(POLY)ESTERAMINE-BASED ANTI-WEAR ADDITIVES
A combination of (poly)esteramines and phosphorus/sulfur additives in lubricating compositions addresses the environmental concerns of existing additives, achieving enhanced friction and wear reduction with lower phosphorus and sulfur content, thus improving mechanical system performance.
Patent Information
- Application Number
- FR2023014883
- Authority / Receiving Office
- FR · FR
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2023-12-21
- Publication Date
- 2025-11-07
- Estimated Expiration
- 2043-12-21
AI Technical Summary
Existing anti-wear and anti-friction additives in lubricating compositions contain high levels of phosphorus and sulfur, which are environmentally harmful and require large quantities, posing a challenge for reducing friction and wear in mechanical systems.
A composition comprising (poly)esteramines, possibly quaternized, derived from fatty amines, fatty acids, polycarboxylic acids, and diols, combined with phosphorus and sulfur additives like zinc dithiophosphates, to form lubricating formulations that reduce friction and wear while minimizing phosphorus and sulfur content.
The composition achieves superior anti-wear and anti-friction properties with reduced additive quantities, minimizing environmental impact and corrosion, and providing improved lubrication performance in mechanical systems.
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Abstract
Description
Title of the invention: (POLY)ESTERAMINE-BASED ANTI-WEAR ADDITIVES
[0001] The present invention relates to the field of lubricants and more specifically 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 higher molecular weights has appeared in the literature. These compounds have a polymeric or oligomeric structure and contain amine and quaternary ammonium functional groups.
[0003] Thus, international application WO2008089906 describes the reaction products of a fatty acid with a diacid and an (alkyl)polyethanolamine, said reaction products being subsequently quaternized. In this international application, these products are defined as surfactants that can be used as collectors for ore flotation. 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 silicate flotation.
[0004] More recently still, 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, it describes quaternized nitrogen compounds used as friction-reducing additives in fuels. These compounds are obtained by quaternization with ethylene oxide. Finally, international application WO2022167756 describes polyester-polyamines and their quaternized versions, usable in various applications, including lubricant 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 One of the most important characteristics of a lubricant when dealing with wear or extreme pressure is its viscosity. However, if the system operates under mixed lubrication conditions, even if the oil film remains, asperities on the opposing metal surfaces will come into contact. Anti-wear additives aim to prevent these contacts from "welding" together. Anti-wear additives thus provide protection through physical or chemical adsorption and / or chemical reaction between the additive and the metal surface.
[0007] Among the most commonly used anti-wear and / or extreme-pressure additives, one can cite, for example, derivatives containing phosphorus, the best-known representatives of which are phosphates in general, such as amine phosphates, phosphate esters, triaryl phosphates, 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, notably metal dithiophosphates, phosphorothionates, and others.
[0008] One of the major drawbacks of these anti-wear additives known today is their bad impact on the environment where the discharge 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 which contain them even improved anti-wear and anti-friction properties.
[0010] Thus, and according to a first objective, the invention proposes lubricating compositions comprising one or more additives enabling the reduction of friction and wear in mechanical systems having parts in relative motion, such as, for example and without limitation, in vehicle transmission systems, in rotor and stator systems, in machines, in turbines, in electric current generation coils as well as in motors, as well as in hydraulic systems, but also during the working of metals and alloys.
[0011] Another objective of the invention is to propose lubricating compositions comprising one or more additives to reduce friction and wear in mechanical systems having parts in relative motion, compositions in which the additives are used in smaller quantities than those found today.
[0012] Another objective of the invention is to provide lubricating compositions that reduce friction and wear in mechanical systems, particularly those with parts in relative motion, compositions in which the additives used are more environmentally friendly.
[0013] Another objective is to propose lubricating compositions comprising one or more additives that reduce friction and wear in systems mechanical components with parts in relative motion, compositions in which the additives are biodegradable and non-ecotoxic, and which reduce associated air pollution due to their low sulfur and / or phosphorus content.
[0014] Other objectives will appear in the following description of the invention.
[0015] In the present invention, the ranges of values are understood to be inclusive of all limits, unless explicitly stated otherwise.
[0016] It has now been discovered that the aforementioned 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, according to a first aspect, the present invention relates to a composition comprising: 1) at least one (poly)esteramine, possibly quaternized, obtained by esterification: (a) of at least one component selected from fatty (poly)amines, possibly alkoxylated, fatty acids, possibly alkoxylated, and fatty alcohols, possibly alkoxylated, the fatty chain being a linear or branched hydrocarbon chain, saturated or unsaturated, comprising from 8 to 30 carbon atoms and possibly an aromatic ring, 1b) of at least one component selected from polycarboxylic acids, polycarboxylic acid anhydrides, said acids or anhydrides comprising a hydrocarbon chain, preferably an alkyl chain, linear or branched, saturated or unsaturated, possibly possessing an aromatic ring, in CrCi6, preferably in C1-C12, preferably also in Ci-C6, the) of at least one component selected from non-fatty (di)alkoxylated amines,
[0018] and
[0019] Id) of possibly at least one component selected from diols comprising a linear or branched CrCi6 alkyl chain, preferably C1-C12, preferably Ci_C6, and 2) at least one additive chosen from among phosphorus additives, sulfur additives, and phosphorus and sulfur additives, preferably from among phosphates, in particular amine phosphates, phosphate esters, phosphites, triaryl phosphates, metallic dithiocarbamates, metallic dithiophosphates and phosphorothionates.
[0020] The respective proportions of components 1) and 2) of the composition according to the present invention can vary in large proportions and are generally between 99:1 and 1:99, by weight, preferably between 75:25 and 25:75, by weight, preferably again between 60:40 and 40:60, by weight.
[0021] Component 1a) of the (poly)esteramine 1) of the composition according to the present invention may optionally be alkoxylated, that is to say, may contain one or more identical or different alkoxy 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 randomly. When component 1a) is alkoxylated, the ethylene-oxy (EO) alkoxy group is preferred.
[0022] Most preferably, component 1a) of the (poly)esteramine 1) of the composition according to the present invention is chosen from alkoxylated fatty (poly)amines, preferably ethoxylated, fatty acids, alkoxylated fatty acids, preferably ethoxylated, fatty alcohols, and alkoxylated fatty alcohols, preferably ethoxylated.
[0023] Among the components adapted within the framework of the present invention, the following may be cited by way of non-limiting examples: - fatty alkoxylated (poly)amines, preferably ethoxylated, and in particular: • 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, • tallow amines, possibly hydrogenated, alkoxylated, preferably ethoxylated, and preferably those comprising 2 to 20 ethylene oxide motifs, preferably 2 to 10 ethylene oxide motifs, and more particularly 2 to 5 ethylene oxide motifs, • alkoxylated oleylamines, preferably ethoxylated, and preferably those comprising 2 to 20 ethylene oxide motifs, preferably 2 to 10 ethylene oxide motifs, and more particularly 2 to 5 ethylene oxide motifs, • Alkoxylated copra diamines, preferably ethoxylated, and preferably those comprising 2 to 20 ethylene oxide units, preferably 2 to 10 ethylene oxide units, and more particularly 2 to 5 ethylene oxide units, • alkoxylated oleic diamines, preferably ethoxylated, and preferably those comprising 2 to 20 ethylene oxide motifs, preferably 2 to 10 ethylene oxide motifs, and more particularly 2 to 5 ethylene oxide motifs, • tallow diamines, possibly hydrogenated, alkoxylated, preferably ethoxylated, and preferably those comprising 2 to 20 ethylene oxide motifs, preferably 2 to 10 ethylene oxide motifs, and more particularly 2 to 5 ethylene oxide motifs, - fatty acids, representatives of which are chosen from coconut fatty acids, oleic acid, tallow fatty acids, hydrogenated tallow fatty acids,
[0024] - alkoxylated fatty acids, preferably ethoxylated, of which representatives are Choose from: • Alkoxylated coconut fatty acids, preferably ethoxylated, and preferably those comprising 1 to 20 ethylene oxide units, preferably 1 to 10 ethylene oxide units, and more particularly 1 to 5 ethylene oxide units, • Alkoxylated oleic acids, preferably ethoxylated, and preferably those comprising 1 to 20 ethylene oxide units, preferably 1 to 10 ethylene oxide motifs, and more specifically 1 to 5 ethylene oxide motifs, • tallow fatty acids, possibly hydrogenated, alkoxylated, preferably ethoxylated, and preferably those comprising 1 to 20 ethylene oxide units, preferably 1 to 10 ethylene oxide units, and more particularly 1 to 5 ethylene oxide units, - fatty alcohols, the main representatives of which are zso-decanol, zso-tridecanol, fatty alcohols whose main components are alcohols in the ranges of C12 to C1M, fatty alcohols whose main components are alcohols in the ranges of C16 to C18, and fatty alcohols whose main components are oleic alcohol,
[0025] - alkoxylated fatty alcohols, preferably ethoxylated, of which representatives are Choose from: • Alkoxylated zsodecanol, preferably ethoxylated, 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, • Alkoxylated zso-tridecanol, preferably ethoxylated, 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, • fatty alcohols whose main components are alkoxylated Ci2 and CM alcohols, preferably ethoxylated, 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, • fatty alcohols whose main components are alkoxylated Ci6 and Ci8 alcohols, preferably ethoxylated, and preferably comprising 1 to 20 ethylene oxide motifs, preferably from 1 to 10 ethylene oxide motifs and more particularly from 1 to 5 ethylene oxide motifs, and • fatty alcohols whose main components are alkoxylated oleic alcohol, preferably ethoxylated, and preferably comprising 1 to 20 ethylene oxide motifs, preferably 1 to 10 ethylene oxide motifs and more particularly 1 to 5 ethylene oxide motifs.
[0026] The polycarboxylic acids 1b) are more specifically chosen from among the dicarboxylic acids, tricarboxylic acids and tetracarboxylic acids, preferably from among the dicarboxylic acids. Examples of dicarboxylic acids particularly suitable within the scope 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.
[0027] By non-fatty (di)alkoxylated amines, mono- or di-alkoxylated amines are meant, where "alkoxylated" includes the terms ethoxylated, propoxylated and / or butoxylated, with a number of alkoxylated motifs ranging from 1 to 20, preferably from 1 to 10, and comprising an optionally but preferably 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.
[0028] According to a preferred embodiment, the compound le) is chosen from among the non-fatty (di)ethoxylated fatty amines of general formula (le):
[0029] [Chem.l] 1 ÏtïlchÆh L ~ -1 m (the)
[0030] in which: • A is chosen from among 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 chain -(CH2CH2O)]pH, and • n and m and p, independently of each other, each represent an integer from 1 to 10, preferably from 1 to 5.
[0031] Representative examples of component le) defined above are advantageously chosen from diethanolamine, methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, α-butyldiethanolamine, pentyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, triethanolamine, and their alkoxylation products corresponding, in particular corresponding ethoxylation products, and typically comprising 1 to 20 ethylene oxide motifs, preferably 1 to 10 ethylene oxide motifs and more particularly 1 to 5 ethylene oxide motifs.
[0032] Particularly suitable representatives of component Id) defined above are advantageously chosen from among the glycols and typically from among 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.
[0033] According to a preferred embodiment of the present invention, component Id) of the (poly)esteramine 1) of the composition according to the present invention does not comprise a nitrogen atom, and preferably does not comprise an amine function.
[0034] As previously stated, the (poly)esteramine 1) obtained by esterification of components a), 1b), le) and optionally Id) 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 the person skilled in the art, generally and most often using at least one alkylating agent, and for example as described in application WO2022167756.
[0035] When the quaternization reaction, partial or total, is carried out using an alkylating agent, the latter is generally and most often chosen from among the most common and well-known alkylating agents, and preferably from among methyl chloride, methyl bromide, methyl iodide, dimethyl sulfate, diethyl sulfate, dimethyl carbonate and benzyl chloride, and preferably again from among methyl chloride, dimethyl sulfate, diethyl sulfate and benzyl chloride, as well as mixtures thereof, most preferably from among methyl chloride, dimethyl sulfate and mixtures thereof.
[0036] It must be understood that the quaternization step, partial or total, can be carried out on component 1a) and / or on the condensation product of component 1a) and component 1b) and / or on the condensation product of component 1a), of component 1b), and of component 1e).
[0037] 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 procedures well known to those skilled in the art.
[0038] As previously stated, component 1) of the composition of the present invention is a compound with a polyesteramine structure, possibly quaternized. Such compounds are well known to those skilled in the art and are, for example, described in application WO2022167756 AL. The present invention relates in particular to compositions comprising such compounds with a polyesteramine structure, possibly quantified, in combination with one or more anti-wear and / or anti-friction additives.
[0039] 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):
[0040] [Chem.2] (R5)t R'-ïpKAO-^-R1 O R4 x- oo R4 O zx A (P)
[0041] in which: - R1 is a linear or branched hydrocarbon chain, saturated or unsaturated, comprising from 8 to 30 carbon atoms, preferably from 8 to 24 carbon atoms and optionally an aromatic ring, - R2 is a linear or branched alkyl chain in CrCi6, preferably in Ci-Ci2, preferably again in Ci_C6, - R4 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 chain -(CH2CH2O)]PH, where p represents an integer from 1 to 10, preferably from 1 to 5, - R5 represents a hydrocarbon chain, linear or branched, comprising from 1 to 6 carbon atoms and possibly substituted by an aromatic radical, - AO represents an alkoxy group chosen from ethoxy, propoxy, and butoxy, preferably AO represents an ethoxy group -(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 even more preferably between 1 and 5, and - X represents the anion of the quaternizing agent, and is preferably chosen from among the halides (chloride, bromide, iodide), carbonates, sulfates and sulfonates.
[0042] Thus, component 2) of the composition of the present invention consists of at least one additive selected from 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.
[0043] Among these, purely illustrative and non-limiting examples include thiophosphoric acid, thiophosphorous acid, esters (in particular phosphate esters) and salts of these acids, alkoxylated phosphoric esters, phosphate amines, dithiophosphates, metal dithiocarbamates and mixtures thereof. Phosphorus and / or sulfur additives are particularly preferred, and more specifically zinc dithiophosphates and metal dithiocarbamates, such as molybdenum dithiocarbamates.
[0044] Quite representative but not limiting examples of such additives include zinc diaryldithiophosphates and zinc dialkyldithiophosphates, also well known by their acronym "ZDDP".
[0045] In one embodiment of the invention, component 2) is chosen from zinc dithiophosphates corresponding to the general formula (I):
[0046] [Chem.3] 10th ■s RO. X ^OR XA XV n R"'OZ "S' 'qr ' in which The radicals R10, R11, R12 and R13, each independently of each other, represent a linear, branched or cyclic hydrocarbon chain comprising from 1 to 24 carbon atoms, possibly including an aromatic ring, 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.
[0047] 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), include: • the composition comprising (1) the reaction product between oleylamine ethoxylated 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, coconut fatty acid ethoxylated with 2 ethylene oxide units, succinic acid and isobutyldiethanolamine 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 oleylamine ethoxylated with 2 ethylene oxide units, oleic acid, oxalic acid and diethanolamine and (2) the phosphoric ester of an oleic alcohol ethoxylated with 5 ethylene oxide units, • the composition comprising (1) the product of the reaction between tallow amine ethoxylated 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 tallow amine ethoxylated with 2 ethylene oxide units, tallow fatty acid, adipic acid and methyldiethanolamine and (2) the phosphoric ester of an oleic alcohol ethoxylated 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 tallow amine ethoxylated with 2 ethylene oxide units, tallow fatty acid, adipic acid and methyldiethanolamine, quaternized with methyl chloride, and (2) the phosphoric ester of an oleic alcohol ethoxylated with 5 ethylene oxide units.
[0048] The composition according to the present invention comprising at least one component 1) and at least one component 2) as just defined is of particular interest and application as an additive in lubricating formulations.
[0049] 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.
[0050] According to yet another aspect, the present invention relates to a lubricating formulation comprising at least one composition according to the invention, that is to say a composition comprising at least one component 1) and at least one component 2), as indicated above.
[0051] The lubricating formulation according to the present invention generally and most often comprises between 0.1% and 20% by mass, inclusive terminals, preferably between 0.1% and 15% by mass, inclusive terminals, preferably again between 0.1% and 10% by mass, inclusive terminals, better still between 0.1% and 5% by mass, inclusive terminals, 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.
[0052] The lubricating formulation according to the invention may be a ready-to-use formulation and in this case most often and advantageously comprises 0.01% to 5%, preferably 0.01% to 3% by weight of component 1) and 0.01% to 5%, preferably 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 0.5% to 20%, preferably 0.5% to 15% by weight of component 1) and 0.5% to 20%, preferably 0.5% to 15% by weight of component 2).
[0053] 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 lubricating formulation proper, a cutting oil that may contain a greater or lesser quantity of water, a fuel, and other substances. Those skilled in the art will be able to adapt the quantity and nature of components 1) and 2) according to the nature of the lubricating formulation of interest.
[0054] It has been observed in a completely surprising way 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, or even excellent, levels of friction and wear reduction, particularly in the concentration ranges mentioned above.
[0055] It has been demonstrated that the composition of the invention, an association 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 prior art lubricating compositions comprising equivalent concentrations of additive(s).
[0056] Another advantage of the formulation of the present invention is that it is possible to obtain levels of anti-wear and anti-friction properties similar to those observed with prior art compositions containing higher concentrations of additive(s). In this case, the lubricating formulation according to the invention offers a clear advantage, particularly for the environment, in that a smaller quantity of sulfur and / or phosphorus compounds will be used and therefore less likely to appear in various discharges and effluents.
[0057] Thus, the combination of components 1) and 2) in the composition of the present invention as defined above provides a level of friction and wear reduction never before achieved with prior art lubrication additives. Indeed, this combination makes it possible to reduce the quantity of components 1) and 2), and in particular the phosphorus and / or sulfur component 2), while providing levels of friction and wear reduction comparable to those of the prior art. known from the prior art with higher quantities of additives, or with levels of friction and wear reduction significantly higher than those known from the prior art with similar quantities of additives. The ability to use additives, particularly phosphorus and / or sulfur anti-wear additives, in smaller quantities in lubricant formulations has a definite, important, and entirely relevant impact on environmental protection.
[0058] For the purposes of the present invention, "lubricating formulation" means any formulation used in mechanical systems comprising parts in relative motion to reduce wear by friction. The lubricating formulation according to the invention generally and most often comprises at least one composition including 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 fuel as defined in the invention includes gasoline, diesel, kerosene, 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 encompassed in the general term "lubricating formulations".
[0059] 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.
[0060] Organosulfur compounds, organochlorine compounds and organophosphorus compounds and mixtures thereof are particularly used as extreme-pressure additives. In a preferred embodiment, extreme-pressure additives include chlorinated paraffins, alkyl or alkylphenol polysulfides, sulfurized olefins, sulfur 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.
[0061] Among the corrosion inhibitors that can be used in formulations according to the present invention, the following may be mentioned, in particular and without limitation: boric acids and their salts, tolyltriazole and its salts, benzotriazoles and their salts, imidazolines and their salts, alkanolamines and amides, sulfonates, alkali and alkanolamine salts of naphthenic acids, amine salts of phosphate esters, alkali nitrites, alkali carbonates, carboxylic acids and their derivatives, acids 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 glycol ether phosphate salts and their mixtures.
[0062] Other additives and / or fillers that can be used in formulations of the present invention include antioxidants, in particular phenolic derivatives, amines and mixtures thereof.
[0063] By way of non-limiting examples of metal deactivators which may be useful in the formulations of the present invention, preference is given to triazoles.
[0064] As previously stated, the formulation of the invention is generally ready for 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 that are compatible with lubricating formulations, and for example, depending on the intended use, diluents are chosen from among organic diluents, such as oils and fuels, and also aqueous or hydro-organic diluents, for example, water, particularly for metalworking applications ("metal working fluid" in English).
[0065] The formulation according to the present invention thus finds very interesting applications as a lubricating formulation, and in this respect 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 mention only the most common and well-known applications.
[0066] The advantages provided by the lubricating formulation of the present invention are numerous and varied and among these, we can mention, by way of non-limiting, the many advantages related to the reduction of the friction of the parts in relative motion in the engines of motor vehicles, and in particular fuel savings, a substantial increase in the autonomy of vehicles, electric or thermal, better efficiency in all lubrication regimes and regardless of engine torque.
[0067] As another 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 are also often responsible for significant corrosion of metal parts, particularly those found in 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 lubricating formulations used today, the corrosion of the metal parts is very limited, or even almost non-existent, and even non-existent.
[0068] Another further advantage is the reduction of air pollution associated with the use of the relatively small quantities of composition according to the present invention, and thus greater ease of compliance with future environmental regulations, especially since the composition of the invention and in particular its component 1) is advantageously a biodegradable and non-ecotoxic additive.
[0069] The invention is now illustrated by means of the following examples, which in no way limit the invention, the scope of which is defined by the claims annexed to this description. Examples
[0070] The following examples use the following components for preparing compositions that will be tested for their anti-wear and anti-friction properties:
[0071] 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:
[0072] [Chem.4] ■ RA (R5), R1............R- AO .....R2.....idpf AO ^-N^ AO p.......K1 0 R* x- OOR* ô
[0073] in which: - R1 is a tallow radical (alkyl chain predominantly with 18 carbon atoms), R2 is -(CH2)2-, - R4 and R5 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 the methyl chloride used as alkylating agent.
[0074] 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.
[0075] 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: [Tables 1] Component CD Ethoxylated fatty amine of formula (I) R1 (AQ^H “I / N—(CH .A--NI " “ XB (AO)nH NoxS2 NoxS5 Mass of (I) (in g) 178.9 311.1 Dicarboxylic acid of formula (I) D< .Y- YTO o Ac. Ad. Ac. Ad. Mass of (II) (in g) 584.6 584.6 Alkanolamine derivative of formula (III) 7 / R—N Ç / WiVH MDEA MDEA Mass of (III) (in g) 476 476 Fatty acid derivative of formula (V) rI1 oh 0 AGS AGS Mass of (V) (in g) 555 555
[0076] 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.
[0077] Component E [component 2) of the composition according to the present invention] is distributed by Additive Chemie Luers GmbH under the brand KUNOX® S8811 and is a zinc dialkyldithiophosphate (ZDDP) known as an anti-wear additive.
[0078] Component F [component 2) of the composition according to the present invention] is an additive available from ARKEMA under the brand name SURF ALINE® PE 684 and is a phosphoric ester (5-mol ethoxylated oleocetyl alcohol phosphate ester of ethylene oxide) known as an anti-wear additive.
[0079] Component G is an ethoxylated tallow amine (2OE) supplied by Arkema under the brand name Noramox® S2, known as a friction-reducing additive. This component G is a component used to prepare a comparative composition. Friction Test Protocol
[0080] The coefficient of friction is measured using the MTM tribometer supplied by PCS Instruments. This is a ball-on-disc tribometer that allows the friction properties of lubricated and unlubricated contacts to be measured over a wide range of rolling and sliding conditions.
[0081] The MTM tribometer allows friction to be evaluated: - depending on the sliding ratio in the contact (rolling / sliding ratio noted SRR for "Slide / Roll Ratio" in English) with a traction curve (here, the speed is fixed), - depending on the rolling speed in the Stribeck curve contact (here, the SRR ratio is fixed), and - as a function of time with curve at iso-conditions (here, fixed SRR ratios and speed).
[0082] The friction generated between the ball and the disk is measured using a torque sensor. The torque sensor is located between the ball's shaft and a fixed point. The friction force is therefore measured perpendicular to the direction of the load. The sliding / rolling ratio is the ratio between the sliding speed and the rolling speed of a contact.
[0083] Test conditions: - Concentration of additive, alone or in mixture: between 0 and 1% by mass in a Group II mineral oil, marketed by Total Energies under the name Torilis HC 1850, which will be the Group II mineral oil used in all the following examples, unless expressly stated otherwise. Test temperature: 120°C Applied load: 37 N Sliding / rolling ratio (SRR): 50%, Rolling speed: measured from 8 mm s 1 to 3200 mm s1.
[0084] The result appears as a curve with the rolling speed (in mm / s) on the x-axis and the coefficient of friction on the y-axis. The interpretation is visual; the lower the coefficient of friction, the more the product is considered to be a friction reducer. Wear Test Protocol
[0085] The tests were carried out in accordance with IP 239 (REF / ISBN IP 239-2936900, February 2014), the test method used to determine the relative wear-preventing properties of lubricating fluids in sliding contact under the prescribed test conditions (four-ball method).
[0086] 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 Trial time: 1 hour
[0087] The wear diameter of the three fixed balls generated by the rotating ball is measured using a binocular microscope. The tests are repeated at least twice, and 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 wear-resistant properties. Results
[0088] 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
[0089] The first set of results corresponds to a friction test carried out with: - Reference formulation 1R: a group II oil,
[0090] - Formulation 1E: a group II oil comprising 0.5% by mass of component E,
[0091] - Formulation lEd: a group II oil comprising 1% by mass of component E,
[0092] - Formulation 1G: a group II oil comprising 0.5% by mass of component G,
[0093] - Comparative formulation: 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).
[0094] The results are presented in [Fig. 1]. It can be observed that Formulation 1E does not provide any friction-reducing effect, this effect being less good than that observed with the reference Formulation 1R.
[0095] Additive G plays its role as a friction reducer in Formulation 1G, but the test carried out with the Comparative Formulation 1Comp shows that the performance of additive G is degraded.
[0096] This example proves that when the Formulation includes a composition not meeting the definition of the present invention, no improvement is observed in this anti-friction test. Wear tests 1
[0097] The results are shown in [Fig. 2]. Formulations 1E and 1Ed confirm that Component E is a good anti-wear additive and that Formulation 1G also provides a suitable anti-wear effect, while Component G is more commonly used as a friction-reducing additive. Formulation 1Comp, on the other hand, provides no improvement in wear reduction. Example 2 (according to the invention)
[0098] 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,
[0099] - Formulation 2C: a Group II oil comprising 0.5% by mass of component C,
[0100] - Formulation 2Cm: a group II oil comprising 0.25% by mass of component C,
[0101] - Formulation 2EC: a group II oil comprising 0.5% by mass of component E and 0.5% by mass of compound C,
[0102] - Formulation 2ECm: a group II oil comprising 0.25% by mass of component E and 0.25% by mass of compound C.
[0103] The results of the anti-friction tests are shown in [Fig. 3] and the results of the wear tests are shown in [Fig. 4]. It can be observed that formulation 2EC provides a lower coefficient of friction, particularly at low speeds. In the wear tests, formulations 2EC and 2ECm give better results than formulations containing only one additive, E or C. Furthermore, the wear levels are lower than with the combination of ethoxylated fatty amine and anti-wear additive (E+G) in comparative Example 1. Example 3 (according to the invention)
[0104] Other wear and friction tests are carried out according to the protocols described above with the following formulations: - Formulation 3E: a group II oil comprising 0.5% by mass of component E (same as formulation 2E),
[0105] - 3D Formulation: a Group II oil comprising 0.5% by mass of component D,
[0106] - Formulation 3Dm: a group II oil comprising 0.25% by mass of component D,
[0107] - Formulation 3ED: a group II oil comprising 0.5% by mass of component E and 0.5% by mass of compound D,
[0108] - Formulation 3EDm: a group II oil comprising 0.25% by mass of component E and 0.25% by mass of compound D.
[0109] The results of the anti-friction tests are shown in [Fig. 5] and the results of the wear tests are shown in [Fig. 6]. It can be observed that formulation 3ED provides a lower coefficient of friction, particularly at low speeds. In the wear tests, formulations 3 and 3D give better results than formulations containing only one additive, E or D. Furthermore, the wear levels are lower than with the combination of ethoxylated fatty amine and anti-wear additive (E+G) in comparative Example 1. Example 4 (according to the invention)
[0110] 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),
[0111] - Formulation 4A: a group II oil comprising 0.5% by mass of component HAS,
[0112] - Formulation 4EA: a Group II oil comprising 0.5% by mass of component E and 0.5% by mass of compound A,
[0113] - Formulation 4EAm: a Group II oil comprising 0.25% by mass of component E and 0.25% by mass of compound A.
[0114] The results of the anti-friction tests are shown in [Fig. 7] and the results of the wear tests are shown in [Fig. 8]. It can be observed that formulation 4EA provides a lower coefficient of friction at virtually all speed ranges. In the wear tests, formulation 4EAm 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)
[0115] Wear and friction tests are carried out in a manner similar 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,
[0116] - Formulation 5B: a Group II oil comprising 0.5% by mass of component B,
[0117] - Formulation 5FB: a group II oil comprising 0.5% by mass of component F and 0.5% by mass of compound B,
[0118] - Formulation 5FBm: a Group II oil comprising 0.25% by mass of component F and 0.25% by mass of compound B.
[0119] The results of the anti-friction tests are shown in [Fig. 9] and the results of the wear tests are shown in [Fig. 10]. It can be observed that the 5FB formulation provides a lower coefficient of friction at virtually all speed ranges. In the wear tests, the 5FBm formulation gives better results than when the additives are used separately in the formulations. Example 6 (according to the invention)
[0120] 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),
[0121] - Formulation 6C: a group II oil comprising 0.5% by mass of component C (identical to composition 2C),
[0122] - Formulation 6FC: a Group II oil comprising 0.5% by mass of component F and 0.5% by mass of compound C,
[0123] - Formulation 6FCm: a Group II oil comprising 0.25% by mass of component F and 0.25% by mass of compound C.
[0124] The results of the anti-friction tests are shown in [Fig. 11] and the results of the wear tests are shown in [Fig. 12]. It can be observed that the 6FC formulation provides a lower coefficient of friction at virtually all speed ranges. In the wear tests, the 6FCm formulation gives better results than when the additives are used separately in the formulations.
[0125] The examples according to the invention and as described above demonstrate the significant advantage of the composition of the present invention, which makes it possible to prepare formulations exhibiting very good anti-wear and anti-friction properties, while drastically reducing, typically by half, the quantity of sulfur and / or phosphorus additives. Formulations comprising a composition according to the present invention are not only effective in terms of anti-wear formulations and anti-friction and are also more environmentally friendly than currently available lubricating formulations.
Claims
Demands
1. Composition comprising: - 1) at least one (poly)esteramine, optionally quaternized, obtained by esterification: a) of at least one component selected 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, 1b) of at least one component selected from polycarboxylic acids, polycarboxylic acid anhydrides, said acids or anhydrides having a hydrocarbon chain, preferably an alkyl chain, linear or branched, saturated or unsaturated, optionally possessing an aromatic ring, in CrCi6, preferably in CrCi2, preferably also in Ci-C6, e) of at least one component selected from non-fatty amines (di)alkoxylated,and (d) possibly at least one component selected from diols having a linear or branched alkyl chain in Ci-Ci6, preferably in Ci-Ci2, preferably also in C, C6, and (2) at least one additive selected from phosphorus additives, sulfur additives, and phosphorus and sulfur additives, preferably from phosphates, in particular amine phosphates, phosphate esters, phosphites, triaryl phosphates, metal dithiocarbamates, metal dithiophosphates and phosphorothionates.
2. Composition according to claim 1, wherein component 1a) of (poly)esteramine 1) optionally contains one or more identical or different alkoxyl 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 randomly, 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 selected from alkoxylated fatty (poly)amines, preferably ethoxylated fatty acids, fatty acids
4. alkoxylated, preferably ethoxylated, fatty alcohols, and alkoxylated fatty alcohols, preferably ethoxylated. Composition according to any one of the preceding claims, wherein component (la) is selected from: O ethoxylated copra 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 tallow amines, possibly hydrogenated, alkoxylated, preferably ethoxylated, and preferably those comprising 2 to 20 ethylene oxide motifs, preferably 2 to 10 ethylene oxide motifs, and more particularly 2 to 5 ethylene oxide motifs, O alkoxylated oleylamines, preferably ethoxylated, and preferably those comprising 2 to 20 ethylene oxide motifs, preferably 2 to 10 ethylene oxide motifs, and more particularly 2 to 5 ethylene oxide motifs, O alkoxylated copra diamines, preferably ethoxylated, and preferably those comprising 2 to 20 ethylene oxide motifs, preferably 2 to 10 ethylene oxide motifs, and more particularly 2 to 5 ethylene oxide motifs, O alkoxylated oleic diamines, preferably ethoxylated, and preferably those comprising 2 to 20 ethylene oxide motifs, preferably 2 to 10 ethylene oxide motifs, and more particularly 2 to 5 ethylene oxide motifs, O tallow diamines, possibly hydrogenated, alkoxylated, preferably ethoxylated, and preferably those comprising 2 to 20 ethylene oxide motifs, preferably 2 to 10 ethylene oxide motifs, and more particularly 2 to 5 ethylene oxide motifs, O coconut fatty acids, and alkoxylated coconut fatty acids, preferably ethoxylated, and preferably those comprising 1 to 20 ethylene oxide units, preferably 1 to 10 ethylene oxide units and more particularly 1 to 5 ethylene oxide units, Oleic acid, and alkoxylated oleic acids, preferably ethoxylated, and preferably those comprising 1 to 20 ethylene oxide units, preferably 1 to 10 oxide units
5. of ethylene, and more specifically of 1 to 5 ethylene oxide motifs, O tallow fatty acids, possibly hydrogenated, and alkoxylated tallow fatty acids, preferably ethoxylated, and preferably those comprising 1 to 20 ethylene oxide units, preferably 1 to 10 ethylene oxide units and more particularly 1 to 5 ethylene oxide units, and hydrogenated tallow fatty acids, O zsodecanol, zsodecanol-tridecanol, fatty alcohols whose main components are alcohols in the C12 to C14 groups, fatty alcohols whose main components are alcohols in the C16 to C18 groups, and fatty alcohols whose main components are oleic alcohol, O alkoxylated zsodecanol, 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, Alkoxylated zso-tridecanol, preferably ethoxylated, and preferably comprising 1 to 20 ethylene oxide motifs, preferably 1 to 10 ethylene oxide motifs, and more particularly 1 to 5 ethylene oxide motifs, Fatty alcohols whose main components are alkoxylated Cn and CM alcohols, preferably ethoxylated, 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, Fatty alcohols whose main components are alkoxylated Ci6 and Cis alcohols, preferably ethoxylated, 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, and Fatty alcohols whose main components are alkoxylated oleic alcohol, preferably ethoxylated, and preferably comprising 1 to 20 ethylene oxide motifs, preferably 1 to 10 ethylene oxide motifs and more particularly 1 to 5 ethylene oxide motifs. Composition according to any one of claims 1 to 4, wherein the polycarboxylic acids 1b) are selected among dicarboxylic acids, tricarboxylic acids and tetracarboxylic acids, preferably among dicarboxylic acids, and preferably further among 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 le) is selected from diethanolamine, methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, viso-butyldiethanolamine, pentyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, triethanolamine, and their corresponding alkoxylation products, in particular corresponding ethoxylation products, and typically comprising from 1 to 20 ethylene oxide motifs, preferably from 1 to 10 ethylene oxide motifs and more particularly from 1 to 5 ethylene oxide motifs.
7. Composition according to any one of the preceding claims, wherein component Id) 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, wherein component 2) is selected from thiophosphoric acid, thiophosphorous acid, phosphate esters and salts of these acids, alkoxylated phosphoric esters, phosphate amines, dithiophosphates and mixtures thereof, preferably further from metal dithiocarbamates, zinc dithiophosphates, and mixtures thereof.
9. Composition according to any one of the preceding claims, wherein component 2) is selected from zinc dithiophosphates corresponding to the general formula (I): [Chem. 5] RR ' X3^ " "'S" "OR1" (|)
10. in which The radicals R10, R11, R12 and R13, each independently of each other, represent a linear, branched or cyclic hydrocarbon chain comprising from 1 to 24 carbon atoms, possibly including an aromatic ring, 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. Composition according to any one of the preceding claims, namely: the composition comprising (1) the reaction product between 5-membered ethylene oxide ethoxylated oleylamine, oleic fatty acid, oxalic acid and diethanolamine and (2) a zinc dithiophosphate, • the composition comprising (1) the product of the reaction between tallow amine, coconut fatty acid ethoxylated with 2 ethylene oxide motifs, succinic acid and rzso-butyldiethanolamine in ethylene glycol and (2) a zinc dithiophosphate, • the composition comprising (1) the product of the reaction between oleylamine ethoxylated with 2 ethylene oxide units, oleic acid, oxalic acid and diethanolamine and (2) the phosphoric ester of an oleic alcohol ethoxylated with 5 ethylene oxide units, • the composition comprising (1) the product of the reaction between tallow amine ethoxylated with 2 ethylene oxide motifs, tallow fatty acid, adipic acid and methyldiethanolamine and (2) a zinc dithiophosphate, • the composition comprising (1) the product of the reaction between tallow amine ethoxylated with 2 ethylene oxide units, tallow fatty acid, adipic acid and methyldiethanolamine and (2) the phosphoric ester of an oleic alcohol ethoxylated with 5 ethylene oxide units, • the composition comprising (1) the product of the reaction between tallow fatty acid, adipic acid and diethanolamine, quantified with methyl chloride and (2) zinc dithiophosphate, • the composition comprising (1) the product of the reaction between tallow amine ethoxylated with 2 ethylene oxide units, fatty acid of tallow, adipic acid and methyldiethanolamine, quantified with methyl chloride, and (2) the phosphoric ester of an oleic alcohol ethoxylated with 5 ethylene oxide motifs.
11. A composition according to any one of the preceding claims, wherein component 1) of the composition of the invention is a quaternized polyesteramine having the general formula (P): [Chem.6] (R5)t (R5)t R1 ( AO )x N ( AO -J R2 qJp(AO^N fAOVp—R1 0 R4 x- 0 0 R4 0 zx A (P) wherein: - R1 is a linear or branched hydrocarbon chain, saturated or unsaturated, comprising from 8 to 30 carbon atoms, preferably from 8 to 24 carbon atoms and optionally an aromatic ring, - R2 is a linear or branched alkyl chain in CrCi6, preferably in CrCi2, preferably also in C, C6, - R4 is selected from a linear or branched hydrocarbon chain, saturated or unsaturated, preferably saturated, and having from 1 to 7 carbon atoms, preferably from 1 to 6 carbon atoms and a chain -(CH2CH2O)]PH,where p represents an integer from 1 to 10, preferably from 1 to 5, - R5 represents a hydrocarbon chain, linear or branched, comprising from 1 to 6 carbon atoms and optionally substituted by an aromatic radical, - AO represents an alkoxy group chosen from ethoxy, propoxy, and butoxy, preferably AO represents an ethoxy group -(CH2CH2O)-, - x is an integer from 1 to 10, preferably from 1 to 5, -1 is equal to 0 or 1, - p represents an integer from 1 to 15, preferably from 1 to 10 and preferably again from 1 to 5, and - X represents 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, inclusive, preferably between 0.1% and 15% by mass, inclusive, preferably again between 0.1% and 10% by mass, inclusive, better still between 0.1% and 5% by mass, inclusive, 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 lubricant formulations for parts in relative motion, for electric current-generating coils, internal combustion or electric vehicle motors, motor vehicles, for metal milling and cutting systems, in fuel compositions.