EP3609986B1 - Des amines alcoxylées pour additifs de carburant - Google Patents

Des amines alcoxylées pour additifs de carburant Download PDF

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EP3609986B1
EP3609986B1 EP18720112.4A EP18720112A EP3609986B1 EP 3609986 B1 EP3609986 B1 EP 3609986B1 EP 18720112 A EP18720112 A EP 18720112A EP 3609986 B1 EP3609986 B1 EP 3609986B1
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propylene
chain
independently
group
ethylene
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EP3609986A1 (fr
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Markus Hansch
Jochen Mezger
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BASF SE
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BASF SE
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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 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
    • C10L10/06—Use of additives to fuels or fires for particular purposes for facilitating soot removal
    • 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 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
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • 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 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
    • C10L1/2222—(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 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
    • 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 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)
    • 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 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)
    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and 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
    • 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
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • 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 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
    • 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 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
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0415—Light distillates, e.g. LPG, naphtha
    • C10L2200/0423—Gasoline
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines
    • C10L2270/023—Specifically adapted fuels for internal combustion engines for gasoline engines

Definitions

  • the present invention describes alkoxylated amines as fuel additives to reduce injector deposits in direct injection gasoline engines.
  • EP 700985 A1 is known to use butoxylated polyetheramines of mono- or polyamines as additives in fuels for gasoline engines.
  • the polyetheramines show a reduction in deposits on the intake valves.
  • the polyetheramines are prepared by butoxylation of alkanols, followed by reductive amination of the products obtained with mono- or polyamines.
  • the polyetheramines therefore do not carry any free hydroxyl groups, but instead carry alkyl-capped butylene oxide chains.
  • WO 2011/076949 discloses the use of mixed ethoxylated/propoxylated polyetheramines of monoamines in alcohol-containing gasoline to improve fuel economy and/or reduce deposits on intake valves and/or injection nozzles.
  • EP 905217 A describes the use of ether group-containing compounds in gasoline for direct-injection gasoline engines to reduce emissions. To further reduce injector deposits or combustion chamber deposits, polyalkylamines or polyetheramines should be added to the fuel.
  • the object of the present invention was to provide compounds with which the formation of deposits on injection nozzles can be avoided or reduced and/or existing deposits can be removed in direct-injection Otto engines.
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently hydrogen or a monovalent organic radical or R 1 and R 2 together and together with the nitrogen atom can form a five- to seven-membered ring.
  • Preferred monovalent organic radicals are C 1 - to C 20 -alkyl, C 5 - to C 12 -cycloalkyl, C 6 - to C 12 -aryl or a radical -[-X i -] n -H, particularly preferably C 1 - to C 10 -alkyl, C 5 - to C 6 -cycloalkyl, C 6 - to C 12 -aryl or a radical -[-X i -] n -H, very particularly preferably particularly preferably C 1 - to C 4 -alkyl , especially methyl.
  • R 1 and R 2 are preferably both the same and are each C 1 - to C 4 -alkyl and particularly preferably methyl.
  • R 1 and R 2 together and together with the nitrogen atom to form a five- to seven-membered ring, particularly a five- or six-membered ring and particularly preferably a six-membered ring.
  • the proviso applies that at least one of the radicals R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is not hydrogen and at least one of the radicals R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is a radical -[-X i -] n -H, preferably at least two of the radicals R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are a radical -[-X i -] n -H .
  • R is a divalent organic radical, preferably an alkylene radical having 2 to 10 carbon atoms, preferably an alkylene radical having 2 to 6 carbon atoms, particularly preferably an alkylene radical having 2 to 4 carbon atoms, very particularly preferably an alkylene radical having 2 or 3 carbon atoms and in particular an alkylene radical having 3 carbon atoms having alkylene radical.
  • R is 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,2-butylene, 1,3-butylene, 1,4-butylene, 1,5-pentylene, 1,6-hexylene , 1,8-octylene or 1,10-decylene, particularly preferably 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,2-butylene, 1,4-butylene or 1,6-hexylene , very particularly preferably 1,2-ethylene, 1,2-propylene or 1,3-propylene and for compounds of the formula (I) or (III) in particular 1,3-propylene and for compounds of the formula (II) in particular 1, 2-ethylene or 1,3-propylene, especially 1,2-ethylene.
  • w is a positive integer, preferably 1, 2, 3 or 4, particularly preferably 1, 2 or 3, very particularly preferably 1 or 2 and in particular 1.
  • x, y and z independently of one another, are positive integers, preferably 1, 2, 3 or 4, particularly preferably 1, 2 or 3, very particularly preferably 1 or 2 and in particular 1.
  • the proviso applies that the sum of x, y and z is not equal to zero, preferably the sum of x, y and z is at least 2, particularly preferably at least 3.
  • the sum of x, y and z is preferably not greater than 10, particularly preferably not greater than 8, very particularly preferably not greater than 6 and in particular not greater than 5.
  • each chain -[-X i -] n - occurring in the compounds the units X i can be statistically distributed, so that both the length of the chains and the distribution of the units X i within the chains are different can be.
  • n, p and q independently of one another are positive integers from 1 to 50, preferably from 1 to 25, particularly preferably from 2 to 20 and very particularly preferably from 5 to 15.
  • the sum of p and q is preferably from 2 to 50, particularly preferably from 5 to 40, very particularly preferably from 10 to 30 and in particular from 12 to 27.
  • C 1 - to C 20 -alkyl are methyl, ethyl, isopropyl , n-propyl, n-butyl, isobutyl , sec -butyl, tert-butyl, n-hexyl, n-heptyl, n-octyl , 2-ethylhexyl, n-decyl, 2-propylheptyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl and n-eicosyl.
  • C 1 - to C 10 -alkyl are methyl, ethyl, isopropyl , n-propyl, n-butyl, isobutyl , sec- butyl, tert -butyl , n-hexyl, n-heptyl, n-octyl , 2-ethylhexyl, n-decyl and 2-propylheptyl.
  • C 1 - to C 4 -alkyl are methyl, ethyl, isopropyl , n-propyl, n-butyl, isobutyl , sec- butyl and tert -butyl , preferably methyl, ethyl and n-butyl, particularly preferred methyl and ethyl and most preferably methyl.
  • C 5 - to C 12 -cycloalkyl examples are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl and cyclododecyl, preference being given to cyclopentyl and cyclohexyl.
  • C 6 to C 12 aryl examples include phenyl, tolyl, ethylphenyl, benzyl, phenethyl, xylyl and naphthyl.
  • reaction products of 1,2-ethylenediamine, diethylenetriamine, triethylenetetramine or 3-(dimethylamino)propylamine preferably diethylenetriamine or 3-(dimethylamino)propylamine and particularly preferably 3-(dimethylamino)propylamine with 10 to 30, preferably 12 to 27, are particularly preferred and more preferably 15 to 25 equivalents of propylene oxide and/or 1,2-butylene oxide.
  • the compounds described are used according to the invention in order to avoid or reduce the formation of deposits on direct-injection injection nozzles and/or to remove or reduce existing deposits when operating direct-injection Otto engines with Otto fuels.
  • Another advantage of the compounds described is that they can act as demulsifiers as an alternative or in addition to the uses described.
  • Another object of the present invention are fuel additive concentrates according to claim 14.
  • alkoxylated amines amines with primary and/or secondary amino groups
  • HL Sanders et al. Journal of the American Oil Chemists Society, 1969, 46, 167-170 and in WO 2013/076024 described.
  • the alkoxylation of amines and polyamines usually takes place in two stages: first, enough alkylene oxide is used to achieve an average degree of alkoxylation of from 0.5 to 1.5, preferably from 0.75 to 1.25, mol of alkylene oxide per NH function. This step is usually carried out in the presence of water (preferably 0.5-10.0% by weight based on the amine used), but can also be carried out in the absence of water.
  • the reaction usually takes place at a temperature of from 50.degree. C. to 180.degree. C., preferably from 90.degree. C. to 160.degree.
  • the alkylene oxide is preferably metered in over a period of 1 to 10 hours.
  • the synthesis of the alkoxylated amines can also take place in one stage, with potassium hydroxide, sodium hydroxide, potassium methoxide, sodium methoxide, potassium acetate or sodium acetate being able to be used as possible catalysts.
  • the reaction can also take place without a catalyst, since the amine used can itself catalyze the alkoxylation (see Mihail Ionescu, Chemistry and Technology of Polyols for Polyurethanes, Rapra Technology Limited, 2005).
  • the alkylene oxides usually contain 2 or more carbon atoms, preferably 2 to 20 carbon atoms, in particular from 2 to 12 carbon atoms.
  • Possible alkylene oxides are ethylene oxide, propylene oxide, isobutylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, 1,2-pentene oxide, 1,2-dodecene oxide, styrene oxide.
  • Possible alkylene oxides also include glycidyl ethers, for example 2-ethylhexyl glycidyl ether. Propylene oxide and 1,2-butylene oxide are particularly preferred.
  • the metal is advantageously removed from the product for use in fuels or lubricants.
  • these methods are known in principle and are described in Mihail Ionescu, Chemistry and Technology of Polyols for Polyurethanes, Rapra Technology Limited, 2005.
  • alkali metals or alkaline earth metals can be removed by adsorption on magnesium silicates (commercial products Ambosol® or Magnesol® ).
  • Potassium ions can be removed as potassium hydrogen phosphate by precipitation with phosphoric acid and subsequent filtration.
  • Alkali metals or alkaline earth metals can also be removed with the aid of regenerable ion exchangers, in which case the alkoxylated amine can also be dissolved in a solvent.
  • the compounds (A) according to the invention can be added to the fuels to which additives are to be added individually or as a mixture with other active additive components (co-additives).
  • the hydrophobic hydrocarbon group in the above detergent additives which provides sufficient solubility in fuel has a number average molecular weight (Mn) of from 85 to 20,000, especially from 113 to 10,000, especially from 300 to 5000.
  • Mn number average molecular weight
  • Amines such as ammonia, monoamines or polyamines such as dimethylaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine can be used for the amination.
  • Corresponding additives based on polypropylene are in particular in the WO-A-94/24231 described.
  • additives containing monoamino groups (a) are the compounds obtainable from polyisobutene epoxides by reaction with amines and subsequent dehydration and reduction of the amino alcohols, as they are used in particular in DE-A-196 20 262 are described.
  • Additives containing carboxyl groups or their alkali metal or alkaline earth metal salts (d) are preferably copolymers of C 2 -C 40 -olefins with maleic anhydride having a total molar mass of 500 to 20,000, all or part of the carboxyl groups to the alkali metal or alkaline earth metal salts and one remaining Rest of the carboxyl groups are reacted with alcohols or amines.
  • Such additives are in particular from EP-A-307 815 known.
  • Such additives are mainly used to prevent valve seat wear and, as in the WO-A-87/01126 described, are used advantageously in combination with conventional fuel detergents such as poly(iso)buteneamines or polyetheramines.
  • Additives containing sulfonic acid groups or their alkali metal or alkaline earth metal salts are preferably alkali metal or alkaline earth metal salts of an alkyl sulfosuccinate, as is found in particular in EP-A-639 632 is described.
  • Such additives serve mainly to prevent valve seat wear and can be used to advantage in combination with conventional fuel detergents such as poly(iso)buteneamines or polyetheramines.
  • Additives containing polyoxy-C 2 -C 4 -alkylene groups (f) are preferably polyethers or polyetheramines, which are obtained by reacting C 2 -C 60 -alkanols, C 6 -C 30 -alkanediols, mono- or di-C 2 -C 30 -alkylamines, C 1 -C 30 -alkylcyclohexanols or C 1 -C 30 -alkylphenols with 1 to 30 mol of ethylene oxide and/or propylene oxide and/or butylene oxide per hydroxyl group or amino group and, in the case of the polyetheramines, by subsequent reductive amination with ammonia, monoamines or polyamines.
  • Such products are used in particular in EP-A-310 875 , EP-A-356 725 , EP-A-700 985 and US-A-4,877,416 described.
  • polyethers such products also have carrier oil properties. Typical examples of these are tridecanol or isotridecanol butoxylates, isononylphenol butoxylates and polyisobutenol butoxylates and propoxylates and the corresponding reaction products with ammonia.
  • Additives containing carboxylic acid ester groups (g) are preferably esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, in particular those with a minimum viscosity of 2 mm 2 /s at 100° C., as is the case in particular in DE-A-38 38 918 are described.
  • Aliphatic or aromatic acids can be used as mono-, di- or tricarboxylic acids, and long-chain representatives having, for example, 6 to 24 carbon atoms are particularly suitable as ester alcohols or ester polyols.
  • esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, isononanol, isodecanol and isotridecanol. Such products also fulfill carrier oil properties.
  • derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
  • Such petrol additives are particularly popular US-A-4,849,572 described.
  • Additives containing groups (i) produced by Mannich reaction of substituted phenols with aldehydes and mono- or polyamines are preferably reaction products of polyisobutene-substituted phenols with formaldehyde and mono- or polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine or dimethylaminopropylamine.
  • Such "polyisobutene Mannich bases" are particularly in the EP-A-831 141 described.
  • additive formulations according to the invention can also be combined with other customary components and additives.
  • the main ones to be mentioned here are carrier oils without a pronounced detergent effect.
  • Suitable mineral carrier oils are fractions obtained during petroleum processing, such as bright stock or base oils with viscosities such as those from the class SN 500-2000; but also aromatic hydrocarbons, paraffinic hydrocarbons and alkoxyalkanols.
  • a fraction known as "hydrocrack oil” and obtained in the refining of mineral oil vacuum distillate cut with a boiling range of about 360 to 500°C, obtainable from natural mineral oil which has been catalytically hydrogenated and isomerized and dewaxed under high pressure
  • mineral carrier oils mentioned above are also suitable.
  • Examples of synthetic carrier oils that can be used according to the invention are selected from: polyolefins (polyalphaolefins or polyinternal olefins), (poly)esters, (poly)alkoxylates, polyethers, aliphatic polyetheramines, alkylphenol-started polyethers, alkylphenol-started polyetheramines and carboxylic acid esters of long-chain alkanols.
  • Examples of particularly suitable synthetic carrier oils are alcohol-started polyethers with about 5 to 35 C 3 - to C 6 -alkylene oxide units, mostly selected from propylene oxide, n-butylene oxide and isobutylene oxide units or mixtures thereof.
  • Non-limiting examples of starter alcohols suitable for this are long-chain alkanols or phenols substituted with long-chain alkyl, where the long-chain alkyl radical is in particular a straight-chain or branched C 6 - to C 18 -alkyl radical. Preferred examples of this are tridecanol, heptadecanol and nonylphenol.
  • the use of the compounds (A) according to the invention can often reduce the use of carrier oils.
  • suitable polyethers or polyetheramines are preferably compounds containing polyoxy-C 2 -C 4 -alkylene groups, which are obtained by reacting C 2 -C 60 -alkanols, C 6 -C 30 -alkanediols, mono- or di-C 2 -C 30 -alkylamines, C 1 -C 30 -alkylcyclohexanols or C 1 -C 30 -alkylphenols with 1 to 30 mol of ethylene oxide and/or propylene oxide and/or butylene oxide per hydroxyl group or amino group and, in the case of polyetheramines, by subsequent reductive amination with ammonia, Monoamines or polyamines are available.
  • poly-C 2 -C 6 -alkylene oxide amines or functional derivatives thereof can be used as polyetheramines.
  • Typical examples of these are tridecanol or isotridecanol butoxylates, heptadecanol or isoheptadecanol butoxylates, isononylphenol butoxylates and polyisobutenol butoxylates and propoxylates and the corresponding reaction products with ammonia.
  • carboxylic acid esters of long-chain alkanols are, in particular, esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, such as those in particular DE-A-38 38 918 are described.
  • Aliphatic or aromatic acids can be used as mono-, di- or tricarboxylic acids, and long-chain representatives having 6 to 24 carbon atoms are particularly suitable as ester alcohols or ester polyols.
  • esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, isononanol, isodecanol and isotridecanol, such as di-(n- or isotridecyl) phthalate or di-(iso-heptadecyl) phthalate .
  • Examples of particularly suitable synthetic carrier oils are alcohol-started polyethers having about 5 to 35, preferably about 5 to 30, particularly preferably 7 to 25, C 3 -C 6 -alkylene oxide units, such as selected from propylene oxide, n-butylene oxide and i-butylene oxide units, or mixtures thereof, preferably selected from propylene oxide and i-butylene oxide units.
  • suitable starter alcohols are long-chain alkanols or phenols substituted with long-chain alkyl, where the long-chain alkyl radical is in particular a straight-chain or branched C 6 -C 18 -alkyl radical.
  • alkanols are decanol, tridecanol, heptadecanol and nonylphenol, particularly preferably branched decanol, tridecanol and heptadecanol.
  • customary additives are corrosion inhibitors, for example based on film-forming ammonium salts of organic carboxylic acids or on heterocyclic aromatics in the case of non-ferrous metal corrosion protection; preferred corrosion inhibitors are mono-, di- and polycarboxylic acids which have at least 12 carbon atoms, preferably at least 14, more preferably at least 16 and most preferably at least 18 carbon atoms and preferably have no other functionalities apart from hydrocarbon radicals and carboxyl groups.
  • fatty acids examples include fatty acids, dimeric fatty acids, alkyl and alkenylsuccinic acids and hydrolyzed olefin-maleic anhydride copolymers, preference being given to dodecanoic acid (lauric acid), tridecanoic acid, tetradecanoic acid (myristic acid), pentadecanoic acid, palmitic acid (hexadecanoic acid), margaric acid (heptadecanoic acid), stearic acid (octadecanoic acid), Nonadecanoic acid, arachidic acid (eicosanoic acid), behenic acid (docosanic acid), tetracosanoic acid (lignoceric acid), cerotic acid (hexacosanoic acid), triacontanoic acid (melissinic acid), palmitoleic acid [(9Z)-hexadec-9-enoic acid], oleic acid [(9Z)
  • antioxidants or stabilizers for example based on amines such as p-phenylenediamine, dicyclohexylamine or derivatives thereof, or on phenols such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4- hydroxyphenylpropionic acid; demulsifiers; antistatic agents; metallocenes such as ferrocene; methylcyclopentadienyl manganese tricarbonyl; lubricity improvers (other than the triazoles of this invention) such as certain fatty acids, alkenyl succinic acid esters, bis(hydroxyalkyl) fatty amines, hydroxyacetamides, or castor oil; and dyes (markers). If necessary, amines are also added to lower the pH of the fuel.
  • amines such as p-phenylenediamine, dicyclohexylamine or derivatives thereof, or on phenols such as 2,4-di-tert
  • solvents are, for example, aromatics, such as solvent naphtha, preferably naphthalene-depleted solvent naphtha, benzene, toluene, xylene, kerosene with an aromatics content of less than 50% by volume, a sulfur content of less than 10 mg/kg and a flash point according to DIN EN ISO 13736: 2000 -04 above 60 °C and higher alcohols which have a flash point according to DIN EN ISO 13736: 2000-04 above 60 °C, preferably 2-ethylhexanol or 2-propylheptanol.
  • aromatics such as solvent naphtha, preferably naphthalene-depleted solvent naphtha, benzene, toluene, xylene, kerosene with an aromatics content of less than 50% by volume, a sulfur content of less than 10 mg/kg and a flash point according to DIN EN ISO 13736: 2000 -04 above 60 °C and higher alcohols which have
  • the components or additives can be added to the fuel individually or as a previously prepared concentrate (additive package) together with the compound (A) according to the invention.
  • additive compositions according to the invention can be used in all conventional gasoline fuels, as described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th edition 1990, volume A16, p. 719 et seq.
  • the petrol is preferably at least one petrol according to DIN EN 228.
  • a gasoline with an aromatics content of no more than 60 such as no more than 42 or no more than 35% by volume and/or a sulfur content of no more than 2000, such as no more than 150 or no more than 10 ppm by weight, is possible.
  • the aromatics content of petrol is, for example, 10 to 50% by volume, such as 30 to 42% by volume, in particular 32 to 40% by volume, or a maximum of 35% by volume.
  • the sulfur content of petrol is, for example, 2 to 500, such as 5 to 100 ppm by weight, or a maximum of 10 ppm by weight.
  • the gasoline can, for example, have an olefin content of up to 50% by volume, such as from 6 to 21% by volume, in particular 7 to 18% by volume; a benzene content of up to 5% by volume, such as 0.5 to 1.0% by volume, in particular 0.6 to 0.9% by volume, and/or an oxygen content of up to 25% by volume , such as up to 10% by weight or 1.0 to 2.7% by weight, in particular from 1.2 to 2.0% by weight.
  • an olefin content of up to 50% by volume, such as from 6 to 21% by volume, in particular 7 to 18% by volume
  • a benzene content of up to 5% by volume, such as 0.5 to 1.0% by volume, in particular 0.6 to 0.9% by volume
  • an oxygen content of up to 25% by volume such as up to 10% by weight or 1.0 to 2.7% by weight, in particular from 1.2 to 2.0% by weight.
  • petrol fuels that can be mentioned by way of example have an aromatics content of no more than 38 or 35% by volume, an olefin content of no more than 21% by volume, a sulfur content of no more than 50 or 10 ppm by weight, a benzene content of no more than 1, 0% by volume and an oxygen content of 1.0 to 2.7% by weight.
  • the content of alcohols and ethers in petrol can vary over a wide range. Examples of typical maximum contents are 15% by volume for methanol, 85% by volume for ethanol, 20% by volume for isopropanol, 15% by volume for tert-butanol, 20% by volume for isobutanol and ether with 5 or more carbon atoms in the molecule, 30% by volume.
  • the summer vapor pressure of petrol is usually a maximum of 70 kPa, in particular 60 kPa (each at 37° C.).
  • the RON of petrol is usually 75 to 105.
  • a typical range for the corresponding MON is 65 to 95.
  • the dosage is such that the compound (A) according to the invention is present in the fuel in amounts of 20-2000 ppm by weight, particularly preferably in amounts of 30-1000 ppm by weight, very particularly preferably in amounts of 40-500 ppm by weight, in particular is present in amounts of 50-300 wppm and especially in amounts of 10-100 wppm.
  • DMAPA methyl methacrylate
  • water 4.1 g, completely desalinated
  • the reactor was rendered inert with nitrogen, then it was heated to 130° C. and a pressure of 2.0 bar absolute was established with nitrogen.
  • Propylene oxide (465 g; 8.0 mol) was metered in over a period of 6 hours. The reaction was allowed to continue for 6 h at 130° C., the mixture was cooled to 50° C., the reactor was flushed with nitrogen and the product was discharged. The product was then freed from low boilers on a rotary evaporator (90° C./10 mbar/2 h).
  • ethylenediamine ⁇ 25 PO was obtained by reacting Quadrol L (ethylenediamine ⁇ 4PO) with 21 equivalents of PO.
  • DMAPA DMAPA (408.8 g; 4.0 mol) was placed in a 3.5 l pressure autoclave with an inclined blade stirrer and the stirrer was switched on.
  • the reactor was rendered inert with nitrogen, then it was heated to 120° C. and a pressure of 2.0 bar absolute was established with nitrogen.
  • 1,2-Butylene oxide (577 g; 8.0 mol) was metered in over a period of 15 hours.
  • the reaction was allowed to continue for 6 h at 120° C., the mixture was cooled to 50° C., the reactor was flushed with nitrogen and the product was discharged. The product was then freed from low boilers on a rotary evaporator (90° C./10 mbar/2 h).
  • the reactor was flushed as well nitrogen and drained the product.
  • the product was freed from low boilers on a rotary evaporator (90° C./10 mbar/2 h).
  • the product was then mixed with 30 g of Ambosol® , stirred at 80° C./100 mbar for 2 h and filtered using a pressure suction filter (Filter medium Seitz K 900 depth filter).
  • the product was obtained in the form of a yellow oil.
  • the fuel was admixed with 80 ppm by weight of the specified products from the synthesis examples or formulations and the FR value was determined over the running time.
  • the FR value is a parameter created by the engine control and corresponds to the fuel injection time into the combustion chamber. If the FR value increases during the test run, this indicates deposits on the injector, the larger the increase, the more deposits have formed. On the other hand, if the FR value remains constant or even falls over the course of the remaining run, the injection nozzle remains free of deposits.

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Claims (15)

  1. Utilisation de composés (A) choisis dans le groupe constitué par la formule (I)
    Figure imgb0015
     et la formule (II)
    Figure imgb0016
     dans lesquelles
    R signifie un radical organique divalent, préférablement un radical alkylène présentant 2 à 10 atomes de carbone, R1, R2, R3, R4, R5 et R6 signifient indépendamment les uns des autres hydrogène ou un radical organique monovalent ou un radical -[-Xi-]n-H ou R1 et R2 peuvent former conjointement et ensemble avec l'atome d'azote un cycle à cinq à sept chaînons, préférablement signifient hydrogène, un radical alkyle présentant 1 à 20 atomes de carbone ou un radical -[-Xi-]n-H.
    w signifie un nombre entier positif et
    x, y et z signifient indépendamment les uns des autres zéro ou un nombre entier positif,
    - dans lequel n signifie un nombre entier positif, et
    - dans lequel chaque Xi pour i = 1 à n, indépendamment les uns des autres, est choisi dans le groupe constitué par -CH2-CH2-O-, -CH2-CH(CH3)-O-, -CH(CH3)-CH2-O-, -CH2-C(CH3)2-O-, -C(CH3)2-CH2-O-, -CH2-CH(C2H5)-O-, -CH (C2H5)-CH2-O- et -CH(CH3)-CH(CH3)-O-, préférablement choisi dans le groupe constitué par -CH2-CH(CH3)-O-, -CH(CH3)-CH2-O-,
    - CH2-C(CH3)2-O-, -C(CH3)2-CH2-O-, -CH2-CH(C2H5)-O-, - CH(C2H5)-CH2-O- et -CH(CH3)-CH(CH3)-O-, plus préférablement choisi dans le groupe constitué par -CH2-CH(CH3)-O-, -CH(CH3)-CH2-O-, -CH2-C(CH3)2-O-, -C(CH3)2-CH2-O-, -CH2-CH(C2H5)-O- et -CH(C2H5)-CH2-O- et le plus préférablement choisi dans le groupe constitué par -CH2-CH(C2H5)-O-, -CH(C2H5)-CH2-O-, -CH2-CH(CH3)-O- et -CH(CH3)-CH2-O-, et en particulier choisi dans le groupe constitué par -CH2-CH(CH3)-O- et -CH(CH3)-CH2-O-
    à la condition que
    - la somme de x, y et z soit différente de zéro
    - au moins l'un des radicaux R1, R2, R3, R4, R5 et R6 ne soit pas hydrogène et
    - au moins l'un des radicaux R1, R2, R3, R4, R5 et R6 représente un radical -[-Xi-]n-H,
    dans des essences pour éviter et/ou diminuer la formation de dépôts au niveau de buses d'injection dans des moteurs à essence à injection directe et/ou pour l'élimination et/ou la diminution de dépôts présents au niveau de buses d'injection dans des moteurs à essence à injection directe.
  2. Utilisation selon la revendication 1, caractérisée en ce que le radical R est choisi dans le groupe constitué par le 1,2-éthylène, le 1,2-propylène, le 1,3-propylène, le 1,2-butylène, le 1,3-butylène, le 1,4-butylène, le 1,5-pentylène, le 1,6-hexylène, le 1,8-octylène et le 1,10-décylène.
  3. Utilisation selon l'une quelconque des revendications précédentes, caractérisée en ce que R1, R2, R3, R4, R5 et R6, dès lors qu'ils ne représentent pas un radical -[-Xi-]n-H, sont choisis indépendamment les uns des autres dans le groupe constitué par hydrogène et un radical alkyle présentant 1 à 12 atomes de carbone.
  4. Utilisation selon la revendication 3, , caractérisée en ce que R1, R2, R3, R4, R5 et R6, dès lors qu'ils ne représentent pas un radical-[-Xi-]n-H, sont choisis indépendamment les uns des autres dans le groupe constitué par méthyle, éthyle, iso-propyle, n-propyle, n-butyle, sec-butyle et tert-butyle.
  5. Utilisation selon l'une quelconque des revendications précédentes, caractérisée en ce que le composé est un composé de formule (I).
  6. Utilisation selon la revendication 5, caractérisée en ce que x = 1 ou 2 et R est 1,2-éthylène, 1,2-propylène ou 1,3-propylène.
  7. Utilisation selon la revendication 5 ou 6, caractérisée en ce que R1 et R2 sont à chaque fois indépendamment l'un de l'autre C1-4 alkyle et R3 et R4 sont à chaque fois indépendamment l'un de l'autre un radical -[-Xi-]n-H.
  8. Utilisation selon la revendication 7, caractérisée en ce que chaque Xi pour i = 1 à n, indépendamment les uns des autres, est choisi dans le groupe constitué par -CH2-CH(CH3)-O-, -CH(CH3)-CH2-O-, -CH2-C(CH3)2-O-, -C(CH3)2-CH2-O-, -CH2-CH(C2H5)-O- et -CH(C2H5)-CH2-O-.
  9. Utilisation selon l'une quelconque des revendications précédentes, caractérisée en ce que le composé (A) satisfait à la formule (III),
    Figure imgb0017
     dans laquelle
    R1, R2 et Xi possèdent les significations mentionnées ci-dessus et
    p et q signifient indépendamment l'un de l'autre un nombre entier positif.
  10. Utilisation selon la revendication 9, caractérisée en ce que la somme de p et q est de 2 à 50.
  11. Utilisation selon la revendication 1, caractérisée en ce que les radicaux dans la formule (I) possèdent les significations suivantes :
    (Ia) R est 1,2-éthylène, w = 1, R1 à R3 sont méthyle et R4 est une chaîne -[-Xi-]n-H
    (Ib) R est 1,2-éthylène, w = 1, R1 et R2 sont méthyle et R3 et R4 sont chacun indépendamment l'un de l'autre une chaîne -[-Xi-]n-H
    (Ic) R est 1,2-propylène, w = 1, R1 et R2 sont méthyle et R3 et R4 sont chacun indépendamment l'un de l'autre une chaîne -[-Xi-]n-H
    (Id) R est 1,3-propylène, w = 1, R1 et R2 sont méthyle et R3 et R4 sont chacun indépendamment l'un de l'autre une chaîne -[-Xi-]n-H
    (Ie) R est 1,3-propylène, w = 1, R1 et R2 sont éthyle et R3 et R4 sont chacun indépendamment l'un de l'autre une chaîne -[-Xi-]n-H
    (If) R est 1,3-propylène, w = 1, R1 et R2 sont n-butyle et R3 et R4 sont chacun indépendamment l'un de l'autre une chaîne -[-Xi-]n-H et
    (Ig) R est 1,2-éthylène, w = 1, R1 à R4 sont une chaîne - [-Xi-]n-H.
  12. Utilisation selon la revendication 1, caractérisée en ce que les radicaux dans la formule (II) possèdent les significations suivantes :
    (IIa) R est 1,2-éthylène, x et y sont 1, z = 0 et R1 à R4 et R6 sont chacun indépendamment les uns des autres une chaîne -[-Xi-]n-H
    (IIb) R est 1,2-propylène, x et y sont 1, z = 0 et R1 à R4 et R6 sont chacun indépendamment les uns des autres une chaîne -[-Xi-]n-H, et
    (IIc) R est 1,3-propylène, x et y sont 1, z = 0 et R1 à R4 étant chacun indépendamment les uns des autres une chaîne -[-Xi-]n-H et R6 est C1- à C20-alkyle.
  13. Utilisation selon la revendication 9, caractérisée en ce que les radicaux dans la formule (III) possèdent les significations suivantes :
    (IIIa) R est 1,2-éthylène et R1 et R2 sont méthyle
    (IIIb) R est 1,2-éthylène et R1 et R2 sont éthyle
    (IIIc) R est 1,2-éthylène et R1 et R2 sont n-butyle
    (IIId) R est 1,2-éthylène et R1 et R2 sont ensemble une chaîne 1,4-butylène
    (IIIe) R est 1,2-éthylène et R1 et R2 sont ensemble une chaîne 1,5-pentylène
    (IIIf) R est 1,2-éthylène et R1 et R2 sont ensemble une chaîne 3-oxa-1,5-pentylène
    (IIIg) R est 1,2-propylène et R1 et R2 sont méthyle
    (IIIh) R est 1,2-propylène et R1 et R2 sont éthyle
    (IIIi) R est 1,2-propylène et R1 et R2 sont n-butyle
    (IIIj) R est 1,2-propylène et R1 et R2 sont ensemble une chaîne 1,4-butylène
    (IIIk) R est 1,2-propylène et R1 et R2 sont ensemble une chaîne 1,5-pentylène
    (IIIl) R est 1,2-propylène et R1 et R2 sont ensemble une chaîne 3-oxa-1,5-pentylène
    (IIIm) R est 1,3-propylène et R1 et R2 sont méthyle
    (IIIn) R est 1,3-propylène et R1 et R2 sont éthyle
    (IIIo) R est 1,3-propylène et R1 et R2 sont n-butyle
    (IIIp) R est 1,3-propylène et R1 et R2 sont ensemble une chaîne 1,4-butylène
    (IIIq) R est 1,3-propylène et R1 et R2 sont ensemble une chaîne 1,5-pentylène, et
    (IIIr) R est 1,3-propylène et R1 et R2 sont ensemble une chaîne 3-oxa-1,5-pentylène.
  14. Concentrés d'additifs pour carburant, contenant,
    (A) 1 à 50 % en poids d'au moins un composé de formule (I), (II) ou (III), tels que décrits dans l'une quelconque des revendications 1 à 13,
    dans lesquelles chaque Xi pour i = 1 à n, indépendamment les uns des autres, est choisi dans le groupe constitué par -CH2-CH(CH3)-O-, -CH(CH3)-CH2-O-, -CH2-C(CH3)2-O-, -C(CH3)2-CH2-O-, -CH2-CH(C2H5)-O- et -CH(C2H5)-CH2-O-, et
    le composé (A) satisfait à la formule (III),
    Figure imgb0018
     dans laquelle
    R1, R2 et Xi possèdent les significations mentionnées ci-dessus et
    p et q signifient indépendamment l'un de l'autre un nombre entier positif
    (B1) 20 à 96,75 % en poids d'au moins un composé (B1a), qui est une polyisobutèneamine, qui peut être obtenue par hydroformylation et amination réductrice ultérieure, tout particulièrement préférablement avec de l'ammoniac, de polyisobutène doté d'un Mn = 300 à 5 000,
    (B2) 2 à 30 % en poids d'au moins une huile porteuse, choisie dans le groupe constitué par des polyoléfines, des (poly)esters, des (poly)alcoxylates, des polyéthers, des polyétheramines aliphatiques, des polyéthers amorcés par un alkylphénol, des polyétheramines amorcées par un alkylphénol et des esters d'acides carboxyliques d'alcanols présentant de 6 à 24 atomes de C, ainsi que (B3) 0,25 à 10 % en poids d'au moins un inhibiteur de corrosion, choisi dans le groupe constitué par des acides monocarboxyliques, des acides dicarboxyliques et des poly(acide carboxylique), des sels d'ammonium d'acides carboxyliques organiques et des composés aromatiques hétérocycliques, présentant au moins 12 atomes de carbone,
    à la condition que la somme de tous les composants totalise toujours 100 % en poids.
  15. Compositions de carburant, contenant,
    (A) 20 à 2 000 ppm en poids d'au moins un composé de formule (I), (II) ou (III), tels que décrits dans l'une quelconque des revendications 1 à 13,
    dans lesquelles chaque Xi pour i = 1 à n, indépendamment les uns des autres, est choisi dans le groupe constitué par -CH2-CH(CH3)-O-, -CH(CH3)-CH2-O-, -CH2-C(CH3)2-O-, -C(CH3)2-CH2-O-, -CH2-CH(C2H5)-O- et -CH(C2H5)-CH2-O-, et
    le composé (A) satisfait à la formule (III),
    Figure imgb0019
     dans laquelle
    R1, R2 et Xi possèdent les significations mentionnées ci-dessus et
    p et q signifient indépendamment l'un de l'autre un nombre entier positif,
    (B1) 50 à 1 000 ppm en poids d'au moins un composé (B1a), qui est une polyisobutèneamine, qui peut être obtenue par hydroformylation et amination réductrice ultérieure, tout particulièrement préférablement avec de l'ammoniac, de polyisobutène doté d'un Mn = 300 à 5 000,
    (B2) au moins une huile porteuse, choisie dans le groupe constitué par des polyoléfines, des (poly)esters, des (poly)alcoxylates, des polyéthers, des polyétheramines aliphatiques, des polyéthers amorcés par un alkylphénol, des polyétheramines amorcées par un alkylphénol et des esters d'acides carboxyliques d'alcanols présentant de 6 à 24 atomes de C,
    (B3) au moins un inhibiteur de corrosion, choisi dans le groupe constitué par des acides monocarboxyliques, des acides dicarboxyliques et des poly(acide carboxylique), des sels d'ammonium d'acides carboxyliques organiques et des composés aromatiques hétérocycliques, présentant au moins 12 atomes de carbone,
    (C) au moins une essence ainsi que
    éventuellement au moins un alcool, préférablement au moins un alcanol en C1-4, particulièrement préférablement le méthanol ou l'éthanol, tout particulièrement préférablement l'éthanol.
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DE4425835A1 (de) 1994-07-21 1996-01-25 Basf Ag Verwendung von Umsetzungsprodukten aus Polyolefinen und Stickoxiden oder Gemischen aus Stickoxiden und Sauerstoff als Additive für Kraftstoffe
DE4432038A1 (de) 1994-09-09 1996-03-14 Basf Ag Polyetheramine enthaltende Kraftstoffe für Ottomotoren
DE19525938A1 (de) 1995-07-17 1997-01-23 Basf Ag Verfahren zur Herstellung von organischen Stickstoffverbindungen, spezielle organische Stickstoffverbindungen und Mischungen aus solchen Verbindungen sowie deren Verwendung als Kraft- und Schmierstoffadditive
DE19620262A1 (de) 1996-05-20 1997-11-27 Basf Ag Verfahren zur Herstellung von Polyalkenaminen
GB9618546D0 (en) 1996-09-05 1996-10-16 Bp Chemicals Additives Dispersants/detergents for hydrocarbons fuels
JP3948796B2 (ja) 1997-09-30 2007-07-25 新日本石油株式会社 筒内直接噴射式ガソリンエンジン用無鉛ガソリン
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JP4330828B2 (ja) * 2001-09-19 2009-09-16 新日本石油株式会社 燃料油添加剤および燃料油組成物
US7435272B2 (en) * 2002-04-24 2008-10-14 Afton Chemical Intangibles Friction modifier alkoxyamine salts of carboxylic acids as additives for fuel compositions and methods of use thereof
US7402185B2 (en) * 2002-04-24 2008-07-22 Afton Chemical Intangibles, Llc Additives for fuel compositions to reduce formation of combustion chamber deposits
DE10316871A1 (de) * 2003-04-11 2004-10-21 Basf Ag Kraftstoffzusammensetzung
WO2008115939A1 (fr) * 2007-03-21 2008-09-25 The Lubrizol Corporation Additifs pour carburant utilisables avec les alcools carburants
BR112012015459A2 (pt) 2009-12-24 2016-03-15 Shell Int Research composição de combustpivel líquido, método para operar um motor de combustão interna, e, uso de uma polieteramina
CA2801643A1 (fr) * 2010-06-28 2012-01-05 Basf Se Alcoxylates et leur utilisation
EP2782985A1 (fr) * 2011-11-23 2014-10-01 Basf Se Mélange d'amines
US9328201B2 (en) 2011-11-25 2016-05-03 Basf Se Alkoxylated polyalkylenepolyamines
WO2014023853A2 (fr) 2012-11-06 2014-02-13 Basf Se Amines tertiaires permettant de réduire l'encrassement des buses d'injecteur et de modifier le frottement dans les moteurs à allumage par étincelle avec injection directe
AU2014294791B2 (en) * 2013-07-26 2018-03-29 Innospec Limited Fuel compositions
PL3099768T3 (pl) 2014-01-29 2020-02-28 Basf Se Inhibitory korozji dla paliw silnikowych

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US11130923B2 (en) 2021-09-28
RU2019135830A (ru) 2021-05-11
AU2018253240A1 (en) 2019-10-17
CN110494534A (zh) 2019-11-22
EP3609986A1 (fr) 2020-02-19
SG11201909437RA (en) 2019-11-28
WO2018188982A1 (fr) 2018-10-18

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