US2321517A - Lubricant composition - Google Patents

Lubricant composition Download PDF

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US2321517A
US2321517A US372839A US37283941A US2321517A US 2321517 A US2321517 A US 2321517A US 372839 A US372839 A US 372839A US 37283941 A US37283941 A US 37283941A US 2321517 A US2321517 A US 2321517A
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oil
compounds
ammonium
lubricant composition
oxygen
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Rosen Raphael
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Standard Oil Development Co
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Standard Oil Development Co
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • C10M2207/404Fatty vegetable or animal oils obtained from genetically modified species
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, 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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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/044Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/062Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/066Arylene diamines
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/14Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/221Six-membered rings containing nitrogen and carbon only
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226Morpholines
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26Amines
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/30Heterocyclic compounds
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06Thio-acids; Thiocyanates; Derivatives thereof
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/086Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/061Metal salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Semi-solids; greasy

Definitions

  • the present invention relates to an improverent in lubricants and similar oils, as well as ther hydrocarbon materials, especially in repect to resistance to decomposition at elevated emperatures and oxidizing conditions such as re encountered in internal combustion engines. he invention will be fully understood from the escription which follows.
  • Greater solubility can be iparted to the compound by increasing the ngth of the aliphatic radicals and compounds ith a total of at least 12 carbon atoms in all the aliphatic radicals are most desired for the moose of the present inventior'i.
  • Compounds lite insoluble may, however, be used by being spersed in the oil or when dissolved by the aid a mutual solvent.
  • the preferred class of :W addition agents includesthe compounds Wing the formula:
  • iere R is a hydrocarbon radical, for example, L alkyl, cycloalkyl, aryl or aralkyl radical
  • X is L inorganic acid radical
  • m is an integer, or or less, chosen according to the valencies the R groups to satisfy four bonds of the trogen atom.
  • the various R groups may be nilar or dissimilar.
  • the radicals R may conin substituent atoms, for example, halogen, trogen, phosphorus, oxygen or sulfur, or subtuent groups, for example, hydroxyl, aroxy, :oxy, keto, amino or mercapto groups.
  • the eferred compounds are those in which the R :nups are alkyl groups.
  • the most preferred mpounds are those in which the total number carbon atoms in all of the hydrocarbon rad- '.ls is at least 12 and preferably at least 16, if ailable.
  • the acid radical ' may be of any type inorganic acid radical, but the salts most preferred are the halides, phosphates, phosphites, thiophosphates, thiophosphites, cyanates and thiocyanates of the ammonium bases. It is desirable to select compounds which are soluble in lubricating oil to the extent of at least 0.5% at temperatures above 30 F.
  • Typical examples of suitable compounds are tetra-n-butyl ammonium iodide, tetra-'n-butyl ammonium bromide, octadecyltributyl ammonium iodide, benzyloctadecyldimethyl ammonium chloride, octadecyl benzyl dimethyl ammonium chloride, cyclohexyl triisobutyl ammonium phosphite, phenyl tridecyl ammonium thiocyanate, triethanol octadecyi ammonium sulfite, methyl pyridonium sulfide and chlorethyl tributyl ammonium nitrate.
  • suitable examples include the nitrites, sulfites, hypophosphites, borates, stannates, arsenates, arsenites, chromates and chromites of various quaternary ammonium bases.
  • the new class of antioxidant compounds are advantageously added to the oils in concentrations ranging from 0.05 to 5%, but the quantity generally preferred is about 0.1 to about 1%.
  • the base stock to be used in the preparation of the lubricants of the present invention may be any refined mineral lubricating oil, preferably having a viscosity from 40 to 150 seconds Saybolt at 210 F.
  • suitable base stocks include those of high paraflinicity and high viscosity index, such as those which have a viscosity index of or more, as well as low parafiin and low viscosity index oils.
  • Base stocks comprising greases, fatty oils or synthetic oils may also be employed.
  • the addition agents of this invention do not have any detrimental effects on thephysical character of the lubricating oil to which they are added, such as viscosity, gravity and flash point.
  • the new additives may be used as the sole blending agents, or they may be added with other ingredients, such as oiliness agents, film strength modifiers, pour depressants, thickeners, viscosity index improvers, detergents, sludge dispersers, solvents, dyes, and the like.
  • the compounds described above may be used as oxidation inhibitors and improving agents in similar concentrations in other lubricating oil products, such as lubricating greases and extreme pressure lubricants.
  • the value of the antioxidants of the present invention when used in lubricating oil blends has been determined by several standard tests, including the oxygen absorption test, the cone test and the Sligh oxidation test.
  • the oxygen absorption test is carried out by bubbling a known amount of oxygen through cc. of the lubricating oil maintained at 200 C. The oxygen is continuously recycled. At the end of succeeding minute periods the amount of oxygen absorbed by the oil is measured. The results are given as the number oi! cubic centimeters of oxygen absorbed during each of these 15 minute periods.
  • the cone test which is a means for determining the tendency of an oil to deposit solid material upon heated metallic surfaces, is carried out by slowly dropping oil to be tested over a heated metal cone having a circumferential groove milled out in a screw iashionon the periphery so as to allow a time of contact of about one minute between the heated metallic surfaces and the oil.
  • a total volume of 60 cc. of oil is dropped from a dropping funnel during a period of two hours, the temperature of the cone being maintained at 250 C.
  • the cone is then washed in naphtha to remove adhering oil and the total deposit determined by difference in weight.
  • the Sligh oxidation test is carried out by heating 10 grams of the oil, contained in a stoppered conical flask from which the air has been displaced by oxygen, at 200 C. in an oil bath for 2 /2 hours.
  • antioxidants of the present invention as addition agents for lubricating oils may be illustrated by the following example.
  • Example A refined mineral lubricating oil of S. A. E. grade was blended, separately, with 0.2% of tetra-n-butyl ammonium iodide and 0.2% 0!- tetra-n-butyl ammonium bromide, and the blends thus formed, as well as a blank sample of thebase oil, were submitted to the cone test, the oxygen absorption test and the Bligh oxidation test,

Description

Patented June 8, 1943 LUBRICANT CODHOSITION Raphael Rosen, Elizabeth, N. l, assignor to Standard Oil Development Company, a corporation of Delaware No Drawing. Application January 2, 1941, Serial No. 372,839
1 Claim.
The present invention relates to an improverent in lubricants and similar oils, as well as ther hydrocarbon materials, especially in repect to resistance to decomposition at elevated emperatures and oxidizing conditions such as re encountered in internal combustion engines. he invention will be fully understood from the escription which follows.
It has been found that mineral oil lubricants in be greatly improved with respect to their ability against decomposition, especially under eat and oxidizing conditions, by the addition ieretc of small amounts of certain substances. 1 the present case, a new group of substances as been discovered which are particularly effecve in reducing the oxidation of oils at the elettecl temperatures encountered in internal comistion engines, 1. e., at temperaturesof 200 C. higher. This group of substances comprises 1e inorganic salts of quaternary ammonium lses. Such compounds are soluble in mineral is to only a small extent when the nitrogen am of the compound is attached to short hywocarbon radicals. Greater solubility can be iparted to the compound by increasing the ngth of the aliphatic radicals and compounds ith a total of at least 12 carbon atoms in all the aliphatic radicals are most desired for the moose of the present inventior'i. Compounds lite insoluble may, however, be used by being spersed in the oil or when dissolved by the aid a mutual solvent.
In its broadest aspects, the preferred class of :W addition agents includesthe compounds Wing the formula:
iere R is a hydrocarbon radical, for example, L alkyl, cycloalkyl, aryl or aralkyl radical, X is L inorganic acid radical, and m is an integer, or or less, chosen according to the valencies the R groups to satisfy four bonds of the trogen atom. The various R groups may be nilar or dissimilar. The radicals R may conin substituent atoms, for example, halogen, trogen, phosphorus, oxygen or sulfur, or subtuent groups, for example, hydroxyl, aroxy, :oxy, keto, amino or mercapto groups. The eferred compounds are those in which the R :nups are alkyl groups. The most preferred mpounds are those in which the total number carbon atoms in all of the hydrocarbon rad- '.ls is at least 12 and preferably at least 16, if ailable. The acid radical 'may be of any type inorganic acid radical, but the salts most preferred are the halides, phosphates, phosphites, thiophosphates, thiophosphites, cyanates and thiocyanates of the ammonium bases. It is desirable to select compounds which are soluble in lubricating oil to the extent of at least 0.5% at temperatures above 30 F. Typical examples of suitable compounds are tetra-n-butyl ammonium iodide, tetra-'n-butyl ammonium bromide, octadecyltributyl ammonium iodide, benzyloctadecyldimethyl ammonium chloride, octadecyl benzyl dimethyl ammonium chloride, cyclohexyl triisobutyl ammonium phosphite, phenyl tridecyl ammonium thiocyanate, triethanol octadecyi ammonium sulfite, methyl pyridonium sulfide and chlorethyl tributyl ammonium nitrate. In addition to the above, suitable examples include the nitrites, sulfites, hypophosphites, borates, stannates, arsenates, arsenites, chromates and chromites of various quaternary ammonium bases.
The new class of antioxidant compounds are advantageously added to the oils in concentrations ranging from 0.05 to 5%, but the quantity generally preferred is about 0.1 to about 1%.
In general, the base stock to be used in the preparation of the lubricants of the present invention may be any refined mineral lubricating oil, preferably having a viscosity from 40 to 150 seconds Saybolt at 210 F., and suitable base stocks include those of high paraflinicity and high viscosity index, such as those which have a viscosity index of or more, as well as low parafiin and low viscosity index oils. Base stocks comprising greases, fatty oils or synthetic oils may also be employed.
The addition agents of this invention do not have any detrimental effects on thephysical character of the lubricating oil to which they are added, such as viscosity, gravity and flash point. The new additives may be used as the sole blending agents, or they may be added with other ingredients, such as oiliness agents, film strength modifiers, pour depressants, thickeners, viscosity index improvers, detergents, sludge dispersers, solvents, dyes, and the like.
The compounds described above may be used as oxidation inhibitors and improving agents in similar concentrations in other lubricating oil products, such as lubricating greases and extreme pressure lubricants.
The value of the antioxidants of the present invention when used in lubricating oil blends has been determined by several standard tests, including the oxygen absorption test, the cone test and the Sligh oxidation test.
The oxygen absorption test is carried out by bubbling a known amount of oxygen through cc. of the lubricating oil maintained at 200 C. The oxygen is continuously recycled. At the end of succeeding minute periods the amount of oxygen absorbed by the oil is measured. The results are given as the number oi! cubic centimeters of oxygen absorbed during each of these 15 minute periods.
The cone test, which is a means for determining the tendency of an oil to deposit solid material upon heated metallic surfaces, is carried out by slowly dropping oil to be tested over a heated metal cone having a circumferential groove milled out in a screw iashionon the periphery so as to allow a time of contact of about one minute between the heated metallic surfaces and the oil. A total volume of 60 cc. of oil is dropped from a dropping funnel during a period of two hours, the temperature of the cone being maintained at 250 C. The cone is then washed in naphtha to remove adhering oil and the total deposit determined by difference in weight.
The Sligh oxidation test is carried out by heating 10 grams of the oil, contained in a stoppered conical flask from which the air has been displaced by oxygen, at 200 C. in an oil bath for 2 /2 hours. The number of milligrams of asphaltenes formed, determined by a solution of the oil in precipitation naphtha and filtration through a Gooch crucible, is termed the Sligh number of the oil.
The value of the antioxidants of the present invention as addition agents for lubricating oils may be illustrated by the following example.
. Example A refined mineral lubricating oil of S. A. E. grade was blended, separately, with 0.2% of tetra-n-butyl ammonium iodide and 0.2% 0!- tetra-n-butyl ammonium bromide, and the blends thus formed, as well as a blank sample of thebase oil, were submitted to the cone test, the oxygen absorption test and the Bligh oxidation test,
The present invention is not to be considered as limited by the herein described example, which is given by way of illustration only, but it is to be limited solely by the terms of the following claim.
I claim:
A lubricant containing dissolved therein 0.05% to 5% of tetra-n-butyl ammonium iodide.
RAPHAEL ROSEN.
US372839A 1941-01-02 1941-01-02 Lubricant composition Expired - Lifetime US2321517A (en)

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2419327A (en) * 1943-06-28 1947-04-22 Shell Dev Corrosion inhibitors-nitrite salts of secondary amines
US2432839A (en) * 1946-10-07 1947-12-16 Shell Dev Corrosion inhibitors-nitrite salts of primary amines
US2432840A (en) * 1946-10-07 1947-12-16 Shell Dev Corrosion inhibitors-nitrite salts of tertiary amines
US2484395A (en) * 1944-03-06 1949-10-11 Shell Dev Nitrite salts of organic nitrogen bases
US2532407A (en) * 1945-09-05 1950-12-05 Johansson Sven Christian Corrosion inhibiting compositions
US2563764A (en) * 1946-08-12 1951-08-07 Shell Dev Prevention of corrosive wear of moving metal parts
US2584086A (en) * 1946-06-08 1952-01-29 Shell Dev Hydraulic fluid composition
US2596450A (en) * 1946-10-28 1952-05-13 Shell Dev Corrosion-inhibiting coating composition containing organic amine nitrites
US2617771A (en) * 1946-09-27 1952-11-11 Hooker Electrochemical Co Corrosion retarder
US2771348A (en) * 1953-07-29 1956-11-20 Standard Oil Co Stabilized cracked petroleum fractions
US3005266A (en) * 1957-03-30 1961-10-24 Philips Corp Method of removing surface water from articles
US3102797A (en) * 1960-07-28 1963-09-03 Standard Oil Co Fuel oil composition
US3301815A (en) * 1962-04-19 1967-01-31 Csaba K Hunyar Stabilization of vinyl resins with organic quaternary ammonium nitrates
US3317291A (en) * 1963-07-16 1967-05-02 Armour & Co Nonclogging fuel oil compositions
US3346353A (en) * 1963-06-20 1967-10-10 Exxon Research Engineering Co Hydrocarbon oils of improved water tolerance and anti-rust characteristics
US3486866A (en) * 1966-01-05 1969-12-30 Petrolite Corp Quaternary ammonium iodide stabilized fuels
US4478730A (en) * 1983-04-01 1984-10-23 Cedric P. Spellman Bowling lane oil composition

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2419327A (en) * 1943-06-28 1947-04-22 Shell Dev Corrosion inhibitors-nitrite salts of secondary amines
US2484395A (en) * 1944-03-06 1949-10-11 Shell Dev Nitrite salts of organic nitrogen bases
US2532407A (en) * 1945-09-05 1950-12-05 Johansson Sven Christian Corrosion inhibiting compositions
US2584086A (en) * 1946-06-08 1952-01-29 Shell Dev Hydraulic fluid composition
US2563764A (en) * 1946-08-12 1951-08-07 Shell Dev Prevention of corrosive wear of moving metal parts
US2617771A (en) * 1946-09-27 1952-11-11 Hooker Electrochemical Co Corrosion retarder
US2432840A (en) * 1946-10-07 1947-12-16 Shell Dev Corrosion inhibitors-nitrite salts of tertiary amines
US2432839A (en) * 1946-10-07 1947-12-16 Shell Dev Corrosion inhibitors-nitrite salts of primary amines
US2596450A (en) * 1946-10-28 1952-05-13 Shell Dev Corrosion-inhibiting coating composition containing organic amine nitrites
US2771348A (en) * 1953-07-29 1956-11-20 Standard Oil Co Stabilized cracked petroleum fractions
US3005266A (en) * 1957-03-30 1961-10-24 Philips Corp Method of removing surface water from articles
US3102797A (en) * 1960-07-28 1963-09-03 Standard Oil Co Fuel oil composition
US3301815A (en) * 1962-04-19 1967-01-31 Csaba K Hunyar Stabilization of vinyl resins with organic quaternary ammonium nitrates
US3346353A (en) * 1963-06-20 1967-10-10 Exxon Research Engineering Co Hydrocarbon oils of improved water tolerance and anti-rust characteristics
US3317291A (en) * 1963-07-16 1967-05-02 Armour & Co Nonclogging fuel oil compositions
US3486866A (en) * 1966-01-05 1969-12-30 Petrolite Corp Quaternary ammonium iodide stabilized fuels
US4478730A (en) * 1983-04-01 1984-10-23 Cedric P. Spellman Bowling lane oil composition

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