EP0100665B1 - Schlammkontrollierende Zusätze in Kohlenwasserstoffbrennstoffen und Schmiermitteln für Innenverbrennungsmotoren - Google Patents

Schlammkontrollierende Zusätze in Kohlenwasserstoffbrennstoffen und Schmiermitteln für Innenverbrennungsmotoren Download PDF

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Publication number
EP0100665B1
EP0100665B1 EP83304397A EP83304397A EP0100665B1 EP 0100665 B1 EP0100665 B1 EP 0100665B1 EP 83304397 A EP83304397 A EP 83304397A EP 83304397 A EP83304397 A EP 83304397A EP 0100665 B1 EP0100665 B1 EP 0100665B1
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EP
European Patent Office
Prior art keywords
additive
polyamine
carbon atoms
hydrocarbyl
internal combustion
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
EP83304397A
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English (en)
French (fr)
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EP0100665A2 (de
EP0100665A3 (en
Inventor
Curtis B. Campbell
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
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Chevron Research 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
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Publication of EP0100665A2 publication Critical patent/EP0100665A2/de
Publication of EP0100665A3 publication Critical patent/EP0100665A3/en
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Publication of EP0100665B1 publication Critical patent/EP0100665B1/de
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Classifications

    • 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
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
    • 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
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
    • 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
    • C10M2215/02—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
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives

Definitions

  • This invention relates to deposit control additives for hydrocarbon fuels and lubricants to be used in internal combustion engines, especially internal combustion engines designed to run on unleaded gasoline.
  • Deposits adversely affect the operation of the engine. For example, deposits on the carburetor throttle body and venturies increase the fuel to air ratio of the gas mixture to the combustion chamber thereby increasing the amount of unburned hydrocarbon and carbon monoxide discharged from the chamber. The high fuel-air ratio also reduces the gas mileage obtainable from the engine.
  • each engine when new, requires a certain minimum octane fuel in order to operate satisfactorily without pinking and/or knocking.
  • this minimum octane increases and, in most cases, if the engine is operated on the same fuel for a prolonged period, will reach an equilibrium. This is apparently caused by an amount of deposits in the combustion chamber. Equilibrium is typically reached after 5000 to 15,000 miles (8047 to 24140 km) of automobile operation.
  • the octane requirement increase in particular engines used with commercial gasolines will vary at equilibrium from 5 or 6 octane units to as high as 12 or 15 units, depending upon the gasoline compositions, engine design and type of operation. The seriousness of the problem is thus apparent.
  • a typical automobile with a research octane requirement of 85, when new, may after a few months of operation require 97 research octane gasoline for proper operation, and little unleaded gasoline of that octane is available.
  • the ORI problem also exists in some degree with engines operated on leaded fuels.
  • the ORI problem is compounded by the fact that the most common method for increasing the octane rating of unleaded gasoline is to increase its aromatic content. This, however, eventually increases even more the necessary octane requirement. Moreover, some of the nitrogen-containing compounds presently used as deposit-control additives and their mineral oil or polymer carriers may also significantly contribute to ORI in engines using unleaded fuels.
  • deposit control additives which, when incorporated in hydrocarbon fuels, are effective in maintaining the cleanliness of engine intake systems.
  • the additives are hydrocarbyl-terminated polyoxyalkylene polyamine ethanes soluble in hydrocarbon fuel boiling in the gasoline range.
  • the hydrocarbyl-terminated polyoxyalkylene chain contains oxyalkylene units of 3 or 4 carbon atoms.
  • the polyoxyalkylene chain contains from 1 to 30 oxyalkylene units and is bonded through a terminal carbon to an ethane chain or connecting group which is in turn bonded to the nitrogen atom of a polyamine having from 2 to 12 amine nitrogens and from 2 to 40 carbon atoms with a carbon-nitrogen ratio in the range from 1:1 to 10:1.
  • the hydrocarbyl-terminating group contains from 1 to 30 carbon atoms and is bonded to the polyoxyalkylene units through an ether oxygen atom.
  • the additives normally have a molecular weight in the range from 300 to 2500, preferably from 800 to 1500.
  • the polyoxyalkylene polyamine ethane additives of the invention can be incorporated in a liquid hydrocarbon fuel generally in an amount of from 30 to 10,000 ppm by weight of said additive.
  • the additive will be incorporated in the hydrocarbon fuel in the form of an additive concentrate comprising the additive and an inert stable oleophilic organic solvent.
  • the additive may also be incorporated in a lubricating oil composition for use as a lubricant in an internal combustion engine.
  • the additive consists of three parts or moieties.
  • the first is the polyamine moiety
  • the second the poly(oxyalkylene) moiety comprising at least one hydrocarbyl-terminated polyoxyalkylene polymer, bonded through the third moiety, an ethane connecting group or linkage, connected in turn to the nitrogen atom of the polyamine.
  • the polyoxyalkylene moiety, the polyamine moiety, and the ethane moiety are selected to provide solubility in the fuel composition and deposit control activity without contributing to octane requirement increase (ORI).
  • the moieties may be selected to provide solubility in lubricating-oil compositions and dispersant activity.
  • the additives may be termed hydrocarbyl poly(oxyalkylene) polyamine ethanes or for convenience, "polyether polyamine ethanes”.
  • the additives may be prepared from the reaction of a suitable halogenating agent containing the desired ethane moiety, such as ethylene chlorohydrin, with the appropriate substituted epoxide, polymerizing to the polyoxyalkylene chain. This is in turn reacted with the appropriate hydrocarbyl cap which is followed by reaction of the capped polyether chloride with the appropriate polyamine to form the required additive.
  • a suitable halogenating agent containing the desired ethane moiety such as ethylene chlorohydrin
  • the polyoxyalkylene moiety is ordinarily prepared by the reaction of an appropriate chlorohydrin containing the ethane connecting group.
  • ethylene chlorohydrin is reacted under polymerization conditions with the lower alkylene oxides or oxiranes such as propylene oxide or butylene oxide.
  • a single type of alkylene oxide may be employed.
  • Copolymers, however, are equally satisfactory and random copolymers are readily prepared by contacting the ethylene chlorohydrin compound with a mixture of alkylene oxides.
  • Blocked copolymers of oxyalkylene units also provide satisfactory polyoxyalkylene polymers for the practice of the present invention. Blocked copolymers are prepared by reacting the chlorohydrin with first one alkylene oxide and then the other in any order, or repetitively, under polymerization conditions.
  • the resulting polyoxyalkylene ethylene chloride is then reacted with the suitable hydrocarbyl cap to complete the precursor of the polyoxyalkylene moiety.
  • the hydrocarbyl cap (R-) contains from 1 to 30 carbon atoms, preferably from 2 to 20 carbon atoms.
  • the hydrocarbyl group may be any straight chain or branched aliphatic, olefinic or alkyl aryl hydrocarbon chain.
  • the hydrocarbyl cap is added to the polyoxyalkylene precursor by the addition of the desired compound group to the polyoxyalkylene ethylene chloride in a catalyzed reaction utilizing an acid ion exchange resin reaction.
  • the hydrocarbyl polyoxyalkylene ethane moiety consists of one or more, preferably 1 or 2, more preferably one hydrocarbyl-terminated poly(oxyalkylene)polymer, composed of oxyalkylene units containing 3 or 4 carbon atoms.
  • the poly(oxyalkylene)polymer contains at least one oxyalkylene unit, generally 1 to 30 units, preferably 5 to 30 units and most preferably 10 to 25 oxyalkylene units.
  • the terminal carbon atom at the hydroxyl end of the polyoxyalkylene chain is bound to the ethane connecting group which is in turn bound to the nitrogen atom- of the polyamine.
  • poly(oxyalkylene) compounds are mixtures of compounds that differ in polymer chain length. However, their properties closely approximate those of a polymer represented by the average composition and molecular weight.
  • the ethane connecting group consists of a 2-carbon chain ethylene group.
  • compositions containing the ethane connecting groups enhances the composition's use as a deposit control additive, ORI inhibitor, or dispersant agent by providing the molecule with less steric hindrance and greater polarity at the amine moiety end of the molecule. This allows the molecule to "bind" better to metal engine surfaces and/or combustion chamber deposits thereby enhancing its detergency effect.
  • the polyamine moiety of the polyether polyamine is derived from a polyamine having from 2 to 12 amine nitrogen atoms and from 2 to 40 carbon atoms.
  • the polyamine preferably has a carbon to nitrogen ratio of from 1:1 to 10:1.
  • the polyamine will contain at least 1 primary or secondary amine nitrogen atom.
  • the polyamine may be substituted with a substituent group selected from (A) hydrogen; (B) hydrocarbyl groups of from 1 to 10 carbon atoms; (C) acyl groups of from 2 to 10 carbon atoms; and (D) monoketo, monohydroxy, monocyano, lower alkyl and lower alkoxy derivatives of (B) or (C).
  • “Lower”, as used in lower alkyl and lower alkoxy, means a group containing from 1 to 6 carbon atoms.
  • “Hydrocarbyl” denotes an organic radical composed of carbon and hydrogen which may be aliphatic, alicyclic, aromatic or combinations thereof, e.g. aralkyl.
  • the hydrocarbyl group will be free of aliphatic unsaturation, i.e. ethylenic and acetylenic, particularly acetylenic unsaturation.
  • the substituted polyamines used in the present invention are generally, but not necessarily, N-substituted polyamines.
  • the acyl groups falling within the definition of the aforementioned (C) substituents are, for example, propionyl or acetyl.
  • the more preferred substituents are hydrogen, C, to C 6 alkyls, and C l -C 6 hydroxyalkyls.
  • the more preferred polyamines finding use in the present invention are polyalkylene polyamines, including alkylene diamine and including substituted polyamines, e.g. alkyl and hydroxyalkyl substituted polyalkylene polyamines.
  • the alkylene groups contain from 2 to 6 carbon atoms, there being preferably 2 or 3 carbon atoms between the nitrogen atoms.
  • Such groups are exemplified by ethyleneamines and include ethylene diamine, diethylene triamine, di(trimethylene) triamine, dipropylenetriamine and triethylenetetramine.
  • Such amines encompass isomers which are the branched- chain polyamines and the previously mentioned substituted polyamines, including hydroxy and hydrocarbyl-substituted polyamines.
  • polyalkylene polyamines those containing 2 to 12 amine nitrogen atoms and 2 to 24 carbon atoms are especially preferred and the C 2 or C 3 alkylene polyamines are most preferred, in particular, the lower polyalkylene polyamines, e.g. ethylene diamine or tetraethylenepentamine.
  • a single compound will not be used as reactant in the preparation of the additives of this invention, in particular the polyamine component. That is, mixtures will be used in which one or two compounds will predominate with the average composition indicated.
  • tetraethylene pentamine prepared by the polymerization of aziridine or the reaction of dichloroethylene and ammonia will have both lower and higher amine numbers, e.g. triethylene tetramine, substituted piperazines and pentaethylene hexamine, but the composition will be mainly tetraethylene pentamine and the empirical formula of the total amine composition will closely approximate that of tetraethylene pentamine.
  • compositions comprising the additives of the present invention are prepared by the reaction on the hydrocarbyl capped polyoxyalkylene-ethane moiety containing a reactable chlorine or other halogen with the appropriately selected amine or polyamine.
  • the basic substitution reaction yields the attachment of the polyamine to the polyoxyalkylene and the elimination of the hydrogen halide.
  • the class of preferred polyether polyamine ethanes may be defined by the following general formula: wherein
  • the polyether ethylene amines can be used as additives in hydrocarbon distillate fuel and, in particular, unleaded gasoline.
  • concentration of the additive necessary in order to achieve the desired deposit control effect or carburetor detergency is dependent upon a variety of factors, including for instance the type of fuel used and the presence of other detergents or dispersants or other additives.
  • the range of concentration of the additive in the base fuel is 30 to 10,000 weight parts per million, preferably from 30 to 2,000 weight parts per million, and most preferably from 100 to 700 parts per million of polyether polyamine ethane per part of base fuel. If other detergents are present, a lesser amount of polyether polyamine ethane may be used.
  • oils which find use in producing lubricating oil compositions containing the additives of this invention are generally oils of lubricating viscosity derived from petroleum or synthetic sources. Oils of lubricating viscosity normally have viscosities in the range from 35 to 50,000 Saybolt Universal Seconds (SUS) at 100°F (37.8°C) and more usually from 50 to 10,000 SUS at 100°F (37.8°C). Examples of such base oils are naphthenic bases, paraffin base and mixed base mineral oils, synthetic oils, for example, alkylene polymers, such as the polymers of propylene or butylene, and mixtures thereof.
  • SUS Saybolt Universal Seconds
  • base oils are naphthenic bases, paraffin base and mixed base mineral oils, synthetic oils, for example, alkylene polymers, such as the polymers of propylene or butylene, and mixtures thereof.
  • oils in addition to the additives of the invention are one or more of such additives as dispersants/detergents, rust inhibitors, antioxidants, oiliness agents, foam inhibitors, viscosity index improvers and pour point depressants.
  • these other additives will be present in amounts of from 0.5 to 15 weight percent of the total composition.
  • each of the additives will be present in the range from 0.01 to 5 weight percent of the total composition.
  • the polyether polyamine ethanes may be used as concentrates, and could be used as additive to fuels or lubricating oils subsequent to their preparation.
  • the weight percent of these additives will usually range from 0.3 to 50, preferably 10 to 50, weight percent.
  • the concentrate would ordinarily comprise an inert stable oleophilic organic solvent generally boiling in the range from 150 to 400°F (65.6 to 204.4°C) and the concentrate would preferably contain from 10 to 50 weight percent of the polyether polyamine ethane compound.
  • the solution was extracted with cold water, then with a saturated solution of sodium bicarbonate and then with additional water.
  • the product was stripped without drying and afforded 23.4 grams of a translucent oil after pumping with high vacuum.
  • the product was redried in diethylether over anhydrous magnesium sulphate and was stripped to afford 22.6 grams of polyoxyalkylene ethane chloride.
  • reaction product was diluted with hexane, filtered and stripped to afford 1.7 grams of a clean oil.
  • the crude product was taken up in diethylether and washed three times with water, dried over magnesium sulphate and stripped to afford 1.4 grams of a clean oil.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Claims (11)

1. Addditiv zur Ablagerungsbekämpfung für eine Verwendung in einem Ottomotor, bei dem es sich um ein Kohlenwasserstoff-terminiertes Polyoxyalkylenpolyaminethan mit einem Molekulargewicht im Bereich von 300 bis 2500 handelt, wobei die Kohlenwasserstoffgruppe 1 bis 30 Kohlenstoffatome enthält, der Polyoxyalkylenanteil 1 bis 30 Oxyalkyleneinheiten aufweist, von denen jede 3 oder 4 Kohlenstoffatome besitzt, und der Polyaminanteil 2 bis 12 Amin-Stickstoffatome und 2 bis 40 Kohlenstoffatome bei einem Kohlenstoff:Stickstoff-Verhältnis im Bereich von 1:1 bis 10:1 aufweist.
2. Additiv nach Anspruch 1, dadurch gekennzeichnet, daß das Kohlenwasserstoff-terminierte Polyoxyalkylenpolyaminethan ein Molekulargewicht im Bereich von 800 bis 1500 besitzt.
3. Additiv nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß die Kohlenwasserstoffgrupe 2 bis 20 Kohlenstoffatome enthält.
4. Additiv nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, daß der Polyaminanteil auf ein niederes Polyalkylenpolyamin zurückgeht und wenigstens ein primäres oder sekundäres Amin-Stickstoffatom enthält.
5. Additiv nach Anspruch 4, dadurch gekennzeichnet, daß das niedere Polyalkylenpolyamin aus Ethylendiamin oder Diethylentriamin besteht.
6. Kohlenwasserstoff-Treibstoffzubereitung für eine Verwendung in einem Ottomotor aus einem Kohlenwasserstoff, der in dem Benzinbereich siedet, und einem eine Ablagerung bekämpfenden Additiv gemäß einem der Ansprüche 1 bis 5.
7. Treibstoffzubereitung nach Anspruch 6, dadurch gekennzeichnet, daß das Additiv in einer Menge von 30 bis 10000 ppm, bezogen auf das Gewicht, vorliegt.
8. Treibstoffzubereitung nach Anspruch 6 oder 7, dadurch gekennzeichnet, daß der Kohlenwasserstoff ein nichtgebleites Benzin ist.
9. Additivkonzentrat aus einem inerten stabilen oliophilen organischen Lösungsmittel und einem Additiv gemäß einem der Ansprüche 1 bis 5.
10. Konzentrat nach Anspruch 9, dadurch gekennzeichnet, daß das organische Lösungsmittel im Bereich von 150 bis 400°F (65,6 bis 204,4°C) siedet und 10 bis 50 Gew.-% des Additivs enthält.
11. Schmier zubereitung für eine Verwendung in einem Ottomotor aus einem Öl mit Schmierviskosität und einem eine Ablagerung bekämpfenden Additiv gemäß einem der Ansprüche 1 bis 5.
EP83304397A 1982-07-30 1983-07-29 Schlammkontrollierende Zusätze in Kohlenwasserstoffbrennstoffen und Schmiermitteln für Innenverbrennungsmotoren Expired EP0100665B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US40360782A 1982-07-30 1982-07-30
US403607 1982-07-30

Publications (3)

Publication Number Publication Date
EP0100665A2 EP0100665A2 (de) 1984-02-15
EP0100665A3 EP0100665A3 (en) 1984-03-28
EP0100665B1 true EP0100665B1 (de) 1987-04-08

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EP83304397A Expired EP0100665B1 (de) 1982-07-30 1983-07-29 Schlammkontrollierende Zusätze in Kohlenwasserstoffbrennstoffen und Schmiermitteln für Innenverbrennungsmotoren

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EP (1) EP0100665B1 (de)
DE (1) DE3370820D1 (de)

Cited By (1)

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Publication number Priority date Publication date Assignee Title
US8100095B2 (en) 2006-11-17 2012-01-24 Mcknight James K Combustion devices for powdered fuels and powdered fuel dispersions

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DE3478696D1 (en) * 1983-08-08 1989-07-20 Chevron Res Diesel fuel and method for deposit control in compression ignition engines
US4778481A (en) * 1983-08-08 1988-10-18 Chevron Research Company Diesel fuel and method for deposit control in compression ignition engines
US4746328A (en) * 1985-07-19 1988-05-24 Kao Corporation Stabilized fuel oil containing a dispersant
US5814110A (en) * 1986-09-24 1998-09-29 Exxon Chemical Patents Inc. Chemical compositions and use as fuel additives
DE3732908A1 (de) * 1987-09-30 1989-04-13 Basf Ag Polyetheramine enthaltende kraftstoffe fuer ottomotoren
DE3826608A1 (de) * 1988-08-05 1990-02-08 Basf Ag Polyetheramine oder polyetheraminderivate enthaltende kraftstoffe fuer ottomotoren
ES2061825T3 (es) * 1988-08-05 1994-12-16 Kao Corp Utilizacion de un aditivo para combustibles.
JPH0662965B2 (ja) * 1990-02-02 1994-08-17 花王株式会社 燃料油添加剤及び燃料油添加剤組成物
TW239158B (de) * 1991-02-15 1995-01-21 Lubrizol Corp
US5354343A (en) * 1992-08-31 1994-10-11 Shell Oil Company Gasoline composition
US5203879A (en) * 1992-09-01 1993-04-20 Texaco Inc. Fuel composition
US5332407A (en) * 1992-10-19 1994-07-26 Texaco Inc. Diesel fuel additive providing clean up detergency of fuel injectors
US5383942A (en) * 1993-06-22 1995-01-24 Texaco Inc. Fuel composition
DE4432038A1 (de) * 1994-09-09 1996-03-14 Basf Ag Polyetheramine enthaltende Kraftstoffe für Ottomotoren
EP1122295A4 (de) * 1998-10-06 2002-02-06 Nippon Mitsubishi Oil Corp Benzinzusatz für einen benzinmotor mit direkteinspritzung
US6217624B1 (en) * 1999-02-18 2001-04-17 Chevron Chemical Company Llc Fuel compositions containing hydrocarbyl-substituted polyoxyalkylene amines
US6346128B1 (en) * 1999-11-30 2002-02-12 Texaco Inc. Two-cycle engine fuel composition and method for using same

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US3373204A (en) * 1964-04-15 1968-03-12 Atlas Chem Ind Process for preparing oxyalkylene amines
US4247301A (en) * 1978-06-19 1981-01-27 Chevron Research Company Deposit control and dispersant additives
US4332595A (en) * 1980-12-05 1982-06-01 Texaco Inc. Ether amine detergent and motor fuel composition containing same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8100095B2 (en) 2006-11-17 2012-01-24 Mcknight James K Combustion devices for powdered fuels and powdered fuel dispersions

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EP0100665A2 (de) 1984-02-15
DE3370820D1 (en) 1987-05-14
EP0100665A3 (en) 1984-03-28

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