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WO2024013127A1 - Diester-based lubricant composition - Google Patents

Diester-based lubricant composition Download PDF

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Publication number
WO2024013127A1
WO2024013127A1 PCT/EP2023/069110 EP2023069110W WO2024013127A1 WO 2024013127 A1 WO2024013127 A1 WO 2024013127A1 EP 2023069110 W EP2023069110 W EP 2023069110W WO 2024013127 A1 WO2024013127 A1 WO 2024013127A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
diester
additives
propanediol
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2023/069110
Other languages
French (fr)
Inventor
Delphine CROZET
Alice LIMOGES
Laurent Dalix
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
TotalEnergies Onetech SAS
Original Assignee
TotalEnergies Onetech SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by TotalEnergies Onetech SAS filed Critical TotalEnergies Onetech SAS
Priority to EP23736152.2A priority Critical patent/EP4555051A1/en
Priority to CN202380051891.0A priority patent/CN119563012A/en
Priority to JP2025500911A priority patent/JP2025522001A/en
Priority to KR1020257004405A priority patent/KR20250035001A/en
Publication of WO2024013127A1 publication Critical patent/WO2024013127A1/en
Priority to MX2025000404A priority patent/MX2025000404A/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32Esters
    • C10M105/38Esters of polyhydroxy compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68Esters
    • C10M129/74Esters of polyhydroxy compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/283Esters of polyhydroxy compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/283Esters of polyhydroxy compounds
    • C10M2207/2835Esters of polyhydroxy compounds used as base material
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01Physico-chemical properties
    • C10N2020/02Viscosity; Viscosity index
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02Pour-point; Viscosity index
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08Resistance to extreme temperature
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/54Fuel economy
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64Environmental friendly compositions
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/04Oil-bath; Gear-boxes; Automatic transmissions; Traction drives

Definitions

  • the present invention relates to the field of compositions for lubricating and/or cooling parts of mobile or stationary systems, such as heavy or light vehicles, public works machinery, or energy storage devices. It concerns more particularly the use of new compounds of the diester type in cooling and/or lubricating compositions, particularly used in heavy or light vehicles, public works machinery, or energy storage devices.
  • Lubricating compositions also called “lubricants” are commonly used in the various components of motor vehicles for the main purposes of reducing the friction forces between the different metal parts moving in these components, in particular the engine, the transmission and the hydraulic circuit. They are also effective in preventing premature wear or even damage to these parts, and in particular to their surface.
  • a lubricating composition is conventionally composed of a base oil to which are generally associated several additives dedicated to stimulating the lubricating performance of the base oil, such as for example friction modifier additives, but also to providing additional performance.
  • Lubricating compositions for transmissions must meet numerous requirements, particularly with regard to the strict specifications imposed by automobile manufacturers. In particular, they must have satisfactory properties in terms of viscosity, viscosity-temperature resistance, cold performance, etc. adapted to their implementation at the level of a transmission member, in particular at the level of the gearbox or the bridges, in a vehicle.
  • Lubricating compositions also called cooling compositions
  • WO 2010/038147 proposes, to generate fuel savings, to formulate lubricating compositions for gearboxes, using at least 30% by weight of a or several methyl esters of fatty acids of formula RCOOCH3, where R is a paraffinic or olefinic group containing from 11 to 23 carbon atoms, in combination with one or more anti-wear and/or extreme pressure additives phosphorus, sulfur or phosphosulfur and polyalphaolefins.
  • the present invention aims to provide a new lubricating composition, having improved properties in terms of friction reduction or cooling properties.
  • the present invention also aims to propose a new lubricating composition, having improved properties in terms of fuel economy (“Fuel Eco” properties), while satisfying the properties required for its implementation for the lubrication of transmission components of motor vehicles, light or heavy, for example gearbox and axles, and in particular having good performance in terms of cold properties.
  • Fuel Eco Fuel economy
  • the subject of the present invention is thus a lubricating composition
  • a lubricating composition comprising: One or more diesters, each of said diesters being formed between: o a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising from 3 to 10 carbon atoms, and o two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms, and at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, point lowering additives (PPD), dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof.
  • a diol chosen from 1,2-propanediol, 1,2-de
  • the lubricating composition according to the invention comprises: from 5 to 95% by weight, preferably from 10 to 90% by weight, more preferably from 20 to 80% by weight, even more preferably from 30 to 70% by weight , or even from 40 to 60% by weight of said diester(s), from 1 to 95% by weight, preferably from 10 to 90% by weight, more preferably from 20 to 80% by weight, even more preferably from 30 to 70% by weight, or even from 40 to 60% by weight of one or more base oils different from said diesters, optionally from 0.01 to 20% by weight, preferably from 0.05 to 15% by weight, more preferably from 0.1 to 10% by weight , even more preferably from 0.5 to 7% by weight, or even from 1 to 5% by weight of one or more additives distinct from the diester and distinct from the base oil(s), relative to the total mass of the composition.
  • the lubricating composition according to the invention comprises: at least 5% by weight, preferably at least 10% by weight, preferably at least 30% by weight, preferably at least 50% by weight, more preferably at least 70% by weight, or even at least 90% by weight, of one or more diesters; from 0.01 to 20% by weight, preferably from 0.05 to 15% by weight, more preferably from 0.1 to 10% by weight, even more preferably from 0.5 to 7% by weight, or even from 1 to 5% mass, of one or more additives chosen from friction modifier additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, additives pour point depressants (PPDs), dispersants, antifoaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof; And
  • said diester contains from 13 to 25 carbon atoms, preferably from 13 to 24 carbon atoms.
  • said diester has a kinematic viscosity at 100°C ranging from 1 to 6 mm 2 /s, preferably ranging from 1 to 4 mm 2 /s.
  • the diol is chosen from 1,2-propanediol, 1,2-decanediol and 1,3-alkanediol containing from 3 to 7 carbon atoms, preferably from 1,2-propanediol and 1, 3-propanediol, more preferably the diol is 1,2-propanediol.
  • said monocarboxylic acids identical or different, comprise a linear hydrocarbon chain comprising from 4 to 10 carbon atoms, preferably from 5 to 9 carbon atoms.
  • said diester(s) is(are) chosen from: a diester formed from 1,2-decanediol and two heptanoic acids, a diester formed from 1,2-decanediol and two pentanoic acids, a diester formed from 1,2-propanediol and two heptanoic acids, a diester formed from 1,2-propanediol and two nonanoic acids, a diester formed from 1,3-propanediol and two heptanoic acids, a diester formed from 1,2-propanediol and two octanoic acids, a diester formed from 1,2-propanediol and two decanoic acids, a diester formed from 1,2-propanediol and an octanoic acid and a decanoic acid, and mixtures thereof.
  • the lubricating composition according to the invention comprises:
  • two monocarboxylic acids identical or different, comprising a linear or branched hydrocarbon chain comprising 4 to 10 carbon atoms, o a diester formed from 1,2-propanediol and two heptanoic acids, o a diester formed from 1,2-propanediol and two octanoic acids, o a diester formed from 1,2-propanediol and two decanoic acids, o a diester formed from 1,2-propanediol and an octanoic acid and a decanoic acid, and mixtures thereof, and at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti-wear additives, extreme pressure additives , detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents, thickeners, corrosion inhibitors, anti-f
  • the invention also relates to the use of at least one diester in a lubricating composition, said diester being formed between: a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising from 3 to 10 carbon atoms, and two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms, said lubricating composition further comprising at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti-wear additives, extreme pressure additives, detergents , antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents , and their mixtures.
  • a diol chosen from 1,2-propanediol, 1,2-decanedio
  • said at least one diester is used to lubricate and/or cool at least one element of a mobile or stationary system, chosen for example from a heavy or light vehicle, a public works machine, and a energy storage system.
  • the mobile system is a vehicle, the lubricating composition being used to reduce the fuel consumption of a vehicle equipped with a transmission member, in particular a gearbox and/or a bridge, lubricated with means of this composition.
  • a transmission member in particular a gearbox and/or a bridge
  • the diester used in the use according to the invention is as defined in the context of the lubricating composition according to the invention and/or the lubricating composition used in the use according to the invention is such as defined in the context of the lubricating composition according to the invention.
  • the invention relates to the use of at least one diester in a lubricating composition for lubricating and/or cooling at least one element of a mobile or stationary system chosen from a public works machine and a energy storage system, said diester being formed between:
  • a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising 3 to 10 carbon atoms, and two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms
  • said lubricating composition further comprising at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti- wear, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents, thickeners, corrosion inhibitors, passivating agents copper, and their mixtures.
  • friction modifier additives anti- wear, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents, thickeners,
  • the invention relates to the use of at least one diester in a lubricating composition for lubricating and/or for cooling at least one element of a mobile system, said mobile system being a vehicle, said diester being formed between:
  • said lubricating composition further comprising at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti- wear, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof, said lubricating composition being used to reduce the fuel consumption of a vehicle equipped with a transmission member, in particular a gearbox and/or a bridge, lubricated using this composition.
  • a transmission member in particular a gearbox and/or a bridge
  • the invention relates to a lubricating composition
  • a lubricating composition comprising: at least one diester formed between: o a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising from 3 to 10 carbon atoms, and o two monocarboxylic acids, identical or different, comprising a linear hydrocarbon chain or branched comprising from 4 to 10 carbon atoms, and at least one ingredient chosen from base oils distinct from the diester, additives distinct from the diester, and mixtures thereof, when present said additive being chosen from friction modifier additives , anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents , thickeners, corrosion inhibitors, copper passivators, and mixtures thereof.
  • a diol chosen from 1,2-propanediol, 1,2-decane
  • the lubricating composition according to the invention may comprise one or more diesters, each of said diesters being formed between: o a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising from 3 to 10 carbon atoms, and o two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising 5 to 10 carbon atoms.
  • the mixture of diesters falling within the scope of the present invention is likely to comprise:
  • the diester(s) used according to the invention is(are) formed between a diol and two monocarboxylic acids.
  • diester formed between a diol and two monocarboxylic acids within the meaning of the present invention, is meant a compound obtained by two esterification reactions, each esterification reaction being carried out between one of the two alcohol functions of the diol and the acid function of one of the two monocarboxylic acids.
  • the diester contains from 13 to 25 carbon atoms, preferably from 15 to 24 carbon atoms.
  • the diol used in the invention is among 1,2-propanediol, 1,2-decanediol and 1,3-diol containing 3 to 10 carbon atoms.
  • diol we mean a compound comprising (exactly) two hydroxyl functions (-OH).
  • 1,3-diol comprising from X to Y carbon atoms
  • hydrocarbon chain within the meaning of the invention, we mean an alkyl or alkylene chain, linear or branched, saturated or unsaturated.
  • the hydrocarbon chain can optionally be interrupted by one or more heteroatoms, in particular by one or more oxygen atoms.
  • the hydrocarbon chain is an alkyl or alkylene chain, linear or branched, saturated or unsaturated, consisting of carbon and hydrogen atoms.
  • the 1,3-diol comprising 3 to 10 carbon atoms is chosen from 1,3-alkanediol comprising 3 to 10 carbon atoms.
  • 1,3-alkanediol comprising from X to Y carbon atoms
  • a diol whose alcohol functions are located respectively in position 1 and in position 3 of an alkane chain comprising from
  • the diol is chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising from 3 to 7 carbon atoms, preferably from 1,2-propanediol and 1,3-alkanediol containing 3 to 7 carbon atoms, more preferably among 1,2-propanediol and 1,3-propanediol, advantageously the diol is 1,2-propanediol.
  • the diol used according to the invention may be available commercially or synthesized according to any method known to those skilled in the art.
  • the diol used according to the invention comprises a carbon content of biological origin of at least 60% by mass, preferably at least 70% by mass, more preferably at least 80%. by mass, even more preferably at least 90% by mass, relative to the total mass of the carbon atoms of the diol.
  • the carbon content of biological origin can be measured according to the ASTM D6866 standard.
  • the diester used according to the invention is obtained from two identical or different monocarboxylic acids.
  • monocarboxylic acid is meant a compound comprising a single carboxyl function (-COOH).
  • the carboxylic acids used to form a diester of the invention are chosen from monocarboxylic acids, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms, preferably from 5 to 9 carbon atoms, more preferably from 5 to 8 carbon atoms.
  • the linear or branched hydrocarbon chain of the monocarboxylic acids is saturated.
  • the monocarboxylic acids identical or different, comprise a linear hydrocarbon chain comprising from 5 to 10 carbon atoms, preferably from 5 to 9 carbon atoms, more preferably from 5 to 8 carbon atoms.
  • the monocarboxylic acids identical or different, comprise a linear and saturated hydrocarbon chain comprising from 5 to 10 carbon atoms, preferably from 5 to 9 carbon atoms, more preferably from 5 to 8 carbon atoms .
  • the monocarboxylic acids used according to the invention may be commercially available or synthesized according to any method known to those skilled in the art.
  • the monocarboxylic acids used according to the invention comprise a carbon content of biological origin of at least 60% by mass, preferably at least 70% by mass, more preferably at least 80% by mass. % by mass, even more preferably at least 90% by mass, relative to the total mass of the carbon atoms of the monocarboxylic acids.
  • the diester used according to the invention is saturated.
  • saturated diester within the meaning of the invention is meant a diester comprising saturated hydrocarbon chains.
  • the diol used according to the invention comprises a saturated hydrocarbon chain and the monocarboxylic acids used according to the invention each comprise a saturated hydrocarbon chain, preferably, said hydrocarbon chain consists of atoms carbon and hydrogen.
  • the diester used in the invention is a branched diester.
  • branched diester within the meaning of the invention is meant a diester comprising a branched hydrocarbon chain which can be located between the two ester functions and/or at one or both ends of the diester.
  • the diester used in the invention is saturated and branched.
  • the diester used according to the invention has a kinematic viscosity, measured at 100°C according to the ASTM D445 standard, ranging from 1 to 6 mm 2 /s, preferably from 1 to 4 mm 2 / s.
  • the diester used according to the invention has a kinematic viscosity, measured at 40°C according to the ASTM D445 standard, ranging from 2 to 20 mm 2 /s, preferably from 3 to 10 mm 2 / s. It is understood that the definitions given above for carboxylic acid and alcohol may be combined, where possible, to define other particular embodiments.
  • a diester used according to the invention may correspond more particularly to one of the following formulas (I), (II) or (III): [Chem 1] in which :
  • R 1 represents a hydrocarbon chain, linear or branched, saturated or unsaturated, preferably saturated, having from 3 to 9 carbon atoms, preferably from 4 to 8 carbon atoms, preferably from 5 to 7 carbon atoms, said hydrocarbon chain being optionally interrupted by one or more heteroatoms, such as oxygen atoms, preferably the hydrocarbon chain consists of carbon and hydrogen atoms;
  • R 2 represents a hydrocarbon chain, linear or branched, saturated or unsaturated, preferably saturated, having from 3 to 9 carbon atoms, preferably from 4 to 8 carbon atoms, preferably from 5 to 7 carbon atoms, said hydrocarbon chain being optionally interrupted by one or more heteroatoms, such as oxygen atoms, preferably the hydrocarbon chain is made up of carbon and hydrogen atoms.
  • the diester(s) corresponding to formula (I), (II) or (III) contain from 13 to 25 carbon atoms, preferably from 15 to 24 carbon atoms.
  • R 1 and R 2 may be identical or different.
  • the diester(s) used according to the invention is(are) chosen from: a diester formed from 1,2-decanediol and two heptanoic acids, a diester formed from 1,2-decanediol and two pentanoic acids, a diester formed from 1,2-propanediol and two heptanoic acids, a diester formed from 1,2-propanediol and two nonanoic acids, a diester formed from 1,3-propanediol and two heptanoic acids, a diester formed from 1,2-propanediol and two octanoic acids, a diester formed from 1,2-propanediol and two decanoic acids, a diester formed from 1,2-propanediol and a mixture of acids including octanoic acid and decanoic acid, and mixtures thereof.
  • the diesters according to the invention can be prepared according to synthesis methods known to those skilled in the art. These synthesis methods more particularly implement two esterification reactions, each esterification reaction being implemented between an alcohol function of the diol and the acid function of the monocarboxylic acid.
  • a diester according to the invention can be in the form of a mixture of at least two diesters according to the invention, in particular as defined above.
  • the diester used according to the invention comprises a carbon content of biological origin of at least 60% by mass, preferably at least 70% by mass, more preferably at least 80%. by mass, even more preferably at least 90% by mass, relative to the total mass of the carbon atoms of the diester.
  • the carbon content of biological origin can be measured according to the ASTM D6866 standard.
  • the diester or mixture of diesters according to the invention may represent at least 5% by weight of the composition according to the invention, preferably at least 10% by weight, preferably at least 30% by weight, more preferably at least 50% by weight. , even more preferably at least 70% by weight, in particular at least 80% by weight, more particularly at least 90% by weight, or even at least 95% by weight, of the total mass of the composition according to the invention.
  • the diester(s) according to the invention can be used with one or more additional base oils (also called co-bases).
  • the composition will comprise: from 5 to 95% by weight, preferably from 5 to 50% by weight, more preferably 10 to 40% by weight, of the diester(s) according to the invention, and from 5 to 95% by mass, preferably from 50 to 95% by mass, preferably from 60 to 90% by mass, of one or more base oils different from the diesters according to the invention, relative to the mass total of diester(s) and base oils other than diesters.
  • a lubricating composition according to the invention may comprise at least 30% by weight of a diester or mixture of diesters according to the invention, more particularly between 50% and 99.5% by weight, preferably between 70%. and 99% by weight, more preferably between 80% and 99% by weight, or even between 80% and 95% by weight, relative to the total mass of said composition.
  • a lubricating composition according to the invention can be formed at more than 95% by weight, in particular at more than 98% by mass, of one or more diesters according to the invention.
  • the composition according to the invention is a composition comprising 100% by mass of a mixture of diester(s) defined in the invention and additional base oil(s). ), preferably in a proportion such that the composition comprises: from 5 to 95% by weight, preferably from 5 to 50% by weight, more preferably 10 to 40% by weight, of the diester(s) according to the invention, and from 5 to 95% by mass, preferably from 50 to 95% by mass, preferably from 60 to 90% by mass, of one or more base oils different from the diesters according to the invention, relative to the mass total composition.
  • This embodiment is particularly advantageous when the composition is used for cooling, as a cooling fluid.
  • the lubricating composition according to the invention may comprise, in addition to one or more diesters according to the invention, one or more base oils distinct from the diesters according to the invention, called “additional base oil”.
  • Said base oil(s), possibly present in the lubricating composition according to the invention, are chosen adequately, with regard to their compatibility with said diester(s) used according to the invention.
  • It can be a mixture of several base oils, for example a mixture of two, three or four base oils.
  • the base oil or mixture of additional base oils, used in the lubricating composition according to the invention can have a kinematic viscosity, measured at 100 ° C according to the ASTM D445 standard, ranging from 1, 5 to 8 mm 2 /s, in particular 1.5 to 6.1 mm 2 /s, more particularly 1.5 to 4.1 mm 2 /s, even more particularly 1.5 to 2.1 mm 2 /s.
  • the base oils can be chosen from oils of mineral or synthetic origin belonging to groups I to V according to the classes defined in the API classification (or their equivalents according to the ATIEL classification) and presented in table 1 below or their mixtures.
  • Mineral base oils include all types of base oils obtained by atmospheric and vacuum distillation of crude oil, followed by refining operations such as solvent extraction, desalphating, solvent dewaxing, hydrotreating, hydrocracking, hydroisomerization and hydrofinishing .
  • Blends of synthetic and mineral oils, which can be biosourced, can also be used.
  • the base oils can also be chosen from synthetic oils, such as certain esters of carboxylic acids and alcohols, distinct from Tester defined according to the invention, from polyalphaolefins (PAO), and from polyalkylene glycol (PAG) obtained by polymerization or copolymerization of alkylene oxides comprising from 2 to 8 carbon atoms, in particular from 2 to 4 carbon atoms.
  • synthetic oils such as certain esters of carboxylic acids and alcohols, distinct from Tester defined according to the invention, from polyalphaolefins (PAO), and from polyalkylene glycol (PAG) obtained by polymerization or copolymerization of alkylene oxides comprising from 2 to 8 carbon atoms, in particular from 2 to 4 carbon atoms.
  • the PAOs used as base oils are for example obtained from monomers comprising 4 to 32 carbon atoms, for example from octene or decene.
  • the weight average molecular weight of PAO can vary quite widely. Preferably, the mass average molecular weight of the PAO is less than 600Da.
  • the mass average molecular mass of the PAO can also range from 100 to 600 Da, from 150 to 600 Da, or even from 200 to 600 Da.
  • the PAOs implemented in the context of the invention having a kinematic viscosity, measured at 100 ° C according to the ASTM D445 standard, ranging from 1.5 to 8 mm 2 /s are sold commercially by Ineos under the brands Durasyn® 162, Durasyn® 164, Durasyn® 166 and Durasyn® 168.
  • the additional base oil or oils are chosen from polyalphaolefins (PAO).
  • a composition according to the invention may comprise from 5 to 95% by weight, preferably from 50 to 95% by weight, more preferably from 60 to 90% by weight, of one or more base oils different from the diesters according to the invention, relative to the total mass of said composition.
  • the lubricating composition according to the invention may optionally also comprise one or more additives known to those skilled in the art in the field of lubrication, in particular for vehicle transmissions, in particular for transmissions of light or heavy vehicles.
  • additives may be chosen in particular from friction modifier additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant additives. (PPD), dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof.
  • the lubricating composition according to the invention may further comprise one or more additives chosen from antioxidants, anti-foaming agents, pour point improvers and anti-corrosion agents. It is understood that the nature and quantity of additives used are chosen so as not to affect the properties of the lubricating composition conferred by the diester according to the invention.
  • additives can be introduced individually and/or in the form of a mixture like those already available for sale for commercial lubricant formulations for vehicle engines, with a performance level as defined by the ACEA ( Association of European Automobile Manufacturers) and/or the API (American Petroleum Institute), well known to those skilled in the art.
  • ACEA Association of European Automobile Manufacturers
  • API American Petroleum Institute
  • Said additive(s) may be present in the lubricating composition according to the invention in a content less than or equal to 10% by weight, in particular less than or equal to 5% by weight, and more particularly ranging from 0.01 to 3% by weight, for example relative to the total mass of said composition.
  • a lubricating composition according to the invention can thus comprise at least one antioxidant additive.
  • the invention thus relates, according to one of its aspects, to a lubricating composition
  • a lubricating composition comprising (i) at least one diester as defined above, and (ii) at least one antioxidant additive.
  • the antioxidant additive generally makes it possible to delay the degradation of the composition in service. This degradation can notably result in the formation of deposits, the presence of sludge or an increase in the viscosity of the composition.
  • Antioxidant additives act in particular as free radical inhibitors or hydroperoxide destroyers.
  • antioxidant additives can generate ash.
  • Phenolic antioxidant additives can be ash-free or in the form of neutral or basic metal salts.
  • the antioxidant additives may in particular be chosen from sterically hindered phenols, sterically hindered phenol esters and sterically hindered phenols comprising a thioether bridge, diphenylamines, diphenylamines substituted by at least one C1-C12 alkyl group, N,N'-dialkyl-aryl-diamines and their mixtures.
  • the sterically hindered phenols are chosen from compounds comprising a phenol group of which at least one vicinal carbon of the carbon carrying the alcohol function is substituted by at least one C1-C10 alkyl group, preferably a CI-C6 alkyl group. , preferably a C4 alkyl group, preferably the tert-butyl group.
  • Amino compounds are another class of antioxidant additives that can be used, possibly in combination with phenolic antioxidant additives.
  • amino compounds are aromatic amines, for example aromatic amines of formula NR 5 R 6 R 7 in which R 5 represents an aliphatic group or an aromatic group, optionally substituted, R 6 represents an aromatic group, optionally substituted, R 7 represents a hydrogen atom, an alkyl group, an aryl group or a group of formula R 8 S(O) Z R 9 in which R 8 represents an alkylene group or an alkenylene group, R 9 represents an alkyl group, a alkenyl group or an aryl group and z represents 0, 1 or 2.
  • Sulfurized alkyl phenols or their alkali and alkaline earth metal salts can also be used as antioxidant additives.
  • a lubricating composition comprises at least one ash-free antioxidant additive.
  • Said additive(s) can be used, in a lubricating composition according to the invention, at a rate of 0.1 to 2% by weight, relative to the total mass of the composition.
  • a lubricating composition according to the invention may comprise at least one anti-wear additive, an extreme pressure additive or mixtures thereof.
  • Anti-wear additives and extreme pressure additives protect rubbing surfaces by forming a protective film adsorbed on these surfaces.
  • the anti-wear additives are chosen from phosphosulfur additives such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP.
  • phosphosulfur additives such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP.
  • the preferred compounds are of formula Zn((SP(S)(OQ 2 )(OQ 3 ))2, in which Q 2 and Q 3 , identical or different, represent independently an alkyl group, preferably an alkyl group comprising from 1 to 18 carbon atoms.
  • the lubricating composition according to the invention is free from phosphite type esters containing sulfur of formula
  • R is a C4 to C20 hydrocarbon group containing sulfur and R 1 is hydrogen, a C4 to C20 hydrocarbon group or a C4 to C20 hydrocarbon group containing sulfur.
  • Amine phosphates are also anti-wear additives which can be used in a composition according to the invention.
  • the phosphorus provided by these additives can act as a poison in the catalytic systems of automobiles because these additives generate ash.
  • additives which do not provide phosphorus such as, for example, polysulphides, in particular sulfur-containing olefins.
  • a lubricating composition may comprise from 0.01 to 6% by weight, preferably from 0.05 to 4% by weight, more preferably from 0.1 to 2% by weight of anti-wear additives and extreme pressure additives, by weight per relative to the total mass of composition.
  • a lubricating composition according to the invention may further comprise an anti-foaming agent.
  • the anti-foaming agent can be chosen from silicones.
  • a lubricating composition may comprise from 0.01 to 2% by weight or from 0.01 to 5% by weight, preferably from 0.1 to 1.5% by weight or from 0.1 to 2% by weight of antifoaming agent, relative to to the total mass of the composition.
  • a lubricating composition according to the invention may comprise at least one friction modifier additive.
  • Friction modifier additives make it possible to limit friction by forming monolayers adsorbed on the surfaces of metals in contact with them. They can be chosen from compounds providing metallic elements and compounds free of ash. Among the compounds providing metallic elements, we can cite transition metal complexes such as Mo, Sb. Sn, Fe, Cu, Zn whose ligands can be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or phosphorus atoms.
  • the ash-free friction modifier additives are generally of organic origin and can be chosen from esters of fatty acids and polyols, distinct from the monoester required according to the invention, alkoxylated amines, alkoxylated fatty amines, fatty epoxides.
  • the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms.
  • the molybdenum-based compounds can be chosen from molybdenum dithiocarbamates (Mo-DTC), molybdenum dithiophosphates (Mo-DTP), and mixtures thereof.
  • a lubricating composition may in particular comprise a molybdenum content of between 1000 and 2500 ppm.
  • a lubricating composition may comprise from 0.01 to 5% by weight, more particularly from 0.1 to 2% by weight or even more particularly from 0.1 to 1.5% by weight of friction modifier additive, relative to the mass total composition.
  • a lubricating composition according to the invention preferably comprises less than 1.5% by weight of molybdenum, more preferably less than 1% by weight, relative to the total mass of the composition, or is even free from molybdenum.
  • a lubricating composition according to the invention may comprise at least one detergent additive.
  • Detergent additives generally help reduce the formation of deposits on the surface of metal parts by dissolving secondary oxidation and combustion products.
  • the detergent additives which can be used in a lubricating composition are generally known to those skilled in the art.
  • the detergent additives can be anionic compounds comprising a lipophilic hydrocarbon group and a hydrophilic head.
  • the associated cation may be a metallic cation of an alkali or alkaline earth metal.
  • 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 include the metal in stoichiometric quantity or in excess, therefore in 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 lubricating composition can for example comprise 2 to 4% by weight of detergent additive, relative to the total mass of the composition.
  • a lubricating composition may also comprise at least one pour point depressant additive (also called “PPD” agent for “Pour Point Depressant” in English).
  • PPD 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 mention may be made of polyalkyl methacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes, alkylated polystyrenes.
  • a lubricating composition according to the invention may comprise from 0.1% to 2%, preferably from 0.2% to 1% by weight of pour point depressant additive(s), relative to the mass. total composition. Also, a lubricating composition may comprise at least one dispersing agent.
  • the dispersing agent can be chosen from Mannich bases, succinimides and their derivatives, such as polyisobutylene succinic anhydride derivatives.
  • a lubricating composition can for example comprise from 0.2 to 10% by weight of dispersing agent, relative to the total mass of the composition.
  • a lubricating composition according to the invention may also comprise at least one additive improving the viscosity index (VI).
  • Viscosity index improvers in particular viscosity index improving polymers, make it possible to guarantee good cold resistance and minimum viscosity at high temperatures.
  • polymers improving the viscosity index mention may be made of polymer esters, homopolymers or copolymers, hydrogenated or non-hydrogenated, of styrene, butadiene and isoprene, homopolymers or copolymers of olefin, such as such as ethylene or propylene, polyacrylates and polymethacrylates (PMA), preferably olefin homopolymers or copolymers, such as ethylene or propylene.
  • polymer esters homopolymers or copolymers, hydrogenated or non-hydrogenated, of styrene, butadiene and isoprene
  • olefin such as such as ethylene or propylene
  • PMA polymethacrylates
  • a lubricating composition according to the invention may comprise from 1 to 15% by weight of additive(s) improving the viscosity index, preferably from 5% to 10% by weight, relative to the total mass of the composition. lubricating.
  • a lubricating composition may also comprise at least one antifoam additive, for example chosen from polar polymers such as polymethylsiloxanes or polyacrylates.
  • a lubricating composition according to the invention may comprise from 0.01 to 3% by weight of anti-foam additive(s), relative to the total mass of the lubricating composition.
  • It may also include at least one anti-corrosion agent or copper passivating agent, for example compounds such as polyisobutenes succinic anhydrides, thiadiazole sulfonates or mercaptobenzothiazoles. They are typically present in a lubricating composition according to the invention at contents of between 0.01% and 1% by weight, relative to the total mass of the composition.
  • at least one anti-corrosion agent or copper passivating agent for example compounds such as polyisobutenes succinic anhydrides, thiadiazole sulfonates or mercaptobenzothiazoles.
  • a lubricating composition according to the invention comprises one or more additives chosen from viscosity index improving agents, pour point lowering agents, anti-wear agents and antioxidant agents.
  • a lubricating composition according to the invention comprises, or even is formed of (i) at least one diester according to the invention and (ii) at least one additive chosen from antioxidants, viscosity index improving additives, pour point depressant additives, anti-wear and/or extreme pressure additives, antifoams, detergents, dispersants, and mixtures thereof, preferably among anti-oxidants, viscosity index improving additives, pour point depressant additives, anti-wear and/or extreme pressure additives, and mixtures thereof.
  • a lubricating composition according to the invention is formed of (i) at least one diester corresponding to one of formulas (I), (II) or (III) as defined above and (ii) at least an antioxidant additive.
  • a lubricating composition according to the invention is formed of (i) at least one diester corresponding to one of formulas (I) or (II) as defined above and (ii) at least one anti- oxidant.
  • composition according to the invention comprises, or even consists of:
  • additives friction modifiers from 0.01 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 the additives friction modifiers, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, agents defoamers, thickeners, corrosion inhibitors, copper passivators, and mixtures thereof; And
  • composition according to the invention comprises, or even consists of:
  • a lubricating composition according to the invention comprises, or even consists of:
  • base oil(s) distinct from the diesters defined according to the invention preferably chosen from group II and/or III base oils according to the API classification ; - optionally from 5% to 15% by weight of at least one additive improving the viscosity index;
  • a lubricating composition according to the invention comprises, or even consists of:
  • diesters preferably chosen from diesters of formula (I) or (II);
  • base oil(s) distinct from the diesters defined according to the invention preferably chosen from group II and/or III base oils according to the API classification ;
  • a composition according to the invention comprises, or even consists of: from 5 to 95% by mass, preferably from 5 to 50% by mass, more preferably 10 to 40% by mass, of said or said diesters corresponding to formula (I) or (II); from 5 to 95% by weight, preferably from 50 to 95% by weight, preferably from 60 to 90% by weight, of one or more base oils different from said diesters; optionally from 0.01 to 20% by weight, preferably from 0.05 to 15% by weight, more preferably from 0.1 to 10% by weight, even more preferably from 0.5 to 7% by weight, or even from 1 to 5 % by mass, of one or more additives chosen from friction modifier additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof, the contents being expressed relative to the total
  • a composition according to the invention advantageously has a kinematic viscosity, measured at 100°C according to the ASTM D445 standard, ranging from 1 to 20 mm 2 /s, preferably from 2 to 15 mm 2 /s.
  • a composition according to the invention advantageously has a kinematic viscosity, measured at 40°C according to the ASTM D445 standard, ranging from 20 to 50 mm 2 /s, preferably from 25 to 40 mm 2 /s.
  • composition according to the invention has good lubricating properties.
  • composition according to the invention also has good properties in terms of cold resistance.
  • composition according to the invention also has good cooling properties.
  • the present invention also relates to the use of a diester in a composition for lubricating and/or cooling at least one part of a mobile or stationary system, said diester being formed between: a diol chosen from 1,2- propanediol, 1,2-decanediol and 1,3-diol comprising 3 to 10 carbon atoms, and two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising 4 to 10 carbon atoms.
  • the composition for lubricating and/or cooling further comprises at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from anti-oxidants, pour point depressant additives, anti-foam agents, anti-corrosion agents, anti-wear and/or extreme pressure additives, friction modifiers, detergents, agents dispersants and mixtures thereof, in particular among anti-oxidants, pour point depressant additives, anti-foaming agents and anti-corrosion agents.
  • additive being chosen from anti-oxidants, pour point depressant additives, anti-foam agents, anti-corrosion agents, anti-wear and/or extreme pressure additives, friction modifiers, detergents, agents dispersants and mixtures thereof, in particular among anti-oxidants, pour point depressant additives, anti-foaming agents and anti-corrosion agents.
  • the characteristic(s) of the diester presented in the context of the composition according to the invention are also applicable to the diester used according to the invention.
  • the lubricated and/or cooled part is a part of a heavy or light vehicle, a public works machine, or an energy storage device (e.g. data center).
  • the diester defined in the present invention makes it possible to reduce the friction coefficients of the lubricating composition.
  • the diester defined in the present invention makes it possible to cool the elements of a mobile or stationary system, such as a heavy or light vehicle, a public works machine, an energy storage device.
  • composition formulated according to the invention in particular as described above, has excellent tribological properties, particularly in terms of reducing friction, which makes it particularly well suited to use as a lubricating fluid.
  • composition formulated according to the invention in particular as described above, has excellent thermal properties, particularly in terms of thermal conductivity, which makes it particularly well suited to use as a cooling fluid.
  • a composition of the invention is suitable for the lubrication of transmission members of motor vehicles, in particular transmissions for light or heavy vehicles, for example gearboxes and/or axles.
  • a lubricating composition according to the invention has performances in particular in terms of cold properties, particularly well suited to its use for the transmission of heavy goods vehicles, in particular for lubricating the manual gearbox and/or the weight axles. heavy.
  • the present invention also relates to a method of lubricating and/or cooling at least one part of a mobile or stationary system, comprising bringing the composition according to the invention into contact with said part.
  • the mobile or stationary system is chosen from a heavy or light vehicle, a public works machine, an energy storage device such as a data center.
  • the present invention also relates to a method of lubricating and/or cooling at least one mechanical part, in particular a motor vehicle transmission member, comprising bringing the lubricating composition according to the invention into contact with said mechanical part. , in particular said motor vehicle transmission member.
  • the diesters defined in the invention can be added to lubricating compositions used in vehicle transmissions in order to improve their “Fuel-Eco” properties, namely their ability to limit the fuel consumption of motor vehicles, without affect their performance, particularly in terms of cold properties.
  • Diester A diester formed from 1,2-decanediol and two heptanoic acids
  • Diester B diester formed from 1,2-decanediol and two pentanoic acids
  • Diester C diester formed from 1,2-propanediol and two heptanoic acids
  • Diester D diester formed from 1,2-propanediol and two nonanoic acids
  • Diester E diester formed from 1,3-propanediol and two heptanoic acids
  • Diester F mixture of diesters formed from 1,2-propanediol and a biosourced cut of C8-C10 acids 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 ester preparation methods.
  • 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) were determined according to the ASTM D445 standard.
  • All the diesters used according to the invention have a viscosity less than 4 mm 2 /s at 100°C.
  • the tribological properties can be evaluated by a test on a rotating ball-disc tribometer (also called ball-plane) of the Linear reciprocating tribometer type. This test makes it possible in particular to evaluate the performance of lubricants in terms of friction in mixed/limit regime depending on the load, pressure or speed conditions applied.
  • a rotating ball-disc tribometer also called ball-plane
  • This test makes it possible in particular to evaluate the performance of lubricants in terms of friction in mixed/limit regime depending on the load, pressure or speed conditions applied.
  • the coefficient of friction of the lubricating compositions tested is determined at 40°C by placing a hardened steel ball of approximately 2 cm in diameter, for example 1.905 cm in diameter, on a hardened steel plane.
  • the tribometer can be a device allowing a steel ball and a steel plane to be put into relative motion in order to determine the coefficients of friction/friction for a given lubricating composition, while varying various properties such as speed, load, and temperature.
  • the hardened steel surface is reference AISI 52100 with a mirror finish and the ball is also reference AISI 52100 made from hardened steel.
  • the applied load is respectively 25 N and the driving speed varies from 10 mm/s to 2500 mm/s.
  • the coefficient of friction is in particular determined at a rotation speed of 10 mm/s.
  • the coefficient is determined at a sliding speed/drive speed ratio (“Slide-to-Roll Ratio” or %SRR) of 5%.
  • the coefficient of friction is measured and recorded via a force sensor.
  • the lubricating compositions tested comprise 100% of each ester defined in Example 1.
  • the mini flash point is measured according to the ASTM D93Ac standard (Cl eaveland open cup method).
  • the flash point is better if the diester is a branched diester.
  • the diester formed from type 1,2 propanediol has a lower flash point than the diester formed from type 1,3 propanediol, with the same number of carbon atoms in total.
  • COT coefficient of traction
  • the measurement conditions were 25 N load, a disk speed of 1.4 m/s for a rated temperature of 100 °C and an SRR of 20%.
  • the thermal conductivity of the compounds described in Example 1 was determined according to standard ASTM D7896-19 at different temperatures.

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Abstract

The present invention relates to a lubricant composition comprising: one or more diesters, each of said diesters being formed between - a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol having 3 to 10 carbon atoms, and - two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain having 4 to 10 carbon atoms; and at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction-modifying additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index improvers (VI), pour point depressant additives (PPD), dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof.

Description

Composition lubrifiante à base de diester Lubricating composition based on diester

Domaine technique Technical area

La présente invention concerne le domaine des compositions pour lubrifier et/ou refroidir des pièces de systèmes mobiles ou stationnaires, tels que les véhicules lourds ou légers, les engins de travaux publics, ou les dispositifs de stockage d’énergie. Elle concerne plus particulièrement l’utilisation de nouveaux composés de type diesters dans des compositions de refroidissement et/ou lubrifiantes notamment mis en œuvre dans les véhicules lourds ou légers, les engins de travaux publics, ou les dispositifs de stockage d’énergie. The present invention relates to the field of compositions for lubricating and/or cooling parts of mobile or stationary systems, such as heavy or light vehicles, public works machinery, or energy storage devices. It concerns more particularly the use of new compounds of the diester type in cooling and/or lubricating compositions, particularly used in heavy or light vehicles, public works machinery, or energy storage devices.

Technique antérieure Prior art

Les compositions lubrifiantes, dites encore « les lubrifiants », sont communément mises en œuvre dans les différents organes des véhicules à moteur à des fins principales de réduction des forces de frottement entre les différentes pièces métalliques en mouvement dans ces organes, en particulier le moteur, la transmission et le circuit hydraulique. Elles sont en outre efficaces pour prévenir une usure prématurée voire un endommagement de ces pièces, et en particulier de leur surface. Pour ce faire, une composition lubrifiante est classiquement composée d’une huile de base à laquelle sont généralement associés plusieurs additifs dédiés à stimuler les performances lubrifiantes de l’huile de base, comme par exemple des additifs modificateurs de frottement, mais aussi à procurer des performances supplémentaires. Lubricating compositions, also called "lubricants", are commonly used in the various components of motor vehicles for the main purposes of reducing the friction forces between the different metal parts moving in these components, in particular the engine, the transmission and the hydraulic circuit. They are also effective in preventing premature wear or even damage to these parts, and in particular to their surface. To do this, a lubricating composition is conventionally composed of a base oil to which are generally associated several additives dedicated to stimulating the lubricating performance of the base oil, such as for example friction modifier additives, but also to providing additional performance.

Les compositions lubrifiantes pour transmissions (par exemple, boîtes de vitesse ou ponts) doivent satisfaire à de nombreuses exigences, au regard notamment des spécifications strictes imposées par les constructeurs automobiles. En particulier, elles doivent présenter des propriétés satisfaisantes en termes de viscosité, de tenue viscosité-température, performances à froid, etc. adaptées à leur mise en œuvre au niveau d’un organe de transmission, notamment au niveau de la boite de vitesse ou des ponts, dans un véhicule. Lubricating compositions for transmissions (for example, gearboxes or axles) must meet numerous requirements, particularly with regard to the strict specifications imposed by automobile manufacturers. In particular, they must have satisfactory properties in terms of viscosity, viscosity-temperature resistance, cold performance, etc. adapted to their implementation at the level of a transmission member, in particular at the level of the gearbox or the bridges, in a vehicle.

Des compositions lubrifiantes aussi appelées compositions de refroidissement peuvent également être mises en œuvre dans ses dispositifs de stockage d’énergie, tels que les datacenter. Il existe un besoin de fournir des compositions lubrifiantes et/ou de refroidissement d’origine végétale renouvelable ayant un faible impact sur l’environnement. Lubricating compositions, also called cooling compositions, can also be used in energy storage devices, such as data centers. There is a need to provide lubricating and/or cooling compositions of renewable plant origin having a low impact on the environment.

En outre, les préoccupations environnementales actuelles, notamment en vue de réduire les émissions de dioxyde de carbone, induisent un besoin urgent de réduire la consommation de carburant des véhicules à moteur. A ce titre, il est connu que les compositions lubrifiantes représentent un moyen efficace pour agir sur la consommation de carburant via leur impact sur les forces de frottements générées entre les différents organes de véhicules à moteur. Ainsi, il existe un besoin de développer des lubrifiants permettant de réduire le frottement dans les boîtes de vitesses et dans les différentiels de ponts. Furthermore, current environmental concerns, particularly with a view to reducing carbon dioxide emissions, induce an urgent need to reduce the fuel consumption of motor vehicles. As such, it is known that lubricating compositions represent an effective means of acting on fuel consumption via their impact on the friction forces generated between the different components of motor vehicles. Thus, there is a need to develop lubricants to reduce friction in gearboxes and axle differentials.

Améliorer les propriétés « Fuel Eco » des lubrifiants pour transmissions, tout en conservant par ailleurs les hauts niveaux de performance requis, demeure un défi. Improving the “Fuel Eco” properties of transmission lubricants, while otherwise maintaining the high levels of performance required, remains a challenge.

A titre d’exemples de lubrifiants pour transmissions, on peut citer le document WO 2010/038147 qui propose, pour générer des économies de carburants, de formuler des compositions lubrifiantes pour boites de vitesse, mettant en œuvre au moins 30 % massique d’un ou plusieurs esters méthyliques d’acides gras de formule RCOOCH3, où R est un groupement paraffinique ou oléfinique contenant de 11 à 23 atomes de carbone, en combinaison avec un ou plusieurs additifs anti-usure et/ou extrême pression phosphorés, soufrés ou phospho soufrés et des polyalphaoléfines. As examples of lubricants for transmissions, we can cite document WO 2010/038147 which proposes, to generate fuel savings, to formulate lubricating compositions for gearboxes, using at least 30% by weight of a or several methyl esters of fatty acids of formula RCOOCH3, where R is a paraffinic or olefinic group containing from 11 to 23 carbon atoms, in combination with one or more anti-wear and/or extreme pressure additives phosphorus, sulfur or phosphosulfur and polyalphaolefins.

On peut encore citer le document US 2017/0145337 qui décrit des compositions lubrifiantes pour transmissions, présentant un gain en « Fuel Eco », à base d’une huile de base ayant une viscosité cinématique à 100°C allant de 1,5 mm2/s à 3,5 mm2/s, et comprenant de 3 % à 10 % d’une huile de type monoester de viscosité cinématique à 100°C allant de 2 mm2/s à 10 mm2/s, ainsi qu’un ester de type phosphite apportant du soufre. We can also cite document US 2017/0145337 which describes lubricating compositions for transmissions, presenting a gain in “Fuel Eco”, based on a base oil having a kinematic viscosity at 100°C ranging from 1.5 mm 2 /s to 3.5 mm 2 /s, and comprising from 3% to 10% of a monoester type oil with kinematic viscosity at 100°C ranging from 2 mm 2 /s to 10 mm 2 /s, as well as a phosphite type ester providing sulfur.

La présente invention vise à proposer une nouvelle composition lubrifiante, présentant des propriétés améliorées en termes de réduction des frottements ou des propriétés de refroidissement. The present invention aims to provide a new lubricating composition, having improved properties in terms of friction reduction or cooling properties.

La présente invention vise également à proposer une nouvelle composition lubrifiante, présentant des propriétés améliorées en termes d’économie de carburant (propriétés « Fuel Eco »), tout en satisfaisant aux propriétés requises pour sa mise en œuvre pour la lubrification des organes de transmission de véhicules automobiles, légers ou lourds, par exemple boîte de vitesse et ponts, et en particulier présentant de bonnes performances en termes de propriétés à froid. The present invention also aims to propose a new lubricating composition, having improved properties in terms of fuel economy (“Fuel Eco” properties), while satisfying the properties required for its implementation for the lubrication of transmission components of motor vehicles, light or heavy, for example gearbox and axles, and in particular having good performance in terms of cold properties.

Résumé de l’invention Summary of the invention

La présente invention a ainsi pour objet une composition lubrifiante comprenant : Un ou plusieurs diesters, chacun desdits diesters étant formé entre : o un diol choisi parmi le 1,2-propanediol, le 1,2-décanediol et les 1 ,3-diol comportant de 3 à 10 atomes de carbone, et o deux acides monocarboxyliques, identiques ou différents, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone, et au moins une huile de base distincte du diester et/ou au moins un additif distinct du diester, ledit additif étant choisi parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges. The subject of the present invention is thus a lubricating composition comprising: One or more diesters, each of said diesters being formed between: o a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising from 3 to 10 carbon atoms, and o two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms, and at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, point lowering additives (PPD), dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof.

Selon un mode de réalisation, la composition lubrifiante selon l’invention comprend : de 5 à 95% massique, de préférence de 10 à 90% massique, de préférence encore de 20 à 80% massique, encore plus préférentiellement de 30 à 70% massique, voire de 40 à 60% massique dudit ou desdits diesters, de 1 à 95% massique, de préférence de 10 à 90% massique, de préférence encore de 20 à 80% massique, encore plus préférentiellement de 30 à 70% massique, voire de 40 à 60% massique d’une ou plusieurs huiles de base différentes desdits diesters, éventuellement de 0,01 à 20% massique, de préférence de 0,05 à 15% massique, de préférence encore de 0,1 à 10% massique, encore plus préférentiellement de 0,5 à 7% massique, voire de 1 à 5% massique d’un ou plusieurs additifs distincts du diester et distincts de(s) huile(s) de base, par rapport à la masse totale de la composition. According to one embodiment, the lubricating composition according to the invention comprises: from 5 to 95% by weight, preferably from 10 to 90% by weight, more preferably from 20 to 80% by weight, even more preferably from 30 to 70% by weight , or even from 40 to 60% by weight of said diester(s), from 1 to 95% by weight, preferably from 10 to 90% by weight, more preferably from 20 to 80% by weight, even more preferably from 30 to 70% by weight, or even from 40 to 60% by weight of one or more base oils different from said diesters, optionally from 0.01 to 20% by weight, preferably from 0.05 to 15% by weight, more preferably from 0.1 to 10% by weight , even more preferably from 0.5 to 7% by weight, or even from 1 to 5% by weight of one or more additives distinct from the diester and distinct from the base oil(s), relative to the total mass of the composition.

Selon un mode de réalisation, la composition lubrifiante selon l’invention comprend : au moins 5% massique, de préférence au moins 10% massique, de préférence au moins 30% massique, de préférence au moins 50% massique, plus préférentiellement au moins 70% massique, voire au moins 90% massique, d’un ou plusieurs diesters ; de 0,01 à 20% massique, de préférence de 0,05 à 15% massique, de préférence encore de 0,1 à 10% massique, encore plus préférentiellement de 0,5 à 7% massique, voire de 1 à 5% massique, d’un ou plusieurs additifs choisi(s) parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges ; et According to one embodiment, the lubricating composition according to the invention comprises: at least 5% by weight, preferably at least 10% by weight, preferably at least 30% by weight, preferably at least 50% by weight, more preferably at least 70% by weight, or even at least 90% by weight, of one or more diesters; from 0.01 to 20% by weight, preferably from 0.05 to 15% by weight, more preferably from 0.1 to 10% by weight, even more preferably from 0.5 to 7% by weight, or even from 1 to 5% mass, of one or more additives chosen from friction modifier additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, additives pour point depressants (PPDs), dispersants, antifoaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof; And

- éventuellement de 5 à 94% massique, de préférence de 10 à 94% massique, de préférence de 15 à 90% massique d’huile(s) de base distincte(s) du diester selon l’invention, par rapport à la masse totale de la composition. - optionally from 5 to 94% by weight, preferably from 10 to 94% by weight, preferably from 15 to 90% by weight of base oil(s) distinct from the diester according to the invention, relative to the mass total composition.

De préférence, ledit diester comporte de 13 à 25 atomes de carbone, de préférence de 13 à 24 atomes de carbone. Preferably, said diester contains from 13 to 25 carbon atoms, preferably from 13 to 24 carbon atoms.

De préférence, ledit diester présente une viscosité cinématique à 100°C allant de 1 à 6 mm2/s, de préférence allant de 1 à 4 mm2/s. Preferably, said diester has a kinematic viscosity at 100°C ranging from 1 to 6 mm 2 /s, preferably ranging from 1 to 4 mm 2 /s.

De préférence, le diol est choisi parmi le 1,2-propanediol, le 1,2-décanediol et le 1,3- alcanediol comportant de 3 à 7 atomes de carbone, de préférence parmi le 1,2-propanediol et le 1,3 -propanediol, de préférence encore le diol est le 1,2-propanediol. Preferably, the diol is chosen from 1,2-propanediol, 1,2-decanediol and 1,3-alkanediol containing from 3 to 7 carbon atoms, preferably from 1,2-propanediol and 1, 3-propanediol, more preferably the diol is 1,2-propanediol.

De préférence, lesdits acides monocarboxyliques, identiques ou différents, comportent une chaîne hydrocarbonée linéaire comportant de 4 à 10 atomes de carbone, de préférence de 5 à 9 atomes de carbone. Preferably, said monocarboxylic acids, identical or different, comprise a linear hydrocarbon chain comprising from 4 to 10 carbon atoms, preferably from 5 to 9 carbon atoms.

De préférence, ledit ou lesdits diester(s) est(sont) choisi(s) parmi : un diester formé à partir de 1,2-décanediol et de deux acides heptanoïques, un diester formé à partir de 1,2-décanediol et de deux acides pentanoïques, un diester formé à partir de 1,2-propanediol et de deux acides heptanoïques, un diester formé à partir de 1,2-propanediol et de deux acides nonanoïques, un diester formé à partir de 1,3 -propanediol et de deux acides heptanoïques, un diester formé à partir de 1,2-propanediol et de deux acides octanoïques, un diester formé à partir de 1,2-propanediol et de deux acides décanoïques, un diester formé à partir de 1,2-propanediol et d’un acide octanoïque et d’un acide décanoïque, et leurs mélanges. Preferably, said diester(s) is(are) chosen from: a diester formed from 1,2-decanediol and two heptanoic acids, a diester formed from 1,2-decanediol and two pentanoic acids, a diester formed from 1,2-propanediol and two heptanoic acids, a diester formed from 1,2-propanediol and two nonanoic acids, a diester formed from 1,3-propanediol and two heptanoic acids, a diester formed from 1,2-propanediol and two octanoic acids, a diester formed from 1,2-propanediol and two decanoic acids, a diester formed from 1,2-propanediol and an octanoic acid and a decanoic acid, and mixtures thereof.

De préférence, la composition lubrifiante selon l’invention comprend : Preferably, the lubricating composition according to the invention comprises:

- Un ou plusieurs diesters choisis parmi : o Les diesters formés entre : - One or more diesters chosen from: o The diesters formed between:

• un diol choisi parmi le 1,2-décanediol et le 1,3 propanediol, et• a diol chosen from 1,2-decanediol and 1,3 propanediol, and

• deux acides monocarboxyliques, identiques ou différents, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone, o un diester formé à partir de 1,2-propanediol et de deux acides heptanoïques, o un diester formé à partir de 1,2-propanediol et de deux acides octanoïques, o un diester formé à partir de 1,2-propanediol et de deux acides décanoïques, o un diester formé à partir de 1,2-propanediol et d’un acide octanoïque et d’un acide décanoïque, et leurs mélanges, et au moins une huile de base distincte du diester et/ou au moins un additif distinct du diester, ledit additif étant choisi parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges. • two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising 4 to 10 carbon atoms, o a diester formed from 1,2-propanediol and two heptanoic acids, o a diester formed from 1,2-propanediol and two octanoic acids, o a diester formed from 1,2-propanediol and two decanoic acids, o a diester formed from 1,2-propanediol and an octanoic acid and a decanoic acid, and mixtures thereof, and at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti-wear additives, extreme pressure additives , detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents, thickeners, corrosion inhibitors, anti-foaming agents, copper passivant, and mixtures thereof.

L’invention concerne également l’utilisation d’au moins un diester dans une composition lubrifiante, ledit diester étant formé entre : un diol choisi parmi le 1,2-propanediol, le 1,2-décanediol et les 1 ,3-diol comportant de 3 à 10 atomes de carbone, et deux acides monocarboxyliques, identiques ou différents, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone, ladite composition lubrifiante comprenant en outre au moins une huile de base distincte du diester et/ou au moins un additif distinct du diester, ledit additif étant choisi parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges. The invention also relates to the use of at least one diester in a lubricating composition, said diester being formed between: a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising from 3 to 10 carbon atoms, and two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms, said lubricating composition further comprising at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti-wear additives, extreme pressure additives, detergents , antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents , and their mixtures.

Selon un mode de réalisation, ledit au moins un diester est utilisé pour lubrifier et/ou pour refroidir au moins un élément d’un système mobile ou stationnaire, choisi par exemple parmi un véhicule lourd ou léger, un engin de travaux public, et un système de stockage d’énergie. According to one embodiment, said at least one diester is used to lubricate and/or cool at least one element of a mobile or stationary system, chosen for example from a heavy or light vehicle, a public works machine, and a energy storage system.

De préférence, le système mobile est un véhicule, la composition lubrifiante étant utilisée pour réduire la consommation de carburant d’un véhicule équipé d’un organe de transmission, notamment d’une boîte de vitesses et/ou d’un pont, lubrifié au moyen de cette composition. Preferably, the mobile system is a vehicle, the lubricating composition being used to reduce the fuel consumption of a vehicle equipped with a transmission member, in particular a gearbox and/or a bridge, lubricated with means of this composition.

De préférence, le diester mis en œuvre dans l’utilisation selon l’invention est tel que défini dans le cadre de la composition lubrifiante selon l’invention et/ou la composition lubrifiante mise en œuvre dans l’utilisation selon l’invention est telle que définie dans le cadre de la composition lubrifiante selon l’invention. Preferably, the diester used in the use according to the invention is as defined in the context of the lubricating composition according to the invention and/or the lubricating composition used in the use according to the invention is such as defined in the context of the lubricating composition according to the invention.

Selon un mode de réalisation, l’invention concerne l’utilisation d’au moins un diester dans une composition lubrifiante pour lubrifier et/ou pour refroidir au moins un élément d’un système mobile ou stationnaire choisi parmi un engin de travaux public et un système de stockage d’énergie, ledit diester étant formé entre : According to one embodiment, the invention relates to the use of at least one diester in a lubricating composition for lubricating and/or cooling at least one element of a mobile or stationary system chosen from a public works machine and a energy storage system, said diester being formed between:

- un diol choisi parmi le 1,2-propanediol, le 1,2-décanediol et les 1 ,3-diol comportant de 3 à 10 atomes de carbone, et deux acides monocarboxyliques, identiques ou différents, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone, ladite composition lubrifiante comprenant en outre au moins une huile de base distincte du diester et/ou au moins un additif distinct du diester, ledit additif étant choisi parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges. - a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising 3 to 10 carbon atoms, and two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms, said lubricating composition further comprising at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti- wear, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents, thickeners, corrosion inhibitors, passivating agents copper, and their mixtures.

Selon un mode de réalisation, l’invention concerne l’utilisation d’au moins un diester dans une composition lubrifiante pour lubrifier et/ou pour refroidir au moins un élément d’un système mobile, ledit système mobile étant un véhicule, ledit diester étant formé entre : According to one embodiment, the invention relates to the use of at least one diester in a lubricating composition for lubricating and/or for cooling at least one element of a mobile system, said mobile system being a vehicle, said diester being formed between:

- un diol choisi parmi le 1,2-propanediol, le 1,2-décanediol et les 1 ,3-diol comportant de 3 à 10 atomes de carbone, et deux acides monocarboxyliques, identiques ou différents, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone, ladite composition lubrifiante comprenant en outre au moins une huile de base distincte du diester et/ou au moins un additif distinct du diester, ledit additif étant choisi parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges, ladite composition lubrifiante étant utilisée pour réduire la consommation de carburant d’un véhicule équipé d’un organe de transmission, notamment d’une boîte de vitesses et/ou d’un pont, lubrifié au moyen de cette composition. - a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising 3 to 10 carbon atoms, and two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms, said lubricating composition further comprising at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti- wear, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof, said lubricating composition being used to reduce the fuel consumption of a vehicle equipped with a transmission member, in particular a gearbox and/or a bridge, lubricated using this composition.

Dans la suite du texte, les expressions « compris entre ... et ... », « allant de . . . à . . . » et « variant de ... à ... » sont équivalentes et entendent signifier que les bornes sont incluses, sauf mention contraire. In the rest of the text, the expressions “between ... and ...”, “ranging from. . . has . . . » and “varying from ... to ...” are equivalent and are intended to mean that the limits are included, unless otherwise stated.

Sauf indication contraire, l’expression « comprenant un(e) » doit être comprise comme « comprenant au moins un(e) ». Unless otherwise indicated, the expression “comprising a(n)” must be understood as “comprising at least one(e)”.

Description détaillée detailed description

En premier lieu, l’invention concerne une composition lubrifiante comprenant : au moins un diester formé entre : o un diol choisi parmi le 1,2-propanediol, le 1,2-décanediol et les 1,3-diol comportant de 3 à 10 atomes de carbone, et o deux acides monocarboxyliques, identiques ou différents, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone, et au moins un ingrédient choisi parmi les huiles de base distinctes du diester, les additifs distincts du diester, et leurs mélanges, lorsqu’il est présent ledit additif étant choisi parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges. Firstly, the invention relates to a lubricating composition comprising: at least one diester formed between: o a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising from 3 to 10 carbon atoms, and o two monocarboxylic acids, identical or different, comprising a linear hydrocarbon chain or branched comprising from 4 to 10 carbon atoms, and at least one ingredient chosen from base oils distinct from the diester, additives distinct from the diester, and mixtures thereof, when present said additive being chosen from friction modifier additives , anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents , thickeners, corrosion inhibitors, copper passivators, and mixtures thereof.

La composition lubrifiante selon l’invention peut comprendre un ou plusieurs diesters, chacun desdits diesters étant formé entre : o un diol choisi parmi le 1,2-propanediol, le 1,2-décanediol et les 1,3-diol comportant de 3 à 10 atomes de carbone, et o deux acides monocarboxyliques, identiques ou différents, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 5 à 10 atomes de carbone. The lubricating composition according to the invention may comprise one or more diesters, each of said diesters being formed between: o a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising from 3 to 10 carbon atoms, and o two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising 5 to 10 carbon atoms.

En particulier, il est possible de préparer un mélange de diesters en faisant réagir un diol et un mélange d’acides monocarboxyliques. In particular, it is possible to prepare a mixture of diesters by reacting a diol and a mixture of monocarboxylic acids.

Par exemple, il est possible de faire réagir un diol et trois acides monocarboxyliques Al, A2 et A3. Ainsi, selon cet exemple, le mélange de diesters entrant dans le cadre de la présente invention est susceptible de comprendre : For example, it is possible to react a diol and three monocarboxylic acids Al, A2 and A3. Thus, according to this example, the mixture of diesters falling within the scope of the present invention is likely to comprise:

- un diester formé entre le diol et deux acides Al, - a diester formed between the diol and two Al acids,

- un diester formé entre le diol et deux acides A2, - a diester formed between the diol and two A2 acids,

- un diester formé entre le diol et deux acides A3, - a diester formed between the diol and two A3 acids,

- un diester formé entre le diol et un acide Al et un acide A2, - a diester formed between the diol and an Al acid and an A2 acid,

- un diester formé entre le diol et un acide Al et un acide A3, - a diester formed between the diol and an Al acid and an A3 acid,

- un diester formé entre le diol et un acide A2 et un acide A3. Diester mis en œuyre selon l ’invention - a diester formed between the diol and an A2 acid and an A3 acid. Diester used according to the invention

Comme évoqué ci-dessus, le ou les diesters mis en œuvre selon l’invention est(sont) formé(s) entre un diol et deux acides monocarboxyliques. As mentioned above, the diester(s) used according to the invention is(are) formed between a diol and two monocarboxylic acids.

Par « diester formé entre un diol et deux acides monocarboxyliques » au sens de la présente invention, on entend un composé obtenu par deux réactions d’estérification, chaque réaction d’estérification étant mise en œuvre entre une des deux fonctions alcool du diol et la fonction acide d’un des deux acides monocarboxyliques. By “diester formed between a diol and two monocarboxylic acids” within the meaning of the present invention, is meant a compound obtained by two esterification reactions, each esterification reaction being carried out between one of the two alcohol functions of the diol and the acid function of one of the two monocarboxylic acids.

Selon un mode de réalisation, le diester comporte de 13 à 25 atomes de carbone, de préférence de 15 à 24 atomes de carbone. According to one embodiment, the diester contains from 13 to 25 carbon atoms, preferably from 15 to 24 carbon atoms.

Le diol mis en œuvre dans l’invention est parmi le 1,2-propanediol, le 1,2-décanediol et les 1 ,3 -diol comportant de 3 à 10 atomes de carbone. The diol used in the invention is among 1,2-propanediol, 1,2-decanediol and 1,3-diol containing 3 to 10 carbon atoms.

Par « diol », on entend un composé comportant (exactement) deux fonctions hydroxyle (-OH). By “diol” we mean a compound comprising (exactly) two hydroxyl functions (-OH).

Par « 1,3 -diol comportant de X à Y atomes de carbone », on entend un diol dont les fonctions alcools sont situées respectivement en position 1 et en position 3 d’une chaine hydrocarbonée comportant de X à Y atomes de carbone. By “1,3-diol comprising from X to Y carbon atoms”, we mean a diol whose alcohol functions are located respectively in position 1 and in position 3 of a hydrocarbon chain comprising from X to Y carbon atoms.

Par « chaîne hydrocarbonée » au sens de l’invention, on entend désigner une chaine alkyle ou alkylène, linéaire ou ramifiée, saturée ou insaturée. La chaîne hydrocarbonée peut éventuellement être interrompue par un ou plusieurs hétéroatomes, en particulier par un ou plusieurs atomes d’oxygène. De préférence la chaîne hydrocarbonée est une chaîne alkyle ou alkylène, linéaire ou ramifiée, saturée ou insaturée, constituée d’atomes de carbone et d’hydrogène. By “hydrocarbon chain” within the meaning of the invention, we mean an alkyl or alkylene chain, linear or branched, saturated or unsaturated. The hydrocarbon chain can optionally be interrupted by one or more heteroatoms, in particular by one or more oxygen atoms. Preferably the hydrocarbon chain is an alkyl or alkylene chain, linear or branched, saturated or unsaturated, consisting of carbon and hydrogen atoms.

Selon un mode de réalisation, le 1 ,3 -diol comportant de 3 à 10 atomes de carbone est choisi parmi les 1,3-alcanediol comportant de 3 à 10 atomes de carbone According to one embodiment, the 1,3-diol comprising 3 to 10 carbon atoms is chosen from 1,3-alkanediol comprising 3 to 10 carbon atoms.

Par « 1,3-alcanediol comportant de X à Y atomes de carbone » on entend un diol dont les fonctions alcools sont situées respectivement en position 1 et en position 3 d’une chaine alcane comportant de X à Y atomes de carbone. By “1,3-alkanediol comprising from X to Y carbon atoms” is meant a diol whose alcohol functions are located respectively in position 1 and in position 3 of an alkane chain comprising from

Selon un mode de réalisation, le diol est choisi parmi le 1,2-propanediol, le 1,2- décanediol et le 1,3 -diol comportant de 3 à 7 atomes de carbone, de préférence parmi le 1,2- propanediol et 1,3-alcanediol comportant de 3 à 7 atomes de carbone, de préférence encore parmi le 1,2-propanediol et le 1,3 -propanediol, avantageusement le diol est le 1,2- propanediol. According to one embodiment, the diol is chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising from 3 to 7 carbon atoms, preferably from 1,2-propanediol and 1,3-alkanediol containing 3 to 7 carbon atoms, more preferably among 1,2-propanediol and 1,3-propanediol, advantageously the diol is 1,2-propanediol.

Le diol mis en œuvre selon l’invention peut être disponible commercialement ou synthétisé selon toute méthode connue de l’homme du métier. The diol used according to the invention may be available commercially or synthesized according to any method known to those skilled in the art.

De préférence, le diol mis en œuvre selon l’invention comprend une teneur en carbone d’origine biologique d’au moins 60% en masse, de préférence d’au moins 70% en masse, de préférence encore d’au moins 80% en masse, encore plus préférentiellement d’au moins 90% en masse, par rapport à la masse totale des atomes de carbone du diol. Preferably, the diol used according to the invention comprises a carbon content of biological origin of at least 60% by mass, preferably at least 70% by mass, more preferably at least 80%. by mass, even more preferably at least 90% by mass, relative to the total mass of the carbon atoms of the diol.

Dans le cadre de la présente invention, la teneur en carbone d’origine biologique peut être mesurée selon la norme ASTM D6866. In the context of the present invention, the carbon content of biological origin can be measured according to the ASTM D6866 standard.

Le diester mis en œuvre selon l’invention est obtenu à partir de deux acides monocarboxyliques identiques ou différents. The diester used according to the invention is obtained from two identical or different monocarboxylic acids.

Par « acide monocarboxylique », on entend un composé comportant une unique fonction carboxyle (-COOH). By “monocarboxylic acid” is meant a compound comprising a single carboxyl function (-COOH).

Les acides carboxyliques mis en œuvre pour former un diester de l’invention sont choisis parmi les acides monocarboxyliques, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone, de préférence de 5 à 9 atomes de carbone, de préférence encore de 5 à 8 atomes de carbone. De préférence, la chaîne hydrocarbonée linéaire ou ramifiée des acides monocarboxyliques est saturée. The carboxylic acids used to form a diester of the invention are chosen from monocarboxylic acids, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms, preferably from 5 to 9 carbon atoms, more preferably from 5 to 8 carbon atoms. Preferably, the linear or branched hydrocarbon chain of the monocarboxylic acids is saturated.

Selon un mode de réalisation, les acides monocarboxyliques, identiques ou différents, comportent une chaîne hydrocarbonée linéaire comportant de 5 à 10 atomes de carbone, de préférence de 5 à 9 atomes de carbone, de préférence encore de 5 à 8 atomes de carbone. According to one embodiment, the monocarboxylic acids, identical or different, comprise a linear hydrocarbon chain comprising from 5 to 10 carbon atoms, preferably from 5 to 9 carbon atoms, more preferably from 5 to 8 carbon atoms.

Selon un mode de réalisation, les acides monocarboxyliques, identiques ou différents, comportent une chaîne hydrocarbonée linéaire et saturée comportant de 5 à 10 atomes de carbone, de préférence de 5 à 9 atomes de carbone, de préférence encore de 5 à 8 atomes de carbone. Les acides monocarboxyliques mis en œuvre selon l’invention peuvent être disponibles commercialement ou synthétisés selon toute méthode connue de l’homme du métier. According to one embodiment, the monocarboxylic acids, identical or different, comprise a linear and saturated hydrocarbon chain comprising from 5 to 10 carbon atoms, preferably from 5 to 9 carbon atoms, more preferably from 5 to 8 carbon atoms . The monocarboxylic acids used according to the invention may be commercially available or synthesized according to any method known to those skilled in the art.

De préférence, les acides monocarboxyliques mis en œuvre selon l’invention comprennent une teneur en carbone d’origine biologique d’au moins 60% en masse, de préférence d’au moins 70% en masse, de préférence encore d’au moins 80% en masse, encore plus préférentiellement d’au moins 90% en masse, par rapport à la masse totale des atomes de carbone des acides monocarboxyliques. Preferably, the monocarboxylic acids used according to the invention comprise a carbon content of biological origin of at least 60% by mass, preferably at least 70% by mass, more preferably at least 80% by mass. % by mass, even more preferably at least 90% by mass, relative to the total mass of the carbon atoms of the monocarboxylic acids.

De préférence, le diester mis en œuvre selon l’invention est saturé. Preferably, the diester used according to the invention is saturated.

Par « diester saturé » au sens de l’invention, on entend un diester comportant des chaines hydrocarbonées saturées. Ainsi, de préférence, le diol mis en œuvre selon l’invention comporte une chaine hydrocarbonée saturée et les acides monocarboxyliques mis en œuvre selon l’invention comportent, chacun, une chaine hydrocarbonée saturée, de préférence, ladite chaine hydrocarbonée est constituée d’atomes de carbone et d’hydrogène. By “saturated diester” within the meaning of the invention is meant a diester comprising saturated hydrocarbon chains. Thus, preferably, the diol used according to the invention comprises a saturated hydrocarbon chain and the monocarboxylic acids used according to the invention each comprise a saturated hydrocarbon chain, preferably, said hydrocarbon chain consists of atoms carbon and hydrogen.

Selon un mode de réalisation préféré, le diester mis en œuvre dans l’invention est un diester ramifié. According to a preferred embodiment, the diester used in the invention is a branched diester.

Par « diester ramifié » au sens de l’invention, on entend un diester comportant une chaîne hydrocarbonée ramifiée qui peut être située entre les deux fonctions ester et/ou à l’une ou aux deux extrémités du diester. By “branched diester” within the meaning of the invention is meant a diester comprising a branched hydrocarbon chain which can be located between the two ester functions and/or at one or both ends of the diester.

Selon un mode de réalisation préféré, le diester mis en œuvre dans l’invention est saturé et ramifié. According to a preferred embodiment, the diester used in the invention is saturated and branched.

Selon un mode de réalisation, le diester mis en œuvre selon l’invention présente une viscosité cinématique, mesurée à 100°C selon la norme ASTM D445, allant de 1 à 6 mm2/s, de préférence de 1 à 4 mm2/s. According to one embodiment, the diester used according to the invention has a kinematic viscosity, measured at 100°C according to the ASTM D445 standard, ranging from 1 to 6 mm 2 /s, preferably from 1 to 4 mm 2 / s.

Selon un mode de réalisation, le diester mis en œuvre selon l’invention présente une viscosité cinématique, mesurée à 40°C selon la norme ASTM D445, allant de 2 à 20 mm2/s, de préférence de 3 à 10 mm2/s. Il est entendu que les définitions données ci-dessus pour l’acide carboxylique et l’alcool peuvent être combinées, dans la mesure du possible, pour définir d’autres modes de réalisation particuliers. According to one embodiment, the diester used according to the invention has a kinematic viscosity, measured at 40°C according to the ASTM D445 standard, ranging from 2 to 20 mm 2 /s, preferably from 3 to 10 mm 2 / s. It is understood that the definitions given above for carboxylic acid and alcohol may be combined, where possible, to define other particular embodiments.

Un diester mis en œuvre selon l’invention peut répondre plus particulièrement à l’une des formules (I), (II) ou (III) suivantes : [Chem 1]

Figure imgf000013_0001
dans lesquelles : A diester used according to the invention may correspond more particularly to one of the following formulas (I), (II) or (III): [Chem 1]
Figure imgf000013_0001
in which :

° R1 représente une chaîne hydrocarbonée, linéaire ou ramifiée, saturée ou insaturée, de préférence saturée, présentant de 3 à 9 atomes de carbone, de préférence de 4 à 8 atomes de carbone, de préférence de 5 à 7 atomes de carbone, ladite chaîne hydrocarbonée étant éventuellement interrompue par un ou plusieurs hétéroatomes, tels que des atomes d’oxygène, de préférence la chaine hydrocarbonée est constituée d’atomes de carbone et d’hydrogène ; et ° R 1 represents a hydrocarbon chain, linear or branched, saturated or unsaturated, preferably saturated, having from 3 to 9 carbon atoms, preferably from 4 to 8 carbon atoms, preferably from 5 to 7 carbon atoms, said hydrocarbon chain being optionally interrupted by one or more heteroatoms, such as oxygen atoms, preferably the hydrocarbon chain consists of carbon and hydrogen atoms; And

° R2 représente une chaîne hydrocarbonée, linéaire ou ramifiée, saturée ou insaturée, de préférence saturée, présentant de 3 à 9 atomes de carbone, de préférence de 4 à 8 atomes de carbone, de préférence de 5 à 7 atomes de carbone, ladite chaîne hydrocarbonée étant éventuellement interrompue par un ou plusieurs hétéroatomes, tels que des atomes d’oxygène, de préférence la chaine hydrocarbonée est constituée d’atomes de carbone et d’hydrogène. De préférence, le(s) diester(s) répondant à la formule (I), (II) ou (III) comportent de 13 à 25 atomes de carbone, de préférence de 15 à 24 atomes de carbone. ° R 2 represents a hydrocarbon chain, linear or branched, saturated or unsaturated, preferably saturated, having from 3 to 9 carbon atoms, preferably from 4 to 8 carbon atoms, preferably from 5 to 7 carbon atoms, said hydrocarbon chain being optionally interrupted by one or more heteroatoms, such as oxygen atoms, preferably the hydrocarbon chain is made up of carbon and hydrogen atoms. Preferably, the diester(s) corresponding to formula (I), (II) or (III) contain from 13 to 25 carbon atoms, preferably from 15 to 24 carbon atoms.

Dans les diesters de formules (I), (II) ou (III), R1 et R2 peuvent être identiques ou différents. In the diesters of formulas (I), (II) or (III), R 1 and R 2 may be identical or different.

Selon un mode de réalisation, le(s) diester(s) mis en œuvre selon l’invention est(sont) choisi(s) parmi : un diester formé à partir de 1,2-décanediol et de deux acides heptanoïques, un diester formé à partir de 1,2-décanediol et de deux acides pentanoïques, un diester formé à partir de 1,2-propanediol et de deux acides heptanoïques, un diester formé à partir de 1,2-propanediol et de deux acides nonanoïques, un diester formé à partir de 1,3 -propanediol et de deux acides heptanoïques, un diester formé à partir de 1,2-propanediol et de deux acides octanoïques, un diester formé à partir de 1,2-propanediol et de deux acides décanoïques, un diester formé à partir de 1,2-propanediol et d’un mélange d’acides comprenant un acide octanoïque et un acide décanoïque, et leurs mélanges. According to one embodiment, the diester(s) used according to the invention is(are) chosen from: a diester formed from 1,2-decanediol and two heptanoic acids, a diester formed from 1,2-decanediol and two pentanoic acids, a diester formed from 1,2-propanediol and two heptanoic acids, a diester formed from 1,2-propanediol and two nonanoic acids, a diester formed from 1,3-propanediol and two heptanoic acids, a diester formed from 1,2-propanediol and two octanoic acids, a diester formed from 1,2-propanediol and two decanoic acids, a diester formed from 1,2-propanediol and a mixture of acids including octanoic acid and decanoic acid, and mixtures thereof.

Les diesters selon l’invention peuvent être préparés selon des méthodes de synthèse connues de l’homme du métier. Ces méthodes de synthèse mettent plus particulièrement en œuvre deux réactions d’estérification, chaque réaction d’estérification étant mise en œuvre entre une fonction alcool du diol et la fonction acide de l’acide monocarboxylique. The diesters according to the invention can be prepared according to synthesis methods known to those skilled in the art. These synthesis methods more particularly implement two esterification reactions, each esterification reaction being implemented between an alcohol function of the diol and the acid function of the monocarboxylic acid.

Bien entendu, il appartient à l’homme du métier d’ajuster les conditions de synthèse pour obtenir un diester selon l’invention. Of course, it is up to those skilled in the art to adjust the synthesis conditions to obtain a diester according to the invention.

Il est entendu que, dans le cadre de la présente invention, un diester selon l’invention peut être sous forme d’un mélange d’au moins deux diesters selon l’invention, en particulier tels que définis précédemment. De préférence, le diester mis en œuvre selon l’invention comprend une teneur en carbone d’origine biologique d’au moins 60% en masse, de préférence d’au moins 70% en masse, de préférence encore d’au moins 80% en masse, encore plus préférentiellement d’au moins 90% en masse, par rapport à la masse totale des atomes de carbone du diester. It is understood that, in the context of the present invention, a diester according to the invention can be in the form of a mixture of at least two diesters according to the invention, in particular as defined above. Preferably, the diester used according to the invention comprises a carbon content of biological origin of at least 60% by mass, preferably at least 70% by mass, more preferably at least 80%. by mass, even more preferably at least 90% by mass, relative to the total mass of the carbon atoms of the diester.

Dans le cadre de la présente invention, la teneur en carbone d’origine biologique peut être mesurée selon la norme ASTM D6866. In the context of the present invention, the carbon content of biological origin can be measured according to the ASTM D6866 standard.

Le diester ou le mélange de diesters selon l’invention peut représenter au moins 5% en masse de la composition selon l’invention, de préférence au moins 10% massique, de préférence au moins 30% massique, plus préférentiellement au moins 50% massique, encore plus préférentiellement au moins 70% massique, en particulier au moins 80% massique, plus particulièrement au moins 90% massique, voire au moins 95% massique, de la masse totale de la composition selon l’invention. The diester or mixture of diesters according to the invention may represent at least 5% by weight of the composition according to the invention, preferably at least 10% by weight, preferably at least 30% by weight, more preferably at least 50% by weight. , even more preferably at least 70% by weight, in particular at least 80% by weight, more particularly at least 90% by weight, or even at least 95% by weight, of the total mass of the composition according to the invention.

Le(s) diester(s) selon l’invention peuvent être utilisés avec une ou plusieurs huiles de base annexes (aussi appelées co-bases). Selon ce mode de réalisation, de préférence, la composition comprendra : de 5 à 95% en masse, de préférence de 5 à 50% en masse, de préférence encore 10 à 40% en masse, du ou des diesters selon l’invention, et de 5 à 95% en masse, de préférence de 50 à 95% en masse, de préférence de 60 à 90% en masse, d’une ou plusieurs huiles de base différentes des diesters selon l’invention, par rapport à la masse totale du ou des diesters et des huiles de base différentes des diesters. The diester(s) according to the invention can be used with one or more additional base oils (also called co-bases). According to this embodiment, preferably, the composition will comprise: from 5 to 95% by weight, preferably from 5 to 50% by weight, more preferably 10 to 40% by weight, of the diester(s) according to the invention, and from 5 to 95% by mass, preferably from 50 to 95% by mass, preferably from 60 to 90% by mass, of one or more base oils different from the diesters according to the invention, relative to the mass total of diester(s) and base oils other than diesters.

Selon un mode de réalisation, une composition lubrifiante selon l’invention peut comprendre au moins 30 % massique d’un diester ou mélange de diesters selon l’invention, plus particulièrement entre 50 % et 99,5 % massique, de préférence entre 70 % et 99 % massique, plus préférentiellement entre 80 % et 99 % massique, voire entre 80 % et 95 % massique, par rapport à la masse totale de ladite composition. Selon un mode de réalisation particulier, une composition lubrifiante selon l’invention peut être formée à plus de 95 % massique, en particulier à plus de 98 % massique, d’un ou plusieurs diesters selon l’invention. According to one embodiment, a lubricating composition according to the invention may comprise at least 30% by weight of a diester or mixture of diesters according to the invention, more particularly between 50% and 99.5% by weight, preferably between 70%. and 99% by weight, more preferably between 80% and 99% by weight, or even between 80% and 95% by weight, relative to the total mass of said composition. According to a particular embodiment, a lubricating composition according to the invention can be formed at more than 95% by weight, in particular at more than 98% by mass, of one or more diesters according to the invention.

Selon un mode de réalisation particulier, la composition selon l’invention est une composition comprenant 100% en masse d’un mélange de diester(s) défini(s) dans l’invention et d’huile(s) de base annexe(s), de préférence en une proportion telle que la composition comprenne : de 5 à 95% en masse, de préférence de 5 à 50% en masse, de préférence encore 10 à 40% en masse, du ou des diesters selon l’invention, et de 5 à 95% en masse, de préférence de 50 à 95% en masse, de préférence de 60 à 90% en masse, d’une ou plusieurs huiles de base différentes des diesters selon l’invention, par rapport à la masse totale de la composition. According to a particular embodiment, the composition according to the invention is a composition comprising 100% by mass of a mixture of diester(s) defined in the invention and additional base oil(s). ), preferably in a proportion such that the composition comprises: from 5 to 95% by weight, preferably from 5 to 50% by weight, more preferably 10 to 40% by weight, of the diester(s) according to the invention, and from 5 to 95% by mass, preferably from 50 to 95% by mass, preferably from 60 to 90% by mass, of one or more base oils different from the diesters according to the invention, relative to the mass total composition.

Ce mode de réalisation est particulièrement avantageux lorsque la composition est utilisée pour refroidir, comme fluide de refroidissement. This embodiment is particularly advantageous when the composition is used for cooling, as a cooling fluid.

Huile(s) de base annexe(s) (co-base(s)) Additional base oil(s) (co-base(s))

La composition lubrifiante selon l’invention peut comprendre, outre un ou plusieurs diesters selon l’invention, une ou plusieurs huiles de base distinctes des diesters selon l’invention, dite « huile de base annexe ». The lubricating composition according to the invention may comprise, in addition to one or more diesters according to the invention, one or more base oils distinct from the diesters according to the invention, called “additional base oil”.

La ou lesdites huiles de base, éventuellement présentes dans la composition lubrifiante selon l’invention, sont choisies de manière adéquate, au regard de leur compatibilité avec le ou lesdits diesters mis en œuvre selon l’invention. Said base oil(s), possibly present in the lubricating composition according to the invention, are chosen adequately, with regard to their compatibility with said diester(s) used according to the invention.

Il peut s’agir d’un mélange de plusieurs huiles de base, par exemple un mélange de deux, trois ou quatre huiles de base. It can be a mixture of several base oils, for example a mixture of two, three or four base oils.

De préférence, l’huile de base ou mélange d’huiles de base annexes, mis en œuvre dans la composition lubrifiante selon l’invention, peut présenter une viscosité cinématique, mesurée à 100 °C selon la norme ASTM D445, allant de 1,5 à 8 mm2/s, en particulier de 1,5 à 6,1 mm2/s, plus particulièrement de 1,5 à 4,1 mm2/s, encore plus particulièrement de 1,5 à 2,1 mm2/s. Les huiles de base peuvent être choisies parmi les huiles d’origines minérales ou synthétiques appartenant aux groupes I à V selon les classes définies dans la classification API (ou leurs équivalents selon la classification ATIEL) et présentées dans le tableau 1 ci- dessous ou leurs mélanges. Preferably, the base oil or mixture of additional base oils, used in the lubricating composition according to the invention, can have a kinematic viscosity, measured at 100 ° C according to the ASTM D445 standard, ranging from 1, 5 to 8 mm 2 /s, in particular 1.5 to 6.1 mm 2 /s, more particularly 1.5 to 4.1 mm 2 /s, even more particularly 1.5 to 2.1 mm 2 /s. The base oils can be chosen from oils of mineral or synthetic origin belonging to groups I to V according to the classes defined in the API classification (or their equivalents according to the ATIEL classification) and presented in table 1 below or their mixtures.

[Tableau 1]

Figure imgf000017_0001
[Table 1]
Figure imgf000017_0001

Les huiles de base minérales incluent tous types d’huiles de base obtenues par distillation atmosphérique et sous vide du pétrole brut, suivies d’opérations de raffinage telles qu’ extraction au solvant, désalphatage, déparaffinage au solvant, hydrotraitement, hydrocraquage, hydroisomérisation et hydrofinition. Mineral base oils include all types of base oils obtained by atmospheric and vacuum distillation of crude oil, followed by refining operations such as solvent extraction, desalphating, solvent dewaxing, hydrotreating, hydrocracking, hydroisomerization and hydrofinishing .

Des mélanges d’huiles synthétiques et minérales, pouvant être biosourcées, peuvent également être employés. Blends of synthetic and mineral oils, which can be biosourced, can also be used.

Les huiles de base peuvent également être choisies parmi les huiles synthétiques, telles certains esters d’acides carboxyliques et d’alcools, distincts de Tester défini selon l’invention, parmi les polyalphaoléfines (PAO), et parmi les polyalkylène glycol (PAG) obtenus par polymérisation ou copolymérisation d’oxydes d’alkylène comprenant de 2 à 8 atomes de carbone, en particulier de 2 à 4 atomes de carbone. The base oils can also be chosen from synthetic oils, such as certain esters of carboxylic acids and alcohols, distinct from Tester defined according to the invention, from polyalphaolefins (PAO), and from polyalkylene glycol (PAG) obtained by polymerization or copolymerization of alkylene oxides comprising from 2 to 8 carbon atoms, in particular from 2 to 4 carbon atoms.

Les PAO utilisées comme huiles de base sont par exemple obtenues à partir de monomères comprenant de 4 à 32 atomes de carbone, par exemple à partir d’octène ou de décène. The PAOs used as base oils are for example obtained from monomers comprising 4 to 32 carbon atoms, for example from octene or decene.

La masse moléculaire moyenne massique de la PAO peut varier assez largement. De manière préférée, la masse moléculaire moyenne massique de la PAO est inférieure à 600 Da. La masse moléculaire moyenne massique de la PAO peut également aller de 100 à 600 Da, de 150 à 600 Da, ou encore de 200 à 600 Da. The weight average molecular weight of PAO can vary quite widely. Preferably, the mass average molecular weight of the PAO is less than 600Da. The mass average molecular mass of the PAO can also range from 100 to 600 Da, from 150 to 600 Da, or even from 200 to 600 Da.

Par exemple, les PAO mises en œuvre dans le cadre de l’invention, présentant une viscosité cinématique, mesurée à 100 °C selon la norme ASTM D445, allant de 1,5 à 8 mm2/s sont vendues commercialement par Ineos sous les marques Durasyn® 162, Durasyn® 164, Durasyn® 166 et Durasyn® 168. For example, the PAOs implemented in the context of the invention, having a kinematic viscosity, measured at 100 ° C according to the ASTM D445 standard, ranging from 1.5 to 8 mm 2 /s are sold commercially by Ineos under the brands Durasyn® 162, Durasyn® 164, Durasyn® 166 and Durasyn® 168.

Avantageusement, l’huile ou les huiles de base additionnelles sont choisies parmi les polyalphaoléfines (PAO). Advantageously, the additional base oil or oils are chosen from polyalphaolefins (PAO).

Il appartient à l’homme du métier d’ajuster la teneur en huile(s) de base annexe (s) présente(s) dans la composition selon l’invention. It is up to those skilled in the art to adjust the content of additional base oil(s) present in the composition according to the invention.

En particulier, une composition selon l’invention peut comprendre de 5 à 95% en masse, de préférence de 50 à 95% en masse, de préférence encore de 60 à 90% en masse, d’une ou plusieurs huiles de base différentes des diesters selon l’invention, par rapport à la masse totale de ladite composition. In particular, a composition according to the invention may comprise from 5 to 95% by weight, preferably from 50 to 95% by weight, more preferably from 60 to 90% by weight, of one or more base oils different from the diesters according to the invention, relative to the total mass of said composition.

Additifs Additives

La composition lubrifiante selon l’invention peut éventuellement comprendre en outre un ou plusieurs additifs connus de l’homme du métier dans le domaine de la lubrification, en particulier pour transmissions de véhicules, notamment pour transmissions de véhicules légers ou lourds. The lubricating composition according to the invention may optionally also comprise one or more additives known to those skilled in the art in the field of lubrication, in particular for vehicle transmissions, in particular for transmissions of light or heavy vehicles.

Ces additifs peuvent être notamment choisis parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges. These additives may be chosen in particular from friction modifier additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant additives. (PPD), dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof.

De préférence, la composition lubrifiante selon l’invention peut comprendre en outre un ou plusieurs additifs choisis parmi les antioxydants, les agents anti-mousse, les améliorants du point d’écoulement et les anti-corrosion. Il est entendu que la nature et la quantité d’additifs mis en œuvre sont choisies de manière à ne pas affecter les propriétés de la composition lubrifiante conférées par le diester selon l’invention. Preferably, the lubricating composition according to the invention may further comprise one or more additives chosen from antioxidants, anti-foaming agents, pour point improvers and anti-corrosion agents. It is understood that the nature and quantity of additives used are chosen so as not to affect the properties of the lubricating composition conferred by the diester according to the invention.

Ces additifs peuvent être introduits isolément et/ou sous la forme d’un mélange à l’image de ceux déjà disponibles à la vente pour les formulations de lubrifiants commerciaux pour moteurs de véhicules, de niveau de performance tels que définis par l’ACEA (Association des Constructeurs Européens d’ Automobiles) et/ou l’ API (American Petroleum Institute), bien connus de l’homme du métier. These additives can be introduced individually and/or in the form of a mixture like those already available for sale for commercial lubricant formulations for vehicle engines, with a performance level as defined by the ACEA ( Association of European Automobile Manufacturers) and/or the API (American Petroleum Institute), well known to those skilled in the art.

Le ou lesdits additifs peuvent être présents dans la composition lubrifiante selon l'invention en une teneur inférieure ou égale à 10 % massique, en particulier inférieure ou égale à 5 % massique, et plus particulièrement allant de 0,01 à 3 % massique, par rapport à la masse totale de ladite composition. Said additive(s) may be present in the lubricating composition according to the invention in a content less than or equal to 10% by weight, in particular less than or equal to 5% by weight, and more particularly ranging from 0.01 to 3% by weight, for example relative to the total mass of said composition.

Une composition lubrifiante selon l’invention peut ainsi comprendre au moins un additif antioxydant. A lubricating composition according to the invention can thus comprise at least one antioxidant additive.

L’invention concerne ainsi, selon un de ses aspects, une composition lubrifiante comprenant (i) au moins un diester tel que défini précédemment, et (ii) au moins un additif anti-oxydant. The invention thus relates, according to one of its aspects, to a lubricating composition comprising (i) at least one diester as defined above, and (ii) at least one antioxidant additive.

L’additif antioxydant permet généralement de retarder la dégradation de la composition en service. Cette dégradation peut notamment se traduire par la formation de dépôts, par la présence de boues ou par une augmentation de la viscosité de la composition. The antioxidant additive generally makes it possible to delay the degradation of the composition in service. This degradation can notably result in the formation of deposits, the presence of sludge or an increase in the viscosity of the composition.

Les additifs antioxydants agissent notamment comme inhibiteurs radicalaires ou destructeurs d’hydropéroxydes. Antioxidant additives act in particular as free radical inhibitors or hydroperoxide destroyers.

Parmi les additifs antioxydants couramment employés on peut citer les antioxydants de type phénolique, les additifs antioxydant de type aminé, les additifs antioxydants phosphosoufrés. Certains de ces additifs antioxydants, par exemple les additifs antioxydants phosphosoufrés, peuvent être générateurs de cendres. Les additifs antioxydants phénoliques peuvent être exempts de cendres ou bien être sous forme de sels métalliques neutres ou basiques. Les additifs antioxydants peuvent notamment être choisis parmi les phénols stériquement encombrés, les esters de phénol stériquement encombrés et les phénols stériquement encombrés comprenant un pont thioéther, les diphénylamines, les diphénylamines substituées par au moins un groupement alkyle en C1-C12, les N,N’-dialkyle- aryle-diamines et leurs mélanges. De préférence, les phénols stériquement encombrés sont choisis parmi les composés comprenant un groupement phénol dont au moins un carbone vicinal du carbone portant la fonction alcool est substitué par au moins un groupement alkyle en C1-C10, de préférence un groupement alkyle en CI-CÔ, de préférence un groupement alkyle en C4, de préférence par le groupement ter-butyle. Les composés aminés sont une autre classe d’additifs antioxydants pouvant être utilisés, éventuellement en combinaison avec les additifs antioxydants phénoliques. Des exemples de composés aminés sont les amines aromatiques, par exemple les amines aromatiques de formule NR5R6R7 dans laquelle R5 représente un groupement aliphatique ou un groupement aromatique, éventuellement substitué, R6 représente un groupement aromatique, éventuellement substitué, R7 représente un atome d’hydrogène, un groupement alkyle, un groupement aryle ou un groupement de formule R8S(O)ZR9 dans laquelle R8 représente un groupement alkylène ou un groupement alkenylène, R9 représente un groupement alkyle, un groupement alcényle ou un groupement aryle et z représente 0, 1 ou 2. Des alkyl phénols sulfurisés ou leurs sels de métaux alcalins et alcalino-terreux peuvent également être utilisés comme additifs antioxydants. Among the commonly used antioxidant additives we can cite phenolic-type antioxidants, amine-type antioxidant additives and phosphosulfur-containing antioxidant additives. Some of these antioxidant additives, for example phosphosulfur antioxidant additives, can generate ash. Phenolic antioxidant additives can be ash-free or in the form of neutral or basic metal salts. The antioxidant additives may in particular be chosen from sterically hindered phenols, sterically hindered phenol esters and sterically hindered phenols comprising a thioether bridge, diphenylamines, diphenylamines substituted by at least one C1-C12 alkyl group, N,N'-dialkyl-aryl-diamines and their mixtures. Preferably, the sterically hindered phenols are chosen from compounds comprising a phenol group of which at least one vicinal carbon of the carbon carrying the alcohol function is substituted by at least one C1-C10 alkyl group, preferably a CI-C6 alkyl group. , preferably a C4 alkyl group, preferably the tert-butyl group. Amino compounds are another class of antioxidant additives that can be used, possibly in combination with phenolic antioxidant additives. Examples of amino compounds are aromatic amines, for example aromatic amines of formula NR 5 R 6 R 7 in which R 5 represents an aliphatic group or an aromatic group, optionally substituted, R 6 represents an aromatic group, optionally substituted, R 7 represents a hydrogen atom, an alkyl group, an aryl group or a group of formula R 8 S(O) Z R 9 in which R 8 represents an alkylene group or an alkenylene group, R 9 represents an alkyl group, a alkenyl group or an aryl group and z represents 0, 1 or 2. Sulfurized alkyl phenols or their alkali and alkaline earth metal salts can also be used as antioxidant additives.

De manière avantageuse, une composition lubrifiante comprend au moins un additif antioxydant exempt de cendres. Advantageously, a lubricating composition comprises at least one ash-free antioxidant additive.

Le ou lesdits additifs peuvent être mis en œuvre, dans une composition lubrifiante selon l’invention, à raison de 0,1 à 2 % massique, par rapport à la masse totale de la composition. Said additive(s) can be used, in a lubricating composition according to the invention, at a rate of 0.1 to 2% by weight, relative to the total mass of the composition.

Une composition lubrifiante selon l’invention peut comprendre au moins un additif anti-usure, un additif extrême-pression ou leurs mélanges. A lubricating composition according to the invention may comprise at least one anti-wear additive, an extreme pressure additive or mixtures thereof.

Les additifs anti-usure et les additifs extrême pression protègent les surfaces en frottement par formation d’un film protecteur adsorbé sur ces surfaces. Anti-wear additives and extreme pressure additives protect rubbing surfaces by forming a protective film adsorbed on these surfaces.

Il existe une grande variété d’additifs anti-usure. De manière préférée, les additifs anti-usure sont choisis parmi des additifs phosphosoufrés comme les alkylthiophosphates métalliques, en particulier les alkylthiophosphates de zinc, et plus spécifiquement les dialkyldithiophosphates de zinc ou ZnDTP. Les composés préférés sont de formule Zn((SP(S)(OQ2)(OQ3))2, dans laquelle Q2 et Q3, identiques ou différents, représentent indépendamment un groupement alkyle, préférentiellement un groupement alkyle comportant de 1 à 18 atomes de carbone. There is a wide variety of anti-wear additives. Preferably, the anti-wear additives are chosen from phosphosulfur additives such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP. The preferred compounds are of formula Zn((SP(S)(OQ 2 )(OQ 3 ))2, in which Q 2 and Q 3 , identical or different, represent independently an alkyl group, preferably an alkyl group comprising from 1 to 18 carbon atoms.

De préférence, la composition lubrifiante selon l’invention est exempte d’esters de type phosphite contenant du soufre de formule Preferably, the lubricating composition according to the invention is free from phosphite type esters containing sulfur of formula

[Chem 4]

Figure imgf000021_0001
dans laquelle R est un groupe hydrocarboné en C4 à C20 contenant du soufre et R1 est un hydrogène, un groupe hydrocarboné en C4 à C20 ou un groupe hydrocarboné en C4 à C20 contenant du soufre. [Chem 4]
Figure imgf000021_0001
wherein R is a C4 to C20 hydrocarbon group containing sulfur and R 1 is hydrogen, a C4 to C20 hydrocarbon group or a C4 to C20 hydrocarbon group containing sulfur.

Les phosphates d’amines sont également des additifs anti -usure qui peuvent être employés dans une composition selon l’invention. Toutefois, le phosphore apporté par ces additifs peut agir comme poison des systèmes catalytiques des automobiles car ces additifs sont générateurs de cendres. On peut minimiser ces effets en substituant partiellement les phosphates d’amines par des additifs n’apportant pas de phosphore, tels que, par exemple, les polysulfures, notamment les oléfines soufrées. Amine phosphates are also anti-wear additives which can be used in a composition according to the invention. However, the phosphorus provided by these additives can act as a poison in the catalytic systems of automobiles because these additives generate ash. These effects can be minimized by partially substituting the amine phosphates with additives which do not provide phosphorus, such as, for example, polysulphides, in particular sulfur-containing olefins.

Une composition lubrifiante peut comprendre de 0,01 à 6 % massique, préférentiellement de 0,05 à 4 % massique, plus préférentiellement de 0,1 à 2 % massique d’additifs anti -usure et d’additifs extrême-pression, massique par rapport à la masse totale de composition. A lubricating composition may comprise from 0.01 to 6% by weight, preferably from 0.05 to 4% by weight, more preferably from 0.1 to 2% by weight of anti-wear additives and extreme pressure additives, by weight per relative to the total mass of composition.

Une composition lubrifiante selon l’invention peut comprendre en outre un agent antimousse. A lubricating composition according to the invention may further comprise an anti-foaming agent.

L’agent antimousse peut être choisi parmi les silicones. The anti-foaming agent can be chosen from silicones.

Une composition lubrifiante peut comprendre de 0,01 à 2 % massique ou de 0,01 à 5 % massique, préférentiellement de 0,1 à 1,5 % massique ou de 0,1 à 2 % massique d’agent antimousse, par rapport à la masse totale de la composition. Une composition lubrifiante selon l’invention peut comprendre au moins un additif modificateur de frottement. A lubricating composition may comprise from 0.01 to 2% by weight or from 0.01 to 5% by weight, preferably from 0.1 to 1.5% by weight or from 0.1 to 2% by weight of antifoaming agent, relative to to the total mass of the composition. A lubricating composition according to the invention may comprise at least one friction modifier additive.

Les additifs modificateurs de frottement permettent de limiter les frottements en formant des monocouches adsorbées sur les surfaces des métaux à leur contact. Ils peuvent être choisis parmi des composés apportant des éléments métalliques et des composés exempts de cendres. Parmi les composés apportant des éléments métalliques, on peut citer les complexes de métaux de transition tels que Mo, Sb. Sn, Fe, Cu, Zn dont les ligands peuvent être des composés hydrocarbonés comprenant des atomes d’oxygène, d’azote, de soufre ou de phosphore. Les additifs modificateurs de frottement exempts de cendres sont généralement d’origine organique et peuvent être choisis parmi les esters d’acides gras et de polyols, distincts du monoester requis selon l’invention, les amines alcoxylées, les amines grasses alcoxylées, les époxydes gras, les époxydes gras de borate, les amines grasses ou les esters de glycérol d’acide gras. Selon l’invention, les composés gras comprennent au moins un groupement hydrocarboné comprenant de 10 à 24 atomes de carbone. En particulier, les composés à base de molybdène peuvent être choisis parmi les dithiocarbamates de molybdène (Mo-DTC), les dithiophosphates de molybdène (Mo-DTP), et leurs mélanges. Une composition lubrifiante peut notamment comprendre une teneur en molybdène comprise entre 1000 et 2500 ppm. Friction modifier additives make it possible to limit friction by forming monolayers adsorbed on the surfaces of metals in contact with them. They can be chosen from compounds providing metallic elements and compounds free of ash. Among the compounds providing metallic elements, we can cite transition metal complexes such as Mo, Sb. Sn, Fe, Cu, Zn whose ligands can be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or phosphorus atoms. The ash-free friction modifier additives are generally of organic origin and can be chosen from esters of fatty acids and polyols, distinct from the monoester required according to the invention, alkoxylated amines, alkoxylated fatty amines, fatty epoxides. , fatty borate epoxides, fatty amines or glycerol esters of fatty acids. According to the invention, the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms. In particular, the molybdenum-based compounds can be chosen from molybdenum dithiocarbamates (Mo-DTC), molybdenum dithiophosphates (Mo-DTP), and mixtures thereof. A lubricating composition may in particular comprise a molybdenum content of between 1000 and 2500 ppm.

Une composition lubrifiante peut comprendre de 0,01 à 5 % massique, plus particulièrement de 0,1 à 2 % massique ou encore plus particulièrement de 0,1 à 1,5 % massique d’additif modificateur de frottement, par rapport à la masse totale de la composition. A lubricating composition may comprise from 0.01 to 5% by weight, more particularly from 0.1 to 2% by weight or even more particularly from 0.1 to 1.5% by weight of friction modifier additive, relative to the mass total composition.

Lorsqu’ils sont utilisés à une teneur trop importante, les composés molybdène peuvent impacter négativement les propriétés à froid de la composition lubrifiante dans laquelle ils sont mis en œuvre. Ainsi, une composition lubrifiante selon l’invention comprend de préférence moins de 1,5 % massique de molybdène, plus préférentiellement moins de 1% massique, par rapport à la masse totale de la composition, voire est exempte de de molybdène. When used at too high a content, molybdenum compounds can negatively impact the cold properties of the lubricating composition in which they are used. Thus, a lubricating composition according to the invention preferably comprises less than 1.5% by weight of molybdenum, more preferably less than 1% by weight, relative to the total mass of the composition, or is even free from molybdenum.

Une composition lubrifiante selon l’invention peut comprendre au moins un additif détergent. Les additifs détergents permettent généralement de réduire la formation de dépôts à la surface des pièces métalliques par dissolution des produits secondaires d’oxydation et de combustion. A lubricating composition according to the invention may comprise at least one detergent additive. Detergent additives generally help reduce the formation of deposits on the surface of metal parts by dissolving secondary oxidation and combustion products.

Les additifs détergents utilisables dans une composition lubrifiante sont généralement connus de l’homme de métier. Les additifs détergents peuvent être des composés anioniques comprenant un groupement hydrocarboné lipophile et une tête hydrophile. Le cation associé peut être un cation métallique d’un métal alcalin ou alcalino- terreux. The detergent additives which can be used in a lubricating composition are generally known to those skilled in the art. The detergent additives can be anionic compounds comprising a lipophilic hydrocarbon group and a hydrophilic head. The associated cation may be a metallic cation of an alkali or alkaline earth metal.

Les additifs détergents sont préférentiellement choisis parmi les sels de métaux alcalins ou de métaux alcalino-terreux d’acides carboxyliques, les sulfonates, les salicylates, les naphténates, ainsi que les sels de phénates. Les métaux alcalins et alcalino-terreux sont préférentiellement le calcium, le magnésium, le sodium ou le baryum. 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.

Ces sels métalliques comprennent généralement le métal en quantité stœchiométrique ou bien en excès, donc en quantité supérieure à la quantité stœchiom étriqué. Il s’agit alors d’additifs détergents surbasés ; le métal en excès apportant le caractère surbasé à l’additif détergent est alors généralement sous la forme d’un sel métallique insoluble dans l’huile, par exemple un carbonate, un hydroxyde, un oxalate, un acétate, un glutamate, préférentiellement un carbonate. These metal salts generally include the metal in stoichiometric quantity or in excess, therefore in quantity greater than the narrow stoichiometric quantity. These are then 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 .

Une composition lubrifiante peut par exemple comprendre de 2 à 4 % massique d’additif détergent, par rapport à la masse totale de la composition. A lubricating composition can for example comprise 2 to 4% by weight of detergent additive, relative to the total mass of the composition.

Une composition lubrifiante peut également comprendre au moins un additif abaisseur de point d’écoulement (dit encore agent « PPD » pour « Pour Point Depressant » en langue anglaise). A lubricating composition may also comprise at least one pour point depressant additive (also called “PPD” agent for “Pour Point Depressant” in English).

En ralentissant la formation de cristaux de paraffine, les additifs abaisseurs de point d’écoulement améliorent généralement le comportement à froid de la composition. Comme exemple d’additifs abaisseurs de point d’écoulement, on peut citer les polyméthacrylates d’alkyle, les polyacrylates, les polyarylamides, les polyalkylphénols, les polyalkylnaphtalènes, les polystyrènes alkylés. By slowing the formation of paraffin crystals, pour point depressant additives generally improve the cold behavior of the composition. As an example of pour point depressant additives, mention may be made of polyalkyl methacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes, alkylated polystyrenes.

Une composition lubrifiante selon l’invention peut comprendre de 0,1 % à 2 %, de préférence de 0,2 % à 1 % massique d’additif(s) abaisseur(s) du point d’écoulement, par rapport à la masse totale de la composition. Également, une composition lubrifiante peut comprendre au moins un agent dispersant. A lubricating composition according to the invention may comprise from 0.1% to 2%, preferably from 0.2% to 1% by weight of pour point depressant additive(s), relative to the mass. total composition. Also, a lubricating composition may comprise at least one dispersing agent.

L’agent dispersant peut être choisi parmi les bases de Mannich, les succinimides et leurs dérivés, tels que les dérivés de polyisobutylène anhydride succinique. The dispersing agent can be chosen from Mannich bases, succinimides and their derivatives, such as polyisobutylene succinic anhydride derivatives.

Une composition lubrifiante peut par exemple comprendre de 0,2 à 10 % massique d’agent dispersant, par rapport à la masse totale de la composition. A lubricating composition can for example comprise from 0.2 to 10% by weight of dispersing agent, relative to the total mass of the composition.

Une composition lubrifiante selon l’invention peut également comprendre au moins un additif améliorant l’indice de viscosité (VI). A lubricating composition according to the invention may also comprise at least one additive improving the viscosity index (VI).

Les améliorants de l’indice de viscosité, en particulier les polymères améliorant l’indice de viscosité, permettent de garantir une bonne tenue à froid et une viscosité minimale à haute température. Viscosity index improvers, in particular viscosity index improving polymers, make it possible to guarantee good cold resistance and minimum viscosity at high temperatures.

Comme exemples de polymère améliorant l’indice de viscosité, on peut citer les esters polymères, les homopolymères ou les copolymères, hydrogénés ou non-hydrogénés du styrène, du butadiène et de l’isoprène, les homopolymères ou les copolymères d’oléfine, telle que l’éthylène ou le propylène, les polyacrylates et polyméthacrylates (PMA), de préférence les homopolymères ou les copolymères d’oléfine, telle que l’éthylène ou le propylène. As examples of polymers improving the viscosity index, mention may be made of polymer esters, homopolymers or copolymers, hydrogenated or non-hydrogenated, of styrene, butadiene and isoprene, homopolymers or copolymers of olefin, such as such as ethylene or propylene, polyacrylates and polymethacrylates (PMA), preferably olefin homopolymers or copolymers, such as ethylene or propylene.

En particulier, une composition lubrifiante selon l’invention peut comprendre de 1 à 15 % massique d’additif(s) améliorant l’indice de viscosité, de préférence de 5 % à 10 % massique, par rapport à la masse totale de la composition lubrifiante. In particular, a lubricating composition according to the invention may comprise from 1 to 15% by weight of additive(s) improving the viscosity index, preferably from 5% to 10% by weight, relative to the total mass of the composition. lubricating.

Une composition lubrifiante peut encore comprendre au moins un additif antimousse, par exemple choisi parmi les polymères polaires tels que les polyméthylsiloxanes ou les polyacrylates. A lubricating composition may also comprise at least one antifoam additive, for example chosen from polar polymers such as polymethylsiloxanes or polyacrylates.

En particulier, une composition lubrifiante selon l’invention peut comprendre de 0,01 à 3% massique d’additif(s) anti-mousse, par rapport à la masse totale de la composition lubrifiante. In particular, a lubricating composition according to the invention may comprise from 0.01 to 3% by weight of anti-foam additive(s), relative to the total mass of the lubricating composition.

Elle peut encore comprendre au moins un agent anticorrosion ou agent passivant du cuivre, par exemple des composés tels que les polyisobutènes anhydrides succiniques, les sulfonates thiadiazoles ou les mercaptobenzothiazoles. Ils sont typiquement présents dans une composition lubrifiante selon l’invention à des teneurs comprises entre 0,01 % et 1 % massique, par rapport à la masse totale de la composition. It may also include at least one anti-corrosion agent or copper passivating agent, for example compounds such as polyisobutenes succinic anhydrides, thiadiazole sulfonates or mercaptobenzothiazoles. They are typically present in a lubricating composition according to the invention at contents of between 0.01% and 1% by weight, relative to the total mass of the composition.

De manière avantageuse, une composition lubrifiante selon l’invention comprend un ou plusieurs additifs choisis parmi les agents améliorants l’indice de viscosité, les agents abaisseurs du point d’écoulement, les agents anti -usure et les agents antioxydant. Advantageously, a lubricating composition according to the invention comprises one or more additives chosen from viscosity index improving agents, pour point lowering agents, anti-wear agents and antioxidant agents.

Selon un mode de réalisation particulier, une composition lubrifiante selon l’invention comprend, voire est formée (i) d’au moins un diester selon l’invention et (ii) d’au moins un additif choisi parmi les anti-oxydants, les additifs améliorant l’indice de viscosité, les additifs abaisseur du point d’écoulement, les additifs anti-usure et/ou extrême-pression, les antimousse, les détergents, les dispersants, et leurs mélanges, de préférence parmi les anti-oxydants, les additifs améliorant l’indice de viscosité, les additifs abaisseur du point d’écoulement, les additifs anti-usure et/ou extrême-pression, et leurs mélanges. According to a particular embodiment, a lubricating composition according to the invention comprises, or even is formed of (i) at least one diester according to the invention and (ii) at least one additive chosen from antioxidants, viscosity index improving additives, pour point depressant additives, anti-wear and/or extreme pressure additives, antifoams, detergents, dispersants, and mixtures thereof, preferably among anti-oxidants, viscosity index improving additives, pour point depressant additives, anti-wear and/or extreme pressure additives, and mixtures thereof.

Avantageusement, une composition lubrifiante selon l’invention est formée (i) d’au moins un diester répondant à l’une des formules (I), (II) ou (III) telles que définies précédemment et (ii) d’au moins un additif anti-oxydant. Advantageously, a lubricating composition according to the invention is formed of (i) at least one diester corresponding to one of formulas (I), (II) or (III) as defined above and (ii) at least an antioxidant additive.

Avantageusement, une composition lubrifiante selon l’invention est formée (i) d’au moins un diester répondant à l’une des formules (I) ou (II) telles que définies précédemment et (ii) d’au moins un additif anti-oxydant. Advantageously, a lubricating composition according to the invention is formed of (i) at least one diester corresponding to one of formulas (I) or (II) as defined above and (ii) at least one anti- oxidant.

Selon un mode de réalisation particulier, une composition selon l’invention comprend, voire est constituée de : According to a particular embodiment, a composition according to the invention comprises, or even consists of:

- au moins 5% massique, de préférence au moins 10% massique, de préférence au moins 30% massique, de préférence au moins 50% massique, plus préférentiellement au moins 70% massique, voire au moins 90% massique, de diester(s) répondant à l’une des formules (I), (II) ou (III) ; - at least 5% by weight, preferably at least 10% by weight, preferably at least 30% by weight, preferably at least 50% by weight, more preferably at least 70% by weight, or even at least 90% by weight, of diester(s) ) corresponding to one of formulas (I), (II) or (III);

- de 0,01 à 20% massique, de préférence de 0,05 à 15% massique, de préférence encore de 0,1 à 10% massique, encore plus préférentiellement de 0,5 à 7% massique, voire de 1 à 5% massique, d’un ou plusieurs additifs choisi(s) parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges ; et - from 0.01 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 the additives friction modifiers, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, agents defoamers, thickeners, corrosion inhibitors, copper passivators, and mixtures thereof; And

- éventuellement de 5 à 94% massique, de préférence de 10 à 94% massique, de préférence de 15 à 90% massique d’huile(s) de base distincte(s) du diester selon l’invention ; les teneurs étant exprimées par rapport à la masse totale de ladite composition. - optionally from 5 to 94% by weight, preferably from 10 to 94% by weight, preferably from 15 to 90% by weight of base oil(s) distinct from the diester according to the invention; the contents being expressed in relation to the total mass of said composition.

Selon un mode de réalisation particulier, une composition selon l’invention comprend, voire est constituée de : According to a particular embodiment, a composition according to the invention comprises, or even consists of:

- de 5 à 95% massique, de préférence de 10 à 90% massique, de préférence encore de 20 à 80% massique, encore plus préférentiellement de 30 à 70% massique, voire de 40 à 60% massique, de diester(s) répondant à l’une des formules (I), (II) ou (III) ;- from 5 to 95% by weight, preferably from 10 to 90% by weight, more preferably from 20 to 80% by weight, even more preferably from 30 to 70% by weight, or even from 40 to 60% by weight, of diester(s) corresponding to one of formulas (I), (II) or (III);

- de 5 à 95% massique, de préférence de 10 à 90% massique, de préférence encore de 20 à 80% massique, encore plus préférentiellement de 30 à 70% massique, voire de 40 à 60% massique d’une ou plusieurs huiles de base différentes desdits diesters ;- from 5 to 95% by weight, preferably from 10 to 90% by weight, more preferably from 20 to 80% by weight, even more preferably from 30 to 70% by weight, or even from 40 to 60% by weight of one or more oils different bases of said diesters;

- éventuellement de 0,01 à 20% massique, de préférence de 0,05 à 15% massique, de préférence encore de 0,1 à 10% massique, encore plus préférentiellement de 0,5 à 7% massique, voire de 1 à 5% massique d’un ou plusieurs additifs distincts du diester et distincts de(s) huile(s) de base, les teneurs étant exprimées par rapport à la masse totale de ladite composition. - optionally from 0.01 to 20% by weight, preferably from 0.05 to 15% by weight, more preferably from 0.1 to 10% by weight, even more preferably from 0.5 to 7% by weight, or even from 1 to 5% by weight of one or more additives distinct from the diester and distinct from the base oil(s), the contents being expressed in relation to the total mass of said composition.

Selon un mode de réalisation particulier, une composition lubrifiante selon l’invention comprend, voire est constituée de : According to a particular embodiment, a lubricating composition according to the invention comprises, or even consists of:

- au moins 5% massique, de préférence de 10% à 40%, plus préférentiellement de 15% à 30% massique, d’un ou plusieurs diesters selon l’invention définis précédemment, de préférence choisis parmi les diesters répondant à la formule (I) ; - at least 5% by weight, preferably from 10% to 40%, more preferably from 15% to 30% by weight, of one or more diesters according to the invention defined previously, preferably chosen from diesters corresponding to the formula ( I);

- de 50% à 95% massique d’huile(s) de base distincte(s) des diesters définis selon l’invention, de préférence choisie(s) parmi les huiles de base de groupe II et/ou III selon la classification API ; - éventuellement de 5% à 15% massique d’au moins un additif améliorant de l’indice de viscosité ; - from 50% to 95% by weight of base oil(s) distinct from the diesters defined according to the invention, preferably chosen from group II and/or III base oils according to the API classification ; - optionally from 5% to 15% by weight of at least one additive improving the viscosity index;

- éventuellement de 0,1% à 1% massique d’au moins un additif abaisseur du point d’écoulement ; - optionally from 0.1% to 1% by weight of at least one pour point depressant additive;

- éventuellement de 0,01% à 6% massique d’au moins un additif anti-usure ; et- optionally from 0.01% to 6% by weight of at least one anti-wear additive; And

- éventuellement de 0,1% à 2% massique d’au moins un additif antioxydant, les teneurs étant exprimées par rapport à la masse totale de ladite composition. - optionally from 0.1% to 2% by weight of at least one antioxidant additive, the contents being expressed in relation to the total mass of said composition.

De préférence, une composition lubrifiante selon l’invention comprend, voire est constituée de : Preferably, a lubricating composition according to the invention comprises, or even consists of:

- moins de 30% massique, en particulier de 1 et 30% massique, notamment de 5 à 30% massique, de préférence de 10 à 30% massique et plus particulièrement de 15 à 30% massique, d’un ou plusieurs diester selon l’invention définis précédemment, de préférence choisis parmi les diesters de formule (I) ou (II) ; - less than 30% by weight, in particular 1 and 30% by weight, in particular 5 to 30% by weight, preferably 10 to 30% by weight and more particularly 15 to 30% by weight, of one or more diesters depending on invention defined above, preferably chosen from diesters of formula (I) or (II);

- de 50% à 85% massique d’huile(s) de base distincte(s) des diesters définis selon l’invention, de préférence choisie(s) parmi les huiles de base de groupe II et/ou III selon la classification API ; - from 50% to 85% by weight of base oil(s) distinct from the diesters defined according to the invention, preferably chosen from group II and/or III base oils according to the API classification ;

- éventuellement de 5% à 15% massique d’au moins un additif améliorant de l’indice de viscosité ; - optionally from 5% to 15% by weight of at least one additive improving the viscosity index;

- éventuellement de 0,1% à 1% massique d’au moins un additif abaisseur du point d’écoulement ; - optionally from 0.1% to 1% by weight of at least one pour point depressant additive;

- éventuellement de 0,01% à 6% massique d’au moins un additif anti-usure ; et- optionally from 0.01% to 6% by weight of at least one anti-wear additive; And

- éventuellement de 0,1% à 2% massique d’au moins un additif antioxydant, les teneurs étant exprimées par rapport à la masse totale de ladite composition. - optionally from 0.1% to 2% by weight of at least one antioxidant additive, the contents being expressed in relation to the total mass of said composition.

Selon un mode de réalisation particulier, une composition selon l’invention comprend, voire est constituée de : de 5 à 95% en masse, de préférence de 5 à 50% en masse, de préférence encore 10 à 40% en masse, dudit ou desdits diesters répondant à la formule (I) ou (II) ; de 5 à 95% en masse, de préférence de 50 à 95% en masse, de préférence de 60 à 90% en masse, d’une ou plusieurs huiles de base différentes desdits diesters ; éventuellement de 0,01 à 20% massique, de préférence de 0,05 à 15% massique, de préférence encore de 0,1 à 10% massique, encore plus préférentiellement de 0,5 à 7% massique, voire de 1 à 5% massique, d’un ou plusieurs additifs choisi(s) parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges, les teneurs étant exprimées par rapport à la masse totale de ladite composition. According to a particular embodiment, a composition according to the invention comprises, or even consists of: from 5 to 95% by mass, preferably from 5 to 50% by mass, more preferably 10 to 40% by mass, of said or said diesters corresponding to formula (I) or (II); from 5 to 95% by weight, preferably from 50 to 95% by weight, preferably from 60 to 90% by weight, of one or more base oils different from said diesters; optionally from 0.01 to 20% by weight, preferably from 0.05 to 15% by weight, more preferably from 0.1 to 10% by weight, even more preferably from 0.5 to 7% by weight, or even from 1 to 5 % by mass, of one or more additives chosen from friction modifier additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, 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.

Une composition selon l’invention présente avantageusement une viscosité cinématique, mesurée à 100°C selon la norme ASTM D445, allant de 1 à 20 mm2/s, de préférence de 2 à 15 mm2/s. A composition according to the invention advantageously has a kinematic viscosity, measured at 100°C according to the ASTM D445 standard, ranging from 1 to 20 mm 2 /s, preferably from 2 to 15 mm 2 /s.

Une composition selon l’invention présente avantageusement une viscosité cinématique, mesurée à 40°C selon la norme ASTM D445, allant de 20 à 50 mm2/s, de préférence de 25 à 40 mm2/s. A composition according to the invention advantageously has a kinematic viscosity, measured at 40°C according to the ASTM D445 standard, ranging from 20 to 50 mm 2 /s, preferably from 25 to 40 mm 2 /s.

La composition selon l’invention présente de bonnes propriétés de lubrification.The composition according to the invention has good lubricating properties.

La composition selon l’invention présente également de bonnes propriétés en termes de tenue à froid. The composition according to the invention also has good properties in terms of cold resistance.

La composition selon l’invention présente également de bonnes propriétés pour refroidir. The composition according to the invention also has good cooling properties.

La présente invention a également pour objet l’utilisation d’un diester dans une composition pour lubrifier et/ou refroidir au moins une pièce d’un système mobile ou stationnaire, ledit diester étant formé entre : un diol choisi parmi le 1,2-propanediol, le 1,2-décanediol et les 1,3-diol comportant de 3 à 10 atomes de carbone, et deux acides monocarboxyliques, identiques ou différents, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone.The present invention also relates to the use of a diester in a composition for lubricating and/or cooling at least one part of a mobile or stationary system, said diester being formed between: a diol chosen from 1,2- propanediol, 1,2-decanediol and 1,3-diol comprising 3 to 10 carbon atoms, and two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising 4 to 10 carbon atoms.

De préférence, la composition pour lubrifier et/ou refroidir comprend en outre, au moins une huile de base distincte du diester et/ou au moins un additif distinct du diester, ledit additif étant choisi parmi les anti-oxydants, les additifs abaisseurs de point d’écoulement, les agents anti-mousse, les agents anticorrosion, les additifs anti-usure et/ou extrême- pression, les modificateurs de frottement, les détergents, les agents dispersants et leurs mélanges, en particulier parmi les anti-oxydants, les additifs abaisseurs de point d’écoulement, les agents anti-mousse et les agents anticorrosion. Preferably, the composition for lubricating and/or cooling further comprises at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from anti-oxidants, pour point depressant additives, anti-foam agents, anti-corrosion agents, anti-wear and/or extreme pressure additives, friction modifiers, detergents, agents dispersants and mixtures thereof, in particular among anti-oxidants, pour point depressant additives, anti-foaming agents and anti-corrosion agents.

La ou les caractéristiques du diester présentées dans le cadre de la composition selon l’invention sont également applicables au diester utilisé selon l’invention. The characteristic(s) of the diester presented in the context of the composition according to the invention are also applicable to the diester used according to the invention.

Selon un mode de réalisation de l’utilisation selon l’invention, la pièce lubrifiée et/ou refroidie est une pièce d’un véhicules lourd ou léger, d’un engin de travaux publics, ou d’un dispositif de stockage d’énergie (ex. datacenter). According to one embodiment of the use according to the invention, the lubricated and/or cooled part is a part of a heavy or light vehicle, a public works machine, or an energy storage device (e.g. data center).

Le diester défini dans la présente invention permet de réduire les coefficients de frottement de la composition lubrifiante. The diester defined in the present invention makes it possible to reduce the friction coefficients of the lubricating composition.

Le diester défini dans la présente invention permet de refroidir les éléments d’un système mobile ou stationnaire, tel qu’un véhicule lourd ou léger, un engin de travaux publics, un dispositif de stockage d’énergie. The diester defined in the present invention makes it possible to cool the elements of a mobile or stationary system, such as a heavy or light vehicle, a public works machine, an energy storage device.

La composition formulée selon l’invention, en particulier telle que décrite précédemment, présente d’excellentes propriétés tribologiques, notamment en termes de réduction des frottements, ce qui la rend particulièrement bien adaptée à une mise en œuvre comme fluide lubrifiant. The composition formulated according to the invention, in particular as described above, has excellent tribological properties, particularly in terms of reducing friction, which makes it particularly well suited to use as a lubricating fluid.

La composition formulée selon l’invention, en particulier telle que décrite précédemment, présente d’excellentes propriétés thermiques, notamment en termes de conductivité thermique, ce qui la rend particulièrement bien adaptée à une mise en œuvre comme fluide de refroidissement. The composition formulated according to the invention, in particular as described above, has excellent thermal properties, particularly in terms of thermal conductivity, which makes it particularly well suited to use as a cooling fluid.

Une composition de l’invention est adaptée pour la lubrification des organes de transmission de véhicules à moteur, notamment de transmission pour véhicules légers ou lourds, par exemple boîtes de vitesse et/ou ponts. A composition of the invention is suitable for the lubrication of transmission members of motor vehicles, in particular transmissions for light or heavy vehicles, for example gearboxes and/or axles.

En particulier, elle peut être mise en œuvre pour lubrifier la boîte de vitesse manuelle et/ou les ponts d’un véhicule léger ou lourd. Avantageusement, une composition lubrifiante selon l’invention présente des performances en particulier en termes de propriétés à froid, particulièrement bien adaptées à son utilisation pour la transmission de véhicules poids lourds, en particulier pour lubrifier la boite de vitesse manuelle et/ou les ponts poids lourds. La présente invention concerne également un procédé de lubrification et/ou de refroidissement d’au moins une pièce d’un système mobile ou stationnaire, comprenant la mise en contact de la composition selon l’invention avec ladite pièce. In particular, it can be used to lubricate the manual gearbox and/or the axles of a light or heavy vehicle. Advantageously, a lubricating composition according to the invention has performances in particular in terms of cold properties, particularly well suited to its use for the transmission of heavy goods vehicles, in particular for lubricating the manual gearbox and/or the weight axles. heavy. The present invention also relates to a method of lubricating and/or cooling at least one part of a mobile or stationary system, comprising bringing the composition according to the invention into contact with said part.

Selon un mode de réalisation, le système mobile ou stationnaire est choisi parmi un véhicule lourd ou léger, un engin de travaux publics, un dispositif de stockage d’énergie tel qu’un datacenter. According to one embodiment, the mobile or stationary system is chosen from a heavy or light vehicle, a public works machine, an energy storage device such as a data center.

La présente invention concerne également un procédé de lubrification et/ou de refroidissement d’au moins une pièce mécanique, en particulier un organe de transmission de véhicule à moteur, comprenant la mise en contact de la composition lubrifiante selon l’invention avec ladite pièce mécanique, en particulier ledit organe de transmission de véhicule à moteur. The present invention also relates to a method of lubricating and/or cooling at least one mechanical part, in particular a motor vehicle transmission member, comprising bringing the lubricating composition according to the invention into contact with said mechanical part. , in particular said motor vehicle transmission member.

Les diesters définis dans l’invention peuvent être ajoutés dans des compositions lubrifiantes mises en œuvre dans des transmissions de véhicules afin d’améliorer leurs propriétés « Fuel-Eco », à savoir leur aptitude à limiter la consommation de carburant des véhicules à moteur, sans affecter leurs performances, notamment en termes de propriétés à froid. The diesters defined in the invention can be added to lubricating compositions used in vehicle transmissions in order to improve their “Fuel-Eco” properties, namely their ability to limit the fuel consumption of motor vehicles, without affect their performance, particularly in terms of cold properties.

L’invention va maintenant être décrite au moyen des exemples suivants, donnés bien entendu à titre illustratif et non limitatif de l’invention. The invention will now be described by means of the following examples, given of course by way of illustration and not limitation of the invention.

Exemple Example

Exemple 1 :

Figure imgf000030_0001
des composé testés Example 1:
Figure imgf000030_0001
compounds tested

Les composés suivants ont été préparés : The following compounds were prepared:

- Diester A : diester formé à partir de 1,2-décanediol et de deux acides heptanoïques- Diester A: diester formed from 1,2-decanediol and two heptanoic acids

- Diester B : diester formé à partir de 1,2-décanediol et de deux acides pentanoïques- Diester B: diester formed from 1,2-decanediol and two pentanoic acids

- Diester C : diester formé à partir de 1,2-propanediol et de deux acides heptanoïques- Diester C: diester formed from 1,2-propanediol and two heptanoic acids

- Diester D : diester formé à partir de 1,2-propanediol et de deux acides nonanoïques- Diester D: diester formed from 1,2-propanediol and two nonanoic acids

- Diester E : diester formé à partir de 1,3 -propanediol et de deux acides heptanoïques- Diester E: diester formed from 1,3-propanediol and two heptanoic acids

- Diester F : mélange de diesters formés à partir de 1,2-propanediol et d’une coupe biosourcée d’acides en C8-C10 monoester formé à partir d’un acide monocarboxylique comportant une chaîne hydrocarbonée saturée de 3 à 14 atomes de carbone ; et un monoalcool comportant une chaîne hydrocarbonée saturée de 3 à 14 atomes de carbone. - Diester F: mixture of diesters formed from 1,2-propanediol and a biosourced cut of C8-C10 acids 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.

Les diesters et le monoester ont été préparés selon des méthodes connues de préparation d’esters. The diesters and monoester were prepared according to known ester preparation methods.

Les compositions testées dans la suite des exemples comprennent 100% de chaque ester (diester ou monoester) défini dans cet exemple 1. The compositions tested in the following examples comprise 100% of each ester (diester or monoester) defined in this example 1.

Exemple 2 : Mesure de viscosité Example 2: Viscosity measurement

La viscosité cinématique à 100°C (KV100) et la viscosité cinématique à 40°C (KV40) ont été déterminées selon la norme ASTM D445. The kinematic viscosity at 100°C (KV100) and the kinematic viscosity at 40°C (KV40) were determined according to the ASTM D445 standard.

Les viscosités sont présentées dans le tableau 2. The viscosities are presented in Table 2.

[Tableau 2]

Figure imgf000031_0001
[Table 2]
Figure imgf000031_0001

Tous les diesters mis en œuvre selon l’invention présentent une viscosité inférieure à 4 mm2/s à 100°C. All the diesters used according to the invention have a viscosity less than 4 mm 2 /s at 100°C.

Exemple 3 : Mesure des coefficients de frottement Example 3: Measuring friction coefficients

Les propriété tribologies peuvent être évaluées par un test sur tribomètre rotatif bille- disque (appelé également bille-plan) de type Tribomètre linéaire alternatif (ou « Linear reciprocating tribometer » en langue anglaise). Ce test permet notamment d’évaluer les performances de lubrifiants en termes de frottements en régime mixte/limite selon les conditions de charge, de pression ou de vitesse appliquées. The tribological properties can be evaluated by a test on a rotating ball-disc tribometer (also called ball-plane) of the Linear reciprocating tribometer type. This test makes it possible in particular to evaluate the performance of lubricants in terms of friction in mixed/limit regime depending on the load, pressure or speed conditions applied.

Le coefficient de friction des compositions lubrifiantes testées est déterminé à 40 °C en mettant en œuvre une bille en acier trempé d’environ 2 cm de diamètre, par exemple de 1,905 cm de diamètre, sur un plan en acier trempé. The coefficient of friction of the lubricating compositions tested is determined at 40°C by placing a hardened steel ball of approximately 2 cm in diameter, for example 1.905 cm in diameter, on a hardened steel plane.

Le tribomètre peut être un dispositif permettant de mettre en mouvement relatif une bille d'acier et un plan en acier afin de déterminer les coefficients de friction/frottement pour une composition lubrifiante donnée, tout en faisant varier diverses propriétés comme la vitesse, la charge, et la température. Le plan en acier trempé est de référence AISI 52100 avec une finition miroir et la bille est également de référence AISI 52100 réalisée en acier trempé. The tribometer can be a device allowing a steel ball and a steel plane to be put into relative motion in order to determine the coefficients of friction/friction for a given lubricating composition, while varying various properties such as speed, load, and temperature. The hardened steel surface is reference AISI 52100 with a mirror finish and the ball is also reference AISI 52100 made from hardened steel.

La charge appliquée est respectivement de 25 N et la vitesse d’entrainement varie de 10 mm/s à 2500 mm/s. Le coefficient de frottement est en particulier déterminé à une vitesse de rotation de 10 mm/s. Le coefficient est déterminé à un ratio vitesse de glissement/vitesse d'entraînement (« Slide-to-Roll Ratio » ou %SRR) de 5%. The applied load is respectively 25 N and the driving speed varies from 10 mm/s to 2500 mm/s. The coefficient of friction is in particular determined at a rotation speed of 10 mm/s. The coefficient is determined at a sliding speed/drive speed ratio (“Slide-to-Roll Ratio” or %SRR) of 5%.

Approximativement 50 ml de composition lubrifiante testée ont été introduits dans le dispositif. La bille est engagée face contre plan, ladite bille et ledit plan étant actionnés indépendamment de sorte à créer un contact mixte roulement/glissement. Approximately 50 ml of tested lubricating composition was introduced into the device. The ball is engaged face against plane, said ball and said plane being actuated independently so as to create a mixed rolling/sliding contact.

Le coefficient de friction est mesuré et enregistré par l’intermédiaire d’un capteur de force. The coefficient of friction is measured and recorded via a force sensor.

Les résultats avec une vitesse d’entrainement de 225 mm2/s sont indiqués dans le tableau 3. The results with a drive speed of 225 mm 2 /s are shown in Table 3.

Les compositions lubrifiantes testées comprennent 100% de chaque ester défini dans l’exemple 1. The lubricating compositions tested comprise 100% of each ester defined in Example 1.

[Tableau 3]

Figure imgf000032_0001
Figure imgf000033_0001
[Table 3]
Figure imgf000032_0001
Figure imgf000033_0001

Ces résultats montrent que les diesters mis en œuvre selon l’invention présentent de très faibles coefficients de frottement, en particulier un coefficient de frottement plus faible que le monoester. These results show that the diesters used according to the invention have very low friction coefficients, in particular a lower friction coefficient than the monoester.

Exemple 4 : Mesure du mini point éclair Example 4: Mini flash point measurement

Le mini point éclair est mesuré selon la norme ASTM D93Ac (méthode de Cl eaveland à vase ouvert). The mini flash point is measured according to the ASTM D93Ac standard (Cl eaveland open cup method).

Les valeurs sont indiquées dans le tableau 4. The values are shown in Table 4.

[Tableau 4]

Figure imgf000033_0002
[Table 4]
Figure imgf000033_0002

Comme le montrent les valeurs du tableau 4, le point éclair est d’autant meilleur que le diester est un diester ramifié. En effet, le diester formé à partir de propanediol de type 1,2 présente un point éclair plus faible que le diester formé à partir de propanediol de type 1,3, à même nombre d’atomes de carbone au total. As shown by the values in Table 4, the flash point is better if the diester is a branched diester. Indeed, the diester formed from type 1,2 propanediol has a lower flash point than the diester formed from type 1,3 propanediol, with the same number of carbon atoms in total.

Exemple 5 : Mesure du mini point d’écoulement Example 5: Measuring the mini pour point

Le mini point d’écoulement est mesuré selon la norme ASTM D7346. Mini pour point is measured according to ASTM D7346.

Les valeurs sont indiquées dans le tableau 5. [Tableau 5]

Figure imgf000034_0001
The values are shown in Table 5. [Table 5]
Figure imgf000034_0001

Les résultats du tableau 5 montrent que les diesters mis en œuvre dans la composition lubrifiante selon l’invention présente un point d’écoulement faible, en particulier plus faible que le monoester. The results in Table 5 show that the diesters used in the lubricating composition according to the invention have a low pour point, in particular lower than the monoester.

Exemple 6 : Mesure du coefficient de traction Example 6: Measurement of the traction coefficient

Le coefficient de traction (COT) a été mesuré à l’aide du tribomètre MTM de PCS instrument. Il permet d'évaluer les performances de lubrifiants en termes de frottement en régime mixte/hydrodynamique. Ce test consiste à mettre en mouvement relatif une bille d'acier et un plan en acier, à des vitesses différentes, permettant de définir le %SSR (Ratio vitesse de glissement/vitesse d'entraînement ou « Slide-to-Roll Ratio » en langue anglaise) qui correspond à la vitesse de glissement/vitesse d'entraînement. The coefficient of traction (COT) was measured using the PCS instrument MTM tribometer. It makes it possible to evaluate the performance of lubricants in terms of friction in mixed/hydrodynamic conditions. This test consists of putting a steel ball and a steel plane into relative motion, at different speeds, making it possible to define the %SSR (Sliding speed/drive speed ratio or “Slide-to-Roll Ratio” in English language) which corresponds to the sliding speed/drive speed.

Les conditions de mesure étaient 25 N de charge, une vitesse du disque de 1,4 m/s pour une température évaluée de 100 °C et un SRR de 20%. The measurement conditions were 25 N load, a disk speed of 1.4 m/s for a rated temperature of 100 °C and an SRR of 20%.

Plus le coefficient de traction est bas pour une composition lubrifiante, et plus les frottements entre les pièces métalliques sont réduits, entraînant ainsi un gain supérieur en termes d’économie de carburant. The lower the traction coefficient for a lubricating composition, the more friction between metal parts is reduced, thus resulting in a greater gain in fuel economy.

Les résultats obtenus sont indiqués dans le tableau 6. The results obtained are shown in Table 6.

[Tableau 6]

Figure imgf000034_0002
Figure imgf000035_0001
[Table 6]
Figure imgf000034_0002
Figure imgf000035_0001

Ces résultats montrent que les diesters mis en œuvre selon l’invention présentent de très faibles coefficients de traction, en particulier un coefficient de traction plus faible que le monoester. These results show that the diesters used according to the invention have very low traction coefficients, in particular a lower traction coefficient than the monoester.

Exemple 7 : Mesure de la conductivité thermique Example 7: Measurement of thermal conductivity

La conductivité thermique des composés décrits dans l’exemple 1 a été déterminée selon la norme ASTM D7896-19 à différentes températures. The thermal conductivity of the compounds described in Example 1 was determined according to standard ASTM D7896-19 at different temperatures.

Les résultats sont indiqués dans le tableau 7. The results are shown in Table 7.

[Tableau 7]

Figure imgf000035_0002
[Table 7]
Figure imgf000035_0002

Ces résultats montrent que les diesters définis dans l’invention présentent de bonnes propriétés thermiques, ce qui permet leur utilisation comme fluide de refroidissement. These results show that the diesters defined in the invention have good thermal properties, which allows their use as a cooling fluid.

Claims

Revendications Claims 1. Composition lubrifiante comprenant : 1. Lubricating composition comprising: - Un ou plusieurs diesters, chacun desdits diesters étant formé entre : o un diol choisi parmi le 1,2-propanediol, le 1,2-décanediol et les 1,3-diol comportant de 3 à 10 atomes de carbone, et o deux acides monocarboxyliques, identiques ou différents, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone, ladite chaine hydrocarbonée étant éventuellement interrompue par un ou plusieurs hétéroatomes et au moins une huile de base distincte du diester et/ou au moins un additif distinct du diester, ledit additif étant choisi parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges. - One or more diesters, each of said diesters being formed between: o a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diols comprising from 3 to 10 carbon atoms, and o two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms, said hydrocarbon chain optionally being interrupted by one or more heteroatoms and at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, point lowering additives (PPD), dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof. 2. Composition lubrifiante selon la revendication 1, dans laquelle la chaine hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone est une chaîne alkyle ou alkylène, linéaire ou ramifiée, saturée ou insaturée, constituée d’atomes de carbone et d’hydrogène. 2. Lubricating composition according to claim 1, in which the linear or branched hydrocarbon chain comprising 4 to 10 carbon atoms is an alkyl or alkylene chain, linear or branched, saturated or unsaturated, consisting of carbon and hydrogen atoms . 3. Composition lubrifiante selon la revendication 1 ou 2, comprenant : de 5 à 95% massique, de préférence de 10 à 90% massique, de préférence encore de 20 à 80% massique, encore plus préférentiellement de 30 à 70% massique, voire de 40 à 60% massique dudit ou desdits diesters, de 1 à 95% massique, de préférence de 10 à 90% massique, de préférence encore de 20 à 80% massique, encore plus préférentiellement de 30 à 70% massique, voire de 40 à 60% massique d’une ou plusieurs huiles de base différentes desdits diesters, éventuellement de 0,01 à 20% massique, de préférence de 0,05 à 15% massique, de préférence encore de 0,1 à 10% massique, encore plus préférentiellement de 0,5 à 7% massique, voire de 1 à 5% massique d’un ou plusieurs additifs distincts du diester et distincts de(s) huile(s) de base, par rapport à la masse totale de la composition. 3. Lubricating composition according to claim 1 or 2, comprising: from 5 to 95% by weight, preferably from 10 to 90% by weight, more preferably from 20 to 80% by weight, even more preferably from 30 to 70% by weight, or even from 40 to 60% by weight of said diester(s), from 1 to 95% by weight, preferably from 10 to 90% by weight, more preferably from 20 to 80% by weight, even more preferably from 30 to 70% by weight, or even from 40 at 60% by weight of one or more base oils different from said diesters, optionally from 0.01 to 20% by weight, preferably from 0.05 to 15% by weight, more preferably from 0.1 to 10% by weight, again more preferably from 0.5 to 7% by weight, or even 1 to 5% by weight of one or more additives distinct from the diester and distinct from the base oil(s), relative to the total mass of the composition. 4. Composition lubrifiante selon l’une des revendications 1 à 3, comprenant : au moins 5% massique, de préférence au moins 10% massique, de préférence au moins 30% massique, de préférence au moins 50% massique, plus préférentiellement au moins 70% massique, voire au moins 90% massique, d’un ou plusieurs diesters ; de 0,01 à 20% massique, de préférence de 0,05 à 15% massique, de préférence encore de 0,1 à 10% massique, encore plus préférentiellement de 0,5 à 7% massique, voire de 1 à 5% massique, d’un ou plusieurs additifs choisi(s) parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges ; et 4. Lubricating composition according to one of claims 1 to 3, comprising: at least 5% by weight, preferably at least 10% by weight, preferably at least 30% by weight, preferably at least 50% by weight, more preferably at least 70% by weight, or even at least 90% by weight, of one or more diesters; from 0.01 to 20% by weight, preferably from 0.05 to 15% by weight, more preferably from 0.1 to 10% by weight, even more preferably from 0.5 to 7% by weight, or even from 1 to 5% mass, of one or more additives chosen from friction modifier additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, additives pour point depressants (PPDs), dispersants, antifoaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof; And - éventuellement de 5 à 94% massique, de préférence de 10 à 94% massique, de préférence de 15 à 90% massique d’huile(s) de base distincte(s) du diester selon l’invention, par rapport à la masse totale de la composition. - optionally from 5 to 94% by weight, preferably from 10 to 94% by weight, preferably from 15 to 90% by weight of base oil(s) distinct from the diester according to the invention, relative to the mass total composition. 5. Composition lubrifiante selon l’une quelconque des revendications précédentes, dans laquelle ledit diester comporte de 13 à 25 atomes de carbone, de préférence de 13 à 24 atomes de carbone. 5. Lubricating composition according to any one of the preceding claims, in which said diester comprises from 13 to 25 carbon atoms, preferably from 13 to 24 carbon atoms. 6. Composition lubrifiante selon l’une quelconque des revendications précédentes, dans laquelle ledit diester présente une viscosité cinématique à 100°C allant de 1 à 6 mm2/s, de préférence allant de 1 à 4 mm2/s. 6. Lubricating composition according to any one of the preceding claims, in which said diester has a kinematic viscosity at 100°C ranging from 1 to 6 mm 2 /s, preferably ranging from 1 to 4 mm 2 /s. 7. Composition lubrifiante selon l’une quelconque des revendications précédentes, dans laquelle le diol est choisi parmi le 1,2-propanediol, le 1,2-décanediol et le 1,3-alcanediol comportant de 3 à 7 atomes de carbone, de préférence parmi le 1,2- propanediol et le 1,3 -propanediol, de préférence encore le diol est le 1,2-propanediol. 7. Lubricating composition according to any one of the preceding claims, in which the diol is chosen from 1,2-propanediol, 1,2-decanediol and 1,3-alkanediol comprising from 3 to 7 carbon atoms, preferably from 1,2-propanediol and 1,3-propanediol, more preferably the diol is 1,2-propanediol. 8. Composition lubrifiante selon l’une quelconque des revendications précédentes, dans laquelle lesdits acides monocarboxyliques, identiques ou différents, comportent une chaîne hydrocarbonée linéaire comportant de 4 à 10 atomes de carbone, de préférence de 5 à 9 atomes de carbone. 8. Lubricating composition according to any one of the preceding claims, in which said monocarboxylic acids, identical or different, comprise a linear hydrocarbon chain comprising from 4 to 10 carbon atoms, preferably from 5 to 9 carbon atoms. 9. Composition lubrifiante selon l’une quelconque des revendications précédentes, dans laquelle ledit ou lesdits diester(s) est(sont) choisi(s) parmi : 9. Lubricating composition according to any one of the preceding claims, in which said diester(s) is(are) chosen from: - les diesters formés entre : - the diesters formed between: • un diol choisi parmi le 1,2-décanediol et le 1,3 propanediol, et • a diol chosen from 1,2-decanediol and 1,3 propanediol, and • deux acides monocarboxyliques, identiques ou différents, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone, ladite chaine hydrocarbonée étant éventuellement interrompue par un ou plusieurs hétéroatomes, • two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms, said hydrocarbon chain possibly being interrupted by one or more heteroatoms, - un diester formé à partir de 1,2-propanediol et de deux acides heptanoïques, - a diester formed from 1,2-propanediol and two heptanoic acids, - un diester formé à partir de 1,2-propanediol et de deux acides octanoïques, - a diester formed from 1,2-propanediol and two octanoic acids, - un diester formé à partir de 1,2-propanediol et de deux acides décanoïques, - a diester formed from 1,2-propanediol and two decanoic acids, - un diester formé à partir de 1,2-propanediol et d’un acide octanoïque et d’un acide décanoïque, et leurs mélanges. - a diester formed from 1,2-propanediol and an octanoic acid and a decanoic acid, and their mixtures. 10. Composition lubrifiante selon l’une quelconque des revendications précédentes, dans laquelle ledit ou lesdits diester(s) est(sont) choisi(s) parmi : 10. Lubricating composition according to any one of the preceding claims, in which said diester(s) is(are) chosen from: - un diester formé à partir de 1,2-décanediol et de deux acides heptanoïques, - a diester formed from 1,2-decanediol and two heptanoic acids, - un diester formé à partir de 1,2-décanediol et de deux acides pentanoïques, - a diester formed from 1,2-decanediol and two pentanoic acids, - un diester formé à partir de 1,2-propanediol et de deux acides heptanoïques,- a diester formed from 1,2-propanediol and two heptanoic acids, - un diester formé à partir de 1,2-propanediol et de deux acides nonanoïques,- a diester formed from 1,2-propanediol and two nonanoic acids, - un diester formé à partir de 1,3 -propanediol et de deux acides heptanoïques,- a diester formed from 1,3-propanediol and two heptanoic acids, - un diester formé à partir de 1,2-propanediol et de deux acides octanoïques, - a diester formed from 1,2-propanediol and two octanoic acids, - un diester formé à partir de 1,2-propanediol et de deux acides décanoïques, - un diester formé à partir de 1,2-propanediol et d’un acide octanoïque et d’un acide décanoïque, et leurs mélanges. - a diester formed from 1,2-propanediol and two decanoic acids, - a diester formed from 1,2-propanediol and an octanoic acid and a decanoic acid, and their mixtures. 11. Utilisation d’au moins un diester dans une composition lubrifiante, ledit diester étant formé entre : 11. Use of at least one diester in a lubricating composition, said diester being formed between: - un diol choisi parmi le 1,2-propanediol, le 1,2-décanediol et les 1 ,3-diol comportant de 3 à 10 atomes de carbone, et deux acides monocarboxyliques, identiques ou différents, comportant une chaîne hydrocarbonée linéaire ou ramifiée comportant de 4 à 10 atomes de carbone, ladite chaine hydrocarbonée étant éventuellement interrompue par un ou plusieurs hétéroatomes, ladite composition lubrifiante comprenant en outre au moins une huile de base distincte du diester et/ou au moins un additif distinct du diester, ledit additif étant choisi parmi les additifs modificateurs de frottement, les additifs anti-usure, les additifs extrême pression, les détergents, les antioxydants, les améliorants de l’indice de viscosité (VI), les additifs abaisseurs du point d’écoulement (PPD), les dispersants, les agents anti-mousse, les épaississants, les inhibiteurs de corrosion, les agents passivant du cuivre, et leurs mélanges. - a diol chosen from 1,2-propanediol, 1,2-decanediol and 1,3-diol comprising 3 to 10 carbon atoms, and two monocarboxylic acids, identical or different, comprising a linear or branched hydrocarbon chain comprising from 4 to 10 carbon atoms, said hydrocarbon chain being optionally interrupted by one or more heteroatoms, said lubricating composition further comprising at least one base oil distinct from the diester and/or at least one additive distinct from the diester, said additive being chosen from friction modifier additives, anti-wear additives, extreme pressure additives, detergents, antioxidants, viscosity index (VI) improvers, pour point depressant (PPD) additives, dispersants, anti-foaming agents, thickeners, corrosion inhibitors, copper passivating agents, and mixtures thereof. 12. Utilisation selon la revendication 11, pour lubrifier et/ou pour refroidir au moins un élément d’un système mobile ou stationnaire, choisi par exemple parmi un véhicule lourd ou léger, un engin de travaux public, et un système de stockage d’énergie. 12. Use according to claim 11, for lubricating and/or cooling at least one element of a mobile or stationary system, chosen for example from a heavy or light vehicle, a public works machine, and a storage system. energy. 13. Utilisation selon la revendication 12, dans laquelle le système mobile est un véhicule, la composition lubrifiante étant utilisée pour réduire la consommation de carburant d’un véhicule équipé d’un organe de transmission, notamment d’une boîte de vitesses et/ou d’un pont, lubrifié au moyen de cette composition. 13. Use according to claim 12, in which the mobile system is a vehicle, the lubricating composition being used to reduce the fuel consumption of a vehicle equipped with a transmission member, in particular a gearbox and/or of a bridge, lubricated by means of this composition. 14. Utilisation selon l’une quelconque des revendications 11 à 13, dans laquelle le diester est tel que défini dans l’une quelconque des revendications 2,5 à 9 et/ou la composition lubrifiante est telle que définie dans la revendication 3 ou 4. 14. Use according to any one of claims 11 to 13, in which the diester is as defined in any one of claims 2.5 to 9 and/or the lubricating composition is as defined in claim 3 or 4 .
PCT/EP2023/069110 2022-07-13 2023-07-11 Diester-based lubricant composition Ceased WO2024013127A1 (en)

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WO2010038147A1 (en) 2008-10-03 2010-04-08 Total Raffinage Marketing Lubricating compositions for transmissions
US20120283162A1 (en) * 2009-12-28 2012-11-08 Idemitsu Kosan Co., Ltd Base oil for cooling of device, device-cooling oil containing the base oil, device to be cooled by the cooling oil, and device cooling method using the cooling oil
US20170145337A1 (en) 2014-06-16 2017-05-25 Jx Nippon Oil & Energy Corporation Lubricating oil composition for transmissions
WO2019025446A1 (en) * 2017-08-03 2019-02-07 Total Marketing Services Lubricating composition comprising a diester
WO2020007853A1 (en) * 2018-07-02 2020-01-09 Total Marketing Services Composition for cooling and lubricating a propulsion system of an electric or hybrid vehicle

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997049786A1 (en) * 1996-06-24 1997-12-31 Perstorp Ab A lubricant ester
US20060019840A1 (en) * 2002-08-22 2006-01-26 New Japan Chemical Co., Ltd. Lubricating oil for bearing
JP2005154726A (en) * 2003-05-19 2005-06-16 New Japan Chem Co Ltd Lubricating oil
WO2010038147A1 (en) 2008-10-03 2010-04-08 Total Raffinage Marketing Lubricating compositions for transmissions
US20120283162A1 (en) * 2009-12-28 2012-11-08 Idemitsu Kosan Co., Ltd Base oil for cooling of device, device-cooling oil containing the base oil, device to be cooled by the cooling oil, and device cooling method using the cooling oil
US20170145337A1 (en) 2014-06-16 2017-05-25 Jx Nippon Oil & Energy Corporation Lubricating oil composition for transmissions
WO2019025446A1 (en) * 2017-08-03 2019-02-07 Total Marketing Services Lubricating composition comprising a diester
WO2020007853A1 (en) * 2018-07-02 2020-01-09 Total Marketing Services Composition for cooling and lubricating a propulsion system of an electric or hybrid vehicle

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