US2540570A - Extreme pressure lubricant - Google Patents
Extreme pressure lubricant Download PDFInfo
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- US2540570A US2540570A US65520A US6552048A US2540570A US 2540570 A US2540570 A US 2540570A US 65520 A US65520 A US 65520A US 6552048 A US6552048 A US 6552048A US 2540570 A US2540570 A US 2540570A
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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
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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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
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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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
-
- 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
- C10N2040/02—Bearings
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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
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
-
- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
-
- 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 pertains to extreme pressure lubricants and compositions for imparting extreme pressure or load carrying properties to.
- Extreme pressure additives containing active sulfur, phosphorus, or chlorine, or two or more of these, are effective to react immediately with the metal surfaces at their higher temperatures to form a protective metal sulfide, phosphide, or chloride film which serves temporarily as a lubricating medium until the normal oil film between the parts can be reestablished. Extreme pressure additives are, therefore, reactive with the metals they lubricate to form extremely thin protective films thereon when the temperature rises due to normal oil film failure.
- compositions having extreme pressure properties and other desirable properties for use in lubricating oil compositions and the like may be prepared from various glycol esters of ordinary rosin and related hydrogenated materials and from fatty acids and other organic acids.
- glycol esters of ordinary rosin and related hydrogenated materials and from fatty acids and other organic acids.
- the structures of the glycols which may vbe employed vary widely in respect to chain length, hydroxyl groups, ether linkages or in other aspects, varying with requirements of oil solubility, reactive oxygen groups, reactive double bonds and the like.
- the glycol esters can be represented by the generalized formula:
- esters used in the present invention have at least one double bond capa- I ble of reacting with sulfur, phosphorus sulfide, a phosphorus halide, oxyhalides, selenides, and the like.
- R and R in the above formula may be aliphatic, aromatic or substituted aromatic, or cyclic, it is necessary that R or R contain an ethylenic bond.
- both R and R contain ethylenic bonds, and contain from 11 to 21 carbon atoms.
- glycols and acids may be esterified in various combinations to form a wide variety of useful esters, which may be used to prepare the additives of the invention. It is to be understood, however, that the compounds listed are given for illustration only and should not be construed as limiting the invention, which is limited only by the appended claims.
- Talloii Mixed rosin acids Lard oil acids
- Sperm oil acids Of these esters those which contain one aliphatic acid and one cyclic or substituted cyclic acid are preferred.
- Acids which have been found to be especially suitable for reaction with the dihydric alcohols to form the esters used in the present invention are the naturally occurring rosin and talloils, and the hydrogenation products thereof.
- the talloils contemplated are by-products from sulfate wood pulp digestion, consisting mainly of rosin acids and fatty acids.
- the ester is sulfurized and phosphorized.
- the ester is first reacted with elemental sulfur, for example, by heating at a temperature somewhat in excess of 250 F. and preferably in the range of 280 to 500 F.
- the reaction time may vary from about one hour to hours although by the addition of a sulfurization catalyst, such as sulfur chloride or sulfur dichloride and the like, the reaction may be hastened somewhat.
- the sulfurized product is then reacted with a bi-elemental phosphorus compound, for example, P453, P487, P255, P013, PCls, P205, etc.
- the phosphorizing reaction is suitably carried out at relatively low temperatures of the order of 150 to 250 F., preferably in the range of 200 to 230 F. A lower temperature is ordinarily required in the case of halides. In general this reaction may be completed in from 6 to 12 hours.
- the sulfurization and phosphorization is carried out simultaneously by reacting the ester with a sulfide of phosphorus, or with a mixture of sulfur and a bielemental phosphorus compound.
- the reactants are heated to 150 to 250 F. preferably to 200 to 230 F. for 2-5 hours, and then further heated to a higher temperature preferably in the range 300-400 F. for several hours, or until a product is obtained which does not blacken copper when tested in the concentration in which the additive is to be employed.
- EXAIVIPLE I An ethylene glycol ester of talloil consisting substantially of esters of the type R-COOCHz-CHzOOC-R' wherein R is a fatty acid and R is a rosin acid, was employed in laboratory investigation.
- the sulfurized product was further reacted with 0.5% by weight of P483 for a period of 12 hours at 210 F. with stirring. The product was then cooled and was found to contain 0.21% phosphorus and 5.71 sulfur.
- This preparation was repeated three times on a larger scale and the products showed essentially the same analyses and performance characteristics.
- a mixture of the three preparations was blended with mineral oil as follows to produce a lubricant for full scale axle driving tests.
- Example III 1.0% a wax-naphthalene pour depressant 34.0% Pennsylvania steam refined cylinder oil of 230.9 vis./210 SUS 55.0% Mid-Continent acid refined lubricating stock of 50.5 vis./210 SUS The resulting lubricant was found to perform satisfactorily in automotive hypoid gears under conditions of either high torque and low speed (truck type operation) or high speed and low torque (passenger car type operation).
- EXAMPLE III A pilot-plant batch of additive was prepared from a commercially available ethylene glycol ester of talloil produced by the Hercules Powder Company, and known as Resin X 4000-43. The proportions of ingredients and the conditions of reaction were the same as in Example II.
- esters free of rosin acids show some improvement in oil solubility and storage stability, especially at elevated temperatures.
- ester just described was treated in the same manner as shown in Example I. After sulfurizing, this ester contained 4.49% sulfur, and after phosphorizing, it contained 0.26% phosphorus and 4.54% sulfur.
- compositions of the type referred to above may be added in various quantities to various types of oils, as will be obvious to those skilled in the art. They may be added to relatively light oils, such as oils of automotive engine grades for the purpose of increasing oxidation stability, although normally they will be used more widely in heavier oils such as those of SAE 80, SAE 90 or SAE 140 grade for the lubrication of hypoid gears and other gears where extreme pressure properties are desired. They may also be used in synthetic lubricating oils, for example those of the ester type and of the polyether type, in cutting oils, and in soluble cutting oils in conjunction with may be marketed straight or in 10% to solutions in mineral oil of appropriate grade. The mineral lubricating oils having viscosities between about 35 S. S. U. and 1,000 8. S. U. at 210 F. are preferred and the useful proportions of the additive are ordinarily between 1% and 20% by. weight, based on the total composition.
- Various conventional additives may be employed in connection with the extreme pressure compound described above, such as thickeners, oiliness agents, oxidation inhibitors, tackiness agents, viscosity index improvers, pour point depressants, and the like. These materials may also be used in greases thickened with soaps, carbon blacks, silica gel and other known greaseforming materials.
- An extreme pressure additive for mineral base lubricating oils consisting essentially of an ester having the formula 0 o R- X(CHZCHZ'X), -Y wherein X is an element selected from the class consisting of oxygen and sulfur; n is an integer ranging from 1 to 4;
- 0 JLY is the combining radical of a rosin acid; It is an unsaturated fatty acid having from 11 to 21 carbon atoms; and p Z and Z are radicals selected from the class consisting of hydrogen and paraflinic hydrocarbons containing from 1 to 4 carbon atoms,
- ester being treated with a suiilcient amount of elemental sulfur at a temperature of from 250 F. to 500 F. for from 1 to 10 hours so that the final product contains from about 4.49% to about 8.1% sulfur, and then treated with a suflicient amount of a phosphorus sulfide at a temfrom about 4.49 to 8.1% sulfur and then reacted with a suiiicient amount of a phosphorus sulfide at a temperature of from F. to 250/F. for from 6 to 12 hours so that the final product contains from about 0.21% to 0.31% phosphorus.
- a lubricating oil composition consisting essentially of a mineral 011 base stock containing combined therein from 1 to 20% by weight, based on the total composition, of an ester having the formula 0 o Rt JX(CHZ-CHZ'-X),.i JY
- X is an element selected from the class consisting of oxygen and sulfur; n is an integer ranging from 1 to 4;
- R is the combining radical of a rosin acid
- R is an unsaturated fatty acid having from 11 to 21 carbon atoms
- Z and Z are radicals selected from the class consisting of hydrogen and parafiinic hydrocar-' bons containing from 1 to 4 carbon atoms,
- ester being treated with a suilicient amount of elemental sulfur at a temperature of from 250 F. to 500 F. for from 1 to 10 hours so that the final product contains from about 4.49% to about 8.1% sulfur, and then treated with a sufllcient amount of a phosphorus sulfide at a temperature of from 150 F. to 250 F. for from 6 to 12 hours so that the final product contains about 0.21% to 0.31% phosphorus.
- a lubricating composition consisting essentially of a mineral oil base stock having combined therein from 1 to 20% by weight based on the total composition of-the ethylene glycol ester of tall oil which has been reacted with an amount of elemental sulfur for from 1 to 10 hours at a temperature of from 250 F, to 500 F. so that the final product contains from about 4.49 to 8.1%
Description
Patented Feb. 6, 1951 UNITED STATES PATENT OFFICEv EXTREME PRESSURE LUBRICANT Elmer B. Cypher-s, Cranford, N. .L, assignor to Standard Oil Development Company, a corporation of Delaware No Drawing. Application December 15, 1948,
Serial No. 65,520
I This invention pertains to extreme pressure lubricants and compositions for imparting extreme pressure or load carrying properties to.
- mineral base lubricating oils and greases which are used to lubricate opposed metal surfaces are likely to fall under extremely heavy load conditions. For example, certain machine elements such as the hypoid gears commonly used in automotive vehicles may be subjected at times to extremely heavy pressures of the order of hundreds of thousands of pounds per square inch. If the film of lubricating oil separating the opposed elements fails, as it is likely to do under such pressure, the surfaces will contact each other directly, generating high temperatures due to friction, with resultant seizure or excessive wear and early failure. Extreme pressure additives containing active sulfur, phosphorus, or chlorine, or two or more of these, are effective to react immediately with the metal surfaces at their higher temperatures to form a protective metal sulfide, phosphide, or chloride film which serves temporarily as a lubricating medium until the normal oil film between the parts can be reestablished. Extreme pressure additives are, therefore, reactive with the metals they lubricate to form extremely thin protective films thereon when the temperature rises due to normal oil film failure.
According to the present invention, it has been discovered that compositions having extreme pressure properties and other desirable properties for use in lubricating oil compositions and the like may be prepared from various glycol esters of ordinary rosin and related hydrogenated materials and from fatty acids and other organic acids. The structures of the glycols which may vbe employed vary widely in respect to chain length, hydroxyl groups, ether linkages or in other aspects, varying with requirements of oil solubility, reactive oxygen groups, reactive double bonds and the like. The glycol esters can be represented by the generalized formula:
wherein X represents oxygen or sulfur, n repreu 4 Claims. (Cl. 252-463) 2 sents an integer from 1 to 4, and Y represents hydrogen or an R--U-group and R and R represent hydrocarbon radicals and Z and Z are radicals consisting of -H or an alkyl hydrocarbon having from 1 to 4 carbon atoms.
It is necessary that the esters used in the present invention have at least one double bond capa- I ble of reacting with sulfur, phosphorus sulfide, a phosphorus halide, oxyhalides, selenides, and the like. Thus, whereas R and R in the above formula may be aliphatic, aromatic or substituted aromatic, or cyclic, it is necessary that R or R contain an ethylenic bond. Preferably, both R and R contain ethylenic bonds, and contain from 11 to 21 carbon atoms.
The following glycols and acids may be esterified in various combinations to form a wide variety of useful esters, which may be used to prepare the additives of the invention. It is to be understood, however, that the compounds listed are given for illustration only and should not be construed as limiting the invention, which is limited only by the appended claims.
Glycols:
Ethylene Diethylene Triethylene Propylene Dipropylene Butylene Thioglycols:
Monothioethylene glycol Dithioethylene glycol Acids:
Aliphatic:
Oleic Stearic Palmitic Lauric Linoleic Linolenic Ricinoleic Aromatic:
Benzoic Toluio Phenyl acetic Phenyl propionlc Dehydroabietic Isopropyl benzoic Tertiary octyl benzoic Phenyl ethanoic Cyclic:
Abietlc Neoabietic Dextropimeric Mixed acids:
Talloii Mixed rosin acids Lard oil acids Sperm oil acids Of these esters, those which contain one aliphatic acid and one cyclic or substituted cyclic acid are preferred.
Acids which have been found to be especially suitable for reaction with the dihydric alcohols to form the esters used in the present invention are the naturally occurring rosin and talloils, and the hydrogenation products thereof. The talloils contemplated are by-products from sulfate wood pulp digestion, consisting mainly of rosin acids and fatty acids.
In producing the additive of the present invention, the ester is sulfurized and phosphorized. In one modification, the ester is first reacted with elemental sulfur, for example, by heating at a temperature somewhat in excess of 250 F. and preferably in the range of 280 to 500 F. The reaction time may vary from about one hour to hours although by the addition of a sulfurization catalyst, such as sulfur chloride or sulfur dichloride and the like, the reaction may be hastened somewhat. The sulfurized product is then reacted with a bi-elemental phosphorus compound, for example, P453, P487, P255, P013, PCls, P205, etc. The phosphorizing reaction is suitably carried out at relatively low temperatures of the order of 150 to 250 F., preferably in the range of 200 to 230 F. A lower temperature is ordinarily required in the case of halides. In general this reaction may be completed in from 6 to 12 hours. In another modification, the sulfurization and phosphorization is carried out simultaneously by reacting the ester with a sulfide of phosphorus, or with a mixture of sulfur and a bielemental phosphorus compound. In this modification the reactants are heated to 150 to 250 F. preferably to 200 to 230 F. for 2-5 hours, and then further heated to a higher temperature preferably in the range 300-400 F. for several hours, or until a product is obtained which does not blacken copper when tested in the concentration in which the additive is to be employed.
The invention will be more fully understood by reference to the following examples:
EXAIVIPLE I An ethylene glycol ester of talloil consisting substantially of esters of the type R-COOCHz-CHzOOC-R' wherein R is a fatty acid and R is a rosin acid, was employed in laboratory investigation.
376 grams of this ethylene glycol ester of talloil were heated to 290 F. and 24 grams of sulfur flowers were added; the mixture was stirred and heated'to 395 F. and maintained between 360 and 395 F. for 2 hours and then cooled. The sulfurized product was analyzed and found to contain 5.64% of sulfur and in a 10% concentration in mineral oil showed no discoloration of a copper strip in one hour at 250 F.
The sulfurized product was further reacted with 0.5% by weight of P483 for a period of 12 hours at 210 F. with stirring. The product was then cooled and was found to contain 0.21% phosphorus and 5.71 sulfur.
10% by weight of each of the above additives was blended in of a mineral lubricating oil having the following characteristics:
Gravity 'API 25.4 Flash FL. 460 Con. carbon 1.754 Sulfur ..-per cent 0.48 Pour F... +10 Vis. 1445.7 Via/210 109.8 V. I. 97.3
The lubricants thus formed showed the following characteristics:
Vis./100 SUS 1736.4 Via/210 SUS 126.7 V. I 101.4 Copper corrosion Bright It will be noted that this additive improves the viscosity index of the base oil to which it is added. This is an advantage in addition to the excellent load-carrying properties shown in Table I.
EXAMPLE H the following characteristics:
Mineral 107 Exam is on 11 iii Mine l al Alone 01] Vis./l00 F. SUS Via/210 F. SUS 351 5 335 Viscosity Index 95. 5 96 2 Copper Corrosion (1 hr. at 250 F.) Bright Bright Performance characteristics of this product are shown in Table I.
This preparation was repeated three times on a larger scale and the products showed essentially the same analyses and performance characteristics. A mixture of the three preparations was blended with mineral oil as follows to produce a lubricant for full scale axle driving tests.
10.0% additive Example III I 1.0% a wax-naphthalene pour depressant 34.0% Pennsylvania steam refined cylinder oil of 230.9 vis./210 SUS 55.0% Mid-Continent acid refined lubricating stock of 50.5 vis./210 SUS The resulting lubricant was found to perform satisfactorily in automotive hypoid gears under conditions of either high torque and low speed (truck type operation) or high speed and low torque (passenger car type operation).
EXAMPLE III A pilot-plant batch of additive was prepared from a commercially available ethylene glycol ester of talloil produced by the Hercules Powder Company, and known as Resin X 4000-43. The proportions of ingredients and the conditions of reaction were the same as in Example II.
Analysis showed this additive to contain 0.26%.
phosphorus and 8.10% sulfur. Performance characteristics of a blend of this product in the same oil as was employed in Example II are shown in Table I.
Another ester of the same type as described in Examples I, H and III was produced by first preparing the half-ester of rosin and-ethylene glycol, followed by further esterification with oleic acid. By this means, a product essentially free of uncombined rosin acids is produced, whereas, in the previous examples, a small amount of free rosin acids remained. Esters free of rosin acids show some improvement in oil solubility and storage stability, especially at elevated temperatures.
The ester just described was treated in the same manner as shown in Example I. After sulfurizing, this ester contained 4.49% sulfur, and after phosphorizing, it contained 0.26% phosphorus and 4.54% sulfur.
The performance of this additive was determined in blends containing small amounts oftricresyl phosphate. Highly efiective extreme pressure lubricants were obtained, as shown in Table II.
It will be understood, of course, that compositions of the type referred to above may be added in various quantities to various types of oils, as will be obvious to those skilled in the art. They may be added to relatively light oils, such as oils of automotive engine grades for the purpose of increasing oxidation stability, although normally they will be used more widely in heavier oils such as those of SAE 80, SAE 90 or SAE 140 grade for the lubrication of hypoid gears and other gears where extreme pressure properties are desired. They may also be used in synthetic lubricating oils, for example those of the ester type and of the polyether type, in cutting oils, and in soluble cutting oils in conjunction with may be marketed straight or in 10% to solutions in mineral oil of appropriate grade. The mineral lubricating oils having viscosities between about 35 S. S. U. and 1,000 8. S. U. at 210 F. are preferred and the useful proportions of the additive are ordinarily between 1% and 20% by. weight, based on the total composition.
Various conventional additives may be employed in connection with the extreme pressure compound described above, such as thickeners, oiliness agents, oxidation inhibitors, tackiness agents, viscosity index improvers, pour point depressants, and the like. These materials may also be used in greases thickened with soaps, carbon blacks, silica gel and other known greaseforming materials.
What is claimed is:
1. An extreme pressure additive for mineral base lubricating oils consisting essentially of an ester having the formula 0 o R- X(CHZCHZ'X), -Y wherein X is an element selected from the class consisting of oxygen and sulfur; n is an integer ranging from 1 to 4;
0 JLY is the combining radical of a rosin acid; It is an unsaturated fatty acid having from 11 to 21 carbon atoms; and p Z and Z are radicals selected from the class consisting of hydrogen and paraflinic hydrocarbons containing from 1 to 4 carbon atoms,
said ester being treated with a suiilcient amount of elemental sulfur at a temperature of from 250 F. to 500 F. for from 1 to 10 hours so that the final product contains from about 4.49% to about 8.1% sulfur, and then treated with a suflicient amount of a phosphorus sulfide at a temfrom about 4.49 to 8.1% sulfur and then reacted with a suiiicient amount of a phosphorus sulfide at a temperature of from F. to 250/F. for from 6 to 12 hours so that the final product contains from about 0.21% to 0.31% phosphorus.
3. A lubricating oil composition consisting essentially of a mineral 011 base stock containing combined therein from 1 to 20% by weight, based on the total composition, of an ester having the formula 0 o Rt JX(CHZ-CHZ'-X),.i JY
wherein X is an element selected from the class consisting of oxygen and sulfur; n is an integer ranging from 1 to 4;
is the combining radical of a rosin acid; R is an unsaturated fatty acid having from 11 to 21 carbon atoms; and Z and Z are radicals selected from the class consisting of hydrogen and parafiinic hydrocar-' bons containing from 1 to 4 carbon atoms,
said ester being treated with a suilicient amount of elemental sulfur at a temperature of from 250 F. to 500 F. for from 1 to 10 hours so that the final product contains from about 4.49% to about 8.1% sulfur, and then treated with a sufllcient amount of a phosphorus sulfide at a temperature of from 150 F. to 250 F. for from 6 to 12 hours so that the final product contains about 0.21% to 0.31% phosphorus.
4. A lubricating composition consisting essentially of a mineral oil base stock having combined therein from 1 to 20% by weight based on the total composition of-the ethylene glycol ester of tall oil which has been reacted with an amount of elemental sulfur for from 1 to 10 hours at a temperature of from 250 F, to 500 F. so that the final product contains from about 4.49 to 8.1%
8 sulfur and then reacted with a sumcient amount of a phosphorus sulfide at a temperature of from 150 F. to 250 F. for from 6 to 12 hours so that the final product contains from about 0.21% to ELMER B. CYPHERS.
REFERENCES CITED The following references are of record in the 5 0.31% Phosphorus.
m file of this patent:
UNITED STATES PATENTS
Claims (1)
- 3. A LUBRICATING OIL COMPOSITION CONSISTING ESSENTIALLY OF A MINERAL OIL BASE STOCK CONTAINING COMBINED THEREIN FROM 1 TO 20% BY WEIGHT, BASED ON THE TOTAL COMPOSITION, OF AN ESTER HAVING THE FORMULA
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Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3156649A (en) * | 1960-04-25 | 1964-11-10 | Shell Oil Co | Functional fluids containing thiocarboxylate esters |
US3189547A (en) * | 1959-07-03 | 1965-06-15 | Shell Oil Co | Lubricating compositions |
US3198737A (en) * | 1960-12-23 | 1965-08-03 | Shell Oil Co | Lubricating compositions and additives therefor |
US3400139A (en) * | 1959-07-03 | 1968-09-03 | Shell Oil Co | Sulfides of higher fatty acids |
US4053427A (en) * | 1971-07-26 | 1977-10-11 | Chevron Research Company | Cross-sulfurized olefins and fatty acid monoesters in lubricating oils |
US4098706A (en) * | 1975-05-07 | 1978-07-04 | Sapchim-Fournier-Cimag | Lubricating agents for thermoplastic materials and process for preparing the same |
US4335004A (en) * | 1980-01-11 | 1982-06-15 | Phillips Petroleum Company | Lubricating compositions containing diesters of dimercapto ethers |
US4344853A (en) * | 1980-10-06 | 1982-08-17 | Exxon Research & Engineering Co. | Functional fluid containing metal salts of esters of hydrocarbyl succinic acid or anhydride with thio-bis-alkanols as antioxidants |
US4702850A (en) * | 1980-10-06 | 1987-10-27 | Exxon Research & Engineering Co. | Power transmitting fluids containing esters of hydrocarbyl succinic acid or anhydride with thio-bis-alkanols |
US4758361A (en) * | 1984-05-18 | 1988-07-19 | Texaco Inc. | Lubricating oil of improved anti-friction properties containing hydroxyhydrocarbyl mercapto ester of a C1 -C40 fatty acid such as that derived from coconut oil |
US4760170A (en) * | 1985-07-01 | 1988-07-26 | Exxon Research & Engineering Co. | Solution process for preparing metal salt esters of hydrocarbyl substituted succinic acid or anhydride and alkanols |
US4909952A (en) * | 1989-01-03 | 1990-03-20 | The Lubrizol Corporation | Sulfur-containing polymeric polyesters and additive concentrates and lubricating oils containing same |
US5573725A (en) * | 1989-05-12 | 1996-11-12 | Texaco Inc. | Corrosion inhibition system featuring the reaction product of a polythioether polyol and fatty acid |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2211306A (en) * | 1935-12-19 | 1940-08-13 | Pure Oil Co | Lubricant and method of preparing same |
US2385912A (en) * | 1943-06-30 | 1945-10-02 | Nat Oil Prod Co | Sulphurized glyceryl esters of tall oil and method for making same |
US2422630A (en) * | 1947-06-17 | Preparation of lubricants | ||
US2469741A (en) * | 1947-06-11 | 1949-05-10 | Standard Oil Dev Co | Soluble cutting oil base |
-
1948
- 1948-12-15 US US65520A patent/US2540570A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2422630A (en) * | 1947-06-17 | Preparation of lubricants | ||
US2211306A (en) * | 1935-12-19 | 1940-08-13 | Pure Oil Co | Lubricant and method of preparing same |
US2385912A (en) * | 1943-06-30 | 1945-10-02 | Nat Oil Prod Co | Sulphurized glyceryl esters of tall oil and method for making same |
US2469741A (en) * | 1947-06-11 | 1949-05-10 | Standard Oil Dev Co | Soluble cutting oil base |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3189547A (en) * | 1959-07-03 | 1965-06-15 | Shell Oil Co | Lubricating compositions |
US3400139A (en) * | 1959-07-03 | 1968-09-03 | Shell Oil Co | Sulfides of higher fatty acids |
US3156649A (en) * | 1960-04-25 | 1964-11-10 | Shell Oil Co | Functional fluids containing thiocarboxylate esters |
US3198737A (en) * | 1960-12-23 | 1965-08-03 | Shell Oil Co | Lubricating compositions and additives therefor |
US4053427A (en) * | 1971-07-26 | 1977-10-11 | Chevron Research Company | Cross-sulfurized olefins and fatty acid monoesters in lubricating oils |
US4098706A (en) * | 1975-05-07 | 1978-07-04 | Sapchim-Fournier-Cimag | Lubricating agents for thermoplastic materials and process for preparing the same |
US4335004A (en) * | 1980-01-11 | 1982-06-15 | Phillips Petroleum Company | Lubricating compositions containing diesters of dimercapto ethers |
US4344853A (en) * | 1980-10-06 | 1982-08-17 | Exxon Research & Engineering Co. | Functional fluid containing metal salts of esters of hydrocarbyl succinic acid or anhydride with thio-bis-alkanols as antioxidants |
US4702850A (en) * | 1980-10-06 | 1987-10-27 | Exxon Research & Engineering Co. | Power transmitting fluids containing esters of hydrocarbyl succinic acid or anhydride with thio-bis-alkanols |
US4758361A (en) * | 1984-05-18 | 1988-07-19 | Texaco Inc. | Lubricating oil of improved anti-friction properties containing hydroxyhydrocarbyl mercapto ester of a C1 -C40 fatty acid such as that derived from coconut oil |
US4760170A (en) * | 1985-07-01 | 1988-07-26 | Exxon Research & Engineering Co. | Solution process for preparing metal salt esters of hydrocarbyl substituted succinic acid or anhydride and alkanols |
US4909952A (en) * | 1989-01-03 | 1990-03-20 | The Lubrizol Corporation | Sulfur-containing polymeric polyesters and additive concentrates and lubricating oils containing same |
WO1990007565A1 (en) * | 1989-01-03 | 1990-07-12 | The Lubrizol Corporation | Sulfur-containing polymeric polyesters and additive concentrates and lubricating oils containing same |
US5573725A (en) * | 1989-05-12 | 1996-11-12 | Texaco Inc. | Corrosion inhibition system featuring the reaction product of a polythioether polyol and fatty acid |
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