US2611744A - Lubrication composition - Google Patents

Lubrication composition Download PDF

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Publication number
US2611744A
US2611744A US133683A US13368349A US2611744A US 2611744 A US2611744 A US 2611744A US 133683 A US133683 A US 133683A US 13368349 A US13368349 A US 13368349A US 2611744 A US2611744 A US 2611744A
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Prior art keywords
fatty acid
lubricating
lubricating composition
additive
weight
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US133683A
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Kipp Egbert Mason
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Howmet Aerospace Inc
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Aluminum Company of America
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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
    • C10M2227/00Organic 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
    • C10M2227/06Organic compounds derived from inorganic acids or metal salts
    • C10M2227/063Complexes of boron halides
    • 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

  • jects are'achieved in substantial part by provide ing a lubricant, the essential, lubricating come ponents of'which area major amount, of; ahy-v drocarbon lubricatingcomponent which may be,
  • ride content will of course depend onsuchimate ters as cost, ease of mixin and thenaturleofthe lubrication problem.
  • Such diluents or'addit-ions may therefore,- for the purposes-ofthis invention;- be regarded; as a 'non-essentialportion of-the composition,- regardless oftheir specifickbene fioial or functionaleffeot.
  • jsubstances-known as extreme pressure additives such, as -substances composed -;of-;ch lorine,;
  • The-- organic- BB3 body which irr-accoldance with this; invention isblendedywi-th the hydro;; carbon ;component; :may "be prepared in various: ways but'is; for the most part;- conveniently ⁇ prepared by exposing the fatty acid esterito diregt contact with; gaseousg-BFr.
  • This can;- be easily c ompli h d un e 'ordinaryfatm snhe ic PIG ur yn bb in the ase us- BFQ: th ou h the. tt cidester n a'li uidi tate ft star s n t: i i a om.
  • e r-et of fatty acid ester may have a different saturation making it darker.
  • fatty acid ester may be exposed tothe gas at higher temperatures and pressures and thus shorten the time required to introduce the desired amount of BF3.
  • the temperature and pressure should be such that the fatty acid esteris not decomposed to any substantial degree.
  • 'Another method of contacting the ester with El 's is to add compounds to the ester which can be decomposed with the release of BFs. Such compounds the invention do not depend" upon' or" are respon cant and, in many instances, to definitely im- The amount of these organic BF: bodies necessarily present prove its anti-wear characteristics.
  • the amounts used should in any case, as menas NH4BF4, BFa-NHs, the heavy metal iiuoboratesor even other organic materials previously treated with BFs may be employed.
  • To effect decomposition it is usually necessary to heat the mixture of fatty acid ester and the BFs-containing substance. Further, it may be desirable to remove any residues resulting from the decomposition.
  • the amount of BF: that can be introduced into different fatty acid esters will vary, as mentioned above, however, from 10 to percent by weight is preferred where the saturation point permits it. In any case, the fatty acid esters should be treated with sufiicient fluoride to provide the desired BF3 content in the lubricating composition as only a minor proportion of the additive is employed.
  • the resultant product may, in some instances,
  • fatty acid esters act as acceptors of BF:: to produce a body or substance having positive advantages as an additive in lubricating compositions.
  • esters of monohydric and polyhydric alcohols are illustrative of the class which when treated with BF3 produce the bodies just described: esters of normal alkyl monohydric alcohols and monocarboxylic acids such as those of methyl through cetyl alcohols with the straight chain fatty acids butyric through stearic; esters of aromatic and cyclic alcohols such as the phenyl, cresyl, resorcinyl, hydroquinyl, furfuryl, benzyl, naphthyl, terpenyl, menthyl and bornyl esters of fatty acids; both symmetrical and unsymmetrical esters of polyhydric alcohols such as those of the glycols and glyceryls with fatty acids, including the ethylene, propylene, butylene, and polyalkylene glycols as well as the polymeric glycols of higher molecular weight and the mono-, di-, and triglyceryl compounds; and such esters of normal alkyl
  • the introduction of the BF: into the fatty acid ester may change the color of the ester, 'often Also, the liquid ester may become thicker as the introduction of BF: proceeds and the melting point of the end product may be higher than that of the original ester.
  • Such changes do not affect the advantages gained from the presence of the BFs-containing bodies in a hydrocarbon lubricant, certainly the results of tioned 'abovefprovide at least 0.001% by weight of.BF3 in the final mixture.
  • the amount of any given BEE-containing body desirably present to produce optimum effects in any particular hydrocarbon lubricant can be readily determined by simple trial, the optimum usually being found within the range of 0.5 to 5 percent by weight of the fatty acid ester BR. body.
  • the organic BF3 additive forms a minor amount or proportion of the lubricating composition. 7
  • Theload' bearing qualities of a lubricant may be relatively determined by various methods.
  • the additive had been'prepared .by passing BF3 through the fatty acid ester until the weight of the body became substantially constant, that is the ester became saturated with the BFz, as has been described hereinabove.
  • Each comparative test was run on two samples, one samplebein the oil containing 1 percent by weight of a fatty acid ester, the other sample being the oil containing the same weight of a BFz-containing body.
  • the nature of the additive is set forth, in the second column is listed the BFs content of the treated material, in the third column is the BF: content of thellubricant, in the fourth column the failure load in pounds is given and in the fifth column is shown the percentage.
  • additive may merely be mixed with the hydrocarbon lubricants, the properties of which are to be improved. Where the additive is insoluble in the lubricant or it is desired to incorporate therein amounts in excess of solubility, emulsions or dispersions may be prepared according to known principles.
  • a lubricating composition comprising a major proportion of a hydrocarbon lubricating oil blended with a minor proportion of a body consisting essentially of a substance selected from the class consisting of the fatty acid esters of monohydrlc alcohols and polyhydric alcohols and BF:;, said fatty acids being those containing from 4 to 18 carbon atoms, said body being prepared by exposing said fatty acid esters to direct contact with a substance selected from the class consistin; of gaseous BF: and decomposable compounds yielding gaseous BR; and being present in such amount that the lubricating composition contains sure characteristics superior to those emibited by a similar composition in which the minor proportion aforesaid consists of fatty acid ester.
  • a lubricatin composition comprising a major proportion of a hydrocarbon lubricating oil blended with a. minor proportion of a body consisting essentially of a butyl ester of a fatty acid containing from 4 to 18 carbon atoms and BFs, said body being prepared by exposing said butyl ester to direct contact with a substance selected from the class consisting of gaseous BE; and decomposable compounds yielding gaseous BF; and being present in such amount that the lubricating composition contains from 0.001 to 3 per cent by weight of BFs, said lubricating composition possessing extreme pressure characteristics superior to those exhibited by a similar composition in which the minor proportion aforesaid consists of butyl ester. 40

Description

Patented Sept. 23, 1952 iniim Company of America';
- Pi tt'sburgh; 2a a -corporation of Pennsylvania momma his, invention relates it improved; lubricants.
such as'oils, greases,orsemhfluidjoils containing as a major lubricating ,compgnentghydro: carbon oil of natural,ror synthetic origin; In". particular, the inventionv r.elates. to.- lubrica ing, compositions of this. typ having improved ,exr,
treme pressure characteristics;
Requirements 'uponlubri'cants by, deyelopmenti in mechanical designiareirigid. and; drastic-I In manyinstances pressures at bearing. surfaces a e.
higher than thosewhichpetrolemnmiIsJWiII'I Qrmally withstand; Illustrative ar e,th,e conditions.
encountered inflth'e' lubrication. of automotive hypoid gears, heavily loaded. milllpin'ion ,lgears,
naval turret gearsand the like. In manylmael i chines operation is, at leastlin'part, under con-V ditions of thin film lubrication, or. under similar, conditions where film strength. oilinessandanti-L wear characteristics of, high order. are required of the lubricating medium.
The principal object of-this. 'invention is'the provision of a new composition .ofnmatter con.-
sisting of a compounded lubricating productposfilm strength, oiliness, andanti-v'vear characteristics.
In accordance with'thi's invention these. ob.-
jects are'achieved in substantial part by provide ing a lubricant, the essential, lubricating come ponents of'which area major amount, of; ahy-v drocarbon lubricatingcomponent which may be,
oil or grease and a minor amount of a :body of boron fluoride-and a substanceselected;from the class consisting of the fatty-acid esters of monohydric alcohols and polyhydric alcohols 'more specifically described beloww Theproportion. of this body to the hydrocarbon-component-should be such, however, that-the-mixture, contains at least 0.001% by, weight of-boronrfluoride (BEs).
while, on the other handymore-than 3%idoes not; improve the lubricant.- Withinthis rangeithas been found that the best resultsjare obtained by providing from 0.1 to'1.0 percent ofboron fluoride,
in the final lubricant'mixture. The choice oijjthe particular body to be employed anditsboron.flue;
ride content will of course depend onsuchimate ters as cost, ease of mixin and thenaturleofthe lubrication problem.
' The a principal advantages and effectiveness of.
thisnew compounded lubricant are maintained (Application Decemblenli 1949, s erialrlslo. 133,:583.
whem in-a-ddition to theabcve mentioned-essen-= tial components there: are-likewise-present in the lubricating composition other components added to improve some specific characteristicor property thereof; "such as viscosity; pour-point,
oiliness; flow, anti -wear- -characteristics;- filrn strength or the like; the effect of" the-definedbo'ron: fluoride-containing:body;when similar, be-' ing largely additive: Such diluents or'addit-ions may therefore,- for the purposes-ofthis invention;- be regarded; as a 'non-essentialportion of-the composition,- regardless oftheir specifickbene fioial or functionaleffeot. The same maybesaid ofjsubstances-known as extreme pressure additives, such, as -substances composed -;of-;ch lorine,;
sulphur or lead, containing cornponnds or ma teriais; it; being observable that the presence of the defined-"boron fluoride-containing bodies: is;' effective toincrease: the :XtIQHl-B" pressure-char acteristics ofithe compositionseverr when other-- eXtreme-pressure additives{are"present'; I
The-- organic- BB3 body, which irr-accoldance with this; invention isblendedywi-th the hydro;; carbon ;component; :may "be prepared in various: ways but'is; for the most part;- conveniently {prepared by exposing the fatty acid esterito diregt contact with; gaseousg-BFr. This can;- be easily c ompli h d un e 'ordinaryfatm snhe ic PIG ur yn bb in the ase us- BFQ: th ou h the. tt cidester n a'li uidi tate ft star s n t: i i a om. m at e" i sh ul the heated o an ma a ned" a a. e er ure sli ntl above t -meltinene n s le orl fiC-l th ushthe. ra e' flqw of t e as is no lcrit pali with respe ti olformation of t e .35 1 additive, you the now shq ld'he on rq ledtoavq d:nnduelossg The rate oflac'ceptanc'e of.,the;.. 3E3} by the fatty.
cidesterisrimprbved; e qllid ssti m a th asnisiintroduced The amour: inns. accepted by, the ester, isindicatd by th in 1385i inlweiahtlofitheltreated mass. Thejin'troductiqn ,ot the gas. may, thereforeflbel continued .luntilr, a predetn-L imd"in .reaed..weig ht, .short or saturation,,has, been..obtained,or,the flowofi asmay lie-prolon ed until no further increase in weight is closer e r-et of fatty acid ester may have a different saturation making it darker.
point or the desired 33% content may differ for various esters. This does not detract from the value of the Bib-containing body in improving the load bearing quality of a hydrocarbon lubricant.
Other methods of introducing BF3 can be employed, of course. For example, the fatty acid ester may be exposed tothe gas at higher temperatures and pressures and thus shorten the time required to introduce the desired amount of BF3. Naturally, the temperature and pressure should be such that the fatty acid esteris not decomposed to any substantial degree. 'Another method of contacting the ester with El 's is to add compounds to the ester which can be decomposed with the release of BFs. Such compounds the invention do not depend" upon' or" are respon cant and, in many instances, to definitely im- The amount of these organic BF: bodies necessarily present prove its anti-wear characteristics.
to produce these specific effects is very small.
, The amounts used, should in any case, as menas NH4BF4, BFa-NHs, the heavy metal iiuoboratesor even other organic materials previously treated with BFs may be employed. To effect decomposition it is usually necessary to heat the mixture of fatty acid ester and the BFs-containing substance. Further, it may be desirable to remove any residues resulting from the decomposition.
The amount of BF: that can be introduced into different fatty acid esters will vary, as mentioned above, however, from 10 to percent by weight is preferred where the saturation point permits it. In any case, the fatty acid esters should be treated with sufiicient fluoride to provide the desired BF3 content in the lubricating composition as only a minor proportion of the additive is employed.
The resultant product may, in some instances,
be an actual compound, there being some evi. 3
dence to indicate that such is its nature, or it may be an additive or coordinate compound or even a, solution or dispersion. I prefer, however, to term the product a body or composition consisting essentially of fatty acid ester and BF: and, therefore not to characterize thestate of association of the fluoride and the ester. In any event, the fatty acid esters act as acceptors of BF:: to produce a body or substance having positive advantages as an additive in lubricating compositions.
The following list of fatty acid esters of monohydric and polyhydric alcohols is illustrative of the class which when treated with BF3 produce the bodies just described: esters of normal alkyl monohydric alcohols and monocarboxylic acids such as those of methyl through cetyl alcohols with the straight chain fatty acids butyric through stearic; esters of aromatic and cyclic alcohols such as the phenyl, cresyl, resorcinyl, hydroquinyl, furfuryl, benzyl, naphthyl, terpenyl, menthyl and bornyl esters of fatty acids; both symmetrical and unsymmetrical esters of polyhydric alcohols such as those of the glycols and glyceryls with fatty acids, including the ethylene, propylene, butylene, and polyalkylene glycols as well as the polymeric glycols of higher molecular weight and the mono-, di-, and triglyceryl compounds; and such esters of polyhydric alcohols as the sterols, cellulose, glucose, sucrose, rafiinose,
and sorbitol.
The introduction of the BF: into the fatty acid ester may change the color of the ester, 'often Also, the liquid ester may become thicker as the introduction of BF: proceeds and the melting point of the end product may be higher than that of the original ester. Such changes do not affect the advantages gained from the presence of the BFs-containing bodies in a hydrocarbon lubricant, certainly the results of tioned 'abovefprovide at least 0.001% by weight of.BF3 in the final mixture. The amount of any given BEE-containing body desirably present to produce optimum effects in any particular hydrocarbon lubricant can be readily determined by simple trial, the optimum usually being found within the range of 0.5 to 5 percent by weight of the fatty acid ester BR. body. Amounts below about 0.01 percent by weight often do not produce sufficient effect to' be usually characterized as commercial, but the effect produced is such as to be useful under exceptional conditions. One may use a relatively small amount of an additive containing a substantial quantity of BF: or a larger amount of the same or another additive which contains a smaller proportion of BFs to introduce a given quantity of BFs into the hydrocarbon component. In any event, the organic BF3 additive forms a minor amount or proportion of the lubricating composition. 7
Theload' bearing qualities of a lubricant may be relatively determined by various methods. The
method used to obtain the comparative data hereinafter set forth is practiced on a Falex machir ie and consists in submitting small quantities of the lubricant to the action of a rotating steel journal rotated in contact with two V shaped bearing blocks. During testing measurable pressure was applied to the rotating journal by use of an automatic loading device. The two bearing blocks and the journal were submerged in the lubricant sample throughout the tests. In each and 300 pounds at higher pressure; the results are not absolute but are comparative with a standard run under the same conditions. In the tests by which the results set forth in the following table were secured, the hydrocarbon oil was in all cases the same, being a straight mineral oil. In all cases 1 percent by weight of additive waspresent in the oil. The additive had been'prepared .by passing BF3 through the fatty acid ester until the weight of the body became substantially constant, that is the ester became saturated with the BFz, as has been described hereinabove. Each comparative test was run on two samples, one samplebein the oil containing 1 percent by weight of a fatty acid ester, the other sample being the oil containing the same weight of a BFz-containing body. In the first column of the table the nature of the additive is set forth, in the second column is listed the BFs content of the treated material, in the third column is the BF: content of thellubricant, in the fourth column the failure load in pounds is given and in the fifth column is shown the percentage.
5 increase in failure load caused by the presence of the BFa-containing body.
6 from 0.001 to 3 per cent by weight of'B-Fs, said lubricating composition possessing extreme pres- Percent Percent Failure Percent- Additive BF: in BF; in Load in age Additive Lubricant Pounds Increase Butyl laurate l, 000 I Butyl laurate+BFs 23. 0. 23 4, 000 Methyl olcate l 0 I 300 Methyl o1eate+BFa Cyclohexyl steal-ate. 0 I 233 Oyclohexyl stearate+B Fa Butyl stearate 0 x 245 Butyl stearate+BFs..... Butyl acetyl ricinoleate 131 Butyl acetyl ricinoleate-l-B Glyceryl laurate l 245 Glyceryl laurate+BF; Diglycol stearate 50 I 433 Diglycol stearate+B Fa Nonaethylene glycol monostearate. l 270 Nonaethylene glycol monostearate+BFa 45. 0. 45 4, 000
1 Greater than.
The machine on which the tests were run had a capacity of 4500 pounds. Where this capacity was approximated or exceeded the failure load is indicated above as being greater than 4000 pounds. These tabulated results are indicative of the improvement obtained by the practice of this invention. In general, torque and tempera- --ture values obtained during these tests indicated that the organic BFa body improved friction qualities and observations simultaneously made indicated increases in anti-Wear characteristics.
In compounding lubricant compositions of the type herein described and claimed the organic BF: additive may merely be mixed with the hydrocarbon lubricants, the properties of which are to be improved. Where the additive is insoluble in the lubricant or it is desired to incorporate therein amounts in excess of solubility, emulsions or dispersions may be prepared according to known principles.
This application is a continuation-in-part of my prior application Serial No. 714,909 filed December 7, 1946 now abandoned, and entitled Lubrication Composition.
Having thus described my invention and the known advantages thereof, I claim:
1. A lubricating composition comprising a major proportion of a hydrocarbon lubricating oil blended with a minor proportion of a body consisting essentially of a substance selected from the class consisting of the fatty acid esters of monohydrlc alcohols and polyhydric alcohols and BF:;, said fatty acids being those containing from 4 to 18 carbon atoms, said body being prepared by exposing said fatty acid esters to direct contact with a substance selected from the class consistin; of gaseous BF: and decomposable compounds yielding gaseous BR; and being present in such amount that the lubricating composition contains sure characteristics superior to those emibited by a similar composition in which the minor proportion aforesaid consists of fatty acid ester.
2. A lubricatin composition comprising a major proportion of a hydrocarbon lubricating oil blended with a. minor proportion of a body consisting essentially of a butyl ester of a fatty acid containing from 4 to 18 carbon atoms and BFs, said body being prepared by exposing said butyl ester to direct contact with a substance selected from the class consisting of gaseous BE; and decomposable compounds yielding gaseous BF; and being present in such amount that the lubricating composition contains from 0.001 to 3 per cent by weight of BFs, said lubricating composition possessing extreme pressure characteristics superior to those exhibited by a similar composition in which the minor proportion aforesaid consists of butyl ester. 40
EGBERT MASON KIPP.
REFERENCES CITED The following references are of record in the file of this patent:
45 UNITED STATES PATENTS OTHER REFERENCES Boron 'Irifluoride and Its Derivatives," Booth et al., John Wiley 8a Sons, 1949, pp. 72-74.

Claims (1)

1. A LUBRICATING COMPOSITION COMPRISING A MAJOR PROPORTION OF A HYDROCARBON LUBRICATING OIL BLENDED WITH A MINOR PROPORTION OF A BODY CONSISTING ESSENTIALLY OF A SUBSTANCE SELECTED FROM THE CLASS CONSISTING OF THE FATTY ACID ESTERS OF MONOHYDRIC ALCOHOLS AND POLYHYDRIC ALCOHOLS AND BF3, SAID FATTY ACIDS BEING THOSE CONTAINING FROM 4 TO 18 CARBON ATOMS, SAID BODY BEING PREPARED BY EXPOSING SAID FATTY ACID ESTERS TO DIRECT CONTACT WITH A SUBSTANCE SELECTED FROM THE CLASS CONSISTING OF GASEOUS BF3 AND DECOMPOSABLE COMPOUNDS YIELDING GASEOUS BF3 AND BEING PRESENT IN SUCH AMOUNT THAT THE LUBRICATING COMPOSITION CONTAINS FROM 0.001 TO 3 PER CENT BY WEIGHT OF BF3, SAID LUBRICATING COMPOSITION POSSESSING EXTREME PRESSURE CHARACTERISTICS SUPERIOR TO THOSE EXHIBITED BY A SIMILAR COMPOSITION IN WHICH THE MINOR PROPORTION AFORESAID CONSISTS OF FATTY ACID ESTER.
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3105400A (en) * 1954-05-10 1963-10-01 Aluminum Co Of America Rolling of aluminous metal foil
US3900297A (en) * 1971-06-07 1975-08-19 James Michaels Fuel for engines
US4024088A (en) * 1974-12-23 1977-05-17 Union Carbide Corporation Compositions and methods useful in forming polyether polyurethanes having release properties
US4301019A (en) * 1980-10-29 1981-11-17 Mobil Oil Corporation Mercaptothiadiazole adducts of unsaturated esters and lubricants containing same

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2053474A (en) * 1934-12-11 1936-09-08 Du Pont Higher alkyl borates and silicates and process for preparing same
US2160917A (en) * 1937-06-10 1939-06-06 Standard Oil Co Lubricant
US2266060A (en) * 1939-12-29 1941-12-16 Aluminum Co Of America Solder flux
GB645202A (en) * 1947-03-29 1950-10-25 Aluminum Co Of America Improvements in or relating to lubricating compositions
GB645425A (en) * 1946-12-07 1950-11-01 Aluminum Co Of America Improvements in or relating to lubricating compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2053474A (en) * 1934-12-11 1936-09-08 Du Pont Higher alkyl borates and silicates and process for preparing same
US2160917A (en) * 1937-06-10 1939-06-06 Standard Oil Co Lubricant
US2266060A (en) * 1939-12-29 1941-12-16 Aluminum Co Of America Solder flux
GB645425A (en) * 1946-12-07 1950-11-01 Aluminum Co Of America Improvements in or relating to lubricating compositions
GB645202A (en) * 1947-03-29 1950-10-25 Aluminum Co Of America Improvements in or relating to lubricating compositions

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3105400A (en) * 1954-05-10 1963-10-01 Aluminum Co Of America Rolling of aluminous metal foil
US3900297A (en) * 1971-06-07 1975-08-19 James Michaels Fuel for engines
US4024088A (en) * 1974-12-23 1977-05-17 Union Carbide Corporation Compositions and methods useful in forming polyether polyurethanes having release properties
US4301019A (en) * 1980-10-29 1981-11-17 Mobil Oil Corporation Mercaptothiadiazole adducts of unsaturated esters and lubricants containing same

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