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US20060094605A1 - Method for producing lubricant additive (variants) - Google Patents

Method for producing lubricant additive (variants) Download PDF

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Publication number
US20060094605A1
US20060094605A1 US10/532,416 US53241605A US2006094605A1 US 20060094605 A1 US20060094605 A1 US 20060094605A1 US 53241605 A US53241605 A US 53241605A US 2006094605 A1 US2006094605 A1 US 2006094605A1
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United States
Prior art keywords
modifier
general formula
molybdenum
derivatives
mixture
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Abandoned
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US10/532,416
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English (en)
Inventor
Viktor Bakunin
Galina Kuz'mina
Oleg Parenago
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AV Topchiev Institute of Petrochemical Synthesis
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AV Topchiev Institute of Petrochemical Synthesis
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Filing date
Publication date
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Assigned to INSTITUT NEFTEKHIMICHESKOGO SINTEZA RAN IM. A.V. TOPCHIEVA (INKHS RAN) reassignment INSTITUT NEFTEKHIMICHESKOGO SINTEZA RAN IM. A.V. TOPCHIEVA (INKHS RAN) ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BAKUNIN, VIKTOR NIKOLAEVICH, KUZ'MINA, GALINA NIKOLAEVNA, PARENAGO, OLEG PAVLOVICH
Publication of US20060094605A1 publication Critical patent/US20060094605A1/en
Abandoned legal-status Critical Current

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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
    • C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/22—Compounds containing sulfur, selenium or tellurium
    • 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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/18—Complexes with metals
    • 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
    • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
    • C—CHEMISTRY; METALLURGY
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06—Metal compounds
    • C10M2201/065—Sulfides; Selenides; Tellurides
    • C10M2201/066—Molybdenum sulfide
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/09—Complexes with metals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/12—Groups 6 or 16
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/055—Particles related characteristics
    • C10N2020/06—Particles of special shape or size
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • the present invention relates to the field of petrochemistry, more particularly to molybdenum compounds comprising sulfur and their use as additives in lubricating materials for reducing friction coefficient.
  • antifriction additives are introduced into lubricating oils.
  • oil-soluble complex molybdenum are used as the friction modifiers, which compounds include sulfur, nitrogen or phosphor atoms as ligands.
  • a method is known [2] in which additives to lubricating oils are prepared by reacting a sulfur-comprising organic compound, having an active hydrogen atom, with molybdenum pentachloride.
  • the product isolated as a result of the reaction contains 3% of molybdenum and about 1% of chlorine, which is undesirable for ecological reasons and because of the possible corrosive activity of the product.
  • a molybdenum-comprising additive to lubricating oils, which exhibits antifriction and antioxidation properties, is prepared as described in US patent [3], in three steps, wherein in the first step a reaction is carried out of a triglyceride of vegetable oil with a nitrogen-comprising compound, then in the second step the product of the first step is reacted with a molybdenum compound, and in the third step the product of the second step is reacted with sulfur or a sulfur-containing compound.
  • the relatively complex manner of synthesis should be considered as drawbacks of the method.
  • a method in accordance with which an additive to oils is prepared based on a mixture of a friction modifier (nitrogen- or oxygen-comprising organic compound) and a trinuclear sulfur-containing molybdenum complex comprising dithiocarbamine groups as the ligands [6].
  • a friction modifier nitrogen- or oxygen-comprising organic compound
  • a trinuclear sulfur-containing molybdenum complex comprising dithiocarbamine groups as the ligands [6].
  • the most similar analog of the claimed invention is the method [7], in which an antifriction additive is prepared in the form of chemically modified nanosized particles of molybdenum trisulfide.
  • the nanosized particles of molybdenum trisulfide are prepared by forming inverted microemulsions of the “water-in-oil” type, stabilized by surfactants, and comprising water-soluble salts of molybdic acid in an aqueous phase, converting them into salts of thiomolybdic acid by reacting with hydrogen sulfide and subsequent isolation of nanosized particles of MoS 3 , preliminarily processed with modifying compounds.
  • nanosized particles of molybdenum trisulfide are obtained, which are stable in hydrocarbon media, including oils, and which exhibit high effectiveness as antifriction additives.
  • the low technological effectiveness of synthesis of the additive which is related to carrying out the process in strongly diluted organic solutions and to the use of hydrogen sulfide as the reagent, should be considered as drawbacks of this method.
  • the object of the proposed invention is to provide a convenient and technological method of preparing an additive for lubricating materials based on chemically modified nanosized particles of molybdenum trisulfide and derivatives thereof.
  • a method of preparing additives for lubricating materials based on chemically modified nanosized particles of molybdenum trisulfide and/or derivatives thereof comprises preparing the nanosized particles of molybdenum trisulfide and/or derivatives thereof from salts of thiomolybdic acid of the general formula M 2 MoS 4-x O x , where M is NH 4 , Na, x is 0-3, in the presence of two modifiers, where tetraalkylammonium salts of the general formula R 1 R 2 R 3 R 4 NX, wherein R 1 , R 2 , R 3 and R 4 are identical or different and are independently selected from the group consisting of C 1 -C 16 alkyl, X is Cl or Br, or mixtures thereof are used as the first modifier, while derivatives of succinimide of the general formula where R 5 is normal or branched alkyl or oligoalkylene with a molecular weight of from 140 to about 1000, R 6
  • the second embodiment of realizing the method according to the present invention consists in that the nanosized particles of molybdenum trisulfide and/or derivatives thereof are prepared from salts of molybdic acid of the general formula M 2 MoO 4 where M is NH 4 , Na, and a sulfur donor which is an inorganic sulfide or polysulfide of the general formula M′ 2 Sn, wherein M′ is NH 4 , Na, n is 1 to 4, or thiourea, in the presence of two modifiers, modifiers, where tetraalkylammonium salts of the general formula R 1 R 2 R 3 R 4 NX, wherein R 1 , R 2 , R 3 and R 4 are identical or different and are independently selected from the group consisting of C 1 -C 16 alkyl, X is Cl or Br, or mixtures thereof are used as the first modifier, while derivatives of succinimide of the general formula where R 5 is normal or branched alkyl or oligoalkylene with
  • the process is carried out by thermally processing a homogenized in a polar solvent mixture of said salt of molybdic acid, said sulfur donor, for which an inorganic sulfide, polysulfide or thiourea is used, and said first or second modifier, cooling the obtained mixture and subsequently adding said second or first modifier, respectively.
  • the thermal processing is carried out at a temperature of 150 to 220° C. for 1 to 2 hours, while methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, 2-butanol, acetone or benzene is used as the solvent.
  • Tetraalkylammonium salt is selected from the group consisting of tricapryl-methylammonium chloride (Alikvat® 336), methyl-trialkyl(C 8 -C 10 )ammonium chloride (Adogen® 464), cetyl-trimethylammonium bromide (CTAB).
  • the product prepared by any variant of carrying out the method is filtered in order to isolate the solid admixtures and to remove the residues of volatile organic solvents under vacuum.
  • the whole process of preparation may be carried out in one pot, without intermediate steps of isolating and/or purifying, without involving large amounts of organic solvents.
  • the prepared product is a viscous liquid of dark brown color, easily miscible with hydrocarbons and petroleum oils to form transparent solutions or compositions, which have a color from reddish-brown to brown.
  • the content of molybdenum in the product is usually from 0.5 to 2.0% by weight.
  • Solutions of the obtained product are stable dispersions of surface-modified nanosized particles of molybdenum trisulfide, which is confirmed by data of electronic spectroscopy in the UV and visual region ( FIG. 1 ) and a small-angle X-ray spread (SAXS) ( FIG. 2 ).
  • the SAXS method makes it possible to determine the dimensions of the inorganic core of the nanosized particles, which are within the range of from 1 to 6 nm and, as different from the surface-modified nanosized particles described in [7], are characterized by monodisperse size distribution. The latter circumstance makes it possible to presume a higher degree of reproducibility of the synthesis.
  • a homogeneous mixture prepared by mixing at 60° C. 0.12 g of ammonium tetrathiomolybdate, 3.0 g of methyltrialkyl(C 8 -C 10 )ammonium chloride (Adogen® 464) and 5 ml of methanol is subjected to thermal processing at 200° C. for 2 hours, the product residue is 30% of the total starting weight of the components.
  • 4.2 g of alkenylsuccinimide and 5 ml of chloroform are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered through a “blue belt” filter, the solvent is removed under vacuum.
  • the content of molybdenum in the product is 1.22%. There are no absorption bands corresponding to ammonium tetrathiomolybdate in the UV spectrum of the prepared product.
  • a homogeneous mixture prepared by mixing at 60° C. 0.12 g of ammonium tetrathiomolybdate, 3.0 g of tricaprylmethylammonium chloride (Alikvat® 336) and 5 ml of methanol is subjected to thermal processing at 200° C. for 2 hours, the product residue o is 29% of the total starting weight of the components.
  • 4.2 g of alkenylsuccinimide and 5 ml of chloroform are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered as in Example 1, the solvent is removed under vacuum.
  • the content of molybdenum in the product is 1.25%.
  • a homogeneous mixture prepared by mixing at 60° C. 0.12 g of ammonium tetrathiomolybdate, 3.0 g of cetyltrimethylammonium bromide (CTAB) and 10 ml of a methanol-chloroform 1:1 mixture is subjected to thermal processing at 200° C. for 2 hours, the residue of the product is 55% of the total original weight of the components.
  • 4.2 g of alkenylsuccinimide and 5 ml of chloroform are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered, the solvent is removed under vacuum.
  • the content of molybdenum in the product is 1.36%.
  • a homogeneous mixture prepared by mixing at 60° C. 0.12 g of ammonium tetrathiomolybdate, 1.5 g of CTAB and 1.5 g of Adogen® and 10 ml of a methanol-chloroform 1:1 mixture is subjected to thermal processing at 200° C. for 2 hours, the product residue is 42% of the total starting weight of the components.
  • 4.2 g of alkenylsuccinimide and 5 ml of chloroform are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered, the solvent is removed under vacuum.
  • the content of molybdenum in the product is 1.38%.
  • a homogeneous mixture prepared by mixing at 60° C. 0.12 g of ammonium tetrathiomolybdate, 3.0 g of Adogen® and 5 ml of methanol is subjected to thermal processing at 180° C. for 2 hours, the product residue is 29% of the starting weight of the components.
  • 4.2 g of alkenylsuccinimide and 5 ml of chloroform are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered, the solvent is removed under vacuum.
  • the content of molybdenum in the product is 1.19%.
  • a homogeneous mixture prepared by mixing at 60° C. 0.12 g of ammonium tetrathiomolybdate, 3.0 g of Adogen® and 5 ml of methanol is subjected to thermal processing at 210° C. for 2 hours, the product residue is 27.5% of the starting weight of the components.
  • 4.2 g of alkenylsuccinimide and 5 ml of chloroform are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered, the solvent is removed under vacuum.
  • the content of molybdenum in the product is 1.25%.
  • a homogeneous mixture prepared by mixing at 60° C. 0.24 g of ammonium tetrathiomolybdate, 3.0 g of Adogen® and 5 ml of acetone is subjected to thermal processing at 200° C. for 2 hours, the product residue is 26.2% of the starting weight of the components.
  • 4.2 g of alkenylsuccinimide and 5 ml of chloroform are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered, the solvent is removed under vacuum.
  • the content of molybdenum in the product is 2.92%.
  • a homogeneous mixture prepared by mixing at 60° C. 0.12 g of ammonium tetrathiomolybdate, 3.0 g of Adogen® and 5 ml of methanol is subjected to thermal processing at 200° C. for 2 hours, the product residue is 28.2% of the starting weight of the components.
  • 4.2 g of alkenylsuccinimide and 5 ml of chloroform are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered, the solvent is removed under vacuum.
  • the content of molybdenum in the product is 1.22%.
  • a homogeneous mixture prepared by mixing at 60° C. 0.24 g of ammonium tetrathiomolybdate, 3.0 g of Adogen® and 5 ml of methanol is subjected to thermal processing at 200° C. for 2 hours, the product residue is 30.1% of the original total weight of the components.
  • 4.2 g of an N-alkylenamino derivative of alkenylsuccinimide and 5 ml of chloroform are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered, the solvent is removed under.
  • the content of molybdenum in the product is 1.19%.
  • a homogeneous mixture prepared by mixing at 60° C. 0.0095 g of ammonium molybdate, 0.0113 g of Na 2 S-9H 2 O and 0.0360 g of Adogen® in 1 ml of benzene is subjected to thermal processing at 200° C. for 30 minutes.
  • the product residue after thermal processing is 48% of the total weight of the starting components.
  • 0.0420 g of alkenylsuccinimide and 1 ml of chloroform are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered through a “blue belt” filter, then the solvent is removed under vacuum.
  • the content of molybdenum in the product is 1.35%.
  • a homogeneous mixture prepared by mixing at 60° C. 0.0102 g of ammonium molybdate, 0.0320 g of Adogen®, 0.0101 g of thiourea and 5 ml of benzene is subjected to thermal processing at 200° C. for 2 hours.
  • the product residue after thermal processing is 43.0% of the total weight of the starting components.
  • 5 ml of chloroform and 0.042 g of alkenylsuccinimide are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered, then the solvent is evaporated under vacuum.
  • the content of molybdenum in the product is 2.35%.
  • a homogeneous mixture prepared by mixing at 60° C. 0.0101 g of ammonium molybdate, 0.0315 g of Adogen®, 0.0145 g of Na 2 S 2 O 3 0.5H 2 O and 5 ml of benzene is subjected to thermal processing at 200° C. for 2 hours.
  • the product residue after thermal processing is 39.0% of the total weight of the starting components.
  • 5 ml of chloroform and 0.042 g of alkenylsuccinimide are added to the product residue, the mixture is stirred with a magnetic stirrer, filtered, and then the solvent is evaporated under vacuum.
  • the content of molybdenum in the product is 1.31%.
  • the tribological properties of the prepared antifriction additives based on surface-modified nanosized particles of molybdenum trisulfide were studied with respect to their composition in turbine oil T46 with the use of a vibrating tribometer SRV (Optimol firm, Germany).
  • Test conditions friction pair—ball-plane; amplitude of oscillations—1 mm, frequency 50 Hz; axial load changes from 20 to 600 N step-by-step, 1 min at each step, the step being 50 N.
  • the value of the coefficient of friction is measured, the test is considered to be finished in the case where the value of the coefficient of friction exceeds 0.22, or if there is a scratch (automatic stop).
  • the oil compositions were prepared by mixing T46 with a 5 wt.
  • the proposed method makes it possible to prepare an antifriction additive on the basis of surface-modified nanosized particles of molybdenum trisulfide, this additive forming transparent, stable dispersions in hydrocarbons and petroleum oils, and also effectively reducing the coefficient of friction between the metal surfaces and increasing the critical load.
  • the whole process may be carried out in one pot without intermediate steps of isolating and/or purifying, without involving large amounts of organic solvents.

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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)
  • Inorganic Chemistry (AREA)
  • Lubricants (AREA)
  • Inorganic Compounds Of Heavy Metals (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
US10/532,416 2002-10-23 2003-10-16 Method for producing lubricant additive (variants) Abandoned US20060094605A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
RU2002128364/04A RU2002128364A (ru) 2002-10-23 2002-10-23 Способ получения присадки к смазочным материалам (варианты)
RU2002128364 2002-10-23
PCT/RU2003/000440 WO2004037957A1 (fr) 2002-10-23 2003-10-16 Procede de fabrication d'un additif pour lubrifiants et variantes

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US20060094605A1 true US20060094605A1 (en) 2006-05-04

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US10/532,416 Abandoned US20060094605A1 (en) 2002-10-23 2003-10-16 Method for producing lubricant additive (variants)

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US (1) US20060094605A1 (uk)
JP (1) JP2006503954A (uk)
CN (1) CN100384969C (uk)
AU (1) AU2003277760A1 (uk)
DE (1) DE10393575T5 (uk)
EA (1) EA008515B1 (uk)
GB (1) GB2411660B (uk)
RU (1) RU2002128364A (uk)
UA (1) UA80727C2 (uk)
WO (1) WO2004037957A1 (uk)

Cited By (5)

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US20080161213A1 (en) * 2007-01-03 2008-07-03 Tze-Chi Jao Nanoparticle additives and lubricant formulations containing the nanoparticle additives
US20080269086A1 (en) * 2007-04-30 2008-10-30 Atanu Adhvaryu Functionalized nanosphere lubricants
US20090009025A1 (en) * 2005-06-24 2009-01-08 Mitsubishi Denki Kabushiki Kaisha Altering-currant dynamolectric machine
US20090036335A1 (en) * 2007-08-02 2009-02-05 Petroleo Brasileiro S.A.- Process for obtaining an intermetallic compound and use thereof in lubricating oils
US20090042751A1 (en) * 2007-08-11 2009-02-12 Jagdish Narayan Lubricant having nanoparticles and microparticles to enhance fuel efficiency, and a laser synthesis method to create dispersed nanoparticles

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RU2302452C2 (ru) * 2004-08-20 2007-07-10 Институт нефтехимического синтеза РАН им. А.В. Топчиева (ИНХС РАН) Способ получения присадки к смазочным материалам
KR101083306B1 (ko) 2009-08-18 2011-11-15 한국전력공사 혼합 나노 윤활유의 제조방법 및 그에 의해 제조된 혼합 나노 윤활유
IT1402163B1 (it) * 2010-10-01 2013-08-28 Univ Degli Studi Salerno Sintesi "one-pot" di nano cristalli 1d, 2d, e 0d di calcogenuri di tungsteno e molibdeno (ws2, mos2) funzionalizzati con ammine e/o acidi grassi a lunga catena e/o tioli

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US4283295A (en) * 1979-06-28 1981-08-11 Chevron Research Company Process for preparing a sulfurized molybdenum-containing composition and lubricating oil containing said composition
US4400282A (en) * 1980-12-05 1983-08-23 Gulf Research & Development Company Lubricating oils containing quaternary ammonium thiomolybdates
US4343746A (en) * 1980-12-10 1982-08-10 Gulf Research & Development Company Quaternary ammonium thiomolybdates
US4474673A (en) * 1982-06-11 1984-10-02 Standard Oil Company (Indiana) Molybdenum-containing friction modifying additive for lubricating oils
US4588829A (en) * 1984-07-27 1986-05-13 Exxon Research & Engineering Company (Disulfido)tris(N,N-substituted dithiocarbamato)Mo(V) complexes
US4765918A (en) * 1986-11-28 1988-08-23 Texaco Inc. Lubricant additive
US6117826A (en) * 1998-09-08 2000-09-12 Uniroyal Chemical Company, Inc. Dithiocarbamyl derivatives useful as lubricant additives
US6245725B1 (en) * 1998-12-24 2001-06-12 Asahi Denka Kogyo K.K. Lubricating compositions
US20040259945A1 (en) * 2002-07-23 2004-12-23 The Regents Of The University Of Michigan Tetrapropylammonium tetrathiomolybdate and related compounds for anti-angiogenic therapies

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US8741821B2 (en) 2007-01-03 2014-06-03 Afton Chemical Corporation Nanoparticle additives and lubricant formulations containing the nanoparticle additives
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GB2411660A (en) 2005-09-07
AU2003277760A1 (en) 2004-05-13
EA008515B1 (ru) 2007-06-29
DE10393575T5 (de) 2005-09-29
WO2004037957A1 (fr) 2004-05-06
GB0510381D0 (en) 2005-06-29
RU2002128364A (ru) 2004-04-27
GB2411660B (en) 2006-07-12
CN1723269A (zh) 2006-01-18
JP2006503954A (ja) 2006-02-02
UA80727C2 (en) 2007-10-25
CN100384969C (zh) 2008-04-30

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