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
  • C10M129/16—Ethers
• • 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
  • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
  • C10M169/04—Mixtures of base-materials and additives
• • 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
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/003—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions 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
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/102—Aliphatic fractions
  • C10M2203/1025—Aliphatic fractions 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
  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
  • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
  • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms 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
  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
• • 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
  • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
  • C10M2207/046—Hydroxy ethers
• • 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/084—Acrylate; Methacrylate
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/064—Di- and triaryl amines
• • 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
  • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
  • C10N2020/01—Physico-chemical properties
  • C10N2020/069—Linear chain compounds
• • 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
  • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
  • C10N2020/01—Physico-chemical properties
  • C10N2020/071—Branched chain compounds
• • 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
  • C10N2030/54—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
• • C10N2220/027—
• • C10N2220/028—
• • C10N2230/54—
• • C10N2240/10—

Definitions

• the invention relates to the field of friction modifiers, and, in particular, organic friction modifiers. More particularly, the invention relates to a lubricating composition comprising a friction modifier selected from glycerol monoethers. The invention also relates to the use of this lubricating composition for lubricating an engine.
• organic friction modifiers are studied and conventionally used. It has been found that glycerol esters are effective, and, in particular, glycerol mono-oleate is the most commonly used commercially. It has the advantage of not containing ash, phosphorus or sulfur and being produced from renewable raw materials. However, its properties as a friction modifier are lower than those of molybdenum dithiocarbamate.
• glycerol ethers as a friction modifier is also known.
• the application JPS5925890 describes the use of glycerol ethers comprising an alkyl chain comprising from 4 to 28 carbon atoms.
• JP2000273481 also discloses the use of glycerol ethers comprising an alkyl chain comprising more than 14 carbons as friction modifiers.
• an object of the present invention is to provide a friction modifier and a lubricating composition comprising this friction modifier that overcome all or some of the aforementioned drawbacks.
• Another object of the present invention is to provide an organic friction modifier derived from renewable raw materials and which does not have the drawbacks of MoDTC and which is effective at low temperature.
• Yet another object of the present invention is to provide a lubricating composition for reducing friction and thus reducing the fuel consumption of the engine, preferably of a motor vehicle.
• the present invention thus relates to a lubricating composition
• a lubricating composition comprising:
• the group R comprises 6 or 7 carbon atoms.
• the composition according to the invention is an engine lubricant.
• the R group of the glycerol monoether according to the invention forms an ether bond with any oxygen atom of glycerol, whether it is bonded to one of the two primary carbons or to the secondary carbon of glycerol.
• the glycerol mono-ether is chosen from glycerol monoethers of formula (I) or (II), taken alone or as a mixture:
• R represents a linear or branched alkyl or alkylene group comprising from 5 to 8 carbon atoms, preferably from 6 to 7 carbon atoms, preferably 6 carbon atoms.
• R represents a linear or branched alkyl or alkylene group comprising 6 or 7 carbon atoms.
• the glycerol mono-ether according to the invention is chosen from the compounds of formula (I).
• the glycerol mono-ether according to the invention is chosen from the compounds of formula (II).
• the glycerol mono-ether according to the invention is a mixture of at least one compound of formula (I) and at least one compound of formula (II).
• the lubricating composition according to the invention comprises from 0.01% to 5% by weight of glycerol mono-ether according to the invention relative to the total weight of the lubricating composition.
• the lubricating composition comprises from 0.01% to 2% by weight, preferably from 0.1% to 1.5% by weight of glycerol mono-ether as defined above, relative to the total weight of the lubricating composition.
• glycerol monoethers according to the invention may be obtained by any technique known to those skilled in the art.
• a preferred synthetic route for the preparation of glycerol monoethers of the invention consists in the reaction between glycerol and an alcohol ROH, wherein R has the definition given above.
• the etherification reaction between glycerol and an alcohol is preferably carried out in the presence of an acid catalyst, preferably an acid heterogeneous catalyst or a homogeneous acid catalyst.
• the acidic heterogeneous catalysts are chosen from zeolites, resins or oxides of alumina.
• perfluorinated polymer resins such as Nafion® NR50, cation exchange resins such as Dowex 50wx8, or among ion exchange resins with acidic properties such as Amberlyst® 15 and 36.
• the acidic heterogeneous catalyst is a zeolite, preferably a mordenite type zeolite, preferably a mordenite with a Si/Al ratio of 11.
• the homogeneous acidic catalysts are chosen from phosphoric acid, para-toluenesulfonic acid (APTS) and triflic acid.
• the acidic homogeneous catalyst is para-toluenesulfonic acid (APTS).
• the amount of acidic homogeneous catalyst involved in the reaction is between 1% and 10 mol% relative to the glycerol content, preferably it is between 1% and 2.5 mol%.
• the amount of heterogeneous catalyst involved in the reaction is between 1 and 5 mol% relative to the glycerol content, preferably it is 3.5 mol%.
• the alcohol/glycerol molar ratio is optimized in order to obtain the best possible yield of glycerol mono-ether while limiting the secondary reactions of glycerol oligomer formation.
• the alcohol/glycerol molar ratio is between 1/6 and 3/1, preferably it is 1/1.
• the etherification reaction may also, in another embodiment, be carried out from the di-ether resulting from the reaction of the alcohol on itself.
• the etherification reaction of glycerol may be carried out in any type of reactor known to those skilled in the art.
• it is conducted in an autoclave.
• the conditions of temperature, pressure and the etherification reaction time of the glycerol can be determined in the usual manner by those skilled in the art.
• the reaction is carried out at a temperature of between 80 and 200° C., preferably between 130 and 160° C., for example it may be carried out at 150° C.
• the reaction is carried out for at least 5 hours, preferably for 5 to 48 hours.
• the reaction time may be 24 hours or 48 hours.
• the method comprises a purification step.
• This purification step may comprise the following steps: liquid-liquid extraction and/or fractional distillation under reduced pressure.
• the liquid-liquid extraction is conducted in the presence of a pair of solvents, which may be determined in the usual manner by those skilled in the art.
• the acetonitrile/heptane pair may be used.
• At least one liquid-liquid extraction is conducted, preferably at least two. Even more preferably, three liquid-liquid extractions are carried out.
• the initial alcohol and the glycerol mono-ether are separated.
• the process according to the invention makes it possible to selectively obtain glycerol monoethers.
• the lubricating composition according to the invention comprises at least one base oil.
• the base oil(s) used in the lubricating compositions according to the invention may be chosen from a wide range.
• the base oil of the lubricating composition used according to the invention may, in particular, be chosen from mineral, synthetic or natural oils, bio-sourced, animal, plant, known to those skilled in the art.
• the base oil(s) according to the invention may be oils of mineral or synthetic origin, chosen from oils of groups I to V according to the classes defined in the API classification (or their equivalents according to the ATIEL classification) (Table A), alone or in mixtures.
• the mineral base oils useful according to the invention include all types of bases obtained by atmospheric and vacuum distillation of crude oil, followed by refining operations such as solvent extraction, desalphating, solvent dewaxing, hydrotreatment, hydrocracking, hydroisomerization and hydrofinishing.
• Mixtures of synthetic and mineral oils may also be used.
• lubricating bases for producing the lubricating compositions used according to the invention, except that they must have properties, in particular viscosity, viscosity index, sulfur, oxidation resistance, adapted for use for engines or for vehicle transmissions.
• the lubricating composition according to the invention may comprise from 50 to 99% of at least one base oil, preferably from 60 to 99%, advantageously from 70 to 99% by weight, relative to the total weight of lubricating composition.
• the lubricating composition according to the invention may also comprise numerous additives.
• the preferred additives for the lubricating composition used according to the invention are chosen from detergents, antiwear additives, extreme pressure additives, viscosity index improvers, dispersants, antioxidants, pour point improvers, anti-foam agents, and inorganic friction modifiers and mixtures thereof.
• the lubricating composition according to the invention may also comprise at least one detergent additive.
• the detergent additives generally make it possible to reduce the formation of deposits on the surface of the metal parts by dissolving the secondary oxidation and combustion products.
• the detergent additives that may be used in the lubricating composition according to the invention are generally known to those skilled in the art.
• the detergent additives may be anionic compounds comprising a long lipophilic hydrocarbon chain and a hydrophilic head.
• the associated cation may be a metal cation of an alkali metal or alkaline earth metal.
• the detergent additives are preferably chosen from the alkali metal or alkaline earth metal salts of carboxylic acids, the sulphonates, the salicylates, the naphthenates and the phenate salts.
• the alkali and alkaline earth metals are preferably calcium, magnesium, sodium or barium.
• metal salts generally comprise the metal in stoichiometric amount or in excess, therefore in an amount greater than the stoichiometric amount.
• overbased detergent additives the excess metal bringing the overbased character to the detergent additive is then generally in the form of an oil-insoluble metal salt, for example a carbonate, a hydroxide, an oxalate, an acetate, a glutamate, preferably a carbonate.
• the lubricating composition according to the invention may comprise from 2 to 4% by weight of detergent additive relative to the total mass of the lubricating composition.
• Anti-wear additives and extreme pressure additives protect friction 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 ZnDTPs.
• the preferred compounds have the formula Zn((SP(S)(OR 11 )(OR 12 2 )), in which R 11 and R 12 , which may be identical or different, independently represent an alkyl group, preferably an alkyl group comprising from 1 to 18 carbon atoms.
• Amine phosphates are also anti-wear additives which may be used in the lubricating composition according to the invention.
• the phosphorus provided by these additives may act as a poison of the catalytic systems of automobiles because these additives are ash generators.
• these effects may be minimized by partially substituting amine phosphates with non-phosphorus additives, such as, for example, polysulfides, especially sulfur-containing olefins.
• the lubricating composition 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 the lubricating composition, anti-wear additives and extreme pressure additives.
• the lubricating composition of the present invention may also comprise at least one viscosity index improving additive.
• additives improving the viscosity index mention may be made of polymeric esters, homopolymers or copolymers, hydrogenated or non-hydrogenated, of styrene, butadiene and isoprene, in particular polyacrylates, polymethacrylates (PMA) or alternatively olefin copolymers, especially ethylene/propylene copolymers.
• the lubricating composition according to the invention may also comprise at least one dispersing agent.
• the dispersing agent may 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 mass of the lubricating composition.
• the lubricating composition according to the invention may comprise at least one antioxidant additive.
• the antioxidant additive generally serves to retard the degradation of the lubricating composition in service. This degradation may notably result in the formation of deposits, the presence of sludge or an increase in the viscosity of the lubricating composition.
• Antioxidant additives act in particular as radical inhibitors or destroyers of hydroperoxides.
• antioxidant additives commonly used, mention may be made of antioxidant additives of the phenolic type, antioxidant additives of the amine type, antioxidant phosphosulfur additives. Some of these antioxidant additives, for example phosphosulfur antioxidant additives, may be ash generators. Phenolic antioxidant additives may be ash-free or may be in the form of neutral or basic metal salts.
• the antioxidant additives may especially be chosen from sterically hindered phenols, sterically hindered phenol esters, and sterically hindered phenols comprising a thioether bridge, diphenylamines, diphenylamines substituted with at least one C 1 -C 12 alkyl group, and N,N′-dialkyl-aryl diamines and mixtures thereof.
• the sterically hindered phenols are chosen from compounds comprising a phenol group in which at least one vicinal carbon of the carbon bearing the alcohol function is substituted by at least one C 1 -C 10 alkyl group, preferably a C 1 -C 6 alkyl group, preferably a C 4 alkyl group, preferably by the ter-butyl group.
• Amino compounds are another class of antioxidant additives that may be used, optionally in combination with phenolic antioxidant additives.
• amine compounds are aromatic amines, for example aromatic amines of formula NR 13 R 14 R 15 in which R 13 represents an optionally substituted aliphatic or aromatic group, R 14 represents an optionally substituted aromatic group, R 15 represents a hydrogen atom, an alkyl group, an aryl group or a group of formula R 16 S(O) 2 R 17 in which R 16 represents an alkylene group or an alkenylene group, R 17 represents an alkyl group, an alkenyl group or an aryl group and z represents 0, 1 or 2.
• Sulfurized alkyl phenols or their alkali and alkaline earth metal salts may also be used as antioxidant additives.
• antioxidant additives is copper compounds, for example copper thio- or dithio-phosphates, copper and carboxylic acid salts, dithiocarbamates, sulphonates, phenates, copper acetylacetonates. Copper salts I and II, succinic acid or anhydride salts may also be used.
• the lubricating composition according to the invention may contain all types of antioxidant additives 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 0.5 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 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 lubricating composition according to the invention.
• pour point depressant additives mention may be made of alkyl polymethacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes and alkylated polystyrenes.
• the lubricating composition may also comprise an anti-foam additive chosen from silicones and their derivatives, such as polysiloxanes and their derivatives.
• an anti-foam additive may be Bluesil 47V12500® marketed by Bluestar Silicones.
• the antifoam additive of the lubricating composition according to the invention may also be chosen from acrylics, such as PC1244® marketed by Mosanto.
• the lubricating composition according to the invention may comprise at least one additional friction-modifying additive, such as an inorganic friction modifier.
• the inorganic friction modifier additive may be selected from a compound providing metal elements and an ash free compound.
• the compounds providing metal elements mention may be made of transition metal complexes such as Mo, Sb, Sn, Fe, Cu and Zn, the ligands of which may be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or phosphorus.
• Molybdenum dithiocarbamate (MoDTC) is the best known compound in this family.
• the lubricating composition according to the invention may comprise from 0.01 to 5% by weight or from 0.01 to 2% by weight, preferably from 0.1 to 1.5% by weight or 0.1 at 2% by weight relative to the total weight of the lubricating composition, of the additional friction modifier additive.
• the invention also relates to the use of a lubricating composition according to the invention for lubricating an engine, preferably a motor vehicle engine.
• the invention also relates to the use of a lubricating composition according to the invention for reducing the friction in an engine, preferably a motor vehicle engine.
• the invention also relates to the use of the lubricating composition according to the invention for reducing the fuel consumption of an engine, preferably of a motor vehicle engine.
• the reduction of friction in an engine or the reduction of the fuel consumption of an engine is measured with respect to the friction or fuel consumption measured with respect to a reference composition.
• the reference composition does not comprise glycerol mono-ether, characterized in that one of the alcohol functions of glycerol forms an ether function with an alkyl or alkylene R group comprising 6 or 7 carbon atoms.
• the invention also relates to the use of the lubricating composition according to the invention for reducing the fuel consumption at the start and during the operating phase of the engine.
• the invention also relates to the use of a glycerol mono-ether as defined above in a lubricating composition for reducing the friction in an engine or for reducing the fuel consumption of an engine, preferably a motor vehicle engine.
• a glycerol mono-ether of formula according to the invention allows a reduction in fuel consumption at startup and during the operating phase of the engine.
• the invention also relates to a method of lubricating an engine, preferably a motor vehicle engine comprising the implementation of a lubricating composition according to the invention.
• the invention also relates to a method for reducing the fuel consumption of an engine, preferably a motor vehicle engine comprising the implementation in the engine of a lubricating composition according to the invention.
• the different glycerol monoethers tested are described in Table I below.
• the synthetic route requires that the glycerol and fatty alcohol used is soluble one in the other. However, any fatty alcohol comprising 8 or more carbon atoms is not soluble in glycerol, wherein the corresponding glycerol ethers can not be synthesized according to the described synthetic route.
• the reactors used are the following:
• the amount of catalyst is a molar amount relative to the amount of glycerol used.
• the amount of glycerol monoethers obtained at the end of the reaction is measured by gas chromatography.
• TGA Thermogravimetric analysis
• glycerol monoethers (MEG C3P and MEG C4P) have a loss of mass of 100% for lower temperatures, and especially less than 190° C. which makes them difficult to use in an engine application or even incompatible with such an application.
• the glycerol monoethers according to the invention have a loss of mass of 100% for higher temperatures, and, in particular, may be greater than 200° C. which makes them fully compatible with use in a lubricating composition for a engine application.
• the HFRR (High Frequency Reciprocating Rig) test is used to evaluate the performance of fuels and lubricants in terms of friction in the mixed/limit regime.
• This test involves fixing a steel plane, on which the lubricating composition to be tested is placed, in a heating block. A steel ball subjected to a certain load is then brought into contact with the lubricating composition and the steel plane before being vibrated. The vibration frequency and the load applied to the ball as well as the temperature at which the lubricating composition is subjected are adjustable. This test makes it possible to obtain a coefficient of friction curve as a function of the duration of the test.
• test lasts 30 min, the ball travels back and forth 2 mm at a frequency of 20 Hz, an average shear rate of 40 mm.s ⁇ 1 (limit regime). At the stop point of the ball, the speed is zero which places this test well in a limited and mixed lubrication regime.
• a load of 200 g is applied on the ball, which corresponds to a pressure of 800 MPa. The oil is heated to 100° C.
• the MTM test (Traction Machine or Mini Traction Machine) makes it possible to evaluate the performance of lubricants in terms of friction in the mixed/hydrodynamic regime. This test consists in setting in relative motion a steel ball and a steel plane, at different speeds, allowing definition of the % SSR (ratio of the speed of slip/drive speed or Slide-to-Roll Ratio) which corresponds at the slip speed/drive speed.
• the tests consist of a 120 min accumulation period where the ball rotates at 100 mm.s ⁇ 1 (hydrodynamic regime) with a % SSR of 50%, for a load of 1.1 GPa and an oil temperature 100° C.
• a friction modifier is considered effective if it lowers the coefficient of friction.
• the different glycerol monoethers are tested in a reference lubricating composition whose composition is given in Table IV below.
• Viscosity modifier Poly(isoprene-styrene- 6.6 hydrogenated)
• Antioxidant Diphenylamine 1.5 Additive package P6003 ® marketed by the 12.3 company Infineum
• Each glycerol mono-ether is added at a content of 1% by weight relative to the total weight of the reference lubricating composition.
• the various lubricating compositions tested are described in Table V below.
• Composition 1 Composition 2 Composition 3 Composition 4 Composition 5 Composition 6 Composition 7 Reference 99 99 99 99 99 99 99 99 99 99 composition MEG C3P 1 MEG C4P 1 MEG C5P 1 MEG C6P 1 MEG C7P 1 MEG C7S 1 Glycerol 1 mono- oleate
• Table VI represents the coefficients of friction of the reference composition and compositions 3, 4, 5 and 6; the values were taken after 900 seconds of testing.
• composition 3 Composition 4
• Composition 5 Composition 6 Coefficient 0.131 0.112 0.119 0.119 0.119 of friction at 900 seconds
• compositions 3 to 6 significantly lower the coefficient of friction on this HFRR test under severe conditions.
• the MTM tests will probe the performance of the friction modifiers under less severe conditions than the HFRR test but are nevertheless representative of operating points of certain driving members.
• Table VII below indicates the values of the coefficients of friction of compositions 1, 2, 4, 5, 6 and 7; the values were taken after 6120 seconds of testing.
• the lubricating compositions 4 to 6 according to the invention significantly lower the coefficient of friction on this MTM test in comparison with the comparative compositions 1 and 2 (comprising respectively a C 3 and C 4 glycerol mono-ether) or comparative composition 7 (comprising glycerol mono-oleate)).
• composition 3 and the composition 6 were evaluated comparatively by the implementation of the motor test described below:
• the fluid temperature water/oil
• the engine is then positioned at a selected operating point (rpm/torque) and the fuel consumption is then measured at this point.
• a consumption map is thus produced by this means.
• the test engine is a Renault R9M engine.
• Table VIII shows the gains in terms of % fuel consumption compared to the reference composition at a temperature (water/oil) set at 90° C.
• the threshold of significance of the test is equal to 0.15%.
• the lubricating compositions according to the invention significantly improve the fuel consumption, especially when hot.

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• 2016
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  • 2017-12-06 EP EP17816626.0A patent/EP3551734A1/de not_active Withdrawn
  • 2017-12-06 WO PCT/EP2017/081746 patent/WO2018104408A1/fr unknown
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