US2154098A - Extreme pressure lubricant - Google Patents
Extreme pressure lubricant Download PDFInfo
- Publication number
- US2154098A US2154098A US159371A US15937137A US2154098A US 2154098 A US2154098 A US 2154098A US 159371 A US159371 A US 159371A US 15937137 A US15937137 A US 15937137A US 2154098 A US2154098 A US 2154098A
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- US
- United States
- Prior art keywords
- extreme pressure
- halogenated
- borate
- pressure lubricant
- lubricant
- Prior art date
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- Expired - Lifetime
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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
- 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
- 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
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty 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
- 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
-
- 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
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
-
- 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
- C10N2040/241—Manufacturing joint-less pipes
-
- 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
- C10N2040/242—Hot working
-
- 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
- C10N2040/243—Cold working
-
- 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
- C10N2040/244—Metal working of specific metals
-
- 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
- C10N2040/244—Metal working of specific metals
- C10N2040/245—Soft metals, e.g. aluminum
-
- 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
- C10N2040/244—Metal working of specific metals
- C10N2040/246—Iron or steel
-
- 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
- C10N2040/244—Metal working of specific metals
- C10N2040/247—Stainless steel
-
- 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
Definitions
- This invention relates to improvements in lubricants, and in particular, to improvements in extreme pressure lubricants adapted for use on bearing surfaces which are subjected to high A pressures and high rubbing velocities during use.
- High unit pressures which are encountered frequently in devices employed for the transmission of power, such as hypo'id .gears, worm gears, heavy duty bearings, planetary automatic shifts and the like, necessitate the use of lubricants having superior load carrying properties. Lubricants possessing superior load.
- extreme pressure lubricants are likewise important 20 in cutting and drawing operations where the 011 must withstand the high pressures encountered under-those conditions of use.
- Another object of this invention isto provide a lubricant which will prevent gear teeth or bearing'failure from scoring or galling caused by the welding of small areas of the matting surfaces due to high pressure and high temperature.
- X is eitherfoxygen or sulfur.
- the lubricating oils are preferably those ranging in viscosity from about 50 to 200 seconds Saybolt at 210. F., or
- oils 60 oils.
- calcium, lead, aluminum or other'soaps of high molecular weight organic acids may be added to the composition to increase the viscosity or the consistency of the lubricant.
- Chlor propyl borate (ClCsI-IeO) 3B Brom propyl borate (BI'C3H60)2B Di ch10! butyl borate (C12C4H'1O) 3B Chlor phenyl borate (CiCsH4O)3B Brom phenyl borate (BrCsH4O) 3B Chlor propyl boron sulfide (ClCzHaShB Chlor propyl metal borate (C1C3H60) B O Chlor phenyl meta borate (C1CcH4O) 3:0
- the standard method of making a test on the Almen machine consists in immersing the test pin and bushings in the lubricant to be tested and then rotating the test pin at 600 R. P. M.
- the load which clamps the two halves of the split bushing, is increased at the rate of 2 lbs. added every 10 seconds.
- a record is made of the torque required to rotate the pin at each load increment and the test is completedeither when 30 lbs. have been added to the loading device or when seizure occurs, whichever happens first.
- M1033 and the halogenated organicmeta borates having the general formula (MX)B X in which M is a substituent selected from the group consisting of a. halogenated alkyl radical, halogenated aryl radical and a halogenated aralkyl radical, and X is an element selected from the group consisting of oxygen and sulfur.
- An extreme pressure lubricant comprising a mineral lubricating oil having a viscosity ranging from about 50 seconds Saybolt to about 200 seconds Saybolt at 210 F. and 0.01% to 5% of a halogenated organic borate having the general formula (MXHB in which M is a substitu'ent selected from the group consisting of a halogenated alkyl radical, a halogenated aryl radical and a halogenated aralkyl radical, and X is an element selected from the group consisting of oxygen and sulfur.
- An extreme pressure lubricant comprising a mineral lubricating oil and 0.01% to about 5% of a halogenated organic borate having the general formula (MO):B in which M is a halogenated alkyl radical.
- An extreme pressure lubricant comprising a mineral lubricating oil and 0.01% to about 5% of a halogenated organic borate having the general formula (MO) 33 in which M is a halogenated aryl radical.
- An extreme pressure lubricant comprising a mineral lubricating'oil having a viscosity from about 50 seconds to about 200'seconds Saybolt at 210 F. and 0.01% to about 5% of chlor propyl borate. v CLARENCE M. LOANE.
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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)
Description
;;- 1T D A STATES PATENT OFFICE 1 2,154,098 I EXTREME PRESSURE LUBRICANT I Clarence M. Loane and Bernard H. Shoemaker,-
Hammond, Ind., assignors to Standard Oil Company, Chicago, 111., a corporation of Indiana No Drawing. Application August 16, 1937, Serial No. 159,371
r 6 Claims. This invention relates to improvements in lubricants, and in particular, to improvements in extreme pressure lubricants adapted for use on bearing surfaces which are subjected to high A pressures and high rubbing velocities during use. High unit pressures which are encountered frequently in devices employed for the transmission of power, such as hypo'id .gears, worm gears, heavy duty bearings, planetary automatic shifts and the like, necessitate the use of lubricants having superior load carrying properties. Lubricants possessing superior load. carrying properties which make them specially adapted for use under conditions of high pressure where the pres- 3-- sures encountered are of such magnitude that the separation of gear teeth or bearing surfaces by an ordinary oil filmis not possible, are known in the art as extreme pressure lubricants. Extreme pressure lubricants are likewise important 20 in cutting and drawing operations where the 011 must withstand the high pressures encountered under-those conditions of use.
It is an object of this invention to provide an I improved extreme pressure lubricant which will 25 give superior lubrication to bearing surfaces which are subjected to high pressures and/or high rubbing velocities.
Another object of this invention isto provide a lubricant which will prevent gear teeth or bearing'failure from scoring or galling caused by the welding of small areas of the matting surfaces due to high pressure and high temperature.
We have found that the foregoing objects can be attained if small amounts of halogenated organlc borates are added to lubricants such as oils and soft greases. We have found that the addi-- tion of small amounts of certain halogenated aryl radical or a halogenated aralkyl radical, and
X is eitherfoxygen or sulfur. The lubricating oils are preferably those ranging in viscosity from about 50 to 200 seconds Saybolt at 210. F., or
60 oils. If desired, calcium, lead, aluminum or other'soaps of high molecular weight organic acids may be added to the composition to increase the viscosity or the consistency of the lubricant.
Specific examplesof the type of halogenated those-oils designated as S. A. E. 20, 30, 40, 50 and.
(Cl. 87- 9)v organic borates which we may use are the following:
Chlor propyl borate (ClCsI-IeO) 3B Brom propyl borate (BI'C3H60)2B Di ch10!" butyl borate (C12C4H'1O) 3B Chlor phenyl borate (CiCsH4O)3B Brom phenyl borate (BrCsH4O) 3B Chlor propyl boron sulfide (ClCzHaShB Chlor propyl metal borate (C1C3H60) B=O Chlor phenyl meta borate (C1CcH4O) 3:0
inch long split bushing with provisions for load ing the bearing thus formed by clamping together the two halves of the splitbushing. Provision is also made to measure the torque required to rotate the journal in the loaded bearing.
The standard method of making a test on the Almen machine consists in immersing the test pin and bushings in the lubricant to be tested and then rotating the test pin at 600 R. P. M. The load, which clamps the two halves of the split bushing, is increased at the rate of 2 lbs. added every 10 seconds. A record is made of the torque required to rotate the pin at each load increment and the test is completedeither when 30 lbs. have been added to the loading device or when seizure occurs, whichever happens first.
The following example will illustrate the effectiveness of the addition of small amounts of halogenated organic borates in lubricating oils under extreme pressure conditions. A mineral lubrieating oil having a viscosity of about 58 seconds at210 F. and the same oil with 0.5% of chlor propyl borate when tested in the Almen testing machine gave the following results:
toad at which seizure I occurred Pounds Pounds Pounds Control 8 8 8 Control-+06% chlor propyl borate 16 20 22 The above results indicate that lubricants containing small amounts of the halogenated organic borates are from 100% to almost 200% better than the oil without the addition of halogenated organic borates.
While we have described our invention with a specific embodiment thereof, it is to be understood that the same is merely illustrative of the invention and not a limitation thereof, except insofar as the same is defined in the appended claims.
general formula (M1033 and the halogenated organicmeta borates having the general formula (MX)B=X in which M is a substituent selected from the group consisting of a. halogenated alkyl radical, halogenated aryl radical and a halogenated aralkyl radical, and X is an element selected from the group consisting of oxygen and sulfur.
3. An extreme pressure lubricant comprising a mineral lubricating oil having a viscosity ranging from about 50 seconds Saybolt to about 200 seconds Saybolt at 210 F. and 0.01% to 5% of a halogenated organic borate having the general formula (MXHB in which M is a substitu'ent selected from the group consisting of a halogenated alkyl radical, a halogenated aryl radical and a halogenated aralkyl radical, and X is an element selected from the group consisting of oxygen and sulfur.
4. An extreme pressure lubricant comprising a mineral lubricating oil and 0.01% to about 5% of a halogenated organic borate having the general formula (MO):B in which M is a halogenated alkyl radical.
5. An extreme pressure lubricant comprising a mineral lubricating oil and 0.01% to about 5% of a halogenated organic borate having the general formula (MO) 33 in which M is a halogenated aryl radical.
6. An extreme pressure lubricant comprising a mineral lubricating'oil having a viscosity from about 50 seconds to about 200'seconds Saybolt at 210 F. and 0.01% to about 5% of chlor propyl borate. v CLARENCE M. LOANE.
BERNARD H. SHOEMAKER.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US159371A US2154098A (en) | 1937-08-16 | 1937-08-16 | Extreme pressure lubricant |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US159371A US2154098A (en) | 1937-08-16 | 1937-08-16 | Extreme pressure lubricant |
Publications (1)
Publication Number | Publication Date |
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US2154098A true US2154098A (en) | 1939-04-11 |
Family
ID=22572324
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US159371A Expired - Lifetime US2154098A (en) | 1937-08-16 | 1937-08-16 | Extreme pressure lubricant |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2462616A (en) * | 1944-12-05 | 1949-02-22 | Standard Oil Dev Co | Lubricating oil containing an antioxidant |
US3014061A (en) * | 1956-08-22 | 1961-12-19 | Ethyl Corp | Complex boron esters |
US3067236A (en) * | 1961-02-20 | 1962-12-04 | Dow Chemical Co | Tris (pentahalophenyl) borates |
US3125527A (en) * | 1964-03-17 | Synergistic combination of extreme pres- | ||
US3125526A (en) * | 1964-03-17 | Lubricating greases containing borate | ||
US3125528A (en) * | 1964-03-17 | Method of lubricating automotive | ||
US3907857A (en) * | 1971-08-05 | 1975-09-23 | Horst Mayerhoefer | Boric acid ester of 2,2,2-tris-(bromomethyl)-ethanol |
-
1937
- 1937-08-16 US US159371A patent/US2154098A/en not_active Expired - Lifetime
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3125527A (en) * | 1964-03-17 | Synergistic combination of extreme pres- | ||
US3125526A (en) * | 1964-03-17 | Lubricating greases containing borate | ||
US3125528A (en) * | 1964-03-17 | Method of lubricating automotive | ||
US2462616A (en) * | 1944-12-05 | 1949-02-22 | Standard Oil Dev Co | Lubricating oil containing an antioxidant |
US3014061A (en) * | 1956-08-22 | 1961-12-19 | Ethyl Corp | Complex boron esters |
US3067236A (en) * | 1961-02-20 | 1962-12-04 | Dow Chemical Co | Tris (pentahalophenyl) borates |
US3907857A (en) * | 1971-08-05 | 1975-09-23 | Horst Mayerhoefer | Boric acid ester of 2,2,2-tris-(bromomethyl)-ethanol |
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