EP0206748B1 - Schmierölzusatz und dieses enthaltende Schmierölzusammensetzung - Google Patents

Schmierölzusatz und dieses enthaltende Schmierölzusammensetzung Download PDF

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Publication number
EP0206748B1
EP0206748B1 EP86304680A EP86304680A EP0206748B1 EP 0206748 B1 EP0206748 B1 EP 0206748B1 EP 86304680 A EP86304680 A EP 86304680A EP 86304680 A EP86304680 A EP 86304680A EP 0206748 B1 EP0206748 B1 EP 0206748B1
Authority
EP
European Patent Office
Prior art keywords
lubricating oil
succinimide
alkyl
borated
catechol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP86304680A
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English (en)
French (fr)
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EP0206748A2 (de
EP0206748A3 (en
Inventor
Thomas V. Liston
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.)
Chevron USA Inc
Original Assignee
Chevron Research and Technology Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US06/745,661 external-priority patent/US4629577A/en
Priority claimed from US06/745,565 external-priority patent/US4629578A/en
Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co
Priority claimed from BR8605801A external-priority patent/BR8605801A/pt
Publication of EP0206748A2 publication Critical patent/EP0206748A2/de
Publication of EP0206748A3 publication Critical patent/EP0206748A3/en
Application granted granted Critical
Publication of EP0206748B1 publication Critical patent/EP0206748B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56—Amides; Imides
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
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    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
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    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
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    • C10M2207/027—Neutral salts thereof
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    • C10M2207/028—Overbased salts thereof
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/26—Overbased carboxylic acid salts
    • C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/086—Imides
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    • C10M2215/28—Amides; Imides
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol fueled engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention relates to lubricating oil additives which serve to reduce friction in internal combustion engines and to the use of such additives in lubricant compositions.
  • U.S. Patent No.2,795,548 discloses the use of lubricating oil compositions containing borated alkyl catechols.
  • the oil compositions are used in the crankcase of an internal combustion engine in order to reduce oxidation of the oil and corrosion of the metal parts of the engine.
  • U.S. Patent No.4,455,243 discloses that a complex prepared by reacting a borated fatty acid ester of glycerol with a succinimide provides reduced friction when present in a lubricating oil for an internal combustion engine.
  • borated alkyl catechols may be stabilized against hydrolysis by reacting the borated alkyl catechol with an alkenyl or alkyl mono or bis succinimide, and that lubricating and the crankcase of an internal combustion engine with a lubricating oil containing such a reaction product reduces the fuel consumption of the engine.
  • a lubricating oil additive comprising a complex obtainable by reacting a borated alkyl catechol with an oil soluble alkyl or alkenyl mono or bis succinimide.
  • a lubricating oil composition comprising an oil of lubricating viscosity and, in an amount effective to reduce friction, an additive prepared by reacting a borated alkyl catechol with an oil soluble alkyl or alkenyl mono or bis succinimide.
  • additives may also be present in the lubricating oil in order to obtain a proper balance of properties such as dispersancy, corrosion, wear and oxidation inhibition which are critical for the proper operation of an internal combustion engine.
  • a method of reducing the fuel consumption of an internal combustion engine comprising treating the moving surface thereof with the lubricating oil composition as described above.
  • improvements in fuel mileage of from 1% to 2% may be obtained by employing the composition of this invention.
  • This fuel economy improvement can be obtained in both compression-ignition engines, that is, diesel engines, and spark-ignition engines, that is, gasoline engines.
  • lubricating oil compositions containing the borated alkyl catechol-succinimide complex of this invention have been found additionally to possess antioxidant properties and when employed in diesel engines they possess diesel deposit inhibition.
  • the complex between the borated alkyl catechol and the alkenyl or alkyl succinimide may be prepared in situ . That is when borated alkyl catechol and a sufficient amount of an alkenyl or alkyl mono or bis succinimide to stabilize the borated alkyl catechol against hydrolysis are added to the lubricating oil, the complex is formed in situ .
  • the present invention relates to a lubricating oil composition
  • a lubricating oil composition comprising an oil of lubricating viscosity and an effective amount to reduce friction of a borated alkyl catechol and an effective amount of an alkenyl mono or bis succinimide to stabilize the borated alkyl catechol against hydrolysis.
  • additives When employed in this manner, other additives may also be present in the lubricating oil in order to obtain a proper balance of properties such as dispersion, corrosion, wear and oxidation which are critical for the proper operation of an internal combustion engine.
  • another aspect of the present invention is a lubricating oil composition especially useful in the crankcase of an internal combustion engine for the purpose of improving the fuel consumption of said engine comprising
  • the borated alkyl catechols may be prepared by borating a alkyl catechol with boric acid with removal of the water of reaction.
  • there is sufficient boron present such that each boron will react with from 1.5 to 2.5 hydroxyl groups present in the reaction mixture.
  • the reaction may be carried out at a temperature in the range of 60°C to 135°C, in the absence or presence of any suitable organic solvent, such as methanol, benzene, xylenes, toluene, or neutral oil.
  • any suitable organic solvent such as methanol, benzene, xylenes, toluene, or neutral oil.
  • the alkyl catechols or mixtures thereof which may be used to prepare the borated alkyl catechols used in this invention are preferably monoalkyl catechols of Formula I wherein R is alkyl containing 10 to 30 carbon atoms and preferably from 16 to 26 carbon atoms. Also, up to 25% by weight but preferably less than 10% by weight of the monoalkyl catechols may have the R group in a position adjacent or ortho to one of the hydroxy groups and has the Formula II wherein R is defined above.
  • alkyl catechols which may be used to prepare the borated alkyl catechols of this invention are dialkyl catechols which are generally of Formula III wherein R is defined above. Trialkyl catechols may also be employed although they are not preferred.
  • alkyl catechols which may be employed are decyl catechol, undecyl catechol, dodecyl catechol, tetradecyl catechol, pentadecyl catechol, hexadecyl catechol, octadecyl catechol, eicosyl catechol, hexacosyl catechol, triacontyl catechol, and the like.
  • a mixture of alkyl catechols may be employed such as a mixture of C14 to C26 alkyl catechols, for example C14-C18 alkyl catechols or C16-C26 alkyl catechols, may be used.
  • the alkyl catechols of the Formula III may be prepared by reacting a C10 to C30 olefin such as a branched olefin or straight-chained alpha-olefin containing 10 to 30 carbon atoms with pyrocatechol in the presence of a sulfonic acid catalyst at a temperature of from about 60°C to 200°C, and preferably 125°C to 180°C in an essentially inert solvent at atmospheric pressure.
  • the inert solvents include benzene, toluene, chlorobenzene and 250 Thinner which is a mixture of aromatics, paraffins and naphthenes.
  • branched olefin means that branching occurs at the double bond.
  • straight chain alpha olefin means that the alpha olefin contains little (less than 10%) or no branching at the double bond or elsewhere.
  • a product which is predominantly monoalkyl catechol may be prepared by using molar ratios of reactants and preferably a 10% by weight molar excess of branched olefin or alpha-olefin over catechol is used. When used at molar ratios, the resulting products are generally monoalkyl catechols but contain some amounts of dialkyl catechol. In any event, molar excess of pyrocatechol (i.e., 2 equivalents of pyrocatechol for each equivalent of olefin) can be used in order to enhance monoalkylation if predominantly monoalkyl catechol is desired. Predominantly dialkyl catechols may be prepared by employing two equivalents to pyrocatechol of the same or different olefin.
  • Use of a branched olefin results in a greater proportion of alkyl catechols of Formula I than use of straight-chain alpha-olefins. Use of such branched olefins generally results in greater than 90% alkyl catechol of Formula I and less than 10% alkyl catechol of Formula II.
  • the borated alkyl catechols are stabilized against hydrolysis by reacting the catechols with an alkyl or alkenyl mono or bis succinimide.
  • an alkyl or alkenyl mono-succinimide is employed.
  • the oil soluble alkenyl or alkyl mono- or bis-succinimides which are employed in this invention are generally known as lubricating oil detergents and are described in for example U.S. Patents Nos. 2,992,708 3,018,291, 3,024,237, 3,100,673, 3,219,666, 3,172,892 and 3,272,746.
  • the alkenyl succinimides are the reaction product of a polyolefin polymer-substituted succinic anhydride with an amine, preferably a polyalkylene polyamine.
  • the polyolefin polymer-substituted succinic anhydrides are obtained by reaction of a polyolefin polymer or a derivative thereof with maleic anhydride.
  • the succinic anhydride thus obtained is reacted with the amine compound.
  • the preparation of the alkenyl succinimides has been described many times in the art. See, for example, U.S. Patent Nos. 3,390,082, 3,219,666 and 3,172,892.
  • Reduction of the alkenyl substituted succinic anhydride yields the corresponding alkyl derivative.
  • a product comprising predominantly mono- or bis-succinimide can be prepared by controlling the molar ratios of the reactants.
  • a predominantly mono-succinimide product will be prepared.
  • two moles of the succinic anhydride are reacted per mole of polyamine, a bis-succinimide will be prepared.
  • the alkenyl succinimide is a mono-succinimide prepared from a polyisobutene-substituted succinic anhydride of a polyalkylene polyamine.
  • the polyisobutene from which the polyisobutene-substituted succinic anhydride is obtained by polymerizing isobutene can vary widely in its compositions.
  • the average number of carbon atoms can range from 30 or less to 250 or more, with a resulting number average molecular weight of about 400 or less to 3,000 or more.
  • the average number of carbon atoms per polyisobutene molecule will range from about 50 to about 100 with the polyisobutenes having a number average molecular weight of about 600 to about 1,500. More preferably, the average number of carbon atoms per polyisobutene molecule ranges from about 60 to about 90, and the number average molecular weight ranges from about 800 to 1,300.
  • polyisobutene is reacted with maleic anhydride according to well-known procedures to yield the polyisobutene-substituted succinic anhydride. See, for example, U.S. Patent Nos. 4,388,471 and 4,450,281.
  • each alkylene radical of the polyalkylene polyamine usually has up to about 8 carbon atoms.
  • the number of alkylene radicals can range up to about 8.
  • the alkylene radical is exemplified by ethylene, propylene, butylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, octamethylene, etc.
  • the number of amino groups generally, but not necessarily, is one greater than the number of alkylene radicals present in the amine, i.e., if a polyalkylene polyamine contains 3 alkylene radicals, it will usually contain 4 amino radicals.
  • the number of amino radicals can range up to about 9.
  • the alkylene radical contains from about 2 to about 4 carbon atoms and all amine groups are primary or secondary. In this case, the number of amine groups exceeds the number of alkylene groups by 1.
  • the polyalkylene polyamine contains from 3 to 5 amine groups.
  • polyalkylene polyamines include ethylenediamine, diethylenetriamine, triethylenetetramine, propylenediamine, tripropylenetetramine, tetraethylenepentamine, trimethylenediamine, pentaethylenehexamine, di-(trimethylene)triamine, tri(hexamethylene)tetramine, etc.
  • amines suitable for preparing the alkenyl succinimide useful in this invention include the cyclic amines such as piperazine, morpholine and dipiperazines.
  • alkenyl succinimides used in the compositions of this invention have the following formula: wherein:
  • the alkenyl succinimide is present in the lubricating oil compositions of the invention in an amount effective to stabilize the borated alkyl catechols against hydrolysis and to act as a dispersant and prevent the deposit of contaminants formed in the oil during operation of the engine.
  • the exact structure of the complex of this invention is not known. For certain, however, while not limiting this invention to any theory, it is believed to be compounds in which boron is either complexed, by or the salt of, one or more nitrogen atoms of the basic nitrogen contained in the succinimide. Therefore, it is preferred that the alkenyl succinimide contain at least 2 and preferably 3-5 basic nitrogens per atoms.
  • the complex may be formed by reacting the borated alkyl catechol and the succinimide together neat at a temperature above the melting point of the mixture of reactants and below the decomposition temperature, or in a diluent in which both reactants are soluble.
  • the reactants may be combined in the proper ratio in the absence of a solvent to form a homogeneous product which may be added to the oil or the reactants may be combined in the proper ratio in a solvent such as toluene or chloroform, the solvent stripped off, and the complex thus formed may be added to the oil.
  • the complex may be prepared in a lubricating oil as a concentrate containing from about 20 to 90% by weight of the complex, which concentrate may be added in appropriate amounts to the lubricating oil in which it is to be used or the complex may be prepared directly in the lubricating oil in which it is to be used.
  • the diluent is preferably inert to the reactants and products formed and is used in an amount sufficient to insure solubility of the reactants and to enable the mixture to be efficiently stirred.
  • Temperatures for preparing the complex may be in the range of from 25°C to 200°C and preferably 25°C to 100°C depending on whether the complex is prepared neat or in a diluent, i.e., lower temperatures may be used when a solvent is used.
  • weight percent ratios of succinimide to borated alkyl catechol used to form the complex are in the range of 3:1 to 16:1 and preferably from 3:1 to 10:1 and most preferably 3:1 to 6:1. This latter ratio is preferred if the complex is made and/or stored neat or in the absence of solvent or lubricating oil and under atmospheric conditions.
  • the term "stabilized against hydrolysis” means that the borated alkyl catechol-succinimide complex does not form a precipitate due to the hydrolysis of the borated catechol for a period of at least three months when stored at room temperature (about 15-25°C) and ambient humidity.
  • the amount of the complex required to be effective for reducing friction in lubricating oil compositions may range from 0.5% to 20% by weight percent. However, in the preferred embodiment, it is desirable to add sufficient complex so that the amount of borated catechol is added at a range from 0.1% to about 4% by weight of the total lubricant composition and preferably is present in the range of from 0.2% to 2% by weight and most preferably 0.5% to 1%.
  • the succinimide is present in the complex of the invention in an amount effective to stabilize the borated alkyl catechol against hydrolysis and which allows the borated alkyl catechol to function as effective friction reducing agents.
  • the succinimide in the complex acts as a dispersant and prevents the deposition of contaminants formed in the oil during operation of the engine.
  • complexes of this invention may also be used in combination with other additive systems in conventional amounts for their known purpose.
  • the base composition described above will be formulated with supplementary additives to provide the necessary stability, detergency, dispersancy, anti-wear and anti-corrosion properties.
  • the lubricating oils to which the complexes prepared by reacting the borated alkyl catechols and succinimides may contain an alkali or alkaline earth metal hydrocarbyl sulfonate, an alkali or alkaline earth metal phenate, and Group II metal salt dihydrocarbyl dithiophosphate.
  • succinimides act as excellent dispersants
  • additional succinimide may be added to the lubricating oil compositions, above the amounts added in the form of the complex with the borated alkyl catechols.
  • the amount of succinimides can range up to about 20% by weight of the total lubricating oil compositions.
  • the alkali or alkaline earth metal hydrocarbyl sulfonates may be either petroleum sulfonate, synthetically alkylated aromatic sulfonates, or aliphatic sulfonates such as those derived from polyisobutylene.
  • One of the more important functions of the sulfonates is to act as a detergent and dispersant. These sulfonates are well known in the art.
  • the hydrocarbyl group must have a sufficient number of carbon atoms to render the sulfonate molecule oil soluble.
  • the hydrocarbyl portion has at least 20 carbon atoms and may be aromatic or aliphatic, but is usually alkylaromatic. Most preferred for use are calcium, magnesium or barium sulfonates which are aromatic in character.
  • Certain sulfonates are typically prepared by sulfonating a petroleum fraction having aromatic groups, usually mono- or dialkylbenzene groups, and then forming the metal salt of the sulfonic acid material.
  • Other feedstocks used for preparing these sulfonates include synthetically alkylated benzenes and aliphatic hydrocarbons prepared by polymerizing a mono- or diolefin, for example, a polyisobutenyl group prepared by polymerizing isobutene.
  • the metallic salts are formed directly or by metathesis using well-known procedures.
  • the sulfonates may be neutral or overbased having base numbers up to about 400 or more.
  • Carbon dioxide and calcium hydroxide or oxide are the most commonly used material to produce the basic or overbased sulfonates.
  • Mixtures of neutral and overbased sulfonates may be used.
  • the sulfonates are ordinarily used so as to provide from 0.3% to 10% by weight of the total composition.
  • the neutral sulfonates are present from 0.4% to 5% by weight of the total composition and the overbased sulfonates are present from 0.3% to 3% by weight of the total composition.
  • the phenates for use in this invention are those conventional products which are the alkali or alkaline earth metal salts of alkylated phenols.
  • One of the functions of the phenates is to act as a detergent and dispersant. Among other things, it prevents the deposit of contaminants formed during high temperature operation of the engine.
  • the phenols may be mono- or polyalkylated.
  • the alkyl portion of the alkyl phenate is present to lend oil solubility to the phenate.
  • the alkyl portion can be obtained from naturally occurring or synthetic sources.
  • Naturally occurring sources include petroleum hydrocarbons such as white oil and wax. Being derived from petroleum, the hydrocarbon moiety is a mixture of different hydrocarbyl groups, the specific composition of which depends upon the particular oil stock which was used as a starting material.
  • Suitable synthetic sources include various commercially available alkenes and alkane derivatives which, when reacted with the phenol, yield an alkylphenol.
  • Suitable radicals obtained include butyl, hexyl, octyl, decyl, dodecyl, hexadecyl, eicosyl, triacontyl, and the like.
  • Other suitable synthetic sources of the alkyl radical include olefin polymers such as polypropylene, polybutylene, polyisobutylene and the like.
  • the alkyl group can be straight-chained or branch-chained, saturated or unsaturated (if unsaturated, preferably containing not more than 2 and generally not more than 1 site of olefinic unsaturation).
  • the alkyl radicals will generally contain from 4 to 30 carbon atoms. Generally when the phenol is monoalkyl-substituted, the alkyl radical should contain at least 8 carbon atoms.
  • the phenate may be sulfurized if desired. It may be either neutral or overbased and if overbased will have a base number of up to 200 to 300 or more. Mixtures of neutral and overbased phenates may be used.
  • the phenates are ordinarily present in the oil to provide from 0.2% to 27% by weight of the total composition.
  • the neutral phenates are present from 0.2% to 9% by weight of the total composition and the overbased phenates are present from 0.2 to 13% by weight of the total composition.
  • the overbased phenates are present from 0.2% to 5% by weight of the total composition.
  • Preferred metals are calcium, magnesium, strontium or barium.
  • the sulfurized alkaline earth metal alkyl phenates are preferred. These salts are obtained by a variety of processes such as treating the neutralization product of an alkaline earth metal base and an alkylphenol with sulfur. Conveniently the sulfur, in elemental form, is added to the neutralization product and reacted at elevated temperatures to produce the sulfurized alkaline earth metal alkyl phenate.
  • Carbon dioxide and calcium hydroxide or oxide are the most commonly used material to produce the basic or "overbased” phenates.
  • a process wherein basic sulfurized alkaline earth metal alkylphenates are produced by adding carbon dioxide is shown in Hanneman, U.S. Patent No. 3,178,368.
  • the Group II metal salts of dihydrocarbyl dithiophosphoric acids exhibit wear, antioxidant and thermal stability properties.
  • Group II metal salts of phosphorodithioic acids have been described previously. See, for example, U.S. Patent No. 3,390,080, columns 6 and 7, wherein these compounds and their preparation are described generally.
  • the Group II metal salts of the dihydrocarbyl dithiophosphoric acids useful in the lubricating oil composition of this invention contain from about 4 to about 12 carbon atoms in each of the hydrocarbyl radicals and may be the same or different and may be aromatic, alkyl or cycloalkyl.
  • Preferred hydrocarbyl groups are alkyl groups containing from 4 to 8 carbon atoms and are represented by butyl, isobutyl, sec.-butyl, hexyl, isohexyl, octyl, 2-ethylhexyl and the like.
  • the metals suitable for forming these salts include barium, calcium, strontium, zinc and cadmium, of which zinc is preferred.
  • the Group II metal salt of a dihydrocarbyl dithiophosphoric acid has the following formula: wherein:
  • the dithiophosphoric salt is present in the lubricating oil compositions of this invention in an amount effective to inhibit wear and oxidation of the lubricating oil.
  • the amount ranges from about 0.1 to about 4 percent by weight of the total composition, preferably the salt is present in an amount ranging from about 0.2 to about 2.5 percent by weight of the total lubricating oil composition.
  • the final lubricating oil composition will ordinarily contain 0.025 to 0.25% by weight phosphorus and preferably 0.05 to 0.15% by weight.
  • the finished lubricating oil may be single or multigrade.
  • Multigrade lubricating oils are prepared by adding viscosity index (VI) improvers.
  • Typical viscosity index improvers are polyalkyl methacrylates, ethylene propylene copolymers, styrene diene copolymers and the like.
  • So-called decorated VI improvers having both viscosity index and dispersant properties are also suitable for use in the formulations of this invention.
  • the lubricating oil used in the compositions of this invention may be mineral oil or in synthetic oils of lubricating viscosity and preferably suitable for use in the crankcase of an internal combustion engine.
  • Crankcase lubricating oils ordinarily have a viscosity of about 1300 cst 0°F to 22.7 cst at 210°F (99°C).
  • the lubricating oils may be derived from synthetic or natural sources.
  • Mineral oil for use as the base oil in this invention includes paraffinic, naphthenic and other oils that are ordinarily used in lubricating oil compositions.
  • Synthetic oils include both hydrocarbon synthetic oils and synthetic esters.
  • Useful synthetic hydrocarbon oils include liquid polymers of alpha olefins having the proper viscosity.
  • the hydrogenated liquid oligomers of C6 ⁇ 12 alpha olefins such as 1-decene trimer.
  • alkyl benzenes of proper viscosity such as didodecyl benzene
  • useful synthetic esters include the esters of both monocarboxylic acid and polycarboxylic acids as well as monohydroxy alkanols and polyols. Typical examples are didodecyl adipate, pentaerythritol tetracaproate, di-2-ethylhexyl adipate, dilaurylsebacate and the like.
  • Complex esters prepared from mixtures of mono and dicarboxylic acid and mono and dihydroxy alkanols can also be used.
  • Blends of hydrocarbon oils with synthetic oils are also useful. For example, blends of 10 to 25 weight percent hydrogenated 1-decene trimer with 75 to 90 weight percent 150 SUS (100°F) mineral oil gives an excellent lubricating oil base.
  • Additive concentrates are also included within the scope of this invention. They usually include from about 90 to 20 weight percent of an oil of lubricating viscosity and from about 20 to 90 weight percent of the complex additive of this invention. Typically, the concentrates contain sufficient diluent to make them easy to handle during shipping and storage. Suitable diluents for the concentrates include any inert diluent, preferably an oil of lubricating viscosity, so that the concentrate may be readily mixed with lubricating oils to prepare lubricating oil compositions.
  • Suitable lubricating oils which can be used as diluents typically have viscosities in the range from about 35 to about 500 Saybolt Universal Seconds (SUS) at 100°F (38°C), although an oil of lubricating viscosity may be used.
  • SUS Saybolt Universal Seconds
  • additives which may be present in the formulation include rust inhibitors, foam inhibitors, corrosion inhibitors, metal deactivators, pour point depressants, antioxidants, and a variety of other well-known additives.
  • the reaction mixture was stripped by heating to 160°C under vacuum (0.4 mm Hg).
  • the product was filtered hot over super cell (SCC) to afford 908.5 gms. of C14-C18 alkyl substituted pyrocatechol.
  • the product had a hydroxyl number of 259.
  • the corresponding alkyl catechols are prepared.
  • An oil blend was prepared as indicated in Table I using CitCon 100N oil and containing 1.0% by weight of the borated alkyl catechol prepared according to Example 3.
  • One part by weight of the borated alkyl catechol prepared according to Example 3 and 3 parts by weight of a 48% by weight of polyisobutenyl succinimide prepared by reacting polyisobutenyl succinic anhydride wherein the number average molecular weight of the polyisobutenyl was about 950 and tetraethylenepentamine in a mole ratio of amine to anhydride of 0.87) solution in oil (CitCon 100N) were heated together with mixing on a hot plate at 100°C for 0.5 hours.
  • the borated alkyl catechol hydrolyzed and formed a skin on its surface as it cooled down (approx. 1/4-hr).
  • the borated alkyl catechol-succinimide complexed material remained bright and clear after one week in storage. Even after three weeks, the sample remained clear.
  • Tests were carried out which demonstrate the improvements in fuel economy obtained by adding lubricating oil compositions of this invention to the crankcase of an automobile engine.
  • crankcase oils each containing 0.5% to 2% by weight of borated C18-C24 monoalkyl catechol, borated C14-C18 dialkyl catechol and the like in the place of borated C14-C18 alkyl catechol of Example 3 in the above formulations are also effective in reducing fuel consumption in an internal combustion engine.

Claims (17)

  1. Schmieröl-Additiv, umfassend einen durch Umsetzung eines borierten Alkyl-Catechins mit einem Öl-löslichen Alkyl- oder Alkenylmono- oder -bissuccinimid erhältlichen Komplex.
  2. Additiv nach Anspruch 1, worin der Alkyl-Rest des borierten Alkyl-Catechins 10 bis 30 C-Atome enthält und das Succinimid ein Polyisobutenylsuccinimid eines Polyalkylenpolyamins ist.
  3. Additiv nach Anspruch 2, worin der Alkyl-Rest des borierten Alkyl-Catechins ein Gemisch Von 14 bis 26 C-Atomen enthaltenden Alkyl-Resten ist.
  4. Additiv nach Anspruch 2 oder 3, worin das Succinimid ein Polyisobutenylsuccinimid von Triethylentetramin oder ein Polyisobutenylsuccinimid von Tetraethylenpentamin ist.
  5. Schmieröl-Mittel, umfassend ein Öl mit Schmierviskosität und in einer wirksamen Menge zur Reibungsreduzierung ein Additiv nach einem der Ansprüche 1 bis 4.
  6. Verfahren zur Reduzierung des Ölverbrauchs eines Verbrennungsmotors, bei dem seine beweglichen Oberflächen mit einem Schmieröl-Mittel nach Anspruch 5 behandelt werden.
  7. Schmieröl-Mittel, umfassend ein Öl mit Schmierviskosität und 0,1 bis 4 Gew.-% eines borierten Alkyl-Catechins und eine wirksame Menge eines Alkenylmono oder -bissuccinimids zur Stabilisierung des borierten Alkyl-Catechins gegenüber Hydrolyse.
  8. Schmieröl-Mittel nach Anspruch 7, worin der Alkyl-Rest des borierten Alkyl-Catechins 10 bis 30 C-Atome enthält und das Alkenylsuccinimid ein Polyisobutenylsuccinimid eines Polyalkylenpolyamins ist.
  9. Schmieröl-Mittel nach Anspruch 8, worin der Alkyl-Rest des borierten Alkyl-Catechins ein Gemisch von 14 bis 18 C-Atomen enthaltenden Alkyl-Resten ist.
  10. Schmieröl-Mittel nach Anspruch 8 oder 9, worin das Alkenylsuccinimid ein Polyisobutenylsuccinimid von Triethylentetramin oder ein Polyisobutenylsuccinimid von Tetraethylenpentamin ist.
  11. Schmieröl-Mittel nach Anspruch 8, worin der Alkyl-Rest des borierten Alkyl-Catechins ein Gemisch von 14 bis 16 C-Atomen enthaltenden Alkyl-Resten ist.
  12. Verfahren zur Reduzierung des Ölverbrauchs eines Verbrennungsmotors, bei dem seine beweglichen Oberflächen mit einem Komplex nach Anspruch 1 behandelt werden.
  13. Schmieröl-Mittel, umfassend
    (a) ein Öl mit Schmierviskosität, und
    (b) eine wirksame Menge von jedem folgenden:
    1. einem Alkenylsuccinimid,
    2. einem borierten Alkyl-Catechin-Reibungsminderer,
    3. einem Gruppe II Metallsalz einer Dihydrocarbyldithiophosphorsäure,
    4. einem neutralen oder überalkalisierten Alkalimetall- oder Erdalkalimetallhydrocarbylsulfonat oder einem Gemisch davon, und
    5. einem neutralen oder überalkalisierten Alkalimetall- oder Erdalkalimetall-alkyliertem Phenat oder einem Gemisch davon.
  14. Schmieröl-Mittel nach Anspruch 13, worin
    (1) das Alkenylsuccinimid ein Polyisobutenylsuccinimid eines Polyalkylenpolyamins ist,
    (2) das borierte Alkyl-Catechin ein boriertes C₁₄-C₁₈-Alkylcatechin ist,
    (3) das Metallsalz der Dihydrocarbyldithiophosphorsäure Zinkdialkyldithiophosphat ist, worin der Alkyl-Rest 4 bis 12 C-Atome enthält,
    (4) das Metall des neutralen oder überalkalisierten Alkalimetall- oder Erdalkalimetallsulfonates Calcium, Magnesium oder Barium oder ein Gemisch davon ist, und
    (5) das Metall des neutralen oder überalkalisierten Alkalimetall- oder Erdalkalimetall-Phenats Calcium, Magnesium oder Barium ist.
  15. Schmieröl-Mittel nach Anspruch 14, worin
    (1) das Alkenylsuccinimid ein Polyisobutenylsuccinimid von Triethylentetramin oder ein Polyisobutenylsuccinimid von Tetraethylenpentamin ist,
    (2) das borierte Alkyl-Catechin ein boriertes C₁₄-C₁₈-Alkylcatechin ist,
    (3) das Metallsalz der Dihydrocarbyldithiophosphorsäure Zink 0,0-Di(2-ethylhexyl)dithiophosphat, Zink-0,0-Di(isobutyl/gemischtes, primäres hexyl)dithiophosphat oder Zink-0,0-Di(sec-butyl/gemischtes, sekundäres hexyl)dithiophosphat ist,
    (4) das Metallsalz des Sulfonats ein überalkalisiertes Magnesium- oder Calciumhydrocarbylsulfonat ist, und
    (5) das Metallsalz des Phenats ein überalkalisiertes, geschwefeltes Calcium- oder Magnesium-monoalkyliertes Phenat ist.
  16. Verfahren zur Reduzierung des Ölverbrauchs eines Verbrennungsmotors, bei dem seine beweglichen Oberflächen mit einem Mittel nach Anspruch 13, 14 oder 15 behandelt werden.
  17. Verwendung eines Schmieröl-Additives nach Anspruch 1, 2, 3 oder 4 als Reibungsminderungs-Additiv in einem Schmieröl-Mittel für einen Verbrennungsmotor.
EP86304680A 1985-06-17 1986-06-17 Schmierölzusatz und dieses enthaltende Schmierölzusammensetzung Expired - Lifetime EP0206748B1 (de)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US745565 1985-06-17
US745661 1985-06-17
US06/745,661 US4629577A (en) 1985-06-17 1985-06-17 Method for improving fuel economy of internal combustion engines
US06/745,565 US4629578A (en) 1985-06-17 1985-06-17 Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same
BR8605801A BR8605801A (pt) 1985-06-17 1986-11-26 Composicao,composicao de oleo lubrificante e processo para reduzir o consumo de combustivel de um motor de combustao interna

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EP0206748A2 EP0206748A2 (de) 1986-12-30
EP0206748A3 EP0206748A3 (en) 1989-04-05
EP0206748B1 true EP0206748B1 (de) 1992-09-02

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EP86304680A Expired - Lifetime EP0206748B1 (de) 1985-06-17 1986-06-17 Schmierölzusatz und dieses enthaltende Schmierölzusammensetzung

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EP (1) EP0206748B1 (de)
AU (1) AU598769B2 (de)
BE (1) BE905818A (de)
CA (1) CA1273344A (de)
NL (1) NL8603048A (de)
SE (1) SE463770B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0854904B2 (de) † 1995-09-27 2007-05-23 Infineum USA L.P. Kurbelgehäuseschmiermittel mit niedrigem chlorgehalt und mit niedrigem aschegehalt

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DE3868949D1 (de) * 1987-01-21 1992-04-16 Amoco Corp Veschleissschutz-schmiermittelzusammensetzungen mit geringem phosphorgehalt.
US4808325A (en) * 1987-03-30 1989-02-28 Amoco Corporation Mannich dispersant VI-improver blended with phenolic compound for improved storage stability
CA1337294C (en) * 1987-11-20 1995-10-10 Dale Robert Carroll Lubricant compositions for enhanced fuel economy
CA1337293C (en) * 1987-11-20 1995-10-10 Emil Joseph Meny Lubricant compositions for low-temperature internal combustion engines
US4975211A (en) * 1989-07-05 1990-12-04 Chevron Research Company Diethylamine complexes of borated alkyl catechols and lubricating oil compositions containing the same
US6767871B2 (en) * 2002-08-21 2004-07-27 Ethyl Corporation Diesel engine lubricants
WO2009042586A1 (en) 2007-09-26 2009-04-02 The Lubrizol Corporation Titanium compounds and complexes as additives in lubricants
US10501702B2 (en) 2015-03-10 2019-12-10 The Lubrizol Corporation Lubricating compositions comprising an anti-wear/friction modifying agent

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US2795548A (en) * 1954-06-29 1957-06-11 California Research Corp Lubricant compositions
US3445498A (en) * 1965-05-25 1969-05-20 Universal Oil Prod Co Boric acid esters
AU550869B2 (en) * 1981-08-03 1986-04-10 Chevron Research Company Lubricating oil with borated long chain 1,2 alkane diol friction modifier
US4563293A (en) * 1981-08-03 1986-01-07 Chevron Research Company Method for improving fuel economy of internal combustion engines using borated 1,2-alkanediols
US4483775A (en) * 1982-10-28 1984-11-20 Chevron Research Company Lubricating oil compositions containing overbased calcium sulfonates
US4455243A (en) * 1983-02-24 1984-06-19 Chevron Research Company Succinimide complexes of borated fatty acid esters of glycerol and lubricating oil compositions containing same
US4632771A (en) * 1984-08-17 1986-12-30 Chevron Research Company Normally liquid C14 to C18 monoalkyl catechols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0854904B2 (de) † 1995-09-27 2007-05-23 Infineum USA L.P. Kurbelgehäuseschmiermittel mit niedrigem chlorgehalt und mit niedrigem aschegehalt

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Publication number Publication date
NL8603048A (nl) 1988-06-16
SE463770B (sv) 1991-01-21
AU598769B2 (en) 1990-07-05
AU6553086A (en) 1988-05-26
BE905818A (fr) 1987-03-16
EP0206748A2 (de) 1986-12-30
SE8605064L (sv) 1988-05-27
SE8605064D0 (sv) 1986-11-26
CA1273344A (en) 1990-08-28
EP0206748A3 (en) 1989-04-05

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