US2959552A - Heavy pressure lubricants - Google Patents

Heavy pressure lubricants Download PDF

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Publication number
US2959552A
US2959552A US488533A US48853355A US2959552A US 2959552 A US2959552 A US 2959552A US 488533 A US488533 A US 488533A US 48853355 A US48853355 A US 48853355A US 2959552 A US2959552 A US 2959552A
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US
United States
Prior art keywords
carbon atom
attached
methyl
acid
terminal carbon
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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
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US488533A
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English (en)
Inventor
Peras Lucien
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Renault SAS
Regie Nationale des Usines Renault
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Renault SAS
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    • 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
    • C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
    • C10M131/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen, halogen and oxygen
    • C10M131/12—Acids; Salts or esters thereof
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • 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
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic 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
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • 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
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters thereof
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • 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
    • C10N2040/10—Running-in-oil ; Grinding

Definitions

  • the lubrification of mechanical elements is most generally effected by the hydrodynamic entrainment of the oil, which iuterposes a film of oil between the metal surfaces which are subjected to relative movements with respect to one another.
  • new lubricants have now been found, whose unctuosity ensures a very low co-efficient of friction and which maintain this unctuosity at a much higher temperature than those which could be reached with hitherto known lubricants.
  • the new lubricants have the remarkable property of both being unctuous and at the same time of ensuring resistance to seizing under strong pressure.
  • the products according to the invention are constituted by mixing with mineral oils or any other complex mixture of inactive hydrocarbons such as are obtained in distillations from coal for example, a long chain fatty ester having a number of carbon atoms greater than 12 and a straight chain fatty ester comprising '4 halogen atoms of which 3 are fixed at the chain end opposite the ester group and 1 in position 2 with respect to the chlorinated terminal group.
  • Methyl tetrachlorolaurate Cl CCH -CHCl(CH CO CH is particularly suitable; it has the greater industrial advantage that it can be prepared easily, with a high efficiency, from undecylenic acid which is itself obtained industrially by cracking castor oil; the reaction is carried out with a good yield when carbon tetrachloride is caused to react on undecylenic acid in the presence of benzoyl peroxide acting as a catalyst.
  • the new properties of the lubricant according to the invention are revealed by laboratory measurements made on the Herschell apparatus, wherein for mean contact pressures of 15 kg./mm. the coeflicients of friction have been measured in a test comprising the entrainment of three balls, bound up in the same set of equipment, by a metallic disc turning in its plane about its axis.
  • the driving torque of the balls is measured by opposing thereto the torque of a spiral spring.
  • the equipment set is wetted with a pure mineral oil, there is no stable position of the needle connected to the opposing spring.
  • the co-eflicient of friction varies between 0.15 and 0.19. The friction becomes stable when the oil contains either a fatty ester or the mixture according to the invention, but -in the first case stability disappears at a lower temperature than in the second case.
  • Figs. 7 to 9 inclusive concern a known mixture of 1% methyl stearate in mineraloil.
  • the curves of Figs. 1 to 6 relate to a mixture according to the inventioncontaining 1% methyl stearate and 0.2% methyl tetrachlorolaurate.
  • Fig. 10 represents the variation of the-co-efficient of friction as a function of temperature in the case of each of these two mixtures.
  • the curves in Fig. 11 show the variation of the seizing delay in kilogrammes in the Boerlage machine, as a function of the loads; the curve corresponding to a mixture according to the invention containing 1% methyl stearate and 1% methyl tetrachlorolaurate is close to the mean curve which would be obtained with most of good commercial oils constituted solely for the purpose of providing protection against seizing at all pressures but having no unctuous property.
  • the mixture which has just been mentioned for its resistance to seizing contains more halogenated products than the preceding mixture which was mentioned by way of example for the measurement of the co-efiicient of friction at moderate load; in this latter measurement the products have identical behaviour.
  • the non-halogenated fatty product is not necessarily methyl stearate; it may as well be resorted to the ethyl ester or any other ester, or to esters of any other fatty acids. Palmitic esters, for example, are suitable.
  • the new lubricants can be used with advantage in all mechanisms which do not include frictionally-driven devices, for example gearbox synchronisation devices, necessitating a high co-etiicient of friction. They are used, for example for the lubrication of internal combustion engines in the running-in period and for the permanent lubrication of transmission members, gear boxes, bevel gears, etc. They considerably reduce the wearing rate and increase the output by reducing the co-efficient of friction.
  • a lubricating composition effective to provide between surfaces in frictional contact a film which will lubricate said surfaces at all pressures comprising a major proportion of a lubricating oil having incorporated therein 0.2 to 2% of a member of the group consisting of the methyl and ethyl esters of palmitic acid and the methyl and ethyl esters of stearic acid and 0.1 to 2% of the methyl ester of tetrachlorolauric acid in which 3 chlorine atoms are attached to the terminal carbon atom opposite the carboxyl group and the other chlorine atom is attached to the carbon atom second from said terminal carbon atom.
  • a lubricating composition effective to provide between surfaces in frictional contact a film which will lubricate said surfaces at all pressures comprising a major proportion of a lubricating oil having incorporated therein 0.2 to 2% of methyl stearate and 0.1 to 2% of the methyl ester of tetrachlorolauric acid in which 3 chlorine atoms are attached to the terminal carbon atom opposite the carboxyl group and the other chlorine atom is attached to the carbon atom second from said terminal carbon atom.
  • a lubricating composition effective to provide between surfaces in frictional contact a film which will lubricate said surfaces at all pressures comprising a major proportion of a lubricating oil having incorporated therein 0.2 to 2% of ethyl stearate and 0.1 to 2% of the methyl ester of tetrachlorolauric acid in which 3 chlorine atoms are attached to the terminal carbon atom opposite the carboxyl group and the other chlorine atom is attached to the carbon atom second from said terminal carbon atom.
  • An extreme pressure lubricating composition effec' tive to provide between surfaces in frictional contact a film which will resist seizing at high pressures comprising a major proportion of a lubricating oil having incorporated therein 1 to 8% of the methyl ester of tetrachlorolauric acid in which 3 chlorine atoms are attached to the terminal carbon atom opposite the carboxyl group and the other chlorine atom is attached to the carbon atom second from said terminal carbon atom, and 0.2 to 2% of ethyl stearate.
  • An extreme pressure lubricating composition effective to provide between surfaces in frictional contact a film which will resist seizing at high pressures comprising a major proportion of a lubricating oil having incorporated therein 1 to 8% of the methyl ester of tetrachlorolauric acid in which 3 chlorine atoms are attached to the terminal carbon atom opposite the carboxyl group and the other chlorine atom is attached to the carbon atom second from said terminal carbon atom, and 0.2 to 2% of a member of the group consisting of the methyl and ethyl esters of palmitic acid and the methyl and ethyl esters of stearic acid.
  • An extreme pressure lubricating composition effective to provide between surfaces in frictional contact a film which will resist seizing at high pressures comprising a major proportion of a lubricating oil having incorporated therein 1 to 8% of the methyl ester of tetrachlorolauric acid in which 3 chlorine atoms are attached to the terminal carbon atom opposite the carboxyl group and the other chlorine atom is attached to the carbon atom second from said terminal carbon atom, and 0.2 to 2% of methyl stearate.

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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)
US488533A 1954-04-13 1955-02-16 Heavy pressure lubricants Expired - Lifetime US2959552A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1041624X 1954-04-13

Publications (1)

Publication Number Publication Date
US2959552A true US2959552A (en) 1960-11-08

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ID=9589608

Family Applications (1)

Application Number Title Priority Date Filing Date
US488533A Expired - Lifetime US2959552A (en) 1954-04-13 1955-02-16 Heavy pressure lubricants

Country Status (5)

Country Link
US (1) US2959552A (de)
DE (1) DE1041624B (de)
FR (1) FR1098408A (de)
GB (1) GB784876A (de)
NL (2) NL89742C (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3260672A (en) * 1964-04-27 1966-07-12 Shell Oil Co Synthetic ester lubricating oil containing certain haloalkyl carboxylic acid esters
US3396114A (en) * 1966-11-03 1968-08-06 Standard Oil Co Combination hydraulic and transmission fluids
US6028038A (en) * 1997-02-14 2000-02-22 Charles L. Stewart Halogenated extreme pressure lubricant and metal conditioner
EP2346970B1 (de) * 2008-10-03 2015-12-16 Total Marketing Services Schmiermittelzusammensetzungen für getriebe

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL244855A (de) * 1958-11-21
DE1107867B (de) * 1959-02-06 1961-05-31 Exxon Research Engineering Co Mineralschmieroel
DE1121257B (de) * 1959-07-31 1962-01-04 Hoechst Ag Zusaetze zu Schmieroelen auf Mineraloelbasis
EP0004957A3 (de) * 1978-04-26 1980-04-16 Ciba-Geigy Ag Stoffzusammensetzungen und Verwendung von chlorierten Derivaten der Buttersäure als Schmiermittelzusätze
DE3317355A1 (de) * 1983-05-13 1984-11-15 Basf Ag, 6700 Ludwigshafen Verwendung von tri- und tetrachlorbutanolderivaten als schmiermittelzusatz sowie schmiermittel, enthaltend solche zusaetze

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1944941A (en) * 1932-06-11 1934-01-30 Continental Oil Co Lubricating oil
US2183294A (en) * 1938-01-12 1939-12-12 Lubri Zol Dev Corp Lubricant
US2272470A (en) * 1936-02-19 1942-02-10 Continental Oil Co Stabilized high film strength lubricating oils
US2425426A (en) * 1947-08-12 Po-yhalogeno aliphatic nitriles
US2812307A (en) * 1952-02-13 1957-11-05 Renault Lubricants

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2425426A (en) * 1947-08-12 Po-yhalogeno aliphatic nitriles
US1944941A (en) * 1932-06-11 1934-01-30 Continental Oil Co Lubricating oil
US2272470A (en) * 1936-02-19 1942-02-10 Continental Oil Co Stabilized high film strength lubricating oils
US2183294A (en) * 1938-01-12 1939-12-12 Lubri Zol Dev Corp Lubricant
US2812307A (en) * 1952-02-13 1957-11-05 Renault Lubricants

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3260672A (en) * 1964-04-27 1966-07-12 Shell Oil Co Synthetic ester lubricating oil containing certain haloalkyl carboxylic acid esters
US3396114A (en) * 1966-11-03 1968-08-06 Standard Oil Co Combination hydraulic and transmission fluids
US6028038A (en) * 1997-02-14 2000-02-22 Charles L. Stewart Halogenated extreme pressure lubricant and metal conditioner
EP2346970B1 (de) * 2008-10-03 2015-12-16 Total Marketing Services Schmiermittelzusammensetzungen für getriebe

Also Published As

Publication number Publication date
NL93256C (de)
NL89742C (de)
FR1098408A (fr) 1955-07-26
GB784876A (en) 1957-10-16
DE1041624B (de) 1958-10-23

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