US2938871A - Aviation gas turbine lubricants - Google Patents

Aviation gas turbine lubricants Download PDF

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US2938871A
US2938871A US630060A US63006056A US2938871A US 2938871 A US2938871 A US 2938871A US 630060 A US630060 A US 630060A US 63006056 A US63006056 A US 63006056A US 2938871 A US2938871 A US 2938871A
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percent
acid
carbon atoms
diester
lubricating oil
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US630060A
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Alfred H Matuszak
Ernest V Wilson
Walter W Gleason
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering 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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2205/022—Ethene
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/14—Synthetic waxes, e.g. polythene waxes
    • C—CHEMISTRY; METALLURGY
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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
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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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
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/22—Acids obtained from polymerised unsaturated 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
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • 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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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C10M2209/112—Complex polyesters having dihydric acid centres
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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
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • C—CHEMISTRY; METALLURGY
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
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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
    • C—CHEMISTRY; METALLURGY
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/10—Phosphatides, e.g. lecithin, cephalin
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention relates to synthetic lubricating compo- 'sitions. Particularly, the invention relates tolubricating compositions comprisinga synthetic ester lubricating oil and minor amounts of certain additives which improve the load carrying ability of the synthetic oil.
  • Synthetic-ester lubricating oils are known to the art. 'In general, these oils are characterized by viscosity properties that are outstandingat both low andhigh temperatures, especially when compared to mineral oils.
  • ';th'e synthetic ester oils have become of increasing importance in the field of lubrication, and one of the most important current applications of. such compounds is in the lubrication of aviation gas-turbine systerns such as are use'd'in'the turbo ⁇ jet1 or turbo-prop 'type' ofaircraftq"
  • the load-carrying' ability of f;t hese ester oils is "notparticularly high.
  • the diesters prepared from the Oxo alcohols which are isomeric mixtures of highly branched-chain aliphatic primary alco- Y hols, are particularly desirable.
  • the Oxo alcohols have a very high degree; of branching in the'hydrocarbon chain, which results in diester oils-having low 'pour'points and low viscosity at low temperature.
  • These alcohols areprepared from olefins, such as polymers and copoly- I mers of C and C monoolefins, which are reacted with hydes.
  • the dicarboxylic acids which may be used as loadcarrying agents arethose' saturated aliphatic dicarbcx-ylic acids having 6' to 10 earbonatoms per molecule. These acids include adipic acid, pim'elic acid, suberic acid, azelaic acid, sebacic acid and isosebacicacid-
  • the isosebacic acid isa mixture of C acids comprising about 60 to 90 wt. percent of a-ethylsuberic acid, about5'to 25 wt. percent'of a,a'-diethyl adipic acid, andabout 5 to 15 wt. percent of sebacic acid.
  • a typical such acid will contain about 75 wt. percent of oz-ethyl suberic acid, about-15 wt. percent of ,a'-diethyl adipic acid and about 10 wt. percent of sebacic acid.
  • aryl. phosphates useful in this; invention are those 1 compounds which have the following general formula:
  • the esteroilsused in the compositions of this invention include diesters of saturated aliphatic dicarboxylic acids esterified with alcohols. These diestersv have the general formula: I a
  • R represents a straight-chain or branched-chain alkyl radical of an alkanol hayingabout 7 to 13 carbon atoms
  • phosphates include triphenyl phosphate, phenyl dicresylphosphate, tricresylphosphate, methyl di-tert. butyl phosphate, etc.
  • halogen-substituted alkylphosphorus compounds 1 useful in this invention may be d ivided into three gen:
  • Halogen e.g. chlorine
  • phosphonates which include saturated and unsaturated, 'mo'no, -di and tri halogensubstituted alkyl phosphonates having the general forethyl) I ethyl 'phosphonate; bis(4-ichloropentyl) Table III Composition of Lubricant (Parts) Diester Oil: 7
  • Triphenyl phosphate 1. 0 Phenyl dicresylghosphate 3.0 1. 0 1.0 Halohosphorus Gompound: Methyl di-tert. butyi phosphate; Tris (2-chloroethyl) hos h 0.3 0.2 BIsOZ-chloroethyl) vinyl phosphonate. 0. 5 Bisw-chloroethyl) ethyl Iphosphonate. 0. 6 Tris 2-o loroethyl) phosphitp 0. 3 Other additives:
  • composition according to claim 1 wherein said dicarboxylic acid is sebacic acid and wherein said halogen-containing phosphonate is bis(fi-chloroethyl) vinyl phosphonate.
  • a synthetic ester lubricating oil composition having improved load-carrying ability consisting essentially of a diester having the formula R0OCR --C0OR where in R represents an alkyl radical of an alcohol having about 7 to 13 carbon atoms, R is a C to C alkylene radical of a dicarboxylic acid, and the total number of carbon atoms in the molecule being about 20 to 36; about 0.01 to 0.10 wt. percent of a saturated aliphatic dicarboxylic acid containing about 6 to 10 carbon atoms per molecule, about 0.5 to 5.0 wt.
  • each R is a radical selected from the group consisting of hydrogen and alkyl groups containing about 1 to 5 carbon atoms; and about 0.1 to 0.8 wt. percent of a halogen-containing phosphonate having the general formula:
  • R, R and R" are selected from the group consisting of aliphatic hydrocarbon radicals and halogensubstituted aliphatic hydrocarbon radicals, said radicals containing 1 to 5 carbon atoms and at least one of said radicals being halogen-substituted.
  • composition according to claim 3 wherein said dicarboxylic acid is sebacic acid; said aryl phosphate is tricresyl phosphate; and wherein said phosphonate is bis(fl-chloroethyl) vinyl phosphate.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Description

additives T Alfred H. Matuszak, WestfieldpErnest v. wn e Cr m 7 ford,;and Walter W. Gleason, Roselle, NJ.,.assignors 'to Esso Research and'Engineering Company, a .corpo-f, ration of Delaware v I No Drawing. Filed Dec. '2-4, 1956, Ser. No. 630,060 7 AClaims. Cl. 252-493) This invention relates to synthetic lubricating compo- 'sitions. Particularly, the inventionrelates tolubricating compositions comprisinga synthetic ester lubricating oil and minor amounts of certain additives which improve the load carrying ability of the synthetic oil.
"Synthetic-ester lubricating oils are known to the art. 'In general, these oils" are characterized by viscosity properties that are outstandingat both low andhigh temperatures, especially when compared to mineral oils. In recent years,';th'e synthetic ester oils have become of increasing importance in the field of lubrication, and one of the most important current applications of. such compounds is in the lubrication of aviation gas-turbine systerns such as are use'd'in'the turbo}jet1 or turbo-prop 'type' ofaircraftq" Howeverfiri general, the load-carrying' ability of f;t hese ester oilsis "notparticularly high. Because of the'increasing severity of theconditions prevailing in the lubrication of aviation gas-turbine systems, itis highly desirable to'form synthetic ester lubricating compositions having higherload-carrying' ability than is inherent in the ester oil itselfgf invention, therefore, isconcerned'with synthetic ester oils containing for increasingjthe 'load-carryingability of the g In generaL-the compositionsof this inventionwill comprise'a synthetic ester lubricating oil and minor loadcarrying improving amount'sof saturated aliphatic dica'rboxylicacids containing 6 to '10carbon atoms per molecule Although these dicarboxylic acids are very elfective asrlo'ad-carryin g agents, the amount in which they canfbje used is limited; since *they are not generally soluble in ester oils in "amountsjgreater than 0.10% by weigh'tp Itfhas'also, been found that small amounts of an phosphate landhalogen substituted alkyl phosphorus compounds-are also very eflfectivejin'increasing the loadcarryingability of the ester lubricant. Surprisingly, it has been further found that the combination of the di- 2,938,871 .pg nted May 731;: 9-
elude di-Z-ethylhexyl sebacate, 'di-n-nonyl adipate, di-ntridecyl azelate, di-n-heptylisosebacate, di-C Oxo trimethyl adipate, (ii-C OXopimelate, etc. The diesters prepared from the Oxo alcohols; which are isomeric mixtures of highly branched-chain aliphatic primary alco- Y hols, are particularly desirable. The Oxo alcohols have a very high degree; of branching in the'hydrocarbon chain, which results in diester oils-having low 'pour'points and low viscosity at low temperature. These alcohols areprepared from olefins, such as polymers and copoly- I mers of C and C monoolefins, which are reacted with hydes.
carbon monoxide and hydrogen, in'the presenceof a cobalt-containing catalyst such as a cobalt carbonyl catalyst, at temperatures of about 300? to 400- F., and under pressures of about 1000 to 3000 p.s.i., to form alde- The resulting aldehyde product is, then hydrogenated to form the alcohol which is then recovered from the hydrogenation product.
The dicarboxylic acids which may be used as loadcarrying agents arethose' saturated aliphatic dicarbcx-ylic acids having 6' to 10 earbonatoms per molecule. These acids include adipic acid, pim'elic acid, suberic acid, azelaic acid, sebacic acid and isosebacicacid- The isosebacic acid isa mixture of C acids comprising about 60 to 90 wt. percent of a-ethylsuberic acid, about5'to 25 wt. percent'of a,a'-diethyl adipic acid, andabout 5 to 15 wt. percent of sebacic acid. A typical such acid will contain about 75 wt. percent of oz-ethyl suberic acid, about-15 wt. percent of ,a'-diethyl adipic acid and about 10 wt. percent of sebacic acid.
' The aryl. phosphates useful in this; invention are those 1 compounds which have the following general formula:
carboxylic acid with small amounts of (a) the halogen- V substituted alkyl phosphorus compound, or (b) a mix ture of both the aryl phosphate and the halogen-substituted alkyl phosphorus compounds, results in an additive combination having a much greater effect on the loadcarrying ability of the synthetic ester lubricant than would be expected from the mere addition of the individ- 'ual. efiect of each component. V I The esteroilsused in the compositions of this invention include diesters of saturated aliphatic dicarboxylic acids esterified with alcohols. These diestersv have the general formula: I a
' ROOC-R COOR- wherein R represents a straight-chain or branched-chain alkyl radical of an alkanol hayingabout 7 to 13 carbon atoms, R -is a straightorvbranched-chain C to C alkylene radical of a dicarboxylic acid, and the total number of carbon atoms in the molecule=being about 20 to 36, preferably 22 to 26. Examples of suchdieste'rs inwherein each R is a-raclical sele'ctedfrom the, group consisting'of hydrogen and alkyl groups containing about l'to 4 carbon atoms, e.'g. methyl groups. Examples of such phosphates include triphenyl phosphate, phenyl dicresylphosphate, tricresylphosphate, methyl di-tert. butyl phosphate, etc.
The halogen-substituted alkylphosphorus compounds 1 useful in this invention may be d ivided into three gen:
eral classes as follows: j 1 Halogen (e.g. chlorine) phosphonates which include saturated and unsaturated, 'mo'no, -di and tri halogensubstituted alkyl phosphonates having the general forethyl) I ethyl 'phosphonate; bis(4-ichloropentyl) Table III Composition of Lubricant (Parts) Diester Oil: 7
Di-2-ethylhexyl sebacate 55 70 30 100 03 0x0 Arc-late C Oxo Adipate. 45 01; 0x0 adipate 30 20 10 Dibasie Acid:
Iso-sebacic acid 70.1 Azelaic acid Adlpic Acid Aryl Phosphate:
Triphenyl phosphate 1. 0 Phenyl dicresylghosphate 3.0 1. 0 1.0 Halohosphorus Gompound: Methyl di-tert. butyi phosphate; Tris (2-chloroethyl) hos h 0.3 0.2 BIsOZ-chloroethyl) vinyl phosphonate. 0. 5 Bisw-chloroethyl) ethyl Iphosphonate. 0. 6 Tris 2-o loroethyl) phosphitp 0. 3 Other additives:
Phenothiazine 1 Phenyl alpha naphthylamine 1 1 1 What is claimed is: 1. A synthetic ester lubricating oil composition having improved load-carrying ability, which comprises a major proportion of a diester having the formula R0\ B0P=O wherein R, R and R" are selected from the-group consisting of aliphatic hydrocarbon radicals and halogensubstituted aliphatic hydrocarbon radicals, each of said radicals containing 1 to 5 carbon atoms and at least one of said radicals being halogen-substituted.
2. A composition according to claim 1 wherein said dicarboxylic acid is sebacic acid and wherein said halogen-containing phosphonate is bis(fi-chloroethyl) vinyl phosphonate.
3. A synthetic ester lubricating oil composition having improved load-carrying ability, consisting essentially of a diester having the formula R0OCR --C0OR where in R represents an alkyl radical of an alcohol having about 7 to 13 carbon atoms, R is a C to C alkylene radical of a dicarboxylic acid, and the total number of carbon atoms in the molecule being about 20 to 36; about 0.01 to 0.10 wt. percent of a saturated aliphatic dicarboxylic acid containing about 6 to 10 carbon atoms per molecule, about 0.5 to 5.0 wt. percent of an aryl wherein each R is a radical selected from the group consisting of hydrogen and alkyl groups containing about 1 to 5 carbon atoms; and about 0.1 to 0.8 wt. percent of a halogen-containing phosphonate having the general formula:
wherein R, R and R" are selected from the group consisting of aliphatic hydrocarbon radicals and halogensubstituted aliphatic hydrocarbon radicals, said radicals containing 1 to 5 carbon atoms and at least one of said radicals being halogen-substituted.
4. A composition according to claim 3 wherein said dicarboxylic acid is sebacic acid; said aryl phosphate is tricresyl phosphate; and wherein said phosphonate is bis(fl-chloroethyl) vinyl phosphate.
References Cited in the file of this patent UNITED STATES PATENTS OTHER REFERENCES Lubrication Engineering, August 1952, pages 97-200.

Claims (2)

1. A SYNTHETIC ESTER LUBRICATING OIL COMPOSITION HAVING IMPROVED LOAD-CARRYING ABILITY, WHICH COMPRISES A MAJOR PROPORTION OF A DIESTER HAVING THE FORMULA
3. A SYNTHENIC ESTER LUBRICATING OIL COMPOSITION HAVING IMPROVED LOAD-CARRYING ABILITY, CONSISTING ESSENTIALLY OF A DIESTER HAVING THE FORMULA ROOC-R1-COOR WHEREIN R REPRESENTS AN ALKYL RADICAL OF AN ALCOHOL HAVING ABOUT 7 TO 13 CARBON ATOMS, R1 IS A C4 TO C8 ALKYLENE RADICAL OF A DICARBOXYLIC ACID, AND THE TOTAL NUMBER OF CARBON ATOMS IN THE MILECULE BEING ABOUT 20 TO 36, ABOUT 0.01 TO 0.10 WT. PERCENT OF A SATURATED ALIPHATIC DICARBOXYLIC ACID CONTAINING ABOUT 6 TO 10 CARBOM ATOMS PER MOLECULE, ABOUT 0.5 TO 5.0 WT. PERCENT OF AN ARYL PHOSPHATE HAVING THE GENERAL FORMULA:
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3090752A (en) * 1960-09-01 1963-05-21 Exxon Research Engineering Co Instrument lubricating oil
US3193570A (en) * 1962-08-03 1965-07-06 Standard Oil Co Dialkyl trihalomethylphosphonateolefin adducts
DE2532795A1 (en) * 1974-07-22 1976-02-12 Fmc Corp FUNCTIONAL FLUID PREPARATIONS
FR2376895A1 (en) * 1977-01-10 1978-08-04 Gen Electric SILICONE LUBRICANT COMPOSITION EFFECTIVE FOR LUBRICATING SOFT METALS
US4440657A (en) * 1982-09-01 1984-04-03 Exxon Research And Engineering Co. Synthetic ester lubricating oil composition containing particular t-butylphenyl substituted phosphates and stabilized hydrolytically with particular long chain alkyl amines
WO2012096940A1 (en) 2011-01-12 2012-07-19 Exxonmobil Research And Engineering Company Systems and methods for improved combustion operations

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Publication number Priority date Publication date Assignee Title
US2573568A (en) * 1948-05-10 1951-10-30 Shell Dev Lubricant composition containing dialkyl trihaloalkane phosphonate as an extreme pressure agent
GB744777A (en) * 1953-04-07 1956-02-15 Shell Res Ltd Improvements in and relating to synthetic lubricating oils
GB757023A (en) * 1953-04-15 1956-09-12 Exxon Research Engineering Co Synthetic lubricant compositions
US2767142A (en) * 1953-06-29 1956-10-16 Shell Dev Lubricating compositions
US2788326A (en) * 1950-12-26 1957-04-09 Shell Dev Extreme pressure lubricant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2573568A (en) * 1948-05-10 1951-10-30 Shell Dev Lubricant composition containing dialkyl trihaloalkane phosphonate as an extreme pressure agent
US2788326A (en) * 1950-12-26 1957-04-09 Shell Dev Extreme pressure lubricant
GB744777A (en) * 1953-04-07 1956-02-15 Shell Res Ltd Improvements in and relating to synthetic lubricating oils
GB757023A (en) * 1953-04-15 1956-09-12 Exxon Research Engineering Co Synthetic lubricant compositions
US2767142A (en) * 1953-06-29 1956-10-16 Shell Dev Lubricating compositions

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3090752A (en) * 1960-09-01 1963-05-21 Exxon Research Engineering Co Instrument lubricating oil
US3193570A (en) * 1962-08-03 1965-07-06 Standard Oil Co Dialkyl trihalomethylphosphonateolefin adducts
DE2532795A1 (en) * 1974-07-22 1976-02-12 Fmc Corp FUNCTIONAL FLUID PREPARATIONS
US4087386A (en) * 1974-07-22 1978-05-02 Fmc Corporation Triaryl phosphate ester functional fluids
FR2376895A1 (en) * 1977-01-10 1978-08-04 Gen Electric SILICONE LUBRICANT COMPOSITION EFFECTIVE FOR LUBRICATING SOFT METALS
US4138349A (en) * 1977-01-10 1979-02-06 General Electric Company Silicone lubricant compositions containing trischloroethyl-phosphite and/or bis-chloroethyl chloroethyl phosphonate
US4440657A (en) * 1982-09-01 1984-04-03 Exxon Research And Engineering Co. Synthetic ester lubricating oil composition containing particular t-butylphenyl substituted phosphates and stabilized hydrolytically with particular long chain alkyl amines
WO2012096940A1 (en) 2011-01-12 2012-07-19 Exxonmobil Research And Engineering Company Systems and methods for improved combustion operations

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