Anti-wear additives based on (POLY)esteramine

Abstract

The present invention relates to a composition comprising at least one optionally quaternized (poly)esteramine, and at least one phosphorus-containing, sulfur-containing or phosphorus and sulfur-containing additive, said composition being advantageously used as an additive composition in lubricating formulations. The invention also relates to lubricating formulations comprising said additive composition, as well as to the use of said lubricating formulation in motor vehicle engines, milling and metal-cutting systems, and fuel compositions.

Description

(POLY)ESTERAMINE-BASED ANTI-WEAR ADDITIVES

[0001] The present invention relates to the field of lubricants and more specifically relates to anti-wear and anti-friction additives in lubricating compositions used in mechanical systems including in particular parts in relative motion.

[0002] Anti-wear and anti-friction additives used in lubricating compositions are now well known. Examples of alkylamines and quaternary ammonium derivatives of alkylamines are already widely known and commonly used. However, the search for new, even more effective molecules with improved properties continues actively. For example, over the last twenty years, another family of nitrogen-containing compounds with a higher molecular weight has appeared in the literature. These compounds have a polymeric or oligomeric structure and contain amine and quaternary ammonium functions.

[0003] Thus, international application WO2008089906 describes the reaction products of a fatty acid with a diacid and an (alkyl)polyethanolamine, said reaction products then being quaternized. In this international application, these products are defined as surfactants that can be used as collectors for the flotation of ores. Similarly, international application WO2011147855 describes quaternary ammonium compounds resulting from the reaction of a fatty alcohol with a diacid and an (alkyl)polyethanolamine. These quaternary ammonium compounds are used for the flotation of silicates.

[0004] More recently, international applications WO2012028542, WO2013038192 and WO2014095797 describe various polyesteramines and polyesterquats which are used as anti-corrosion agents, as ore flotation agents or as depressants.

[0005] As for international application WO2017144376, this describes quaternized nitrogen compounds used as friction wear reducing additives in fuels. These compounds are obtained by quaternization with ethylene oxide. Finally, international application WO2022167756 describes polyester-polyamines as well as their quaternized versions, usable in various applications including lubricating compositions.

[0006] Furthermore, the protection of metal surfaces against mechanical damage due to a rupture of the lubricating film is a very important topic when discussing lubricants and, for example, extreme pressure lubricants. One of the most important parameters for a lubricant when it comes to wear or extreme pressure is its viscosity. However, if the system operates under mixed lubrication conditions, even if the oil film still exists, asperities on the opposing metal surfaces come into contact. Anti-wear additives are intended to prevent "welding" of these contacts. Anti-wear additives thus form a protection, by physical or chemical adsorption and / or by chemical reaction between the additive and the metal surface.

[0007] Among the most commonly used anti-wear and / or extreme pressure additives, we can cite for example derivatives containing phosphorus, the best known representatives of which are phosphates in general, such as amine phosphates, phosphate esters, triarylphosphates, and phosphites. Other known anti-wear / extreme pressure additives are compounds containing sulfur, such as sulfur esters, sulfur fatty acids and sulfur olefins. Finally, there are anti-wear additives containing both phosphorus and sulfur, including metal dithiophosphates, phosphorothionates, and others.

[0008] One of the major drawbacks of these anti-wear additives known today is their negative impact on the environment where the release of phosphorus and / or sulfur derivatives is now strictly controlled, or even banned.

[0009] There therefore remains a need for additives capable of giving the lubricating compositions containing them even better anti-wear and anti-friction properties.

[0010] Thus, and according to a first objective, the invention provides lubricating compositions comprising one or more additives making it possible to reduce friction and wear in mechanical systems having parts in relative motion, such as for example and without limitation in vehicle transmission systems, in systems with rotor and stator, in machines, in turbines, in electric coils for generating current as well as in motors, as well as in hydraulic systems, but also when working metals and alloys.

[0011] Another objective of the invention is to provide lubricating compositions comprising one or more additives for reducing friction and wear in mechanical systems having parts in relative motion, compositions in which the additives are used in smaller quantities than those observed today.

[0012] Another objective of the invention is to provide lubricating compositions for reducing friction and wear in mechanical systems, in particular those having parts in relative motion, compositions in which the additives used are more environmentally friendly.

[0013] Yet another objective is to provide lubricating compositions comprising one or more additives for reducing friction and wear in mechanical systems having parts in relative motion, compositions in which the additives are biodegradable and non-ecotoxic, and make it possible to reduce the associated atmospheric pollution by their low sulfur and / or phosphorus contents.

[0014] Still other objects will appear in the description of the invention which follows.

[0015] In the present invention, the value ranges are understood to be inclusive of all limits, unless explicitly stated otherwise.

[0016] It has now been discovered that the above-mentioned objectives are achieved in whole or at least in part by means of the present invention which is now detailed in the following description.

[0017] Thus, and according to a first aspect, the present invention relates to a composition comprising: 1) at least one (poly)esteramine, optionally quaternized, obtained by esterification: la) of at least one component chosen from fatty (poly)amines, optionally alkoxylated, fatty acids, optionally alkoxylated, and fatty alcohols, optionally alkoxylated, the fatty chain being a linear or branched, saturated or unsaturated hydrocarbon chain, comprising from 8 to 30 carbon atoms and optionally an aromatic ring, lb) of at least one component chosen from polycarboxylic acids, polycarboxylic acid anhydrides, said acids or anhydrides comprising a hydrocarbon chain, preferably a linear or branched, saturated or unsaturated alkyl chain, optionally having an aromatic ring, C1-C16, preferably C1-C12, more preferably C1-C6, lc) of at least one component chosen from non-fatty (di)alkoxylated amines, and 1 d) optionally at least one component chosen from diols comprising a linear or branched C1-C16, preferably C1-C12, more preferably C1-C6, alkyl chain, and 2) at least one additive chosen from amine additives, chlorinated paraffins, fatty esters, phosphorus additives, sulfur additives, and phosphorus and sulfur additives, preferably among phosphates, in particular amine phosphates, phosphate esters, phosphites, triarylphosphates, metal dithiocarbamates, metal dithiophosphates, phosphorothionates, thioethers, polysulfides and sulfur-containing fatty esters.

[0018] The respective proportions of components 1) and 2) of the composition according to the present invention can vary within large proportions and are generally between 99:1 and 1:99, by weight, preferably between 75:25 and 25:75, by weight, more preferably between 60:40 and 40:60, by weight.

[0019] Component 1 a) of the (poly)esteramine 1 ) of the composition according to the present invention may optionally be alkoxylated, i.e. may contain one or more identical or different alkoxylated groups selected from ethylene-oxy (EO), propylene-oxy (PO) butylene-oxy (BO), and mixtures of two or more of them, in blocks, in series, or random. When component 1 a) is alkoxylated, the ethylene-oxy (EO) alkoxyl group is preferred.

[0020] Most preferably, component 1a) of the (poly)esteramine 1) of the composition according to the present invention is chosen from alkoxylated, preferably ethoxylated, fatty (poly)amines, fatty acids, alkoxylated, preferably ethoxylated fatty acids, fatty alcohols, and alkoxylated, preferably ethoxylated fatty alcohols.

[0021] Among the components 1 a) suitable within the framework of the present invention, the following may be cited as non-limiting examples: - alkoxylated fatty (poly)amines, preferably ethoxylated, and in particular: o ethoxylated coconut amines, comprising from 2 to 20 ethylene oxide units, preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units, o optionally hydrogenated tallow amines, alkoxylated, preferably ethoxylated, and preferably those comprising from 2 to 20 ethylene oxide units, preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units, o alkoxylated oleylamines, preferably ethoxylated, and preferably those comprising from 2 to 20 ethylene oxide units, preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units ethylene, o alkoxylated coconut diamines, preferably ethoxylated, and preferably those comprising from 2 to 20 ethylene oxide units,preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units, o alkoxylated oleic diamines, preferably ethoxylated, and preferably those comprising from 2 to 20 ethylene oxide units, preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units, o optionally hydrogenated tallow diamines, alkoxylated, preferably ethoxylated, and preferably those comprising from 2 to 20 ethylene oxide units, preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units, - fatty acids, representatives of which are chosen from copra fatty acids, oleic acid, tallow fatty acids, hydrogenated tallow fatty acids, - alkoxylated fatty acids, preferably ethoxylated, representatives of which are chosen from: o alkoxylated copra fatty acids, preferably ethoxylated, and preferably those comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, o alkoxylated oleic acids, preferably ethoxylated, and preferably those comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, o optionally hydrogenated tallow fatty acids, alkoxylated, preferably ethoxylated, and preferably those comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units of ethylene, - fatty alcohols, the main representatives of which are / so-decanol, / so-tridecanol, fatty alcohols the main components of which are C12 to C14 alcohols, fatty alcohols the main components of which are C to C alcohols, and fatty alcohols the main components of which are oleyl alcohol, - alkoxylated fatty alcohols, preferably ethoxylated, representatives of which are chosen from: o alkoxylated / so-decanol, preferably ethoxylated, and preferably comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, o alkoxylated / so-tridecanol, preferably ethoxylated, and preferably comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, o fatty alcohols whose main components are alkoxylated C12 and C14 alcohols, preferably ethoxylated, and preferably comprising from 1 to 20 units of ethylene oxide, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, o fatty alcohols whose main components are alkoxylated C and C alcohols, preferably ethoxylated, and preferably comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, and o fatty alcohols whose main components are alkoxylated oleyl alcohol, preferably ethoxylated, and preferably comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units.

[0022] The polycarboxylic acids 1 b) are more specifically chosen from dicarboxylic acids, tricarboxylic acids and tetracarboxylic acids, preferably from dicarboxylic acids. Examples of dicarboxylic acids which are particularly suitable in the context of the present invention include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, phthalic acid and its isomers, tetrahydrophthalic acid, malic acid, tartaric acid and itaconic acid.

[0023] By non-fatty (di)alkoxylated amines is meant mono- or dialkoxylated amines, where "alkoxylated" includes the terms ethoxylated, propoxylated and / or butoxylated, with a number of alkoxylated units ranging from 1 to 20, preferably from 1 to 10, and optionally but preferably comprising a hydrocarbon chain, preferably an alkyl chain, linear or branched, saturated or unsaturated, having from 1 to 7 carbon atoms, preferably from 1 to 6 carbon atoms.

[0024] According to a preferred embodiment, compound 1c) is chosen from non-fatty fatty (di)ethoxylated amines of general formula (1c): in which: o A is chosen from the hydrogen atom, a hydrocarbon chain, linear or branched, saturated or unsaturated, preferably saturated, and having from 1 to 7 carbon atoms, preferably from 1 to 6 carbon atoms and a -(CH2CH2O)] chain P-H, and on and m and p, independently of each other, each represent an integer ranging from 1 to 10, preferably from 1 to 5.

[0025] Representative examples of component 1 c) defined above are advantageously chosen from diethanolamine, methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, / so-butyldiethanolamine, pentyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, triethanolamine, as well as their corresponding alkoxylation products, in particular corresponding ethoxylation products, and typically comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units.

[0026] Particularly suitable representatives of component 1d) defined above are advantageously chosen from glycols and typically from ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol and propylene glycol and its derivatives, ethylene glycol monobutyl ether, di(ethylene glycol) monobutyl ether, butylene glycol and its derivatives.

[0027] According to a preferred embodiment of the present invention, component 1 d) of the (poly)esteramine 1 ) of the composition according to the present invention does not comprise a nitrogen atom, and more preferably does not comprise an amine function.

[0028] As indicated previously, the (poly)esteramine 1) obtained by esterification of components 1 a), 1 b), 1 c) and optionally 1 d) may optionally be engaged in a quaternization reaction of all or part of the nitrogen functions present in said (poly)esteramine 1), according to any method well known to those skilled in the art, generally and most often using at least one alkylating agent, and for example as described in application WO2022167756.

[0029] When the quaternization reaction, partial or total, is carried out using an alkylating agent, the latter is generally and most often chosen from the most common and best known alkylating agents, and preferably from methyl chloride, methyl bromide, methyl iodide, dimethyl sulfate, diethyl sulfate, dimethyl carbonate and benzyl chloride, and more preferably from methyl chloride, dimethyl sulfate, diethyl sulfate and benzyl chloride, as well as their mixtures, most preferably from methyl chloride, dimethyl sulfate and their mixtures.

[0030] It should be understood that the quaternization step, partial or total, can be carried out on component 1 a) and / or on the condensation product of component 1 a) and component 1 b) and / or on the condensation product of component 1 a), component 1 b), and component 1 c).

[0031] The quaternization reaction(s) is(are) generally carried out in water and / or in one or more organic solvent(s), at a temperature ranging from 20°C to 120°C, for a duration ranging from several tens of minutes to several tens of hours, according to the operating methods well known to those skilled in the art.

[0032] As indicated above, component 1) of the composition of the present invention is a compound with a polyesteramine structure, optionally quaternized. Such compounds are well known to those skilled in the art and are for example described in application WO2022167756 A1. The present invention relates in particular to compositions comprising such compounds with a polyesteramine structure, optionally quaternized, in combination with one or more anti-wear and / or anti-friction additives.

[0033] Thus, and according to a preferred embodiment, component 1) of the composition of the invention is a quaternized polyesteramine corresponding to the general formula (P): in which: R 1 is a linear or branched, saturated or unsaturated hydrocarbon chain, comprising from 8 to 30 carbon atoms, preferably from 8 to 24 carbon atoms and optionally an aromatic cycle, R 2 is a linear or branched C1-C16, preferably C1-C12, more preferably C1-C6, alkyl chain, R 4 is chosen from a hydrocarbon chain, linear or branched, saturated or unsaturated, preferably saturated, and having from 1 to 7 carbon atoms, preferably from 1 to 6 carbon atoms and a -(CH2CH2O)] chain P -H, where p represents an integer ranging from 1 to 10, preferably from 1 to 5, R 5represents a linear or branched hydrocarbon chain, comprising from 1 to 6 carbon atoms and optionally substituted by an aromatic radical, AO represents an alkoxylated unit chosen from ethoxy, propoxy, and butoxy, preferably AO represents an ethoxy unit -(CH2CH2O)-, x is an integer between 1 and 10, preferably between 1 and 5, t is equal to 0 or 1, p represents an integer between 1 and 15, preferably between 1 and 10 and more preferably between 1 and 5, and X' represents the anion of the quaternizing agent, and is preferably chosen from halides (chloride, bromide, iodide), carbonates, sulfates and sulfonates.

[0034] Thus, component 2) of the composition of the present invention consists of at least one additive chosen from amine additives, chlorinated paraffins, fatty esters, phosphorus additives, sulfur additives, and phosphorus and sulfur additives. These additives are generally known and used as extreme pressure additives and / or anti-wear additives and / or anti-friction additives.

[0035] Among these, mention may be made, in a purely illustrative and non-limiting manner, of cocoamine, cocoamide, oleylamine, oleylamide, tallow amine, tallow amide, hydrogenated tallow amine, hydrogenated tallow amide and their derivatives such as cocoamide DEA, PEG-2 tallowamine or PEG-2 oleylamine among the best known, C14-C16 chloroalkanes, C16-C18 chloroalkanes, acylglycerols such as, for example, glycerol stearate or glycerol oleate, 2-ethylhexyl palmitate, pentaerythryl esters, polyester polyols, polyether ester polyols, thiophosphoric acid, thiophosphorous acid, esters (in particular phosphate esters) and salts of these acids, phosphoric esters alkoxylated, phosphate amines, dithiophosphates, metal dithiocarbamates and their mixtures.Particularly preferred are phosphorus and / or sulfur additives, and more particularly zinc dithiophosphates, and metal dithiocarbamates, such as, for example, molybdenum dithiocarbamates.

[0036] Fully representative but non-limiting examples of such additives include zinc diaryldithiophosphates and zinc dialkyldithiophosphates, also well known by their acronym "ZDDP", dibenzyl disulfide, di-tert-dodecyl polysulfides, di-tert-butyl trisulfide, sulfurized rapeseed oil, sulfurized palm oil.

[0037] In one embodiment of the invention, component 2) is chosen from zinc dithiophosphates corresponding to the general formula (I): in which the radicals R 10 , R 11 , R 12 and R 13, each independently of the others, represent a linear, branched or cyclic hydrocarbon chain comprising from 1 to 24 carbon atoms, optionally comprising an aromatic nucleus, preferably a linear or branched hydrocarbon chain comprising from 1 to 24 carbon atoms, plus preferably a linear or branched hydrocarbon chain comprising from 3 to 12 carbon atoms, for example a linear or branched hydrocarbon chain comprising from 6 to 10 carbon atoms.

[0038] In one embodiment of the invention, examples of compositions according to the invention comprising at least one (poly)esteramine 1) and at least one additive 2), comprise: • the composition comprising (1) the reaction product between ethoxylated oleylamine with 5 ethylene oxide units, oleic fatty acid, oxalic acid and diethanolamine and (2) a zinc dithiophosphate, preferably corresponding to the general formula (I) defined above, • the composition comprising (1) the product of the reaction between tallow amine, ethoxylated coconut fatty acid with 2 ethylene oxide units, succinic acid and / so-butyldiethanolamine in ethylene glycol and (2) a zinc dithiophosphate, preferably corresponding to the general formula (I) defined above, • the composition comprising (1) the product of the reaction between ethoxylated oleylamine with 2 ethylene oxide units, oleic acid, oxalic acid and diethanolamine and (2) the phosphoric ester of an ethoxylated oleyl alcohol with 5 ethylene oxide units, • the composition comprising (1) the product of the reaction between ethoxylated tallow amine with 2 ethylene oxide units, tallow fatty acid, adipic acid and methyldiethanolamine and (2) a zinc dithiophosphate, preferably corresponding to the general formula (I) defined above, • the composition comprising (1) the product of the reaction between ethoxylated tallow amine with 2 ethylene oxide units, tallow fatty acid, adipic acid and methyldiethanolamine and (2) the phosphoric ester of an ethoxylated oleyl alcohol with 5 ethylene oxide units, • the composition comprising (1) the product of the reaction between tallow fatty acid, adipic acid and diethanolamine, quaternized with methyl chloride and (2) zinc dithiophosphate, preferably corresponding to the general formula (I) defined above, • the composition comprising (1) the product of the reaction between ethoxylated tallow amine with 2 ethylene oxide units, tallow fatty acid, adipic acid and methyldiethanolamine, quaternized with methyl chloride, and (2) the phosphoric ester of an ethoxylated oleyl alcohol with 5 ethylene oxide units, • the composition comprising (1) the product of the reaction between tallow amine, ethoxylated coconut fatty acid with 2 ethylene oxide units, succinic acid and iso-butyldiethanolamine in ethylene glycol and (2) di-tert-butyl trisulfide, • the composition comprising (1) the product of the reaction between tallow fatty acid, adipic acid and diethanolamine, quaternized with methyl chloride and (2) cocoamide DEA, • the composition comprising (1) the product of the reaction between ethoxylated oleylamine with 5 ethylene oxide units, oleic acid, oxalic acid and diethanolamine and (2) a C16-C18 chlorinated paraffin.

[0039] The composition according to the present invention comprising at least one component 1) and at least one component 2) as just defined finds a very particular interest and a very particular application as an additive in lubricating formulations.

[0040] Thus, and according to another aspect, the present invention relates to the use of a composition comprising at least one component 1) and at least one component 2), as an additive in a lubricating formulation.

[0041] According to yet another aspect, the present invention relates to a lubricating formulation comprising at least one composition according to the invention, i.e. a composition comprising at least one component 1) and at least one component 2), as indicated previously.

[0042] The lubricating formulation according to the present invention generally and most often comprises between 0.1% and 20% by mass, limits included, preferably between 0.1% and 15% by mass, limits included, more preferably between 0.1% and 10% by mass, limits included, better still between 0.1% and 5% by mass, limits included, of the composition of the invention comprising at least one component 1) and at least one component 2), as they have just been defined, relative to the total mass of the lubricating composition.

[0043] The lubricant formulation according to the invention may be a ready-to-use formulation and in this case most often and advantageously comprises from 0.01% to 5%, preferably from 0.01% to 3% by weight of component 1) and from 0.01% to 5%, preferably from 0.01% to 3% by weight of component 2). The formulation according to the present invention may also be in the form of a concentrate to be diluted before use and in this case the dilutable concentrate most often and advantageously comprises from 0.5% to 20%, preferably from 0.5% to 15% by weight of component 1) and from 0.5% to 20%, preferably from 0.5% to 15% by weight of component 2).

[0044] In addition to the composition of the invention, comprising at least one component 1) and at least one component 2), the lubricating formulation of the invention may be a formulation lubricating oil itself, a cutting oil which may contain a greater or lesser quantity of water, a fuel, and others. Those skilled in the art will know how to adapt the quantity and nature of components 1) and 2) according to the nature of the lubricating formulation of interest.

[0045] It has been observed in a completely surprising manner that the presence of at least one component 1) and at least one component 2) in the lubricating formulation gives said formulation completely unexpected anti-wear and anti-friction properties, making it possible to achieve very good, even excellent levels of friction and wear reduction, in particular in the concentration ranges mentioned above.

[0046] It has been demonstrated that the composition of the invention, a combination of at least one component 1) and at least one component 2) defined previously, allows the development of a lubricating formulation whose anti-wear and anti-friction properties are greatly improved compared to lubricating compositions of the prior art comprising equivalent concentrations of additive(s).

[0047] Another advantage of the formulation of the present invention is that it is possible to obtain anti-wear and anti-friction levels similar to those observed with compositions known from the prior art but which contain higher concentrations of additive(s). In this case, the lubricating formulation according to the invention has an obvious advantage, in particular on the environment, in that a smaller quantity of sulfur and / or phosphorus compounds will be used and therefore likely to appear in the various discharges and effluents.

[0048] Thus, the combination of components 1) and 2) in the composition of the present invention as defined above, provides a level of friction reduction and wear reduction never before achieved with the lubrication additives of the prior art. Indeed, this combination makes it possible to reduce the quantity of components 1) and 2), and in particular of the phosphorus and / or sulfur component 2), while providing levels of friction and wear reduction comparable to the levels known from the prior art with higher quantities of additives, or even levels of friction and wear reduction well above the levels known from the prior art with similar quantities of additives. The fact of being able to use additives, and in particular phosphorus and / or sulfur anti-wear additives, in smaller quantities in lubricating formulations has a certain, significant and entirely relevant impact for the protection of the environment.

[0049] For the purposes of the present invention, the term "lubricating formulation" means any formulation used in mechanical systems comprising parts in relative motion allowing the reduction of wear by friction. The lubricating formulation according to the invention generally and most often comprises at least one composition comprising at least one component 1) and at least one component 2) as defined above and at least one lubricating oil and / or at least one fuel. For the purposes of the present invention, the term "fuel" means any type of fuel, liquid or gaseous, preferably liquid, comprising at least one alkane and preferably the fuel for the purposes of the invention includes gasolines, diesels, kerosenes, and others. The fuels included in the present invention are often used in mechanical systems including in particular parts in relative motion, and can thus be included in the general term "lubricating formulations".

[0050] The formulation according to the invention may further comprise one or more additives and / or fillers well known to those skilled in the art and commonly used in such formulations. Such additives and / or fillers include, for example and without limitation, extreme pressure additives, corrosion inhibitors, antioxidants, metal deactivators, and others.

[0051] Organosulfur compounds, organochlorine compounds and organophosphorus compounds and mixtures thereof are particularly useful as extreme pressure additives. In a preferred embodiment, the extreme pressure additives comprise chlorinated paraffins, alkyl or alkylphenol polysulfides, sulfurized olefins, sulfur-containing esters, metal dithiocarbamates, thiadiazoles and benzothiazoles, as well as alkyl phosphates or alkyl phosphonates, phosphoric acid, phosphorous acid, mono-, di- and triesters of phosphorous acid and phosphoric acid and their salts.

[0052] Among the corrosion inhibitors that can be used in the formulations according to the present invention, mention may be made in particular and without limitation of boric acids and their salts, tolyltriazole and its salts, benzotriazoles and their salts, imidazolines and their salts, alkanolamines and amides, sulfonates, alkali metal and alkanolamine salts of naphthenic acids, amine salts of phosphate esters, alkali metal nitrites, alkali metal carbonates, carboxylic acids and their derivatives, alkylsulfonamide-carboxylic acids, arylsulfonamide-carboxylic acids, phenoxy derivatives, molybdates and in particular sodium molybdate, alkoxylated amines, tertiary polyamines such as pentamethyldipropyltriamine and their salts, alkyl polyalkylene ether phosphate salts glycol and their mixtures.

[0053] As other additives and / or fillers that can be used in the formulations of the present invention, mention may be made of antioxidants and in particular phenolic derivatives, amines and their mixtures.

[0054] As non-limiting examples of metal deactivators which may be useful in the formulations of the present invention, preference is given to triazoles.

[0055] As indicated above, the formulation of the invention is generally ready to use but can also be in the form of a concentrate to be diluted before use. The most common and usually used diluents are those which are compatible with lubricating formulations, and for example, and depending on the use for which they are intended, the diluents are chosen from organic diluents, such as oils and fuels and also aqueous or hydro-organic diluents, for example water, in particular for applications in cutting oils (“metal working fluid” in English).

[0056] The formulation according to the present invention thus finds very interesting applications as a lubricating formulation, and as such the present invention also relates to the use of the formulation according to the present invention in mechanical systems comprising parts in relative motion allowing the reduction of wear by friction, and consequently less heating, for example in lubricating formulations in motor vehicle engines, in heat transfer formulations, for milling and metal cutting systems, but also in fuel compositions, to name only the most common and best-known applications.

[0057] The advantages provided by the lubricating formulation of the present invention are numerous and varied and among these, mention may be made, without limitation, of the numerous advantages linked to the reduction of friction of parts in relative movement in motor vehicle engines, and in particular fuel savings, a substantial increase in the autonomy of vehicles, electric or thermal, better efficiency in all lubrication regimes and whatever the engine torque.

[0058] As a further advantage, the composition of the present invention and the formulations containing it make it possible to substantially reduce the quantities of phosphorus and / or sulfur additives which can be harmful to the environment but which are often also responsible for significant corrosion of metal parts, present in particular in the engines of electric vehicles. Thanks to the composition of the present invention, where the corrosive compounds that are the anti-wear and / or extreme pressure additives are present in much smaller quantities than in the lubricant formulations used today, the corrosion of metal parts is very limited, or even almost non-existent, and even non-existent.

[0059] Yet another advantage is the reduction of atmospheric pollution associated with the use of relatively small quantities of composition according to the present invention, and thus greater ease of compliance with future environmental regulations, all the more so since the composition of the invention and in particular its component 1) is advantageously a biodegradable and non-ecotoxic additive.

[0060] The invention is now illustrated with the aid of the examples which follow and which in no way limit the invention, the scope of which is defined by the claims appended to this description. Examples

[0061] In the following examples the following components are used for the preparation of compositions which will be tested for their anti-wear and anti-friction properties:

[0062] Component A [component 1) of the composition according to the present invention] is a quaternized polyesteramine corresponding to the general formula described below and prepared as indicated in application WO2012028542: in which: R 1 is a tallow radical (alkyl chain mainly with 18 carbon atoms), - R 2 is -(CH2)2-, R 4 and R 5 each represent the methyl radical (-CH3), - AO represents -(CH2CH2O)-, - x is equal to 1, and t is equal to 1, and p is equal to 3, and X' represents the chloride ion from methyl chloride used as an alkylating agent.

[0063] Component B [component 1) of the composition according to the present invention] is a quaternized polyesteramine resulting from the reaction between triethanolamine, tallow fatty acid and adipic acid in accordance with the description of international application WO2008089906. The quaternizing agent is methyl chloride.

[0064] Components C and D [components 1) of the composition according to the present invention] are polyesteramines as described in application WO2022167756 and prepared from the compounds indicated in the following Table 1: -- Table 1 --

[0065] In Table 1 above: - NoxS2 is Noramox® S2: ethoxylated tallow amine (2OE) marketed by Arkema, - NoxS5 is Noramox® S5: ethoxylated tallow amine (5OE) marketed by Arkema, - MDEA is methyldiethanolamine (purity grade > 99%) supplied by Taminco, - Ac. Ad. is adipic acid, - AGS is tallow fatty acid.

[0066] Component E [component 2) of the composition according to the present invention] is distributed by Additive Chemie Luers GmbH under the brand name KUNOX® S8811 and is a zinc dialkyldithiophosphate (ZDDP) known as an anti-wear additive.

[0067] Component F [component 2) of the composition according to the present invention] is an additive available from ARKEMA under the brand SURFALINE® PE 684 and is a phosphoric ester (phosphate ester of oleocetyl alcohol ethoxylated with 5 moles of ethylene oxide) known as an anti-wear additive.

[0068] Component G is an ethoxylated tallow amine (2EO) supplied by Arkema under the brand name Noramox® S2, known as a friction reducing additive. This component G is a component for preparing a comparative composition. Friction Test Protocol

[0069] The friction coefficient is measured using the MTM tribometer supplied by PCS Instruments. This is a ball-on-disc tribometer that can measure the friction properties of lubricated and unlubricated contacts under a wide range of rolling and sliding conditions.

[0070] The MTM tribometer allows friction to be assessed: as a function of the sliding rate in the contact (rolling / sliding ratio noted SRR for "Slide / Roll Ratio" in English) with a traction curve (here, the speed is fixed), as a function of the rolling speed in the contact with a Stribeck curve (here, the SRR ratio is fixed), and as a function of time with a curve at iso-conditions (here, SRR ratios and speed fixed).

[0071] The friction generated between the ball and the disc is measured using a torque sensor. The torque sensor is located between the ball shaft and a fixed point. The friction force is therefore measured perpendicular to the direction of the load. The sliding-to-rolling ratio is the ratio of the sliding speed to the rolling speed of a contact. Test conditions: - Concentration of additive, alone or in mixture: between 0 and 1% by mass in a Group II mineral oil, marketed by Total Énergies under the name Torilis HC 1850, which will be the Group II mineral oil used in all the examples which follow, unless expressly stated otherwise. - Test temperature: 120°C, - Applied load: 37 N, - Sliding / rolling ratio (SRR): 50%, - Rolling speed: 8 mm s measurement -1 at 3200 mm s -1 .

[0072] The result appears in the form of a curve with the rolling speed (in mm / s) on the abscissa and the friction coefficient measurement on the ordinate. The interpretation is done visually; the lower the friction coefficient, the more the product is considered to be a friction reducer (or friction reducer). Wear Test Protocol

[0073] The tests were conducted according to IP 239 (REF / ISBN IP 239-2936900, February 2014), a test method used to determine the relative wear prevention properties of lubricating fluids in sliding contact under prescribed test conditions (four-ball method). Test conditions: - Concentration of additive, alone or in mixture: between 0 and 1% in a Group II mineral oil, - Applied load: 40 kgF, or 392 N - Test time: 1 hour

[0074] The wear diameter of the three fixed balls generated by the rotating ball is measured using a binocular magnifier. The tests are repeated at least twice, the average value of these wear diameters (in mm) is given as the result. The smaller the wear diameter, the better the product is considered to have anti-wear properties. Results

[0075] The tests are carried out with the aim of comparing the anti-friction and anti-wear effectiveness of various oils and oil-based formulations containing either an additive known from the prior art, or a composition according to the invention, or a comparative composition. Example 1 (comparative) Friction tests 1

[0076] The first set of results corresponds to a friction test carried out with: - Reference formulation 1 R: a group II oil, - Formulation 1 E: a group II oil comprising 0.5% by mass of component E, - Formulation 1 Ed : a group II oil comprising 1% by mass of component E, - Formulation 1 G : a group II oil comprising 0.5% by mass of component G, - Comparative formulation 1com P : a group II oil comprising 0.5% by mass of component E and 0.5% by mass of component G (composition according to the invention).

[0077] The results are presented in Figure 1. It is observed that Formulation 1 E does not provide any friction reducing effect, this effect being less good than that observed with Reference Formulation 1 R.

[0078] Additive G plays its role as a friction reducer in Formulation 1G, but the test carried out with the Comparative Formulation 1com P shows that the performance of additive G is degraded.

[0079] This example proves that when the Formulation comprises a composition not meeting the definition of the present invention, no improvement is observed in this anti-friction test. Wear tests 1

[0080] The results are shown in Figure 2. Formulations 1 E and 1 Ed confirm that Component E is a good anti-wear additive and that Formulation 1 G also provides a suitable anti-wear effect, while Component G is more generally used as a friction reducing additive. Formulation 1com P does not provide any improvement in reducing wear. Example 2 (according to the invention)

[0081] Wear and friction tests are carried out according to the protocols described above with the following formulations: - Formulation 2E: a group II oil comprising 0.5% by mass of component E, - Formulation 2c: a group II oil comprising 0.5% by mass of component C, - Formulation 2cm: a group II oil comprising 0.25% by mass of component C, - Formulation 2EC: a group II oil comprising 0.5% by mass of component E and 0.5% by mass of compound C, - Formulation 2Ecm: a group II oil comprising 0.25% by mass of component E and 0.25% by mass of compound C.

[0082] The results of the anti-friction tests are presented in Figure 3 and the results of the wear tests are presented in Figure 4. It is observed that the 2EC formulation allows to obtain a lower coefficient of friction, particularly at low speeds. In the wear tests, the 2EC formulations E c and 2 Ecm give better results than for formulations comprising only one additive E or C. In addition, the wear levels are lower than with the ethoxylated fatty amine and anti-wear additive pair (E+G) of comparative example 1. Example 3 (according to the invention)

[0083] Further wear and friction tests are carried out according to the protocols described previously with the following formulations: - Formulation 3E: a group II oil comprising 0.5% by mass of component E (same as formulation 2E), - 3D formulation: a group II oil comprising 0.5% by mass of component D, - Formulation 3om: a group II oil comprising 0.25% by mass of component D, - Formulation 3ED: a group II oil comprising 0.5% by mass of component E and 0.5% by mass of compound D, - Formulation 3EDm: a group II oil comprising 0.25% by mass of component E and 0.25% by mass of compound D.

[0084] The results of the anti-friction tests are presented in Figure 5 and the results of the wear tests are presented in Figure 6. It is observed that the 3ED formulation allows to obtain a lower coefficient of friction, particularly at low speeds. In the wear tests, the 3ED and 3EDm formulations give better results than for the formulations comprising only one additive E or D. In addition, the wear levels are lower than with the ethoxylated fatty amine and anti-wear additive (E+G) pair of comparative example 1. Example 4 (according to the invention)

[0085] Further wear and friction tests are carried out according to the protocols described above with the following formulations: - Formulation 4E: a group II oil comprising 0.5% by mass of component E (same as formulation 2E), - Formulation 4A: a group II oil comprising 0.5% by mass of component A, - Formulation 4EA: a group II oil comprising 0.5% by mass of component E and 0.5% by mass of compound A, - Formulation 4EAm: a group II oil comprising 0.25% by mass of component E and 0.25% by mass of compound A.

[0086] The results of the anti-friction tests are shown in Figure 7 and the results of the wear tests are shown in Figure 8. It is observed that formulation 4 E A allows for a lower coefficient of friction at virtually all speeds. In wear tests, formulation 4 EAm gives better results than when the additives are used separately in the formulations. The formulation with the A+E mixture (Formulation 4EAm) is more effective than the formulation containing product G used at the same dosage. Example 5 (according to the invention)

[0087] Wear and friction tests are carried out in a similar manner to those carried out in Example 4, with the following formulations: - Formulation 5F: a group II oil comprising 0.5% by mass of component F, - Formulation 5B: a group II oil comprising 0.5% by mass of component B, - Formulation 5FB: a group II oil comprising 0.5% by mass of component F and 0.5% by mass of compound B, - Formulation 5FBITI: a group II oil comprising 0.25% by mass of component F and 0.25% by mass of compound B.

[0088] The results of the anti-friction tests are shown in Figure 9 and the results of the wear tests are shown in Figure 10. It is observed that the 5FB formulation achieves a lower coefficient of friction at practically all speed regimes. In the wear tests, the ÔFBm formulation gives better results than when the additives are used separately in the formulations. Example 6 (according to the invention)

[0089] In this other example, similar to example 5, wear and friction tests are carried out with the following formulations: - Formulation 6F: a group II oil comprising 0.5% by mass of component F (identical to composition 5F), - Formulation 6 C : a group II oil comprising 0.5% by mass of component C (identical to composition 2c), - Formulation 6FC: a group II oil comprising 0.5% by mass of component F and 0.5% by mass of compound C, - ÔFCm formulation: a group II oil comprising 0.25% by mass of component F and 0.25% by mass of compound C.

[0090] The results of the anti-friction tests are shown in Figure 11 and the results of the wear tests are shown in Figure 12. It is observed that the 6FC formulation achieves a lower coefficient of friction at practically all speed regimes. In the wear tests, the ÔFCm formulation gives better results than when the additives are used separately in the formulations.

[0091] The examples according to the invention and as described above show the very great advantage of the composition of the present invention which makes it possible to prepare formulations having very good anti-wear and anti-friction properties, and this, while drastically reducing, and typically by half, the quantity of sulfur and / or phosphorus additives. The formulations comprising a composition according to the present invention are not only effective in terms of anti-wear and anti-friction formulations and are also more environmentally friendly than the lubricant formulations known today.

Claims

CLAIMS 1. Composition comprising: - 1) at least one (poly)esteramine, optionally quaternized, obtained by esterification: la) of at least one component chosen from fatty (poly)amines, optionally alkoxylated, fatty acids, optionally alkoxylated, and fatty alcohols, optionally alkoxylated, the fatty chain being a linear or branched, saturated or unsaturated hydrocarbon chain, comprising from 8 to 30 carbon atoms and optionally an aromatic ring, lb) of at least one component chosen from polycarboxylic acids, polycarboxylic acid anhydrides, said acids or anhydrides comprising a hydrocarbon chain, preferably a linear or branched, saturated or unsaturated alkyl chain, optionally having an aromatic ring, C1-C16, preferably C1-C12, more preferably C1-C6, lc) of at least one component chosen from non-fatty (di)alkoxylated amines,and ld) optionally at least one component chosen from diols comprising a linear or branched C1-C16, preferably C1-C12, more preferably C1-C6, alkyl chain, and, 2) at least one additive chosen from amine additives, chlorinated paraffins, fatty esters, phosphorus additives, sulfur additives, and phosphorus and sulfur additives, preferably from phosphates, in particular amine phosphates, phosphate esters, phosphites, triarylphosphates, metal dithiocarbamates, metal dithiophosphates, phosphorothionates, thioethers, polysulfides and sulfur fatty esters.

2. Composition according to claim 1, wherein component 1a) of (poly)esteramine 1) optionally contains one or more identical or different alkoxyl groups chosen from ethylene-oxy (EO), propylene-oxy (PO) butylene-oxy (BO), and mixtures of two or more of them, in blocks, in series, or random, preferably one or more ethylene-oxy (EO) groups.

3. Composition according to claim 1 or claim 2, wherein component 1a) of the (poly)esteramine 1) of the composition according to the present invention is chosen from alkoxylated, preferably ethoxylated, fatty (poly)amines, fatty acids, alkoxylated, preferably ethoxylated fatty acids, fatty alcohols, and alkoxylated, preferably ethoxylated fatty alcohols.

4. Composition according to any one of the preceding claims, in which component 1 a) is chosen from: o ethoxylated coconut amines, comprising from 2 to 20 ethylene oxide units, preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units, o optionally hydrogenated tallow amines, alkoxylated, preferably ethoxylated, and preferably those comprising from 2 to 20 ethylene oxide units, preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units, o alkoxylated oleylamines, preferably ethoxylated, and preferably those comprising from 2 to 20 ethylene oxide units, preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units ethylene, o alkoxylated coconut diamines, preferably ethoxylated, and preferably those comprising from 2 to 20 ethylene oxide units,preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units, o alkoxylated oleic diamines, preferably ethoxylated, and preferably those comprising from 2 to 20 ethylene oxide units, preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units, o optionally hydrogenated tallow diamines, alkoxylated, preferably ethoxylated, and preferably those comprising from 2 to 20 ethylene oxide units, preferably from 2 to 10 ethylene oxide units and more particularly from 2 to 5 ethylene oxide units, o copra fatty acids, and alkoxylated copra fatty acids, preferably ethoxylated, and preferably those comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, o oleic acid, and alkoxylated oleic acids, preferably ethoxylated,and preferably those comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, o optionally hydrogenated tallow fatty acids, and alkoxylated tallow fatty acids, preferably ethoxylated, and preferably those comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, and hydrogenated tallow fatty acids, o / so-decanol, / so-tridecanol, fatty alcohols whose main components are C12 to C14 alcohols, fatty alcohols whose main components are C16 to C18 alcohols, and fatty alcohols whose main components are oleyl alcohol, o alkoxylated / so-decanol, preferably ethoxylated, and preferably comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, o / so-alkoxylated tridecanol, preferably ethoxylated, and preferably comprising from 1 to 20 ethylene oxide units,preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, o fatty alcohols whose main components are alkoxylated, preferably ethoxylated, C12 and C14 alcohols, and preferably comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, o fatty alcohols whose main components are alkoxylated, preferably ethoxylated, C16 and C18 alcohols, and preferably comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units, and o fatty alcohols whose main components are alkoxylated, preferably ethoxylated, oleyl alcohol, and preferably comprising 1 to 20 ethylene oxide units, preferably 1 to 10 ethylene oxide units and more particularly 1 to 5 ethylene oxide units., 5. Composition according to any one of claims 1 to 4, in which the polycarboxylic acids 1 b) are chosen from dicarboxylic acids, tricarboxylic acids and tetracarboxylic acids, preferably from dicarboxylic acids, and more preferably from oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, phthalic acid and its isomers, tetrahydrophthalic acid, malic acid, tartaric acid and itaconic acid.

6. Composition according to any one of claims 1 to 5, wherein component 1 c) is selected from diethanolamine, methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, / so-butyldiethanolamine, pentyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, triethanolamine, as well as their corresponding alkoxylation products, in particular corresponding ethoxylation products, and typically comprising from 1 to 20 ethylene oxide units, preferably from 1 to 10 ethylene oxide units and more particularly from 1 to 5 ethylene oxide units.

7. A composition according to any one of the preceding claims, wherein component 1 d) is selected from ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol and propylene glycol, ethylene glycol monobutyl ether, di(ethylene glycol) monobutyl ether, and butylene glycol.

8. Composition according to any one of the preceding claims, in which component 2) is chosen from thiophosphoric acid, thiophosphorous acid, phosphate esters and salts of these acids, alkoxylated phosphoric esters, phosphate amines, dithiophosphates and mixtures thereof, more preferably from metal dithiocarbamates, zinc dithiophosphates, and mixtures thereof.

9. Composition according to any one of the preceding claims, in which component 2) is chosen from zinc dithiophosphates corresponding to the general formula (I): in which the radicals R 10 , R 11 , R 12 and R 13, each independently of the others, represent a linear, branched or cyclic hydrocarbon chain comprising from 1 to 24 carbon atoms, optionally comprising an aromatic nucleus, preferably a linear or branched hydrocarbon chain comprising from 1 to 24 carbon atoms, more preferably a linear or branched hydrocarbon chain comprising from 3 to 12 carbon atoms, for example a linear or branched hydrocarbon chain comprising from 6 to 10 carbon atoms.

10. Composition according to one of the preceding claims which is: the composition comprising (1) the reaction product between ethoxylated oleylamine with 5 ethylene oxide units, oleic fatty acid, oxalic acid and diethanolamine and (2) a zinc dithiophosphate, • the composition comprising (1) the reaction product between tallow amine, ethoxylated coconut fatty acid with 2 ethylene oxide units, succinic acid and / so-butyldiethanolamine in ethylene glycol and (2) a zinc dithiophosphate, • the composition comprising (1) the product of the reaction between ethoxylated oleylamine with 2 ethylene oxide units, oleic acid, oxalic acid and diethanolamine and (2) the phosphoric ester of an ethoxylated oleyl alcohol with 5 ethylene oxide units, • the composition comprising (1) the reaction product between ethoxylated tallow amine with 2 ethylene oxide units, tallow fatty acid, adipic acid and methyldiethanolamine and (2) a zinc dithiophosphate, • the composition comprising (1) the product of the reaction between ethoxylated tallow amine with 2 ethylene oxide units, tallow fatty acid, adipic acid and methyldiethanolamine and (2) the phosphoric ester of an ethoxylated oleyl alcohol with 5 ethylene oxide units, • the composition comprising (1) the product of the reaction between tallow fatty acid, adipic acid and diethanolamine, quaternized with methyl chloride and (2) zinc dithiophosphate, • the composition comprising (1) the product of the reaction between ethoxylated tallow amine with 2 ethylene oxide units, tallow fatty acid, adipic acid and methyldiethanolamine, quaternized with methyl chloride, and (2) the phosphoric ester of an ethoxylated oleyl alcohol with 5 ethylene oxide units.

11. Composition according to any one of the preceding claims, in which component 1) of the composition of the invention is a quaternized polyesteramine corresponding to the general formula (P): in which: R 1 is a linear or branched, saturated or unsaturated hydrocarbon chain, comprising from 8 to 30 carbon atoms, preferably from 8 to 24 carbon atoms and optionally an aromatic cycle, R 2 is a linear or branched C1-C16, preferably C1-C12, more preferably C1-C6, alkyl chain, R 4 is chosen from a hydrocarbon chain, linear or branched, saturated or unsaturated, preferably saturated, and having from 1 to 7 carbon atoms, preferably from 1 to 6 carbon atoms and a -(CH2CH2O)] chain P -H, where p represents an integer ranging from 1 to 10, preferably from 1 to 5, R 5represents a linear or branched hydrocarbon chain comprising from 1 to 6 carbon atoms and optionally substituted by an aromatic radical, AO represents an alkoxylated unit chosen from ethoxy, propoxy, and butoxy, preferably AO represents an ethoxy unit -(CH2CH2O)-, x is an integer between 1 and 10, preferably between 1 and 5, - t is equal to 0 or 1, p represents an integer between 1 and 15, preferably between 1 and 10 and more preferably between 1 and 5, and X- represents the anion of the quaternizing agent, and is preferably chosen from halides (chloride, bromide, iodide), carbonates, sulfates and sulfonates.

12. Use of a composition as defined in any one of the preceding claims as an additive in a lubricating formulation.

13. Lubricating formulation comprising at least one composition according to any one of claims 1 to 11.

14. Formulation according to claim 13 comprising between 0.1% and 20% by mass, limits included, preferably between 0.1% and 15% by mass, limits included, more preferably between 0.1% and 10% by mass, limits included, better still between 0.1% and 5% by mass, limits included, of the composition according to any one of claims 1 to 10, relative to the total mass of the lubricating composition.

15. Use of a formulation according to claim 13 or claim 14, in lubricating formulations for parts in relative motion, for electric current generation coils, thermal or electric vehicle engines, automobile engines, for metal milling and cutting systems, in fuel compositions.

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