US3007873A - Stable mineral oil compositions - Google Patents

Stable mineral oil compositions Download PDF

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Publication number
US3007873A
US3007873A US822758A US82275859A US3007873A US 3007873 A US3007873 A US 3007873A US 822758 A US822758 A US 822758A US 82275859 A US82275859 A US 82275859A US 3007873 A US3007873 A US 3007873A
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United States
Prior art keywords
ditert
mineral
mineral oil
borate
oil compositions
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Expired - Lifetime
Application number
US822758A
Inventor
William W Reynolds
Low Hans
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Shell USA Inc
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Shell Oil Co
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Filing date
Publication date
Priority to NL252953D priority Critical patent/NL252953A/xx
Priority to BE592213D priority patent/BE592213A/xx
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US822758A priority patent/US3007873A/en
Priority to GB21990/60A priority patent/GB892786A/en
Priority to FR830897A priority patent/FR1269139A/en
Priority to JP2867260A priority patent/JPS374423B1/ja
Priority to DES69082A priority patent/DE1233525B/en
Application granted granted Critical
Publication of US3007873A publication Critical patent/US3007873A/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
    • 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
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl 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
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl 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
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/066—Arylene diamines
    • 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
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or 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
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
    • 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
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/17—Electric or magnetic purposes for electric contacts

Definitions

  • This invention relates to improved lubricating oil compositions, and more particularly to mineral lubricating oil compositions which are resistant to oxidative deterioration under storage or use in equipment subjected to adverse operating conditions of temperature and pressure.
  • Lubricating oils such as mineral oils in the lubricating viscosity range tend to deteriorate and break down due to oxidation both in storage and during use, particularly at extremely high temperatures, such as above 400 F. and higher, resulting in the formation of undesirable products such as gums, sludges, resins, acidic products and other deleterious products which decrease the useful life of'the oil or render it useless Within a short period of time.
  • Mineral oils of this type include aircraft, truck and automobile mineral lubricating oils, industrial oils such as gear oils, transformer oils, hydraulic oils and the like.
  • the oil-soluble aromatic amines represented by Formula I include diphenyl, dinaphthyl, phenyl alphanaphthyl, phenyl beta-naphthyl amines and mixtures thereof.
  • the boron esters represented by Formula II (RO) B are compounds wherein at least one R is a branched chain alkyl radical such as a tert-alkylaryl radical, e.g., tert-butylphenyl, tert-amylphenyl, tert-octylphenyl, ditertbutylphenyl, ditert-amylphenyl, ditert-octylphenyl, methylter-t butylphenyl, methylditert butylphenyl, ditertbutylnaphthyl, tert-butylnaphthyl, 2 ethylexylphenyl, etc.
  • a tert-alkylaryl radical e.g., tert-butylphenyl, tert-amylphenyl, tert-octylphenyl, ditertbutylphenyl,
  • Boron esters of this type which are particularly preferred are borate esters containing a ditert-alkylphenyl group in the molecule such as 2,6-ditert-butyl-4-methylphenyl di-nbutyl borate, 2,6-ditert-butylphenyl di-n-butyl borate, 2,6- ditert-buty1-4-methylpheny1 di-n-octylborate, 2,6-ditert- 2 butyl-4-methylphenyl diphenyl borate, Z-ethylhexylphenyl dibutyl borate and the like.
  • a ditert-alkylphenyl group in the molecule such as 2,6-ditert-butyl-4-methylphenyl di-nbutyl borate, 2,6-ditert-butylphenyl di-n-butyl borate, 2,6- ditert-buty1-4-methylpheny1 di-n-octylborate
  • the additive combination of this invention effectively stabilizes a variety of petroleum lubricating stocks such as paraflinic, naphthenic and mixed base mineral oils having a viscosity range of from 50 SUS at F. to 250 SUS at 210 F.
  • a typical oil is a refined mineral lubricating oil (X) having the following properties:
  • Another typical oil (Y) is an Oklahoma neutral petroleum fraction having the following properties:
  • compositions were prepared and evaluated in a micro-oxidation test of the MIL-L- 7808 oxidation test under the following test condition: air flow of l liter/hour oxidizing agent, 400 F., solid metal catalyst (Ag, Ti, Cu, Mg, Fe), with the results as shown in Table I.
  • Lubricating oil compositions of this invention such as 4 4.
  • a mineral lubricating oil containing from about 0.001% to about 2% each of dinaphthylamine and 2,6- ditert-butylphenyl di-n-butyl borate.
  • a mineral lubricating oil containing from about 5 0.001% to about 2% each of dinaphthylamine and 2,6-

Description

3,007,873 Patented Nov. 7, 1961 This invention relates to improved lubricating oil compositions, and more particularly to mineral lubricating oil compositions which are resistant to oxidative deterioration under storage or use in equipment subjected to adverse operating conditions of temperature and pressure.
Lubricating oils such as mineral oils in the lubricating viscosity range tend to deteriorate and break down due to oxidation both in storage and during use, particularly at extremely high temperatures, such as above 400 F. and higher, resulting in the formation of undesirable products such as gums, sludges, resins, acidic products and other deleterious products which decrease the useful life of'the oil or render it useless Within a short period of time. Mineral oils of this type include aircraft, truck and automobile mineral lubricating oils, industrial oils such as gear oils, transformer oils, hydraulic oils and the like.
It is known that certain aromatic amines are useful as oxidation inhibitors for mineral oils. However, their application is limited because of their tendency to discolor mineral oils and form deposits, particularly at elevated temperatures. Other types of anti-oxidants such as alkyl phenols, such as diand trialkylphenols, e.g., 2,4- diamylphenol and 2,6-ditert-buty1-4-methylphenol are effective only in certain type of mineral oil and are oxidatively unstable at elevated temperatures.
It is an object of this invention to inhibit or prevent oxidation of mineral oil. Still another object is to inhibit or prevent deterioration, discoloration and deposit formation in mineral oil during storage and use over a wide temperature range, particularly at elevated temperatures. Other objects of the invention will be apparent from the following description of the invention.
It has now been discovered that various types of mineral lubricating oil including those which contain substantial amounts of aromatic (30% can be effectively stabilized even at temperatures above 400 F. without undesirable side efiects by addition thereto of small amounts (0.001- 2%, preferably 0.002-1% by weight) each of an oilsoluble aromatic amine having the Formula I RR NH, wherein the Rs are the same or different monoor diaromatic radicals, and an oil-soluble boron ester having the Formula II (RO) B, wherein at least one R is an aryl radical having attached thereto at least 1 and preferably 2 branched-chain alkyl radicals such as tert-alkyl groups and the other Rs are the same or different hydrocarbyl radicals such as alkyl, aryl, alkaryl, aralkyl or cycloalkyl radicals. Boron esters represented by Formula II which contain at least two tert-alkyl-phenol Rs are preferred. 0
The oil-soluble aromatic amines represented by Formula I include diphenyl, dinaphthyl, phenyl alphanaphthyl, phenyl beta-naphthyl amines and mixtures thereof.
The boron esters represented by Formula II (RO) B are compounds wherein at least one R is a branched chain alkyl radical such as a tert-alkylaryl radical, e.g., tert-butylphenyl, tert-amylphenyl, tert-octylphenyl, ditertbutylphenyl, ditert-amylphenyl, ditert-octylphenyl, methylter-t butylphenyl, methylditert butylphenyl, ditertbutylnaphthyl, tert-butylnaphthyl, 2 ethylexylphenyl, etc. Boron esters of this type which are particularly preferred are borate esters containing a ditert-alkylphenyl group in the molecule such as 2,6-ditert-butyl-4-methylphenyl di-nbutyl borate, 2,6-ditert-butylphenyl di-n-butyl borate, 2,6- ditert-buty1-4-methylpheny1 di-n-octylborate, 2,6-ditert- 2 butyl-4-methylphenyl diphenyl borate, Z-ethylhexylphenyl dibutyl borate and the like.
The additive combination of this invention effectively stabilizes a variety of petroleum lubricating stocks such as paraflinic, naphthenic and mixed base mineral oils having a viscosity range of from 50 SUS at F. to 250 SUS at 210 F. A typical oil is a refined mineral lubricating oil (X) having the following properties:
Pour point, F 29-31 Flash point, F. (COC) Min. 420 Viscosity SUS, 100 F 345-355 Unsulfonated residue Min. 98
Another typical oil (Y) is an Oklahoma neutral petroleum fraction having the following properties:
Specific gravity 0.876 Pour point, F +10 Viscosity at 100 F., cs 56.88 93.9 450 490 23.7
To illustrate the pronounced superiority of the additive combination in stabilizing and preventing oxidation of mineral oil, the following compositions were prepared and evaluated in a micro-oxidation test of the MIL-L- 7808 oxidation test under the following test condition: air flow of l liter/hour oxidizing agent, 400 F., solid metal catalyst (Ag, Ti, Cu, Mg, Fe), with the results as shown in Table I.
reali n EoE iIIIIIIII:III: Fire point, F Aromatics, percent Table I [Base=retined mineral lubricating oil X. Amount of inhlbitor=0.02M=
0.002 mole/100 g.]
Hours to Gain Due Inhibitor Absorb 1 To mlllirnole Inhibitor,
Og/g. oil Hrs.
(1) None 11 (2) Phenyl-alpha-naphthylamine 19 8 (3) Beta-beta-dinapl1thylami11e 17 6 (4) Diphenylamine 15 4 (5) 2,6-ditert-butyl-4-methyl-phenyl di-nbutyl borate 18 7 2 5 62 51 29 18 46 35 The unexpected results which the additive combinations of the present invention produce were further demonstrated when oil compositions shown in Table II were tested in the Dornte Oxidation Test described in the National Petroleum News, September 17, 1941, pages R-294-296, with the results as shown in Table II.
Table II [Base=refined mineral oil (X). Oonditinns=302 F., 1800 ml., On cat, time, min. Amount of inhibitor=0.0025 mole/100 g. oi1=0.025 M] Inhibitor Time (min) (2) Pllenyl-alpha-naphthylamine 8, 340 (5) 2,6-ditert-butylphenyl-4-rnethylphenyl di-n-butyl borate. 1, 043 (6) 2+5 22,500
Lubricating oil compositions of this invention such as 4 4. A mineral lubricating oil containing from about 0.001% to about 2% each of dinaphthylamine and 2,6- ditert-butylphenyl di-n-butyl borate.
5. A mineral lubricating oil containing from about 5 0.001% to about 2% each of dinaphthylamine and 2,6-
ditert-butyl-4-methylphenyl di-n-butyl borate.
References Cited in the file of this patent UNITED STATES PATENTS 2,410,652 Griffin et a1 Nov. 2, 1946 2,497,521 Trautman Feb. 14, 1950 2,813,830 Trautman Nov. 19, 1957

Claims (1)

1. A MINERAL LUBRICATING OIL CONTAINING FROM ABOUT 0.001% TO ABOUT 2% EACH OF AN ARYL AMINE OF THE GROUP CONSISTING OF PHENYL-ALPHA-NAPHTHYLAMINE AND DINAPHTHYLAMINE AND A BORATE OF THE GROUP CONSISTING OF 2,6-DITERTBUTYLPHENYL DI-N-BUTYL BORATE AND 2,6-DITERT-BUTYL-4METHYLPHENYL DI-N-BUTYL BORATE.
US822758A 1959-06-25 1959-06-25 Stable mineral oil compositions Expired - Lifetime US3007873A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
NL252953D NL252953A (en) 1959-06-25
BE592213D BE592213A (en) 1959-06-25
US822758A US3007873A (en) 1959-06-25 1959-06-25 Stable mineral oil compositions
GB21990/60A GB892786A (en) 1959-06-25 1960-06-23 Stable mineral oil compositions
FR830897A FR1269139A (en) 1959-06-25 1960-06-23 Stable mineral oil compositions
JP2867260A JPS374423B1 (en) 1959-06-25 1960-06-23
DES69082A DE1233525B (en) 1959-06-25 1960-06-23 Lubricating oil additive

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US822758A US3007873A (en) 1959-06-25 1959-06-25 Stable mineral oil compositions

Publications (1)

Publication Number Publication Date
US3007873A true US3007873A (en) 1961-11-07

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ID=25236890

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US822758A Expired - Lifetime US3007873A (en) 1959-06-25 1959-06-25 Stable mineral oil compositions

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US (1) US3007873A (en)
JP (1) JPS374423B1 (en)
BE (1) BE592213A (en)
DE (1) DE1233525B (en)
FR (1) FR1269139A (en)
GB (1) GB892786A (en)
NL (1) NL252953A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125526A (en) * 1964-03-17 Lubricating greases containing borate
US4328113A (en) * 1980-01-14 1982-05-04 Mobil Oil Corporation Friction reducing additives and compositions thereof
US4623360A (en) * 1985-10-31 1986-11-18 Ethyl Corporation Fuel compositions
US8343901B2 (en) 2010-10-12 2013-01-01 Chevron Oronite Company Llc Lubricating composition containing multifunctional hydroxylated amine salt of a hindered phenolic acid

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4741088B2 (en) * 2001-02-02 2011-08-03 Ｊｘ日鉱日石エネルギー株式会社 Lubricating oil composition
JP2004083746A (en) 2002-08-27 2004-03-18 Nippon Oil Corp Lubricant oil composition for internal combustion engine

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2410652A (en) * 1943-09-15 1946-11-05 Shell Dev Compounded lubricating oil
US2497521A (en) * 1947-12-03 1950-02-14 Gulf Research Development Co Oil compositions containing amine salts of boro-diol complexes
US2813830A (en) * 1953-11-07 1957-11-19 Gulf Research Development Co Hydrocarbon oil compositions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB748430A (en) * 1953-11-07 1956-05-02 Gulf Research Development Co Hydrocarbon oil compositions and processes for preparing the same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2410652A (en) * 1943-09-15 1946-11-05 Shell Dev Compounded lubricating oil
US2497521A (en) * 1947-12-03 1950-02-14 Gulf Research Development Co Oil compositions containing amine salts of boro-diol complexes
US2813830A (en) * 1953-11-07 1957-11-19 Gulf Research Development Co Hydrocarbon oil compositions

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125526A (en) * 1964-03-17 Lubricating greases containing borate
US4328113A (en) * 1980-01-14 1982-05-04 Mobil Oil Corporation Friction reducing additives and compositions thereof
US4623360A (en) * 1985-10-31 1986-11-18 Ethyl Corporation Fuel compositions
US8343901B2 (en) 2010-10-12 2013-01-01 Chevron Oronite Company Llc Lubricating composition containing multifunctional hydroxylated amine salt of a hindered phenolic acid

Also Published As

Publication number Publication date
FR1269139A (en) 1961-08-11
BE592213A (en)
DE1233525B (en) 1967-02-02
GB892786A (en) 1962-03-28
NL252953A (en)
JPS374423B1 (en) 1962-06-13

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