EP0020037B1 - Öllöslicher reibungsvermindernder Zusatzstoff, Verfahren zu dessen Herstellung und Schmieröl- oder Kraftstoff-Zusammensetzung, die den Zusatzstoff enthält - Google Patents

Öllöslicher reibungsvermindernder Zusatzstoff, Verfahren zu dessen Herstellung und Schmieröl- oder Kraftstoff-Zusammensetzung, die den Zusatzstoff enthält Download PDF

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Publication number
EP0020037B1
EP0020037B1 EP80301487A EP80301487A EP0020037B1 EP 0020037 B1 EP0020037 B1 EP 0020037B1 EP 80301487 A EP80301487 A EP 80301487A EP 80301487 A EP80301487 A EP 80301487A EP 0020037 B1 EP0020037 B1 EP 0020037B1
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EP
European Patent Office
Prior art keywords
additive
oil
linear
succinimide
mixture
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
Application number
EP80301487A
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English (en)
French (fr)
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EP0020037A1 (de
Inventor
Andrew George Papay
Joseph Peter O'brien
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Edwin Cooper Inc
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Edwin Cooper Inc
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Publication of EP0020037B1 publication Critical patent/EP0020037B1/de
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/06—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing conjugated dienes
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/086—Imides
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26—Amines
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/043—Mannich bases
    • C—CHEMISTRY; METALLURGY
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbasedsulfonic acid salts
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • C—CHEMISTRY; METALLURGY
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    • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10M2225/041—Hydrocarbon polymers
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
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    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol fueled engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C10N2040/255—Gasoline engines
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    • 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

Definitions

  • This invention is in the field of lubricants and lubricant additives. More particularly, the invention deals with additives to lubricants especially for crankcase use for internal combustion engines, which provide a reduction of friction of the operating engine.
  • Another way to improve fuel mileage is to reduce engine friction.
  • the present invention is concerned with this latter approach.
  • the present invention utilizes the finding that oil soluble, C 12-36 aliphatic hydrocarbyl succinimides or succinimides containing a certain hydrocarbon 'grouping which has been formed by a particular isomerization technique provide a friction reducing effect when they are incorporated in lubricating oil.
  • an oil-soluble friction-reducing additive which comprises at least one compound having the structure: or wherein
  • the aliphatic hydrocarbon group is derived from a linear a-olefin which has been isomerized to form a mixture of internal olefins.
  • the additive can also be used in the engine fuel.
  • a preferred embodiment of the invention is a lubricating oil composition or fuel composition containing a friction-reducing amount of an additive as above defined.
  • the aliphatic substituent Z on the succinic group can be any unsaturated aliphatic hydrocarbon group containing from 12 to 36 carbon atoms including alkenyl and polyunsaturated hydrocarbon groups.
  • Examples of the above additive include:
  • R, and R 2 are straight chain aliphatic hydrocarbon groups. These additives have improved solubility in lubricating oil. Examples of these additives are: 1-propyltridecenyl succinimide
  • the above highly preferred additives are made from linear a-olefins containing from 12 to 36 carbon atoms by isomerizing the a-olefins to form a mixture of internal olefins and-reacting this mixture of internal olefins with maleic acid, anhydride or ester forming an intermediate and reacting the intermediate with ammonia to form amide, imide, or mixtures thereof.
  • Additives made from isomerized linear a-olefins have greatly improved oil solubility compared with additives made with linear a-olefins.
  • Isomerization of the linear a-olefin can be carried out using conventional methods.
  • One suitable method is to heat the linear a-olefin with an acidic catalyst.
  • acid catalysts are the sulfonated styrenedivinylbenzene copolymers.
  • Such catalysts are commercially available and are conventionally used as cation exchange resins. In the present method they are used in their acid form.
  • Typical resins are Amberlyst 15, XN-1005 and XN-1010 (registered trademarks) available from Rohm and Haas Company. Use of such resins for isomerizing linear a-olefins is described in US-A-4,108,889.
  • the additives are added to the lubricating oil in an amount which reduces the fraction of the engine operating with the oil in the crankcase.
  • a useful concentration is about 0.05 to 3 weight percent.
  • a more preferred range is about 0.1 to 1.0 weight percent.
  • an embodiment of the invention is an improved motor oil compostion formulated for use as a crankcase lubricant in an internal combustion engine wherein the improvement comprises including in the crankcase oil an amount sufficient to reduce fuel consumption of the engine of the friction-reducing additive herein described.
  • such improved motor oil also contains an ashless uispersant and an alkaline earth metal salt of a petroleum sulfonic acid or an alkaryl sulfonic acid (e.g. alkylbenzene sulfonic acid).
  • an alkaline earth metal salt of a petroleum sulfonic acid or an alkaryl sulfonic acid e.g. alkylbenzene sulfonic acid.
  • the additives can be used in mineral oil or in synthetic oils of viscosity suitable for use in the crankcase of an internal combustion engine.
  • Crankcase lubricating oils have a viscosity up to about 16 8 10- 3 m 2 /S (80 SUS) at 100°C (210°F).
  • Mineral oils include those of suitable viscosity refined from crude oil from all sources including Gulfcoast, midcontinent, Pennsylvania, California, Alaska and the like. Various standard refinery operations can be used in processing the mineral oil.
  • Synthetic oil includes both hydrocarbon synthetic oil and synthetic esters.
  • Useful synthetic hydrocarbon oils including liquid polymers of a-olefins having the proper viscosity.
  • the hydrogenated liquid oligomers of C 6 -C 12 a-olefins such as a-decene trimer.
  • alkylbenzenes of proper viscosity can be used, such as didoecylbenzene.
  • Useful synthetic esters include the esters of both monocarboxylic acid and polycarboxylic acid as well as monohydroxy alkanols and polyols. Typical examples are didoceyl adipate, trimethylol propane tripelargonate, pentaerythritol tetracaproate, di(2-ethylhexyl)adipate, dilauryl sebacate and the like. Complex esters prepared from mixtures of mono- and dicarboxylic acid and mono- and polyhydroxyl alkanols can also be used.
  • Blends of mineral oil with synthetic oil are particularly useful. For example, blends of 5 to 25 weight percent hydrogenated ⁇ -decene trimer with 75 to 95 weight percent 32 x 10- 3 m 2 /S (150 SUS 38°C (100°F)) mineral oil results in an excellent lubricant. Likewise, blends of about 5 to 25 weight percent di(2-ethylhexyl)adipate with mineral oil of proper viscosity results in a superior lubricating oil. Also blends of synthetic hydrocarbon oil with synthetic esters can be used. Blends of mineral oil with synthetic oil are especially useful when preparing low viscosity oil (e.g., SAE 5W 20) since they permit these low viscosities without contributing excessive volatility.
  • low viscosity oil e.g., SAE 5W 20
  • the more preferred lubricating oil compositions include zinc dihydrocarbyidithiophosphate (ZDDP) in combination with the present additives.
  • ZDDP zinc dihydrocarbyidithiophosphate
  • Both zinc dialkyldithiophosphates and zinc dialkaryldithio- phosphates as well as mixed alkyl-aryl dithiophosphates can be used.
  • alkyl-type ZDDP are those in which the hydrocarbyl groups are a mixture of isobutyl and isoamyl alkyl groups.
  • Zinc di-(nonylphenyl)-dithiophosphate is an example of an aryl-type ZDDP.
  • Good results are achieved using sufficient zinc dihydrocarbyldithiophosphate to provide about 0.01 to 0.5 weight percent zinc.
  • a preferred concentration supplies about 0.05 to 0.3 weight percent zinc.
  • alkaline earth metal petroleum sutfonate or alkaline earth metal alkaryl sulfonates are the alkaline earth metal petroleum sutfonate or alkaline earth metal alkaryl sulfonates.
  • alkaline earth metal petroleum sutfonate or alkaline earth metal alkaryl sulfonates are calcium petroleum suifonates, magnesium petroleum sulfonates, barium alkaryl sulfonates, calcium alkaryl sulfonates or magnesium alkaryl sulfonates.
  • Both the neutral and the overbased sulfonates having base numbers up to about 400 can be beneficially used. These are used in an amount to provide about 0.05 to 1.5 weight percent alkaline earth metal and more preferably about 0.1 to 1.0 weight percent.
  • Viscosity index improvers can be included such as the polyalkylmethacrylate type or the ethylenepropylene copolymer type. Likewise, styrene-diene VI improvers can be used. Alkaline earth metal salts of phosphosulfurized polyisobutylene are useful.
  • Preferred crankcase oils also contain an ashless dispersant such as the polyolefin succinamides and succinimides of polyethylene polyamines such as tetraethylenepentamine.
  • the polyolefin succinic substituent is preferably a polyisobutene group having a molecular weight of from about 800 to 5,000. Such ashless dispersants are more fully described in U.S. 3,172,892 and U.S. 3,219,666 incorporated herein by reference.
  • ashless dispersants include the Mannich condensation products of polyolefin- substituted phenols, formaldehyde and polyethylene polyamine.
  • the polyolefin phenol is a polyisobutylene-substituted phenol in which the polyisobutylene group has a molecular weight of from about 800 to 5,000.
  • the preferred polyethylene polyamine is tetrathylene pentamine.
  • Mannich ashless dispersants are more fully described in U.S. 3,368,972; U.S. 3,413,347; U.S. 3,442,808; U.S. 3,448,047; U.S. 3,539,633; U.S. 3,591,598; U.S.
  • the friction-reducing additives of this invention are also useful in fuel compositions. Fuel injected or inducted into a combustion chamber wets the walls of the cylinder. Fuels containing a small amount of the present additive reduce the friction due to the piston rings sliding against the cylinder wall.
  • the additives can be used in both diesel fuel and gasoline used to operate internal combustion engines. Fuels containing about 0.001 to 0.25 weight percent of the friction-reducing additives can be used.
  • Fuels used with the invention can contain any of the additives conventionally added to such fuels.
  • gasoline it can include dyes, antioxidants, detergents, antiknocks (e.g. tetraethyllead, methylcyclopentadienylmanganese tricarbonyl, rare earth metal chelates, methyl tert-butylether and the like).
  • antiknocks e.g. tetraethyllead, methylcyclopentadienylmanganese tricarbonyl, rare earth metal chelates, methyl tert-butylether and the like.
  • diesel fuels the compositions can include pour point depressants, detergents, ignition improvers (e.g. hexanitrate) and the like.
  • Tests were conducted using a 1977 U.S. production automobile. These were shortened versions of the Federal City EPA cycle. This is referred to as the "Hot 505" cycle. It consists of the first 5.8 km (3.6 miles) of the Federal EPA City cycle started with a warmed-up engine instead of a cold engine. The car with a fully formulated SE grade oil in its crankcase is operated on a chassis dynamometer for about one hour at about 88 km/hr. (55 mph) to stabilize oil temperature. It is then run through four consecutive "Hot 505" cycles measuring fuel economy of the base oil. Results of the four cycles are averaged. Then one-half of the base oil is drained from the crankcase and replaced with the same base oil containing a double dose of the test additive.
  • the car is then run at about 88 km/hr. (55 mph) for about one hour to again stabilize temperature.
  • a second series of four consecutive "Hot 505" cycles is run to measure initial fuel economy of the base oil containing the test additive.
  • the car is then run about 805 km (500 miles) at constant speed of about 88 km/hr. (55 mph).
  • a third series of four consecutive "Hot 505" cycles are run to measure fuel economy after about 805 km (500 miles) operation on the oil containing the test additive.
  • the crankcase is then drained hot and filled with flushing oil which is run for a short time and then drained.
  • the crankcase is then filled with the base oil which is run for a short time and then drained.
  • crankcase is then filled a second time with a base oil. This is run about one hour at about 88 km/hr. (55 mph) to a stable temperature. Then a fourth series of four consecutive "Hot 505" cycles are run measuring fuel economy. This gives a second base line thus bracketing the test carried out with the friction additive between two base line tests.
  • the following table shows the percent improvement in fuel economy over the base oil obtained using 1 weight percent of the friction-reducing additive.

Claims (10)

1. Öllösliches reibungsminderndes Zusatzmittel, welches mindestens eine Verbindung der folgenden Strukturen enthält
Figure imgb0012
oder
Figure imgb0013
worin n eine ganze Zahl von 2 bis 4 ist und worin Z die Struktur
Figure imgb0014
besitzt, worin R, und R2 jeweils unabhängig geradkettige oder verzweigtkettige Kohlenwasserstoffreste mit 1 bis 34 Kohlenstoffatomen derart sind, daß die Gesamtzahl der Kohlenstoffatome in den Resten R, und R2 von 11 bis 35 beträgt, der Kohlenwasserstoffrest Z ungesättigt ist und durch Umsetzung von Maleinsäure, -anhydrid oder -ester mit einem inneren Olefin, welches 12 bis 36 Kohlenstoffatome enthält, hergestellt wird, wobei das innere Olefin durch Isomerisierung der olefinischen Doppelbindung eines linearen α-Olefins oder eines Gemisches davon gebildet wird, um ein Gemisch innerer Olefine zu erhalten.
2. Öllösliches reibungsminderndes Zusatzmittel nach Anspruch 1, worin R, und Rz geradkettige aliphatische Kohlenwasserstoffreste mit einer Gesamtzahl von 15 bis 21 Kohlenstoffatomen sind.
3. Öllösliches reibungsminderndes Zusatzmittel nach Anspruch 1, welches 1-Propyltridecenylsuccinimid, 1-Pentyltridecenylsuccinimid, 1-Tridecylpentadecenylsuccinimid oder 1-Tetradecyleicosuccinimid ist.
4. Verfahren zur Herstellung eines öllöslichen Zusatzmittels nach Anspruch 1, wobei (a) die olefinische Doppelbindung eines linearen a-Olefins oder eines Gemisches davon mit 12 bis 36 Kohlenstoffatomen isomerisiert wird, um ein Gemisch von inneren Olefinen zu erhalten, (b) das Gemisch von inneren Olefinen mit Maleinsäure, -anhydrid oder -ester umgesetzt wird, um eine intermediäre Kohlenwasserstoff-substituierte Succinsäure, -anhydrid oder -ester zu erhalten und (c) die Zwischenverbindung mit Ammoniak umgesetzt wird, um ein Amid, Imid oder ein Gemisch davon zu bilden.
5. Verfahren nach Anspruch 4, worin das a-Olefin hauptsächlich aus linearem α-Tetradecen, linearem a-Hexadecen, linearem a-Octadecen oder linearem α-Eicosen besteht.
6. Verfahren nach Anspruch 4 oder Anspruch 5, worin die Isomerisierung des linearen a-Olefins durch Erhitzen des linearen α-Olefins mit einem sauren Katalysator durchgeführt wird.
7. Schmieröl-oder Brennstoffzusammensetzung, die eine reibungsmindernde Menge eines Zusatzmittels nach einem der Ansprüche 1 bis 3 enthalten oder nach einem Verfahren gemäß einem der Ansprüche 4 bis 6 hergestellt sind.
8. Schmieröl-oder Brennstoffzusammensetzung nach Anspruch 7, worin das Zusatzmittel Tetradecenylsuccinimid, Hexadecenylsuccinimid, Octadecenylsuccinimid oder Eicosenylsuccinimid ist.
9. Schmieröl-Zusammensetzung nach Anspruch 7 oder Anspruch 8, worin das Zusatzmittel darin in einer Menge von 0,05 bis 3 Gew.-% enthalten ist.
10. Brennstoff-Zusammensetzung nach Anspruch 7 oder Anspruch 8, worin das Zusatzmittel darin in einer Menge von 0,001 bis 0,25 Gew.-% enthalten ist.
EP80301487A 1979-05-18 1980-05-07 Öllöslicher reibungsvermindernder Zusatzstoff, Verfahren zu dessen Herstellung und Schmieröl- oder Kraftstoff-Zusammensetzung, die den Zusatzstoff enthält Expired EP0020037B1 (de)

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US4661275A (en) * 1985-07-29 1987-04-28 The Lubrizol Corporation Water-based functional fluid thickening combinations of surfactants and hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products
WO1987002663A1 (en) * 1985-10-25 1987-05-07 The Lubrizol Corporation Compositions, concentrates, lubricant compositions, fuel composition and methods for improving fuel economy of internal combustion engines
US4664834A (en) * 1985-07-29 1987-05-12 The Lubrizol Corporation Hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products, and aqueous systems containing same
EP0389237A2 (de) * 1989-03-20 1990-09-26 Ethyl Petroleum Additives Limited Reibungsmodifiziermittel
EP0399764A1 (de) * 1989-05-22 1990-11-28 Ethyl Petroleum Additives Limited Schmiermittel-Zusammensetzungen
EP0448207A1 (de) * 1990-02-16 1991-09-25 Ethyl Petroleum Additives, Inc. Schmiermittelzusammensetzungen
EP0459656A1 (de) * 1990-05-17 1991-12-04 Ethyl Petroleum Additives, Inc. Schmiermittelzusammensetzungen
US5122616A (en) * 1989-09-11 1992-06-16 Ethyl Petroleum Additives, Inc. Succinimides
US5225093A (en) * 1990-02-16 1993-07-06 Ethyl Petroleum Additives, Inc. Gear oil additive compositions and gear oils containing the same
USRE34459E (en) * 1989-03-20 1993-11-30 Ethyl Petroleum Additives, Limited Friction modifier
US5358651A (en) * 1985-10-25 1994-10-25 The Lubrizol Corporation Compositions, concentrates, lubricant compositions, fuel composition and methods for improving fuel economy of internal combustion engines
US5498355A (en) * 1994-09-20 1996-03-12 Ethyl Corporation Lubricant compositions of enhanced performance capabilities
US5516444A (en) * 1994-10-13 1996-05-14 Exxon Chemical Patents Inc Synergistic combinations for use in functional fluid compositions
US5750476A (en) * 1995-10-18 1998-05-12 Exxon Chemical Patents Inc. Power transmitting fluids with improved anti-shudder durability
US5767045A (en) * 1995-12-01 1998-06-16 Ethyl Petroleum Additives Limited Hydraulic fluids
US5840662A (en) * 1995-10-18 1998-11-24 Exxon Chemical Patents Inc. Lubricating oils of improved friction durability
WO2000043596A2 (de) 1999-01-25 2000-07-27 Betek Bergbau- Und Hartmetall-Technik Karl-Heinz Simon Gmbh & Co. Kg Werkzeug mit verschleissschutzelement für eine strassenfräs-, schrämm-, bergbaumaschine oder dgl
US6096691A (en) * 1993-04-09 2000-08-01 Ethyl Corporation Gear oil additive concentrates and lubricants containing them
US8557752B2 (en) 2005-03-23 2013-10-15 Afton Chemical Corporation Lubricating compositions
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US5328619A (en) * 1991-06-21 1994-07-12 Ethyl Petroleum Additives, Inc. Oil additive concentrates and lubricants of enhanced performance capabilities
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US8690968B2 (en) 2008-04-04 2014-04-08 Afton Chemical Corporation Succinimide lubricity additive for diesel fuel and a method for reducing wear scarring in an engine
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US4661275A (en) * 1985-07-29 1987-04-28 The Lubrizol Corporation Water-based functional fluid thickening combinations of surfactants and hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products
US4664834A (en) * 1985-07-29 1987-05-12 The Lubrizol Corporation Hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products, and aqueous systems containing same
WO1987002663A1 (en) * 1985-10-25 1987-05-07 The Lubrizol Corporation Compositions, concentrates, lubricant compositions, fuel composition and methods for improving fuel economy of internal combustion engines
US5358651A (en) * 1985-10-25 1994-10-25 The Lubrizol Corporation Compositions, concentrates, lubricant compositions, fuel composition and methods for improving fuel economy of internal combustion engines
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EP0454180A3 (en) * 1985-10-25 1991-12-11 Lubrizol Corp Compositions, concentrates, lubricant compositions, fuel composition and methods for improving fuel economy of internal combustion engines
EP0389237A2 (de) * 1989-03-20 1990-09-26 Ethyl Petroleum Additives Limited Reibungsmodifiziermittel
EP0389237A3 (en) * 1989-03-20 1990-10-31 Ethyl Petroleum Additives Limited Friction modifier
USRE34459E (en) * 1989-03-20 1993-11-30 Ethyl Petroleum Additives, Limited Friction modifier
EP0399764A1 (de) * 1989-05-22 1990-11-28 Ethyl Petroleum Additives Limited Schmiermittel-Zusammensetzungen
US5126064A (en) * 1989-05-22 1992-06-30 Ethyl Petroleum Additives, Ltd. Lubricant compositions
US5122616A (en) * 1989-09-11 1992-06-16 Ethyl Petroleum Additives, Inc. Succinimides
US5225093A (en) * 1990-02-16 1993-07-06 Ethyl Petroleum Additives, Inc. Gear oil additive compositions and gear oils containing the same
EP0448207A1 (de) * 1990-02-16 1991-09-25 Ethyl Petroleum Additives, Inc. Schmiermittelzusammensetzungen
US5942470A (en) * 1990-05-17 1999-08-24 Ethyl Petroleum Additives, Inc. Lubricant compositions
EP0459656A1 (de) * 1990-05-17 1991-12-04 Ethyl Petroleum Additives, Inc. Schmiermittelzusammensetzungen
US6096691A (en) * 1993-04-09 2000-08-01 Ethyl Corporation Gear oil additive concentrates and lubricants containing them
US5498355A (en) * 1994-09-20 1996-03-12 Ethyl Corporation Lubricant compositions of enhanced performance capabilities
US5516444A (en) * 1994-10-13 1996-05-14 Exxon Chemical Patents Inc Synergistic combinations for use in functional fluid compositions
US5840662A (en) * 1995-10-18 1998-11-24 Exxon Chemical Patents Inc. Lubricating oils of improved friction durability
US5750476A (en) * 1995-10-18 1998-05-12 Exxon Chemical Patents Inc. Power transmitting fluids with improved anti-shudder durability
US5767045A (en) * 1995-12-01 1998-06-16 Ethyl Petroleum Additives Limited Hydraulic fluids
WO2000043596A2 (de) 1999-01-25 2000-07-27 Betek Bergbau- Und Hartmetall-Technik Karl-Heinz Simon Gmbh & Co. Kg Werkzeug mit verschleissschutzelement für eine strassenfräs-, schrämm-, bergbaumaschine oder dgl
US6619757B1 (en) 1999-01-25 2003-09-16 Betek Bergbau- Und Hartmettall-Technik Karl-Heinz Simon Gmbh & Co. Kg Tool for a street milling, coal-cutting or mining machine
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