US3287266A - Lubricating composition - Google Patents

Lubricating composition Download PDF

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Publication number
US3287266A
US3287266A US355949A US35594964A US3287266A US 3287266 A US3287266 A US 3287266A US 355949 A US355949 A US 355949A US 35594964 A US35594964 A US 35594964A US 3287266 A US3287266 A US 3287266A
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United States
Prior art keywords
bis
acid
chloromethyl
carbon atoms
phenyl
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US355949A
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Southern Derek
Francis H Waight
Alexander C B Macphail
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Shell USA Inc
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Shell Oil Co
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • 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 System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • C10M137/105—Thio derivatives not containing metal
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
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    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

Description

United States Patent 3,287,266 LUBRICATING COMPOSITION Derek Southern, Heswall, Wirral, Francis H. Waight, Little Sutton, Wirral, and Alexander C. B. MacPhail, Eastham, Wirral, England, assignors to Shell Oil Company, New York, N.Y., a corporation of Delaware No Drawing. Filed Mar. 30, 1964, Ser. No. 355,949
Claims priority, application Great Britain, Apr. 23, 1963, 15,953/63 Claims. (Cl. 25246.7)
This invention relates to lubricating oil compositions having improved extreme-pressure properties. In particular, this invention concerns synthetic lubricants containing certain diaryl haloalkyl phosphates.
In recent years, various types of synthetic lubricants have become available to satisfy stringent requirements not met by conventional mineral oils. For example, a major application for synthetic lubricants has been in aircraft turbine engines, which must perform at temperatures as low as -65 F., and maintain stability at tem peratures as high as 400 to 500 F.
One of the most diflicult problems encountered in the formulation of synthetic lubricants is imparting extremepressure properties to the oil. Various additives have been proposed for making these compositions suitable for lubrication at the high pressures, temperatures, and speeds normally encountered in their use. Although some com pounds have successfully contributed good antiwear characteristics, few have also met the equally important requirements of low sludge and deposit formation and thermal stability.
It is an object of the present invention to provide a lubri eating composition with excellent extreme-pressure properties which is resistant to sludge and deposit formation and which :has good thermal stability.
It has now been discovered that certain diaryl haloalkyl phosphates improve the extreme-pressure properties of lubricating oils to a substantially greater extent than was possible With other known EP agents. Lubricants of the invention contain 0.1 to 10%, preferably 2 to 6% by weight, of a diaryl haloalkyl phosphate of the formula wherein R is monoto di-nuclear aryl which is substituted with from 0 to 5, especially -0 to 2 alkyl groups having from 1 to 10 carbons; X is a chalcogen having an atomic number from 8 to 16; R is nonto di-alkyl methylene wherein alkyl has 1 to 4 carbons; n is an integer from 1 to 6, preferably 1 to 3, especially 1; Y is nonto perchloroalkyl having 1 to 2 carbons; and Z is monoto trichloromethyl. Preferred com-positions comprise a synthetic base with one or more additives of the invention wherein the above formula one or more of the following is true: R is a phenyl group substituted with from 0 to 2 alkyl groups having 1 to 10 carbons, X is a chalcogen having an atomic number from 8 to 16 (i.e., oxygen or sulfur), R is methylene, n is 1, Y is nonto tri-chloroalkyl having 1 to 2 carbons (i.e., CH CH Cl, ChCl CCl C2H5, C H4Cl, C H Cl 0r C H Cl and Z is monochloromethyl.
Examples of additives of the invention are phenyl naphthyl 5,5-dichloropentyl 4,4-bis(chloromethyl) phosphate; octylphenyl hexyl-phenyl 7,7,7-trichloroheptyl -6-chloromethyl 6-dichloromethyl phosphorothionate; (dioctyl) phenyl phenyl 3,3-bis(chloromethyl) 4-chlorobutyl phosphate; dioctylphenyl 2,2-bis(trichloromethyl) 3,3-dichl0ropropyl phosphorothionate; diphenyl 3,3-bis (chloromethyl) 4,5-dichloropentyl phosphate.
Particularly preferred diaryl haloalkyl phosphates are diphenyl 2,2 bis (chlorornethyl) 3 chloropropyl phosphate; diphenyl 2,2 bis(chloromethyl) 3-chloropropyl phosphoro thionate; dioctylphenyl-2,2-'bis (chloromethyl) 3-chloropropyl phosphate; and dioctylphenyl-2,2-bis(chloromethyl) -3-chloropropyl phosphorothionate.
The additives of the invention may be used to impart EP properties to either synthetic or mineral oils, but are preferably used in synthetic ester bases. The ester lubricant bases are preferably aliphatic carboxylic acid esters. These may be esters of a rn'onohydric aliphatic alcohol having from 3 to 18 carbon atoms with a monobasic aliphatic acid having from 4 to 18 carbon atoms, for example, isodecyl pelargonate A further class of aliphatic carboxylic acid esters which may be used is the aliphatic esters of monobasic carboxylic acids having 4 to 18 carbon atoms and a glycol having 4 to 20 carbon atoms, for example esters of neopentyl glycol, Z-butyl-Z-ethyl-propanediol and dipropylene glycol with heptylic acid, n-octoic acid, and pelargonic acid.
A particularly preferred class of aliphatic carboxylic acid esters for use in the lubricating oil compositions of the invention is the aliphatic diester of dibasic carboxylic acids having from 6 to 20 carbon atoms and monohydric alcohols having from 1 to 12 carbon atoms, for example esters of adipic acid, pimelic acid, suberic acid, azelaic acid and sebacic acid with lauryl alcohol, heptyl alcohol, octyl alcohol and nonyl alcohol. Particularly preferred aliphatic diesters of dicarboxylic acids are those derived from monohydric alcohols having a branched chain, for example Z-ethyl hexanol and especially those having no hydrogen on the beta carbon atom, for example 2,2-dimethyl pentanol, 2,2,4-trimethyl pentanol, 2,2,3-trimethyl pentanol, 2,2-dimethylhexanol, and 2-methyl-2-ethyl hexanol.
As examples of other aliphatic carboxylic acid esters which may be used there are mentioned aliphatic esters of monocarboxylic acids having from 3 to 10 carbon atoms, for example, propionic acid, butyric acid, valeric acid, capric acid, caprylic acid, lauric acid and pelargonic acid and polyols, for example, pentaerythritol, dipentaerythritol and trimethylolpropane.
Examples of such esters are pentaerythrityl butyrate, pentaerythrityl tetrabntyrate, pentaerythrityl tetravalerate, pentaerythrityl tetracaproate, pentaerythrityl dibutyratedicaproate, pentaerythrityl butyratecaproate divalerate, pentaerythrityl butyrate trivalerate, pentaerythrityl butyrate tricaproate, pentaerythrityl tributyrate-caproate, mixed C saturated fatty acid esters of pentaerythritol, dipentaerythrityl hexavalerate, dipentaerythrityl hexacaproate, dipentaerythrityl hexaheptoate, dipentaerythrityl hexa caprylate, dipentaerythrityl tributyratecaproate, dipentaerythrityl trivalerate trinonylate, dipentaerythrityl mixed hexaesters of C C fatty acids, and trimethylolpropane heptylate.
To illustrate the improved lubricating oil compositions of the present invention the compositions as shown in Table I (Examples IV-VII) were made, tested and compared against the base oil (Example I) and a composition containing the same amounts of a known extreme pressure additive (Examples 11 and III).
These compositions were tested for their load-carrying capacity on an I.A.E. Gear Rig as described in the Institute of Petroleum Method 166/ 60T using BSS-EN 34 steel gears and operating at an oil temperature of either 60 C. or C. The mean failure loads at 2000 rpm. and 6000 r.p.m. at both the aforementioned temperatures were determined and recorded in Table II.
TABLE I Composition of Example (percent Wt.) I
Di(isooetyl azelate) Aroclor 1254 (chlorinated diphenyl) Diphenyl-2,2-bischloromethyl-IS-chloropropyl Dioetyl phenyl-2,2-bis-chloromethyl-3-ehloropropy] phnsphnh:
3 ,7-dioctyl phenoi'hiarinp Phenyl-alphanaphthylamine 5-1nethyl benzotriazole, p.p.m Azelaic acid Silicone MS 200/12,500, ppm
TABLE II Example I II III VI VII I.A.E. Sending Load (lbs):
2,000 r.p.m.:
Sum or Scufling Load (lbs) /1io1 R0 X wherein R and X are as defined above.
The following preparations are illustrative of the method of preparing the novel phosphates for use as extremepressure additives in the compositions of the present invention.
Preparation 1.DiphenyZ-2,2-bis(chloromelhyl) -3- chloropropyl phosphate Chlorine, percent wt 53.9 (theory 55.6% wt.).
Hydroxyl value (rneq./ g.) 5.12 (theory 5.22).
100 grams (0.52 mole) of 2,2-bis(chloromethyl)-3-chloropropanol, 134 grams (0.5 mole) of diphenyl phosphorochloridate and 50 grams (0.63 mole) of pyridine are placed in a flask and shaken. The mixture temperature slowly rises and thus the reaction fiask is water-cooled until the reaction ceases. Toluene (50 ml.) is added and the resulting mixture is refluxed for four hours. When cool, the reaction mixture is further diluted with 50 ml. light petroleum spirit (B.P. 100-120 C.), benzene (50 ml.) and water (50 ml.). washed successively with water, dilute sodium bicarbonate The resulting organic layer is solution and Water until neutral. Water and organic solvent are removed by distillation and the final product is distilled under reduced pressure and on cooling this product crystallizes to a White solid which is diphenyl-2,2-bis (chloromethyl) -3-chloropropyl phosphate and which gave on analysis:
Acid value Nil. Free chloride Nil. Chlorine (percent wt.) 24.8 (theory 25.1% wt.).
Preparation II.Dioctylphenyl-2,2-bis(chl0r0methyl)-3- chloropropyl phosphate Distilled p-octyl phenol (116 g., 0.56 mole) and distilled phosphoryl chloride (43.2 g., 0.28 mole) are placed in a flask fitted with a thermometer and a stirrer. The temperature of the reaction mixture is slowly increased to 228 C. over a period of 2 hours and so maintained for a further 2 hours. The resulting product is distilled through a 12" x Vigreux column which is lagged with a heating tape, and the fraction boiling up to 240 C. at 15 mm. Hg pressure analyzed for di-p-octyl phenyl phosphorochloridate. A sample of the phosphorochloridate prepared in this manner gave on analysis: Chlorine (percent wt.), 7.20 (theory 7.20% wt.).
27.6 grams (0.06 mole) of di-p-octylphenyl phosphorochloridate, 13.8 grams (0.07 mole) of 2,2-bis(chloromethyl)-3-chloropropanol as prepared in Preparation I and 6 grams pyridine (0.08 mole) are placed in a flask, the contents shaken and the flask cooled. Toluene is added (50 ml.) and the mixture is refluxed for four hours; two distinct layers are formed in the reaction flask. The product is diluted with ml. of a mixture of light petroleum spirit (B.P. 100-120 C.) and benzene and is then washed with water, dilute sodium bicarbonate solution and water until neutral. The solvent is then distilled. The residue, containing free chloride, is diluted with toluene and the resulting solution is slurried with Amberlite IRA-400 ion exchange resin (activated by washing with NaOH solution). After filtering, the solvent is removed by distillation, leaving an amber-colored liquid product which is dip-0ctylphenyl-2,2-bis(chloromethyl)-3-chloropropyl phosphate and which had the following analysis:
Acid value 0.7 mg. KOH/ g. Free chloride Nil. Chlorine (percent wt.) 16.45 (theory 16.42% wt.).
The lubricating oil compositions of the present invention may also contain any of the known additives for aliphatic carboxylic acid ester lubricating oils, for example, thickeners, antioxidants, anti-lacquering agents, anti-foaming agents, dyes, anti-corrosion agents, metal deactivators and additional extreme-pressure additives if so desired.
Suitable thickeners are polyalkylene glycols and their monoor di-ethers and esters and the polymers of esters of acrylic or l-alkyl acrylic acids. Examples of antioxidants which may be used in the lubricating oil compositions according to this invention are alkylated phenols, for example 2,6-diter-tiary butyl-4-methyl phenol; alkylated bis phenols, for example, 4,4-methylene bis(2,6-ditertiary butyl phenol); aromatic amines, e.g., phenyl-ocnaphthylamine, phenyl-B-naphthylamine,. 2,2'-dipyridylamine, diphenylamine and alkyl substituted derivatives thereof. An especially preferred class of antioxidants is the thiodiarylamines, for example, phenothiazine and 3,7- dioctyl phenothiazine. Mixtures of antioxidants may also be used, particularly mixture containing a thiodiarylamine, e.g., a mixture of phenothiazine and phenyl-anaphthylamine.
Suitable anti-forming agents are the polydimethyl siloxanes having viscosities from 100 to 100,000 centistokes at 25 C. Examples of anti-corrosion agents and metal deactivators are benzotriaz-ole, S-methyl benzotriazole and low molecular weight dicarboxylic acids, e.g., azelaic acid, pimelic acid.
Other extreme-pressure additives which may be used if so desired are, for example, the chloronated dior polypheuyls and the triaryl esters of phosphorothionic acid.
We claim as our invention:
1. A lubricating oil composition comprising a major proportion of a base lubricating oil and from 0.1 to 10% by weight of a diaryl haloalkyl phosphate of the formula wherein R is monoto di-nuclear aryl which is substituted with from to alkyl groups having 1 to carbon atoms; X is a chalcogen having an atomic number of from 8 to 16; R is nonto di-alkyl methylene, where alkyl has 1 to 4 carbon atoms; n is an integer from 1 to 6; Y is nonto per-chloroalkyl having 1 to 2 carbon atoms; and Z is monoto tri-chloromethyl.
2. The composition of claim 1 wherein R is phenyl, R' is methylene, and n is 1.
3. The composition of claim 1 wherein X is oxygen.
4. The composition of claim 1 wherein X is sulfur.
5. A lubricating oil composition comprising a major proportion of a synthetic lubricating oil base and from 0.1 to 10% by weight of a diaryl haloalkyl phosphate of the formula wherein R is monoto di-nuclear aryl which is substituted with from 0 to 5 alkyl groups having 1 to 10 carbon atoms; X is a chalcogen having an atomic number of from 8 to 16; R is nonto di-alkyl methylene, where alkyl has 1 to 4 carbon atoms; n is an integer from 1 to 6; Y is nonto per-chloroalkyl having 1 to 2 carbon atoms; and Z is monoto tri-chloromethyl.
6. The composition of claim 5 wherein the synthetic lubricating oil base is the aliphatic diester of dibasic carboxylic acids having from 6 to 20 carbon atoms and monohydric alcohols having from 1 to 12 carbon atoms.
7. A synthetic lubricating oil composition having improved extreme-pressure properties which comprises a major proportion of a synthetic ester base and from 0.1 to 10% by weight of a diaryl haloalkyl phosphate of the formula wherein R is monoto di-nuclear aryl substituted with from 0 to 2 alkyl groups, alkyl having from 1 to 10 carbon atoms; X is a chalcogen having an atomic number from 8 to 16; Y is nonto per-chloroalkyl having 1 to 2 carbon atoms; and Z is monoto tri-chloromethyl.
8. The composition of claim 7 wherein R is phenyl.
9. A lubricating oil composition comprising a major proportion of a synthetic ester lubricating oil base and from 0.1 to 10% of a diaryl haloalkylphosphate selected from the group consisting of diphenyl-2,2-bis(chloromethyl)-3-chloropropyl phosphate; diphenyl-2,2-bis(chloromethyl)-3-chloropropyl phosphor-othionate; dioctylphenyl-2,2-bis chloromethyl) -3 -chloropropyl phosphate; and dioctylphenyl-2,2-bis chlorornethyl) -3 -chloropropyl phosphorothionate.
10. The composition of claim 4 containing anantioxidant selected from the group consisting of 2,6-ditertiarybutyl-4-methyl phenol; 4,4'-methylene bis(2,6-ditertiarybutyl phenol); phenyl-alpha-naphthylarnine; phenyl-betanaphthylarnine; 2,2'-dipyridylamine; and diphenylamine.
References Cited by the Examiner UNITED STATES PATENTS 2,289,509 7/ 1942 Malisofl 25249.9 2,656,373 10/1953 Gamrath 260965 2,758,091 8/1956 Webber 25249.9 2,760,937 8/1956 McDermott 25246.7 3,218,256 11/1965 Edwards et a1. 25247.5
DANIEL E. WYMAN, Primary Examiner.
L. G. XIARHOS, Assistant Examiner.

Claims (1)

1. A LUBRICATING OIL COMPOSITION COMPRISING A MAJOR PROPORTION OF A BASE LUBRICATING OIL AND FROMM 0.1 TO 10% BY WEIGHT OF A DIARYL HALOALKYL PHOSPHATE OF THE FORMULA
US355949A 1963-04-23 1964-03-30 Lubricating composition Expired - Lifetime US3287266A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4159960A (en) * 1977-05-02 1979-07-03 Mobil Oil Corporation Lubricant compositions
US5279752A (en) * 1989-02-22 1994-01-18 Nippon Oil Co., Ltd. Composition for lubricating oil

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2289509A (en) * 1933-11-01 1942-07-14 Atlantic Refining Co Lubricant
US2656373A (en) * 1950-04-14 1953-10-20 Monsanto Chemicals Process for producing mixed diaryl esters of ortho-phosphoric acid
US2758091A (en) * 1947-10-28 1956-08-07 Shell Dev Lubricating compositions
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US3218256A (en) * 1959-01-14 1965-11-16 Castrol Ltd Lubricating compositions

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US5279752A (en) * 1989-02-22 1994-01-18 Nippon Oil Co., Ltd. Composition for lubricating oil

Also Published As

Publication number Publication date
BE646836A (en) 1964-10-21
NL6404323A (en) 1964-10-26
DE1282828B (en) 1968-11-14
GB1035984A (en) 1966-07-13

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