EP2260091B1 - Utilisation d' une composition de graisse lubrifiante à base de liquides ioniques - Google Patents
Utilisation d' une composition de graisse lubrifiante à base de liquides ioniques Download PDFInfo
- Publication number
- EP2260091B1 EP2260091B1 EP09728560A EP09728560A EP2260091B1 EP 2260091 B1 EP2260091 B1 EP 2260091B1 EP 09728560 A EP09728560 A EP 09728560A EP 09728560 A EP09728560 A EP 09728560A EP 2260091 B1 EP2260091 B1 EP 2260091B1
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- EP
- European Patent Office
- Prior art keywords
- grease composition
- lubricating grease
- application
- accordance
- group
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/06—Mixtures of thickeners and additives
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/041—Carbon; Graphite; Carbon black
- C10M2201/0416—Carbon; Graphite; Carbon black used as thickening agents
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/06—Metal compounds
- C10M2201/061—Carbides; Hydrides; Nitrides
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- C10M2201/06—Metal compounds
- C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
- C10M2201/0626—Oxides; Hydroxides; Carbonates or bicarbonates used as thickening agents
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- C10M2201/06—Metal compounds
- C10M2201/065—Sulfides; Selenides; Tellurides
- C10M2201/066—Molybdenum sulfide
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- C10M2201/085—Phosphorus oxides, acids or salts
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- C10M2201/1036—Clays; Mica; Zeolites used as thickening agents
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- C10M2201/1056—Silica used as thickening agents
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- C10M2207/1265—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids monocarboxylic used as thickening agent
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- C10M2207/128—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids containing hydroxy groups; Ethers thereof
- C10M2207/1285—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids containing hydroxy groups; Ethers thereof used as thickening agents
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- C10M2211/063—Perfluorinated compounds used as base material
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- C10M2213/062—Polytetrafluoroethylene [PTFE]
- C10M2213/0626—Polytetrafluoroethylene [PTFE] used as thickening agents
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/041—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms used as base material
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- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
Definitions
- the invention relates to a lubricating grease composition based on ionic liquids, for the protection treatment of components used in the automotive sector, in wind turbines, as well as in processing and working machines and which are exposed to continuous contact with water.
- the invention relates to a water-resistant grease composition which is used in a temperature range of at least -30 ° C to at least 180 ° C in order to protect the components provided with this lubricant against oxidation and corrosion.
- Ionic liquids in lubrication
- IL Ionic Liquid
- RTIL Room Temperature Ionic Liquid
- Ionic liquids have an extremely low vapor pressure, are nonflammable and are often thermally stable up to temperatures above 260 ° C and, in addition, can be lubricated.
- Japanese Patent Application No. Hei. 2005-185718 describes a grease composition containing as base grease a mixture of an ionic liquid, a thickener and other additives. This grease is used for rolling or ball bearings.
- Japanese Patent Application No. Hei. 2005-112597 discloses a grease composition used in electronic devices containing an ionic liquid as the base oil and a thickening agent having a dropping point of 260 ° C.
- Japanese Patent Application No. Hei. 2003-376010 relates to a semi-solid grease composition containing as part of a base oil an ionic liquid and thickener. This grease composition is suitable for vacuum applications.
- Japanese Patent Application No. Hei. 2007-231987 A describes an ionic liquid-based grease composition which may contain a urea compound as a thickener.
- the anions of the ionic liquids used may be, inter alia, Cl and Br, which are corrosive.
- the ionic liquids are water-soluble with a Cl or Br anion.
- the tetrafluoroborates and hexafluoroborates described herein are not resistant to hydrolysis and release corrosive HF, the tetrafluoroborates also being water-soluble. Information on the water resistance of the lubricant compositions is not provided.
- Japanese Patent Application No. Hei. 2005-197958 refers to a lubricating grease composition for rolling bearing machines which contains an ionic liquid as a part of a base oil.
- Japanese Patent Application No. Hei. 2005-294405 describes an electrically conductive bearing grease used in a printer or copier and consisting of a carbonaceous thickener and a base oil containing an ionic liquid.
- the known grease compositions described above have the following drawbacks from a tribological point of view. Due to the salt-like nature of the ionic liquids, lubricant additives such as antioxidants, antifriction agents, anticorrosion additives, anti-wear agents, extreme pressure additives, and the like are, in most cases, insoluble in ionic liquids. However, many tribological applications require that ionic liquids be provided with such additives to improve the properties. However, the development of new additives represents a high technical complexity, so that it is desirable for cost reasons that standard additives can be used in ionic liquids.
- Another disadvantage of using the known grease compositions is the tendency to absorb water and / or react with water through the ionic liquids.
- anions such as sulfate, chloride, bromide or tetrafluoroborate are present in the ionic liquids, this usually results in water-soluble ionic liquids.
- tetrafluoroborate and hexafluorophosphate can form hydrofluoric acid under the influence of water, which can lead to a strong tendency to corrode. This also applies when chloride is present.
- the low-temperature properties of the ionic liquids used are insufficiently taken into account in the known grease compositions.
- the JP 2003-376010 Bis (trifluoromethylsulfonyl) imide-containing ionic liquids with N-alkyl pyridinium cations or N, N'-Dialkylimidazoliumkationen called which are prone to the formation of supercooled melts.
- 1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide is an ionic liquid of low viscosity and high tendency to hypothermia;
- the relevant melting point for tribological applications is -16 ° C (low temperature DSC measurements).
- Ionic liquids such as 1-ethyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide, also have the disadvantage that they can spontaneously solidify at low temperatures, which can lead to failure of the lubricated component.
- Ionic liquids containing, for example, the anion tris (perfluoroethyl) trifluorophosphate generally show lower water absorption capacity than ionic liquids with the bis (trifluoromethylsulfonyl) imide anion, but the melting points are higher. Therefore, these tris (perfluoroethyl) trifluorophosphate-containing ILs are generally unsuitable for low temperature behavior to be used as the sole base oil for lubricants having good low temperature performance.
- the object of the present invention is to provide a water resistant, oxidation and corrosion inhibiting lubricating grease composition which can be used over a wide range of application temperatures.
- ionic liquids used in the grease composition are the ionic liquids containing as cations a quaternary ammonium cation or a phosphonium cation containing an anion containing fluorine selected from the group consisting of bis (perfluoromethylsufonyl) imide, especially Bis (trifluoromethylsulfonyl) imide, tris (perfluoroalkyl) methides, is combined.
- anions individual fluorine atoms can be exchanged for hydrogen.
- the cations have a sufficiently long hydrophobic alkyl chain, aryl group or alkylaryl group of at least 8 to 25 carbon atoms, and the number of such hydrophobizing groups of the cation must be at least 15 to 60 carbon atoms. Comparable nonpolar groups such as aryl or alkylated aryl groups are also conceivable.
- the ionic liquids used in the invention have no viscosity-changing phase transitions to below -40 ° C. This will be among others achieved by the fact that the cations have low symmetry, ie long and short substituents are combined.
- ionic liquids with highly fluorinated anions since these usually have high thermal stability.
- the ability to absorb water can be significantly reduced by such anions, for example, the bis (trifluoromethylsulfonyl) imidanion.
- the grease compositions of the present invention may comprise a single ionic liquid or a mixture of two or more ionic liquids, wherein the second ionic liquid may not necessarily be water resistant.
- the amount distribution of the ionic liquids used is in the range of at least 75 to 95% of the first long-chain ionic liquid to 5 to 25% of the second ionic liquid.
- the second ionic liquid is advantageously selected from the group consisting of ionic liquids containing fluorinated anions such as bis (fluoroalkylsulfonyl) imides, especially bis (trifluoromethylsulfonyl) imides, bis (fluoroaryl) imides, tris (perfluoroalkyl) triphosphates, and fluorinated alkylsulfonates any cation or alternatively ionic liquids with any anions, but with the long-chain cations described above.
- fluorinated anions such as bis (fluoroalkylsulfonyl) imides, especially bis (trifluoromethylsulfonyl) imides, bis (fluoroaryl) imides, tris (perfluoroalkyl) triphosphates, and fluorinated alkylsulfonates any cation or alternatively ionic liquids with any anions, but with the long-chain cations described above.
- the grease compositions according to the invention contain conventional additives or additive mixtures which are selected from corrosion inhibitors, such as oxalines, tiazoles, succinic acid, zinc carboxylates, sodium sulfonates, calcium sulfonates, barium sulfonates, antioxidants, such as aromatic amines, aromatic phenols, phosphites, sulfur-containing compounds, such as dialkyldithiophosphates, Anti-wear agents and extreme pressure additives, such as phosphorus- and sulfur-containing compounds, eg zinc dialkyldithiophosphate, sulphurised fatty acids and fatty acid esters, dialkyl sulphide and dialkyloligo- and polysulphides, boric acid ester agents for reducing friction, such as glycerol mono- and di-esters, agents for protection against metal influences, which are present as chelate compounds, radical scavengers, UV stabilizers, reaction layer formers.
- corrosion inhibitors such as ox
- Viscosity improvers such as polyisobutylene, polymethacrylate, and inorganic or organic solid lubricants such as polyimide, polytetrafluoroethylene (PTFE), graphite, metal oxides, boron nitride, molybdenum disulfide, and phosphate.
- Suitable thickeners are PTFE, bentonite, aerosols, water-insoluble carboxylic acid salts and mixtures thereof, water-insoluble sulfonic acid salts and mixtures thereof, ureas, carbon blacks, graphites, metal oxides such as titanium and zinc oxide and mixtures thereof.
- additives in the form of phosphorus and sulfur compounds e.g. Zinc dialkyldithiophosphate, dithiocarbamates sulphurised hydrocarbons and fatty acids, phosphorus and sulfur-free substances, such as boric acid esters used as wear protection agents and agents for reducing friction; Metal salts, esters, phenols, nitrogen-containing compounds such as aromatic amines, aromatic heterocyclic compounds, sulfonate salts, organic acid and salts are used as anti-corrosive agents, glycerol mono- or diesters as friction inhibitors, and polyisobutylene, polymethacrylate as viscosity improvers.
- Zinc dialkyldithiophosphate dithiocarbamates sulphurised hydrocarbons and fatty acids, phosphorus and sulfur-free substances, such as boric acid esters used as wear protection agents and agents for reducing friction
- Metal salts, esters, phenols, nitrogen-containing compounds such as aromatic amines, aromatic heterocyclic compounds
- the grease composition of the present invention contains 60 to 90% by weight of ionic liquid, 10 to 40% by weight of water-resistant thickener, and 0.1 to 10% by weight of additives.
- the cation of the ionic liquid is selected from the group consisting of a quaternary ammonium cation or a phosphonium cation and the anion is selected from the group consisting of a bis (perfluoroalkylsulfonyl) imide, in particular bis (trifluoromethylsulfonyl) imide, Bis (perfluoroaryl) imide, tris (perfluoroalkyl) triphosphate, wherein the cation of the ionic liquid has a long hydrophobic alkyl chain, aryl group or alkylaryl group of at least 8 to 25 carbon atoms and all hydrophobic alkyl.
- Aryl or alkylaryl groups of the cation comprise at least 15 to 60 carbon atoms and have a melting point of ⁇ -30 ° C.
- Preferred additives are aminic and phenolic antioxidants, anti-corrosion additives, such as amine phosphates, heterocyclic compounds, succinic acid half esters, zinc dialkyldithiophosphates and extreme pressure / anti-wear additives, such as phosphorus and / or sulfur carriers.
- the lubricant compositions of the invention can be used at high temperatures of at least 180 ° C, they can also be used by lowering the electrical resistance of the oils in areas where it is repeatedly flowing through current through current breakdown, as in Railway wheel bearings, rolling bearings with passage of current, in the automotive sector or in electric motors to damage.
- a particularly preferred ionic liquid is trihexyltetradecyphosphonium bis (trifluoromethylsulfonyl) imide, hereinafter referred to as HDPimide, which is represented by the following formula (I):
- the grease composition according to the present invention contains trihexyltetradecylphosphonium bis (trifluoromethylsulfonyl) imide as the ionic liquid.
- a grease composition contains an ionic liquid having the identical anion, referred to as butylmethylpyrrolidinium bis (trifluoromethylsulfonyl) imide, hereinafter referred to as MBPimide, represented by the following formula (II)
- Bis (trifluoromethylsulfonyl) imide is counted among the hydrophobic anions. MBPimid, in contrast to HDPimid, does not have long alkyl chains.
- MBPimid can remain liquid with simple cooling down to temperatures of -40 ° C, which is according to DSC certain melting point but at -6 ° C. Thus, MBPimide has a strong tendency to form a supercooled melt.
- the two ILs are thickened with PTFE powder to a fat consistency (stirring, rolling) and tested according to DIN 51807 Part 1 at 3 h / 90 ° C.
- a succinic acid half ester, an oxazoline derivative and an acetic acid derivative In HDPimid, all substances are 1% soluble at room temperature. In MBPimid, only the oxazoline derivative dissolves after heating to about 150 ° C, but separates on cooling again.
- HDPimid 1% of a p, p'-dialkyl-diphenylamine is dissolved as an antioxidant. The mixture remains clear even after prolonged standing at room temperature.
- a DSC run under oxygen under conditions as indicated in Table 1 the onset of oxidation is 223 ° C. This represents an increase of 55 ° C when compared to HDPimid without additive.
- HDPimid conventional additives for improving corrosion protection properties and oxidation stability are solved. It is a zinc-containing corrosion protection additive and an amine antioxidant. In addition, an insoluble zinc-containing anticorrosive pigment is used. The mixture is thickened with PTFE powder by conventional methods to a fat consistency.
- Table 2 shows that the grease composition of the invention achieves good high and low temperature properties, good anticorrosion properties for steel and copper with resistance to water in both the static and dynamic experiment.
- Table 3 shows that not only ionic liquids with phosphonium as cation, but also ammonium-water-resistant formulations allow.
- Another advantage of the lubricating grease compositions according to the present invention with the ionic liquids used herein is the density lowered by the hydrocarbon groups, which results in a lower price per volume of lubricant and thus at a lower cost per component to be lubricated.
- HDPimide and MBPimide are used to prepare mixtures with different contents relative to the two ILs.
- the mixtures are thickened with approx. 30% PTFE powder and homogenized by rolling, resulting in fats with penetration corresponding to a consistency level of 2.
- the fats are tested for their static water resistance and partly for dynamic water resistance.
- the results are shown in Table 4. ⁇ b> Table 4 ⁇ / b> template 1 2 3 4 5
- Table 4 shows that a lubricating grease composition according to the invention using a combination of ionic liquids which, from a tribological point of view, such as MBPimide, exhibit inadequate water resistance, is possible.
- ionic liquids which, from a tribological point of view, such as MBPimide, exhibit inadequate water resistance
- at least 10% of the insufficiently hydrophobic IL MBPimide may be used relative to the base oil content while maintaining very good water resistance. Up to 25% base oil content is given a partial water resistance.
- a mixture of equal parts of the ionic liquids is no longer water resistant.
- the critical or acceptable mixing ratios depend on the ionic liquids used and therefore can not be generalized.
- HDPimid 89% HDPimid is mixed with 10% lithium 12-hydroxystearate (soap thickener) and brought into the melt. After cooling, 1% of a conventional amine antioxidant is added. The mixture is homogenized by repeated intensive rolling over a roller mill.
- HPDimid cyclohexylamine and bis (paraisocyantophenyl) methane (MDI) are dissolved in a molar ratio of 2: 1 and the solutions are reacted by combining. After heating to 180 ° C and subsequent cooling, 1% of a typical amine antioxidant is added and the fat is homogenized by rolling through a roller mill.
- Examples 7 and 8 show that by using an ionic liquid together with either a urea thickener or a soap thickener, water-resistant formulations are possible which can be applied as a protective film to a wide variety of corrosion and oxidation protection materials and give these materials consistent protection against water .
- This grease composition is particularly useful in automotive applications for water pump bearings, wheel bearings, cardan shafts, clutch release bearings, center bearings, thrust bearings, electro-mechanical brakes, fan bearings, miniature bearings, exhaust gas recirculation systems, generator bearings, windscreen wiper bearings, and the like necessary to ensure that during operation oxidation or corrosion of the coated surface is avoided.
- the water-resistant grease composition is used in wind turbines, main bearings, generator bearings, blade bearings, azimuth bearings, as well as in all components and surfaces that are exposed to constant water contact.
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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)
- Rolling Contact Bearings (AREA)
Abstract
Claims (12)
- Utilisation d'une composition de lubrifiant résistante à l'eau, comprenant(a) 60 à 95 % en poids d'un liquide ionique, dont le cation est choisi parmi le groupe constitué d'un cation d'ammonium quaternaire ou d'un cation de phosphonium et dont l'anion est choisi parmi le groupe constitué d'un bis(perfluoralkylsulfonyl)imide, en particulier de bis(trifluorméthylsulfonyl)-imide, de bis(perfluoraryl)imide, de tris(per-fluoralkyl)trifluorphosphate, le cation du liquide ionique présentant une chaîne alkyle hydrophobe longue, un groupe aryle ou un groupe alkylaryle avec 8 à 25 atomes de carbone au moins et tous les groupes alkyle, aryle ou alkylaryle hydrophobants du cation comprenant 15 à 60 atomes de carbone au moins et présentant un point de fusion de <-30°C,(b) 0,1 à 10 % en poids d'additifs solubles habituellement utilisés dans des lubrifiants et(c) 5 à 60% d'un agent épaississant résistant à l'eau, pour le traitement de protection contre la corrosion et l'oxydation à des températures de -30°C au moins à 180°C au moins.
- Utilisation de la composition de lubrifiant suivant la revendication 1, le liquide ionique étant une combinaison choisie parmi le groupe constitué de trihexyltétradécylphosphoniumbis(trifluorméthylsulfonyl)imide (HDPimid), de méthyltrioctylammoniumbis(trifluorméthylsulfonyl)imide (Moimid), trihexyltétradécylphosphoniumtris(perfluoréthyl)trifluorphosphate.
- Utilisation de la composition de lubrifiant suivant une des revendications 1 ou 2, contenant en outre un mélange de deux ou plusieurs liquides ioniques, le second liquide ionique ne devant pas être nécessairement résistant à l'eau.
- Utilisation de la composition de lubrifiant suivant une des revendications 1 à 3, le mélange à base du premier liquide ionique à chaîne longue par rapport au second liquide ionique se situant dans une plage allant de 75 à 95% à 5 à 25%.
- Utilisation de la composition de lubrifiant suivant une des revendications 1 à 4, le second liquide ionique contenant un anion fluoré choisi parmi le groupe constitué de bis(fluoralkylsulfonyl)imide, en particulier de bis(trifluorméthylsulfonyl)imide, de bis(fluoraryl)imide, de tris(perfluoralkyl)tri-phosphate ou de sulfonates d'alkyle fluorés en présence de cations quelconques ou un cation à chaîne longue choisi parmi le groupe constitué d'un cation d'ammonium quaternaire ou d'un cation de phosphonium et d'un anion quelconque.
- Utilisation de la composition de lubrifiant suivant une des revendications 1 à 5, les additifs étant choisis parmi le groupe constitué d'agents anti-rouille, d'antioxydants, d'agents anti-usure, d'agents extrême-pression, d'agents de réduction de friction, d'agents protégeant contre l'influence de métaux, des stabilisateurs UV, des lubrifiants solides anorganiques ou organiques choisis parmi le polyimide, le polytétrafluoréthylène (PTFE), le graphite, des oxydes métalliques, le nitrure de bore, le disulfure de molybdène et le phosphate.
- Utilisation de la composition de lubrifiant suivant une des revendications 1 à 5, les antioxydants étant choisis parmi le groupe des amines aromatiques, phénols ou transporteurs de soufre.
- Utilisation de la composition de lubrifiant suivant une des revendications 1 à 5, les agents anti-rouille étant choisis parmi le groupe constitué par des hétérocycles aromatiques, des sels de sulfonate, des acides organiques et des sels organiques.
- Utilisation de la composition de lubrifiant suivant une des revendications 1 à 5, les agents de réduction de pression extrême, les agents anti-usure et les agents de réduction de friction étant choisis parmi le groupe constitué de phosphates, de transporteurs de soufre, de combinaisons contenant du phosphore et du soufre, de combinaisons contenant du bore et de combinaisons hétérocycliques.
- Utilisation de la composition de lubrifiant suivant une des revendications 1 à 9, l'agent épaississant étant choisi parmi le PTFE, la bentonite, des aérosils, des sels d'acide carbonique insolubles dans l'eau et/ou leurs mélanges, des sels d'acide sulfonique insolubles dans l'eau et leurs mélanges, des urées, des noirs de carbone, des graphites, des oxydes métalliques, tels que le titan et l'oxyde de zinc et/ou leurs mélanges.
- Utilisation de la composition de lubrifiant suivant une des revendications 1 à 10 qui, sous forme de liquide ionique, contient une combinaison de cations de trialkyltétradécylphosphonium et des anions hautement fluorés, qui sont utilisés en combinaison avec des épaississants insolubles dans l'eau et des additifs.
- Utilisation de la composition de lubrifiant suivant une des revendications 1 à 11 pour le traitement de protection de composants dans des pièces automobiles, dans des pièces d'éoliennes, dans des machines intervenant dans des processus industriels et dans des machines de travail, ainsi que dans des articles ménagers contre l'oxydation et la corrosion et pour améliorer la résistance à l'eau du film de protection.
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| PCT/EP2009/002051 WO2009121494A1 (fr) | 2008-04-04 | 2009-03-19 | Composition de graisse lubrifiante à base de liquides ioniques |
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| SE535675C2 (sv) | 2011-03-22 | 2012-11-06 | Högprestandasmörjmedel och tillsatser till smörjmedel för järnhaltiga och icke järnhaltiga material | |
| JP5818075B2 (ja) * | 2011-07-22 | 2015-11-18 | 協同油脂株式会社 | 潤滑グリース組成物 |
| CN103160363B (zh) * | 2011-12-16 | 2014-06-04 | 中国科学院兰州化学物理研究所 | 含有离子液体的润滑剂组合物及其制备方法 |
| US9725669B2 (en) * | 2012-05-07 | 2017-08-08 | Board Of Regents, The University Of Texas System | Synergistic mixtures of ionic liquids with other ionic liquids and/or with ashless thiophosphates for antiwear and/or friction reduction applications |
| US11440815B2 (en) | 2013-02-22 | 2022-09-13 | Anschutz Exploration Corporation | Method and system for removing hydrogen sulfide from sour oil and sour water |
| US9364773B2 (en) | 2013-02-22 | 2016-06-14 | Anschutz Exploration Corporation | Method and system for removing hydrogen sulfide from sour oil and sour water |
| CA2843041C (fr) | 2013-02-22 | 2017-06-13 | Anschutz Exploration Corporation | Methode et systeme d'extraction de sulfure d'hydrogene de petrole acide et d'eau acide |
| US9708196B2 (en) | 2013-02-22 | 2017-07-18 | Anschutz Exploration Corporation | Method and system for removing hydrogen sulfide from sour oil and sour water |
| CN104141695B (zh) * | 2013-05-07 | 2019-11-26 | 道儒伯润滑科技南京有限公司 | 水和谐轴承 |
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| US9957460B2 (en) | 2014-02-20 | 2018-05-01 | Ut-Battelle, Llc | Ionic liquids containing symmetric quaternary phosphonium cations and phosphorus-containing anions, and their use as lubricant additives |
| JP5955905B2 (ja) * | 2014-07-31 | 2016-07-20 | 出光興産株式会社 | 潤滑油組成物 |
| CN104450020B (zh) * | 2014-10-28 | 2016-09-28 | 宁波春蕊润滑油有限公司 | 一种抗极压耐磨型长效润滑油组合物及其制备方法 |
| JP2017008335A (ja) * | 2016-10-21 | 2017-01-12 | 出光興産株式会社 | グリース組成物 |
| CN109135884A (zh) * | 2017-06-16 | 2019-01-04 | 上海滏兴工贸有限公司 | 一种盾构机盾尾密封油脂及其制备方法 |
| US11370988B2 (en) | 2018-05-15 | 2022-06-28 | Ut-Battelle, Llc | Metal nanoparticles as lubricant additives |
| JP7218242B2 (ja) * | 2019-05-29 | 2023-02-06 | Eneos株式会社 | 導電性グリース組成物 |
| US11970764B2 (en) | 2019-11-06 | 2024-04-30 | Ut-Battelle, Llc | Superlubricity coating containing carbon nanotubes |
| DE102020102462A1 (de) * | 2020-01-31 | 2021-08-05 | IoLiTec Ionic Liquids Technologies GmbH | Ionische Flüssigkeiten enthaltende Schmierstoffzusammensetzung |
| JP7494611B2 (ja) * | 2020-07-14 | 2024-06-04 | 株式会社ジェイテクト | グリース組成物および転がり軸受 |
| US11760766B2 (en) | 2020-07-28 | 2023-09-19 | Ut-Battelle, Llc | Ionic liquids containing quaternary ammonium and phosphonium cations, and their use as environmentally friendly lubricant additives |
| CN112625803B (zh) * | 2020-12-16 | 2022-06-03 | 正大国际科技(常德)集团有限公司 | 一种环保型生物基润滑脂的制备方法 |
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2009
- 2009-03-19 US US12/736,385 patent/US8455407B2/en active Active
- 2009-03-19 JP JP2011502255A patent/JP5532265B2/ja active Active
- 2009-03-19 WO PCT/EP2009/002051 patent/WO2009121494A1/fr not_active Ceased
- 2009-03-19 EP EP09728560A patent/EP2260091B1/fr active Active
- 2009-03-19 CN CN200980111912.3A patent/CN101983231B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009121494A1 (fr) | 2009-10-08 |
| US20110092399A1 (en) | 2011-04-21 |
| JP2011518897A (ja) | 2011-06-30 |
| DE102008017144A1 (de) | 2009-10-15 |
| EP2260091A1 (fr) | 2010-12-15 |
| HK1150621A1 (en) | 2012-01-06 |
| CN101983231A (zh) | 2011-03-02 |
| JP5532265B2 (ja) | 2014-06-25 |
| CN101983231B (zh) | 2014-08-20 |
| US8455407B2 (en) | 2013-06-04 |
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