EP4179047A1 - Additifs de carburant pour atténuer l'encrassement d'une buse d'injecteur et réduire les émissions de particules - Google Patents

Additifs de carburant pour atténuer l'encrassement d'une buse d'injecteur et réduire les émissions de particules

Info

Publication number
EP4179047A1
EP4179047A1 EP21740216.3A EP21740216A EP4179047A1 EP 4179047 A1 EP4179047 A1 EP 4179047A1 EP 21740216 A EP21740216 A EP 21740216A EP 4179047 A1 EP4179047 A1 EP 4179047A1
Authority
EP
European Patent Office
Prior art keywords
amine
detergent
ppm
fuel
fuel composition
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.)
Pending
Application number
EP21740216.3A
Other languages
German (de)
English (en)
Inventor
Chung-Hao Kuo
William Raymond RUHE JR.
Man Kit Ng
Peter A. Fuentes-Afflick
Andrew M. ICKES
Carrie Y. Chan
Theresa L. GUNAWAN
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
Chevron Oronite Co LLC
Original Assignee
Chevron USA Inc
Chevron Oronite Co LLC
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 USA Inc, Chevron Oronite Co LLC filed Critical Chevron USA Inc
Publication of EP4179047A1 publication Critical patent/EP4179047A1/fr
Pending legal-status Critical Current

Links

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
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—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, 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0438—Middle or heavy distillates, heating oil, gasoil, marine fuels, residua
    • C10L2200/0446—Diesel
    • 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
    • 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

  • This disclosure relates to fuel components that can improve engine performance. More specifically, this disclosure describes compositions and methods for mitigating injector nozzle fouling and reducing particulate emissions in direct injection spark ignition engines.
  • a fuel composition comprising: a hydrocarbon-based fuel boiling in the gasoline or diesel range; an amine-based detergent given by formula Ri-0-(CH2)m-NHR2, wherein the detergent is present in about 10 ppm to about 750 ppm by weight based on total weight of the fuel composition; wherein Ri is a hydrocarbyl group having 8 to 20 carbons, is hydrogen or (CH2) n NH2 moiety, and wherein m, n are independently integers having a value of 3 or greater; and one or more nitrogen-containing detergent.
  • a concentrate composition comprising: about 30 to 90 wt % of an organic solvent boiling in a range of from 65°C to 205°C and; about 10 to 70 wt % of a detergent mixture comprising: (1) an amine- based detergent given by formula Ri-0-(CH 2 )m-NHR 2 , wherein Ri is a hydrocarbyl group having 8 to 20 carbons, R2 is hydrogen or (CF j n NF moiety, and wherein m, n are independently integers having a value of 3 or greater; and (2) one or more nitrogen-containing detergent.
  • a method of controlling injector fouling comprising: supplying to a direct injection engine a fuel composition comprising: a hydrocarbon-based fuel boiling in the gasoline or diesel range; an amine-based detergent given by formula Ri-0-(CH 2 )m-NHR 2 , wherein the amine-based detergent is present in about 10 ppm to about 750 ppm by weight based on total weight of the fuel composition; wherein Ri is a hydrocarbyl group having 8 to 20 carbons, R2 is hydrogen or (CF j n NF moiety, and wherein m, n are independently integers having a value of 3 or greater; and one or more nitrogen-containing detergent.
  • FIG. 1 is an illustration described in the Example section.
  • FIG. 2 is an illustration described in the Example section.
  • FIG. 3 is an illustration described in the Example section.
  • FIG. 4 is an illustration described in the Example section.
  • FIGS. 5A-5C are illustrations described in the Example section.
  • FIGS. 6A-6C are illustrations described in the Example section.
  • FIGS. 7A-7C are illustrations described in the Example section.
  • FIGS. 8A-8C are illustrations described in the Example section.
  • FIGS. 9A-9C are illustrations described in the Example section.
  • FIGS. 10A-10C are illustrations described in the Example section.
  • FIGS. 11A-11 B are illustrations described in the Example section.
  • FIG. 12 is an illustration described in the Example section.
  • the present invention describes compositions and methods for deposit control in direct injection engines. More specifically, the present invention provides detergent additive compositions that can be utilized as components of fuel compositions and methods of using the compositions thereof.
  • the fuel composition of the present invention comprises (i) a hydrocarbon-based fuel, (ii) a primary fuel additive and (iii) one or more secondary fuel additives.
  • the hydrocarbon-based fuel includes gasoline and diesel.
  • Gasoline fuel refers to a composition containing at least predominantly C4-C12 hydrocarbons.
  • gasoline or gasoline boiling range components is further defined to refer to a composition containing at least predominantly C4-C12 hydrocarbons and further having a boiling range of from about 37.8°C (100°F) to about 204°C (400°F).
  • gasoline is defined to refer to a composition containing at least predominantly C4-C12 hydrocarbons, having a boiling range of from about 37.8°C (100°F) to about 204°C (400°F), and further defined to meet ASTM D4814.
  • Diesel fuel refers to middle distillate fuels containing at least predominantly C10-C25 hydrocarbons.
  • diesel is further defined to refer to a composition containing at least predominantly C10-C25 hydrocarbons, and further having a boiling range of from about 165.6°C (330°F) to about 371.1°C (700°F).
  • diesel is as defined above to refer to a composition containing at least predominantly C10-C25 hydrocarbons, having a boiling range of from about 165.6°C (330°F) to about 371.1°C (700°F), and further defined to meet ASTM D975.
  • the hydrocarbon-based fuel is present in a major amount by weight % of the total fuel composition.
  • the hydrocarbon-based fuel is present in about 50 wt% or greater, 55 wt% or greater, 60 wt% or greater, 65 wt% or greater, 70 wt% or greater, 75 wt% or greater, 80 wt% or greater, 85 wt% or greater, 90 wt% or greater, 95 wt% or greater or between any range from about 50 wt% to up to below 100 wt%.
  • the gasoline employed in the present invention may be clean burning gasoline (CBG).
  • CBG refers to gasoline formulations that contain reduced levels of sulfur, aromatics and olefins. The exact formulation may vary depending on local regulatory definitions.
  • a fuel-soluble, non-volatile carrier fluid or oil may also be used with compounds of this disclosure.
  • the carrier fluid is a chemically inert hydrocarbon- soluble liquid vehicle which substantially increases the non-volatile residue (NVR), or solvent-free liquid fraction of the fuel additive composition while not overwhelmingly contributing to octane requirement increase.
  • the carrier fluid may be a natural or synthetic oil, such as mineral oil, refined petroleum oils, synthetic polyalkanes and alkenes, including hydrogenated and unhydrogenated polyalphaolefins, synthetic polyoxyalkylene-derived oils, such as those described in U.S. Patent Nos. 3,756,793; 4,191,537; and 5,004,478; and in European Patent Appl. Pub. Nos. 356,726 and 382,159.
  • the carrier fluids may be employed in amounts ranging from 35 to 5000 ppm by weight of the hydrocarbon fuel (e.g., 50 to 3000 ppm of the fuel). When employed in a fuel concentrate, carrier fluids may be present in amounts ranging from 20 to 60 wt % (e.g., 30 to 50 wt %).
  • the primary fuel additive of the present invention is an amine-based detergent (more specifically, a linear/branched aliphatic ether amine) having the following formula: Ri-0-(CH 2 )m-NHR 2 Formula I where Ri is a hydrocarbyl group having 8 to 20 carbons, R 2 is hydrogen or (CH 2 ) n NH 2 moiety, and m, n are independently integers having a value of 3 or greater.
  • the hydrocarbyl group may be saturated or unsaturated. In some embodiments, the hydrocarbyl group may contain more than one unsaturated bond.
  • the fuel additives of the present invention can deliver more basic nitrogen at the same treat rate compared to conventional amine-based fuel detergents (such as polyisobutylamine, polyether amine, etc.). This feature is important in determining detergency.
  • conventional amine-based fuel detergents such as polyisobutylamine, polyether amine, etc.
  • the low molecular weight of the additives of the present invention along with their low decomposition temperature and high volatility prevents the additives from generating harmful deposits.
  • Particularly illustrative aliphatic ether amines compatible with the present invention include isotridecyloxypropylamine and 2-ethylhexyloxypropyl amine. These are illustrative examples that are not intended to be limiting.
  • the primary fuel additive can be present in about 10 ppm to about 750 ppm (such as 20 to 700, 30 to 650, 50 to 600, 100 to 500, 200 to 400, 250 to 350, and so forth) based on the total fuel composition.
  • the fuel composition of the present invention includes one or more secondary fuel additives.
  • the secondary fuel additive is a nitrogen-containing detergent that provides enhanced detergency when paired with the primary fuel additive of the present invention.
  • Suitable secondary fuel additives may be classified as aliphatic hydrocarbyl-substituted amines, hydrocarbyl-substituted poly(oxyalkylene)amines, hydrocarbyl-substituted succinimides, Mannich reaction products, polyalkylphenoxyaminoalkanes, nitro and amino aromatic esters of polyalkylphenoxyalkanols, and nitrogen-containing carburetor/injector detergents.
  • Each class of secondary fuel additive will be described in more detail herein.
  • the aliphatic hydrocarbyl-substituted amines employed in the present invention may be straight or branched chain hydrocarbyl-substituted amines having at least one basic nitrogen and wherein the hydrocarbyl group has a number average molecular weight of about 700 to 3,000.
  • Specific examples of aliphatic hydrocarbyl-substituted amines include polyisobutenyl amines and polyisobutyl amines. These amines can be derived as monoamines or polyamines. Preparation of aliphatic amines are generally known and described in detail in U.S. Pat. Nos. 3,438,757; 3,565,804; 3,574,576; 3,848,056; 3,960,515; 4,832,702; and 6,203,584, all of which are hereby incorporated by reference.
  • the hydrocarbyl-substituted poly(oxyalkylene)amines employed in the present invention may include hydrocarbyl poly(oxyalkylene)amines (monoamines or polyamines) wherein the hydrocarbyl group contains from about 1 to about 30 carbon atoms.
  • the number of oxyalkylene units can range from about 5 to about 100.
  • the amine moiety is derived from ammonia, primary alkyl or secondary dialkyl monoamine, or polyamine having a terminal amino nitrogen atom.
  • the oxyalkylene moiety may be oxypropylene or oxybutylene or a mixture thereof.
  • Hydrocarbyl-substituted poly(oxyalkylene)amines are described in U.S. Pat. No. 6,217,624, and U.S. Pat. No. 5,112,364, which are hereby incorporated herein by reference.
  • Specific examples of hydrocarbyl-substituted poly(oxyalkylene)monoamine include alkylphenyl poly(oxyalkylene)monoamine wherein the poly(oxyalkylene) moiety contains oxypropylene units or oxybutylene units or mixtures of oxypropylene and oxybutylene units.
  • the alkyl group on the alkylphenyl moiety is a straight or branched-chain alkyl of about 1 to about 24 carbon atoms.
  • a preferred alkylphenyl moiety is tetrapropenylphenyl where the alkyl group is a branched-chain alkyl of 12 carbon atoms derived from a propylene tetramer.
  • additional hydrocarbyl-substituted poly(oxyalkylene)amines include hydrocarbyl-substituted poly(oxyalkylene)aminocarbamates disclosed in U.S. Pat. Nos. 4,288,612; 4,236,020;
  • hydrocarbyl poly(oxyalkylene)aminocarbamates contain at least one basic nitrogen atom and have an average molecular weight of about 500 to 10,000, preferably about 500 to 5,000, and more preferably about 1,000 to 3,000.
  • a preferred aminocarbamate is alkylphenyl poly(oxybutylene)aminocarbamate wherein the amine moiety is derived from ethylene diamine or diethylene triamine.
  • the hydrocarbyl-substituted succinimides employed in the present invention include polyalkyl and polyalkenyl succinimides wherein the polyalkyl or polyalkenyl group has an average molecular weight of about 500 to 5,000, and preferably about 700 to 3,000.
  • the hydrocarbyl-substituted succinimides are typically prepared by reacting a hydrocarbyl-substituted succinic anhydride with an amine or polyamine having at least one reactive hydrogen bonded to an amine nitrogen atom.
  • Preferred hydrocarbyl-substituted succinimides include polyisobutenyl and polyisobutanyl succinimides, and derivatives thereof.
  • the Mannich reaction products employed in the present invention include products typically obtained from Mannich condensation of a high molecular weight alkyl-substituted hydroxyaromatic compound, an amine containing at least one reactive hydrogen, and an aldehyde.
  • the high molecular weight alkyl- substituted hydroxyaromatic compounds are preferably polyalkylphenols, such as polypropylphenol and polybutylphenol, especially polyisobutylphenol, wherein the polyakyl group has an average molecular weight of about 600 to 3,000.
  • the amine reactant is typically a polyamine, such as alkylene polyamines, especially ethylene or polyethylene polyamines, for example, ethylene diamine, diethylene triamine, triethylene tetramine, and the like.
  • the aldehyde reactant is generally an aliphatic aldehyde, such as formaldehyde, including paraformaldehyde and formalin, and acetaldehyde.
  • a preferred Mannich reaction product is obtained by condensing a polyisobutylphenol with formaldehyde and diethylene triamine, wherein the polyisobutyl group has an average molecular weight of about 1,000.
  • the Mannich reaction products suitable for use in the present invention are described, for example, in U.S. Pat. Nos. 4,231,759 and 5,697,988, the disclosures of each of which are incorporated herein by reference.
  • a still further class of detergent additive suitable for use in the present invention are polyalkylphenoxyaminoalkanes.
  • Preferred polyalkylphenoxyaminoalkanes include those having the following formula:
  • R3 ⁇ 4 is a polyalkyl group having an average molecular weight in the range of about 600 to 5,000; [3 ⁇ 4 and R 7 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; and A is amino, N-alkyl amino having about 1 to about 20 carbon atoms in the alkyl group, N,N-dialkyl amino having about 1 to about 20 carbon atoms in each alkyl group, or a polyamine moiety having about 2 to about 12 amine nitrogen atoms and about 2 to about 40 carbon atoms.
  • the polyalkylphenoxyaminoalkanes of Formula II above and their preparations are described in detail in U.S. Pat. No. 5,669,939, which is hereby incorporated herein by reference.
  • Certain detergent mixtures may be particularly useful as secondary additives in accordance with the present invention.
  • mixtures of polyalkylphenoxyaminoalkanes and poly(oxyalkylene)amines may be employed. These mixtures are described in detail in U.S. Pat. No. 5,851,242, which is hereby incorporated by reference.
  • mixtures of nitro and amino aromatic esters of polyalkylphenoxyalkanols may be employed.
  • Preferred nitro and amino aromatic esters of polyalkylphenoxyalkanols include those having the formula:
  • Preferred hydrocarbyl-substituted poly(oxyalkylene)amines which may be employed as detergent additives in the present invention include those having the following formula: Formula IV wherein: R17 is a hydrocarbyl group having from about 1 to about 30 carbon atoms; R18 and R19 are each independently hydrogen or lower alkyl having about 1 to about 6 carbon atoms and each R18 and R19 is independently selected in each — O — CHR18 — CHR19 — unit; m is from about 5 to about 100; B is amino, N-alkyl amino having about 1 to about 20 carbon atoms in the alkyl group, N,N-dialkyl amino having about 1 to about 20 carbon atoms in each alkyl group, or a polyamine moiety having about 2 to about 12 amine nitrogen atoms and about 2 to about 40 carbon atoms; and m is an integer from about 5 to about 100.
  • R17 is a hydrocarbyl group having from about 1 to about 30 carbon atoms
  • hydrocarbyl-substituted poly(oxyalkylene)amines of Formula IV above and their preparations are described in detail in U.S. Pat. No. 6,217,624, which is hereby incorporated by reference.
  • the hydrocarbyl-substituted poly(oxyalkylene)amines of Formula IV are preferably utilized either by themselves or in combination with other detergent additives, particularly with the polyalkylphenoxyaminoalkanes or the nitro and amino aromatic esters of polyalkylphenoxyalkanols. More preferably, the detergent additives employed in the present invention will be combinations of the hydrocarbyl-substituted poly(oxyalkylene)amines with the nitro and amino aromatic esters of polyalkylphenoxyalkanols.
  • a particularly preferred hydrocarbyl-substituted poly(oxyalkylene)amine detergent additive is dodecylphenoxy poly(oxybutylene)amine and a particularly preferred combination of detergent additives is the combination of dodecylphenoxy poly(oxybutylene)amine and 4- polyisobutylphenoxyethyl para-aminobenzoate.
  • Another class of detergent additive suitable for use in the present invention include nitrogen-containing carburetor/injector detergents.
  • the carburetor/injector detergent additives are typically low molecular weight compounds having a number average molecular weight of about 100 to about 600 and possessing at least one polar moiety and at least one non-polar moiety.
  • the non-polar moiety is typically a linear or branched-chain alkyl or alkenyl group having about 6 to about 40 carbon atoms.
  • the polar moiety is typically nitrogen-containing.
  • Typical nitrogen- containing polar moieties include amines (for example, as described in U.S. Pat. No. 5,139,534 and PCT International Publication No.
  • WO 90/10051 ether amines (for example, as described in U.S. Pat. No. 3,849,083 and PCT International Publication No. WO 90/10051), amides, polyamides and amide-esters (for example, as described in U.S. Pat. Nos. 2,622,018; 4,729,769; and 5,139,534; and European Patent Publication No. 149,486), imidazolines (for example, as described in U.S. Pat. No. 4,518,782), amine oxides (for example, as described in U.S. Pat. Nos. 4,810,263 and 4,836,829), hydroxyamines (for example, as described in U.S. Pat. No. 4,409,000), and succinimides (for example, as described in U.S. Pat. No. 4,292,046).
  • amides for example, as described in U.S. Pat. No. 3,849,083 and PCT International Publication No. WO 90/
  • Each secondary fuel additive can be present in about 50 ppm to about 2500 ppm (such as 100 to 2000, 200 to 1500, 300 to 1000 and the like) by weight of the fuel composition. More preferably, the secondary fuel additive is present in about 50 ppm to about 1000 ppm by weight of the fuel composition.
  • the fuel composition may comprise other generally known fuel additives. Suitable examples include, but are not limited to, antioxidants, metal deactivators, demulsifiers, oxygenates, antiknock agents, dispersants and other detergents. In diesel fuel, other well-known additives can be employed such as pour point depressants, flow improvers, and the like.
  • each of the foregoing additives when used, is used at a functionally effective amount to impart the desired properties to the fuel composition.
  • concentration of each of these additives, when used may range, unless otherwise specified, from about 0.001 to about 20 wt. %, such as about 0.01 to about 10 wt. %.
  • the compounds of the present disclosure may be formulated as a concentrate using an inert stable oleophilic (i.e., soluble in hydrocarbon fuel) organic solvent boiling in a range of 65°C to 205°C.
  • An aliphatic or an aromatic hydrocarbon solvent may be used, such as benzene, toluene, xylene, or higher-boiling aromatics or aromatic thinners.
  • Aliphatic alcohols containing 2 to 8 carbon atoms, such as ethanol, isopropanol, methyl isobutyl carbinol, n-butanol and the like, in combination with the hydrocarbon solvents are also suitable for use with the present additives.
  • the amount of the additive may range from 10 to 70 wt % (e.g., 20 to 40 wt %).
  • Table 1 summarizes the additives used to test injector fouling and/or deposit control performance. Additives used in the following tests include isotridecyloxypropylamine (Example 1), and polyoxybutylene amine (Example 2). Base Fuel is unadditized gasoline composition.
  • Example 1 was blended in gasoline and tested for their ability to mitigate DISI injector fouling in a test vehicle using the test method described herein.
  • a 2017 VW Jetta SE equipped with 1.4L turbocharged DISI 4-cylinder gasoline was the test vehicle used in this Example.
  • FIG. 1 illustrates engine speed and load test conditions observed during a vehicle drive cycle.
  • the vehicle drive cycle is based on 10 hills extracted from the transient phase of the Environmental Protection Agency (EPA) Urban Dynamometer Drive Schedule (UDDS) with additional idle periods added.
  • Total drive cycle is 20 minutes in duration and the overall test duration is 2,000-miles.
  • EPA Environmental Protection Agency
  • UDDS Urban Dynamometer Drive Schedule
  • Additive testing is conducted in a "keep clean" configuration which starts with a clean injector and combustion chamber. This test configuration evaluates the ability of a given deposit control additive to keep the injector and combustion chamber clean over the duration of the test.
  • test fuel samples were formulated with the target deposit control additive.
  • Three injector "keep clean" tests were performed: (i) two tests using the unadditized base fuel and (ii) one test using the same base fuel as in (i) blended with 200 ppmw of Example 1.
  • Injector fuel restriction (average) after the designated drive cycles are summarized in Table 2 below.
  • the injector fuel restriction substantially decreased during additized fuel use as compared to during nonadditized fuel use.
  • Injector fuel restriction measures the decrease in fuel flow from the injector, representing the presence of deposits in the injector orifices.
  • Injector restriction can force the engine controller to make additional control adjustments to maintain proper engine fuel delivery, and the presence of deposits in the injector orifices can impact fuel mixing, leading to decreased engine performance and increased particulate emissions.
  • Injector face images of each formulation after completion of test are shown in FIG. 2 and correspond to Table 2.
  • a test engine was also used to evaluate PM emissions of Example 1.
  • the engine drive cycle is 360s in duration with engine speeds ranging from idle to 3000-RPM, and load varying up to 100-Nm.
  • the overall test duration is 96 hours.
  • FIG. 3 illustrates engine speed and load test conditions.
  • MSS Micro Soot Sensor
  • FIGS. 5A-5C illustrate the results of PM emissions trendlines (96 hour test) for fuel compositions with 150 ppmw of Example 2 (FIG. 5A), with 150 ppmw of Example 2 and 150 ppmw of Example 1 (FIG. 5B), and with 150 ppmw of Example 2 and 750 ppmw of Example 1 (FIG. 5C).
  • FIGS. 6A-6C illustrate the results of the PM emissions trendlines (96 hour test) for fuel compositions with 2000 ppmw of Example 3 (FIG. 6A), with 2000 ppmw of Example 2 and 150 ppmw of Example 1 (FIG. 6B), and with 2000 ppmw of Example 2 and 750 ppmw of Example 1 (FIG. 6C).
  • FIGS. 7A-7C and FIGS. 8A-8C illustrate results of direct injection spark- ignition (DISI) rig injector flow tests. These graphs show percent restriction relative to clean injector flow for various pulse widths (1.5 ms, 2.5 ms, 3.5 ms, and 4.5 ms) at 100 bar injection pressure.
  • the samples tested include fuel compositions with 150 ppmw of Example 2 (FIG. 7A), with 150 ppmw of Example 2 and 150 ppmw of Example 1 (FIG. 7B), and with 150 ppmw of Example 2 and 750 ppmw of Example 1 (FIG. 7C).
  • the samples also include fuel compositions with 2000 ppmw of Example 2 (FIG. 8A), with 2000 ppmw of Example 2 and 150 ppmw of Example 1 (FIG. 8B), and with 2000 ppmw of Example 2 and 750 ppmw of Example 1 (FIG. 8C).
  • FIGS. 9A-9C show injector face images that were taken after end of vehicle or engine test (prior to flow tests) corresponding to samples containing fuel compositions with 150 ppmw of Example 2 (FIG. 9A), with 150 ppmw of Example 2 and 150 ppmw of Example 1 (FIG. 9B), and with 150 ppmw of Example 2 and 750 ppmw of Example 1 (FIG. 9C).
  • FIGS. 10A-10C show injector face images that were taken after end of vehicle or engine test (prior to flow tests) corresponding to samples containing fuel compositions with 2000 ppmw of Example 2 (FIG. 10A), with 2000 ppmw of Example 2 and 150 ppmw of Example 1 (FIG. 10B), and with 2000 ppmw of Example 2 and 750 ppmw of Example 1 (FIG. 10C).
  • FIG. 11 A shows average injector tip deposit volume (mm 3 ) for fuel compositions with 150 ppmw of Example 2 (left bar), with 150 ppmw of Example 2 and 150 ppmw of Example 1 (middle bar), and with 150 ppmw of Example 2 and 750 ppm of Example 1 (right bar).
  • FIG. 11 B shows average injector tip deposit volume (mm 3 ) for fuel compositions with 2000 ppmw of Example 2 (left bar), with 2000 ppmw of Example 2 and 150 ppmw of Example 1 (middle bar), and 2000 ppmw of Example 2 and 750 ppmw of Example 1 (right bar). These measurements were taken end of vehicle or engine test (prior to flow tests).
  • Table 3 summarizes samples that were tested and rated for anti corrosion property using NACE TM0172 standard test method.
  • Base fuel is unadditized fuel.
  • FIG. 12 provides visual confirmation of the anti-corrosion test.
  • ranges from any lower limit may be combined with any upper limit to recite a range not explicitly recited, as well as, ranges from any lower limit may be combined with any other lower limit to recite a range not explicitly recited, in the same way, ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited.
  • ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited.
  • within a range includes every point or individual value between its end points even though not explicitly recited. Thus, every point or individual value may serve as its own lower or upper limit combined with any other point or individual value or any other lower or upper limit, to recite a range not explicitly recited.
  • compositions, an element or a group of elements are preceded with the transitional phrase “comprising,” it is understood that we also contemplate the same composition or group of elements with transitional phrases “consisting essentially of,” “consisting of,” “selected from the group of consisting of,” or “is” preceding the recitation of the composition, element, or elements and vice versa.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Nozzles For Spraying Of Liquid Fuel (AREA)

Abstract

La présente invention concerne une composition de carburant qui comprend : un carburant à base d'hydrocarbures bouillant dans la plage de l'essence ou du diesel ; un détergent à base d'amine donné par la formule R1-O-(CH2)m-NHR2, l'additif étant présent à raison d'environ 10 ppm à environ 750 ppm en poids sur la base du poids total de la composition de carburant ; R1 représentant un groupe hydrocarbyle comprenant 8 à 20 atomes de carbone, R2 représentant hydrogène ou un fragment (CH2)nNH2 et m, n représentant indépendamment des nombres entiers présentant une valeur de 3 ou plus ; et un ou plusieurs détergents contenant de l'azote.
EP21740216.3A 2020-07-07 2021-07-07 Additifs de carburant pour atténuer l'encrassement d'une buse d'injecteur et réduire les émissions de particules Pending EP4179047A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202063048922P 2020-07-07 2020-07-07
PCT/IB2021/056075 WO2022009105A1 (fr) 2020-07-07 2021-07-07 Additifs de carburant pour atténuer l'encrassement d'une buse d'injecteur et réduire les émissions de particules

Publications (1)

Publication Number Publication Date
EP4179047A1 true EP4179047A1 (fr) 2023-05-17

Family

ID=76859668

Family Applications (1)

Application Number Title Priority Date Filing Date
EP21740216.3A Pending EP4179047A1 (fr) 2020-07-07 2021-07-07 Additifs de carburant pour atténuer l'encrassement d'une buse d'injecteur et réduire les émissions de particules

Country Status (10)

Country Link
US (1) US20220145199A1 (fr)
EP (1) EP4179047A1 (fr)
JP (1) JP2023533737A (fr)
KR (1) KR20230035330A (fr)
CN (1) CN116134116A (fr)
AU (1) AU2021304467A1 (fr)
CA (1) CA3188758A1 (fr)
CO (1) CO2023001087A2 (fr)
MX (1) MX2023000329A (fr)
WO (1) WO2022009105A1 (fr)

Family Cites Families (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2622018A (en) 1949-10-19 1952-12-16 Socony Vacuum Oil Co Inc Motor fuel
US3574576A (en) 1965-08-23 1971-04-13 Chevron Res Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine
GB1346765A (en) 1970-06-16 1974-02-13 Shell Int Research Fuel compositions
US3849083A (en) * 1972-04-14 1974-11-19 Ethyl Corp Gasoline additive
US3848056A (en) 1972-09-05 1974-11-12 Continental Oil Co Molten alkaline alkanoic mixtures for absorption of sulfur oxides
US4231759A (en) 1973-03-12 1980-11-04 Standard Oil Company (Indiana) Liquid hydrocarbon fuels containing high molecular weight Mannich bases
US3960515A (en) 1973-10-11 1976-06-01 Chevron Research Company Hydrocarbyl amine additives for distillate fuels
GB1486144A (en) 1974-03-13 1977-09-21 Cities Service Oil Co Gasoline additive
US4191537A (en) 1976-06-21 1980-03-04 Chevron Research Company Fuel compositions of poly(oxyalkylene) aminocarbamate
US4236020A (en) 1976-06-21 1980-11-25 Chevron Research Company Carbamate deposit control additives
US4288612A (en) 1976-06-21 1981-09-08 Chevron Research Company Deposit control additives
US4160648A (en) 1976-06-21 1979-07-10 Chevron Research Company Fuel compositions containing deposit control additives
US4233168A (en) 1978-06-19 1980-11-11 Chevron Research Company Lubricant compositions containing dispersant additives
US4197409A (en) 1978-08-08 1980-04-08 Chevron Research Company Poly(oxyalkylene)aminocarbomates of alkylene polyamine
US4243798A (en) 1979-08-09 1981-01-06 Chevron Research Company Process for the production of a polymeric carbamate
US4292046A (en) 1979-08-10 1981-09-29 Mobil Oil Corporation Detergent compositions
US4270930A (en) 1979-12-21 1981-06-02 Chevron Research Company Clean combustion chamber fuel composition
US4518782A (en) 1981-08-10 1985-05-21 Texaco Inc. Fuel compositions containing N-alkyl glycyl imidazoline
US4392866A (en) * 1981-11-05 1983-07-12 Texaco Inc. Etheramine corrosion inhibitor for alcohols
US4409000A (en) 1981-12-14 1983-10-11 The Lubrizol Corporation Combinations of hydroxy amines and carboxylic dispersants as fuel additives
EP0149486A3 (fr) 1984-01-17 1986-10-08 Atlantic Richfield Company Détergents et composition de carburant les contenant
US4836829A (en) 1986-03-14 1989-06-06 Exxon Research And Engineering Company Fuel composition and process for multi-port fuel injection systems (PNE-509)
DE3611230A1 (de) 1986-04-04 1987-10-08 Basf Ag Polybutyl- und polyisobutylamine, verfahren zu deren herstellung und diese enthaltende kraft- und schmierstoffzusammensetzungen
US4810263A (en) 1986-04-11 1989-03-07 Exxon Research And Engineering Company Fuel composition
US4729769A (en) 1986-05-08 1988-03-08 Texaco Inc. Gasoline compositions containing reaction products of fatty acid esters and amines as carburetor detergents
US4881945A (en) 1987-10-23 1989-11-21 Chevron Research Company Fuel compositions containing very long chain alkylphenyl poly(oxyalkylene) aminocarbonates
DE3826608A1 (de) 1988-08-05 1990-02-08 Basf Ag Polyetheramine oder polyetheraminderivate enthaltende kraftstoffe fuer ottomotoren
DE3826797A1 (de) 1988-08-06 1990-02-08 Basf Ag Kraftstoffzusammensetzungen, die polycarbonsaeureester langkettiger alkohole enthalten
DE3838918A1 (de) 1988-11-17 1990-05-23 Basf Ag Kraftstoffe fuer verbrennungsmaschinen
EP0382159A1 (fr) 1989-02-06 1990-08-16 E.I. Du Pont De Nemours And Company Désencrassage d'appareils à combustible
WO1990010051A1 (fr) 1989-02-21 1990-09-07 Union Oil Company Of California Composition de carburant permettant la regulation de depots sur des soupapes d'admission
GB9007431D0 (en) 1990-04-03 1990-05-30 Shell Int Research Diesel fuel additives
EP0557516B1 (fr) 1991-09-13 1996-07-17 Chevron Chemical Company Compositions additives pour carburant contenant des succinimides de polyisobutenyle
US5697988A (en) 1991-11-18 1997-12-16 Ethyl Corporation Fuel compositions
GB9208034D0 (en) 1992-04-10 1992-05-27 Bp Chem Int Ltd Fuel composition
US5620486A (en) 1994-12-30 1997-04-15 Chevron Chemical Company Fuel compositions containing aryl succinimides
US5669939A (en) 1996-05-14 1997-09-23 Chevron Chemical Company Polyalkylphenoxyaminoalkanes and fuel compositions containing the same
US5618320A (en) 1996-05-14 1997-04-08 Chevron Chemical Company Aromatic esters of polyalkylphenoxyalkanols and fuel compositions containing the same
US6203584B1 (en) 1998-03-31 2001-03-20 Chevron Chemical Company Llc Fuel composition containing an amine compound and an ester
US5954843A (en) 1998-08-28 1999-09-21 Chevron Chemical Company Llc Aminocarbamates of polyalkyl or polyalkenyl N-hydroxyalkyl succinimides and fuel compositions containing the same
US6114542A (en) 1998-08-28 2000-09-05 Chevron Chemical Company Llc Ethers of polyalkyl or polyalkenyl N-hydroxyalkyl succinimides and fuel compositions containing the same
US5993497A (en) 1998-08-28 1999-11-30 Chevron Chemical Company Llc Esters of polyalkyl or polyalkenyl N-hydroxyalkyl succinimides and fuel compositions containing the same
US5916825A (en) 1998-08-28 1999-06-29 Chevron Chemical Company Llc Polyisobutanyl succinimides and fuel compositions containing the same
US6217624B1 (en) 1999-02-18 2001-04-17 Chevron Chemical Company Llc Fuel compositions containing hydrocarbyl-substituted polyoxyalkylene amines
US6361573B1 (en) * 1999-08-31 2002-03-26 Ethyl Corporation Fuel dispersants with enhanced lubricity
US6746495B2 (en) * 2000-10-24 2004-06-08 Exxonmobil Research And Engineering Company Method for controlling deposit formation in gasoline direct injection engine by use of a fuel having particular compositional characteristics
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
US8231695B2 (en) * 2006-08-09 2012-07-31 Afton Chemical Corporation Fuel compositions comprising hydrocarbon oil carriers and methods for using the same
BR112012030330A2 (pt) * 2010-06-01 2016-08-09 Basf Se composição de aditivo de combustível, composição de combustível, e, uso

Also Published As

Publication number Publication date
WO2022009105A1 (fr) 2022-01-13
CN116134116A (zh) 2023-05-16
CO2023001087A2 (es) 2023-02-06
US20220145199A1 (en) 2022-05-12
JP2023533737A (ja) 2023-08-04
AU2021304467A1 (en) 2023-02-23
KR20230035330A (ko) 2023-03-13
MX2023000329A (es) 2023-03-27
CA3188758A1 (fr) 2022-01-13

Similar Documents

Publication Publication Date Title
US7901470B2 (en) Gasoline additives
AU689585B2 (en) Fuel additive compositions containing an aliphatic amine, a polyolefin and a poly(oxyalkylene) monool
EP3887488B1 (fr) Composé amidoamine gras quaternaire destiné à être utilisé en tant qu'additif pour carburant
CA2165305C (fr) Compositions d'additif pour carburant contenant une amine aliphatique, une polyolefine et un ester aromatique
US20220145199A1 (en) Fuel additives for mitigating injector nozzle fouling and reducing particulate emissions
CA2440548C (fr) Methode de reduction des emissions de particules dans des moteurs a combustion interne
EP4214297B1 (fr) Aryloxy alkylamines utilisées comme additifs de carburant pour réduire l'encrassement des injecteurs dans des moteurs à essence, allumage par étincelle et injection directe
EP4413100A1 (fr) Additifs de carburant pour abaisser le dépôt et l'émission de particules
JP4330828B2 (ja) 燃料油添加剤および燃料油組成物
AU2003219078B2 (en) Gasoline additives
CA2533001A1 (fr) Compositions d'essence
WO2008054368A9 (fr) Composition de type additif synergique pour les combustibles pétroliers

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20230103

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
RIC1 Information provided on ipc code assigned before grant

Ipc: C10L 10/04 20060101ALI20240104BHEP

Ipc: C10L 1/2383 20060101ALI20240104BHEP

Ipc: C10L 1/22 20060101ALI20240104BHEP

Ipc: C10L 1/2387 20060101ALI20240104BHEP

Ipc: C10L 1/238 20060101ALI20240104BHEP

Ipc: C10L 1/23 20060101ALI20240104BHEP

Ipc: C10L 1/224 20060101ALI20240104BHEP

Ipc: C10L 1/222 20060101ALI20240104BHEP

Ipc: C10L 10/06 20060101ALI20240104BHEP

Ipc: C10L 10/02 20060101ALI20240104BHEP

Ipc: C10L 1/10 20060101AFI20240104BHEP

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17Q First examination report despatched

Effective date: 20240207

RAP3 Party data changed (applicant data changed or rights of an application transferred)

Owner name: CHEVRON U.S.A. INC.

Owner name: CHEVRON ORONITE COMPANY LLC

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

INTG Intention to grant announced

Effective date: 20240909