US3579449A - Lubricant composition - Google Patents

Lubricant composition Download PDF

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Publication number
US3579449A
US3579449A US762966A US3579449DA US3579449A US 3579449 A US3579449 A US 3579449A US 762966 A US762966 A US 762966A US 3579449D A US3579449D A US 3579449DA US 3579449 A US3579449 A US 3579449A
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Prior art keywords
extreme pressure
additives
oil
group
additive
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US762966A
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Robert Earl Wann
Denzel Allan Nicholson
Ted Joe Logan
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Procter and Gamble Co
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Procter and Gamble 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4025—Esters of poly(thio)phosphonic acids
    • C07F9/4037—Esters of poly(thio)phosphonic acids containing halogen or nitro(so) substituents
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    • C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
    • C10M131/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen and halogen only
    • C10M131/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen and halogen only aliphatic
    • C—CHEMISTRY; METALLURGY
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    • C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
    • C10M131/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen, halogen and oxygen
    • C10M131/12—Acids; Salts or esters thereof
    • C—CHEMISTRY; METALLURGY
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/24—Nitriles
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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
    • C10M2201/02—Water
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04—Elements
    • C10M2201/041—Carbon; Graphite; Carbon black
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    • C10M2201/04—Elements
    • C10M2201/041—Carbon; Graphite; Carbon black
    • C10M2201/042—Carbon; Graphite; Carbon black halogenated, i.e. graphite fluoride
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
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    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/022—Well-defined aliphatic compounds saturated
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    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/024—Well-defined aliphatic compounds unsaturated
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/04—Well-defined cycloaliphatic compounds
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    • C10M2203/06—Well-defined aromatic compounds
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2203/102—Aliphatic fractions
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    • C10M2203/104—Aromatic fractions
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    • C10M2203/106—Naphthenic fractions
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    • C10M2205/026—Butene
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    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10N2040/247—Stainless steel

Definitions

  • Lubricant compositions comprising a major amount of a lubricating base fluid and a minor amount of extreme pressure additives which contain either a methylene, monohalomethylene or dihalomethylene group between two moieties selected from the group consisting of phosphono, dihydrocarbylphosphoryl, phenyl, substituted phenyl, keto, cyano, and carboxylate ester moieties.
  • This invention relates to lubricant compositions comprising (1) a major amount of a lubricating base fluid and (2) a minor amount suflicient to increase the loadbearing properties of said compositions of a compound having the formula:
  • each X is selected from the group consisting of hydrogen, chlorine, iodine and bromine atoms
  • each Y is selected from the group consisting of moieties having the following formulas wherein each R is selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, alkenyl, haloalkyl, haloaryl, haloalkaryl, haloaralkyl, haloalkenyl and nitroaryl moieties containing from 1 to about 22 carbon atoms and each R is selected from the group consisting of R, a halogen atom and a hydrogen atom, the above selections being made so that both Xs can be hydrogen atoms only when both Ys are and that one X can be hydrogen only when each Y is selected from the group consisting of THE LUBRICATING BASE FLUID
  • the extreme pressure additives of this invention will impart improved load-bearing characteristics to a wide variety of base fluids which are used for a variety
  • the base fluid can be either a petroleum hydrocarbon, a fatty acid triglyceride, a synthetic fluid, an aqueous based fluid, or mixtures thereof.
  • Petroleum hydrocarbons include mineral oil (including light solvents, neutral oils, heavy, bright and refined stocks, and asphaltic residual stocks), greases and waxes.
  • the lubricating base fluid can also comprise suspensions of graphite in oils.
  • Synthetic fluids include such disparate materials as polymerized olefins, organic carbonates, organic esters and/or ethers, polyglycols, silicones, modified organic materials (halogenated, phosphated, sulfurized, etc.) polymers, e.g., alkylmethacrylate polymers and synthetic resins, e.g., resins formed by esterification of polyhydric alcohols with polycarboxylic acids.
  • base fluids which can be used in the practice of this invention include those disclosed in US. Pat. 2,599,761, especially columns 9-11; US. Pat. 2,725,359, especially columns 2, and 7-8; US. Pat. 2,767,142 especially column 4; US. Pat. 2,882,228, especially columns 6-7; US.
  • the finished lubricant composition containing the above lubricating base fluids and the extreme pressure additives disclosed hereinbefore and specifically described hereinafter, can be used for lubricants for automobiles, aircraft, etc. as gear and bearing lubricants; as industrial metal working lubricants, e.g., for metal cutting and extrusion of steel, aluminum, titanium and its alloys, etc., (cutting fluids, drawing fluids, drawing compounds, extrusion lubricants, forging lubricants, rolling oils, machine tool lubricants, and other similar lubricants); and as fluids for the transmission of power, e.g., in car transmissions or hydraulic systems.
  • the extreme pressure additives of this invention are characterized by the presence of a methylene or halo (chloro, iodo, or bromo) substituted methylene group.
  • This methylene group is attached to two other groups, each of which can be either a phosphono (phosphonate diester), carboxylate ester, keto, cyano, phosphoryl (e.g., dialkylphosphine oxide), phenyl or substituted phenyl group.
  • These groups are essential to the good performance of the extreme pressure additives. These groups are also important in modifying the solubility of the extreme pressure additives in various lubricating base fluids.
  • those groups whch contain alkyl groups can, by selecting the length of the alkyl groups, be modified to give various hydrophilic and hydrophobic properties to the extreme pressure additives. It will be noted that there is an optimum chain length for each extreme pressure additive for each lubricating base fluid.
  • the dihalo and monohalo extreme pressure additives of this invention can, in general, be prepared by reacting the non-halogenated compounds with the desired sodium hypohalite. See, e.g., O. T. Quimby et al., J. Or ganometallic Chemistry, 13, 199 (1968).
  • the methylene diphosphonate esters can be prepared according to the teachings of US. Pat. 3,251,907.
  • the dihalodicyanomethane extreme pressure additives can be prepared by reaction of the dicyanomethane with molecular halogen and subsequent decomposition of the alkali metal halide complex according to the teaching of Organic Synthesis, vol. 39, page 64, M. Tishler, ed. and L. Ramberg and S.
  • the extreme pressure additives of this invention there is a considerable variation in effectiveness with respect to extreme pressure properties and there is considerable variation with respect to other properties such as corrosivity, antiwear properties and, of course, solubility or dispersibility.
  • the nonhalogenated methylenediphosphonate esters are the least corrosive of the additives. However, in general, they are also the least effective with respect to the extreme pressure properties. In general, the most effective extreme pressure additives are those which contain a dibromomethylene group. However, they tend to be more corrosive than the other additives.
  • the more effective extreme pressure additives are the dichloro-, diiodoand dibromomethylenediphosphonates, the dibromomalonates, dibromomalonitrile, the tetrabromoglutarates, diphenyldichloromethane dibenzoyldibromomethane, and the dibromoand dichlorophosphonoacetates.
  • the dichlorophosphonacetates are equal to or slightly better than the dibromophosphonoacetates. This is a surprising reversal of the general trend in which the dibromo compounds are more effective than the dichloro compounds.
  • the alkyl groups should contain from 1 to about 6 carbon atoms. However, in the case of the malonates, it is preferred that the alkyl groups contain at least about 5 carbon atoms since the malonates containing alkyl groups with less than about 5 carbon atoms tend to be more corrosive.
  • extreme pressure additives have a difierent primary activity.
  • the alkyl groups contain from about 7 to about 22 carbon atoms, they are effective antiwear additives. This is especially true of the methyleneand halomethylenediphosphonate esters.
  • additives which contain long chain alkyl groups are more effective as antiwear additives, they also are as effective as the shorter chain compounds, on a molar basis, as extreme pressure additives and the longer chains are quite often more compatible with lubricants which are greases and waxes.
  • the iodo compounds which are normally a mixture of monoand diiodo compounds, are good additives for metal working lubricants, especially lubricants which are used in the working of titanium and titanium alloys.
  • Finished lubricant compositions containing the extreme pressure additives of this invention can also contain other known additives, e.g., antioxidants, corrosion inhibitors, metal deactivators, viscosity index improvers, dispersing materials, dyes, thickeners, etc.
  • antioxidants include 2,6-ditertiarybutyl-4-methylphenol; 2,6-ditertiarybutyl phenol; 2,6-ditertiaryamyl-4-methylphenol; 2,6-diisopropyl-4-methylphenol; phenylnaphthylamine; phenylenediamine; and diphenylamine.
  • EXAMPLE I The following compositions were tested in a standard four ball tester for weld point (extreme pressure test) and wear scar (wear test).
  • the weld point is defined as that pressure where the balls weld together in two successive runs of one minute under the indicated pressure.
  • the wear scar is the average, based on three balls, of the average of both length and Width of the scars when the balls are run under a 40 kg. load for one hour at 1200 r.p.m. and at a temperature of All of the indicated additives in the following table were added to a Kendall SAE 10, parafiin base, additive free oil (lubricating base fluid) at the indicated level.
  • Composition 13-19, 23-25, and 40-51 show the effect' of varying the level of six representative extreme pressure additives of this invention.
  • TCP Tricresyl phosphate
  • Benzyl disulfide 7- Hexachloroethane 9 Trichloroacetic acid 2 10 Randomly chlorinated paraffin, 11- Lead naphthenates e 12 Molybdenum disulfide 13 Tetraisopropyl dichloromethy]enediphosphonate (iPnChMDP).
  • EtlBliluDP 1 Tetraisopropyl dibromomethylenediphosphonate 5 (iP14Bl2l ⁇ L[D P) g; Tetrgisopropyl monobromomethylenediphosph0nate 5 0 5 Tetraisopropyl methylenediph0sphonate 5 30- Tetraethyl methylenediphosphonate u 5 31 Tetrakis(stearyl)mcthylenediphosphonate 5 (CiaMDP). 32 Diethyl trichloromethylphosphonate.
  • nC BrzMal Di(n-pentyl) dibromomalonate (nC BrzMal) 5 800 41 do 3 500 42 2 380 43 1 280 44- 5 800 45 3 380 46- 2 320 47 1 280 48 5 800 49- 3 800 50 2 780 51 do 1 500 52- Tris(decyl) dibrornophosphonoacetate (CwBnPA) 5 240 53- Triethyl chlorophosphonoacetate (Et; CIPA) 5 260 54- Triethyl phosphonoacetate (Eta PA) 5 120 55- Tetrakis(decyl) methylenediphosphonate (CmMDP) 5 140 56 a Tetrabenzyl methylenediphosphonate (benzyl MD P) 5 120 57 Tetrabenzyl dichloromethylcnediphosphonate (Benzyl 5 220 ChMD P).
  • Compositions 2-12 and 32 demonstrate the effectiveness of certain representative prior art extreme pressure additives. It should be noted that, with the exception of the trichloroacetic acid and the diethyl trichloromethylphosphonate, the weld points are well under 400 kg. at an additive level of about 5%. The trichloroacetic acid and trichloromethylphosphonate, however, are quite corroslve.
  • Compositions 20-22 show the efiect of changing the length of the alkyl chain.
  • the longer alkyl chains merely dilute the extreme pressure additive effect, since on a molar basis the improvements of the additives of Compositions 20-22 are about the same.
  • There is a major ditference however in anti-wear properties since the tetrakis(decyl) and tetrakis(stearyl) additives provide a major improvement as demonstrated by the wear scar.
  • the tetramethyl additive does not help the antiwear properties of the base fluid.
  • a comparison of Compositions 17 and 23; 14 and 26; and 37 and 38 shows that, in general, the dibromo additives are more efiective than the dichloro additives. This is especially true with the malonates.
  • a comparison of Compositions 14, 26 and 8 shows that for the particular tetraisopropyl methylenediphosphonate additives the diiodo derivative is better than the dibromo derivative which is better than the dichloro derivative.
  • the ranking of the diiodo compound is undoubtedly aitected by the fact it contained a substantial amount of monoiodomethylenediphosphonate.
  • a comparison of Compositions 26, 27 and 29; 14, 28 and 29; 17 and 30; 21 and 55; 23 and 30; 37 and 39; 38 and 39; and 34, 53 and 54 shows the effect of going from a nonhalogenated to a monohalogenatcd to a dihalogenated extreme pressure additive having the same basic structure.
  • the nonhalogenated compounds are not efl ective extreme pressure additives.
  • the methylenediphosphonate esters have substantial extreme pressure activity.
  • the monohalogenated compounds in general are not much better than the nonhalogenated compounds as extreme pressure additives and it is only with the dihalogenated compounds that the best extreme pressure activity is achieved. It is surprising that the change from monohalogenated to dihalogenated compounds would give such a tremendous increase in extreme pressure activity.
  • compositions 22 and 31 show the antiwear properties are affected only slightly by the presence or absence of the halogen atoms on a compound. Also, in Composition 33 a mixture of an extreme pressure additive (iPr Cl MDP) and an anti wear additive (C MDP) gives both good extreme pressure activity and anti-wear activity.
  • iPr Cl MDP extreme pressure additive
  • C MDP anti wear additive
  • the dimethyl 3 keto 2,2,4,4-tetrabromoglutarate (Composition 59) is a difunctional dibromomethylene compound which shows that more than one YCX Y group can be present in a molecule of the extreme pressure additives of this invention.
  • Tetrabenzyl methylenediphosphonates are not very soluble in the base fluid of this example and accordingly are not as effective in this fluid as some of the other extreme pressure additives.
  • the diethyl dibromomalonate e.g., Composition 37 and 48-51 are extremely corrosive.
  • the dipentyl and diisopentyl esters of the dichloroand dibromomalonates, e.g., Compositions 40-47 are not corrosive.
  • the base fluid was water.
  • dibromomethylenediphos 7O phonate dibromomethylenediphos 7O phonate, triethyl dichloro phosphonacetate, and bis(2- ethylhexyDdichloromalonate.
  • Decyl decanoate 5 59 Tetrab enzyl dichloromethyl- Naphthalene 3 enediphosphonate. 60- Tris(p-nitrobenzyl)diiodo- Soybean oil 3 phosphonoacetate. 61 Bis[bis(fluoromethyD-Dhos- Parallin 4 phorylldichloromethane. 62. Bis(2,4-dichlorobenzoyl) di- Tripropylene glycol 5 bromomethane. didecanoate. 63 Dioleyl dibromomalonate. Stearyl stearate 8 64- Bls(p-dodecylbenzoyl) di- Stearyl benzoate 10 chloromethane.
  • soybean oil 76. cyanodibromophenylme- Tallow 8 thane. 77. Dicyelohexyl bromomalonate. Methyl stearate 5 78- Ethyl(perfluorophenyl)di- Fluorinated polyprog bromoacetate. gyfiege (M.W.
  • EXAMPLE IV The following table compares the base oil of Example I with compositions containing the indicated amounts of the indicated additives in a four ball tester, a Timken tester, and a Falex tester. All three tests should be used to determine if the extreme pressure additive has wide utility. The representative additives of this invention are all clearly superior to the commercially available additives.
  • each X is selected from the group consisting of chlorine,” iodine" and bromineatoms'
  • each R is selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, alkenyl, haloalkyl, haloaryl, haloalkaryl, haloaral-kyl, haloalkenyl'and nitroaryl moieties containing from 1 to about 22 carbon atoms.
  • component (2) is selected from the group consisting of dibromomethylenediphosphonate esters, diiodomethylenediphosphonate esters, and dichloromethylenediphosphonate esters,
  • each R is an alkyl group containing from 1 to about 6 carbon atoms.
  • composition of claim 1 wherein there is from about 1% to about of component (2).
  • composition of claim 1 wherein there is from about 2% to about 10% of component (2).
  • each R is an alkyl group containing from about 7 to about 22 carbon atoms.
  • each R is an alkyl group contairn'ng from 1 to about 6 carbon atoms.
  • composition of claim 1 wherein the lubricating base fluid is a lubricating oil.
  • Example IV All parts, percentages, and ratios herein are by weight unless otherwise sgecified.
  • the four ball results in Example IV were obtained on a diflerent testing machine than the results in the other examples W R0 OR ieh caused the discrepancy.

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US762966A 1968-09-26 1968-09-26 Lubricant composition Expired - Lifetime US3579449A (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3720614A (en) * 1970-09-25 1973-03-13 Monsanto Co Polyphenyl thioether lubricating compositions
US4108783A (en) * 1974-04-09 1978-08-22 The Lubrizol Corporation Haloalkyl hydroxy-aromatic condensation products as fuel and lubricant additives
US4138349A (en) * 1977-01-10 1979-02-06 General Electric Company Silicone lubricant compositions containing trischloroethyl-phosphite and/or bis-chloroethyl chloroethyl phosphonate
US4179449A (en) * 1974-04-09 1979-12-18 The Lubrizol Corporation Haloalkyl hydroxy-aromatic condensation products as fuel and lubricant additives
US4194886A (en) * 1974-04-09 1980-03-25 The Lubrizol Corporation Haloalkyl hydroxy-aromatic condensation products as fuel additives
WO2017193174A1 (en) * 2016-05-11 2017-11-16 Commonwealth Scientific And Industrial Research Organisation Polysiloxane hydraulic fluids
US12227713B2 (en) 2016-05-11 2025-02-18 The Boeing Company Polysiloxane hydraulic fluids

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3784297A (en) * 1970-03-11 1974-01-08 Canon Kk Photocopying machine
DE2747608A1 (de) * 1976-10-28 1978-05-03 Ciba Geigy Ag Wirksame fluessigkeitszusammensetzung

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3720614A (en) * 1970-09-25 1973-03-13 Monsanto Co Polyphenyl thioether lubricating compositions
US4108783A (en) * 1974-04-09 1978-08-22 The Lubrizol Corporation Haloalkyl hydroxy-aromatic condensation products as fuel and lubricant additives
US4179449A (en) * 1974-04-09 1979-12-18 The Lubrizol Corporation Haloalkyl hydroxy-aromatic condensation products as fuel and lubricant additives
US4194886A (en) * 1974-04-09 1980-03-25 The Lubrizol Corporation Haloalkyl hydroxy-aromatic condensation products as fuel additives
US4138349A (en) * 1977-01-10 1979-02-06 General Electric Company Silicone lubricant compositions containing trischloroethyl-phosphite and/or bis-chloroethyl chloroethyl phosphonate
WO2017193174A1 (en) * 2016-05-11 2017-11-16 Commonwealth Scientific And Industrial Research Organisation Polysiloxane hydraulic fluids
JP2019515120A (ja) * 2016-05-11 2019-06-06 コモンウェルス サイエンティフィック アンド インダストリアル リサーチ オーガニゼーション ポリシロキサン流体圧流体
US11299688B2 (en) 2016-05-11 2022-04-12 The Boeing Company Polysiloxane hydraulic fluids
US12227713B2 (en) 2016-05-11 2025-02-18 The Boeing Company Polysiloxane hydraulic fluids

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GB1287593A (en) 1972-08-31

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