US2375222A - Aviation lubricating oil - Google Patents

Aviation lubricating oil Download PDF

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Publication number
US2375222A
US2375222A US502706A US50270643A US2375222A US 2375222 A US2375222 A US 2375222A US 502706 A US502706 A US 502706A US 50270643 A US50270643 A US 50270643A US 2375222 A US2375222 A US 2375222A
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US
United States
Prior art keywords
oil
aviation
sulfur
lubricating oil
salt
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US502706A
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English (en)
Inventor
Jr John R Griffin
Paul R Van Ess
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Development Co
Original Assignee
Shell Development Co
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Filing date
Publication date
Priority to NL66836D priority Critical patent/NL66836C/xx
Priority to US23229D priority patent/USRE23229E/en
Application filed by Shell Development Co filed Critical Shell Development Co
Priority to US502706A priority patent/US2375222A/en
Priority to GB19683/44A priority patent/GB594960A/en
Priority to US591404A priority patent/US2410652A/en
Application granted granted Critical
Publication of US2375222A publication Critical patent/US2375222A/en
Priority to GB21744/47A priority patent/GB681091A/en
Priority to DEN1690A priority patent/DE865343C/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/18—Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
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    • C10M2207/02—Hydroxy compounds
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04—Oxidation, e.g. ozonisation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention relates to addition agents which contribute valuable properties to lubricating oil. It also relates to improved lubricating compositionscontaining the herein described additives.
  • the problem 'of engine deposits is particularly acute in aviatio and similar engines, in which the high temperatures developed in the cylinders tend to act upon lubricating oils to cause the deposition of resinous and varnish-like products on the pistons and elsewhere and to produce lacquer-like coatings and carbonaceous materials, which in time tend to cause ring and valve sticking and interfere with engine operation.
  • High piston temperatures found especially in aviation engine promote t formation of deposits which, in turn, aggravate the situation by reducing the heat transfer.
  • fuel residues from incomplete combustion of fuel contribute to the deposition of lacquer-like and carbonaceous materials in the engine.
  • lubricating oil compositions which have improved properties in one or more of the following qualities: high temperature detergency, decreased piston ring sticking, wear reduction, corrosion resistance; stability in presence of copper or crankcase catalyst, oxidation stability, and the like.
  • Another purpose is to produce a superior heavy duty lubricant particularly suit able for use in aircraft and other internal combustion engines operating at relatively high cylinder temperatures.
  • the first of these additives is an oil-miscible metal salt of the condensation product of a low molecular weight aldehyde with a hydrocarbon substituted phenol.
  • the second additive is an organic sulfur-containing antioxidant (as will be more fully described hereinafter).
  • the first additive is more fully described by the following. It is initially a condensation product of a phenol with an aldehyde.
  • the phenol must have an available ortho position, i. e. an unsubstituted p 'ition ortho to the hydroxyl radical, and also such substituent groups, preferably in the 4 or 2,4 positions, as will promote oil solubility.
  • alkyl, cycloalkyl or aryl groups such as butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, lauryl, stearyl, oleyl, cyclohexyl, methylcyclohexyl, ethylcyclohexyl, dimethylcyclohexyl, propylcyclohexyl, trimethylcyclohexyl, dicyclohexyl, methylated dicyclohexyl, benzyl, ethylphenyl, etc., are effective.
  • the aromatic nucleus as well as attached hydrocarbon radicals may also contain chlorine.
  • the aromatic nucleus may be monoor di-cyclic, resulting in such nuclei as naphthalene, tetraline, diphenyl, etc.
  • A. lower molecular weight aldehyde preferably formaldehyde or acetaldehyde
  • iscondensed with the phenol at the ortho position by ways known to the art, for example by heating with acid or basic catalyst, whereby a resinous condensation product is obtained.
  • the products vary in appearance from viscous liquids to more or less brittle solids which may or may not be crystallized.
  • a number of such resinous condensation products are commercially available, and since their methods of manufacture are generally known, further details regarding such manufacture will not be recounted here.
  • the phenolic resin is in turn converted to the metallic salt, for example by heating with hydrated lime to produce the calcium salt.
  • the alkaline earth metals are preferred to form the salt, although other polyvalent metals such as Cu, Zn, Al, Pb, Fe, Ni, Co, Mn, Cr and Sn may be employed.
  • the resultant metal phenates may be difiicultly soluble, in oil. However, they may be incorporated in oil by the procedure described by Corthen be diluted with further oil'to give the desired salt concentration when needed. On the other hand, the salt may often be incorporated in alubricating oil, without preparing an intermediate concentrate, by simply adding the desired concentration of the salt to the oil at an elevated temperature with agitation.
  • the amounts of the phenol-aldehyde resin salt which may be added to aviation and similar high temperature lubricating oils must not exceed about 0.2% ash, because ash in these lubricating oils eventually accumulates in the combustion chamber of the aviation engine by leaking past the piston and piston rings, or else leaking into the super-charger (with which most aviation engines are now equipped) whence it returns with the air to the combustion chamber. About of the oil lost in aviation engines is normally by way of the super-charger.
  • phenol-aldehyde resin salts act as anti-oxidants "in lubricating oils.
  • aviation lubricating oils containing these salts in the perimissible amounts are not only oxidation unstable, but may also be corrosive, and to overcome these detrimental efiects.
  • the second additive is an oil-soluble, relatively stable, organic sulfur antioxidant, free from corrosive sulfur, having preferably not more than a single polar radical (if any) other than a sulfur containing radical.
  • Sulfurantioxidants should contain at least about 7 carbon atoms, and preferably 10 or more, and are characterized by containing the sulfur, in a form so that it is somewhat reactive, but not too reactive, with heavy metals such as copper, lead, iron, etc., at temperatures between, say, C. and 300 C.
  • Antioxidant sulfur may be in the form of mercaptans, as in decyl mercaptans, dodecyl mercaptans, cetyi mercaptans, oleyl mercaptans, stearyl mercantans, butyl or other higher alkyl thiophenes, thionaphthols, alkyl thionaphthols, etc.; or of disulfides (RSSR, as in diamyl disulfide and higher dialkyl disulfides, e. g.
  • RSSR disulfides
  • wax disulfides diphenyl disulfides, dibenzyl disulfide, dinaphthyl disulfides, etc); or of sulfur compounds formed by attaching sulfur to an olefinic double bond (as by reacting sulfur with olefins at temperatures of about 150 C. to 300 C.) which compounds are believed to contain the structure (sulfur in epithio linkage).
  • olefins normally gaseous olefins ;o produce gasoline or the like (e. g. sulfurized nethyl pentadiene polymer); sulfurized esters of msaturated fatty acids with monohydrie alco- 1o1s, as methyl, ethyl, propyl, etc., oleate, or inoleate; sulfurized sperm oil; sulfurized jojoba )il; etc.
  • normally gaseous olefins e. g. sulfurized nethyl pentadiene polymer
  • sulfurized esters of msaturated fatty acids with monohydrie alco- 1o1s as methyl, ethyl, propyl, etc., oleate, or inoleate
  • sulfurized sperm oil sulfurized jojoba
  • vsulfurized fatty oils vhich contain three ester radicals and hence tend cause excessive carbon formation under the iigh temperature conditions of aviation engines
  • Higher polysulfides such as compounds of the ;ype RSnR' where n is a whole number of 3 or iigher, as -well as other sulfur compounds con- .aining corrosive sulfur, are so reactive that they tttack bearing metals, causing a build-up of a .hick sulfide film which eventually breaks off, eaving behind a severely damaged bearing surace.
  • Effective amounts of the sulfur containing addiives in an aviation lubricating oil are in the order if 0.025% to 0.30% by weight of added sulfur, a1: hough quantities of between 0.05% and 0.1% are lsually sufllcient. Amounts of the metallic
  • ring sticking is one of themost I requent causes of damage to aviation engines hich are lubricated by straight mineral lubriating oils. While ring sticking can be overcome a a certain extent by the use of tapered piston ings, this advantage is gained at the expense f .a. new difliculty, namely, ring feathering. Ring ticking in aviation engines is a high tempera- .ll'e detergency problem, while ring'feathering L a wear problem.
  • antioxidants overcome corrosiveness induced by detergents. ever, this does not always appear to be true.
  • the aldehyde-phenol condensate salts are known to exhibit antioxidant action at low temperature and therefore might be expected to inhibit this corrosiveness.
  • 0.2% (sulfate ash) of the additive was found not to be the case when employing 0.2% (sulfate ash) of the additive.
  • Certain other antioxidants like secondary aromatic amines, e. g. diphenylamine, etc., do to some extent in hibitthis corrosiveness, but have the disadvantage of causing at least a partial'loss of the carbon softening properties.
  • these inhibitors like the ordinary phenolic inhibitors, such as the 2,6-di-tertiary-butyl-4-methyl-phenol, or the amino phenols as para-benzylaminophenol, fail to have any effect on the wear properties.
  • the present oil will ameliorate high temperaturedifiiculties whetherdue to ring sticking-or ring feathering, so that it may be employed advantageously with either the straight or tapered type of piston ring.
  • this lubricating oil composition by its reduction of ring sticking and wear, offers a unique and-
  • the preparation of a typical aldehyde-phenol condensate salt is illustrated by reference to the use of calcium salts of methylene bis p-isooctylphenol. This compound was prepared by condensing phenol and di-isobutylene to yield an (principally para) isooctylphenol. This was then condensed with formaldehyde to yield the resinous condensation product containing about five molecules of isooctylphenol per molecule of resin, .1
  • sulfate ash values of different batches varied from about 20% to 22%.
  • the doped and undoped oils were then further tested by a test known as the thrustbearing corrosion test (described in the National Petroleum News, September 17, 1941, pp. 12294-296) which is carried out as follows: A hardened steel disc is made to rotate for 20 hours under constant pressure against three flat copper-lead bearings. The bearing assembly rests in a steel cup filled with the oil to be tested, and the temperature of the oil is maintained at a predetermined figure by thermostatic control. The bearings are weighed before and after the test, the difference in weight representing the loss sustained durin the test.
  • Oxidation curve shows induction period.
  • additive B additive A+0.05% sulfate ash of calcium petroleum one o.
  • Norm-Test is normally 50 hours in length. Undoped oils fail at lorter times due to severe wear of piston rings resulting in excessive low-by and oil consumption.
  • bases as primary, secondary, tertiary and quaternary amines.
  • detergent forming acids are the various fatty acids of, say, 10 to 30 carbon atoms,
  • wool fat acids parafiin wax acids (produced by oxidation of parafl'in wax), chlorinated fatty acids, rosin acids, aromatic carboxylic acids including aromatic'fatty acids, aromatic hydroxy fatty acids, parafiin wax benzoic acids, various alkyl salicylic acids, phthalic acid mono-esters, aromatic keto acids, aromatic" ether acids; diphenols as di-(alkylphenel) sulfides and disulfides, methylenebis alkylphenols; sulfonic acids such as may be produced by .treatment of alkyl aryl hydrocarbons or high boiling petroleum oils with sulfuric acid; sulfuric acid mono-esters; phosphoric, arsenic and antimony acid monoand (ii-esters, including the corresponding thio phosphoric, arsenic and antimony acids; phosphonic and arsonic acids, etc.
  • Additional detergents are the alkaline earth phosphate di-esters, including the thiophosphate di-esters; the alkaline earth diphenolates, specifically the calcium and barium salts of diphenol 0 mono and poly sulfides.
  • Non-metallic detergents include compounds such as the phosphatides (e. g. lecithin), certain fatty oils as rapeseed oils, voltolized fatty or mineral oils, etc.
  • phosphatides e. g. lecithin
  • certain fatty oils as rapeseed oils
  • voltolized fatty or mineral oils etc.
  • An excellent metallic detergent for the present purpose is the calcium salt of oil soluble petroleum sulfonic acids. This may be present advantageously in the amount of about 0.025% to 0.2% sulfate ash.
  • Antioxidants comprise several types, for example alkyl phenols such as 2,4,6-trimethylphenol, pentamethylphenol, 2,4-dimethyl-6-tertiarybutylphenol, 2,4-dimethyl-6-octylphenol, 2,6-di-tertiary-butyl-4-methylphenol, 2,4,6 tritertiary-butylphenol, etc.; amino phenols as benzyl amino phenols; amines such as dibutyl' containing a minimum of carbon atoms.
  • alkyl phenols such as 2,4,6-trimethylphenol, pentamethylphenol, 2,4-dimethyl-6-tertiarybutylphenol, 2,4-dimethyl-6-octylphenol, 2,6-di-tertiary-butyl-4-methylphenol, 2,4,6 tritertiary-butylphenol, etc.
  • amino phenols as benzyl amino phenols
  • amines such as dibutyl' containing
  • a low ash content lubricating oil for high temperature internal combustion engines containing an oil-miscible metal salt of the condensation product of an aldehyde and an arcmatic hydroxy compound in amount sufiicient to give high temperature detergent action, but not exceeding about 0.2%, based on sulfate ash, and an oxidation-inhibiting quantity of an oilsoluble, sulfur-containing, organic compound possessing antioxidant, properties, which sulfur compound is free from metallic radicals, has not more than a single polar radical and possesses a minimum of '7 carbonatoms.
  • An aviation lubricating oil containing from about 0.04% to 0.2 based on sulfate ash, of an oil-miscible metal salt of the condensation product of a low molecular weight aldehyde and an aromatic hydroxy compound and from-about 0.05% to 0.2%, based on added sulfur, of an oil-soluble, organic, sulfur-containing antioxidant, substantially free from polar and 'metallic radicals and the the
  • composition of claim 2 wherein the aro-- matic hydroxy compound is an oil-soluble alkyl phenol.
  • composition of claim'2 wherein the aromatic hydroxy compound is an alkyl naphthol.
  • composition of claim 2 wherein the aromatic hydroxy compound is an octyl phenol.
  • composition of claim 2 wherein the antioxidant is a sulfurized wax olefin having a molecular weight of about 225 to 425.
  • composition of claim 2 wherein the antioxidant is a, compound of the formula RSSR' wherein R and R are hydrocarbon radicals.
  • composition ,of claim 2 which additionally contains a detergent quantity of calcium salt of oil-soluble petroleum sulfonic acid.
  • composition of claim 1 wherein the oil is an aviation lubricating oil having a Sayboll Universal viscosity of about -125 seconds at 210 F.
  • composition of claim 13 which additionally contains an oil-soluble detergent.
  • composition of claim 2 wherein the sulfur-containing antioxidant is a wax disulfide 15.
  • An aviation mineral lubricating oil containing from about 0.04% to, 0.2%, based on sulfate ash, of an oil-solublecalcium salt of the condensation product of formaldehyde and an oil soluble alkyl phenol, and from about 0.025% tc 0.30%, based on added sulfur, of an oil-soluble sulfur-containing, parafiln wax, oxidatior inhibitor.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US502706A 1943-09-15 1943-09-15 Aviation lubricating oil Expired - Lifetime US2375222A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
NL66836D NL66836C (xx) 1943-09-15
US23229D USRE23229E (en) 1943-09-15 Compounded lubricating oil
US502706A US2375222A (en) 1943-09-15 1943-09-15 Aviation lubricating oil
GB19683/44A GB594960A (en) 1943-09-15 1944-10-12 Compounded lubricating oil
US591404A US2410652A (en) 1943-09-15 1945-05-01 Compounded lubricating oil
GB21744/47A GB681091A (en) 1943-09-15 1947-08-07 Compounded lubricating oil
DEN1690A DE865343C (de) 1943-09-15 1950-08-18 Schmieroele

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US502706A US2375222A (en) 1943-09-15 1943-09-15 Aviation lubricating oil
US591404A US2410652A (en) 1943-09-15 1945-05-01 Compounded lubricating oil

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US591404A Expired - Lifetime US2410652A (en) 1943-09-15 1945-05-01 Compounded lubricating oil

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2452320A (en) * 1944-12-02 1948-10-26 Texas Co Oxidation-inhibited lubricating compositions
US2493216A (en) * 1944-06-09 1950-01-03 Socony Vacuum Oil Co Inc Mineral oil composition
US2629693A (en) * 1947-07-01 1953-02-24 Shell Dev Lubricating composition
US2647873A (en) * 1948-07-07 1953-08-04 Shell Dev Lubricating compositions
US2656316A (en) * 1950-07-17 1953-10-20 Union Oil Co Lubricating oils containing metal salts of a condensation product of a substituted phenol and a vinyl compound
US2656317A (en) * 1950-07-17 1953-10-20 Union Oil Co Lubricating oils containing metal salts of a condensation product of a substituted phenol and an allyl compound
US2736701A (en) * 1952-04-22 1956-02-28 Union Oil Co Lubricating oil composition
US2915466A (en) * 1956-09-17 1959-12-01 Shell Dev Improved mineral lubricating oil composition
US3036003A (en) * 1957-08-07 1962-05-22 Sinclair Research Inc Lubricating oil composition
WO2003066294A2 (de) * 2002-02-07 2003-08-14 Lonza Ag Nichtwässrige holzschutzmittel

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DE1075776B (de) * 1960-02-18 Berlin-Weißensee Wilhelm E. Müller Verfahren zur Herstellung von Schmierfetten auf Mineralölbasis
GB658243A (en) * 1947-02-27 1951-10-03 Wakefield & Co Ltd C C Improvements in or relating to lubricating compositions and additives therefor
US2580274A (en) * 1947-03-08 1951-12-25 Shell Dev Lubricant
FR966140A (xx) * 1947-05-13 1950-09-30
US2560202A (en) * 1948-07-24 1951-07-10 Standard Oil Dev Co Rust inhibiting composition
US2545114A (en) * 1948-07-30 1951-03-13 Gulf Oil Corp Lubricating grease composition
US2619459A (en) * 1949-03-03 1952-11-25 Union Oil Co Lubricating oil composition
US2619460A (en) * 1949-03-26 1952-11-25 Union Oil Co Lubricating oil composition
US2707172A (en) * 1949-06-16 1955-04-26 Gulf Oil Corp Stabilized mineral oil lubricant compositions
US2707173A (en) * 1949-06-17 1955-04-26 Gulf Oil Corp Stabilized mineral oil lubricant compositions
US2707174A (en) * 1949-06-20 1955-04-26 Gulf Oil Corp Stabilized mineral oil lubricant compositions
BE503233A (xx) * 1950-05-12
US2661335A (en) * 1951-09-28 1953-12-01 Monsanto Chemicals Lubricating composition
US2688001A (en) * 1952-12-23 1954-08-31 Shell Dev Low-temperature lubricating composition
US2715107A (en) * 1953-04-14 1955-08-09 Shell Dev Lubricating compositions
US2786030A (en) * 1954-04-13 1957-03-19 Gulf Oil Corp Detergent lubricating oils
US2789092A (en) * 1954-04-22 1957-04-16 Gulf Oil Corp Detergent lubricating oils
US2795551A (en) * 1954-06-29 1957-06-11 California Research Corp Lubricant compositions
US2795552A (en) * 1954-06-29 1957-06-11 California Research Corp Lubricant compositions
US2795548A (en) * 1954-06-29 1957-06-11 California Research Corp Lubricant compositions
US2943053A (en) * 1954-08-19 1960-06-28 Gulf Oil Corp Lubricants containing mixed metal salts
US2833719A (en) * 1955-03-25 1958-05-06 Rohm & Haas Lubricating oil additive compositions and lubricating oil compositions
US2916450A (en) * 1957-12-11 1959-12-08 Exxon Research Engineering Co Lubricating oil containing an alkaline earth metal sulfonate, a co-neutralized nonyl phenate, and a metal diamyldithiocarbamate
US2954344A (en) * 1957-12-11 1960-09-27 Exxon Research Engineering Co Heavy duty lubricating oil
BE592213A (xx) * 1959-06-25
US3282842A (en) * 1964-03-06 1966-11-01 Mobil Oil Corp Lubricating oil compositions
US3352780A (en) * 1965-06-23 1967-11-14 Labofina Sa Fire resistant-extreme pressure and hydrolysis resistant lubricant comprising polychlorinated diphenyl and triaryl phosphates
US4110234A (en) * 1975-11-05 1978-08-29 Uniroyal, Inc. Antioxidant stabilized lubricating oils
US4122033A (en) * 1976-11-26 1978-10-24 Black James F Oxidation inhibitor and compositions containing the same
US4534873A (en) * 1983-09-28 1985-08-13 Clark Gary G Automotive friction reducing composition
US4770802A (en) * 1986-02-04 1988-09-13 Nippon Oil Co., Ltd. Lubricating oil compositions
US6310011B1 (en) * 1994-10-17 2001-10-30 The Lubrizol Corporation Overbased metal salts useful as additives for fuels and lubricants
US6340659B1 (en) * 1995-12-13 2002-01-22 The Lubrizol Corporation Metal salts of lactones as lubricant additives
WO2010017030A1 (en) * 2008-08-08 2010-02-11 Albemarle Corporation Octylated phenyl-alpha-naphthylamine product mixtures and production of such mixtures having a high content of octylated phenyl-alpha-naphthylamine

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2493216A (en) * 1944-06-09 1950-01-03 Socony Vacuum Oil Co Inc Mineral oil composition
US2493217A (en) * 1944-06-09 1950-01-03 Socony Vacuum Oil Co Inc Mineral oil composition
US2452320A (en) * 1944-12-02 1948-10-26 Texas Co Oxidation-inhibited lubricating compositions
US2629693A (en) * 1947-07-01 1953-02-24 Shell Dev Lubricating composition
US2647873A (en) * 1948-07-07 1953-08-04 Shell Dev Lubricating compositions
US2656316A (en) * 1950-07-17 1953-10-20 Union Oil Co Lubricating oils containing metal salts of a condensation product of a substituted phenol and a vinyl compound
US2656317A (en) * 1950-07-17 1953-10-20 Union Oil Co Lubricating oils containing metal salts of a condensation product of a substituted phenol and an allyl compound
US2736701A (en) * 1952-04-22 1956-02-28 Union Oil Co Lubricating oil composition
US2915466A (en) * 1956-09-17 1959-12-01 Shell Dev Improved mineral lubricating oil composition
US3036003A (en) * 1957-08-07 1962-05-22 Sinclair Research Inc Lubricating oil composition
WO2003066294A2 (de) * 2002-02-07 2003-08-14 Lonza Ag Nichtwässrige holzschutzmittel
WO2003066294A3 (de) * 2002-02-07 2004-01-15 Lonza Ag Nichtwässrige holzschutzmittel

Also Published As

Publication number Publication date
GB594960A (en) 1947-11-24
NL66836C (xx)
US2410652A (en) 1946-11-05
USRE23229E (en) 1950-05-09
DE865343C (de) 1953-02-02
GB681091A (en) 1952-10-15

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