US3127347A - Lubricating composition - Google Patents

Lubricating composition Download PDF

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US3127347A
US3127347A US3127347DA US3127347A US 3127347 A US3127347 A US 3127347A US 3127347D A US3127347D A US 3127347DA US 3127347 A US3127347 A US 3127347A
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urea
lubricating
tetraalkyl
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ureas
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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
    • C10M115/00—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof
    • C10M115/08—Lubricating compositions characterised by the thickener being a non-macromolecular organic compound other than a carboxylic acid or salt thereof containing nitrogen
    • 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
    • C10M2201/10—Compounds containing silicon
    • C10M2201/105—Silica
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
    • 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
    • C10N2010/02—Groups 1 or 11
    • 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
    • C10N2010/04—Groups 2 or 12
    • 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
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • the present invention relates to a lubricating composition. More particularly, this invention relates to the use of tetraalkyl ureas as lubricating compounds.
  • Another object of this invention is to provide a new and improved lubricating composition. It is another object of this invention to provide a new and improved lubricating composition comprised of particular nitrogen containing compounds.
  • a more specific object of this invention is to provide a new and improved lubricating oil comprised of a tetraalkyl urea.
  • Another specific object of this invention is to provide a new and improved lubricating grease comprised of a tetraalkyl urea and a minor amount of a thickening agent.
  • Still another object of this invention is to provide a new and improved lubricating composition compirsed of a tetraalkyl urea and a conventional petroleum lubricating composition. Additional objects will become apparent from the description of the invention.
  • tetraalkyl ureas possess very good lubricating properties and are especially adapted to utility as high temperature lubricants.
  • the tetraalkyl ureas of this invention are represented by the formula:
  • R R R and R represent alkyl radicals each containing at least two carbon atoms, but not more than 18 carbon atoms.
  • These ureas can be used per se as high temperature lubricants and also as the fluid base for high temperature greases.
  • the tetraalkyl lubricants of this invention are useful at temperatures ranging from 62 to 325 C. and higher.
  • a -78 inch spindle with a polished, stainless steel head was placed in the socket of a drill press which was set at 1000 r.p.m. Enough of the indicated urea was placed in a 1 oz. tin to sufiiciently cover the bottom of the tin.
  • the rotating spindle was lowered into the tin and held in position with a nine-pound weight attached to the horizontal bar of the drill press. I he spindle was allowed to run in this position for two minutes, after which time it was raised and the results of the test observed. After each test the spindle was polished with No. 3 emery cloth.
  • the criterion for judging the lubricating qualities of the ureas is a comparison with a General Electric silicone oil, No. 81406. The results of this testing of several representative tetraalkyl ureas are given in the following table.
  • Lubricating composition Lubricating quality 1,1-di-n-octyl-3,3-di-n-octadecy1 urea Good 1,1-di-n heXyl-3,3-di-n-octadecyl urea Good 1,1-di-n-butyl-3,3-di-n-octadecyl urea z- Good l,l-di-n-dodecyl-3,3-di-n-octyl urea Fair 1,1-di-n-dodecyl-3,3-di-2-ethylhexyl urea Fair 1,1,3,3-tetra-n-octyl urea Fair G.E. silicone oil Poor EXAMPLE III Since thermal stability is necessary for high temperature lubricants, the following test was used to determine the amount of decomposition of several representative tetraalkyl ureas.
  • tetraalkyl urea was placed in a 10 x mm. test tube which was immersed in a metal (Woods alloy) bath. The temperature of the bath was raised to 200 C. and maintained for 20 minutes, after which time the temperature was raised to 250 C. for 20 minutes, and then to 300 C. for 20 minutes. At five minute intervals the tubes were checked for discoloration and decomposition. At such intervals the vapors from the sample were tested for free amine with ammonia test paper dipped in ethanol.
  • a grease was prepared from 1,l-di-n-dodecyl-3,3-di-noctyl urea by thickening with 15 by weight of finely divided (less than 1 micron particle size) SlOg. A 1 gram sample of this was then placed in a bicycle hearing. The conditions of the test were 430 F. and 1800 r.p.m. The grease showed low loss, good coating characteristics and no separation.
  • EXAMPLE V A grease was prepared from 1,1-di-n-heXyl-3,3-di-noctadecyl urea by thickening with 15% by weight of finely divided (less than 1 micron particle size) SiO A 1 gram sample of this was then placed in a bicycle bearing. The conditions of the test were 430 F. and 1800 r.p.m. The grease showed low loss, good coating characteristics and no separation.
  • Table I lists the viscosity index and pour point for a number of representative tetraalkyl ureas.
  • 1,1,3,3 tetra ethyl urea 54 -81 1,1 d1-ethyl3,3 di-2, ethyl hexyl urea... 80 80 1,1,di-n-buty1 3,3,-di-n-octyl urea 68. l 81 1,1,3,3 tetra n-hexyl urea 68 69 1,1-di n-hexyl 3,3-di-n-oetyl 1111251.. 110 20 1,1-di-n-butyl 3,3-di-ndodeeyl urea...
  • the tetraalkyl urea lubricating compounds of this invention may be prepared by reacting a dialkyl carbamyl chloride having the formula with a dialkylamine having the formula wherein R R R and R represent alkyl radicals each containing at least tWo carbon atoms preferably at an elevated temperature and in an inert diluent on reaction medium.
  • the procedure for preparing the novel ureas of this invention can be varied substantially.
  • the reaction is preferably, but not necessarily, carried out in an inert diluent or reaction medium.
  • Aliphatic and aromatic hydrocarbons are particularly useful in this regard.
  • the temperature of the reaction can be varied substantially. Elevated temperatures in the range of from about 50 C. to 200 C. are preferred.
  • any conventional thickening agent may be used.
  • thickening agents are SiO calcium base soap, sodium base soaps, etc.
  • l of soap thickening agent with the tetraalkyl lubricants at 235 F. a sodium base grease made with 1,1-d-i-n octyl- 3,3-di-n-octadecyl urea performed just as Well as a sodium base grease made from a commercial lube oil.
  • the amount of thickening agent will be dependent upon the agent employed and the thickness desired for the grease. :In the practice of the present invention, no thickening agent is necessary, although if used, an amountof thickening agent of from 5 to 20% by weight is preferred, although more or less may be used.
  • the lubricants of this invention may find utility in a host of applications.
  • applications are lubricating oils, lubricating greases, hydrau'lic fluids or in any other utility requiring compounds having the physical characteristics set forth in the examples.
  • the lubricating compositions of this invention can be used in admixture with petroleum lubricating oils and greases. These tetraalkyl ureas may be present in such mixture in quantities ranging from 1 to percent by Weight. By addition of tetraa'lkyl lubricants to petroleum lubricants, certain properties of the petroleum lubricants may be improved.
  • a lubricating grease consisting essentially of a major amount of a tetraalkyl urea having the formula wherein R R R and R represent alkyl radicals containing at least 2 carbon atoms and not more than 18 carbon atoms, thickened to grease-like consistency with a minor amount of a thickening agent.
  • a lubricating grease as described in claim 1 wherein the urea is 1,1-di-n-dodecyl-3,3-d-i-n octyl urea.
  • a lubricating grease as described in claim 1 wherein the urea is 1,1-di-n-'heXyl-3,3-di-n-octadecyl urea.

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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)

Description

United States Patent 3,127,347 LUBRICATIN G COMPOSITION Raymond A. Franz, El Dorado, Ark., assignor to Monsanto Chemical Company, St. Louis, M0,, :1 corporation of Delaware No Drawing. Filed May 20, 1960, Ser. No. 30,431 4 Claims. ((31. 252-48) The present invention relates to a lubricating composition. More particularly, this invention relates to the use of tetraalkyl ureas as lubricating compounds.
The lubricating properties of nitrogen containing compounds have been rather extensively investigated. As a result many of these compounds have been found to exhibit excellent lubricating properties while others have shown very poor results.
It is then an object of this invention to provide a new and improved lubricating composition. It is another object of this invention to provide a new and improved lubricating composition comprised of particular nitrogen containing compounds. A more specific object of this invention is to provide a new and improved lubricating oil comprised of a tetraalkyl urea. Another specific object of this invention is to provide a new and improved lubricating grease comprised of a tetraalkyl urea and a minor amount of a thickening agent. Still another object of this invention is to provide a new and improved lubricating composition compirsed of a tetraalkyl urea and a conventional petroleum lubricating composition. Additional objects will become apparent from the description of the invention.
In fulfillment of these objects, it has been found that tetraalkyl ureas possess very good lubricating properties and are especially adapted to utility as high temperature lubricants. The tetraalkyl ureas of this invention are represented by the formula:
wherein R R R and R represent alkyl radicals each containing at least two carbon atoms, but not more than 18 carbon atoms. These ureas can be used per se as high temperature lubricants and also as the fluid base for high temperature greases. The tetraalkyl lubricants of this invention are useful at temperatures ranging from 62 to 325 C. and higher.
To facilitate understanding of the invention herein disclosed, the following examples are presented. It is to be understood, of course, that these examples are in no 1 way to be construed as limiting the application, conditions, or operations of this invention.
EXAMPLE I A sample of 1,1-di-n-dodecyl-3,3-di-2-ethyl hexyl urea was subjected to a standard Four Ball Wear Test. The test was carried out at 1250 r.p.m. for two hours, steel on steel. The results were as follows:
Scar Diameters These low scar diameters indicate good lubricating characteristics, superior to mineral oil and the more conventional high temperature hydraulic fluids.
3,127,343 Patented Mar. 31, 1964 EXAMPLE n The following additional test was used for determining the lubricating qualities of tetra-substituted ureas:
A -78 inch spindle with a polished, stainless steel head was placed in the socket of a drill press which was set at 1000 r.p.m. Enough of the indicated urea was placed in a 1 oz. tin to sufiiciently cover the bottom of the tin. The rotating spindle was lowered into the tin and held in position with a nine-pound weight attached to the horizontal bar of the drill press. I he spindle was allowed to run in this position for two minutes, after which time it Was raised and the results of the test observed. After each test the spindle was polished with No. 3 emery cloth. The criterion for judging the lubricating qualities of the ureas is a comparison with a General Electric silicone oil, No. 81406. The results of this testing of several representative tetraalkyl ureas are given in the following table.
Lubricating composition: Lubricating quality 1,1-di-n-octyl-3,3-di-n-octadecy1 urea Good 1,1-di-n heXyl-3,3-di-n-octadecyl urea Good 1,1-di-n-butyl-3,3-di-n-octadecyl urea z- Good l,l-di-n-dodecyl-3,3-di-n-octyl urea Fair 1,1-di-n-dodecyl-3,3-di-2-ethylhexyl urea Fair 1,1,3,3-tetra-n-octyl urea Fair G.E. silicone oil Poor EXAMPLE III Since thermal stability is necessary for high temperature lubricants, the following test was used to determine the amount of decomposition of several representative tetraalkyl ureas.
One gram of tetraalkyl urea was placed in a 10 x mm. test tube which was immersed in a metal (Woods alloy) bath. The temperature of the bath was raised to 200 C. and maintained for 20 minutes, after which time the temperature was raised to 250 C. for 20 minutes, and then to 300 C. for 20 minutes. At five minute intervals the tubes were checked for discoloration and decomposition. At such intervals the vapors from the sample were tested for free amine with ammonia test paper dipped in ethanol.
The results of the testing of several representative tetraalkyl ureas is given in the following table:
Visible Decomposition ,l-di-nbctyl-S,3-di-n-octadseyl urea ,I-di-n-hexyl-3,3 di-n-oetadecyl urea ,i-din-butyl-3,3-di-n-octadecyl urea- -d ,1d 1 3 Negative Negative. o Do.
Do. Do.
Do. Slight/300.
i-n-dodeeyl-3,3 di-n-octyl urea i-n-dodecyl-3,3-di2-ethy1hexyl urea 1 1 1 1 1 1, ,3 tetra-n-octyl urea EXAMPLE IV A grease was prepared from 1,l-di-n-dodecyl-3,3-di-noctyl urea by thickening with 15 by weight of finely divided (less than 1 micron particle size) SlOg. A 1 gram sample of this was then placed in a bicycle hearing. The conditions of the test were 430 F. and 1800 r.p.m. The grease showed low loss, good coating characteristics and no separation.
EXAMPLE V A grease was prepared from 1,1-di-n-heXyl-3,3-di-noctadecyl urea by thickening with 15% by weight of finely divided (less than 1 micron particle size) SiO A 1 gram sample of this was then placed in a bicycle bearing. The conditions of the test were 430 F. and 1800 r.p.m. The grease showed low loss, good coating characteristics and no separation.
To further exemplify the utility of the tetraalkyl ureas as lubricating oils, Table I lists the viscosity index and pour point for a number of representative tetraalkyl ureas.
Table I Compound Viscosity Pour Index Point, F.
1,1,3,3 tetra ethyl urea 54 -81 1,1 d1-ethyl3,3 di-2, ethyl hexyl urea... 80 80 1,1,di-n-buty1 3,3,-di-n-octyl urea 68. l 81 1,1,3,3 tetra n-hexyl urea 68 69 1,1-di n-hexyl 3,3-di-n-oetyl 1111251.. 110 20 1,1-di-n-butyl 3,3-di-ndodeeyl urea... 129 -30 1,1-ki-2-ethyl hexyl 3,3-di-n-oetyl me 91. 6 -59 1,1,3, -tetran-ootyl urea 127. +5 1,1-di-n-dodccyl 3,3-di-n-hexyl urea 1 136 40 1,l-din-dodoeyl 3,3-di-2-ethyl hexyl urea 110. 1 -28 1,l-di-n-dodeoyl 3,3-di-n-octyl urea 137. 41 +14 1,1-di-n-butyl 3,3-di-n-octadecyl urea a 139 +40 1,1-di-n-hexyl 3,3-di-n-octadecyl urea... 136 +25 1,1-di-n-octyl 3,3-di-nbetadecyl urea 138 4 +35 The tetraalkyl urea lubricating compounds of this invention may be prepared by reacting a dialkyl carbamyl chloride having the formula with a dialkylamine having the formula wherein R R R and R represent alkyl radicals each containing at least tWo carbon atoms preferably at an elevated temperature and in an inert diluent on reaction medium. The procedure for preparing the novel ureas of this invention can be varied substantially. While equiinolecular proportions of the reactants are advantageously used, excessive quantities of either can be used if desired as dictated by economic or yield considerations. While it is not necessary to do so, the reaction is best carried out in the presence of an HCl-acceptor. Any alkaline agent Which does not react to any serious degree with either of the reactants can be used. Tertiary alkylamines are particularly useful.
The reaction is preferably, but not necessarily, carried out in an inert diluent or reaction medium. Aliphatic and aromatic hydrocarbons are particularly useful in this regard.
The temperature of the reaction can be varied substantially. Elevated temperatures in the range of from about 50 C. to 200 C. are preferred.
When it is desired to use the tetraalkyl urea lubricants disclosed herein as lubricating greases, any conventional thickening agent may be used. Several non-limiting examples of such thickening agents are SiO calcium base soap, sodium base soaps, etc. As illustrative of the use l of soap thickening agent, with the tetraalkyl lubricants at 235 F. a sodium base grease made with 1,1-d-i-n octyl- 3,3-di-n-octadecyl urea performed just as Well as a sodium base grease made from a commercial lube oil.
The amount of thickening agent will be dependent upon the agent employed and the thickness desired for the grease. :In the practice of the present invention, no thickening agent is necessary, although if used, an amountof thickening agent of from 5 to 20% by weight is preferred, although more or less may be used.
The lubricants of this invention may find utility in a host of applications. Several non-limiting examples of applications are lubricating oils, lubricating greases, hydrau'lic fluids or in any other utility requiring compounds having the physical characteristics set forth in the examples.
The lubricating compositions of this invention can be used in admixture with petroleum lubricating oils and greases. These tetraalkyl ureas may be present in such mixture in quantities ranging from 1 to percent by Weight. By addition of tetraa'lkyl lubricants to petroleum lubricants, certain properties of the petroleum lubricants may be improved.
What is claimed is:
1. A lubricating grease consisting essentially of a major amount of a tetraalkyl urea having the formula wherein R R R and R represent alkyl radicals containing at least 2 carbon atoms and not more than 18 carbon atoms, thickened to grease-like consistency with a minor amount of a thickening agent.
2. A lubricating grease as described in claim 1 wherein the urea is 1,1-di-n-dodecyl-3,3-d-i-n octyl urea.
3. A lubricating grease as described in claim 1 wherein the urea is 1,1-di-n-'heXyl-3,3-di-n-octadecyl urea.
4. A lubricating grease as described in claim 1 wherein the minor amount of a thickening agent is a minor amount of SiO References Cited in the file of this patent UNITED STATES PATENTS 1,437,027 Tanberg Nov. 28, 1922 2,050,582 Orthner et al Aug. 11, 1936 2,195,167 Egerton Mar. 26, 1940 2,257,717 Olin Sept. 30, 1941 2,276,696 Olin Mar. 17, 1942 2,668,758 Roos Feb. 9, 1954 2,710,841 Swakbn et a1. June 14, 1955 FOREIGN PATENTS 17,501 Great Britain Feb. 11, 1915 802,941 Great Britain Oct. 15, 1958

Claims (1)

1. A LUBRICATING GREASE CONSISTING ESSENTIALLY OF A MAJOR AMOUNT OF A TETRAALKYL UREA HAVING THE FORMULA
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3296128A (en) * 1964-12-23 1967-01-03 Chevron Res Monohydroxyhydrocarbyl ureas as lubricating oil detergents
NL7810136A (en) * 1970-08-07 1979-01-31 Pfizer METHOD OF GENERATING ENDOGENIC INTERFERON.
US5607906A (en) * 1995-11-13 1997-03-04 Kyodo Yushi Co., Ltd. Grease composition for constant velocity joints

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB191517501A (en) * 1915-12-14 1916-12-14 Elton Amerst Wright Improvements in Valves for Internal Combustion Engines.
US1437027A (en) * 1918-09-11 1922-11-28 Du Pont Process of producing tetra-substituted ureas
US2050582A (en) * 1933-04-15 1936-08-11 Ig Farbenindustrie Ag Process of mercerizing cellulose material
US2195167A (en) * 1936-12-18 1940-03-26 Egerton Alfred Charles Glyn Method of preventing the formation of gumlike products in oils
US2257717A (en) * 1941-03-24 1941-09-30 Sharpies Chemicals Inc Manufacture and purification of urea derivatives
US2276696A (en) * 1939-10-06 1942-03-17 Sharples Chemicals Inc Manufacture of homologues of urea
US2668758A (en) * 1952-07-03 1954-02-09 Monsanto Chemicals Defoliant compositions
US2710841A (en) * 1953-11-18 1955-06-14 Standard Oil Co Method of preparing substituted urea-thickened greases
GB802941A (en) * 1956-07-10 1958-10-15 Exxon Research Engineering Co Lubricating composition

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB191517501A (en) * 1915-12-14 1916-12-14 Elton Amerst Wright Improvements in Valves for Internal Combustion Engines.
US1437027A (en) * 1918-09-11 1922-11-28 Du Pont Process of producing tetra-substituted ureas
US2050582A (en) * 1933-04-15 1936-08-11 Ig Farbenindustrie Ag Process of mercerizing cellulose material
US2195167A (en) * 1936-12-18 1940-03-26 Egerton Alfred Charles Glyn Method of preventing the formation of gumlike products in oils
US2276696A (en) * 1939-10-06 1942-03-17 Sharples Chemicals Inc Manufacture of homologues of urea
US2257717A (en) * 1941-03-24 1941-09-30 Sharpies Chemicals Inc Manufacture and purification of urea derivatives
US2668758A (en) * 1952-07-03 1954-02-09 Monsanto Chemicals Defoliant compositions
US2710841A (en) * 1953-11-18 1955-06-14 Standard Oil Co Method of preparing substituted urea-thickened greases
GB802941A (en) * 1956-07-10 1958-10-15 Exxon Research Engineering Co Lubricating composition

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3296128A (en) * 1964-12-23 1967-01-03 Chevron Res Monohydroxyhydrocarbyl ureas as lubricating oil detergents
NL7810136A (en) * 1970-08-07 1979-01-31 Pfizer METHOD OF GENERATING ENDOGENIC INTERFERON.
US5607906A (en) * 1995-11-13 1997-03-04 Kyodo Yushi Co., Ltd. Grease composition for constant velocity joints

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