl)imide [00020] [(CF.sub.3SO.sub.2).sub.2N].sup.− nd >330 33 3-(2-hydroxypropyl)-2,3-dimethyl- imidazolium bis(trifluoromethylsulfonyl)imide [00021] 436 >330 34 1-ethyl-2,3-dimethyl-imidazolium bis(trifluoromethylsulfonyl)imide [00022] [(CF.sub.3SO.sub.2).sub.2N].sup.− 457 >330 35 1-ethyl-2,3-dimethyl-imidazolium [(CF.sub.3CF.sub.2SO.sub.2).sub.2N].sup.− 415 >330 bis(pentafluoroethylsulfonyl)imide 36 3-allyl-1,2-dimethyl-imidazolium bis(trifluoromethylsulfonyl)imide [00023] [(CF.sub.3SO.sub.2).sub.2N].sup.− 431 >330 37 1,2-dimethyl-3-((trimethylsilyl)methyl)- imidazolium bis(trifluoromethylsulfonyl)imide [00024] [(CF.sub.3SO.sub.2).sub.2N].sup.− 439 >330 38 1,2-dimethyl-3-((trimethylsilyl)methyl)- [(CF.sub.3CF.sub.2SO.sub.2).sub.2N].sup.− 412 >330 imidazolium bis(pentafluoroethylsulfonyl)imide 39 1,2-dimethyl-3-((trimethylsilyl)propyl)- imidazolium bis(trifluoromethylsulfonyl)imide [00025] [(CF.sub.3SO.sub.2).sub.2N].sup.− 401 >330 40 2,3-dimethyl-1-propyl-imidazolium bis(trifluoromethylsulfonyl)imide [00026] [(CF.sub.3SO.sub.2).sub.2N].sup.− 459 >330 41 2,3-dimethyl-1-propyl-imidazolium [(CF.sub.3CF.sub.2SO.sub.2).sub.2N].sup.− 412 >330 bis(pentafluoroethylsulfonyl)imide 42 2,3-dimethyl-1-propyl-imidazolium [(CF.sub.3CF.sub.2CF.sub.2CF.sub.2SO.sub.2).sub.2N].sup.− nd >330 bis(nonafluorobutanesulfonyl)imide 43 2,3-dimethyl-1-propyl-imidazolium [(CF.sub.2CF.sub.2CF.sub.2S.sub.2O.sub.4)N].sup.− nd >330 1,1,2,2,3,3-hexafluoropropane-1,3- disulfonyl-imide 44 3-(2-methoxyethyl)-1,2-dimethyl- imidazolium bis(trifluoromethylsulfonyl)imide [00027] [(CF.sub.3SO.sub.2).sub.2N].sup.- 431 >330 45 3-(2-methoxyethyl)-1,2-dimethyl- [(CF.sub.3CF.sub.2SO.sub.2).sub.2N].sup.- 410 >330 imidazolium bis(pentafluoroethylsulfonyl) imide 46 2,3-dimethyl-1-propanolimidazolium bis(trifluoromethylsulfonyl)imide [00028] [(CF.sub.3SO.sub.2).sub.2N]— 436 >330 47 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [00029] [(CF.sub.3SO.sub.2).sub.2N]— 434 >330 48 1-propyl-3,5-dimethyl-pyridinium bis(trifluoromethylsulfonyl) imide [00030] [(CF.sub.3SO.sub.2).sub.2N— 403 >330 49 1-(2-hydroxyethyl)-3,5-dimethyl- pyridinium bis(trifluoromethylsulfonyl)imide [00031] 396 >330 50 ethyldimethylpropylammonium bis(trifluoromethylsulfonyl)imide [00032] [(CF.sub.3SO.sub.2).sub.2N— 408 >330 51 N-ethyl-2-hydroxy-N,N-dimethylethan- ammonium bis(trifluoromethylsulfonyl)imide [00033] [(CF.sub.3SO.sub.2).sub.2N— 390 >330 52 N-ethyl-2-hydroxy-N,N- [(CF.sub.3CF.sub.2SO.sub.2).sub.2N— ? >330 dimethylethaneammonium bis(pentafluoromethylsulfonyl)imide 53 N-(2-hydroxyethyl)-N,N- dimethylpropaneammonium bis(trifluoromethylsulfonyl)imide [00034] [(CF.sub.3SO.sub.2).sub.2N— 388 >330 54 80% [00035] [(CF.sub.3SO.sub.2).sub.2N].sup.− 439 >330 20% [00036] [(CF.sub.3CF.sub.2SO.sub.2).sub.2N].sup.− 55 80% [00037] [(CF.sub.3SO.sub.2).sub.2N].sup.− 455 >330 20% [00038] [(CF.sub.3SO.sub.2).sub.2N].sup.− 56 80% [00039] [(CF.sub.3SO.sub.2).sub.2N].sup.− 455 >330 20% [00040] [(CF.sub.3CF.sub.2SO.sub.2).sub.2N].sup.− 57 80% [00041] [(CF.sub.3SO.sub.2).sub.2N].sup.− 456 >330 20% [00042] [(CF.sub.3SO.sub.2).sub.2N].sup.− 58 90% [00043] [(CF.sub.3SO.sub.2).sub.2N].sup.− 456 >330 10% [00044] [(CF.sub.3SO.sub.2).sub.2N].sup.− 59 ethyldimethylpropylammonium [(CF.sub.3SO.sub.2).sub.2N].sup.− 420 >330 bis(trifluoromethylsulfonyl)imide 60 1-propyl-4-methylpyridin-1-ium [(CF.sub.3SO.sub.2).sub.2N].sup.− 411 >330 bis(trifluoromethylsulfonyl)imide 61 1-ethyl-3-methylpyridin-1-ium bis(trifluoromethylsulfonyl)imide [00045] [(CF.sub.3SO.sub.2).sub.2N].sup.− nd >330 62 1-propyl-3,5-dimethylpyridinium bis(trifluoromethylsulfonyl)imide [00046] [(CF.sub.3SO.sub.2).sub.2N].sup.− 361 >330 63 1-(2-hydroxyethyl)-3,5- dimethylpyridinium bis(trifluoromethylsulfonyl)imide [00047] [(CF.sub.3SO.sub.2).sub.2N].sup.− 388 >330

[0220] Thus, the selection of the cations and of their specific substituents, as well as the selection of the anions and of their specific substituents make it possible to obtain an ionic liquid having a deposition start temperature, determined by MCT, higher than 330° C.

[0221] E. Examples of Ionic Liquids Having a Degradation Start Temperature Determined by MCT Higher Than 350° C. (Table 4)

TABLE-US-00003 TABLE 4 TGA MCT Ex Nomenclature Cation Anion (10° C./mn) (250-300° C.) 64 1-ethyl-2,3-dimethyl-imidazolium bis(trifluoromethylsulfonyl)imide [00048] [(CF.sub.3SO.sub.2).sub.2N].sup.− 434 >350 65 1,2-dimethyl-3-((trimethylsilyl)methyl)- imidazolium bis(trifluoromethylsulfonyl)imide [00049] 439 >350 66 1,2-dimethyl-3-((trimethylsilyl)methyl)- [(CF.sub.3SO.sub.2).sub.2N]— 412 >350 imidazolium bis(trifluoromethylsulfonyl) imide

[0222] Thus, as Table 4 above shows, a drastic selection of the cations and of the anions has made it possible to obtain ionic liquids having a deposition start temperature, determined by MCT, higher than 350° C.

[0223] F. Thermal Stability of Some Oils Available on the Market as Determined by MCT (Table 5)

[0224] As Table 5 here below shows, the conventional oils available on the market have a less good thermal stability and resistance to coking than the specific ionic liquids according to the invention.

TABLE-US-00004 TABLE 5 TDD for MCT Nomenclature 250-300(° C.) Turbonycoil 600 <250 Mobil Jet Oil II <250 Turbonycoil 640 294 BP Turbo Oil 2197 294

[0225] G. Comparison of the Thermal Stability Determined by TGA and MCT of Some Ionic Liquids Described in the Prior Art Patents (Table 6)

TABLE-US-00005 TABLE 6 TGA MCT Nomenclature Cation Anion (10° C./mn) 250-300° C. Ref. 1-ethyl-3-methylimidazolium methylsulfate [00050] CH.sub.3SO.sub.4.sup.− 350 <250 WO2011/026990A1 trihexyltetradecylphosphonium bis(trifluoromethylsulfonyl)imide [00051] [(CF.sub.3SO.sub.2).sub.2N].sup.− 396 274 WO2011/026990A1 1-butyl-4-methylpyridinium hexafluorophosphate [00052] BF.sub.4.sup.− 392 <250 US2010/0227785A1 1-butyl-4-methylpyridinium PF.sub.6.sup.− 341 <250 US2010/0227785A1 tetrafluoroborate 1-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide [00053] [(CF.sub.3SO.sub.2).sub.2N]— 442 296 EP2602307 1-(2-methoxyethyl)-1- methylpyrrolidinium bis(trifluoromethylsulfonyl)imide [00054] [(CF.sub.3SO.sub.2).sub.2N].sup.− TDD very probably lower than 330° C. US2009/0069204 1-butyl-pryridinium bis(trifluoromethylsulfonyl)imide [00055] [(CF.sub.3SO.sub.2).sub.2N].sup.− TDD very probably lower than 330° C. US2009/0069204 N,N-diethyl-2-methoxy-N- methylethaneammonium bis(trifluoromethylsulfonyl)imide [00056] [(CF.sub.3SO.sub.2).sub.2N].sup.− Not very stable ionic liquid US2009/0069204 3-hexyl-1-methylimidazolium bis(trifluoromethylsulfonyl)imide [00057] [(CF.sub.3SO.sub.2).sub.2N].sup.− 421 254 US2009/0069204 3-butyl-1-methylimidazolium hexafluorophosphate [00058] PF.sub.6.sup.− 338 <250 US2009/0069204 3-butyl-1-methylimidazolium BF.sub.4.sup.− 424 <250 US2009/0069204 tetrafluoroborate 3-ethyl-1-methylimidozalium bis(fluorosulfonyl)imide [00059] [(FSO.sub.2).sub.2N].sup.− 281 <250 US2013/0053287A1 1-methyl-3-octylimidazolium bis(trifluoromethylsulfonyl)imide [00060] [(CF.sub.3SO.sub.2).sub.2N].sup.− TDD very probably lower than 330° C. US2013/0053287A1

[0226] Likewise, the ionic liquids described in the prior art mentioned above have a less good thermal stability and resistance to coking than the specific ionic liquids according to the invention. Thus, both ionic liquids disclosed in the patent application US 2010/0227785A1 do not have a particular resistance to thin-film coking.

[0227] It has also been noted that the ionic liquids described in the document WO2011/026990A1 have a very bad thin-film coking behavior; which clearly illustrates the difference between an additive reducing coking and a lubricant reducing deposits in thin film.

[0228] Moreover, as is represented in FIG. 2, which shows the result of the MCT test (250-300° C.) of 3-butyl-1-methylimidazolium hexafluorophosphate (TDD lower than 250° C.), carbonaceous deposits are visible. This compound therefore has a low resistance to coking. On the contrary, FIG. 3 illustrates the result of the MCT test (300-350° C.) of an ionic liquid according to the invention, 1,2-dimethyl-3-((trimethylsilyl)methyl)imidazolium bis(pentafluoromethylsulfonyl)imide (TDD >350° C.) where no deposit of carbonaceous residues is detected. This compound is thus highly resistant to coking.