WO2009121494A1 - Schmierfettzusammensetzung auf basis von ionischen flüssigkeiten - Google Patents

Schmierfettzusammensetzung auf basis von ionischen flüssigkeiten Download PDF

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Publication number
WO2009121494A1
WO2009121494A1 PCT/EP2009/002051 EP2009002051W WO2009121494A1 WO 2009121494 A1 WO2009121494 A1 WO 2009121494A1 EP 2009002051 W EP2009002051 W EP 2009002051W WO 2009121494 A1 WO2009121494 A1 WO 2009121494A1
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WIPO (PCT)
Prior art keywords
grease composition
ionic liquid
group
bis
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2009/002051
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German (de)
English (en)
French (fr)
Inventor
Martin Schmidt-Amelunxen
Dieter Sohn
Stefan Grundei
Andrea HÖPKE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Klueber Lubrication Muenchen GmbH and Co KG
Original Assignee
Klueber Lubrication Muenchen GmbH and Co KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Klueber Lubrication Muenchen GmbH and Co KG filed Critical Klueber Lubrication Muenchen GmbH and Co KG
Priority to EP09728560A priority Critical patent/EP2260091B1/de
Priority to HK11104522.6A priority patent/HK1150621B/xx
Priority to US12/736,385 priority patent/US8455407B2/en
Priority to JP2011502255A priority patent/JP5532265B2/ja
Priority to CN200980111912.3A priority patent/CN101983231B/zh
Publication of WO2009121494A1 publication Critical patent/WO2009121494A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
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    • 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—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 lubricating grease composition which is used in a temperature range of at least -30 0 C to at least 180 0 C in order to protect the components provided with this lubricant to oxidation and corrosion.
  • Ionic liquids in lubrication
  • IL lonic liquid
  • Ionic liquids are defined as materials that consist of Cations and anions are composed and have melting points less than 100 C C.
  • RTIL Room Temperature Ionic Liquid
  • Ionic liquids have an extremely low vapor pressure, are nonflammable and often thermally stable up to more than 260 0 G and, in addition, can be lubricated.
  • Japanese Patent Application No. 2005-185718 describes a grease composition containing as a 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. 2005-112597 discloses a grease composition used in electronic devices containing an ionic liquid as a base oil and a thickener having a dropping point of 260 ° C.
  • Japanese Patent Application No. 2003-376010 relates to a semi-solid grease composition containing as part of a base oil an ionic liquid and thickening agents. This grease composition is suitable for vacuum applications.
  • Japanese Patent Application No. 2005-197958 relates 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. 2005-294405 describes an electrically conductive bearing grease used in a printer or a copier and composed 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, antiwear 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.
  • Yet another disadvantage is that even the use of hydrophobic anions such as bis (trifluoromethylsulfonyl) imide is not sufficient to provide sufficiently water-stable fats from a tribological point of view.
  • 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 for example, the anion
  • Tris (perfluoroethyl) trifluorophosphate usually show a lower water absorption capacity than ionic liquids with the bis (trifluoromethylsulfonyl) imide as the anion, but the melting points are higher. Therefore, these are tris (perfluoroethyl) trifluorophosphate containing IL's usually from the low-temperature behavior not suitable to be used as the sole base oil for lubricants with good low-temperature behavior.
  • 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.
  • the ionic liquids used in this invention have at low temperature DSC experiments, no melting points or glass transitions or other phase transitions above a temperature of -30 0 C, leading to a strong increase in the viscosity of the ionic liquid.
  • 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 (perfluoroalkylsulfonyl) 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 this invention have the viscosity changing phase transitions to below -40 0 C. This is inter alia 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 (thfluoromethylsulfonyl) imidanion.
  • the grease compositions of the present invention may be a single ionic liquid or a mixture of two or more ionic liquids
  • the second ionic liquid does not necessarily have to 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, in particular
  • Bis (trifluoromethylsulfonyl) imides bis (fluoroaryl) imides, tris (perfluoroalkyl) triphosphates, and fluorinated alkylsulfonates of 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, 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, as chelated compounds, radical scavengers ,.
  • corrosion inhibitors such as oxalines, tiazoles, succinic acid, zinc carb
  • UV stabilizers, reaction layerers present are ....
  • 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.
  • the cation of the ionic liquid comprises a long hydrophobic alkyl chain, aryl group or alkylaryl group having at least 8 to 25 carbon atoms and all hydrophobicizing alkylklyl 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 0 C, they can also be used by lowering the electrical resistance of the oils in areas where it by flowing current again and again by electrical breakdown, as in Railway wheel bearings, rolling bearings with passage of current, in the automotive sector or in electric motors to damage.
  • a particularly preferable ionic liquid is thhexyltetradecyphosphonium bis (trifluoromethylsulfonyl) imide, hereinafter referred to as HDPimide, 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.
  • MBPimide can be up to temperatures from -40 0 C to remain liquid with simple cooling which is after certain DSC melting point but at -6 0 C. MBPimide therefore has a strong tendency to form a supercooled melt.
  • methyltrioctylammonium bis (trifluoromethylsulfonyl) imide hereinafter called moimide, having an ammonium cation and long hydrocarbon chains.
  • a first, minor oxidation starts slightly above 200 0 C, but only from about 24O 0 C sets a clearer oxidation.
  • the two IL 's are PTFE powder thickened to a grease consistency (stirring, rolling) and according to DIN 51807 Part 1 in 3 h / 90 ° C tested.
  • separation of the strip occurs.
  • 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.
  • 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 0 C and then cooling 1% of a typical aminic 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 in water pump bearings, wheel bearings,
  • 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)
PCT/EP2009/002051 2008-04-04 2009-03-19 Schmierfettzusammensetzung auf basis von ionischen flüssigkeiten Ceased WO2009121494A1 (de)

Priority Applications (5)

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EP09728560A EP2260091B1 (de) 2008-04-04 2009-03-19 Verwendung einer schmierfettzusammensetzung auf basis von ionischen flüssigkeiten
HK11104522.6A HK1150621B (en) 2008-04-04 2009-03-19 Lubricating grease composition on basis of ionic fluids
US12/736,385 US8455407B2 (en) 2008-04-04 2009-03-19 Lubricating grease composition based on ionic liquids
JP2011502255A JP5532265B2 (ja) 2008-04-04 2009-03-19 イオン液体ベースのグリース組成物
CN200980111912.3A CN101983231B (zh) 2008-04-04 2009-03-19 基于离子液体的润滑脂组合物

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CN113201384A (zh) * 2020-01-31 2021-08-03 克鲁勃润滑剂慕尼黑两合欧洲公司 含有离子液体的润滑剂组合物
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JP2012136649A (ja) * 2010-12-27 2012-07-19 Idemitsu Kosan Co Ltd グリース組成物
WO2012090846A1 (ja) * 2010-12-27 2012-07-05 出光興産株式会社 グリース組成物
WO2012128714A1 (en) * 2011-03-22 2012-09-27 Antzutkin Oleg N Ionic-liquid-based lubricants and lubrication additives comprising ions
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JP2017008335A (ja) * 2016-10-21 2017-01-12 出光興産株式会社 グリース組成物
CN113201384A (zh) * 2020-01-31 2021-08-03 克鲁勃润滑剂慕尼黑两合欧洲公司 含有离子液体的润滑剂组合物
CN113201384B (zh) * 2020-01-31 2023-10-24 克鲁勃润滑剂慕尼黑两合欧洲公司 含有离子液体的润滑剂组合物
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CN101983231A (zh) 2011-03-02
EP2260091B1 (de) 2012-06-13
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US8455407B2 (en) 2013-06-04
EP2260091A1 (de) 2010-12-15

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