Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
  • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
  • C10M129/68—Esters
  • C10M129/72—Esters of polycarboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
  • C10M105/32—Esters
  • C10M105/36—Esters of polycarboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
  • C10M2207/2825—Esters of (cyclo)aliphatic oolycarboxylic acids used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/02—Pour-point; Viscosity index
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/74—Noack Volatility

Definitions

• Cooling and/or lubricating composition for at least one element of a mobile or stationary system
• the present invention relates to the field of compositions for cooling and/or lubricating at least one element of a mobile or stationary system.
• the present invention relates in particular to compositions for cooling and/or lubricating a heavy or light vehicle, a public works machine, stationary systems such as energy storage systems, charging stations, chargers, data centers, 5G antennas, photovoltaic panels, wind turbines, turbines, switching devices, inverters and medical devices. It aims in particular to propose a cooling and/or lubricating composition compatible with its implementation at the level of transmissions in thermal engines and/or reducers in electric motors.
• a battery is an electricity-generating device in which chemical energy is converted into electrical energy.
• the chemical energy consists of electrochemically active compounds deposited on at least one face of electrodes arranged in the electrochemical generator.
• the electrical energy is produced by electrochemical reactions during a discharge of an electrochemical cell.
• a battery consists of several electrochemical cells.
• a lithium-ion electrochemical cell is based on the principle of reversible insertion of lithium into a host structure in an electrochemically active manner.
• the temperature of the cells In the field of electrochemical cells such as lithium-ion cells, the temperature of the cells must be managed in order to maintain the temperature within an adequate range of the cell.
• the term “electric vehicle” means a vehicle comprising an electric motor as the sole means of propulsion, whereas a hybrid vehicle comprises a combustion engine and an electric motor as combined means of propulsion.
• the term “propulsion system” means a system comprising the mechanical parts required for the propulsion of an electric vehicle.
• the propulsion system thus more particularly includes an electric motor comprising the rotor-stator assembly of the power electronics (dedicated to speed regulation), a transmission (also called a reducer, and when the reducer is attached to the motor, it is then referred to as a geared motor) and a battery.
• the battery itself is generally made up of a set of electrical accumulators, called cells.
• Lubricating compositions have been proposed to ensure the dual function of lubrication and cooling.
• Lubricating compositions are conventionally composed of one or more base oils, to which are generally associated several additives dedicated to boosting the lubricating performance of the base oils, such as for example friction modifier additives.
• document WO 2018/078290 proposes to implement, for cooling and/or lubricating a motorization system of an electric vehicle, a composition comprising at least one polyalkylene glycol obtained by polymerization or copolymerization of alkylene oxides comprising from 2 to 8 carbon atoms.
• the invention aims precisely to propose a new composition, suitable for its implementation for the cooling and/or lubrication of at least one element of a mobile or stationary system, of the propulsion systems of electric or hybrid vehicles, in particular to reduce the fuel consumption of a vehicle equipped with a transmission member.
• the present invention thus relates to the use of a composition comprising one or more diester(s) of formula (1), for cooling and/or lubricating at least one element of a mobile and/or stationary system,
• R represents a divalent alkylene or alkenylene radical, linear or branched, containing from 2 to 8 carbon atoms;
• R 1 and R 2 represent, independently of one another, a monovalent hydrocarbon radical optionally comprising one or more heteroatoms, it being understood that at least one of R 1 and R 2 comprises at least one ether function.
• R 1 and R 2 have one or more of the following characteristics:
• R 1 and/or R 2 comprise(s) from 1 to 6 ether functions, preferably from 1 to 4 ether functions, even more preferably from 1 to 3 ether functions;
• R 1 and/or R 2 contain(s) from 2 to 20 carbon atoms, preferably from 3 to 16 carbon atoms, even more preferably from 8 to 10 carbon atoms;
• R 1 and/or R 2 are chosen from a radical of formula (CHR 3 CH2O)nR 4 , where R 3 represents a hydrogen atom or a methyl, preferably a hydrogen atom; R 4 represents an alkyl having from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, preferably chosen from a methyl, an ethyl, a propyl or a butyl; and n is an integer ranging from 1 to 4, preferably from 1 to 3;
• R 1 and/or R 2 are chosen from CH3(CH2)3O(CH2)2-, CH3(CH2)3(OCH2CH2)2-, CH3(OCH 2 CH 2 )3- and CH3(CH2)3(OCH 2 CH 2 )3-.
• the radical R is chosen from the radicals -(CH2) X -, x ranging, more preferably from 2 to 8, even more preferably x ranging from 4 to 7.
• said diester(s) of formula (1) is (are) formed between: - two alcohols R 1 -OH and R 2 -OH, identical or different, at least one of said alcohols comprising at least one ether function, and
• dicarboxylic acid R[C(O)OH]2 comprising a linear or branched alkyl or alkenyl chain comprising 4 to 8 carbon atoms.
• said diester(s) is (are) chosen from:
• diester formed from a mono-, di- or tri-ethylene glycol monoalkyl ether and succinic acid
• a diester formed from a mono-, di- or tri-ethylene glycol monoalkyl ether and adipic acid
• diester formed from a mono-, di- or tri-ethylene glycol monoalkyl ether and glutaric acid
• diester formed from a mono-, di- or tri-ethylene glycol monoalkyl ether and pimelic acid
• diester formed from a mono-, di- or tri-ethylene glycol monoalkyl ether and suberic acid
• a diester formed from a mono-, di- or tri-ethylene glycol monoalkyl ether and azelaic acid
• a diester formed from a mono-, di- or tri-ethylene glycol monoalkyl ether and sebacic acid, and mixtures thereof, said alkyl group preferably having from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, more preferably from 1 to 4 carbon atoms.
• said diester(s) of formula (1) are formed from at least one alcohol chosen from monoethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether and triethylene glycol monobutyl ether.
• said diester of formula (1) has a kinematic viscosity at 100°C ranging from 1 to 6 mm 2 /s, preferably ranging from 1 to 5 mm 2 /s.
• the composition used according to the invention comprises at least 5% by mass, preferably at least 10% by mass, more preferably from 10% to 100% of said diester(s), relative to the total mass of the composition.
• the composition used according to the invention comprises, in addition to said diester(s), at least one additive chosen from antioxidants, pour point lowering additives, anti-foaming agents, anti-corrosion agents, anti-wear and/or extreme pressure additives, friction modifiers, detergents, dispersing agents, viscosity index improvers, thickeners, copper passivating agents and mixtures thereof, preferably said at least one additive is chosen from viscosity index improvers, pour point lowering additives, anti-wear additives, antioxidants and mixtures thereof.
• at least one additive chosen from antioxidants, pour point lowering additives, anti-foaming agents, anti-corrosion agents, anti-wear and/or extreme pressure additives, friction modifiers, detergents, dispersing agents, viscosity index improvers, thickeners, copper passivating agents and mixtures thereof.
• the composition used according to the invention comprises: from 5 to 90% by mass, preferably from 10 to 70% by mass, more preferably from 10 to 50% by mass, of said diester(s) of formula (1),
• the base oil(s) preferably representing a proportion of 10 to 95% by mass, preferably 30 to 90% by mass, more preferably 50 to 90% by mass
• the additive(s) preferably representing a proportion of up to 20% by mass, preferably 0.05 to 15% by mass, more preferably 0.1 to 10% by mass, even more preferably 0.5 to 7% by mass, or even 1 to 5% by mass, relative to the total mass of the composition.
• the diester according to the invention is formed between a dicarboxylic acid chosen from succinic acid, adipic acid, glutaric acid, pimelic acid, suberic acid, azelaic acid, sebacic acid and mixtures thereof, and a mono-, di- or tri-ethylene glycol monoalkyl ether, in particular when said diester of formula (1) is formed with at least one alcohol chosen from monoethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether and triethylene glycol monobutyl ether, the composition comprising the diester exhibits both very good thermal properties and very good lubricating properties (in friction and in traction) compared to the diesters of the prior art.
• a dicarboxylic acid chosen from succinic acid, adipic acid, glutaric acid, pimelic acid, suberic acid, azelaic acid, sebacic acid and mixtures thereof
• composition comprising a diester according to the invention surprisingly makes it possible to cool at least one element of a mobile or stationary system, the composition comprising the diester having both very good thermal conductivity and a good pour point compared to the diesters of the prior art.
• composition comprising a diester according to the invention can be advantageously used to simultaneously cool and lubricate at least one element of a mobile or stationary system as defined in the present invention.
• the diesters according to the invention make it possible to simultaneously obtain a pour point below -20°C (or even below -30°C) and a thermal conductivity at 30°C of at least 150 mW.m'fK' 1 (or even at least 155 mW.m'hK' 1 ), while having improved lubrication properties (lower coefficients of friction and traction).
• the mobile or stationary system is selected from a heavy or light vehicle, public works machinery, an energy storage system, charging stations, chargers, data centers, 5G type antennas, photovoltaic panels, wind turbines, turbines, switching devices, inverters and medical devices, or a combination of these systems.
• the composition is used to lubricate and/or cool transmissions in thermal engines and/or reducers in electric motors of a mobile system.
• the mobile system is a vehicle with a thermal engine, the composition being used to reduce the fuel consumption of said vehicle equipped with a transmission member, in particular a gearbox and/or an axle, lubricated using this composition.
• the mobile system is an electric or hybrid vehicle, the composition being used to improve the efficiency of reducers in electric motors.
• the mobile system is an electric or hybrid vehicle, the composition being used to extend the battery life of the electric or hybrid vehicle and/or to cool the battery and/or the power electronics of the electric or hybrid vehicle, in particular a lithium-ion or nickel-cadmium battery.
• the present invention makes it possible to provide diesters having excellent properties, in particular the diesters according to the invention having both very good thermal properties and very good lubricating properties (in friction and traction).
• FIG 1 schematically represents an electric or hybrid vehicle propulsion system.
• the invention relates to the use of a composition comprising one or more diester(s) of formula (1), for cooling and/or lubricating at least one element of a mobile and/or stationary system,
• R represents a divalent alkylene or alkenylene radical, linear or branched, containing from 2 to 8 carbon atoms;
• R 1 and R 2 represent, independently of one another, a monovalent hydrocarbon radical optionally comprising one or more heteroatoms, it being understood that at least one of R 1 and R 2 comprises at least one ether function.
• the invention relates to the use of a composition comprising one or more diester(s) of formula (1), for cooling at least one element of a mobile and/or stationary system,
• R represents a divalent alkylene or alkenylene radical, linear or branched, containing from 2 to 8 carbon atoms;
• R 1 and R 2 represent, independently of one another, a monovalent hydrocarbon radical optionally comprising one or more heteroatoms, it being understood that at least one of R 1 and R 2 comprises at least one ether function.
• the invention relates to the use of a composition comprising one or more diester(s) of formula (1), for cooling at least one element of a mobile and/or stationary system,
• R represents a divalent alkylene or alkenylene radical, linear or branched, containing from 2 to 8 carbon atoms;
• R 1 and R 2 represent, independently of each other, a monovalent hydrocarbon radical optionally comprising one or more heteroatoms, it being understood that at least one of R 1 and R 2 comprises at least one ether function, said diester(s) of formula (1) being formed with at least one alcohol chosen from monoethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether and triethylene glycol monobutyl ether.
• the invention relates to a use of a composition comprising one or more diester(s) of formula (1), for cooling and/or lubricating at least one element of a mobile and/or stationary system, [Chem 1] in which
• R represents a divalent alkylene or alkenylene radical, linear or branched, containing from 2 to 8 carbon atoms;
• R 1 and R 2 represent, independently of each other, a monovalent hydrocarbon radical optionally comprising one or more heteroatoms, it being understood that at least one of R 1 and R 2 comprises at least one ether function, use in which the mobile system is a vehicle with a thermal engine, the composition being used to reduce the fuel consumption of said vehicle equipped with a transmission member, in particular of a gearbox and/or an axle, lubricated by means of this composition; and/or the mobile system is an electric or hybrid vehicle, the composition being used to improve the efficiency of the reducers in electric motors; and/or the mobile system is an electric or hybrid vehicle, the composition being used to extend the autonomy of the battery of the electric or hybrid vehicle and/or to cool the battery and/or the power electronics of the electric or hybrid vehicle, in particular a lithium-ion or nickel-cadmium battery.
• said diester(s) have a kinematic viscosity at 100°C ranging from 1 to 6 mm 2 /s.
• the invention can use one or more diesters, each of said diesters being formed between: two alcohols R 1 -OH and R 2 -OH, identical or different, at least one of said alcohols comprising at least one ether function, and a dicarboxylic acid R[C(O)OH]2 comprising a linear or branched alkyl or alkenyl chain, comprising from 4 to 8 carbon atoms.
• a mixture of diesters used according to the invention by reacting a dicarboxylic acid with a mixture of alcohols, preferably chosen from mono-alcohols and diols.
• diol we mean a compound containing (exactly) two hydroxyl (-OH) functions.
• alcohol comprising at least one ether function is meant a compound comprising at least one hydroxyl function (-OH) and at least one ether function (-O-).
• compound comprising at least one ether function is meant that the compound comprises at least one oxygen atom linked by single bonds to two carbon atoms.
• diester formed between two alcohols and a dicarboxylic acid means a compound obtained by two esterification reactions, each esterification reaction being carried out between one of the two carboxylic functions of the diacid and a hydroxyl function of one of the two alcohols.
• At least one of the two alcohols comprises at least one ether function, the other alcohol being able to be an aliphatic alcohol or an alcohol comprising at least one ether function.
• the alcohols comprising at least one ether function may be identical or different.
• aliphatic alcohol is meant an alcohol devoid of heteroatoms except for the oxygen atom forming the hydroxyl function.
• the mixture of diesters falling within the scope of the present invention is likely to comprise:
• At least one of said diester(s) used according to the invention is (are) typically formed between two alcohols and a dicarboxylic acid, at least one alcohol comprising at least one ether function.
• a diester according to the invention is defined by the formula (1):
• R represents a divalent alkylene or alkenylene radical, linear or branched, containing from 2 to 8 carbon atoms;
• R 1 and R 2 represent, independently of one another, a monovalent hydrocarbon radical optionally comprising one or more heteroatoms, it being understood that at least one of R 1 and R 2 comprises at least one ether function.
• the term “monovalent hydrocarbon radical” means a linear or branched alkyl or alkenyl chain, optionally comprising one or more heteroatoms, in particular one or more oxygen atoms.
• R 1 or R 2 do not contain any heteroatom.
• R 1 and/or R 2 comprise at least one heteroatom, preferably from 1 to 6 heteroatoms, preferentially from 1 to 4 heteroatoms, even more preferentially from 1 to 3 heteroatoms.
• R 1 and/or R 2 comprise at least one oxygen atom, preferably from 1 to 6 oxygen atoms, preferentially from 1 to 4 oxygen atoms, even more preferentially from 1 to 3 oxygen atoms,
• R 1 and/or R 2 comprise(s) from 1 to 6 ether functions, preferably from 1 to 4 ether functions, even more preferably from 1 to 3 ether functions.
• R 1 and/or R 2 comprise a hydroxyl function.
• the hydroxyl function of R 1 and/or R 2 is carried by a primary carbon atom.
• a carbon atom is said to be primary when it is linked to only one other carbon atom.
• the radicals R 1 and/or R 2 are chosen independently of one another from a radical of formula -(CHR 3 CH2O) n R 4 , where R 3 represents a hydrogen atom or a methyl, preferably a hydrogen atom; R 4 represents an alkyl having from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, preferably chosen from a methyl, an ethyl, a propyl or a butyl; and n is an integer ranging from 1 to 4, preferably from 1 to 3.
• R 1 and/or R 2 are independently selected from 043(042)30(042)2-, 043(042)3(0042042)2-, 043(0042042)3- and 043(042)3(0042042)3-. According to a particular embodiment, R 1 and R 2 are identical.
• radicals R 1 and R 2 are radicals resulting from the reaction of two alcohols of formula R 1 -OH and R 2 -OH, identical or different, with a diacid, at least one alcohol among R 1 -OH and R 2 -OH comprises at least one ether function.
• Said alcohols R 1 -OH and R 2 -OH, identical or different, can be chosen from monoalcohols and diols, preferably monoalcohols.
• said at least one alcohol comprising an ether function is chosen from a monoethylene glycol monoalkyl ether, a diethylene glycol monoalkyl ether or a triethylene glycol monoalkyl ether, preferably from a diethylene glycol monoalkyl ether or a triethylene glycol monoalkyl ether, said alkyl groups preferably having from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, more preferably from 1 to 4 carbon atoms.
• said at least one alcohol is chosen from a diethylene glycol monoalkyl ether or a triethylene glycol monoalkyl ether, the alkyl groups are from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, more preferably from 1 to 4 carbon atoms.
• the alcohols used according to the invention may be commercially available or synthesized according to any method known to those skilled in the art.
• divalent alkylene radical means a saturated, linear or branched hydrocarbon chain, consisting of carbon and hydrogen atoms (therefore not containing any heteroatoms).
• the term “divalent alkenylene radical” means an unsaturated, linear or branched hydrocarbon chain, consisting of carbon and hydrogen atoms (therefore not containing any heteroatoms).
• the radical R contains from 2 to 8 carbon atoms, more preferably from 3 to 8 carbon atoms, even more preferably from 4 to 7 carbon atoms.
• R is chosen from the radicals -(CH2) X -, x being an integer ranging from 2 to 8, even more preferably x ranges from 4 to 7.
• said diesters are formed from the same dicarboxylic acid.
• all the radicals R of the diesters of formula (1) are identical.
• dicarboxylic acid is meant an acid comprising (exactly) 2 carboxyl functions -(C(O)OH).
• the dicarboxylic acid comprises a linear or branched alkylene or alkenylene chain comprising 4 to 8 carbon atoms, preferably a linear or branched alkyl chain comprising 4 to 8 carbon atoms, more preferably a linear alkyl chain comprising 4 to 8 carbon atoms.
• the dicarboxylic acid is chosen from succinic acid, adipic acid, glutaric acid, pimelic acid, suberic acid, azelaic acid, sebacic acid and mixtures thereof, preferentially from azelaic acid and adipic acid.
• dicarboxylic acids used according to the invention may be commercially available or synthesized according to any method known to those skilled in the art.
• composition according to the invention comprises at least one diester of formula (1) in which:
• the radical R contains from 2 to 8 carbon atoms, more preferably from 3 to 8 carbon atoms, even more preferably from 4 to 7 carbon atoms.
• the invention uses at least one diester of formula (1) formed between: two alcohols R 1 -OH and R 2 -OH, identical or different, at least one of said alcohols comprising at least one ether function, and a dicarboxylic acid R[C(O)OH]2 comprising a linear or branched alkylene or alkenylene chain, comprising from 4 to 8 carbon atoms.
• the diester(s) used according to the invention is (are) saturated.
• saturated diester means a diester comprising saturated hydrocarbon chains where the carbon-carbon bonds are single carbon-carbon bonds.
• the alcohols used according to the invention each comprise a saturated hydrocarbon chain and the dicarboxylic acids used according to the invention each comprise a saturated hydrocarbon chain, preferably, said hydrocarbon chain is made up of carbon and hydrogen atoms.
• the diester of formula (1) used according to the invention consists of carbon atoms, oxygen atoms and hydrogen atoms.
• the diester comprises from 12 to 60 carbon atoms, preferably from 16 to 50 carbon atoms.
• the diester used in the invention is a linear or branched diester.
• branched diester means a diester comprising a branched hydrocarbon chain, said branching being able to be located between the two ester functions and/or at one or both ends of the diester.
• the diester used in the invention is a linear diester.
• the diester used in the invention is saturated and linear.
• At least one diester of formula (1) used according to the invention is chosen from:
• diester formed from a triethylene glycol monoalkyl ether and suberic acid
• a diester formed from a triethylene glycol monoalkyl ether and sebacic acid, and mixtures thereof, said alkyl group preferably having from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, more preferably from 1 to 4 carbon atoms.
• At least one diester of formula (1) used according to the invention is chosen from:
• diester formed from a triethylene glycol monobutyl ether and sebacic acid, and mixtures thereof.
• At least one diester of formula (1) used according to the invention is chosen from:
• kinematic viscosity may be measured according to ASTM D445.
• the invention thus relates, according to another of its aspects, to a cooling and/or lubricating composition, in particular capable of cooling a propulsion system, in particular the engine or the geared motor, the battery and/or the power electronics of an electric or hybrid vehicle, said composition comprising (i) at least one diester as defined above, and (ii) at least one antioxidant additive.
• a cooling and/or lubricating composition according to the invention may also comprise at least one additive improving the viscosity index (VI).
• the friction-modifying additive may be chosen from a compound providing metallic elements and an ash-free compound.
• the compounds providing metallic elements mention may be made of transition metal complexes such as Mo, Sb, Sn, Fe, Cu, Zn, the ligands of which may be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or phosphorus atoms.
• the ash-free friction-modifying additives are generally of organic origin and may be chosen from fatty acid and polyol monoesters, alkoxylated amines, alkoxylated fatty amines, fatty epoxides, borate fatty epoxides; fatty amines or fatty acid glycerol esters.
• the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms.
• a cooling and/or lubricating composition according to the invention may comprise at least one detergent additive.
• Detergent additives generally reduce the formation of deposits on the surface of metal parts by dissolving secondary oxidation and combustion products.
• the detergent additives are preferably chosen from alkali metal or alkaline earth metal salts of carboxylic acids, sulfonates, salicylates, naphthenates, as well as phenate salts.
• the alkali and alkaline earth metals are preferably calcium, magnesium, sodium or barium.
• metal salts generally comprise the metal in stoichiometric quantity or in excess, therefore in a quantity greater than the narrow stoichiometric quantity.
• overbased detergent additives the excess metal providing the overbased character to the detergent additive is then generally in the form of a metal salt insoluble in oil, for example a carbonate, a hydroxide, an oxalate, an acetate, a glutamate, preferably a carbonate.
• a cooling and/or lubricating composition may for example comprise from 2 to 4% by weight of detergent additive, relative to the total weight of the composition.
• a cooling and/or lubricating composition may also include at least one pour point depressant additive.
• pour point depressant additives By slowing the formation of paraffin crystals, pour point depressant additives generally improve the cold behavior of the composition.
• pour point depressant additives include polyalkyl methacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes, alkylated polystyrenes.
• the cooling and/or lubricating composition according to the invention may, for example, comprise from 0.05 to 2% by mass of pour point lowering additive, relative to the total mass of the composition.
• cooling and/or lubricating composition according to the invention may comprise at least one dispersing agent.
• the dispersing agent may be selected from Mannich bases, succinimides and their derivatives.
• a cooling composition may, for example, comprise from 0.2 to 10% by weight of dispersing agent, relative to the total weight of the composition.
• the cooling and/or lubricating composition according to the invention comprises, or even consists of (i) at least one diester corresponding to formula (I) as defined above and (ii) at least one additive chosen from antioxidants, anti-foaming agents, pour point lowering additives, anti-corrosion agents, anti-wear and/or extreme pressure additives, friction modifiers, detergents, dispersing agents and mixtures thereof, preferably from antioxidants, pour point lowering additives, anti-foaming agents and anti-corrosion agents, and mixtures thereof.
• a cooling and/or lubricating composition according to the invention is formed (i) from at least one diester corresponding to formula (I) as defined above and (ii) from at least one antioxidant additive.
• the diester(s) used according to the invention may be used with one or more additional base oils and/or one or more additives.
• the composition will preferably comprise: from 5 to 90% by mass, preferably from 10 to 70% by mass, more preferably from 10 to 50% by mass, of diester(s) corresponding to formula (1),
• the base oil(s) preferably representing a proportion of 10 to 95% by mass, preferably 30 to 90% by mass, more preferably 50 to 90% by mass
• the additive(s) preferably representing a proportion of up to 20% by mass, preferably 0.05 to 15% by mass, more preferably 0.1 to 10% by mass, even more preferably 0.5 to 7% by mass, or even 1 to 5% by mass, relative to the total mass of the composition.
• the composition comprises: from 5 to 90% by mass, preferably from 10 to 70% by mass, more preferably from 10 to 50% by mass, of diester(s) corresponding to formula (1),
• one or more base oils different from said diester(s) preferably in a proportion of 10 to 95% by mass, preferably 30 to 90% by mass, more preferably 50 to 90% by mass,
• the composition according to the invention comprises, or even consists of: from 5 to 90% by mass, preferably from 10 to 70% by mass, more preferably from 10 to 50% by mass, of diester(s) corresponding to formula (1) in which: the radicals R 1 and/or R 2 are chosen independently of one another from -(CHR 3 CH2O) n R 4 , where R 3 represents a hydrogen atom or a methyl, preferably a hydrogen atom; R 4 represents an alkyl having from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, preferably chosen from a methyl, an ethyl, a propyl or a butyl; and n is an integer ranging from 1 to 4, preferably from 1 to 3, the radical R comprises from 2 to 8 carbon atoms, more preferably from 3 to 8 carbon atoms, even more preferably from 4 to 7 carbon atoms;
• one or more base oils different from said diester(s) preferably in a proportion of 10 to 95% by mass, preferably 30 to 90% by mass, more preferably 50 to 90% by mass;
• a cooling and/or lubricating composition according to the invention comprises, or even consists of:
• additives chosen from friction modifying additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressants (PPD), dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivators, and mixtures thereof, the contents being expressed relative to the total mass of said composition.
• a cooling and/or lubricating composition according to the invention comprises, or even consists of: from 5 to 90% by mass, preferably from 10 to 70% by mass, more preferably from 10 to 50% by mass, of diester(s) corresponding to formula (1),
• one or more base oils different from said diesters preferably in a proportion of 10 to 95% by mass, preferably 30 to 90% by mass, more preferably 50 to 90% by mass; optionally up to 20% by mass, preferably from 0.05 to 15% by mass, more preferably from 0.1 to 10% by mass, even more preferably from 0.5 to 7% by mass, or even from 1 to 5% by mass, of one or more additives chosen from friction modifying additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressants (PPD), dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivators, and mixtures thereof, the contents being expressed relative to the total mass of said composition.
• one or more additives chosen from friction modifying additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressants (PPD), dispersants, anti-foaming agents,
• a cooling and/or lubricating composition according to the invention comprises, or even consists of:
• additives distinct from the diester and distinct from the base oil(s), among friction modifying additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, viscosity point lowering additives, flow (PPD), dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof, the contents being expressed relative to the total mass of said composition.
• a cooling and/or lubricating composition according to the invention advantageously has a kinematic viscosity, measured at 100°C, ranging from 1 to 6 mm 2 /s, preferably from 1 to 5 mm 2 /s.
• a cooling and/or lubricating composition according to the invention advantageously has a kinematic viscosity, measured at 40°C, ranging from 5 to 20 mm 2 /s, preferably from 8 to 18 mm 2 /s.
• the cooling and/or lubricating composition according to the invention can be prepared by mixing the ingredients according to any method known to those skilled in the art.
• composition according to the invention can be implemented as a cooling and/or lubricating fluid for a mobile and/or stationary system.
• the mobile or stationary system can be chosen from a heavy or light vehicle, public works machinery, an energy storage system, charging stations, chargers, data centers, 5G antennas, photovoltaic panels, wind turbines, turbines, switching devices, inverters and medical devices, or a combination of these systems.
• the composition can be used to lubricate and/or cool transmissions in thermal engines and/or reducers in electric motors of a mobile system.
• the mobile system is a vehicle with a thermal engine, the cooling and/or lubricating composition then preferably being used to reduce the fuel consumption of said vehicle equipped with a transmission member, in particular a gearbox and/or an axle, lubricated using this composition.
• the composition according to the invention is implemented in an electric vehicle as a single fluid in the entire lubrication system in said electric vehicle.
• the lubricating composition is implemented to lubricate and cool all the organs of the propulsion system of the electric vehicle.
• a system according to the invention may be a propulsion system of an electric or hybrid vehicle, the composition then preferably being used to improve the efficiency of the reducers in the electric motors and/or to extend the autonomy of the battery of the electric or hybrid vehicle and/or to cool the battery and/or the power electronics of the electric or hybrid vehicle, in particular a lithium-ion or nickel-cadmium battery.
• the propulsion system of an electric or hybrid vehicle includes in particular the electric motor part (1), an electric battery (2) and a transmission, and in particular a speed reducer (3).
• the electric motor typically comprises power electronics (11) connected to a stator (13) and a rotor (14).
• the stator comprises coils, in particular copper coils, which are alternately supplied with an electric current. This makes it possible to generate a rotating magnetic field.
• the rotor itself comprises coils, permanent magnets or other magnetic materials, and is rotated by the rotating magnetic field.
• the power electronics (11), stator (13) and rotor (14) of a propulsion system (1) are parts whose structure is complex and generates a large amount of heat during operation of the engine. It is therefore imperative to ensure cooling of the electric motor and the power electronics.
• a bearing (12) is generally integrated between the stator (13) and the rotor (14).
• a transmission, and in particular a speed reducer (3) makes it possible to reduce the rotation speed at the output of the electric motor and to adapt the speed transmitted to the wheels, allowing at the same time to control the speed of the vehicle.
• a composition according to the invention can be implemented to cool the battery of an electric or hybrid vehicle or the batteries of an energy storage system. In particular, according to this embodiment, it is intended to be placed in direct contact with the battery or batteries.
• Li-ion batteries or nickel-cadmium batteries As batteries suitable for the propulsion systems of an electric or hybrid vehicle, we can cite in particular Li-ion batteries or nickel-cadmium batteries.
• the invention also relates, according to another of its aspects, to a method for cooling and/or lubricating at least one element of a mobile and/or stationary system, said method comprising at least one step of bringing at least said element into contact with a composition comprising one or more diester(s) of formula (1) according to the invention.
• composition implemented within the framework of the methods according to the invention may comprise one or more of the characteristics described within the framework of the lubricating and/or cooling composition according to the invention.
• the mobile or stationary system can be chosen from heavy or light vehicles, public works machinery, energy storage systems, charging stations, chargers, data centers, 5G antennas, photovoltaic panels, wind turbines, turbines, switching devices, inverters and medical devices, or a combination of these systems.
• the invention also relates, according to another of its aspects, to a method for cooling at least one part of a propulsion system of an electric or hybrid vehicle, in particular the battery, comprising at least one step of bringing at least said part, in particular said battery, for example a lithium-ion or nickel-cadmium battery, into contact with a composition comprising at least one diester of formula (1) according to the invention, as defined above.
• Bringing the cooling composition according to the invention into contact with the battery may consist of immersion or semi-immersion of the battery in said composition or even injection of said composition onto the surface of the battery.
• immersion is meant that the entire battery is surrounded by the cooling composition according to the invention.
• sub-immersion is meant that only a portion of the battery is in contact with said composition.
• Cooling can be implemented by any method known to those skilled in the art.
• the battery can be immersed or semi-immersed, static or circulating, in said composition.
• Examples of direct contact include cooling by injection, jet, spraying, immersion or semi-immersion in a bath, or by forming a mist from the composition according to the invention under pressure and by gravity on the battery.
• the composition is injected by jet under fairly high pressure into the areas to be cooled of the propulsion system.
• the shear resulting from this injection makes it possible to reduce the viscosity of the fluid at the injection zone, compared to the kinematic viscosity at rest, and thus to further increase the cooling potential of the composition.
• oil circulation systems commonly used in electric motors may be employed, as for example described in WO 2015/116496.
• a composition according to the invention can also be used to cool the electric motor of an electric or hybrid vehicle, in particular to cool the power electronics and/or the rotor and/or the stator of the electric motor and/or the geared motor.
• the cooling composition according to the invention has in particular electrical insulation properties which are particularly satisfactory for use in electric or hybrid vehicles.
• composition according to the invention can simultaneously be used to lubricate the various parts of a stationary or mobile system such as a propulsion system of an electric or hybrid vehicle, in particular bearings located between the rotor and stator of an electric motor, or the transmission, in particular the reducer, in an electric or hybrid vehicle.
• a stationary or mobile system such as a propulsion system of an electric or hybrid vehicle, in particular bearings located between the rotor and stator of an electric motor, or the transmission, in particular the reducer, in an electric or hybrid vehicle.
• a cooling composition according to the invention advantageously further comprises one or more additives chosen from anti-wear additives, friction modifiers, detergents, dispersants, extreme pressure additives, and mixtures thereof.
• Diester A diester formed from succinic acid and a diethylene glycol monobutyl ether with the following molar proportions: 2 moles of diethylene glycol monobutyl ether and 1 mole of succinic acid;
• Diester B diester formed from adipic acid and a diethylene glycol monobutyl ether with the following molar proportions: 2 moles of diethylene glycol monobutyl ether and 1 mole of adipic acid;
• Diester C diester formed from azelaic acid and a diethylene glycol monobutyl ether with the following molar proportions: 2 moles of diethylene glycol monobutyl ether and 1 mole of azelaic acid;
• Diester D diester formed from glutaric acid and a diethylene glycol monobutyl ether with the following molar proportions: 2 moles of diethylene glycol monobutyl ether and 1 mole of glutaric acid;
• Diester E diester formed from azelaic acid and a triethylene glycol monomethyl ether with the following molar proportions: 2 moles of triethylene glycol monomethyl ether and 1 mole of azelaic acid;
• - Diester F mixture of diesters formed from azelaic acid and a triethylene glycol monobutyl ether with the following molar proportions: 2 moles of triethylene glycol monobutyl ether and 1 mole of azelaic acid
• - Diester G diester formed from azelaic acid and a monoethylene glycol monobutyl ether with the following molar proportions: 2 moles of monoethylene glycol monobutyl ether and 1 mole of azelaic acid;
• Diester H diester formed from succinic acid and a triethylene glycol monobutyl ether with the following molar proportions: 2 moles of triethylene glycol monobutyl ether and 1 mole of succinic acid;
• Diester I diester formed from adipic acid and a monoethylene glycol monohexyl ether with the following molar proportions: 2 moles of monoethylene glycol monohexyl ether and 1 mole of adipic acid; monoester formed from a monocarboxylic acid comprising a saturated hydrocarbon chain of 3 to 14 carbon atoms; and a monoalcohol comprising a saturated hydrocarbon chain of 3 to 14 carbon atoms.
• the diesters and monoester were prepared according to known methods of ester preparation.
• compositions tested in the following examples comprise 100% of each ester (diester or monoester) defined in this example 1.
• the kinematic viscosity at 100°C (KV100) and the kinematic viscosity at 40°C (KV40) of the compounds of Example 1 were determined according to ASTM D445.
• Viscosities are shown in Table 2.
• the thermal conductivity of the compounds described in Example 1 was determined according to ASTM D7896-19 at 30°C.
• the diesters used according to the invention have good thermal properties, which allows their use as a cooling fluid. Indeed, the diesters have a thermal conductivity greater than 150 mW. m' 1 . K' 1 or even at least 155 mW.m'hK' 1 .
• the tribometer may be a device for setting a steel ball and a steel plane in relative motion in order to determine the friction coefficients for a given lubricant composition, while varying various properties such as speed, load, and temperature.
• the hardened steel plane is of AISI 52100 reference with a mirror finish and the ball is also of AISI 52100 reference made of hardened steel.
• the diester B has a lower coefficient of friction than the diester I which implies better lubrication properties, thus allowing in particular to reduce fuel consumption or to extend the battery life, but also a lower coefficient of traction than the diester I and this whatever the SRR implying that the friction between metal parts are further reduced which results in a greater gain in terms of fuel economy.

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• Chemical & Material Sciences (AREA)
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• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Lubricants (AREA)

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• 2023
  • 2023-04-26 FR FR2304228A patent/FR3148239A1/fr active Pending
• 2024
  • 2024-04-25 EP EP24722028.8A patent/EP4702111A1/de active Pending
  • 2024-04-25 WO PCT/EP2024/061485 patent/WO2024223793A1/fr not_active Ceased
  • 2024-04-25 CN CN202480027750.XA patent/CN121002157A/zh active Pending

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