EP3027719A1 - Compositions lubrifiantes pour transmissions - Google Patents

Compositions lubrifiantes pour transmissions

Info

Publication number
EP3027719A1
EP3027719A1 EP14745153.8A EP14745153A EP3027719A1 EP 3027719 A1 EP3027719 A1 EP 3027719A1 EP 14745153 A EP14745153 A EP 14745153A EP 3027719 A1 EP3027719 A1 EP 3027719A1
Authority
EP
European Patent Office
Prior art keywords
compound
group
carbon atoms
dithiocarbamate
independently
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP14745153.8A
Other languages
German (de)
English (en)
French (fr)
Inventor
Goulven BOUVIER
Blandine BRIZARD
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
TotalEnergies Marketing Services SA
Original Assignee
Total Marketing Services SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Total Marketing Services SA filed Critical Total Marketing Services SA
Publication of EP3027719A1 publication Critical patent/EP3027719A1/fr
Withdrawn legal-status Critical Current

Links

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
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02—Well-defined hydrocarbons
    • C10M105/04—Well-defined hydrocarbons aliphatic
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/44—Five-membered ring containing nitrogen and carbon 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
    • C10M137/14—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond containing sulfur
    • 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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • 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
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon 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
    • 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
    • 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
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/049—Phosphite
    • 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
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions

Definitions

  • the present invention is applicable to the field of lubricants, and more particularly to the field of lubricants for motor vehicles, especially in the field of lubricants for transmission members of motor vehicles, in particular for manual gearboxes, bridges or double clutches.
  • the invention relates to a lubricating composition
  • a lubricating composition comprising the combination of phosphorus, sulfur and phospho-sulfur compounds with an anticorrosive agent, as well as a process for their preparation.
  • the lubricant composition according to the invention has in particular good extreme-pressure, anti-wear properties, and more particularly against synchronizers present in the gearboxes, as well as a low coefficient of friction.
  • the present invention also relates to a method of reducing the wear of a mechanical part employing this lubricant composition.
  • the present invention also relates to a method of reducing seizure of a mechanical part implementing this lubricant composition.
  • the present invention also relates to a method for reducing the peeling of a mechanical part employing this lubricant composition.
  • the present invention also relates to a concentrated additive type composition comprising the combination of phosphorus, sulfur and phospho-sulfur compounds with an anti-corrosion agent.
  • extreme pressure additives or friction modifying additives all do not have the same effectiveness, some may improve a property and at the same time damage a second property.
  • the chemistry of these additives is complex and the additives can react with each other to form new chemical species whose ultimate influence on the properties of extreme pressure, wear, friction and galling is not known.
  • additives such as diphosphites, which may be both friction modifiers and anti-wear components, react with the sulfur atoms contained in the extreme pressure additives to form thiophosphonic derivatives for example, whose properties are significantly different from those of the original molecules.
  • US 2009/01 1964, US 5674820 and US 5872085 disclose a lubricating composition comprising a compound comprising a dithiocarbamate moiety, a compound comprising a phosphite moiety and a compound comprising a dithiophosphate moiety.
  • a compound comprising a dithiophosphate group is likely to cause significant wear of the synchronizers.
  • these documents do not describe the presence of a thiadiazole compound.
  • WO 03/035810 discloses a lubricating composition
  • a lubricating composition comprising a base oil, an amino salt of a phosphorus-containing acid, a metal salt of an organic acid.
  • the lubricating composition may further comprise a metal deactivator compound, which may be a dimercaptothiadiazole compound and a boron dispersant.
  • a metal deactivator compound which may be a dimercaptothiadiazole compound and a boron dispersant.
  • this document does not disclose the presence of compounds comprising a dithiocarbamate group or compounds comprising a dithiophosphate group.
  • the lubricating composition described in this document must comprise less than 0.1% by weight of non-metallic and sulfur-containing anti-wear / extreme pressure compounds, which may correspond to compounds comprising a dithiocarbamate group or to compounds comprising a dithiophosphate group.
  • a lubricating composition in particular for motor vehicles, which simultaneously has good extreme-pressure, friction and anti-wear properties, in particular against synchronizers, as well as good anti-seizing properties.
  • a lubricating composition especially for motor vehicles, which is both stable and has good extreme pressure, friction, anti-wear and anti-seizing properties.
  • An object of the present invention is to provide a lubricant composition overcoming all or in part the aforementioned drawbacks.
  • Another object of the invention is to provide a lubricating composition which is stable and easy to implement.
  • Another object of the invention is to provide a lubrication method that notably makes it possible to reduce the wear of the synchronizers in the gearboxes.
  • the subject of the invention is thus a lubricating composition
  • a lubricating composition comprising:
  • At least one amine dithiocarbamate of general formula (I) (compound A-1)
  • R 1 and R 2 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms,
  • R 3 , R 4 and R 5 represent, independently of one another, a hydrogen atom or a hydrocarbon group of 1 to 30 carbon atoms, it being understood that at least one of the groups R 3 , R 4 and R 5 is not a hydrogen atom, and
  • At least one metal dithiocarbamate of general formula (II) (compound A-2),
  • R 6 and R 7 represent, independently of one another, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms
  • M represents a metal cation
  • n is the valency of this metal cation
  • the compound D comprising a thiadiazole group being chosen from the group formed by:
  • R27 and R 2 identical or different, independently represent a hydrogen atom or an alkyl group, saturated or unsaturated, linear or branched, comprising 1 to 30 carbon atoms,
  • a represents an integer ranging from 1 to 3
  • b represents an integer ranging from 1 to 3
  • - F1 ⁇ 2 represents a hydrogen atom or a linear or branched, saturated or unsaturated alkyl group comprising from 1 to 30 carbon atoms,
  • b represents an integer ranging from 1 to 3
  • the ratio by weight (compound C comprising a dithiophosphate group: compound D comprising a thiadiazole group) ranging from 5: 1 to 1: 10.
  • the Applicant has found that the presence of at least one compound comprising a dithiophosphate group, of at least one compound comprising a phosphite group, of at least one compound comprising a dithiocarbamate group in the form of a mixture specific for a compound of formula (I) and a compound of formula (II) and at least one compound comprising a thiadiazole group selected from the group consisting of a compound of formula (Va), a compound of formula ( Vb) and a mixture of at least one compound of formula (Va) and at least one compound of formula (Vb) in a lubricating composition makes it possible to confer on the lubricant composition simultaneously good properties of extreme pressure and friction. and anti-wear, especially against synchronizers, as well as good anti-seizure properties.
  • the present invention makes it possible to formulate lubricating compositions comprising a reduced content of compounds comprising a dithiophosphate group and yet having outstanding extreme-pressure, friction, anti-wear and anti-seizing properties.
  • the lubricant compositions according to the invention have improved anti-wear properties against synchronizers present in the gearboxes.
  • the lubricant compositions according to the invention also have good anti-peeling properties.
  • the lubricant compositions according to the invention also have good antioxidant and anti-corrosion properties.
  • the lubricant compositions according to the invention have improved storage stability and a viscosity that does not vary or is very little.
  • the lubricant composition consists essentially of:
  • At least one amine dithiocarbamate of general formula (I) (compound -1)
  • R 1 and R 2 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms,
  • R 3 , R 4 and R 5 represent, independently of one another, a hydrogen atom or a hydrocarbon group of 1 to 30 carbon atoms, it being understood that at least one of the groups R 3 , R 4 and R 5 is not a hydrogen atom, and
  • Re and 7 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms
  • M represents a metal cation and n is the valence of this metal cation
  • the compound D comprising a thiadiazole group being chosen from the group formed by:
  • 27 and F1 ⁇ 2 which may be identical or different, independently represent a hydrogen atom or an alkyl group, saturated or unsaturated, linear branched, comprising from 1 to 30 carbon atoms,
  • a represents an integer ranging from 1 to 3
  • b represents an integer ranging from 1 to 3
  • - 2 8 represents a hydrogen atom or an alkyl group, saturated or unsaturated, linear or branched, comprising 1 to 30 carbon atoms,
  • b represents an integer ranging from 1 to 3
  • the invention also relates to a process for the preparation of a lubricating composition as defined above.
  • the invention also relates to a transmission oil comprising a lubricating composition as defined above.
  • the invention also relates to the use of a lubricant composition as defined above for the lubrication of transmissions such as gearboxes or bridges, preferably motor vehicle gearboxes, advantageously for the lubrication of gearboxes. manual speeds.
  • the invention also relates to the use of a lubricant composition according to the invention for reducing the fuel consumption of vehicles, in particular motor vehicles.
  • the invention also relates to the use of a lubricant composition according to the invention for reducing the seizure of a mechanical part, preferably present in a transmission member, more preferably in a gearbox, even more preferably in a gearbox. manual speeds.
  • the invention also relates to the use of a lubricant composition according to the invention for reducing the wear of a gearbox synchronizer, preferably of manual gearboxes.
  • the invention also relates to the use of a lubricant composition according to the invention for reducing the peeling of a mechanical part, preferably present in a transmission member, more preferably in a gearbox, even more preferably in a box. manual gear.
  • the invention also relates to a method for lubricating transmissions such as gearboxes, bridges, preferably manual gearboxes of motor vehicles, said method comprising at least one step of contacting the lubricant composition according to the invention. invention.
  • the invention also relates to a method for reducing the seizure of a mechanical part, preferably present in a transmission member, more preferably in a gearbox, even more preferably in a manual gearbox, comprising at least contacting. of the mechanical part with a lubricating composition according to the invention.
  • the invention also relates to a method for reducing the wear of a gearbox synchronizer, preferably of manual gearboxes, comprising at least putting the synchronizer into contact with a lubricant composition according to the invention.
  • the invention also relates to a method for reducing the peeling of a mechanical part, preferably present in a transmission member, more preferably in a gearbox, even more preferably in a manual gearbox, comprising at least the setting in contact with the mechanical part with a lubricating composition according to the invention.
  • the invention also relates to the use of at least one compound A comprising a dithiocarbamate group, at least one compound B comprising a phosphite group, at least one compound C comprising a dithiophosphate group and at least one compound D comprising a thiadiazole group in a base oil for improving the anti-wear, extreme-pressure, friction and anti-seizing properties of a lubricating composition, the compound A comprising a dithiocarbamate group being a mixture:
  • At least one amine dithiocarbamate of general formula (I) (compound A-1)
  • R 1 and R 2 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms,
  • R 3 , R 4 and R 5 represent, independently of one another, a hydrogen atom or a hydrocarbon group of 1 to 30 carbon atoms, it being understood that at least one of the groups R 3 , R 4 and R 5 is not a hydrogen atom, and
  • At least one metal dithiocarbamate of general formula (II) (compound A-2),
  • R 6 and R 7 represent, independently of one another, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms
  • M represents a metal cation and n is the valence of this metal cation
  • the compound D comprising a thiadiazole group being chosen from the group formed by:
  • R- R-27 and R 2 identical or different, independently represent a hydrogen atom or an alkyl group, saturated or unsaturated, linear or branched, comprising 1 to 30 carbon atoms,
  • a represents an integer ranging from 1 to 3
  • b represents an integer ranging from 1 to 3
  • - 2 8 represents a hydrogen atom or an alkyl group, saturated or unsaturated, linear or branched, comprising 1 to 30 carbon atoms,
  • b represents an integer ranging from 1 to 3
  • the invention also relates to a concentrate-type composition of additives comprising:
  • At least one compound D comprising a thiadiazole group is at least one compound D comprising a thiadiazole group.
  • the lubricating composition according to the invention comprises at least one compound A comprising a metal dithiocarbamate group and at least one compound comprising an amine dithiocarbamate group.
  • the compound comprising a metal dithiocarbamate group is called “metal dithiocarbamate” and the compound comprising an amine dithiocarbamate is called “amine dithiocarbamate” in the following description.
  • the metal dithiocarbamate is a metal dithiocarbamate of general formula (II) (compound A-2), in which R 6 and R 7 represent, independently of one another, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms. carbon, M represents a metal cation and n is the valence of this metal cation:
  • the metal is selected from the group consisting of zinc, aluminum, copper, iron, mercury, silver, cadmium, tin, lead, antimony, bismuth, thallium, chromium, molybdenum, cobalt, nickel, tungsten, sodium, calcium, magnesium, manganese and arsenic.
  • the metal is selected from zinc, molybdenum and antimony, preferably zinc and molybdenum, preferably zinc. Mixtures of metals can be used.
  • R 6 and R 7 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably from 3 to 18 carbon atoms, even more preferably from 4 to 12 carbon atoms. carbon atoms.
  • R 6 and R 7 represent, independently of each other, unsubstituted hydrocarbon groups, said hydrocarbon groups possibly being alkyl, alkenyl, alkynyl, aryl, preferably phenyl groups. or benzyls.
  • the alkyl, alkenyl, alkynyl and aryl groups comprise from 2 to 24 carbon atoms, more preferably from 3 to 18 carbon atoms, even more preferentially from 4 to 12 carbon atoms.
  • R 6 and R 7 represent, independently of each other, linear or branched alkyl hydrocarbon groups, more preferably linear alkyl hydrocarbon groups comprising from 2 to 24 carbon atoms. more preferably 3 to 18 carbon atoms, more preferably 4 to 12 carbon atoms.
  • R 6 and R 7 represent, independently of one another, hydrocarbon groups optionally substituted by one or more heteroatoms such as the oxygen atom, the atom of nitrogen, the sulfur atom, the phosphorus atom, preferably by one or more oxygen atoms.
  • Useful metal dithiocarbamates are compounds well known to those skilled in the art. One of the processes for the preparation of these compounds is described in US Pat. No. 249,223. Suppliers of such additives are, for example, Vanderbilt, Rhein Chemie, Adeka and King Industries.
  • Vanlube ® AZ Vanlube ® EZ
  • Vanlube ® 73 Vanlube ® 73 Super Plus
  • Molyvan ® A Molyvan ® 807, Molyvan ® 822
  • Additin ® RC 6301 Additin ® RC 6320
  • Sakura-Lube ® 200 Sakura-Lube ® 165
  • Sakura-Lube ® 525 Sakura-Lube ® 600, Na-Lube ® ADTC.
  • These compounds are marketed in particular by one of the suppliers mentioned above.
  • the metal dithiocarbamate is a zinc dithiocarbamate of formula (II-a), in which 6 and R 7 have the same meaning as in formula (II):
  • Particularly preferred compounds having the formula (II-a) are such that F3 ⁇ 4 and R 7 are, independently of one another, linear alkyl hydrocarbon groups having from 4 to 12 carbon atoms and are, for example, diamyldithiocarbamate. zinc and zinc dibutyldithiocarbamate.
  • the metal dithiocarbamate is a molybdenum dithiocarbamate of formula (II-b), in which R 6 and R 7 have the same meaning as in formula (II):
  • the amine dithiocarbamate is an amine dithiocarbamate of the general formula (I), in which R 1 and R 2 represent, independently of one another, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms, R 3 , R 4 and R 5 represent, independently of one another, a hydrogen atom or a hydrocarbon group of 1 to 30 carbon atoms, it being understood that at least one of the groups R 3 , R 4 and R 5 n is not a hydrogen atom:
  • R 1 and R 2 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably from 3 to 18 carbon atoms. carbon, more preferably 4 to 12 carbon atoms.
  • R 1 and R 2 represent, independently of one another, hydrocarbon groups, not substituted, said hydrocarbon groups may be alkyl, alkenyl, alkynyl, aryl, preferably phenyl or benzyl groups.
  • These alkyl, alkenyl, alkynyl and aryl groups comprise from 2 to 24 carbon atoms, more preferably from 3 to 18 carbon atoms, even more preferentially from 4 to 12 carbon atoms.
  • R 1 and R 2 represent, independently of each other, linear or branched alkyl hydrocarbon groups, more preferably linear alkyl hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably preferably 3 to 18 carbon atoms, more preferably 4 to 12 carbon atoms.
  • R 2 independently of one another represent hydrocarbon groups optionally substituted with one or more heteroatoms such as the oxygen atom, the nitrogen atom, the sulfur atom, the phosphorus atom, preferably with one or more oxygen atoms.
  • R 3 , R 4 and R 5 represent, independently of one another, a hydrocarbon group comprising from 2 to 24 carbon atoms, more preferably from 3 to 18 carbon atoms. more preferably 4 to 12 carbon atoms.
  • Particularly preferred compounds are diamyl amine diamyldithiocarbamate and diamyl amine dibutyldithiocarbamate.
  • the dithiocarbamate is a mixture of at least one amine dithiocarbamate of general formula (I) and at least one metal dithiocarbamate of general formula (II-a) described herein. - above.
  • the dithiocarbamate is a mixture of zinc dithiocarbamate and diamylammonium diamyldithiocarbamate.
  • composition according to the invention may further comprise another compound comprising a dithiocarbamate group other than a dithiocarbamate of formula (I) or a dithiocarbamate of formula (II).
  • this other compound comprising a dithiocarbamate group is chosen from the group consisting of bisdithiocarbamates, ammonium dithiocarbamates and ester dithiocarbamates, alone or as a mixture.
  • this other dithiocarbamate compound is a bisdithiocarbamate of general formula (VI-a), in which R 29, R 30, R 31 and R 32 represent, independently of one another, optionally substituted hydrocarbon groups, comprising from 1 to 30 carbon atoms, R33 represents a hydrocarbon group of 1 to 8 carbon atoms:
  • R 2 g, R 30, R 31 and R 32 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably from 3 to to 18 carbon atoms, more preferably 5 to 12 carbon atoms.
  • R29, R30, R31 and F28 independently of one another are unsubstituted hydrocarbon groups, said hydrocarbon groups being alkyl, alkenyl, alkynyl, aryl groups. preferably phenyl or benzyl.
  • R29, R30, R31 and R3 ⁇ 42 represent, independently of one another, linear or branched alkyl hydrocarbon groups, more preferably linear alkyl hydrocarbon groups.
  • R 2 g, R 30, R 31 and R 32 represent, independently of one another, hydrocarbon groups optionally substituted with one or more oxygen, nitrogen, sulfur and / or phosphorus, preferably one or more oxygen atoms.
  • R 33 represents a hydrocarbon group of 2 to 6 carbon atoms.
  • this other dithiocarbamate compound is an ammonium dithiocarbamate of general formula (VI-b), in which R34 and R35 represent, independently of one another, optionally substituted hydrocarbon groups comprising from 1 to at 30 carbon atoms:
  • R 34 and R 35 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably from 3 to 18 carbon atoms. more preferably 5 to 12 carbon atoms.
  • R 34 and R 35 represent, independently of each other, unsubstituted hydrocarbon groups, said hydrocarbon groups possibly being alkyl, alkenyl, alkynyl or aryl groups, preferably phenyls or benzyls.
  • R 34 and R 35 represent independently of each other linear or branched alkyl hydrocarbon groups, more preferably linear alkyl hydrocarbon groups.
  • R 34 and R 35 represent, independently of each other, hydrocarbon groups optionally substituted by one or more oxygen, nitrogen, sulfur and / or phosphorus, preferably with one or more oxygen atoms.
  • this other dithiocarbamate compound is an ester dithiocarbamate of general formula (VI-c), in which R 36 and R 37 represent, independently of each other, optionally substituted hydrocarbon groups, comprising from 1 to 30 carbon atoms, R 38 and R 39 represent, independently of one another, hydrocarbon groups comprising from 1 to 18 carbon atoms:
  • R 36 and R 37 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably from 3 to 18 carbon atoms. more preferably 5 to 12 carbon atoms.
  • R 36 and R 37 represent, independently of each other, unsubstituted hydrocarbon groups, said hydrocarbon groups possibly being alkyl, alkenyl, alkynyl or aryl groups, preferably phenyls or benzyls.
  • R 36 and R 37 represent independently of each other linear or branched alkyl hydrocarbon groups, more preferably linear alkyl hydrocarbon groups.
  • R 36 and R 37 represent, independently of one another, hydrocarbon groups optionally substituted with one or more oxygen, nitrogen, sulfur and / or phosphorus, preferably with one or more oxygen atoms.
  • R 38 and R 39 represent, independently of one another, hydrocarbon groups of 2 to 6 carbon atoms.
  • the lubricating composition comprises from 0.1 to 5% by weight of compounds A comprising a dithiocarbamate group, relative to the total mass of lubricating composition, preferably from 0.2 to 4% more preferably from 0.3 to 2%, advantageously from 0.5 to 1%.
  • the lubricating composition comprises from 0.1 to 3% by weight of the mixture of amine dithiocarbamate corresponding to formula (I) (compound A-1) and of metal dithiocarbamate corresponding to formula (II) (compound A-2), preferably from 0.1 to 2% by weight, preferably from 0.5 to 2% by weight, relative to the total mass of the lubricating composition.
  • the lubricating composition according to the invention comprises at least one compound B comprising a phosphite group.
  • the compound B comprising a phosphite group is called "phosphite" in the following description.
  • the phosphite is chosen from phosphite monoesters, phosphite diesters or phosphite triesters, taken alone or as a mixture.
  • Phosphite monoesters are found in two equilibrium forms, a "ketone” form and an “alcohol” form. It is the same for phosphite diesters.
  • the phosphite may be a phosphite monoester of general formula (III-a) in its alcohol and / or ketone form, wherein R 8 represents an optionally substituted hydrocarbon group comprising from 1 at 30 carbon atoms:
  • R 8 represents an optionally substituted hydrocarbon group comprising from 2 to 24 carbon atoms, more preferably from 3 to 20 carbon atoms, even more preferably from 4 to 18 carbon atoms. more preferably 6 to 16 carbon atoms, even more preferably 8 to 15 carbon atoms.
  • R 8 represents an unsubstituted hydrocarbon group, said hydrocarbon group possibly being an alkyl, alkenyl, alkynyl, aryl, preferably phenyl or benzyl group.
  • R 8 represents a linear or branched alkyl hydrocarbon group, more preferably a linear alkyl hydrocarbon group.
  • R 8 represents a hydrocarbon group substituted with oxygen, nitrogen, sulfur and / or phosphorus atoms, preferably oxygen atoms.
  • the phosphite may also be a phosphite diester of the general formula (III-b) in its alcohol and / or ketone form, in which R and R independently represent one of the other hbbone groups:
  • R 9 and R 10 represent optionally substituted hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably from 3 to 20 carbon atoms, even more preferably from 4 to 18 carbon atoms. carbon atoms, more preferably 6 to 16 carbon atoms, more preferably 8 to 12 carbon atoms.
  • R 9 and R 10 represent, independently of each other, unsubstituted hydrocarbon groups, said hydrocarbon groups possibly being alkyl, alkenyl, alkynyl or aryl groups, preferably phenyls or benzyls.
  • R 9 and R 10 represent, independently of one another, linear or branched alkyl hydrocarbon groups, more preferably linear alkyl hydrocarbon groups.
  • R g and R o represent hydrocarbon groups substituted with one or more oxygen, nitrogen, sulfur and / or phosphorus atoms, preferably by one or more atoms. oxygen.
  • phosphite diesters examples include dimethyl phosphite, diethyl phosphite, diisopropyl phosphite, dibutyl phosphite, dihexyl phosphite, dicylohexyl phosphite, diisodecyl phosphite, di-n-octyl phosphite, dibenzyl phosphite, diphenyl phosphite or dioleyl phosphite.
  • the phosphite may also be a phosphite triester of general formula (III-c) in which Ru, R12 and R13 represent, independently of each other, optionally substituted hydrocarbon groups , comprising from 1 to 30 carbon atoms:
  • Ru, R 12 and R 13 represent optionally substituted hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably from 3 to 20 carbon atoms, even more preferably from 4 to 20 carbon atoms. to 18 carbon atoms, more preferably 6 to 16 carbon atoms, even more preferably 8 to 12 carbon atoms.
  • Ru, R 12 and R 13 represent, independently of each other, unsubstituted hydrocarbon groups, said hydrocarbon groups possibly being alkyl, alkenyl, alkynyl or aryl groups, preferably phenyls or benzyls.
  • Ru, R 12 and R 13 represent independently of each other linear or branched alkyl hydrocarbon groups, more preferably linear alkyl hydrocarbon groups.
  • Ru, R 12 and R 13 represent hydrocarbon groups substituted with one or more oxygen, nitrogen, sulfur and / or phosphorus atoms, preferably one or more oxygen atoms.
  • phosphite triesters examples include diphenyl isodecyl phosphite, diphenyl isooctyl phosphite, tridimethylphenyl phosphite, diphenyl ethylhexyl phosphite, phenyl diisodecyl phosphite, triisodecyl phosphite, trilauryl phosphite, triphenyl phosphite, tris (dipropylene glycol).
  • phosphite tris (nonylphenyl) phosphite, tris (2,4-di-t-butylphenyl) phosphite, tris (5-norbornene-2-methyl) phosphite, tris (tridecyl) phosphite, trimethyl phosphite, triethyl phosphite, triisopropyl phosphite, tributyl phosphite, triisoctyl phosphite, tribenzyl phosphite, triphenyl phosphite, poly (dipropylene glycol) phenyl phosphite or tris (dipropylene glycol) phosphite.
  • the lubricating composition comprises from 0.1 to 5% by weight of phosphite, relative to the total weight of the lubricating composition, preferably from 0.2 to 4%, more preferably from 0.3 to 2%, even more preferably 0.5 to 1%.
  • the lubricating composition according to the invention comprises at least one compound C comprising a dithiophosphate group.
  • the compound C comprising a dithiophosphate group is called "dithiophosphate" in the following description.
  • the dithiophosphate may be selected from the group consisting of ammonium dithiophosphates, amine dithiophosphates, ester dithiophosphates and metal dithiophosphates, alone or in admixture.
  • Ammonium dithiophosphates, amine dithiophosphates and ester dithiophosphates have the advantage of being dithiophosphate without ash and in particular without zinc.
  • the dithiophosphate is an ammonium dithiophosphate of general formula (IV-a),
  • Ru and Ri 5 represent, independently of one another, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms.
  • R 14 and R 15 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably from 3 to 24 carbon atoms. 18 carbon atoms, more preferably 5 to 12 carbon atoms.
  • R 4 and R 15 represent, independently of each other, unsubstituted hydrocarbon groups, said hydrocarbon groups possibly being alkenyl, alkynyl, aryl, preferably phenyl, alkyl groups. or benzyls.
  • R 4 and R 15 represent independently of each other linear or branched alkyl hydrocarbon groups, more preferably linear alkyl hydrocarbon groups.
  • R 14 and R 15 independently of one another represent hydrocarbon groups optionally substituted with one or more oxygen, nitrogen, sulfur and / or phosphorus, preferably with one or more oxygen atoms.
  • dithiophosphates examples include ammonium dimethyl dithiophosphates, ammonium diethyl dithiophosphates or ammonium dibutyl dithiophosphates.
  • the dithiophosphate is an amine dithiophosphate of the general formula (IV-b), in which R 1 and R 17 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 1 to at 30 carbon atoms, R-
  • Ri 6 and R 17 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably from 3 to 18 carbon atoms, still more preferably from 5 to 12 carbon atoms.
  • R 6 and R i7 represent independently of the other hydrocarbon groups, unsubstituted, said hydrocarbon groups may be alkyl, alkenyl, alkynyl, aryl, preferably phenyls or benzyls.
  • Ri 6 and R represent independently of each other linear or branched alkyl hydrocarbon groups, more preferably linear alkyl hydrocarbon groups.
  • Ri 6 and R represent, independently of one another, hydrocarbon groups optionally substituted with one or more oxygen, nitrogen, sulfur and / or phosphorus atoms, preferably by one or more oxygen atoms.
  • R 18 , R 19 and R 20 represent, independently of one another, a hydrocarbon group comprising from 2 to 24 carbon atoms, more preferably from 3 to 18 carbon atoms, still more preferably from 5 to 12 carbon atoms.
  • the dithiophosphate is an ester dithiophosphate of general formula (IV-c), in which R 21 and R 22 represent, independently of one another, optionally substituted hydrocarbon groups comprising from 1 to at 30 carbon atoms, R 23 and R 24 represent, independently of one another, hydrocarbon groups comprising from 1 to 18 carbon atoms:
  • R 2 i and R 22 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably from 3 to 18 carbon atoms. carbon, more preferably 5 to 12 carbon atoms.
  • R 21 and R 22 independently of one another represent hydrocarbon groups, substituted, said hydrocarbon groups may be alkyl, alkenyl, alkynyl, aryl, preferably phenyl or benzyl groups.
  • R21 and R22 represent independently of each other linear or branched alkyl hydrocarbon groups, more preferably linear alkyl hydrocarbon groups.
  • R 21 and R 22 represent, independently of one another, hydrocarbon groups optionally substituted with one or more oxygen, nitrogen, sulfur and / or phosphorus atoms, preferably by one or more oxygen atoms.
  • R 21 and R 22 represent, independently of one another, a hydrocarbon group of 2 to 6 carbon atoms.
  • R 23 and R 24 represent, independently of one another, hydrocarbon groups comprising from 2 to 6 carbon atoms.
  • Nrgalube 63 ® Commercial compounds are, for example Nrgalube 63 ® marketed by BASF.
  • the dithiophosphate is a metal dithiophosphate of general formula (IV-d), in which R 25 and R 26 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms, M represents a metal cation and n is the valence of this metal cation:
  • the metal is selected from the group consisting of zinc, aluminum, copper, iron, mercury, silver, cadmium, tin, lead, antimony, bismuth, thallium, chromium, molybdenum, cobalt, nickel, tungsten, sodium, calcium, magnesium, manganese and arsenic.
  • the metal is selected from zinc, molybdenum, antimony, preferably zinc and molybdenum, preferably zinc. Mixtures of metals can be used.
  • Metal dithiophosphates are neutral as exemplified in formula (IV-d) or basic when a stoichiometric excess of metal is present.
  • R 2 and R 2 represent, independently of one another, optionally substituted hydrocarbon groups comprising from 2 to 24 carbon atoms, more preferably from 3 to 18 carbon atoms. carbon atoms, more preferably from 5 to 12 carbon atoms.
  • R 2 5 and 2 represent, independently of each other, unsubstituted hydrocarbon groups, said hydrocarbon groups possibly being alkyl, alkenyl, alkynyl, aryl, preferably phenyls or benzyls.
  • R 25 and R 26 represent independently of each other linear or branched alkyl hydrocarbon groups, more preferably linear alkyl hydrocarbon groups.
  • R 25 and R 26 represent, independently of each other, hydrocarbon groups optionally substituted with one or more oxygen, nitrogen, sulfur and / or phosphorus, preferably with one or more oxygen atoms.
  • Useful metal dithiophosphates are compounds well known to those skilled in the art.
  • Additin ® RC 3038 Commercial compounds are, for example, Additin ® RC 3038, Additin ®
  • the metal dithiophosphate is a molybdenum dithiophosphate of formula (IV-d-1), in which R 25 and R 26 have the same meaning as in formula (IV-d):
  • the metal dithiophosphate is a zinc dithiophosphate of formula (IV-d-2), wherein F 1 and R 2 6 have the same meaning as in formula (IV). d):
  • the lubricating composition comprises from 0.1 to 5% by weight of dithiophosphate, relative to the total weight of the lubricating composition, preferably from 0.2 to 4%, more preferably from 0.3 to 2%, even more preferably 0.5 to 1%.
  • the lubricating composition according to the invention comprises at least one compound D comprising a thiadiazole group.
  • the compound D comprising a thiadiazole group is called "thiadiazole" in the following description.
  • thiadiazole is a compound of formula (Va)
  • R 27 and R 2 identical or different, independently represent a hydrogen atom or an alkyl group, saturated or unsaturated, linear or branched, comprising 1 to 30 carbon atoms,
  • a represents an integer ranging from 1 to 3
  • R 27 and R 28 represent a linear or branched, saturated or unsaturated alkyl group comprising from 1 to 20 carbon atoms, preferably from 1 to 15 carbon atoms, more preferably from 5 to 20 carbon atoms. to 15 carbon atoms, preferably 10 to 15 carbon atoms.
  • R 27 and R 2 8 are a saturated alkyl group, linear or branched, comprising 12 carbon atoms.
  • a represents an integer equal to 1 or 2 and b represents an integer equal to 1 or 2.
  • thiadiazole is a compound of formula (V-b)
  • - 2 8 represents a hydrogen atom or an alkyl group, saturated or unsaturated, linear or branched, comprising 1 to 30 carbon atoms,
  • b represents an integer ranging from 1 to 3.
  • R 2 s represents linear or branched, saturated or unsaturated alkyl group comprising from 1 to 20 carbon atoms, preferentially from 1 to 15 carbon atoms, more preferably from 5 to 15 carbon atoms. carbon atoms, preferably from 10 to 15 carbon atoms.
  • R 28 represents a saturated alkyl group, linear or branched, comprising 12 carbon atoms.
  • b represents an integer equal to 1 or 2.
  • the thiazole is a mixture of at least one compound of formula (V-a) and at least one compound of formula (V-b) as defined above.
  • the thiazole is a mixture:
  • R 27 and R 28 represent a saturated, linear or branched alkyl group comprising 12 carbon atoms, a represents an integer equal to 1 or 2 and b represents an integer equal to 1 or 2;
  • R 2 8 represents a saturated alkyl group, linear or branched, comprising 12 carbon atoms and b represents an integer equal to 1 or 2.
  • the lubricating composition comprises from 0.1 to 5% by weight of thiadiazole, relative to the total weight of the lubricating composition, preferably from 0.2 to 4%, more preferably from 0.3 to 2%, even more preferably 0.5 to 1%.
  • the ratio by weight ranges from 3: 1 to 1: 8, preferably from 2: 1 to 1: 5, advantageously from 1: 1 to 1: 5
  • the lubricant compositions according to the invention may contain any type of mineral, synthetic or natural, animal or vegetable lubricating base oil adapted for their use.
  • the base oil or oils used in the lubricant compositions according to the present invention may be oils of mineral or synthetic origin of groups I to V according to the classes defined in the API classification (or their equivalents according to the ATI EL classification) such that summarized below, alone or as a mixture.
  • the mineral base oils 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, deasphalting, solvent dewaxing, hydrotreatment, hydrocracking and hydroisomerization, hydrofinishing.
  • the base oils of the lubricating compositions according to the invention may also be synthetic oils, such as certain carboxylic acid esters and alcohols, or polyalphaolefins.
  • the polyalphaolefins used as base oils are obtained from monomers having from 4 to 32 carbon atoms (for example octene, decene), and a viscosity at 100 ° C. of between 1.5 and 15 cSt measured according to US Pat. ASTM D445 standard. Their weight average molecular weight is typically between 250 and 3000 measured according to ASTM D5296. Mixtures of synthetic and mineral oils can also be used.
  • a particular lubricating base for producing the lubricating compositions according to the invention must have properties, in particular viscosity, viscosity index, sulfur, oxidation resistance, suitable for use in a gearbox, in particular in a gearbox of motor vehicles, especially in a manual gearbox.
  • the lubricating bases represent at least 50% by weight, relative to the total mass of the lubricating composition, preferably at least 60%, or at least 70%. Typically, they represent between 75 and 99.9% by weight, relative to the total mass of the lubricating compositions according to the invention.
  • the lubricating compositions comprise Group I and / or III mineral bases, or Group IV synthetic bases according to the API classification.
  • the lubricating compositions have a kinematic viscosity at 100 ° C. measured according to ASTM D445 of between 4 and 41 cSt, according to classification SAE J 306, preferably between 4.1 and 32.5 cSt, advantageously from 6 to 18.5 cSt.
  • Preferred grades are all grades from 75W to 140, including 75W, 75W80 and 75W90.
  • the lubricating compositions have a viscosity index (VI) greater than 120 (ASTM 2270).
  • the lubricating compositions according to the invention may also contain any type of additive suitable for use in transmission oil formulations, for example one or more additives chosen from polymers, antioxidants, anti-corrosion additives, dispersants present at the usual contents required for the application.
  • the polymers are selected from the group of shear-stable polymers, preferably from the group consisting of copolymers of ethylene and alpha-olefin, polyacrylates such as polymethacrylates, copolymer olefins (OCP), ethylene propylene diene Monomers (EPDM), polybutenes, copolymers of styrene and olefin, hydrogenated or not, or copolymers of styrene and acrylate.
  • the preferred polymers are polymethacrylates (PMA).
  • the lubricating composition further comprises at least one dispersant.
  • Preferred dispersants are polyisobutylenes (PIB) or polyisobutene derivatives. More preferably, the lubricant composition according to the invention may comprise a dispersant derived from polyisobutene.
  • a polyisobutene derivative there may be mentioned polyisobutylenes of succinic anhydride, amino derivatives of polyisobutylenes of succinic anhydride (PIB succinimides).
  • Preferred antioxidants are, for example, amine antioxidants.
  • the lubricating composition according to the invention may comprise an antioxidant chosen from the group of aromatic amines, for example diphenylamines, in particular dialkylphenylamines, such as octadiphenylamines, phenyl-alpha-naphthylamines.
  • an antioxidant chosen from the group of aromatic amines, for example diphenylamines, in particular dialkylphenylamines, such as octadiphenylamines, phenyl-alpha-naphthylamines.
  • the lubricating composition may comprise an antioxidant derived from phenol (dibutylhydroxytoluene BHT and derivatives) or a sulfur antioxidant (sulfurized phenates).
  • the lubricant composition comprises an antioxidant selected from the group consisting of aromatic amines or phenol derivatives.
  • the preferred anti-corrosion additives are phenolic derivatives, in particular ethoxylated phenol derivatives substituted with ortho-position alkyl groups.
  • the lubricating composition further comprises at least one dispersant and at least one other additive selected from those mentioned above.
  • the lubricant composition comprises:
  • the lubricant composition comprises: from 75 to 99.6% of a base oil,
  • the lubricant composition comprises:
  • the ratio by weight (compound C comprising a dithiophosphate group: compound D comprising a thiadiazole group) ranging from 5: 1 to 1: 10.
  • the lubricant composition comprises:
  • the ratio by weight (compound C comprising a dithiophosphate group: compound D comprising a thiadiazole group) ranging from 5: 1 to 1: 10.
  • the lubricant composition consists essentially of:
  • a compound A comprising a dithiocarbamate group this compound being a mixture of an amine dithiocarbamate of general formula (I) as described above and of a metal dithiocarbamate of general formula ( II) as described above,
  • a compound D comprising a thiadiazole group 0.1 to 5% of a compound D comprising a thiadiazole group, the ratio by weight (compound C comprising a dithiophosphate group: compound D comprising a thiadiazole group) ranging from 5: 1 to 1: 10.
  • the lubricant composition consists essentially of:
  • the lubricant composition consists essentially of:
  • the ratio by weight (compound C comprising a dithiophosphate group: compound D comprising a thiadiazole group) ranging from 5: 1 to 1: 10.
  • the lubricant composition consists essentially of:
  • the ratio by weight (compound C comprising a dithiophosphate group: compound D comprising a thiadiazole group) ranging from 5: 1 to 1: 10.
  • the percentages are expressed by weight relative to the total mass of the lubricating composition.
  • the set of characteristics and preferences presented for the base oil, the compound comprising a phosphite group, the compound comprising a thiophosphate group, the compound comprising a dithiocarbamate group, the compound comprising a thiadiazole group and the additional additive applies. also to the lubricant compositions above.
  • the lubricating composition is not an emulsion.
  • the lubricating composition is an anhydrous composition.
  • the invention also relates to a process for preparing a lubricating composition as defined above.
  • the method comprises at least the following steps:
  • the temperature of step (a) ranges from 40 to 70 ° C. In another embodiment, the temperature of step (b) ranges from 40 to
  • step (b) further comprises adding at least one additional additive.
  • step (c) is identical to that of step (a).
  • the base oil of step (c) is different from that of step (a).
  • the invention also relates to the use of a lubricant composition as defined above for the lubrication of transmissions such as gearboxes, bridges, preferably manual gearboxes of motor vehicles.
  • the subject of the invention is the use of a lubricant composition as defined above for the lubrication of a brass mechanical part, preferably present in a transmission member, more preferably in a box. speeds, even more preferably in a manual gearbox.
  • the subject of the invention is the use of a lubricant composition as defined above for the lubrication of synchronizers present in a transmission member, more preferably in a gearbox, even more preferably in a manual gearbox.
  • the invention also relates to the use of a lubricant composition as defined above for reducing the fuel consumption of vehicles, particularly motor vehicles.
  • the invention also relates to the use of a lubricant composition as defined above for reducing the wear of gearbox synchronizers, preferably manual gearboxes.
  • the subject of the invention is also the use of a lubricant composition as defined above for reducing the peeling of a mechanical part, preferably present in a transmission member, more preferably in a gearbox, and even more so. preferentially in a manual gearbox.
  • the invention also relates to a method of lubricating transmissions such as gearboxes, bridges, preferably manual gearboxes of motor vehicles, said method comprising at least one step of contacting a lubricant composition as defined above with the transmissions.
  • the subject of the invention is a method of lubricating a brass mechanical part, preferably present in a transmission member, more preferably in a gearbox, even more preferably in a manual gearbox.
  • the invention relates to a method of lubricating synchronizers present in a transmission member, more preferably in a gearbox, even more preferably in a manual gearbox.
  • the invention also relates to a method for reducing seizure of a mechanical part, preferably present in a transmission member, more preferably in a gearbox, even more preferably in a manual gearbox, comprising at least the setting in contact with the mechanical part with a lubricating composition as defined above.
  • the subject of the invention is also a process for reducing the wear of a gearbox synchronizer, preferably of manual gearboxes, comprising at least putting the synchronizer into contact with a lubricant composition as defined above.
  • the invention also relates to a method for reducing the peeling of a mechanical part, preferably present in a transmission member, more preferably in a gearbox, even more preferably in a manual gearbox, comprising at least bringing the mechanical part into contact with a lubricating composition as defined above.
  • the subject of the invention is also a process for reducing galling, wear and spalling of a mechanical part, preferably present in a transmission member, more preferably in a gearbox, even more preferably in a gearbox.
  • manual gearbox said method comprising at least one step of contacting the mechanical part with a lubricant composition as defined above.
  • the mechanical part is a synchronization device (synchronizer).
  • the set of characteristics and preferences presented for the lubricating composition also applies to the above processes.
  • the subject of the invention is also the use of at least one compound A comprising a dithiocarbamate group, at least one compound B comprising a phosphite group, at least one compound C comprising a dithiophosphate group and at least one a compound D comprising a thiadiazole group in a base oil for improving the wear, extreme-pressure, friction and anti-seizing properties of a lubricating composition, the compound A comprising a dithiocarbamate group being a mixture:
  • At least one amine dithiocarbamate of general formula (I) (compound A-1)
  • R 1 and R 2 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms
  • R 3, R 4 and R 5 represent, independently of one another, a hydrogen atom or a hydrocarbon group of 1 to 30 carbon atoms, it being understood that at least one of the groups R 3 , R 4 and R 5 is not a hydrogen atom, and
  • At least one metal dithiocarbamate of general formula (II) (compound A-2)
  • R 6 and R 7 represent, independently of each other, optionally substituted hydrocarbon groups comprising from 1 to 30 carbon atoms
  • M represents a metal cation and n is the valency of this metal cation
  • the compound D comprising a thiadiazole group being chosen from the group formed by
  • R27 and R 2 identical or different, independently represent a hydrogen atom or an alkyl group, saturated or unsaturated, linear or branched, comprising 1 to 30 carbon atoms,
  • a represents an integer ranging from 1 to 3
  • b represents an integer ranging from 1 to 3
  • - R 2 8 represents a hydrogen atom or an alkyl group, saturated or unsaturated, linear or branched, comprising 1 to 30 carbon atoms
  • b represents an integer ranging from 1 to 3
  • the set of characteristics and preferences presented for the base oil, the compound comprising a phosphite group, the compound comprising a thiophosphate group, the compound comprising a dithiocarbamate group and the compound comprising a thiadiazole group also applies to the use above.
  • the use of these five additives in a lubricating composition also makes it possible to maintain good anti-peeling properties of the lubricating composition.
  • the subject of the invention is also a composition of the additive concentrate type comprising at least one compound A comprising a dithiocarbamate group, at least one compound B comprising a phosphite group, at least one compound C comprising a dithiophosphate group and at least one compound D comprising a thiadiazole group.
  • a comprising a dithiocarbamate group, for the compound B comprising a phosphite group, for the compound C comprising a thiophosphate group and the compound D comprising a thiadiazole group also applies to the composition of the additive concentrate type above.
  • a PAO group IV base oil having a viscosity at 100 ° C. of 6 cSt measured according to ASTDM D445, and a viscosity index of 125 measured according to ASTM 2270,
  • phosphite which is di-n-octyl phosphite sold under the name Irgafos OPH by the company BASF,
  • dispersant which is a derivative of the polyisobutylene succinimide sold under the name Doversperse H1015-P by the company DoverChemical,
  • antioxidant which is a diphenyl amine sold under the name Irganox L57 by the company BASF,
  • an anti-corrosion A1 which is a benzotriazole marketed under the name RC 5800 by Rhein Chemie
  • An anti-corrosion A2 which is a mixture of a C12-C16 alcohol and an alkyl ether of carboxylic acid, the content by weight of alcohol being at most 20% relative to the total weight of the mixture and the content by weight of alkyl ether being at least 70% relative to the total weight of the mixture (Irgacor 843 marketed by BASF).
  • Lubricating compositions Nos. 1 to 7 are described in Table II: the percentages indicated are percentages by weight.
  • Lubricating compositions No. 1 to No. 3 and No. 6 to No. 7 are comparative compositions, lubricating compositions No. 4 and No. 5 are according to the invention.
  • the purpose of this test is to evaluate the anti-wear properties of lubricating compositions against synchronizers.
  • the wear tests of the synchronizers on the lubricant compositions 1 to 5 were performed on a cone / ring couple under the following conditions (SYNC-13 procedure, SAE 2-A):
  • Threaded brass ring 54 mm (for example reference 7700 708 152 or 7700 869 430,
  • Oil 125 ml of the lubricant composition to be tested, oil level on the lower part of the ring
  • This test makes it possible more particularly to evaluate the anti-wear properties of a lubricant composition in the steel / brass surface contacts, corresponding to the type of contacts used at the level of the synchronizers.
  • composition No. 4 makes it possible to significantly reduce the wear of the synchronizers with respect to a lubricating composition comprising a combination of a dithiocarbamate, a dithiophosphate and a phosphite but not including thiadiazole (composition No. 1) or with respect to lubricating compositions comprising a combination of a dithiocarbamate, a dithiophosphate and a phosphite and an anti-corrosion different from a thiadiazole (compositions No. 2 and No. 3).
  • the results relating to the lubricant composition No. 5 according to the invention show a very clear reduction in the wear of the synchronizers with respect to a lubricating composition comprising a combination of a dithiocarbamate, a dithiophosphate and a dithiocarbamate.
  • phosphite but not comprising thiadiazole composition No. 1
  • compositions comprising a combination of a dithiocarbamate, a dithiophosphate and a phosphite and an anti-corrosion other than a thiadiazole
  • Test No. 2 Evaluation of the anti-wear properties of a composition according to the invention on gearbox synchronizers
  • the purpose of this test is to confirm the anti-wear properties of a lubricant composition according to the invention against synchronizers.
  • Threaded brass ring 54 mm (eg reference 7700 708 152 or 7700
  • Oil 250 ml of lubricant composition No. 5, oil level in the middle of the pinion and the ring
  • the synchronizer locking test is considered satisfactory if, during the 10125 gearshift cycles, the number of cycles in which the disengagement between the cone and the ring requires the application of a counter torque greater than 2 mN is at most 100 cycles.
  • the result of the test with the lubricating composition No. 5 is 32, which confirms the very good anti-wear properties of this lubricant composition according to the invention against synchronizers.
  • the anti-wear properties of lubricant compositions No. 1, No. 5, No. 6 and No. 7 were evaluated by a 4-ball wear test according to Standard D55 1078; this test including implementing steel balls. A value greater than 0.8mm corresponding to a level of wear that is not acceptable.
  • This test makes it possible more particularly to evaluate the anti-wear properties of a lubricant composition in the steel / steel surface contacts corresponding to the majority of the contacts used in a gearbox.
  • composition No. 5 a lubricating composition according to the invention
  • composition No. 5 has satisfactory anti-wear and extreme pressure properties, even improved with respect to compositions comprising a combination of a dithiocarbamate, a dithiophosphate and a dithiocarbamate.
  • a phosphite according to the invention but not including thiadiazole compositions No. 1, No. 6 and No. 7.
  • Test n ° 4 evaluation of the anti-seizing properties of lubricating compositions
  • the purpose of this test is to evaluate the anti-seizing properties of lubricating compositions.
  • the anti-seizing properties of lubricant compositions No. 1, No. 5, No. 6 and No. 7 were evaluated by an FZG test according to CEC standard L84 (A / 16, 6R / 120); the higher the value obtained after the test, the better the anti-seizing properties.
  • compositions no. 5 The results show that a lubricant composition according to the invention (compositions no. 5) has anti-seizing properties which are equivalent to, or even improved over, lubricating compositions comprising a combination of a dithiocarbamate, a dithiophosphate and a dithiocarbamate. phosphite but not including thiadiazole (compositions No. 1, No. 6 and No. 7).
  • Test No. 5 Evaluation of anti-scaling properties of lubricating compositions
  • the purpose of this test is to evaluate the anti-scaling properties of lubricating compositions.
  • the purpose of this test is to evaluate the ability of a lubricant composition to protect gear surfaces against pitting damage.
  • PT-C gearing was used and tested on an FZG machine.
  • a constant rotation speed at 1440 rpm has been set, with a constant load also (step 9).
  • the temperature of the lubricating composition to be tested was regulated at 120 ° C.
  • the test was then run by "run” 8 hours at the beginning, then the appearance of the first scratches on the teeth, the duration of these "run” was decreased.
  • the ultimate goal is to determine the service life of a lubricating gear lubricated by evaluating the flaking surface on each tooth of the gear.
  • the failure criterion is achieved when the surface comprising scales for all teeth ⁇ 1 mm 2 .
  • composition No. 5 a lubricating composition according to the invention exhibits anti-scaling properties which are equivalent to, or even improved over, lubricating compositions comprising a combination of a dithiocarbamate, a dithiophosphate and a phosphite but not including thiadiazole (compositions No. 1, No. 6 and No. 7).

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • General Details Of Gearings (AREA)
EP14745153.8A 2013-08-02 2014-08-01 Compositions lubrifiantes pour transmissions Withdrawn EP3027719A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1357713A FR3009309B1 (fr) 2013-08-02 2013-08-02 Compositions lubrifiantes pour transmissions
PCT/EP2014/066596 WO2015014986A1 (fr) 2013-08-02 2014-08-01 Compositions lubrifiantes pour transmissions

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EP3027719A1 true EP3027719A1 (fr) 2016-06-08

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US (1) US20160168505A1 (enExample)
EP (1) EP3027719A1 (enExample)
JP (1) JP2016525623A (enExample)
KR (1) KR20160040255A (enExample)
CN (1) CN105579564A (enExample)
FR (1) FR3009309B1 (enExample)
WO (1) WO2015014986A1 (enExample)

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FR3018079B1 (fr) 2014-02-28 2017-06-23 Total Marketing Services Composition lubrifiante a base de nanoparticules metalliques
US10526287B2 (en) 2015-04-23 2020-01-07 Constellation Pharmaceuticals, Inc. LSD1 inhibitors and uses thereof
EP3532459B1 (en) 2016-10-26 2023-08-02 Constellation Pharmaceuticals, Inc. Lsd1 inhibitors and medical uses thereof
EP3676358A4 (en) * 2017-08-29 2021-05-12 Basf Se LUBRICATING COMPOSITION FOR GEARS
EP3683290B1 (en) 2019-01-16 2023-09-06 Afton Chemical Corporation Lubricant containing thiadiazole derivatives
US10808198B2 (en) 2019-01-16 2020-10-20 Afton Chemical Corporation Lubricant containing thiadiazole derivatives
KR102089942B1 (ko) 2019-05-09 2020-03-18 (주)에코시즌 트랜스미션오일 조성물
FR3097870B1 (fr) * 2019-06-28 2022-01-14 Total Marketing Services Utilisation d’un composé de type amine aromatique ou phénol stériquement encombré à titre d’additif anticorrosion dans une composition lubrifiante
CN114436825B (zh) * 2020-10-30 2024-12-06 中国石油化工股份有限公司 一种铅化合物及其制备方法、用途和润滑油组合物
EP4368687B1 (en) 2022-11-10 2025-06-25 Afton Chemical Corporation Corrosion inhibitor and industrial lubricant including the same
FR3154414A1 (fr) * 2023-10-18 2025-04-25 Totalenergies Onetech Composition lubrifiante pour transmission automobile.

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Publication number Publication date
FR3009309B1 (fr) 2016-10-07
CN105579564A (zh) 2016-05-11
FR3009309A1 (fr) 2015-02-06
JP2016525623A (ja) 2016-08-25
WO2015014986A1 (fr) 2015-02-05
US20160168505A1 (en) 2016-06-16
KR20160040255A (ko) 2016-04-12

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