US2307307A - Extreme pressure lubricant - Google Patents
Extreme pressure lubricant Download PDFInfo
- Publication number
- US2307307A US2307307A US229523A US22952338A US2307307A US 2307307 A US2307307 A US 2307307A US 229523 A US229523 A US 229523A US 22952338 A US22952338 A US 22952338A US 2307307 A US2307307 A US 2307307A
- Authority
- US
- United States
- Prior art keywords
- extreme pressure
- lubricant
- tetrathio
- pressure lubricant
- group
- 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 24
- -1 alkali-metal xanthate Chemical class 0.000 description 14
- 229920001021 polysulfide Polymers 0.000 description 9
- 239000005077 polysulfide Substances 0.000 description 9
- 150000008117 polysulfides Polymers 0.000 description 9
- 150000003254 radicals Chemical group 0.000 description 8
- 125000005323 thioketone group Chemical group 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- KYLIZBIRMBGUOP-UHFFFAOYSA-N Anetholtrithion Chemical group C1=CC(OC)=CC=C1C1=CC(=S)SS1 KYLIZBIRMBGUOP-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- AWIJRPNMLHPLNC-UHFFFAOYSA-N methanethioic s-acid Chemical compound SC=O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 description 4
- 239000010688 mineral lubricating oil Substances 0.000 description 4
- 239000012991 xanthate Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 2
- HNEVHBHRLCAKKQ-UHFFFAOYSA-N s-ethyl propanethioate Chemical compound CCSC(=O)CC HNEVHBHRLCAKKQ-UHFFFAOYSA-N 0.000 description 2
- VCQYDZJGTXAFRL-UHFFFAOYSA-N s-phenyl benzenecarbothioate Chemical compound C=1C=CC=CC=1C(=O)SC1=CC=CC=C1 VCQYDZJGTXAFRL-UHFFFAOYSA-N 0.000 description 2
- 229910018105 SCl2 Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 101001135436 Urodacus yaschenkoi Antimicrobial peptide scorpine-like-2 Proteins 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- FGAFEZAKEOFARV-UHFFFAOYSA-N s-propyl butanethioate Chemical compound CCCSC(=O)CCC FGAFEZAKEOFARV-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 238000003466 welding Methods 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
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
-
- 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
- C10N2040/20—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
Definitions
- lubricant which will 4 consisting of alkyl, chloralkyl,
- Thi 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 pressures and high rubbin velocities during use.
- Extreme pressure lubricants are likewise important in cutting and drawing operations where the oil must withstand the high pressures encountered under those conditions of use.
- Another object of this invention is to provide ing failure from scoring or galling caused by the welding of small areas of th matting surfaces due to highpressure and high temperature.
- R is a radical selected from the group aryl and chloraryl radicals
- X is an element selected from the group consisting of oxygen and sulfur
- n is an integer greater than 2.
- These compounds may b prepared by reacting an alkali metal xanthate with a sulfur chloride.
- the tetrathio derivative may be prepared by reacting twenty-eight grams of potassium ethyl xanthate, suspended in hexane, or any other suitable diluent, with a little less than the calculated required amount of S2012, and refluxing the reactants on a steam bath for about two hours. lieved to take place:
- Tetrathio diethylthioformate Tetrathio dibutylthioformate Tetrathio diamyldithioformate Tetrathio dilaurylthioformate Tetrathio dilauryl dithioformate Tetrathio dichlorbutylthioformate Tetrathio dichlorlauryldithioformate Tetrathio diphenylthioformate.
- Tetrathio dichlorphenyldithioformate Trithio dipropylthioformate Trithio dichlorbutylthioformate Trithio diphenylthioformate Trithio di-octyldithioformate
- the following reaction is beat Houston, Texas, November 1'7, 1932.
- test pin or journal made of A, inch diameter drill rod which can be rotated in a V2 inch long split bushing with provisions for loading the bearing thus formed by clamping together the two halves of the split bushing. Provision is also made to measure the torque required to rotate the journal in the loaded hear-
- 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 completed either when 30 lbs. have been added to the loading device or when seizure occurs, whichever happens first.
- An extreme pressure lubricant containing a lubricant and a tetrathio alkyl thioformate in small but sufficient quantity to impart extreme pressure propertiesto said lubricant.
- a lubricating composition comprising a lubricating oil base stock and at least .01% of a soluble xanthogen sulfide having the general formula:
- R-X- (S) -XR where R and R are like or unlike alkyl or aryl radicals, and X is either oxygen or sulfur.
- a composition of matter comprising an oil and a small amount of organic xanthogen tetra- 9.
- a lubricating composition comprising a mineral lubricating oil and at least about 0.01% of a soluble organic xanthogen tetrasulfide.
Landscapes
- 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
'a lubricant which will 4 consisting of alkyl, chloralkyl,
Patented Jan. 5, 1943 UNITED STATES PATENT OFFICE 2,307,307 EXTREME PRESSURE LUBRICANT Bernard H. Shoemaker, Hammond, Ind., assignor to Standard Oil Company, Chicago, por'ation of Indiana 111., a cor- No Drawing. Application September 12, 1938,
Serial No. 229,523
11 Claims. (Cl. 252-46) Thi 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 pressures and high rubbin velocities during use.
High unit pressures which are encountered frequently in devices employed for the transmission of power, such as hypoid gears, worm gears, heavy duty bearings, planetary automatic shifts and the like, necessitate the use of lubriproperties, which make them specially adapted for use under conditions of high pressure where the pressures encountered are of such magnitude that the separation of gear teeth or bearing surfaces by an ordinary oil film is not possible, are
known in the art as extreme pressure lubricants.
Extreme pressure lubricants are likewise important in cutting and drawing operations where the oil must withstand the high pressures encountered under those conditions of use.
It is an object of this invention to provide an improved extreme pressure lubricant which will 7 ive superior lubrication to bearing surfaces which are subjected to high' pressures and/or high rubbing velocities.
Another object of this invention is to provide ing failure from scoring or galling caused by the welding of small areas of th matting surfaces due to highpressure and high temperature.
I have found that the foregoing objects can be attained if small amounts, preferably from about 0.01% to about 2%, of thioketopolysulfides, of the type obtained by reacting an alkali-metal xanthate with a sulfur chloride, are added to lubricants, such as oils and greases. These comprevent gear teeth or bearpounds have the general formula (RXC=S)2S1|,
in which R is a radical selected from the group aryl and chloraryl radicals, X is an element selected from the group consisting of oxygen and sulfur, and n is an integer greater than 2.
These compounds may b prepared by reacting an alkali metal xanthate with a sulfur chloride. For example, the tetrathio derivative may be prepared by reacting twenty-eight grams of potassium ethyl xanthate, suspended in hexane, or any other suitable diluent, with a little less than the calculated required amount of S2012, and refluxing the reactants on a steam bath for about two hours. lieved to take place:
KS 2 C=S+SzCh (RO )aS4+2KCl To obtain the trithio derivatives the alkali metal xanthate i reacted with SCl2.
Because of the presence of the thio-keto group i in these compounds I have called them thioketopolysulfides, but more specificallyl believe them to be thioformate polysulfides, and while I refer to them hereinafteras thioformates, I do not wish to limit the scope of this inventionto thioformates, but to the reaction product of an alkalimetal xanthate and a sulfur chloride.
Specific examples of the type of compounds which I may use are the following:
Tetrathio diethylthioformate Tetrathio dibutylthioformate Tetrathio diamyldithioformate Tetrathio dilaurylthioformate Tetrathio dilauryl dithioformate Tetrathio dichlorbutylthioformate Tetrathio dichlorlauryldithioformate Tetrathio diphenylthioformate. Tetrathio dichlorphenyldithioformate Trithio dipropylthioformate Trithio dichlorbutylthioformate Trithio diphenylthioformate Trithio di-octyldithioformate The following reaction is beat Houston, Texas, November 1'7, 1932. Briefly, it consists of a test pin or journal made of A, inch diameter drill rod which can be rotated in a V2 inch long split bushing with provisions for loading the bearing thus formed by clamping together the two halves of the split bushing. Provision is also made to measure the torque required to rotate the journal in the loaded hear- 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 completed either 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 thioformate polysulfides in lubricating oils under extreme pressure conditions. A mineral lubricating oil having a viscosity of about 1'70 seconds at 130 F. and the same oil with 0.5% of tetrathio diethylthioformate when tested in the Almen testing machine gave the following results:
Load at which seizure occurred Pounds Pounds iii 30 Control 6 Control-+% tetrathio diothylthinformate. 30+
While I have described my 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,- which are to be interpreted as broadly as the prior art will permit.
1 claim:
1. An extreme pressure lubricant containing a lubricant and a thioketo polysulfide having the general formula (RXC=S) 2Sn. in which R is a radical selected from the group consisting of alkyl, chloralkyl, aryl and chloraryl radicals, X is an element selected from the group consisting of oxygen and sulfur and n is an integer greater than 2, said thioketo polysulfide being used in small but sufllcient quantities to impart extreme pressure properties to said lubricant.
2. An extreme pressure lubricant containing a than 2.
mineral lubricating oil and from about 0.01% to about 2% of a thloketo polysulfide having thean element selected from the group consisting of oxygen and sulfur and n is aninteger greater 3. An extreme pressure lubricant containing a mineral lubricating oil and from about 0.01% to about 2% of tetrathio diethylthioiormate.
4. An extreme pressure lubricant containing a lubricant and a thioketo polysulfide having the general formula (RXC=S)2S3 in which R is a radical selected from the group consisting of alkyl, chloralkyl, aryl and chloraryl radicals, and X is an element selected from the group consisting of oxygen and sulfur, being used in small but sufflcient quantity to impart extreme pressure properties to said lubricant.
5. An extreme pressure lubricant containing a lubricant and a thioketo polysulfide having-the general formula (RXC=S)2S4 in which R is a radical selected from the group consisting of alkyl, chloralkyl, aryl and chloraryl radicals, and X is an element selected from the group consisting of oxygen and sulfur, said thioketo polysulfide being used in small but sufiicient quantity to impart extreme pressure properties to said lubricant.
6. An extreme pressure lubricant containing a lubricant and a tetrathio alkyl thioformate in small but sufficient quantity to impart extreme pressure propertiesto said lubricant.
7. A lubricating composition comprising a lubricating oil base stock and at least .01% of a soluble xanthogen sulfide having the general formula:
R-X- (S) -XR where R and R are like or unlike alkyl or aryl radicals, and X is either oxygen or sulfur.
8. A composition of matter comprising an oil and a small amount of organic xanthogen tetra- 9. A lubricating composition comprising a mineral lubricating oil and at least about 0.01% of a soluble organic xanthogen tetrasulfide.
10. A lubricating composition according to claim 9 in which the tetrasulfide is an alkyl xanthogen tetrasulfide.
11. A ubricating composition according to claim 9 in which the tetrasulfide is ethyl xanthyltetrasulflde.
BERNARD H. SHOEMAKER.
consisting of said thioketo polysulfide'.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US229523A US2307307A (en) | 1938-09-12 | 1938-09-12 | Extreme pressure lubricant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US229523A US2307307A (en) | 1938-09-12 | 1938-09-12 | Extreme pressure lubricant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2307307A true US2307307A (en) | 1943-01-05 |
Family
ID=22861608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US229523A Expired - Lifetime US2307307A (en) | 1938-09-12 | 1938-09-12 | Extreme pressure lubricant |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2307307A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2431010A (en) * | 1941-07-19 | 1947-11-18 | Standard Oil Dev Co | Soluble cutting oil |
| US2580695A (en) * | 1950-12-01 | 1952-01-01 | Rohm & Haas | Alpha, alpha'-dithiodialdehydes |
| US3862975A (en) * | 1973-07-31 | 1975-01-28 | Goodrich Co B F | Process for preparing liquid xanthate-terminated polymers |
| US4218332A (en) * | 1977-09-16 | 1980-08-19 | The United States Of America As Represented By The Secretary Of Agriculture | Tetrasulfide extreme pressure lubricant additives |
| US5705458A (en) * | 1995-09-19 | 1998-01-06 | The Lubrizol Corporation | Additive compositions for lubricants and functional fluids |
| US5834407A (en) * | 1996-08-21 | 1998-11-10 | The Lubrizol Corporation | Lubricants and functional fluids containing heterocyclic compounds |
-
1938
- 1938-09-12 US US229523A patent/US2307307A/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2431010A (en) * | 1941-07-19 | 1947-11-18 | Standard Oil Dev Co | Soluble cutting oil |
| US2580695A (en) * | 1950-12-01 | 1952-01-01 | Rohm & Haas | Alpha, alpha'-dithiodialdehydes |
| US3862975A (en) * | 1973-07-31 | 1975-01-28 | Goodrich Co B F | Process for preparing liquid xanthate-terminated polymers |
| US4218332A (en) * | 1977-09-16 | 1980-08-19 | The United States Of America As Represented By The Secretary Of Agriculture | Tetrasulfide extreme pressure lubricant additives |
| US5705458A (en) * | 1995-09-19 | 1998-01-06 | The Lubrizol Corporation | Additive compositions for lubricants and functional fluids |
| US5834407A (en) * | 1996-08-21 | 1998-11-10 | The Lubrizol Corporation | Lubricants and functional fluids containing heterocyclic compounds |
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