US2750341A - Lubricating grease comprising a synthetic oil and a complex thickener - Google Patents

Lubricating grease comprising a synthetic oil and a complex thickener Download PDF

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Publication number
US2750341A
US2750341A US263971A US26397151A US2750341A US 2750341 A US2750341 A US 2750341A US 263971 A US263971 A US 263971A US 26397151 A US26397151 A US 26397151A US 2750341 A US2750341 A US 2750341A
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Prior art keywords
acid
soap
complex
grease
oil
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US263971A
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Arnold J Morway
David W Young
Jr Paul V Smith
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Priority to NLAANVRAGE7710829,A priority Critical patent/NL173612B/xx
Priority to NL105177D priority patent/NL105177C/xx
Application filed by Exxon Research and Engineering Co filed Critical Exxon Research and Engineering Co
Priority to US263971A priority patent/US2750341A/en
Priority to GB21767/52A priority patent/GB714895A/en
Priority to FR1081109D priority patent/FR1081109A/fr
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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
    • C10M7/00—Solid or semi-solid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single solid or semi-solid substances
    • 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
    • C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
    • 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
    • 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
    • C10M2203/102—Aliphatic fractions
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • 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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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • 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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    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C10M2209/111—Complex polyesters having dicarboxylic acid centres
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C10M2209/112—Complex polyesters having dihydric acid centres
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
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    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043—Polyoxyalkylene ethers with a thioether group
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    • C10M2229/02—Unspecified siloxanes; Silicones
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    • C10M2229/04—Siloxanes with specific structure
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    • C10M2229/04—Siloxanes with specific structure
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
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    • C10N2010/02—Groups 1 or 11
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    • 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
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    • C10N2040/13—Aircraft turbines
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    • 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

  • the present invention relates to improved lubricating greases and particularly to lubricating greases of improved stability at high temperatures and under adverse conditions. It relates more especially to greases using a non-hydrocarbon or synthetic oil as the liquid constituent and employing a complex thickener.
  • An important aspect of the present invention is the discovery that certain complex soap-salt thickeners, e. g. a fatty acid soap and low molecular weight organic salt complex of lithium has outstanding properties as a thickener for some of the new types of synthetic materials which have been very difficult in the past to convert to lubricating greases.
  • certain complex soap-salt thickeners e. g. a fatty acid soap and low molecular weight organic salt complex of lithium has outstanding properties as a thickener for some of the new types of synthetic materials which have been very difficult in the past to convert to lubricating greases.
  • Another aspect of the present invention is the discovery of a grease composition of exceptional stability and fine lubricating properties at high temperatures composed primarily of a complex type aliphatic ester thickened to grease consistency with a lithium soap-salt complex of the type mentioned above.
  • the complex ester mentioned is preferably of the type prepared by esterifying dibasic acids and dihydric alcohols, adding a monovalent substituent to complete the esterification.
  • One type of such a lubricant is prepared by esterifying a glycol 01 nite States Patent 2,750,341 Patented June 12, 1956 a thioglycol with adipic acid or seba'cic acid or one of their homologues or thio equivalents, to produce an ester having, for example, a dihydric alcohol residue at the center and two dibasic acid residues attached, one on either side of the center.
  • the end groups of the acid residues are esterified with a monohydric alcohol.
  • a dibasic acid center may be esterified with two mols of dihydric alcohol which in turn have their esterification completed by treatment with two mols of monobasic acid.
  • Simple soaps e. g. the sodium or calcium soaps of C12 to C22 fatty acids
  • Simple soaps are entirely too soluble in the com.- plex esters described above to make a good grease structure. Furthermore, they cannot be prepared in situ in such esters because the basic saponifying agent, 6. g. metal oxide, hydroxide or carbonate, hydrolyzes or decomposes the ester.
  • greases employing synthetic ester oils may be made by forming a soap in a small quantity of mineral oil and thereafter blending in the ester, e. g. di-Z-ethyl hexyl sebacate, or dialkyl esters of adipic acid, etc.
  • ester e. g. di-Z-ethyl hexyl sebacate, or dialkyl esters of adipic acid, etc.
  • This technique apparently can be employed with many of the esters where the soaps used are not too soluble, but even in these cases the superior viscosity index and high flash point or low volatility characteristics of the synthetic oil are at least partially lost.
  • complex esters of the type mentioned above where these properties are very important, mineral oil dilution is most objectionable, aside from the fact that simple soaps are not effective thickeners.
  • a complex ester as described above may be thickened by the use of 5 to 25% by weight, based on the total composition, of the complex soap thickener.
  • This complex thickener may consist of various soaps, a preferred material being about 0.5 to 2 mols lithium soap of fatty acid in the C12 to C22 range, combined with about 1 mol of the lithium soap of a lower carboxylic acid, i. e., having a molecular weight below about 100.
  • the low molecular weight salt is preferably the acetate, but may be a propionate or formate, or it may be an unsaturated material of similar molecular weight range such as an acrylate, methacrylate or crotonate.
  • the formates are diflicult to disperse and higher acids than the propionate do not form good complexes.
  • the saturated materials are preferred for the long chain fatty acids.
  • For the low molecular weight acids either saturated or unsaturated are about equally desirable.
  • the most suitable fatty acids are of about C18 average chain length.
  • the acetate or acrylate (the lower molecular weight salts) are preferred for the low molecular weight component of the complex which appears to be of the Werner type.
  • the specific preferred thickener for the complex ester greases of the present invention is composed approximately of one mol of the lithium soap of fatty acids of approximately the stearic acid chain length (C13) in combination with about one mol of lithium acetate.
  • the fatty acids resulting from the hydrogenation of fish oils e. g. Hydrofol Acids 54 are very satisfactory for making the soaps. These average about C18, though they may range from C12 to C22.
  • the quantity of soap complex required may vary somewhat depending upon the desired consistency of the grease. in general, proportions will be not less than 5 nor more than of the Weight of the total composities as the complex esters but they do have excellent high temperature stability.
  • a very satisfactory grease has been prepared using about half and half of the complex ester and silicone.
  • the product of the present invention is best made by using a dry preformed soap complex.
  • the latter is prepared by direct neutralization of a mixture of the fatty acid (stearic acid or hydrogenated fish oil acids) and low molecular weight acid (preferably acetic acid) with the base in an aqueous medium.
  • Alkali metal bases are preferred, lithium being preferred and sodium next.
  • the hydroxides are employed. Proportions of base should be suflicicnt to neutralize the high and low molecular weight acids Without substantial excess or deficiency, although a minor degree of free acidity or alkalinity may be tolerated.
  • the acetate, or other low molecular weight salt, and the soap may be formed separately, dried and ground into fine powders, and the powdered materials mixed together before adding to the synthetic oil.
  • a soap-salt complex apparently is formed, much as in the procedure described in the preceding paragraph. The invention will be more fully understood by reference to the following specific examples.
  • Example I A complex ester oil of moderately high lubricating viscosity at ordinary temperatures, was prepared by coesterifying sebacic acid and glycol, using a monohydric alcohol to complete the esterification.
  • One mol of glycol and two mols of dibasic acid were used, along with two mols of monohydric alcohol such as the commercial alcohol mixture derived from coconut oil and sold under the trade name Lorol B. 1
  • This ester was thickened to a grease consistency by using 15% of a one-to-one mol ratio lithium acetate-lithium soap complex.
  • the soap was a hydrofolate, being derived from Hydrofol Acids 54, or commercial substantially saturated hydrogenated fish oil acids which have the general average chain length and chemical properties of stearic acid.
  • the dry soap-salt compound or complex and the complex ester were m xed together and heated with continuous stirring to a temperature of about 500 F, or until all soap-salt complex had melted.
  • the molten grease was then cooled without stirring. It had a smooth buttery appearance, with an unworked penetration value of 200 mm./l0 in the ASTM penetrometer. When worked 60 strokes in the standard ASTM grease worker, it showed a penetration value of 220 mm./ 10. It was still stable after working 100,000 strokes in the grease worker. Its dropping point was 408 F. and it showed no water solubility.
  • a part of such ester may be replaced by an ordinary simple diester of dibasic acid such as di-Z-ethylhexyl sebacate or adipate. in any case, however, the latter simple ester should not exceed in quantity the amount of complex ester in the oil blend.
  • an oxidation inhibitor for example 1% by weight, based on the total composition, of phenothiazine.
  • a grease prepared as just described was found to have a dropping point of 440 F., a worked penetration of 200 mm./ 10 after 60 strokes, complete stability after l00,000 strokes, and just a bare trace of water solubility.
  • Example II A grease was prepared using 14.3% by weight of lithium stearate, 14.3% of di-2-ethylhexyl sebacate, 28.6% of a complex ester derived from two mols of adipic acid, one mol of triethylene glycol, and two mols of ethyl hexanol, and 42.8% of a silicone oil, specifically a fairly viscous polymethyl phenylsiloxane, and 1% of phenothiazine.
  • the mixtures of lithium soap and simple diester were first heated to 350 F. while stirring. The complex ester was then added and the grease was heated further to 400 F. Thereafter the product was allowed to cool in thin layers.
  • the silicone oil was blended into the cool grease and the product was homogenized under conditions of high shear rates.
  • the product had a smooth buttery appearance, a dropping point of 390 F no measurable solubility in boiling water, an unworked penetration of 285 mm./ 10 at the standard test temperature of 77 F. and a worked penetration after 60 strokes that was unchanged, 285 mm./ 10. After working 100,000 strokes, the penetration number increased only slightly to 305 mm./ 10.
  • the product was tested also for its resistance to oxidation with the following results:
  • Example IV instead of using lithium stearate, a complex soap was prepared as the thickening agent using 66.2% of substantially saturated fatty acids of about C18 average chain length sold under the trade name Hydrofol Acids 53 which are hydrogenated fish oil acids. To these acids were added 13.3% by Weight based on the total soap composition, of glacial acetic acid and 20.5% of lithium hydroxide monohydrate. The fatty acid was melted in water at 150 F., and the glacial acetic acid was added thereto. The mixture was neutralized with a slight excess of the lithium hydroxide dissolved in boiling water. The soap was dried and powdered.
  • substantially saturated fatty acids of about C18 average chain length sold under the trade name Hydrofol Acids 53 which are hydrogenated fish oil acids.
  • To these acids were added 13.3% by Weight based on the total soap composition, of glacial acetic acid and 20.5% of lithium hydroxide monohydrate. The fatty acid was melted in water at 150 F., and the glacial acetic acid was added thereto.
  • Example V A product was made as in Example IV, except that di-2-ethylhexyl sebacate was used as the oily ester instead of the complex ester of Example IV. It was found that the soap became preferentially dispersed in the diester forming a hard coke-like material and leaving the silicone oil quite separate and unthickened. No grease product of smooth consistency could be prepared, the diester by itself being quite unsuitable for the purposes of this invention. On the other hand the product of Example IV formed an excellent grease of good structural stability. The product was smooth and hard and it required no homogenization. On the other hand the products of Examples II and HI had some disadvantages. The product of Example II had a good grease structure but required mechanical homogenization.
  • Example III It showed a tendency also to become crystalline at high temperatures.
  • the product of Example III became semi-fluid upon storage and showed no structural stability.
  • the complex ester should form a very substantial part of the liquid lubricant material.
  • the silicone oils may be used for a part, but preferably not for a very major part of the liquid portion.
  • Conventional modifiers such as antioxidants of various types, tackiness agents, metal deactivators, plasticizers, extreme pressure agents and the like, may be incorporated in the usual proportion as will be apparent to those skilled 1n the art.
  • a lubricating grease composition comprising a major proportion of a substantially completely esterified complex dibasic acid-dihydric alcohol-monovalent substituent aliphatic ester oil base of lubricating grade and viscosity, said dibasic acid being selected from the group consisting of sebacic and adipic acid, said dihydnc alcohol being triethylene glycol and said monovalent substituent being selected from the group consisting of ethyl hexanoic acid, ethyl hexanol and a mixture of C10 to C18 alcohols having an average of 13.5 carbon atoms, and 5 to 25% by weight, based on the total composition, of a preformed complex soap thickener consisting essentially of alkali metal soap of fatty acid in the C10 to C22 range and alkali metal salt of a carboxylic acid having a molecular weight of below about 100, the molar ratio of said fatty acid soap to said carboxylic acid salt being in the range of about 0.5 :
  • composition according to claim 1 wherein up to about one-half of the base oil is a silicone oil of lubricating viscosity.
  • composition according to claim 1 wherein the oil base comprises substantially equal proportions of complex ester and silicone oil.
  • composition according to claim 1 wherein said alkali metal is lithium.
  • composition according to claim 1 wherein said alkali metal is sodium.
  • composition according to claim 1 wherein the soap and salt. are present in about equimolar proportions.
  • composition according to claim 1 wherein the salt is lithium acetate.
  • a lubricating grease composition consisting essentially of a substantially completely esterified dibasic aciddihydric alcohol-monovalent substituent aliphatic ester oil of lubricating grade and viscosity, said dibasic acid being selected from the group consisting of sebacic acid and adipic acid, said dihydric alcohol being triethylene glycol and said monovalent substituent being selected from the group consisting of ethyl hexanoic acid, ethyl hexanol and a mixture of C10 to C12 alcohols having an average of 13.5 carbon atoms, and 5 to 25% by weight, based on the total composition, of a lithium soap of saturated fatty acids in the C12 to C22 range complexed with lithium salt of carboxylic acids, of the C1 to C3 range selected from the group consisting of formic acid, acetic acid, propionic acid and acrylic acid.
  • composition according to claim 9 wherein the soap and salt are present in substantially equimolar proportions.
  • composition according to claim 9 wherein the salt is of saturated carboxylic acid.
  • composition according to claim 9 wherein the soap is predominantly of an average of C18 fatty acid.
  • a lubricating grease composition consisting essentially of a mixed base vehicle of a substantially completely esterified dibasic acid-dihydric alcohol-monovalent substituent aliphatic ester oil of lubricating grade and viscosity, said dibasic acid being selected from the group consisting of sebacic acid and adipic acid, said dihydric alcohol being triethylene glycol and said monovalent substituent being selected from the group consisting of ethyl hexanoic acid, ethyl hexanol and a mixture of C10 to C18 alcohols having an average of 13.5 carbon atoms, and a dimethyl silicone polymer oil of lubricating viscosity, said silicone oil amounting to not more than onehalf of said mixed base vehicle, said vehicle being thickened to a grease consistency with about 15 by weight, based on the total composition, of a preformed complex of about 1 mol of lithium soap of saturated fatty acids in the C12 to C22 range and about 1 mol of lithium acetate.

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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)
US263971A 1951-12-28 1951-12-28 Lubricating grease comprising a synthetic oil and a complex thickener Expired - Lifetime US2750341A (en)

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NLAANVRAGE7710829,A NL173612B (nl) 1951-12-28 Zeefdruksjabloon met periodiek gatenpatroon.
NL105177D NL105177C (enrdf_load_stackoverflow) 1951-12-28
US263971A US2750341A (en) 1951-12-28 1951-12-28 Lubricating grease comprising a synthetic oil and a complex thickener
GB21767/52A GB714895A (en) 1951-12-28 1952-08-29 Improvements in or relating to lubricating grease
FR1081109D FR1081109A (fr) 1951-12-28 1952-11-28 Graisse lubrifiante

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US2889281A (en) * 1956-03-21 1959-06-02 Exxon Research Engineering Co Synthetic lubricating composition
US2892777A (en) * 1954-06-23 1959-06-30 Exxon Research Engineering Co Process for preparing improved synthetic ester based grease compositions
US4410435A (en) * 1979-08-16 1983-10-18 Nippon Seiko Kabushiki Kaisha Lithium complex grease and its producing method
US4879054A (en) * 1988-02-29 1989-11-07 Amoco Corporation Process for producing low temperature high performance grease
ITTV20100093A1 (it) * 2010-06-30 2011-12-31 Benedetto Mauro De Liquido specifico sintetico,idoneo alla formazione di una propria pellicola super lubrificante tra meccanismi in attrito, per diminuire frizione ed usura in condizioni di lubrificazione in alta temperatura

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US2455892A (en) * 1946-08-27 1948-12-07 Internat Lubricant Corp Lubricating greases and method of making the same
US2508741A (en) * 1948-04-12 1950-05-23 Texas Co Lubricating grease composition
US2551931A (en) * 1948-09-29 1951-05-08 Dow Corning Polysiloxane grease and method of preparation
US2575196A (en) * 1948-10-01 1951-11-13 Standard Oil Dev Co Mixed estirs of polyhydric alcohols and dibasic acids
US2575195A (en) * 1948-10-01 1951-11-13 Standard Oil Dev Co Dibasic acid esters and method for producing them
US2581127A (en) * 1950-01-25 1952-01-01 Standard Oil Dev Co High-temperature lubricating grease
US2586693A (en) * 1949-11-01 1952-02-19 Standard Oil Dev Co Lubricating grease
US2607735A (en) * 1949-03-12 1952-08-19 Standard Oil Dev Co Alkaline earth metal soap greases
US2628974A (en) * 1948-03-27 1953-02-17 Texas Co Polyester synthetic lubricants
US2639266A (en) * 1951-04-07 1953-05-19 Texas Co Lubricating grease comprising a complex ester base and sodium myristate

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Publication number Priority date Publication date Assignee Title
US2455892A (en) * 1946-08-27 1948-12-07 Internat Lubricant Corp Lubricating greases and method of making the same
US2628974A (en) * 1948-03-27 1953-02-17 Texas Co Polyester synthetic lubricants
US2508741A (en) * 1948-04-12 1950-05-23 Texas Co Lubricating grease composition
US2551931A (en) * 1948-09-29 1951-05-08 Dow Corning Polysiloxane grease and method of preparation
US2575196A (en) * 1948-10-01 1951-11-13 Standard Oil Dev Co Mixed estirs of polyhydric alcohols and dibasic acids
US2575195A (en) * 1948-10-01 1951-11-13 Standard Oil Dev Co Dibasic acid esters and method for producing them
US2607735A (en) * 1949-03-12 1952-08-19 Standard Oil Dev Co Alkaline earth metal soap greases
US2586693A (en) * 1949-11-01 1952-02-19 Standard Oil Dev Co Lubricating grease
US2581127A (en) * 1950-01-25 1952-01-01 Standard Oil Dev Co High-temperature lubricating grease
US2639266A (en) * 1951-04-07 1953-05-19 Texas Co Lubricating grease comprising a complex ester base and sodium myristate

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2892777A (en) * 1954-06-23 1959-06-30 Exxon Research Engineering Co Process for preparing improved synthetic ester based grease compositions
US2889281A (en) * 1956-03-21 1959-06-02 Exxon Research Engineering Co Synthetic lubricating composition
US4410435A (en) * 1979-08-16 1983-10-18 Nippon Seiko Kabushiki Kaisha Lithium complex grease and its producing method
US4879054A (en) * 1988-02-29 1989-11-07 Amoco Corporation Process for producing low temperature high performance grease
ITTV20100093A1 (it) * 2010-06-30 2011-12-31 Benedetto Mauro De Liquido specifico sintetico,idoneo alla formazione di una propria pellicola super lubrificante tra meccanismi in attrito, per diminuire frizione ed usura in condizioni di lubrificazione in alta temperatura
WO2012001720A1 (en) * 2010-06-30 2012-01-05 Mauro De Benedetto A synthetic liquid, suitable for formation of a superior lubricating film between mechanisms in friction and for reduction of friction and wear under high temperature lubrication conditions, to be used as an integrator of the base oils

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FR1081109A (fr) 1954-12-16
NL173612B (nl)
GB714895A (en) 1954-09-01

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