Classifications

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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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
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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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
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  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • 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)
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  • 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
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  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/06—Well-defined aromatic compounds
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  • 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
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
  • 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
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  • 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
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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
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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
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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
  • C10M2207/283—Esters of polyhydroxy compounds
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/286—Esters of polymerised unsaturated acids
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  • 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
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  • 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
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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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  • 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 [having hydrocarbon substituents containing less than thirty carbon atoms]
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
  • C10M2215/26—Amines
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
  • C10M2215/28—Amides; Imides
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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
  • C10M2217/042—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
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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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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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—Overbased sulfonic acid salts
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  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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
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  • 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
  • C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
  • C10M2225/041—Hydrocarbon polymers
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  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • 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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  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/25—Internal-combustion engines
  • C10N2040/251—Alcohol-fuelled 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
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  • 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

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 a material which is an oil soluble, C12-36 aliphatic hydrocarbyl succinimideor succinamide provides a friction reducing effect where it is incorporated in lubricating oil.
• the aliphatic hydrocarbon group is derived from a linear ⁇ -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 containing a friction-reducing amount of an additive selected from the group consisting of oil soluble aliphatic hydrocarbon-substituted succinimide and succinamide and mixtures thereof wherein said hydrocarbon substituent contains about 12 to 36 carbon atoms.
• the aliphatic substituent on the succinic group can be any aliphatic hydrocarbon group containing about 12 to 36 carbon atoms including alkyl, alkenyl and polyunsaturated hydrocarbon groups.
• Examples of the above additives include:
• the aliphatic hydrocarbon group is bonded to the succinic group at a secondary carbon atom.
• These compounds have the formula: or wherein n is a small integer from 2 to about 4 and Z is the group: wherein R 1 and R 2 are independently selected from the group consisting of branched and straight chain hydrocarbon groups containing 1 to about 34 carbon atoms such that the total number of carbon atoms in R i and R 2 is about 11 to 35. Examples of these additives are:
• R 1 and R 2 are straight chain aliphatic hydrocarbon groups. These additives have improved solubility in lubricating oil.
• the above highly preferred additives are preferably made from linear a-olefins containing about 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 styrene-divinylbenzene 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 U. S. 4,108,889, incorporated herein by reference.
• the additives are added to the lubricating oil in an amount which reduces the friction 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 composition 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 dispersant 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 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 - 12 a-olefins such as a-decene trimer.
• alkylbenzenes of proper viscosity can be used, such as didodecylbenzene.
• Useful synthetic esters include the esters of both monocarboxylic acid and polycarboxylic acid as well as monohydroxy alkanols and polyols. Typical examples are didocecyl 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 a-decene trimer with 75 to 95 weight percent 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 dihydrocarbyldithiophosphate (ZDDP) in combination with the present additives.
• ZDDP zinc dihydrocarbyldithiophosphate
• Both zinc dialkyl- dithiophosphates and zinc dialkaryldithiophosphates 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 sulfonate or alkaline earth metal alkaryl sulfonates are the alkaline earth metal petroleum sulfonate or alkaline earth metal alkaryl sulfonates.
• alkaline earth metal petroleum sulfonate or alkaline earth metal alkaryl sulfonates are examples of these.
• 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 ethylene-propylene 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 tetraethylene pentamine.
• Mannich ashless dispersants are more fully descirbed 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, methylcyclopenta- dienylmanganese tricarbonyl, rare earth metal chelates, methyl tert-butylether and the like).
• antiknocks e. g., tetraethyllead, methylcyclopenta- dienylmanganese 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., hexyl- nitrate) 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 3.6 miles (5.8 km) 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.

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• 1980
  • 1980-04-22 CA CA000350389A patent/CA1139740A/fr not_active Expired
  • 1980-05-07 DE DE8080301487T patent/DE3068942D1/de not_active Expired
  • 1980-05-07 EP EP80301487A patent/EP0020037B1/fr not_active Expired
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