EP3959296B1 - Graisses de lubrification comprenant des savons métalliques et des complexes de savons métalliques à base d'acide r-10-hydroxyoctadécanoïque - Google Patents

Graisses de lubrification comprenant des savons métalliques et des complexes de savons métalliques à base d'acide r-10-hydroxyoctadécanoïque Download PDF

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Publication number
EP3959296B1
EP3959296B1 EP20725070.5A EP20725070A EP3959296B1 EP 3959296 B1 EP3959296 B1 EP 3959296B1 EP 20725070 A EP20725070 A EP 20725070A EP 3959296 B1 EP3959296 B1 EP 3959296B1
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EP
European Patent Office
Prior art keywords
acid
lubricating grease
composition according
grease composition
metal
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EP20725070.5A
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German (de)
English (en)
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EP3959296A1 (fr
Inventor
Thomas Litters
Florian Hahn
Rolf Luther
Markus Urban
Angela ROBBEN
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Fuchs SE
Original Assignee
Fuchs Petrolub SE
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Priority to RS20230042A priority Critical patent/RS63900B1/sr
Priority to HRP20230066TT priority patent/HRP20230066T1/hr
Publication of EP3959296A1 publication Critical patent/EP3959296A1/fr
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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
    • C10M117/00—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof
    • C10M117/02—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof having only one carboxyl group bound to an acyclic carbon atom, cycloaliphatic carbon atom or hydrogen
    • C10M117/04—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof having only one carboxyl group bound to an acyclic carbon atom, cycloaliphatic carbon atom or hydrogen containing hydroxy 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
    • 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
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C10M129/26—Carboxylic acids; 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
    • 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
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no 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
    • C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M141/12—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 compound containing atoms of elements not provided for in groups C10M141/02 - C10M141/10
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
    • C—CHEMISTRY; METALLURGY
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04—Elements
    • C10M2201/05—Metals; Alloys
    • C10M2201/056—Metals; Alloys used as thickening agents
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    • C10M2201/087—Boron oxides, acids or salts
    • C10M2201/0876—Boron oxides, acids or salts used as thickening agent
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/102—Silicates
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    • C10M2201/10—Compounds containing silicon
    • C10M2201/102—Silicates
    • C10M2201/103—Clays; Mica; Zeolites
    • C10M2201/1036—Clays; Mica; Zeolites used as thickening agents
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
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    • C10M2201/105—Silica
    • C10M2201/1056—Silica used as thickening agents
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    • 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
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
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    • 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
    • C10M2215/26—Amines
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    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/045—Polyureas; Polyurethanes
    • C10M2217/0456—Polyureas; Polyurethanes used as thickening agents
    • 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
    • C10M2223/026—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds used as thickening agents
    • 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
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/12—Groups 6 or 16
    • 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
    • C10N2030/02—Pour-point; 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
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • 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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2030/40—Low content or no content compositions
    • 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
    • C10N2030/68—Shear stability
    • 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
    • C10N2040/02—Bearings
    • 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
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for 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
    • C10N2040/14—Electric or magnetic purposes
    • 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
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • the invention relates to lubricating greases based on alkali and/or alkaline earth metal soaps and metal complex soaps based on R-10-hydroxyoctadecane acid and their use.
  • Lubricating oils have a liquid and flowable consistency
  • lubricating greases have a semi-solid to solid - often gel-like - consistency.
  • a characteristic of a lubricating grease is that a liquid oil component is absorbed and held by a thickener component.
  • the pasty nature of a lubricating grease and its property of being spreadable and easily plastically deformable, together with the property of being adhesive, ensure that the lubricating grease wets the lubricating point and the lubricating effect unfolds on the tribologically stressed surfaces.
  • Lubricating greases contain a thickener that is homogeneously distributed in a base oil. Additional auxiliaries, such as emulsifiers, are often used so that the thickener disperses stably in the base oil. Various substances are known as base oils. Organic and inorganic compounds are used as thickeners. Additives are often added to the lubricating grease to improve wear protection, friction behavior, aging stability and corrosion protection, among other things.
  • the most important viscoelastic properties of a lubricating grease include the yield point and the shear viscosity. Both have a major impact on the efficiency of grease-lubricated drives or bearings, especially when elastohydrodynamic lubrication (EHL) is present at high sliding speeds or speeds. Especially at low application temperatures, the yield point and shear viscosity have a major impact on the so-called breakaway torque and running torque of grease-lubricated components and assemblies.
  • EHL elastohydrodynamic lubrication
  • Greases are widely used for lubrication purposes in the automotive and aerospace industries. Compared to oils, they have numerous advantages in terms of design and maintenance. Therefore, they are used to lubricate a large number of moving parts in passenger cars and airplanes where oil lubrication fails.
  • the viscoelastic behavior of lubricating greases also has disadvantages, which can be seen in particular when lubricated components are operated at very low temperatures.
  • the "breakaway torque" is particularly noticeable when grease-lubricated vehicle components such as steering, sunroofs, window regulators, side mirror adjusters or door locks have to be operated manually or are operated with low servo-electric drive power.
  • lubricating greases In the automotive industry, lubricating greases must therefore generally work reliably down to a temperature of at least -40 °C.
  • lubricating greases In aviation, lubricating greases have to work reliably at temperatures down to -54 °C, sometimes even down to -73 °C.
  • the grease in the landing gear wheel bearings must not fail during landing, even if the aircraft has been at high altitude for a long time and the landing gear has been exposed to very low temperatures.
  • the "breakaway torque" of aircraft greases must not exceed a certain value.
  • Hydroxyoctadecanoic acid in particular 12-hydroxyoctadecanoic acid (12-hydroxystearic acid), is a fatty acid that has been used for some time for the production of metal soap greases, in particular lithium soap greases and lithium complex soap greases.
  • the starting product for 12-hydroxyoctadecanoic acid or its esters or triglycerides is ricinoleic acid ((9Z,12R)-12-hydroxy-9-octadecenoic acid) and its triglyceride, the so-called castor oil, which is mainly obtained from the castor plant.
  • the unsaturated hydroxy fatty acid ricinoleic acid or its triglyceride is converted into a saturated hydroxy fatty acid by hydrogenation in order to make it storage-stable and thermally stable.
  • other hydroxyoctadecane fatty acids such as 10-hydroxyoctadecanoic acid, have hardly any technical significance, even if they are casually cited again and again in intellectual property rights or in the literature, such as, for example, in US4802999A , EP 3461901 A1 or Matthias Engelder et al. "Structure-Based Mechanism of Oleate Hydratase from Elizabethkingia meningoseptica", ChemBioChem., 16 (2015), pp. 1730-1734 , without the R-form being advertised or actually being used as a component of the thickener.
  • the object of the invention is to minimize the disadvantages described above in terms of efficiency and low-temperature behavior.
  • 10-hydroxyocatadecanoic acid (10-hydroxystearic acid, CAS 638-26-6 ) can be produced enzymatically, as is already the case G. Schroepfer in Biological Chemistry (1966), 241 (22 ) published. Both the R and S form can be used for the production of lubricating grease.
  • the structural form of the R form is:
  • the substrate for the enzymatic conversion is predominantly (9Z)-octadeca-9-enoic acid (oleic acid), which can be obtained from local "high-oleic" sunflower oil, for example with a purity of greater than 92% (9Z)-octadeca-9-enoic acid, but can also be produced from technical quality with a purity of more than 60% (9Z)-octadeca-9-enoic acid.
  • oleic acid 9Z-octadeca-9-enoic acid
  • hexadecanoic acid (palmitic acid), hexadecenoic acid (palmitoleic acid), octadecanoic acid (stearic acid) or polyunsaturated fatty acids such as linoleic acid ((9Z,12Z)-octadeca-9,12-dienoic acid) or linolenic acid ((9Z,12Z, 15Z)-octadeca-9,12,15-trienoic acid).
  • One advantage of this enzymatic process is that local raw materials can be used, thereby expanding the supply chain to include local raw materials.
  • carbon-rich waste streams containing unsaturated C18 acids or esters for the production of 10-hydroxyocatadecanoic acid.
  • carbon-rich waste streams can be used on the one hand as nutrients for enzyme production and on the other hand as "feedstock” for the preparation of the target products.
  • Used cooking fats and oils, residues from biodiesel production (e.g. glycerol, fatty acids, methyl esters) and other industrial by-products can be used as raw materials for material use.
  • 12-hydroxyocatadecanoic acid (12-hydroxystearic acid, CAS 106-14-9 ) is commercially available, for example, from Sigma-Aldrich or from Nidera BV. 12-Hydroxyoctadecanoic acid is chemically produced from castor oil by hydrolysis and hydrogenation. Castor oil is mainly produced in India, Brazil and China. The purity of the commercially available 12-hydroxyocatadecanoic acid is generally 80-98% by weight.
  • R-10-hydroxyoctadecanoic acid is also given, for example, when other fatty acids with a chain length of C16 to C18, such as hexadecanoic acid (palmitic acid) (C16:0), 9-hydroxyhexadecanoic acid, octadecanoic acid (stearic acid), (9Z)-octadeca -9-enoic acid (oleic acid) or polyunsaturated fatty acids such as linoleic acid ((9Z,12Z)-octadeca-9,12-dienoic acid) or linolenic acid ((9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid) in unhydroxylated or hydroxylated form are also used in the production of metal soaps, in particular together with R-10-hydroxyoctadecanoic acid.
  • other fatty acids with a chain length of C16 to C18 such as hexa
  • lubricating greases based on R-10-hydroxyoctadecanoic acid have significantly lower thickener contents with the same consistency and preferably require at least 30% by weight less thickener and at least 30% by weight less lithium hydroxide monohydrate for production.
  • Lubricating greases produced in this way have significantly lower flow pressures, yield points and significantly lower starting torques in plain bearings, roller bearings and gears, especially at low temperatures.
  • production costs can be saved by reducing the use of lithium hydroxide monohydrate.
  • lithium R-10-hydroxyoctadecanate soap in situ, i.e. by reacting lithium hydroxide monohydrate with R-10-hydroxyoctadecanoic acid, but lithium 10-hydroxyoctadecanate prepared in a separate step can also be mixed into a base oil and subsequently thermal and mechanical processing can be brought to thickening.
  • the % by weight data relate to the overall composition and are each valid independently of one another.
  • the base oil has in particular a kinematic viscosity of 14 to 2500 mm 2 /s, preferably 30 to 500 mm 2 /s, in each case at 40°C.
  • the base oils can be classified as mineral oils or synthetic oils.
  • Mineral oils are considered to be naphthenic mineral oils and paraffin-based mineral oils, according to classification according to API Group I. Chemically modified, aromatic and low-sulphur mineral oils with a low proportion of saturated compounds and improved viscosity/temperature behavior compared to Group I oils, classified according to API Group II III, Group III+ and synthetic oils (GTL oils) produced from natural gas using the so-called gas-to-liquid process are also suitable.
  • di- or polyethers Mentioned as synthetic oils are di- or polyethers, esters, polyalphaolefins, polyglycols and alkylaromatics and mixtures thereof.
  • the di-ether compound can be a compound having aliphatic groups and/or aromatic groups (e.g., alkylated diphenyl ethers).
  • the polyether compound can have free hydroxyl groups, but can also be fully etherified or end groups esterified and/or be made from a starting compound having one or more hydroxyl and/or carboxyl groups (-COOH).
  • Diphenyl ethers or polyphenyl ethers, optionally alkylated are also possible as sole components or, even better, as mixed components.
  • Esters of an aromatic di-, tri- or tetracarboxylic acid with one or a mixture of C2 to C30 alcohols esters of adipic acid, sebacic acid, trimethylolopropane, neopentyl glycol, pentaerythritol or dipentaerythritol with aliphatic branched or unbranched, saturated or unsaturated C2 are suitable to C22 carboxylic acids, C18 dimer acid esters with C2 to C22 alcohols, complex esters, as individual components or in any mixture.
  • LAO linear alpha olefin
  • metal R-10-hydroxyoctadecanate based greases particularly in base oils containing or consisting of polyalphaolefins, have an unexpected advantage in low temperature performance and efficiency.
  • the soaps used according to the invention differ significantly from conventional 12-hydroxyoctadecanate soaps.
  • metal salts such as metal hydroxides
  • metal salts such as metal hydroxides
  • these may be alkali metal or alkaline earth metal salts of one or more saturated or unsaturated monocarboxylic acids having 10 to 15 and/or 19 to 24 carbon atoms, optionally substituted, such as corresponding hydroxycarboxylic acids.
  • suitable carboxylic acids are lauric acid, myristic acid or behenic acid.
  • saturated or unsaturated branched-chain fatty acids can also be used. Naphthenic acids, neodecanoic acids or comparable neoacids can also be used.
  • metal soaps can also be simple, mixed or complex soaps based on Al, Bi, Ti salts and carboxylic acids or on Li, Na, Mg, Ca, Al, Bi, Ti salts and sulfonic acids, added during base fat manufacture or later as an additive.
  • these soaps can also be formed in situ during the production of the metal soaps used according to the invention.
  • corresponding lower alcohol esters can also be used with saponification in the production of the respective metal soaps, e.g. corresponding triglycerides and the methyl, ethyl, propyl, isopropyl or sec to achieve better dispersion.
  • the complexing agent (a) is preferred.
  • Acetic acid and propionic acid are particularly suitable as monocarboxylic acids.
  • hydroxybenzoic acids such as parahydroxybenzoic acid, salicylic acid, 2-hydroxy-4-hexylbenzoic acid, metahydroxybenzoic acid, 2,5-dihydroxybenzoic acid (gentisic acid), 2,6-dihydroxybenzoic acid (gamma-resorcylic acid) or 4-hydroxy-4-methoxybenzoic acid.
  • Particularly suitable dicarboxylic acids are adipic acid (C 6 H 10 O 4 ), sebacic acid (C 10 H 18 O 4 ), azelaic acid (C 9 H 16 O 4 ) and/or 3- tert -butyladipic acid (C 10 H 18 O4 ).
  • Metaborate, diborate, tetraborate or orthoborate, such as monolithium orthoborate, for example, can be used as borate (b).
  • Possible phosphates are alkali metal (preferably lithium) and alkaline earth metal (preferably calcium) dihydrogen phosphate, hydrogen phosphate or pyrophosphate, or calcium or lithium hydroxyapatite.
  • Esters of boric acid and phosphoric acid which can be used are those having unbranched or branched alkyl groups of 2 to 32, preferably 8 to 32, carbon atoms.
  • bentonites such as montmorillonite (the sodium ions of which may have been replaced or partially replaced by organically modified ammonium ions), aluminosilicates, alumina, hydrophobic and hydrophilic silicic acid, oil-soluble polymers (e.g. polyolefins, poly(meth)acrylates, Polyisobutylene, polybutene or polystyrene copolymers), polyurea or polyurea-polyurethane or PTFE can be used.
  • the bentonites, aluminosilicates, clays, silicic acid and/or oil-soluble polymers can be added to make the base grease or added later as an additive in the second step.
  • lignin derivatives can also be added as a co-thickener or as an additive.
  • Lignin derivatives are active ingredients in lubricating greases and can be used to improve anti-wear properties and scuffing load properties.
  • the lignin derivatives can represent multifunctional components. Because of their high number of polar groups and aromatic structures, their polymeric structure and their low solubility in all types of lubricating oils, powdered lignins and/or lignin sulfonates are also suitable as solid lubricants in lubricating greases and lubricating pastes. In addition, the phenolic hydroxyl groups contained in lignin and lignin sulfonates ensure an anti-aging effect. In the case of lignin sulfonates, the sulfur content in lignin sulfonates promotes the EP/AW effect in lubricating greases.
  • Lignins and/or calcium and/or sodium lignin sulfonate or mixtures thereof are preferably used.
  • Kraft lignins, soda lignins or Organosolv lignins can also be used.
  • bio-based oligomers or polymers as solid lubricants or co-thickeners such as triterpenes, cellulose or modified cellulose, chitin and/or chitosan.
  • the thickener (metal soaps according to the invention, other metal soaps and co-thickeners) is used in such a way that the composition contains enough thickener for a cone penetration value (worked penetration) of 210 to 475 mm/10 (at 25° C.), preferably 230 to 385 mm/10 (at 25° C.) (determined according to DIN ISO 2137 or ASTM D 0217-97).
  • compositions according to the invention may also contain additives as additives.
  • Customary additives for the purposes of the invention are antioxidants, antiwear agents, anticorrosive agents, detergents, dyes, lubricity improvers, adhesion promoters, viscosity additives, friction reducers, extreme pressure additives and metal deactivators.
  • soot or other carbon-based solid lubricants such as nanotubes.
  • Lignin derivatives can also be used as a thickener component or solid lubricant.
  • Bio-based oligomers or polymers such as triterpenes, modified cellulose, chitin, chitosan or polypeptides are also possible.
  • the lubricating greases according to the invention are particularly suitable for use in plain and roller bearings, transmissions and/or constant velocity drive shafts in industrial and automotive applications. It is a particular aspect of the present invention to arrive at low-friction lubricating greases, in particular at low temperatures, at which low breakaway torques and running torques are required and at which a low yield point and shear viscosity are advantageous. In the special case of lubricating plain and roller bearings and gears and constant velocity drive shafts in automotive engineering, smaller and lighter drives can be used and efficiency advantages can be achieved.
  • Lubricating greases produced according to the present invention have yield points that are up to 43% lower at -35° C., measured with the oscillation rheometer according to DIN 51810-2, and shear viscosities that are up to 50% lower, determined with the shear viscometer according to DIN 51810-1 than comparable lubricating greases.
  • the lubricating greases produced according to the present invention show values at -40°C that are at least 50% lower than comparable lubricating greases.
  • the lubricating greases according to the invention have coefficients of sliding friction which are up to 37% lower than with a comparable lubricating grease based on 12-hydroxyoctadecanoic acid.
  • a method for determining the yield point using an oscillation rheometer is DIN 51810-2.
  • the flow pressure method according to DIN 51805-2 is also used to determine the lower service temperature of lubricating greases.
  • the flow pressure is the differential pressure to atmospheric pressure required to force a strand of lubricating grease out of a test nozzle under the conditions specified in this standard. It is a measure of the stiffness of a lubricating grease at the respective test temperature and can be used as a measure of the yield point in addition to the test according to DIN 51810-2.
  • IP 186 and ASTM D 1478 describe the determination of the starting and running torque of ball bearings. With these test methods, the functionality of lubricating greases can be tested at low temperatures, e.g. -40°C or -73 °C.
  • the lubricating greases can be produced, for example, as follows: Mixing the salt/metal compound into the carboxylic acid compound, which can optionally be extended with the base oil component, plus, if necessary, the complexing agent and, if necessary, simultaneous heating of the mixture to a temperature above 100 °C, especially above 170°C, to form a thickened grease product, cooling the grease product and optionally adding water, subjecting the mixture to shearing forces, e.g., with a toothed colloid mill, a high pressure homogenizer and/or a three-roll mill.
  • the thickener is synthesized in-situ in the base oil under pressure and at elevated temperature in a closed reaction vessel such as an autoclave.
  • the lubricating grease composition can be used to lubricate gears, constant velocity drive shafts, plain bearings and roller bearings, sliding guides, spindle drives, linear drives, ball screw drives, in particular with a lower operating temperature of less than -20° C. and/or in automobiles, airplanes, drones or helicopters. Further applications are the lubrication of steering systems, sunroofs, window regulators, side mirror adjusters, door locks, undercarriage wheel bearings, especially in automobiles, airplanes, drones or helicopters.
  • the lubricating grease composition is also suitable for lubricating electric motor bearings, in particular in hybrid vehicles or purely electric vehicles.
  • Lithium 12-hydroxyoctadecanoic acid grease with polyalphaolefin Lithium 12-hydroxyoctadecanoic acid grease with polyalphaolefin
  • the lubricating grease was then homogenized using a 3-roller mill and adjusted to the desired consistency by gradually adding more polyalphaolefin.
  • the lubricating grease produced in this way had a thickener content of 12.13% by weight and a worked penetration of 332 0.1 mm.
  • Lithium 10-hydroxyoctadecanoic acid greases with polyalphaolefin Lithium 10-hydroxyoctadecanoic acid greases with polyalphaolefin
  • the lubricating greases produced in this way had thickener proportions of 4.64% by weight (B1), 4.97% by weight (B2) and 5.06% by weight (B3) and worked penetrations of 339 0.1 mm (B1), 332 0. 1mm (B2) and 320 0.1mm (B3).
  • Lithium 12-hydroxyoctadecanoic acid complex grease with polyalphaolefin Lithium 12-hydroxyoctadecanoic acid complex grease with polyalphaolefin
  • the lubricating grease was homogenized with a 3-roller mill and adjusted to the desired consistency by gradually adding more polyalphaolefin.
  • the lubricating grease produced in this way had a thickener content of 10.52% and a worked penetration of 328 0.1 mm as well as a dropping point of >300°C.
  • Lithium R-10-hydroxyocatedecanoic acid grease with ester oil Lithium R-10-hydroxyocatedecanoic acid grease with ester oil
  • the lubricating greases according to the invention produced with R-10-hydroxyoctadecanoic acid showed a thickening effect which was up to 62% better than with 12-hydroxyoctadecanoic acid.

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

Claims (23)

  1. - Composition de graisse lubrifiante comportant :
    a) au moins une huile de base ;
    b) au moins un additif ;
    c) au moins un épaississant, ledit au moins un épaississant étant un savon métallique et/ou un savon complexe métallique, qui est constitué d'au moins un ion de métal alcalin et/ou alcalino-terreux et d'au moins un carboxylate formé à partir d'un acide gras en C16 à C18, l'acide gras en C16 à C18 comportant au moins de l'acide R-10-hydroxyoctadécanoïque et l'acide 10-hydroxyoctadécanoïque ayant une pureté énantiomérique par rapport à l'isomère R de plus de 80 % en poids ;
    l'acide gras en C16 à C18 se composant à plus de 50% en poids d'acide 10-hydroxyoctadécanoïque, et
    la composition contenant :
    a) 55 à 98 % en poids de l'huile de base ;
    b) 0,5 à 40 % en poids du/des additifs ; et
    c1) 1,5 à 25 % en poids du savon métallique, ou
    c2) 1,5 à 40 % en poids du savon complexe métallique comportant 0,1 à 20 % en poids d'agent complexant.
  2. - Composition de graisse lubrifiante selon la revendication 1, dans laquelle
    i. l'acide gras en C16 à C18 se compose à plus de 80 % en poids, et en particulier à plus de 95 % en poids, d'acide 10-hydroxyoctadécanoïque et/ou
    ii. l'acide 10-hydroxyoctadécanoïque a une pureté énantiomérique par rapport à l'isomère R de plus de 90 % en poids et en particulier de plus de 98 % en poids.
  3. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle l'acide gras en C16 à C18 contient de l'acide hexadécanoïque, en particulier plus de 0,5 % en poids, de préférence plus de 1,0 % en poids, et de façon particulièrement préférée 1 à 10 % en poids.
  4. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle l'acide gras en C16 à C18 contient de l'acide hydroxyhexadécanoïque, en particulier de l'acide 9-hydroxyhexadécanoïque, en particulier plus de 0,2 % en poids, de préférence plus de 0,5 % en poids, et de façon particulièrement préférée 1 à 10,0 % en poids.
  5. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle l'acide gras en C16 à C18 contient de l'acide octadécanoïque, en particulier plus de 0,2 % en poids, de préférence plus de 0,5 % en poids, et de façon particulièrement préférée 1 à 10,0 % en poids.
  6. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle l'acide gras en C16 à C18 contient de l'acide octadécénoïque, en particulier de l'acide (9Z)-octadéca-9-énoïque, en particulier plus de 0,2 % en poids, de préférence plus de 0,5 % en poids, et de façon particulièrement préférée 1,0 à 10 % en poids.
  7. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle l'acide gras en C16 à C18 contient de l'acide octadécadiénoIque, en particulier de l'acide (9Z,12Z)-octadéca-9,12-diénoïque, en particulier plus de 0,2 % en poids, de préférence plus de 0,5 % en poids, et de façon particulièrement préférée 1 à 10 % en poids.
  8. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle l'acide gras en C16 à C18 contient moins de 1 % en poids d'acide 12-hydroxy-9-octadécénoïque, en particulier d'acide (9Z, 12R)-12-hydroxy-9-octadécénoïque, de préférence moins de 0,2 % en poids.
  9. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle l'acide gras en C16 à C18 contient moins de 1 % en poids d'acide 12-hydroxyoctadécanoïque, en particulier moins de 0,2 % en poids.
  10. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle les acides gras en C16 à C18 contiennent des acides gras en C16 à C18 substitués par hydroxy, susceptibles d'être obtenus à partir d'une conversion enzymatique de l'acide gras en C16 à C18 insaturé correspondant.
  11. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle les acides gras en C16 à C18 sont susceptibles d'être obtenus à partir de graisses alimentaires, en particulier de graisses alimentaires usagées, ou de biodiesel, comportant au moins une conversion enzymatique.
  12. - Composition selon au moins l'une des revendications précédentes, dans laquelle le savon métallique ou le savon métallique complexe est
    - un savon au lithium ou un savon complexe au lithium ; ou
    - un savon au lithium/calcium ou un savon complexe au lithium/calcium.
  13. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle l'agent complexant est choisi parmi :
    - les sels alcalins et/ou alcalino-terreux
    a) d'un acide monocarboxylique saturé ou insaturé ou encore d'acides hydroxycarboxyliques ayant 2 à 8, en particulier 2 à 4 atomes de carbone ou
    b) d'un acide dicarboxylique ayant 2 à 16, en particulier 2 à 12 atomes de carbone, chacun éventuellement substitué ; et/ou
    - les sels alcalins ou alcalino-terreux de l'acide borique et/ou de l'acide phosphorique, en particulier les produits de réaction avec LiOH et/ou Ca(OH)2 ou le produit de réaction d'hydroxyde alcalin ou alcalino-terreux, en particulier LiOH et/ou Ca(OH)2, avec des esters de l'acide borique ou de l'acide phosphorique ; et/ou
    - les esters de l'acide borique et de l'acide phosphorique avec des groupes alkyle non ramifiés ou ramifiés, ayant 2 à 32 atomes de carbone, de préférence 8 à 32 atomes de carbone.
  14. - Composition selon au moins l'une des revendications précédentes, dans laquelle la composition comprend :
    a) 70 à 95 % en poids de l'huile de base ;
    b) 2 à 20 % en poids du/des additifs ; et
    c1) 3 à 10 % en poids du savon métallique ou
    c2) 1,5 à 40 % en poids du savon complexe métallique comportant 0,1 à 10 % en poids de l'agent complexant.
  15. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle la composition de graisse lubrifiante contient un autre savon métallique et/ou un autre savon complexe métallique d'acides monocarboxyliques saturés ou insaturés ou encore d'acides hydroxycarboxyliques ayant 10 à 15 et/ou 19 à 24 atomes de carbone, éventuellement incluant des agents complexants, les autres savons métalliques représentant de préférence moins de 50 % en poids du total des savons métalliques et/ou des savons complexes métalliques, en particulier de préférence moins de 20 % en poids.
  16. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle la composition de graisse lubrifiante contient en outre des co-épaississants choisis parmi un ou plusieurs membres du groupe : aluminosilicates, alumines, silice hydrophobe et hydrophile, polymères, di/poly-urées, di/poly-urée-uréthanes et PTFE.
  17. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle ladite composition présente une valeur de pénétration de cône (pénétrabilité travaillée) de 210 à 475 mm/10 (à 25°C), de préférence de 230 à 385 mm/10 (à 25°C), déterminée selon ISO 2137.
  18. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle l'huile de base présente une viscosité cinématique de 14 à 2500 mm2 /s, de préférence de 30 à 500 mm2 /s, à 40°C.
  19. - Composition de graisse lubrifiante selon au moins l'une des revendications précédentes, dans laquelle l'additif est choisi parmi un ou plusieurs membres du groupe suivant :
    - les anti-oxydants, comme les composés amines, les composés phénols, les antioxydants soufrés, le dithiocarbamate de zinc ou le dithiophosphate de zinc ;
    - les additifs haute pression, comme les composés organiques chlorés, le soufre, le phosphore ou le borate de calcium, le dithiophosphate de zinc, les composés organiques du bismuth ou du molybdène ;
    - les polyols en C2 à C6, les acides gras, les esters d'acides gras ou les huiles animales ou végétales ;
    - les agents anticorrosion, comme le sulfonate de pétrole, le naphtalène sulfonate de dinonyle ou les esters de sorbitan ;
    - les désactivateurs de métaux, comme le benzotriazole ou le nitrite de sodium ;
    - les agents améliorant la viscosité, comme le polyméthacrylate, le polyisobutylène, l'oligo-déc-l-ène et les polystyrènes ;
    - les additifs anti-usure, comme les di-alkyl-dithiocarbamates de molybdène ou les di-alkyl-dithiocarbamates de sulfure de molybdène, les amines aromatiques ;
    - les modificateurs de frottement (« Friction Modifier »), comme les polymères fonctionnels comme par exemple les oléylamides, les composés organiques à base de polyéther et d'amide ou le dithiocarbamate de molybdène, et
    - les lubrifiants solides, comme par exemple les poudres de polymère comme les polyamides, les polyimides ou le PTFE, le graphite, les oxydes métalliques, le nitrure de bore, les dérivés de lignine (par exemple les sulfonates de lignine, l'organosolvlignine), les sulfures métalliques comme par exemple le disulfure de molybdène, le disulfure de tungstène ou les sulfures mixtes à base de tungstène, de molybdène, de bismuth, d'étain et de zinc, les sels inorganiques des métaux alcalins et alcalino-terreux, comme par exemple le carbonate de calcium, les phosphates de sodium et de calcium.
  20. - Utilisation de la composition de graisse lubrifiante selon au moins l'une des revendications 1 à 19 pour la lubrification d'engrenages, d'arbres de transmission homocinétique, de paliers lisses et à roulement, de glissières, d'entraînements de broches, d'entraînements linéaires, d'entraînements à vis à billes, en particulier à chaque fois avec une température d'utilisation de moins de -20°C et/ou dans des automobiles, des avions, des drones ou des hélicoptères.
  21. - Utilisation de la composition de graisse lubrifiante selon au moins l'une des revendications 1 à 19 pour la lubrification de directions, de toits ouvrants, de lève-vitres, de mécanismes de réglage de rétroviseurs latéraux, de serrures de porte, de paliers de roues de trains d'atterrissage, en particulier dans des automobiles, des avions, des drones ou des hélicoptères.
  22. - Utilisation de la composition de graisse lubrifiante selon au moins l'une des revendications 1 à 19 pour la lubrification de paliers de moteurs électriques, en particulier dans des véhicules hybrides ou des véhicules purement électriques.
  23. - Procédé de fabrication d'une composition de graisse lubrifiante selon au moins l'une des revendications 1 à 19 par mise en contact de :
    a) au moins une huile de base ;
    b) au moins un additif ;
    c) au moins un épaississant, ledit au moins un épaississant étant un savon métallique ou un savon complexe métallique qui est constitué d'ions de métaux alcalins ou alcalino-terreux et d'un acide R-10-hydroxyoctadécanoïque, le savon métallique ou le savon complexe métallique étant, de préférence, préparé dans l'huile de base sous chauffage à au moins 170°C et l'additif étant en outre de préférence ajouté après le refroidissement à au-dessous de 100°C.
EP20725070.5A 2019-04-26 2020-04-24 Graisses de lubrification comprenant des savons métalliques et des complexes de savons métalliques à base d'acide r-10-hydroxyoctadécanoïque Active EP3959296B1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
RS20230042A RS63900B1 (sr) 2019-04-26 2020-04-24 Masti za podmazivanje koje sadrže sapune metala i sapune metalnih kompleksa na bazi r-10 hidroksioktadekanske kiseline
HRP20230066TT HRP20230066T1 (hr) 2019-04-26 2020-04-24 Masti za podmazivanje koje sadrže metalne sapune i kompleksne metalne sapune na bazi r-10-hidroksioktadekanoične kiseline

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102019110921.3A DE102019110921A1 (de) 2019-04-26 2019-04-26 Schmierfette umfassend Metallseifen und Metallkomplexseifen auf Basis von R-10-Hydroxyoctadecansäure
PCT/DE2020/100338 WO2020216417A1 (fr) 2019-04-26 2020-04-24 Graisses de lubrification comprenant des savons métalliques et des complexes de savons métalliques à base d'acide r-10-hydroxyoctadécanoïque

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DE102023112511B3 (de) 2023-05-11 2024-03-14 Tunap Gmbh & Co. Kg Festschmierstoffzusammensetzung und deren Verwendung, Verfahren zum Schmieren einer Kette

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CA2042196A1 (fr) * 1991-05-09 1992-11-10 Nicolas Samman Procede de preparation de metal alcalin et graisses a savon complexe a base de metal alcalino-terreux
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WO2008040383A1 (fr) 2006-10-07 2008-04-10 Gkn Driveline International Gmbh Composition de graisse pour liaisons homocinétiques fonctionnant à vitesse constante, c comprenant au moins un composé de molybdène tri-nucléaire et un épaississant dérivé de l'urée
WO2008119735A1 (fr) * 2007-04-02 2008-10-09 Georg-August-Universität Göttingen Procédé de fabrication d'acide gras hydroxy
DE102008034959A1 (de) * 2008-07-25 2010-01-28 Fuchs Petrolub Ag Calcium/Lithium-Komplexfette und gekapseltes Gleichlaufgelenk enthaltend diese sowie deren Anwendung
US9708521B2 (en) * 2010-03-08 2017-07-18 Georgetown University Systems and methods employing low molecular weight gelators for crude oil, petroleum product or chemical spill containment and remediation
EP2702122B1 (fr) * 2011-06-17 2021-09-01 Biosynthetic Technologies, LLC Compositions de graisses comprenant des huiles de base contenant des estolides
JP6717593B2 (ja) * 2015-12-10 2020-07-01 株式会社日立製作所 エレベーターロープ用グリース、エレベーターロープおよびトラクション式エレベーター
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KR102321759B1 (ko) * 2016-04-13 2021-11-05 디에스엠 아이피 어셋츠 비.브이. 10-하이드록시스테아르산 조성물
EP3461901A1 (fr) * 2017-09-29 2019-04-03 Technische Universität München Procédé pour la production enzymatique acellulaire d'acide 10-hydroxyoctadécanoïque à partir d'huiles d'origines biologiques et son utilisation dans une formulation lubrifiante

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DE102023112511B3 (de) 2023-05-11 2024-03-14 Tunap Gmbh & Co. Kg Festschmierstoffzusammensetzung und deren Verwendung, Verfahren zum Schmieren einer Kette

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HUE060842T2 (hu) 2023-04-28
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BR112021021093A2 (pt) 2021-12-14
RS63900B1 (sr) 2023-02-28
CN113748188B (zh) 2023-08-29
US11591537B2 (en) 2023-02-28
ES2934988T3 (es) 2023-02-28
AU2020263515A1 (en) 2021-12-23
HRP20230066T1 (hr) 2023-03-17
CA3134723A1 (fr) 2020-10-29
EP3959296A1 (fr) 2022-03-02
WO2020216417A1 (fr) 2020-10-29
PL3959296T3 (pl) 2023-04-03
CN113748188A (zh) 2021-12-03
JP2022530618A (ja) 2022-06-30
KR20220002920A (ko) 2022-01-07
US20220186135A1 (en) 2022-06-16
MX2021013093A (es) 2022-01-24

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