EP4232534B1 - Verwendung von dialkylenglycolester zur reibungsminderung in fahrzeugen mit hybridmotoren - Google Patents

Verwendung von dialkylenglycolester zur reibungsminderung in fahrzeugen mit hybridmotoren Download PDF

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Publication number
EP4232534B1
EP4232534B1 EP21798327.9A EP21798327A EP4232534B1 EP 4232534 B1 EP4232534 B1 EP 4232534B1 EP 21798327 A EP21798327 A EP 21798327A EP 4232534 B1 EP4232534 B1 EP 4232534B1
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Prior art keywords
carbon atoms
linear
alkyl group
groups
diester
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EP21798327.9A
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English (en)
French (fr)
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EP4232534A1 (de
Inventor
Gael Robineau
Nicolas BORD
Paula USSA ALDANA
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TotalEnergies Onetech SAS
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TotalEnergies Onetech SAS
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/74—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C10M2219/068—Thiocarbamate metal salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/54—Fuel economy
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • the present invention relates to the use of dialkylene glycol ester in a lubricating composition for a vehicle equipped with a hybrid engine, to reduce the coefficient of friction when using the engine at low speed and/or when cold.
  • Hybrid vehicles have particular constraints, particularly at low speeds and when cold, i.e. over specific periods that can be described as the "start of the cycle", after starting the vehicle. Over these cycles, the temperatures of the oils used in a hybrid vehicle are low, lower than those used in a vehicle comprising a heat engine, and it is of essential interest to propose a formulation demonstrating gains over these particular periods of use.
  • FR 3083244 describes the use, for cooling and lubricating a propulsion system of an electric or hybrid vehicle, of a composition comprising at least one base oil and at least one alkylene glycol diester.
  • An objective of the present invention is therefore to provide an additive for a lubricating composition for a vehicle equipped with a hybrid engine, to reduce the coefficient of friction when using the engine at low speed.
  • Another objective of the present invention is also to provide an additive for a lubricating composition for a vehicle equipped with a hybrid engine, to reduce the coefficient of friction when using the engine when cold.
  • low speed means a specific engine speed.
  • the engine speed designates the rotational speed of the engine and is expressed in revolutions per minute.
  • the low speed is characterized by a number of revolutions per minute (rpm) of between 600 and 2000 rpm, preferably between 900 and 1500 rpm.
  • cold means the use of the engines during start-up and during phase 1 of the WLTC cycle, the engine is then at a temperature below 50°C, preferably between 20 and 50°C, preferably between 25 and 40°C.
  • the reduction in the coefficient of friction should be understood as a reduction compared to what would be observed with the lubricating composition not comprising the diester of the invention.
  • n 2 or 3, preferably 2.
  • At least one of the R groups represents an alkyl group, linear or branched, comprising from 1 to 5 carbon atoms, preferably from 1 to 4 carbon atoms, more preferably methyl, ethyl or propyl, advantageously methyl.
  • At least one of the groups R or R' in the diester of formula (I') represents an alkyl group, linear or branched, comprising from 1 to 5 carbon atoms, preferably from 1 to 4 carbon atoms, preferably methyl, ethyl, or propyl, advantageously methyl.
  • Ra and Rb have a linear chain of 7 to 14 carbon atoms, preferably of 8 to 12 carbon atoms, more particularly of 8 to 11 carbon atoms, in particular 9 or 11 carbon atoms.
  • s, in formulas (I) or (I'), represents 2.
  • At least one of the R groups represents an alkyl group, linear or branched, comprising from 1 to 5 carbon atoms, preferably methyl, ethyl or propyl, preferably methyl; and at least one of the R' represents an alkyl group, linear or branched, comprising from 1 to 5 carbon atoms, preferably methyl, ethyl or propyl, preferably methyl.
  • one of the R groups represents a linear or branched alkyl group comprising from 1 to 5 carbon atoms, preferably methyl, ethyl or propyl, preferably methyl; and one of the R' represents a linear or branched alkyl group comprising from 1 to 5 carbon atoms, preferably methyl, ethyl or propyl, preferably methyl; the other groups R and R' representing hydrogen atoms.
  • At least one of the R represents an alkyl group, linear or branched, comprising from 1 to 5 carbon atoms, preferably methyl, ethyl or propyl, preferably methyl.
  • one of the R groups represents an alkyl group, linear or branched, comprising from 1 to 5 carbon atoms, preferably methyl, ethyl or propyl, preferably methyl, the others represent hydrogen atoms.
  • linear chain of x to y carbon atoms should be understood to mean a carbon chain, saturated or unsaturated, preferably saturated, comprising from x to y carbon atoms, one after the other, the carbon atoms possibly present at the branches of the carbon chain not being taken into account in the number of carbon atoms (x-y) constituting the linear chain.
  • Ra and Rb are of plant, animal or petroleum origin.
  • Ra and Rb identical or different, represent saturated groups.
  • Ra and Rb identical or different, represent linear groups.
  • Ra and Rb identical or different, represent saturated linear hydrocarbon groups comprising from 6 to 18 carbon atoms, preferably from 7 to 17 carbon atoms, in particular from 7 to 14 carbon atoms, preferably from 8 to 12 carbon atoms, in particular 9 or 12 carbon atoms.
  • Ra and Rb represent saturated linear alkyl groups comprising from 6 to 18 carbon atoms, preferably from 7 to 17 carbon atoms, in particular from 7 to 14 carbon atoms, preferably from 8 to 12 carbon atoms, in particular 9 or 12 carbon atoms.
  • Ra and Rb are identical.
  • diesters of formula (I) may be commercially available or prepared according to synthesis methods described in the literature and known to those skilled in the art, in particular according to methods described in WO2019025446 .
  • the diester of formula (I) is added in a proportion of 1 to 40% by mass relative to the total mass of the lubricating composition, preferably 10 to 30%.
  • the base oil used in the lubricating compositions of the invention may be oils of mineral or synthetic origin belonging to groups I to V according to the classes defined by the API classification (or their equivalents according to the ATIEL classification (Table 1) or their mixtures.
  • the mineral base oils of the invention include any type of base oil obtained by atomospheric and vacuum distillation of crude oil, followed by refining operations such as solvent extraction, deasphalting, solvent dewaxing, hydrotreating, hydrocracking, hydroisomerization and hydrofinishing.
  • Mixtures of synthetic and mineral oils can also be used.
  • the base oils of the lubricating compositions according to the invention may also be chosen from synthetic oils, such as certain esters of carboxylic acids and alcohols, and polyalphaolefins.
  • the polyalphaolefins used as base oils are for example obtained from monomers comprising from 4 to 32 carbon atoms, for example from octene or decene, and for which the viscosity at 100°C is between 1.5 and 15 mm2.s-1 according to the ASTM D445 standard. Their average molar mass is generally between 250 and 3000 according to the ASTM D5296 standard.
  • the lubricating composition according to the invention may comprise at least 50% by weight of base oil relative to the total weight of the composition. More advantageously, the lubricating composition according to the invention comprises at least 60% by weight, or even at least 70% by weight, of base oils relative to the total weight of the lubricating composition. More preferably, the lubricating composition according to the invention comprises from 75 to 97% by weight of base oils relative to the total weight of the composition.
  • composition of the invention may also comprise at least one additive.
  • the preferred additives for the lubricating composition according to the invention are chosen from detergent additives, friction modifying additives different from the molybdenum compounds defined above, extreme pressure additives, dispersants, pour point activators, anti-foaming agents, thickeners and their mixtures.
  • the lubricating compositions according to the invention comprise at least one extreme pressure additive, or a mixture.
  • Anti-wear additives and extreme pressure additives protect surface friction by forming a protective film adsorbed on its surfaces.
  • the anti-wear additives are chosen from additives comprising phosphorus and sulfur such as alkylthiophosphate metals, in particular zinc alkylthiophosphate, and more precisely zinc dialkyldithiophosphate or ZnDTP.
  • the preferred compounds are of formula Zn((SP(S)(OR)(OR'))2, in which R and R', identical or different, independently represents an alkyl group, preferably an alkyl group comprising from 1 to 18 carbon atoms.
  • Amine phosphates are also anti-wear additives that can be used in the lubricating compositions of the invention.
  • the phosphorus atoms provided by these additives can act as a poison for automobile catalytic systems since they generate ash. It is possible to minimize these effects by substituting a portion of the amine phosphates with additives that do not provide phosphorus, such as, for example, polysulfides, in particular sulfur-containing olefins.
  • the lubricating compositions according to the invention 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 relative to the total weight of lubricating composition, of anti-wear and extreme pressure additives.
  • the lubricating compositions according to the invention 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 relative to the total weight of lubricating composition, of anti-wear additives (or anti-wear compound).
  • compositions according to the invention may comprise at least one friction-modifying additive different from the molybdenum compounds of the invention.
  • the friction-modifying additives may in particular be chosen from compounds providing metallic elements and ashless compounds.
  • the compounds providing metallic elements mention may be made of transition metal complexes such as Mo, Sb, Sn, Fe, Cu, Zn for which the ligands may be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or phosphorus atoms.
  • the ashless friction-modifying additives are generally of organic origin or may be chosen from fatty acid monoesters and polyols, alkoxylated amines, alkoxylated fatty amines, fatty epoxides, fatty epoxide borates, fatty amines or glycerol acid esters.
  • the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms.
  • the lubricating composition according to the invention 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 relative to the total weight of the lubricating composition, of friction modifying additive other than the molybdenum compounds according to the invention.
  • the lubricating composition according to the invention can comprise at least one antioxidant additive.
  • Antioxidant additives generally delay the degradation of the lubricating composition. This degradation is most often expressed by the formation of deposits, by the presence of sludge or by an increase in the viscosity of the lubricating composition.
  • Antioxidant additives generally act as radical inhibitors or hydroperoxide destructive inhibitors. Commonly used antioxidants include phenolic antioxidants, amine antioxidants, sulfur and phosphorus-containing antioxidants. Some of these antioxidants, for example those comprising sulfur and phosphorus, can generate ash. Phenolic antioxidant additives may be ash-free or in the form of neutral or basic metal salts.
  • Antioxidant additives may in particular be selected from sterically hindered phenols, sterically hindered phenol esters, sterically hindered phenols comprising a thioether bridge, diphenylamines, diphenylamines substituted with at least one C1 to C12 alkyl group, N,N'-dialkyl-aryl-diamines and mixtures thereof.
  • the sterically hindered phenols are chosen from compounds comprising a phenol group for which at least one of the carbon atoms in the vicinity of the carbon atom carrying the alcohol function is substituted by at least one C1 to C10 alkyl group, preferably a C1 to C6 alkyl group, preferably a C4 alkyl group, preferably a tert-butyl group.
  • Amine compounds are another class of antioxidant additives that can be used, optionally in combination with phenolic antioxidant additives.
  • amine compounds are aromatic amines, for example aromatic amines of the formula NRaRbRc in which Ra represents an aliphatic group or an aromatic group, optionally substituted, Rb represents an aromatic group, optionally substituted, Rc represents a hydrogen atom, an alkyl group, an aryl group or a group of the formula RdS(O)zRe in which Rd represents an alkylene or alkenylene group, Re represents an alkyl group, an alkenyl group or an aryl group and z represents 0, 1 or 2.
  • Sulfur-containing alkylphenols or their alkali or alkaline earth metal salts can also be used as antioxidant additives.
  • antioxidant additives are compounds comprising copper, for example copper thio- or dithio-phosphate, copper salts of carboxylic acids, dithiocarbamates, sulfonates, phenates, copper acetylacetonates. Copper I and II salts, succinic acid or anhydride salts may also be used.
  • the lubricating compositions according to the invention may also comprise any type of antioxidant known to those skilled in the art.
  • the lubricating composition comprises at least one ash-free antioxidant additive.
  • the lubricating composition according to the invention comprises from 0.1 to 2% by weight relative to the total weight of the composition, of at least one antioxidant additive.
  • the lubricating composition according to the invention may also comprise at least one detergent additive.
  • Detergent additives generally reduce the formation of deposits on the surface of metal parts by dissolving secondary oxidation and combustion products.
  • the detergent additives that can be used in the lubricating compositions according to the invention are generally known to those skilled in the art.
  • the detergent additives can be anionic compounds comprising a long lipophilic hydrocarbon chain and a hydrophobic head.
  • the associated cation can be a metal cation of an alkali or alkaline-earth metal.
  • the detergent additives are preferably selected from alkali or alkaline earth metal salts of carboxylic acids, sulfonates, salicylates, naphthenates, and phenate salts.
  • the alkali and alkaline earth metals are preferably calcium, magnesium, sodium or barium.
  • metal salts generally comprise the metal in stoichiometric or excess amount, i.e. in a content greater than the stoichiometric content.
  • overbased detergents the excess metal implying the overbased nature of the detergent additive is generally in the form of an oil-insoluble metal salt, for example carbonate, hydroxide, oxalate, acetate, glutamate, preferably carbonate.
  • the lubricating composition according to the invention may comprise from 0.5 to 8% or from 2 to 4% by weight of overbased detergent additives relative to the total weight of the lubricating composition.
  • the lubricating composition according to the invention may also comprise a pour point lowering additive.
  • the pour point lowering additive By slowing down the formation of paraffin crystals, the pour point lowering additive generally improves the cold behavior of the lubricating composition according to the invention.
  • pour point lowering additives examples include alkyl polymethacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes, alkyl polystyrenes.
  • the lubricating composition according to the invention can also comprise a dispersing agent.
  • the dispersing agents can be chosen from Mannich bases, succinimides and their derivatives.
  • the lubricating composition according to the invention may comprise from 0.2 to 10% by weight of dispersing agent relative to the total weight of lubricating composition.
  • the lubricating composition according to the invention may also further comprise at least one other additional polymer improving the viscosity index.
  • additional polymer improving the viscosity index mention may be made of polymeric esters, homopolymers or copolymers, hydrogenated or not, of styrene, butadiene, and isoprene, polymethacrylates (PMA).
  • the lubricating composition according to the invention may comprise from 1 to 15% by weight relative to the total weight of lubricating composition, of additive improving the viscosity index.
  • the lubricating composition according to the invention may also comprise at least one thickening agent.
  • the lubricating composition according to the invention may also comprise an antifoaming agent and a demulsifying agent.
  • the lubricating composition of the invention further comprises at least one anti-wear agent, in particular based on Zinc, in particular ZnDTP.
  • hybrid-powered vehicles or vehicles equipped with a hybrid engine are understood to mean vehicles using two separate energy sources for their operation.
  • hybrid vehicles combine a thermal internal combustion engine and an electric motor, said electric motor participating in the traction of the vehicle.
  • the invention also relates to a method for reducing friction when using a hybrid engine at low speed and/or when cold, comprising the addition to the lubricating composition of said engine of a diester according to the invention.
  • the invention also relates to a method for reducing friction when using a hybrid engine at low speed and/or when cold, comprising lubricating said engine with a lubricating composition comprising a diester according to the invention.
  • Example 1 Preparation of lubricating compositions
  • a PMF (Mean Friction Pressure) bench is used to measure the friction of an engine.
  • the engine is driven using a generator and the torque that this generator must provide is measured (this torque is thus the image of the engine friction).
  • the engine does not burn any fuel, it is just driven exactly as if it were in the engine brake life situation of a vehicle.
  • the engine speed sequences tested are as follows: 900, 1450, 2000, 2500, 3000, 3500, 4000, 4500
  • the test consists of drawing up a complete map of engine friction according to the different rotation speeds and the different water and oil temperatures.
  • the friction map created at the end of the test will be made up of 8 engine speeds and 4 temperatures.
  • the time to complete this mapping is approximately 11 hours.
  • This mapping is then compared to that of a so-called reference oil which will be measured before and after testing the candidate oil in order to qualify any drift in the test method and integrate it into the interpretation of the results.
  • the so-called reference oil has the following composition: Table 5 PAO 10.00 PAO 10.00 MoDTC 0.50 Pour point depressant 0.20 Base oil 61.70 Additive package 12.70 Amino antioxidant 0.50 Viscosity index improving polymer 4.40 It is in relation to the latter that the friction gain percentages are calculated.

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

Claims (9)

  1. Verwendung eines Diesters mit der Formel (I) in einer Schmiermittelzusammensetzung für ein Fahrzeug, das mit einem Hybridmotor ausgestattet ist, um die Reibungen bei der Verwendung des Motors mit niedriger Drehzahl zu reduzieren, gekennzeichnet durch eine Anzahl von Umdrehungen pro Minute (U/min), die im Bereich zwischen 600 und 2000 U/min und/oder im Kaltzustand liegt,

            Ra-C(O)-O-([C(R)2]n-O)s-C(O)-Rb     (I)

    wobei
    R unabhängig voneinander ein Wasserstoffatom oder eine lineare oder verzweigte Alkylgruppe, umfassend 1 bis 5 Kohlenstoffatome, darstellen;
    s 1 oder 2 darstellt;
    n 1, 2 oder 3 darstellt, wobei, wenn s verschieden von 1 ist, die n identisch oder verschieden sein können;
    Ra und Rb, identisch oder verschieden, unabhängig voneinander gesättigte oder ungesättigte, lineare oder verzweigte Kohlenwasserstoffgruppen darstellen, die eine lineare Verkettung von 6 bis 18 Kohlenstoffatomen darstellen;
    vorausgesetzt dass, wenn s den Wert 2 aufweist und n, identisch, den Wert 2 aufweisen, mindestens eine der Gruppen R eine lineare oder verzweigte Alkylgruppe, umfassend 1 bis 5 Kohlenstoffatome, darstellt; und
    vorausgesetzt dass, wenn s den Wert 1 aufweist und n den Wert 3 aufweist, mindestens eine der Gruppen R, die an den Kohlenstoff in der Betaposition der Sauerstoffatome der Esterfunktionen gebunden ist, ein Wasserstoffatom darstellt.
  2. Verwendung nach Anspruch 1, wobei, wenn s verschieden von 1 ist, alle n identisch sind.
  3. Verwendung nach einem der Ansprüche 1 oder 2, wobei n 2 oder 3 darstellt.
  4. Verwendung nach einem der Ansprüche 1 bis 3, wobei mindestens eine der Gruppen R eine lineare oder verzweigte Alkylgruppe darstellt, umfassend von 1 bis 5 Kohlenstoffatome.
  5. Verwendung nach einem der Ansprüche 1 bis 4, wobei der Diester mit der Formel (I) gemäß der Erfindung ein Diester mit der folgenden Formel (I') ist:

            Ra-C(O)-O-([C(R)2]n-OH[C(R')2]m-O)s-1-C(O)-Rb     (I')

    wobei
    R und R' unabhängig voneinander ein Wasserstoffatom oder eine lineare oder verzweigte Alkylgruppe darstellen, umfassend von 1 bis 5 Kohlenstoffatome;
    s 1 oder 2 darstellt;
    n 2 darstellt;
    m 2 darstellt;
    Ra und Rb, identisch oder verschieden, unabhängig voneinander gesättigte oder ungesättigte, lineare oder verzweigte Kohlenwasserstoffgruppen darstellen, die eine lineare Verkettung von 6 bis 18 Kohlenstoffatomen darstellen;
    vorausgesetzt dass, wenn s den Wert 1 aufweist mindestens eine der Gruppen R oder R' eine lineare oder verzweigte Alkylgruppe darstellt, umfassend von 1 bis 5 Kohlenstoffatome.
  6. Verwendung nach einem der Ansprüche 1 bis 5, wobei der Diester eine Verbindung mit der Formel (I"a) ist

            Ra-C(O)-O-CHR1-CHR2-O-CHR3-CHR4-O-C(O)-Rb     (I"a)

    wobei
    eine der Gruppen R1 und R2 eine lineare oder verzweigte Alkylgruppe darstellt, umfassend von 1 bis 5 Kohlenstoffatome, wobei die andere ein Wasserstoffatom darstellt; eine der Gruppen R3 und R4 eine lineare oder verzweigte Alkylgruppe darstellt, umfassend von 1 bis 5 Kohlenstoffatome, wobei die andere ein Wasserstoffatom darstellt Ra und Rb, identisch oder verschieden, wie in Anspruch 1 definiert sind.
  7. Verwendung nach einem der Ansprüche 1 bis 6, wobei der Diester mit der Formel (I) in einer Proportion von 1 bis 40 Gew.-% mit Bezug auf die Gesamtmasse der Schmiermittelzusammensetzung hinzugefügt wird.
  8. Verfahren zum Reduzieren der Reibungen bei der Verwendung eines Hybridmotors mit niedriger Drehzahl, gekennzeichnet durch eine Anzahl von Umdrehungen pro Minute (U/min), die im Bereich zwischen 600 und 2000 U/min und/oder im Kaltzustand liegt, umfassend das Hinzufügen in die Schmiermittelzusammensetzung

            Ra-C(O)-O-([C(R)2]n-O)s-C(O)-Rb     (I)

    des Motors eines Diesters mit der Formel (I),
    wobei
    R unabhängig voneinander ein Wasserstoffatom oder eine lineare oder verzweigte Alkylgruppe, umfassend 1 bis 5 Kohlenstoffatome, darstellen;
    s 1 oder 2 darstellt;
    n 1, 2 oder 3 darstellt, wobei, wenn s verschieden von 1 ist, die n identisch oder verschieden sein können;
    Ra und Rb, identisch oder verschieden, unabhängig voneinander gesättigte oder ungesättigte, lineare oder verzweigte Kohlenwasserstoffgruppen darstellen, die eine lineare Verkettung von 6 bis 18 Kohlenstoffatomen darstellen;
    vorausgesetzt dass, wenn s den Wert 2 aufweist und n, identisch, den Wert 2 aufweisen, mindestens eine der Gruppen R eine Alkylgruppe darstellt umfassend von 1 bis 5 Kohlenstoffatome; und
    vorausgesetzt dass, wenn s den Wert 1 aufweist und n den Wert 3 aufweist, mindestens eine der Gruppen R, die an den Kohlenstoff in der Betaposition der Sauerstoffatome der Esterfunktionen gebunden ist, ein Wasserstoffatom darstellt.
  9. Verfahren nach Anspruch 8, wobei der Diester wie in Anspruch 2 bis 7 definiert ist.
EP21798327.9A 2020-10-20 2021-10-19 Verwendung von dialkylenglycolester zur reibungsminderung in fahrzeugen mit hybridmotoren Active EP4232534B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2010736A FR3115291B1 (fr) 2020-10-20 2020-10-20 Utilisation d’ester de dialkylène glycol pour diminuer le frottement dans les véhicules équipés de moteur hybride
PCT/EP2021/078956 WO2022084320A1 (fr) 2020-10-20 2021-10-19 Utilisation d'ester de dialkylène glycol pour diminuer le frottement dans les véhicules équipés de moteur hybride

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EP4232534A1 EP4232534A1 (de) 2023-08-30
EP4232534B1 true EP4232534B1 (de) 2024-12-11

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US (1) US20230383210A1 (de)
EP (1) EP4232534B1 (de)
CN (1) CN116472330A (de)
ES (1) ES3009500T3 (de)
FR (1) FR3115291B1 (de)
WO (1) WO2022084320A1 (de)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2454349A (en) * 2007-10-30 2009-05-06 Ford Global Tech Llc Heating hybrid vehicle engine oil
FR2951456A1 (fr) * 2009-10-16 2011-04-22 Total Raffinage Marketing Lubrifiant moteur

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3686243A (en) * 1970-11-12 1972-08-22 Texaco Inc Process for preparation of zinc dialkyl dithiophosphates
EP2440640A1 (de) * 2009-06-12 2012-04-18 Evonik RohMax Additives GmbH Fluid mit verbessertem viskositätsindex
KR101301343B1 (ko) * 2011-05-06 2013-08-29 삼성전기주식회사 윤활유 조성물
CA2929468A1 (en) * 2013-11-26 2015-06-04 Basf Se The use of polyalkylene glycol esters in lubricating oil compositions
FR3048976B1 (fr) * 2016-03-15 2020-02-07 Total Marketing Services Composition lubrifiante a base de polyalkylene glycols
FR3069864B1 (fr) 2017-08-03 2019-08-16 Total Marketing Services Composition lubrifiante comprenant un diester
US20190106651A1 (en) * 2017-10-06 2019-04-11 Chevron Japan Ltd. Passenger car lubricating oil compositions for fuel economy
FR3083244B1 (fr) * 2018-07-02 2020-07-17 Total Marketing Services Composition pour refroidir et lubrifier un systeme de propulsion d'un vehicule electrique ou hybride

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2454349A (en) * 2007-10-30 2009-05-06 Ford Global Tech Llc Heating hybrid vehicle engine oil
FR2951456A1 (fr) * 2009-10-16 2011-04-22 Total Raffinage Marketing Lubrifiant moteur

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Publication number Publication date
FR3115291A1 (fr) 2022-04-22
US20230383210A1 (en) 2023-11-30
ES3009500T3 (en) 2025-03-27
WO2022084320A1 (fr) 2022-04-28
CN116472330A (zh) 2023-07-21
EP4232534A1 (de) 2023-08-30
FR3115291B1 (fr) 2023-11-17

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