US2715107A - Lubricating compositions - Google Patents

Lubricating compositions Download PDF

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Publication number
US2715107A
US2715107A US348806A US34880653A US2715107A US 2715107 A US2715107 A US 2715107A US 348806 A US348806 A US 348806A US 34880653 A US34880653 A US 34880653A US 2715107 A US2715107 A US 2715107A
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United States
Prior art keywords
oil
acid
weight
viscosity
sae
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US348806A
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English (en)
Inventor
Samuel K Talley
Frederick M Fowkes
Alfredo G Cattaneo
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Shell Development Co
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Shell Development Co
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Application filed by Shell Development Co filed Critical Shell Development Co
Priority to US348806A priority Critical patent/US2715107A/en
Priority to FR1097961D priority patent/FR1097961A/fr
Priority to GB10683/54A priority patent/GB752383A/en
Priority to DEN8754A priority patent/DE942585C/de
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Publication of US2715107A publication Critical patent/US2715107A/en
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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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027—Neutral salts thereof
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • 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
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    • C10M2207/128—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 containing hydroxy groups; Ethers thereof
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    • 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
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    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
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    • C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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    • C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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Definitions

  • Additives of this invention can be prepared by any suitable means such as described in U. S. Patents 2,606,206, 2,567,011, 2,583,415, 2,514,473, and 2,407,315, and in Ind. and Eng. Chem., vol. 43, No. 10, 2332 (1951).
  • Specific compounds which are particularly suitable as oil consumption inhibitors as well as mixtures thereof include: perfluoroacetic acid, perfluoropropionic acid, perfluorobutyric acid, perfluorovaleric acid, perfluorocaproic acid, perfluoroheptanoic acid, perfluorocaprylic acid, perfiuorocapric acid, perfluoromyristic acid, perfluorocyclohexane carboxylic acid, fl-perfluorocyclohexaneacetic acid, perfluorosebacic acid, perfluorosuccinic acid, per fluorobutyryl fluoride, perfluorocapryl fluoride, perfluorocyclohexyl fluoride, perfluoropropionyl chloride, perfluorocapryl chloride; perfluorobutyryl amide, perfluorocapryl amide, perfluorocyclohexaneformamide, u-dichlo- Col Patented Aug.
  • the perhalo compounds of this invention are suitably used in amounts varying from 0.01 to 5%, and preferably from about 0.1 to 1% by weight of the oil composition.
  • the perhalo-compounds are compatible with various conventional lubricating oil additives, which can be incorporated in the composition, such as blooming agents, pour-point depressors, detergent viscosity improvers, antifoaming agents, and the like.
  • oilsoluble detergents which include oil-soluble salts of various bases with detergent-forming acids.
  • bases include metal-containing as well as organic bases.
  • Suitable metallic bases include those of the alkali metals and of polyvalent metals such as Ca, Mg, Cu, Sr, Ba, Zn, Cd, Al, Sn, Pb, Cr, Mn, Fe, Ni, Co, etc.
  • Organic bases include various nitrogen bases such as primary, secondary, tertiary amines and quaternary ammonium compounds, e. g., benzyl trimethyl ammonium hydroxide.
  • Suitable detergent-forming acids are the fatty acids of say, 10 to 30 carbon atoms, tall-oil acids, rosin acids, wool-fat acids, paraflin-wax acids (produced by oxidation of paraflin wax), chlorinated fatty acids, aromatic hydroxy fatty acids, paraffinwax alkylated benzoic acids, various alkyl salicylic acids, phthalic acid monoesters, aromatic keto acids, aromatic ether acids, diphenols such as di-(alkylphenol) sulfides and disulfides, methylene bis-alkyl phenols; sulfonic acids such as may be produced by treatment of alkyl aryl hydrocarbons or high-boiling petroleum oils with sulfuric acid; sulfuric acid monoesters; esters of acids of phosphorus, arsenic and antimony, including the corresponding thiophosphoric and thioarsonic acids and the like.
  • Illustrative specific detergents which are especially effective in combination with the perfiuorocompounds in mineral lubricating oils are: oil-soluble alkaline earth metal petroleum sulfonates, particularly the calcium and barium sulfonates, including normal and basic salts; alkaline earth metal (particularly calcium and barium) alkylphenates, including simple phenates (calcium cetyl phenate) and dior poly-phenates (barium salt of di- (octylphenol) sulfide, calcium salt of polyoctylphenolpolymethylene such as obtained by the condensation of octylphenol and an aldehyde such as formaldehyde to form products such as penta(octylhydroxyphenylene) tetramethylene, etc.; alkaline earth metal alkylsalicylates such as calcium cetylsalicylate, calcium C14 1s-alkylsalicylate; divalent metal salts of Group II have metals with phosphorus
  • divalent metal salts of Group II have metals with carbamic and thiocarbamic acids, e. g., zinc dibutyl dithiocarbamate, and calcium dicyclohexyl dithiocarbamate.
  • the metal containing detergents are advantageously used in an amount of from about 0.025% to about 0.2% by weight, determined as sulfate ash of the metal content.
  • Corrosion inhibitors or anti-rusting compounds may also be present, such as alkyl or alkenyl dicarboxylic acids of 16 or more carbon atoms (octadecylsuccinic acid); alkali metal and alkaline earth metal salts of sulfonic acids and of fatty acids, organic compounds containing an acidic radical in close proximity to a nitrile, nitro, or nitroso group (e. g., alphacyanostearic acid), glycidyl phenyl ether, wax disulfide, etc.
  • alkyl or alkenyl dicarboxylic acids of 16 or more carbon atoms octadecylsuccinic acid
  • alkali metal and alkaline earth metal salts of sulfonic acids and of fatty acids organic compounds containing an acidic radical in close proximity to a nitrile, nitro, or nitroso group (e. g., alphacyanostearic acid),
  • Additional ingredients may comprise oil-soluble urea or thiourea derivatives, e. g., urethanes, allophanates, carbazides, carbazones, etc., alkylene polymers such as polyisobutylene, unsaturated polymerized esters of fatty acids and monohydric alcohols and other high-molecular-weight oil-soluble compounds.
  • oil-soluble urea or thiourea derivatives e. g., urethanes, allophanates, carbazides, carbazones, etc.
  • alkylene polymers such as polyisobutylene, unsaturated polymerized esters of fatty acids and monohydric alcohols and other high-molecular-weight oil-soluble compounds.
  • the amount of additive used may vary from 0.01 to 2% or higher. However, substantial improvement is obtained by using amounts ranging from 0.1 to 0.5% in combination with the primary additive of this invention.
  • Base oils with which additives of this invention are combined include light lubricating oil having a Saybolt Universal viscosity at 210 P. not in excess of around 45 seconds and include natural and synthetic oils such as esters of polycarboxylic acid (Z-ethylhexylsebacate), Ucon fluids (polyalkylene oxides) organic silicone fluids, etc., as well as mixtures thereof.
  • a typical oil of this type is an SAE SW petroleum motor oil having the following properties:
  • compositions of this invention wherein the SAE W motor designates an oil having the characteristics given above:
  • Example 1 Per cent weight Perfluorocaprylamide 0.2 SAE 5W motor oil Balance
  • Example 2 Per cent weight Perfluorocaprylamide 0.2 SAE 5W motor oil Balance
  • Composition Y SAE 30 motor oil+0.2% perfiuorocaprylamide.
  • Example 2 In another test a CRC L-4 engine was run on lubricant identified as Example 2 and around 60% reduction in oil consumption was noted. The oil was removed and the engine operated with a straight SAE 5W oil. A reduction of around 25% in oil consumption was noted demonstrating the carryover eiTect of compositions of this invention.
  • compositions of this invention in addition to effectively reducing oil consumption, inhibit wear, corrosion, sludge and lacquer formation.
  • Lubricants of this invention also are particularly advantageous during starting and particularly eliminate the necessity of engine warm-up.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 F. not in excess of 45 seconds and between about 0.01% and about 5% by weight, of a perfluoro-organic compound selected from the group consisting of perfiuoro-organic acids, and amides thereof, said compound containing between 2 and 14 carbon atoms per molecule.
  • a lubricating composition comprising a major amount of a low viscosity petroleum oil having a Saybolt Universal viscosity at 210 P. not in excess of 45 seconds and between about 0.01% and about 5% by weight, of a perfiuoroaliphatic acid, said acid contain ing between 2 and 14 carbon atoms per molecule.
  • a lubricating composition comprising a major amount of a low viscosity petroleum oil having a Saybolt Universal viscosity at 210 P. not in excess of 45 seconds and between about 0.01% and about 5% by weight, of a perfiuoroamide having between 2 and 14 carbon atoms per molecule.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 P. not in excess of 45 seconds and from 0.1% to 1% by weight of perfluorocaprylic acid.
  • a lubricating composition comprising a major amount of alow viscosity oil having a Saybolt Universal viscosity at 210 P. not in excess of 45 seconds and from 0.1% to 1% by weight of perfiuorocaprylamide.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 P. not in excess of 45 seconds and from 0.1% to 1% by Weight of perfluorocaprylic acid and from 0.01% to 2% by weight of a detergent.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 P. not in excess of 45 seconds and from 0.1% to 1% by weight of perfluorocaprylamide and from 0.01% to 2% by weight of an anti-wear agent.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 F. not in excess of 45 seconds and from 0.1% to 1% by weight of perfiuorocaprylic acid and from 0.01% to 2% by Weight of an oil-soluble sulfonate.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 P. not in excess of 45 seconds and from 0.1% to 1% by weight of perfluorocaprylamide and from 0.01% to 2% by weight of an oil-soluble metal phenate.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 F. not in excess of 45 seconds and from 0.1% to 1% by weight of perfluorocaprylic acid and from 0.01% to 2% by weight each of an oil-soluble metal sulfonate and an oil-soluble metal phenate.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 P. not in excess of 45 seconds and from 0.1% to 1% by weight of a perfluorocaprylamide and from 0.01% to 2% by weight each of a metal sulfonate and a metal phenate.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 P. not in excess of 45 seconds and from 0.1% to 1% by weight of a perfiuorocaprylic acid and from 0.1% to 0.5% by Weight each of an oilsoluble calcium petroleum sulfonate and an oil-soluble calcium salt of alkyl phenol-formaldehyde condensation product.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 P. not in excess of seconds and from 0.1% to 1% by weight of a perfiuorocaprylamide and from 0.1% to 0.5% by weight each of oil-soluble calcium petroleum sulfonate and oil-soluble calcium salt of alkyl phenol-formaldehyde condensation product.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 P. not in excess of 45 seconds and containing about 0.2% perfluorocaprylamide and about 0.4% calcium petroleum sulfonate.
  • a lubricating composition comprising a major amount of a low viscosity oil having a Saybolt Universal viscosity at 210 F. not in excess of 45 seconds and containing about 0.2% perfluorocaprylic acid, 0.1% calcium petroleum sulfonate and 0.3% calcium salt of octyl phenol-formaldehyde condensation product.

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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)
US348806A 1953-04-14 1953-04-14 Lubricating compositions Expired - Lifetime US2715107A (en)

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US348806A US2715107A (en) 1953-04-14 1953-04-14 Lubricating compositions
FR1097961D FR1097961A (fr) 1953-04-14 1954-04-12 Compositions d'huile lubrifiante
GB10683/54A GB752383A (en) 1953-04-14 1954-04-12 Lubricating oil compositions
DEN8754A DE942585C (de) 1953-04-14 1954-04-13 Schmieroel

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2915471A (en) * 1956-04-16 1959-12-01 Shell Dev Lubricating oil compositions
US2977306A (en) * 1958-03-31 1961-03-28 California Research Corp Lubricant composition
US3269948A (en) * 1963-08-30 1966-08-30 Exxon Research Engineering Co Amine salts of perhalogenated monobasic carboxylic acids
US3284355A (en) * 1963-09-12 1966-11-08 Mobil Oil Corp Lubricating compositions
US3329611A (en) * 1965-03-17 1967-07-04 Sinclair Research Inc Lubricating oil composition
US3436348A (en) * 1966-10-20 1969-04-01 Sinclair Research Inc Ester base lubricating oil containing a stabilizing mixture of alkali metal organic compound and an aromatic amine
US4079012A (en) * 1976-10-04 1978-03-14 Bosniack David S Synthetic ester oil compositions containing organic sulfonic acid ammonium salts as load-carrying agents
US4263157A (en) * 1978-04-26 1981-04-21 Ciba-Geigy Corporation Chlorinated derivatives of butyric acid as useful lubricant additives and lubricants containing same
US5182039A (en) * 1991-03-29 1993-01-26 Exxon Chemical Patents, Inc. Synergistic fluorinated ore flotation aids
WO2000020539A1 (fr) * 1998-10-02 2000-04-13 E.I. Du Pont De Nemours And Company Additif pour lubrifiants
US6642186B2 (en) 1998-10-02 2003-11-04 E. I. Du Pont De Nemours And Company Additive for lubricants

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1107867B (de) * 1959-02-06 1961-05-31 Exxon Research Engineering Co Mineralschmieroel
US3226323A (en) * 1963-04-30 1965-12-28 Monsanto Res Corp Lubricant composition containing a haloalkanoic compound

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2411159A (en) * 1943-07-22 1946-11-19 Du Pont Lubricant
US2456176A (en) * 1944-12-30 1948-12-14 Du Pont Monomeric addition products of azobisformates and polyfluoroethylenes
USRE23229E (en) * 1943-09-15 1950-05-09 Compounded lubricating oil
US2567011A (en) * 1949-01-10 1951-09-04 Minnesota Mining & Mfg Fluorocarbon acids and derivatives
US2606212A (en) * 1944-07-28 1952-08-05 Purdue Research Foundation Perfluoro-alkyl-cyclohexanes
US2616927A (en) * 1950-05-12 1952-11-04 Minnesota Mining & Mfg Fluorocarbon tertiary amines
US2680717A (en) * 1953-02-12 1954-06-08 Du Pont Salts of polymeric amines with perfluorocarboxylic acids

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2411159A (en) * 1943-07-22 1946-11-19 Du Pont Lubricant
USRE23229E (en) * 1943-09-15 1950-05-09 Compounded lubricating oil
US2606212A (en) * 1944-07-28 1952-08-05 Purdue Research Foundation Perfluoro-alkyl-cyclohexanes
US2456176A (en) * 1944-12-30 1948-12-14 Du Pont Monomeric addition products of azobisformates and polyfluoroethylenes
US2567011A (en) * 1949-01-10 1951-09-04 Minnesota Mining & Mfg Fluorocarbon acids and derivatives
US2616927A (en) * 1950-05-12 1952-11-04 Minnesota Mining & Mfg Fluorocarbon tertiary amines
US2680717A (en) * 1953-02-12 1954-06-08 Du Pont Salts of polymeric amines with perfluorocarboxylic acids

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2915471A (en) * 1956-04-16 1959-12-01 Shell Dev Lubricating oil compositions
US2977306A (en) * 1958-03-31 1961-03-28 California Research Corp Lubricant composition
US3269948A (en) * 1963-08-30 1966-08-30 Exxon Research Engineering Co Amine salts of perhalogenated monobasic carboxylic acids
US3284355A (en) * 1963-09-12 1966-11-08 Mobil Oil Corp Lubricating compositions
US3329611A (en) * 1965-03-17 1967-07-04 Sinclair Research Inc Lubricating oil composition
US3436348A (en) * 1966-10-20 1969-04-01 Sinclair Research Inc Ester base lubricating oil containing a stabilizing mixture of alkali metal organic compound and an aromatic amine
US4079012A (en) * 1976-10-04 1978-03-14 Bosniack David S Synthetic ester oil compositions containing organic sulfonic acid ammonium salts as load-carrying agents
US4263157A (en) * 1978-04-26 1981-04-21 Ciba-Geigy Corporation Chlorinated derivatives of butyric acid as useful lubricant additives and lubricants containing same
US5182039A (en) * 1991-03-29 1993-01-26 Exxon Chemical Patents, Inc. Synergistic fluorinated ore flotation aids
WO2000020539A1 (fr) * 1998-10-02 2000-04-13 E.I. Du Pont De Nemours And Company Additif pour lubrifiants
US6642186B2 (en) 1998-10-02 2003-11-04 E. I. Du Pont De Nemours And Company Additive for lubricants

Also Published As

Publication number Publication date
FR1097961A (fr) 1955-07-13
GB752383A (en) 1956-07-11
DE942585C (de) 1956-05-03

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