WO2023016908A1 - Utilisation d'esters d'acide hémimellitique en tant qu'huile de base pour des compositions lubrifiantes - Google Patents

Utilisation d'esters d'acide hémimellitique en tant qu'huile de base pour des compositions lubrifiantes Download PDF

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Publication number
WO2023016908A1
WO2023016908A1 PCT/EP2022/071929 EP2022071929W WO2023016908A1 WO 2023016908 A1 WO2023016908 A1 WO 2023016908A1 EP 2022071929 W EP2022071929 W EP 2022071929W WO 2023016908 A1 WO2023016908 A1 WO 2023016908A1
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Prior art keywords
weight
group
formula
lubricant composition
acid ester
Prior art date
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PCT/EP2022/071929
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German (de)
English (en)
Inventor
Stefan Seemeyer
Thomas Kilthau
Ling Ma
Nataliya Panagiotidou
Original Assignee
Klueber Lubrication Muenchen Se & Co. Kg
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Filing date
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Application filed by Klueber Lubrication Muenchen Se & Co. Kg filed Critical Klueber Lubrication Muenchen Se & Co. Kg
Priority to JP2024508629A priority Critical patent/JP2024529150A/ja
Priority to EP22764322.8A priority patent/EP4384589A1/fr
Priority to KR1020247006229A priority patent/KR20240038052A/ko
Priority to CN202280055477.2A priority patent/CN117940537A/zh
Priority to CA3227839A priority patent/CA3227839A1/fr
Priority to US18/682,523 priority patent/US20240343988A1/en
Priority to AU2022327545A priority patent/AU2022327545A1/en
Publication of WO2023016908A1 publication Critical patent/WO2023016908A1/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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/36—Esters of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C10M107/08—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing butene
    • 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
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • C10M2205/0265—Butene used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C10M2207/2825—Esters of (cyclo)aliphatic oolycarboxylic acids 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
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/285—Esters of aromatic polycarboxylic acids
    • C10M2207/2855—Esters of aromatic polycarboxylic acids 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
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C10M2207/2865—Esters of polymerised unsaturated acids 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
    • C10M2215/1026—Ureas; Semicarbazides; Allophanates used as thickening material
    • 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
    • C10N2030/02—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
    • C10N2030/10—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
    • C10N2030/26—Waterproofing or water resistance
    • 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
    • C10N2030/64—Environmental friendly 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/74—Noack Volatility
    • 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
    • C10N2030/76—Reduction of noise, shudder, or vibrations
    • 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

Definitions

  • Lubricants are essential components of many industrial processes where two or more surfaces move in close contact.
  • the range of applications for lubricating oils is very wide, including automotive lubricants, two-stroke and four-stroke petrol engine lubricants, diesel engine lubricants, gas engine oils, gas turbine oils, automatic transmission fluids, gear oils, etc.
  • Lubricants can be embodied as lubricating oils and lubricating greases.
  • Industrial lubricating oils include but are not limited to industrial gear oils, pneumatic tool lubricants, high temperature oils, air and gas compressor oils for all types of compressors, machine tool oils, textile oils, steam turbine oils, hydraulic fluids, paper machine oils, food machine oils, steam cylinder oils, metalworking fluids for metal cutting, metal rolling, metal drawing, metal forging and metal stamping.
  • lubricating greases also include one or more thickeners. With regard to the sustainability of lubricants, it is desirable if they contain at least a proportion of bio-based base oils.
  • a lubricant contains a base oil that can be obtained from both (at least in part) biological and petrochemical sources.
  • a high level of flexibility in lubricant production can be combined with the option of providing an environmentally friendly, sustainable lubricant.
  • bio-based oils are not suitable for lubricant applications because they do not have the desired property profile, for example in terms of oxidation stability and low-temperature behavior.
  • trimellitic acid ester as a base oil for lubricants is known and is used in practice. However, this ester is not currently produced on an industrial scale from biological raw materials.
  • WO2012159738 A1 discloses a high-temperature oil for lubricating chains, chain rollers and belts of continuous presses, comprising 40 to 91.9% by weight of a compound of the general formula (II) where R is a linear or branched alkyl group having a chain length of 8 to 16 carbon atoms and 5 to 50% by weight of a hydrogenated polyisobutylene, a fully hydrogenated polyisobutylene or a mixture of a fully hydrogenated and a hydrogenated polyisobutylene.
  • R is a linear or branched alkyl group having a chain length of 8 to 16 carbon atoms and 5 to 50% by weight of a hydrogenated polyisobutylene, a fully hydrogenated polyisobutylene or a mixture of a fully hydrogenated and a hydrogenated polyisobutylene.
  • the two-component system described has very good performance with regard to thermal stability and residue formation or residue behavior.
  • this ester is not currently produced on an industrial scale from biological
  • the object of the present invention is to provide a base oil for a lubricant composition that consists of both biological as well as from petrochemical sources. Furthermore, the resulting lubricant composition should have good oxidation stability, lubricating action and good low-temperature behavior. In addition, it should have a good lubricating effect over a long period of time even at a constantly high temperature. Furthermore, the lubricant composition should be able to be provided in different viscosities, depending on the desired application.
  • hemimellitic acid ester of the following general formula I where Ri , R2 and R3 are independently a) an unsubstituted, branched or unbranched C1 to C20 alkyl group or b) a C1 to C5 alkyl group having at least one substituent selected from the group consisting of cycloalkyl groups and aromatic groups has, or c) are a C5 to C20 aromatic group or a C5 to C20 cycloalkyl group, where the hemimellitic acid ester can be present as a mixture of different compounds of the formula I, dissolved as the base oil of a lubricant composition for lubricating tribological systems.
  • hemimellitic acid ester of the above formula I makes it possible to obtain a lubricant composition with good oxidation stability, lubricating action and good low-temperature behavior.
  • it also shows at a constantly high temperature over a long period of time Period good lubricating properties.
  • the lubricant composition can be provided in different viscosities, depending on the desired application. This was surprising because hemimellitic acid ester can be obtained from biological sources and bio-based lubricants, as explained above, usually do not have the desired range of properties in terms of oxidation stability, lubricating effect and low-temperature behavior.
  • hemimellitic acid ester starting from biomass is known and is described, for example, in US10562875B2.
  • the hemimellitic acid ester obtained can contain a high proportion of bio-based carbon or be completely bio-based.
  • hemimellitic acid ester can also be easily obtained from petroleum or petrochemical sources, which increases flexibility in lubricant production.
  • the hemimellitic acid ester is at least partially bio-based.
  • the hemimellitic acid ester is made, at least in part, from raw materials derived from biological sources and/or renewable agricultural materials (including plant, animal, and man-made materials) and not from petroleum or petrochemical sources.
  • biological sources are agriculture, forestry, plant breeding or animal raw materials.
  • Preferred biological sources are straw, animal waste products, agricultural and forestry waste.
  • hemimellitic acid ester can be present as the only base oil or in a mixture with other base oils.
  • a tribological system is understood to be a technical construction whose function is realized by mechanically moving structural elements that are subject to friction and wear. Tribological systems have the task of movements, energy and material transform, transport and make technically usable.
  • Preferred tribological systems are tribological systems that have metallic and/or non-metallic materials, such as roller and plain bearings, in particular roller and plain bearings in automotive engineering, conveyor technology, mechanical engineering and/or office technology, gears, chains, sliding guides and Joints, in particular wheel bearings in motor vehicles, bearings in wind turbines, in particular rotor bearings, in wind turbines and/or rotating plain bearings, for example fan bearings, or linearly guided plain bearings and/or ball joints, especially ball joints for use in the automotive sector.
  • Possible tribological systems also include sliding partners in industrial plants and machines, but also in the areas of household machines, entertainment electronics, especially in oil-lubricated systems, lubrication of chains, chain rollers and steel belts of continuous wood presses.
  • the tribological systems have surfaces that contain metallic and/or non-metallic materials, preferably composite materials, aluminum, aluminum alloys, steel, stainless steel and cast materials, non-ferrous metals, plastics, fiber-reinforced plastics and/or polymers.
  • the lubricant composition has at least 10% by weight, for example from 10 to 100% by weight and/or 10 to 95% by weight, preferably at least 15% by weight, for example from 15% by weight to 95% by weight. %, in particular at least 20% by weight, for example from 20% by weight to 95% by weight, of bio-based carbon based on the total weight of organic carbon in the lubricant composition.
  • the content of bio-based carbon can be determined using the ASTM International Radioisotope Standard Method D 6866. The latest version of the standard on the filing date applies.
  • This method determines the bio-based content of a material based on the amount of bio-based carbon in the material as a percentage of the weight of the total organic carbon in the material under study. The method is based on the fact that bio-based products have carbon isotope ratios of 13C/12C and 14C/12C, which are different from those found in petroleum-derived materials.
  • the hemimellitic acid ester of the formula I has at least 30% by weight, for example from 30 to 100% by weight, preferably at least 40% by weight, for example from 40% by weight to 100% by weight, in particular at least 50 % by weight, for example from 50% by weight to 100% by weight of bio-based carbon, based on the total weight of the hemimellitic acid ester of the formula I, in the lubricant composition, in each case measured using the ASTM International Radioisotope Standard Method D 6866. The latest on the filing date applies version of the standard.
  • the acid component of the hemimellitic acid ester of the formula I has at least 30% by weight, for example from 30 to 100% by weight, preferably at least 40% by weight, for example from 40% by weight to 100% by weight, in particular at least 50% by weight, for example from 50% by weight to 100% by weight, bio-based carbon based on the total weight of the acid component of the hemimellitic acid ester of the formula I in the lubricant composition, in each case measured using the ASTM International Radioisotope Standard Method D 6866. The applies latest version of the standard on the filing date.
  • At least one radical Ri, R2 and/or R3 is an unsubstituted, branched or unbranched C1 to C20 alkyl group, more preferably a C5 to C20 alkyl group, more preferably a C6 to C18 alkyl group, and in particular a C8 to C18 alkyl group.
  • at least one R 1 , R 2 and/or R 3 radical is selected from the group consisting of octanyl, ethylhexanyl, nonanyl, decanyl, undecanyl and dodecanyl.
  • At least one R 1 , R 2 and/or R 3 radical is selected from the group consisting of octanyl, 2-ethylhexan-1-yl, 1-nonanyl, decanyl, 1-undecanyl, 1-dodecanyl.
  • At least one radical Ri, R2 and/or Rs is a C1 - to C5-alkyl group, preferably a C1 - to C3-alkyl group, more preferably a C1 - to C2-alkyl group, and in particular a C1 - Alkyl group each having at least one substituent selected from the group consisting of cycloalkyl groups and aromatic groups.
  • the number of carbon atoms in the alkyl group mentioned does not include the number of carbon atoms in the substituents.
  • cycloalkyl groups include both monocyclic and polycyclic compounds.
  • the substituents independently have from 5 to 19 carbon atoms, more preferably from 5 to 17 carbon atoms, and most preferably from 5 to 15 carbon atoms. More preferably, the substituents are independently selected from C5 to C19 cycloalkyl groups, or C5 to C19 aromatic groups, more preferably from C5 to C17 cycloalkyl groups or C5 to C17 aromatic groups, and especially from C5 to C15 cycloalkyl groups or C5 to C15 aromatic groups.
  • At least one radical Ri, R2 and/or Rs is a C5 to C20 aromatic group or a C5 to C20 cycloalkyl group.
  • At least one R 1 , R 2 and/or R 3 radical is preferably selected from phenyl, cyclopentyl, cyclohexyl, naphthyl, isotridecyl, tricyclodecanemethyl and furfuryl.
  • At least one radical R1, R2 and/or R3, preferably at least two radicals R1, R2 and/or R3, and in particular all radicals R1, R2 and R3 are selected from the group consisting of octanyl, ethylhexanyl, nonanyl, decanyl, undecanyl, dodecanyl, isotridecyl, tricyclodecanemethyl, furfuryl.
  • At least one radical Ri, R2 and/or R3, preferably at least two radicals Ri, R2 and/or R3, and in particular all radicals Ri, R2 and R3 are selected from the group consisting of octanyl, 2-ethylhexan-1-yl, 1-nonanyl, decanyl, 1-undecanyl, 1-dodecanyl, isotridecyl, tricyclodecanemethyl, furfuryl.
  • radicals Ri, R2 and R3 can be the same or different.
  • the hemimellitic ester of the formula I has R 1 , R 2 and R 3 radicals which are at least partly different from one another.
  • the hemimellitic acid ester of the formula I is also preferably a mixture of different compounds of the formula I.
  • the radicals R1, R2 and R3 independently of one another have no atoms other than carbon and hydrogen.
  • the lubricant composition contains the hemimellitic acid ester of the formula I in an amount of from 20% to 90% by weight, more preferably from 25% to 70% by weight, even more preferably from 25% to 60% by weight % by weight and in particular from 30% by weight to 50% by weight, in each case based on the total weight of the lubricant composition.
  • the hemimellitic ester of the formula I has a kinematic viscosity at 40° C. [mm 2 /sec] in the range from 30 mm 2 /s to 150 mm 2 /s, preferably from 30 mm 2 /s to 100 mm 2 /s, more preferably from 50 mm 2 /s to 150 mm 2 /s and in particular 50 mm 2 /s to 90 mm 2 /s.
  • the lubricant composition is present as a grease formulation and the hemimellitic ester of the formula I and/or a mixture of hemimellitic ester of the formula I and other base oils has a kinematic viscosity at 40° C. [mmVsec] in the range of 80 mm 2 / s to 460 mm 2 /s, preferably from 100 mm 2 /s to 320 mm 2 /s.
  • the lubricant composition contains 5 to 50% by weight, more preferably from 15 to 35% by weight and in particular from 15 to 30% by weight, polyisobutylene, based in each case on the total weight of the lubricant composition.
  • polyisobutylene is that it can be used to adjust the viscosity of the lubricant composition in a particularly simple manner.
  • a particularly good residue behavior can be achieved after complete evaporation.
  • the polyisobutylene has a number-average molecular weight of 115 to 15,000 g/mol, preferably 160 to 5,000 g/mol, measured according to DIN 55672-1:2016-03 (gel permeation chromatography (GPC) - part 1: tetrahydrofuran (THF ) as eluent).
  • GPC gel permeation chromatography
  • the lubricant composition can be present both as a fat formulation and as an oil formulation.
  • the lubricating composition When the lubricating composition is in the form of a grease formulation, it contains a thickening agent. Consequently, in a preferred embodiment of the invention, the lubricant composition contains from 3 to 30% by weight of thickener.
  • the thickening agent is preferably a reaction product of a diisocyanate, preferably 2,4-diisocyanatotoluene, 2,6-diisocyanatotoluene, 4,4-diisocyanatodiphenylmethane, 2,4'-diisocyanatophenylmethane, 4,4'-diisocyanatodiphenyl, 4,4 '-Diisocyanato-3,3'-dimethylphenyl, 4,4-diisocyanato-3,3'-dimethylphenylmethane, which can be used individually or in combination, with an amine of the general formula R'2-N-R, or a diamine of the general formula Formula R'2-N-R-NR'2 where R is aryl, alkyl or alkylene having from 2 to 22 carbon atoms and R' is identical or different hydrogen, alkyl, alkylene or aryl, or with mixtures of amines and di
  • the thickener is selected from Al complex soaps, metal simple soaps of the elements of the first and second main group of the periodic table, metal complex soaps of the elements of the first and second main group of the periodic table, bentonites, sulfonates, silicates, aerosil, polyimides or PTFE or a mixture of the aforementioned thickeners.
  • the lubricant composition can also contain at least one other base oil.
  • the proportion of the additional base oil is preferably from 10% by weight to 50% by weight, more preferably from 10% by weight to 40% by weight, more preferably from 20% by weight .% to 40% by weight and in particular from 25% by weight to 40% by weight, based in each case on the total weight of the lubricant composition.
  • the lubricant composition is in the form of a grease formulation and contains at least one additional base oil
  • the proportion of the additional base oil is preferably from 10% by weight to 50% by weight, more preferably from 25% by weight to 50% by weight and in particular from 30% by weight. % to 50% by weight, based in each case on the total weight of the lubricant composition.
  • the lubricant composition contains at least one other base oil
  • the lubricant composition preferably contains the hemimellitic acid ester of the formula I in an amount of from 20% by weight to 70% by weight, more preferably from 25% by weight to 70% by weight, even more preferably from 25% by weight .% to 60% by weight and in particular from 30% by weight to 50% by weight, based in each case on the total weight of the lubricant composition.
  • base oils are customary lubricating oils that are liquid at room temperature (20° C.).
  • the further base oil preferably has a kinematic viscosity of 18 mm 2 /s to 20000 mm 2 /s, in particular 30 mm 2 /s to 400 mm 2 /s at 40°C.
  • base oils a distinction is made between mineral and synthetic oils.
  • base oil are meant the usual base fluids used in the manufacture of lubricants, particularly oils belonging to Groups I, II, II+, III, IV or V according to the American Petroleum Institute (API) classification [NLGI Spokesman, N. Samman, Volume 70, Number 11, p.14ff] can be assigned to understand. Mineral oils are after classified by the API Group.
  • Synthetic oils which may be mentioned are polyethers, esters, polyesters, preferably polyalphaolefins, in particular metallocene polyalphaolefins, perfluoropolyalkyl ethers (PFPAE), alkylated naphthalenes, silicone oils and alkylaromatics and mixtures thereof.
  • the polyether compound can have free hydroxyl groups, but can also be fully etherified or end groups esterified and/or made from a starting compound with one or more hydroxyl and/or carboxyl groups (-COOH).
  • Polyphenyl ethers, optionally alkylated are also possible as sole components or, even better, as mixed components.
  • Silicone oils, native oils and derivatives of native oils are also suitable.
  • esters which are particularly preferred according to the invention are esters, in particular esters of an aromatic and/or aliphatic di-, tri- or tetracarboxylic acid with one or a mixture of C7 to C22 Alcohols, esters of trimethylolpropane, pentaerythritol or dipentaerythritol with aliphatic C7 to C22 carboxylic acids, esters of C18 dimer acids with C7 to C22 alcohols, complex esters, as individual components or in any mixture, as well as triglycerides and/or estolides, polyalphaolefins, polyethers and /or mineral oils.
  • esters in particular esters of an aromatic and/or aliphatic di-, tri- or tetracarboxylic acid with one or a mixture of C7 to C22 Alcohols, esters of trimethylolpropane, pentaerythritol or dipentaerythritol with aliphatic C7 to C
  • the lubricant composition can contain inorganic or organic solid lubricants, preferably in a proportion of 0.1% by weight to 5% by weight, preferably 0.1% by weight to 3% by weight, based on the total weight of the lubricant composition.
  • Solid lubricants are preferably selected from PTFE, BN, pyrophosphate, Zn oxide, Mg oxide, pyrophosphate, thiosulfate, Mg carbonate, Ca carbonate, Ca stearate, Zn sulfide, Mo sulfide, W sulfide, Sn Sulfide, Graphite, Graphene, Nano-Tubes, SiO2 modifications or a mixture thereof.
  • the lubricant composition contains 0.1 to 8% by weight of additives selected from the group consisting of anti-corrosion additives, antioxidants, anti-wear additives, metal deactivators, ion complexing agents and/or UV stabilizers.
  • antioxidants are the following compounds: styrenated diphenylamines, diaromatic amines, phenolic resins, thiophenolic resins, phosphites, butylated hydroxytoluene, butylated hydroxyanisole, phenyl-alpha-naphthylamine, phenyl-beta-naphthylamine, octylated/butylated diphenylamine, di-alpha-tocopherol , di-tert-butyl-phenyl, benzenepropanoic acid, sulphur-containing phenolic compounds and mixtures of these components.
  • antioxidants are compounds containing sulfur, nitrogen and/or phosphorus in the molecule.
  • Preferred compounds containing sulfur, nitrogen and/or phosphorus in the molecule are selected from the group consisting of aromatic amines
  • Antioxidants such as alkylated phenyl-alpha-naphthylamine, dialkyldiphenylamine, sterically hindered phenols such as butylated hydroxytoluene (BHT), phenolic antioxidants with thioether groups, Zn- or Mo- or W-dialkyldithiophosphates and phosphites.
  • Preferred anti-corrosion additives, metal deactivators and/or ion complexing agents are triazoles, imidazolines, N-methylglycine (sarcosine), benzotriazole derivatives, N,N-bis(2-ethylhexyl)-ar-methyl-1H-benzotriazole-1-methanamine; n-Methyl-N(1-oxo-9-octadecenyl)glycine, mixture of phosphoric acid and mono- and diisooctyl ester reacted with (C11-14)-alkylamines, mixture of phosphoric acid and mono- and diisooctyl ester reacted with tert-alkylamine and primary ( C12-14) amines, dodecanoic acid, triphenyl phosphorothioate and amine phosphates and mixtures thereof.
  • IRGAMET® 39 IRGACOR® DSS G, Amine O; SARKOSYL® O (Ciba), COBRATEC® 122, CUVAN® 303, VANLUBE® 9123, CI-426, CI-426EP, CI-429 and CI-498.
  • Anti-wear additives preferred according to the invention are amines, amine phosphates, phosphates, thiophosphates, phosphorothioates and mixtures of these components.
  • Preferred anti-wear additives are selected from the group consisting of anti-wear additives based on diphenyl cresyl phosphate, amine neutralized phosphates, alkylated and non-alkylated triaryl phosphates, alkylated and non-alkylated triaryl thiophosphates, zinc or Mo or W dialkyl dithiophosphates, carbamates, thiocarbamates, zinc or mo or W-dithiocarbamates, dimercapto-thiadiazole, calcium sulfonates and benzotriazole derivatives.
  • anti-wear additives include IRGALUBE® TPPT, IRGALUBE® 232, IRGALUBE® 349, IRGALUBE® 211 and ADDITIN® RC3760 Liq 3960, FIRC-SHUN® FG 1505 and FG 1506, NA-LUBE® KR-015FG, LUBEBOND®, FLUORO ® FG, SYNALOX® 40-D, ACHESON® FGA 1820 and ACHESON® FGA 1810.
  • Another object of the invention is a lubricant composition designed as an oil formulation comprising:
  • Ri , F and R3 are independently a) a branched or unbranched C1 to C20 alkyl group or b) a C1 to C5 alkyl group having at least one substituent selected from the group consisting of cycloalkyl groups and aromatic groups , or c) a C5 to C20 aromatic group or a C5 to C20 cycloalkyl group, wherein the hemimellitic ester of the formula I as a mixture of different
  • the lubricant composition designed as an oil formulation additionally has 10% by weight to 45% by weight, preferably 30% by weight to 45% by weight, of at least one further base oil.
  • Another object of the invention is a lubricant composition designed as a grease formulation comprising: - 20% to 90% by weight, preferably 30% to 90% by weight, more preferably 40% to 90% by weight, of hemimellitic acid esters of the following general formula I where Ri , R2 and R3 are independently a) a branched or unbranched C1 to C20 alkyl group or b) a C1 to C5 alkyl group having at least one substituent selected from the group consisting of cycloalkyl groups and aromatic groups , or c) a C5 to C20 aromatic group or a C5 to C20 cycloalkyl group, wherein the hemimellitic ester of the formula I as a mixture of different
  • Another object of the invention is a lubricant composition designed as a grease formulation comprising:
  • hemimellitic acid esters of the following general formula I where Ri, R2 and R3 are independent of each other d) a branched or unbranched C1 to C20 alkyl group or e) a C1 to C5 alkyl group having at least one substituent selected from the group consisting of cycloalkyl groups and aromatic groups, or f) a C5 to C20 aromatic group or a C5 to C20 cycloalkyl group, where the hemimellitic acid ester of the formula I can be present as a mixture of different compounds of the formula I, as a base oil,
  • the lubricant composition designed as a grease formulation contains 10% by weight to 40% by weight of polyisobutylene.
  • the lubricant composition designed as a grease formulation has 0.1% by weight to 5% by weight of inorganic or organic solid lubricants.
  • Preferred components of the lubricant compositions according to the invention are those mentioned in relation to the use according to the invention.
  • particularly preferred thickeners for the lubricant composition designed as a grease formulation are a reaction product of a diisocyanate, preferably 2,4-diisocyanatotoluene, 2,6-diisocyanatotoluene, 4,4'-diisocyanatodiphenylmethane, 2,4'-
  • diisocyanatophenylmethane 4,4'-diisocyanatodiphenyl, 4,4'-diisocyanato-3,3'-dimethylphenyl, 4,4'-diisocyanato-3,3'-dimethylphenylmethane, which can be used individually or in combination, with an amine of the general formula R'2-NR, or a diamine of the general formula R'2-NR-NR'2, where R is an aryl, alkyl or alkylene radical having from 2 to 22 carbon atoms and R' is identical or different a hydrogen, alkyl, alkylene or aryl radical, or with mixtures of amines and diamines.
  • the thickener is selected from Al complex soaps, metal simple soaps of the elements of the first and second main group of the periodic table, metal complex soaps of the elements of the first and second main group of the periodic table, bentonites, sulfonates, silicates, aerosil, polyimides or PTFE or a mixture of the aforementioned thickeners.
  • esters particularly preferred other base oils for the lubricant compositions according to the invention designed as a grease formulation or as an oil formulation are esters, in particular esters of an aromatic and/or aliphatic di-, tri- or tetracarboxylic acid with one or a mixture of C7 to C22 alcohols, esters of trimethylolpropane, Pentaerythritol or dipentaerythritol with aliphatic C7 to C22 carboxylic acids, esters of C18 dimer acids with C7 to C22 alcohols, complex esters, as individual components or in any mixture, as well as triglycerides and/or estolides, polyalphaolefins, polyethers and/or mineral oils.
  • esters in particular esters of an aromatic and/or aliphatic di-, tri- or tetracarboxylic acid with one or a mixture of C7 to C22 alcohols, esters of trimethylolpropane, Pentaerythritol
  • FIG. 2 shows the average friction of several lubricant compositions containing hemimellitic acid esters of the formula I according to the invention compared to lubricant compositions containing trimellitic acid esters as a function of temperature, determined by means of SRV. measurement methods
  • the viscosity measurement is carried out with DIN 51562 (2016) using a Stabinger viscometer SVM 3000 (Anton Paar).
  • the bio-based carbon content is determined using the ASTM International Radioisotope Standard Method D 6866 in the version valid on the filing date.
  • the hemimellitic acid ester 1 is prepared via the following reaction:
  • a mixture of 150 g organic. Hemimellitic acid, 353.2 g 2-ethylhexan-1-ol and 40 mL xylene in a 1 L three-necked flask combined with a water separator is refluxed at 1 atm. Within 8 hours the internal temperature rises from 124°C to 210°C and 0.025 g of tetraisopropyl orthotitanate (0.005 wt%) is added at an internal temperature of 145°C. The clear reaction mixture is then refluxed at 210° C. for 5.5 h. A total of 39.1 g of water is continuously distilled off. The xylene and the excess Alcohol is distilled off under reduced pressure (tinn. 205° C., 16 mbar). The product (404.4 g) is obtained as a light yellow oil.
  • the basic data of the lubricant compositions are shown in Table 2. Tab.2 It is found that the lubricant composition 2 according to the invention based on hemimellitic ester shows comparable basic data as the comparison composition 1 based on trimellitic ester. The different viscosities observed can be explained by the different initial viscosities of the base oils used.
  • Example 7 Determination of the oxidation stability of the lubricant compositions from example 6
  • oxidation stability and the evaporation loss of the lubricant compositions from example 6 are determined by means of differential scanning calorimetry in accordance with DIN 51007 (04.2019) and thermogravimetric analysis in accordance with DIN 51006 (07.2005). The results are shown in Table 3.
  • Example 6 The lubricant compositions from Example 6 are examined with regard to their evaporation behavior and the increase in their apparently dynamic viscosity under thermal stress.
  • the evaporation behavior and the change in the apparently dynamic viscosity [mPas] as a criterion for progressive oxidation under thermal stress are determined as a comparative measurement.
  • the sample quantity is 5 g (+/- 0.1 g) per test. After 72 hours of storage in an aluminum dish at 230°C in a convection oven, the samples are compared with one another.
  • the residue behavior after complete evaporation is determined using the Eisenmann test (250°C / 72h).
  • the sample to be tested is weighed out with 5 g on a steel sheet that has previously been bent and cleaned with solvent and then evaporated at 250 °C in a circulating air drying cabinet for at least 72 hours.
  • the square sheet metal is manually bent on all four sides to create a bowl shape. After cooling, the results of the backweigh are documented.
  • Essential for this test is the determination of the solubility of the residue with fresh oil and the amount of residue formed. For this purpose, a drop of the fresh oil is applied to the residue and gently rubbed in using a rounded glass rod in circular movements.
  • Lubricant compositions 2 according to the invention based on hemimellitic ester show comparably good or better evaporation behavior and an even smaller increase in dynamic viscosity after 72 hours at 230° C. than comparative composition 1 based on trimellitic ester.
  • the lubricant composition according to the invention forms fewer residues. All residues can be easily dissolved with fresh oil.
  • Example 9 Measurement of the frictional wear of the lubricant compositions from example 6
  • the lubricant compositions from Example 6 are examined to measure the fretting using an oscillating fretting wear test (SRV).
  • SRV oscillating fretting wear test
  • the coefficient of friction can be examined with the SRV.
  • the SRV is standardized in DIN 51 834.
  • the lubricant compositions examined are measured in accordance with DIN 51 834 at 250N load, 50Hz, 165 min in a temperature step run (50 to 250°C). A steel ball is moved in an oscillating manner against a fixed steel disc on the front side. This allows the effect, resilience and service life of the lubricant compositions to be determined in oscillating movements under mixed friction conditions.
  • lubricant compositions according to the invention based on hemimellitic ester exhibit a coefficient of friction that is comparably good to comparison composition 1 based on trimellitic ester.
  • the fat formulation 3 according to the invention based on hemimellitic acid ester and the comparison fat formulation 4 based on trimellitic acid ester are formulated with the compositions shown in the table below.
  • Example 4 Table 6a is used as the hemellitic ester and TMA ester 4', Table 6a, as the trimellitic ester.
  • Both fat formulation 3 and comparison fat formulation 4 show comparably good flexing stability and shear stability.
  • the water resistance, oil separation, noise ratio and water content of all formulations are on the same level.

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

Abstract

L'invention concerne l'utilisation d'esters d'acide hémimelitique de formule générale : (I), dans laquelle R1, R2 et R3 représentent indépendamment les uns des autres a) un groupe alkyle en C1-C20 non substitué, ramifié ou non ramifié ou b) un groupe alkyle en C1-C5 qui comporte au moins un substituant sélectionné dans le groupe constitué de groupes cycloalkyle et de groupes aromatiques, ou c) un groupe aromatique en C5-C20 ou un groupe cycloalkyle en C5-C20, l'ester d'acide hémimelitique de formule (I) pouvant se présenter sous la forme d'un mélange de différents composés de formule (I), en tant qu'huile de base d'une composition lubrifiante pour la lubrification de systèmes tribologiques.
PCT/EP2022/071929 2021-08-12 2022-08-04 Utilisation d'esters d'acide hémimellitique en tant qu'huile de base pour des compositions lubrifiantes WO2023016908A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
JP2024508629A JP2024529150A (ja) 2021-08-12 2022-08-04 潤滑剤組成物の基油としてのヘミメリット酸エステルの使用
EP22764322.8A EP4384589A1 (fr) 2021-08-12 2022-08-04 Utilisation d'esters d'acide hémimellitique en tant qu'huile de base pour des compositions lubrifiantes
KR1020247006229A KR20240038052A (ko) 2021-08-12 2022-08-04 윤활제 조성물들의 기유로서 헤미멜리트산 에스테르의 용도
CN202280055477.2A CN117940537A (zh) 2021-08-12 2022-08-04 半苯三酸酯作为润滑剂组合物的基础油的用途
CA3227839A CA3227839A1 (fr) 2021-08-12 2022-08-04 Utilisation d'esters d'acide hemimellitique en tant qu'huile de base pour des compositions lubrifiantes
US18/682,523 US20240343988A1 (en) 2021-08-12 2022-08-04 Use of hemimellitic acid ester as a base oil for lubricant compositions
AU2022327545A AU2022327545A1 (en) 2021-08-12 2022-08-04 Use of hemimellitic ester as a base oil for lubricant compositions

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DE102021121037 2021-08-12

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2356631A1 (de) * 1972-11-13 1974-05-16 Tenneco Chem Schmiermittelgemisch
GB1549254A (en) * 1975-11-05 1979-08-01 Lochner K Damping composition
EP0059936A1 (fr) * 1981-03-03 1982-09-15 Schiedel GmbH & Co. Agent d'amortissement pâteux, procédés pour sa préparation et son utilisation
WO2006014950A2 (fr) * 2004-07-27 2006-02-09 The Lubrizol Corporation Compositions lubrifiantes contenant un ester d'un agent d'acylation polycarboxylique
US20100323934A1 (en) * 2006-12-28 2010-12-23 Shinya Kondo Grease composition for constant velocity joint and constant velocity joint
WO2012159738A1 (fr) 2011-05-26 2012-11-29 Klüber Lubrication München Se & Co. Kg Huile haute température

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2356631A1 (de) * 1972-11-13 1974-05-16 Tenneco Chem Schmiermittelgemisch
GB1549254A (en) * 1975-11-05 1979-08-01 Lochner K Damping composition
EP0059936A1 (fr) * 1981-03-03 1982-09-15 Schiedel GmbH & Co. Agent d'amortissement pâteux, procédés pour sa préparation et son utilisation
WO2006014950A2 (fr) * 2004-07-27 2006-02-09 The Lubrizol Corporation Compositions lubrifiantes contenant un ester d'un agent d'acylation polycarboxylique
US20100323934A1 (en) * 2006-12-28 2010-12-23 Shinya Kondo Grease composition for constant velocity joint and constant velocity joint
WO2012159738A1 (fr) 2011-05-26 2012-11-29 Klüber Lubrication München Se & Co. Kg Huile haute température

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NLGI SPOKESMANN. SAMMAN, PETROLEUM INSTITUTE (API, vol. 70, no. 11, pages 14ff

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KR20240038052A (ko) 2024-03-22
CN117940537A (zh) 2024-04-26
CA3227839A1 (fr) 2023-02-16
JP2024529150A (ja) 2024-08-01
AU2022327545A1 (en) 2024-03-28
EP4384589A1 (fr) 2024-06-19

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