US3309314A - Lubricant compositions - Google Patents

Lubricant compositions Download PDF

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Publication number
US3309314A
US3309314A US371184A US37118464A US3309314A US 3309314 A US3309314 A US 3309314A US 371184 A US371184 A US 371184A US 37118464 A US37118464 A US 37118464A US 3309314 A US3309314 A US 3309314A
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US
United States
Prior art keywords
salt
acid
amines
amine
oil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US371184A
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English (en)
Inventor
James R Price
Robert C Spillman
Kenneth T Wendler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell USA Inc
Original Assignee
Shell Oil Co
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Filing date
Publication date
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US371184A priority Critical patent/US3309314A/en
Priority to DE1965S0097348 priority patent/DE1594584B2/de
Priority to BE664644D priority patent/BE664644A/xx
Priority to GB22787/65A priority patent/GB1086886A/en
Priority to NL656506779A priority patent/NL140008B/nl
Priority to AT488465A priority patent/AT257792B/de
Priority to FR18741A priority patent/FR1434861A/fr
Application granted granted Critical
Publication of US3309314A publication Critical patent/US3309314A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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
    • 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
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/284—Esters of aromatic monocarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/285—Esters of aromatic polycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy 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
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    • 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
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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
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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
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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
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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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
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
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    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
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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
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    • C10M2215/064—Di- and triaryl amines
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    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
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    • C10M2215/066—Arylene diamines
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    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11

Definitions

  • This invention relates to improved synthetic lubricating compositions which are oxidation-stable and non-corrosive, and which have excellent extreme-pressure and antiwear properties.
  • Synthetic lubricants have gained prominence in the field of lubrication because of stringent requirements of certain new applications. These lubricants, which are frequently esters, ethers, silicones, or hydrocarbon polymers, are generally designed, and may be tailored for special applications where conventional mineral oils are not satisfactory. Synthetic lubricants have low pour points and desirable viscosity characteristics, and can generally be used at temperatures considerably above the decomposition temperatures of most mineral oils. Accordingly, these oils have found use in jet aircraft, missiles, automatic Weapons, etc., Where wide temperature ranges and extreme operating conditions are likely to be encountered. Proper lubrication of aircraft gas turbines, for example, requires ability to function at bulk oil temperatures as low as -65 F. to as high as 450 to 500 F. for some applications.
  • synthetic lubricants containing 1) 0.01 to by weight of a C to C oilsoluble aliphatic amine salt of a monoto per-haloalkyl phosphonic acid, the haloalkyl radical of which contains 1 to 4 carbon atoms, and (2) 0.01 to 10% by weight of a primary to tertiary amine of which each non-hydrogen substituent is a monoto di-nuclear unsaturated cyclic radical containing from 4 to 10 carbons and from 0 to 2 nitrogens, have excellent antiwear, oxidation and anticorrosion properties.
  • unsaturated cyclic radical used herein includes radicals of heterocyclic groups salt (hereinafter also called the salt) and the cyclic amine exhibit surprising oxidation stability, non-corrosivity, and cleanliness.
  • Aryl amines are, of course, well known as lubricating oil oxidation inhibitors.
  • phosphonic acid-amine salts are known antiwear additives, they are not known to increase oxidation stability; indeed, these salts do not, by themselves, have antioxidant properties. It has now been found, however, that these salts cooperate with cyclic amine antioxidants to produce increased oxidation resistance. This effect is illustrated in Table I, below, which illustrates the results of an air oxidation test conducted at 400 F. Air was passed at a rate of ml./ min. through a 20-gram sample which contained 20 ppm. copper and 20 p.p.m. iron (as soluble octoates) as catalysts.
  • the base stock, designated -Oil E consisted of about 60% C C, 'alphatic-acid esters of pentaerythritol and about 40% C C aliphatic acid esters of dipentaerythritol.
  • AIR OXIDATION TEST l Salt A is a mixed salt of monochloromethyl phosphonic acid and a mixture oftert-O1aCna1ky1 primary amines.
  • Table I illustrate the cooperative effect of an amine-phosphonic acid salt and a cyclic amine antioxidant in promoting oxidation stability of a synthetic base oil.
  • the introduction period of the cyclic-aminestabilized base is almost doubled by addition of the salt, which is shown to be ineffective, independent of the cyclic amine, as an oxidation inhibitor.
  • Oil B (about C -C aliphatic acid esters of pentaerythritol, 5% C -C aliphatic aicd esters of dipentaerythritol), was subjected alone, andwith the additives of the invention individually and in combination, to a test similar to that described in Federal Test Method Standard No. 791a as method 5308.4. Fluid samples cc.) were heated at a temperature of 450 F. for 72 hours in the presence of 1.0 square inch of each of the metals listed in the table. Air was bubbled through the sample at the rate of 5 liters per hours. Corrosion was measured in weight loss per unit of surface area.
  • Salt A is a mixed salt of monochloromethyl phosphonic acid and a mixture or tart-01543 alkyl primary amines.
  • Oils containing the cyclic amine-salt combination of the invention also have a particular advantage in exhibiting extremely low lead (Pb) corrosion.
  • synthetic lubricants containing cyclic amine antioxidants have generally been corrosive to lead, in the absence of lead-corrosion inhibitors such as 2,6-di-tert-butyl-4-dimethylamine-p-cresol.
  • Lead is corroded much more easily than other metals, such as steel, aluminum, magnesium, copper, and silver; also, lead corrosion is not predictable from corrosion results of other metals.
  • the difference of the lead corrosion function from the normal corrosion function is apparent from a comparison of Run 3 in Table III, below, with Run 2 in Table II.
  • each non-hydrogen substituent of which is a monoto dinuclear unsaturated cyclic radical containing from 4 to 10 carbon atoms and from 0 to 2, preferably 0 to l nitrogen atoms.
  • Primary to secondary, especially secondary, amines are preferred; the cyclic radicals are preferably aromatic. Included are aryl amines and amines having nitrogen-containing heterocyclic substituents. Many of these amines are well known antioxidants for both synthetic and mineral lubricating oils.
  • Suitable aryl amines are phenyl-u-naphthylamine, phenyl-B-naphthylamine, diphenylamine, di-u-naphthylarnine, di-fi-naphthylamine, di-u,;8-napl1thylamine, triphenylamine, and diphenyl naphthylamine.
  • suitable amines having a nitrogen-containing heterocyclic constituent are dipyridyl amines, aminopyrides, aminoquinolines, etc.
  • amines are phenyl-a-naphthylamine, diphenylamine, 2-2'dipyridylamine and the aminopyridines.
  • the cyclic amines are used in amounts of from 0.01 to 10% by weight, preferably 0.025% by weight of the final lubricating composition.
  • the salt to be used in combination with the cyclic amine described above is a salt of (D -C alkylamine and a monoto per-haloalkyl phosphonic acid, the haloalkyl group containing 1 to 4, preferably 1 to 2 carbon atoms.
  • the haloalkyl phosphonic acids used for preparing the salts for use in the invention generally have the formula where R is monoto per-haloalkyl containing 1 to 4, preferably 1 to 2 carbon atoms. R preferably contains 1 to 2 halogen atoms, more preferably 1 chlorine atom; it is also preferred to have at least one of the halogens substituted on the alpha carbon atom.
  • Preferred halogens are fluorine, chlorine, and bromine, especially chlorine.
  • suitable phosphonic acids are monochloromethylphosphonic acid, 1-monochloroethylphosphonic acid, 1,1 dichloropropylphosphonic acid, perchloroethylphos phonic acid, dichloromethylphosphonic acid, perchlorornethylphosphonic acid, monobromomethylphosphonic acid, 1,1-chlorobromopropylphosphonic acid, dibromomethylphosphonic acid, Inonofluoromethylphosphonic acid, and 1,l-difiuoroethylphosphonic acid.
  • Amines which form effective salts of the phosphonic acids are primary to secondary alkyl amines having at least 8, preferably 8 to 30, and more preferably 12 to 24 carbon atoms per molecule.
  • Branched tertiary-alkyl primary amines are preferred; branched in this context 1 About 04-01 alkanoic acid esters of pentaerythritol, 5% 05-010 alkanoic acid esters of dipentaerythritol.
  • Suitable cyclic amines to be used in the amine-salt combination of the invention are primary to tertiary amines,
  • tertiary-alkyl radical the radical of polyisobutylene and polypropylene, and mixtures of these are particularly preferred.
  • these amines are 1,1,3,3-tetramethylbutylamine, 1,1,3, 3,5,5 hexamethylhexylamine, 1,l,3,3,5,5,7,7-octamethyloctylamine, and 1,1,3,3,5,5,7,7,9,9-decamethyldecylamine.
  • Tertiary alkyl methyl primary amines such as 2,2,4,4- tetramethylpentylamine and 2,2,4,4,6,6-hexamethyl hexylamine are also suitable.
  • the amine may also be a polyamine, such as a diamine or triamine, and may contain other non-reactive groups, such as amide or ether groups, in the carbon chain.
  • secondary amines for making the phosphonic acid salts are diamylamine, dihexylamine, di(2-ethylhexyl)-amine, dioctylamine, didecylamine, didodecylamine, ditetradecylamine, dihexadecylamine, dioctadecylamine, dibromodioctadecylamine, isopropyloleylamine, diricinoelylamine, butylricinoleylamine, butyl-2- ethylhexylamine, dilaurylamine, methyloleylamine, ethyloctaylarnine, isoamylhexylamine, dicyclohexylamine, dicyclopentylamine, cyclohexyloctylamine, cyclohexylbenzylamine, benzyloctylamine, benzyl-2-ethylhe
  • the phosphonic acid-amine salts for use in the invention can be prepared by direct neutralization of haloalkylphosphonic acid with a substantially stoichiometric amount of amine.
  • the reaction occurs at normal or moderately elevated temperatures and may be carried out in the presence of an inert diluent or solvent, such as a hydrocarbon, alcohol, ether, ketone, etc. Preparation of these salts is described in Watson et al., U.S. 2,858,332, issued Oct. 28, 1958.
  • the phosphonic acid-amine salts useful in the invention may also be modified with an alkali metal as described in Price et al., US. 3,112,267, issued Nov. 26, 1963.
  • the full amine salt of the phosphonic acid is prepared and is then treated in a low-boiling solvent with an alkali metal hydroxide, carbonate, or alcoholate such that one of the amine groups is replaced with an alkali metal.
  • Preferred alkali metals are sodium, potassium, and lithium.
  • the amine-phosphonic acid salts are used in amounts of from about 0.005 to 5% by weight, preferably about 0.01 to 5% by weight of the lubricating composition.
  • Weight ratios of the amount of salt to the amount of cyclic amine used in the combination of the invention are from about 0.01/1 to about /1, preferably from about 0.1/1 to about 5/1.
  • the combination may be added as a package to lubricating oils.
  • the additive combination of the invention is appropriate in mineral as well as synthetic lubricating oils, but is particularly useful in synthetic oils which are used under more extreme conditions where the particular advantages of the additives of the invention become more pronounced.
  • Synthetic lubricants suitable for the invention are of various types, such as aliphatic esters, silicones, polyalkylene oxides, polyphenyl ethers, fiuorinated hydrocarbons, polyolefins, and phosphate esters.
  • silicones include methyl silicone, methylphenyl silicone, methylchlorophenyl silicone, etc.
  • polyalkylene oxides 6 are polyisopropylene oxide, polyisopropylene oxide diether, and polyisopropylene oxide diester.
  • Fluorinated hydrocarbons include fluorinated oils and perfluorinated hydrocarbons.
  • Preferred synthetic lubricant base stocks are esters of alcohols having 1 to 20, especially 4 to 12, carbon atoms and aliphatic carboxylic acids having from 3 to 20, especially 4 to 12, carbon atoms.
  • the ester base may be a simple ester (reaction product of a monohydroxy alcohol and a monocarboxylic acid), a polyester (reaction product of an alcohol and an acid, one of which has more than one functional group), or a complex ester (reaction product of a polyfunctional acid with more than one alcohol, or of a polyfunctional alcohol with more than one acid).
  • excellent synthetic lubricants may be formulated from mixtures of esters, such as major proportions of complex esters and minor amounts of diesters.
  • Monohydric alcohols suitable for making ester base stocks include methyl, h-utyl, isooctyl, dodecyl and octadecyl alcohols.
  • OX0 alcohols prepared by the reaction of olefins with carbon monoxide and hydrogen are suitable.
  • Neo alcohols, i.e., alcohols having no hydrogens on the beta carbon atom are preferred. Examples of such alcohols are 2,2,4-trimethylpentan-ol-1 and 2,2-dimethyl propanol.
  • Polyalcohols used for the production of base oil esters preferably contain 1 to 12 carbons.
  • dialco- 11015 are 2-ethyl-l,3-hexanedi0l, 2-propyl-3,3-heptanedi0l, 2-butyl-l,3-butanediol, 2,4-d-imesityl-1,3-butanediol, and polypropylene glycols having molecular Weights of from about 100 to 300.
  • Alcohols having 3, 4, 5 or more bydroxyl groups per molecule are also suitable and are preferred; examples of these polyols are pentaerythritol, dipentaerythritol, and trimethylolpropane. Mixtures of alcohols may also be used.
  • Suitable carboxylic acids for making the ester base oils include monoand di-basic aliphatic carboxylic acids.
  • appropriate acids are butyric, valeric, sebacic, azelaic, suberic, succinic, caproic, adipic, ethyl suberic, diethyl adipic, oxalic, malonic, glutaric, pentadecanedicarboxylic, diglycolic, thiodiglycolic, acetic, propionic, caprylic, lauric, palmitic, pimelic, and mixtures thereof.
  • Preferred acids are sebacic, azelaic, glutaric, adipic, and their mixtures.
  • ester base oils examples include ethyl palmitate, ethyl laurate, butyl stearate, di(2-ethylhexyl) sebacate, di-(Z-ethylhexyl) azelate, ethyl glycol dilaurate, di-(2- ethylhexyl) phthalate, di-(1,3-methylbutyl) adipate, di- (l-ethylpropyl) azelate, diisopro-pyloxylate, dicyclohexyl sebacate, glycerol tri-n-heptoate, di(undecyl) azelate, and tetraethylene glycol di-(2-ethylene caproate), and mixtures thereof.
  • An especially preferred mixture of esters consists of about 50 to wt. bis(2,2,4-trimethylpentyl) azelate and 20 to 50% wt. 1,1,1-trimethylyl
  • esters for use as base stocks in the present invention are esters of monocar-boxylic acids having 3 to 12 carbons and polyalcohols such as pentaerythritol, dipentaerythritol, and trimethylolpropane.
  • esters examples include pentaerythrityl butyrate, pentaerythrityl tetrabutyrate, pentaerythrityl tetravalerate, pentaerythrityl tetracaproate, pentaerythrityl dibutyra-tedicaproate, pentaerythrityl butyratecaproate divalerate, pentaerythrityl butyrate trivalerate, pentaerythrityl butyrate tricaproate, pentaerythrityl tributyratecaproate, mixed C saturated fatty acid esters of pentaerythritol, dipentaerythrityl hexavalerate, dipentaerythrityl hexacaproate, dipentaerythrityl hexaheptoate, dipentaerythrityl hexacaprylate, dipentaerythrityl tributyratecaproate,
  • Ester oils may be prepared by simple reaction of the Composition 1 Base A:
  • a lubricant composition comprising a major amount of a synthetic ester lubricating oil and (1) 0.01 to 5% by Weight of a salt of an alkyl amine selected from the group consisting of alkyl primary and alkyl secondary amines having from 8 to 30 carbon atoms and a monoto per-haloalkyl phosphonic acid, wherein the haloalkyl radical contains 1 to 2 carbon atoms, and
  • composition of claim 1 wherein the salt is a mixed salt of an alkyl primary amine having 8 to 30 carbon atoms and moonchloromethylphosphonic acid.
  • composition of claim 1 wherein the phosphonic acid is monochloromethylphosphonic acid.
  • composition of claim 1 wherein the synthetic ester lubricating oil comprises esters of monocarboxylic acids having from 4 to 12 carbon atoms and pentaerythritol.
  • composition of claim 1 wherein the synthetic ester lubricating oil comprises a mixture of from to by weight bis(2,2,4-trirnethylpentyl)azelate and 20 to 50% by Weight 1,1,1-trimethyl propane triheptanoate.
  • a lubricant additive composition consisting essentially of (1) a salt of an alkyl amine selected from the group consisting of alkyl primary and alkyl secondary amines having from 8 to 30 carbon atoms and a monoto per-haloalkyl phosphonic acid, wherein the haloalkyl radical contains 1 to 2 carbon atoms, and

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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)
US371184A 1964-05-29 1964-05-29 Lubricant compositions Expired - Lifetime US3309314A (en)

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US371184A US3309314A (en) 1964-05-29 1964-05-29 Lubricant compositions
DE1965S0097348 DE1594584B2 (de) 1964-05-29 1965-05-28 Oxydations- und bleikorrosionsbestaendiges esterschmieroel
BE664644D BE664644A (nl) 1964-05-29 1965-05-28
GB22787/65A GB1086886A (en) 1964-05-29 1965-05-28 Lubricant compositions containing additives
NL656506779A NL140008B (nl) 1964-05-29 1965-05-28 Werkwijze ter bereiding van een smeermiddelmengsel.
AT488465A AT257792B (de) 1964-05-29 1965-05-28 Schmiermittelgemisch und Zusatzgemisch für ein Schmieröl
FR18741A FR1434861A (fr) 1964-05-29 1965-05-28 Perfectionnements au graissage

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3432433A (en) * 1965-11-15 1969-03-11 Shell Oil Co Lubricant compositions
DE2233542A1 (de) * 1971-11-17 1973-05-24 Mobil Oil Corp Schmiermittelgemisch
US3793199A (en) * 1970-06-08 1974-02-19 Texaco Inc Friction reducing agent for lubricants

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2559754A (en) * 1950-06-29 1951-07-10 Du Pont Fluoroalkanephosphonic compounds
US2683691A (en) * 1951-08-18 1954-07-13 Shell Dev Extreme pressure lubricants
US2777819A (en) * 1954-04-27 1957-01-15 Shell Dev Lubricating compositions
US3121691A (en) * 1960-05-24 1964-02-18 Sinclair Research Inc Lubricant composition
US3126344A (en) * 1961-01-03 1964-03-24 Synthetic ester lubricating oil

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2559754A (en) * 1950-06-29 1951-07-10 Du Pont Fluoroalkanephosphonic compounds
US2683691A (en) * 1951-08-18 1954-07-13 Shell Dev Extreme pressure lubricants
US2777819A (en) * 1954-04-27 1957-01-15 Shell Dev Lubricating compositions
US3121691A (en) * 1960-05-24 1964-02-18 Sinclair Research Inc Lubricant composition
US3126344A (en) * 1961-01-03 1964-03-24 Synthetic ester lubricating oil

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3432433A (en) * 1965-11-15 1969-03-11 Shell Oil Co Lubricant compositions
US3793199A (en) * 1970-06-08 1974-02-19 Texaco Inc Friction reducing agent for lubricants
DE2233542A1 (de) * 1971-11-17 1973-05-24 Mobil Oil Corp Schmiermittelgemisch

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BE664644A (nl) 1965-11-29
NL140008B (nl) 1973-10-15
AT257792B (de) 1967-10-25
DE1594584B2 (de) 1976-09-16
DE1594584A1 (de) 1970-08-06
GB1086886A (en) 1967-10-11
NL6506779A (nl) 1965-11-30

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