US2824839A - Lubricants - Google Patents

Lubricants Download PDF

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US2824839A
US2824839A US415961A US41596154A US2824839A US 2824839 A US2824839 A US 2824839A US 415961 A US415961 A US 415961A US 41596154 A US41596154 A US 41596154A US 2824839 A US2824839 A US 2824839A
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lubricant
mineral
composition
linked
film strength
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US415961A
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Glen C Templeman
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Ohio Oil Co
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Ohio Oil Co
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Semi-solids; greasy

Definitions

  • This invention is that of mineral-type lubricant compositions having improved extreme pressure characteristics especially improved film strength, and containing a major portion of a mineral-type lubricant and a small amount, sufficient to increase the film strength of the lubricant, of a film strength enhancer of a particular type.
  • the particular type of film strength enhancer broadly viewed is a di(halogen-substituted aliphatic hydrocarbon radical) aliphatic hydrocarbon phosphonate that is sufiiciently soluble in the mineral-type lubricant to provide in it a sufiicient concentration of the phosphonate significantly to enhance the film strength of the lubricant.
  • Such phosphonates are described more specifically below.
  • mineral-type lubricant oils and greases of petroleum pounded oils and greases that cal characteristics similar to eating oils and greases.
  • the mineral-type lubricant compositions of the invention lack these various shortcomings, by their containing dissolved in the mineral-type lubricant a film strength improving concentration of a film strength enhancer of the invention.
  • a film strength improving concentration of a film strength enhancer of the invention is a di(halogen-substituted aliphatic hydrocarbon radical) aliphatic hydrocarbon radical phosphonate soluble in the mineral-type lubricant in a quantity sufficient significantly to enhance its film strength characteristics, inert to Water, stable at elevated temperatures and non-corrosive to ferrous and non-ferrous metals and their alloys, used in machinery requiring lubricants, and having the general formula Patented Feb.
  • R is a monovalent aliphatic hydrocarbon radical, beneficially lower-alkyl and advantageously unsaturated.
  • the divalent radical R advantageously is straight chain lower-alkylene with one end carbon linked to the oxygen and the other to the halogen.
  • di(halo-loWer-alkylene) lower-alkenyl phosphonates having the halogen linked to the outer end carbon are particularly advantageous among them.
  • the invention more specifically is that of mineral-type lubricant compositions containing a film strength improving quantity of a di(halo-alkyl) alkenyl phosphonate, with the halogen linked to the outer end carbon of the halo-alkyl radical, and the phosphonate having the characteristics of solubility in the lubricant, inertness to water, heat stability, and non-corrosiveness, as above described.
  • the mineral-type lubricant compositions of the invention can consist of the mineral-type lubricant and merely the film strength enhancer dissolved in it from a quantity just about sufiicient significantly to enhance the film strength up to about ten percent by Weight.
  • conventional additives such as antioxidants, dyes, pour point improvers, and agents to influence vicosity index, any or all of such substances compatible With their film strength enhancers can be included in the lubricant compositions of the invention.
  • the mineral-type lubricant is not the only ingredient other than the film strength enhancer, because the composition contains one or more of the various conventional additives as just described. Accordingly, while the lubricant ingredient can be present in an amount under ninety percent, it should, in any event, be the greater or major portion of the composition, that is to say, at least more than half of it by weight.
  • di(halo-alkyl) lower-alkenyl phosphonate of the type described above as applicable can be present in the lubricant compositions of the invention in an amount for example, with di(beta-chloroethyl) vinyl phosphonate, as little as one one-hundredth percent by weight up to the maximum given above.
  • compositions are prepared by incorporating the selected film strength enhancer in the mineral-type lubricant by dissolving it in any that is liquid. It can be incorporated into any that is not liquid or any of the suitable greases, for example, by warming the grease till it is fluid enough to be stirred and then adding the enhancer and stirring till it is dissolved. The solution can then cool till it again is an unctuous grease.
  • Example J In ninety-nine and one-half pounds of SAE #20 solvent extracted Mid-Continent lubricating oil there was homogeneously dissolved one-half pound of di(beta-chloroethyl) vinyl phosphonate.
  • Example 2 ninety-nine pounds of the oil of Example 1 there was similarly dissolved one pound of di(beta-chloroethyl) vinyl phosphonate.
  • Example 3 ninety-eight parts of the. oil of Example 1 there were similarly dissolved two pounds of di(beta-chloroethyl) vinyl phosphonate.
  • the lubricant composition ofeach of the examples was tested on the Burns-type Almen machine for evaluating film strength.
  • the limit of the weight. load (twenty-four pounds) was added to the weight. carrier suspended from the beam, but no betwee the bearin an the shaftan the MGM! ceeding 94,746 pounds per V the same proportions 7 'alkyl) vinyl phosphonate'or w an outer'endcarbon,
  • Burns-type Almen in that the Burns-type permits greater pressures film strength enhancer can constitute, for example, from 'aboutone one-hundredth to about 7 weightof the lubricant'composition.
  • the di(beta-chloro-ethyl) vinyl phosphonate film strength enhancer used in the examples can be replaced by. a comparable amount of any. other suitable" di(beta-halo-ethyl) vinyl phosphonate or di(halo-lowerdi(halo-lower-alkyl) lower alkenyl phosphonate, in which the halogen is linked to and which phosphonates' are soluble in the mineral-type lubricauts up toabout ten percent of the total weight, are inert to- Water, stable'at elevated temperatures, and non-corrosive to the surfaces of the metals of the type above described.
  • any of the lubricating oil compositions of the examples-or'of any of the. above described possible modifications of them, of any. one'or more of the conventional additivesjsuch as antioxidants, dyes, pour points improvers, a'nd agents 7 index, 'so long as it is compatiblewith the film strength a V has been explained by detailed description of certain specific embodiments ofit, it is canjbeirnade'in the lubricant compositions embraced by theinvention withinthescope of the appendedclaims which are intended to cover also equivalents of the specific embodiments;
  • composition a small amount, 'suflicienttoenhance e lubricant, of a di(halo-alkyl),
  • V V rnono-olefinic. aliphatic hydrocarbon radical-Sribstitutd phosphonate additive wherein the mono-olefin'ic hydro- ,is linked by acarbon directly to the phosphorus and each of thetwo' halo-alkyl radicals is linked respectively to a separateo'neof the oxygens linked additive is soluble in the square inch (thejlimit' of thei Zuidemas The Performance of Lubri source mineral.
  • lubricant selected V class'consisting of mineral oils and greases, .and (b) as the filmstrength enhancing constituent of "composition having. enhanced filni lubricant ingredient at least, in said small amount and, in. such small concentration in the lubricant, is inert to water, stable at elevated temperatures, and non-corrosive to the ferrous and non-ferrous metals. and their alloys 'that are used in devices requiring lubricants; said composition having enhanced ,film strength over that which i the mineral-type lubricant itself'has without this additive.
  • cal is lower aliphatic, and the: thus substituted phos-.
  • phouate is present in the range. of from about one onehundredth to about- .ten percent 7 by weight 'of the composition.
  • A'mineral V V a major proportion of a mineral oil lubricant selected from the class consistingloflmineral; oils; and greases,
  • lubricant is inert to Water, stable, atfelevatedtemperatures, and non-.corrosiveto. the. ferrous and non-ferrous:
  • a mineral oil'lubricant composition comprising-"( a)" or a major proportion of a miueral .oililubr'icant selected: from the class consistiugyofniineral oil's. andgreases,
  • composition a small amounnfsufricient to enhance.
  • a lubricant composition as claimed in claim '4;
  • lubricantingredient is a mineral lubricating oil.
  • a lubricant composition as; wherein therlubricant ingredient, is fa .mineral'oil.
  • lubricant ingredient is 7 SALE #20 solvent ex-s tracted,Mid-Continentilubricating oil.
  • a mineral oil lubricantcomposition comprising (a) i a major proportion of a mineral oil lubricant selected; from the. classconsisting: of mineral oils and greases; and (b) asv the" film strength enhancing constituentbfi about one one-hundredth 'tol a about; tenpercent by weight of the composition, said-f.

Description

LUBRICANTS 11L, assignor to The Ohio a corporation of Ohio Glen (3. Templeman, Robinson, Oil Company, Findlay, Ohio,
9 Claims. (Cl. 25249.9)
This invention is that of mineral-type lubricant compositions having improved extreme pressure characteristics especially improved film strength, and containing a major portion of a mineral-type lubricant and a small amount, sufficient to increase the film strength of the lubricant, of a film strength enhancer of a particular type. The particular type of film strength enhancer broadly viewed is a di(halogen-substituted aliphatic hydrocarbon radical) aliphatic hydrocarbon phosphonate that is sufiiciently soluble in the mineral-type lubricant to provide in it a sufiicient concentration of the phosphonate significantly to enhance the film strength of the lubricant. Such phosphonates are described more specifically below.
By mineral-type lubricant oils and greases of petroleum pounded oils and greases that cal characteristics similar to eating oils and greases.
The many difiicult lubricating problems presented by the drastic conditions to which modern machines with moving parts are subjected have created a great demand for lubricants that provide tough, compression resistant films on metal surfaces. In addition, these films must hold up at high temperatures, be inert to water and non-corrosive to the parts they contact. As long as the film is not ruptured, metal to metal contact is avoided and seizure between the parts moving against one another does not occur.
Numerous compounds have been proposed for inclusion in mineral-type lubricants to improve their extreme pressure characteristics. However, many of them are not suificiently soluble in the lubricant to enable including a concentration sufiicient to provide suitable enhancement of these characteristics. Others are unstable as the is intended the lubricating origin as well as the comhave chemical and physithe petroleum origin lubritemperature 1s elevated. Many are corrosive to the surfaces to be lubricated, and still others are adversely efiected by water. Then also, many exhibit several and even all of these and other shortcomings.
The mineral-type lubricant compositions of the invention lack these various shortcomings, by their containing dissolved in the mineral-type lubricant a film strength improving concentration of a film strength enhancer of the invention. Considered broadly, the latter is a di(halogen-substituted aliphatic hydrocarbon radical) aliphatic hydrocarbon radical phosphonate soluble in the mineral-type lubricant in a quantity sufficient significantly to enhance its film strength characteristics, inert to Water, stable at elevated temperatures and non-corrosive to ferrous and non-ferrous metals and their alloys, used in machinery requiring lubricants, and having the general formula Patented Feb. 25, 1958 rated or unsaturated; and R is a monovalent aliphatic hydrocarbon radical, beneficially lower-alkyl and advantageously unsaturated. The divalent radical R advantageously is straight chain lower-alkylene with one end carbon linked to the oxygen and the other to the halogen.
Advantageously eifective among these film strength enhancers are the di(halo-loWer-alkylene) lower-alkenyl phosphonates having the halogen linked to the outer end carbon. Strikingly advantageous among them are the di(beta-halo-ethyl) vinyl phosphonates and especially di(beta-chlorethyl) vinyl phosphonate.
Accordingly, the invention more specifically is that of mineral-type lubricant compositions containing a film strength improving quantity of a di(halo-alkyl) alkenyl phosphonate, with the halogen linked to the outer end carbon of the halo-alkyl radical, and the phosphonate having the characteristics of solubility in the lubricant, inertness to water, heat stability, and non-corrosiveness, as above described.
The mineral-type lubricant compositions of the invention can consist of the mineral-type lubricant and merely the film strength enhancer dissolved in it from a quantity just about sufiicient significantly to enhance the film strength up to about ten percent by Weight. However, since there can be admixed with mineral-type lubricants conventional additives such as antioxidants, dyes, pour point improvers, and agents to influence vicosity index, any or all of such substances compatible With their film strength enhancers can be included in the lubricant compositions of the invention.
Thus, in many of the embraced lubricant compositions, the mineral-type lubricant is not the only ingredient other than the film strength enhancer, because the composition contains one or more of the various conventional additives as just described. Accordingly, while the lubricant ingredient can be present in an amount under ninety percent, it should, in any event, be the greater or major portion of the composition, that is to say, at least more than half of it by weight.
The di(halo-alkyl) lower-alkenyl phosphonate of the type described above as applicable can be present in the lubricant compositions of the invention in an amount for example, with di(beta-chloroethyl) vinyl phosphonate, as little as one one-hundredth percent by weight up to the maximum given above.
The compositions are prepared by incorporating the selected film strength enhancer in the mineral-type lubricant by dissolving it in any that is liquid. It can be incorporated into any that is not liquid or any of the suitable greases, for example, by warming the grease till it is fluid enough to be stirred and then adding the enhancer and stirring till it is dissolved. The solution can then cool till it again is an unctuous grease.
The invention may be illustrated by, but not restricted to, the following examples:
Example J.In ninety-nine and one-half pounds of SAE #20 solvent extracted Mid-Continent lubricating oil there was homogeneously dissolved one-half pound of di(beta-chloroethyl) vinyl phosphonate.
Example 2.ln ninety-nine pounds of the oil of Example 1 there was similarly dissolved one pound of di(beta-chloroethyl) vinyl phosphonate.
Example 3.ln ninety-eight parts of the. oil of Example 1 there were similarly dissolved two pounds of di(beta-chloroethyl) vinyl phosphonate.
The lubricant composition ofeach of the examples was tested on the Burns-type Almen machine for evaluating film strength. In each case the limit of the weight. load (twenty-four pounds) was added to the weight. carrier suspended from the beam, but no betwee the bearin an the shaftan the MGM! ceeding 94,746 pounds per V the same proportions 7 'alkyl) vinyl phosphonate'or w an outer'endcarbon,
, can containia suitable amount enhancer'used.
' 'While the invention understood thatiyarious "amajjor'proportion ofa mineral oil the film'strength of th carboniradieal 7 to the phosphorus, which of the shaft was not sheared off. This showed that the film strength of the composition of each of these examples withstands a projected bearing surface pressure exmachine) catingi'Oils (1952), Reinhold Publishing'corporation;
New York, N. Y., describes the Almen machine; There 7 between it. and the Burns-type Almen, in that the Burns-type permits greater pressures film strength enhancer can constitute, for example, from 'aboutone one-hundredth to about 7 weightof the lubricant'composition.
ten percent of the The di(beta'-chloro-ethyl) vinyl mercially readily available and is especially effective be cause of its liquidity, ready solubility in the mineral oils and greases, high boiling point and low vapor pres sure, stability at elevated temperatures, inertness to water,
7 non-'corrosiveness'to the metals of the types above de-. scribed, 'mild pleasant odor, andwater-white color. In
addition to the vastly improved film strength imparted by. it to'the lubricant, the resulting composition shows markedly reduced coefiicient of friction. 1
' -'Moreove r, the di(beta-chloro-ethyl) vinyl phosphonate film strength enhancer used in the examples can be replaced by. a comparable amount of any. other suitable" di(beta-halo-ethyl) vinyl phosphonate or di(halo-lowerdi(halo-lower-alkyl) lower alkenyl phosphonate, in which the halogen is linked to and which phosphonates' are soluble in the mineral-type lubricauts up toabout ten percent of the total weight, are inert to- Water, stable'at elevated temperatures, and non-corrosive to the surfaces of the metals of the type above described. V V
o In addition. to'the film strength enhancer, any of the lubricating oil compositions of the examples-or'of any of the. above described possible modifications of them, of any. one'or more of the conventional additivesjsuch as antioxidants, dyes, pour points improvers, a'nd agents 7 index, 'so long as it is compatiblewith the film strength a V has been explained by detailed description of certain specific embodiments ofit, it is canjbeirnade'in the lubricant compositions embraced by theinvention withinthescope of the appendedclaims which are intended to cover also equivalents of the specific embodiments;
. What is claimed is:
. l.-Amineral'oil lubricant composition comprising (a) fi om the;
said composition a small amount, 'suflicienttoenhance e lubricant, of a di(halo-alkyl),
V V rnono-olefinic. aliphatic hydrocarbon radical-Sribstitutd phosphonate additive wherein the mono-olefin'ic hydro- ,is linked by acarbon directly to the phosphorus and each of thetwo' halo-alkyl radicals is linked respectively to a separateo'neof the oxygens linked additive is soluble in the square inch (thejlimit' of thei Zuidemas The Performance of Lubri source mineral.
to enhance the viscosity.
phosphonate is 7 comsubstitutions and modifications:
lubricant selected V class'consisting of mineral oils and greases, .and (b) as the filmstrength enhancing constituent of "composition having. enhanced filni lubricant ingredient at least, in said small amount and, in. such small concentration in the lubricant, is inert to water, stable at elevated temperatures, and non-corrosive to the ferrous and non-ferrous metals. and their alloys 'that are used in devices requiring lubricants; said composition having enhanced ,film strength over that which i the mineral-type lubricant itself'has without this additive.
, 2. A mineral oil lubricant composition as claimed in claim 1, wherein the halo-alkyl groups are halo-lower-,
'alkyl and each with its halogen linked to its outer end carbon, and the mono-'olefinic aliphatic hydrocarbon radi-.
cal is lower aliphatic, and the: thus substituted phos-.
phouate is present in the range. of from about one onehundredth to about- .ten percent 7 by weight 'of the composition.
3. A'mineral V V a major proportion of a mineral oil lubricant selected from the class consistingloflmineral; oils; and greases,
and (b) as thefilm strength enhancing constituentot' enhance I thefilm strength of'the lubricant, of a dl(ChlQ1'O-l0WI- said, composition a small amount, sufiicient to' alkyl) vinyl phosphonate additive wherein the vinyl group is linked directly to alkyl. group has its carbon and is linked respectively to a. separate one of v the oxygens linked to. the phosphorus,: which, additive} is soluble. in the lubricant. ingredient at leasttinisaidi small amount, and in such. small concentration in the."
lubricant, is inert to Water, stable, atfelevatedtemperatures, and non-.corrosiveto. the. ferrous and non-ferrous:
metals and their' alloys that are used in devices-requiring. lubricants;
has without this additive.
4. A mineral oil'lubricant composition comprising-"( a)" or a major proportion of a miueral .oililubr'icant selected: from the class consistiugyofniineral oil's. andgreases,
and (b) as .thefilm strength enhancing constituent 0f:
'said compositiona small amounnfsufricient to enhance.
the film strength of the lubricant'ingredient; of'di(betachloro-ethyl) vinyl phosphonate, said composition hav-- ing enhanced film strengthover that eithe mineralioil lubricant itself. a V
5.. A lubricant composition. as claimed in claim '4;
. wherein the lubricantingredientis a mineral lubricating oil.
saidcomposition di(beta-chloroethyl) vinyl phosphonatewithin the. range ofv from the mineral oil'lubricantzitself, V
7. A lubricant compositionas wherein thelubrica'nt ingredientis a. mineral. oil'and the di(chloro-'ethyl) vinyl phosphcnateis present as one, per! cent of the, compositionby weight." j 7 j 8. A lubricant composition as; wherein therlubricant ingredient, is fa .mineral'oil.
9. A lubricant composition asfclaimed' inclainr 8,." 1
wherein the lubricant ingredient is 7 SALE #20 solvent ex-s tracted,Mid-Continentilubricating oil.
-References Cited inthe file of this atem I 7 UNITED PATENTS-x 'oil'lubricant composition comprising (a) i V the phosphorus and each chl'oro chlorine linked to theouter end.
said 'composition' having enhanced film strength'over that:which the mineral. oil lubricant itsfeli 6. A mineral oil lubricantcomposition comprising (a) i a major proportion of a mineral oil lubricant selected; from the. classconsisting: of mineral oils and greases; and (b) asv the" film strength enhancing constituentbfi about one one-hundredth 'tol a about; tenpercent by weight of the composition, said-f.
strength over that. of. j
claimed in claim id;
laiined in; anti-In,

Claims (1)

1. A MINERAL OIL LUBRICANT COMPOSITION COMPRISING (A) A MAJOR PROPORTION OF A MINERAL OIL LUBRICANT SELECTED FROM THE CLASS CONSISTING OF MINERAL OIL AND GREASES, AND (B) AS THE FILM STRENGHT ENHANCING CONSTITUENT OF SAID COMPOSITION A SMALL AMOUNT, SUFFICIENT TO ENHANCE THE FILM STRENGHT OF THE LUBRICANT, OF A DI-(HALO-ALKYL), MONO-OLEFINIC ALIPHATIC HYDROCARBON-RADICAAL-SUBSITUTED PHOSPHONATE ADDITIVE WHERIN THE MONO-OLEFINIC HYDROCARBON RADICAL IS LINKED BY A CARBON DIRECTLY TO THE PHOSPHORUS AND EACH OF THE TWO HALO-ALKYL RADICALS IS LINKED RESPECTIVELY TO A SEPARATE ONE OF THE OXYGENS LINKED TO THE PHOSPHORUS. WHICH ADDITIVE IS SOLUBLE IN THE LUBRICANT INGREDIENT AT LEAST IN SAID SMALL AMOUNT AND, IN SUCH SMALL CONCENTRATION IN THE LUBRICANT, IS INERT ALLOYS WATER, STABLE AT ELEVATED TEMPERATURES, AND NON-CORROSIVE TO THE FERROUS AND NON-FERROUS METALS AND THIE ALLOYS THAT ARE USED IN DEVICES REQUIRING LUBRICANTS: SAID COMPOSITION HAVING ENHANCED FILM STRENGTH OVER THAT WHICH THE MINERAL-TYPE LUBRICANT ITSELF HAS WITHOUT THIS ADDITIVED
US415961A 1954-03-12 1954-03-12 Lubricants Expired - Lifetime US2824839A (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2956952A (en) * 1955-08-08 1960-10-18 Exxon Research Engineering Co Lubricating oil compositions containing polymers of bis-(beta chloroethyl) vinyl phosphonate
US2961405A (en) * 1956-02-17 1960-11-22 Shell Oil Co Lubricating compositions containing phosphorus compounds for lubrication of silver bearings
US2993859A (en) * 1958-07-29 1961-07-25 Texaco Inc Synergistic extreme pressure agent and lubricant composition
US3053769A (en) * 1959-03-13 1962-09-11 Standard Oil Co Thickening of greases with organo phosphorus compounds
US3151078A (en) * 1960-02-26 1964-09-29 Shell Oil Co Oil compositions and phosphonocontaining polymer additives
US5514292A (en) * 1992-04-28 1996-05-07 Tonen Corporation Lubricating oil composition

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2614990A (en) * 1949-10-11 1952-10-21 Shell Dev Lubricating composition of matter

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2614990A (en) * 1949-10-11 1952-10-21 Shell Dev Lubricating composition of matter

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2956952A (en) * 1955-08-08 1960-10-18 Exxon Research Engineering Co Lubricating oil compositions containing polymers of bis-(beta chloroethyl) vinyl phosphonate
US2961405A (en) * 1956-02-17 1960-11-22 Shell Oil Co Lubricating compositions containing phosphorus compounds for lubrication of silver bearings
US2993859A (en) * 1958-07-29 1961-07-25 Texaco Inc Synergistic extreme pressure agent and lubricant composition
US3053769A (en) * 1959-03-13 1962-09-11 Standard Oil Co Thickening of greases with organo phosphorus compounds
US3151078A (en) * 1960-02-26 1964-09-29 Shell Oil Co Oil compositions and phosphonocontaining polymer additives
US5514292A (en) * 1992-04-28 1996-05-07 Tonen Corporation Lubricating oil composition

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