US2268608A - Lubricants - Google Patents

Lubricants Download PDF

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Publication number
US2268608A
US2268608A US307588A US30758839A US2268608A US 2268608 A US2268608 A US 2268608A US 307588 A US307588 A US 307588A US 30758839 A US30758839 A US 30758839A US 2268608 A US2268608 A US 2268608A
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US
United States
Prior art keywords
lubricant
amine
oil
sulfur
chlorine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US307588A
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English (en)
Inventor
George M Mcnulty
John C Zimmer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Standard Oil Development Co
Original Assignee
Standard Oil Development Co
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Filing date
Publication date
Application filed by Standard Oil Development Co filed Critical Standard Oil Development Co
Priority to US307588A priority Critical patent/US2268608A/en
Priority to GB16378/40A priority patent/GB545355A/en
Priority to FR886040D priority patent/FR886040A/fr
Application granted granted Critical
Publication of US2268608A publication Critical patent/US2268608A/en
Priority to FR54665D priority patent/FR54665E/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04—Elements
    • C10M2201/043—Sulfur; Selenenium; Tellurium
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • 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
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    • 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
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/16—Naphthenic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
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    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/40—Fatty vegetable or animal oils
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C—CHEMISTRY; METALLURGY
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    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
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    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
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    • C10M2211/06—Perfluorinated compounds
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    • C10M2211/08—Halogenated waxes
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
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    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2215/10—Amides of carbonic or haloformic acids
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    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • 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
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • 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—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • This invention relates to improved lubricants and more particularly to oil and grease lubricating compositions intended for lubricating moving metal parts which contact each other under high pressures,.such as high film strength'oils for bearings and engines, extreme pressure lubricants forgears, and cutting oils as used for machining various metals, etc.
  • Example 1 An E. P. (extreme pressure). lubricant was made of the following composition:
  • Example 2 A small amount of trie'thanolamine was added to the same lubricating composition and found to be eliective in eliminating corrosion and stain-
  • Example 3 Small amounts of cyclohexylamine, triamylamine and dicyclohexylamine were similarly tested and found to be excellent in their efiectiveness in eliminating corrosion and staining.
  • Example 4 A cutting oil was prepared having the following composition:
  • This cutting oil is suitable for machining bronze metal parts but it causes darkening of the bronze.
  • Example 5 A lubricant containing sulfur or chlorine or both treated with a phosphorous-bearing oil-soluble base towhich trlamylamine has been added is non-reactive to ferrous and cuprous alloys.
  • Example 7 The polymerization product formed by reacting sodium polysulfide with a halogenated hydrocarbon following blending with mineral oil and containing a product such as cyclohexylamine, dicyclohexylamine, or triethanolamine does not corrode or stain steel.
  • a cutting oil containing dissolved sulfur and chlorine or other halogen which can be used on cutting machines containing bronze gibs and used for cutting operations on ferrous or cuprous alloys, causes staining or rusting or corrosion, but this is prevented by adding a small amount of an amine such as phenylethanol amine, hexyl amine or amyl cyclohexyl amine.
  • the amines and substituted amines arepreferred, particularly those having an ionization constant greater than about 1 10 or having a pKH value above about 7.0. (The higher the numerical figure for the value pKH, the more basic is the compound.)
  • the amines to be used are preferably selected from the group consisting of mono-, (11-, and trialkyl and cyclo-alkyl amines, dialkyl aryl amines. and hydroxy, aryl and 1 double bond (meaning corresponding oleflnic) derivatives thereof.
  • the amines to be used should have an ionization constant between the approximate limits of 1X 10 and 1X or a pH range of 7.0-11.1, and preferably an ionization constant between .lxlO- and 1 l0 or a pH of 9.0-11.0, and should preferably also have a boiling point between the approximate limits of 150 and 400 C. at atmospheric pressure.
  • Phenyl ethanolamine has a pKH value of 7.35 and a boiling point of 286 C. and dicyclohexylamine has a pKH value of 10.74. and a boiling point of 115 C. (at 8 m. 121.). Both of these amines were shown above to be particularly satisfactory, both in laboratory cor-
  • the term pKH is a reciprocal measurement of the hydrogen ion concentration determined after a partial nciltrnliznflon, as described in J. A. C. 8., vol. 54. p. 8469 et seq. (1932).
  • TABLI 6.-Phenul uuanidines pKH 5o Guanldine 13.65 Phenylguanidine 10.77 Diphenylguanidine 10.12 Triphenylguanidine 9.10
  • TABLI 7.Miscellaneous amines in order accord- Di-isopropylamhie 11.05
  • cyclo-alkylamines in which one or 20 more of the hydrogens on the cyclic nucleus is replaced by alkyl groups.
  • Some of the hydroxy, 'aryl and 1 double bond or olefinic derivatives of the alkyl and cycloalkyl amines include the following:
  • Mono-cetyl diethanol amine Phenyl ethanol amine (the phenyl group being attached to the ethanol group but not directly to the nitrogen) Di-cyclo hexylene amine Mono-oleyl amine Di-oleyl amine Cyclohexyl oleyl amine Diethyl benzyl amine 5 a -Mono and dialkyl mono aryl amines e. g. N-diethyl phenyl amine, N-octadecyl benzyl ammonium hydroxide, dibenzyloctadecyl sulfonium hydroxide, etc., and their salts or 4 soaps may also be used.
  • the amount of the oil-soluble organic base to be used should be between the approximate limits of 0.01% and 1.0% depending upon the type and the amount of chlorine and sulfur or other active and corrosive load-carrying elementsin the lubricant but generally an amount between the approximate limits of 0.05% and 0.5% will sufiice.
  • the invention is particularly applicable to extreme pressure lubricants containing corrosive chlorine compounds, for instance, chlorinated aliphatic or aromatic hydrocarbons such as chlorinated paraffin wax, kerosene, aromatic, petroleum, or coal tar solvents and derivatives in which a portion of the chlorine has been replaced by sulfur.
  • chlorine especially the active chlorine
  • the amount of chlorine, especially the active chlorine, to be used will, of course, depend upon the severity of the conditions under which the lubricant is to be used but 05 will generally vary between the approximate limits of 5% to 50% in the chlorinated organic compounds or between the approximate limits of .05% and 10% based on the total weight of lubricant (exclusive of any water which may be used as in the preparation of water-soluble type cutting oil).
  • sulfur compounds especially to increase Y the stability of the lubricantat high temperature and for this purpose a sulfurized fatty or mineral oil or a sulfur compound such as an organic sulfide, mercaptan, dior poly-sulfides, xanthates, xanthogen sulfides, thio carbonates, etc., may be used in which generally from about 1% to 30% of sulfur is incorporated in the active or combined state. Based on the total weight I of lubricant, the proportion of sulfur should normally be between the of about 0.2% and 10%.
  • ferric chloride which prevent metal to metal contact and resultant welding and scoring.
  • These films particularly in the presence of moisture which is almost always present in gear cases tend to hydrolyze into metal oxides and hydrochloric acid.
  • the chlorine compounds in the lubricant itself tend to hydrolyze with the liberation of hydrochloric acid (H01) and this acid in turn attacks the metal surface because iron and steel and various alloys in general are quite susceptible to attack or corrosion by hydrochloric acid and other strong halogen acids.
  • oil-soluble organic amines of this inven tlon are believed to have .some effect in preventing hydrolysis of the metal chloride films and they also apparently neutralize any nascent hydrochloric acid which may tend to form, and these organic amines act diiferently in oil than they do in aqueous media and have some unexpected ability to alter the chemical reactions which take place when the lubricant is subjected to extreme pressure conditions, permitting the desired film formation and lubrication under high pressures without substantial corrosion of the adjacent metal surfaces.
  • lubricant prepared according to the present invention
  • fatty, fatty acid or naphthenic acid soaps, esters, thickeners such as polyisobutylene having a molecular weight above 1,000, pour dewell as hetero-cyclo-aliphatic amines, such as the alkyl piperidines disclosed in Table 4.
  • a lubricant comprising an active halogen in a form normally corrosive to metals but capable of greatly increasing the load-carrying capacity of the lubricant and also comprising a, small amount of an oil-soluble cycle-aliphatic amine having a pKH value greater than about 7.0.
  • An extreme pressure lubricant comprising a major proportion of a mineral 011 base stock. a substantial amount of an organic compound containing a substantial amount of halogen in an active condition, and a small amount of an oilsoluble cyclo-alkylamine having a pKH value between the approximate limits of about 9.0 and 11.1.
  • An extreme pressure lubricant comprising a' major proportion of a mineral 011 base stock, a substantial amount of an organic compound containing a substantial amount of chlorine and sulfur in an active condition. and a small amount of an oil-soluble cyclo-alkylamine having a'pKH value between the approximate limits of 8.0 and 11.0.
  • Lubricant according to claim 3 in which the amount of amine present is enough to substantially prevent corrosion of metals coming in contact therewith.
  • Lubricant according to claim 3 in which the amine has a boiling point between the approximate limits of 150 to 400 C.
  • Lubricant according to claim 3 in which the amine contains at least one cyclo-hexyl group.
  • Lubricant according to claim 3 in which 0.01 to 1.0% of dicyclohexylamine is used.
  • An extreme. pressure lubricant comprising a major proportion of a mineral oil base stock, a substantial amount of an organic compound containing a substantial amount of chlorine and phosphorus in an active condition, and a small amount or an oil-soluble cycle-aliphatic amine having a pH value greater than about 7.0.
  • An extreme pressure lubricant comprising a major proportion of a mineral oil base stock, a substantial amount of an organic compound containing a substantial amount of halogen, sulfur and phosphorus in an active condition, and a small amount of an oil-soluble cycle-aliphatic amine having a pH value greater than about 7.0-.
  • An extreme pressure lubricant comprising a major proportion of mineral oil base stock, a substantial amount of a compound containing halogen in an active condition, and a small amount of a cycle-aliphatic amine having attached to the nitrogen atom one hydrogen atom and at least one cycle-aliphatic hydrocarbon group.
  • Lubricant according to claim 12 in which the amine has the general formula NHRz, in which R represents a cyclo-alkyl group.
  • An extreme pressure lubricant comprising a major proportion of mineral oil bas stock, a substantial amount oiv constituents containing chlorine and sulfur in an active condition, said active chlorine being present in an amo nt of about .05% to 10% based on the total lubricant, and said active sulfur being present in an amount of about 0.2% to 10% based on the total lubricant and said lubricant also containing about .01% to 1.0% of a cyclo-alkylamine having the property of preventing corrosion and staining of metals coming in contact therewith, due to said active chlorine and sulfur.
  • An extreme pressure lubricant comprising a major proportion of a mineral 011 base stock, a substantial amount of an organic compound containing chlorine in active condition, the
  • chlorine present being at least about 2.8% by weight of the total lubricant, and a small amount of an oil-soluble cyclo-aliphatic amine having a pKH value greater than about 7.0.
  • An extreme pressure lubricant comprising about 83% of mineral lubricating oil, about 10% of sulfurized non-corrosive fatty oil base containing 10% of sulfur, and about 7% of chicrinated wax containing about 40% of chlorine,

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US307588A 1939-12-05 1939-12-05 Lubricants Expired - Lifetime US2268608A (en)

Priority Applications (4)

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US307588A US2268608A (en) 1939-12-05 1939-12-05 Lubricants
GB16378/40A GB545355A (en) 1939-12-05 1940-11-12 An improved manufacture of lubricants
FR886040D FR886040A (fr) 1939-12-05 1940-11-18 Lubréfiants
FR54665D FR54665E (fr) 1939-12-05 1946-01-29 Lubrifiants

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Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2434978A (en) * 1944-04-15 1948-01-27 William A Zisman Anticorrosion additives for synthetic lubricants
US2447483A (en) * 1944-04-15 1948-08-24 Us Navy Additives for silicone oils
US2453850A (en) * 1941-12-03 1948-11-16 Standard Oil Dev Co Lubricating compositions
US2460259A (en) * 1946-01-22 1949-01-25 W H And L D Betz Method of protecting systems for transporting media corrosive to metal
US2468520A (en) * 1947-08-30 1949-04-26 Standard Oil Dev Co Extreme pressure lubricating compositions
US2476271A (en) * 1946-05-29 1949-07-19 Standard Oil Co Lubricating oil additive
US2511250A (en) * 1947-11-14 1950-06-13 Gulf Research Development Co Stabilized extreme pressure lubricants
US2580005A (en) * 1947-12-31 1951-12-25 Standard Oil Dev Co Extreme pressure lubricating compositions
US2591570A (en) * 1949-04-08 1952-04-01 Socony Vacuum Oil Co Inc Cutting oil
US2596425A (en) * 1947-09-11 1952-05-13 Cities Service Oil Co Method of inhibiting hydrogen sulfide corrosion of metals
US2602049A (en) * 1948-12-24 1952-07-01 Gulf Oil Corp Antioxidants for mineral oil lubricants and compositions containing the same
US2626240A (en) * 1949-06-25 1953-01-20 Texas Co Noncorrosive soluble oil containing active sulfur
US2655478A (en) * 1949-06-25 1953-10-13 Texas Co Noncorrosive soluble oil containing active sulfur
US2672484A (en) * 1945-05-01 1954-03-16 Macy Rudolph Stabilization of levinstein mustard gas
US2696473A (en) * 1951-06-20 1954-12-07 Texas Co Halogen containing extreme pressure lubricant stabilized with a polyalkylene polyamine
US2701237A (en) * 1950-09-26 1955-02-01 Harry Sokol Extreme pressure lubricant
US2711396A (en) * 1953-11-25 1955-06-21 Sinclair Refining Co Cutting oil composition
US2735817A (en) * 1956-02-21 Stabilized lubricating oil additives
US2809935A (en) * 1954-12-22 1957-10-15 Pure Oil Co Extreme pressure lubricant
US2820013A (en) * 1956-01-13 1958-01-14 Pure Oil Co Stabilized extreme pressure lubricant
US2830024A (en) * 1953-09-09 1958-04-08 Pure Oil Co Extreme pressure gear lubricant
US3201349A (en) * 1960-11-18 1965-08-17 Sinclair Research Inc Emulsifiable oil composition
US3211653A (en) * 1958-12-31 1965-10-12 Exxon Research Engineering Co Hypoid gear lubricants for slip-lock differentials
US3238130A (en) * 1958-09-23 1966-03-01 Sinclair Research Inc Anti-chatter lubricant for limited slip differential
US3398095A (en) * 1967-11-13 1968-08-20 Shell Oil Co Vapor-space inhibitors
US3499839A (en) * 1967-06-27 1970-03-10 Standard Oil Co Amine-stabilized iodine-containing lubricants
US3779920A (en) * 1971-02-05 1973-12-18 Atlantic Richfield Co Lubricating oil composition

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2735817A (en) * 1956-02-21 Stabilized lubricating oil additives
US2453850A (en) * 1941-12-03 1948-11-16 Standard Oil Dev Co Lubricating compositions
US2447483A (en) * 1944-04-15 1948-08-24 Us Navy Additives for silicone oils
US2434978A (en) * 1944-04-15 1948-01-27 William A Zisman Anticorrosion additives for synthetic lubricants
US2672484A (en) * 1945-05-01 1954-03-16 Macy Rudolph Stabilization of levinstein mustard gas
US2460259A (en) * 1946-01-22 1949-01-25 W H And L D Betz Method of protecting systems for transporting media corrosive to metal
US2476271A (en) * 1946-05-29 1949-07-19 Standard Oil Co Lubricating oil additive
US2468520A (en) * 1947-08-30 1949-04-26 Standard Oil Dev Co Extreme pressure lubricating compositions
US2596425A (en) * 1947-09-11 1952-05-13 Cities Service Oil Co Method of inhibiting hydrogen sulfide corrosion of metals
US2511250A (en) * 1947-11-14 1950-06-13 Gulf Research Development Co Stabilized extreme pressure lubricants
US2580005A (en) * 1947-12-31 1951-12-25 Standard Oil Dev Co Extreme pressure lubricating compositions
US2602049A (en) * 1948-12-24 1952-07-01 Gulf Oil Corp Antioxidants for mineral oil lubricants and compositions containing the same
US2591570A (en) * 1949-04-08 1952-04-01 Socony Vacuum Oil Co Inc Cutting oil
US2655478A (en) * 1949-06-25 1953-10-13 Texas Co Noncorrosive soluble oil containing active sulfur
US2626240A (en) * 1949-06-25 1953-01-20 Texas Co Noncorrosive soluble oil containing active sulfur
US2701237A (en) * 1950-09-26 1955-02-01 Harry Sokol Extreme pressure lubricant
US2696473A (en) * 1951-06-20 1954-12-07 Texas Co Halogen containing extreme pressure lubricant stabilized with a polyalkylene polyamine
US2830024A (en) * 1953-09-09 1958-04-08 Pure Oil Co Extreme pressure gear lubricant
US2711396A (en) * 1953-11-25 1955-06-21 Sinclair Refining Co Cutting oil composition
US2809935A (en) * 1954-12-22 1957-10-15 Pure Oil Co Extreme pressure lubricant
US2820013A (en) * 1956-01-13 1958-01-14 Pure Oil Co Stabilized extreme pressure lubricant
US3238130A (en) * 1958-09-23 1966-03-01 Sinclair Research Inc Anti-chatter lubricant for limited slip differential
US3211653A (en) * 1958-12-31 1965-10-12 Exxon Research Engineering Co Hypoid gear lubricants for slip-lock differentials
US3201349A (en) * 1960-11-18 1965-08-17 Sinclair Research Inc Emulsifiable oil composition
US3499839A (en) * 1967-06-27 1970-03-10 Standard Oil Co Amine-stabilized iodine-containing lubricants
US3398095A (en) * 1967-11-13 1968-08-20 Shell Oil Co Vapor-space inhibitors
US3779920A (en) * 1971-02-05 1973-12-18 Atlantic Richfield Co Lubricating oil composition

Also Published As

Publication number Publication date
GB545355A (en) 1942-05-21
FR886040A (fr) 1943-10-01
FR54665E (fr) 1950-07-27

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