US20230024398A1 - Lubricant composition for limiting friction - Google Patents

Lubricant composition for limiting friction Download PDF

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Publication number
US20230024398A1
US20230024398A1 US17/784,702 US202017784702A US2023024398A1 US 20230024398 A1 US20230024398 A1 US 20230024398A1 US 202017784702 A US202017784702 A US 202017784702A US 2023024398 A1 US2023024398 A1 US 2023024398A1
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carboxylic acid
acid
esters
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Mickael DEBORD
Catherine CHARRIN
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TotalEnergies Onetech SAS
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    • 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
    • C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular 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
    • 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
    • C10M129/76—Esters containing free hydroxy or carboxyl groups
    • 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
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • 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
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/18—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/24—Polyethers
    • C10M145/26—Polyoxyalkylenes
    • C10M145/36—Polyoxyalkylenes etherified
    • 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
    • C10M157/00—Lubricating compositions characterised by the additive being a mixture of two or more macromolecular compounds covered by more than one of the main groups C10M143/00 - C10M155/00, each of these compounds being essential
    • 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
    • C10M161/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • 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
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • 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
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • 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
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • 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
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • the present application relates to new lubricant compositions, in particular for reducing friction between mechanical parts, preferably between two parts of an engine, such as a vehicle engine.
  • the lubricant compositions according to the invention can be used to lubricate an internal combustion engine, in particular a vehicle engine, in particular a motor vehicle engine.
  • lubricants are to reduce friction and wear of mechanical parts, especially in vehicle engines, and more particularly in motor vehicles.
  • organomolybdenum compounds represent a family of compounds whose friction-reducing properties have been widely described.
  • organomolybdenum compounds in particular organomolybdenum compounds comprising a dithiocarbamate group, can worsen the wearing of mechanical parts.
  • Other solutions were then proposed to reduce friction between two mechanical parts.
  • polymeric organic friction modifiers are currently sometimes used.
  • WO2011/116049 describes one type of polymeric organic friction modifier of interest.
  • This type of polymeric friction modifier makes it possible to achieve coefficients of friction between mechanical parts that are sometimes too high for the applications envisaged.
  • One objective of the present application is to provide lubricant compositions for reducing friction between mechanical parts.
  • a lubricant composition comprising, based on the total weight of the lubricant composition:
  • a polymeric organic friction modifier of the above type and an ester preferably selected from glycerol esters, citric acid esters, tartaric acid esters and mixtures thereof significantly improves the friction coefficient between mechanical parts.
  • ester chosen more particularly among glycerol esters, citric acid esters, tartaric acid esters and their mixture allows to boost surprisingly the effect of the polymeric organic friction modifier.
  • the polymeric organic friction modifier has a weight average molecular weight of from 3,000 to 8,000 Daltons.
  • the weight average molecular weight can be measured by steric exclusion chromatography.
  • Application WO2011/116049 describes, for example, polymeric organic friction modifiers.
  • the polymeric organic friction modifier is built around a central group R 1 .
  • the central group R 1 is the residue of a compound containing at least m hydrogen atoms, obtained after removal of said m hydrogen atoms.
  • the m hydrogen atoms are hydrogen atoms of groups selected from amino groups and hydroxyl groups, and are advantageously hydrogen atoms of hydroxyl groups.
  • the central group R 1 is the residue of a substituted hydrocarbyl group, in particular a C3 to C30 substituted hydrocarbyl compound.
  • the central group R 1 is a residue of a compound containing at least m hydrogen atoms, obtained after removal of m hydrogen atoms, said compound being selected from:
  • the central group R 1 is a residue of a compound containing at least m hydrogen atoms, obtained after removal of m hydrogen atoms, said compound having at least 3, preferably 4 to 10, in particular 5 to 8, advantageously 6 groups selected from amino groups and hydroxyl groups.
  • the central group R 1 is a residue of a compound comprising at least 3, preferably 4 to 10, in particular 5 to 8, advantageously 6 hydroxyl groups.
  • the central group R 1 comprises a C4 to C7 linear chain, more preferably C6.
  • hydroxyl or amino groups are preferably directly linked to the carbon atoms of the linear chain of the central group R 1 .
  • the central group R 1 is a residue of a compound selected from open chain tetratol, open chain pentitol, open chain hexitol and open chain heptitol, or an anhydro compound derived from a compound selected from tetratol, pentitol, hexitol and heptitol, for example an anhydro cycloether group derived from a compound selected from tetratol, pentitol, hexitol and heptitol.
  • the central group R 1 is a residue of a sugar, more preferably of a monosaccharide, preferably selected from glucose, fructose and sorbitol, of a disaccharide, preferably selected from maltose, palitose, lactitol and lactose, or of an oligosaccharide with a degree of polymerisation higher than 2.
  • the central group R 1 is the residue of a monosaccharide, preferably selected from glucose, fructose and sorbitol, and in particular a sorbitol residue.
  • the central group R 1 is preferably in open chain form. However, the central group R 1 may also comprise an internal cyclic ether function when the central group R 1 synthesis pathway exposes it to relatively high temperatures or other conditions that favour such cyclisation.
  • the index m is a measure of the functionality of the central group R 1 .
  • the index m is preferably greater than 3, preferably greater than or equal to 4 and less than or equal to 10, in particular greater than or equal to 5 and less than or equal to 8, advantageously greater than or equal to 5 and less than or equal to 6.
  • the index m can be a whole number or a decimal.
  • the R 2 groups are the terminal groups of the (poly)alkylene oxide chains of the polymeric organic friction modifier of formula (I).
  • R 2 is a hydrogen atom or a C—(O)—R 3 group with R 3 being a residue of a polyhydroxyalkyl carboxylic acid, a residue of a polyhydroxyalkenyl carboxylic acid, a residue of a hydroxyalkyl carboxylic acid, a residue of a hydroxyalkenyl carboxylic acid, a residue of an oligomer of a hydroxyalkyl carboxylic acid and/or a residue of an oligomer of a polyhydroxyalkenyl carboxylic acid.
  • Hydroxyalkyl carboxylic acid and hydroxyalkenyl carboxylic acid have the formula HO—X—COOH, wherein X is a divalent saturated or unsaturated, preferably saturated, aliphatic radical containing at least 8 and at most 20 carbon atoms, typically from 11 to 17 carbon atoms, and in which there are at least 4 carbon atoms between the hydroxyl group and the carboxylic acid group.
  • the hydroxyalkyl carboxylic acid is 12-hydroxystearic acid.
  • hydroxyalkyl carboxylic acids are commercially available as mixtures of the hydroxylic acid and the corresponding unsubstituted fatty acid.
  • 12-hydroxystearic acid is typically made by hydrogenating castor oil fatty acids comprising the unsaturated C18 hydroxyl acid and the unsubstituted fatty acids (oleic and linoleic acids) which, on hydrogenation, give a mixture of 12-hydroxystearic acid and stearic acid.
  • 12-hydroxystearic acid typically contains about 5-8% unsubstituted stearic acid.
  • Polyhydroxyalkyl carboxylic acid and polyhydroxyalkenyl carboxylic acid are manufactured by polymerisation of hydroxyalkyl carboxylic acid or hydroxyalkenyl carboxylic acid, respectively. Hydroxyalkyl carboxylic acid and hydroxyalkenyl carboxylic acid are as defined above.
  • the presence of the corresponding unsubstituted fatty acid in commercially available hydroxyalkyl carboxylic acids acts as a terminating agent and thus limits the chain length of the polymer.
  • the number of monomer units in the polyhydroxyalkyl carboxylic acid and in the polyhydroxyalkenyl carboxylic acid is on average from 2 to 10, preferably from 4 to 8 and advantageously about 7.
  • the molecular weight of the polyhydroxyalkyl carboxylic acid and polyhydroxyalkenyl carboxylic acid is typically 600 to 3000 g/mol, in particular 900 to 2700 g/mol, more particularly 1500 to 2400 g/mol and advantageously about 2100 g/mol.
  • Polyhydroxyalkyl carboxylic acid and polyhydroxyalkenyl carboxylic acid are characterised by a residual acid number of less than 50 mg KOH/g, preferably between 30 and 35 mg KOH/g.
  • the hydroxyl value of the polyhydroxyalkyl carboxylic acid and the polyhydroxyalkenyl carboxylic acid is less than or equal to 40 mg KOH/g, advantageously between 20 and 30 mg KOH/g.
  • the hydroxyalkyl carboxylic acid oligomer and polyhydroxyalkenyl carboxylic acid oligomer differ from polyhydroxyalkyl carboxylic acid and polyhydroxyalkenyl carboxylic acid in that the terminus is not the corresponding unsubstituted fatty acid.
  • the hydroxyalkyl carboxylic acid oligomer and the polyhydroxyalkenyl carboxylic acid oligomer are dimers of hydroxylalkyl carboxylic acid and hydroxyalkenyl carboxylic acid, respectively.
  • the alkylene oxide residue AO is a group of the formula —(C r H 2r O), where r is 2, 3 or 4, preferably 2 or 3, i.e. an ethylene oxide residue (—C 2 H 4 O—) or a propylene oxide residue (—C 3 H 6 O—).
  • AO can represent different groups along the alkylene oxide chain (AO) n .
  • (AO) n is a homopolymeric chain of the formula (—C 2 H 4 O—) n , n being between 1 and 100.
  • (AO) n is a homopolymeric chain of porpylene oxide group of the formula (—C 3 H 6 O—) n , where n is between 1 and 100.
  • (AO) n is a block or random copolymer chain containing both ethylene oxide (—C 2 H 4 O—) and propylene oxide (—C 3 H 6 O—) residues.
  • the molar proportion of ethylene oxide units (—C 2 H 4 O—) in the copolymer chain is at least 50%, preferably at least 70%.
  • the parameter n represents the number of alkylene oxide residues in the (poly)alkylene oxide (AO) n chains.
  • n is between 2 and 50, preferably between 3 and 20, advantageously between 5 and 10.
  • the total of the indices n (i.e. n x m) is preferably between 10 and 300, preferably between 20 and 100, in particular between 5 and 70, advantageously between 30 and 50.
  • the value of the index n is an average value, which includes the statistical variation of the length of the chain.
  • the central group R 1 is derived from pentaerythritol
  • the alkoxylation of pentaerythritol is evenly distributed over the four available sites to remove one hydrogen, and the distribution of acyl groups is close to the expected random distribution.
  • the polymeric organic friction modifier of formula (I) is prepared from the compound containing at least m hydrogen atoms.
  • the first step in the preparation of the polymeric organic friction modifier of formula (I) is an alkoxylation of the groups containing the at least m hydrogen atoms.
  • Alkoxylation is carried out by techniques well known to the skilled person, for example by reacting the compound containing at least m hydrogen atoms with the required amounts of alkylene oxide, for example ethylene oxide and/or propylene oxide.
  • the second step in the preparation of the polymeric organic friction modifier of formula (I) is to react the alkoxylated species obtained from the first step with a polyhydroxyalkyl carboxylic acid and/or a polyhydroxyalkenyl carboxylic acid and/or a hydroxyalkyl carboxylic acid and/or a hydroxyalkenyl carboxylic acid under standard catalysed esterification conditions at temperatures up to 250° C.
  • the lubricant composition according to the invention comprises from 0.005 to 10 wt %, preferably from 0.05 to 5 wt %, more preferably from 0.1 to 3 wt %, more preferably from 0.2 to 2 wt %, of polymeric organic friction modifier(s) as defined above, based on the total weight of the lubricant composition
  • the lubricant composition according to the invention comprises from 0.005 to 10% by weight, preferably from 0.05 to 5% by weight, preferably from 0.1 to 3% by weight, more preferably from 0.2 to 2% by weight, of at least one ester selected from glycerol esters, citric acid esters, tartaric acid esters, and mixtures thereof, based on the total weight of the lubricant composition.
  • the ester used according to the invention may be a mono-, di- or tri-ester. It can be a mixture of mono-, di- and/or tri-esters. Preferably, the ester used according to the invention comprises at least one triester.
  • the ester is selected from glycerol esters, citric acid esters and mixtures thereof.
  • the glycerol ester is an ester of glycerol and a carboxylic acid having from 1 to 10 carbon atoms, preferably from 2 to 8 carbon atoms.
  • the carboxylic acid is a monocarboxylic acid.
  • the glycerol ester is selected from glycerol heptanoates and mixtures thereof.
  • the carboxylic acids used to prepare the glycerol ester are saturated or unsaturated, linear, cyclic or branched carboxylic acids, optionally substituted with hydroxyl and/or epoxy groups.
  • the carboxylic acid used to prepare the glycerol ester is linear and saturated and has a hydrocarbon chain consisting of carbon and hydrogen atoms.
  • the carboxylic acid used to prepare the glycerol ester does not comprise any heteroatoms other than those of the acid function.
  • the glycerol ester is obtained from raw materials of renewable origin.
  • the carboxylic acids that can be used to form the glycerol ester are, for example, carboxylic acids derived from vegetable oils, fats, of animal or vegetable origin, such as butyric acid, valeric acid, caproic acid, heptylic acid, caprylic acid, pelargonic acid, capric acid, crotonic acid, iso-crotonic acid, sorbic acid, isovaleric acid, taken alone or mixed.
  • the glycerol ester is obtained from raw materials of fossil origin. These are known as synthetic carboxylic acids.
  • Synthetic carboxylic acids such as butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, taken alone or mixed, may also be used.
  • glycerol esters used in the invention can be obtained by methods well known to the skilled person, for example by reacting carboxylic acids with glycerol. These chemical reactions, which are well known to the skilled person, can take place with or without a catalyst, with or without a solvent.
  • the glycerol ester used in the lubricant composition according to the invention is glycerol triheptanoate.
  • the tartaric acid ester is an ester of tartaric acid and an alcohol having from 1 to 10 carbon atoms, preferably from 2 to 8 carbon atoms.
  • the alcohol used to prepare the tartaric acid ester is a monoalcohol.
  • the tartaric acid ester is selected from tartaric acid triesters.
  • the citric acid ester is an ester of citric acid and an alcohol having 1 to 10 carbon atoms, preferably 2 to 8 carbon atoms.
  • the alcohol used to prepare the citric acid ester is a monoalcohol.
  • the citric acid ester is selected from citric acid triesters.
  • the alcohols used to prepare the citric acid ester or tartaric acid ester are saturated or unsaturated, linear, cyclic or branched alcohols, optionally substituted by acid and/or epoxy groups.
  • the alcohol used to prepare the citric acid ester or tartaric acid ester is linear and saturated and has a hydrocarbon chain consisting of carbon and hydrogen atoms.
  • the alcohol used to prepare the citric acid ester or tartaric acid ester does not comprise any heteroatoms other than those of the hydroxyl function.
  • citric acid esters or tartaric acid esters used in the invention can be obtained by methods well known to the person skilled in the art, for example by reacting citric acid or tartaric acid with one or more alcohols. These chemical reactions, which are well known to the skilled person, can take place with or without a catalyst, with or without a solvent.
  • the citric acid ester is selected from triethylcitrate, tributylcitrate and mixtures thereof.
  • the ester of the lubricant composition is selected from:
  • the ester of the lubricant composition is selected from glycerol triheptanoate, triethylcitrate, tributylcitrate and mixtures thereof.
  • the lubricant composition according to the invention comprises one or more base oils, preferably in an amount of at least 50% by weight, more preferably at least 60% by weight or even at least 70% by weight, based on the total weight of the lubricant composition.
  • the base oil(s) may be selected from the mineral, synthetic or natural, animal or vegetable lubricating base oils known to the skilled person.
  • the base oils used in the lubricant compositions according to the invention may be 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) (table 1) or mixtures thereof.
  • Mineral base oils according to the invention include all types of base oils obtained by atmospheric and vacuum distillation of crude oil, followed by refining operations such as solvent extraction, de-alkalization, solvent dewaxing, hydrotreating, hydrocracking, hydroisomerization and hydrofining.
  • Mixtures of synthetic and mineral oils can also be used.
  • lubricating bases there is generally no limitation on the use of different lubricating bases to make the lubricant compositions according to the invention, except that they must have properties, in particular viscosity, viscosity index, sulphur content, resistance to oxidation, suitable for their use.
  • the base oils of the lubricant compositions according to the invention may also be chosen from synthetic oils, such as certain esters of carboxylic acids and alcohols, and from polyalphaolefins.
  • Polyalphaolefins used as base oils are for example obtained from monomers with 4 to 32 carbon atoms, for example from octene or decene, and whose viscosity at 100° C. is between 1.5 and 15 mm 2 .s ⁇ 1 according to ASTM D445.
  • Their average molecular weight is generally between 250 and 3,000 according to ASTM D5296.
  • the lubricant composition according to the invention comprises from 60% to 99.5% by weight of base oils, preferably from 70% to 99.5 by weight of base oils, relative to the total weight of the composition.
  • Preferred additional additives for the lubricant composition according to the invention are selected from detergent additives, anti-wear additives other than phospho-sulphur additives, friction modifying additives other than the polymeric organic friction modifiers defined above, extreme pressure additives, dispersants, pour point depressants, anti-foaming agents, thickeners and mixtures thereof.
  • the lubricant composition according to the invention comprises, based on the total weight of lubricant composition:
  • Amine phosphates are anti-wear additives which can be used in the lubricant composition according to the invention.
  • the phosphorus provided by these additives can act as a poison for automotive catalytic systems as these additives are ash generators.
  • the lubricant composition according to the invention may comprise from 0.01 to 6 wt. %, preferably from 0.05 to 4 wt. %, more preferably from 0.1 to 2 wt. % based on the total weight of lubricant composition, anti-wear additives and extreme pressure additives.
  • the lubricant composition according to the invention may comprise at least one additional friction modifier additive different from the polymeric organic friction modifiers defined above.
  • the additional friction modifier additive may be selected from a compound providing metallic elements and an ash-free compound.
  • the compounds providing metallic elements we can mention transition metal complexes such as Sb, Sn, Fe, Cu, Zn, Mo whose ligands can be hydrocarbon compounds comprising oxygen, nitrogen, sulphur or phosphorus atoms.
  • the lubricant composition according to the invention may comprise at least one antioxidant additive.
  • the antioxidant additive generally delays the degradation of the lubricant composition in service. This degradation may result in the formation of deposits, the presence of sludge or an increase in the viscosity of the lubricant composition.
  • Antioxidant additives act as radical inhibitors or hydroperoxide destroyers. Commonly used antioxidant additives include phenolic antioxidant additives, amine antioxidant additives and phosphosulphur antioxidant additives. Some of these antioxidant additives, e.g. phosphosulphur antioxidant additives, can be ash-forming. Phenolic antioxidant additives can be ash-free or in the form of neutral or basic metal salts.
  • the antioxidant additives may in particular be selected from sterically hindered phenols, sterically hindered phenol esters and sterically hindered phenols comprising a thioether bridge, diphenylamines, diphenylamines substituted by at least one C 1 -C 12 , alkyl group, 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 can be used, possibly in combination with phenolic antioxidant additives.
  • Examples of amino compounds are aromatic amines, for example aromatic amines of the formula NR 7 R 8 R 9 where R 7 represents an aliphatic group or an aromatic group, optionally substituted, R 8 represents an aromatic group, optionally substituted, R 9 represents a hydrogen atom, an alkyl group, an aryl group or a group of formula R 10 S(O) z R 11 in which R 19 represents an alkylene group or an alkenylene group, R 11 represents an alkyl group, an alkenyl group or an aryl group and z represents 0, 1 or 2.
  • Sulphurised alkyl phenols or their alkali and alkaline earth metal salts can also be used as antioxidant additives.
  • antioxidant additives are copper compounds, e.g. copper thio- or dithio-phosphates, copper salts of carboxylic acids, dithiocarbamates, sulphonates, phenates, copper acetylacetonates. Copper I and II salts, succinic acid or anhydride salts can also be used.
  • the lubricant composition according to the invention may contain any type of antioxidant additives known to the person skilled in the art.
  • the lubricant composition comprises at least one ash-free antioxidant additive.
  • the lubricant composition according to the invention comprises from 0.5 to 2% by weight, based on the total mass of the composition, of at least one antioxidant additive.
  • the lubricant 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 oxidation and combustion by-products.
  • detergent additives used in the lubricant composition according to the invention are generally known to the person skilled in the art.
  • Detergent additives can be anionic compounds comprising a long lipophilic hydrocarbon chain and a hydrophilic head.
  • the associated cation may be a metal cation of an alkali or alkaline earth metal.
  • the detergent additives are preferably selected from alkali or alkaline earth metals of carboxylic acids, sulphonates, salicylates, naphthenates, and phenate salts.
  • the alkali and alkaline earth metals are preferably calcium, magnesium, sodium or barium.
  • metal salts generally contain the metal in a stoichiometric amount or in excess, i.e. in an amount greater than the stoichiometric amount.
  • overbased detergent additives the excess metal giving the overbased character to the detergent is generally in the form of oil-insoluble metal salts, e.g. carbonate, hydroxide, oxalate, acetate, glutamate, preferably carbonate.
  • the lubricant composition according to the invention may comprise from 2% to 4% by weight of detergent additive relative to the total weight of the lubricant composition.
  • the lubricant composition according to the invention may also comprise at least one pour point depressant additive.
  • pour point depressant additives By slowing down the formation of paraffin crystals, pour point depressant additives generally improve the cold behaviour of the lubricant composition according to the invention.
  • pour point depressant additives examples include alkyl polymethacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes, alkylated polystyrenes.
  • the lubricant composition according to the invention may also comprise at least one dispersing agent.
  • the dispersing agent may be selected from Mannich bases, succinimides and derivatives thereof.
  • the lubricant composition according to the invention may comprise from 0.2% to 10% by weight of dispersant(s) based on the total weight of the lubricant composition.
  • the lubricant composition of the present invention may also comprise at least one additional polymer that can improve the viscosity index.
  • additional viscosity index improving polymers are polymeric esters, hydrogenated or non-hydrogenated homopolymers or copolymers of styrene, butadiene and isoprene, polymethacrylates (PMA).
  • the present invention also relates to the use of the lubricant composition as defined above for the lubrication of metal parts, in particular for the lubrication of engines, in particular internal combustion engines, for example vehicle engines.
  • the lubricant composition according to the invention makes it possible to reduce friction, in particular between two mechanical parts, for example two parts of an engine, in particular an internal combustion engine, for example a vehicle engine.
  • the invention relates to the use of the lubricant composition according to the invention to reduce the wear of mechanical parts, for example parts of an engine, in particular a vehicle engine.
  • the present application also relates to a method of lubricating mechanical parts, particularly in an engine, such as an internal combustion engine, comprising at least one step of bringing a part into contact with the lubricating composition according to the invention.
  • compositions in Table 2 were prepared by mixing at 60° C. the ester and/or polymeric friction modifier in a composition comprising base oil, viscosity index improver and additive package, to give the proportions shown in Table 2. The percentages shown are based on 100% by weight of the lubricant composition including the ester and/or polymeric friction modifier.
  • Lubricant compositions according to the invention and comparative ones LC6 CC2 Lubricating composition (% by weight) (% by weight) triethylcitrate 1 1
  • Organic friction modifier 0.5 — according to the invention* Additive package 1** 14.2 13.8 Viscosity index improver (olefin 6.0 6.1 copolymer)
  • Group III base oil 78.3 79.1 *An organic friction modifier which is a compound of formula (I): R 1 •[(AO) n• -AO—R 2 ] m (I) wherein R 1 is a residue of a group having at least m hydrogen atoms, m being greater than 2 AO is an alkylene oxide residue n is between 0 and 100 R 2 is a hydrogen atom or a C—(O)—R 3 group with R 3 being a residue selected from the list consisting of a polyhydroxyalkyl carboxylic acid residue, a polyhydroxyalkenyl carboxylic acid residue, a hydroxyalky
  • the coefficient of friction of the lubricant compositions tested is determined at 100° C. using an MTM (Mini Traction Machine) device using a 2 cm diameter hardened steel ball on a hardened steel plane.
  • the MTM device can be a PCS Instruments device. This device allows a steel ball and a steel plane to be moved relative to each other in order to determine the coefficients of friction for a given lubricant composition while varying various properties such as speed, load, and temperature.
  • the hardened steel plane is AISI 52100 with a mirror finish (Ra less than 0.01 ⁇ m) and the ball is also AISI 52100 made of hardened steel.
  • the applied load is 30 N (0.96 Gpa) and the rotation speed varies from 0.007 m/s to 3 m/s.
  • the coefficient of friction is measured and recorded by means of a force sensor.
  • the test is conducted for a duration of 121 minutes (alternating between slip-slip and Stribeck periods).
  • the velocity is initially held constant at 0.1 m/s and at each interval defined in the table, the velocity is increased from 3 to 0.007 m/s for one minute before returning to a velocity of 0.1 m/s at the end of said defined period.
  • the coefficient of friction is thus measured as a function of the defined speed.
  • Table 4 gives the results for the compositions in Table 2, expressed in terms of coefficient of friction versus slip speed.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US17/784,702 2019-12-13 2020-12-11 Lubricant composition for limiting friction Pending US20230024398A1 (en)

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FR1914410 2019-12-13
FR1914410A FR3104608B1 (fr) 2019-12-13 2019-12-13 Composition lubrifiante pour limiter le frottement
PCT/EP2020/085748 WO2021116401A1 (fr) 2019-12-13 2020-12-11 Composition lubrifiante pour limiter le frottement

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120329690A1 (en) * 2009-12-18 2012-12-27 Totle Raffinage Marketing Additive composition for engine oil
US9321979B2 (en) * 2012-03-13 2016-04-26 Chemtura Corporation Friction modifier composition for lubricants
US20160264907A1 (en) * 2013-10-29 2016-09-15 Croda, Inc. Lubricant composition comprising hydroxycarboxylic acid derived friction modifier

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10314776A1 (de) * 2003-03-31 2004-10-14 Rohmax Additives Gmbh Schmierölzusammensetzung mit guten Reibeigenschaften
ES2688798T3 (es) 2010-03-17 2018-11-07 Croda, Inc. Tensioactivo polimérico
FR2992655B1 (fr) * 2012-06-29 2015-07-31 Total Raffinage Marketing Composition lubrifiante
WO2014124698A1 (fr) * 2013-02-18 2014-08-21 Amril Ag Lubrifiant d'ester destiné à des applications de lubrifiant de champ pétrolier et d'autres d'applications de lubrifiant industriel
WO2014184068A1 (fr) * 2013-05-14 2014-11-20 Basf Se Composition d'huile lubrifiante à rendement énergétique amélioré
GB201609713D0 (en) * 2016-06-03 2016-07-20 Croda Int Plc Lubricant composition
WO2018144166A1 (fr) * 2017-02-01 2018-08-09 Exxonmobil Research And Engineering Company Huile lubrifiante pour moteur et procédé d'amélioration du rendement de carburant de moteur

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120329690A1 (en) * 2009-12-18 2012-12-27 Totle Raffinage Marketing Additive composition for engine oil
US9321979B2 (en) * 2012-03-13 2016-04-26 Chemtura Corporation Friction modifier composition for lubricants
US20160264907A1 (en) * 2013-10-29 2016-09-15 Croda, Inc. Lubricant composition comprising hydroxycarboxylic acid derived friction modifier

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EP4073212A1 (fr) 2022-10-19
JP2023505729A (ja) 2023-02-10
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FR3104608B1 (fr) 2021-12-24
WO2021116401A1 (fr) 2021-06-17
KR20220112829A (ko) 2022-08-11

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