WO2001088066A1 - Additif pour carburant diesel et composition de carburant diesel - Google Patents

Additif pour carburant diesel et composition de carburant diesel Download PDF

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Publication number
WO2001088066A1
WO2001088066A1 PCT/JP2001/004170 JP0104170W WO0188066A1 WO 2001088066 A1 WO2001088066 A1 WO 2001088066A1 JP 0104170 W JP0104170 W JP 0104170W WO 0188066 A1 WO0188066 A1 WO 0188066A1
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group
carbon atoms
branched
general formula
substituted isomers
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PCT/JP2001/004170
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English (en)
Japanese (ja)
Inventor
Katsuhiko Haji
Masaki Nagao
Tadahide Sone
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Nippon Mitsubishi Oil Corporation
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Priority to AU2001256775A priority Critical patent/AU2001256775A1/en
Priority to JP2001585275A priority patent/JP4537642B2/ja
Publication of WO2001088066A1 publication Critical patent/WO2001088066A1/fr

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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, 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
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • 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
    • C10L10/06—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, 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones
    • 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
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • 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)

Definitions

  • the present invention provides a fuel oil additive having excellent solubility in fuel oil, particularly excellent cleanliness in an intake system and a combustion chamber of a gasoline engine, and excellent cleanliness of an injection nozzle of a diesel engine, and contains the additive.
  • the present invention relates to a fuel oil composition comprising:
  • An object of the present invention is to provide a novel fuel oil additive which has performance exceeding that of conventional gasoline detergents, is excellent in cleanliness of injection nozzles of diesel engines, and is not itself sludged.
  • An object of the present invention is to provide a fuel oil composition containing an additive.
  • the present inventors have conducted studies to find a fuel oil additive that is more excellent in the cleanliness of the intake system and combustion chamber of a gasoline engine and the injection nozzle of diesel engines. It has been found that a detergent comprising a heterocyclic compound and a polyetheramine and / or a polyalkenylamine has a much higher performance than a conventional gasoline detergent.
  • the present invention has a pyrrolidine, pyrrolidone, pyrrole, furan, tetrahydrofuran, lactone, piperidine, piperazine, pyridine, tetrahydropyran, morpholin, dioxolan, and pyridone structure. (These compounds may have a substituent.)
  • the fuel oil additive comprises at least one heterocyclic compound selected from the group consisting of:
  • the present invention also resides in a fuel oil additive comprising the above specific heterocyclic compound and polyetheramine and / or polyalkenylamine.
  • the present invention is also a fuel oil composition comprising the above-mentioned specific additive in a fuel oil for an internal combustion engine.
  • the present invention will be described in more detail.
  • the fuel oil additive of the present invention includes pyrrolidine, pyrrolidone (2-pyrrolidinone), pyrrol (pyrrol, 2H-, 4H-pyrrol), furan (Dihydrofuran, furan), tetrahydrofuran (oxolan), lactone (aractone, (5-lactone), piperidine, piperazine, pyridine (pyridine, 1,2-, 1,4-dihydropyridine) ), Tetrahydropyran, morpholin, dioxolan, or pyridone ((5-lactam, 2-piridone, 4-biridone)) compounds (these compounds have substituents May be included).
  • the heterocyclic compound of the present invention may have the above-mentioned monocyclic structure or a polycyclic (condensed ring) structure of two or more rings formed by condensing another ring with this structure.
  • the compound is preferably a monocyclic compound (which may have a substituent).
  • the heterocyclic compound is particularly preferably a saturated heterocyclic compound.
  • two or more compounds having these structures can be used in combination.
  • the heterocyclic compound of the present invention is preferably a compound having a pyrrolidone, tetrahydrofuran, lactone, piperidine, piperazine, morpholine or dioxolane structure. Most preferred are compounds having a pyrrolidone structure.
  • Examples of the substituents of the heterocyclic compound having the above structure include a hydroxyl group, a carboxyl group (COOH), an aldehyde group, a cyano group, a nitro group, a hydrocarbon group having 1 to 30 carbon atoms, OR 27, -COR 28, one CO OR 2 9, - OCOR 3 Q, - NHC 0 R 3 - CO NH R 3 2, one NH C_ ⁇ OR 33, - 0 C 0 NHR 34 ( above] R 27, R 2 R 2 9, R 3 ° , R 3 i, R 32, R 33, and R 3 4 is a hydrocarbon group with carbon number from 1 to 3 0 each independently), a heterocyclic group, and the following general formula ( Group represented by 13):
  • Y represents an alkylene group having 2-1 8 carbon atoms
  • R 3 5 is a hydrogen atom or a hydrocarbon group having a carbon number of 1-3
  • h is an integer of. 1 to 2 0
  • the heterocyclic compound of the present invention may be substituted by two or more of the above-mentioned substituents, and when these substituents are substitutable, the above-mentioned substituents (carbons among the above-mentioned substituents) It may be further substituted by a hydrocarbon group represented by Formulas 1 to 30 and a group represented by the above formula (13).
  • the tool body example, R 2 7 ⁇ R 3 4 can be given if the human Dorokishiru group substituted by a hydrocarbon group.
  • the above substituent will be described in detail.
  • Preferred examples of the hydrocarbon group having 1 to 30 carbon atoms include a linear or branched alkyl group having 1 to 24 carbon atoms, a cycloalkyl group or an alkylcycloalkyl group having 5 to 13 carbon atoms ( An alkyl-substituted chloroalkyl group, the same applies hereinafter), a linear or branched alkenyl group having 2 to 24 carbon atoms, an aryl group or an alkyl aryl group having 6 to 18 carbon atoms A substituted aryl group; the same applies hereinafter); and an arylalkyl group having 7 to 19 carbon atoms (an aryl substituted alkyl group; the same applies hereinafter).
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a linear or branched pentyl group, Chain or branched hexyl, straight or branched heptyl, straight or branched octyl, straight or branched nonyl, straight or branched decyl, straight or branched undecyl, straight Chain or branched dodecyl, straight or branched tridecyl, straight or branched tetradecyl, straight or branched pendecyl, straight or branched hexadecyl, straight or branched Decyl decyl group, linear or branched decyl group, linear or branched nona Examples include a decyl
  • Preferable examples of the above-mentioned alkyl group include a pentyl grave, a cyclohexyl group, and a cycloheptyl group. Also, preferable examples of the above-mentioned alkyl group include a methylcyclopentyl group and a dimethyl group.
  • Cyclopentyl group (including all substituted isomers), ethylcyclopentyl group (including all substituted isomers), linear or branched propylcyclopentyl group (including all substituted isomers), ethylmethylcyclopentyl Group (including all substituted isomers), trimethylcyclopentyl group (including all substituted isomers), getylcycline pentyl group (including all substituted isomers), ethyldimethylcyclopentyl group (including all substituted isomers) Linear or branched propyl methylcyclopentyl group (including isomers) All substituted isomers), linear or branched propylethylcyclopentyl group (including all substituted isomers), di-linear or branched propylcyclopentyl group (including all substituted isomers) , Linear or branched propylethylmethylcyclopentyl group (including all substituted isomers) , Line
  • alkenyl group examples include a vinyl group, a propenyl group, an isopropyl group, a linear or branched butenyl group, a linear or branched pentenyl group, a linear or branched hexenyl group, and a linear group.
  • heptenyl straight or branched octenyl, straight or branched nonenyl, straight or branched decenyl, straight or branched decenyl, straight or branched dodecenyl, straight Chain or branched tridecenyl, straight or branched tetradecenyl, straight or branched pentadecenyl, straight or branched hexadecenyl, straight or branched heptadenyl, oleyl, etc.
  • a bushenyl group having two double bonds can also be mentioned as a preferable example.
  • Preferred examples of the aryl group include a phenyl group and a naphthyl group.
  • preferred examples of the alkylaryl group include a tolyl group (including all substituted isomers) and a xylyl group.
  • Preferred examples of the above arylalkyl group include a benzyl group, a methylpentyl group (including all substituted isomers), a dimethylpentyl group (including all substituted isomers), a phenethyl group, and a methylphenethyl group (including all substituted isomers). Isomers) and dimethylphenethyl group (including all substituted isomers).
  • the hydrocarbon group having 1 to 30 carbon atoms is preferably a linear or branched alkyl group, cycloalkyl group, or alkyl-substituted cycloalkyl group having 1 to 24 carbon atoms, more preferably, A linear or branched alkyl group having 1 to 12 carbon atoms, particularly preferably a linear alkyl group having 1 to 8 carbon atoms, and most preferably a linear alkyl group having 1 to 6 carbon atoms.
  • Preferred examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R 31 , R 32 , R 33 and R 34 are the same as the specific examples of the hydrocarbon group having 1 to 30 carbon atoms described above. It is.
  • Examples of the heterocyclic group include, for example, specific examples (skeleton) of the heterocyclic compound.
  • the group represented by the general formula (13) will be described in detail.
  • Y is preferably an alkylene group having 2 to 6 carbon atoms, and more preferably an alkylene group having 2 to 4 carbon atoms.
  • alkylene group having 2 to 4 carbon atoms include, for example, ethylene group, propylene group (1-methylethylene group, 2-methylethylene group), butylene group (1-ethylethylene group, 2-ethylethylene group) , 1,2-dimethylethylene group, 1,1-dimethylethylene group and 2,2-dimethylethylene group.
  • h is 2 or more, a plurality of Ys may be the same or different in the same molecule.
  • (YO) represents a polymer skeleton derived from an alkylene oxide.
  • alkylene oxide include ethylene oxide, propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide and isobutylene oxide.
  • These alkylene oxides may be composed of one type of structural unit or a mixture of a plurality of structural units. sand That is, it may be a homopolymer of alkylene oxide or a copolymer (random polymer or block polymer).
  • h is preferably an integer of 1 to 100, more preferably an integer of 1 to 50, and an integer of 1 to 20 in particular, most preferably an integer of 1 to 10 and most preferably Is an integer of 1 to 5.
  • hydrocarbon group of H 3 carbon atoms represented by 5 1-3 0 are the same as the embodiment described above explained.
  • R 35 is a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a carbon atom having 6 carbon atoms.
  • Substituents of the heterocyclic compounds of the present invention heat Dorokishiru group, 1 carbon atoms 3 0 hydrocarbon group, one OR 2 7 (R 2 7 good carbon atoms which may have a substituent 1 to 3 0 And particularly preferably a hydrocarbon group having 1 to 30 carbon atoms substituted with a hydryl xyl group), or a group represented by the general formula (13) And most preferably a group represented by the general formula (13).
  • the heterocyclic compound of the present invention is particularly preferably a compound having a virolidone structure substituted with a group represented by the above general formula (13).
  • Most preferred as the heterocyclic compound of the present invention is a compound represented by the general formula (A).
  • Y and R 3 5 in the general formula (1 3) represents Y and R 3 5 the same group in, h and i, and h and i which in the general formula (1 3) Represents the same integer.
  • the complex compound represented by the general formula (A) preferably has the following structure.
  • Y is alkylene of 2-6 carbon atoms
  • R 35 is a hydrogen atom, carbon number 1-1 2 linear or branched alkyl group, ⁇ Li Ichiru group 6-1 8 carbon atoms Or a straight-chain or branched alkylaryl group having 6 to 18 carbon atoms
  • h is an integer of 1 to 100
  • i is 0 or 1.
  • the heterocyclic compound represented by the general formula (A) has the following structure.
  • Y is an alkylene group having 2 to carbon atoms 4
  • H 35 is a hydrogen atom, a linear or branched alkyl group having a carbon number of 1-6, also linear Fuweniru group or a carbon number of 7-1 5 Or a branched alkylaryl group
  • h is an integer of 1 to 50
  • i is 0 or 1.
  • the heterocyclic compound represented by the general formula (A) is more preferably a compound represented by the following general formula (A-1).
  • ⁇ is an alkylene group having 2 to 4 carbon atoms
  • h is an integer of 1 to 20.
  • h is particularly preferably an integer of 1 to 10, and most preferably h is an integer of 1 to 5.
  • the fuel oil additive of the present invention can exhibit its effect more by combining the heterocyclic compound with polyetheramine and / or polyalkenylamine. It is possible.
  • the polyetheramine referred to in the present invention is a polymer containing at least one basic nitrogen and an ether bond.
  • the weight average molecular weight of the polyetheramine is not particularly limited, but is usually from 100 to 1500.
  • the ratio (Mw Mn) between the weight average molecular weight and the number average molecular weight is not particularly limited, but usually a ratio of 1.0 to 1.5 is used.
  • the polyetheramine of the present invention is a polymer having a basic nitrogen and an ether bond, but may have other polar groups and bonding groups in the molecule. Specifically, for example, a glycidyl group or the like may be contained in a side chain of a bonding group such as an amide group, a urethane group, an ester group, or a carbonate group, or a polyester skeleton.
  • the polyetheramine of the present invention is preferably, for example, a compound represented by the following general formula (1).
  • R 1 represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms
  • R 2 , H 3 , R 4 and R 5 each independently represent a hydrogen atom
  • R 6 represents an alkylene group having 1 to 10 carbon atoms;
  • Z represents a group selected from the following group A
  • X represents a group selected from the following group B, a is an integer of 1 to 200, b is 0 or 1, c is 0 or 1, and d is an integer of 1 to 3.
  • R 8 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms or an alkoxyalkyl group having 2 to 10 carbon atoms
  • R 9 represents 2 to 9 carbon atoms.
  • 6 represents an alkylene group having 6 to 10 carbon atoms or an alkylene group having an alkoxyalkyl group as a substituent
  • R 1Q represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms, and: Indicates an integer of 50.
  • B 2 a hydrocarbon group having 1 to 30 carbon atoms
  • B4 a nitrogen-containing group represented by the following general formula (4)
  • R 15 represents an alkylene group having 2 to 6 carbon atoms
  • R 16 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a group represented by the general formula (3)
  • R 17 represents a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms or a group represented by the above general formula (3)
  • g represents an integer of 1 to 5.
  • R 1 is a hydrogen atom, or a linear or branched alkyl group having 1 to 24 carbon atoms, a cycloalkyl group or an alkylcycloalkyl group having 5 to 13 carbon atoms, and a carbon atom having 2 to 24 carbon atoms.
  • Preferred alkyl groups represented by R 1 include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, and straight chain.
  • Preferred examples of the cycloalkyl group represented by R 1 include a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • Examples of the same preferred alkylcycloalkyl group include, for example, methyl Cyclopentyl, dimethylcyclopentyl (including all substituted isomers), ethylcyclopentyl (including all substituted isomers), linear or branched propylcyclopentyl (including all substituted isomers), d Tylmethylcyclopentyl group (including all substituted isomers), trimethylcyclopentyl group (including all substituted isomers), getylcyclopentyl group (including all substituted isomers), ethyldimethylcyclopentyl group (including all substituted isomers) Including all substituted isomers), linear or branched propylmethyl Cyclobentyl (including all substituted isomers), linear or branched prop
  • Preferred alkenyl groups represented by R 1 include, for example, vinyl group, propenyl group, isopropyl group, linear or branched butenyl group, linear or branched pentenyl group, linear or branched hexenyl Group, linear or branched heptenyl group, linear or branched octenyl group, linear or branched nonenyl group, linear or branched decenyl group, linear or branched undecenyl group, linear or branched dodecenyl group Group, linear or branched tridecenyl group, linear or branched tetradecenyl group, linear or branched pentadecenyl group, linear or branched hexadecenyl group, linear or branched hepdecenyl group, oleyl Linear or branched octenyl decenyl group, linear or branched nonadecenyl group, linear
  • Preferred aryl groups represented by R 1 include, for example, a phenyl group And a naphthyl group.
  • Preferred examples of the alkylaryl group also include, for example, a tolyl group (including all substituted isomers), a xylyl group (including all substituted isomers), and an ethylphenyl group (including all substituted isomers).
  • Preferred arylalkyl groups represented by are, for example, a benzyl group, a methylpentyl group (including all substituted isomers), a dimethylpentyl group (including all substituted isomers), a phenethyl group, a methylphenethyl group ( Dimethylphenethyl group (including all substituted isomers) and dimethylphenethyl group (including all substituted isomers).
  • R 1 is a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, or an alkyl group More preferably a reel group, hydrogen atom, charcoal If it is a linear or branched alkyl group with a prime number of 1 to 6, if it is a phenyl group, or if it has carbon atoms? ⁇ Particularly preferably represents 1 5 straight or branched Arukirua aryl group, o the R 2, RR 4 and R 5 correct the most preferred case is a hydrogen atom, it then independently hydrogen, carbon 1 A hydrocarbon group of 1 to 16 or a group represented by the general formula (2).
  • the hydrocarbon group having 1 to 16 carbon atoms referred to herein includes, for example, a linear or branched alkyl group having 1 to 16 carbon atoms, a cycloalkyl group having 5 to 16 carbon atoms, or an alkylcycloalkyl group.
  • Preferred alkyl groups include, for example, methyl, ethyl, n-propyl, 'isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, linear or branched pentyl, Straight or branched hexyl group, straight or branched heptyl group, straight or branched octyl group, straight or branched nonyl group, straight or branched decyl group, straight or branched decyl group, Straight or branched decyl group, Straight or branched dodecyl, straight or branched tridecyl, straight or branched tetradecyl, straight or branched pendecyl, and straight or branched hexadecyl; It is.
  • Preferred cycloalkyl groups include, for example, cyclopentyl group, cyclohexyl group, and cycloheptyl group.
  • Preferred alkylcycloalkyl groups include, for example, methylcyclopentyl group (including all substituted isomers).
  • Preferred alkenyl groups include, for example, a vinyl group, a propenyl group, an isopropyl group, a linear or branched butenyl group, a linear or branched pentenyl group, a linear or branched hexenyl group, a linear or branched hexenyl group, Branched heptenyl, straight or branched octenyl, straight or branched nonenyl, straight or branched decenyl, straight or branched decenyl, straight or branched dodecenyl, straight Or branched tridecenyl groups, straight or branched Examples include a branched tetradecenyl group, a linear or branched pendecenyl group, and a linear or branched hexadecenyl group.
  • a bushenyl group having two double bonds is also a preferred example.
  • Preferred aryl groups include, for example, a phenyl group and a naphthyl group.
  • Preferred alkylaryl groups include, for example, a tolyl group (including all substituted isomers), a xylyl group (including all substituted isomers) ), Ethyl phenyl group (including all substituted isomers)
  • Linear or branched propylphenyl group including all substituted isomers
  • ethylmethylphenyl group including all substituted isomers
  • trimethyl phenyl group including all substituted isomers
  • Chain or branched butyl phenyl including all substituted isomers
  • linear or branched propylmethyl phenyl including all substituted isomers
  • getyl phenyl including all substituted isomers
  • Examples include a tyldimethylphenyl group (including all substituted isomers) and a tetramethylphenyl group (including all substituted isomers).
  • Preferable arylalkyl groups include, for example, a pendyl group, a methylpentyl group (including all substituted isomers), a dimethylbenzyl group (including all substituted isomers), a phenethyl group, a methylphenethyl group (including all substituted isomers) ), And a dimethylphenethyl group (including all substituted isomers).
  • hydrocarbon groups having 1 to 16 carbon atoms represented by R 2 , R 3 , R 4 and R 5 it is particularly preferable that the hydrocarbon group is a linear or branched alkyl group having 1 to 8 carbon atoms, Most preferably, it is a linear or branched alkyl group having 1 to 3 carbon atoms.
  • the polarity of the nitrogen-containing polar group is large, one to several hydrocarbon groups having 8 to 16 carbon atoms may be contained in the whole molecule. preferable.
  • R 7 and R 8 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or an alkoxyalkyl group having 2 to 10 carbon atoms.
  • the hydrocarbon group having 1 to 10 carbon atoms includes a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group or an alkylcycloalkyl group having 5 to 10 carbon atoms, A linear or branched alkenyl group having 2 to 10 carbon atoms, an aryl group or an alkyl aryl group having 6 to 10 carbon atoms, and an arylalkyl group having 7 to 10 carbon atoms; Included.
  • Preferred alkyl groups include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, linear or branched pentyl group, straight chain Or a branched hexyl group, a straight or branched heptyl group, a straight or branched octyl group, a straight or branched nonyl group, and a straight or branched decyl group.
  • cycloalkyl group examples include a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • alkylcycloalkyl group examples include a methylcyclopentyl group (including all substituted isomers) and dimethyl Cyclopentyl group (including all substituted isomers), ethylcyclopentyl group (including all substituted isomers), linear or branched pentyl pentyl group (including all substituted isomers), and ethylmethylcyclopentyl group (Including all substituted isomers), trimethylcyclopentyl group (including all substituted isomers), getyl cyclopentyl group (including all substituted isomers), and ethyl dimethylcyclopentyl group (including all substituted isomers) , Straight or branched Propylmethylcyclopentyl (including all substituted isomers), linear or branched propyleth
  • Preferred alkenyl groups include, for example, vinyl group, propenyl group, isopropyl group, linear or branched butenyl group, linear or branched pentenyl group, linear or branched hexenyl group, linear or branched hexenyl group. Examples include a branched heptenyl group, a straight or branched octenyl group, a straight or branched nonenyl group, and a straight or branched decenyl group. In addition, a bushenyl group having two double bonds is also a preferred example.
  • Preferred aryl groups include, for example, phenyl and naphthyl groups
  • preferred alkylaryl groups include, for example, a tolyl group (including all substituted isomers), a xylyl group (for all Ethyl phenyl group (including all substituted isomers) ), Linear or branched propylphenyl group (including all substituted isomers), ethylmethylphenyl group (including all substituted isomers), trimethyl phenyl group (including all substituted isomers) , Linear or branched butyl phenyl group (including all substituted isomers), linear or branched propyl methyl phenyl group (including all substituted isomers), getyl phenyl group (including all substituted isomers) And ethyl dimethyl phenyl group (including all substituted isomers), and tetramethyl phenyl group (including all substituted isomers).
  • Preferred arylalkyl groups include, for example, a benzyl group, a methylbenzyl group (including all substituted isomers), a dimethylbenzyl group (including all substituted isomers), a phenethyl group, a methylphenethyl group (including all substituted isomers) ), And a dimethylphenethyl group (including all substituted isomers).
  • alkoxyalkyl group having 2 to 10 carbon atoms examples include, for example, methoxymethyl group, ethoxymethyl group, n-propoxymethyl group, isopropoxymethyl group, n-butoxymethyl group, isobutoxymethyl group, sec-butoxy Methyl, tert-butoxymethyl, pentoxymethyl (including all isomers), hexoxymethyl
  • —H 7 and: 8 in the general formula (2) are preferably or independently of each other a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 6 carbon atoms. Particularly preferably, it is an alkyl group having the number of 1 to 3.
  • R 9 represents an alkylene group having 2 to 6 carbon atoms or an alkylene group having a total of 4 to 10 carbon atoms having an alkoxyalkyl group as a substituent.
  • alkylene group having 2 to 6 carbon atoms include an ethylene group, Propylene group (1-methylethylene group, 2-methylethylene group), trimethylene group, butylene group (1-ethylethylene group, 2-ethylethylene group), 1,2-dimethylethylene group, 2,2-dimethylethylene group , 1-methyltrimethylene group, 2-methyltrimethylene group, 3-methyltrimethylene group, tetramethylene group, pentylene group (1-butylethylene group, 2-butylethylethylene group), 1-ethyl-1-methylethylene group , 1-Ethyl-1-methylethylene group, 1,1,2—Trimethylethylene group, 1,2,2-Trimethylethylene group, 1-Ethyltrimethylene group, 2-Ethyltrimethylene group, 3-Ethylt Limethylene group, 1,1-dimethyl
  • Trimethyl trimethylene group 1, 1, 3 — Trimethyl trimethylene 1,2,2—trimethyltrimethylene group, 1,2,3—trimethyltrimethylene group, 1,3,3—trimethyltrimethylene group, 2,2,3-trimethyltrimethylene group , 2,3,3—trimethyltrimethylene group, 1—ethylethyltramethylene group, 2-ethyltetramethylene group, 3-ethylethyltramethylene group, 4-ethylethyltramethylene group, 1,1—dimethyltetramethylene group, 1,2-dimethyltetramethylene 1,3-Dimethyltetramethylene group, 1,4-Dimethyltetramethylene group, 2,2-Dimethyltetramethylene group, 2,3-Dimethyltetramethylene group, 2,4-Dimethyltetramethylene group, 3,3-Dimethyltetramethylene group Group, 3,4-dimethyltetramethylene group, 4,4-dimethyltetramethylene group, 1-methylmethylte
  • the alkylene group having a total carbon number of 4 to 10 containing the alkoxyalkyl group represented by R 9 as a substituent is preferably an alkoxyalkyl group-substituted ethylene group having a total carbon number of 4 to 8, and examples of these include: — (Methoxymethyl) ethylene group, 2 — (Methoxymethyl) ethylene group, 1- (Methoxyxethyl) ethylene group, 2— (Methoxyxethyl) ethylene group, 1 — (Ethoxymethyl).
  • R 9 in the general formula (2) is particularly preferably an alkylene group having 2 to 4 carbon atoms or an alkylene group substituted with an alkoxyalkyl group having 4 to 6 carbon atoms in total.
  • R 1 (3 is a hydrogen atom, or a linear or branched alkyl group having 1 to 24 carbon atoms and a cycloalkyl having 5 to 13 carbon atoms described above for R 1; Group or alkylcycloalkyl group, linear or branched alkenyl group having 2 to 24 carbon atoms, aryl group or alkylaryl group having 6 to 18 carbon atoms, or 7 to 19 carbon atoms
  • R 1 ° is more preferably an alkyl group having 1 to 24 carbon atoms, particularly preferably an alkyl group having 1 to 12 carbon atoms.
  • F in the general formula (2) is preferably an integer of 0 to 30, more preferably 0 to 20. Therefore, in the group represented by the general formula (2), R 7 and R 8 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 6 carbon atoms, R 9 is an alkylene group having 2 to 6 carbon atoms or an alkoxyalkyl group-substituted ethylene group having 4 to 8 carbon atoms, R 10 is an alkyl group having 1 to 24 carbon atoms, and f is 0 Those which are integers of up to 30 are preferred.
  • substituent group (2a) such a group (represented by the general formula (2) For convenience) is referred to as “preferred substituent group (2a)” for convenience.
  • R 7 and R 8 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • R 9 is an alkylene group having 2 to 4 carbon atoms
  • R 1 Q is a carbon atom having 1 to 12 carbon atoms. Is more preferably an alkyl group of the formula: wherein and is an integer of 0 to 20.
  • such a group (not indicating the group represented by the general formula (2)) is referred to as a “more preferred substituent group (2b)” for convenience.
  • R 2 , R 3 , R 4 and R 5 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or the above-mentioned “preferred” R 2 , RR 4 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or the above-mentioned “substituent group (2a)”. Preferred substituent group (2b) ".
  • R 6 in the general formula (1) represents an alkylene group having 1 to 10 carbon atoms, preferably an alkylene group having 1 to 6 carbon atoms, and more preferably an alkylene group having 1 to 3 carbon atoms. It is.
  • alkylene group having 1 to 10 carbon atoms include methylene group, ethylene group, 1-methylethylene group, 2-methylethylene group, trimethylene group, 1-methyltrimethylene group, and 2-methyltrimethylene.
  • A2 one CO - A3 -O-CO- 11 - A4 -O-CO-O- 12 - A5 -CO-O- 13 -.
  • the above-mentioned I 11 , R 12 and R 13 each independently represent an alkylene group having 1 to 6 carbon atoms.
  • examples of the above R b ′ can be given.
  • 11 , R 12 , and; 13 are each independently preferably an alkylene group having 1 to 4 carbon atoms.
  • Preferred specific examples thereof include a methylene group, an ethylene group, and a propylene group ( 1-methylethylene group, 2-methylethylene group, trimethylene group, butylene group (1-1-ethylethylene group, 2-ethylethylene group), 1,2-dimethylethylene group, 2,2-dimethylethylene group, 1-methyltrimethylene Group, 2-methyltrimethylene group, 3-methyltrimethylene group, and tetramethylene group.
  • More preferred I 11 , R 12 and: 13 are each independently an alkylene group having 1 to 3 carbon atoms, and specific preferred examples thereof include a methylene group, an ethylene group and a propylene group (1-methylethylene group, 2-methylethylene group) and trimethylene group.
  • — Z in the general formula (1) is preferably Al, A2 or A4.
  • a is preferably an integer of 2 to 100.
  • b and c are each independently 0 or 1.
  • RUR 3 R 4 R 5 R 6 X and Z in the general formula (17) represent the same groups as I 1 R 2 R 3 RR ⁇ R 6 X and Z in the general formula (1), and ad And e are the same integers as ad and e in the general formula (1).
  • c is preferably 0.
  • X represents a group selected from the following group B: Show.
  • B 1 hydrogen atom
  • B 2 a hydrocarbon group having 1 to 30 carbon atoms
  • R 14 represents an alkylene group having 1 to 6 carbon atoms.
  • B4 a nitrogen-containing group represented by the following general formula (4)
  • R 15 represents an alkylene group having 2 to 6 carbon atoms
  • R 1 S represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a group represented by the general formula (3)
  • R 17 represents a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms or a group represented by the above general formula (3)
  • g represents an integer of 1 to 5.
  • Preferred as the hydrocarbon group having 1 to 3 ° C carbon atoms of B2 are the linear or branched alkyl groups having 1 to 24 carbon atoms described above for R 1 , and 5 to 5 carbon atoms. 13 cycloalkyl or alkylcycloalkyl, linear or branched alkenyl having 2 to 24 carbons, aryl or alkylaryl having 6 to 18 carbons, 7 to 1 carbon 9 arylalkyl groups and the like.
  • B 2 is more preferably a linear or branched alkyl group having 1 to 12 carbon atoms, or an aryl group or an arylalkyl group having 6 to 12 carbon atoms.
  • H 14 is An alkylene group having 1 to 6 carbon atoms is shown, and specific examples of such an alkylene group include the groups described above as I 11 , R 12 , and R 13 .
  • R 14 is preferably an alkylene group having 1 to 4 carbon atoms, specifically, a methylene group, an ethylene group, a propylene group (1-methylethylene group, 2-methylethylene group), a trimethylene group, Butylene group (1-ethylethylene group, 2-ethylethylene group), 1,2-dimethylethylene group, 2,2-dimethylethylene group, 1-methyltrimethylene group, 2-methyltrimethylene group, 3-methylmethyl group
  • Preferable examples include a limethylene group and a tetramethylene group.
  • R 1 4 is particularly be an alkylene group having a carbon number of 1 to-3, specifically a methylene group, Echire down, propylene (1-methylethylene group, 2-methylethylene group), or preparative Rimechiren group preferable.
  • R 15 represents an alkylene group having 2 to 6 carbon atoms.
  • Such an alkylene group is specifically described above as R 9
  • the following groups are mentioned.
  • R 15 is preferably an alkylene group having 2 to 4 carbon atoms, specifically, an ethylene group, a propylene group (1-methylethylene group, 2-methylethylene group), a trimethylene group, and a butylene group.
  • R 1 K in the general formula (4) represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a group represented by the above general formula (3).
  • R 16 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom, a methyl group or an ethyl group.
  • R 17 in the general formula (4) represents a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms or a group represented by the above general formula (3).
  • hydrocarbon group having 1 to 30 carbon atoms are the linear or branched alkyl group having 1 to 24 carbon atoms described above for R 1 and 5 to 1 carbon atoms.
  • arylalkyl groups and the like are included.
  • R 17 is a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, an aryl group or an arylalkyl group having 6 to 12 carbon atoms, or
  • the group represented by the general formula (3) is more preferred, and particularly preferably a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group, and a C 7 to C 9 alkyl group. It is a reel alkyl group or a group represented by the general formula (3).
  • —G in the general formula (4) represents an integer of 1 to 5, preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.
  • the group represented by the following general formula (19) contained in the group represented by the general formula (4) has 1 to 5 structural units represented by the following general formula (20), It preferably has 1 to 4, more preferably 1 to 3.
  • R 1 6 and g is the formula in (4): 15,; R 16 and g the same group, shows the integer to.
  • the group represented by the general formula (19) represents a group obtained by bonding the structural units represented by the general formula (20) as follows.
  • R 15 is an alkylene group having 2 to 4 carbon atoms
  • R 16 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a general formula ( 3) wherein R 17 is a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, an aryl group or an alkyl aryl having 6 to 12 carbon atoms.
  • R 15 is preferably a group represented by the general formula (3) and g is 1 to 4, and R 15 is an ethylene group or a propylene group (1-methylethylene group, 2-methylethylene group).
  • R 16 is a hydrogen atom, a methyl group, an ethyl group or a group represented by the general formula (3)
  • R 17 is a hydrogen atom, a straight-chain having 1 to 6 carbon atoms. Or branched alkyl, phenyl, carbon number? Most preferred are alkylaryl groups of 9 to 9 or groups represented by the general formula (3), and g is 1 to 3.
  • the general formula (1) representing the polyether amine of the present invention as a whole is Although the substituents are individually described, the polyetheramine of the present invention has the general formula (1)
  • the substituent of (1) preferably has the following structure.
  • R 1 is a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or an aryl group or an alkyl aryl group having 6 to 18 carbon atoms,
  • R 2 , R 3 , R 4 and R s are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a group represented by the general formula (2),
  • R 7 and R 8 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 6 carbon atoms, and R 9 is alkylene group or aralkyl Kokishiarukiru substituted Echiren group der total carbon number of 4 to 8 6 Ri,: R 1 alpha is an alkyl group of 1-24 carbon atoms, and f is an integer from 0 to 30
  • R 6 is an alkylene group having a prime number of 1 to 6,
  • Z is a group selected from group A,
  • R 1 R 12 , and; R 13 each independently represents an alkylene group having 1 to 4 carbon atoms;
  • X is: a group selected from Group B,
  • B 2 is a linear or branched alkyl group having 1 to 12 carbon atoms or an aryl group or an arylalkyl group having 6 to 12 carbon atoms,
  • R 14 is an alkylene group having 1 to 4 carbon atoms
  • R 15 is an alkylene group having 2 to 4 carbon atoms
  • R 16 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a general formula (3).
  • R 17 is a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, an aryl group or an arylalkyl group having 6 to 12 carbon atoms, or A group represented by the general formula (3)
  • g is an integer from 1 to 4.
  • the substituent of the general formula (1) has the following structure.
  • R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group or an alkylaryl group having 7 to 15 carbon atoms,
  • R 2 , 3 , R 4 and R 5 are each independently a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a group represented by the general formula (2),
  • R 8 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • R 9 is an alkylene group having 2 to 4 carbon atoms
  • R 1 Q is a carbon atom.
  • R 6 is an alkylene group having 1 to 6 carbon atoms
  • a is an integer of 2 to 100, b and c are each independently 0 or 1, d is 1, e is 2,
  • Z is a group selected from A1, A2 and A4,
  • R 12 is an alkylene group having 1 to 3 carbon atoms
  • X is a group selected from among Bl, B3 and B4,
  • an alkylene group R 1 5 is 2 carbon number 3
  • R 1 6 is hydrogen atom, a methyl group, a group represented by Echiru group or the general formula (3) Yes
  • R 17 is a hydrogen atom, carbon number:!
  • g is an integer from 1 to 3.
  • the substituent of the general formula (1) has the following structure. Is a hydrogen atom,
  • RR; R 4 and R 5 are each independently a hydrogen atom or an alkyl group having 1 to 2 carbon atoms;
  • R 6 is an alkylene group having 1 to 3 carbon atoms
  • X is B 1 (hydrogen atom)
  • a is an integer from 2 to 50, b is 0 or 1, c is 0, d is 1, and e is 2.
  • the substituent of the general formula (1) most preferably has the following structure.
  • R 1 is a hydrogen atom
  • R 2 , R 3 R 4 and R 5 are each independently a hydrogen atom or an alkyl group having 1 to 2 carbon atoms,
  • X is B 1 (hydrogen atom)
  • a is an integer from 2 to 50, b and c are 0, d is 1 and e is 2. Next, the polyalkenylamine will be described.
  • the polyalkenylamine referred to in the present invention is a compound obtained by polymerizing one or more alkylene compounds and modifying the terminal of the polyalkylene compound with an amine.
  • the polyalkylene moiety constituting the polyalkenylamine compound of the present invention includes ethylene, propylene, n-butene, 2-butene and isobutene, pentene (including all isomers), hexene (all isomers) ), Heptene (including all isomers), octene (including all isomers), decene (including all isomers), dodecene (including all isomers), tetradecene (including all isomers) ) And hexadecene (including all isomers), and may be a homopolymer using only one type, or a copolymer using two or more types.
  • the copolymer may be a random copolymer, an alternating polymer, or a block copoly
  • any alkylene can be used, but more excellent detergency Therefore, it is preferable to use H HH CCCIIII using butenes (n-butene, 2-butene and isobutene).
  • an oxygen-containing group such as a 33 hydrocarbon group or an alkanol group, or a nitrogen-containing group such as an aminoalkyl group may be bonded.
  • Specific examples of the polyalkenylamine compound of the present invention include a polybutenylamine compound represented by the following general formula (5).
  • A represents an n-butyl group, a sec-butyl group or a tert-butyl group
  • R 18 , R ig , R 2 Q and R 21 each independently represent a hydrogen atom, a methyl group or Echiru group, and an R 18, R 19, 1 2 ( Oyobi 11 21 total number of carbon atoms of 2
  • B is represented by either of the following formulas (6) - (11)
  • R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, an alkanol group having 1 to 8 carbon atoms, or a group represented by the following general formula (12)
  • m represents an integer of 1 to 100.
  • R 24 represents an alkylene group having 2 to 6 carbon atoms
  • R 25 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
  • : 26 represents a hydrogen atom or a carbon number.
  • A is preferably a t tert -butyl group, since more excellent detergency can be obtained.
  • R 18 and R 2 Q are hydrogen atoms and R 19 and R 21 are methyl groups, or when R 18 and R 20 are methyl groups And R 19 and R 21 are preferably hydrogen atoms.
  • the group represented by the following formula (21) has a group represented by the following formula (22) as a constituent unit, and is a polymer skeleton of a polyptenylamine-based compound represented by the general formula (5). Is shown.
  • the m groups represented by the above formula (22) may be the same or different in the same molecule. That is, the compound represented by the above formula (5) and the group represented by the above formula (21) may be a homopolymer or a copolymer.
  • the copolymer may be a random copolymer, an alternating polymer, or a block copolymer.
  • B is preferably a group represented by the formula (6) or (10), and more preferably a group represented by the formula (10), since more excellent detergency is obtained. .
  • R 22 and R 23 it shows that independently hydrogen atom, a hydrocarbon group having 1-10 carbon atoms, a group represented by Al force Nord group or the general formula having 1 to 8 carbon atoms (12).
  • hydrocarbon group having 1 to 10 carbon atoms represented by R 22 and R 23 straight-chain or branched alkyl group having 1 to 10 carbon atoms, or alkylcycloalkyl cycloalkyl group having 5 to 10 carbon atoms Alkyl group, linear or branched alkenyl group having 2 to 10 carbon atoms, aryl group or alkylaryl group having 6 to 10 carbon atoms, carbon number? To 10 arylalkyl groups.
  • alkyl group having 1 to 10 carbon atoms examples include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isoptyl group, sec-butyl group, t-butyl group, Straight or branched pentyl group, straight or branched hexyl group, straight or branched heptyl group, straight or branched octyl group, straight or branched nonyl group, and straight or branched decyl group And the like.
  • cycloalkyl group or alkylcycloalkyl group of -10 include, for example, cyclopentyl group, cyclohexyl group, cycloheptyl group, methylcyclopentyl group, dimethylcyclopentyl group (including all substituted isomers), Ethylcyclopentyl group (including all substituted isomers), linear or branched propylcyclopentyl group (including all substituted isomers), ethylmethylcyclyl Mouth pentyl group (including all substituted isomers), trimethylcyclopentyl group (including all substituted isomers), getylcyclopentyl group (including all substituted isomers), ethylmethylcyclopentyl group (all To a straight-chain or branched propylmethylcyclopentyl group (including all substituted isomers), a straight-chain or branched propylethylcyclopentyl group (including all substituted isomers
  • alkenyl group having 2 to 10 carbon atoms examples include, for example, ethenyl group, n-propenyl group, isopropyl group, n-butenyl group, isobutenyl group, sec-butenyl group, tert-butenyl group A linear or branched pentenyl group, a linear or branched hexenyl group, a linear or branched heptenyl group, a linear or branched octenyl group, a linear or branched nonenyl group, and a linear or branched nonenyl group; A decenyl group.
  • Examples of the aryl or alkylaryl group having 6 to 10 carbon atoms include a phenyl group, a tolyl group (including all substituted isomers), a xylyl grave (including all substituted isomers), and an ethylphenyl group ( Including all substituted isomers), linear or Branched propylphenyl group (including all substituted isomers), ethylmethylphenyl group (including all substituted isomers), trimethylphenyl group (including all substituted isomers), straight chain Or branched butylphenyl group (including all substituted isomers), straight-chain or branched propylmethylphenyl group (including all substituted isomers), getylphenyl group (including all substituted isomers), ethyl Examples include a dimethylphenyl group (including all substituted isomers) and a tetramethylphenyl group (including all substituted isomers).
  • alkylaryl group having 7 to 10 carbon atoms examples include a benzyl group, a methylbenzyl group (including all substituted isomers), a dimethylbenzyl group (including all substituted isomers) , A phenylethyl group, a methylphenethyl group (including all substituted isomers), and a dimethylphenethyl group (including all substituted isomers).
  • the alkanol Ichiru group R 2 2 and R 2 3 carbon atoms represented by 1-8, specifically, for example, hydroxymethyl group, hydroxyethyl E methyl group, straight or branched hydro Kishipuropiru group, straight chain Or a branched hydroxybutyl group, a straight or branched hydroxypentyl group, a straight or branched hydroxyhexyl group, a straight or branched hydroxyheptyl group, a straight or branched hydroxyoctyl group, a straight or branched Examples include a branched hydroxynonyl group, and a straight-chain or branched hydroxydecyl group.
  • the group represented by the general formula (12) will be described.
  • R 2 4 carbon atoms represented by 2-6, there can be mentioned the same groups as the groups represented by R 1 5 in the general formula (4). That,: R 2 4 is include the groups described above as R 9, preferably, an alkylene group having 2 to 4 carbon atoms. Specific examples of these are ethylene, propylene (1-methylethylene, 2-methylethylene), trimethylene, butylene (1-ethylethylene, 2-ethylethylene), 1,2-diethylene Methyl ethylene group, 2,2-dimethyl ethylene group, 1-methyl trim Preferred examples include a tylene group, a 2-methyltrimethylene group, a 3-methyltrimethylene group, and a tetramethylene group. More preferably, it is an alkylene group having 2 to 3 carbon atoms, and specific examples include an ethylene group, a propylene group (1-methylethylene group, 2-methylethylene group) and a trimethylene group.
  • Alkyl group having 1 to 4 carbon atoms represented by R 25 there can be mentioned the same groups as alkyl group having 1 to 4 carbon atoms which is table with R 16 in the general formula (4). That is, specific examples of the alkyl group having 1 to 4 carbon atoms represented by R 25 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a sec group. —Butyl group and tert-butyl group.
  • R 25 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom, a methyl group or an ethyl group.
  • R 26 is more preferably a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or an aryl group or an aryl alkyl group having 6 to 12 carbon atoms.
  • Preferred and particularly preferred are a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group, and an arylalkyl group having 7 to 9 carbon atoms.
  • N in the general formula (12) represents an integer of 1 to 5, preferably 1 And an integer of 1 to 3, and more preferably an integer of 1 to 3.
  • Formula (1 2) a group represented by the structural unit (an R 24 N (R 2 5) -) is may be one composed of one kind, or may be also the consist of two or more . When two or more types of structural units are used, these structural units can take any of a random bond, an alternate bond, and a block bond.
  • R 22 and R 23 are each independently a hydrogen atom or a group represented by the general formula (12), since more excellent cleanliness can be obtained.
  • m is required to be 1 or more, preferably 5 or more, more preferably 10 or more, from the viewpoint of maintaining dispersibility in gasoline and maintaining cleanliness. preferable.
  • it is necessary to be 100 or less, preferably 50 or less, more preferably 40 or less. .
  • polyalkenylamine compound of the present invention only one compound represented by the general formula (5) may be used alone, or a mixture of two or more compounds having different structures may be used.
  • the number average molecular weight of the polyalkenylamine compound of the present invention is not particularly limited, but is preferably 200 or more, and more preferably 400 or more from the viewpoint of maintaining dispersibility in gasoline and maintaining cleanliness. Is more preferable, and particularly preferably 700 or more. Further, from the viewpoint of the effect on the valve stick due to the increase in viscosity and the combustion chamber deposit due to the deterioration of thermal decomposition, it is preferably 6000 or less, more preferably 3000 or less, and particularly preferably 2400 or less. .
  • the fuel oil additive of the present invention is a very useful compound especially as a gasoline and gas oil additive, and is a gasoline composition, a pace gas oil and a gasoline composition obtained by mixing with a base gasoline and optionally other gasoline additives. It is used as a gas oil composition obtained by mixing with other gas oil additives as required.
  • the fuel oil additive of the present invention is also a very useful compound as a gasoline additive for a direct injection gasoline engine and a light oil additive for a direct injection diesel engine. It is also used as a gasoline composition for a gasoline engine and a light oil composition for a direct injection type diesel engine.
  • the content (total amount) of the fuel oil additive of the present invention in gasoline and gas oil compositions is not particularly limited, but is usually in the range of 0.001 to 10% by mass based on the total gasoline or gas oil composition. is there.
  • the lower limit of the content is 0.001% by mass, preferably 0.003% by mass, more preferably 0.05% by mass, particularly preferably 0.01% by mass, and most preferably 0.1% by mass. 0 15% by mass.
  • the upper limit of the content is 10% by mass, preferably 5% by mass, from the viewpoint that the various properties of gasoline and light oil are not adversely affected, and the effect is not expected to increase even if added more.
  • it is 4% by weight, most preferably 3% by weight.
  • the content (total amount) of polyetheramine and / or polyalkenylamine in gasoline and gas oil compositions, which exhibits a higher cleaning effect when combined with the heterocyclic compound of the present invention is not particularly limited, but is usually limited. It is in the range of 0.001-1% by mass, based on the total amount of gasoline or gas oil composition.
  • the lower limit of the amount is 0.001% by mass, preferably 0.003% by mass, more preferably 0.05% by mass, particularly preferably 0.01% by mass, and most preferably 0.01% by mass. 15% by mass
  • the upper limit of the content is 10% by mass, preferably 5% by mass, more preferably 4% by mass, and most preferably 3% by mass, from the viewpoint that improvement of the fruit cannot be expected.
  • the mixing ratio between the heterocyclic compound of the present invention and polyetheramine and / or polyalkenylamine is arbitrary. First, a gasoline composition containing the additive of the present invention will be described.
  • Base gasoline can be produced by any conventionally known method.
  • gasoline M include light naphtha, which has any properties and is obtained by distilling crude oil under normal pressure; cracked gasoline obtained by catalytic cracking, hydrocracking, etc .; Reformed gasoline; polymerized gasoline obtained by polymerization of olefin; alkylate obtained by adding (alkylation) lower olefin to hydrocarbon such as isobutane; light naphtha is converted to isoparaffin by isomerization unit.
  • a typical blending example of unleaded gasoline is shown below.
  • Butane 0 to 10% by volume
  • the method of reducing benzene at this time is not particularly limited and is optional, but particularly, benzene is contained in a large amount in the reformed gasoline, so the mixing ratio of the modified gasoline is reduced, and the following method is used. It is preferable to use a reformed gasoline that has been treated to reduce the benzene concentration in the reformed gasoline.
  • Desulfurized heavy naphtha obtained by distilling and removing hydrocarbon compounds having 6 carbon atoms is used as the raw material for the catalytic reformer.
  • gasoline additives include, for example, detergents and dispersants such as succinic acid imids and polyethers; Antioxidants; metal deactivators, such as Schiff-type compounds and thioamide-type compounds; surface ignition inhibitors, such as organic phosphorus compounds; anti-freezing agents, such as polyhydric alcohols and their ethers; A flame retardant such as a salt or an alkaline earth metal salt, a higher alcohol sulfate ester; an antistatic agent such as an anionic surfactant, a cationic surfactant, an amphoteric surfactant; a coloring agent such as an azo dye; Rust inhibitors such as alkenyl succinate; discriminants such as Kirizan and coumarin; and odorants such as natural essential oil synthetic fragrance.
  • detergents and dispersants such as succinic acid imids and polyethers
  • Antioxidants such as Schiff-type compounds and thioamide-type compounds
  • surface ignition inhibitors such as organic phosphorus compounds
  • anti-freezing agents
  • One or more of these additives can be added, and the total amount thereof is preferably 0.1% by mass or less based on the total amount of the gasoline composition.
  • the properties and composition of the gasoline composition comprising the base gasoline, the additive of the present invention, and other gasoline additives as required are not particularly limited. However, it is desirable that the distillation properties measured by JISK 2254 “Petroleum products-Distillation test method” are as follows.
  • the lower limit of the initial boiling point is preferably 20 ° (more preferably 25 ° C. If it is lower than 20 ° C, the startability may deteriorate under high temperature conditions.
  • the upper limit of the initial boiling point is preferably 45 ° C, more preferably 40 ° C, and still more preferably 35 ° C. is there.
  • the lower limit of T 10 is preferably 35 ° C, more preferably 40 ° C. If the temperature is lower than 35 ° C, startability may deteriorate under high temperature conditions.
  • the upper limit of the T 10 is preferably 55 ° C, more preferably 50 ° C, even more preferably 48 ° C. If the temperature exceeds 55 ° C, there is a possibility that a problem may occur in low-temperature startability.
  • the lower limit of T 30 is preferably 55 ° C, more preferably 60 ° C. If the temperature is lower than 55 ° C, there is a possibility that high-temperature driving performance may be impaired or gasoline coking may occur in the injector.
  • T 3. Is preferably 75 ° C, more preferably 70 ° C, and even more preferably 68 ° C. If the temperature exceeds 75 ° C, there is a possibility that the low-temperature operability will be defective.
  • the lower limit of T 50 is preferably 75 ° C, more preferably 80 ° C. If the temperature is lower than 75 ° C, there is a possibility that high-temperature operability may be impaired.
  • Kirichi on the T 50 is preferably 100 ° C, more preferably 95 ° C, even more preferably 93 ° C. If the temperature exceeds 100 ° C, there is a possibility that the low-temperature and normal-temperature operability may be defective.
  • the lower limit of T 70 is preferably 100 ° C.
  • the upper limit is preferred properly is 130 ° C of T 70, and more preferably 125 ° C, even more preferably 123 ° C, and most preferably 120 ° C. If the temperature exceeds 130 ° C, there is a possibility that the low-temperature and normal-temperature operability may be deteriorated.
  • the lower limit of T 90 is preferably 1 10 ° (, more preferably 120 ° C. If less than 1 1 0 ° C is likely to fuel consumption is reduced.
  • the upper limit of the T 90 is 160 ° C, more preferably 150 ° C, from the viewpoint that deterioration in low-temperature and normal-temperature operation, increase in exhaust gas, deterioration of engine oil and generation of sludge can be suppressed. Is more preferably 140 PC .
  • the lower limit of the distillation end point is preferably 130 ° C.
  • the upper limit of the distillation end point is preferably 210 ° C, more preferably 200 ° C, still more preferably 195 ° C, and most preferably 190 ° C. If the end point exceeds 210 ° C, there is a possibility that normal-temperature operability may suffer.
  • the vapor pressure of the gasoline composition is not particularly limited, the vapor pressure is 7 OkPa because no gasoline coking problem occurs in the injector and the amount of evaporation is suppressed. Or less, more preferably 65 kPa or less, even more preferably 6 OkPa or less, and most preferably 55 kPa It is less than Pa.
  • the vapor pressure means the vapor pressure (Lead vapor pressure (RVP)) measured by JIS K 2258 “Crude oil and fuel oil vapor pressure test method (Reed method)”.
  • the density (15 ° C.) of the gasoline composition is not particularly limited, but is preferably from 0.73 to 0.77 g / cm 3 .
  • the lower limit of the density is more preferably 0.735 g / cm 3 in terms of fuel economy.
  • the upper limit of the density is more preferably 0.76 g / cm 3 from the viewpoint of acceleration and smoldering of the plug.
  • the density refers to the density measured by JISK 2249 “Density Test Method for Crude Oil and Petroleum Products and Density“ Mass-Capacity Conversion Table ”.
  • the above gasoline composition is gasoline substantially free of alkyl lead compounds such as tetraethyl lead, and even if it contains a trace amount of lead compounds, the content is JISK 2255 “Gasoline. Or lower than the applicable category of “Test method for lead in air”.
  • the octane number of the above gasoline composition is not particularly limited, but is preferably 89 or more, more preferably 90 or more, in order to further enhance anti-noking property. Even more preferably, it is 90.5 or more, most preferably 91 or more. Further, in order to enhance the anti-knock property during high-speed driving, the MO value is preferably 80 or more, more preferably 80.5 or more, and most preferably 81 or more. .
  • the research method octane number and the unit octane number are, respectively, the research method octane number and the unit octane number measured according to JIS K 2280 “Test method for unit number and unit number”.
  • Each means octane number.
  • the content of each of the saturated component, the olefin component, and the aromatic component is not particularly limited, but is desirably the following ratio.
  • V (P) 50-100% by volume
  • V (Ar) Aromatic (V (Ar)) 0-35% by volume V (P) prevents coking of gasoline in the injector, reduces smoldering of the plug, keeps the ozone generation capability of the exhaust gas low, reduces the benzene concentration in the exhaust gas, does not generate soot
  • the value is more preferably 60 to 100% by volume, still more preferably 70 to 100% by volume, and most preferably 75 to 100% by mass.
  • V ( ⁇ ) is more preferably 0 to 10% by volume, still more preferably 0 to 7% by volume, and most preferably 0 to 5% from the viewpoint of preventing gasoline phosphorus coking in the injector. %.
  • V (Ar) is more preferably 0 from the viewpoints of reducing the smoldering of the plug, suppressing the ozone generation ability of the exhaust gas, reducing the benzene concentration in the exhaust gas, and not generating soot. -30% by volume, still more preferably 0-25% by volume, and most preferably 0-20% by volume.
  • V (P), V (0) and V (Ar) are all values measured by the fluorescent indicator adsorption method of JIS K 2536 “Testing method for petroleum products-hydrocarbon type”. Further, the content of each component of the gasoline composition is not particularly limited, but it is desirable to satisfy the following conditions.
  • the above V (Bz) indicates the benzene content based on the total amount of the gasoline composition.
  • the benzene concentration in the exhaust gas can be kept low. Its value is preferably from 0 to 1% by volume, more preferably from 0 to 0.5% by volume.
  • V (To 1) and V (C8A) respectively indicate the toluene content and the aromatic hydrocarbon compound content having 8 carbon atoms based on the total gasoline composition
  • the value of V (To 1) is preferably Is from 0 to 30% by volume, more preferably from 0 to 20% by volume
  • the value of V (C8A) is preferably from 0 to 20% by volume, more preferably from 0 to 15% by volume.
  • the aromatic hydrocarbon compound having 8 carbon atoms include ethylbenzene and xylene (including all substituted isomers).
  • V (C9A) indicates the content of aromatic hydrocarbon compounds having 9 carbon atoms based on the total amount of the gasoline composition.
  • the value is preferably 0 to 5 volumes. %, More preferably 0 to 3% by volume.
  • the aromatic hydrocarbon having 9 carbon atoms include n-propylbenzene, isopropylbenzene (cumene), ethylmethylbenzene (including all substituted isomers), and trimethylbenzene (including all substituted isomers). And the like.
  • V (C10 + A) indicates the content of aromatic hydrocarbon compounds having 10 or more carbon atoms based on the total amount of the gasoline composition, and is preferably 0 to 10% in order to suppress the ozone generation ability of the exhaust gas. 3% by volume, more preferably 0 to 1% by volume, and most preferably 0% by volume.
  • aromatic hydrocarbon compound having 10 or more carbon atoms include dimethylethylbenzene (including all substituted isomers) and dimethylethylbenzene.
  • V (MA) and V (PA) are the monoalkyl-substituted aromatic hydrocarbon compound content (% by volume) based on the total gasoline composition and the aromatic substituted with two or more alkyl groups, respectively. Shows the hydrocarbon compound content (% by volume). If V (PA) is 0, or if V (PA) is not 0, the ratio of the former content to the latter content, the value of V (MA) / V (PA) is preferably 1 As mentioned above, it is more preferably maintained at 1.5 or more, and still more preferably at 2 or more.
  • V (Bz), V (Tol), V (C8A), V (C9A), V (C10 + A), V (MA) and V (PA) are all JISK 2536. It is a value obtained by quantification by the gas chromatograph method of “Petroleum product-hydrocarbon type test method”.
  • V (C4) indicates the content of a hydrocarbon compound having 4 carbon atoms based on the total amount of the gasoline composition.
  • the value of V (C4) is preferably 0 to 10% by volume, more preferably 0 to 5% by volume, and still more preferably 0 to 3% by volume, because the amount of evaporation can be kept lower.
  • Examples of the hydrocarbon compound having 4 carbon atoms include n-butane, 2-methylbutane (isobutane), 1-butene, 2-butene and 2-methylpropene.
  • V (C5) indicates the content of an aliphatic hydrocarbon compound having 5 carbon atoms based on the total amount of gasoline, and the lower limit is preferably 1% by volume, more preferably 15% by volume, and the upper limit. The value is preferably 35% by volume, more preferably 30% by volume.
  • the content of unsaturated hydrocarbon compounds (V (C5o)) (volume%) in aliphatic hydrocarbon compounds having 5 carbon atoms is 0%.
  • the value of V (C5o) is preferably 1 or more, more preferably 1.5 or more, even more preferably 2 or more, and most preferably 3 or more.
  • Examples of the hydrogenated saturated aliphatic carbon compound having 5 carbon atoms include n-pentane, 2-methylbutane (isopentane), and 2,2-dimethylpropane (neopentane).
  • unsaturated aliphatic hydrocarbons examples include 1-pentene, 2-pentene, 2-methyl-11-butene, 2-methyl-2-butene, and 3-methyl-1-butene.
  • the above V (C 6) indicates the content of the aliphatic hydrocarbon compound having 6 carbon atoms based on the total amount of the gasoline composition, and the lower limit thereof is preferably 10% by volume, more preferably 15% by volume. The upper limit is preferably 30% by volume, more preferably 25% by volume.
  • the content of the aliphatic hydrocarbon compound having 6 carbon atoms By setting the content of the aliphatic hydrocarbon compound having 6 carbon atoms to 10% by volume or more, a gasoline composition excellent in normal-temperature operability can be obtained. Further, by setting the content to 30% by volume or less, a gasoline composition excellent in high-temperature drivability can be obtained. From the viewpoint of preventing gasoline coking during injection, the content of saturated hydrocarbon compounds (V (C6o)) (volume%) in the aliphatic hydrocarbon compounds having 6 carbon atoms is 0.
  • V (C6p) volume% of the saturated hydrocarbon compound in the aliphatic hydrocarbon compound having 6 carbon atoms to V (C6 o), that is, V ( The value of C6p) / V (C6o) is preferably 2 or more, more preferably 3 or more, still more preferably 5 or more, and most preferably 10 or more.
  • the saturated aliphatic hydrocarbon compound having 6 carbon atoms include n-hexane, 2-methylpentane, 3-methylpentane, 2,2-dimethylbutane, and 2,3-dimethylbutane.
  • Examples of unsaturated aliphatic hydrocarbon compounds include 1 ⁇ xen, 2-hexene, 3-hexene, 2-methyl-1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2- Methyl-1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2,3-dimethyl-1-butene, 3,3-dimethyl-1-butene and 2,3-dimethyl-1-butene And the like.
  • the above V (C7 + p) indicates the content of the saturated aliphatic hydrocarbon compound having 7 or more carbon atoms based on the total amount of the gasoline composition, and the lower limit thereof is preferably 10% by volume, more preferably Is 20% by volume.
  • the upper limit is preferably 50% by volume, more preferably 45% by volume.
  • a gasoline composition excellent in normal-temperature operability can be obtained.
  • an excellent gasoline composition can be obtained.
  • a saturated aliphatic hydrocarbon compound having 7 or more carbon atoms for example, For example, n-heptane, 2-methylhexane, 3-methylhexane, 2,2-dimethylpentane, 2,3-dimethylpentane, 2,4-dimethylpentane, 3,3-dimethylpentane, 3-ethylpentane and 2, 2, 3-trimethylbutane and the like.
  • V (C9 +) indicates the content of hydrocarbon compounds having 9 or more carbon atoms based on the total amount of gasoline composition.In terms of low-temperature and normal-temperature operability, it also reduces gasoline dilution of engine oil and reduces emissions. This value is preferably 0 to 10% by volume, more preferably 0 to 5% by volume, and still more preferably 0% by volume, because it can prevent an increase in gas, deterioration of engine oil and generation of sludge. .
  • V (C4), V (C5), V (C5p), V (C5o), V (C6), V (C6p), V (C6o), V (C7 +) p) and V (C9 +) mean values determined by the gas chromatography method shown below.
  • a methyl silicon capillary column, a helium or nitrogen carrier gas, and a hydrogen ionization detector (FID) are used as the detector.
  • the column length is 25 to 50 m
  • the carrier gas flow is 0.5 to 1.
  • the content of the oxygen-containing compound in the gasoline composition is not particularly limited, but is preferably 0 to 2.7% by mass, more preferably 0 to 2.0% by mass in terms of oxygen element based on the total amount of the gasoline composition. %. If the content exceeds 2.7% by mass, the fuel efficiency of the gasoline composition may deteriorate and the NOx in the exhaust gas may increase.
  • the oxygen-containing compound means alcohols having 2 to 4 carbon atoms, ethers having 4 to 8 carbon atoms, and the like.
  • oxygen-containing compound examples include, for example, ethanol, methyl ethyl shale butyl ether (MTBE), ethyl ethyl shale butyl ether, and yuichi shale amyl methyl ether (TAME). And MT-1 and amyl ethyl ether. Among them, MTBE and TAME are preferable, and MTBE is most preferable. In addition, methanol Is preferable because it may increase the aldehyde concentration in the exhaust gas and is corrosive.
  • the sulfur content in the gasoline composition is not particularly limited, but is preferably 50 ppm or less, more preferably 50 ppm or less, based on the total amount of the gasoline composition. Is at most 3 Oppm, more preferably at most 2 Oppm, most preferably at most 1 Oppm. If the sulfur content exceeds 5 Oppm, the performance of the exhaust gas treatment catalyst will be adversely affected, and the concentration of NOx, C0, and HC in the exhaust gas may increase, and the amount of benzene emitted will also increase. there is a possibility.
  • the sulfur content means a sulfur content measured according to JISK 2541 "Test method for one sulfur content of crude oil and petroleum products".
  • the above gasoline composition generally has an unwashed real gum content of 2 OmgZl 0 OmL or less as measured by JISK 2261 “Petroleum products—Automobile gasoline and aviation fuel oil—Real gum test method-Injection evaporation method”.
  • the content of the washed real gum is generally 3 mg / l OmL or less, preferably 1 mg / 10 OmL or less. If the unwashed real gum and the washed real gum exceed the above values, there is a concern that deposits will be formed in the fuel introduction system and that the suction valve will stick.
  • the total calorific value of the above gasoline composition measured by JIS K 2279 "Crude oil and petroleum products-Estimation method by calorific value test method and calculation" is generally 40,000 J / g or more, preferably 45,000 J / g or more. .
  • (Induction period method)] is generally 480 minutes or more, preferably 1440 minutes or more. If the oxidative stability is less than 480 minutes, gums may form during storage.
  • the gasoline composition has a copper plate corrosion (50 ° C, 3h) of generally 1 and preferably 1a. If the copper plate corrosion exceeds 1, the fuel system conduit may corrode.
  • copper plate corrosion is measured in accordance with JISK 2513 “Petroleum products—Copper plate corrosion test method” (test temperature 50 ° C, test time 3 hours).
  • the gasoline composition desirably has a kerosene contamination amount of 4% by volume or less.
  • the amount of kerosene mixed refers to the carbon number of 13-14 based on the total amount of gasoline composition. Represents the hydrocarbon content (% by volume), which can be determined by gas chromatography as described below.
  • a methyl silicon capillary column is used for the column, helium or nitrogen is used for the carrier gas, and a hydrogen ionization detector (FID) is used for the detector. 5 to 1.5 mL / min, separation ratio 1:50 to 1: 250, inlet temperature 150 to 250 ° C, initial column temperature 1 to 10 to 10 ° C, final column Temperature measured at 150 to 250 ° C, detector temperature at 150 to 250 ° C.
  • FID hydrogen ionization detector
  • Pace gas oil can be manufactured by any method.
  • the gas oil base include, for example, straight-run gas oil obtained from an atmospheric distillation unit for crude oil; and vacuum gas oil obtained by subjecting a straight-run heavy oil or residual oil obtained from an atmospheric distillation unit to a vacuum distillation unit.
  • additives other than the additive of the present invention can be used in combination.
  • Examples of the light oil additives other than the additives of the present invention include a lubricity improver and a cetane improver.
  • lubricity improver for example, one or more of carboxylic acid type, ester type, alcohol type and phenol type lubricity improvers can be arbitrarily used. Among these, carboxylic acid-based and ester-based lubricity improvers are preferred.
  • carboxylic acid-based lubricity improvers include linoleic acid, oleic acid, salicylic acid, palmitic acid, myristic acid, hexadecenoic acid and the above carboxylic acids. Examples thereof include a mixture of two or more kinds.
  • ester-based lubricity improver examples include carboxylic acid esters of glycerin.
  • the carboxylic acid constituting the carboxylic acid ester may be one kind or two or more kinds. Specific examples thereof include linoleic acid, oleic acid, salicylic acid, palmitic acid, myristic acid, and hexadecenoic acid. Is mentioned.
  • the amount of the lubricity improver is preferably at least 35 ppm by mass, more preferably at least 50 ppm by mass, based on the total amount of the composition.
  • the upper limit of the amount of the compound is preferably 150 mass ppm or less, more preferably 100 mass ppm or less, since an effect commensurate with the addition amount cannot be obtained even if it is added more. .
  • a commercially available product called a lubricity improver is generally obtained in a state where an active ingredient contributing to lubricity improvement is diluted with an appropriate solvent.
  • the blending amount described above for the lubricity improver means the blending amount as an active ingredient.
  • Various compounds known in the art as sesin number improvers can be arbitrarily used as the selenium number improver.
  • nitrate esters and organic peroxides can be used.
  • Nitrate esters include, for example, 2-chloroethyl nitrate, 2-ethoxyxyl nitrate, isopropyl nitrate, butyl nitrate, 1st amylnyt, 2nd amylnyt, isoamylny Treat, first hexyl nitrate, second hexyl nitrate, n-heptyl nitrate, n-octyl nitrate, 2-ethylhexyl nitrate, cyclohexyl nitrate, ethylene glycol dinitrate, etc.
  • Various nitrates and the like are included.
  • alkyl nitrate having 6 to 8 carbon atoms is preferable.
  • Selenium number improver is a compound of one of the above compounds The compound may be used alone, or two or more compounds may be used in combination.
  • the content of the cetane number improver in the gas oil composition containing the additive of the present invention is based on the total amount of the composition in order to further reduce the NOx concentration, PM concentration, aldehyde concentration, etc. of the diesel engine exhaust gas. It is preferably at least 500 ppm by mass, more preferably at least 600 ppm by mass, even more preferably at least 700 ppm by mass, and even more preferably at least 800 ppm by mass. Even more preferably, it is most preferably at least 900 ppm by mass.
  • the upper limit of the content of the cetane number improver is not particularly limited, but the content of the cetane number improver is preferably 1400 mass ppm or less based on the total amount of the gas oil composition, and 1 2 It is more preferably at most 500 ppm by mass, more preferably at most 100 ppm by mass, and most preferably at most 100 ppm by mass.
  • selenium number improvers are obtained as active ingredients that contribute to the improvement of selenium number, that is, diluted with an appropriate solvent. It is customary.
  • the content of the cetane number improver indicates the content of the active ingredient in the gas oil composition.
  • Detergents other than the additives of the present invention include, for example, polyethers; polyalkylene oxides; imid compounds; polybutenyl succinates synthesized from polybutenyl succinic anhydrides and ethylene polyamines; Alkenyl succinic acid imid; succinic acid ester such as polybutenyl succinic acid ester synthesized from polyhydric alcohol such as pentaerythritol and polybutenyl succinic anhydride; dialkylaminoethyl methacrylate, polyethylene glycol methacrylate, Copolymer polymers such as a copolymer of vinylpyrrolidone and an alkyl methacrylate; and ashless detergents such as a reaction product of a carboxylic acid and an amine.
  • alkenyl succinimide examples include the use of an alkenyl succinate imid having a molecular weight of about 1,000 to 3,000 alone, and the use of an alkenyl succinic imid having a molecular weight of about 700 to 2,000 and an alkyne having a molecular weight of about 10,000 to 20,000. In some cases, kenyl succinimide is mixed and used.
  • the carboxylic acid constituting the reaction product of the carboxylic acid and the amine may be one kind or two or more kinds. Specific examples thereof include fatty acids having 12 to 24 carbon atoms and carbon numbers? To 24 aromatic carboxylic acids. Examples of the fatty acid having 12 to 24 carbon atoms include, but are not limited to, linoleic acid, oleic acid, palmitic acid, and myristic acid. Examples of the aromatic carboxylic acid having 7 to 24 carbon atoms include, but are not limited to, benzoic acid and salicylic acid.
  • the amine constituting the reaction product of the carboxylic acid and the amine may be one type or two or more types.
  • the amount of the detergent other than the additive of the present invention is not particularly limited. In order to bring out the effect of combining the detergent of the present invention with the additive of the present invention, specifically, the effect of suppressing the clogging of the fuel injection nozzle, the amount of the detergent other than the present invention is required. Is preferably at least 30 ppm by mass, more preferably at least 60 ppm by mass, even more preferably at least 80 ppm by mass, based on the total amount of the composition. Adding less than 30 parts per million by weight may have no effect.
  • the compounding amount of the detergent is 300 mass ppm or less, and more preferably 180 mass ppm or less.
  • additives examples include low-temperature fluidity improvers such as ethylene-vinyl acetate copolymer and alkenyl succinic amide; phenolic and amine-based antioxidants; metal deactivators such as salicylidene derivatives Antifreezing agents such as polyglycol ether; corrosion inhibitors such as aliphatic amines and alkenyl succinates; antistatic agents such as anionic, cationic and amphoteric surfactants; coloring agents such as azo dyes; Examples include silicone-based antifoaming agents.
  • low-temperature fluidity improvers such as ethylene-vinyl acetate copolymer and alkenyl succinic amide
  • phenolic and amine-based antioxidants metal deactivators such as salicylidene derivatives
  • Antifreezing agents such as polyglycol ether
  • corrosion inhibitors such as aliphatic amines and alkenyl succinates
  • antistatic agents such as anionic, cationic and amphoteric sur
  • the addition amount of the above-mentioned additives is not particularly limited and can be arbitrarily determined.
  • the addition amount of each additive is preferably 0.5% by mass or less, more preferably 0% by mass, based on the total amount of light oil and the composition. 2% by mass or less.
  • the properties and composition of the gas oil composition comprising the base gas oil, the additive of the present invention comprising a complex compound, and other gas oil additives are not particularly limited. However, it is desirable that the distillation properties satisfy the following properties.
  • the initial boiling point of the gas oil composition is preferably 135 ° C or higher, more preferably 140 ° C or higher, Even more preferred is 145 C or higher.
  • the initial boiling point is desirably 200 ° C or less.
  • T 10 of the gas oil composition is too low, the an increase in amount of hydrocarbons entrained when the same reason or Raa exhaust initial boiling point is too low there is a risk, I. Is preferably 155 ° C. or higher, more preferably 165 ° C. or higher. On the other hand, if this is too high, there is a concern that the low-temperature startability and low-temperature operability may cause problems.
  • ⁇ 0 is desirably 230 ° C or less.
  • the value of 30 is preferably 175 ° C or more, more preferably 180 ° C or more, and even more preferably 185 ° C or more.
  • the temperature be 260 ° C or less, since there is a possibility of causing problems in low-temperature startability and low-temperature operation.
  • the T 50 of the gas oil composition is preferably 19 CTC or more, more preferably 195 ° C. or more, and still more preferably 200 ° C. or more, from the viewpoint of fuel efficiency and engine output.
  • the T 50 is preferably 300 ° C. or less so as not to increase the concentration of particulate matter (PM) in the exhaust gas.
  • T7Q is preferably above 220 ° C, more preferably above 225 ° C, even more preferably above 230 ° C.
  • T 70 is desirably 330 ° C. or less in view of low-temperature drivability and not to increase the PM concentration in the exhaust gas.
  • T g of the gas oil composition Is preferably 250 ° C. or higher, more preferably 270 ° C. or higher, from the viewpoint of lubricity in the fuel injection pump. It is desirable that the temperature be 350 ° C or less from the viewpoint of low-temperature operation and not to increase the PM concentration in the exhaust gas.
  • T 95 of the gas oil composition is increased from the viewpoint of lubricity in fuel injection pump, preferably from the 270 ° C or more, the PM concentration from the viewpoint of low-temperature operability and exhaust gas In order to prevent the, T 95 is preferably at most 360 ° C.
  • the distillation end point of the gas oil composition is preferably 330 ° C. or more from the viewpoint of lubricity in the fuel injection pump. From the viewpoint of low-temperature operability and not to increase the PM concentration in the exhaust gas, the distillation end point is preferably 370 ° C or lower.
  • distillation characteristics initial boiling point, T 10, T 30, T 50, T 70, T go, ⁇ 95, distillation endpoint
  • all JISK 2254 - refers to a value measured by "Petroleum products distillation test method" I do.
  • the sulfur content of the gas oil composition is not particularly limited. However, the sulfur content is preferably 0.05% by mass or less from the viewpoint of the durability of the exhaust gas after-treatment device and the suppression of corrosion inside the engine.
  • the sulfur content means the sulfur content measured by J ISK 2541 “Sulfur content test method”.
  • the cetane index and cetane number of the gas oil composition are not particularly limited. However, in order to further reduce the concentrations of ⁇ , ⁇ , and aldehyde in the exhaust gas, the cetane index is preferably 45 or more, more preferably 48 or more, and even more preferably 50 or more. preferable.
  • the sunset value is preferably 45 or more, more preferably 48 or more, and even more preferably 50 or more.
  • the cetane index is calculated according to “8.4 Calculation method of cetane index using 4-variable equation” in JIS ⁇ 2280 “Test method for petroleum products, fuel oil, octane number and cetane number, and calculation method for cetane index”. Mean value.
  • the sunset value is defined in accordance with JIS ⁇ 2280 “Petroleum products—fuel oil—Octane number and sunset value test method and sunset index calculation method”, “7. Sunset value test method”. Means the cetane number measured.
  • the kinematic viscosity of the gas oil composition containing the additive of the present invention is not particularly limited. However, from the viewpoint of fuel injection timing control and lubrication of the distribution type fuel injection pump attached to the engine. Kinematic viscosity at 3 0 ° C is 1. Preferably 7 is mm 2 / sec or more, 1. 9 mm, more preferably 2 / sec or more, it 2. Is 0 mm 2 / sec or more Even more preferred.
  • the kinematic viscosity at 30 ° C should be 6.0 Omm 2 / sec or less in order not to increase the PM concentration in the exhaust gas and to reduce the effect on startability at low temperatures. Is preferably 5.0 mm 2 / sec or less, more preferably 4.5 mm 2 / sec or less.
  • the kinematic viscosity refers to the kinematic viscosity measured by JISK2283 “Crude oil and petroleum products—Kinematic viscosity test method and viscosity index calculation method”.
  • the density of the gas oil composition containing the additive of the present invention at 15 ° C. is not particularly limited. However, in order to further improve the fuel consumption rate and acceleration, the value is preferably 800 kgZm 3 or more. On the other hand, the density at 15 ° C is preferably 86 O kg / m 3 or less, and more preferably 85 O kg / m 3 or less, in order to further reduce the PM concentration in the exhaust gas. More preferred.
  • the density means the density measured by JISK2249 "Density test method for crude oil and petroleum products and density / mass / volume conversion table".
  • the content of each of the saturated component, the olefin component and the aromatic component is not particularly limited, but is desirably the following ratio.
  • Olefin content 0-5% by volume ⁇ Aromatic content 5-40% by volume
  • the content of the saturated component of the gas oil composition is preferably at least 60% by volume, more preferably at least 70% by volume, in order to reduce the concentrations of ⁇ 0X ⁇ and ⁇ in the exhaust gas. And still more preferably 75% by volume or more.
  • the saturated content is preferably 95% by volume or less, more preferably 90% by volume or less. Is less than 80% by volume.
  • the olefin content of the gas oil composition is preferably in the range of 0 to 5% by volume, more preferably 0 to 3% by volume, from the viewpoint of the stability of the composition. More preferably, it is in the range of 0 to 1% by volume.
  • the aromatic content of the gas oil composition is related to the fuel consumption rate and the engine output.
  • this aromatic content is preferably at least 5% by volume, more preferably at least 10% by volume, even more preferably at least 20% by volume, most preferably at least 25% by volume.
  • this aromatic content is preferably 40% by volume or less, more preferably 35% by volume or less. Is less than 30% by volume.
  • the saturated content, the olefin content, and the aromatic content are defined as the saturated content, the olefin content, and the aromatic content measured in accordance with the fluorescent indicator adsorption method of “Petroleum products-component test method” specified in JISK2536. It means the volume percentage of aromatics (% by volume).
  • the gas oil composition containing the additive of the present invention is not particularly limited with respect to its pour point (PP).
  • the PP of the composition is preferably 0 ° C or lower, more preferably 15 ° C or lower, still more preferably 110 ° C or lower.
  • PP means the pour point measured by JIS K 2269 "Pour point of crude oil and petroleum products and cloud point test of petroleum products".
  • the gas oil composition containing the additive of the present invention has no particular restriction on its clogging point (CFPP).
  • the CFPP of the yarn composition is preferably 0 ° C or less, more preferably 5 ° C or less, still more preferably 1 10 ° C or less, and 1-20 ° C. It is most preferred that: Where 0 1 3 A (113 K 2288? - means the filter plugging point, which is measured by the "light oil filter plugging point test method".
  • the light oil composition containing the additive of the present invention is not particularly limited with respect to its cloud point (CP).
  • the cloud point is preferably below 0 ° C.
  • the cloud point means a cloud point measured by JIS K 2269 "Pour point of crude oil and petroleum products and cloud point test method of petroleum products".
  • a base gasoline (gasoline for an internal combustion engine) having the following properties was prepared by mixing 60 parts by volume of catalytic reforming gasoline, 30 parts by volume of catalytic cracking gasoline, and 10 parts by volume of alkylate.
  • Example 1 The above gasoline and the test sample of the present invention (samples 1 to 22) were mixed (base gasoline 99.96% by mass / test sample 0.04% by mass). Composition) was prepared.
  • Active ingredient polybutenyl acetylene triamine (number average molecular weight about 3000)
  • the engine used for the evaluation was disassembled before each test, and after completely removing the deposits in the combustion chamber and the intake system, the new intake valves, exhaust valves, and spark plugs whose weights were measured were installed, assembled, and assembled. The test was performed after filling with new engine oil.
  • Olefin content 0.1% by volume
  • Aromatic content 26.4% by volume
  • the nozzle residual flow rate ratio indicates the ratio of the nozzle flow rate after the test to the flow rate of the new nozzle before the test.
  • the nozzle flow rate was measured at a needle valve lift of 0.1 mm. In this test, the larger the value of the nozzle residual flow rate ratio, the better the cleanliness.
  • the fuel oil additive containing the heterocyclic compound of the present invention has performance that surpasses conventional gasoline detergents, and is also excellent in the cleanliness of injection nozzles of diesel engines, and almost never becomes sludge itself. Ray.

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  • 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)

Abstract

Cette invention se rapporte à un additif pour carburant diesel, qui comprend un composé hétérocyclique à cinq ou six éléments spécifiques, qui possède des performances supérieures aux détergents à essence classiques, qui a une excellente action de nettoyage de la buse d'injection d'un moteur diesel et qui ne se transforme guère en suspension épaisse; ainsi qu'à une composition de carburant diesel contenant cet additif.
PCT/JP2001/004170 2000-05-19 2001-05-18 Additif pour carburant diesel et composition de carburant diesel WO2001088066A1 (fr)

Priority Applications (2)

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AU2001256775A AU2001256775A1 (en) 2000-05-19 2001-05-18 Fuel oil additive and fuel oil composition
JP2001585275A JP4537642B2 (ja) 2000-05-19 2001-05-18 燃料油添加剤及び燃料油組成物

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2182048A1 (fr) * 2008-10-31 2010-05-05 Denso Corporation Composition additive de carburant diesel et procédé de récurage l'utilisant
WO2013175711A1 (fr) * 2012-05-23 2013-11-28 株式会社大丸テクノ Agent de nettoyage
US8968426B2 (en) * 2007-01-15 2015-03-03 Technische Universiteit Eindhoven Liquid fuel composition and the use thereof
US20150101241A1 (en) * 2009-09-08 2015-04-16 Techniche Universiteit Eindhoven Liquid Fuel Composition and the Use Thereof

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US4397750A (en) * 1979-12-17 1983-08-09 Mobil Oil Corporation N-Hydroxyalkyl pyrrolidinone esters as detergent compositions and lubricants and fuel containing same
EP0349369A1 (fr) * 1988-06-29 1990-01-03 Institut Français du Pétrole Compositions obtenues à partir d'hydroxymidazolines et de polyamines et leur utilisation comme additif pour carburants
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EP0405270A1 (fr) * 1989-06-29 1991-01-02 Hoechst Aktiengesellschaft Procédé d'amélioration de la fluidité d'huiles minérales et de distillats d'huiles minérales
WO1991007578A1 (fr) * 1989-11-15 1991-05-30 Petro Chemical Products Inc. Composition servant a nettoyer un moteur a combustion interne
WO1994022984A1 (fr) * 1993-03-30 1994-10-13 Shell Internationale Research Maatschappij B.V. Compositions combustibles
JPH07224288A (ja) * 1994-02-09 1995-08-22 Cosmo Sogo Kenkyusho:Kk ディーゼルエンジン用燃料油組成物
EP0723985A1 (fr) * 1995-01-23 1996-07-31 Nippon Oil Co. Ltd. Additif pour combustible
WO1997036971A1 (fr) * 1996-03-29 1997-10-09 Exxon Research And Engineering Company Procede de reduction des depots presents dans une chambre de combustion et sur une soupape d'admission dans des moteurs a combustion interne a allumage par etincelle
EP0801128A1 (fr) * 1996-04-12 1997-10-15 Nippon Oil Co. Ltd. Additif pour combustible
EP0819753A1 (fr) * 1996-07-18 1998-01-21 Nippon Oil Co. Ltd. Additif pour combustible
JPH10279964A (ja) * 1997-04-04 1998-10-20 Sanyo Chem Ind Ltd 燃料油添加剤
WO1999013027A1 (fr) * 1997-09-11 1999-03-18 Nippon Mitsubishi Oil Corporation Additif pour mazout et composition a base de mazout contenant cet additif
WO2000020537A1 (fr) * 1998-10-06 2000-04-13 Nippon Mitsubishi Oil Corporation Additif pour essence destinee a un moteur a essence a injection directe
JP2000119668A (ja) * 1998-10-15 2000-04-25 Nippon Mitsubishi Oil Corp 軽油組成物

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Publication number Priority date Publication date Assignee Title
US4397750A (en) * 1979-12-17 1983-08-09 Mobil Oil Corporation N-Hydroxyalkyl pyrrolidinone esters as detergent compositions and lubricants and fuel containing same
JPS5880386A (ja) * 1981-11-06 1983-05-14 Nippon Cooper Kk 燃料油添加剤
EP0349369A1 (fr) * 1988-06-29 1990-01-03 Institut Français du Pétrole Compositions obtenues à partir d'hydroxymidazolines et de polyamines et leur utilisation comme additif pour carburants
EP0391735A1 (fr) * 1989-04-06 1990-10-10 Exxon Chemical Patents Inc. Compositions d'huiles combustibles
EP0405270A1 (fr) * 1989-06-29 1991-01-02 Hoechst Aktiengesellschaft Procédé d'amélioration de la fluidité d'huiles minérales et de distillats d'huiles minérales
WO1991007578A1 (fr) * 1989-11-15 1991-05-30 Petro Chemical Products Inc. Composition servant a nettoyer un moteur a combustion interne
WO1994022984A1 (fr) * 1993-03-30 1994-10-13 Shell Internationale Research Maatschappij B.V. Compositions combustibles
JPH07224288A (ja) * 1994-02-09 1995-08-22 Cosmo Sogo Kenkyusho:Kk ディーゼルエンジン用燃料油組成物
EP0723985A1 (fr) * 1995-01-23 1996-07-31 Nippon Oil Co. Ltd. Additif pour combustible
WO1997036971A1 (fr) * 1996-03-29 1997-10-09 Exxon Research And Engineering Company Procede de reduction des depots presents dans une chambre de combustion et sur une soupape d'admission dans des moteurs a combustion interne a allumage par etincelle
EP0801128A1 (fr) * 1996-04-12 1997-10-15 Nippon Oil Co. Ltd. Additif pour combustible
EP0819753A1 (fr) * 1996-07-18 1998-01-21 Nippon Oil Co. Ltd. Additif pour combustible
JPH10279964A (ja) * 1997-04-04 1998-10-20 Sanyo Chem Ind Ltd 燃料油添加剤
WO1999013027A1 (fr) * 1997-09-11 1999-03-18 Nippon Mitsubishi Oil Corporation Additif pour mazout et composition a base de mazout contenant cet additif
WO2000020537A1 (fr) * 1998-10-06 2000-04-13 Nippon Mitsubishi Oil Corporation Additif pour essence destinee a un moteur a essence a injection directe
JP2000119668A (ja) * 1998-10-15 2000-04-25 Nippon Mitsubishi Oil Corp 軽油組成物

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8968426B2 (en) * 2007-01-15 2015-03-03 Technische Universiteit Eindhoven Liquid fuel composition and the use thereof
EP2182048A1 (fr) * 2008-10-31 2010-05-05 Denso Corporation Composition additive de carburant diesel et procédé de récurage l'utilisant
JP2010106173A (ja) * 2008-10-31 2010-05-13 Denso Corp ディーゼル燃料添加剤組成物及びそれを用いた洗浄方法
US20150101241A1 (en) * 2009-09-08 2015-04-16 Techniche Universiteit Eindhoven Liquid Fuel Composition and the Use Thereof
US9476004B2 (en) * 2009-09-08 2016-10-25 Technische Universiteit Eindhoven Liquid fuel composition and the use thereof
WO2013175711A1 (fr) * 2012-05-23 2013-11-28 株式会社大丸テクノ Agent de nettoyage
JP2013245246A (ja) * 2012-05-23 2013-12-09 Daimaru Tekuno Co Ltd 洗浄剤

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