US2862883A - Lubricating oil compositions containing acylated polyamine salts - Google Patents

Lubricating oil compositions containing acylated polyamine salts Download PDF

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US2862883A
US2862883A US633518A US63351857A US2862883A US 2862883 A US2862883 A US 2862883A US 633518 A US633518 A US 633518A US 63351857 A US63351857 A US 63351857A US 2862883 A US2862883 A US 2862883A
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percent
acid
naphthenamide
lubricating oil
kerex
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Houghes John
Garner Philip James
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Shell Development Co
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Shell Development Co
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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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60T—VEHICLE BRAKE CONTROL SYSTEMS OR PARTS THEREOF; BRAKE CONTROL SYSTEMS OR PARTS THEREOF, IN GENERAL; ARRANGEMENT OF BRAKING ELEMENTS ON VEHICLES IN GENERAL; PORTABLE DEVICES FOR PREVENTING UNWANTED MOVEMENT OF VEHICLES; VEHICLE MODIFICATIONS TO FACILITATE COOLING OF BRAKES
    • B60T13/00—Transmitting braking action from initiating means to ultimate brake actuator with power assistance or drive; Brake systems incorporating such transmitting means, e.g. air-pressure brake systems
    • B60T13/10—Transmitting braking action from initiating means to ultimate brake actuator with power assistance or drive; Brake systems incorporating such transmitting means, e.g. air-pressure brake systems with fluid assistance, drive, or release
    • B60T13/58—Combined or convertible systems
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08—Inorganic acids or salts thereof
    • C10M2201/082—Inorganic acids or salts thereof containing nitrogen
    • C10M2201/083—Inorganic acids or salts thereof containing nitrogen nitrites
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
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    • C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
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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
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/146—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent 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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    • C10M2207/402—Castor oils
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    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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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
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/28—Amides; Imides
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling

Definitions

  • lubricating oil detergents or dispersants were generally polyvalent metal salts or soaps of organic carboxylic or sulfonic acids such as organic naphthenic or organic sulfonic acids. Detergents of this type are relatively ineffective at extremely low or extremely high temperatures and do not improve the spreading pressure of lubricating oils on various surfaces.
  • acylated polyamine salts of aromatic acidic compounds particularly of one which is a sulfonic acid, carboxylic acid or phenolic compound, such as a petroleum or a synthetic alkaryl sulfonic acid, an alkyl salicylic acid, a simple alkylphenol or a poly(alkylphenol).
  • acylated polyamine salts are, thus, amido alkylene amine salts of the aromatic acid.
  • the N-acyl radical forming the amido group(s) is an acyl radical of a carboxylic acid, preferably an aliphatic (cyclic or acyclic) monocarboxylic acid.
  • the polyamines from which the amido alkylene amines are derivable are aliphatic polyamines which may be simple polyaminoalkanes, such as the diaminoalkanes, 1,2-diaminoethane, 1,2- or 1,3-diaminopropane, 1,2-, 1,3- or 1,4-diaminobutane, 2,3-diaminohexane, poly(alkylenediamines), such as diethylene triamine, triethylene tetramine, tetraethylene pentamine, dipropylene triamine, tripropylene tetramine, N-alkyldiaminoalkanes such as N- butyl ethylene diamine, diaminoalkyl ethers, including thioethers, such as di-(2-aminoethyl)sulphide, and the like.
  • simple polyaminoalkanes such as the diaminoalkanes, 1,2-di
  • the N-acyl group (s) (Elia of the amido group(s) corresponds to acyl radicals of any carboxylic acid, such as benzoic acid, salicylic acid, octyl salicylic acid, naphthoic acid, naphthenic acids, caproic acid, lauric acid, stearic acid or palmitic acid.
  • carboxylic acid such as benzoic acid, salicylic acid, octyl salicylic acid, naphthoic acid, naphthenic acids, caproic acid, lauric acid, stearic acid or palmitic acid.
  • naphthenic acids obtained as by-products in the refining of petroleum fractions, such as kerosene, gas oil and lubricating oil
  • the partially acylated aliphatic dior poly-amines may be prepared by the action of a corboxylic acid or a halide, nitrile or ester thereof on the dior poly-amine by methods which are well-known in the art.
  • the preferred method involves mixing equimolecular parts of acid and amine and heating in an autoclave at a temperature of from about 170 C. to about 200 C. for about 5 to 8 hours.
  • the crude reaction mixtures so obtained may be used as such to form the salts which are used in accordance with the present invention.
  • These salts may be prepared by any of the methods known for preparing salts of amines.
  • a solution of the partially acylated dior poly-amine in a solvent such as petroleum spirit may be mixed with a stoichiometric proportion of the acid, preferably dissolved in the same solvent.
  • the salt can be prepared by metathesis of, for example, the hydrochloride or sulphate of the partially acylated dior poly-amine with the alkali metal salt of the acid in a solvent which facilitates the removal of the inorganic salt produced.
  • aromatic acidic compounds from which the oilsoluble acylated polyamine salts are derived include aromatic sulfonic acids such as the nonyl or dodecyl benzene sulphonic acids, di-isopropyl naphthalene sulphonic acid, butyl phenol sulphonic acid and sulphonic acids derived from aromatic fractions from petroleum oils or the alkylation products of such fractions; alkyl salicylic acids such as octadecyl and diisopropyl salicylic acids and mixtures of alkylated salicylic acids in which the alkyl groups contain 8 to 18 carbon atoms; or phenols such as octyl and dodecyl phenols, the butyl and amyl naphthols or polyphenols obtained by condensing simple phenols at open positions ortho and/or para to the phenolic hydroxy group through alkylidene (methylene) radicals such as are obtained by condensing alkylated phenol
  • acylated polyamines (amidoamines) and their salts is illustrated in the following examples.
  • parts by weight referred to hereinafter as p. b. W.
  • parts by volume referred to hereinafter as p. b. v.
  • the naphthenic acid used to prepare the following naphthenamides was a mixture of acids obtained by distilling a petroleum lubricating oil fraction over caustic soda and recovering the naphthenic acids from the residue containing sodium naphthenates.
  • the acid had an acid value of 170 milligrams of potassium hydroxide per gram, corresponding to an average molecular weight of about 4.35, the naphthenic acids being essentially monocarboxylic acids.
  • Example I N (2 aminoethyl)naphthenamide was prepared by heating naphthenic acids (1.5 p. b. w.) with ethylene diamine (1.09 p. b. w.), in a mol ratio of l to 4, respectively, at reflux for 160 hours, at the end of which time the reaction was about percent complete. Most of the excess ethylene diamine was then removed under reduced pressure. The crude material (about 2 p. b. w.) was dissolved in 50 percent aqueous isopropyl alcohol (3 p. b. v.) and neutralized to bromophenol blue with concentrated hydrochloric acid (ca 1.5 p. b. v.). Petroleum spirit (1 p. b. v.) and Water (1.
  • the bottom layer was washed six times with petroleum spirit (1 p. b. v. portions) and the combined petroleum spirit extracts were back extracted with 35 percent aqueous isopropyl alcohol (1 p. b. v.).
  • the combined aqueous alcoholic layers were made alkaline to phenolphthalein with 40 percent sodium hydroxide solution and petroleum spirit (5 p. b. v.) was added.
  • a brown petroleum spirit layer separated, the aqueous layer was run oil? and washed once with petroleum spirit (0.5 p. b. v.).
  • the combined petroleum spirit solutions were washed three times with water (0.1 p. b. v. portions) and thesolvent removed.
  • Example II N-(Z-aminoethyl) naphthenamide was prepared by heating naphthenic acid (331 p. b. W.) and commercial grade ethylene diamine (279 p. b. w.) containing 14 percent by weight of water, at 180 C. under a pressure of about 7 atmospheres for 6 hours. The reaction mixture was stripped of excess ethylene diamine under reduced pressure and worked up as described under Example I. The yield of N -(Z-aminoethyl)naphthenamide was 252 p. b. w. (67.5 percent of theory). The product had a neutralization value equivalent to 152 milligrams of potassium hydroxide per gram (theory 151 mg. KOH/g.).
  • the amount of imidazoline derivative formed during the reaction by cyclization of the N-aminoethyl naphthenamide was about 1.5 percent by weight.
  • the neutralization value agreed with that required theoretically and the color of the product was good. Longer reaction times and higher reaction temperatures tended to increase the proportion of imidazoline derivative formed.
  • Example III N-(3-aminopropyl)naphthenamide was prepared by heating 1,3-diaminopropane (29.6 p. b. w.) and naphthenic acid (33.1 p. b. w.) at 150 C. for 160 hours at atmospheric pressure. The reaction mixture was worked up as described in Example I to,give 22 p. b. w. of naphthenamide having a neutralization value equivalent to 141 milligrams of potassium hydroxide per gram (theory 141 mg. KOH/g.) and nitrogen content 7.9 percent (theory 7.2 percent).
  • N-(S-aminooctyl)naphthenamide was prepared in a similar manner.
  • Example IV 1,2-diaminopropane (29.6 p. b. w.) and naphthenic acid (33.1 p. b. w.) were heated together at 150 C. for 160 hours, and the reaction mixture worked up in the manner described in Example I to give 17.7 p. b. w. of naphthenamide having a neutralization value equivalent to 121 milligrams of potassium hydroxide per gram (theory 145 mg. KOH/g.) and nitrogen content 7.2 percent (theory 7.2 percent).
  • Example V Naphthenic acid (13.8 p. b. w.) and diethylene triamine (9.1 p. b. w.) were heated together at 180 -C. for 6 hours at atmospheric pressure and the reaction mixture was worked up as described in Example I to give a 69 percent yield of N-(5-amino-3-azapentyl)naphthenamide.
  • Kerex for kerosene extract, is an aromatic extract of kerosene obtained by treating kerosene with liquid sulphur dioxide in the Edeleanu process. It has an A. S. T. M. boiling range of 165 to 270 C. and contains approximately 70 percent by weight of aromatic hydrocarbons.
  • the sodium Kerex sulphonate was extracted from it by means of normal butanol.
  • the butanol extract was dried azeotropically, filtered to remove inorganic salts and evaporated under reduced pressure, the residual salt being washed with ether and dried.
  • the solid sodium Kerex sulphonate contained 10 percent by weight of sodium and was obtained in 70 percent yield based on the Kerex consumed or 39 percent yield on total Kerex used.
  • the residual salt (146 p. b. w.; 96 percent yield) had a nitrogen content of 5.2 percent (theory 4.9 percent).
  • N-(aminopropyl)naphthenamide Kerex sulphonate This salt was prepared in percent yield by a method similar to that described under (a) above from N-(aminopropyl)naphthenamide hydrochloride (derived from 1:2-diaminopropane) and sodium Kerex sulphonate in aqueous alcohol, and extracting the amine Kerex sulphonate with benzene. The product had a nitrogen content of 4.6 percent (theory 4.5 percent).
  • N-(3-aminopropyl)naphthenamide Kerex sulphonate containing 4.8 percent nitrogen (theory 4.5 percent) and N-(8-aminooctyl)naphthenamide Kerex sulphonate containing 4.8 percent nitrogen (theory 4.0 percent) were prepared by the procedure similar to that described under (a). The latter product contained some 1:8-diaminooctane as impurity.
  • Example VII In this example is described the preparation of the alkyl Kerex sulphonate of N-(Z-aminoethyDnaphthenamide.
  • the sodium alkyl Kerex sulphonate used for this purpose was prepared as follows:
  • a Kerex fraction boiling at approximately 114 C. at 20 millimeters pressure was used. It had a molecular weight of 157 and contained 70 percent by weight of aromatics.
  • the alkylation was effected by adding powdered anhydrous aluminum chloride (3.3 p. b. w.) to the Kerex fraction (278.5 p. b. W.) at 25 C. and adding gradually to the stirred mixture 44.8 p. b. w. of a cracked petroleum fraction consisting mainly of straight chain olefins containing 8 carbon atoms in the molecule and which had a bromine number of 119 (theory for C H 143).
  • the hydrocarbon layer was distilled giving 124 p. b. W. of a fraction boiling at 96 to 122 C. at 18 millimeters pressure, molecular weight 166, which was mainly unreacted Kerex, and 758 p. b. w. of a second fraction boilmg at 118 to 144 C. and 0.5 millimeter pressure, molecular weight 232 which was the desired alkyl Kerex. There was a small residue.
  • the C -alkyl Kerex (70 p. b. w.) was reacted with 100 percent sulphuric acid (70 p. b. w.) at 30 to 35 C. for 1 hour.
  • the reaction mixture was poured into ice water and then warmed to 70 to 80 C. to break the emulsion which formed.
  • the lower aqueous layer containing very little sulphonate was discarded.
  • 95 percent ethanol (90 p. b. v.) was then added and the upper layer of unreacted hydrocarbon which separated on standing was removed.
  • the aqueous alcoholic layer was neutralized at 60 C. with solid sodium hydroxide (10 p. b. w.), using phenolphthalein as indicator, and 95 percent ethanol (4 p. b. v. added.
  • the cooled solution was filtered from inorganic salts and the solvent removed by distillation under reduced pressure.
  • An 84 percent yield of sodium C -alkyl Kerex sulphonate (81 p. b. w.) was obtained containing 96 percent by weight of the salt.
  • N-(2-aminoethyl)naphthenarnide alkyl Kerex sulphonate was prepared from the above sodium C -alkyl Kerex sulphonate (34 p. b. w.) and the hydrochloride from N (2-aminoethyl)naphthenamide (31.1 p. b. w.) in aqueous alcoholic solution.
  • the product was extracted with and desalted in benzene and yielded N-(2-amin0- ethyl)naphthenamide C -alkyl Kerex sulphonate (58 p. b. w.; 96 percent yield) having a nitrogen content of 4.1 (theory 4.1 percent).
  • Example VIII N (Z-aminoethyl)naphthenamide dodecylbenzene sulphonate was prepared by a method similar to that described under Example VI(a) by reacting sodium dodecylbenzene sulphonate (35 p. b. w.) and the hydrochloride from N (2 aminoethyDnaphthenamide (34.2 p. b. w.) in aqueous alcohol, the desired salt being extracted with and desalted in benzene and finally obtained by evaporation of the benzene solution (59.6 p. b. w., 90 percent theory). It had a nitrogen content of 4.0 percent (theory 4.2 percent). The dodecyl benzene sulphonic acid was obtained by sulphonating benzene which had been alkylated with propylene-tetramer.
  • N-(Z-aminoethyl)naphthenamide benzene sulphonate was prepared in a similar manner from the naphthenamide and sodium benzene sulphonate.
  • Example IX N (2 aminoethyl)naphthenamide naphthasulphonate was prepared by reacting the hydrochloride from N-(2- aminoethyl)naphthenamide with sodium naphthasulphonates in aqueous isopropyl alcohol.
  • the sodium naphthasulphonates used are obtained as byproducts in the refining of technical white oils and medicinal oils in the petroleum industry. They are oil-soluble salts and are available in a range of molecular weights. Normally they contain a minor proportion of oil which can be removed by washing an aqueous alcoholic solution of the sodium naphthasulphonates with light petroleum. Both oiled and de-oiled sodium naphthasulphonates were used to prepare the naphthenamide sulphonates. The preparations are summarized in the following table.
  • N-(Z-a-minoethyl)naphthenamide di-isopropyl salicylate was prepared by mixing a solution of di-isopropyl salicylic acid (33.6 p. b. w.) in light petroleum (B. P. 40 to 60 C.) with a solution of N-(2-aminoethyl)naphthenamide (56 p. :b. w.) also in light petroleum. A curdy precipitate formed. The solvent was removed by distillation leaving 98 p. b. w. of the salicylate which had a nitrogen content of 4.7 percent (theory 4.7 percent).
  • the di-isopropyl salicylic acid used was obtained by carboxylating di-isopropyl phenol which had been obtained by alkylating phenol with 2 molecular proportions of propylene in presence of anhydrous aluminum chloride.
  • N-(2-aminoethyl)naphthena-mide C C alkyl salicylate was obtained in 99 percent yield by reacting equivalent proportions of sodium C -C -alkyl salicylate and N-(Z-aminoethyl)naphthenamide hydrochloride in ethyl alcoholic solution.
  • the sodium chloride precipitated was filtered off and the filtrate treated with decolorizing charcoal, filtered and evaporated to dryness under reduced pressure.
  • the product contained 3.7 percent nitrogen (theory 3.8 percent).
  • the alkyl salicylic acids used in this preparation were obtained by carboxylating phenol which had been alkylated with a mixture of G to C alkenes-l in the presence of anhydrous aluminum chloride.
  • the proportion of the oil-soluble salts derived from a partially acylated aliphatic dior poly-amine and an aromatic acid used in accordance with this invention will vary greatly depending upon the eifectiveness of the particular salt employed and the degree of improvement of the properties of the base lubricating oil required.
  • the salt will be used in a proportion of from 0.1 to 5% by weight of the base oil. More usually, the proportion used will be between 0.2 and 2% by weight.
  • the lubricating oil used in the compositions of this invention may be any natural (hydrocarbon and polar containing oils) or synthetic oil (olefin polymers, esters, ethers, etc.) having lubricating properties.
  • it may be a mineral lubricating oil obtained from a parafiinic, naphthenic, asphaltic or mixed base crude petroleum.
  • the viscosities of these mineral lubricating oils may vary over a wide range such as from 40 SUS at F. to 1000 SUS at 210 F.
  • Typical synethetic lubricating oils which may be used are polymerized olefins, organic esters such as di(2-ethylhexyl)sebacate, dioctyl phthalate and trioctyl phosphate and silicon polymers.
  • the base lubricating oil may be a mineral lubricating oil mixed with a synethetic lubricating oil or with a fatty oil such as castor oil or lard oil.
  • a typical lubricating composition of the present invention is a solvent-refined mineral lubricating oil having a viscosity of 330 seconds Redwood I at 140 F. (hereinafter called oil A), to which has been added from 0.2 to 2% by weight of the N-(2- amino-ethyl)naphthenamide C14C18 alkyl salicylate described in Example XI.
  • oil A solvent-refined mineral lubricating oil having a viscosity of 330 seconds Redwood I at 140 F.
  • oil A solvent-refined mineral lubricating oil having a viscosity of 330 seconds Redwood I at 140 F.
  • Spreading pressure (dynes/square Cone. of additive 01 Example XI, percent w. centimeter) on- Steel Water Compositions of this invention can be used as engine oils, turbine oils, gear oils, cutting oils and various other fields of lubrication where detergency and stability are essential.
  • a lubricating oil composition comprising a major amount of a mineral lubricating oil and a minor but detergent amount of an oil-soluble mono-acylated aliphatic polyamine salt of an aromatic acidic compound wherein the acidic radical is selected from the group consisting of phenolic hydroxy group, carboxylic acid and sulfonic acid.
  • a lubricating oil composition comprising a major amount of a mineral lubricating oil and a minor, but detergent amount of an oil-soluble mono-acylated aliphatic polyamine salt of an aromatic sulfonic acid.
  • a lubricating oil composition comprising a major amount of a mineral lubricating oil and a minor, but detergent amount of an oil-soluble mono-acylated aliphatic polyamine salt of an alkyl salicylic acid.
  • a lubricating oil composition comprising a major amount of a mineral lubricating oil and a minor, but detergent amount of an oil-soluble mono-acylated aliphatic polyamine salt of a phenol.
  • composition of claim 2 wherein the salt is N-(2- amino ethyl)naphthenamide salt of dodecyl benzene sulfonic acid.
  • composition of claim 3 wherein the salt is N-(2- amino ethyl)naphthenamide salt of C -C alkyl salicylic acid.
  • composition of claim 4 wherein the salt is N-(2- amino ethyl)naphthenamide salt of octyl phenol-formaldehyde condensation product.

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US2992081A (en) * 1957-07-30 1961-07-11 Sinclair Refining Co Corrosion inhibited composition
US3189544A (en) * 1962-12-19 1965-06-15 Shell Oil Co Non-ash-containing lubricating oil composition
US4162223A (en) * 1978-03-21 1979-07-24 Phillips Petroleum Company Residue of hydrogenation product of branched aliphatic dinitriles as lubricant additive
US4200545A (en) * 1976-01-28 1980-04-29 The Lubrizol Corporation Amino phenol-detergent/dispersant combinations and fuels and lubricants containing same
US4249912A (en) * 1978-04-27 1981-02-10 Phillips Petroleum Company Aminoamide fuel detergents
US4861504A (en) * 1988-01-25 1989-08-29 Atlantic Richfield Company Oil additive having reduced lacquer forming tendencies
US20060281643A1 (en) * 2005-06-03 2006-12-14 Habeeb Jacob J Lubricant and method for improving air release using ashless detergents
WO2006132964A3 (en) * 2005-06-03 2007-04-26 Exxonmobil Res & Eng Co Ashless detergents and formulated lubricating oil contraining same
US20110059881A1 (en) * 2003-01-21 2011-03-10 The Lubrizol Corporation Sulphur Free Composition And Lubricant Composition And Methods Thereof

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US3267034A (en) * 1965-05-27 1966-08-16 Shell Oil Co Lubricating oil composition containing polyalkylene imine salicylate salts
CN109852797B (zh) * 2017-12-16 2020-12-29 虔东稀土集团股份有限公司 一种用于萃取分离锂元素的萃取溶剂及其萃取分离锂元素的方法

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US2336070A (en) * 1942-09-18 1943-12-07 Du Pont Lubricating oil
US2481585A (en) * 1945-09-17 1949-09-13 Michael W Freeman Lubricating oil composition
US2493483A (en) * 1948-04-26 1950-01-03 Shell Dev Marine engine lubricant

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US2604451A (en) * 1948-09-16 1952-07-22 Gulf Research Development Co Mineral oil compositions
US2580881A (en) * 1949-05-21 1952-01-01 Du Pont Stabilized petroleum products and stabilizing compositions
US2568472A (en) * 1950-01-12 1951-09-18 Gulf Research Development Co Oil compositions containing amine salts of acid compounds of boric acid and hydroxy carboxylic acids
US2668100A (en) * 1951-11-15 1954-02-02 Nat Aluminate Corp Corrosion inhibitor for liquid hydrocarbons
US2693448A (en) * 1952-12-30 1954-11-02 Socony Vacuum Oil Co Inc Demulsified antirust turbine oil

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US2336070A (en) * 1942-09-18 1943-12-07 Du Pont Lubricating oil
US2481585A (en) * 1945-09-17 1949-09-13 Michael W Freeman Lubricating oil composition
US2493483A (en) * 1948-04-26 1950-01-03 Shell Dev Marine engine lubricant

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2992081A (en) * 1957-07-30 1961-07-11 Sinclair Refining Co Corrosion inhibited composition
US3189544A (en) * 1962-12-19 1965-06-15 Shell Oil Co Non-ash-containing lubricating oil composition
US4200545A (en) * 1976-01-28 1980-04-29 The Lubrizol Corporation Amino phenol-detergent/dispersant combinations and fuels and lubricants containing same
US4162223A (en) * 1978-03-21 1979-07-24 Phillips Petroleum Company Residue of hydrogenation product of branched aliphatic dinitriles as lubricant additive
US4249912A (en) * 1978-04-27 1981-02-10 Phillips Petroleum Company Aminoamide fuel detergents
US4861504A (en) * 1988-01-25 1989-08-29 Atlantic Richfield Company Oil additive having reduced lacquer forming tendencies
US20110059881A1 (en) * 2003-01-21 2011-03-10 The Lubrizol Corporation Sulphur Free Composition And Lubricant Composition And Methods Thereof
US20060281643A1 (en) * 2005-06-03 2006-12-14 Habeeb Jacob J Lubricant and method for improving air release using ashless detergents
WO2006132964A3 (en) * 2005-06-03 2007-04-26 Exxonmobil Res & Eng Co Ashless detergents and formulated lubricating oil contraining same
US7820600B2 (en) 2005-06-03 2010-10-26 Exxonmobil Research And Engineering Company Lubricant and method for improving air release using ashless detergents
US7851418B2 (en) 2005-06-03 2010-12-14 Exxonmobil Research And Engineering Company Ashless detergents and formulated lubricating oil containing same

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