US2316903A - Addition agent for lubricants - Google Patents

Addition agent for lubricants Download PDF

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Publication number
US2316903A
US2316903A US424543A US42454341A US2316903A US 2316903 A US2316903 A US 2316903A US 424543 A US424543 A US 424543A US 42454341 A US42454341 A US 42454341A US 2316903 A US2316903 A US 2316903A
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Prior art keywords
compounds
oil
allophanate
radicals
lubricants
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Expired - Lifetime
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US424543A
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Paul R Van Ess
Ellis R White
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Shell Development Co
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Shell Development Co
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Priority to US424543A priority Critical patent/US2316903A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/06—Use of additives to fuels or fires for particular purposes for facilitating soot removal
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • C10M133/18—Amides; Imides of carbonic or haloformic acids
    • C10M133/20—Ureas; Semicarbazides; Allophanates
    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/16—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiourea type, i.e. containing the group
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • 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
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • 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
    • 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
    • C10M2215/16—Nitriles
    • 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
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/064—Thiourea type 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
    • 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
    • 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

  • This invention relates to improved compositions of matter comprised of normally liquid or solid organic substances containing an added ingredient which improves their properties in one or more important respects. More particularly,
  • X represents oxygen or sulfur
  • R2 and R are hydrogen or hydrocarbon radicals, preferably hydrogen
  • R1 may be an aliphatic, alicyclic, aromatic, or mixed cyclic and chain radical.
  • the hydrocarbon radicals R2 and R3 may contain (preferably not more than one) polar, neutral, or basic substituent. Suitable substituents are, for example, halogen, CN, 0H, OR', -COR', --COOR', --N'H2, -NHR., NRR", -SR1, wherein R and R" are hydrocarbon radicals such as alkyl, aryl, aralkyl and cyclo-alkyl radicals.
  • the compounds of this invention be soluble in the material to be improved.
  • some of the compounds otherwise complying with the above general formula are only slightly soluble, for example, in mineral oils because they possess oil solubilizing radicals which are too small or which are present in insufflcient numbers.
  • Effective oil-solubilizing radicals are in general hydrocarbon radicals possessing at least 6 and preferably 10 or more carbon atoms, such as hexyl, etc., heptyl, octyl, iso-octyl, decyl, dodecyl, tetradecyl, cetyl wax, etc., radicals; aromatic radicals such as phenyl, tolyl, xylyl, benzyl, etc., radicals.
  • Solubility is not always essential.
  • compounds having extreme pressure properties may merely be suspended in lubricating oils and yet be effective.
  • Suspensions of little soluble or insoluble addition agents may be particularly useful in greases, such as soda soap greases, calcium soap greases, aluminum soap greases, petrolatum greases, etc., with which they may form substantially stable plastic mixtures.
  • the amounts of our compounds to be added to the hydrocarbon oils effectively to improve their properties will vary with the type of, improvement to be achieved. In general, when added to lubricating oils to improve wear resistance, the amounts required normally vary from .1% to 10%, preferably 5% to 5%, depending upon the conditions to be met. If complete solubility of the addition agent is required, its solubility limits frequently set the upper limits of the amounts which can be safely incorporated.
  • methyl allophanate and similar allophanates such as propyl allophanate, isopropyl allophanate, tertiary butyl allophanate, amyl allophanate, etc.
  • the allophanates may be obtained, for example, by reacting 1 mol of chlor carbonic esters with 2 mols of urea or thiourea, or by passing cyanic acid vapors into anhydrous alcohols; or by the reaction of carbamic esters or urethanes or thiourethanes with urea chloride, etc., or by the reaction of saturated alcohols with carbamyl or urea chloride.
  • butyl allophanate was prepared as follows:
  • Carbamyl chloride was dissolved in benzene and added to a benzene solution of butyl alcohol in the ratio of 2 mols oi carbamyl chloride to 1 mol of alcohol. The reaction took place at room tem-- perature. The mixture was then washed with water to extract hydrogen chloride. The water layer was withdrawn and the remaining benzene solution was evaporated by heating.
  • oils containing the improving agents may in addition also contain other addition agents normally added to hydrocarbon oils; thus the compounds of this invention may be used, for example, in gasoline together with antiknock compounds and conventional anti-oxidants, or in lubricating oils together with conventional antioxidants, blooming agents, anticorrosives, extreme pressure compounds, detergents, wedging compounds, i. e., long-chain polar compounds, etc., or in Diesel fuels together with knock suppressors, conventional antioxldants, anti-corrosives. etc.
  • mutual solvents such as alcohols, ethers, amines, etc., of suitable boiling temperatures may be used.
  • Example I A sample of white oil was divided into two portions. Naphthenyl allophanate in an amount of 1% by weight was dissolved in one portion.
  • the doped and undoped oils were then tested on the multiple four-ball machine similar in principle to the Boerlage apparatus described in the magazine, Engineering, vol. 136, July 14, 1933, to determine their ability to prevent wear.
  • This apparatus comprises four steel balls arranged in pyramid formation. The top balls are rotated by spindles against the three bottom balls which are clamped in a stationary ball holder. The balls are immersed in the oil to be tested. Six tests were run simultaneously at a controlled temperature of 130 C. The diameters of the wear scars worn on the three balls forming the base of each pyramid were measured and the average taken as the true indication of wear.
  • Unblended oil Blended oil Iii The oil improving agents contemplated by this invention may be single compounds or mixtures of these compounds.
  • An improved hydrocarbon oil selected from the group consisting of Diesel fuel and lubricants containing a minor amount of a compound selected from the group consisting of the esters of allophanic acids and thio-allophanic acids.
  • An improved lubricant comprising a mineral lubricating oil having admixed therewith a minor proportion of a compound selected from the group consisting of the esters of allophanlc acids and thio-allophanic acids.
  • composition of claim 1 which contains .1% to 10% by weight of the ester.
  • An improved lubricating oil comprising a mineral lubricating oil containing dissolved therein a small amount of an oil-soluble compound selected from the group consisting of the esters of allophanic acids and thio-allophanic acids.
  • An improved lubricating oil comprising a mineral lubricating oil containing dissolved therein a small amount of naphthenyl allophana e.
  • An improved grease composition comprising a soap and a mineral lubricating oil having admixed therewith a small amount of a compound selected from the group consisting of the esters of allophanic acids and thio-allophanic acids.
  • An improved lubricating oil comprising a mineral lubricating oil containing dissolved therein a small amount of an allophanate having the general formula Illl RzXHX wherein R1 and R2 are radicals selected from the group consisting of hydrogen and hydrocarbon radicals, R3 is a radical having at least 6 carbon atoms selected from the group consisting of aliphatic, alicyclic, aromatic, and mixed cyclic and chain radicals, and X is a radical selected from the group consisting of oxygen and sulfur.

Description

Patented Apr. 20, 1943 UNITED STATS AT E ADDITION AGENT FOR LUBRICANTS of Delaware No Drawing. Application December 26, 1941, Serial No. 424,548
7 Claims.
This application is a continuation-in-part of our copending application Serial No. 376,380, filed January 28, 1941.
This invention relates to improved compositions of matter comprised of normally liquid or solid organic substances containing an added ingredient which improves their properties in one or more important respects. More particularly,
- it relates to improved lubricating oil and greases.
Within recent years many difierent substances have been added to lubricating oils and greases to impart to them properties not ordinarily possessed by such materials or to improve certain characteristics already possessed by them or to imhibit the development of undesirable properties latently present in the oil. It is customary, for example, where the lubricant is subjected to oxidizing conditions as. in an automobile crankcase, to add an agent which will inhibit oxidation of the oil. It is also customary to improve the protective efiect on rubbing surfaces by the addition of certain substances which reduce corrosive or abrasive wear, scufiing, and seizure which normally follow a break in the continuity of the lubricating films due to extreme pressure or unfavorable speed conditions.
We have discovered that allophanates and certain related compounds are useful in bringing about various improvements in hydrocarbon oils when added thereto in relatively small amounts.
Therefore, it is an object of this invention to provide addition agents which, when added to lubricating oil, Diesel fuel oil, etc., will reduce wear, scoring and seizure of metal bearing surfaces. Another object is to reduce corrosiveness of hydrocarbon oils.
According to this invention, allophanates which are of the general formula N-R; Rs
are added to lubricating oils and greases. In this formula X represents oxygen or sulfur, R2 and R: are hydrogen or hydrocarbon radicals, preferably hydrogen, and R1 may be an aliphatic, alicyclic, aromatic, or mixed cyclic and chain radical.
The hydrocarbon radicals R2 and R3 may contain (preferably not more than one) polar, neutral, or basic substituent. Suitable substituents are, for example, halogen, CN, 0H, OR', -COR', --COOR', --N'H2, -NHR., NRR", -SR1, wherein R and R" are hydrocarbon radicals such as alkyl, aryl, aralkyl and cyclo-alkyl radicals.
To be useful, it is normally desirable that the compounds of this invention be soluble in the material to be improved. Under normal conditions, some of the compounds otherwise complying with the above general formula are only slightly soluble, for example, in mineral oils because they possess oil solubilizing radicals which are too small or which are present in insufflcient numbers.
Effective oil-solubilizing radicals are in general hydrocarbon radicals possessing at least 6 and preferably 10 or more carbon atoms, such as hexyl, etc., heptyl, octyl, iso-octyl, decyl, dodecyl, tetradecyl, cetyl wax, etc., radicals; aromatic radicals such as phenyl, tolyl, xylyl, benzyl, etc., radicals.
Solubility, however, is not always essential. For example, compounds having extreme pressure properties may merely be suspended in lubricating oils and yet be effective. Suspensions of little soluble or insoluble addition agents may be particularly useful in greases, such as soda soap greases, calcium soap greases, aluminum soap greases, petrolatum greases, etc., with which they may form substantially stable plastic mixtures. The amounts of our compounds to be added to the hydrocarbon oils effectively to improve their properties will vary with the type of, improvement to be achieved. In general, when added to lubricating oils to improve wear resistance, the amounts required normally vary from .1% to 10%, preferably 5% to 5%, depending upon the conditions to be met. If complete solubility of the addition agent is required, its solubility limits frequently set the upper limits of the amounts which can be safely incorporated.
Specific compounds of this group are methyl allophanate and similar allophanates such as propyl allophanate, isopropyl allophanate, tertiary butyl allophanate, amyl allophanate, etc. Also, benzyl allophanate HNC-N-C=O tttt naphthenyl allophanate HNCNC=0 Hittite \CHI H Ha.H:
The allophanates may be obtained, for example, by reacting 1 mol of chlor carbonic esters with 2 mols of urea or thiourea, or by passing cyanic acid vapors into anhydrous alcohols; or by the reaction of carbamic esters or urethanes or thiourethanes with urea chloride, etc., or by the reaction of saturated alcohols with carbamyl or urea chloride.
For example, butyl allophanate was prepared as follows:
Carbamyl chloride was dissolved in benzene and added to a benzene solution of butyl alcohol in the ratio of 2 mols oi carbamyl chloride to 1 mol of alcohol. The reaction took place at room tem-- perature. The mixture was then washed with water to extract hydrogen chloride. The water layer was withdrawn and the remaining benzene solution was evaporated by heating.
If desired, oils containing the improving agents may in addition also contain other addition agents normally added to hydrocarbon oils; thus the compounds of this invention may be used, for example, in gasoline together with antiknock compounds and conventional anti-oxidants, or in lubricating oils together with conventional antioxidants, blooming agents, anticorrosives, extreme pressure compounds, detergents, wedging compounds, i. e., long-chain polar compounds, etc., or in Diesel fuels together with knock suppressors, conventional antioxldants, anti-corrosives. etc. If desired, in order to raise the solubilities of some oi. the compounds, mutual solvents such as alcohols, ethers, amines, etc., of suitable boiling temperatures may be used.
The uses to which some of these compounds may be applied and the highly satisfactory results obtained are further illustrated by the following examples:
Example I A sample of white oil was divided into two portions. Naphthenyl allophanate in an amount of 1% by weight was dissolved in one portion. The doped and undoped oils were then tested on the multiple four-ball machine similar in principle to the Boerlage apparatus described in the magazine, Engineering, vol. 136, July 14, 1933, to determine their ability to prevent wear. This apparatus comprises four steel balls arranged in pyramid formation. The top balls are rotated by spindles against the three bottom balls which are clamped in a stationary ball holder. The balls are immersed in the oil to be tested. Six tests were run simultaneously at a controlled temperature of 130 C. The diameters of the wear scars worn on the three balls forming the base of each pyramid were measured and the average taken as the true indication of wear.
Results were as follows:
Scar diameters Material 130 0., 7 kg.
load
- .Mm. Undoped oii 0.68 il+naphthenyl allophanate 1% 0. 21
Example II Scar diameters Material 0., 7 kg.
load
Unblended oil Blended oil Iii The oil improving agents contemplated by this invention may be single compounds or mixtures of these compounds.
We claim as our invention:
1. An improved hydrocarbon oil selected from the group consisting of Diesel fuel and lubricants containing a minor amount of a compound selected from the group consisting of the esters of allophanic acids and thio-allophanic acids.
2. An improved lubricant comprising a mineral lubricating oil having admixed therewith a minor proportion of a compound selected from the group consisting of the esters of allophanlc acids and thio-allophanic acids.
3. The composition of claim 1 which contains .1% to 10% by weight of the ester.
4. An improved lubricating oil comprising a mineral lubricating oil containing dissolved therein a small amount of an oil-soluble compound selected from the group consisting of the esters of allophanic acids and thio-allophanic acids.
5. An improved lubricating oil comprising a mineral lubricating oil containing dissolved therein a small amount of naphthenyl allophana e.
6. An improved grease composition comprising a soap and a mineral lubricating oil having admixed therewith a small amount of a compound selected from the group consisting of the esters of allophanic acids and thio-allophanic acids.
v7. An improved lubricating oil comprising a mineral lubricating oil containing dissolved therein a small amount of an allophanate having the general formula Illl RzXHX wherein R1 and R2 are radicals selected from the group consisting of hydrogen and hydrocarbon radicals, R3 is a radical having at least 6 carbon atoms selected from the group consisting of aliphatic, alicyclic, aromatic, and mixed cyclic and chain radicals, and X is a radical selected from the group consisting of oxygen and sulfur.
' PAUL R. VAN ESS.
ELLIS R. WHITE.
US424543A 1941-12-26 1941-12-26 Addition agent for lubricants Expired - Lifetime US2316903A (en)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2429905A (en) * 1943-09-10 1947-10-28 Sun Oil Co Lubricant composition
US2462616A (en) * 1944-12-05 1949-02-22 Standard Oil Dev Co Lubricating oil containing an antioxidant
US2599736A (en) * 1948-08-27 1952-06-10 Shell Dev Lubricating composition containing the reaction product of biuret and aliphatic esters of hydroxy acids
US2848444A (en) * 1955-05-25 1958-08-19 Exxon Research Engineering Co Diphenylamine-metal polysulfide reaction products and method of preparing same
US3330780A (en) * 1965-06-03 1967-07-11 Chevron Res Allophanates as viscosity index improvers
US5084195A (en) * 1988-12-28 1992-01-28 Ciba-Geigy Corporation Lubricant composition comprising an allophanate extreme-pressure, anti-wear additive
EP0590880A1 (en) * 1992-10-01 1994-04-06 Texaco Development Corporation Composition of matter for allophanate encapsulation in an aromatic-aliphatic calixarene
US5509943A (en) * 1992-09-01 1996-04-23 Texaco Inc. Motor fuel detergent additives-hydrocarbyloxypolyether allophonate esters of 2-hydroxy ethane
US8447313B2 (en) 2008-11-27 2013-05-21 Lg Electronics Inc. Method of determining an access mode of cell in a wireless communication system

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2429905A (en) * 1943-09-10 1947-10-28 Sun Oil Co Lubricant composition
US2462616A (en) * 1944-12-05 1949-02-22 Standard Oil Dev Co Lubricating oil containing an antioxidant
US2599736A (en) * 1948-08-27 1952-06-10 Shell Dev Lubricating composition containing the reaction product of biuret and aliphatic esters of hydroxy acids
US2848444A (en) * 1955-05-25 1958-08-19 Exxon Research Engineering Co Diphenylamine-metal polysulfide reaction products and method of preparing same
US3330780A (en) * 1965-06-03 1967-07-11 Chevron Res Allophanates as viscosity index improvers
US5084195A (en) * 1988-12-28 1992-01-28 Ciba-Geigy Corporation Lubricant composition comprising an allophanate extreme-pressure, anti-wear additive
US5300243A (en) * 1988-12-28 1994-04-05 Ciba-Geigy Corporation Lubricant composition
US5629440A (en) * 1988-12-28 1997-05-13 Ciba-Geigy Corporation Lubricant composition
US5726339A (en) * 1988-12-28 1998-03-10 Ciba Specialty Chemicals Corporation Thiocarbonyl allophanate derivatives used as lubricants
US5509943A (en) * 1992-09-01 1996-04-23 Texaco Inc. Motor fuel detergent additives-hydrocarbyloxypolyether allophonate esters of 2-hydroxy ethane
EP0590880A1 (en) * 1992-10-01 1994-04-06 Texaco Development Corporation Composition of matter for allophanate encapsulation in an aromatic-aliphatic calixarene
US8447313B2 (en) 2008-11-27 2013-05-21 Lg Electronics Inc. Method of determining an access mode of cell in a wireless communication system

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