US2157873A - Process for extreme pressure lubricants - Google Patents
Process for extreme pressure lubricants Download PDFInfo
- Publication number
- US2157873A US2157873A US110930A US11093036A US2157873A US 2157873 A US2157873 A US 2157873A US 110930 A US110930 A US 110930A US 11093036 A US11093036 A US 11093036A US 2157873 A US2157873 A US 2157873A
- Authority
- US
- United States
- Prior art keywords
- extreme pressure
- acids
- phosphorus
- acid
- esters
- 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
Links
- 239000000314 lubricant Substances 0.000 title description 12
- 238000000034 method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 150000003017 phosphorus Chemical class 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000010688 mineral lubricating oil Substances 0.000 description 4
- 239000001384 succinic acid Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- -1 alkenyl succinic acid Chemical compound 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- HZLCGUXUOFWCCN-UHFFFAOYSA-N 2-hydroxynonadecane-1,2,3-tricarboxylic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)(C(O)=O)CC(O)=O HZLCGUXUOFWCCN-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 229940040563 agaric acid Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- BOSMZFBHAYFUBJ-UHFFFAOYSA-N tris(4-methylphenyl) phosphate Chemical class C1=CC(C)=CC=C1OP(=O)(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 BOSMZFBHAYFUBJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- 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
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/22—Acids obtained from polymerised unsaturated acids
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- 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
- C10M2209/082—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 monocarboxylic
-
- 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
-
- 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
-
- 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
-
- 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
- C10M2223/042—Metal salts thereof
Definitions
- This invention relatesto lubricants suitable for lubrication under extreme pressure conditions.
- esters of phosphorus acids have been suggested.
- the terms phosphorus acids or phosphorus esters as herein used refer to the acids and esters respectively of the three and five valent phosphorus, such as phosphorous and phosphoric acids, or esters thereof.
- phosphorus alkyl and aryl esters which have proven to be particularly useful as extreme pressure dopes:
- tri-alkyl phosphites or phosphates in which the alkyl groups contain from 8 to 20 carbon atoms, tri-phenyl and tri-cresyl phosphates, reaction products of phosphoric acid and castor oil, etc.
- extreme pressure properties of extreme pressure compounds can be considerably enhanced by adding to the mineral oil containing same a relatively small amount of a higher polycarboxylic acid, i. e. a polycarboxylic acid which has at least 10 carbon atoms.
- Suitable carboxylic acids are, for instance,
- Polymerized fatty acids may be used, such as are obtained by polymerizing fatty acids with a catalyst of the type of boron fluoride, aluminum chloride, etc. or with silent electric discharges; or by polymerizing a fat and liberating polymerized fatty acids from the polymerized fat by hydrolysis or saponiflcationand acidification; or by chlorinating a fatty acid and subjecting the chlorinated product to the action of an alkali metal oran alkali alcoholate under conditions to effect complete removal of the chlorine and condensation of the fatty acid.
- Natural polycarboxylic acids of the requisite number of carbon atoms, such as agaric acid, are suitable as well.
- oils containing certain extreme pressure compounds such as phosphorus esters or sulfochlorides are used under conditions during which water can accumulate and mix therewith, there is great danger of hydrolyzing such esters or chlorides and liberating mineral acids, which acids are highly corrosive. Since the high molecular weight polycarboxylic acids are powerful corrosion inhibitors, this danger of possible corrosion by free mineral acid is practically eliminated, or at least greatly reduced.
- Example 1 A mineral lubricating oil containing 10% of a metal organic double compound of the type described in the Van Peski-Van Melsen application Serial No. 31,712, filed May 25, 1936, consisting of cupro-bromide and di-normal butyl sulfide, showed in the Timken extreme pressure apparatus an O K value of 25. Upon addition of 2 oi voltolized oleic acid and of cetenyl succinic acid the O K value rose to 50.
- Example 2 The addition of 1% of a voltolized oleic acid to an extreme pressure lubricant consisting of a mineral oil containing 2% paratoluene sulfochloride caused the O K value on the Timken apparatus to rise from 45 to 52, aside from completely inhibiting a slight corrosive action 01 the lubricant.
- Example 3 A mineral lubricating oil containing 2% oi tri-cresyl phosphate, when subjected to the Floyd's test, gave rupture of the film at 200 F. and a pressure of 325 lbs. after minute. Upon addition of /270 by weight oi voltolized oleic acid the lubricant stood the complete Floyd's test; when raising the pressure after the test, rupture only occurred at a pressure exceeding 475 lbs.
- An extreme pressure lubricant comprising a predominant quantity of a mineral lubricating oil, an organic compound having extreme pressure properties containing at least one of the elements oi the group consisting of phosphorus, sulfur and chlorine, and a small quantity of an alkenyl succinic acid having at least 10 carbon atoms.
- An extreme pressure lubricant comprising a mineral lubricating oil containing from .1 to 10% by weight of an organic compound having extreme pressure properties which contains at least one of the elements of the group consisting of phosphorus, sulfur and chlorine, and less than 5% oi' an alkenyl succinic acid having at least 10 carbon atoms.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL2157873X | 1935-12-02 | ||
| GB75438A GB488409A (en) | 1938-01-10 | 1938-01-10 | A process for the manufacture of lubricants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2157873A true US2157873A (en) | 1939-05-09 |
Family
ID=32071204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US110930A Expired - Lifetime US2157873A (en) | 1935-12-02 | 1936-11-14 | Process for extreme pressure lubricants |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2157873A (enrdf_load_stackoverflow) |
| NL (1) | NL43896C (enrdf_load_stackoverflow) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2452319A (en) * | 1943-12-08 | 1948-10-26 | Texas Co | Rust and oxidation inhibited lubricating compositions |
| US2938870A (en) * | 1956-08-03 | 1960-05-31 | Sinclair Refining Co | Extreme pressure lubricating oil containing sulfur-chlorinated esters of chlorendic acid |
| US2969326A (en) * | 1956-08-03 | 1961-01-24 | Sinclair Refining Co | Lubricant composition |
| US3050466A (en) * | 1955-12-19 | 1962-08-21 | Texaco Inc | Roll oil containing a phosphorus acid ester and an oil-miscible dicarboxylic acid |
| US3074886A (en) * | 1958-12-05 | 1963-01-22 | Texaco Inc | Lubricating composition |
| US3130159A (en) * | 1959-05-22 | 1964-04-21 | Stedt Tore Per Gustav | Lubricant for working of metals |
| US3249545A (en) * | 1962-03-23 | 1966-05-03 | Shell Oil Co | Lubricating composition containing non-ash forming additives |
| US3357920A (en) * | 1961-08-18 | 1967-12-12 | Shell Oil Co | Non-ash containing lubricating oil compositions |
| US3720614A (en) * | 1970-09-25 | 1973-03-13 | Monsanto Co | Polyphenyl thioether lubricating compositions |
| US3909429A (en) * | 1973-03-08 | 1975-09-30 | Continental Oil Co | Cutting oil composition |
-
0
- NL NL43896D patent/NL43896C/xx active
-
1936
- 1936-11-14 US US110930A patent/US2157873A/en not_active Expired - Lifetime
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2452319A (en) * | 1943-12-08 | 1948-10-26 | Texas Co | Rust and oxidation inhibited lubricating compositions |
| US3050466A (en) * | 1955-12-19 | 1962-08-21 | Texaco Inc | Roll oil containing a phosphorus acid ester and an oil-miscible dicarboxylic acid |
| US2938870A (en) * | 1956-08-03 | 1960-05-31 | Sinclair Refining Co | Extreme pressure lubricating oil containing sulfur-chlorinated esters of chlorendic acid |
| US2969326A (en) * | 1956-08-03 | 1961-01-24 | Sinclair Refining Co | Lubricant composition |
| US3074886A (en) * | 1958-12-05 | 1963-01-22 | Texaco Inc | Lubricating composition |
| US3130159A (en) * | 1959-05-22 | 1964-04-21 | Stedt Tore Per Gustav | Lubricant for working of metals |
| US3357920A (en) * | 1961-08-18 | 1967-12-12 | Shell Oil Co | Non-ash containing lubricating oil compositions |
| US3249545A (en) * | 1962-03-23 | 1966-05-03 | Shell Oil Co | Lubricating composition containing non-ash forming additives |
| US3720614A (en) * | 1970-09-25 | 1973-03-13 | Monsanto Co | Polyphenyl thioether lubricating compositions |
| US3909429A (en) * | 1973-03-08 | 1975-09-30 | Continental Oil Co | Cutting oil composition |
Also Published As
| Publication number | Publication date |
|---|---|
| NL43896C (enrdf_load_stackoverflow) |
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