US2976238A - Oil-based compositions - Google Patents

Oil-based compositions Download PDF

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Publication number
US2976238A
US2976238A US703753A US70375357A US2976238A US 2976238 A US2976238 A US 2976238A US 703753 A US703753 A US 703753A US 70375357 A US70375357 A US 70375357A US 2976238 A US2976238 A US 2976238A
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Prior art keywords
oil
complex
zinc
compound
compositions
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US703753A
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Elliott John Scotchford
Edwards Eric Descamp
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Castrol Ltd
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Castrol Ltd
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/18—Complexes with metals
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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
    • C10M2203/108—Residual fractions, e.g. bright stocks
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/18—Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
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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
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • 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
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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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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/066—Arylene diamines
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    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • 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
    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • 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
    • C10M2227/09—Complexes with metals
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/08—Groups 4 or 14
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/10—Groups 5 or 15
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/12—Groups 6 or 16
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/14—Group 7
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/16—Groups 8, 9, or 10
    • 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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2040/135—Steam engines or 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/26—Two-strokes or two-cycle engines
    • 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—Semi-solids; greasy
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention is for improvements in or relating to oil-based compositions and is particularly concerned with lubricating compositions.
  • a further object of the present invention is to provide oil-based compositions having anti-corrosive properties.
  • a cylinder lubricant for marine diesel engines operating on boiler fuel or other fuel of high sulphur content which lubricant comprises a mineral lubricating oil having incorporated therein an oilsoluble organic nonaromatic amine having not less than 7 carbon atoms or an oil-soluble non-aromatic amine salt of a weak acid, said organic non-aromatic amine or amine salt being present in an amount sufficient to provide at least of amine in the oil.
  • the non-aromatic amines of this application effectively reduce cylinder Wear and improve piston cleanliness of marine diesels operating on boiler fuel, but they suffer from certain disadvantages in that they possess strong odours and have a caustic action on the skin, are prone to cause the removal of paint from surfaces with which they come into contact, and tend to react with carbon dioxide in the atmosphere with the consequent formation of oil-insoluble carbonates or carbamates which form an undesirable skin on the surface.
  • the amine salts on the other hand, those which have adequate oil-solubility, while free from these objections, have rather low neutralisation equivalents which necessitate their use in inconveniently large amounts.
  • compositions of the present invention incorporate oil-soluble compounds of mild odour which compounds are substantially neutral in reaction, yet they have higher neutralisation equivalents and can therefore be used in smaller amounts.
  • compositions of the present invention may be employed as lubricants for small two-stroke engines. While conventional mineral lubricating oils may be used for this purpose, the presence of additives to improve piston cleanliness and disperse or soften carbon deposits is often desirable.
  • oil-based compositions of the present invention may also be used as storage oils, slushing compositions and general rust-preventing compositions such compositions including, if desired, conventional additives such as metal petroleum (mahogany) sulphonates, wool grease and the like.
  • compositions of the present invention may also be employed as lubricants for steam turbines, such lubricants possessing good rust-preventive properties in the presence of water or salt water; conventional antioxidants will also generally be present in such compositions.
  • an oil-based composition comprising a mineral or synthetic oil having incorporated therein a proportion of a compound having the general formula wherein M is a polyvalent metal capable of forming ammino co-ordination complexes, A is the residue of an organic acid, B is an organic dior poly-amine, x and y are small integers satisfying the valency of M and A, z is a small integer such that the co-ordination number of M is partially or completely satisfied, and A and B are selected so that the compound is soluble in the oil.
  • M is a polyvalent metal capable of forming ammino co-ordination complexes
  • A is the residue of an organic acid
  • B is an organic dior poly-amine
  • x and y are small integers satisfying the valency of M and A
  • z is a small integer such that the co-ordination number of M is partially or completely satisfied
  • a and B are selected so that the compound is soluble in the oil.
  • the radical A has preferably one of the following where R and R are alkly, cycloalkyl, aralkyl, alkaryl or aryl groupings, and may carry substituents such as hydroxyl or ester groups or halogen atoms.
  • the metal M must be a metal capable of forming relatively stable ammino co-ordination complexes, and is desirably also a metal which is not prone to increase the oxidation rate of the oil in which it is dissolved.
  • the preferred metals are zinc, cadmium, cobalt, tin, lead, nickel and chromium, although others, such as copper, iron (ferrous), mercury, silver, manganese and the rare or comparatively rare elements of group VIII of the periodic table, e.g. platinum, palladium, ruthenium, osmium or iridium, may be used if desired.
  • the complex amino compounds employed as the additives in the present invention may be prepared by reacting a salt M A with the organic dior poly-amine.
  • Suitable salts M A are the acetates,
  • ctoates laurates, oleates, naphthenates, benzoates, alicylates, petroleum sulphonates, alklated aryl sulhonates and long chain alkyl and alkylated aryl hosphates.
  • di or poly-amines B examples are ethylene dimine, diethylene triamine, triethylene tetramine, tetrathylene pentamine, mixtures of higher polyethylene olyamines, piperazine, p-phenylene diamine and various ommercially available long-chain diamines of the genral formula R"--NHCH CH CH NH wherein R rep- :sents an alkyl group derived from a fatty acid, e.g. iuric acid or from mixed fatty acids obtained from oconut oil, soya bean oil or tallow, these diamines being Jld under the registered trademark Duomeen.
  • a fatty acid e.g. iuric acid or from mixed fatty acids obtained from oconut oil, soya bean oil or tallow
  • heterocyclic dior poly-amines may be emloyed, examples of suitable compounds being. sold uner the trademark Bitran.
  • the complex ammino compounds When the complex ammino compounds are intended I be employed as additives for lubricating oils which re to be subjected to relatively high temperatures, it is ecessary to select compounds derived from long-chain ior poly-amines, since compounds derived, for exmple, from the polyethylene polyamines tend to decomose with the formation of resinous substances which :nd to form objectionable gums on pistons, etc. Thus hen, for example, the complex compounds are to be nployed in lubricating compositions for 1.0. engine oils is desirable to select those derived from the )uomeens or other long-chain dior poly-amines.
  • the complex ammino compounds may be prepared by my means known to the art.
  • those made from il-soluble metal soaps or salts may conveniently be repared in solution, e.g. in mineral oil, by simply warmg with the dior poly-amine in the appropriate proporans, Generally the molar ratio of amine to metal salt ill not exceed 1:1, and it is often advantageous tohave l Ilid oil-insoluble metal salts, a convenient method is i reflux a solution of the dior poly-amine in petroleum her or benzene with a slight excess of the salt until the tter passes into solution, after which the solution is tered and the solvent removed by distillation.
  • Comex compounds of this type are in general readily solue in hot mineral oil but tend to separate to some exnt on cooling.
  • More useful mixed complexes can be 'epared by further reacting the oil-insoluble metal lt/amine complex with a proportion of an oil-soluble etal salt in such amounts that the molar ratio of total etal salts to the dior poly-amine is at least l:0.8.
  • oil-soluble complex ammino umpounds of the present invention are:
  • nc naphthenate/diethylene triamine complex (1:0.8 molar ratio) nc acetate/Duomeen C complex nc naphthenate/Duomeen C complex nc naphthenate/Bitran P complex nc oleate/Duomeen C complex :ad naphthenate/Duomeen C complex :ad naphthenate/triethylene tetramine complex nc naphthenate/p-phenylene diamine complex Nickel petroleum sulphonate/Duomccn C complex Cadmium octyl phosphate/Duomeen C complex
  • the complex ammino compound is of the type described in British patent application No. 39,206/56. Specific examples of complex compounds of this type are:
  • complex compounds may be prepared from certain commercially available materials having a relatively high organic acidity, e.g. crude wool grease. These may be neutralised directly with a suitable metal oxide or hydroxide, e.g. zinc oxide, and then complexed with the desired amine.
  • a suitable metal oxide or hydroxide e.g. zinc oxide
  • the most generally useful complex compounds are those prepared from freely oil-soluble metal salts e.g. the laurates, oleates and, particularly, the naphthenates of metals such as zinc, nickel, cobalt, tin and chromium and long-chain diamines, particularly the Duomeens.
  • the Duomeens have the general formula R"-NHCH CH CH NH the radical R" being derived from a fatty acid, and substances are commercially available in which R" is derived from coconut fatty acids (Duomeen C), soya fatty acids (Duomeen S) and tallow fatty acids (Duomeen T).
  • Duomeen C any of these substances may be employed in the production of the complex compounds, but it is generally preferred to use Duomeen C as this substance has the best oilsolubility and the highest neutralisation equivalent.
  • Zinc is generally the preferred metal both for economic reasons and because the zinc salts of organic acids can readily be prepared by direct neutralisation of the acids with zinc oxide in the presence of a little water. To obtain the maximum oil-solubility, particularly at low temperatures, it is generally desirable to have a small excess jofthe metal salt present, a molar ratio of saltzamine'of 1:0.8 being particularly suitable.
  • Complex compounds of this general type are suitable for use in a variety of lubricating compositions in accordance with the present invention.
  • Complex compounds having adequate oil-solubility may also be prepared from freely oil-soluble metal salts, e.g. zinc naphthenate, and diethylene triamine or other polyethylene polyamines. These may be used equally well'as corrosion inhibitors in steam turbine oils, but as already indicated their use should not be considered in lubricants liable to be subjected to relatively high temperatures.
  • the additives of the present invention may be employed, if desired, in conjunction with other additives commonly used in lubricating oils.
  • oils for internal combustion engines there may be present conventional detergents such as metal petroleum (mahogany) sulphonates, and antioxidants such as zinc dialkyl dithiophosphates, metal alkyl phenol sulphides or phosphorised sulphurised terpenes.
  • the additives may be employed not only in mineral lubricating oils but also in synthetic oils, e.g. the dicarboxylic acid diester type and the polyglycol ether type of synthetic lubricant.
  • oil-based compositions of the present invention are employed as lubricants for the cylinders of marine diesel engines operating on boiler fuel or other fuel of high sulphur content they may contain from 2 percent to 20 percent by weight of the complex ammino compound.
  • the additive is preferably used in a proportion of from 0.5 to 2 percent.
  • additives For use in turbine oils, selected additives may be used in concentrations ranging from 0.02% to 2.0% and preferably from 0.05% to 0.2%. In general rust-preventive compositions the additives may be employed in widely differing amounts depending on the application which is in mind; thus from about 0.1% up to or even 20% may be used depending on the severity of the conditions.
  • EXAMPLE 1 Zinc naphthenate diethylene triamine complex (Compound A) To 709 grams (0.55 mol) of an approximately 50% solution of zinc naphthenate in mineral oil were added 51.5 grams (0.5 mol) of diethylene triamine. An exothermic reaction took place, following which the material was stirred at 110 C. for minutes. The product was a brown oil containing 4.8% zinc and 2.7% nitrogen, and was freely soluble in mineral oil although diethylene triamine itself was quite insoluble.
  • the reserve alkalinity of this complex compond was found to be 176 mgs. KOH per gram, the reserve alkalinity of the original zinc naphthenate concentrate being about 80 mgs. KOH per gram.
  • Reserve alkalinity was determined by refluxing a weighed quantity of the sample with a known excess of 0.1 N HQ in a solution consisting of 5% methanol 45% ethanol 50% water and back-titrating with 0.1 N NaOH using screened methyl orange as indicator.
  • the product was freely miscible with mineral oil although the oil-solubility of Duomeen C itself was very limited. It contained 4.3% zinc and had a reserve alkalinity" of about 110.
  • the product contained 13.6% zinc and had a reserve alkalinity of about 550 mgs. KOH per gm. It was readily soluble in hot mineral oil but some separation occurred on cooling.
  • EXAMPLE 4 Zinc acetate-naphthenate Duomeen C complex (1:0.5:1 molar ratio) A mixture of 18.35 gms. (0.1 mol) of anhydrous Zinc acetate and 25.0 gms. (0.1 mol) of Duomeen C were stirred together in a beaker and heated slowly to 130 C. Most of the zinc acetate appeared to react in the temperature range to C. yielding a butt opaque viscous liquid. 53.6 grams (0.05 mol) of an approximately 50% oil solution of zinc naphthenate was now added and heating and stirring continued for a few minutes. The zinc naphthenate employed contained 12% zinc. The product was mixed with filter-aid and filtered hot. On dilution with an equal weight of mineral oil a clear stable 36% oil concentrate was obtained containing 5.2% of zinc and having a reserve alkalinity of about mgs. KOH per gram.
  • the product was a dark brown solid containing 3.04%
  • Example 3 By the general procedure outlined above, a large number of complex compounds suitable for use in the oilbased compositions of the present invention, may be prepared.
  • the direct heating method of Examples 1 and 2 is generally the preferred method, but various compounds derived from oil-insoluble metal salts, e.g. zinc benzoate, zinc salicylate, may be made by the method of Example 3.
  • the amount to be complexed ith the metal salt was calculated from a determination Ethe basicity of the amine.
  • Oil A was a mineral oil having a viscosity of about i seconds Redwood I at 140 F. and oil B was a lvent-refined oil of viscosity about 65 seconds Redwood it 140 F.
  • compositions of the present vention were subjected to a very severe test applicable anticorrosive engine lubricating oils designed to pro- :t aero-engines from corrosion during storage and shipent overseas.
  • Mineral oil C was a conventionally refined paraffinic brightstock of viscosity about 600 seconds Redwood I at F.
  • No. 1 cylinder was lubricated mechanically, the rate of feed of the test oil to this cylinder being 20 cc. per hour per lubricator Le. 40 cc. per hour total.
  • Mineral oil D was a solvent-refined mineral oil of viscosity approximately seconds Redwood l at 140 F.
  • compositions of the present invention have only a mild odour, are without caustic action on the skin and do not remove paint. Furthermore, they are stable on storage over long periods and do not react with carbon dioxide in the atmosphere. They are also without significant action on metals such as copper, brass, Phosphor bronze, zinc and aluminium at the temperatures encountered in service.
  • An oil-based composition consisting essentially of a lubricating oil having incorporated therein from 2% to 30% by weight of an oil-soluble complex ammino compound having the general formula M A B wherein M is selected from the group consisting of zinc, cadmium, cobalt, tin, lead, nickel and chromium; A is selected from the group consisting of engine tests. Results of the tests are summarized in R.0 o 0- R.SOz- RO-P-0- Table V. 0
  • composition as claimed in claim 1 herein the ubricating oil is a mineral oil.
  • composition as claimed in claim 1 wherein the lbricating oil is selected from the'groupconsisting of icarboxylic acid diester oils and pblyglycolether oils.
  • composition as claimed in claim 1 wherein the omplex ammino compound is a complex consisting of inc naphthenate/R"-NHCH CH CH NH wherein R" a an alkyl group having from 8 to l8 carbon atoms.
  • composition as claimed in claim 1 wherein the omplex ammino compound is a complex consisting of inc oleate/R"NHCH CI I CH NH wherein R" is an lkyl group having from 8 to 18 atoms.
  • composition as claimed in claim 1 wherein the omplex ammino compound is a complex consisting of :ad naphthenate/ "NHCH CH CH NH wherein R" i an alkyl group having from 8 to 18 carbon atoms.

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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)
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3093585A (en) * 1960-06-06 1963-06-11 Shell Oil Co Ester base lubricant compositions
US3192158A (en) * 1962-04-18 1965-06-29 Shell Oil Co Lubricating compositions containing a detergent copolymer and an alkaline earth petroleum sulfonate-trialkyl amine complex
US3331774A (en) * 1965-08-13 1967-07-18 Pennsalt Chemicals Corp Grease compositions
US3331775A (en) * 1966-10-04 1967-07-18 Pennsalt Chemicals Corp Lubricating compositions
US3332873A (en) * 1965-08-13 1967-07-25 Pennsalt Chemicals Corp Phosphate ester greases
US3791804A (en) * 1969-10-10 1974-02-12 Standard Oil Co Fuel and lubricating oil additives transition metal complexes
WO1987004454A3 (en) * 1986-01-21 1987-09-11 Lubrizol Corp Lubricant composition containing transition metals for viscosity control
WO1991018075A1 (en) * 1990-05-16 1991-11-28 N.V. Bekaert S.A. Additive for lubricants containing a metal complex
US5650382A (en) * 1993-01-14 1997-07-22 N.V. Bekaert S.A. Additive for lubricants containing a metal complex

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GB696064A (en) * 1950-02-27 1953-08-26 Wakefield & Co Ltd C C Lubricating compositions
US2684292A (en) * 1951-03-13 1954-07-20 Shell Dev Fuel oil composition
US2692858A (en) * 1950-05-12 1954-10-26 Wakefield & Co Ltd C C Castor oil lubricating composition
US2696473A (en) * 1951-06-20 1954-12-07 Texas Co Halogen containing extreme pressure lubricant stabilized with a polyalkylene polyamine
US2736658A (en) * 1952-07-23 1956-02-28 Armour & Co Method of protecting metal surfaces from corrosion and corrosion inhibitor compositions
US2737492A (en) * 1952-03-26 1956-03-06 American Cyanamid Co Lubricating oil compositions
US2752311A (en) * 1952-07-26 1956-06-26 Texas Co Lubricant containing a metal derivative of a hydroxyarylakyl polaymine and a metal dithiocarbamate
US2798045A (en) * 1954-09-27 1957-07-02 Shell Dev Lubricating compositions
US2805996A (en) * 1954-09-20 1957-09-10 Pennsalt Chemicals Corp Process for the production of oil soluble amine complexes and compositions containing such complexes
US2808376A (en) * 1955-12-29 1957-10-01 California Research Corp Corrosion inhibited lubricant composition

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GB696064A (en) * 1950-02-27 1953-08-26 Wakefield & Co Ltd C C Lubricating compositions
US2692858A (en) * 1950-05-12 1954-10-26 Wakefield & Co Ltd C C Castor oil lubricating composition
US2684292A (en) * 1951-03-13 1954-07-20 Shell Dev Fuel oil composition
US2696473A (en) * 1951-06-20 1954-12-07 Texas Co Halogen containing extreme pressure lubricant stabilized with a polyalkylene polyamine
US2737492A (en) * 1952-03-26 1956-03-06 American Cyanamid Co Lubricating oil compositions
US2736658A (en) * 1952-07-23 1956-02-28 Armour & Co Method of protecting metal surfaces from corrosion and corrosion inhibitor compositions
US2752311A (en) * 1952-07-26 1956-06-26 Texas Co Lubricant containing a metal derivative of a hydroxyarylakyl polaymine and a metal dithiocarbamate
US2805996A (en) * 1954-09-20 1957-09-10 Pennsalt Chemicals Corp Process for the production of oil soluble amine complexes and compositions containing such complexes
US2798045A (en) * 1954-09-27 1957-07-02 Shell Dev Lubricating compositions
US2808376A (en) * 1955-12-29 1957-10-01 California Research Corp Corrosion inhibited lubricant composition

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3093585A (en) * 1960-06-06 1963-06-11 Shell Oil Co Ester base lubricant compositions
US3192158A (en) * 1962-04-18 1965-06-29 Shell Oil Co Lubricating compositions containing a detergent copolymer and an alkaline earth petroleum sulfonate-trialkyl amine complex
US3331774A (en) * 1965-08-13 1967-07-18 Pennsalt Chemicals Corp Grease compositions
US3332873A (en) * 1965-08-13 1967-07-25 Pennsalt Chemicals Corp Phosphate ester greases
US3331775A (en) * 1966-10-04 1967-07-18 Pennsalt Chemicals Corp Lubricating compositions
US3791804A (en) * 1969-10-10 1974-02-12 Standard Oil Co Fuel and lubricating oil additives transition metal complexes
WO1987004454A3 (en) * 1986-01-21 1987-09-11 Lubrizol Corp Lubricant composition containing transition metals for viscosity control
WO1991018075A1 (en) * 1990-05-16 1991-11-28 N.V. Bekaert S.A. Additive for lubricants containing a metal complex
BE1004265A3 (nl) * 1990-05-16 1992-10-20 Bekaert Sa Nv Additief voor smeermiddelen omvattende een metaalcomplex.
TR25289A (tr) * 1990-05-16 1993-01-01 Bekaert Sa Nv Yaglayicilar icin bir metal kompleksi iceren katki maddesi
AU653522B2 (en) * 1990-05-16 1994-10-06 N.V. Bekaert S.A. Additive for lubricants containing a metal complex
US6150308A (en) * 1990-05-16 2000-11-21 Deruyck; Frank Additive for lubricants containing a metal complex
US5650382A (en) * 1993-01-14 1997-07-22 N.V. Bekaert S.A. Additive for lubricants containing a metal complex

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