US2796400A - Lubricating compositions - Google Patents

Lubricating compositions Download PDF

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Publication number
US2796400A
US2796400A US405500A US40550054A US2796400A US 2796400 A US2796400 A US 2796400A US 405500 A US405500 A US 405500A US 40550054 A US40550054 A US 40550054A US 2796400 A US2796400 A US 2796400A
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Prior art keywords
oil
castor oil
viscosity
blend
esters
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US405500A
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Thornley George Herbert
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CC Wakefield and Co Ltd
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CC Wakefield and Co Ltd
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125Carboxylix 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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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129Carboxylix 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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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/281Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/283Esters of polyhydroxy compounds
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    • C10M2207/40Fatty vegetable or animal oils
    • C10M2207/402Castor oils
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    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10N2010/00Metal present as such or in compounds
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Definitions

  • Castor oil and blends of castor oil with mineral lubri. cating oil have been extensively used for the lubrication of internal combustion engines, especially those operating under high loads and at high speeds.
  • the viscosity of castor oil has in the past been modified to a certain extent by blending with mineraloils of different viscosities, but it has not been found possible to bring about more than minor alterations. in viscosity by this means, owing to the limited solubility of mineral oil in castor oil (about maximum).
  • viscosity of an oil which is to be used for lubricating an internal combustion enfi gine will depend on the design of the engine.
  • certain engines designed to operate in conjunction with lubrieating oils of relatively low viscosity e. g., in the S. A. E. 10W or category
  • some of these engines e. g. the engines of certain racing cars, cannot be lubricated so satisfactorily by mineral oils owing to the high piston speeds involved.
  • a lubricating composition comprises a mixture of castor oil and at least one relatively non-volatile substantially neutral organic ester, with or without the further addition of a, mineral lubricating oil.
  • esters to be employed should be relatively non-volatile, i. e., should have a boiling point of at least 200 C., and they should be readily miscible with castor oil at normal operating temperatures.
  • the esters employed are the aliphatic or cycloaliphatic alcohol esters of organic dicarboxylic acids and may be represented by the general formula COORi where R is an alkyl, aryl, alkaryl or cycloalkyl radical, and R1 and R2 are the same or different, and are alkyl or cycl-oalkyl radicals.
  • R (CH2)n where n is a small integer from 2 to 8 and R1 and R2 are identical, and are branched-chain alkyl radicals having: at least 5 carbon atoms.
  • organic dicarboxylic acids from which the esters may be derived are: phthalic, succinic,
  • pimelic, suberic, azelaic, sebacic and picnic acids It is preferred to use saturated acids.
  • the alcohols used in esterifying the dicarboxylic. acids should. be saturated aliphatic or cycloaliphatic alcohols such as methyl, ethyl, n-butyl and isobutyl alcohols, or, preferably, the higher branched-chain alcohols such as Z-ethyl n-heXyl, 3:5 :S-trimethyl-hexyl and capryl (1- methyl n-heptyl) alcohols, or a commercially available mixture of branched-chain C7 to C9 alcohols known as Alphanol 79.
  • cycloaliphatic alcohols such as. methyl and dimethyl cyclohexanol may be used.
  • ethers or esters of polyhydric alcohols containing at least one free hydroxyl group e. g., ethylene glycol monobutyl ether or diethylene glycol monobutyl ether.
  • esters of dicarboxylic acids other esters having a boiling point above about 200 C. may be used if desired.
  • simple esters such as 'amyl lactate or tricresyl phosphate, or the esters of polyhydric alcohols, especially dihydric alcohols, with monocarboxylic acids, especially those containing more than five carbon atoms.
  • esters of polyalkylene glycols and glycol ethers such as the Ucon synthetic fluids. In selecting an ester it is preferred to avoid those containing unsaturated groupings, which are more prone to oxidation and decomposition, and those which are easily hydrolysed by Water yielding corrosive acids of low molecular weight.
  • the relative proportions of castor oil and ester or esters which are to be employed will depend upon the desired viscosity of the final blend. Any blends may be employed within the range of 10% castor oil and ester to 90% castor oil and 10% ester.
  • the composition includes one or more additives to retard oxidation and gum formation.
  • additives to retard oxidation and gum formation.
  • a preferred combination of additives is that disclosed in patent application No. 221,538, now Patent No. 2,692,858, in which an aromatic or heterocyclic secondary monoor poly-amine containing at least three cyclic nuclei at least two of which nuclei are aromatic nuclei attached directly to the nitrogen atom, is used in conjunction with an organic compound of tin .or antimony.
  • amines such as phenyl-wnaphthylamine, phenyl-fl-naphthylamine, fifi-dinaphthylamine, di-(B-naphthyl) -p-phenylene diam i-ne, phenothiazine, benzonaphthathiazine or Xylyl-fi-naphthylamine in conjunction with tin laurate, tin oleate, tin p-tertiary amyl phenol thioether, or preferably Ifill or antimony petroleum sulphonate.
  • amines such as phenyl-wnaphthylamine, phenyl-fl-naphthylamine, fifi-dinaphthylamine, di-(B-naphthyl) -p-phenylene diam i-ne, phenothia
  • additives which may be included with advantage are the triaryl phosphites and especially the phosphite esters of aromatic hydroxy-substituted thioethers and disulphides disclosed in Patent No. 2,396,839 which not only provide protection against corrosion of composite metal, e, g., copper lead bearings, but also serve to increase the load-carrying capacity of the composition.
  • Auxiliary additives which may be included in the composition are the reaction products of aldehydes or ketones with basic water-soluble primary or secondary amines, :as more fully described in our British patent specification No. 588,864.
  • An example of such a compound is dimorpholinyl phenyl methane.
  • the composition may include detergents such as calcium petroleum sulphonate or basic barium petroleum sulphonate, or antioxidants such as oilsoluble metal salts of organic dithiophosphoric acids or metal derivatives of alkylated phenol thioethers or disulphides.
  • detergents such as calcium petroleum sulphonate or basic barium petroleum sulphonate
  • antioxidants such as oilsoluble metal salts of organic dithiophosphoric acids or metal derivatives of alkylated phenol thioethers or disulphides.
  • Oil B mineral oil of viscosity about 70 seconds Redwood, at 140 F.
  • Blend A consisted of:
  • Blend B 13.6 20 8. 2 1st and 2nd rings 50% stuck, soft gum on inlet underhead and exhaust valve stem. Blend A 9.2 29 8. 3 Top ring, lightly pinched, other rings free, soft gum on inlet underhead. Blend A... 38 7. 8 Top ring 55% stuck, (after 20 others free. No hours). change in inlet valve condition. Trace hard black deposit on exhaust valve neck.
  • blend A not only gave a performance equivalent to that of blend B in the normal Lauson and Chevrolet tests, but also effected a significant reduction in frictional horsepower. In the high temperature Lauson tests it also showed a marked improvement in ring sticking.
  • blend A has been subjected to trials in a variety of highly-stressed motor cycle and motor car engines used in racing and record-breaking, and has given highly satisfactory results, the engines stripping in a very clean condition after test. For one new type of racing engine it was the only lubricant tried which gave a satisfactory performance.
  • a lubricating composition consisting essentially of a mixture of castor oil, mineral oil and at least one ester selected from the group consisting of the aliphatic and cycle-aliphatic alcohol esters of organic dicarboxylic acids represented by the formula GOORi COORz where n is an integer from 2 to 8 inclusive and R1 and R2 are identical and are selected from the group consisting of branched-chain alkyl radicals and alkyl-substituted cycloalkyl radicals having at least 5 carbon atoms, the castor oil and organic ester each being present in the amount of at least 10% and the mineral oil being present in the mixture in an amount up to about 35% and in greater amount than would nomally be used in conjunction with the castor oil alone, the ester acting as a mutual solvent for the two oils.
  • ester selected from the group consisting of the aliphatic and cycle-aliphatic alcohol esters of organic dicarboxylic acids represented by the formula GOORi COORz where n is an integer from 2 to 8
  • a lubricating composition as claimed in claim 1 in which there is also incorporated a small amount of a compound selected from the group consisting of aromatic secondary mono-amines, aromatic secondary polyamines, heterocyclic secondary mono-amines and heterocyclic secondary polyamines containing at least three cyclic nuclei at least two of which nuclei are aromatic nuclei attached directly to the nitrogen atom in conjunction with an organic compound selected from the group consisting of tin and antimony organic compounds.
  • a lubricating composition as claimed in claim 1 in which there is also incorporated a small amount of a compound selected from the group consisting of a triaryl phosphite, a phosphite ester of an aromatic hydroxysubstituted thioether and a phosphite ester of an aromatic hydroxy-substituted disulphide.
  • ester constituent consists at least in part of di(2-ethy1hexy1) sebacate.
US405500A 1953-01-28 1954-01-21 Lubricating compositions Expired - Lifetime US2796400A (en)

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MY (1) MY5700003A (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3108961A (en) * 1959-12-21 1963-10-29 Pure Oil Co Improved anti-wear lubricating composition
US6156228A (en) * 1994-11-16 2000-12-05 Houghton International, Inc. Trialkoxyalkylphosphate-based fire resistant fluid containing triglyceride
US20050198894A1 (en) * 2004-03-11 2005-09-15 Crompton Corporation Lubricant and fuel compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters
WO2011022266A3 (fr) * 2009-08-18 2011-05-19 The Lubrizol Corporation Composition lubrifiante contenant un agent anti-usure

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US2156130A (en) * 1933-11-18 1939-04-25 Smith William Percival Compositions for fluid transmission of power
US2340073A (en) * 1942-03-02 1944-01-25 Cities Service Oil Co Lubricating oil
US2460035A (en) * 1946-01-25 1949-01-25 Standard Oil Dev Co Synthetic lubricant
US2499984A (en) * 1948-12-16 1950-03-07 Rohm & Haas Oily complex esters
US2534803A (en) * 1946-01-11 1950-12-19 Automotive Prod Co Ltd Power transmission fluids
US2539504A (en) * 1945-02-03 1951-01-30 William A Zisman Lubricating composition
US2671758A (en) * 1949-09-27 1954-03-09 Shell Dev Colloidal compositions and derivatives thereof
US2692858A (en) * 1950-05-12 1954-10-26 Wakefield & Co Ltd C C Castor oil lubricating composition

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US2417281A (en) * 1944-11-10 1947-03-11 Standard Oil Dev Co Instrument lubricant
US2570038A (en) * 1948-12-29 1951-10-02 Standard Oil Dev Co Phenylenediacetate ester
US2599510A (en) * 1950-12-08 1952-06-03 Minshall Estey Organ Inc Keying device for electronic organs
GB779698A (en) * 1952-12-10 1957-07-24 Exxon Research Engineering Co Lubricant

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2156130A (en) * 1933-11-18 1939-04-25 Smith William Percival Compositions for fluid transmission of power
US2340073A (en) * 1942-03-02 1944-01-25 Cities Service Oil Co Lubricating oil
US2539504A (en) * 1945-02-03 1951-01-30 William A Zisman Lubricating composition
US2534803A (en) * 1946-01-11 1950-12-19 Automotive Prod Co Ltd Power transmission fluids
US2460035A (en) * 1946-01-25 1949-01-25 Standard Oil Dev Co Synthetic lubricant
US2499984A (en) * 1948-12-16 1950-03-07 Rohm & Haas Oily complex esters
US2671758A (en) * 1949-09-27 1954-03-09 Shell Dev Colloidal compositions and derivatives thereof
US2692858A (en) * 1950-05-12 1954-10-26 Wakefield & Co Ltd C C Castor oil lubricating composition

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3108961A (en) * 1959-12-21 1963-10-29 Pure Oil Co Improved anti-wear lubricating composition
US6156228A (en) * 1994-11-16 2000-12-05 Houghton International, Inc. Trialkoxyalkylphosphate-based fire resistant fluid containing triglyceride
US6521142B1 (en) 1994-11-16 2003-02-18 Houghton Technical Corp. Fire-resistant hydraulic fluid compositions
US20050198894A1 (en) * 2004-03-11 2005-09-15 Crompton Corporation Lubricant and fuel compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters
WO2005087904A2 (fr) * 2004-03-11 2005-09-22 Chemtura Corporation Compositions de lubrifiant et de combustible contenant des esters de l'acide carboxylique et de l'acide polycarboxylique hydroxyle
WO2005087904A3 (fr) * 2004-03-11 2006-01-19 Chemtura Corp Compositions de lubrifiant et de combustible contenant des esters de l'acide carboxylique et de l'acide polycarboxylique hydroxyle
US7696136B2 (en) * 2004-03-11 2010-04-13 Crompton Corporation Lubricant compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters
CN1946833B (zh) * 2004-03-11 2012-07-04 科聚亚公司 含有羟基多羧酸酯的润滑剂和燃料组合物
WO2011022266A3 (fr) * 2009-08-18 2011-05-19 The Lubrizol Corporation Composition lubrifiante contenant un agent anti-usure
US9738849B2 (en) 2009-08-18 2017-08-22 The Lubrizol Corporation Lubricating composition containing an antiwear agent

Also Published As

Publication number Publication date
GB750402A (en) 1956-06-13
FR1092725A (fr) 1955-04-26
DE1018572B (de) 1957-10-31
MY5700003A (en) 1957-12-31
BE526014A (fr)

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