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  • 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
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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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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
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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
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—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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  • 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
  • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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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
  • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
  • C10M2215/226—Morpholines
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  • C10M2215/30—Heterocyclic compounds
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  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
  • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
  • C10M2219/108—Phenothiazine
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  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
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  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/041—Triaryl phosphates
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  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/042—Metal salts thereof
• • C—CHEMISTRY; METALLURGY
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  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
  • C10M2223/063—Ammonium or amine salts
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  • 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
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  • 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

Definitions

• This invention relates to synthetic ester lubricating oils having excellent corrosion resistance, oxidation stability and load-carrying properties. More particularly it relates to synthetic ester oils containing a combination of 1) a trihydrocarbyl phosphate, (2) an alkyl amine salt of a monohaloalkylphosphonic acid and (3) a dicarboxylic acid.
• Synthetic ester base oils are particularly suitable for use in high temperature-high speed lubricating applications such as in the lubrication of gas turbine engines because of their inherently good thermal stability and desirable viscosity properties.
• ester base lubricants are superior to mineral lubricating oils in many respects, they have a tendency to be slightly more corrosive and Will undergo oxidation and decompose at elevated temperatures. It is known that the thermal decomposition of synthetic ester oils is significantly accelerated by the presence of minute quantities of dissolved metals such as iron which can result from the dissolution of steel components by the ester base stocks or additives incorporated into these oils.
• lubricant compositions comprising a major amount of a synthetic ester lubricating oil and minor amounts each of (l) a trihydrocarbyl phosphate, (2) an alkyl amine salt of a monohaloalkylphosphonic acid and (3) a dicarboxylic acid have excellent anticorrosion, antioxidation and load-carrying properties.
• the aforementioned compositions have been found to be remarkably effective in passivating steel surfaces, thus substantially preventing dissolution of the metal, which correspondingly also increases the oxidation stability of the oil.
• the present compositions have been found to possess excellent load-carrying properties and are eminently suited for use in high temperature-high speed lubricating applications.
• hydrocarbyl groups can be alkyl, aryl, alkaryl and templated for use in the present compositions include those represented by the formula:
• R R and R are the same or different hydrocarbyl groups having from 1 to about 15 carbon atoms.
• the hydrocarbyl groups can be alkyl, aryl, alkaryl and aralkyl radicals. Aryl or alkaryl groups having from 1 to 10 carbon atoms are especially preferred.
• trihydrocarbyl phosphate compounds include tricresyl phosphate, tri(2,4-dimethylphenyl) phosphate, tri-(p-ethylphenyl) phosphate, tri-(Z-methyl-4-isopropylphenyl) phosphate, tri(p-tert butylphenyl) phosphate, tri-(2,6 dimethyl 4-tert-butylphenyl) phos phate, tri (4 methyl-l-naphthyl)phosphate, ethyl di- (p-cresyl) phosphate, 2,6-xylenyl di-(n-butyl) phosphate, triphenyl phosphate, cresyl diphenyl phosphate, dicresyl phenyl phosphate, xylyl dicresyl phosphate, trixylyl phosphate, dimethyl xylyl phosphate, dimethyl tolyl
• Amine salts which are suitable for use in the present compositions are the salts of C alkyamines and monohaloalkylphosphonic acids.
• Haloalkylphosphonic acid which can be used in forming these salts have the .general formula wherein R is a monohaloalkyl group containing 1 to 4, preferably 1 to 2 carbon atoms. Preferred halogens are fluorine, chlorine and bromine. Acids wherein the R group contains a chlorine atom substituted on the alpha carbon atom are especially advantageous for the purposes of the invention.
• acids examples include monochloromethylphosphonic acid, u-monochloroethylphosphonic acid, a-monochloropropylphosphonic acid, oc-ChlO- ro-u-methyl-ethylphosphonic acid, a-chloro-butylphosphonic acid and a-chloro-a-methyl-propylphosphonic acid.
• the anhydrides of the aforementioned acids can also be 'used to prepare suitable amine salts.
• Amines which form eifective salts with the above-described acids are primary or 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 means having at least 2 hydrocarbon substituents attached to the main carbon chain.
• the tertiary-alkyl radical the radical of polyisobutylene and polypropylene, and mixtures of these are particularly preferred.
• Examples of these amines are 1,l,3,3-tetramethylbutylamine, l,l,3,3, 5,S-hexamethylhexylamine, l,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.
• CgH5 (l-CaH17-C
• Primary amines of this type are commercially available from Rohm and Haas Company under the trade name of Primenes.
• the amine may also be a polyamine, such as a diamine or triamine, and
• amide or ether groups 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, diricinoleylamine, butylricinoleylamine, butyl-2- ethylhexylamine, dilaurylamine, methyloleylamine, ethyloctylamine, isoamylhexylamine, dicyclohexylamine, dicyclopentylamine, cyclohexyloctylamine, cyclohexylabenzylamine, benzyloctylamine, benzyl-Z-ethylhexylamine
• 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., US. 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.
• Dicarboxylic acids which can be effectively used in combination with the previously described trihydrocarbyl phosphates and amine salts are those dicarboxylic acids having from 4 to 14 carbon atoms. While it is contemplated that other dicarboxylic acids can be used, aliphatic dicarboxylic acids are preferred. Examples of these include adipic, pimelic, suberic, azelaic, sebacic, brassylic, and the like. Azelaic acid has been found to be particularly effective in the compositions of the invention.
• Suitable synthetic lubricant base stocks for the practice of the invention 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 14 carbon atoms.
• the ester base may comprise a simple ester (reaction product of a monohydroxyalcohol 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 with mixtures of esters, such as major proportions of complex esters and minor amounts of diesters.
• ester base oils examples include ethyl palmitate, ethyl laurate, butyl stearate, di-(2ethylhexyl)sebacate, di-(2-ethylhexyl) azelate, ethyl glycol dilaurate, di-(2- ethylhexyl)phthalate, di-(1,3-methylbutyl) adipate, di(1- ethylpropyl) azelate, diisopropyloxylate, dicyclohexyl sebacate, glycerol tri-n-heptoate, di(undecyl) azelate, and tetraethylene glycol di-(Z-ethylene caproate), and mixtures thereof.
• a preferred mixture of such esters consists of about 50-80% bis (2,2,4-trimethylpentyl) azelate and 20 to 50% 1,1,1-trimethylyl propane triheptanoate.
• esters for use as base stocks in the present invention are esters of monocarboxylic acids having 4 to 14 carbons and polyalcohols such as pentaerythritol, dipentaerythritol, and trimethylolpropane.
• esters examples include pentaerythrityl tetrabutyrate, pentaerythrityl tetravalerate, pentaerythrityl tetracaproate, pentearythrityl dibutyratedicaproate, 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 tributyratetricaproate, dipentaerythrityl trivalerate tripelargonate dipentaerythrityl mixed hexaesters of C fatty acids and trimethylolpropane heptoate.
• Mixtures of C monocarboxylic acid esters of pentaerythritol and dipentaerythritol are particularly advantageous base oils and are commercially available from Hercules, Inc.
• the trihydrocarbyl phosphate is employed in the present compositions in amounts of from 0.005 to 10% by weight, preferably from 0.01 to 3% based on the total composition weight.
• the amine salt of the monohaloalkylphosphonic acid can be used in amounts of from 0.005% to 10% by weight, but preferably is employed in the amounts of from 0.01 to 2% by composition weight.
• the dicarboxylic acid constituent is generally present in quantities of from 0.001 to 2% by weight, preferably from 0.005 to 0.1% by composition weight.
• additives can also be incorporated into the compositions according to the invention.
• examples of such additives are viscosity index improvers, e.g. methacrylate polymers and copolymers; antioxidants, e.g. aryl amines, phosphorous compounds or phenolic compounds; and corrosion inhibitors, antifoam agents, detergents or any other additive recognized in the art to perform a particular function or functions.
• Additive A C1s22 tertiary alkyl primary amino salt of monochloromethylphosphonic acid.
• Additive B Tricresyi phosphate
• Additive C Azelaie acid.
• Base Oil P Mixed C4-1o acid esters of pentacrythritol and dipentacrythritoi containing 2.5% w. of amine antioxidants, 0.1% w. of triazole corrosion inhibitors, 0.25% ⁇ v. of a copolymerie dispersant and 10 p.p.n1. silicone fluid antii'oamant.
• Base Oil Q Base oil P minus 0.025% w. triazolc corrosion inhibitor.
• Base Oil R Base 011 P plus 0.5% W. amine antioxidant.
• Base Oil T Base Oil S minus 0.05% w. triazole corrosion inhibitor.
• Base Oil U Base 011 T minus 0.5% w. amine antioxidant.
• Base Oil V Base Oil 8 plus 1% W. of the amine antioxidants
• compositions IX Relative rating p 3 ,3 and X compositions IX Relative rating p 3 ,3 and X
• composition VII an acid-amine salt alone Naval Thermal Stability-Corrosivity
• Composition VIII a combination of an acid-amine gig fi g fifi g ig L2 11.5 salt with a triaryl phosphate
• Composition VI Rlg test runs ditive A than does Composition VI.
• Compositions IV and shown are the load-carrying capacities of these composi- V exploded during the Naval Thermal stability cor Hons as i f' by of the Ryder Gear test rosivity test indicating acid-amine salts or azelaic acid complete description of this latter test may be found in individually do not impart the requisite Stabi1ity cor ASTM Bunetm September 1952' rosivity properties to ester base compositions.
• these additives are used in combination with a trihydrocarbyl TABLE In phosphate, however, a significantly improved product results, possessing excellent extreme-pressure, thermal stacomPosmm bility and anticorrosivity properties.
• Test mootedre I II We claim as our invention: igtstssitstatrfttziniassatsritai .37 .2 45 A i gg ti F t ma or amoun o a syn e c car xy 1c aci es er u n- Ryder Gear Test, load carrying capacity, lbs/in 3, 640 3, 055 eating Oil and (i) from 0.005 to 10% by Weight of a tri-C hydrocarbyl phosphate, (2) from 0.005 to 10% by weight of a salt of a C primary or secondary alkyl
• the composition of claim'l wherein the h h p osp ate Ryder Gear Test reslilts g gi gg. ihere 1 a compound is selected from the group consisting of triarylcomPleniemary reactlon etweel ⁇ e a ⁇ fives e 5 phosphates and trialkaryl phosphates, said aryl and m i f to load'canyilig capaclty' This Is evialkaryl groups having from 1 to 10 carbon atoms each. dent since Addltlv? and Addmve C by themsekes do 3.
• the composition of claim 2 wherein the acid-amine P2 ⁇ .
• 3 m glgmficant aim/Hy as salt is the saltof a monochloroalkylphosphonic acid and i gz h 2 5 2 3 31 g g g g zfi z an amine selected from the group consisting of primary amines and secondary amines having from 12 to 24 carsubstantial increase in load-carrying exceeding that of bons per molecule ggililiiosition I containing a larger amount of Additive A
• the cfmpositionl f claim 1 h ein the phosphate EXAMPLE IV compound is present in the amount of from 0.01 to 3% by weight, the acid-amine salt is present in the amount
• the efiicacy of the present addiof from 0.01 to 2% by weight
• the dicarboxylic acid tive combination in improving the load-carrying properties is present in the amount of from 0.01 to 1% by weight.
• compositions III, IV, V, and VI were 5.
• the composition of claim 4 wherein the ester lubrialso subjected to the Ryder Gear test.
• the composition of claim 5 wherein the phosphate
• the base oils used in the preparation of these blends were compound is tricresyl phosphate. identical.
• composition of claim 6 wherein the acid-amine 9.
• ester base 5 oil is a mixture of C monocarboxylic acid esters of pentaerythritol and dipentaerythritol.

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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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  • BE BE755588D patent/BE755588A/nl unknown
• 1969
  • 1969-09-08 US US856159A patent/US3634239A/en not_active Expired - Lifetime
• 1970
  • 1970-09-07 JP JP45077840A patent/JPS491889B1/ja active Pending
  • 1970-09-07 NL NLAANVRAGE7013175,A patent/NL169344C/xx not_active IP Right Cessation
  • 1970-09-07 DE DE2044257A patent/DE2044257C3/de not_active Expired
  • 1970-09-07 FR FR707032451A patent/FR2061606B1/fr not_active Expired
  • 1970-09-07 GB GB4266970A patent/GB1318380A/en not_active Expired

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