US2576031A - Lubricating grease containing soaps of tall oil - Google Patents

Lubricating grease containing soaps of tall oil Download PDF

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Publication number
US2576031A
US2576031A US86586A US8658649A US2576031A US 2576031 A US2576031 A US 2576031A US 86586 A US86586 A US 86586A US 8658649 A US8658649 A US 8658649A US 2576031 A US2576031 A US 2576031A
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United States
Prior art keywords
tall oil
oil
acids
acid
grease
Prior art date
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Expired - Lifetime
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US86586A
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English (en)
Inventor
Arnold J Morway
John J Kolfenbach
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Standard Oil Development Co
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Standard Oil Development Co
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Publication date
Priority to NL73227D priority Critical patent/NL73227C/xx
Priority to NL75829D priority patent/NL75829C/xx
Priority to NL149599D priority patent/NL149599C/xx
Priority claimed from US57565A external-priority patent/US2516136A/en
Priority to US60616A priority patent/US2516138A/en
Priority to US60615A priority patent/US2516137A/en
Application filed by Standard Oil Development Co filed Critical Standard Oil Development Co
Priority to US86586A priority patent/US2576031A/en
Priority to GB24741/49A priority patent/GB669947A/en
Priority to FR998260D priority patent/FR998260A/fr
Priority to DEST150A priority patent/DE845228C/de
Priority to GB7576/50A priority patent/GB684697A/en
Publication of US2576031A publication Critical patent/US2576031A/en
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    • C10M2209/104Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
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    • C10M2211/044Acids; Salts or esters thereof
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    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2219/106Thiadiazoles
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    • C10M2229/00Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02Unspecified siloxanes; Silicones
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    • C10M2229/04Siloxanes with specific structure
    • C10M2229/05Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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    • C10N2010/00Metal present as such or in compounds
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    • C10N2010/02Groups 1 or 11
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    • C10N2010/04Groups 2 or 12
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    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08Resistance to extreme temperature
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    • C10N2040/02Bearings
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    • C10N2040/12Gas-turbines
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    • C10N2040/13Aircraft turbines
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    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Semi-solids; greasy
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    • C10N2070/00Specific manufacturing methods for lubricant compositions

Definitions

  • the present invention relates to lubricating greases and particularly to lubricating greases which contain as thickening agents mixtures of high and low molecular weight metal salts of organic acids.
  • the saponifying agent for example sodium hydroxide, forms a sodium furoate along with the usual sodium soap.
  • the patent points out that other cyclic acids of comparable molecular weight and structure may be used in lieu of furoic acid. For example, derivatives of thiophene may be used and the salts of other low molecular weight acids having similar properties are contemplated.
  • the present invention is based upon the discovery that greases of the general type set forth in said patent may be produced very economically by substituting tall oil for the fatty oils or acids Certain unexpected advantages accrued from such use and constitute a major aspect of the present invention, as will be more fully pointed out hereinafter.
  • lubricating greases may be prepared by the same process, the essential difference being that tall oil is used in lieu of conventional fatty acids, the salts of low molecular weight being produced by the Cannizzaro reaction which results when aldehydes such as furfural or thiophene aldehyde, benzaldehyde, and the like, are treated with a strong base such as sodium hydroxide.
  • lubricating greases containing the soaps of tall oil are particularly effective in combination with the corresponding salts of the lower cyclic acids, e. g. those containing 4 to about 7 carbon atoms such as furoic acid, thiophene carboxylic acid, benzoic acid, salicylic acid, and the like.
  • tall oil soaps may also be combined with other low molecular weight salts than the furoates, e. g. with acrylates, acetates, and other lower aliphatic salts.
  • the cyclic or other low molecular weight acid may be added directly to the composition if the Cannizzaro reaction is not desirable, or if the aldehydes are not available.
  • the use of the corresponding aldehyde, particularly furfural is justiiied economically as a source of the low molecular weight acid which forms the salt component. because of the availability and cheapness of this material.
  • the neutral or substantially neutral salts and soaps are derived from relatively inexpensive aldehyde and the relatively inexpensive tall oil, either as the principal or as the total thickening ingredients, the resulting grease product is quite inexpensive and has very useful properties.
  • Tall oil acids or tall oil saponified with sodium hydroxide and dispersed in mineral oil gives greases of low dropping point, undesirably fibrous, and poor oxidation and structural stability.
  • Furfural is a widely available and inexpensive material, widely used as a selective solvent in industry.
  • Tall oil is a by-product of the paper pulp industry as noted above.
  • Another by-product obtained in the sulfate-paper process is sulfate turpentine, a product objectionable for use in lubricants because of its odor and color.
  • Trimble, in U. S. Patent 2,310,046, describes the refining of sulfate turpentine simultaneously with crude tall oil by using furfural. Separation of the turpentine and tall oil is accomplished by distillation under reduced pressure. Any furfural remaining in the tall oil, either as the monomer or polymer, may be determined and this residue may be left in the refined tall oil.
  • the salts of furoic acid are also produced. Sufficient furfural may be added if needed, to form the required proportions of low molecular weight salts required for the grease.
  • tall oil acids Any commercial type of tall oil acids may be employed in carrying out this invention. However, the acids obtained by at least one complete distillation of the crude tall oil are preferred.
  • the temperature was next raised by external heating to 400 F. while adding the balance of the mineral oil in small portions.
  • the phenyl alpha naphthylamine, used as an antioxidant was added and the grease was drawn into pans for cooling. It could be worked down in the kettle while cooling if desired.
  • the cold grease was then homogenized by working in the grease kettle to a smooth, uniform product, after which it was filtered and packaged. This grease contained about 6% sodium furoate and about soda soap of tall oil.
  • composition lost its solid consistency and broke down after working in a standard grease worker for 50,000 strokes to a semifluid mass which could be poured.
  • Acid value 175.0 Composition (approx.) fatty acids as oleic and linoleic acids per cent 30 Rosis acids do 70 In this example the tall oil was mixed with equal portions of hydrogenated fish oil acids (HydIOfOl Acids 54) Properties of Grease Free alkalinity 0.32% as NaOH. Worked penetration mm./ 10 210. Structural stability Excellent. (Penetration a f t e r 100,000
  • the proportions of the various ingredients may be varied over wide limits provided that the ratio between the low molecular weight salt and the soap of tall oil is maintained between predetermined limits.
  • a very satisfactory modified soap may be made by using substantially equal parts of saturated fatty acids, such as C12 to C22 hydrogenated fish oil acids, with tall oil.
  • saturated fatty acids such as C12 to C22 hydrogenated fish oil acids
  • 1 to 3 molar parts of soap should be used with about 1 to 2 molar parts of salt.
  • 2 parts of furfural can be used with 3 parts combined fatty acid and/or tall oil.
  • tall oil consists essentially of a mixture of rosin acids and oleic acid the soaps which result are partly rosin soaps and partly oleates.
  • the total proportions of such soaps may be within the limits of about 5 to 20% by weight, based on the total composition, the salt of low molecular weight acid being in proportions of about 2 to generally speaking.
  • Proportions of 3 to 7% salts of cyclic acid (such as furoic acid) combined with 8 to of the soaps of tall oil acids are specifically preferred, the remainder of the composition being lubricating oil.
  • the grade of mineral oil may be varied over wide limits as is well-known in the art. It may comprise from about 60 to 93% of the total composition and should be of appropriate lubricating grade for the' lubrication requirements. Its viscosity may be from about S. U. S. to about 150 S. U. S. at 210 F. or about 50 to 1,000 S. U. S. at 100 F. Either naphthenic or paraffinic oils, or mixtures thereof, may be used.
  • a lubricating grease composition consisting essentially of lubricating oil thickened to a grease consistency with a combination of 5 to 20% by weight based on the total composition, of the sodium soap of tall oil combined with 2 to 10% of the sodium salt of a low molecular weight cyclic carboxylic acid containing 4 to about '1 carbon atoms.
  • composition as in claim 1 wherein the cyclic acid is furoic acid.
  • composition as in claim 1 wherein the cyclic acid is thiophene carboxylic acid.
  • composition as in claim 1 wherein the salt of low molecular weight acid is a benzoa'te.
  • a lubricating grease composition consisting essentially of to 93% by Weight of mineral base lubricating oil, 5 to 20% of a soda soap of tall oil and 2 to 10% of sodium furoate.
  • a lubricating grease composition consisting essentially of mineral lubricating oil having a viscosity between 35 and S. U. S. at 210 F., thickened to a grease consistency with a combination of about 15% by weight, based on the total composition, of the soda soap of high molecular weight organic material of the class consisting of higher saturated fatty acids and their esters and tall oil and comprising a substantial proportion of tall oil and about 6% of sodium furoate.
  • composition as in claim 6 wherein the nonmetal radical of the high molecular weight soap is composed of substantially equal parts of substantially saturated fatty acids of 12 to 22 carbon atoms and tall oil.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US86586A 1948-10-30 1949-04-09 Lubricating grease containing soaps of tall oil Expired - Lifetime US2576031A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
NL73227D NL73227C (pt) 1948-10-30
NL75829D NL75829C (pt) 1948-10-30
NL149599D NL149599C (pt) 1948-10-30
US60616A US2516138A (en) 1948-10-30 1948-11-17 Use of furfural in grease manufacture
US60615A US2516137A (en) 1948-10-30 1948-11-17 High-temperature lubricating greases
US86586A US2576031A (en) 1948-10-30 1949-04-09 Lubricating grease containing soaps of tall oil
GB24741/49A GB669947A (en) 1948-10-30 1949-09-27 Improvements in or relating to lubricating grease compositions
FR998260D FR998260A (fr) 1948-10-30 1949-10-27 Perfectionnements aux compositions de graisses lubrifiantes
DEST150A DE845228C (de) 1948-10-30 1949-11-01 Verfahren zur Herstellung von Schmierfetten
GB7576/50A GB684697A (en) 1948-10-30 1950-03-27 Lubricating grease containing soaps of tall oil

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US57565A US2516136A (en) 1948-10-30 1948-10-30 Lubricating grease compositions
US86586A US2576031A (en) 1948-10-30 1949-04-09 Lubricating grease containing soaps of tall oil

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US2576031A true US2576031A (en) 1951-11-20

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US86586A Expired - Lifetime US2576031A (en) 1948-10-30 1949-04-09 Lubricating grease containing soaps of tall oil

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US (1) US2576031A (pt)
DE (1) DE845228C (pt)
FR (1) FR998260A (pt)
GB (2) GB669947A (pt)
NL (3) NL73227C (pt)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2790770A (en) * 1957-04-30 Grease composition
US2801974A (en) * 1952-12-22 1957-08-06 Exxon Research Engineering Co Grease process utilizing the alkali fusion products of cyclic alcohols
US2834732A (en) * 1954-11-29 1958-05-13 Standard Oil Co Extreme pressure lubricant
US2946748A (en) * 1956-05-08 1960-07-26 Swift & Co Liquid hydrocarbon gels and uses thereof
US3252906A (en) * 1963-06-07 1966-05-24 Standard Oil Co Grease
US11760952B2 (en) 2021-01-12 2023-09-19 Ingevity South Carolina, Llc Lubricant thickener systems from modified tall oil fatty acids, lubricating compositions, and associated methods

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2182137A (en) * 1937-02-01 1939-12-05 Shell Dev Soda soap grease
US2444720A (en) * 1944-10-17 1948-07-06 Shell Dev Manufacture of lithium base greases
US2514286A (en) * 1947-12-31 1950-07-04 Standard Oil Dev Co Lubricating grease and method of preparing same
US2516136A (en) * 1948-10-30 1950-07-25 Standard Oil Dev Co Lubricating grease compositions
US2516137A (en) * 1948-10-30 1950-07-25 Standard Oil Dev Co High-temperature lubricating greases

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2182137A (en) * 1937-02-01 1939-12-05 Shell Dev Soda soap grease
US2444720A (en) * 1944-10-17 1948-07-06 Shell Dev Manufacture of lithium base greases
US2514286A (en) * 1947-12-31 1950-07-04 Standard Oil Dev Co Lubricating grease and method of preparing same
US2516136A (en) * 1948-10-30 1950-07-25 Standard Oil Dev Co Lubricating grease compositions
US2516137A (en) * 1948-10-30 1950-07-25 Standard Oil Dev Co High-temperature lubricating greases

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2790770A (en) * 1957-04-30 Grease composition
US2801974A (en) * 1952-12-22 1957-08-06 Exxon Research Engineering Co Grease process utilizing the alkali fusion products of cyclic alcohols
US2834732A (en) * 1954-11-29 1958-05-13 Standard Oil Co Extreme pressure lubricant
US2946748A (en) * 1956-05-08 1960-07-26 Swift & Co Liquid hydrocarbon gels and uses thereof
US3252906A (en) * 1963-06-07 1966-05-24 Standard Oil Co Grease
US11760952B2 (en) 2021-01-12 2023-09-19 Ingevity South Carolina, Llc Lubricant thickener systems from modified tall oil fatty acids, lubricating compositions, and associated methods

Also Published As

Publication number Publication date
FR998260A (fr) 1952-01-16
GB684697A (en) 1952-12-24
DE845228C (de) 1952-07-31
NL149599C (pt)
GB669947A (en) 1952-04-09
NL73227C (pt)
NL75829C (pt)

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