EP3344734B1 - Mélange à action lubrifiante contenant des glycérides - Google Patents

Mélange à action lubrifiante contenant des glycérides Download PDF

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Publication number
EP3344734B1
EP3344734B1 EP16754476.6A EP16754476A EP3344734B1 EP 3344734 B1 EP3344734 B1 EP 3344734B1 EP 16754476 A EP16754476 A EP 16754476A EP 3344734 B1 EP3344734 B1 EP 3344734B1
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EP
European Patent Office
Prior art keywords
lubricating
mixture
glycerides
mixture according
mass fraction
Prior art date
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EP16754476.6A
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German (de)
English (en)
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EP3344734A1 (fr
Inventor
Peter Eisner
Thomas HERFELLNER
Andreas STÄBLER
Andreas Malberg
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Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
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Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • 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
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C10M2207/2815—Esters of (cyclo)aliphatic monocarboxylic 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
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C10M2207/2895—Partial esters containing free hydroxy groups 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
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/401—Fatty vegetable or animal oils used as base 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—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
    • C10N2040/25—Internal-combustion engines

Definitions

  • the invention relates to a lubricating mixture which contains at least a proportion by mass of ⁇ 50% of glycerides of natural origin and a proportion of fatty acid alkyl esters and is particularly suitable for use in gears, electric motors or internal combustion engines.
  • lubricating liquids made from mineral oils, synthetic oils, vegetable oils or water, to which additives are usually added to improve the lubricating properties.
  • the task of the liquids is to generate a liquid film on the surface of components, thereby reducing friction losses between components that move against one another and minimizing wear.
  • natural raw materials are increasingly being used, which are often modified before being used as a lubricant (e.g. cellulose in the DE202009018507U1 ) and/or additives can be added.
  • Very high demands are placed on gear or engine oils in the lubricant sector in particular, since they should be chemically stable over a long period of time and are often exposed to high temperature fluctuations, which can affect the lubricating properties. Those high In many cases, requirements cannot be met by either synthetic or natural fats and oils.
  • viscosity index describes the temperature dependency of the kinematic viscosity of a lubricating oil. Oils with a low viscosity index show a greater change in viscosity with temperature than those with a high viscosity index. The latter are particularly desirable in lubricating applications.
  • Vegetable oils are an environmentally friendly alternative to products based on Petroleum based and based on renewable natural resources.
  • the use of vegetable oils as lubricants is limited by the property of some oils to solidify at low temperatures, due to a low viscosity index and because of the often lacking oxidative stability.
  • EP2350240A1 describes the use of vegetable oil with a high proportion of unsaturated fatty acids as gear oil or hydraulic fluid to improve the viscosity properties, the oil having a natural viscosity index (VI) of greater than or equal to 200 and a proportion of monounsaturated fatty acids of greater than 80%, a proportion twice unsaturated fatty acids of a maximum of 1-10% and a proportion of triunsaturated fatty acids of less than 1%.
  • a part of the vegetable oil can be used in the form of an unsaturated ester of the vegetable oil.
  • gear oils or hydraulic oils should be thin at low temperatures ( ⁇ 40°C) in order to be easier to pump, which is achieved by using vegetable oil such as rapeseed or sunflower oil with a high proportion of unsaturated fatty acids.
  • vegetable oil such as rapeseed or sunflower oil with a high proportion of unsaturated fatty acids.
  • the occurrence of a solid phase in the lubricating medium should be avoided according to the description.
  • Industrial oils should also exhibit high oxidative stability, which is generally related to the unsaturated fatty acids present in vegetable fatty acid alkyl chains.
  • the reaction of a vegetable oil with oxygen can lead to polymerization and crosslinking of the fatty acid alkyl chains and reduced oxidative stability.
  • Oils based on saturated hydrocarbons contain little or no unsaturated fatty acids and therefore have high oxidative stability.
  • DE60031505T2 describes a method for increasing the oxidative stability and improving the lubricating properties of a vegetable oil.
  • the vegetable oil is transesterified with a short-chain fatty acid ester and volatile components are separated after transesterification.
  • the vegetable oil can have a monounsaturated fatty acid content of at least 50% and can be selected, for example, from the group consisting of corn oil, rapeseed oil, soybean oil and sunflower oil.
  • the short chain fatty acid ester can be saturated and is four to 10 carbon atoms in length. This type of transesterification with different synthetic components is an expensive process and therefore has economic disadvantages.
  • Hydraulic oils based on mineral oil are known. These usually have a viscosity index of around 100. Additives are added to the mineral oil to ensure protection against corrosion and increase its resistance to aging.
  • viscosity index improvers are added. These are long-chain synthetic hydrocarbon compounds that are homogeneously distributed in cold oils and only slightly increase viscosity, but unfold at higher operating temperatures and increase in volume when dissolved in the oil. This thickens the oil and increases the viscosity index.
  • Such viscosity index improvers have the disadvantage, however, that the long-chain hydrocarbon compounds are broken down into smaller fragments under stress, as a result of which their original thickening effect is sometimes significantly altered. This effect is also known as permanent shear loss.
  • a lubricant based on fatty acid esters is described.
  • vegetable or animal fats are transesterified with monohydric alcohols, which have a chain length of between three and six carbon atoms.
  • glycerol is a by-product and is separated because it is insoluble in the fatty acid alkyl esters.
  • the Indian DE20305164U1 The lubricant described therefore contains no glycerides.
  • the lubricant consists of natural or synthetic triglycerides, one organic solvent and an antioxidant. Lactic acid ethyl ester (ethyl lactate), mineral oils and mixtures of both are suggested as solvents.
  • fatty acid methyl esters from soybean oil can optionally be added.
  • partial glycerides is not described. Since this lubricant is explicitly a penetrating oil, i.e. a medium with low viscosity and good penetration properties, a solids content is undesirable.
  • a lubricant consisting of palm oil and palm oil by-products.
  • Base fluid for this lubricating medium is palm olein, a liquid fraction of palm oil.
  • the iodine value of the palm olein used must be at least 56 in order to avoid the formation of fat crystals.
  • Other lubricant components are tocopherols from palm oil and fatty acid alkyl esters. The latter are synthesized from free fatty acids and hindered polyhydric alcohols. Neopentyl glycol, trimethylolpropane, pentaerythritol and dipentylerythritol are used as hindered alcohols. Thus, the resulting esters are not mono- and diglycerides. Due to the use of palm olein, the lubricant has no solid fraction.
  • WO 2010/118891 A1 describes a lubricating fluid and a method for its production. This is a mixture of mono-, di- and triacylglycerides, free fatty acids and fatty acid alkyl esters. This lubricant is explicitly a liquid. A solid content is not described.
  • the object of the present invention is to provide a lubricating medium with a high viscosity index, which can be used advantageously in gears, engines or other units to be lubricated, which can be produced inexpensively and can also consist entirely of renewable raw materials and thus does not present a high hazard potential if released into the environment.
  • the proposed mixture contains at least a mass fraction of ⁇ 50% natural glycerides Origin and a proportion of fatty acid alkyl esters with 1 to 4 carbon atoms in the alkyl group.
  • the glycerides are at least partly mono- and/or diglycerides, which form a mass fraction of ⁇ 10% in the mixture, and the mixture has a temperature range of > 10°C to at least 15°C, preferably to at least 20°C, a liquid phase with a solids content of ⁇ 1% by volume, which is formed from a proportion of the glycerides and/or the fatty acid alkyl esters.
  • the occurrence of the solid phase is characterized by the fact that the light transmission of the mixture is 10% to 90% lower than that of a completely liquid reference of the same composition at a correspondingly higher temperature.
  • the proportion of solids is preferably selected in such a way that the light transmission is 10% to 50%, ideally 10% to 20%, lower than that of the reference.
  • Methods for determining the light transmission are, for example, photometers or measuring devices that work according to the TURBISCAN ® principle.
  • the lubricating mixture according to the invention also referred to below as lubricant, thus fulfills the lubricating effect of two systems at once by combining the properties of lubricating oils (liquid phase) and lubricating greases (solid phase).
  • the mixture has a predominantly liquid consistency, so the volume fraction of liquid in the mixture is >40%, advantageously >80%, especially advantageously >90%.
  • the mixture can also be formed or produced entirely from renewable raw materials, in particular vegetable oils and fats.
  • the proportion of solids does not impair the properties of the lubricant, or only insignificantly, but leads to better chemical resistance of the lubricant than when using pure vegetable oils.
  • the lubricant can therefore be used in technical lubrication applications without any problems.
  • the size of the solid particles that form the solids content of the proposed mixture have an edge length in the range between 4 ⁇ m and 5 mm. They show a good lubricating effect, since they get into the space between the gear wheels in transmissions, for example, and can develop an advantageous lubricating effect there. This significantly reduces the wear between the metal surfaces compared to other non-lubricating solid particles in the lubricant and prevents abrasive components from penetrating between the gears or into gaps and developing their abrasive effect there.
  • the lubricant according to the invention consists predominantly of triglycerides and partial glycerides natural oils and fats and fatty acid alkyl esters with 1 to 4 carbon atoms in the alkyl group.
  • Particularly advantageous properties result when the mass fraction of the triglycerides in the lubricant is >30%, preferably >40%, ideally >50%.
  • the mass fraction of fatty acid alkyl esters is >10%, ideally >15%.
  • Particularly advantageous properties result when the proportion of diglycerides is >10%, ideally >15%, and that of monoglycerides is >5%.
  • the lubricant contains a proportion of unbound monohydric or polyhydric alcohol. This proportion is preferably between 0.1 and 4%, ideally between 0.1 and 2%.
  • the solids content will advantageously consist of components that are contained in the natural raw material (fat, oil) from which the glycerides for the mixture are obtained or that are obtained from this raw material.
  • the lubricant contains, in addition to the above-mentioned solids based on fats and oils and/or fatty acid alkyl esters, other organic or inorganic components which do not come from the natural raw material and which remain active even at high temperatures of at least 90°C are always fixed.
  • These particles preferably have a diameter of 0.1 to 1.5 ⁇ m, ideally 0.2 to 1 ⁇ m, and surprisingly improve the running-in properties of gears.
  • the proportion of this solid fraction in the lubricant is preferably between 0.1 and 3%, ideally between 0.15 and 2%.
  • foreign particles are non-oxidative metals and metal compounds such as iron or aluminum oxides, inert silicon-based compounds such as silicon oxide, and synthetic and natural polymers such as polystyrene, polyethylene, polyethylene terephthalate, polypropylene, polycarbonate, polyhydroxyalkanoates, polylactic acid, proteins, starches, Celluloses and their derivatives.
  • the composition of the solid particles from the glycerides differs from the composition of the liquid phase.
  • the monoglyceride content in the solid phase is ideally higher by a factor of >1.5, advantageously by a factor of >2, particularly advantageously by a factor of >5, than in the liquid phase.
  • fats containing a high proportion of saturated fatty acids being used at least in part as the raw material.
  • These can be vegetable fats such as palm oil, palm kernel oil or coconut fat or other fats that contain a high proportion of saturated fatty acids >30% by mass, particularly advantageously >80% by mass and are still solid at a temperature of 20°C.
  • a very oxidation-stable lubricant is obtained, which is largely liquid at a temperature of 20°C, so that pumping is possible and a surprisingly high lubricating effect is achieved . This is not the case with untreated vegetable fat.
  • the use of unrefined or only partially refined vegetable oils and fats as raw material is particularly advantageous.
  • the lubricant obtained from this has particularly good oxidation stability.
  • the lubricant has particularly advantageous properties if only the hydratable phospholipids are removed in the refining process or if fat components, which are usually separated off in vegetable oil refining, are not removed or added back.
  • examples of such compounds are carotenoids, non-hydratable lecithins, phenols and phenolic acids, tocopherols, phorbol esters, etc.
  • the mixture of triglycerides and partial glycerides and fatty acid esters according to the invention has a higher viscosity index of >200 compared to the untreated oils and fats.
  • oils that are liquid at this temperature and contain long-chain unsaturated fatty acids in addition to the fat components that are still solid at a temperature of 20°.
  • This can be achieved by adding oils that a contain a high content of unsaturated fatty acids, such as rapeseed or sunflower oil, with the proportion of these oils being selected to be less than 50% by mass, advantageously less than 10% by mass, in order to maintain oxidation stability. It is possible to add the low-viscosity oil before the conversion of the triglycerides or after the conversion.
  • Such mixtures can also be fractions of vegetable oils in the form of pumpable residues which are separated off as minor components during the winterization of oils. At a temperature of 20°C, these contain both liquid and solid components, which have a surprisingly good lubricating effect. Further configurations can be mixtures of these winterization residues with fats or oils, which are optionally also subjected to a partial transesterification.
  • antioxidant substances to further increase the oxidation stability.
  • plant ingredients are used to advantage, which are also contained in natural fats and are also soluble there. These can be carotenes, tocopherols, tocotrienols and other oil-soluble substances with an antioxidant effect.
  • antioxidant plant substances between 0.1 and 10% by mass of antioxidant plant substances should be used for technical applications.
  • the lubricant has particularly advantageous properties if it has a low proportion of inorganic particles ( ⁇ 1.5 ⁇ m). These serve as nuclei for fat crystallization and accelerate the formation of the solid phase.
  • composition and application of the proposed lubricant are shown below using an example.

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

Claims (18)

  1. Mélange à action lubrifiante, notamment destiné à être utilisé dans les transmissions et les moteurs, qui contient au moins
    - une fraction massique en glycérides d'origine naturelle de ≥ 50 %, dans lequel au moins une partie des glycérides est issue de matières grasses végétales, qui contiennent une fraction massique en acides gras saturés d'au moins 30 % et sont solides à une température de 20°C, et
    - une fraction d'esters alkyliques d'acides gras avec 1 à 4 atomes C dans le groupe alkyle,
    dans lequel
    - les glycérides sont au moins en partie des mono et/ou diglycérides, qui forment une fraction massique de ≥ 10 % dans le mélange, et
    - le mélange présente dans une plage de température > 10°C à au moins 15°C, une phase liquide avec une fraction solide de ≥ 1 % en volume,
    - qui est formé par une fraction des glycérides et/ou des esters alkyliques d'acide gras et par des particules solides, qui présentent une extension comprise entre 4 µm et 5 mm, et
    - dans lequel une fraction de liquide dans le mélange s'élève à > 40 % en volume dans la plage de température de > 10°C à au moins 15°C.
  2. Mélange à action lubrifiante selon la revendication 1, caractérisé en ce que
    le mélange contient la phase liquide avec la fraction solide de ≥ 1 % en volume dans la plage de température de > 10°C à au moins 20°C.
  3. Mélange à action lubrifiante selon la revendication 1 ou 2, caractérisé en que
    le mélange présente une phase liquide avec une fraction solide de ≥ 50 % en volume dans la plage de température de > 10°C à au moins 15°C ou jusqu'à au moins 20°C.
  4. Mélange à action lubrifiante selon la revendication 1 ou 2, caractérisé en ce que
    la phase liquide dans la plage de température de > 10°C à au moins 15°C ou à au moins 20°C présente une fraction de ≥ 80 % en volume du mélange.
  5. Mélange à action lubrifiante selon une des revendications 1 à 4,
    caractérisé en ce que
    le mélange contient > 30 % en masse de triglycérides.
  6. Mélange à action lubrifiante selon une des revendications 1 à 5,
    caractérisé en ce que
    le mélange contient > 10 % en poids de diglycérides et > 5 % en poids de monoglycérides.
  7. Mélange à action lubrifiante selon la revendication 5 ou 6, caractérisé en ce que
    la fraction massique en triglycérides est > 40 %, de préférence > 50 %.
  8. Mélange à action lubrifiante selon la revendication 6 ou 7, caractérisé en ce que
    la fraction massique en diglycérides s'élève à > 15 %.
  9. Mélange à action lubrifiante selon une des revendications 1 à 8,
    caractérisé en ce que
    le mélange contient une fraction massique > 10 %, de préférence > 15 %, en esters alkyliques d'acides gras.
  10. Mélange à action lubrifiante selon une des revendications 1 à 9,
    caractérisé en ce que
    le mélange contient une fraction massique comprise entre 0,1 % et 4 % d'alcool mono ou polyhydrique non lié.
  11. Mélange à action lubrifiante selon une des revendications 1 à 10,
    caractérisé en ce que
    le mélange, en plus de la fraction solide des glycérides et/ou esters alkyliques d'acides gras, contient des particules solides d'autres substances organiques et/ou inorganiques qui sont encore solides même à une température d'au moins 90°C.
  12. Mélange à action lubrifiante selon la revendication 11,
    caractérisé en ce que
    les particules solides des autres substances organiques et/ou inorganiques sont contenues dans le mélange dans une fraction massique comprise entre 0,1 % et 3 %.
  13. Mélange à action lubrifiante selon la revendication 11 ou 12, caractérisé en ce que
    les particules solides issues des autres substances organiques et/ou inorganiques présentent une extension dans la plage comprise entre 0,1 µm et 1,5 µm.
  14. Mélange à action lubrifiante selon une des revendications 1 à 13,
    caractérisé en ce que
    les glycérides de la fraction solide ont une fraction de monoglycérides au moins 1,5 fois supérieure aux glycérides de la phase liquide.
  15. Mélange à action lubrifiante selon une des revendications 1 à 14,
    caractérisée en ce qu'
    au moins une partie des glycérides est obtenue à partir de graisse de palme et/ou de graisse de coco.
  16. Mélange à action lubrifiante selon une des revendications 1 à 15, caractérisé en ce que
    certains des glycérides sont obtenus à partir d'huiles végétales liquides à une température de 20°C.
  17. Utilisation du mélange à action lubrifiante selon une ou plusieurs des revendications précédentes comme lubrifiant.
  18. Utilisation selon la revendication 17 comme lubrifiant pour transmissions ou moteurs.
EP16754476.6A 2015-08-31 2016-08-16 Mélange à action lubrifiante contenant des glycérides Active EP3344734B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102015011148 2015-08-31
PCT/EP2016/069395 WO2017036785A1 (fr) 2015-08-31 2016-08-16 Mélange à action lubrifiante contenant des glycérides

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EP3344734A1 EP3344734A1 (fr) 2018-07-11
EP3344734B1 true EP3344734B1 (fr) 2022-10-26

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US (1) US10640722B2 (fr)
EP (1) EP3344734B1 (fr)
JP (1) JP7053454B2 (fr)
KR (1) KR102604851B1 (fr)
CN (1) CN108138065B (fr)
AU (1) AU2016315409B2 (fr)
BR (1) BR112018002095B1 (fr)
CA (1) CA2992150C (fr)
ES (1) ES2933622T3 (fr)
MX (1) MX2018002472A (fr)
MY (1) MY191237A (fr)
PH (1) PH12018500243A1 (fr)
RU (1) RU2018111249A (fr)
SG (1) SG11201800960XA (fr)
WO (1) WO2017036785A1 (fr)

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DE102019210061A1 (de) * 2019-07-09 2021-01-14 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Auf Gleitreibung beanspruchtes System

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RU2018111249A (ru) 2019-10-04
RU2018111249A3 (fr) 2019-10-04
MX2018002472A (es) 2018-06-15
JP2018526511A (ja) 2018-09-13
KR102604851B1 (ko) 2023-11-21
SG11201800960XA (en) 2018-03-28
MY191237A (en) 2022-06-10
BR112018002095A2 (pt) 2018-09-18
WO2017036785A1 (fr) 2017-03-09
BR112018002095B1 (pt) 2020-11-24
US20180245009A1 (en) 2018-08-30
ES2933622T3 (es) 2023-02-10
PH12018500243A1 (en) 2018-07-30
CA2992150C (fr) 2023-06-27
AU2016315409B2 (en) 2019-07-18
JP7053454B2 (ja) 2022-04-12
CA2992150A1 (fr) 2017-03-09
EP3344734A1 (fr) 2018-07-11
US10640722B2 (en) 2020-05-05
CN108138065B (zh) 2021-01-12
KR20180044880A (ko) 2018-05-03
AU2016315409A1 (en) 2018-03-08
CN108138065A (zh) 2018-06-08

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