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EP0151621B1 - Additifs quaternaires regulateurs de depots - Google Patents

Additifs quaternaires regulateurs de depots Download PDF

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Publication number
EP0151621B1
EP0151621B1 EP19840903020 EP84903020A EP0151621B1 EP 0151621 B1 EP0151621 B1 EP 0151621B1 EP 19840903020 EP19840903020 EP 19840903020 EP 84903020 A EP84903020 A EP 84903020A EP 0151621 B1 EP0151621 B1 EP 0151621B1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
quaternized
group
amine
polyoxyalkylene
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
EP19840903020
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German (de)
English (en)
Other versions
EP0151621A4 (fr
EP0151621A1 (fr
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
Original Assignee
Chevron Research and Technology Co
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
Application filed by Chevron Research and Technology Co, Chevron Research Co filed Critical Chevron Research and Technology Co
Publication of EP0151621A1 publication Critical patent/EP0151621A1/fr
Publication of EP0151621A4 publication Critical patent/EP0151621A4/fr
Application granted granted Critical
Publication of EP0151621B1 publication Critical patent/EP0151621B1/fr
Expired legal-status Critical Current

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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
    • 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
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
    • 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
    • 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
    • C10M133/18—Amides; Imides of carbonic or haloformic 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/20—Thiols; Sulfides; Polysulfides
    • C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M135/24—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
    • 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
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043—Polyoxyalkylene ethers with a thioether group

Definitions

  • This invention relates to quaternary salts of various polyether polyamines, to fuel compositions and lubricating oil compositions containing these compounds and to their use as either fuel additives or detergents or dispersancy additives in lubricating oils.
  • Deposits adversely affect the operation of the vehicle. 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 vehicle.
  • this application also relates to lubricting oil compositions containing quaternary polyether amine additives which contribute dispersancy and detergency to the compositions.
  • Lubricating oil compositions particularly for use in internal combustion engines, have long performed many functions other than simply lubricating moving parts. Modern-day, highly compounded lubricating oil compositions provide anti-wear, anti-oxidant, extreme-pressure and anti-rust protection in addition to maintaining the cleanliness of the engine by detergency and dispersancy. Many lubricating oil additives are well-known for accomplishing these functions.
  • Deposit control additives including polyether amines are disclosed in U.S. Patent No. 3,864,098 and hydrocarbyl polyoxyalkylene polyamines in U.S. Patent No. 4,247,301.
  • U.S. Patent No. 4,160,648 discloses deposit control additives comprised of polyoxyalkylene carbamates;
  • EP-A-0100665 discloses polyether polyamine ethanes as deposit control additives.
  • carboxylic and other acid salts, as well as the quaternary salts of basic nitrogen-containing polymers are known in the art as deposit control and/or carburetor detergent additives in fuel compositions. See, for example, U.S. Patent No. 3,468,640. These additives are also known to have improved corrosion inhibition properties relative to the pure basic nitrogen-containing polymers.
  • additives are provided which, when added to fuel or used as fuel concentrates, are effective in maintaining the cleanliness of the engine and its intake systems.
  • the additives consist of the quaternary salts of various polyether polyamines soluble in hydrocarbon fuel boiling in the gasoline range. These quaternary salts show enhanced dispersancy and corrosion inhibition and therefore serve well as deposit control and/or carburetor dispersants. The nature of the anion in these various salts has also been found to affect their performance.
  • the polyoxyalkylene moiety comprises at least 5 oxyalkylene units of from 2 to 4 carbon atoms and may be terminated or "capped” with a hydrocarbyl group.
  • the hydrocarbyl terminating group of the polyoxyalkylene moiety may contain from between 5 to 30 carbon atoms.
  • the polyoxyalkylene chain is bonded through a terminal oxygen to the appropriate connecting group which is in turn bonded to an amino nitrogen atom in the amine or polyamine group.
  • the polyamine preferably contains from 2 to 12 amine nitrogens and from 2 to 40 carbon atoms, with a carbon-nitrogen ratio of between 1:1 and 10:1. At least one nitrogen atom is quaternized with a hydrocarbyl halide.
  • the compounds have a molecular weight in the range of 500 to 2500, and preferably from 800 to 1500.
  • the hydrocarbyl halides finding use as the quaternizing agents include alkyl groups containing from 1 to 20 carbon atoms and may be or contain aromatic groups such as phenyl or benzyl groups.
  • the halides of the alkyl halide group ordinarily consist of chloride, bromide and iodide. Certain of the additives of the present invention are believed to be useful as dispersant additives in lubricating oils as well.
  • the present invention herein consists of a fuel additive, a quaternized polyoxyalkylene polyamine or polyether polyamine, and a fuel composition containing a liquid hydrocarbon fuel boiling in the gasoline range and from 30 to 10,000 rpm of said additive.
  • the quaternized polyether polyamine has a molecular weight of from 500 to 2500, and preferably from 800 to 1500.
  • the additive consists of three parts or moieties. The first is the polyether .or polyoxyalkylene moiety, which may or may not be hydrocarbyl terminated or "capped”.
  • the polyether moiety is bound through the second moiety, a connecting group or linkage to the nitrogen atom of the third moiety, the amine, which is quaternized by an appropriate alkyl halide.
  • the polyoxyalkylene moiety and the quaternized amino moiety are selected to provide solubility in the fuel composition, deposit control activity, and corrosion inhibition within a vehicle's fuel system and engine.
  • the moieties are selected to provide solubility in a lubricating oil composition with dispersant activity and corrosion inhibition properties.
  • the moieties are selected to provide solubility in a lubricating oil composition with dispersant activity and corrosion inhibition properties.
  • the polyoxyalkylene moiety is ordinarily comprised of polyoxyalkylene polymers containing 5 to 30 oxyalkylene units, and most preferably 10 to 25 oxyalkylene units. When polymerized in the polymerization reaction, a single type of alkylene oxide may be employed. Copolymers, however, are equally satisfactory and random copolymers are readily prepared. Blocked copolymers of oxyalkylene units also provide satisfactory polyoxyalkylene polymers for the practice of the present invention.
  • the polyoxyalkylene moiety may ordinarily be prepared in a variety of ways, the most common for the practice of the present invention being by the reaction of an appropriate lower alkylene oxide containing from 2 to 4 carbon atoms with an appropriate initiator; for example, chlorohydrin or an alkyl phenol. In the preferred embodiment, ethylene chlorohydrin is used.
  • Copolymers may be readily prepared by contacting the initiator compound with a mixture of alkylene oxides, while the blocked copolymers may be prepared by reacting the initiator first with one alkylene oxide and then another in any order or repetitively under polymerization conditions.
  • the polyoxyalkylene moiety derived from an alkyl phenol initiated polymerization detailed above is prepared as an alcohol containing a terminal hydroxyl group.
  • the polyether moiety is then attached through the appropriate connecting group to the polyamine moiety by a variety of ways, one of which includes reacting the hydroxyl group of the polyoxyalkylene unit with phosgene to form a polyoxyalkylene chloroformate and then reacting the polyoxyalkylene chloroformate with an amine.
  • the hydroxyl group may be reacted with epichlorohydrin to give a methylol-substituted ethyl chloride end group.
  • the resulting polyoxyalkylene alkyl chloride is then reacted with an amine or polyamine to produce the composition to be quaternized, resulting in the composition of the present invention.
  • connecting group which results and is used in the present composition is ordinarily a function of the method by which the compositions are formed and/or by which components of the polyoxyalkylene moiety and the polyamine moiety are joined together.
  • the amine moiety of the quaternized polyether amine is derived from ammonia or, more preferably, 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 about 1:1 to about 10:1.
  • the polyamine may be substituted with a substituent group selected from (A) hydrogen; (B) hydrocarbyl groups from 1 to 10 carbon atoms; (C) acyl groups from 2 to 10 carbon atoms; and (D) monoketo, monocyano, lower alkyl and lower alkoxy derivatives of (B), (C).
  • “Lower", as used in lower alkyl and lower alkoxy, means a group containing 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 substituted polyamines of the present invention are generally, but not necessarily, N-substituted polyamines.
  • the acyl groups falling within the definition of the aforementioned (C) substituents are such as propionyl, acetyl, etc.
  • the more preferred substituents are hydrogen, C 1 to C 6 alkyls, and C l -C e hydroxyalkyls.
  • polyalkylene polyamines including alkylene diamine and substituted polyamines, e.g. alkyl and hydroxyalkyl- substituted polyalkylene polyamines.
  • alkylene groups contain from 2 to 6 carbon atoms, there being preferably from 2 to 3 carbon atoms between the nitrogen atoms.
  • Such groups are exemplified by ethyleneamines and include ethylene diamine, diethylene triamine, di(trimethylene)triamine, dipropylenetriamine, triethylenetetramine, etc.
  • 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 to C 3 alkylene polyamines are most preferred, in particular, the lower polyalkylene polyamines, e.g. ethylene diamine, tetraethylenepentamine, etc.
  • compositions of the present invention are prepared by the quaternization of the polyether polyamines using alkyl halides.
  • Quaternary ammonium compounds are generally prepared by the reaction of amines with alkyl halides. These compounds have 4 carbon atoms linked directly to a nitrogen atom through covalent bonding. The anion in the original alkylating agent is therefore linked to the nitrogen through an electrovalent bond.
  • the compositions are prepared by reacting the appropriate polyether polyamine with an alkyl halide containing from 1 to 20 carbon atoms.
  • the alkyl halide may also contain aromatics such as benzyl, etc.
  • the halides utilized in the alkyl halides of the present invention ordinarily consist of chloride, bromide and iodide.
  • oils which find use in this invention are oils of lubricating oil viscosity derived from petroleum or synthetic sources.
  • Oils of lubricating viscosity normally have viscosities in the range of 35 to 50,000 Saybolt Universal Seconds (SUS) at 37.8°C, and more usually from about 50 to 10,000 SUS at 37.8°C.
  • base oils are naphthenic bases; paraffin bases; mixed-base mineral oils; and synthetic oils, for example, alkylene polymers such as polymers of propyiene, butylene, etc.; and mixtures thereof.
  • oils besides the subject additives are such additives as dispersants/detergents, rust inhibitors, anti-oxidants, oiliness agents, foam inhibitors, viscosity index improvers, pour point depressants, etc.
  • these other additives will be present in amounts of from about 0.5 to 15.0 weight percent of the total composition.
  • each of the additives will be present in the range from about 0.01 to 5.0 weight percent of the total composition.
  • the quaternized polyether polyamines may be used as concentrates, and could be used as additives to fuels or lubricating oils subsequent to their preparation.
  • the weight percent of these additives will usually range from 10 to 50 weight percent.
  • the concentrate would ordinarily comprise an inert, stable oleophilic, organic solvent and the carrier of said solvent, boiling in the range of from about 65.6°C to 204.4°C.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Composition de carburant contenant de 30 à 10000 parties par million d'un additif comprenant des sels d'amines de polyoxyalkylène rendus quaternaires de poids moléculaire compris entre 500 et 2500 environ, la moitié de polyoxyalkylène comprenant de 1 à 30 unités d'oxyalkylène, les unités possédant de 2 à 4 atomes de carbone et l'amine comprenant de 1 à 12 atomes d'azote d'amine et de 2 à 40 atomes de carbone et possédant une moitié de connexion unissant la moitié de polyoxyalkylène à la moitié amine. Sont également décrites des compositions d'huile lubrifiante contenant l'additif, des concentrés de cet additif et la composition de l'additif lui-même.

Claims (12)

1. Sels quaternisés de polyoxyalkylène-amines de poids moléculaire compris dans la plage de 500 à 2500 et comprenant un groupement polyoxyalkylène attaché par un groupe de jonction à un groupement amine, ledit groupement polyoxyalkylène comportant 5 à 30 motifs oxyalkylène choisis entre des motifs oxyalkylène ayant 2 à 4 atomes de carbone; ledit groupe de jonction étant un diradical contenant un ou plusieurs atomes choisis entre des atomes d'hydrogène, de carbone, d'oxygène, de soufre et d'azote, et ledit groupement amine étant dérivé d'ammoniac ou d'une polyamine ayant 2 à 12 atomes d'azote d'amine et 2 à 40 atomes de carbone, et étant quaternisé avec des groupes hydrocarbyle choisis parmi des groupes alkyle contenant 1 à 20 atomes de carbone, des groupes aralkyle contenant 7 à 20 atomes de carbone, des groupes alkaryle contenant 7 à 20 atomes de carbone et le groupe phényle.
2. Sels quaternisés de polyoxyalkylène-amines suivant la revendication 1, dans lesquels le groupement amine est quaternisé avec des groupes alkyle.
3. Sels quaternisés de polyoxyalkylène-amines suivant la revendication 1, représentés par la formule générale:
Figure imgb0027
dans laquelle R représente un groupe alkyle de 5 à 30 atomes de carbone, un groupe aryle de 6 à 30 atomes de carbone, un groupe alkaryle de 7 à 30 atomes de carbone, un groupe aralkyle de 7 à 30 atomes de carbone ou un groupe alkyle à substituant méthylol de 5 à 30 atomes de carbone;
R' et R" représentent indépendamment l'hydrogène, un groupe méthyle ou éthyle; n a une valeur de 5 à 30;
X représente un groupe de jonction choisi entre:
Figure imgb0028
Figure imgb0029
Figure imgb0030
où Z et Z' représentent l'hydrogène ou un groupe méthyle ou éthyle; Riii représente une liaison chimique, un groupe alkylène ou alkylène à substituant hydroxy ayant 2 à 12 atomes de carbone, ou un groupe (NH-CH2CH2)x, dans lequel x a une valeur de 0 à 5;
Riv et R" représentent indépendamment un groupe alkyle de 1 a 20 atomes de carbone, un groupe aralkyle de 7 à 20 atomes de carbone, un groupe alkaryle de 7 à 20 atomes de carbone ou un groupe phényle;
R" représente un groupe alkyle de 1 à 20 atomes de carbone, un groupe aralkyle de 7 à 20 atomes de carbone, un groupe alkaryle de 7 à 20 atomes de carbone, un groupe phényle ou un groupe (CH2 CH2 NH)xH, dans lequel x a une valeur de 1 à 5; et
Y représente un halogénure, un anion carboxylate en C2 à C12, ou un phénate en C6 à C30 ou phénate à substituant alkyle.
4. Sels quaternisés de polyoxyaikylène-amines suivant la revendication 3, dans lesquels Riv, Rv et Rvi sont tous des groupes alkyle.
5. Sel d'amine quaternisé suivant la revendication 1, représenté par la formule:
Figure imgb0031
6. Sel d'amine quaternisé suivant la revendication 1, représenté par la formule:
Figure imgb0032
7. Sel d'amine quaternisé suivant la revendication 1, représenté par la formule:
Figure imgb0033
8. Composition de carburant, comprenant un carburant hydrocarboné liquide bouillant dans la plage de l'essence ét 30 à 10 000 ppm en poids d'un sel d'amine quaternisé l'une quelconque des revendications 1 à 7.
9. Composition de carburant suivant la revendication 8, dans laquelle le sel d'amine quaternisé est présent à une concentration de 100 à 700 ppm en poids.
10. Composition d'huile lubrifiante comprenant une huile de viscosité propre à la lubrification et 0,01 à 10,0 pour cent en poids de la composition totale, d'un sel d'amine quaternisé suivant l'une quelconque des revendications 1 à 7.
11. Concentré comprenant un solvant organique oléophile stable, inerte, bouillant dans la plage de 65,6°C à 204,4°C et 10 à 50 pour cent en poids d'un sel d'amine quaternisé suivant l'une quelconque des revendications 1 à 7.
12. Utilisation comme additif inhibant la formation de dépôts dans une composition de carburant hydrocarboné ou dans une composition d'huile lubrifiante destinée à être utilisée dans un moteur à combustion interne, d'un sel quaternisé d'amine polyoxyalkylénique suivant l'une quelconque des revendications 1 à 7.
EP19840903020 1983-07-29 1984-07-23 Additifs quaternaires regulateurs de depots Expired EP0151621B1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US51850583A 1983-07-29 1983-07-29
US51850683A 1983-07-29 1983-07-29
US518506 1983-07-29
US518505 1983-07-29

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EP0151621A1 EP0151621A1 (fr) 1985-08-21
EP0151621A4 EP0151621A4 (fr) 1986-08-21
EP0151621B1 true EP0151621B1 (fr) 1990-05-02

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GB8710955D0 (en) * 1987-05-08 1987-06-10 Shell Int Research Gasoline composition
GB8712442D0 (en) * 1987-05-27 1987-07-01 Exxon Chemical Patents Inc Diesel fuel composition
US5055607A (en) * 1988-09-09 1991-10-08 Chevron Research Company Long chain aliphatic hydrocarbyl amine additives having an oxy-carbonyl connecting group
IT1245738B (it) * 1990-11-15 1994-10-14 Euron Additivo detergente per carburanti.
FR2682684A1 (fr) * 1991-10-22 1993-04-23 Rouet Jean Procede de traitement des hydrocarbures paraffiniques.
IT1270656B (it) 1994-10-13 1997-05-07 Euron Spa Composizione di carburante
US5814111A (en) * 1995-03-14 1998-09-29 Shell Oil Company Gasoline compositions
US5817593A (en) * 1995-06-02 1998-10-06 The Dow Chemical Company Catalyst and process for producing amines
KR19990063939A (ko) * 1995-10-04 1999-07-26 그레이스 스티븐 에스. 아민 캡핑된 폴리에테르 및 이의 제조방법
EP2589647A1 (fr) 2011-11-04 2013-05-08 Basf Se Polyétheramines quaternisées et leur utilisation en tant qu'additifs dans des carburants et des lubrifiants
BR112015008703A2 (pt) 2012-10-23 2017-07-04 Lubrizol Corp detergente de diesel sem penalidade de peso molecular baixo

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US4294714A (en) * 1979-07-25 1981-10-13 Chevron Research Company Carboxylic acid salt containing deposit control additives and fuel and lube oil compositions containing them

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DE3482122D1 (de) 1990-06-07
EP0151621A4 (fr) 1986-08-21
WO1985000620A1 (fr) 1985-02-14
EP0151621A1 (fr) 1985-08-21

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