US2174019A - Lubricant - Google Patents

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US2174019A
US2174019A US112985A US11298536A US2174019A US 2174019 A US2174019 A US 2174019A US 112985 A US112985 A US 112985A US 11298536 A US11298536 A US 11298536A US 2174019 A US2174019 A US 2174019A
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oils
corrosion
compounds
sulfur
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US112985A
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Jr Frederick W Sullivan
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Standard Oil Co
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Standard Oil Co
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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
    • 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
    • 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
    • C10M2207/129—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
    • 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
    • C10M2207/16—Naphthenic acids
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/061—Metal salts
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/06—Groups 3 or 13

Definitions

  • This invention relates to lubricants and, in particular, to addition agents imparting to lubricants improved properties.
  • My invention has particular utility in preventing and/or inhibiting the corrosion of hard metal alloy bearing such as copper-lead, cadmium-nickel, and cadmium-silver bearings which, to a large extent, have replaced soft metal bearingssuch as Babbitt metal in the trend toward internal combustion engines having high compression ratios and increased acceleration and increased speed characteristics.
  • hard metal alloy bearing such as copper-lead, cadmium-nickel, and cadmium-silver bearings
  • soft metal bearings such as Babbitt metal in the trend toward internal combustion engines having high compression ratios and increased acceleration and increased speed characteristics.
  • the use of the hard metal bearings has created lubricating and corrosion .probiems, particularly in connecl tion with highly refined oils, some of which may be very corrosive to the hard metal" bearings.
  • highly refined lubricating oils mean vis cous oils which have a minimum viscosity in the 0 range of S. A. E. 10 oils, and which have been subjected to such refining processes such as, for example, solvent extraction, that the parafiinicity of the oil is markedly increased. It has been found that highly refined lubricating oils cause corrosion to alloy bearings of the cadmium silver type to the extent of 5 mg/cm and even greater when such bearings are submerged for 25 hours or less in an air agitated oil which has been preoxidized at about 340 F. for 25 to 50 hours.
  • the motor oils may be highly refined lubricating oils as such or mixtures of highly refined lubrieating oils with less'highly refined lubricating oils, or stated in another way, mixtures of corrosive oils and non-corrosive oils, examples of the latter being lubricating oil fractions from Winkler crude or crudes of the Winkler type.
  • My invention is practised by adding to highly refined lubricating oils up to 5%, but preferably from 0.0005 to 0.01 gram mols to 100 grams of oil of certain organic phosphorous compounds derived from phosphinic and phosphinous acids, said organic phosphorous compounds having the general formula 2 xiv in which R and R" are hydrocarbon radicals such as alkyl, aryl, aralkyl or alkaryl or mixtures thereof and/or said hydrocarbon radicals having substituted mercapto, hydroxy, amino, alkyl substituted amino, thiocyano, isothiocyano, or halogen group or groups; X is oxygen, sulfur or selenium; Z is either absent or is oxygen, sulfur,
  • Ethyl diphenylphosphinite Ethyl diphenylthiophosphinite Isopropyl diphenylthiophosphinite Iso diphenylphosphinite Amyl diamylphosphinite Isoamyl dibutylthiophosphinite Phenyl diphenylphosphinite Phenyl diphenylthiophosphinite Listedbelow are specific examples of the di esters of R-phosphinic acid having the general formula in which R", R", X are as hereinbefore defined and Z is oxygen, sulfur or selenium:
  • esters of the di R-phosphinic acid having the general formula I '):-P( in which R, R", X are as hereinbefore defined and Z is oxygen, sulfur or selenium are illustrated by the. following representative compounds:
  • Ethyl phenylethylphosphinate Ethyl diphenylphosphinate Ethyl 4-methyl-4 carboxy diphenylphosphinate Butyl di-p-tolylthiophosphinate Methyl phenylmethylphosphinate Amyl phenylhydroxyethylphosphinate, etc.
  • R and R" are as hereinbefore defined, contemplated within the scope of my invention.
  • Contemplated within the scope of my invention are also the mono esters of the R-phosphinous acid having the general formula and R" are as hereinbeiore defined. Examples of such compounds are ethyl phenylphosphinite and phenyl butyl phosphinite.
  • My invention further contemplates the use of the foregoing compounds in concentrations up to 10% in oils whether highly refined or not for the purpose of improving the film strength of said oils and to impart to lubricants improved extreme pressure characteristics. These compounds may also be used to impart other desirable properties to lubricating oils such as nonsticking ring properties and the like.
  • Some of the hereinbefore named compounds may not be completely soluble in the lubricant, in which case effective results may be obtained by suspending the inhibitor in the lubricant and by means of a small amount of a peptizlng agent such as aluminum naphthenate, aluminum stearate and the like.
  • a peptizlng agent such as aluminum naphthenate, aluminum stearate and the like.
  • a corrosion inhibited motor oil comprising a mineral lubricating oil and a small amount but not more than 5% of an ester of phosphinous acid having the general formula (R).-P(XR)
  • R and R" represent members selected from the group consisting of alkyl, aryl, aralkyl, alkaryl and halogen-substituted alkyl, aryl and aralkyl groups
  • X is an element selected from the group consisting of oxygen, sulfur and selenium
  • a and b are integers selected from the group of numbers consisting of l and 2; and in which a+b is always equal to 3.
  • a corrosion inhibited motor oil comprising a mineral lubricating oil and a small amount but not more than 5% of an ester of phosphinic acid having the general formula in which R and R" represent members selected from the group consisting of alkyl, aryl, aralkyl. alkaryl and halogen-substituted alkyl, aryl and aralkyl groups; Z is an element selected from the group consisting of oxygen, sulfur and selenium; X is an element selected from the group consisting of oxygen, sulfur and selenium; a and b are integers selected from the group of numbers consisting of l and 2; and in which (1+!) is always equal to 3.
  • the method of preventing the corrosion of metal alloy bearings selected from the group consisting of cadmium-silver,-cadmium-nickel, copper-lead alloys in the presence of highly refined lubricating oils in internal combustion engines which comprises adding an ester of phosphinous acid having the general formula lenium; a and b are integers selected from the group of numbers consisting of l and 2; and in which a+b is always equal to 3, said esters being added in a small but sufilclent quantity to inhibit the corrosion of said metal alloy bearings.
  • a corrosion inhibited motor oil comprising a mineral lubricating oil and a small amount but not more than 5% of a mono ester of a substituted phosphinic acid having the general formula in which R and R" are radicals selected from the group consisting of alkyl, aryl, aralkyl, alkaryl and halogen substituted alkyl and aryl radicals.
  • a corrosion inhibited motor oil comprising a mineral lubricating oil and an organic phosphorous compound selected from the group consisting of compounds having the general formulas in which R and R" represent members selected from the group consisting of alkyl, aryl, aralkyl, alkaryl and halogen-substituted alkyl, aryl and aralkyl groups;
  • Z is an element selected from the group consisting of oxygen, sulfur and selenium;
  • X is an element selected from the group consisting of oxygen, sulfur and selenium;
  • a and b are integers selected from the group of numbers consisting of 1 and 2;
  • c is a number selected from the group of numbers consisting of and 1; and in which a+b+c is always equal to 3, said organic phosphorous compound being added in small but suflicient quantities to inhibit corrosion by said mineral lubricating oil.

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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)

Description

Patented Sept. 26, 1939 PATENT OFFICE LUBRICANT Frederick W. Sullivan, Jr., Flossmoor, Ill., assignor to Standard Oil Company, Chicago, 111., a corporation of Indiana No Drawing.
Application November 27, 1936,
Serial No. 112,985 6 Claims. (01. 87-9) This invention relates to lubricants and, in particular, to addition agents imparting to lubricants improved properties.
My invention has particular utility in preventing and/or inhibiting the corrosion of hard metal alloy bearing such as copper-lead, cadmium-nickel, and cadmium-silver bearings which, to a large extent, have replaced soft metal bearingssuch as Babbitt metal in the trend toward internal combustion engines having high compression ratios and increased acceleration and increased speed characteristics. The use of the hard metal bearings has created lubricating and corrosion .probiems, particularly in connecl tion with highly refined oils, some of which may be very corrosive to the hard metal" bearings.
By highly refined lubricating oils I mean vis cous oils which have a minimum viscosity in the 0 range of S. A. E. 10 oils, and which have been subjected to such refining processes such as, for example, solvent extraction, that the parafiinicity of the oil is markedly increased. It has been found that highly refined lubricating oils cause corrosion to alloy bearings of the cadmium silver type to the extent of 5 mg/cm and even greater when such bearings are submerged for 25 hours or less in an air agitated oil which has been preoxidized at about 340 F. for 25 to 50 hours.
i The motor oils may be highly refined lubricating oils as such or mixtures of highly refined lubrieating oils with less'highly refined lubricating oils, or stated in another way, mixtures of corrosive oils and non-corrosive oils, examples of the latter being lubricating oil fractions from Winkler crude or crudes of the Winkler type.
My invention is practised by adding to highly refined lubricating oils up to 5%, but preferably from 0.0005 to 0.01 gram mols to 100 grams of oil of certain organic phosphorous compounds derived from phosphinic and phosphinous acids, said organic phosphorous compounds having the general formula 2 xiv in which R and R" are hydrocarbon radicals such as alkyl, aryl, aralkyl or alkaryl or mixtures thereof and/or said hydrocarbon radicals having substituted mercapto, hydroxy, amino, alkyl substituted amino, thiocyano, isothiocyano, or halogen group or groups; X is oxygen, sulfur or selenium; Z is either absent or is oxygen, sulfur,
in which R, R and X are as defined above:
Diethyl isoamyl thiophosphinite Diamyl methyl phosphinite Diethyl propylphosphinite Diethyl phenylphosphinite Diethyl phenylthiophosphinite Diphenyl ethylphosphinite Dithiophenyl ethylphosphinite Di isobutyl phenylthiophosphinite Diethyl chlor-phenylphosphinite The following compounds are examples of the esters of the di R-phosphinous acid having the eneral formula in which R, R" and X are as hereinbefore defined:
Ethyl diphenylphosphinite Ethyl diphenylthiophosphinite Isopropyl diphenylthiophosphinite Iso diphenylphosphinite Amyl diamylphosphinite Isoamyl dibutylthiophosphinite Phenyl diphenylphosphinite Phenyl diphenylthiophosphinite Listedbelow are specific examples of the di esters of R-phosphinic acid having the general formula in which R", R", X are as hereinbefore defined and Z is oxygen, sulfur or selenium:
Diethyl phenylphosphinate Diethyl paratolylphosphinate Dibutyl m-carboxy phenylphosphinate Diethyl p-bromo phenylphosphinate Dimethyl alpha hydroxy benzylphosphinate Dibutyl alpha hydroxy isopropylphosphinate Di isoamyl hydroxy methylphosphinate.
in which R The esters of the di R-phosphinic acid having the general formula I '):-P( in which R, R", X are as hereinbefore defined and Z is oxygen, sulfur or selenium are illustrated by the. following representative compounds:
Ethyl phenylethylphosphinate Ethyl diphenylphosphinate Ethyl 4-methyl-4 carboxy diphenylphosphinate Butyl di-p-tolylthiophosphinate Methyl phenylmethylphosphinate Amyl phenylhydroxyethylphosphinate, etc.
Compounds such as ethyl phenylphosphinate, butyl isoamyl thiophosphinate are examples of the mono esters of the R-phosphinic acid having the general formula,
in which R and R" are as hereinbefore defined, contemplated within the scope of my invention. Contemplated within the scope of my invention are also the mono esters of the R-phosphinous acid having the general formula and R" are as hereinbeiore defined. Examples of such compounds are ethyl phenylphosphinite and phenyl butyl phosphinite.
In addition to the compounds hereinbefore mentioned my invention further contemplates the use of the isomers of the di R-phosphinous acid having the general formula R nh X in which R, R" and X are as hereinbefore defined. Examples of compounds falling within this class are:
As has been heretofore mentioned many of the 'recent models of automobiles now in use are equipped with bearings of the hard metal" alloy type such as cadmium-silver alloy, cadmiumnickel alloy, nickel-lead alloy, etc. for the purpose of permitting increased speed characteristics and increased acceleration. In recent years mineral lubricating oils adapted for use in internal combustion engines have been given refining treatments, such as solvent extraction, which are more drastic than those of the past, for the purpose of increasing the viscosity index of such oils. While oils so refined give satisfactory performance in many respects, they have been found to cause more or less trouble in internal combustion engines equipped with bearings of the cadmiumsilver type due to the corrosion of such alloys. This condition is remedied by the addition of very small amounts, such as 0.0005 to 0.01 gram mols per grams of oil of any of the foregoing compounds or mixtures thereof to corrosive highly refined motor oils will inhibit the corrosion of the hard metal alloy bearings.
My invention further contemplates the use of the foregoing compounds in concentrations up to 10% in oils whether highly refined or not for the purpose of improving the film strength of said oils and to impart to lubricants improved extreme pressure characteristics. These compounds may also be used to impart other desirable properties to lubricating oils such as nonsticking ring properties and the like.
Some of the hereinbefore named compounds may not be completely soluble in the lubricant, in which case effective results may be obtained by suspending the inhibitor in the lubricant and by means of a small amount of a peptizlng agent such as aluminum naphthenate, aluminum stearate and the like.
I do not wish to limit myself to'the specific embodiments of my invention herein described except as defined by the appended'claims.
I claim: 1
1. A corrosion inhibited motor oil comprising a mineral lubricating oil and a small amount but not more than 5% of an ester of phosphinous acid having the general formula (R).-P(XR)|,
' in which R and R" represent members selected from the group consisting of alkyl, aryl, aralkyl, alkaryl and halogen-substituted alkyl, aryl and aralkyl groups; X is an element selected from the group consisting of oxygen, sulfur and selenium; a and b are integers selected from the group of numbers consisting of l and 2; and in which a+b is always equal to 3.
2. A corrosion inhibited motor oil comprising a mineral lubricating oil and a small amount but not more than 5% of an ester of phosphinic acid having the general formula in which R and R" represent members selected from the group consisting of alkyl, aryl, aralkyl. alkaryl and halogen-substituted alkyl, aryl and aralkyl groups; Z is an element selected from the group consisting of oxygen, sulfur and selenium; X is an element selected from the group consisting of oxygen, sulfur and selenium; a and b are integers selected from the group of numbers consisting of l and 2; and in which (1+!) is always equal to 3.
3. The method of preventing the corrosion of metal alloy bearings selected from the group consisting of cadmium-silver,-cadmium-nickel, copper-lead alloys in the presence of highly refined lubricating oils in internal combustion engines which comprises adding an ester of phosphinous acid having the general formula lenium; a and b are integers selected from the group of numbers consisting of l and 2; and in which a+b is always equal to 3, said esters being added in a small but sufilclent quantity to inhibit the corrosion of said metal alloy bearings.
4. The method of preventing the corrosion of metal alloy bearings selected from the group consisting of cadmium-silver, cadmium-nickel and copper-lead alloys of the cadmium-silver al- 1 (R) P(XR) a in which R and R" represent members selected from the group consisting of alkyl, aryl, aralkyL- alkaryl and halogen-substituted alkyl, aryl and aralkyl groups; Z is an'element selected from the group consisting of oxygen, sulfur and selenium; X is an element selected from the group consisting of oxygen, sulfur and selenium; a and b are integers selected from the group of numbers consisting of 1 and 2; and in which a+b-is always equal to 3, said esters being added in small but sumcient quantities to retard the corrosion to said metal alloy bearings.
5. A corrosion inhibited motor oil comprising a mineral lubricating oil and a small amount but not more than 5% of a mono ester of a substituted phosphinic acid having the general formula in which R and R" are radicals selected from the group consisting of alkyl, aryl, aralkyl, alkaryl and halogen substituted alkyl and aryl radicals.
6. A corrosion inhibited motor oil comprising a mineral lubricating oil and an organic phosphorous compound selected from the group consisting of compounds having the general formulas in which R and R" represent members selected from the group consisting of alkyl, aryl, aralkyl, alkaryl and halogen-substituted alkyl, aryl and aralkyl groups; Z is an element selected from the group consisting of oxygen, sulfur and selenium; X is an element selected from the group consisting of oxygen, sulfur and selenium; a and b are integers selected from the group of numbers consisting of 1 and 2; c is a number selected from the group of numbers consisting of and 1; and in which a+b+c is always equal to 3, said organic phosphorous compound being added in small but suflicient quantities to inhibit corrosion by said mineral lubricating oil.
FREDERICK W. SULLIVAN, JR.
CERTIFICATE OF CORRECTION.
Patent No. 2,l7Li,Ol9.v
September 26, 1959.
FREDERICK w. SULLIVAN, JR.
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 2, 0nd column, line YE, and page 5, first column, line 1, claim ii,
sec-
strike out the words "of the cadmium-silver alloy type; and that the said letters Patent shouldbe read with this correction therein that the same may conform to the record of the case in the Patent Office. I
Signedand sealed this 51st day of October, A. D. 1959.
(Seal) Henry Van Arsdale, Acting Commissioner of Patents.
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Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2466647A (en) * 1945-11-05 1949-04-05 Shell Dev Lubricating oil composition
US2573568A (en) * 1948-05-10 1951-10-30 Shell Dev Lubricant composition containing dialkyl trihaloalkane phosphonate as an extreme pressure agent
US2599761A (en) * 1949-02-21 1952-06-10 Shell Dev Extreme pressure lubricant
US2614990A (en) * 1949-10-11 1952-10-21 Shell Dev Lubricating composition of matter
US2662917A (en) * 1951-11-24 1953-12-15 Continental Oil Co Production of thionophosphorus compounds
US2708204A (en) * 1950-08-11 1955-05-10 Shell Dev Halogen- and phosphorus-containing compounds
US2725359A (en) * 1951-03-07 1955-11-29 Shell Dev Lubricating oil composition
US2825695A (en) * 1956-06-15 1958-03-04 Shell Dev Lubricating compositions
US2913415A (en) * 1956-01-30 1959-11-17 Shell Dev Method of inhibiting squawking in mineral oil transmission fluids
US2963437A (en) * 1955-02-17 1960-12-06 Standard Oil Co Lubricant compositions
US2965460A (en) * 1955-02-17 1960-12-20 Standard Oil Co Distillate hydrocarbon compositions
US2977308A (en) * 1952-04-23 1961-03-28 Bayer Ag Tetrahydronaphthylamino compounds
US2993859A (en) * 1958-07-29 1961-07-25 Texaco Inc Synergistic extreme pressure agent and lubricant composition
US3060127A (en) * 1957-06-27 1962-10-23 American Cyanamid Co Method of solubilizing iron
US3113973A (en) * 1960-08-24 1963-12-10 American Cyanamid Co Organophosphorus oxides and method of preparing them
US3189636A (en) * 1961-12-08 1965-06-15 Lubrizol Corp Allenic phosphorus compounds
US3201436A (en) * 1962-05-31 1965-08-17 Standard Oil Co Halogenated derivatives of dialkyl cyclododecadienephosphonates
US3206401A (en) * 1961-01-03 1965-09-14 Exxon Research Engineering Co Lubricating oil compositions containing ester of mercapto acid and a phosphonate
US3226322A (en) * 1961-12-28 1965-12-28 Shell Oil Co Liquid hydrocarbon composition and additives therefor
US3249447A (en) * 1962-01-23 1966-05-03 Lubrizol Corp Coating compositions
US3271313A (en) * 1961-12-08 1966-09-06 Lubrizol Corp Lubricants containing allenic phosphinyl compounds
US3287275A (en) * 1963-12-30 1966-11-22 Douglas Aircraft Co Inc Inhibition of corrosion of hydraulic fluids
US3294500A (en) * 1954-05-15 1966-12-27 Bayer Ag Fuel for internal combustion engines
US3331779A (en) * 1963-12-30 1967-07-18 Douglas Aircraft Co Inc Inhibition of corrosion of hydraulic fluids
US3352783A (en) * 1963-12-30 1967-11-14 Mc Donnell Douglas Corp Hydraulic fluid
US3371046A (en) * 1963-12-30 1968-02-27 Douglas Aircraft Co Inc Inhibition of corrosion of hydraulic fluids
US3376365A (en) * 1964-12-28 1968-04-02 Mobil Oil Corp Phosphinothioate ester
US3515537A (en) * 1967-11-29 1970-06-02 Hooker Chemical Corp Polychloro-alpha-hydroxybenzylphosphonic and phosphinic derivatives as plant growth control agents
US3718590A (en) * 1970-09-25 1973-02-27 Monsanto Co Polyphenyl thioether lubricating compositions
US3844961A (en) * 1970-12-30 1974-10-29 Monsanto Co Polyphenyl thioether lubricating compositions
US4158633A (en) * 1978-03-30 1979-06-19 Edwin Cooper, Inc. Lubricating oil
US4356097A (en) * 1978-03-30 1982-10-26 Edwin Cooper, Inc. Alkylphosphonate lubricating oil
US4501667A (en) * 1983-03-03 1985-02-26 Ciba-Geigy Corporation Process of inhibiting corrosion of metal surfaces and/or deposition of scale thereon
US5514292A (en) * 1992-04-28 1996-05-07 Tonen Corporation Lubricating oil composition
US5824628A (en) * 1995-05-18 1998-10-20 Castrol Limited Lubricating compositions

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2466647A (en) * 1945-11-05 1949-04-05 Shell Dev Lubricating oil composition
US2573568A (en) * 1948-05-10 1951-10-30 Shell Dev Lubricant composition containing dialkyl trihaloalkane phosphonate as an extreme pressure agent
US2599761A (en) * 1949-02-21 1952-06-10 Shell Dev Extreme pressure lubricant
US2614990A (en) * 1949-10-11 1952-10-21 Shell Dev Lubricating composition of matter
US2708204A (en) * 1950-08-11 1955-05-10 Shell Dev Halogen- and phosphorus-containing compounds
US2725359A (en) * 1951-03-07 1955-11-29 Shell Dev Lubricating oil composition
US2662917A (en) * 1951-11-24 1953-12-15 Continental Oil Co Production of thionophosphorus compounds
US2977308A (en) * 1952-04-23 1961-03-28 Bayer Ag Tetrahydronaphthylamino compounds
US3294500A (en) * 1954-05-15 1966-12-27 Bayer Ag Fuel for internal combustion engines
US2963437A (en) * 1955-02-17 1960-12-06 Standard Oil Co Lubricant compositions
US2965460A (en) * 1955-02-17 1960-12-20 Standard Oil Co Distillate hydrocarbon compositions
US2913415A (en) * 1956-01-30 1959-11-17 Shell Dev Method of inhibiting squawking in mineral oil transmission fluids
US2825695A (en) * 1956-06-15 1958-03-04 Shell Dev Lubricating compositions
US3060127A (en) * 1957-06-27 1962-10-23 American Cyanamid Co Method of solubilizing iron
US2993859A (en) * 1958-07-29 1961-07-25 Texaco Inc Synergistic extreme pressure agent and lubricant composition
US3113973A (en) * 1960-08-24 1963-12-10 American Cyanamid Co Organophosphorus oxides and method of preparing them
US3206401A (en) * 1961-01-03 1965-09-14 Exxon Research Engineering Co Lubricating oil compositions containing ester of mercapto acid and a phosphonate
US3189636A (en) * 1961-12-08 1965-06-15 Lubrizol Corp Allenic phosphorus compounds
US3271313A (en) * 1961-12-08 1966-09-06 Lubrizol Corp Lubricants containing allenic phosphinyl compounds
US3226322A (en) * 1961-12-28 1965-12-28 Shell Oil Co Liquid hydrocarbon composition and additives therefor
US3249447A (en) * 1962-01-23 1966-05-03 Lubrizol Corp Coating compositions
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