US2343831A - Lubricating composition - Google Patents

Lubricating composition Download PDF

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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
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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
Application number
US399945A
Inventor
John L Osborne
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Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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Publication date
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Priority to US399945A priority Critical patent/US2343831A/en
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Publication of US2343831A publication Critical patent/US2343831A/en
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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
    • 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;

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  • 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.
US399945A 1941-06-26 1941-06-26 Lubricating composition Expired - Lifetime US2343831A (en)

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Cited By (16)

* Cited by examiner, † Cited by third party
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
EP0825246A2 (en) * 1996-08-21 1998-02-25 The Lubrizol Corporation Lubricants and functional fluids containing heterocyclic compounds

Cited By (19)

* Cited by examiner, † Cited by third party
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
EP0825246A2 (en) * 1996-08-21 1998-02-25 The Lubrizol Corporation Lubricants and functional fluids containing heterocyclic compounds
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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