US2343831A - Lubricating composition - Google Patents
Lubricating composition Download PDFInfo
- Publication number
- US2343831A US2343831A US399945A US39994541A US2343831A US 2343831 A US2343831 A US 2343831A US 399945 A US399945 A US 399945A US 39994541 A US39994541 A US 39994541A US 2343831 A US2343831 A US 2343831A
- Authority
- US
- United States
- Prior art keywords
- extreme pressure
- dithiophosphoric acid
- lubricating composition
- lubricant
- butyl
- 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
- 230000001050 lubricating effect Effects 0.000 title description 12
- 239000000203 mixture Substances 0.000 title description 10
- 239000000314 lubricant Substances 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 5
- 239000010688 mineral lubricating oil Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- SXFUPIWGUVVUOC-UHFFFAOYSA-N butan-2-yloxy-butan-2-ylsulfanyl-hydroxy-sulfanylidene-lambda5-phosphane Chemical compound CCC(C)OP(O)(=S)SC(C)CC SXFUPIWGUVVUOC-UHFFFAOYSA-N 0.000 description 2
- WCOKRIFVIGTVBN-UHFFFAOYSA-N butoxy-butylsulfanyl-hydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCOP(O)(=S)SCCCC WCOKRIFVIGTVBN-UHFFFAOYSA-N 0.000 description 2
- YJNALOLHXQQOIK-UHFFFAOYSA-N di(butan-2-yloxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCC(C)OP(S)(=S)OC(C)CC YJNALOLHXQQOIK-UHFFFAOYSA-N 0.000 description 2
- XPRULOZMJZDZEF-UHFFFAOYSA-N dibutoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCOP(S)(=S)OCCCC XPRULOZMJZDZEF-UHFFFAOYSA-N 0.000 description 2
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001500 aryl chlorides Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- DFVPPGZSXADRCW-UHFFFAOYSA-N bis(2-methylphenoxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC1=CC=CC=C1OP(S)(=S)OC1=CC=CC=C1C DFVPPGZSXADRCW-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- -1 diaryl dithiophosphoric acid derivatives Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XSASGTJDJIAGMI-UHFFFAOYSA-N hydroxy-(2-methylphenoxy)-(2-methylphenyl)sulfanyl-sulfanylidene-lambda5-phosphane Chemical compound Cc1ccccc1OP(O)(=S)Sc1ccccc1C XSASGTJDJIAGMI-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- 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
- C10M2223/045—Metal containing thio derivatives
-
- 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
- C10M2223/047—Thioderivatives not containing metallic elements
-
- 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
Definitions
- This invention relates to extreme pressure lubricating compositions, and more particularly to the use of dialkyl and diaryl dithiophosphoric acid derivatives as extreme pressure lubricant bases.
- the standard lubricants for heavy duty service for example in gear transmissions with high tooth pressures as in hypoid gears, are mostly hydrocarbon oils. These mineral oils when properly refined are very stable under heat but they are deficient in oiliness and in the strength of the oil film which is formed between metal surfaces in bearings or at other points where lubrication takes place. Insuflicient film strength will result in metal to metal contact even when an adequate quantity of lubricant is supplied to the bearing and insufiicient oiliness will prevent retention of an oil film in the bearing when for any reason the lubricant supply becomes insuflicient. Thus, both deficient oiliness and deficient film strength result in metal to metal contact and consequently higher wear and rapid development of heat.
- reaction products of dialkyl and diaryl dithiophosphoric acids or their alkali metal or ammonium salts with chlorine compounds or oxidizers such as air capable of chemically removing hydrogen from a dithiophosphoric acid make excellent extreme pressure lubricant bases.
- the reaction products which are the subject of Romieux and Ashley Reissue Patent No. 20,411, are preferably prepared as set out in that patent.
- Dialkyl and diaryl dithiophosphate poiysulfldes having the following general formula are preferred:
- R is alkayl or ary1 and a: is zero or a small whole number.
- the invention is not intended to be limited to this specific embodiment.
- Lubricating compositions containing small amounts of these dialkyl and diaryl dithiophosphoric acid derivatives form very tenacious oil films on metal surfaces and, at the same time, have satisfactory oiliness properties. They are therefore superior extreme pressure lubricants for use in hypoid gears, particularly since the running temperature of hypoid gears rarely exceeds about C. and therefore no corrosion problem arises due to decomposition of the lubricant base to form corrosive acids.
- the lubricating compositions of the present invention are best suited for use in hypoid gears, they are not limited to this application and may also be used in high compression ratio automobile engines and other internal combustion engines.
- Example 1 10% of di-secondary-butyl dithiophosphate tetrasulfide having the following formula:
- the di-secondary-butyl dithiophosphate tetrasulfide was prepared by reacting di-secondary-- butyl dithiophosphoric acid with sulfur monochloride.
- Example 2 A test similar to that of Example 1 was made of a lubricating composition containing 10% of di-n-butyl dithiophosphate disulfide having the following formula:
- the di-n-butyl dithiophosphate disulfide was prepared by reacting an ethylene chloride solution of di-n-butyl dithiophosphoric acid with chlorine.
- Example 3 A test similar to that of Example 1 was made of a lubricating composition containing of di-o-cresyl dithiophosphate tetrasulfide having the following formula:
- An extreme pressure lubricant comprising a mineral lubricating oil and a small amount of the reaction product of a dithiophosphoric acid derivative and a chlorine containing compound capable of chemically removing hydrogen from a dithiophosphoric acid.
- An extreme pressure lubricant comprising a mineral lubricating oil-.and a small amount of the reaction product of a member of the group consisting of dialkyl and diaryl dithiophosphoric acids and alkali metal and ammonium dialkyl and diaryl dithiophosphates, and a chlorine containing compound capable of chemically removing hydrogen from a dithiophosphoric acid.
- An extreme pressure lubricant comprising a mineral lubricating oil and a small amount of a compound having the following general formula:
- R is a member of the group consisting of alkyl and aryl radicals and a: is zero or a small whole number.
- An extreme pressure lubricant comprising a mineral lubricating oil and a small amount of di-secondary-butyl dithiophosphoric acid tetrasulfide having the formula:
- An extreme pressure lubricant comprising a mineral lubricating oil and a small amount of di-n-butyl dithiophosphoric acid disulflde having the formula:
- An extreme pressure lubricant comprising a mineral lubricating oil and a small amount of di-o-cresyl dithiophosphoric acid tetrasuliide having the formula;
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
Patented Mar. 7, 1944 LUBRICATING COMPOSITION John L. Osborne, Elizabeth, N. J., asslgnor'to American Cyanamid Company New York,
N. Y., a corporation of Maine No Drawing. Application June 26, 1941 Serial N0. 399,945
6 Claims.
This invention relates to extreme pressure lubricating compositions, and more particularly to the use of dialkyl and diaryl dithiophosphoric acid derivatives as extreme pressure lubricant bases.
The standard lubricants for heavy duty service, for example in gear transmissions with high tooth pressures as in hypoid gears, are mostly hydrocarbon oils. These mineral oils when properly refined are very stable under heat but they are deficient in oiliness and in the strength of the oil film which is formed between metal surfaces in bearings or at other points where lubrication takes place. Insuflicient film strength will result in metal to metal contact even when an adequate quantity of lubricant is supplied to the bearing and insufiicient oiliness will prevent retention of an oil film in the bearing when for any reason the lubricant supply becomes insuflicient. Thus, both deficient oiliness and deficient film strength result in metal to metal contact and consequently higher wear and rapid development of heat.
In the past various substances have been inco'rporated with extreme pressure lubricants in an attempt to solve the problem outlined above. Some of these substances have resulted in slightly increased oiliness and/or film strength; only a few have achieved commercial success and none of these has been entirely satisfactory due to still deficient oiliness properties and/or film strength.
I have found that reaction products of dialkyl and diaryl dithiophosphoric acids or their alkali metal or ammonium salts with chlorine compounds or oxidizers such as air capable of chemically removing hydrogen from a dithiophosphoric acid make excellent extreme pressure lubricant bases. The reaction products, which are the subject of Romieux and Ashley Reissue Patent No. 20,411, are preferably prepared as set out in that patent.
Dialkyl and diaryl dithiophosphate poiysulfldes having the following general formula are preferred:
s /OR s-s,s on
in which R is alkayl or ary1 and a: is zero or a small whole number. The invention, however, is not intended to be limited to this specific embodiment.
Lubricating compositions containing small amounts of these dialkyl and diaryl dithiophosphoric acid derivatives form very tenacious oil films on metal surfaces and, at the same time, have satisfactory oiliness properties. They are therefore superior extreme pressure lubricants for use in hypoid gears, particularly since the running temperature of hypoid gears rarely exceeds about C. and therefore no corrosion problem arises due to decomposition of the lubricant base to form corrosive acids. Although the lubricating compositions of the present invention are best suited for use in hypoid gears, they are not limited to this application and may also be used in high compression ratio automobile engines and other internal combustion engines.
While the invention is not limited to lubricating compositions containing any definite amount or proportion of the dithiophosphoric acid derivatives, I have found that excellent lubricating results are obtained when about 10% lubricant base is used.
The following specific examples demonstrate the excellent results obtained by the use of the extreme pressure lubricating compositions of the present invention.
Example 1 10% of di-secondary-butyl dithiophosphate tetrasulfide having the following formula:
cant carried the full load of the machine, i. e.,'
600 lbs., at a rubbing speed of 1000 R. P. M.
The di-secondary-butyl dithiophosphate tetrasulfide was prepared by reacting di-secondary-- butyl dithiophosphoric acid with sulfur monochloride.
Example 2 A test similar to that of Example 1 was made of a lubricating composition containing 10% of di-n-butyl dithiophosphate disulfide having the following formula:
cmcmcmomo s s CHaCHzCHiCHIO SS OCHzCHaCHzCHa ocmcmcmc n The lubricating composition carried the full load of 600 lbs. at a rubbing speed of 1000 R. P. M.
The di-n-butyl dithiophosphate disulfide was prepared by reacting an ethylene chloride solution of di-n-butyl dithiophosphoric acid with chlorine.
Example 3 A test similar to that of Example 1 was made ofa lubricating composition containing of di-o-cresyl dithiophosphate tetrasulfide having the following formula:
CHI
- acids and salts may be reacted with sulfur dichloride, ethyl chlorcarbonate, aryl chlorides, phosgene, and the like, as well as with the chlorine and sulfur monochloride of the examples. The resulting polysulfldes make substantially equally effective extreme pressure lubricant bases.
What I claim is:
1. An extreme pressure lubricant comprising a mineral lubricating oil and a small amount of the reaction product of a dithiophosphoric acid derivative and a chlorine containing compound capable of chemically removing hydrogen from a dithiophosphoric acid. r
2. An extreme pressure lubricant comprising a mineral lubricating oil-.and a small amount of the reaction product of a member of the group consisting of dialkyl and diaryl dithiophosphoric acids and alkali metal and ammonium dialkyl and diaryl dithiophosphates, and a chlorine containing compound capable of chemically removing hydrogen from a dithiophosphoric acid.
3. An extreme pressure lubricant comprising a mineral lubricating oil and a small amount of a compound having the following general formula:
no s on -s.-s on in which R is a member of the group consisting of alkyl and aryl radicals and a: is zero or a small whole number.
4. An extreme pressure lubricant comprising a mineral lubricating oil and a small amount of di-secondary-butyl dithiophosphoric acid tetrasulfide having the formula:
5. An extreme pressure lubricant comprising a mineral lubricating oil and a small amount of di-n-butyl dithiophosphoric acid disulflde having the formula:
6. An extreme pressure lubricant comprising a mineral lubricating oil and a small amount of di-o-cresyl dithiophosphoric acid tetrasuliide having the formula;
CHI
OCHaCHaCBaCH:
JOHN L. OSBORNE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US399945A US2343831A (en) | 1941-06-26 | 1941-06-26 | Lubricating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US399945A US2343831A (en) | 1941-06-26 | 1941-06-26 | Lubricating composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2343831A true US2343831A (en) | 1944-03-07 |
Family
ID=23581575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US399945A Expired - Lifetime US2343831A (en) | 1941-06-26 | 1941-06-26 | Lubricating composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2343831A (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2443264A (en) * | 1944-02-19 | 1948-06-15 | Standard Oil Dev Co | Compounded lubricating oil |
| US2471115A (en) * | 1946-09-19 | 1949-05-24 | Standard Oil Dev Co | Lubricating oil |
| US2502400A (en) * | 1947-06-14 | 1950-03-28 | California Spray Chemical Corp | Method of making diphosphoric esters |
| US2502401A (en) * | 1947-06-18 | 1950-03-28 | California Spray Chemical Corp | Manufacture of diphosphoric esters |
| US2526497A (en) * | 1946-09-19 | 1950-10-17 | Standard Oil Dev Co | Mineral lubricating oil containing polysulfides of thiophosphorous and thiophosphoric acid esters |
| US2599341A (en) * | 1947-10-29 | 1952-06-03 | Standard Oil Dev Co | New phosphorus containing compounds |
| US2606182A (en) * | 1947-06-07 | 1952-08-05 | Standard Oil Co | Lubricating oil additive |
| US2645657A (en) * | 1949-03-30 | 1953-07-14 | Standard Oil Dev Co | Thiophosphate esters |
| US2715136A (en) * | 1949-04-29 | 1955-08-09 | Victor Chemical Works | Method of preparing dialkyl thionochlorophosphates |
| US2736737A (en) * | 1950-08-22 | 1956-02-28 | Texas Co | Phosphate partial ester-aldehyde condensation product and lubricant containing the same |
| US3013971A (en) * | 1955-01-27 | 1961-12-19 | Lubrizol Corp | Gear lubricant improving agents |
| US3850822A (en) * | 1972-07-14 | 1974-11-26 | Exxon Research Engineering Co | Ashless oil additive combination composed of a nitrogen-containing ashless dispersant phosphosulfurized olefin and phosphorothionyl disulfide |
| US4826629A (en) * | 1987-04-20 | 1989-05-02 | Mobil Oil Corporation | Non-metallic multifunctional lubricant additives and compositions thereof |
| EP0764714A1 (en) * | 1995-09-19 | 1997-03-26 | The Lubrizol Corporation | Low-viscosity lubricating oil and functional fluid compositions |
| US5674820A (en) * | 1995-09-19 | 1997-10-07 | The Lubrizol Corporation | Additive compositions for lubricants and functional fluids |
| EP0825246A3 (en) * | 1996-08-21 | 1998-04-15 | The Lubrizol Corporation | Lubricants and functional fluids containing heterocyclic compounds |
-
1941
- 1941-06-26 US US399945A patent/US2343831A/en not_active Expired - Lifetime
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2443264A (en) * | 1944-02-19 | 1948-06-15 | Standard Oil Dev Co | Compounded lubricating oil |
| US2471115A (en) * | 1946-09-19 | 1949-05-24 | Standard Oil Dev Co | Lubricating oil |
| US2526497A (en) * | 1946-09-19 | 1950-10-17 | Standard Oil Dev Co | Mineral lubricating oil containing polysulfides of thiophosphorous and thiophosphoric acid esters |
| US2606182A (en) * | 1947-06-07 | 1952-08-05 | Standard Oil Co | Lubricating oil additive |
| US2502400A (en) * | 1947-06-14 | 1950-03-28 | California Spray Chemical Corp | Method of making diphosphoric esters |
| US2502401A (en) * | 1947-06-18 | 1950-03-28 | California Spray Chemical Corp | Manufacture of diphosphoric esters |
| US2599341A (en) * | 1947-10-29 | 1952-06-03 | Standard Oil Dev Co | New phosphorus containing compounds |
| US2645657A (en) * | 1949-03-30 | 1953-07-14 | Standard Oil Dev Co | Thiophosphate esters |
| US2715136A (en) * | 1949-04-29 | 1955-08-09 | Victor Chemical Works | Method of preparing dialkyl thionochlorophosphates |
| US2736737A (en) * | 1950-08-22 | 1956-02-28 | Texas Co | Phosphate partial ester-aldehyde condensation product and lubricant containing the same |
| US2736738A (en) * | 1950-08-22 | 1956-02-28 | Texas Co | Phosphate partial ester-aldehyde-amine condensation product and lubricant containing the same |
| US3013971A (en) * | 1955-01-27 | 1961-12-19 | Lubrizol Corp | Gear lubricant improving agents |
| US3850822A (en) * | 1972-07-14 | 1974-11-26 | Exxon Research Engineering Co | Ashless oil additive combination composed of a nitrogen-containing ashless dispersant phosphosulfurized olefin and phosphorothionyl disulfide |
| US4826629A (en) * | 1987-04-20 | 1989-05-02 | Mobil Oil Corporation | Non-metallic multifunctional lubricant additives and compositions thereof |
| EP0764714A1 (en) * | 1995-09-19 | 1997-03-26 | The Lubrizol Corporation | Low-viscosity lubricating oil and functional fluid compositions |
| US5674820A (en) * | 1995-09-19 | 1997-10-07 | The Lubrizol Corporation | Additive compositions for lubricants and functional fluids |
| EP0825246A3 (en) * | 1996-08-21 | 1998-04-15 | The Lubrizol Corporation | Lubricants and functional fluids containing heterocyclic compounds |
| US5834407A (en) * | 1996-08-21 | 1998-11-10 | The Lubrizol Corporation | Lubricants and functional fluids containing heterocyclic compounds |
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