EP0531585A1 - Öladditivkonzentrate und Schmieröle mit verbesserten Leistungen - Google Patents

Öladditivkonzentrate und Schmieröle mit verbesserten Leistungen Download PDF

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Publication number
EP0531585A1
EP0531585A1 EP19910308198 EP91308198A EP0531585A1 EP 0531585 A1 EP0531585 A1 EP 0531585A1 EP 19910308198 EP19910308198 EP 19910308198 EP 91308198 A EP91308198 A EP 91308198A EP 0531585 A1 EP0531585 A1 EP 0531585A1
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EP
European Patent Office
Prior art keywords
acid
oil
soluble
concentrate
amine
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.)
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Application number
EP19910308198
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English (en)
French (fr)
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EP0531585B1 (de
Inventor
Ian Macpherson
F. Sieberth John
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.)
Afton Chemical Ltd
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Afton Chemical Ltd
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Publication date
Application filed by Afton Chemical Ltd filed Critical Afton Chemical Ltd
Priority to EP91308198A priority Critical patent/EP0531585B1/de
Priority to DE69130450T priority patent/DE69130450T2/de
Priority to CA002076921A priority patent/CA2076921A1/en
Priority to AU22804/92A priority patent/AU657563B2/en
Priority to JP4265540A priority patent/JPH05209186A/ja
Publication of EP0531585A1 publication Critical patent/EP0531585A1/de
Application granted granted Critical
Publication of EP0531585B1 publication Critical patent/EP0531585B1/de
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    • C10M169/04—Mixtures of base-materials and additives
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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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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    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/108—Phenothiazine
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    • C10M2223/10—Phosphatides, e.g. lecithin, cephalin
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    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention relates to additive concentrates and oleaginous compositions (e.g., lubricating oils and functional fluids) having enhanced performance properties.
  • oleaginous compositions e.g., lubricating oils and functional fluids
  • additive concentrates containing, inter alia, sulphur-containing antiwear and/or extreme pressure additives, phosphorus-containing antiwear and/or extreme pressure additives, and other additive components have been proposed and used.
  • other additive components include acidic components such as carboxylic acids, hydrocarbyl phosphoric acids, and hydrocarbyl thiophosphoric acids; basic components such as amines; and ashless dispersants such as boronated succinimides.
  • the quality of automotive gear oils can be assessed by evaluating their performance in a number of tests. There are many tests which can be used to evaluate the antiwear, extreme pressure, oxidation, corrosion, etc., properties of the oil.
  • API GL-5 is one such designated classification which particularly relates to hypoid gears and other automotive equipment which may be operated under high-speed, shock-load; high-speed, low-torque; and low-speed, high-torque conditions.
  • CRC L-60 examines the oxidative stability of a lubricant when subjected to extreme oxidative and thermal conditions.
  • CRC L-60 test which is not part of API GL-5, is that the test may also be used to assess the deposit forming characteristics of the lubricant. Any sludge or/and varnish which is deposited on the gear faces during the test may be rated by an industry established procedure as a numerical rating from 1 to 10. A rating of 1 is very high sludge and/or varnish whilst 10 is no sludge or varnish.
  • This invention relates in part to the control of deposits in the CRC L-60 oxidation stability test using additive systems capable of providing good antiwear and/or extreme pressure performance.
  • one objective of this invention is to fulfill these requirements.
  • Still another need is for an ashless or low-ash lubricant additive package affording high dispersancy and high wear resistance to lubricants, such as crankcase lubricants, gear lubricants, manual and automatic transmission fluids, oil-based hydraulic fluids, wet brake fluids, and similar lubricants and functional fluids.
  • lubricants such as crankcase lubricants, gear lubricants, manual and automatic transmission fluids, oil-based hydraulic fluids, wet brake fluids, and similar lubricants and functional fluids.
  • an additive concentrate which comprises a diluent oil and a plurality of additive components, said additive components comprising at least one oil-soluble Mannich base ashless dispersant; at least one oil-soluble metal-free sulphur-containing antiwear and/or extreme pressure agent; and at least one oil-soluble metal-free phosphorus-containing antiwear and/or extreme pressure agent.
  • the Mannich base employed includes or, alternatively, consists of boronated Mannich base ashless dispersant.
  • Another embodiment of this invention involves the provision of an additive concentrate which comprises a diluent oil and at least 20% by weight, and preferably at least 50% by weight, of additive components, said additive components comprising at least one oil-soluble Mannich base ashless dispersant (preferably a boronated Mannich base ashless dispersant) and at least one oil-soluble metal-free sulphur-containing antiwear and/or extreme pressure agent in proportions such that the mass ratio (wt/wt) of nitrogen in the Mannich base dispersant to sulphur in the sulphur-containing antiwear and/or extreme pressure agent is in the range of about 0.0005:1 to about 0.5:1, and preferably in the range of about 0.003:1 to about 0.2:1.
  • an additive concentrate which comprises a diluent oil and at least 20% by weight, and preferably at least 50% by weight, of additive components, said additive components comprising at least one oil-soluble Mannich base ashless dispersant (preferably a boronated Mannich base ash
  • Still another embodiment of this invention comprises an additive concentrate which comprises a diluent oil and at least 20% by weight, and preferably at least 50% by weight, of additive components, said additive components comprising at least one oil-soluble Mannich base ashless dispersant (preferably a boronated Mannich base ashless dispersant), and at least one oil-soluble metal-free phosphorus-containing anti-wear and/or extreme pressure agent in proportions such that the mass ratio (wt/wt) of nitrogen in the Mannich base dispersant to phosphorus in the metal-free phosphorus-containing antiwear and/or extreme pressure agent is in the range of about 0.005:1 to about 5:1, and preferably in the range of about 0.01:1 to about 2:1.
  • any of the above additive concentrates further comprise at least one oil-soluble demulsifying agent.
  • any of the above additive concentrates further comprise at least one oil-soluble amine salt of a sulphur-free hydrocarbyl phosphoric acid.
  • any of the fore-going additive concentrates further comprise at least one oil-soluble amine salt of a carboxylic acid, and optionally free amine.
  • lubricant compositions which comprise a major proportion of at least one oil of lubricating viscosity and a minor amount of the various additive combinations referred to hereinabove.
  • the finished lubricant compositions of this invention are ashless or low-ash compositions, that is, they contain at most 100 parts by weight of metal introduced as one or more additive components per million parts by weight of base oil ("ppm"), preferably no more than 50 ppm of metal, and most preferably zero to at most 25 ppm of metal introduced as one or more additive components.
  • ppm base oil
  • the additive concentrates of this invention are preferably proportioned such that if one or more metal-containing components (e.g., zinc dihydrocarbyldithiophosphate and/or metal detergent) are included therein, the additive concentrate when employed in a base oil at the selected or recommended dosage level will yield a finished lubricant having at most 100 ppm, preferably at most 50 ppm, and more preferably at most 25 ppm of added metal. Compositions devoid of added metal content are most especially preferred. In this connection, neither boron nor phosphorus is subject to these preferred limitations on metal content, as neither such element is a metal. Thus the mere fact that boron and/or phosphorus components may leave residues during usage, is of no relevance as regards these preferred limitations on metal content.
  • metal-containing components e.g., zinc dihydrocarbyldithiophosphate and/or metal detergent
  • the additive combinations of this invention have the capability of contributing greatly improved performance properties to base oils of lubricating viscosity, including animal, vegetable, mineral, and synthetic oils.
  • significantly improved properties can be achieved in lubricant compositions of this invention when subjected to various API GL-5 test procedures, such as enhanced extreme pressure properties as seen in the standard CRC L-42 test, improved antirust performance as seen in the standard CRC L-33 test, and/or clean gears as seen in the standard CRC L-60 test.
  • particularly preferred compositions of this invention are those which satisfy all of the requirements of the API GL-5 test procedures.
  • particularly preferred compositions of this invention exhibit superior performance in the planetary spur gear test wherein a system of spur-type gears is driven under variable and very heavy loads.
  • the lubricating fluid is circulated around the system by a pump and is maintained at between 95°C and 130°C. Samples of the lubricating fluid are removed periodically and analyzed for iron content. The test is terminated when excessive wear is recorded either by high iron levels in the oil, or by gear tooth breakage.
  • Still another feature of this invention is that the preferred additive combinations are capable of exhibiting superior (e.g., GL-5) performance properties even when blended with synthetic lubricants, a result which has seldom been achievable heretofore.
  • Mannich base dispersants are condensation products formed by condensing a long chain hydrocarbon-substituted phenol with one or more aliphatic aldehydes, usually formaldehyde or a formaldehyde precursor, and one or more polyamines, usually one or more polyalkylene polyamines.
  • the resultant Mannich base is preferably (but not necessarily) boronated (sometimes called "borated") by reaction with a suitable boron compound such a boron acid, a boron ester, a boron oxide, a salt of a boron acid, or the like.
  • Mannich condensation products including in many cases boronated Mannich base dispersants, and methods for their production are described in the following U.S. Patents: 2,459,112; 2,962,442; 2,984,550; 3,036,003; 3,166,516; 3,236,770; 3,368,972; 3,413,347; 3,442,808; 3,448,047; 3,454,497; 3,459,661; 3,493,520; 3,539,633; 3,558,743; 3,586,629; 3,591,598; 3,600,372; 3,634,515; 3,649,229; 3,697,574; 3,703,536; 3,704,308; 3,725,277; 3,725,480; 3,726,882; 3,736,357; 3,751,365; 3,756,953; 3,793,202; 3,798,165; 3,798,247; 3,803,039; 3,872,019; 3,904,595; 3,957,746; 3,980,
  • the polyamine group of the Mannich polyamine dispersants is derived from polyamine compounds characterized by containing a group of the structure -NH- wherein the two remaining valances of the nitrogen are satisfied by hydrogen, amino, or organic radicals bonded to said nitrogen atom. These compounds include aliphatic, aromatic, heterocyclic and carbocyclic polyamines.
  • the source of the oil-soluble hydrocarbyl group in the Mannich polyamine dispersant is a hydrocarbyl-substituted hydroxy aromatic compound comprising the reaction product of a hydroxy aromatic compound, according to well known procedures, with a hydrocarbyl donating agent or hydrocarbon source.
  • the hydrocarbyl substituent provides substantial oil solubility to the hydroxy aromatic compound and, preferably, is substantially aliphatic in character.
  • the hydrocarbyl substituent is derived from a polyolefin having at least about 40 carbon atoms.
  • the hydrocarbon source should be substantially free from pendant groups which render the hydrocarbyl group oil insoluble. Examples of acceptable substituent groups are halide, hydroxy, ether, carboxy, ester, amide, nitro and cyano. However, these substituent groups preferably comprise no more than about 10 weight percent of the hydrocarbon source.
  • the preferred hydrocarbon sources for preparation of the Mannich polyamine dispersants are those derived from suitable petroleum fractions or from olefin polymers, preferably polymers of mono-olefins having from 2 to about 30 carbon atoms.
  • the hydrocarbon source can be derived, for example, from polymers of olefins such as ethylene, propene, 1-butene, isobutene, 1-octene, 1-methylcyclohexene, 2-butene and 3-pentene. Also useful are copolymers of such olefins with other polymerizable olefinic substances such as styrene.
  • these copolymers should contain at least 80 percent and preferably about 95 percent, on a weight basis, of units derived from the aliphatic mono-olefins to preserve oil solubility.
  • the hydrocarbon source generally contains at least about 40 and preferably at least about 50 carbon atoms to provide substantial oil solubility to the dispersant.
  • the olefin polymers having a number average molecular weight between about 600 and 5,000 are preferred for reasons of easy reactivity and low cost. However, polymers of higher molecular weight can also be used.
  • Especially suitable hydrocarbon sources are isobutylene polymers.
  • the Mannich polyamine dispersants are generally prepared by reacting a hydrocarbyl-substituted hydroxy aromatic compound with an aldehyde and a polyamine.
  • the aldehyde is typically an aliphatic aldehyde containing 1 to 7 carbon atoms, and in most cases is formaldehyde or a compound such as formalin or a polyformaldehyde from which formaldehyde is derived during the reaction.
  • the substituted hydroxy aromatic compound is contacted with from about 0.1 to about 10 moles of polyamine and about 0.1 to about 10 moles of aldehyde per mole of substituted hydroxy aromatic compound.
  • the reactants are mixed and heated to a temperature above about 80°C. to initiate the reaction.
  • the reaction is carried out at a temperature from about 100° to about 250°C.
  • the resulting Mannich product has a predominantly benzylamine linkage between the aromatic compound and the polyamine.
  • the reaction can be carried out in an inert diluent such as mineral oil, benzene, toluene, naphtha, ligroin, or other inert solvents to facilitate control of viscosity, temperature, and reaction rate.
  • Suitable polyamines for use in preparation of the Mannich polyamine dispersants include, but are not limited to, methylene polyamines, ethylene polyamines, propylene polyamines, butylene polyamines, pentylene polyamines, hexylene polyamines and heptylene polyamines. The higher homologs of such amines and related aminoalkyl-substituted piperazines are also useful.
  • polyamines include ethylene diamine, triethylene tetramine, tris(2-aminoethyl)amine, propylene diamine, pentamethylene diamine, hexamethylene diamine, heptamethylene diamine, octamethylene diamine, decamethylene diamine, di(heptamethylene) triamine, pentaethylene hexamine, di(trimethylene) triamine, 2-heptyl-3-(2-aminopropyl)imidazoline, 1,3-bis(2-aminoethyl)imidazoline, 1-(2-aminopropyl)piperazine, 1,4-bis(2-aminoethyl)piperazine and 2-methyl-1-(2-aminobutyl)piperazine. Higher homologs, obtained by condensing two or more of the above mentioned amines, are also useful, as are the polyoxyalkylene polyamines.
  • the most preferred amines are the ethylene polyamines which can be depicted by the formula H2N(CH2CH2NH) n H wherein n is an integer from one to about ten. These include: ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, and the like, including mixtures thereof in which case n is the average value of the mixture.
  • ethylene polyamine mixtures usually contain minor amounts of branched species and cyclic species such as N-aminoethyl piperazine, N,N'-bis(aminoethyl)piperazine, N,N'-bis(piperazinyl)ethane, and like compounds.
  • the preferred commercial mixtures have approximate overall compositions falling in the range corresponding to diethylene triamine to pentaethylene hexamine, mixtures generally corresponding in overall makeup to tetraethylene pentamine being most preferred.
  • Methods for producing polyalkylene polyamines are known and reported in the literature. See for example U.S. Pat. Nos. 4,827,037; and 4,983,736; and EP Pub. Nos. 412,611; 412,612; 412,613; 412,614; and 412,615, and references cited therein.
  • the polyalkylene polyamines are especially useful in preparing the Mannich polyamine dispersants for reasons of cost and effectiveness.
  • Such polyamines are described in detail under the heading "Diamines and Higher Amines" in Kirk-Othmer, Encyclopedia of Chemical Technology , Second Edition, Vol. 7, pp. 22-39. They are prepared most conveniently by the reaction of an ethylene imine with a ring-opening reagent such as ammonia. These reactions result in the production of somewhat complex mixtures of polyalkylene polyamines which include cyclic condensation products such as piperazines. Because of their availability, these mixtures are particularly useful in preparing the Mannich polyamine dispersants. However, it will be appreciated that satisfactory dispersants can also be obtained by use of pure polyalkylene polyamines.
  • Alkylene diamines and polyalkylene polyamines having one or more hydroxyalkyl substituents on the nitrogen atom are also useful in preparing the Mannich polyamine dispersants. These materials are typically obtained by reaction of the corresponding polyamine with an epoxide such as ethylene oxide or propylene oxide.
  • Preferred hydroxyalkyl-substituted diamines and polyamines are those in which the hydroxyalkyl groups have less than about 10 carbon atoms.
  • hydroxyalkyl-substituted diamines and polyamines include, but are not limited to, N-(2-hydroxyethyl)ethylenediamine, N,N'-bis(2-hydroxyethyl)ethylenediamine, mono(hydroxypropyl)diethylenetriamine, di(hydroxypropyl)tetraethylenepentamine and N-(4-hydroxybutyl)tetramethylenediamine.
  • Higher homologs obtained by condensation of the above mentioned hydroxyalkyl-substituted diamines and polyamines through amine groups or through ether groups are also useful.
  • Amido-amine adducts such as are described in U.S. Pat. No. 5,034,018 can also be used in forming the Mannich base dispersants used in the practice of this invention.
  • Any conventional formaldehyde yielding reagent is useful for the preparation of the Mannich polyamine dispersants.
  • formaldehyde yielding reagents are trioxane, paraformaldehyde, trioxymethylene, aqueous formalin and gaseous formaldehyde.
  • Other aldehydes which can be used include acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, hexanal, heptanal, and mixtures of two or more of these.
  • Typical procedures for producing boronated Mannich base ashless dispersants involve heating one or more such dispersants with at least one boron compound under conditions yielding a boron-containing composition.
  • Suitable compounds of boron useful in forming boronated ashless dispersants suitable for use in the compositions of this invention include, for example, boron acids, boron oxides, boron esters, and amine or ammonium salts of boron acids.
  • Illustrative compounds include boric acid (sometimes referred to as orthoboric acid), boronic acid, tetraboric acid, metaboric acid, pyroboric acid, esters of such acids, such as mono-, di-, and tri-organic esters with alcohols or polyols having up to 20 or more carbon atoms (e.g., methanol, ethanol, 2-propanol, propanol, butanols, pentanols, hexanols, ethylene glycol, propylene glycol, trimethylol propane, diethanol amine, etc.), boron oxides such as boric oxide and boron oxide hydrate, and ammonium salts such as ammonium borate, ammonium pyroborate, etc.
  • boric acid sometimes referred to as orthoboric acid
  • boronic acid such as tetraboric acid, metaboric acid, pyroboric acid
  • esters of such acids such as mono-, di-, and
  • boron halides such as boron trifluoride, boron trichloride, and the like, are undesirable as they tend to introduce halogen atoms into the boronated dispersant, a feature which is detrimental from the environmental, toxicological and conservational standpoints.
  • Amine borane addition compounds and hydrocarbyl boranes can also be used, although they tend to be relatively expensive.
  • the preferred boron reagent is boric acid, H3BO3.
  • Mannich base dispersants for use in this invention are boronated Mannich base ashless dispersants formed by condensing about one molar proportion of long chain hydrocarbon-substituted phenol with from about 1 to 2.5 moles of formaldehyde and from about 0.5 to 2 moles of polyalkylene polyamine, and by boronating the resultant condensation product.
  • a variety of oil-soluble metal-free sulphur-containing antiwear and/or extreme pressure additives can be used in the practice of this invention. Examples are included within the categories of dihydrocarbyl polysulphides; sulphurized olefins; sulphurized fatty acid esters of both natural and synthetic origins; trithiones; sulphurized thienyl derivatives; sulphurized terpenes; sulphurized oligomers of C2-C8 monoolefins; and sulphurized Diels-Alder adducts such as those disclosed in U.S. reissue patent Re 27,331.
  • Specific examples include sulphurized polyisobutene of M ⁇ n 1,100, sulphurized isobutylene, sulphurized diisobutylene, sulphurized triisobutylene, dicyclohexyl polysulphide, diphenyl polysulphide, dibenzyl polysulphide, dinonyl polysulphide, and mixtures of di-tert-butyl polysulphide such as mixtures of di-tert-butyl trisulphide, di-tert-butyl tetrasulphide and di-tert-butyl pentasulphide, among others.
  • Combinations of such categories of sulphur-containing antiwear and/or extreme pressure agents can also be used, such as a combination of sulphurized isobutylene and di-tert-butyl trisulphide, a combination of sulphurized isobutylene and dinonyl trisulphide, a combination of sulphurized tall oil and dibenzyl polysulphide, and the like.
  • sulphur-containing antiwear and/or extreme pressure agents is comprised of the oil-soluble active sulphur-containing antiwear and/or extreme pressure agents.
  • these are substances which possess a linkage of two or more sulphur atoms (e.g., -S-S-, -S-S-S-, -S-S-S-S-, S-S-S-S-S-, etc.).
  • a sulphur-containing material is an active sulphur-containing material
  • the dried coupon is then rubbed with a paper towel moistened with acetone to remove any surface flakes formed by copper corrosion.
  • the coupon is then air-dried and weighed to the nearest 0.1 mg.
  • the difference in weight between the initial copper coupon and the coupon after the test represents the extent to which the copper was corroded under the test conditions. Therefore the larger the weight difference, the greater the copper corrosion, and thus the more active the sulphur compound. If the coupon weight loss is 30 milligrams or more, the sulphur-containing agent is considered "active".
  • Non-active sulphur-containing additives are materials which when subjected to the above copper coupon corrosion test give a weight loss of less than 30 milligrams. Examples of materials falling in this category include Anglamol 33 additive (a sulphurized isobutylene product of The Lubrizol Corporation), distilled di-tert-butyl trisulphide, and the like.
  • oil-soluble sulphur-containing antiwear and/or extreme pressure agents and more preferably oil-soluble active sulphur-containing antiwear and/or extreme pressure agents, that yield less than 25 ppm, and more preferably less than 10 ppm, of vapor space H2S when heated in the concentrated state for one week at 65°C.
  • materials of this type which yield no detectable vapor space H2S when tested under these conditions.
  • the most preferred oil-soluble metal-free sulphur-containing antiwear and/or extreme pressure agents from the cost-effectiveness standpoint are the sulphurized olefins containing at least 30% by weight of sulphur, the dihydrocarbyl polysulphides containing at least 25% by weight of sulphur, and mixtures of such sulphurized olefins and polysulphides.
  • sulphurized isobutylene having a sulphur content of at least 40% by weight and a chlorine content of less than 0.2% by weight is the most especially preferred material.
  • a component which contains both phosphorus and sulphur in its chemical structure is deemed a phosphorus-containing antiwear and/or extreme pressure agent rather than a sulphur-containing antiwear and/or extreme pressure agent.
  • the preferred phosphorus-containing antiwear and/or extreme pressure agents for use in the compositions of this invention are those which contain both phosphorus and nitrogen.
  • phosphorus- and nitrogen-containing antiwear and/or extreme pressure additives which can be employed in the practice of this invention are the phosphorus- and nitrogen-containing compositions of the type described in G.B. 1,009,913; G.B. 1,009,914; U.S. 3,197,405 and/or U.S. 3,197,496.
  • these compositions are formed by forming an acidic intermediate by the reaction of a hydroxy-substituted triester of a phosphorothioic acid with an inorganic phosphorus acid, phosphorus oxide or phosphorus halide, and neutralizing a substantial portion of said acidic intermediate with an amine or hydroxy-substituted amine.
  • Another type of phosphorus- and nitrogen-containing antiwear and/or extreme pressure additive which can be used in the compositions of this invention is the amine salts of hydroxy-substituted phosphetanes or the amine salts of hydroxy-substituted thiophosphetanes.
  • salts are derived from compounds of the formula wherein each of R1, R2, R3, R4, R5 and R6 is a hydrogen atom or a carbon-bonded organic group such as a hydrocarbyl group or a substituted hydrocarbyl group wherein the substituent(s) do(es) not materially detract from the predominantly hydrocarbonaceous character of the hydrocarbyl group;
  • X is a sulphur or an oxygen atom and Z is a hydroxyl group or an organic group having one or more acidic hydroxyl groups.
  • antiwear and/or extreme pressure agent examples include the amine salts hydroxyphosphetanes and the amine salts of hydroxy-thiophosphetanes typified by Irgalube 295 additive (Ciba-Geigy Corporation).
  • Another useful category of phosphorus- and nitrogen-containing antiwear and/or extreme pressure agents is comprised of the amine salts of partial esters of phosphoric and thiophosphoric acids.
  • Such compounds may be collectively represented by the formulas I, II, and III as follows: or mixtures thereof.
  • each of R1, R2, R3, R4, R5, R6,and R7 is, independently, a hydrocarbyl group and each of X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X11, and X12 is, independently, an oxygen atom or a sulphur atom.
  • the amine salts are formed with one or more partially esterified monothiophosphoric acids.
  • These are compounds of Formulas (I), (II), and (III) above wherein only one of X1, X2, X3, and X4, only one of X5, X6, X7, and X8, and only one of X9, X10, X11, and X12 is a sulphur atom.
  • the amine salts are formed with one or more partially esterified phosphoric acids.
  • These are compounds of Formulas (I), (II), and (III) above wherein all of X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X11, and X12 are oxygen atoms.
  • Another preferred sub-category of amine salts are those formed with one or more partially esterified dithiophosphoric acids. These are compounds of Formulas (I), (II), and (III) above wherein two of X1, X2, X3, and X4, two of X5, X6, X7, and X8, and two of X9, X10, X11, and X12 are sulphur atoms.
  • amine salts of Formulas (I), (II), and (III) above wherein three or four of X1, X2, X3, and X4, three or four of X5, X6, X7, and X8, and three or four of X9, X10, X11, and X12 are sulphur atoms.
  • oil-soluble amine salts are useful as components in the compositions of this invention, it is most preferred to include at least one oil-soluble amine salt of a dihydrocarbyl monothiophosphoric acid (one sulphur atom per molecule), either alone or in combination with at least one oil-soluble amine salt of a dihydrocarbyl phosphoric acid (no sulphur atom in the molecule).
  • Suitable salts or amine adducts of the partially esterified monothiophosphoric acids include such compounds as: Octylamine salt of O-monobutylthiophosphoric acid Octylamine salt of S-monobutylthiophosphoric acid Octylamine salt of O-monobutylthionophosphoric acid Octylamine salt of O,O-dibutylthiophosphoric acid Octylamine salt of O,S-dibutylthiophosphoric acid Octylamine salt of O,O-dibutylthionophosphoric acid Octylamine salt of O-monoisobutylthiophosphoric acid Octylamine salt of S-monoisobutylthiophosphoric acid Octylamine salt of O-monoisobutylthionophosphoric acid Octylamine salt of O,O-diisobutylthiophosphoric acid Octylamine salt of O,S-diisobutylthiophosphoric acid Octylamine
  • O,O-dihydrocarbylthionophosphoric acid is also known as O,O-dihydrocarbylphosphorothioic acid, (RO)2P(S)(OH).
  • O,O-dihydrocarbylphosphorothioic acid (RO)2P(S)(OH).
  • RO O,O-dihydrocarbylphosphorothioic acid
  • monothiophosphoric acid is used generically herein to refer to phosphoric acid having only one sulphur atom, and that sulphur atom can be bonded to the phosphorus atom either by a single bond or by a double bond.
  • dithiophosphoric acid refers to phosphoric acid having two sulphur atoms both of which can be bonded to the phosphorus atom by single bonds, or one of which is bonded to the phosphorus atom by a double bond and the other of which is bonded to the phosphorus atom by single bond.
  • trithiophosphoric acid wherein two of the three sulphur atoms can be bonded to the phosphorus atom by single bonds and the third by either a single or double bond.
  • amine salts of partial esters of phosphoric acid include the following: Octylamine salt of monobutylphosphoric acid Octylamine salt of dibutylphosphoric acid Octylamine salt of monoisobutylphosphoric acid Octylamine salt of diisobutylphosphoric acid Octylamine salt of monoamylphosphoric acid Octylamine salt of diamylphosphoric acid Octylamine salt of monohexylphosphoric acid Octylamine salt of dihexylphosphoric acid Octylamine salt of monoheptylphosphoric acid Octylamine salt of diheptylphosphoric acid Octylamine salt of mono-2-ethylhexylphosphoric acid Octylamine salt of di-2-ethylhexylphosphoric acid Octylamine salt of monooctylphosphoric acid Octylamine salt of dioctylphosphoric acid Octylamine salt of monononylphosphoric acid Octylamine salt of dinonyl
  • Octylamine salts or adducts have been set forth in the above two listings merely for purposes of illustration.
  • use can be made of nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, cyclohexylamine, phenylamine, mesitylamine, oleylamine, cocoamine, soyamine, C8 tertiary alkyl primary amine, C12 ⁇ 14 tertiary alkyl primary amine, C22 ⁇ 24 tertiary alkyl primary amine, phenethylamine, etc., salts or adducts of partially esterified phosphoric, monothiophosphoric, dithiophosphoric, trithi
  • the preferred amine salts are salts of aliphatic amines, especially the saturated or olefinically unsaturated aliphatic primary amines, such as n-octylamine, 2-ethylhexylamine, tert-octylamine, n-decylamine, the C10, C12, C14 and C16 tertiary alkyl primary amines (either singly or in any combinations thereof, such as a mixture of the C12 and C14 tertiary alkyl primary amines), n-undecylamine, a mixture of C14 to C18 tertiary alkyl primary amines, lauryl amine, hexadecylamine, heptadecylamine, octadecylamine, the C22 and C24 tertiary alkyl primary amines (either singly or in combination), decenylamine, dodecenylamine,
  • Secondary hydrocarbyl amines and tertiary hydrocarbyl amines can also be used either alone or in combination with each other or in combination with primary amines.
  • any combination of primary, secondary and/or tertiary amines, whether monoamine or polyamine, can be used in forming the salts or adducts.
  • the amines used can be in the form of polyalkylene polyamines; functionally-substituted polyamines such as a succinimide or succinamide of a polyalkylene polyamines such as a polyisobutenyl succinimide of diethylene triamine, a polyisobutenyl succinimide of triethylene tetramine, a polyisobutenyl succinimide of tetraethylene pentamine, a polyisobutenyl succinimide of pentaethylene hexamine (including succinimides made from commercially available polyethylene polyamine mixtures which contain linear, branched and cyclic species); and Mannich bases derived from polyalkylene polyamines of the types just described.
  • functionally-substituted polyamines such as a succinimide or succinamide of a polyalkylene polyamines such as a polyisobutenyl succinimide of diethylene triamine, a polyisobuteny
  • the polyalkylene polyamines whether in the free state or in the form of a succinimide, succinamide, or Mannich base, can be partially boronated, partially phosphorylated, or partially acylated with a reagent such as maleic anhydride, malic acid, itaconic acid, itaconic anhydride, thiomalic acid, fumaric acid, and the like, provided that such boronated or phosphorylated or acylated amine or amine moiety contains at least sufficient residual basicity to enable it to form a salt with the partially esterified phosphoric or thiophosphoric acid.
  • Alkylene polyamines in the form of succinimides, succinamides or Mannich bases which have been boronated and phosphorylated are described for example in U.S. Pat. No. 4,857,214.
  • Especially preferred amines are alkyl monoamines and alkenyl monoamines having from about 8 to about 24 carbon atoms in the molecule.
  • Amines having less than 8 carbon atoms can be used, including methyl amine, etc., provided the resultant amine salt is oil-soluble.
  • amines having more than 24 carbon atoms can be used, again with the proviso that the resultant amine salt is oil soluble.
  • amine salts of partially esterified monothiophosphoric acids are usually made by reacting a mono- and/or dihydrocarbyl phosphite with sulphur or an active sulphur-containing compound such as are referred to above under the caption "Sulphur-Containing Antiwear and/or Extreme Pressure Agents" and one or more primary or secondary amines. Such reactions tend to be highly exothermic reactions which can become uncontrollable, if not conducted properly.
  • One preferred method of forming these amine salts involves a process which comprises (i) introducing, at a rate such that the temperature does not exceed about 60°C, one or more dihydrocarbyl hydrogen phosphites, such as a dialkyl hydrogen phosphite, into an excess quantity of one or more active sulphur-containing materials, such as sulphurized branched-chain olefin (e.g., isobutylene, diisobutylene, triisobutylene, etc.), while agitating the mixture so formed, (ii) introducing into this mixture, at a rate such that the temperature does not exceed about 60°C, one or more aliphatic primary or secondary amines, preferably one or more aliphatic primary monoamines having in the range of about 8 to about 24 carbon atoms per molecule while agitating the mixture so formed, and (iii) maintaining the temperature of the resultant agitated reaction mixture at between about 55 and about 60°C until reaction is substantially complete.
  • Another suitable way of producing these amine salts is to concurrently introduce all three of the reactants into the reaction zone at suitable rates and under temperature control such that the temperature does not exceed about 60°C.
  • Another preferred way of forming amine salts of partially esterified monothiophosphoric acids is to pre-react elemental sulphur with the amine for a short period of time and then add thereto the appropriate dihydrocarbyl hydrogen phosphite at a rate such that the temperature does not become excessive and the reaction uncontrollable.
  • Another component for use in the compositions of this invention is one or more amine salts of one or more long chain carboxylic acids.
  • the acids can be monocarboxylic acids or polycarboxylic acids. Generally speaking, these acids contain from about 8 to about 50 carbon atoms in the molecule and thus the salts are oil-soluble.
  • a variety of amines can be used in forming such salts, including primary, secondary and tertiary amines, and the amines can be monoamines, or polyamines. Further, the amines may be cyclic or acyclic aliphatic amines, aromatic amines, heterocyclic amines, or amines containing various mixtures of acyclic and cyclic groups.
  • Preferred amine salts include the alkyl and alkenyl amine salts of alkanoic acids and/or alkenoic acids, the alkyl and alkenyl amine salts of alkanedioic acids and/or alkenedioic acids and any combination of the foregoing.
  • the amine salts are formed by classical chemical reactions, namely, the reaction of an amine or mixture of amines, with the appropriate acid or mixture of acids. Accordingly, further discussion concerning methods for the preparation of such materials would be redundant.
  • amine salts of long-chain acids that may be used are the following: the octyl amine salt of C36 dimer acid (made by dimerization of linoleic acid), lauryl ammonium laurate (i.e.
  • lauryl amine salt of lauric acid stearyl ammonium laurate, cyclohexyl ammonium laurate, octyl ammonium laurate, pyridine laurate, aniline laurate, lauryl ammonium stearate, stearyl ammonium stearate, cyclohexyl ammonium stearate, octylammonium stearate, pyridine stearate, aniline stearate, lauryl ammonium octanoate, stearyl ammonium octanoate, cyclohexyl ammonium octanoate, octyl ammonium octanoate, pyridine octanoate, aniline octanoate, nonyl ammonium laurate, nonyl ammonium stearate, nonyl ammonium octanoate, lauryl ammoni
  • amine salts for use in practice of this invention are the primary amine salts of long chain monocarboxylic acids in which the amine thereof is a monoalkyl monoamine, RNH2; the secondary amine salts of long chain monocarboxylic acids in which the amine thereof is a dialkyl monoamine, R2NH; the tertiary amine salts of long chain monocarboxylic acids in which the amine thereof is a trialkyl monoamine, R3N; the bis primary amine salts of long chain dicarboxylic acids in which the amine thereof is a monoalkyl monoamine, RNH2; the bis secondary amine salts of long chain dicarboxylic acids in which the amine thereof is a dialkyl monoamine, R2NH; the bis tertiary amine salts of long chain dicarboxylic acids in which the amine thereof is a trialkyl monoamine, R3N; and mixtures thereof.
  • R is an alkyl group which contains
  • the free amines which can be used in forming the compositions of this invention can be any of the amines referred to above in connection with the amine salts of partial esters of phosphoric acid or thiophosphoric acids or in connection with the amine salts of carboxylic acids, provided that the amines are oil-soluble.
  • the preferred type is composed of alkyl primary monoamines, and alkenyl primary monoamines, especially those containing from about 6 to about 24 carbon atoms.
  • amines examples include hexylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, eicosylamine, docosylamine, tetracosylamine, oleylamine, cocoamine, soyamine, C12 ⁇ 14 tertiary alkyl primary amine, C22 ⁇ 24 tertiary alkyl primary amine, and the like.
  • the free amine used in the compositions will correspond to the amine used in forming either the amine salt of the phosphorus acid or the amine salt of the carboxylic acid, or both.
  • free amine refers to the form of the amine as it is charged into the blender or mixing vessel in which the additive concentrate or the lubricating oil or functional fluid composition is being formed. Some or all of the free amine may complex with or react with other components being used in the product being formed, such as acidic additive components. Thus the term “free amine” does not signify or imply that the amine must remain free -- all or part of it may remain uncomplexed and unreacted, but this is not a requirement.
  • components such as amine salts of phosphorus acids and amine salts of carboxylic acid can be preformed prior to being formulated in a composition of this invention, or such components can, in whole or in part, be formed in situ.
  • This group of compounds is composed of O,O-dihydrocarbyl-S-hydrocarbyl thiothionophosphates (also known as O,O-dihydrocarbyl-S-hydrocarbyl phosphorothiothionates) which can be represented by the general formula: wherein each of R1, R2, and R3 is independently a hydrocarbyl group, especially where R3 is an alicyclic hydrocarbyl group. Particularly preferred are the O,O-dialkyl-S-hydrocarbyl phosphorothiothionates wherein R3 is an alicyclic group an R1 and R2 are alkyl groups each having up to about 18 carbon atoms and most preferably up to about 12 carbon atoms.
  • Exemplary compounds suitable for use in the compositions of this invention include such compounds as trioctylphosphorothiothionate, tridecylphosphorothiothionate, trilaurylphosphorothiothionate, O,O-diethyl bicyclo[2.2.1]-hepten-2-yl phosphorothiothionate, O,O-diethyl 7,7-dimethyl-bicyclo[2.2.1]-5-hepten-2-yl phosphorothiothionate, the product formed by reaction of dithiophosphoric acid-O,O-dimethyl ester with cis-endomethylene-tetrahydrophthalic acid dimethyl ester, the product formed by reaction of dithiophosphoric acid-O,O-dimethyl ester with cis-endomethylene-tetrahydrophthalic acid dibutyl ester, the product formed by reaction of dithiophosphoric acid-O,O-dibutyl ester with cis-endomethylene
  • Typical additives which may be employed as demulsifiers include alkyl benzene sulphonates, polyethylene oxides, polypropylene oxides, block copolymers of ethylene oxide and propylene oxide, salts and esters or oil soluble acids, and the like.
  • oxyalkylated trimethylol alkanes with molecular weights in the range of 1,000 to 10,000, and preferably in the range of 3,000 to 8,000.
  • the oxyalkylated trimethylol alkane is an oxyalkylated trimethylol ethane or propane, especially where the oxyalkylene groups are composed of a mixture of propyleneoxy and ethylenoxy groups and where these groups are so disposed as to form relatively hydrophobic blocks adjacent the trimethylol group and relatively hydrophilic blocks remote the trimethylol group.
  • Typical oxyalkylated trimethylol propane demulsifiers are described in U.S. Pat. No. 3,101,374.
  • Pluradot HA-510 has an average molecular weight of 4,600 and Pluradot HA-530 has an average molecular weight of about 5,300.
  • Pluradot additives are propoxylated and ethoxylated trimethylol propanes.
  • demulsifers are oxyalkylated alkyl phenol-formaldehyde condensation products. Typically, these products have molecular weights in the range of about 4,000 to about 6,000 and are comprised of lower alkyl substituted phenol moieties joined together by methylene groups and in which the hydroxyl groups of the phenolic moieties have been ethoxylated.
  • One such commercial product is marketed by Ceca S.A. of Paris, France under the "Prochinor GR77" trade name.
  • the product is supplied as a concentrate in an aromatic solvent and the active ingredient is believed to be an ethoxylated nonylphenol-formaldehyde condensate of molecular weight 4,200 (by gel permeation chromatography calibrated with polystyrene).
  • demulsifier is comprised of the tetra-polyoxyalkylene derivatives of ethylene diamine, especially the tetra-poly(oxyethylene)-poly(oxypropylene) derivatives of ethylene diamine.
  • Materials of this type are available commercially from BASF Corporation under the "Tetronics" trademark. Materials of this general type are described in U.S. Pat. No. 2,979,528.
  • TOLAD 286K a proprietary product, identified as TOLAD 286K, is understood to be a mixture of these components dissolved in a solvent composed of alkyl benzenes.
  • TOLAD 286 is believed to be a similar product wherein the solvent is composed of a mixture of heavy aromatic naphtha and isopropyl alcohol.
  • Preferred demulsifiers are proprietary materials available from BASF Corporation under the Pluronic trademark. These are block copolymers of propylene oxide and ethylene oxide.
  • One type of such additives is comprised of thiazoles, triazoles and thiadiazoles.
  • examples of such compounds include benzotriazole, tolyltriazole, octyltriazole, decyltriazole, dodecyltriazole, 2-mercaptobenzothiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-5-hydrocarbylthio-1,3,4-thiadiazoles, 2-mercapto-5-hydrocarbyldithio-1,3,4-thiadiazoles, 2,5-bis(hydrocarbylthio)-1,3,4-thiadiazoles, and 2,5-bis(hydrocarbyldithio)-1,3,4-thiadiazoles.
  • the preferred compounds are the 1,3,4-thiadiazoles, especially the 2-hydrocarbyldithio-5-mercapto-1,3,4-dithiadiazoles and the 2,5-bis(hydrocarbyldithio)-1,3,4-thiadiazoles, a number of which are available as articles of commerce.
  • Such compounds are generally synthesized from hydrazine and carbon disulfide by known procedures. See for example U.S. Pat. Nos. 2,749,311; 2,760,933; 2,765,289; 2,850,453; 2,910,439; 3,663,561; 3,862,798; 3,840,549; and 4,097,387.
  • Suitable inhibitors of copper corrosion include ether amines; polyethoxylated compounds such as ethoxylated amines, ethoxylated phenols, and ethoxylated alcohols; imidazolines; and the like. Materials of these types are well known to those skilled in the art and a number of such materials are available as articles of commerce.
  • the oleaginous fluids and additive concentrates of this invention can and preferably will contain additional components in order to partake of the properties which can be conferred to the overall composition by such additional components.
  • additional components will, to a large extent, be governed by the particular use to which the ultimate oleaginous composition (lubricant or functional fluid) is to be subjected.
  • the additive combinations of this invention can be incorporated in a wide variety of lubricants and functional fluids in effective amounts to provide suitable active ingredient concentrations.
  • the base oils not only can be hydrocarbon oils of lubricating viscosity derived from petroleum (or tar sands, coal, shale, etc.), but also can be natural oils of suitable viscosities such as rapeseed oil, etc., and synthetic oils such as hydrogenated polyolefin oils; poly- ⁇ -olefins (e.g., hydrogenated or unhydrogenated ⁇ -olefin oligomers such as hydrogenated poly-1-decene); alkyl esters of dicarboxylic acids; complex esters of dicarboxylic acid, polyglycol and alcohol; alkyl esters of carbonic or phosphoric acids; polysilicones; fluorohydrocarbon oils; and mixtures of mineral, natural and/or synthetic oils in any proportion, etc.
  • base oil for this disclosure includes all the foregoing.
  • the additive combinations of this invention can thus be used in lubricating oil and functional fluid compositions, such as automotive crankcase lubricating oils, automatic transmission fluids, gear oils, hydraulic oils, cutting oils, etc., in which the base oil of lubricating viscosity is a mineral oil, a synthetic oil, a natural oil such as a vegetable oil, or a mixture thereof, e.g. a mixture of a mineral oil and a synthetic oil.
  • the base oil of lubricating viscosity is a mineral oil, a synthetic oil, a natural oil such as a vegetable oil, or a mixture thereof, e.g. a mixture of a mineral oil and a synthetic oil.
  • Suitable mineral oils include those of appropriate viscosity refined from crude oil of any source including Gulf Coast, Midcontinent, Pennsylvania, California, Alaska, Middle East, North Sea and the like. Standard refinery operations may be used in processing the mineral oil.
  • general types of petroleum oils useful in the compositions of this invention are solvent neutrals, bright stocks, cylinder stocks, residual oils, hydrocracked base stocks, paraffin oils including pale oils, and solvent extracted naphthenic oils. Such oils and blends of them are produced by a number of conventional techniques which are widely known by those skilled in the art.
  • the base oil can consist essentially of or comprise a portion of one or more synthetic oils.
  • suitable synthetic oils are homo- and inter-polymers of C2-C12 olefins, carboxylic acid esters of both monoalcohols and polyols, polyethers, silicones, polyglycols, silicates, alkylated aromatics, carbonates, thiocarbonates, orthoformates, phosphates and phosphites, borates and halogenated hydrocarbons.
  • oils are homo- and interpolymers of C2-C12 monoolefinic hydrocarbons, alkylated benzenes (e.g., dodecyl benzenes, didodecyl benzenes, tetradecyl benzenes, dinonyl benzenes, di-(2-ethylhexyl)benzenes, wax-alkylated naphthalenes); and polyphenyls (e.g., biphenyls, terphenyls).
  • alkylated benzenes e.g., dodecyl benzenes, didodecyl benzenes, tetradecyl benzenes, dinonyl benzenes, di-(2-ethylhexyl)benzenes, wax-alkylated naphthalenes
  • polyphenyls e.g., biphenyls,
  • Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc. constitute another class of synthetic oils. These are exemplified by the oils prepared through polymerization of alkylene oxides such as ethylene oxide or propylene oxide, and the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methyl polyisopropylene glycol ether having an average molecular weight of 1000, diphenyl ether of polyethylene glycol having a molecular weight of 500-1000, diethyl ether of polypropylene glycol having a molecular weight of 1000-1500) or mono- and polycarboxylic esters thereof, for example, the acetic acid ester, mixed C3-C6 fatty acid esters, or the C13 Oxo acid diester of tetraethylene glycol.
  • alkylene oxides such as ethylene oxide or propylene oxide
  • Another suitable class of synthetic oils comprises the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol).
  • dicarboxylic acids e.g., phthalic acid, succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer
  • alcohols e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol.
  • esters include dibutyl adipate, di(2-ethylhexyl) adipate, didodecyl adipate, di(tridecyl) adipate, di(2-ethylhexyl) sebacate, dilauryl sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, di(eicosyl) sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid.
  • esters which may be used include those made from C3-C18 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol and dipentaerythritol.
  • Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils comprise another class of synthetic lubricants (e.g., tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl) silicate, tetra-(p-tert-butylphenyl) silicate, poly(methyl)siloxanes, and poly(methylphenyl)siloxanes.
  • synthetic lubricants e.g., tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl) silicate, tetra-(p-tert-butylphenyl) silicate, poly(methyl)siloxanes, and poly(methylphenyl)siloxanes.
  • Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, triphenyl phosphite, and diethyl ester of decane phosphonic acid.
  • liquid esters of phosphorus-containing acids e.g., tricresyl phosphate, trioctyl phosphate, triphenyl phosphite, and diethyl ester of decane phosphonic acid.
  • Also useful as base oils or as components of base oils are hydrogenated or unhydrogenated liquid oligomers of C6-C16 ⁇ -olefins, such as hydrogenated or unhydrogenated oligomers formed from 1-decene.
  • Methods for the production of such liquid oligomeric 1-alkene hydrocarbons are known and reported in the literature. See for example U. S. Pat. Nos. 3,749,560; 3,763,244; 3,780,128; 4,172,855; 4,218,330; 4,902,846; 4,906,798; 4,910,355; 4,911,758; 4,935,570; 4,950,822; 4,956,513; and 4,981,578.
  • hydrogenated 1-alkene oligomers of this type are available as articles of commerce, e.g., under the trade designations ETHYLFLO 162, ETHYLFLO 164, ETHYLFLO 166, ETHYLFLO 168, ETHYLFLO 170, ETHYLFLO 174, and ETHYLFLO 180 poly- ⁇ -olefin oils (Ethyl Corporation; Ethyl Canada Limited; Ethyl S.A.). Blends of such materials can also be used in order to adjust the viscometrics of the given base oil. Suitable 1-alkene oligomers are also available from other suppliers. As is well known, hydrogenated oligomers of this type contain little, if any, residual ethylenic unsaturation.
  • Preferred oligomers are formed by use of a Friedel-Crafts catalyst (especially boron trifluoride promoted with water or a C1 ⁇ 20 alkanol) followed by catalytic hydrogenation of the oligomer so formed using procedures such as are described in the foregoing U.S. patents.
  • a Friedel-Crafts catalyst especially boron trifluoride promoted with water or a C1 ⁇ 20 alkanol
  • catalyst systems which can be used to form oligomers of 1-alkene hydrocarbons, which, on hydrogenation, provide suitable oleaginous liquids include Ziegler catalysts such as ethyl aluminum sesquichloride with titanium tetrachloride, aluminum alkyl catalysts, chromium oxide catalysts on silica or alumina supports and a system in which a boron trifluoride catalyst oligomerization is followed by treatment with an organic peroxide.
  • Ziegler catalysts such as ethyl aluminum sesquichloride with titanium tetrachloride, aluminum alkyl catalysts, chromium oxide catalysts on silica or alumina supports and a system in which a boron trifluoride catalyst oligomerization is followed by treatment with an organic peroxide.
  • unhydrogenated 1-alkene oligomers can be used as the base oil or as a component in a base oil blend.
  • various proprietary synthetic lubricants such as KETJENLUBE synthetic oil of Akzo Chemicals can be employed either as the sole base lubricant or as a component of the base lubricating oil.
  • Typical natural oils that may be used as base oils or as components of the base oils include castor oil, olive oil, peanut oil, rapeseed oil, corn oil, sesame oil, cottonseed oil, soybean oil, sunflower oil, safflower oil, hemp oil, linseed oil, tung oil, oiticica oil, jojoba oil, and the like. Such oils may be partially or fully hydrogenated, if desired.
  • the base oils used in the compositions of this invention may be composed of (i) one or more mineral oils, (ii) one or more synthetic oils, (iii) one or more natural oils, or (iv) a blend of (i) and (ii), or (i) and (iii), or (ii) and (iii), or (i), (ii) and (iii) does not mean that these various types of oils are necessarily equivalents of each other.
  • Certain types of base oils may be used in certain compositions for the specific properties they possess such as biodegradability, high temperature stability, non-flammability or lack of corrosivity towards specific metals (e.g. silver or cadmium).
  • the components of the additive compositions of this invention are employed in the oleaginous liquids (e.g., lubricating oils and functional fluids) in minor amounts sufficient to improve the performance characteristics and properties of the base oil or fluid.
  • the amount employed is most preferably the amount sufficient to render the pH (determined as described hereinafter) of the finished additive concentrate as formed within the range of 6 to 8.
  • the amounts of the other components will vary in accordance with such factors as the viscosity characteristics of the base oil or fluid employed, the viscosity characteristics desired in the finished product, the service conditions for which the finished product is intended, and the performance characteristics desired in the finished product.
  • Typical Range Preferred Range Mannich base 0.1 - 3 0.2 - 2 S-contg antiwear/E.P. agent 0.1 - 6 1 - 4 P-contg antiwear/E.P.
  • additives are multifunctional additives capable of contributing more than a single property to the blend in which they are used.
  • the amount used should of course be sufficient to achieve the function(s) and result(s) desired therefrom.
  • the individual components can be separately blended into the base oil or fluid or can be blended therein in various subcombinations, if desired. Moreover, such components can be blended in the form of separate solutions in a diluent. Except for viscosity index improvers and/or pour point depressants (which in many instances are blended apart from other components), it is preferable to blend the other selected components into the base oil by use of an additive concentrate of this invention, as this simplifies the blending operations, reduces the likelihood of blending errors, and takes advantage of the compatibility and solubility characteristics afforded by the overall concentrate.
  • the additive concentrates of this invention will contain the individual components in amounts proportioned to yield finished oil or fluid blends consistent with the concentrations tabulated above.
  • the additive concentrate will contain one or more diluents such as light mineral oils, to facilitate handling and blending of the concentrate.
  • concentrates containing up to 80% by weight of one or more diluents or solvents can be used.
  • the oleaginous liquids provided by this invention can be used in a variety of applications.
  • they can be employed as crankcase lubricants, gear oils, hydraulic fluids, manual transmission fluids, automatic transmission fluids, cutting and machining fluids, brake fluids, shock absorber fluids, heat transfer fluids, quenching oils, transformer oils, and the like.
  • the compositions are particularly suitable for use as automotive and industrial gear oils.
  • compositions of this invention one either purchases or synthesizes each of the respective individual components to be used in the formulation or blending operation. Unless one is already in the commercial manufacture of one or more such components, it is usually simpler and thus preferable to purchase, to the extent possible, the ingredients to be used in the compositions of this invention. If it is desired to synthesize one or more components, use may be made of synthesis procedures referred to in the literature, including, but by no means limited to, the applicable references cited herein. In some cases, the components can be formed in situ by in situ reactions between or among components introduced into the mixture.
  • amine salts of monothiophosphoric acid esters can be formed in situ by introducing into the blending vessel a material such as sulphurized isobutylene and one or more amines, followed by the introduction of one or more dihydrocarbyl hydrogen phosphites.
  • the formulation or blending operations are relatively simple and involve mixing together in a suitable container or vessel, using a dry, inert atmosphere where necessary or desirable, appropriate proportions of the selected ingredients.
  • Those skilled in the art are cognizant of and familiar with the procedures suitable for formulating and blending additive concentrates and lubricant compositions.
  • the order of addition of components to the blending tank or vessel is not critical provided of course, that the components being blended at any given time are not incompatible or excessively reactive with each other. Agitation such as with mechanical stirring equipment is desirable to facilitate the blending operation.
  • the additive ingredients When forming the lubricant compositions of this invention, it is usually desirable to introduce the additive ingredients into the base oil with stirring and application of mildly elevated temperatures, as this facilitates the dissolution of the components in the oil and achievement of product uniformity.
  • reaction vessel To a reaction vessel are charged 38.0 parts of sulphurized isobutylene, 14.0 parts of a product formed by reaction of dicyclopentadiene with dithiophosphoric acid-0,0-dialkyl ester in which on a molar basis 40% of the alkyl groups are isopropyl, 40% are isobutyl and 20% are 2-ethylhexyl, 4.76 parts of dibutyl hydrogen phosphite, and 1.75 parts of 2-ethylhexyl acid phosphate. Throughout this addition, the components of the reaction vessel are agitated and maintained at 30°C for 10 minutes.
  • Primene® 81-R amine a tert-alkyl primary amine mixture in the C12-C14 range; Rohm & Haas
  • the mixture is stirred for 20 minutes without application of heat.
  • another 4.9 parts of this tertiary alkyl monoamine product is added and the contents of the reaction vessel are maintained at 50°C for 1 hour with continuous stirring.
  • 4.31 parts of oleic acid and 0.58 part of M530 defoamer an antifoam concentrate of Monsanto Company
  • reaction vessel To a reaction vessel are charged 38.3 parts of sulphurized isobutylene, 14.3 parts of di-tert-nonyl polysulphide, 5.7 parts of dibutyl hydrogen phosphite, 0.1 part of tolyltriazole, and 2.9 parts of amyl acid phosphate. Throughout this addition, the components of the reaction vessel are agitated and maintained at 30°C for 10 minutes. To this mixture are added 3.7 parts of Primene 81-R amine, 3.7 parts of C16 and C18 primary amines, 1.0 part of octyl amine, and 3.2 parts of process oil, and the mixture is stirred for 20 minutes while maintaining the contents of the reaction vessel at 50°C for 1 hour with continuous stirring.
  • reaction vessel To a reaction vessel are charged 35.8 parts of sulphurized isobutylene, 3.6 parts of dibutyl hydrogen phosphite, 18.9 parts of a product formed by reaction of dicyclopentadiene with dithiophosphoric acid-0,0-dialkyl ester in which on a molar basis 40% of the alkyl groups are isopropyl, 40% are isobutyl and 20% are 2-ethylhexyl, and 1.7 parts of 2-ethylhexyl acid phosphate. Throughout this addition, the components of the reaction vessel are agitated and maintained at 30°C for 10 minutes.
  • reaction vessel To a reaction vessel are charged 35.1 parts of sulphurized isobutylene, 3.8 parts of dibutyl hydrogen phosphite, 16.6 parts of a product formed by reaction of dicyclopentadiene with dithiophosphoric acid-0,0-dialkyl ester in which on a molar basis 40% of the alkyl groups are isopropyl, 40% are isobutyl and 20% are 2-ethylhexyl, and 1.0 part of 2-ethylhexyl acid phosphate. Throughout this addition, the components of the reaction vessel are agitated and maintained at 30°C for 10 minutes.
  • An SAE 80W-90 mineral oil blend of this invention is formed by blending together the following components in the amounts specified: 6.5% of the additive package of Example 1; 40.0% of high viscosity index 115 Solvent Neutral base oil (Shell Oil Company); 52.5% of high viscosity index 650b bright stock base oil (Shell Oil Company); and 1.0% of HiTEC® 623 additive; (an alkyl polymethacrylate pour point depressant; Ethyl Petroleum Additives, Inc.; Ethyl Petroleum Additives, Ltd.; Ethyl S.A.; Ethyl Canada Ltd.)
  • An SAE 80W-90 mineral oil blend of this invention is formed by blending together the following components in the amounts specified: 3.2% of the additive package of Example 1; 95.8% of high viscosity index 115 Solvent Neutral base oil (Shell Oil Company); 1.0% of HiTEC® 623 additive.
  • a synthetic oil-based lubricating oil composition of this invention is formed by blending together the following components in the amounts specified: 6.5% of the additive package of Example 1; 39.9% of ETHYLFLO 168 poly- ⁇ -olefin oligomer oil (an 8 cSt base oil) (ETHYLFLO is a trademark of Ethyl Corporation); 43.6% of a low chlorine version of ETHYLFLO 174 poly- ⁇ -olefin oligomer oil (a 40 cSt base oil); and 10.0% of KETJENLUBE synthetic oil (KETJENLUBE is a trademark of Akzo Chemicals).
  • the procedure used in determining pH of preferred additive concentrates of this invention involves diluting the sample of the composition in a mixture of methanol and toluene and then assaying "non-aqueous" pH with a conventional pH probe as used in aqueous systems.
  • the basic equipment used is a potentiometer such as Beckman Zeromatic IV pH meter, Beckman Instruments Inc., available from CMS, catalog number 257-902, or equivalent; a glass indicating electrode 0-11 pH range, available from CMS, catalog number 39322 or equivalent; indicating electrode cable, available from Beckman Instruments Inc., catalog number 598979, or equivalent; saturated calomel reference electrode with ground glass sleeve junction, available from CMS, catalog number 39420, or equivalent; and reference electrode cable, available from Beckman Instruments Inc., catalog number 598982, or equivalent.
  • a potentiometer such as Beckman Zeromatic IV pH meter, Beckman Instruments Inc., available from CMS, catalog number 257-902, or equivalent
  • a glass indicating electrode 0-11 pH range available from CMS, catalog number 39322 or equivalent
  • indicating electrode cable available from Beckman Instruments Inc., catalog number 598979, or equivalent
  • saturated calomel reference electrode with ground glass sleeve junction available from CMS, catalog number 39
  • the reagents used in this procedure are reagent grade toluene; potassium chloride; reagent grade methanol; buffer solution, pH 7.00, available from CMS, catalog number 061-622, or equivalent; buffer solution, pH 10.00, available from CMS, catalog number 061-648, or equivalent; and buffer solution, pH 4.00, available from CMS, catalog number 061-614, or equivalent.
  • the steps used in the procedure are as follows:
  • Copper corrosion ratings for the purposes of this invention are conducted using the standard ASTM D-130 procedure modified to the extent that the additive concentrate to be tested is first stored in an oven for 120 hours at 65°C. Then the concentrate is blended into the test oil to the selected test concentration and the test is conducted at 121°C.
  • oil-soluble is used in the sense that the component in question has sufficient solubility in the selected base oil in order to dissolve therein at ordinary temperatures to a concentration at least equivalent to the minimum concentration specified herein for use of such component.
  • solubility of such component in the selected base oil will be in excess of such minimum concentration, although there is no requirement that the component be soluble in the base oil in all proportions.
  • certain useful additives do not completely dissolve in base oils but rather are used in the form of stable suspensions or dispersions. Additives of this type can be employed in the compositions of this invention, provided they do not significantly interfere with the performance or usefulness of the composition in which they are employed.
  • the lubricant compositions of this invention may be used in a wide variety of automotive and industrial gear applications. Examples of such applications include use in hypoid axles and in mechanical steering devices in passenger cars and in cross-country vehicles. Further examples include use in hypoid axles, planetary hub reaction axles, mechanical steering and transfer gear boxes in utility vehicles such as trucks.
  • lubricant compositions of this invention may additionally be used include pinion and planetary hub reduction gear boxes, synchromesh gear boxes, power take-off gears and limited slip rear axles, and synchroniser type gear boxes.
  • the oleaginous compositions of this invention may also be used in transmission systems, including manual and automatic transmissions, and hydraulic systems operating under heavy loads and pressures. Vehicular crankcase usage is also possible using compositions of this invention. Other uses include cutting, shaping, and machining fluids, annealing fluids, transformer oils, and the like.
  • the lubricants of this invention are of particular usefulness in gear oil applications.

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EP91308198A 1991-09-09 1991-09-09 Öladditivkonzentrate und Schmieröle mit verbesserten Leistungen Expired - Lifetime EP0531585B1 (de)

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EP91308198A EP0531585B1 (de) 1991-09-09 1991-09-09 Öladditivkonzentrate und Schmieröle mit verbesserten Leistungen
DE69130450T DE69130450T2 (de) 1991-09-09 1991-09-09 Öladditivkonzentrate und Schmieröle mit verbesserten Leistungen
CA002076921A CA2076921A1 (en) 1991-09-09 1992-08-26 Oil additive concentrates and lubricants of enhanced performance capabilities
AU22804/92A AU657563B2 (en) 1991-09-09 1992-09-07 Oil additive concentrates and lubricants of enhanced performance capabilities
JP4265540A JPH05209186A (ja) 1991-09-09 1992-09-09 増強された性能の油添加剤濃縮物および潤滑剤

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EP91308198A EP0531585B1 (de) 1991-09-09 1991-09-09 Öladditivkonzentrate und Schmieröle mit verbesserten Leistungen

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EP0531585A1 true EP0531585A1 (de) 1993-03-17
EP0531585B1 EP0531585B1 (de) 1998-11-04

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JP (1) JPH05209186A (de)
AU (1) AU657563B2 (de)
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Cited By (26)

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EP0578435A1 (de) * 1992-07-09 1994-01-12 Ethyl Petroleum Additives Limited Modifizierung der Reibung synthetischer Getriebeöle
EP0620268A1 (de) * 1993-03-16 1994-10-19 Ethyl Petroleum Additives Limited Getriebeschmieröle mit verbesserten Reibungseigenschaften
EP0692012A1 (de) * 1993-04-01 1996-01-17 Ethyl Corporation Zahnradölzusammensetzung
EP0695799A3 (de) * 1994-08-03 1996-04-03 Lubrizol Corp Ein Kombination von einer Schwefelverbindung und Phosphorverbindungen und ihre Verwendung in Schmierölzusammensetzungen, Konzentrate und Schmierfette
EP0744456A2 (de) * 1995-05-22 1996-11-27 Ethyl Petroleum Additives Limited Schmiermittelzusammensetzungen
EP0767236A1 (de) * 1995-10-04 1997-04-09 Ethyl Petroleum Additives Limited Modifizierung der Reibung synthetischer Getriebeöle
WO1997014771A1 (en) * 1995-10-18 1997-04-24 Exxon Chemical Patents Inc. Power transmitting fluids with improved shift durability
WO1997014770A1 (en) * 1995-10-18 1997-04-24 Exxon Chemical Patents Inc. Power transmitting fluids of improved antiwear performance
EP0780462A3 (de) * 1995-12-22 1997-07-02 Exxon Research And Engineering Company Turboöl mit hohen Lastaufnahmeeigenschaften, enthaltend Aminphosphat und Schwefelhaltige Carbonsäure
US5691283A (en) * 1994-03-01 1997-11-25 Ethyl Petroleum Additives Limited Use of transmission and gear oil lubricants having enhanced friction properties
US5763372A (en) * 1996-12-13 1998-06-09 Ethyl Corporation Clean gear boron-free gear additive and method for producing same
EP1188813A1 (de) * 2000-09-19 2002-03-20 Ethyl Corporation Schmiermittel mit reibungsverändernden Zusätzen
SG94669A1 (en) * 1995-08-11 2003-03-18 Lubrizol Corp Combination of a sulfur compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases
US6645920B1 (en) 2002-11-14 2003-11-11 The Lubrizol Corporation Additive composition for industrial fluid
US6861851B2 (en) 2002-10-16 2005-03-01 The Lubrizol Corporation Method for on-line monitoring of quality and condition of non-aqueous fluids
EP1518919A1 (de) 2003-09-25 2005-03-30 Afton Chemical Corporation Borfreies Getriebeöl für Kraftfahrzeuge
US7259575B2 (en) 2005-04-08 2007-08-21 The Lubrizol Corporation Method for on-line fuel-dilution monitoring of engine lubricant
US7355415B2 (en) 2004-05-07 2008-04-08 The Lubrizol Corporation Method for on-line monitoring of condition of non-aqueous fluids
US7648948B2 (en) 2005-04-08 2010-01-19 Exxonmobil Chemical Patents Inc. Additive system for lubricants
EP2147967A1 (de) * 2008-07-14 2010-01-27 Afton Chemical Corporation Thermisch stabiles, zinkfreies Verschleißschutzmittel
US7803332B2 (en) 2005-05-31 2010-09-28 Exxonmobil Chemical Patents Inc. Reactor temperature control
CN101864336A (zh) * 2010-06-23 2010-10-20 北京泽华化学工程有限公司 一种工业齿轮润滑油添加剂组合物
CN101870904A (zh) * 2010-06-23 2010-10-27 北京泽华化学工程有限公司 一种抗乳化性能优异的齿轮油添加剂组合物
CN101880570A (zh) * 2010-06-22 2010-11-10 北京泽华化学工程有限公司 一种抗乳化性能优异的抗磨液压油添加剂组合物
EP1191087B2 (de) † 2000-09-22 2013-12-18 Chevron Oronite Company LLC Wasser enthaltende funktionelle Flüssigkeiten die öllösliche Dimercaptothiadiazole oder Derivate davon enthalten
US20210071309A1 (en) * 2018-01-19 2021-03-11 Qmaxx Products Group, Inc. Metal cleaning compositions comprising furoate esters and uses therefor

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US7452851B2 (en) 2003-10-24 2008-11-18 Afton Chemical Corporation Lubricant compositions
US7759294B2 (en) 2003-10-24 2010-07-20 Afton Chemical Corporation Lubricant compositions
DE102006026742A1 (de) * 2006-06-07 2007-12-13 Addinol Lube Oil Gmbh Hochleistungs-Industrie-Getriebeöl mit verbesserten Gebrauchswert-Eigenschaften
CN103221523B (zh) * 2010-11-19 2016-06-22 雪佛龙美国公司 用于冲击设备的润滑剂
JP2019123818A (ja) * 2018-01-18 2019-07-25 Ｅｍｇルブリカンツ合同会社 潤滑油組成物

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WO1990009386A1 (en) * 1989-02-08 1990-08-23 The Lubrizol Corporation Hydroxyalkane phosphonic acids and derivatives thereof and lubricants containing the same
EP0391653A2 (de) * 1989-04-03 1990-10-10 Ethyl Petroleum Additives Limited Schmiermittelzusammensetzungen
EP0430624A1 (de) * 1989-11-27 1991-06-05 Ethyl Petroleum Additives, Inc. Getriebeöle und Zusätze dafür
EP0459656A1 (de) * 1990-05-17 1991-12-04 Ethyl Petroleum Additives, Inc. Schmiermittelzusammensetzungen
EP0399764B1 (de) * 1989-05-22 1992-03-25 Ethyl Petroleum Additives Limited Schmiermittel-Zusammensetzungen

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WO1990009386A1 (en) * 1989-02-08 1990-08-23 The Lubrizol Corporation Hydroxyalkane phosphonic acids and derivatives thereof and lubricants containing the same
EP0391653A2 (de) * 1989-04-03 1990-10-10 Ethyl Petroleum Additives Limited Schmiermittelzusammensetzungen
EP0399764B1 (de) * 1989-05-22 1992-03-25 Ethyl Petroleum Additives Limited Schmiermittel-Zusammensetzungen
EP0430624A1 (de) * 1989-11-27 1991-06-05 Ethyl Petroleum Additives, Inc. Getriebeöle und Zusätze dafür
EP0459656A1 (de) * 1990-05-17 1991-12-04 Ethyl Petroleum Additives, Inc. Schmiermittelzusammensetzungen

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0578435A1 (de) * 1992-07-09 1994-01-12 Ethyl Petroleum Additives Limited Modifizierung der Reibung synthetischer Getriebeöle
EP0620268A1 (de) * 1993-03-16 1994-10-19 Ethyl Petroleum Additives Limited Getriebeschmieröle mit verbesserten Reibungseigenschaften
AU668015B2 (en) * 1993-03-16 1996-04-18 Ethyl Petroleum Additives Limited Gear oil lubricants of enhanced friction properties
EP0692012A1 (de) * 1993-04-01 1996-01-17 Ethyl Corporation Zahnradölzusammensetzung
EP0692012A4 (de) * 1993-04-01 1996-01-24
US5691283A (en) * 1994-03-01 1997-11-25 Ethyl Petroleum Additives Limited Use of transmission and gear oil lubricants having enhanced friction properties
EP0695799A3 (de) * 1994-08-03 1996-04-03 Lubrizol Corp Ein Kombination von einer Schwefelverbindung und Phosphorverbindungen und ihre Verwendung in Schmierölzusammensetzungen, Konzentrate und Schmierfette
US6489271B1 (en) 1994-08-03 2002-12-03 The Lubrizol Corporation Combination of a sulfur compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases
EP0744456A2 (de) * 1995-05-22 1996-11-27 Ethyl Petroleum Additives Limited Schmiermittelzusammensetzungen
EP0744456A3 (de) * 1995-05-22 1996-12-11 Ethyl Petroleum Additives Limited Schmiermittelzusammensetzungen
GB2301113A (en) * 1995-05-22 1996-11-27 Ethyl Petroleum Additives Ltd Extreme pressure gear lubricant
SG94669A1 (en) * 1995-08-11 2003-03-18 Lubrizol Corp Combination of a sulfur compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases
EP0767236A1 (de) * 1995-10-04 1997-04-09 Ethyl Petroleum Additives Limited Modifizierung der Reibung synthetischer Getriebeöle
WO1997014771A1 (en) * 1995-10-18 1997-04-24 Exxon Chemical Patents Inc. Power transmitting fluids with improved shift durability
WO1997014770A1 (en) * 1995-10-18 1997-04-24 Exxon Chemical Patents Inc. Power transmitting fluids of improved antiwear performance
EP0780462A3 (de) * 1995-12-22 1997-07-02 Exxon Research And Engineering Company Turboöl mit hohen Lastaufnahmeeigenschaften, enthaltend Aminphosphat und Schwefelhaltige Carbonsäure
US5763372A (en) * 1996-12-13 1998-06-09 Ethyl Corporation Clean gear boron-free gear additive and method for producing same
EP1188813A1 (de) * 2000-09-19 2002-03-20 Ethyl Corporation Schmiermittel mit reibungsverändernden Zusätzen
CN1313580C (zh) * 2000-09-19 2007-05-02 乙基公司 磨擦改性润滑剂
EP1191087B2 (de) † 2000-09-22 2013-12-18 Chevron Oronite Company LLC Wasser enthaltende funktionelle Flüssigkeiten die öllösliche Dimercaptothiadiazole oder Derivate davon enthalten
US6861851B2 (en) 2002-10-16 2005-03-01 The Lubrizol Corporation Method for on-line monitoring of quality and condition of non-aqueous fluids
US6645920B1 (en) 2002-11-14 2003-11-11 The Lubrizol Corporation Additive composition for industrial fluid
EP1518919A1 (de) 2003-09-25 2005-03-30 Afton Chemical Corporation Borfreies Getriebeöl für Kraftfahrzeuge
US7355415B2 (en) 2004-05-07 2008-04-08 The Lubrizol Corporation Method for on-line monitoring of condition of non-aqueous fluids
US7902132B2 (en) 2005-04-08 2011-03-08 The Lubrizol Corporation Additive system for lubricants
US7648948B2 (en) 2005-04-08 2010-01-19 Exxonmobil Chemical Patents Inc. Additive system for lubricants
US7259575B2 (en) 2005-04-08 2007-08-21 The Lubrizol Corporation Method for on-line fuel-dilution monitoring of engine lubricant
US7803332B2 (en) 2005-05-31 2010-09-28 Exxonmobil Chemical Patents Inc. Reactor temperature control
EP2147967A1 (de) * 2008-07-14 2010-01-27 Afton Chemical Corporation Thermisch stabiles, zinkfreies Verschleißschutzmittel
CN101629119B (zh) * 2008-07-14 2014-03-19 雅富顿公司 热稳定无锌抗磨剂
CN101880570B (zh) * 2010-06-22 2013-07-10 北京泽华化学工程有限公司 一种抗乳化性能优异的抗磨液压油添加剂组合物
CN101880570A (zh) * 2010-06-22 2010-11-10 北京泽华化学工程有限公司 一种抗乳化性能优异的抗磨液压油添加剂组合物
CN101870904A (zh) * 2010-06-23 2010-10-27 北京泽华化学工程有限公司 一种抗乳化性能优异的齿轮油添加剂组合物
CN101864336A (zh) * 2010-06-23 2010-10-20 北京泽华化学工程有限公司 一种工业齿轮润滑油添加剂组合物
US20210071309A1 (en) * 2018-01-19 2021-03-11 Qmaxx Products Group, Inc. Metal cleaning compositions comprising furoate esters and uses therefor
US11987892B2 (en) * 2018-01-19 2024-05-21 North American Products Group, Llc Metal cleaning compositions comprising furoate esters and uses therefor

Also Published As

Publication number Publication date
CA2076921A1 (en) 1993-03-10
EP0531585B1 (de) 1998-11-04
AU657563B2 (en) 1995-03-16
JPH05209186A (ja) 1993-08-20
AU2280492A (en) 1993-03-11
DE69130450D1 (de) 1998-12-10
DE69130450T2 (de) 1999-04-08

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