US3720614A - Polyphenyl thioether lubricating compositions - Google Patents

Polyphenyl thioether lubricating compositions Download PDF

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Publication number
US3720614A
US3720614A US00075751A US3720614DA US3720614A US 3720614 A US3720614 A US 3720614A US 00075751 A US00075751 A US 00075751A US 3720614D A US3720614D A US 3720614DA US 3720614 A US3720614 A US 3720614A
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bis
sulfide
weight
polyphenyl
trichloroacetic acid
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US00075751A
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F Clark
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Monsanto Co
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Monsanto Co
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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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10J—PRODUCTION OF PRODUCER GAS, WATER-GAS, SYNTHESIS GAS FROM SOLID CARBONACEOUS MATERIAL, OR MIXTURES CONTAINING THESE GASES; CARBURETTING AIR OR OTHER GASES
    • C10J2300/00—Details of gasification processes
    • C10J2300/09—Details of the feed, e.g. feeding of spent catalyst, inert gas or halogens
    • C10J2300/0913—Carbonaceous raw material
    • C10J2300/093—Coal
    • C10J2300/0936—Coal fines for producing producer gas
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters thereof
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/043—Mannich bases
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/061—Metal salts
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • 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
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

Definitions

  • compositions are useful as lubricants over 3,510,426 5/1970 Papay ..252/49.8 X wide temperature ranges. I 2,157,873 5/1939 van Peski ..252/49.8 X 2,262,773 11/1941 Lincoln et a1. ..252/54.6 7 Claims, No Drawings POLYPHENYL THIOETHER LUBRICATING COMPOSITIONS
  • This invention relates to improved lubricating compositions comprising polyphenyl thioethers, mixed polyphenyl ethers-thioethers and mixtures thereof, containing from three to eight aromatic groups and a small amount of trichloroacetic acid as a lubricating additive.
  • Polyphenyl thioethers and polyphenyl etherthioethers combinations have found wide application as functional fluids due to their excellent thermal stability and lubricity. For example they have been found to be valuable as hydraulic fluids and as lubricants in motor operation, particularly in jet engines.
  • An object of the present invention is to provide for improved lubricating compositions employing polyphenyl thioethers, polyphenyl ether-thioethers, or mixtures thereof as base stocks.
  • compositions consisting essentially of a major amount of a polyphenyl thioether base fluid having the formula R--Y(R'-Y),.R (I) wherein R is a phenyl group, an alkyl-substituted phenyl group wherein the alkyl group contains one to four carbon atoms, an alkoxy-substituted phenyl group wherein the alkoxy group contains one to four carbon atoms or a halogenated phenyl group wherein the halogen is bromine, fluorine or chlorine, R is a phenylene group, an alkyl or alkoxy-substituted phenylene group where the alkyl group contains one to four carbon atoms or a halogenated phenylene group wherein the halogen is fluorine, bromine or chlorine, and Y is selected from oxygen and sulfur but at least one of the Ys is sulfur and n is an integer having a value of from one to six
  • the amount of trichloroacetic acid employed in the compositions of this invention can range from 0.01 to about 0.02 percent by weight. It is preferred to employ trichloroacetic acid in the compositions of this invention in amounts of from 0.03 to 0.07 percent by weight based upon the total composition.
  • the improvement in lubricity characteristics achieved by the addition of the trichloroacetic acid to the polyphenyl thioether base fluid is unusual and surprising. Wear on a bearing is especially decreased at test temperatures of 600F. whereas when the base fluid is tested without the additive the lubricity of the base fluid is not sufficient and the bearing fails after a short time.
  • the polyphenyl thioethers employed in the composition of this invention have from three to eight benzene rings and from one to seven sulfur atoms with the sulfur atoms joining the benzene rings in chains as ether linkages.
  • polyphenyl thioether as used herein is meant a compound or physical mixture of compounds represented by Formula I.
  • the term includes compounds wherein all of the Ys in Formula I are sulfur.
  • the term also includes those compounds which contain both oxygen and sulfur linkages between the benzene rings.
  • compositions of this invention contain a major amount of the polyphenyl thioether base stock, i.e., at least 50 percent by weight of the total composition comprises a polyphenyl thioether. It is preferred that at least 60 percent by weight of the composition be a polyphenyl thioether base stock and even more preferred that at least 85 percent by weight of the total composition comprise a polyphenyl thioether.
  • compositions of this invention can also contain from'0.01 to 10 percent by weight of the total composition of a dialkyl hydrogen phosphite extreme pressure additive.
  • the dialkyl hydrogen phosphites useful are those wherein the alkyl groups contain from one to 12 carbon atoms. These alkyl groups are for example, methyl, ethyl, propyl, isopropyl, butyl, secbutyl-t-butyl, hexyl, decyl, isodecyl, dodecyl and the like.
  • Illustrations of the alkyl-substituents present in the phenyl and phenylene groups of the polyphenyl thioethers are for example, methyl, ethyl, propyl, butyl and the like. Illustrations of the alkoxy-substituents are, for example, methoxy, ethoxy, propoxy, butoxy and their isomers.
  • polyphenyl thioethers which can be employed as base stocks for the compositions of this invention are the bis(phenylmercapto)benzenes.
  • compositions of the this invention are for example,
  • the phenyl and phenylene groups of such compounds can contain substituents, such as alkyl of one to four carbon atoms, alkoxy of one to four carbon atoms and halogen such as chlorine, bromine and fluorine. Examples of such compounds are as follows:
  • compositions of this invention are useful as lubricants under extreme conditions.
  • the compositions 65 are especially useful for steel on steel lubrication.
  • a polyphenyl thioether polyphenyl ether-thioether lubricant composition is prepared by combining trichloroacetic acid (0.05 grams) with 100 grams of a thioether of the following composition:
  • Example l The composition of Example l was able to complete 100 hours testing with no excessive galling of the bearings or races.
  • compositions of this invention in addition to the polyphenyl thioether base fluid and the trichloroacetic acid additive, may also contain other additives, such as oxidation inhibitors, rust and corrosion inhibitors, antifoaming agents, detergents, viscosity index improvers such as polymeric materials for example, polyacrylate alkyl esters, polymethacrylate alkyl esters, polyoxyalkylene compounds, polyurethanes and the like.
  • additives are usually employed in amounts as low as 10 parts per mil- I While this invention has been described with respect to various specific examples and embodiments, it is understood that the invention is not limited thereto and that it can be variously practiced within the scope of the following claims.
  • a lubricant composition consisting essentially of a major amount of a polyphenyl thioether having the formula cent by weight of trichloroacetic acid.
  • a composition of claim 1 wherein n is from 1 to 3. 4.
  • a lubricant composition consisting essentially of a major amount of a polyphenyl thioether having the formula wherein R is a phenyl group or a substituted phenyl group, R is a phenylene group or substituted phenylene group, in which the substituents on said phenyl and phenylene groups are halogen, alkyl or alkoxy containing from one to four carbon atoms, n is an integer of from l to 6, Y is sulfur or oxygen provided that at least one of the groups represented by Y is sulfur, and mixtures of such thioethers, from 0.01 to 0.2 percent by weight of trichloroacetic acid and from 0.1 to 10 percent by weight of a dialkyl hydrogen phosphite in which the alkyl groups contain from one to 12 carbon atoms.

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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)
US00075751A 1970-09-25 1970-09-25 Polyphenyl thioether lubricating compositions Expired - Lifetime US3720614A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US7575170A 1970-09-25 1970-09-25
US10215270A 1970-12-28 1970-12-28
US10215470A 1970-12-28 1970-12-28

Publications (1)

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US3720614A true US3720614A (en) 1973-03-13

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US00075751A Expired - Lifetime US3720614A (en) 1970-09-25 1970-09-25 Polyphenyl thioether lubricating compositions
US102154A Expired - Lifetime US3677944A (en) 1970-09-25 1970-12-28 Polyphenyl thioether lubricating compositions
US00102152A Expired - Lifetime US3718590A (en) 1970-09-25 1970-12-28 Polyphenyl thioether lubricating compositions

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US102154A Expired - Lifetime US3677944A (en) 1970-09-25 1970-12-28 Polyphenyl thioether lubricating compositions
US00102152A Expired - Lifetime US3718590A (en) 1970-09-25 1970-12-28 Polyphenyl thioether lubricating compositions

Country Status (8)

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US (3) US3720614A (nl)
JP (1) JPS544025B1 (nl)
BE (1) BE773019A (nl)
CA (1) CA952509A (nl)
DE (1) DE2147807C3 (nl)
FR (2) FR2107992B1 (nl)
GB (3) GB1351651A (nl)
NL (1) NL7113060A (nl)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6326337B1 (en) * 2001-04-04 2001-12-04 The United States Of America As Represented By The Secretary Of The Air Force Perfluoropolyalkylether lubricant formulation with improved stability
US6789341B1 (en) 2002-05-07 2004-09-14 Mark L. Badura Firearm safety device

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1399236A (en) * 1971-06-02 1975-06-25 Shell Int Research Phosphorus acid esters and oil compositions containing them
JP3964471B2 (ja) 1995-06-16 2007-08-22 東燃ゼネラル石油株式会社 耐熱性潤滑油組成物

Citations (8)

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US2157873A (en) * 1935-12-02 1939-05-09 Shell Dev Process for extreme pressure lubricants
US2262773A (en) * 1937-03-19 1941-11-18 Lubri Zol Dev Corp Lubrication
US2921874A (en) * 1958-01-21 1960-01-19 Aluminum Res Corp Cold forming lubricant and method of applying same
GB851651A (en) * 1957-12-09 1960-10-19 Bataafsche Petroleum Polyphenyl ether compositions and their use as lubricants
US3226323A (en) * 1963-04-30 1965-12-28 Monsanto Res Corp Lubricant composition containing a haloalkanoic compound
US3284355A (en) * 1963-09-12 1966-11-08 Mobil Oil Corp Lubricating compositions
US3510426A (en) * 1966-11-10 1970-05-05 Mobil Oil Corp Lubricants comprising alkyl phosphites and sulfurized olefins
US3579449A (en) * 1968-09-26 1971-05-18 Procter & Gamble Lubricant composition

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US2174019A (en) * 1936-11-27 1939-09-26 Standard Oil Co Lubricant
US2274291A (en) * 1938-11-26 1942-02-24 Standard Oil Co Compounded mineral oil
US2957931A (en) * 1949-07-28 1960-10-25 Socony Mobil Oil Co Inc Synthesis of compounds having a carbonphosphorus linkage
US2730499A (en) * 1951-08-01 1956-01-10 Exxon Research Engineering Co Lubricants for heavy journal bearings operating at elevated temperatures
US3116248A (en) * 1960-12-23 1963-12-31 Shell Oil Co Lubricating oil composition
NL272801A (nl) * 1960-12-23
US3426075A (en) * 1964-07-01 1969-02-04 Monsanto Co Mixed polyphenyl ethers-thioethers
IL23789A (en) * 1964-07-01 1969-05-28 Monsanto Co Functional fluid compositions
DE1275535B (de) * 1966-09-03 1968-08-22 Zentrales Buero Fuer Neuererwe Verfahren zur Herstellung von Gemischen aus fluessigen Polyphenylthioaethern

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2157873A (en) * 1935-12-02 1939-05-09 Shell Dev Process for extreme pressure lubricants
US2262773A (en) * 1937-03-19 1941-11-18 Lubri Zol Dev Corp Lubrication
GB851651A (en) * 1957-12-09 1960-10-19 Bataafsche Petroleum Polyphenyl ether compositions and their use as lubricants
US2921874A (en) * 1958-01-21 1960-01-19 Aluminum Res Corp Cold forming lubricant and method of applying same
US3226323A (en) * 1963-04-30 1965-12-28 Monsanto Res Corp Lubricant composition containing a haloalkanoic compound
US3284355A (en) * 1963-09-12 1966-11-08 Mobil Oil Corp Lubricating compositions
US3510426A (en) * 1966-11-10 1970-05-05 Mobil Oil Corp Lubricants comprising alkyl phosphites and sulfurized olefins
US3579449A (en) * 1968-09-26 1971-05-18 Procter & Gamble Lubricant composition

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6326337B1 (en) * 2001-04-04 2001-12-04 The United States Of America As Represented By The Secretary Of The Air Force Perfluoropolyalkylether lubricant formulation with improved stability
US6789341B1 (en) 2002-05-07 2004-09-14 Mark L. Badura Firearm safety device

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Publication number Publication date
US3677944A (en) 1972-07-18
FR2107992A1 (nl) 1972-05-12
GB1353315A (en) 1974-05-15
DE2147807C3 (de) 1982-04-22
JPS544025B1 (nl) 1979-03-01
CA952509A (en) 1974-08-06
FR12427E (nl)
DE2147807A1 (de) 1972-03-30
GB1351651A (en) 1974-05-01
DE2147807B2 (de) 1981-06-25
GB1352828A (en) 1974-05-15
US3718590A (en) 1973-02-27
BE773019A (fr) 1972-03-24
NL7113060A (nl) 1972-03-28
FR2107992B1 (nl) 1974-03-29

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