US3052632A - High temperature grease compositions - Google Patents

High temperature grease compositions Download PDF

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Publication number
US3052632A
US3052632A US792463A US79246359A US3052632A US 3052632 A US3052632 A US 3052632A US 792463 A US792463 A US 792463A US 79246359 A US79246359 A US 79246359A US 3052632 A US3052632 A US 3052632A
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United States
Prior art keywords
grease
greases
consistency
high temperature
indanthrene
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
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US792463A
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English (en)
Inventor
Donald E Loeffler
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Shell USA Inc
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Shell Oil Co
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Publication date
Priority to NL248188D priority Critical patent/NL248188A/xx
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US792463A priority patent/US3052632A/en
Priority to GB4538/60A priority patent/GB901918A/en
Priority to FR818033A priority patent/FR1247727A/fr
Priority to BE587413A priority patent/BE587413A/nl
Priority to CH140760A priority patent/CH387210A/de
Application granted granted Critical
Publication of US3052632A publication Critical patent/US3052632A/en
Anticipated expiration legal-status Critical
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    • C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
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    • 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
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
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    • 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
    • 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
    • C10M2223/042—Metal salts 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
    • 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
    • C10M2229/00—Organic 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
    • C10M2229/04—Siloxanes with specific structure
    • 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
    • C10M2229/00—Organic 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
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • 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
    • C10M2229/00—Organic 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
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
    • 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
    • C10M2229/00—Organic 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
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
    • 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
    • C10M2229/00—Organic 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
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/32—Light or X-ray resistance
    • 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
    • C10N2040/02—Bearings
    • 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
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • diarylamines to increase consistency appears to be restricted to greases gelled with indanthrene compounds, since addition of the same amines to greases gelled with other high temperature gelling agents either had no effect on consistency or actually softened the grease.
  • the chief benefit derived from the present invention comprises a drastic reduction in the cost of the subject greases.
  • This is material since the principal gelling agent, namely, the dyes are extremely expensive materials while the amines are far less costly.
  • the indanthrene dyes at the present time cost in the order of $11.00 a pound while the amines are currently priced at 60-70 cents a pound. Consequently, any reduction in the dye content of the grease by a corresponding addition of the amine results in an approximate twenty-fold saving in grease thickener cost.
  • this cost reduction a principal factor but also the unexpected improvement in bearing life caused by the presence of the large quantities of amines present constitutes an impressive improvement in lubricating greases of this particular class.
  • Suitable diaryl-amines include the following:
  • Phenyl-alpha-naphthylamine Phenyl beta-naphthylamine Diphenylamine Di alpha-naphthyl) amine Di(beta-naphthyl) amine (Alpha-naphthyl) (beta-naphthyl) amine Di(tert-butylphenyl) amine (Sec-amylphenyl phenylamine (Methylphenyl naphthylamine
  • any alkyl substituents on the aryl nuclei have 1-10 carbon atoms each.
  • the amines are preferably incorporated by homogenizing them with the finished grease containing the principal thickening agent and the lubricating oil.
  • the amines may be incorporated with the thickener at the time the grease is originally prepared or may be dispersed in lubricating oil prior to addition of the principal .thickening component.
  • indanthrene itself
  • indanthrene compounds in their non-metallic form, that is, without neutralization of the carbonyl groups in said compounds with such ions as sodium or potassium, calcium, etc.
  • partially or fully neutralized indanthrene compounds as grease thickening agents
  • greases having maximum lubricating life at elevated temperaures are those in which the carbonyl groups are free of any metallic substituents.
  • Typical indanthrene compounds suitable for the present purpose include the following:
  • indanthrene Flavanthrone Pyranthrone Violanthrone 3,3'-dichloroindanthrene 3-chloroindanthrene
  • the indanthrene dyes which are used as the gelling agents in the subject greases, contain two units of the following essential typical grouping per molecule:
  • groups as in flavanthrone
  • NH groups as in indanthrone blue
  • CH groups as in pyranthrone
  • condensed ring systems as in violanthrone.
  • Another characteristic of the indanthrone dyes is that nitrogen is not a nuclear element present in the rings making up the essential tricyclic nuclei.
  • the lubricating oil chosen to form the greases of invention may be Widely varied.
  • the oil chosen to prepare the grease composition should be capable of performing the lubricating function if it could be used as a liquid.
  • Mineral lubricating oils having a viscosity within the range of from about 35 to about 200 SUS at 210 F. may be used for most applications.
  • the mineral oil may be of a paraffinic or of a naphthenic nature depending upon the crude source, and ony of the various distillates refined by the various refinery techniques are operable.
  • Synthetic lubricating oils may also be utilized in preparing the lubricating greases of this invention.
  • Synthetic lubricating oils having a viscosity within the range stated above are operable. These oils include esters of monobasic acids, such as the C Oxo alcohol ester of C Oxo acid, esters of C Oxo alcohol and octanoic acid, etc.; esters of dibasic acids, such as di-Z-ethylhexyl sebacate, di-nonyl-adipate, etc., esters of glycols, e.g., the C Oxo acid diester of tetraethylene glycol, etc., complex esters, such as the complex ester formed by reacting one mol of sebacic acid with two mols of tetraethylene glycol and two mols of 2-ethyl hexanoic acid; other types include complex esters formed by reacting one mol of tetraethylene glycol with two mols of sebacic acid and
  • a recently developed class namely diaryl dialkyl silanes (e.g., diphenyl didodecyl silane) may be employed.
  • Esters of phosphoric acid may be used, such as the ester formed by contacting three mols of the monomethyl ether of ethylene glycol with one mol of phosphorus oxychloride.
  • Halocarbon oils such the polymers of chlorotrifluorethylene may be employed, as well as alkyl silicon compounds, such as methyl polysiloxanes, ethyl polysiloxanes, methylphenyl polysiloxanes, ethyl-phenyl polysiloxanes, chlorophenyl silicones, and the like.
  • Sulfite esters such as those formed by reacting one mol of sulfur oxychloride with two mols of the methyl ether of ethylene glycol and the like also are useful, as are carbonates such as those formed by reacting C Oxo alcohol with ethyl carbonate to form a half ester and reacting this half ester with tetraethylene glycol, mercaptals such as those formed by reacting Z-ethylhexyl mercaptan with formaldehyde, formals such as those formed by reacting C Oxo alcohol with formaldehyde, polyglycols, such as those formed by condensing butyl alcohol with up to fifty units of propylene oxide, or mixtures of any of the above synthetic oils in an proportions.
  • a recent development in the high temperature lubricating field and in the allied field of lubrication under conditions of ionizing radiation comprises the use of polyphenyl ethers as lubricants or as lubricant components.
  • the maximum stability obtained if the polyphenyl ethers are unsubstituted but highly stable lubricants are also prepared when alpha-cumyl or tertiary-butyl substituents are employed.
  • ortho, meta or para linkages between phenyl radicals may be utilized, it is preferred that at least 25% of the ether linkages be in the meta position relative to each other. As the meta linkage proportion increases, the pour point of the resulting lubricating oils decreases.
  • polyphenyl ethers which are all meta linked but which may instead comprise meta linkages With varying proportions of ortho or para linkages. It is preferred that the polyphenyl ether contain from 3 to 6 phenyl radicals per molecule.
  • the addition of the amines to the subject class of greases may be utilized for the purpose of increasing the consistency of the grease on the one hand or for decreasing the major thickener requirements such as dye for a given grease consistency on the other hand.
  • the following examples illustrate the unexpected increase in consistency of an indanthrene blue (indanthrone) grease, 28% by weight of the grease being indanthrone, the balance of the grease being a residual petroleum lubricating oil, namely, a bright stock.
  • a grease composition comprising a major amount of bright stock mineral lubricating oil gelled to a grease consistency with a combination of 5-35 by weight of indanthrone and 25-20% by weight of a diarylamine having the general configuration H ArN--Ar wherein each Ar is an aromatic hydrocarbon radical of the group consisting of phenyl, naphthyl, alkylated phenyl and alkylated naphthyl radicals.
  • a grease composition comprising a major amount of bright stock mineral lubricating oil gelled to a grease consistency with a combination of 5-35% by weight of indanthrone and 25-20% by weight of a phenyl naphthylamine, the amount of said amine being sufiicient to substantially increase the consistency of the grease.
  • a grease composition comprising a major amount of bright stock mineral lubricating oil gelled to a grease consistency with a combination of 5-35 by weight of indanthrone and 25-20% by weight of a dinaphthylamine;
  • the lubricating oil is a polyphenyl ether.
  • a grease composition comprising a major amount of References Cited in the file of this Patent a lubricating oil gelled to a grease consistency with a combination of 5-30% by weight of an indanthrene com- 5 UNITED STATES PATENTS pound and 15-20% by weight of a diarylamine having 2,351,384 Woods et a1 June 13, 1944 the general configuration 2,403,104 Lien July 2, 1946 H 2,663,690 Eckert Dec. 22, 1953 2,848,417 Armstrong et a1. Aug. 19, 1958 10 2,851,418 Lyons et a1 Sept.
  • each Ar is an aromatic hydrocarbon radical of 2,392,776 Lyons et aL June 30, 1959 the group consisting of p y nap thyl, al ylat d phenyl 2,908,644 od n et a1 1958 and alkylated naphthyl radicals. 2,946,750 Odell et a1. July 26, 1960

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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)
US792463A 1959-02-11 1959-02-11 High temperature grease compositions Expired - Lifetime US3052632A (en)

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Application Number Priority Date Filing Date Title
NL248188D NL248188A (enrdf_load_html_response) 1959-02-11
US792463A US3052632A (en) 1959-02-11 1959-02-11 High temperature grease compositions
GB4538/60A GB901918A (en) 1959-02-11 1960-02-09 Lubricating grease compositions
FR818033A FR1247727A (fr) 1959-02-11 1960-02-09 Compositions de graisses pour hautes températures
BE587413A BE587413A (nl) 1959-02-11 1960-02-09 Tegen hoge temperaturen bestendige smeervetcomposities.
CH140760A CH387210A (de) 1959-02-11 1960-02-09 Hochtemperatur-Schmierfett

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BE (1) BE587413A (enrdf_load_html_response)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3137653A (en) * 1961-03-14 1964-06-16 Socony Mobil Oil Co Inc Oxazole grease
US3655559A (en) * 1969-04-11 1972-04-11 Ciba Geigy Corp Alkylated diphenylamines as stabilizers
US3655561A (en) * 1969-06-24 1972-04-11 Mobil Oil Corp Lubricant compositions containing aryl-indano secondary amines
US3696851A (en) * 1964-02-11 1972-10-10 Geigy Chem Corp Chemical compounds and compositions

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2351384A (en) * 1942-11-18 1944-06-13 Shell Dev Lithium soap grease
US2403104A (en) * 1942-10-17 1946-07-02 Union Oil Co Lithium greases
US2663690A (en) * 1951-02-16 1953-12-22 Texas Co High-temperature sodium myristate grease containing n, n'diphenyl para-phenylene diamine
US2848417A (en) * 1955-08-15 1958-08-19 Shell Dev Extreme high temperature grease compositions
US2851418A (en) * 1956-12-28 1958-09-09 Texas Co Lubricating greases thickened with 3-nu-aryl-carbamyl-2-hydroxy-1-naphthyleneazoarenes
US2892776A (en) * 1957-08-13 1959-06-30 Texaco Inc Lubricating grease thickened with ultramarine blue
US2908644A (en) * 1957-11-25 1959-10-13 Texaco Inc Lubricating greases thickened with metal salts of sulfonated hydroxy azo compounds
US2946750A (en) * 1957-08-13 1960-07-26 Texaco Inc Lubricating greases thickened with reaction products of arylamine dyes with phosphomolybdic, phosphotungstic and phosphotungstomolybdic acids

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2403104A (en) * 1942-10-17 1946-07-02 Union Oil Co Lithium greases
US2351384A (en) * 1942-11-18 1944-06-13 Shell Dev Lithium soap grease
US2663690A (en) * 1951-02-16 1953-12-22 Texas Co High-temperature sodium myristate grease containing n, n'diphenyl para-phenylene diamine
US2848417A (en) * 1955-08-15 1958-08-19 Shell Dev Extreme high temperature grease compositions
US2851418A (en) * 1956-12-28 1958-09-09 Texas Co Lubricating greases thickened with 3-nu-aryl-carbamyl-2-hydroxy-1-naphthyleneazoarenes
US2892776A (en) * 1957-08-13 1959-06-30 Texaco Inc Lubricating grease thickened with ultramarine blue
US2946750A (en) * 1957-08-13 1960-07-26 Texaco Inc Lubricating greases thickened with reaction products of arylamine dyes with phosphomolybdic, phosphotungstic and phosphotungstomolybdic acids
US2908644A (en) * 1957-11-25 1959-10-13 Texaco Inc Lubricating greases thickened with metal salts of sulfonated hydroxy azo compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3137653A (en) * 1961-03-14 1964-06-16 Socony Mobil Oil Co Inc Oxazole grease
US3696851A (en) * 1964-02-11 1972-10-10 Geigy Chem Corp Chemical compounds and compositions
US3655559A (en) * 1969-04-11 1972-04-11 Ciba Geigy Corp Alkylated diphenylamines as stabilizers
US3655561A (en) * 1969-06-24 1972-04-11 Mobil Oil Corp Lubricant compositions containing aryl-indano secondary amines

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NL248188A (enrdf_load_html_response)
CH387210A (de) 1965-01-31
GB901918A (en) 1962-07-25
FR1247727A (fr) 1960-12-02

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