US2910437A - Stabilization of lubricants - Google Patents

Stabilization of lubricants Download PDF

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Publication number
US2910437A
US2910437A US570420A US57042056A US2910437A US 2910437 A US2910437 A US 2910437A US 570420 A US570420 A US 570420A US 57042056 A US57042056 A US 57042056A US 2910437 A US2910437 A US 2910437A
Authority
US
United States
Prior art keywords
grease
inhibitor
stabilization
lubricants
diaminodiphenyl ether
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
US570420A
Inventor
Symon Ted
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.)
Universal Oil Products Co
Original Assignee
Universal Oil Products Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to NL102710D priority Critical patent/NL102710C/xx
Application filed by Universal Oil Products Co filed Critical Universal Oil Products Co
Priority to US570420A priority patent/US2910437A/en
Priority to GB7219/57A priority patent/GB819024A/en
Priority to DEU4409A priority patent/DE1113785B/en
Priority to ES0234133A priority patent/ES234133A1/en
Priority to FR1172914D priority patent/FR1172914A/en
Application granted granted Critical
Publication of US2910437A publication Critical patent/US2910437A/en
Priority to GB43340/60A priority patent/GB899024A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
    • G01R17/00—Measuring arrangements involving comparison with a reference value, e.g. bridge
    • G01R17/10—AC or DC measuring bridges
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/62—Use of additives, e.g. for stabilisation
    • 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
    • C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
    • C11B5/005—Amines or imines
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
    • G01R17/00—Measuring arrangements involving comparison with a reference value, e.g. bridge
    • 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
    • C10M2201/041—Carbon; Graphite; Carbon black
    • 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
    • C10M2201/102—Silicates
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • 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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    • 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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    • C10M2207/40—Fatty vegetable or animal oils
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    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
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    • 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
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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    • 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
    • C10M2227/02—Esters of silicic acids
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    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
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    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
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    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04—Oxidation, e.g. ozonisation

Definitions

  • the synthetic greases generally'are referred to as lithium base grease, sodium base-grease, calcium base grease, barium base-grease, strontium base 'grease, aluminum base grease, etc.
  • These greases are solid or semi-solid gels and, in generaL-are prepared by the addition to mineral or synthetic oils of hydrocarbon-soluble metal soaps or salts of higher fatty acids as, for example, lithium stearate, calcium stearate, aluminum naphthenate, etc.
  • the grease may contain thickening agents such as silica, carbon black, polyacrylatesftalc, etc.
  • Another type of grease is prepared from oxidized petroleum wax, to which the saponifiable base is combined with the proper amount of the desired sapom'fying agent, and the resultant mixture processed to produce a grease.
  • Other types of greases in which the features of the present invention are usable include petroleum grease, whale grease, wool grease, etc., and those made from inedible fats, tallow, butchers waste, etc.
  • the present invention also is particularly applicable to the stabilization of lubricating oils, including those of petroleum or synthetic origin.
  • the synthetic lubricants are of varied types including aliphatic esters, polyalkylene oxides, silicones, esters of phosphoric and silicic acids,
  • aliphatic esters di-(Z-ethylhexyl) sebacate is being used on a comparatively large commercial scale.
  • Other aliphatic esters include dialkyl azelates, dialkyl suberates,
  • the inhibitor may be used along with other additives incorporated in the organic substance.
  • the inhibitor may be used along with higher alcohols, esters, organic amines, poly butene, suI-furized fatty materials, sulfur chlorine compounds, 'dyes, perfumed materials, fillers, etc.
  • a metal include methyl silicone, methylphenyl silicone, etc.
  • the silicates include, for example, tetraisooctyl silicate, etc.
  • the highly fiuorinated hydrocarbons include fluo rinated oil, perfiuorohydrocarbons, etc.
  • the present invention relates to a method of stabilizing synthetic grease which comprises incorporating therein from about 0.1 to about 5% by weight of 2,4'-,diaminod.iphenyl ether.
  • the present invention relates to a method of stabilizing lubricating oil against oxida tive deterioration which comprises incorporating therein a stabilizing concentration of a 2,4'-diaminodiphenyl ether.
  • the present invention comprises a 2,4-diaminodipheny l ether.
  • a preferred inhibitor is 2,4-diaminodiphenyl ether. 7
  • the inhibitor will be utilized in a concentration of from about 0.0001% to about 5% by weight of the organic substance, although in some cases higher trial-kyl deactivator as, for example, disalicylal diamino propane, ethylene diamine tetra-acetic acid tetrasodium salt, etc., or to include other additives such as tricresyl phosphate,
  • the inhibitor of the present invention may be prepared as amixture with one or more of these other additives and incorporated in this manner in the organic substance or components thereof.
  • the inhibitor of the present invention may be incorporatedin the organic substance in any suitable manner and at any suitable stage of preparation.
  • the inhibitor in an organic substance which comprises a mixture of several components, as for example, grease, the inhibitor may be added to one or more of the components of the grease prior to compositing and processing thereof or it may be added to the mix at any time, preferably before final processing in order to obtain intimate mixing and dissolving of the inhibitor in the grease.
  • Example I 2,4'-diaminodiphenyl ether was utilized as an inhibitor in a lithium grease.
  • the grease was prepared by mixing 91% of a Pennsylvania bright stock with 8% of lithium stearate. The mixture was heated at about 450 F. while agitating the same. Subsequently, the grease was cooled while agitating to 320 F. and, at this'temperature, 1% of 2,4'-diaminodiphenyl ether was added. Agitationwas continued and the mixture was allowed to cool to about 250 F. and the grease then further cooled slowly to room temperature.
  • the stability of the grease was tested according to a modified Norma Hoffman method, 'in which a sample of I the grease is placed in a bomb in the presence of brass discs acting as an oxidation catalyst and oxygen is charged thereto. The bomb then is heated to 212 F., and the time required for a drop of 5 pounds pressure is taken as the induction period. In this run, a control sample of the grease (not containing this additive) had an induction period of 10.5 hours. On the other hand, a sample of the grease containing 1% by weight of 2,4- diaminodiphenyl ether had an induction period of 260 hours.
  • the inhibitor of the present invention was exceptionally eliective in improving the stability of the grease.
  • Example 11 This grease had a control (not containing this additive).
  • Example Ill The grease used in this example was a syntheticgrease prepared in substantially the same manner described in Example I, except that 87% of di-Z-ethylhexyl sebacate was mixed with 12% lithium stearate. 1% by weight of 2,4- diaminodiphenyl ether was incorporated in the syn thetic grease. A control sample of the grease (not containing this additive) had an induction period of 17 hours. On the other hand, a sample of the grease containing 1% by weight of 2,4-diamino-dipheny1 ether did not undergo a pressure drop of one pound per square inch until after 318 hours exposure.
  • a method of stabilizing a lubricant normally subject to oxidative deterioration which comprises incorporating 25 therein a stabilizing concentration otza' diniiaadiphen r ether.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Lubricants (AREA)

Description

2,910,437 STABILIZATION F LUBRICANTS Ted Symon, Hinsdale, Ill., assignor, byxmesne assignmentsyto Universal Oil Products Company, Des -Pla1nes, Ill.,.a corporation-of Delaware 'No'DraWing; Application March 9, 1956 Serial No. 570,420 4 Claims. 3 01. 252-32 "The invention isparticularly applicable to the stabilizati'on of greases, either of synthetic orpetroleum origin.
The synthetic greases generally'are referred to as lithium base grease, sodium base-grease, calcium base grease, barium base-grease, strontium base 'grease, aluminum base grease, etc. These greases are solid or semi-solid gels and, in generaL-are prepared by the addition to mineral or synthetic oils of hydrocarbon-soluble metal soaps or salts of higher fatty acids as, for example, lithium stearate, calcium stearate, aluminum naphthenate, etc. The grease may contain thickening agents such as silica, carbon black, polyacrylatesftalc, etc. Another type of grease is prepared from oxidized petroleum wax, to which the saponifiable base is combined with the proper amount of the desired sapom'fying agent, and the resultant mixture processed to produce a grease. Other types of greases in which the features of the present invention are usable include petroleum grease, whale grease, wool grease, etc., and those made from inedible fats, tallow, butchers waste, etc.
The present invention also is particularly applicable to the stabilization of lubricating oils, including those of petroleum or synthetic origin. The synthetic lubricants are of varied types including aliphatic esters, polyalkylene oxides, silicones, esters of phosphoric and silicic acids,
highly fluorine-substituted hydrocarbons, etc. Of the aliphatic esters, di-(Z-ethylhexyl) sebacate is being used on a comparatively large commercial scale. Other aliphatic esters include dialkyl azelates, dialkyl suberates,
2,910,437. e r Patented Oct. 2'7, 1959 ICC or lower concentrations may be employed. The exact concentration to be used will depend upon the particular organic substance being treated. a In most cases concentrations of from about 0.01% to about 3% by weight generally will be employed.
Itis understood that the inhibitor may be used along with other additives incorporated in the organic substance. For example, in grease the inhibitor may be used along with higher alcohols, esters, organic amines, poly butene, suI-furized fatty materials, sulfur chlorine compounds, 'dyes, perfumed materials, fillers, etc. In some 7 cases, it may be of advantage to also include a metal include methyl silicone, methylphenyl silicone, etc., and
the silicates include, for example, tetraisooctyl silicate, etc. The highly fiuorinated hydrocarbons include fluo rinated oil, perfiuorohydrocarbons, etc.
In a specific embodiment the present invention relates to a method of stabilizing synthetic grease which comprises incorporating therein from about 0.1 to about 5% by weight of 2,4'-,diaminod.iphenyl ether.
In another embodiment the present invention relates to a method of stabilizing lubricating oil against oxida tive deterioration which comprises incorporating therein a stabilizing concentration of a 2,4'-diaminodiphenyl ether.
In one embodiment the present invention comprises a 2,4-diaminodipheny l ether. A preferred inhibitor is 2,4-diaminodiphenyl ether. 7
In general, the inhibitor will be utilized in a concentration of from about 0.0001% to about 5% by weight of the organic substance, although in some cases higher trial-kyl deactivator as, for example, disalicylal diamino propane, ethylene diamine tetra-acetic acid tetrasodium salt, etc., or to include other additives such as tricresyl phosphate,
fphenols including 2,6di-tert-butyl-4-rnethylphenol, '2,-4-di-methyl-6-tert-butylphenol, alkylated diphenyl amines, phenyl naphthyl amines, dialkyl phen ylene diamines, phenothiazine, organic selenium compounds, etc., aswell as corrosion inhibitors, extreme pressure additives, viscosity index improvers, etc. When desired, the inhibitor of the present invention may be prepared as amixture with one or more of these other additives and incorporated in this manner in the organic substance or components thereof.
The inhibitor of the present invention may be incorporatedin the organic substance in any suitable manner and at any suitable stage of preparation. For example, in an organic substance which comprises a mixture of several components, as for example, grease, the inhibitor may be added to one or more of the components of the grease prior to compositing and processing thereof or it may be added to the mix at any time, preferably before final processing in order to obtain intimate mixing and dissolving of the inhibitor in the grease.
The following examples are introduced to illustrate further the novelty and utility of the present invention but not with the intention of unduly limiting the same.
Example I 2,4'-diaminodiphenyl ether was utilized as an inhibitor in a lithium grease. The grease was prepared by mixing 91% of a Pennsylvania bright stock with 8% of lithium stearate. The mixture was heated at about 450 F. while agitating the same. Subsequently, the grease was cooled while agitating to 320 F. and, at this'temperature, 1% of 2,4'-diaminodiphenyl ether was added. Agitationwas continued and the mixture was allowed to cool to about 250 F. and the grease then further cooled slowly to room temperature.
The stability of the grease was tested according to a modified Norma Hoffman method, 'in which a sample of I the grease is placed in a bomb in the presence of brass discs acting as an oxidation catalyst and oxygen is charged thereto. The bomb then is heated to 212 F., and the time required for a drop of 5 pounds pressure is taken as the induction period. In this run, a control sample of the grease (not containing this additive) had an induction period of 10.5 hours. On the other hand, a sample of the grease containing 1% by weight of 2,4- diaminodiphenyl ether had an induction period of 260 hours. Thus, it will be noted that the inhibitor of the present invention was exceptionally eliective in improving the stability of the grease.
Example 11 This grease had a control (not containing this additive).
induction period of 10.5 hours. On the other hand,
a sample of this grease containing 1 by weight a" 2,4,'-diaminodiphenyl ether had an induction period of 370 hours. Here again, it will be noted that the inhibitor Example Ill The grease used in this example was a syntheticgrease prepared in substantially the same manner described in Example I, except that 87% of di-Z-ethylhexyl sebacate was mixed with 12% lithium stearate. 1% by weight of 2,4- diaminodiphenyl ether was incorporated in the syn thetic grease. A control sample of the grease (not containing this additive) had an induction period of 17 hours. On the other hand, a sample of the grease containing 1% by weight of 2,4-diamino-dipheny1 ether did not undergo a pressure drop of one pound per square inch until after 318 hours exposure.
From the above data, it will be noted that this inhibitor was very efiective in improving the stability of thesynthetic grease.
I claim as my invention: a p
1. A method of stabilizing a lubricant normally subject to oxidative deterioration which comprises incorporating 25 therein a stabilizing concentration otza' diniiaadiphen r ether.
References Cited in the file of this patent UNITED STATES PATENTS 2,048,362 Stoesser et al. July 21, 1936 2,269,265 Hamilton et al. Jan. 6, 1942 2,290,860 Burk et al. July 28, 1942 2,350,746 Fuller June 6, 1944 2,367,264 Burk et a1. Jan. 16, 1945 2,440,530- Yates Apr. 27, 1948 2,523,100
Eby Sept. 19, 1950

Claims (1)

  1. 2. A LUBRICANT NORMALLY SUBJECT TO OXIDATIVE DETERIORATION CONTAINING, AS AN INHIBITOR AGAINST SAID DETERIORATION, A STABILIZING CONCENTRATION OF 2,4''-DIAMINODIPHENYL ETHER.
US570420A 1956-03-09 1956-03-09 Stabilization of lubricants Expired - Lifetime US2910437A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
NL102710D NL102710C (en) 1956-03-09
US570420A US2910437A (en) 1956-03-09 1956-03-09 Stabilization of lubricants
GB7219/57A GB819024A (en) 1956-03-09 1957-03-05 Improvements in or relating to the stabilizing of lubricating greases
DEU4409A DE1113785B (en) 1956-03-09 1957-03-07 Lubricating grease based on mineral, animal or synthetic oils
ES0234133A ES234133A1 (en) 1956-03-09 1957-03-08 Stabilization of lubricants
FR1172914D FR1172914A (en) 1956-03-09 1957-03-09 Process for the stabilization of organic substances
GB43340/60A GB899024A (en) 1956-03-09 1960-12-16 Alternating current bridge

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ES (1) ES234133A1 (en)
FR (1) FR1172914A (en)
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NL (1) NL102710C (en)

Cited By (8)

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US2982729A (en) * 1958-04-02 1961-05-02 Universal Oil Prod Co High temperature lubricating grease containing a p, p'-diaminodiphenylether
US3169926A (en) * 1961-11-29 1965-02-16 Universal Oil Prod Co Stabilization of organic substances
US3208944A (en) * 1962-11-19 1965-09-28 Universal Oil Prod Co Stabilization of lubricants
US3240706A (en) * 1963-01-24 1966-03-15 Universal Oil Prod Co Stabilization of organic substances
US3330777A (en) * 1966-03-16 1967-07-11 Universal Oil Prod Co Stabilization of organic substances
US4378298A (en) * 1981-05-12 1983-03-29 Uop Inc. Imines of 2,4-diaminodiphenyl ethers as antioxidants for lubricating oils and greases
US4380497A (en) * 1981-05-12 1983-04-19 Uop Inc. Amines of alkoxydiphenyl esthers as antioxidants and lubricating oils and greases containing same
US4386002A (en) * 1981-05-12 1983-05-31 Uop Inc. Imines of aminodiphenyl esthers as antioxidants and lubricating oils and greases containing same

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Publication number Priority date Publication date Assignee Title
CN114892176B (en) * 2022-05-12 2024-03-26 中山大学 Application of organic selenium in inhibiting corrosion of carbon steel in acid solution and carbon steel corrosion inhibitor

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US2048362A (en) * 1934-05-04 1936-07-21 Dow Chemical Co Acid composition for treatment of deep wells
US2269265A (en) * 1939-12-14 1942-01-06 Socony Vacuum Oil Co Inc Stabilized refined petroleum product
US2290860A (en) * 1940-04-26 1942-07-28 Standard Oil Co Beneficiation of lubricating oils
US2350746A (en) * 1941-11-26 1944-06-06 Socony Vacuum Oil Co Inc Mineral oil composition
US2367264A (en) * 1940-09-30 1945-01-16 Standard Oil Co Beneficiating lubricants, etc.
US2440530A (en) * 1944-11-04 1948-04-27 Shell Dev Stabilized organic compositions
US2523100A (en) * 1947-05-17 1950-09-19 Standard Oil Dev Co Mineral oil composition and additive therefor

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DE929385C (en) * 1952-04-23 1955-06-27 Bayer Ag Additives for lubricants

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US2048362A (en) * 1934-05-04 1936-07-21 Dow Chemical Co Acid composition for treatment of deep wells
US2269265A (en) * 1939-12-14 1942-01-06 Socony Vacuum Oil Co Inc Stabilized refined petroleum product
US2290860A (en) * 1940-04-26 1942-07-28 Standard Oil Co Beneficiation of lubricating oils
US2367264A (en) * 1940-09-30 1945-01-16 Standard Oil Co Beneficiating lubricants, etc.
US2350746A (en) * 1941-11-26 1944-06-06 Socony Vacuum Oil Co Inc Mineral oil composition
US2440530A (en) * 1944-11-04 1948-04-27 Shell Dev Stabilized organic compositions
US2523100A (en) * 1947-05-17 1950-09-19 Standard Oil Dev Co Mineral oil composition and additive therefor

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2982729A (en) * 1958-04-02 1961-05-02 Universal Oil Prod Co High temperature lubricating grease containing a p, p'-diaminodiphenylether
US3169926A (en) * 1961-11-29 1965-02-16 Universal Oil Prod Co Stabilization of organic substances
US3208944A (en) * 1962-11-19 1965-09-28 Universal Oil Prod Co Stabilization of lubricants
US3240706A (en) * 1963-01-24 1966-03-15 Universal Oil Prod Co Stabilization of organic substances
US3330777A (en) * 1966-03-16 1967-07-11 Universal Oil Prod Co Stabilization of organic substances
US4378298A (en) * 1981-05-12 1983-03-29 Uop Inc. Imines of 2,4-diaminodiphenyl ethers as antioxidants for lubricating oils and greases
US4380497A (en) * 1981-05-12 1983-04-19 Uop Inc. Amines of alkoxydiphenyl esthers as antioxidants and lubricating oils and greases containing same
US4386002A (en) * 1981-05-12 1983-05-31 Uop Inc. Imines of aminodiphenyl esthers as antioxidants and lubricating oils and greases containing same

Also Published As

Publication number Publication date
DE1113785B (en) 1961-09-14
ES234133A1 (en) 1957-08-16
NL102710C (en)
GB819024A (en) 1959-08-26
FR1172914A (en) 1959-02-17

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