JP2000109861A - Additive to gasoline - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an additive to gasoline which is made to exhibit an excellent effect on the cleaning of a combustion chamber inside, especially of a cavity inside, by using a nitrogen-contg. compd. having a hydrocarbyl group. SOLUTION: An additive to a gasoline available in a cylinder direct injection- type gasoline engine uses a nitrogen-contg. compd. expressed by formula I. In formula I, R1 is H or a 1-30C hydrocarbyl group; R2, R3, R4 and R5 are each independently H, a 1-16C hydrocarbyl group, or a group expressed by formula II; (a) is 1-200; R6 is a 1-10C hydrocarbyl group; (b) is 0 or 1; Z is a group selected from group A; (c) is 0 or 1; X is a group selected from group B; (d) is 1-3; (e) is 0-2, and (d+e) is 3. The group A consists of O-CO, CO, or the like; the group B, H, a 1-30C hydrocarbyl group, an alkanol group, or the like. In formula II, R7 and R8 are each independently H, a 1-10C hydrocarbyl group, or a 2-10C alkoxyalkyl group; R9 is a 2-6C alkylene group; and R10 is H or a hydrocarbyl group.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a gasoline additive having excellent solubility in gasoline, and particularly excellent cleanliness in a combustion chamber of a direct injection gasoline engine.

[0002]

2. Description of the Related Art From the viewpoint of resource saving and suppression of global warming, it is required to reduce the use of fossil fuels worldwide, and improvement of fuel efficiency is the biggest issue for gasoline vehicles. On the other hand, in some urban areas, pollutants such as NOx do not meet environmental standards, and gasoline vehicles are required to further reduce pollutants. In order to simultaneously improve fuel efficiency and reduce environmental pollutants in exhaust gas in response to such demands, a direct injection gasoline engine is considered to be the most effective. A conventional gasoline engine forms a uniform premixed gasoline and air by injecting gasoline into an intake port. On the other hand, a direct injection gasoline engine injects gasoline directly into a combustion chamber like a diesel engine. This makes it possible to form a stratified mixture that is rich in the vicinity of the spark plug but is super-lean in the entire combustion chamber. By forming such a stratified air-fuel mixture, combustion in a super-lean state (stratified combustion) becomes possible, and it becomes possible to improve fuel efficiency to the level of a diesel engine. Further, since gasoline is directly injected into the combustion chamber, there is no delay in gasoline evaporation which occurs in a conventional engine, and a more accurate fuel injection amount control can be performed.

[0003]

However, in a direct injection type gasoline engine, gasoline is injected into the combustion chamber, so that a new problem different from the conventional gasoline engine may occur. One of them is deposits that accumulate in the combustion chamber, especially in the cavity. In stratified combustion characteristic of a direct injection gasoline engine, fuel is sprayed into a piston cavity while the piston is rising, and the rebounded fuel forms a rich mixture near the spark plug and burns. At this time, if deposits accumulate in the cavity of the piston, a part of the sprayed fuel is adsorbed on the deposits, and the fuel near the spark plug decreases or the arrival time is delayed, so that the air / fuel ratio is disturbed. As a result, the driving performance is affected, the exhaust gas deteriorates, and smoke is generated. SUMMARY OF THE INVENTION In view of such circumstances, an object of the present invention is to provide a gasoline additive made of a special nitrogen-containing compound having excellent cleanliness in a combustion chamber, particularly in a cavity, of a direct injection gasoline engine.

[0004]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, it has been found that a nitrogen-containing compound having a specific structure is produced in a combustion chamber of a direct injection gasoline engine, especially in a combustion chamber. It was found that the cleanliness in the cavity was excellent. That is, the gasoline additive according to the present invention comprises a nitrogen-containing compound represented by the following general formula (1).

Embedded image (In the general formula (1), R ¹ is hydrogen or carbon number 1 to
R ² , R ³ , R ⁴ and R ⁵ each independently represent hydrogen, a hydrocarbon group having 1 to 16 carbon atoms or a group represented by the following general formula (2); Is 1 to 200
R ⁶ represents a hydrocarbon group having 1 to 10 carbon atoms, b represents 0 or 1, Z represents a group selected from Group A, c represents 0 or 1, and X represents Represents a group selected from the following group B, d is an integer of 1 to 3, e is an integer of 0 to 2, and d + e = 3. )

Embedded image (In the general formula (2), R ⁷ and R ⁸ are each independently hydrogen, a hydrocarbon group having 1 to 10 carbon atoms or 2 to 2 carbon atoms.
10 represents an alkoxyalkyl group, and R ⁹ has 2 to 2 carbon atoms.
6 represents an alkylene group or a C 4-10 alkylene group having an alkoxyalkyl group as a substituent; R ¹⁰ represents hydrogen or a hydrocarbon group having 1-30 carbon atoms; Indicates an integer of 50. A group: A1: —O—CO— A2: —CO— A3: —O—CO—R ¹¹ — (R ¹¹ represents an alkylene group having 1 to 6 carbon atoms) A4: —O—CO—O—R ¹² - (R ¹² represents an alkylene group having 1 to 6 carbon atoms) A5: -CO-O-R 13 - (R 13 represents an alkylene group having 1 to 6 carbon atoms) B group B1: hydrogen B2: carbon A hydrocarbon group of Formulas 1 to 30 B3: an alkanol group represented by the following general formula (3) -R ¹⁴ -OH (3) (In the general formula (3), R ¹⁴ represents an alkylene group having 1 to 6 carbon atoms. B4: Nitrogen-containing group represented by the following general formula (4)

Embedded image (In the 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 hydrogen, a hydrocarbon group having 1 to 30 carbon atoms, or a group represented by the above general formula (3), and g represents an integer of 1 to 5.) B5: represented by the following general formula (5) Group

Embedded image (In the general formula (5), R ¹⁸ represents an alkylene group having 2 to 6 carbon atoms, and R ¹⁹ , R ²⁰ , R ²¹ and R ²² each independently represent hydrogen, a hydrocarbon group having 1 to 10 carbon atoms or a hydroxyl group. And Y represents a methylene group, a methylene group substituted with a hydrocarbon group having 1 to 10 carbon atoms or a hydroxyl group, an imino group, an imino group substituted with a hydrocarbon group having 1 to 10 carbon atoms or a hydroxyl group, or oxygen. , H is 1 when e = 1, 0 or 1 when e = 2 (however, when h = 0, N (nitrogen) in the general formula (5) is represented by the general formula (1 The gasoline additive of the present invention comprising the nitrogen-containing compound of the general formula (1) has the ability to keep the combustion chamber of a direct injection gasoline engine, especially the cavity, clean. Excellent, especially under severe conditions such as when the engine is cold Exhibits Oite excellent cleaning effect, yet itself is not able to sludge.

[0005]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the contents of the present invention will be described in more detail. General formula (1) representing the nitrogen-containing compound of the present invention
In the formula, R ¹ represents hydrogen or a hydrocarbon group having 1 to 30 carbon atoms, and R ¹ is hydrogen, or a linear or branched alkyl group having 1 to 24 carbon atoms,
To 24 linear or branched alkenyl groups, 5 carbon atoms
It is preferably any of a cycloalkyl group or an alkylcycloalkyl group having 13 to 13 carbon atoms, an aryl group or an alkylaryl group having 6 to 18 carbon atoms, and an arylalkyl group having 7 to 19 carbon atoms. Preferred alkyl groups as R ¹ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and s.
an ec-butyl group, a tert-butyl group, a linear or branched pentyl group, a linear or branched hexyl group, a linear or branched heptyl group, a linear or branched octyl group, a linear or branched nonyl group, Straight or branched decyl group, straight or branched undecyl group, straight or branched dodecyl group, straight or branched tridecyl group, straight or branched tetradecyl group,
Linear or branched pentadecyl, linear or branched hexadecyl, linear or branched heptadecyl, linear or branched octadecyl, linear or branched nonadecyl, linear or branched icosyl, linear Or a branched henicosyl group, a straight or branched docosyl group, a straight or branched tricosyl group, a straight or branched tetracosyl group, and the like. Alkenyl groups preferred as R ¹ include vinyl groups,
Propenyl, isopropenyl, straight or branched butenyl, butadienyl, straight or branched pentenyl, straight or branched hexenyl, straight or branched heptenyl, straight or branched octenyl, Straight or branched nonenyl group, straight or branched decenyl group, straight or branched undecenyl group, straight or branched dodecenyl group, straight or branched tridecenyl group, straight or branched tetradecenyl group, straight chain Or a branched or branched pentadecenyl group, a straight or branched hexadecenyl group, a straight or branched octadecenyl group such as a straight or branched heptadecenyl group, an oleyl group, a straight or branched nonadecenyl group, a straight or branched icosenyl group, Straight or branched henicocenyl group, straight or branched docosenyl group, straight or branched tricosenyl group, straight or branched Such as Rakoseniru group, and the like. Preferred cycloalkyl groups as R ¹ include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and the like, and similarly preferred alkylcycloalkyl groups include a methylcyclopentyl group, a dimethylcyclopentyl group (including all substituted isomers), Ethylcyclopentyl group (including all substituted isomers), straight-chain or branched propylcyclopentyl group (including all substituted isomers), ethylmethylcyclopentyl group (including all substituted isomers), trimethylcyclopentyl group (including all ), Diethylcyclopentyl group (including all substituted isomers), ethyldimethylcyclopentyl group (including all substituted isomers), linear or branched propylmethylcyclopentyl group (including all substituted isomers) ), Linear or Branched propylethylcyclopentyl (including all substituted isomers), di-linear or branched propylcyclopentyl (including all substituted isomers), linear or branched propylethylmethylcyclopentyl (including all substituted isomers) Isomer), methylcyclohexyl group (including all substituted isomers), dimethylcyclohexyl group (including all substituted isomers), ethylcyclohexyl group (including all substituted isomers), linear or branched propyl Cyclohexyl group (including all substituted isomers), ethylmethylcyclohexyl group (including all substituted isomers), trimethylcyclohexyl group (including all substituted isomers), diethylcyclohexyl group (including all substituted isomers) ), Ethyldimethylcyclohexyl group (including all substituted isomers) A straight or branched propylmethylcyclohexyl group (including all substituted isomers), a straight or branched propylethylcyclohexyl group (including all substituted isomers), a di-linear or branched propylcyclohexyl group (including all substituted isomers) Straight or branched propylethylmethylcyclohexyl group (including all substituted isomers), methylcycloheptyl group (including all substituted isomers), dimethylcycloheptyl group (including all substituted isomers) Ethylcycloheptyl group (including all substituted isomers), linear or branched propylcycloheptyl group (including all substituted isomers), ethylmethylcycloheptyl group (including all substituted isomers) Isomer), trimethylcycloheptyl group (including all substituted isomers), diethylcycloheptyl group All substituted isomers), ethyldimethylcycloheptyl group (including all substituted isomers), straight-chain or branched propylmethylcycloheptyl group (including all substituted isomers), straight-chain or branched propyl Ethylcycloheptyl group (including all substituted isomers), di-linear or branched propylcycloheptyl group (including all substituted isomers), linear or branched propylethylmethylcycloheptyl group (including all substituted isomers) Including isomers). Preferred aryl groups for R ¹ include a phenyl group and a naphthyl group, and similarly preferred alkylaryl groups include a tolyl group (including all substituted isomers) and a xylyl group (including all substituted isomers). , An ethylphenyl group (including all substituted isomers), a linear or branched propylphenyl group (including all substituted isomers), an ethylmethylphenyl group (including all substituted isomers), a trimethylphenyl group (including Linear or branched butylphenyl groups (including all substituted isomers), linear or branched propylmethylphenyl groups (including all substituted isomers),
Diethylphenyl group (including all substituted isomers), ethyldimethylphenyl group (including all substituted isomers), tetramethylphenyl group (including all substituted isomers), linear or branched pentylphenyl group (including Straight or branched hexylphenyl group (including all substituted isomers), straight or branched heptylphenyl group (including all substituted isomers), straight or branched An octylphenyl group (including all substituted isomers), a linear or branched nonylphenyl group (including all substituted isomers), a linear or branched decylphenyl group (including all substituted isomers), Chain or branched undecylphenyl group (including all substituted isomers), linear or branched dodecylphenyl group (including all substituted isomers)
And the like. The same preferred arylalkyl group includes a benzyl group, a methylbenzyl group (including all substituted isomers), a dimethylbenzyl group (including all substituted isomers), a phenethyl group, a methylphenethyl group (all Dimethylphenethyl group (including all substituted isomers), and the like. Among them, when R ¹ is hydrogen, and when it is a linear or branched alkyl group having 1 to 12 carbon atoms, it has 6 to 18 carbon atoms.
And more preferably an alkyl group or an alkylaryl group. In particular, hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group or 7 carbon atoms It is more preferably a straight-chain or branched alkylaryl group of from 15 to 15, and most preferably hydrogen.

In the general formula (1), R ² , R ³ , R ⁴ and R ⁵ each independently represent hydrogen, a hydrocarbon group having 1 to 16 carbon atoms or a group represented by the general formula (2). Here, the hydrocarbon group having 1 to 16 carbon atoms includes 1 to 16 carbon atoms.
A linear or branched alkyl group, a linear or branched alkenyl group having 2 to 16 carbon atoms, a cycloalkyl group or an alkylcycloalkyl group having 5 to 16 carbon atoms, An aryl group or an alkylaryl group,
An arylalkyl group having 7 to 16 carbon atoms is included. Preferred alkyl groups include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group,
Isobutyl group, sec-butyl group, tert-butyl group, linear or branched pentyl group, linear or branched hexyl group, linear or branched heptyl group, linear or branched octyl group, linear or branched Nonyl, straight or branched decyl, straight or branched undecyl, straight or branched dodecyl, straight or branched tridecyl, straight or branched tetradecyl, straight or branched pentadecyl A straight-chain or branched hexadecyl group, etc., and similarly preferred alkenyl groups include vinyl, propenyl, isopropenyl, straight-chain or branched butenyl, butadienyl, straight-chain or branched pentenyl, Chain or branched hexenyl, straight or branched heptenyl, straight or branched octenyl, straight or branched nonenyl, straight or branched decenyl Group, straight or branched undecenyl, straight or branched dodecenyl, straight or branched tridecenyl, straight or branched tetradecenyl,
A straight-chain or branched pentadecenyl group, a straight-chain or branched hexadecenyl group and the like can be mentioned. Similarly, preferred cycloalkyl groups include a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. Examples of the alkylcycloalkyl group include a methylcyclopentyl group (including all substituted isomers) and a dimethylcyclopentyl group (all ), Ethylcyclopentyl group (including all substituted isomers), linear or branched propylcyclopentyl group (including all substituted isomers), ethylmethylcyclopentyl group (including all substituted isomers) Including), trimethylcyclopentyl group (including all substituted isomers), diethylcyclopentyl group (including all substituted isomers), ethyldimethylcyclopentyl group (including all substituted isomers), linear or branched propylmethyl Cyclopentyl group (all substituted isomers Straight-chain or branched propylethylcyclopentyl group (including all substituted isomers), methylcyclohexyl group (including all substituted isomers), dimethylcyclohexyl group (including all substituted isomers), ethylcyclohexyl Group (including all substituted isomers), linear or branched propylcyclohexyl group (including all substituted isomers), ethylmethylcyclohexyl group (including all substituted isomers), trimethylcyclohexyl group (including all substituted isomers) Isomer), diethylcyclohexyl group (including all substituted isomers), ethyldimethylcyclohexyl group (including all substituted isomers), linear or branched propylmethylcyclohexyl group (including all substituted isomers) ), Methylcycloheptyl group (including all substituted isomers), Tylcycloheptyl group (including all substituted isomers), ethylcycloheptyl group (including all substituted isomers), linear or branched propylcycloheptyl group (including all substituted isomers), ethylmethylcyclo Examples include a heptyl group (including all substituted isomers) and a trimethylcycloheptyl group (including all substituted isomers). Preferred aryl groups include
A phenyl group, a naphthyl group and the like are mentioned, and preferred alkylaryl groups are a tolyl group (including all substituted isomers), a xylyl group (including all substituted isomers), and an ethylphenyl group (all substituted isomers). ), Linear or branched propylphenyl groups (including all substituted isomers), ethylmethylphenyl groups (including all substituted isomers), trimethylphenyl groups (including all substituted isomers), Chain or branched butylphenyl group (including all substituted isomers), linear or branched propylmethylphenyl group (including all substituted isomers), diethylphenyl group (including all substituted isomers), ethyl Dimethylphenyl group (including all substituted isomers),
Tetramethylphenyl group (including all substituted isomers)
And the like. Preferred arylalkyl groups include benzyl, methylbenzyl (including all substituted isomers), dimethylbenzyl (including all substituted isomers), phenethyl, and methylphenethyl (all substituted isomers). And a dimethylphenethyl group (including all substituted isomers). Among the above-mentioned hydrocarbon groups having 1 to 16 carbon atoms, those having 1 to 1 carbon atoms
A straight-chain or branched alkyl group having 8 carbon atoms is even more preferable, and a straight-chain or branched alkyl group having 1 to 3 carbon atoms is most preferable. However, when the polarity of the nitrogen-containing polar group is large, it is preferable that one to several hydrocarbon groups having 8 to 16 carbon atoms be contained in the whole molecule.

[0007] R ^2, R ^3, R ⁴ and R ⁵ in the general formula (1) may be a group represented by the general formula (2), in that the general formula (2), R ⁷ and R ⁸ individually represents hydrogen, 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 referred to herein includes a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkenyl group having 2 to 10 carbon atoms, Examples include cycloalkyl groups or alkylcycloalkyl groups having 5 to 10 carbon atoms, aryl groups or alkylaryl groups having 6 to 10 carbon atoms, and arylalkyl groups having 7 to 10 carbon atoms.
Preferred alkyl groups include a methyl group, an ethyl group and n
-Propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, straight or branched pentyl, straight or branched hexyl, straight or branched heptyl, straight A chain or branched octyl group,
A straight-chain or branched nonyl group, a straight-chain or branched decyl group, and the like, and similarly preferred alkenyl groups include a vinyl group, a propenyl group, an isopropenyl group, a straight-chain or branched butenyl group, a butadienyl group, and a straight-chain Or a branched pentenyl group, a straight or branched hexenyl group, a straight or branched heptenyl group, a straight or branched octenyl group, a straight or branched nonenyl group, a straight or branched decenyl group, and the like. Similarly, preferred cycloalkyl groups include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like. As the alkylcycloalkyl groups, a methylcyclopentyl group (including all substituted isomers) and a dimethylcyclopentyl group (all ), 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),
Diethylcyclopentyl group (including all substituted isomers), ethyldimethylcyclopentyl group (including all substituted isomers), linear or branched propylmethylcyclopentyl group (including all substituted isomers), linear or branched Branched propylethylcyclopentyl group (including all substituted isomers), methylcyclohexyl group (including all substituted isomers), dimethylcyclohexyl group (including all substituted isomers), ethylcyclohexyl group (including all substituted isomers) ), Linear or branched propylcyclohexyl group (including all substituted isomers), ethylmethylcyclohexyl group (including all substituted isomers), trimethylcyclohexyl group (including all substituted isomers), diethyl Cyclohexyl group (including all substituted isomers), Rucyclohexyl group (including all substituted isomers), linear or branched propylmethylcyclohexyl group (including all substituted isomers), methylcycloheptyl group (including all substituted isomers), dimethylcycloheptyl group (Including all substituted isomers),
Ethylcycloheptyl group (including all substituted isomers), linear or branched propylcycloheptyl group (including all substituted isomers), ethylmethylcycloheptyl group (including all substituted isomers), trimethylcyclo And a heptyl group (including all substituted isomers). Preferred aryl groups include a phenyl group,
Examples of a naphthyl group include a preferable alkylaryl group such as a tolyl group (including all substituted isomers),
Xylyl group (including all substituted isomers), ethylphenyl group (including all substituted isomers), linear or branched propylphenyl group (including all substituted isomers), ethylmethylphenyl group (including all substituted isomers) Including substituted isomers),
Trimethylphenyl group (including all substituted isomers),
Linear or branched butylphenyl groups (including all substituted isomers), linear or branched propylmethylphenyl groups (including all substituted isomers), diethylphenyl groups (including all substituted isomers), Examples include an ethyldimethylphenyl group (including all substituted isomers) and a tetramethylphenyl group (including all substituted isomers). Preferred arylalkyl groups include benzyl, methylbenzyl (including all substituted isomers), dimethylbenzyl (including all substituted isomers), phenethyl, and methylphenethyl (all substituted isomers). And a dimethylphenethyl group (including all substituted isomers). Examples of the above-mentioned alkoxyalkyl group having 2 to 10 carbon atoms include, for example, methoxymethyl group, ethoxymethyl group, n-propoxymethyl group, isopropoxymethyl group, n-butoxymethyl group, isobutoxymethyl group, sec- Butoxymethyl group, tert-butoxymethyl group, pentoxymethyl group (including all isomers), hexoxymethyl group (including all isomers), heptoxymethyl group (including all isomers), octoxymethyl group ( Nonyloxymethyl group (including all isomers), methoxyethyl group (including all isomers),
Ethoxyethyl group (including all isomers), propoxyethyl group (including all isomers), butoxyethyl group (including all isomers), pentoxyethyl group (including all isomers), hexoxyethyl Group (including all isomers), heptoxyethyl group (including all isomers), octoxyethyl group (including all isomers), methoxypropyl group (including all isomers),
Ethoxypropyl group (including all isomers), propoxypropyl group (including all isomers), butoxypropyl group (including all isomers), pentoxypropyl group (including all isomers), Soxypropyl group (including all isomers), heptoxypropyl group (including all isomers), methoxybutyl group (including all isomers), ethoxybutyl group (including all isomers), propoxy Butyl group (including all isomers),
Butoxybutyl group (including all isomers), pentoxybutyl group (including all isomers), hexoxybutyl group (including all isomers), methoxypentyl group (including all isomers), ethoxypentyl Group (including all isomers), propoxypentyl group (including all isomers), butoxypentyl group (including all isomers), pentoxypentyl group (including all isomers), methoxyhexyl group (Including all isomers),
Ethoxyhexyl group (including all isomers), propoxyhexyl group (including all isomers), butoxyhexyl group (including all isomers), methoxyheptyl group (including all isomers), ethoxyheptyl Group (including all isomers), propoxyheptyl group (including all isomers), methoxyoctyl group (including all isomers), ethoxyoctyl group (including all isomers), methoxynonyl group (including all isomers) And all isomers).

It is preferable that R ⁷ and R ⁸ in the general formula (2) be, or individually, hydrogen, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 6 carbon atoms, particularly hydrogen or carbon atom. It is even more preferable that the alkyl group has the number of 1 to 3. R ⁹ in the general formula (2)
Represents an alkylene group having 2 to 6 carbon atoms or a total of 4 to 1 carbon atoms having an alkoxyalkylene group as a substituent.
And 0 represents an alkylene group. Examples of the alkylene group having 2 to 6 carbon atoms include an ethylene group, a propylene group (1-methylethylene group, 2-methylethylene group), a trimethylene group, and a butylene group (1-ethylethylene group, 2-ethyl group). Ethylene 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-butylethylene group), 1-ethyl-1-methylethylene group, 1-ethyl-2-methylethylene group, 1,1,2-trimethylethylene group,
2,2-trimethylethylene group, 1-ethyltrimethylene group, 2-ethyltrimethylene group, 3-ethyltrimethylene group, 1,1-dimethyltrimethylene group, 1,2-dimethyltrimethylene group, 1,3 -Dimethyltrimethylene group, 2,3-dimethyltrimethylene group, 3,3-dimethyltrimethylene group, 1-methyltetramethylene group, 2-
Methyltetramethylene group, 3-methyltetramethylene group, 4-methyltetramethylene group, pentamethylene group,
Hexylene group (1-butylethylene group, 2-butylethylene group), 1-methyl-1-propylethylene group, 1-
Methyl-2-propylethylene group, 2-methyl-2-propylethylene group, 1,1-diethylethylene group, 1,
2-diethylethylene group, 2,2-diethylethylene group, 1-ethyl-1,2-dimethylethylene group, 1-ethyl-2,2-dimethylethylene group, 2-ethyl-1,
1-dimethylethylene group, 2-ethyl-1,2-dimethylethylene group, 1,1,2,2-tetramethylethylene group, 1-propyltrimethylene group, 2-propyltrimethylene group, 3-propyltrimethylene Group, 1-ethyl-
1-methyltrimethylene group, 1-ethyl-2-methyltrimethylene group, 1-ethyl-3-methyltrimethylene group, 2-ethyl-1-methyltrimethylene group, 2-ethyl-2-methyltrimethylene group 2-ethyl-3-methyltrimethylene group, 3-ethyl-1-methyltrimethylene group, 3-ethyl-2-methyltrimethylene group, 3-ethyl-3-methyltrimethylene group, 1,1,2 -Trimethyl trimethylene group, 1,1,3-trimethyl trimethylene group, 1,2,2-trimethyl trimethylene group, 1,
2,3-trimethyl trimethylene group, 1,3,3-trimethyl trimethylene group, 2,2,3-trimethyl trimethylene group, 2,3,3-trimethyl trimethylene group,
1-ethyltetramethylene group, 2-ethyltetramethylene group, 3-ethyltetramethylene group, 4-ethyltetramethylene group, 1,1-dimethyltetramethylene group, 1,
2-dimethyltetramethylene group, 1,3-dimethyltetramethylene group, 1,4-dimethyltetramethylene group,
2,2-dimethyltetramethylene group, 2,3-dimethyltetramethylene group, 2,4-dimethyltetramethylene group, 3,3-dimethyltetramethylene group, 3,4-dimethyltetramethylene group, 4,4-dimethyl Examples thereof include a tetramethylene group, a 1-methylpentamethylene group, a 2-methylpentamethylene group, a 3-methylpentamethylene group, a 4-methylpentamethylene group, a 5-methylpentamethylene group, and a hexamethylene group. Examples of the alkylene group having a total number of carbon atoms of 4 to 10 containing the alkoxyalkylene group for R ⁹ as a substituent include, for example, 1-
(Methoxymethyl) ethylene group, 2- (methoxymethyl) ethylene group, 1- (methoxyethyl) ethylene group,
2- (methoxyethyl) ethylene group, 1- (ethoxymethyl) ethylene group, 2- (ethoxymethyl) ethylene group, 1-methoxymethyl-2-methylethylene group, 1,
1-bis (methoxymethyl) ethylene group, 2,2-bis (methoxymethyl) ethylene group, 1,2-bis (methoxymethyl) ethylene group, 1,1-bis (methoxyethyl) ethylene group, 2,2- Bis (methoxyethyl) ethylene group, 1,2-bis (methoxyethyl) ethylene group,
1,1-bis (ethoxymethyl) ethylene group, 2,2-
Bis (ethoxymethyl) ethylene group, 1,2-bis (ethoxymethyl) ethylene group, 1-methyl-2-methoxymethylethylene group, 1-methoxymethyl-2-methylethylene group, 1-ethyl-2-methoxymethyl Ethylene group, 1-methoxymethyl-2-ethylethylene group, 1-
Methyl-2-ethoxymethylethylene group, 1-ethoxymethyl-2-methylethylene group, 1-ethyl-2-ethoxymethylethylene group, 1-ethoxymethyl-2-ethylethylene group, 1-methyl-2-methoxyethyl Ethylene group, 1-methoxyethyl-2-methylethylene group, 1
A preferred example is an alkoxyalkylene group-substituted ethylene group having 2 to 8 carbon atoms, such as an -ethyl-2-methoxyethylethylene group and a 1-methoxyethyl-2-ethylethylene group. R ⁹ in the general formula (2) is particularly preferably an alkylene group having 2 to 4 carbon atoms or an ethylene group substituted with an alkoxyalkylene group having 2 to 6 carbon atoms in total.

In the general formula (2), R ¹⁰ represents hydrogen or a hydrocarbon group having 1 to 30 carbon atoms, and R ¹⁰ is hydrogen, or ¹ to 24 carbon atoms described above for R 1.
A linear or branched alkyl group, a linear or branched alkenyl group having 2 to 24 carbon atoms, a cycloalkyl group or an alkylcycloalkyl group having 5 to 13 carbon atoms, An aryl group or an alkylaryl group,
It is preferably any of arylalkyl groups having 7 to 19 carbon atoms. Further, R ¹⁰ is more preferably an alkyl group having 1 to 24 carbon atoms, and
Particularly preferred is an alkyl group of General formula (2)
F may be any integer in the range of 0 to 50, but is preferably 0 to 30, more preferably 0 to 30.
It is an integer of 20.

Accordingly, the group represented by the general formula (2)
⁷And R⁸Are each independently hydrogen, an alkyl having 1 to 6 carbon atoms
A kill group or an alkoxyalkyl group having 2 to 6 carbon atoms.
R⁹Is an alkylene group having 2 to 6 carbon atoms or the total number of carbon atoms
2 to 8 alkoxyalkylene-substituted ethylene groups
R^TenIs an alkyl group having 1 to 24 carbon atoms, and f
Is preferably an integer of 0 to 30. Hereafter
Such a group (referring to a group represented by the general formula (2)) is, for convenience,
It is referred to as “preferred substituent group (2a)”. And R ⁷and
R⁸Are each independently hydrogen or an alkyl having 1 to 3 carbon atoms.
R⁹Is an alkylene group having 2 to 4 carbon atoms
R^TenIs an alkyl group having 1 to 12 carbon atoms, and f
Is more preferably an integer of 0 to 20. Less than
Below, such a group (refers to a group represented by the general formula (2))
Is referred to as “more preferred substituent group (2b)” for convenience.
The nitrogen-containing compound of the present invention is a compound represented by the general formula (1)^Two,
R^Three, R^FourAnd R^FiveIs hydrogen or an alkyl having 1-8 carbon atoms
A alkyl group or the above-mentioned “preferred substituent group (2a)”
Preferably. Further, R^Two, R^Three, R^FourAnd R
^FiveIs hydrogen or an alkyl group having 1 to 3 carbon atoms or the above
It is more preferable that the “substituent group (2b)” is
preferable. Also, R^Two, R^Three, R^FourAnd R^FiveFew of
At least one is a group represented by the general formula (2)
Preferably, R^Two, R^Three, R^FourAnd R^FiveOne of the general formulas
Group represented by (2), and the other three are individually
It may be hydrogen or a hydrocarbon group having 1 to 16 carbon atoms.
Is more preferable.

R ⁶ in the general formula (1) has 1 to 1 carbon atoms.
Shows 10 hydrocarbon groups, and as the hydrocarbon groups,
As for R ⁷ and R ⁸ , a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a straight-chain or branched alkenyl group having 2 to 10 carbon atoms, and a C ⁵ to 10 carbon atom described above. A cycloalkyl group or an alkylcycloalkyl group, an aryl group or an alkylaryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 10 carbon atoms, and the like are included. R ⁶ is preferably an alkylene group having 1 to 6 carbon atoms, more preferably an alkylene group having 3 to 6 carbon atoms, and specifically, trimethylene group, 1-methyltrimethylene group, 2-methyltrimethylene group. Methylene group, 3-methyltrimethylene group, tetramethylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 3-methyltetramethylene group, 4-methyltetramethylene group, pentamethylene group, 1-methylpentane Methylene, 2-methylpentamethylene, 3-methylpentamethylene, 4-methylpentamethylene, 5-methylpentamethylene, hexamethylene and the like are preferred.

Z in the general formula (1) represents a group selected from the following group A. Group A A1: —O—CO— A2: —CO— A3: —O—CO—R ¹¹ — (R ¹¹ represents an alkylene group having 1 to 6 carbon atoms) A4: —O—CO—O—R ¹² - (R ¹² represents an alkylene group having 1 to 6 carbon atoms) A5: -CO-O-R 13 - (R 13 represents an alkylene group having 1 to 6 carbon atoms) of the group a R ^11, R ¹² , R ¹³ is an alkylene group having 1 to 6 carbon atoms, examples of the alkylene group include a methylene group, an ethylene group, a propylene group (1-methylethylene group, 2-methylethylene group), trimethylene group, butylene Groups (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- Chiruechiren group, 2-butyl ethylene group), 1-ethyl-1-methylethylene group, 1-ethyl-2-methylethylene group, 1,1,2
Trimethylethylene group, 1,2,2-trimethylethylene group, 1-ethyltrimethylene group, 2-ethyltrimethylene group, 3-ethyltrimethylene group, 1,1-dimethyltrimethylene group, 1,2-dimethyltrimethylene group Methylene group,
1,3-dimethyltrimethylene group, 2,3-dimethyltrimethylene group, 3,3-dimethyltrimethylene group, 1-
Methyltetramethylene group, 2-methyltetramethylene group, 3-methyltetramethylene group, 4-methyltetramethylene group, pentamethylene group, hexylene group (1-butylethylene group, 2-butylethylene group), 1-methyl-
1-propylethylene group, 1-methyl-2-propylethylene group, 2-methyl-2-propylethylene group, 1,
1-diethylethylene group, 1,2-diethylethylene group, 2,2-diethylethylene group, 1-ethyl-1,2
-Dimethylethylene group, 1-ethyl-2,2-dimethylethylene group, 2-ethyl-1,1-dimethylethylene group, 2-ethyl-1,2-dimethylethylene group, 1,
1,2,2-tetramethylethylene group, 1-propyltrimethylene group, 2-propyltrimethylene group, 3-propyltrimethylene group, 1-ethyl-1-methyltrimethylene group, 1-ethyl-2-methyl Trimethylene group, 1-
Ethyl-3-methyltrimethylene group, 2-ethyl-1-
Methyltrimethylene group, 2-ethyl-2-methyltrimethylene group, 2-ethyl-3-methyltrimethylene group, 3
-Ethyl-1-methyltrimethylene group, 3-ethyl-2
-Methyltrimethylene group, 3-ethyl-3-methyltrimethylene group, 1,1,2-trimethyltrimethylene group,
1,1,3-trimethyltrimethylene group, 1,2,2-
Trimethyl trimethylene group, 1,2,3-trimethyl trimethylene group, 1,3,3-trimethyl trimethylene group, 2,2,3-trimethyl trimethylene group, 2,3
3-trimethyltrimethylene group, 1-ethyltetramethylene group, 2-ethyltetramethylene group, 3-ethyltetramethylene group, 4-ethyltetramethylene group, 1,1-
Dimethyltetramethylene group, 1,2-dimethyltetramethylene group, 1,3-dimethyltetramethylene group, 1,4
-Dimethyltetramethylene group, 2,2-dimethyltetramethylene group, 2,3-dimethyltetramethylene group, 2,
4-dimethyltetramethylene group, 3,3-dimethyltetramethylene group, 3,4-dimethyltetramethylene group,
4,4-dimethyltetramethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 4-methylpentamethylene group, 5-
Examples thereof include a methylpentamethylene group and a hexamethylene group. Among them, R ¹¹ , R ¹² and R ¹³ are preferably an alkylene group having 1 to 4 carbon atoms, and specifically, a methylene group, an ethylene group and a 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 and the like. Further, as R ¹¹ , R ¹² and R ¹³ , an alkylene group having 1 to 3 carbon atoms, specifically, a methylene group, an ethylene group, a propylene group (1-methylethylene group, 2-methylethylene group) or a trimethylene group Most preferred. Z in the general formula (1) is A
It is preferably 1, A2 or A4.

The general formula (1) representing the nitrogen-containing compound of the present invention
In the above, a is an integer of 1 to 200, preferably 2 to 100. In the general formula (1), b and c are each independently 0 or 1. That is, b is 0, c
Is 0, represents a compound represented by the following general formula (6), b is 0, and c is 1 represents a compound represented by the following general formula (7), b is 1, and c is 0 Is a compound represented by the following general formula (8), and when b is 1 and c is 1, a compound represented by the following general formula (9) is represented.

Embedded image (R ¹ in the general formula ^{(6), R 2, R} 3, R 4, R 5 and X, R ¹ in the general formula ^{(1), R 2, R} 3, R 4, R
^It represents the same groups as ⁵ and X, and a, d and e are also the same integers as a, d and e in the general formula (1). (R ¹ , R ² , R ³ , R ⁴ , R ⁵ and X, Z in the general formula (7) are the same as R ¹ , R ² , R ³ ,
R ⁴ , R ⁵ and the same groups as X and Z are shown, and a, d and e are also the same integers as a, d and e in the general formula (1). (R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ in the general formula (8)
And X represent R ¹ , R ² , R ³ ,
The same groups as R ⁴ , R ⁵ , R ⁶ and X are shown, and a, d and e are also the same integers as a, d and e in the general formula (1). (R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ in the general formula (9)
And X and Z represent R ¹ , R ² ,
R ³ , R ⁴ , R ⁵ , R ⁶ and the same groups as X and Z
a, d and e are also a, d and e in the general formula (1).
Is the same integer as. As described above, c in the general formula (1) may be either 0 or 1, but it is preferable that c = 0. D in the general formula (1) is 1 to 3, preferably 1 to
2, e is an integer of 0-2, preferably 1-2, and d + e is 3, most preferably d = 1 and e = 2
It is. In addition, in the nitrogen-containing compound represented by the general formula (1), when d is 2, the compound has two groups represented by the following general formula (10) in one molecule.
These groups may have the same structure or different structures.

Embedded image (R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
R ⁶ and Z represent R ¹ , R ² , R ³ ,
It represents the same group as R ⁴ , R ⁵ , R ⁶ and Z, and a, b and c are also the same integers as a, b and c in formula (1). )

The general formula (1) representing the nitrogen-containing compound of the present invention
In the above, X represents a group selected from the following group B. Group B B1: Hydrogen B2: Hydrocarbon group having 1 to 30 carbon atoms B3: Alkanol group represented by the following general formula (3) —R ¹⁴ —OH (3) (In the general formula (3), R ¹⁴ is carbon B4: a nitrogen-containing group represented by the following general formula (4)

Embedded image (In the 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 hydrogen, a hydrocarbon group having 1 to 30 carbon atoms, or a group represented by the above general formula (3), and g represents an integer of 1 to 5.) B5: represented by the following general formula (5) Group

Embedded image (In the general formula (5), R ¹⁸ represents an alkylene group having 2 to 6 carbon atoms, and R ¹⁹ , R ²⁰ , R ²¹ and R ²² each independently represent hydrogen, a hydrocarbon group having 1 to 10 carbon atoms or a hydroxyl group. And Y represents a methylene group, a methylene group substituted with a hydrocarbon group having 1 to 10 carbon atoms or a hydroxyl group, an imino group, an imino group substituted with a hydrocarbon group having 1 to 10 carbon atoms or a hydroxyl group, or oxygen. , H is 1 when e = 1, 0 or 1 when e = 2 (however, when h = 0, N (nitrogen) in the general formula (5) is represented by the general formula (1 (Corresponds to N (nitrogen) in))

Preferred examples of the above-mentioned B2 hydrocarbon group having 1 to 30 carbon atoms include a linear or branched alkyl group having 1 to 24 carbon atoms and a C2 to C24 alkyl group as described above for R ^1. Linear or branched alkenyl group, C5-C13 cycloalkyl group or alkylcycloalkyl group, C6-C18 aryl group or alkylaryl group, C7-C19 arylalkyl group, etc. Is included. B2 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,
Particularly, a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group or an arylalkyl group having 7 to 9 carbon atoms is most preferable.

In the general formula (3) representing the alkanol group of B3, R ¹⁴ represents an alkylene group having 1 to 6 carbon atoms. Examples of such an alkylene group include R ¹¹ , R ¹² , R ¹³ includes the groups described above.
Among them, 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, and butylene. Groups (1-ethylethylene group, 2-ethylethylene group), 1,2-dimethylethylene group, 2,2-dimethylethylene group, 1-methyltrimethylene group, 2-methyltrimethylene group, 3-
A methyl trimethylene group, a tetramethylene group and the like are preferable. Further, as R ¹⁴ , an alkylene group having 1 to 3 carbon atoms, specifically, a methylene group, an ethylene group, a propylene group (1-methylethylene group, 2-methylethylene group) or a trimethylene group is most preferred.

In the general formula (4) representing the nitrogen-containing group represented by B4, R ¹⁵ represents an alkylene group having 2 to 6 carbon atoms. Examples of such an alkylene group include R ⁹
And the groups described above. Among these, R
¹⁵ is preferably an alkylene group having 2 to 4 carbon atoms,
Specifically, 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 A methylene group, a tetramethylene group and the like are preferable, and an alkylene group having 2 to 3 carbon atoms, specifically, an ethylene group, a propylene group (1-methylethylene group, a 2-methylethylene group), and a trimethylene group are more preferable.

R ¹⁶ in the general formula (4) represents hydrogen, an alkyl group having 1 to 4 carbon atoms or a group represented by the above general formula (3). As the alkyl group having 1 to 4 carbon atoms, specifically, for example, a methyl group, an ethyl group, an n-propyl group,
Isopropyl group, n-butyl group, isobutyl group, sec
-Butyl group, tert-butyl group and the like,
Preferably, an alkyl group having 1 to 3 carbon atoms is mentioned, and a methyl group or an ethyl group is more preferable. R ¹⁷ in the general formula (4) represents hydrogen, a hydrocarbon group having 1 to 30 carbon atoms, or a group represented by the general formula (3). Preferred as the hydrocarbon group having 1 to 30 carbon atoms here are those having 1 to 2 carbon atoms described above for R ^1.
4 linear or branched alkyl groups having 2 to 24 carbon atoms
A straight-chain or branched alkenyl group having 5 to 13 carbon atoms
A cycloalkyl group or an alkylcycloalkyl group,
An aryl group or an alkylaryl group having 6 to 18 carbon atoms, an arylalkyl group having 7 to 19 carbon atoms, and the like are included. R ¹⁷ is more preferably hydrogen, 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). In particular, hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group, an arylalkyl group having 7 to 9 carbon atoms, or a group represented by the general formula (3) is most preferable. G in the general formula (4) is 1
To 5, preferably 1 to 4, more preferably 1 to 3. The group represented by the following general formula (11), which is included in the group represented by the general formula (4), has 1 to 5 structural units represented by the following general formula (12), Preferably, it has 1 to 4, more preferably 1 to 3.

Embedded image (Formula (11) and R ¹⁵ in (12), R ¹⁶ and g illustrate the general formula in (4) R ^15, R ¹⁶ and g the same group, the integers.) Thus, the general formula (11) The group represented by the general formula (1)
The structural unit represented by 2) represents a group obtained by bonding as described below. One in which one kind of structural unit represented by the general formula (12) is bonded Two or more different structural units included in the general formula (12) are randomly bonded, alternately bonded, or the nitrogen-containing group represented by the general formula (4) which are classified in B4 that is blocked binding, R ¹⁵ is an alkylene group having 2 to 4 carbon atoms, R ¹⁶
Is hydrogen, an alkyl group having 1 to 3 carbon atoms or a general formula (3)
Wherein R ¹⁷ is hydrogen, a linear or branched alkyl group having 1 to 12 carbon atoms, an aryl group or an alkylaryl group having 6 to 12 carbon atoms, or a general formula (3). R ¹⁵ is an ethylene group, a propylene group (1-methyl ethylene group, 2-methyl ethylene group) or a trimethylene group, and R ¹⁶ is hydrogen, methyl R ¹⁷ is hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group, or an alkylaryl having 7 to 9 carbon atoms. Most preferably, it is a group or a group represented by the general formula (3), and g is 1 to 3.

In the general formula (5) corresponding to the above B5,
In the group¹⁸Represents an alkylene group having 2 to 6 carbon atoms
are doing. As the alkylene group here, specifically,
Is R ^FifteenAnd the same groups as those described above.
Among these, R¹⁸As an alkylene having 2 to 4 carbon atoms
Preferred are ethylene groups, specifically, ethylene groups, propylene
Groups (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-methyltrimethyl
Len, 2-methyltrimethylene, 3-methyltrimethyl
Tylene group, tetramethylene group and the like are preferable, and carbon number 2
To 3 alkylene groups, specifically, an ethylene group,
Len group (1-methylethylene group, 2-methylethylene
Groups) or trimethylene groups are more preferred. General formula
R in (5)¹⁹, R²⁰, R^{twenty one}And R^{twenty two}Each
Individually hydrogen, a hydrocarbon group having 1 to 10 carbon atoms or hydroxyl
Group. The hydrocarbon having 1 to 10 carbon atoms referred to here
As a group, R⁷And R⁸The carbon number explained earlier for
1-10 linear or branched alkyl groups, 2 carbon atoms
Linear or branched alkenyl group of 10 to 10, carbon number 5
10 to 10 cycloalkyl groups or alkylcycloalkyl
Group, aryl group having 6 to 10 carbon atoms or alkyl ant
And arylalkyl groups having 7 to 10 carbon atoms.
I can do it. Among these, R¹⁹, R²⁰, R^{twenty one}And R
^{twenty two}Are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms.
Or a group represented by a hydroxyl group.
Each independently hydrogen, an alkyl group having 1 to 3 carbon atoms or a hydroxyl group
Is more preferable. Y in general formula (5)
Is a methylene group, a hydrocarbon group having 1 to 10 carbon atoms or
Methylene group substituted with a group represented by a hydroxyl group, imino
Group, substituted with a hydrocarbon group having 1 to 10 carbon atoms or a hydroxyl group
Represents an imino group or oxygen. Charcoal here
As the hydrocarbon group having a prime number of 1 to 10, R⁷And R⁸Nitsu
And linear or branched having 1 to 10 carbon atoms as described above.
An alkyl group having 2 to 10 carbon atoms, which is linear or branched
Alkenyl group, cycloalkyl group having 5 to 10 carbon atoms or
Is an alkylcycloalkyl group, an aryl having 6 to 10 carbon atoms
Group or alkylaryl group, ant having 7 to 10 carbon atoms
Alkyl group and the like.
Alkyl groups having 1 to 6 carbon atoms are preferred, and alkyl groups having 1 to 3 carbon atoms are preferred.
Alkyl groups are more preferred. Among these, as Y
Methylene group, alkyl group having 1 to 6 carbon atoms or hydroxyl group
Methylene group, imino group,
Imino group or acid substituted by alkyl group or hydroxyl group
And an imino group, an alkyl group having 1 to 3 carbon atoms.
Imino group or acid substituted by alkyl group or hydroxyl group
Is most preferred.

H in the group represented by the general formula (5) is
When e = 1 in the general formula (1), h = 1, and when e = 2 in the general formula (1), h = 0 or h = 1.
It is. However, when e = 2 and h = 0, N (nitrogen) in the general formula (5) is also N (nitrogen) in the general formula (1). That is, when e = 2 and h = 0, as represented by the general formula (13), N
(Nitrogen) is a member constituting the heterocyclic ring represented by the general formula (5).

Embedded image (R ¹ , R ² , R ³ , R ⁴ , R ⁵ in the general formula (13)
R ⁶ and Z represent R ¹ , R ² , R ³ ,
R ⁴ , R ⁵ , R ⁶ and Z represent the same groups, a, b and c are the same integers as a, b and c in the general formula (1), and R ¹⁹ , R ²⁰ , R ²¹ , R ²² and Y represents ^{R 19, R 20, R 21} , R 22 and Y the same group in the general formula (5). As the group represented by the general formula (5) classified into B5,
R ¹⁸ is an alkylene group having 2 to 4 carbon atoms, R ^19,
R ²⁰ , R ²¹ and R ²² each independently represent hydrogen, carbon number 1
And m is an alkylene group or a hydroxyl group, wherein Y is a methylene group, a methylene group substituted with an alkyl group or a hydroxyl group having 1 to 6 carbon atoms, an imino group, an imino group substituted with an alkyl group or a hydroxyl group having 1 to 6 carbon atoms. A group or oxygen, h is h = 1 when e = 1, h = 0 or h = 1 when e = 2 (however, when h = 0, N in the general formula (5) Nitrogen) is more preferably N (nitrogen) in the general formula (1), and R ¹⁸ is an ethylene group, a propylene group (1-methylethylene group, a 2-methylethylene group) or a trimethylene group. , R ¹⁹ ,
R ²⁰ , R ²¹ and R ²² each independently represent hydrogen, carbon number 1
And Y is an imino group,
An imino group or an oxygen substituted with an alkyl group or a hydroxyl group having 1 to 3 carbon atoms, and when h is e = 1, h = 1
And when e = 2, h = 0 or h = 1 (where h
In the case where = 0, N (nitrogen) in the general formula (5) is also N (nitrogen) in the general formula (1). In the general formula (1) representing the nitrogen-containing compound of the present invention, X can be arbitrarily selected from the above B1 to B5. When e = 2, that is, when two Xs are selected, the two may be the same or different. X is preferably B1, B3, B4 or B5.

The substituents of the general formula (1) which generally represent the nitrogen-containing compound of the present invention have been individually described above. The nitrogen-containing compound of the present invention is preferably represented by the general formula (1) Is hydrogen or a linear or branched alkyl group having 1 to 12 carbon atoms, or has 6 to ¹ carbon atoms.
8 is an aryl group or an alkylaryl group,
² , R ³ , R ⁴ and R ⁵ are hydrogen or an alkyl group having 1 to 8 carbon atoms or a group represented by the general formula (2), and in the general formula (2), R ⁷ and R ⁸ are each independently Is hydrogen, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 6 carbon atoms, and R ⁹ is an alkylene group having 1 to 6 carbon atoms or an alkoxyalkylene group substituted with an alkoxyalkylene group having 2 to 8 carbon atoms. There is R ¹⁰ is an alkyl group having 1 to 24 carbon atoms, and f is an integer of 0 to 30, R ⁶ is C 1 -C
And R ¹¹ , R ¹² and R ¹³ are an alkylene group having 1 to 4 carbon atoms, a is an integer of 1 to 200, and b and c are each independently 0 or 1. , D is 1
E is an integer of 1-2, and d is an integer of 1-2.
+ E = 3, and Z is a group selected from Group A;
X is a group selected from the group B, and B2 is a linear or branched alkyl group having 1 to 12 carbon atoms or an aryl or arylalkyl group having 6 to 12 carbon atoms; In general formula (3), R ¹⁴ is an alkylene group having 1 to 4 carbon atoms, and in general formula (4) corresponding to B4, R ¹⁵ is an alkylene group having 2 to 4 carbon atoms, and R ¹⁶ is Hydrogen, an alkyl group having 1 to 3 carbon atoms or a group represented by the general formula (3), wherein R ¹⁷ is hydrogen,
12 linear or branched alkyl groups, having 6 to 1 carbon atoms
2 is an aryl group or an arylalkyl group, or a group represented by the general formula (3), g is an integer of 1 to 4, and in the general formula (5) corresponding to B5, R ¹⁸ has 2 to 2 carbon atoms.
4, R ¹⁹ , R ²⁰ , R ²¹ and R ²²
Are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms or a hydroxyl group, and Y is a methylene group, a methylene group substituted with an alkyl group having 1 to 6 carbon atoms or a hydroxyl group, an imino group, An imino group or an oxygen substituted with an alkyl group or a hydroxyl group, and when e = 1, h = 1
And when e = 2, h = 0 or h = 1 (however, when h = 0, the general formula (5) and the general formula (1) share the same N (nitrogen)) Such a nitrogen-containing compound.

Further preferred as the nitrogen-containing compound of the present invention
The reason is that R in the general formula (1)¹Is hydrogen or carbon number
Alkyl group of 1 to 6, phenyl group or 7 to 15 carbon atoms
An alkylaryl group of R^Two, R^Three, R^FourAnd R^Five
Is hydrogen or an alkyl group having 1 to 3 carbon atoms or a general formula
The group represented by (2) (R ^Two, R^Three, R^FourAnd R^FiveOne of
The group is a group represented by the general formula (2), and the remaining three
Each independently represents hydrogen or an alkyl group having 1 to 3 carbon atoms)
In general formula (2), R⁷And R⁸Are individually
Hydrogen or an alkyl group having 1 to 3 carbon atoms;⁹But charcoal
An alkylene group having a prime number of 2 to 4,^TenHas 1 to 1 carbon atoms
And f is an integer of 0 to 20
R⁶Is an alkylene group having 3 to 6 carbon atoms;¹¹,
R¹², R¹³Is an alkylene group having 1 to 3 carbon atoms, and a is
An integer of 2 to 100, wherein b and c are independently 0 or
Is 1, d is 1, e is 2, Z is A1, A
2, a group selected from A4, and X is B1, B3,
It is a group selected from B4 and B5, and corresponds to B3.
In general formula (3), R¹⁴Is an alkylene group having 1 to 3 carbon atoms
In general formula (4) corresponding to B4, R^FifteenHas 2 carbon atoms
3 to 3 alkylene groups;¹⁶Is hydrogen, methyl, d
A tyl group or a group represented by the general formula (3),¹⁷But
Hydrogen, linear or branched alkyl having 1 to 6 carbon atoms
Group, phenyl group, arylalkyl group having 7 to 9 carbon atoms,
Or a group represented by the general formula (3), wherein g is 1 to 3
In general formula (5) corresponding to B5, R is an integer.¹⁸But charcoal
An alkylene group having a prime number of 2 to 3,¹⁹, R²⁰, R^{twenty one}You
And R^{twenty two}Are each independently hydrogen, alkyl having 1 to 3 carbon atoms
And Y is an imino group, having 1 to 3 carbon atoms.
An imino group substituted with an alkyl group or a hydroxyl group, or
Is oxygen and h is 0 or 1 (provided that h = 0
In the case of the general formula (5) and the general formula (1), the same N (nitrogen
Nitrogen-containing compounds).

The nitrogen-containing compound according to the present invention can be produced by any method. As an example, it is possible to synthesize the nitrogen-containing compound of the present invention represented by the general formula (1) through the following (A) ketimination step, (B) polymerization step and (C) hydrolysis step. it can. (A) A compound having two or more amino groups or a compound having at least one amino group and another active hydrogen group such as an alkanol group, an imino group, a carboxyl group, or the like as a starting material, A ketimine compound is obtained by heating and dehydrating a ketone. Compounds having two or more amino groups in the molecule include diamines such as ethylenediamine, propylenediamine (1,2-diaminopropane) and trimethylenediamine (1,3-diaminopropane), diethylenetriamine, dipropylenetriamine, Polyamines such as (trimethylene) triamine, dimethylaminopropylenediamine, triethylenetetramine, tripropylenetetramine, tetraethylenepentamine, tetrapropylenepentamine, pentaethylenehexamine, pentapropylenehexamine, etc.
Or more). Examples of the compound having an amino group and an alkanol group in the molecule include monomethanolamine, monoethanolamine, mono-n-propanolamine, monoisopropanolamine, mono (linear or branched) butanolamine (the position of the hydroxyl group is arbitrary. Is present), mono (linear or branched) pentanolamine (position of hydroxyl group is arbitrary), mono (linear or branched) hexanolamine (position of hydroxyl group is arbitrary), 2-
Alkanolamines such as (2-aminoethylamino) ethanol and the like can be mentioned. Examples of the compound having an amino group and an imino group in the molecule include the above-mentioned polyamine and 4
-Aminomethylpiperidine and the like. As the compound having an amino group and a carboxyl group in the molecule,
Amino acids such as alanine, β-alanine, N- (2-aminoethyl) glycine and the like can be mentioned. As the ketone, one represented by the following general formula (14) is usually used.

Embedded image (In the above formula (14), R ²³ and R ²⁴ each independently represent a linear or branched alkyl group having 1 to 10, preferably 1 to 5 carbon atoms.) In addition, the above general formula (14) Among the compounds represented by),
Ketones having a branched alkyl group and having large steric hindrance are preferred, and isobutyl methyl ketone, isobutyl ethyl ketone, diisobutyl ketone and the like are suitably used. By reacting an alkanolamine with a ketone, a ketimine compound represented by the following general formula (15) can be obtained.

Embedded image In (the above formula (15), R ⁶ represents the same group as R ⁶ in the general formula (1), R ²³ and R ²⁴ Formula (1
The same groups as R ²³ and R ²⁴ in 4) are shown. When an amino acid is reacted with a ketone, the following general formula (16)
Can be obtained.

Embedded image(In the above formula (16), R¹¹Is R in group A3
¹¹Represents the same group as ^{twenty three}And R^{twenty four}Is the general formula (14)
R in^{twenty three}And R^{twenty four}And the same group. In addition, when a diamine and a ketone are reacted, the following general formula is obtained.
A ketimine compound represented by (17) can be obtained.
You.

Embedded image In (the above formula (17), R ¹⁵ is formula (represent the same group as R ¹⁵ in 4), R ²³ and R ²⁴ Formula (1
The same groups as R ²³ and R ²⁴ in 4) are shown. In addition, when a polyamine (having 3 or more N atoms) is reacted with a ketone, a ketimine compound represented by the general formula (18) or (19) can be obtained.

Embedded image(In the above formulas (18) and (19), R^Fifteenand
R¹⁶Is R in the general formula (4)^FifteenAnd R¹⁶The same group as
And g, g ′ and g ″ are the same as g in the general formula (4).
Represents one integer, R^{twenty three}And R^{twenty four}Is expressed by the general formula (14).
R^{twenty three}And R ^{twenty four}And the same group. ) Reaction of starting amine with ketone of general formula (14)
In this case, the molar ratio of the amino group to be protected is
Preferably, a ketone is reacted. Alkanolami
Equimolar for amino acids, amino acids and diamines, polyamines
(3 or more N atoms) in the case of equimolar or
Preferably, the tons are reacted. Also ketiminization process
The reaction temperature is arbitrary, but usually is 40 to 180 ° C.
Preferably, it is more preferably 80 to 150 ° C.
New(B) Polymerization step For example, bases such as potassium hydroxide and sodium hydroxide
Obtained in the ketimination step (A) using
A compound represented by the general formula (20)
Formation Obtained by Polymerizing Epoxy Compounds
Product (in the form of metal alkoxide)
Alternatively, a halogen compound represented by the general formula (21)
After stopping the reaction, treat it with an inorganic acid or solid acid.
To the terminal represented by the general formulas (22) to (26).
Polyoxyalkylene glycol having thymine compound
Obtain the derivative.

Embedded image (In the general formulas (20) and (21), R ¹ , R ² ,
R ³ , R ⁴ and R ⁵ represent R ¹ , R ² , R ³ and R in the formula (1)
⁴ and R ⁵ represent the same groups, and T represents chlorine, bromine or iodine. )

Embedded image(In the above general formulas (22), (23) and (24)
A, R¹, R^Two, R^Three, R ^Four, R^FiveAnd R⁶Is the general formula
A, R in (1)¹, R^Two, R^Three, R^Four, R^FiveAnd R⁶
Is the same as¹¹Is R in group A3¹¹Same as
R^FifteenIs R in the general formula (4)^FifteenIs the same as
^{twenty three}, R^{twenty four}Is R in the general formula (14)^{twenty three}, R^{twenty four}Same as
And i represents an integer such that d + i = 2. )

Embedded image (A in the formula ^{(25), R 1, R} 2, R 3, R 4 and R ^5, a in the general formula ^{(1), R 1, R} 2, R 3, R
^4, and R ⁵ and are ^{identical, R 15, R 16, g} ' and g "are the same as R ^15, R ^16, g in the general formula (4), R
²³ and R ²⁴ are the same as R ²³ and R ²⁴ in formula (14).

Embedded image (A, d, R ¹ , R ² , R ³ , R ⁴ in the above formula (26)
And R ⁵ are a, d, R ¹ ,
The same as R ² , R ³ , R ⁴ and R ⁵ , g, R ¹⁵ , R ¹⁶
Is the same as g, R ¹⁵ and R ¹⁶ in the general formula (4),
R ²³ and R ²⁴ are the same as R ²³ and R ²⁴ in Formula (14), and i represents an integer such that d + i = 2. )

Preferred examples of the epoxy compound represented by the general formula (20) include ethylene oxide, propylene oxide, isobutylene oxide,
2-butylene oxide, 2,3-butylene oxide, trimethylethylene oxide, tetramethylethylene oxide, 1,2-epoxyhexane, 1,2-epoxyheptane, 1,2-epoxyoctane, 1,2-epoxydecane, 1,2 Epoxide decane, 1,2-epoxytetradecane, 1,2-epoxyhexadecane, 1,2
-Epoxy octadecane, methyl glycidyl ether,
Ethyl glycidyl ether, n-propyl glycidyl ether, isopropyl glycidyl ether, n-butyl glycidyl ether, isobutyl glycidyl ether,
sec-butyl glycidyl ether, tert-butyl glycidyl ether, linear or branched pentyl glycidyl ether, linear or branched hexyl glycidyl ether, linear or branched heptyl glycidyl ether, linear or branched octyl glycidyl Ether, straight or branched nonyl glycidyl ether, straight or branched decyl glycidyl ether, straight or branched undecyl glycidyl ether, straight or branched dodecyl glycidyl ether, straight or branched tri Decyl glycidyl ether, linear or branched tetradecyl glycidyl ether, linear or branched pentadecyl glycidyl ether, linear or branched hexadecyl glycidyl ether, linear or branched heptadecyl glycidyl ether, linear Also Branched hexadecyl glycidyl ether, straight or branched octadecyl glycidyl ether, vinyl glycidyl ether, straight or branched propenyl glycidyl ether, straight or branched butenyl glycidyl ether, straight or branched pentenyl Glycidyl ether, linear or branched hexenyl glycidyl ether, linear or branched heptenyl glycidyl ether, linear or branched octenyl glycidyl ether, linear or branched nonenyl glycidyl ether,
Linear or branched decenyl glycidyl ether, linear or branched undecenyl glycidyl ether, linear or branched dodecenyl glycidyl ether, linear or branched tridecenyl glycidyl ether, Chain or branched tetradecenyl glycidyl ether, straight or branched pentadecenyl glycidyl ether, straight or branched hexadecenyl glycidyl ether, straight or branched heptadecenyl glycidyl ether Linear or branched hexadecenyl glycidyl ether, linear or branched octadecenyl glycidyl ether, phenyl glycidyl ether, tolyl glycidyl ether, xylyl glycidyl ether, linear or branched propyl phenyl glycidyl ether , Linear or branched butylphenylglycidyl ether Linear or branched pentyl phenyl glycidyl ether, linear or branched hexyl phenyl glycidyl ether, linear or branched heptyl phenyl glycidyl ether, linear or branched octyl phenyl glycidyl ether, linear or branched Nonylphenyl glycidyl ether, linear or branched decylphenyl glycidyl ether, linear or branched undecylphenyl glycidyl ether, linear or branched dodecylphenyl glycidyl ether, linear or branched tridecylphenyl glycidyl Ether, linear or branched dodecylphenyl glycidyl ether, 1,2-epoxy-3-methoxy-5-oxahexane, 1,2-
Epoxy-4,7-dioxaoctane, 4,5-epoxy-2,7-dioxaoctane, 1,2-epoxy-5
-Methyl-4,7-dioxaoctane, 1,2-epoxy-6-methyl-4,7-dioxaoctane, 1,2-
Epoxy-5- (2-oxapropyl) -4,7-dioxaoctane, 1,2-epoxy-3,5-bis (2-
Oxapropyl) -4,7-dioxaoctane, 1,2
-Epoxy-3,6-bis (2-oxapropyl)-
4,7-dioxaoctane, 1,2-epoxy-6-methoxy-4,8-dioxanonane, 1,2-epoxy-
4,7,10-trioxaundecane, 1,2-epoxy-5-methyl-4,7,10-trioxaundecane, 1,2-epoxy-8-methyl-4,7,10-trioxaundecane, 4,5-epoxy-9-methyl-
2,7,10-trioxaundecane, 1,2-epoxy-6,9-dimethyl-4,7,10-trioxaundecane, 1,2-epoxy-6,9-bis (2-oxapropyl)- 4,7,10-trioxaundecane,
1,2-epoxy-4,7,10,13-tetraoxatetradecane, 4,5-epoxy-2,7,10,13
-Tetraoxatetradecane, 7,8-epoxy-2,
5,10,13-tetraoxatetradecane, 7,8-
Epoxy-3,12-dimethyl-2,5,10,13-
Tetraoxatetradecane, 1,2-epoxy-6
9,12-trimethyl-4,7,10,13-tetraoxatetradecane and the like.

When the ketimine compound is reacted with the epoxy compound of the general formula (20), the molar ratio can be arbitrarily selected. Usually, 5 to 100 moles of the epoxy compound is added to 1 mole of the ketimine compound. It is preferred to react. The reaction temperature in the polymerization step is also arbitrary, but is usually preferably from 60 to 180 ° C, and preferably from 80 to 15 ° C.
More preferably, it is 0 ° C. (C) Hydrolysis Step The polyoxyalkylene glycol derivative having a ketimine compound at the terminal obtained in the above step is subjected to a heat treatment in the presence of excess water, thereby containing the present invention represented by the general formula (1). Nitrogen compounds can be obtained. The reaction temperature in the hydrolysis step is also arbitrary, but is usually 40 to 150 ° C.
And more preferably 50 to 100 ° C. Further, by adding an epoxy compound of the general formula (20) to a terminal amino group obtained by hydrolyzing a polyoxyalkylene glycol derivative having a ketimine compound at a terminal, an alkanolamine-type nitrogen-containing compound is terminated. You can also get. Also, morpholine, N-
β-hydroxyethylmorpholine, N- (2-hydroxypropyl) morpholine, piperidine, 1- (2-hydroxyethyl) piperidine, 2-dimethylaminoethanol, 2-dimethylamino-1-propanol, 1-dimethylamino-2- Propanol, 4-dimethylamino-1-butanol, 2-dimethylamino-2-methyl-
1-propanol, 2-diethylaminoethanol, 3
-Diethylamino-1-propanol, 1-diethylamino-2-propanol, 2-diisopropylaminoethanol, 2-dimethylaminoethylamine, 3-dimethylaminopropylamine, 2-diethylaminoethylamine, 3-diethylaminopropylamine, 2-diisopropylaminoethylamine , 1-aminopiperidine, 1- (2-aminoethyl) piperidine, 4- (2-
Aminoethyl) morpholine, 4- (3-aminopropyl) morpholine, piperazine, 1-methylpiperazine,
When 1- (2-aminoethyl) piperazine or the like is used, the (B) polymerization step can be directly performed without the necessity of performing the (A) ketimination step and the (C) hydrolysis step,
The nitrogen-containing compound of the present invention represented by the general formula (1) can be obtained. As another method, the nitrogen-containing compound of the present invention represented by the general formula (1) is synthesized through the following (D) polymerization step, (E) chloroformate step and (F) carbamate step. be able to. (D) Polymerization Step For example, using a base such as potassium hydroxide or sodium hydroxide or an alkoxide thereof as a catalyst, an oxygen-containing compound represented by the general formula (27) as a reaction initiator, and a compound represented by the general formula (20) A polymerization product (in the form of a metal alkoxide) is obtained by polymerizing the epoxy compound to be obtained, and the resulting product is neutralized with an acid such as hydrochloric acid, thereby obtaining a polymer represented by the general formula (28). An oxyalkylene glycol derivative is obtained.

Embedded image In general formulas (27) and (28), a, R ¹ , R ² ,
R ³ , R ⁴ and R ⁵ represent a, R ¹ ,
It is the same as R ² , R ³ , R ⁴ and R ⁵ . General formula (27)
When the oxygen-containing compound is reacted with the epoxy compound of the general formula (20), the molar ratio can be arbitrarily selected. Usually, 5 to 100 mol of the epoxy compound is added to 1 mol of the oxygen-containing compound. It is preferred to react. The reaction temperature in the polymerization step is also arbitrary, but is usually 60 to 1
The temperature is preferably 80 ° C, more preferably 80 to 150 ° C. (E) Chloroformating step The polyoxyalkylene glycol derivative of the general formula (28) obtained in the above-mentioned polymerization step or the metal alkoxide compound before neutralization thereof is treated with an excess amount of phosgene, for example, at room temperature for chloroformating. To obtain a chlorine-containing compound represented by the general formula (29).

Embedded image A in the general formula ^{(29), R 1, R} 2, R 3, R 4 and R ^5, a in the general formula ^{(1), R 1, R} 2, R 3, R 4
And R ⁵ are the same. (F) Carbamate Step The general formula (2) obtained in the above chloroformate step
The nitrogen-containing compound of the present invention can be obtained by reacting the chlorine-containing compound of 9) with the amine compound represented by the general formula (30).

Embedded image X in the general formula (30) is e in the general formula (1).
= Indicates X the same group in the case of 2, R ¹² represents the same group as R ¹² in the group A A4, j is 0 or 1. In addition, as the amine compound represented by the general formula (30),
Ethylenediamine, propylenediamine (1,2-diaminopropane), trimethylenediamine (1, -diaminopropane), dimethylaminopropylamine, diethylenetriamine, dipropylenetriamine, di (trimethylene) triamine, dimethylaminopropylenediamine, triethylenetetramine, Tripropylenetetramine, tetraethylenepentamine, tetrapropylenepentamine, pentaethylenehexamine, pentapropylenehexamine, piperidine, 1-aminopiperidine, 4-
Aminomethylpiperidine, 1- (2-aminoethyl) piperidine, morpholine, 4-aminomorpholine, 4-
(2-aminoethyl) morpholine, 4- (3-aminopropyl) morpholine, piperazine, 1-amino-4-methylpiperazine, 1- (2-aminoethyl) piperazine, 1- (3-aminopropyl) piperazine, mono Methanolamine, monoethanolamine, mono-n-propanolamine, monoisopropanolamine, mono (linear or branched) butanolamine (position of hydroxyl group is arbitrary), mono (linear or branched) pentanolamine ( The position of the hydroxyl group is arbitrary; mono (linear or branched) hexanolamine (the position of the hydroxyl group is arbitrary); 2- (2-aminoethyl) ethanol (see formula a); D-glucamine (formula b) reference)

Embedded image Dimethanolamine, diethanolamine, di-n-propanolamine, diisopropanolamine, di (linear or branched) butanolamine (position of hydroxyl group is arbitrary), di (linear or branched) pentanolamine (hydroxyl group) Can be in any position), di (linear or branched)
Hexanolamine (position of hydroxyl group is arbitrary), monohydroxypyrrolidine, monohydroxypyrroline (position of hydroxyl group is arbitrary), monohydroxypyrrole (position of hydroxyl group is arbitrary), monohydroxypyrazolidine (position of hydroxyl group) Position is arbitrary), monohydroxypyrazoline (position of hydroxyl group is arbitrary), monohydroxypyrazole (position of hydroxyl group is arbitrary), monohydroxyimidazolidine (position of hydroxyl group is arbitrary), monohydroxy Imidazoline (position of hydroxyl group is arbitrary), monohydroxyimidazole (position of hydroxyl group is arbitrary), monohydroxyfuroxane (position of hydroxyl group is arbitrary), monohydroxypiperidine (position of hydroxyl group is arbitrary) , Monohydroxypiperazine (position of hydroxyl group is optional Monohydroxymorpholine (position of hydroxyl group is arbitrary), monohydroxyindoline (position of hydroxyl group is arbitrary), monohydroxyindole (position of hydroxyl group is arbitrary), monohydroxyisoindole (position of hydroxyl group) Is optional),
Monohydroxypurine (the position of the hydroxyl group is arbitrary),
Monohydroxycarbazole (position of hydroxyl group is arbitrary), monohydroxy-β-carboline (position of hydroxyl group is arbitrary), monohydroxyphenoxazine (position of hydroxyl group is arbitrary), monohydroxyperimidine (position of hydroxyl group) Position is arbitrary), dihydroxypyrrolidine, dihydroxypyrroline (position of hydroxyl group is arbitrary), dihydroxypyrrole (position of hydroxyl group is arbitrary), dihydroxypyrazolidine (position of hydroxyl group is arbitrary), dihydroxypyrazine Zoline (position of hydroxyl group is arbitrary), dihydroxypyrazole (position of hydroxyl group is arbitrary), dihydroxyimidazolidine (position of hydroxyl group is arbitrary), dihydroxyimidazoline (position of hydroxyl group is arbitrary), dihydroxyimidazole (The position of the hydroxyl group is optional. ), Dihydroxyfuroxan (position of hydroxyl group is arbitrary), dihydroxypiperidine (position of hydroxyl group is arbitrary), dihydroxypiperazine (position of hydroxyl group is arbitrary), dihydroxymorpholine (position of hydroxyl group is arbitrary) ), Dihydroxyindoline (position of hydroxyl group is arbitrary), dihydroxyindole (position of hydroxyl group is arbitrary), dihydroxyisoindole (position of hydroxyl group is arbitrary), dihydroxypurine (position of hydroxyl group is arbitrary) , Dihydroxycarbazole (the position of the hydroxyl group is arbitrary),
Dihydroxy-β-carboline (the position of the hydroxyl group is arbitrary), dihydroxyphenoxazine (the position of the hydroxyl group is arbitrary), dihydroxyperimidine (the position of the hydroxyl group is arbitrary), trimethanolamine, methyldimethanolamine, Ethyl dimethanolamine, triethanolamine, methyldiethanolamine, ethyldiethanolamine, tri-n-propanolamine, methyl-di-n-propanolamine, ethyl-di-n-propanolamine, triisopropanolamine, methyldiisopropanolamine, ethyl Diisopropanolamine, tri (linear or branched) butanolamine, methyldi (linear or branched) butanolamine, ethyldi (linear or branched) butanolamine, tri (linear or branched) pentano Triethanolamine, methyl di (straight or branched) pentanol amine, ethyl di (straight or branched)
Pentanolamine and the like can be mentioned. The molar ratio in the case of reacting the chlorine-containing compound of the general formula (29) and the amine compound of the general formula (30) in the carbamate formation step can be arbitrarily selected. The amine compound is preferably reacted at least 1 mol or more, more preferably 1 to 20 mol. In addition, the reaction temperature in the carbamate formation step is also arbitrary, but is usually preferably −20 to 150 ° C., and more preferably −10 to 80 ° C.

The nitrogen-containing compound represented by the general formula (1)
It is a very useful compound as a gasoline additive for in-cylinder direct injection gasoline engines, and is used as a gasoline composition obtained by mixing with base gasoline and optionally other gasoline additives. The content of the nitrogen-containing compound represented by the general formula (1) in the gasoline composition is not particularly limited, but is usually 0.001 to 10% by mass based on the total amount of the gasoline composition. Is chosen. In order to improve the cleanliness of the combustion chamber, in particular, the cavity of the direct injection gasoline engine, the lower limit of the content is 0.001% by mass, preferably 0.003% by mass, more preferably 0.005% by mass. mass%,
It is still more preferably 0.01% by mass, most preferably 0.015% by mass. In addition, the upper limit of the content is 10% by mass, preferably 5% by mass, more preferably 4% by mass, since it does not adversely affect the various properties of gasoline and the effect cannot be expected to be improved even if added more. %, Most preferably 3% by weight.

The above base gasoline can be produced by any method. Specific examples of the gasoline base material used at this time include, for example, light naphtha having arbitrary properties and obtained by distilling crude oil under normal pressure; cracked gasoline obtained by catalytic cracking, hydrocracking, etc .; Reformed gasoline obtained by the reforming method; polymerized gasoline obtained by polymerization of olefin; alkylate obtained by adding (alkylating) lower olefin to hydrocarbon such as isobutane; light naphtha is converted to isoparaffin by isomerization unit Isomerized gasoline obtained by inversion; de-n-paraffinized oil; butane; aromatic hydrocarbon compound; and a paraffin fraction obtained by dimerizing propylene followed by hydrogenation. A typical blending example is as follows. Unleaded gasoline includes, for example, (1) reformed gasoline: 0 to 70% by volume (2) light fraction of reformed gasoline (boiling point range: 25 to 12%)
(About 0 ° C): 0 to 35% by volume (3) Heavy fraction of reformed gasoline (boiling point range: 110 ° C to
(About 200 ° C.): 0 to 45% by volume (4) Cracked gasoline: 0 to 50% by volume (5) Light fraction of cracked gasoline (boiling point range: 25 to 90)
Degree): 0 to 45% by volume (6) Heavy fraction of cracked gasoline (boiling point range: 90 to 20)
(About 0 ° C.): 0 to 40% by volume (7) Alkylate: 0 to 40% by volume (8) A paraffin fraction obtained by dimerizing propylene and subsequently hydrogenating it: 0 to 30% by volume (9 ) Isomerized gasoline: 0 to 30% by volume (10) MTBE: 0 to 15% by volume (11) Light naphtha: 0 to 20% by volume (12) Butane: 0 to 10% by volume . Further, when producing base gasoline, it may be necessary to reduce the benzene content. The method of reducing the benzene at this time is optional. In particular, since the benzene is contained in a large amount in the reformed gasoline, the blending ratio of the reformed gasoline should be reduced. (2) Extract benzene in reformed gasoline using a solvent such as sulfolane (3) Convert benzene in reformed gasoline to other compounds (A) Hydrogenate benzene and cyclohexane (B) Reacts with benzene and an aromatic hydrocarbon compound having 9 or more carbon atoms to convert to toluene, xylene, ethylbenzene, etc. (C) Converts benzene to lower olefins (ethylene, propylene, etc.) Alternatively, alkylate using a lower alcohol (methanol, ethanol, etc.). 6. Use desulfurized heavy naphtha obtained by distilling and removing the hydrocarbon compound of (6). (5) Change the operating conditions of the catalytic reformer to reduce the benzene concentration in the reformed gasoline. It is preferable to use as a gasoline base material.

Further, as other gasoline additives,
Specifically, detergents and dispersants other than the nitrogen-containing compound represented by the general formula (1), such as succinimide and polyalkylamine; antioxidants such as phenolic and amine-based compounds; Schiff-type compounds and thioamide-type compounds Metal deactivators such as organic phosphorus compounds; anti-freezing agents such as polyhydric alcohols and ethers thereof; alkali metal salts or alkaline earth metal salts of organic acids, higher alcohol sulfates, etc. Antioxidants such as anionic surfactants, cationic surfactants and amphoteric surfactants; coloring agents such as azo dyes; rust inhibitors such as alkenyl succinates; discriminating agents such as chirizanine and coumarin; Odorants such as natural essential oil synthetic flavors and the like can be mentioned. 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 a gasoline composition comprising a base gasoline, a nitrogen-containing compound represented by the general formula (1) and, if necessary, other gasoline additives are not particularly limited. However, usually, JIS K 2254 "Petroleum products-Distillation test method"
It is desirable that the distillation property measured by the above satisfies the following. 10% by volume distillation temperature (T ₁₀ ): 35 to 55 ° C. 30% by volume distillation temperature (T ₃₀ ): 55 to 75 ° C. 50% by volume distillation temperature (T ₅₀ ): 75 to 100 ° C. 70% by volume distillation Temperature (T ₇₀ ): 100 to 130 ° C. 90% by volume Distillation temperature (T ₉₀ ): 110 to 160 ° C. Distillation end point: 130 to 210 ° C. The lower limit of T ₁₀ is desirably 35 ° C., preferably 40 ° C. . If the temperature is lower than 35 ° C., gasoline coking may occur in the injector. On the other hand, the upper limit of the T ₁₀ is 55 ° C., preferably 50 ° C., more preferably 4
Desirably, the temperature is 8 ° C. If it exceeds 55 ° C,
There is a possibility of causing a problem in low-temperature startability. The lower limit of T ₃₀ is 55 ° C., it is desirable that preferably 60 ° C..
If the temperature is lower than 55 ° C., there is a possibility that high-temperature operability may be deteriorated or gasoline coking may occur in the injector. On the other hand, the upper limit of the T ₃₀ is 75 ° C., it is desirable that preferably 70 ° C., more preferably 68 ° C.. If the temperature exceeds 75 ° C., a problem may occur in low-temperature operability. The lower limit of T ₅₀ is 75 ° C., it is desirable that preferably 80 ° C.. If the temperature is lower than 75 ° C., there is a possibility that high-temperature operability may be deteriorated. On the other hand, T ₅₀
Is preferably 100 ° C., preferably 95 ° C., and more preferably 93 ° C. If the temperature exceeds 100 ° C., there is a possibility that the low-temperature and normal-temperature operability may cause a problem. The lower limit of T ₇₀ is desirably 100 ° C..
On the other hand, the upper limit of the T ₇₀ is 130 ° C., preferably 125 ° C.,
More preferably, the temperature is 123 ° C, most preferably 120 ° C. When the temperature exceeds 130 ° C., there is a possibility that the low-temperature and normal-temperature operability may be inferior. The lower limit of T ₉₀ is 110 ° C., it is desirable that preferably 120 ° C.. On the other hand, the upper limit of the T _90, from the viewpoint of the low temperature and room temperature operability and reduce dilution with gasoline engine oil, increased emissions, such as it is possible to prevent degradation and generation of sludge in the engine oil From the point, 1
60 ° C, preferably 150 ° C, more preferably 140 ° C
It is desirable that The lower limit of the distillation end point is desirably 130 ° C. On the other hand, the upper limit of the distillation end point is 21
0 ° C, preferably 200 ° C, more preferably 195 ° C,
Most preferably, it is desirably 190 ° C. When the end point exceeds 210 ° C., there is a possibility that a malfunction occurs at normal temperature operability.

Although the vapor pressure of the gasoline composition is not limited, the vapor pressure is preferably 70 kPa or less, since no gasoline coking problem occurs in the injector and the amount of evaporative emission is suppressed. Is 65 kPa or less, more preferably 60 kPa or less,
Most preferably, it is desirable to be 55 kPa or less.
The term “vapor pressure” as used herein means a vapor pressure (lead vapor pressure (RVP)) measured by JIS K 2258 “Crude oil and fuel oil vapor pressure test method (lead method)”. Density of the gasoline composition without any restriction on the (15 ° C.), it is desirable that the 0.73~0.77g / cm ^3. the lower limit value of the density is 0.73 g / cm ^3, there preferably 0.735 g / cm ³ If it is less than 0.73 g / cm ³ , the fuel efficiency may be deteriorated, while the upper limit of the density is 0.77 g / cm ³ , preferably 0.76 g / cm ³ .
cm ³ , and when it exceeds 0.77 g / cm ³ , there is a possibility that acceleration may deteriorate or smoldering of the plug may occur. Here, the density means a density measured according to JIS K 2249 "Determination of density of crude oil and petroleum products and conversion table of density / mass / capacity". The gasoline composition,
Gasoline that does not substantially contain an alkyl lead compound such as tetraethyl lead, and even if it contains a trace amount of a lead compound, the content is lower than the applicable category of JIS K 2255 “Test method for lead content in gasoline”. It is less than or equal to the value.

In the above gasoline composition, the octane number is not limited at all. However, in order to further improve the anti-knocking property, the octane number according to the research method (RON) is set to 8 (RON).
9 or more, preferably 90 or more, more preferably 90.5
As described above, it is most preferable that the ratio be 91 or more. Further, in order to enhance the anti-knock property during high-speed running, it is desirable that the octane number by motor method (MON) is 80 or more, preferably 80.5 or more, and most preferably 81 or more. Here, the research octane number and the motor octane number are JIS K 2, respectively.
280 means the octane number of the research method and the octane number of the motor method measured by "Octane number and cetane number test method". There are no particular restrictions on the content of the saturated component, olefin component and aromatic component in the gasoline composition, but the saturated component (V (P)): 50 to 100% by volume Olefin component (V (O)): 0 １５15% by volume Aromatic component (V (Ar)): desirably 0 to 35% by volume. V (P) prevents gasoline coking in the injector, reduces smoldering of the plug, suppresses the ozone generation capability of the exhaust gas,
From the viewpoint of reducing the benzene concentration in the exhaust gas and preventing the generation of soot, the content is desirably 50 to 100% by volume, preferably 60 to 100% by volume, and more preferably 70 to 100% by volume. V (O) is 0 from the viewpoint of preventing gasoline coking in the injector.
It is desirable that the content be from 15 to 15% by volume, preferably from 0 to 10% by volume, more preferably from 0 to 7% by volume, and most preferably from 0 to 5% by volume. Further, V (Ar) is 0 to 35% by volume from the viewpoint 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 preventing soot from being generated. It is preferably 0 to 30% by volume, more preferably 0 to 25% by volume, and most preferably 0 to 20% by volume. The above V (P), V (O) and V (Ar) are all JI
It is a value measured by a fluorescent indicator adsorption method of SK 2536 “Petroleum products-hydrocarbon type test method”.

The content of each component of the gasoline composition is not particularly limited, but it is desirable that the following conditions be satisfied. (1) V (Bz): 0 to 1% by volume (2) V (Tol): 0 to 30% by volume (3) V (C ₈ A): 0 to 20% by volume (4) V (C ₉ A) : 0 to 5% by volume (5) V (C ₁₀ + A): 0 to 3% by volume (6) V (MA) / V (PA) when V (PA) = 0 or V (PA) ≠ 0: 1 or more _{(7) V (C 4)} : 0~10 _{volume% (8) V (C 5} ): 10~35 _{volume% (9) V (C 6} ): 10~30 volume% (10) V (C ₇ ⁺ p): 10 to 50% by volume (11) V (C ₉ ⁺ ): 0 to 10% by volume The above V (Bz) indicates the benzene content based on the total amount of the gasoline composition, and the value is 0 to 0%. 1% by volume, preferably 0%
It is desirably about 0.5% by volume. By setting the benzene content to 0 to 1% by volume, the benzene concentration in the exhaust gas can be kept low. The above V (To
1) and V (C ₈ A) indicate the toluene content and the content of the aromatic hydrocarbon compound having 8 carbon atoms, respectively, based on the total amount of the gasoline composition, and V (Tol) is 0 to 30% by volume, preferably 0 -20% by volume, V (C ₈ A) is 0-2
It is desirably 0% by volume, preferably 0 to 15% by volume. The aromatic hydrocarbon compound having 8 carbon atoms includes ethylbenzene, xylene (including all substituted isomers), and the like. The above V (C ₉ A) indicates the content of an aromatic hydrocarbon compound having 9 carbon atoms based on the total amount of the gasoline composition, and the value is 0 to 5% by volume in order to suppress the ozone generation ability of the exhaust gas. It is preferable that the content be suppressed to 0 to 3% by volume. The aromatic hydrocarbon having 9 carbon atoms includes n
-Propylbenzene, isopropylbenzene (cumene), ethylmethylbenzene (including all substituted isomers), trimethylbenzene (including all substituted isomers)
Etc. are included. The V (C ₁₀ ⁺ A) of, in order to suppress low ozone formation potential of the exhaust gases an aromatic hydrocarbon compound content of 10 or more carbon atoms of gasoline based on the total amount of the composition, the amount is 0-3 volume %, Preferably 0 to 1% by volume,
More preferably, it is desirable to be suppressed to 0% by volume.
The aromatic hydrocarbon compounds having 10 or more carbon atoms include diethylbenzene (including all substituted isomers), dimethylethylbenzene (including all substituted isomers), tetramethylbenzene (including all substituted isomers), n -Butylmethylbenzene (including all substituted isomers) and the like.

The above V (MA) and V (PA) are each substituted with a monoalkyl-substituted aromatic hydrocarbon compound content (% by volume) based on the total amount of the gasoline composition and two or more alkyl groups. The content (volume%) of the aromatic hydrocarbon compound is shown. In the present invention, when V (PA) is 0 or V (PA) is not 0, the content of the former and the content of the latter are used. Volume ratio, V (MA) / V (PA)
Is maintained at 1 or more, preferably 1.5 or more, more preferably 2 or more. Note that V (B
z), V (Tol), V (C ₈ A), V (C ₉ A), V
^{_{(C 10 + A), V}} (MA) and V (PA) are both JIS K 2536 - is a value obtained by quantitatively analyzed by gas chromatography in "Petroleum Product hydrocarbon Type Test Method". The above V (C ₄ ) indicates the content of the hydrocarbon compound having 4 carbon atoms based on the total amount of the gasoline composition. Since the amount of evaporative emission can be kept lower, V
(C ₄ ) is 0 to 10% by volume, preferably 0 to 5% by volume,
More preferably, it is desirably 0 to 3% by volume. Examples of the hydrocarbon compound having 4 carbon atoms include n-butane, 2-methylbutane (isobutane), 1-butene, 2-butene,
2-methylpropene and the like. The above V (C ₅ ) indicates the content of an aliphatic hydrocarbon compound having 5 carbon atoms based on the total amount of gasoline, the lower limit of which is 10% by volume, preferably 15% by volume, the upper limit is 35% by volume, Preferably, it is in the range of 30% by volume. By setting the content of the aliphatic hydrocarbon compound having 5 carbon atoms to 10% by volume or more, a gasoline composition having excellent room-temperature operability can be obtained. Further, by setting this to 35% by volume or less, a gasoline composition excellent in high-temperature operability can be obtained. Then, from the viewpoint of preventing coking of gasoline in the injector, the content (V (C ₅ o)) (volume%) of the unsaturated hydrocarbon compound in the aliphatic hydrocarbon compound having 5 carbon atoms is 0. Or
Alternatively, the content (V (C ₅ p)) (volume%) of the saturated hydrocarbon compound in the aliphatic hydrocarbon compound having 5 carbon atoms and V
(C ₅ o), that is, V (C ₅ p) / V (C
It is further desirable that ₅ o) be 1 or more, preferably 1.5 or more, more preferably 2 or more, and most preferably 3 or more. The saturated aliphatic hydrocarbon compound having 5 carbon atoms includes n
-Pentane, 2-methylbutane (isopentane), 2,
2-dimethylpropane (neopentane) and the like,
Similarly, unsaturated aliphatic hydrocarbon compounds include 1-pentene, 2-pentene, 2-methyl-1-butene, 2-methyl-2-butene, 3-methyl-1-butene and the like.

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, the lower limit of which is 10% by volume, preferably 15% by volume, and the upper limit. It is desirable that the value be in the range of 30% by volume, preferably 25% by volume. By setting the content of the aliphatic hydrocarbon compound having 6 carbon atoms to 10% by volume or more, a gasoline composition having excellent room-temperature operability can be obtained. Further, by setting the content to 30% by volume or less, a gasoline composition excellent in high-temperature operability is obtained. From the viewpoint of preventing gasoline coking in the injector, the content (V (C ₆ o)) (volume%) of the saturated hydrocarbon compound in the aliphatic hydrocarbon compound having 6 carbon atoms is 0. Or the ratio of the content (V (C ₆ p)) (volume%) of the saturated hydrocarbon compound in the aliphatic hydrocarbon compound having 6 carbon atoms to V (C ₆ o), that is, V ( C ₆ p) / V (C ₆ o) is 2 or more,
More preferably, it is 3 or more, more preferably 5 or more, and most preferably 10 or more. As the saturated aliphatic hydrocarbon compound having 6 carbon atoms, n-hexane, 2
-Methylpentane, 3-methylpentane, 2,2-dimethylbutane, 2,3-dimethylbutane, and the like, and unsaturated aliphatic hydrocarbon compounds also include 1-hexene,
2-hexene, 3-hexene, 2-methyl-1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 2-methyl-2-pentene, 3-methyl-2-pentene, 4- Methyl-2-pentene, 2,3-dimethyl-1-butene, 3,3-dimethyl-1-butene, 2,3
-Dimethyl-2-butene and the like. The above V (C ₇ ⁺ p)
Indicates the content of a saturated aliphatic hydrocarbon compound having 7 or more carbon atoms based on the total amount of the gasoline composition, and the lower limit is 10% by volume, preferably 20% by volume, and the upper limit is 50% by volume, preferably It is desirable to be in the range of 45% by volume. By setting the content of the saturated aliphatic hydrocarbon compound having 7 or more carbon atoms to 10% by volume or more, a gasoline composition having excellent operability at normal temperature can be obtained. Thus, an excellent gasoline composition can be obtained. Examples of the saturated aliphatic hydrocarbon compound having 7 or more carbon atoms include n-heptane, 2-methylhexane, 3-methylhexane, 2,2-dimethylpentane, 2,3-dimethylpentane, 2,4-dimethylpentane, , 3-dimethylpentane, 3-ethylpentane, 2,2,3-trimethylbutane and the like. The above V (C ₉ ⁺ ) indicates the content of a hydrocarbon compound having 9 or more carbon atoms based on the total amount of the gasoline composition. Increased emissions,
This value is 0 to 10% by volume, preferably 0 to 10% by volume, because deterioration of engine oil and generation of sludge can be prevented.
-5% by volume, more preferably 0% by volume. Note that V (C ₄ ), V (C ₅ ), and V (C _{5
p), V (C 5 o} ), V (C 6), V (C 6 p), V (C 6
o), V (C ₇ ⁺ p) and V (C ₉ ⁺ ) are values quantified by the following gas chromatography method. That is, a methyl silicon capillary column is used as the column, helium or nitrogen is used as the carrier gas, and a hydrogen ionization detector (FID) is used as the detector.
~ 50m, carrier gas flow rate 0.5 ~ 1.5ml / mi
n, division ratio 1: 50-1: 250, inlet temperature 150-
It is a value measured under the conditions of 250 ° C, initial column temperature of -10 to 10 ° C, final column temperature of 150 to 250 ° C, and detector temperature of 150 to 250 ° C.

In the above gasoline composition, the content of the oxygen-containing compound is not limited at all.
It is desirably about 2.0% by mass. If the content exceeds 2.7% by mass, the fuel efficiency of the gasoline composition may deteriorate, and NOx in the exhaust gas may increase. Here, the oxygen-containing compound is an alcohol having 2 to 4 carbon atoms, 4 carbon atoms.
To 8 ethers. Examples of oxygenates that can be added to the gasoline composition according to the present invention include ethanol,
There are methyl tertiary butyl ether (MTBE), ethyl tertiary butyl ether, tertiary amyl methyl ether (TAME), tertiary amyl ethyl ether, and the like. Among them, MTBE and TAME are preferable, and MTBE is most preferable. In addition, methanol is not preferable because the concentration of aldehyde in the exhaust gas may be high and corrosive. The gasoline composition has no limitation on the sulfur content, but is 50 ppm or less, preferably 30 ppm, based on the total amount of the gasoline composition.
pm or less, more preferably 20 ppm or less, and most preferably 10 ppm or less. If the sulfur content exceeds 50 ppm, the performance of the exhaust gas treatment catalyst may be adversely affected, the concentrations of NOx, CO, and HC in the exhaust gas may increase, and the benzene emission may increase. There is. Here, the sulfur content is defined by JIS
K 2541 means crude oil and petroleum products-sulfur content as measured by the sulfur content test method.

The above gasoline composition is JIS K22
61 Unwashed real gum is less than or equal to 20 mg / 100 ml, and washed real gum is less than or equal to 3 mg / 100 ml, preferably 1 mg, as measured by "Petroleum products-Automotive gasoline and aviation fuel oil-Real gum test method-Injection evaporation method". / 10
It is desirably 0 ml or less. When the unwashed actual gum and the washed actual gum exceed the above-mentioned values, there is a concern that deposits may be formed in the fuel introduction system or the suction valve may stick. JIS K 2279 of the above gasoline composition
The total calorific value measured by "Crude oil and petroleum products-Calorific value test method and estimation method by calculation" is 40000 J / g.
Or more, preferably 45,000 J / g or more. JIS K 2287 of the above gasoline composition
The oxidation stability measured by the "gasoline oxidation stability test method (induction period method)" is 480 minutes or more, preferably 1
It is desirable that the time is 440 minutes or more. Oxidation stability of 48
If less than 0 minutes, gums may form during storage. The gasoline composition has a copper plate corrosion (50 ° C., 3
h) is preferably 1, preferably 1a. If the copper plate corrosion exceeds 1, the fuel system conduit may corrode. Here, copper plate corrosion refers to JIS K 25
13 "Petroleum products-Copper plate corrosion test method" (test temperature 50
C., test time 3 hours).

Further, the gasoline composition desirably has a kerosene mixing amount of 0 to 4% by volume. Here, the amount of kerosene mixed refers to a carbon number of 13 to 1 based on the total amount of the gasoline composition.
4 represents the hydrocarbon content (% by volume), which is obtained by quantification by the gas chromatography method shown below. That is, 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.
1.5 ml / min, split ratio 1: 50-1: 250, inlet temperature 150-250 ° C, initial column temperature -10-1
0 ° C, final column temperature 150-250 ° C, detector temperature 15
It is a value measured under the condition of 0 to 250 ° C.

[0038]

EXAMPLES Examples of the present invention will be described below, but these examples do not limit the present invention. First, an example of synthesizing the nitrogen-containing compound used in the examples is shown below. Synthesis Example 1 6.1 g (0.1 g) of monoethanolamine was placed in a pressure-resistant reaction vessel equipped with a thermometer, a stirrer, a reflux condenser, and a nitrogen inlet.
Mol), 10 g (0.1 mol) of methyl isobutyl ketone
And 100 ml of toluene, and the inside of the reaction vessel was purged with nitrogen, and then heated at 120 ° C. for 5 hours to cause a dehydration and a ketimine reaction. After the ketimine reaction, the reaction mixture was cooled to room temperature, 5.6 g of potassium hydroxide was added as an addition catalyst, and the mixture was purged with nitrogen gas and heated to 120 ° C. 108.2 g (1.5 mol) of butylene oxide was added, and 5
After reacting for an hour, the reaction product solution was neutralized with an acid and filtered to remove the additional catalyst. Add 5g of water and add 90g
The hydrolysis reaction was performed at a temperature of 3 ° C. for 3 hours. Subsequently, by removing excess water, toluene and ketone, 180 g of the desired nitrogen-containing compound was obtained. This nitrogen-containing compound was an oily liquid having a number average molecular weight of about 2,000, and exhibited a pale yellow color. As a result of ¹³ C-NMR analysis, this nitrogen-containing compound was a random copolymer having an average structure represented by the formula (31).

Embedded image Synthesis Example 2 6.1 g (0.1 g) of monoethanolamine was placed in a pressure-resistant reaction vessel equipped with a thermometer, a stirrer, a reflux condenser, and a nitrogen inlet.
Mol), 14.2 g (0.1 mol) of diisobutyl ketone
And 100 ml of toluene, and the inside of the reaction vessel was purged with nitrogen, and then heated at 120 ° C. for 5 hours to cause a dehydration and a ketimine reaction. After the ketimine reaction, the mixture was cooled to room temperature, 5.6 g of potassium hydroxide was added thereto as an addition catalyst, and the mixture was replaced with nitrogen gas and heated to 120 ° C.
After adding 216.3 g (3.0 mol) of butylene oxide and reacting for 5 hours, the reaction product solution was neutralized with an acid and filtered to remove the additional catalyst. Further, 5 g of water was added, and a hydrolysis reaction was performed at 90 ° C. for 3 hours. Subsequently, by removing excess water, toluene and ketone, 205 g of the target nitrogen-containing compound was obtained. This nitrogen-containing compound was an oily liquid having a number average molecular weight of about 2200, and exhibited a pale yellow color. As a result of ¹³ C-NMR analysis, this nitrogen-containing compound was a polymer having an average structure represented by the formula (32).

Embedded image Synthesis Example 3 6.1 g (0.1 g) of monoethanolamine was placed in a pressure-resistant reaction vessel equipped with a thermometer, a stirrer, a reflux condenser, and a nitrogen inlet.
Mol), 10 g (0.1 mol) of methyl isobutyl ketone
And 100 ml of toluene, and the inside of the reaction vessel was purged with nitrogen, and then heated at 120 ° C. for 5 hours to cause a dehydration and a ketimine reaction. After the ketimine-forming reaction, the reaction mixture was cooled to room temperature, 5.6 g of potassium hydroxide was added as an addition catalyst, the mixture was replaced with nitrogen gas, and heated to 120 ° C. 130.4 g (0.7 mol) of ether
Was added and reacted for 5 hours. Next, after adding 9.3 g (0.1 mol) of 2-chlorobutane and reacting for 2 hours, the reaction product solution was purified and filtered to remove the additional catalyst. Further, 5 g of water was added, and a hydrolysis reaction was performed at 90 ° C. for 3 hours. Subsequently, after removing excess water, toluene and ketone, 8.8 g (0.2 mol) of ethylene oxide was added to obtain 160 g of the target nitrogen-containing compound. This nitrogen-containing compound was an oily liquid having a number average molecular weight of about 1900, and exhibited a pale yellow color. ¹³ C-NM
As a result of R analysis, this nitrogen-containing compound was a random copolymer having an average structure represented by the formula (33).

Embedded image Synthesis Example 4 In a pressure-resistant reaction vessel equipped with a thermometer, a stirrer, a reflux condenser, and a nitrogen inlet, 10.3 g of diethylenetriamine (0.
1 mol), 28.4 g (0.2 mol) of diisobutyl ketone, and 100 ml of toluene. After the atmosphere in the reaction vessel was replaced with nitrogen, the reaction vessel was heated at 120 ° C. for 5 hours to cause a dehydration and ketimination reaction. After the ketimine-forming reaction, the reaction mixture was cooled to room temperature, 5.6 g of potassium hydroxide was added thereto as an addition catalyst, and the atmosphere was replaced with nitrogen gas.
130.2 g (1.0 mol) of butyl glycidyl ether
Was added, and the mixture was reacted for 5 hours. Thereafter, the reaction product solution was neutralized with an acid and filtered to remove the additional catalyst. Further, 5 g of water was added, and a hydrolysis reaction was performed at 90 ° C. for 3 hours. Subsequently, by removing excess water, toluene and ketones,
165 g of the desired nitrogen-containing compound was obtained. This nitrogen-containing compound is an oily liquid having a number average molecular weight of about 1800,
It was pale yellow. As a result of ¹³ C-NMR analysis, this nitrogen-containing compound was a random copolymer having an average structure represented by the formula (34).

Embedded image Synthesis Example 5 6.1 g (0.1 g) of monoethanolamine was placed in a pressure-resistant reaction vessel equipped with a thermometer, a stirrer, a reflux condenser, and a nitrogen inlet.
Mol), 14.2 g (0.1 mol) of diisobutyl ketone
And 100 ml of toluene, and the inside of the reaction vessel was purged with nitrogen, and then heated at 120 ° C. for 5 hours to cause a dehydration and a ketimine reaction. After the ketimine reaction, the mixture was cooled to room temperature, 5.6 g of potassium hydroxide was added thereto as an addition catalyst, and the mixture was replaced with nitrogen gas and heated to 120 ° C.
After adding 180.3 g (2.5 mol) of butylene oxide and reacting for 5 hours, further adding 24.0 g (0.1 mol) of 1,2-epoxyhexadecane and reacting for 2 hours, the reaction product solution was added. Neutralized with an acid and filtered to remove the additional catalyst. Further, 5 g of water was added, and a hydrolysis reaction was performed at 90 ° C. for 3 hours. Subsequently, after removing excess water, toluene and ketone, 4.4 g of ethylene oxide was obtained.
(0.1 mol) was added to obtain 190 g of the desired nitrogen-containing compound. This nitrogen-containing compound was an oily liquid having a number average molecular weight of about 2150, and had a yellow color. As a result of ¹³ C-NMR analysis, this nitrogen-containing compound was a polymer having an average structure represented by the formula (35).

Embedded image Synthesis Example 6 4.45 g (0.06 mol) of tert-butanol and 3.37 g (0.06 mol) of potassium hydroxide were placed in an autoclave having a content of 1 liter, and the system was replaced with nitrogen gas. Heat. Then, 100m of toluene
1, 67.1 g of 2-ethylhexyl glycidyl ether
(0.36 mol), 62.7 g of propylene oxide
(1.08 mol) was added thereto, and the reaction temperature was 5 ° C at 120 ° C.
Allowed to react for hours. After completion of the reaction, the reaction product solution was neutralized with hydrochloric acid, and then extracted with toluene and the solvent toluene was distilled off to obtain a polyoxyalkylene compound 1
20 g were obtained. Next, 8.0 g (0.081 mol) of liquid phosgene was added to a mixed solution of 89.4 g (equivalent to 0.04 mol: calculated from the weight average molecular weight) of this polyoxyalkylene compound and 100 ml of toluene at 0 ° C. ,
The reaction was carried out at room temperature for 12 hours while cooling the reflux tube with dry ice. After the completion of the reaction, excess phosgene was removed, and toluene as a solvent was distilled off to obtain 88 g of a chlorine-containing compound.
Then 100 ml of toluene and 24. ethylenediamine.
After cooling 0 g (0.4 mol) of the mixed solution to 5 ° C., 85.0 g of the above-mentioned chlorine-containing compound (equivalent to 0.037 mol: calculated from the weight average molecular weight) was added dropwise, and the system was kept at 5 ° C. The reaction was allowed to proceed for 3 hours and then at room temperature for 2 hours. After completion of the reaction, unreacted ethylenediamine, generated hydrochloride, and toluene as a solvent were removed, and the residue was purified to obtain 82 g of a target nitrogen-containing compound. This nitrogen-containing compound was an oily liquid having a number average molecular weight of about 2300, and had a deep orange color. As a result of ¹³ C-NMR analysis, this nitrogen-containing compound was a random copolymer having an average structure represented by the formula (36).

Embedded image Synthesis Example 7 4.45 g (0.06 mol) of tert-butanol and 3.37 g (0.06 mol) of potassium hydroxide were placed in an autoclave having a content of 1 liter, and the system was replaced with nitrogen gas. Heat. Then, 100m of toluene
1, 64.9 g (0.90 mol) of 1,2-butylene oxide, 52.2 g (0.90 mol) of propylene oxide
Was added thereto and reacted at a reaction temperature of 120 ° C. for 5 hours.
After completion of the reaction, the reaction product solution was neutralized with hydrochloric acid, and then extracted with toluene and the solvent toluene was distilled off to obtain 108 g of a polyoxyalkylene compound. Next, 81.0 g of this polyoxyalkylene compound (0.
04 mol equivalent: calculated from weight average molecular weight) and toluene 1
8.0 g of liquid phosgene (0.0 g) was added to 00 ml of the mixed solution.
81 mol) was added at 0 ° C., and the reaction was carried out at room temperature for 12 hours while cooling the reflux tube with dry ice. After completion of the reaction, excess phosgene was removed, and toluene as a solvent was distilled off to obtain 76 g of a chlorine-containing compound. Then toluene 1
After cooling a mixed solution of 00 ml, 100 ml of pyridine and 59.6 g (0.4 mol) of triethanolamine to 5 ° C.,
73.1 g of the above-mentioned chlorine-containing compound (equivalent to 0.035 mol: calculated from the weight average molecular weight) was added dropwise, reacted for 3 hours while maintaining the system at 5 ° C, and then reacted for 2 hours at room temperature. After completion of the reaction, unreacted triethanolamine, generated hydrochloride, and toluene as a solvent were removed and purified to obtain 68 g of the target nitrogen-containing compound. This nitrogen-containing compound was an oily liquid having a number average molecular weight of about 2200, and had a dark orange color. As a result of ¹³ C-NMR analysis, this nitrogen-containing compound was a random copolymer having an average structure represented by the formula (37).

Embedded image Synthesis Example 8 3.37 g (0.06 mol) of potassium hydroxide contained 1
After placing in a liter autoclave and replacing the system with nitrogen gas, the system is heated to 90 ° C. Then, 100m of toluene
12,9.8 g of 1,1,2-butylene oxide (1.80
Mol) was added thereto and reacted at a reaction temperature of 120 ° C. for 5 hours. After completion of the reaction, the reaction product solution was neutralized with hydrochloric acid, and then extracted with toluene and the solvent toluene was distilled off to obtain 115 g of a polyoxyalkylene compound. Next, this polyoxyalkylene compound 87.3
g (equivalent to 0.04 mol: calculated from the weight average molecular weight) and 100 ml of toluene in a mixed solution of 8.0 g of liquid phosgene.
(0.081 mol) was added at 0 ° C., and the reaction was carried out at room temperature for 12 hours while cooling the reflux tube with dry ice. After completion of the reaction, excess phosgene was removed, and toluene as a solvent was distilled off to obtain 80 g of a chlorine-containing compound. Then 100 ml of toluene, 100 ml of pyridine and morpholine 3
After cooling 4.8 g (0.4 mol) of the mixed solution to 5 ° C., 78.5 g of the above chlorine-containing compound (equivalent to 0.035 mol:
(Calculated from the weight average molecular weight), and the mixture was reacted for 3 hours while maintaining the system at 5 ° C., and then reacted at room temperature for 2 hours.
After the completion of the reaction, unreacted morpholine, generated hydrochloride and toluene as a solvent were removed and purified to obtain 73 g of a desired nitrogen-containing compound. This nitrogen-containing compound was an oily liquid having a number average molecular weight of about 2300, and had a deep orange color. As a result of ¹³ C-NMR analysis, this nitrogen-containing compound was a polymer having an average structure represented by the formula (38).

Embedded image

Examples 1 to 8 and Comparative Example 1 60 parts by volume of catalytic reforming gasoline, 30 parts by volume of catalytic cracking gasoline, and 10 parts by volume of alkylate were mixed to form a base gasoline (gasoline for an internal combustion engine) having the following properties: Was prepared. Base gasoline properties Reed vapor pressure: 0.65 kgf / cm2 Specific gravity: 0.727 Boiling range: 30 to 190 ° C. Octane number: 98.1 Using the compound, the fuel oil composition according to the present invention was prepared according to the formulation shown in each example (Examples 1 to 8) in Table 1. The following engine evaluation tests were performed on each of these fuel oil compositions. The results are shown in Table 1.

[Engine Evaluation Test] Using a passenger car equipped with a direct injection gasoline engine having a displacement of 1.8 L and repeating the 10.15 mode for 400 hours,
Exhaust gas is collected according to the 0.15 mode, and THC
(Total HydroCarbon) emissions were measured. Furthermore, drive at a constant speed of 40 km / h, and Bosch
The amount of smoke is measured by sampling 5 times the amount with a formula smoke meter, then the engine is disassembled and the amount of deposit in the combustion chamber is measured.
The difference between the amount of smoke and the amount of deposit in the combustion chamber was determined.

[0041]

[Table 1]

As is clear from the results of the engine evaluation test shown in Table 1, the gasoline compositions of Examples 1 to 8 according to the present invention can reduce deposits in the combustion chamber in any direct injection type gasoline engine. it can. In particular, the rate of reduction of the amount of deposit in the cavity to which the fuel directly hits during stratified combustion is large, and an increase in the amount of THC and the amount of smoke, which is considered to be caused by control disturbance caused by adsorption of fuel to the deposit and the like, can be suppressed. .

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Atsushi Akimoto, Inventor at 8 Chidori-cho, Naka-ku, Yokohama-shi, Kanagawa Prefecture Inside Japan Petroleum Research Institute, Inc. (72) Inventor Masahiro Yoshida 8 Chidori-cho, Naka-ku, Yokohama-shi, Kanagawa Japan Petroleum Co., Ltd.

Claims (1)

[Claims] 1. A gasoline additive for a direct injection gasoline engine comprising a nitrogen-containing compound represented by the following general formula (1). Embedded image (In the general formula (1), R ¹ is hydrogen or carbon number 1 to
R ² , R ³ , R ⁴ and R ⁵ each independently represent hydrogen, a hydrocarbon group having 1 to 16 carbon atoms or a group represented by the following general formula (2); Is 1 to 200
R ⁶ represents a hydrocarbon group having 1 to 10 carbon atoms, b represents 0 or 1, Z represents a group selected from Group A, c represents 0 or 1, and X represents Represents a group selected from the following group B, d is an integer of 1 to 3, e is an integer of 0 to 2, and d + e = 3. ) (In the general formula (2), R ⁷ and R ⁸ are each independently hydrogen, a hydrocarbon group having 1 to 10 carbon atoms or 2 to 2 carbon atoms.
10 represents an alkoxyalkyl group, and R ⁹ has 2 to 2 carbon atoms.
6 represents an alkylene group or a C 4-10 alkylene group having an alkoxyalkyl group as a substituent; R ¹⁰ represents hydrogen or a hydrocarbon group having 1-30 carbon atoms; Indicates an integer of 50. A group: A1: —O—CO— A2: —CO— A3: —O—CO—R ¹¹ — (R ¹¹ represents an alkylene group having 1 to 6 carbon atoms) A4: —O—CO—O—R ¹² - (R ¹² represents an alkylene group having 1 to 6 carbon atoms) A5: -CO-O-R 13 - (R 13 represents an alkylene group having 1 to 6 carbon atoms) B group B1: hydrogen B2: carbon A hydrocarbon group of Formulas 1 to 30 B3: an alkanol group represented by the following general formula (3) -R ¹⁴ -OH (3) (In the general formula (3), R ¹⁴ represents an alkylene group having 1 to 6 carbon atoms. B4: Nitrogen-containing group represented by the following general formula (4): (In the 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 hydrogen, a hydrocarbon group having 1 to 30 carbon atoms, or a group represented by the above general formula (3), and g represents an integer of 1 to 5.) B5: represented by the following general formula (5) Group (In the general formula (5), R ¹⁸ represents an alkylene group having 2 to 6 carbon atoms, and R ¹⁹ , R ²⁰ , R ²¹ and R ²² each independently represent hydrogen, a hydrocarbon group having 1 to 10 carbon atoms or a hydroxyl group. And Y represents a methylene group, a methylene group substituted with a hydrocarbon group having 1 to 10 carbon atoms or a hydroxyl group, an imino group, an imino group substituted with a hydrocarbon group having 1 to 10 carbon atoms or a hydroxyl group, or oxygen. , H is 1 when e = 1, 0 or 1 when e = 2 (however, when h = 0, N (nitrogen) in the general formula (5) is represented by the general formula (1 (Corresponds to N (nitrogen) in))