US3696036A - Organic compositions containing tetraoctyl-(dimethyl-amino) methylene diphosphonate as antiwear agent - Google Patents

Organic compositions containing tetraoctyl-(dimethyl-amino) methylene diphosphonate as antiwear agent Download PDF

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US3696036A
US3696036A US30573A US3696036DA US3696036A US 3696036 A US3696036 A US 3696036A US 30573 A US30573 A US 30573A US 3696036D A US3696036D A US 3696036DA US 3696036 A US3696036 A US 3696036A
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amino
dimethyl
tetraoctyl
methylene diphosphonate
organic compositions
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US30573A
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Axel Klaus Commichau
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ExxonMobil Oil Corp
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Mobil Oil Corp
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • 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
    • C07F9/405—Esters of poly(thio)phosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
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    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • 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
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/286—Esters of 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
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
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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
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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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
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
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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
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2223/06—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
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02—Esters of silicic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
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    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
    • C10M2227/081—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds with a metal carbon bond belonging to a ring, e.g. ferocene
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    • C10M2229/04—Siloxanes with specific structure
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    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention relates to organic compositions, and in one of its aspects, relates more particularly to improved organic compositions, such as mineral oil-based organic compositions, in the form of fuel oils, lubricating oils and greases which normally exhibit poor antiwear properties during performance.
  • the present invention in its preferred applications, contemplates organic compositions of the abovedescribed types which contain a small amount of the aforementioned tetraoctyl-(dimethyl-amino) methylene diphosphonate antiwear improving agent, preferably in an amount of at least about 0.1% and usually, for most applications, in an amount from about 0.1 to about 5%, by weight of the total weight of such compositions.
  • the organic compositions improved in accordance with the present invention may comprise any materials that normally exhibit poor antiwear properties.
  • a field of specific applicability is the improvement of liquid hydrocarbons boiling from about 75 F. to about 1000 F. Of particular significance is the treatment of petroleum distillate fuel oils having an initial boiling point from about 75 F. to about 135 F. and an end boiling point from about 250 F. to about 750 F.
  • distillate fuel oils is not intended to be restricted to straight-run distillate fractions. These distillate fuel oils can be straight-run distillate fuel oils, catalytically or thermally cracked (including hy- 3,696,036 Patented Oct. 3, 1972 ice?
  • drocracked distillate fuel oils or mixtures of straightrun distillate fuel oils, naphthas and the like, with cracked distillate stocks.
  • fuel oils can be treated in accordance with well known commercial methods, such as acid or caustic treatment, hydrogenation, solvent-refining, clay treatment and the like.
  • distillate fuel oils are characterized by their relatively low viscosity, pour point and the like.
  • the principal property which characterizes these hydrocarbons, however, is their distillation range. As hereinbefore indicated, this range will lie between about F. and about 750 F. Obviously, the distillation range of each individual fuel oil will cover a narrower boiling range, falling nevertheless within the above-specified limits. Likewise, each fuel oil will boil substantially, continuously throughout its distillation range.
  • fuel oils are Nos. 1, 2 and 3 fuel oils, used in heating and as diesel fuel oils, gasoline, turbine oil and jet combustion fuels.
  • the domestic fuel oils generally conform to the specifications set forth in ASTM Specification D396-48T.
  • Specifications for diesel fuels are defined in ASTM Specification D975- 48T.
  • Typical jet fuels are defined in Military Specification MIL-F-5624B.
  • hydrocarbon lubricating oils of varying viscosity and pour points, falling both within the aforementioned range and as high as 1000 F. or higher, may also be effectively treated through the use of the aforementioned additive.
  • the aforementioned additive of the present invention may also be incorporated as antioxidants or antiwear agents in grease compositions.
  • Such greases may comprise a combination of a wide variety of lubricating vehicles and thickening or gelling agents.
  • greases in which the aforementioned additive is particularly efiective may comprise any of the conventional hydrocarbon oils of lubricating viscosity, as the oil vehicle, and may include mineral or synthetic lubricating oils, aromatic and aliphatic phosphates, esters and diesters, silicates, siloxanes and oxalkyl ethers and esters.
  • Mineral lubricating oils, employed as the lubricating vehicle may be of any suitable lubricating viscosity range from about 45 SSU at 100 F.
  • oils may have viscosity indexes varying from below 0 to about 100 or higher. Viscosity indexes from about 70 to about are preferred. The average molecular weights of these oils may range from about 250 to about 800.
  • the lubricating oil is employed in the grea e composition in an amount sufficient to constitute the balance of the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease formulation.
  • the oil vehicles employed in the novel grease formulations of the present invention may comprise mineral or synthetic oils of lubricating viscosity.
  • mineral oils having a viscosity of at least 40 SSU at F., and particularly those falling within the range from about 60 SSU to about 6,000 SSU at 100 F., may be employed.
  • synthetic vehicles are employed rather than mineral oils, or in combination therewith, as the lubricating vehicle, various compounds of this type may be successfully utilized.
  • Typical synthetic vehicles include: polypropylene, polyisobutylene, polybutenes, hydrogenated polydecenes, polypropylene glycol, polyethylene glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di(Z-ethyl hexyl) sebacate, di(2-ethyl hexyl) adipate, di(butyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorus-containing acids,
  • liquid ureas liquid ureas, ferrocene derivatives, hydrogenated mineral oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes), alkyl-substituted diphenyl ethers typified by a butyl-substituted bis (p-phenoxy phenyl) ether, phenoxy phenylethers, etc.
  • the lubricating vehicles of the aforementioned improved greases of the present invention containing the above-described tetraoctyl-(dimethyl-amino) methylene diphosphonate as an additive is combined with a greaseforming quantity of a thickening agent.
  • a thickening agent for this purpose, a wide variety of materials may be employed.
  • These thickening or gelling agents may include any of the conventional metal salts or soaps, which are dispersed in the lubricating vehicle in grease-forming quantities in such degree as to impart to the resulting grease composition the desired consistency.
  • thickening agents that may be employed in the grease formulation may comprise the non-soap thickeners, such as surface-modified clays and silicas, aryl ureas, calcium complexes and similar materials.
  • grease thickeners may be employed which do not melt and dissolve when used at the required temperature within a particular environment; however, in all other respects any material which is normally employed for thickening or gelling hydrocarbon fluids for forming grease can be used in preparing the aforementioned improved grease in accordance with the present invention.
  • tetraoctyl-(dimethyl-amino) methylene diphosphonate additive of the present invention may be prepared, in general, by the reaction of di-n-octylphosphite and dimethylformamiddimethylacetal, in accordance with stoichiometrical requirements, as shown by the following equation:
  • reaction may be carried out under ambient conditions of room temperature and pressure, although elevated temperature and pressure may be also utilized for increasing the rate of reaction.
  • Example 1 The main run of Table I comprised the desired tetraoctyl-(dimethyl-amino) methylene diphosphonate (hereinafter designated as TDMP, for convenience) and upon analysis exhibited the characteristics shown in the following Table H:
  • Example 3 In order to evaluate the performance of the antiwear additive TDMP of the present invention, the standard Four Ball Test was employed. In this test the run was made at 60 kg. level for a period of three minutes at a temperature of 390 F. and at 1800 r.p.m. An ester base oil, comprising a pentaerythritol base ester of 5 cs. at 210 F. was subjected to test and displayed a Wear scar diameter of 2.24 mm.
  • the novel TDMP additive of the present invention exhibits an ability to impart outstanding antiwear properties to organic compositions.
  • An organic composition selected from the group consisting of lubricating oils, fuel oils, and greases containing, in an amount sufiicient to exhibit antiwear properties, tetraoctyl- (dimethyl-amino) methylene diphosphonate.
  • composition as defined in claim 1 wherein said composition comprises a liquid hydrocarbon boiling within the range from about 75 F. to about 1000" F.
  • composition as defined in claim 1 wherein said composition comprises a petroleum distillate fuel oil having an initial boiling point from about 75 F. to about 135 F. and an end boiling point from about 250 F. to about 750 F.
  • composition as defined in claim 1 wherein said tetraoctyl-(dimethyl-amino) methylene diphosphonate is present in an amount of at least about 0.1% by weight.

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Abstract

ORGANIC COMPOSITIONS ARE PROVIDED CONTAINING TETRAOCTYL-(DIMETHYL-AMINO) METHYLENE DIPHOSPHONATE, AS AN ANTIWEAR AGENT. PARTICULARLY COMTEMPLATED ARE MINERAL OILBASED ORGANIC CIMPOSITIONS SUCH AS FUEL OILS, LUBRICATING OIL AND GREASES CONTAINING ANTI-WEAR AMOUNTS OF TETROOCTYL-(DIMETHYL-AMINO) METHYLENE DIPHOSPHONATE.

Description

Unitd states Patent 3,696,036 ORGANIC COMPOSITIONS CONTAINING TETRA- OCTYL-(DlMETHYL-AMINO) METHYLENE DI- PHOSPHONATE AS ANTIWEAR AGENT Axel Klaus Commichau, Hamburg-Rissen, Germany, assignor to Mobil Oil Corporation, New York, N.Y. No Drawing. Filed Apr. 21, 1970, Ser. No. 30,573 Int. Cl. C10m 1/46, /24 US. Cl. 252-493 12 Claims ABSTRACT OF THE DISCLOSURE Organic compositions are provided containing tetraoctyl-(dimethyl-amino) methylene diphosphonate, as an antiwear agent. Particularly contemplated are mineral oilbased organic compositions such as fuel oils, lubricating oils and greases containing anti-wear amounts of tetraoctyl-(dimethyl-amino) methylene diphosphonate.
BACKGROUND OF THE INVENTION (1) Field of the invention This invention relates to organic compositions, and in one of its aspects, relates more particularly to improved organic compositions, such as mineral oil-based organic compositions, in the form of fuel oils, lubricating oils and greases which normally exhibit poor antiwear properties during performance.
(2) Description of the prior art It is well known that certain types of organic compositions normally exhibit poor antiwear properties during the course of their performance. This is particularly apparent when organic fuel compositions are employed such as liquid hydrocarbon fuels, including gasolines, jet fuels and turbine oils. Furthermore, it is also known that various organic compositions, when employed in the form of lubricating oils or greases, in many instances, tend to exhibit the aforementioned antiwear properties, thus clearly indicating the necessity for incorporating into such fuels and lubricants effective antiwear improving agents.
SUMMARY OF THE INVENTION It has now been found that antiwear properties of the aforementioned organic compositions, particularly in the form of fuels and lubricants, can be effectively improved by incorporating therein small amounts of tetraoctyl-(dimethyl-amino) methylene diphosphonate, prepared in accordance with the process more fully hereinafter described.
In general, the present invention in its preferred applications, contemplates organic compositions of the abovedescribed types which contain a small amount of the aforementioned tetraoctyl-(dimethyl-amino) methylene diphosphonate antiwear improving agent, preferably in an amount of at least about 0.1% and usually, for most applications, in an amount from about 0.1 to about 5%, by weight of the total weight of such compositions.
The organic compositions improved in accordance with the present invention may comprise any materials that normally exhibit poor antiwear properties. A field of specific applicability is the improvement of liquid hydrocarbons boiling from about 75 F. to about 1000 F. Of particular significance is the treatment of petroleum distillate fuel oils having an initial boiling point from about 75 F. to about 135 F. and an end boiling point from about 250 F. to about 750 F. It should be noted, in this respect, that the term distillate fuel oils is not intended to be restricted to straight-run distillate fractions. These distillate fuel oils can be straight-run distillate fuel oils, catalytically or thermally cracked (including hy- 3,696,036 Patented Oct. 3, 1972 ice? drocracked) distillate fuel oils, or mixtures of straightrun distillate fuel oils, naphthas and the like, with cracked distillate stocks. Moreover, such fuel oils can be treated in accordance with well known commercial methods, such as acid or caustic treatment, hydrogenation, solvent-refining, clay treatment and the like.
The distillate fuel oils are characterized by their relatively low viscosity, pour point and the like. The principal property which characterizes these hydrocarbons, however, is their distillation range. As hereinbefore indicated, this range will lie between about F. and about 750 F. Obviously, the distillation range of each individual fuel oil will cover a narrower boiling range, falling nevertheless within the above-specified limits. Likewise, each fuel oil will boil substantially, continuously throughout its distillation range.
Particularly contemplated among the fuel oils are Nos. 1, 2 and 3 fuel oils, used in heating and as diesel fuel oils, gasoline, turbine oil and jet combustion fuels. The domestic fuel oils generally conform to the specifications set forth in ASTM Specification D396-48T. Specifications for diesel fuels are defined in ASTM Specification D975- 48T. Typical jet fuels are defined in Military Specification MIL-F-5624B. In addition, as previously indicated, hydrocarbon lubricating oils of varying viscosity and pour points, falling both within the aforementioned range and as high as 1000 F. or higher, may also be effectively treated through the use of the aforementioned additive.
As previously indicated, the aforementioned additive of the present invention may also be incorporated as antioxidants or antiwear agents in grease compositions. Such greases may comprise a combination of a wide variety of lubricating vehicles and thickening or gelling agents. Thus, greases in which the aforementioned additive is particularly efiective, may comprise any of the conventional hydrocarbon oils of lubricating viscosity, as the oil vehicle, and may include mineral or synthetic lubricating oils, aromatic and aliphatic phosphates, esters and diesters, silicates, siloxanes and oxalkyl ethers and esters. Mineral lubricating oils, employed as the lubricating vehicle, may be of any suitable lubricating viscosity range from about 45 SSU at 100 F. to about 6,000 SSU at 100 F., and, preferably, from about 50 to about 250 SSU at 210 F. These oils may have viscosity indexes varying from below 0 to about 100 or higher. Viscosity indexes from about 70 to about are preferred. The average molecular weights of these oils may range from about 250 to about 800. The lubricating oil is employed in the grea e composition in an amount sufficient to constitute the balance of the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease formulation.
As previously indicated, the oil vehicles employed in the novel grease formulations of the present invention, in which the aforementioned additive is incorporated as an antiwear agent, may comprise mineral or synthetic oils of lubricating viscosity. When high temperature stability is not a requirement of the finished grease, mineral oils having a viscosity of at least 40 SSU at F., and particularly those falling within the range from about 60 SSU to about 6,000 SSU at 100 F., may be employed. In instances where synthetic vehicles are employed rather than mineral oils, or in combination therewith, as the lubricating vehicle, various compounds of this type may be successfully utilized. Typical synthetic vehicles include: polypropylene, polyisobutylene, polybutenes, hydrogenated polydecenes, polypropylene glycol, polyethylene glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di(Z-ethyl hexyl) sebacate, di(2-ethyl hexyl) adipate, di(butyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorus-containing acids,
liquid ureas, ferrocene derivatives, hydrogenated mineral oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes), alkyl-substituted diphenyl ethers typified by a butyl-substituted bis (p-phenoxy phenyl) ether, phenoxy phenylethers, etc.
The lubricating vehicles of the aforementioned improved greases of the present invention containing the above-described tetraoctyl-(dimethyl-amino) methylene diphosphonate as an additive is combined with a greaseforming quantity of a thickening agent. For this purpose, a wide variety of materials may be employed. These thickening or gelling agents may include any of the conventional metal salts or soaps, which are dispersed in the lubricating vehicle in grease-forming quantities in such degree as to impart to the resulting grease composition the desired consistency. Other thickening agents that may be employed in the grease formulation may comprise the non-soap thickeners, such as surface-modified clays and silicas, aryl ureas, calcium complexes and similar materials. In general, grease thickeners may be employed which do not melt and dissolve when used at the required temperature within a particular environment; however, in all other respects any material which is normally employed for thickening or gelling hydrocarbon fluids for forming grease can be used in preparing the aforementioned improved grease in accordance with the present invention.
The tetraoctyl-(dimethyl-amino) methylene diphosphonate additive of the present invention may be prepared, in general, by the reaction of di-n-octylphosphite and dimethylformamiddimethylacetal, in accordance with stoichiometrical requirements, as shown by the following equation:
CaHivO CHa di-n-octylphosphite dimethylformamiddimethylacetal CHzO C HN C Hz) 2 Q CBHITO nCs 2CHaOH methanol tetraoctyl-(dimethyl-amino) methylene diphosphonate The reaction may be carried out under ambient conditions of room temperature and pressure, although elevated temperature and pressure may be also utilized for increasing the rate of reaction.
DESCRIPTION OF SPECIFIC EMBODIMENTS The following data and examples will serve to illustrate the novel antiwear additive of the present invention and its efficacy as improving agent in organic compositions. It will be understood, however, that it is not intended the invention be limited to the particular method of preparation of this additive, as described. Various modifications thereof can be employed and may be readily apparent to those skilled in the art.
Example 1 The main run of Table I comprised the desired tetraoctyl-(dimethyl-amino) methylene diphosphonate (hereinafter designated as TDMP, for convenience) and upon analysis exhibited the characteristics shown in the following Table H:
TABLE II Main run TDMP TDMP theoretical Percent:
Nitrogen 2. 4; 2. 4 2. 1 Carbon 61.9; 60.5 63.0 Hydrogen 9.9; 10.2 11. 2 Mol. weight 794 667 Example 2 In order to evaluate the performance of the antiwear additive TDMP of the present invention, the standard FZG Test A8.3- was employed. In this test, the ability of the oil to pass the maximum number of stages is a relative indication of its load-carrying capability. In accordance with the test, a sample of hydrogenated polydecene gear oil was run in accordance with the standard provisions of the test and was found to exhibit an ability to pass 8 stages.
'For purposes of comparison another test gear oil was prepared comprising 99.5%, by weight, of the aforementioned identical hydrogenated polydecene gear oil and 0.5%, by Weight, of the above-described TDMP. This gear oil, when subjected to the same FZG Test exhibited markedly improved load-carrying capability, in that it was able to pass 11 stages of the test.
Example 3 In order to evaluate the performance of the antiwear additive TDMP of the present invention, the standard Four Ball Test was employed. In this test the run was made at 60 kg. level for a period of three minutes at a temperature of 390 F. and at 1800 r.p.m. An ester base oil, comprising a pentaerythritol base ester of 5 cs. at 210 F. was subjected to test and displayed a Wear scar diameter of 2.24 mm.
For purposes of comparison, another gear oil was prepared comprising the above-described ester base oil but containing a sufficient amount of the above-described TDMP to obtain an 0.04%, by weight, phosphorus level. In contrast, it was found as a result of the test that this TDMP-containing oil displayed a wear scar diameter of only 0.8 mm.
As will be seen from the foregoing comparative data and results obtained, the novel TDMP additive of the present invention exhibits an ability to impart outstanding antiwear properties to organic compositions. Although the present invention has been described with preferred embodiments, it will be understood that various modifications and adaptations thereof may be resorted to without departing from the spirit and scope of the invention as those skilled in the art will readily understand.
I claim:
1. An organic composition selected from the group consisting of lubricating oils, fuel oils, and greases containing, in an amount sufiicient to exhibit antiwear properties, tetraoctyl- (dimethyl-amino) methylene diphosphonate.
2. A composition as defined in claim 1 wherein said composition comprises a mineral oil-based composition.
3. A composition as defined in claim 1 wherein said composition comprises a liquid hydrocarbon boiling within the range from about 75 F. to about 1000" F.
4. A composition as defined in claim 1 wherein said composition comprises a lubricating oil.
5. A composition as defined in claim 1 wherein said composition comprises a grease.
6. A composition as defined in claim 1 wherein said composition comprises a petroleum distillate fuel oil having an initial boiling point from about 75 F. to about 135 F. and an end boiling point from about 250 F. to about 750 F.
7. A composition as defined in claim 1 wherein said composition comprises a gasoline.
8. A composition as defined in claim 1 wherein said composition comprises a jet fuel.
9. A composition as defined in claim 1 wherein said composition comprises a turbine oil.
10. A composition as defined in claim 1 wherein said composition comprises a diesel fuel.
11. A composition as defined in claim 1 wherein said tetraoctyl-(dimethyl-amino) methylene diphosphonate is present in an amount of at least about 0.1% by weight.
12. A composition as defined in claim 1 wherein said tetraoctyl-(dimethyl-amino) methylene diphosphonate is present in an amount from about 0.1 to about 5% by weight.
References Cited UNITED STATES PATENTS 3,553,131 1/1971 Hepplewhite et al. 252--49.9 2,635,112 4/1953 Fields 252-499 3,549,728 12/1970 Balde et al. 25.2-49.9
DANIEL E. WYMAN, Primary Examiner I. VAUGHN, Assistant Examiner U.S. Cl. X.R.
44-DIG 4, 72; 252-400
US30573A 1970-04-21 1970-04-21 Organic compositions containing tetraoctyl-(dimethyl-amino) methylene diphosphonate as antiwear agent Expired - Lifetime US3696036A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3909430A (en) * 1972-08-07 1975-09-30 Chevron Res Lubricating composition
US5630852A (en) * 1994-11-23 1997-05-20 Fmc Corporation Organophosphorus additives for improved fuel lubricity

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3909430A (en) * 1972-08-07 1975-09-30 Chevron Res Lubricating composition
US5630852A (en) * 1994-11-23 1997-05-20 Fmc Corporation Organophosphorus additives for improved fuel lubricity

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