JPH1036864A - Fuel oil additive and fuel oil composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To effectively clean the deposit on an inlet system by compounding gasoline for internal combustion engines with a specified amt. of an amine compd. represented by a specific formula as a fuel oil additive. SOLUTION: A mixture of an epoxy compd. and an oxirane compd. is polymerized by using a basic catalyst and a reaction initiator to give a polyoxyalkylene compd., which is reacted with phosgene to give a chlorine-contg. compd. This compd. is added to an alkanolamine soln. and is reacted therewith to give an amine compd. represented by formula I [wherein R<1> is H or a 1-30C hydrocarbon group; R<2> to R<5> are each H, a 1-10C hydrocarbon group, or a group represented by formula II (wherein R<9> and R<10> are each H, a 1-10C hydrocarbon group, etc.; R<11> is a 2-6C alkylene, etc.; R<12> is H, a 1-30C hydrocarbon group, etc.; and f is 0-50); R<6> is a 2-6C alkylene; R<7> and R<8> are each a 1-6C alkylene; (a) is 1-100; (b) is 0-100, etc.; (c) is 0 or 1; (d) and (e) are each 1, 2, etc.; and X is a group represented by formula III (wherein R<3> is a 1-6C lakylene)]. A fuel oil compsn. is prepd. by adding 0.005-5 mass % fuel oil additive contg. the amine compd. to gasoline for internal combustion engines.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a fuel oil additive and a fuel oil composition containing the additive, and more particularly to a fuel oil having excellent solubility in fuel oil, and particularly to cleaning of the intake system and combustion chamber of a gasoline engine. The present invention relates to a fuel oil additive having excellent properties and a fuel oil composition containing the additive.

[0002]

2. Description of the Related Art When deposits such as sludge and deposits are formed in a fuel system or a combustion chamber of an internal combustion engine, the function of the engine is reduced, and the concentrations of carbon monoxide and unburned hydrocarbons in exhaust gas are increased. Inconveniences such as occur. For this reason, fuel oils such as gasoline are typically represented by gasoline detergents such as polyetheramines and polyamines, mainly for the purpose of removing deposits and preventing adhesion of vaporizers, electronically controlled injection devices, and intake valves. Often, added fuel additives are added. Among such fuel additives, US Pat. No. 4,247,301 and US Pat.
The polyether-based gasoline detergent disclosed in U.S. Pat. No. 0,648 and the like has exhibited excellent performance in removing deposits and preventing adhesion of intake valves.

[0003]

However, in recent years, there has been an interest in reducing the fuel consumption of automobiles and eliminating the adverse effects of automobile exhaust gas on the human body and the environment. Against this background, compared to conventional gasoline detergents such as polyetheramines and polyamines, cleanliness in the intake system and combustion chamber of gasoline engines is much better, especially in severe conditions such as when the engine is cold. The development of fuel oil additives that exhibit excellent cleaning effects even under difficult conditions has been awaited.
The present inventors have conducted studies to develop a fuel oil additive having better cleanliness in the intake system and the combustion chamber of a gasoline engine. The present inventors have found that they have excellent performance, and have completed the present invention. Accordingly, one of the objects of the present invention is to provide a novel fuel oil additive comprising a special amine compound which has performance exceeding that of conventional gasoline detergents and does not itself become sludge. is there. Another object of the present invention is to provide a fuel oil composition containing a novel fuel oil additive.

[0004]

The fuel oil additive according to the present invention comprises an amine compound represented by the following general formula (1). The fuel oil composition according to the present invention is applicable to gasoline for internal combustion engines. On the other hand, the amine compound represented by the general formula (1) is
0.005 to 5% by mass based on the total amount of the composition.

Embedded image In the general formula (1), R ¹ is hydrogen or a group having 1 to 3 carbon atoms.
0 represents a hydrocarbon group, and R ² , R ³ , R ⁴ and R ⁵ each independently represent hydrogen, a hydrocarbon group having 1 to 10 carbon atoms or a group represented by the following general formula (2) ( Where R ² ,
At least one of R ³ , R ⁴ and R ⁵ is a group represented by the general formula (2)), R ⁶ is an alkylene group having 2 to ⁶ carbon atoms, and R ⁷ and R ⁸ are each independently Carbon number 1
A represents 1 to 100, b represents 0 to 1
An integer of 00, a + b = 1 to 200, and c is 0
Or 1, d and e are each independently an integer of 1 or 2, and d + e = 3, and when e = 1, X is a group represented by the following general formula (3); When = 2, at least one is a group represented by the general formula (3), and the other is a hydrocarbon group having 1 to 30 carbon atoms or a group represented by the general formula (3).

Embedded image In the general formula (2), R ⁹ and R ¹⁰ are each independently hydrogen, a hydrocarbon group having 1 to 10 carbon atoms, or a hydrocarbon group having 2 to 2 carbon atoms.
10 represents an alkoxyalkyl group, and R ¹¹ 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 ¹² represents hydrogen or a hydrocarbon group having 1 to 30 carbon atoms; Indicates an integer of 50.

Embedded image In the general formula (3), R ¹³ represents an alkylene group having 1 to 6 carbon atoms.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION In the general formula (1) representing the amine compound of the present invention, R ¹ is hydrogen or a group having 1 to 3 carbon atoms.
0 represents a hydrocarbon group, wherein R ¹ is hydrogen, or a linear or branched alkyl group having 1 to 24 carbon atoms;
A linear or branched alkenyl group having 2 to 24 carbon atoms,
It is preferably any of a cycloalkyl group or an alkylcycloalkyl group having 5 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,
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 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,
Straight or branched pentadecyl group, straight or branched hexadecyl group, straight or branched heptadecyl group, straight or branched octadecyl group, straight or branched nonadecyl group, straight or branched icosyl group, straight chain 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 icodecenyl group, Straight or branched henicocenyl, straight or branched docosenyl, straight or branched tricosenyl, straight or branched Such as Rakoseniru groups are included. 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), linear 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 group (including all substituted isomers), di-linear or branched propylcyclopentyl group (including all substituted isomers), linear or branched propylethylmethylcyclopentyl group (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), Chain or branched propylmethylcyclohexyl groups (including all substituted isomers), linear or branched propylethylcyclohexyl groups (including all substituted isomers), di-linear or branched propylcyclohexyl groups (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) ), An ethylcycloheptyl group (including all substituted isomers), a linear or branched propylcycloheptyl group (including all substituted isomers), and an ethylmethylcycloheptyl group (including all substituted isomers). ), Trimethylcycloheptyl group (including all substituted isomers), diethylcycloheptyl group (including All substituted isomers), ethyldimethylcycloheptyl group (including all substituted isomers), linear or branched propylmethylcycloheptyl group (including all substituted isomers), linear 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) and the like. Preferred aryl groups as R ¹ include a phenyl group, a naphthyl group and the like, 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 Straight or branched butylphenyl group (including all substituted isomers), straight or branched propylmethylphenyl group (including all substituted isomers), diethylphenyl group (including all substituted isomers) All substituted isomers), ethyldimethylphenyl group (including all substituted isomers), tetramethylphenyl group (including all substituted isomers) ), A linear or branched pentylphenyl group (including all substituted isomers), a linear or branched hexylphenyl group (including all substituted isomers), a linear or branched heptylphenyl group (including all substituted isomers). Straight or branched octylphenyl group (including all substituted isomers), straight or branched nonylphenyl group (including all substituted isomers), straight or branched Decylphenyl group (including all substituted isomers), linear or branched undecylphenyl group (including all substituted isomers), linear or branched dodecylphenyl group (including all substituted isomers), etc. And also preferred arylalkyl groups include benzyl, methylbenzyl (including all substituted isomers), dimethylbenzyl (including all substituted isomers), Examples include a phenethyl group, a methylphenethyl group (including all substituted isomers), a dimethylphenethyl group (including all substituted isomers), and the like. Among these,
R ¹ is more preferably a straight-chain or branched alkyl group having 1 to 12 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms or an alkylaryl group. Most preferably, it is a linear or branched alkyl group having 1 to 6, a phenyl group, or a linear or branched alkylaryl group having 7 to 9 carbon atoms.

R ² , R ³ , R ⁴ and R ⁵ in the general formula (1) each independently represent hydrogen, a hydrocarbon group having 1 to 10 carbon atoms or a group represented by the general formula (2) ( However,
At least one of R ² , R ³ , R ⁴ and R ⁵ is a group represented by the general formula (2)). 1 to 1 carbon atoms
The 10 hydrocarbon groups include a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkenyl group having 2 to 10 carbon atoms, and a cycloalkyl having 5 to 10 carbon atoms. Group or alkylcycloalkyl group, aryl group or alkylaryl group having 6 to 10 carbon atoms, 7 to 10 carbon atoms
Arylalkyl group and the like. And preferred alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,
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 group, A straight-chain or branched decyl group and the like are mentioned, and similarly preferred alkenyl groups include a vinyl group,
Propenyl, isopropenyl, straight or branched butenyl, butadienyl, straight or branched pentenyl, straight or branched hexenyl, straight or branched heptenyl, straight or branched octenyl, A straight-chain or branched nonenyl group, a straight-chain or branched decenyl group and the like can be mentioned. 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 propylethylcyclopentyl group (including all substituted isomers) ), A methylcyclohexyl group (including all substituted isomers), a dimethylcyclohexyl group (including all substituted isomers), an ethylcyclohexyl group (including all substituted isomers), a linear or branched propylcyclohexyl group (including All substituted isomers), ethylmethylcyclohexyl group (including all substituted isomers), trimethylcyclohexyl group (including all substituted isomers), diethylcyclohexyl group (including all substituted isomers), ethyl Dimethylcyclohexyl group (including all substituted isomers), straight chain 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), trimethylcycloheptyl group (including all And the like.) Preferred aryl groups include a phenyl group and a naphthyl group. Preferred alkylaryl groups include a tolyl group (including all substituted isomers), a xylyl group (including all substituted isomers), and ethyl. Phenyl group (including all substituted isomers), linear or branched propylphenyl group (including all substituted isomers), ethylmethylphenyl group (including all substituted isomers), trimethylphenyl group (including all substituted isomers) Straight or branched butylphenyl group (including all substituted isomers), linear or branched propylmethylphenyl group (including all substituted isomers), diethylphenyl group (including all substituted isomers) Ethyldimethylphenyl group (including all substituted isomers), tetramethylphenyl group (including all substituted isomers) The included), and the like. Preferred arylalkyl groups include a benzyl group, a methylbenzyl group (including all substituted isomers),
Examples include a dimethylbenzyl group (including all substituted isomers), a phenethyl group, a methylphenethyl group (including all substituted isomers), and a dimethylphenethyl group (including all substituted isomers). Among the above-mentioned hydrocarbon groups having 1 to 10 carbon atoms, straight-chain or branched alkyl groups having 1 to 6 carbon atoms are even more preferable, and particularly, straight-chain or branched alkyl groups having 1 to 3 carbon atoms. Is most preferred.

One of R ² , R ³ , R ⁴ and R ^{5 in} the general formula (1) is a group represented by the general formula (2). ⁹ and R ¹⁰ Waso respectively individually represent a hydrogen, an alkoxyalkyl group or a hydrocarbon group having 2 to 10 carbon atoms having 1 to 10 carbon atoms.
Here, the hydrocarbon group having 1 to 10 carbon atoms includes R ^{2 to} R ⁵
A linear or branched alkyl group having 1 to 10 carbon atoms described above, a linear or branched alkenyl group having 2 to 10 carbon atoms, a cycloalkyl group or alkyl having 5 to 10 carbon atoms Cycloalkyl group, aryl group having 6 to 10 carbon atoms or alkylaryl group and 7 to 7 carbon atoms
All 10 arylalkyl groups and the like are included. The above-mentioned alkoxyalkyl group having 2 to 10 carbon atoms includes, 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 (all Octoxymethyl group (including all isomers), 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), methoxy (Including all isomers) propyl group, an ethoxypropyl group (including all isomers),
Propoxypropyl group (including all isomers), butoxypropyl group (including all isomers), pentoxypropyl group (including all isomers), hexoxypropyl group (including all isomers), Heptoxypropyl group (including all isomers), methoxybutyl group (including all isomers), ethoxybutyl group (including all isomers), propoxybutyl group (including all isomers), butoxy Butyl 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), (Including all isomers) Tokishipenchiru group, (including all isomers) methoxy hexyl, ethoxy hexyl (including all isomers),
Propoxyhexyl group (including all isomers), butoxyhexyl group (including all isomers), methoxyheptyl group (including all isomers), ethoxyheptyl group (including all isomers), propoxyheptyl Groups (including all isomers), methoxyoctyl groups (including all isomers), ethoxyoctyl groups (including all isomers), methoxynonyl groups (including all isomers), and the like. R ⁹ and R ¹⁰ in the general formula (2) are preferably 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 1 to 6 carbon atoms. Even more preferably, it is an alkyl group of 3. R ¹¹ in the general formula (2) is an alkylene group having 2 to 6 carbon atoms or a total of 4 to 4 carbon atoms having an alkoxyalkylene group as a substituent.
And 10 alkylene groups. Examples of the alkylene group having 2 to 6 carbon atoms include an ethylene group, a propylene group (1-methylethylene group, a 2-methylethylene group), a trimethylene group, and a butylene group (1-ethylethylene group,
-Ethylethylene group), 1,2-dimethylethylene group,
2,2-dimethylethylene group, 1-methyltrimethylene group, 2-methyltrimethylene group, 3-methyltrimethylene group, tetramethylene group, pentylene group (1-butylethylene group, 2-butylethylene group), -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, 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, -Propyl trimethylene group,
3-propyl trimethylene group, 1-ethyl-1-methyl trimethylene group, 1-ethyl-2-methyl trimethylene group, 1-ethyl-3-methyl trimethylene group, 2-ethyl-1-methyl trimethylene 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-dimethyl Tetramethylene group, 2,4-dimethyltetramethylene group, 3,3-dimethyltetramethylene group, 3,4-dimethyltetramethylene group, 4,4-dimethyltetramethylene group, 1-methylpentamethylene group, 2-methyl Pentamethylene group, 3
-Methylpentamethylene group, 4-methylpentamethylene group, 5-methylpentamethylene group, hexamethylene group and the like. Examples of the alkylene group having a total number of carbon atoms of 4 to 10 containing the alkoxyalkylene group as R ¹¹ 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-methoxymethylethylene 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-
Total carbon number 2 exemplified by a methyl-2-methoxyethylethylene group, a 1-methoxyethyl-2-methylethylene group, a 1-ethyl-2-methoxyethylethylene group, a 1-methoxyethyl-2-ethylethylene group, and the like. ~ 8 alkoxyalkylene-substituted ethylene groups are preferred. And
R ^{11 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. R ¹² in the general formula (2) represents hydrogen or a hydrocarbon group having 1 to 30 carbon atoms, and R ¹² is hydrogen or a linear or linear group having 1 to 24 carbon atoms described above for R ^1. A 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 having 6 to 18 carbon atoms It is preferably any one of a group and an arylalkyl group having 7 to 19 carbon atoms. Further, R ¹¹ is more preferably an alkyl group having 1 to 24 carbon atoms, and particularly preferably an alkyl group having 1 to 12 carbon atoms. F in the general formula (2) may be any integer in the range of 0 to 50,
It is preferably an integer of 0 to 30, more preferably 0 to 20. Accordingly, in the group represented by the general formula (2), R ⁹ and R ¹⁰ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 6 carbon atoms,
R ¹¹ is an alkylene group having 2 to 6 carbon atoms or a total of 2 to 2 carbon atoms;
8 is an alkoxyalkylene-substituted ethylene group,
¹² is an alkyl group having 1 to 24 carbon atoms, and f is 0 to
It is preferably an integer of 30 (hereinafter, this group is referred to as “preferred substituent” for convenience). And R ⁹ and R
¹⁰ is each independently hydrogen or an alkyl group having 1 to 3 carbon atoms, R ¹¹ is an alkylene group having 2 to 4 carbon atoms,
R ¹² is an alkyl group having 1 to ¹² carbon atoms, and f is 0
Those having an integer of from 20 to 20 are more preferable (hereinafter, this group is referred to as "more preferable substituent" for convenience). The amine compound of the present invention is a compound represented by the general formula (1) wherein R ² , R ³ , R
It is important that at least one of ⁴ and R ⁵ is a group represented by the general formula (2), but R ² , R ³ , R ⁴ and R ⁵
Is preferably a group selected from the groups represented by the general formula (2), and the remaining three or two are preferably each independently hydrogen or an alkyl group having 1 to 6 carbon atoms. More specifically, one of R ² , R ³ , R ⁴ and R ⁵ is the above “preferred substituent” or “more preferred substituent”, and the other three are each independently hydrogen or a group having 1 to 3 carbon atoms. Even more preferably, it is an alkyl group.

In the general formula (1), R ⁶ has 2 to ⁶ carbon atoms.
The alkylene group includes, for example, ethylene group, propylene group (1-methylethylene group, 2-methylethylene group), trimethylene group, butylene group (1-ethylethylene group, 2-ethylethylene group). Group), 1,2-dimethylethylene group, 2,2-dimethylethylene group, 1-methyltrimethylene group, 2-methyltrimethylene group, 3-methyltrimethylene group, tetramethylene group, pentylene group (1-butyl Ethylene group, 2-butylethylene 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-methylpentamethylene group, hexamethylene group and the like are included. Among these, an alkylene group having 2 to 4 carbon atoms is preferable, and specifically, an ethylene group, a propylene group (1-methylethylene group, a 2-methylethylene group), a trimethylene group, a butylene group (1-ethylethylene group) , 2
-Ethylethylene group), 1,2-dimethylethylene group,
Preferred are a 2,2-dimethylethylene group, a 1-methyltrimethylene group, a 2-methyltrimethylene group, a 3-methyltrimethylene group, a tetramethylene group and the like.

R ⁷ and R ⁸ in the general formula (1) each independently represent 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), a trimethylene group, a butylene group (1-ethylethylene group, 2-ethylethylene group), , 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, 1,2,2-trimethylethylene group, 1-ethyltrimethylene group, 2-ethyltrimethylene group, 3-ethyltrimethylene group, 1,1-dimethyl Trimethylene 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, 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 A 2,2-diethylethylene group, a 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-trimethyltrimethylene group, 1,1,3-trimethyltrimethylene group, 1,2,2-trimethyltrimethylene group,
1,2,3-trimethyltrimethylene 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-dimethyl Tetramethylene 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-methylpentamethylene group, hexamethylene group and the like. Among them, R ⁷
And R ⁸ are each independently 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), trimethylene group, butylene group (1
-Ethylethylene group, 2-ethylethylene group), 1,2
-Dimethylethylene group, 2,2-dimethylethylene group,
Preferred are a 1-methyltrimethylene group, a 2-methyltrimethylene group, a 3-methyltrimethylene group, a tetramethylene group and the like. Further, R ⁷ and R ⁸ are each independently 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.

The general formula (1) representing the amine compound of the present invention
In the above, a represents an integer of 1 to 100, preferably 5 to 50, b represents an integer of 0 to 100, preferably 0 to 50, and a + b is in the range of 1 to 200, preferably 5 to 100. That is, in the amine compound of the present invention, the group represented by the following general formula (4) has 1 to 100, preferably 5 to 50, structural units represented by the following general formula (5), It preferably contains 5 to 30, and contains 0 to 100, preferably 0 to 50, more preferably 0 to 30, structural units represented by the following general formula (6),
And a total of 1 to 200, preferably 5 structural units represented by general formula (5) and structural units represented by general formula (6)
Contains ~ 100.

Embedded image R ² , R ³ , R ⁴ , R ⁵ and R in the general formula (4)
⁶ represents the same group as R ² , R ³ , R ⁴ , R ⁵ and R ^{6 in the} general formula (1), and a and b also represent the same integer as a and b in the general formula (1).

Embedded image R ^2, R ^3, R ⁴ and R ⁵ in the general formula (5) shows the general formula of (1) to R ^2, R ^3, R ⁴ and R ⁵ the same group.

Embedded image R ⁶ in the general formula (6), R ⁶ in the general formula (1)
And the same group.

The group represented by the general formula (4) is as follows:
Means a group derived from the polymer of Homopolymer composed of one kind of structural unit represented by the general formula (5) (when b = 0) Random copolymer composed of two or more different structural units included in the general formula (5), alternating Copolymer or block copolymer (when b = 0) A random copolymer composed of one type of structural unit represented by general formula (5) and one type of structural unit represented by general formula (6) Combined, alternating copolymer or block copolymer (when b ≠ 0) From two or more different structural units contained in general formula (5) and one type of structural unit represented by general formula (6) A random copolymer, an alternating copolymer or a block copolymer (when b ≠ 0): one structural unit represented by the general formula (5) and two or more structural units represented by the general formula (6) Random copolymers, alternating copolymers or block copolymers composed of different structural units (b ≠ 0 Case) A random copolymer, an alternating copolymer or a block copolymer composed of two or more different structural units included in the general formula (5) and two or more different structural units included in the general formula (6). (When b ≠ 0) When the amine compound according to the present invention is represented by the chemical formula, the amine compound according to the general formula (5) is represented by the general formula (1).
Is bonded to the R ¹ —O— group, However, this display is for the sake of convenience, and the bonding order of the structural unit of the general formula (5) and the structural unit of the general formula (6) is, as shown in (1) to (4) above, Not limited to

In the general formula (1), c represents an integer of 0 or 1. When c = 0, the amine compound represented by the general formula (1) is a compound in which a group represented by the following general formula (7) is directly bonded to a carbon atom of a carbonyl group, It means an amine compound represented by the following general formula (8).

Embedded image R ¹ in the general formula ^{(7), R 2, R} 3, R 4, R 5 and R ^6, R ¹ in the general formula ^{(1), R 2, R} 3, R 4, R 5
And R ⁶ represent the same group, and a and b also represent the same integer as a and b in formula (1).

Embedded image In general formula (8), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ ,
R ⁸ and X represent R ¹ , R ² , R ³ ,
R ⁴ , R ⁵ , R ⁶ , R ⁸ and X represent the same group as
b, d, and e also represent the same integer as a, b, d, and e in the general formula (1). In the case of c = 1, the amine compound represented by the general formula (1), the general formula (7) a group represented by an alkylene group -R ⁷ - to the carbon atom of the carbonyl group through an It refers to a bound compound, that is, an amine compound represented by the following general formula (9).

Embedded image In general formula (9), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ ,
R ⁷ , R ⁸ and X represent R ¹ , R ² ,
R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and X represent the same groups, and a, b, d and e also represent a in formula (1)
, B, d, and e.

In the general formula (1), d and e each independently represent 1 or 2, and each represents an integer such that d + e = 3. Most preferably, d = 1 and e = 2. In the amine compound represented by the general formula (1), d
Is 2, the compound has two groups represented by the following general formula (10) in one molecule. In this case, those groups may have the same structure or different structures. There may be.

Embedded image In general formula (10), R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
R ⁶ , R ⁷ and R ⁸ represent R ¹ , R ² in the general formula (1)
R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 represent the} same groups, and a, b and c also represent the same integers as a, b and c in formula (1). .

The general formula (1) representing the amine compound of the present invention
In the formula, X represents a group represented by the following general formula (3) when e = 1, and at least one represents a group represented by the general formula (3) when e = 2; Represents a hydrocarbon group having 1 to 30 carbon atoms or a group represented by the general formula (3). However, it is particularly preferred that both X's are groups represented by the general formula (3).

Embedded image In the general formula (3), R ¹³ represents an alkylene group having 1 to 6 carbon atoms. In the above general formula (3), specific examples of the alkylene group represented by R ¹³ include the alkylene groups described above for R ⁸ .
4 is preferred, and specifically, methylene, ethylene, propylene (1-methylethylene, 2-methylethylene), trimethylene, butylene (1-ethylethylene, 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, R ¹³ has 1 carbon atom
Most preferred are alkylene groups (1) to (3), specifically, methylene, ethylene, propylene (1-methylethylene, 2-methylethylene) or trimethylene. Preferred examples of the hydrocarbon group having 1 to 30 carbon atoms that X can take include the linear or branched alkyl group having 1 to 24 carbon atoms described above for R ^{1 in the} general formula (1). 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 having 6 to 18 carbon atoms, 19 arylalkyl groups and the like. Among them, carbon number 1 to 1
A linear or branched alkyl group of 2 or 6 carbon atoms
An aryl group or an alkylaryl group having 12 to 12 carbon atoms is more preferable, and an alkyl group having 1 to 6 carbon atoms, a phenyl group or an alkylaryl group having 7 to 9 carbon atoms is most preferable.

The substituents of the general formula (1), which generally represent the amine compound of the present invention, have been individually described above. Preferred examples of the amine compound of the present invention are those represented by the general formula (1) ¹ is a linear or branched alkyl group having 1 to 12 carbon atoms, or an aryl group or an alkylaryl group having 6 to 12 carbon atoms, and R ² , R ³ , R
1 and 2 of ⁴ and R ⁵ are a group represented by the general formula (2), and the other 3 to 2 are each independently a hydrogen or an alkyl group having 1 to 6 carbon atoms; In 2), R ⁹ and R ¹⁰ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 6 carbon atoms, and R ¹¹ is an alkylene group having 2 to 6 carbon atoms or the total number of carbon atoms. 2 to 8, an alkoxyalkylene-substituted ethylene group, R ¹² is an alkyl group having 1 to 24 carbon atoms, and f
Is an integer of 0 to 30; R ⁶ is a group selected from alkylene groups having 2 to 4 carbon atoms; R ⁷ and R ⁸ are each independently an alkylene group having 1 to 4 carbon atoms; 1 to 10
0 and b are integers of 0 to 100, and a + b = 1 to
200, c is an integer of 0 or 1, and d is 1 to
2, when e is an integer of 1 to 2 and d + e = 3, and d = 1 and e = 2, one of X is a group represented by the general formula (3) or a carbon number of 1 And another one is a group represented by the general formula (3),
When d = 2 and e = 1, X is a group represented by the general formula (3), and in the general formula (3), R ¹³ is an alkylene group having 1 to 4 carbon atoms. It is.

[0016] Even more preferred as the amine compound of the invention, R ¹ in the general formula (1) is an alkyl group, a phenyl group or an alkyl aryl group having a carbon number of 7 to 9 from 1 to 6 carbon atoms, R ^2, One of R ³ , R ⁴ and R ⁵ is a group represented by the general formula (2), and the remaining three are each independently hydrogen or an alkyl group having 1 to 3 carbon atoms. )), R ⁹ and R ¹⁰ are each independently hydrogen or an alkyl group having 1 to 3 carbon atoms, and R ¹¹ is a group having 2 to 2 carbon atoms.
4, R ¹² is an alkyl group having 1 to 12 carbon atoms, f is an integer of 0 to 20, and R ⁶ is an ethylene group, a propylene group (1-methylethylene group, 2
-Methylethylene group), trimethylene group, butylene group (1-ethylethylene group, 2-ethylethylene group),
Alkylene having 2 to 4 carbon atoms selected from 1,2-dimethylethylene group, 2,2-dimethylethylene group, 1-methyltrimethylene group, 2-methyltrimethylene group, 3-methyltrimethylene group, and tetramethylene group R ⁷
And R ⁸ are each independently a methylene group, an ethylene group,
A propylene group (1-methylethylene group, 2-methylethylene group), an alkylene group having 1 to 3 carbon atoms selected from a trimethylene group, a is an integer of 5 to 50, b is an integer of 0 to 50, and a + b = 5 to 100, c is an integer of 0 or 1, d = 1 and e = 2, and X is (A) a group represented by the general formula (3); In (3), R ¹³ is an alkylene group having 1 to 3 carbon atoms.
Such an amine compound.

The amine compound according to the present invention can be produced by any method. For example,
The amine compound of the present invention represented by the aforementioned general formula (8) can be synthesized through (A) a polymerization step, (B) a chloroformate step, and (C) a carbonic esterification step. (A) 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 (11) as a reaction initiator, and a compound represented by the general formula (12) The oxygen-containing compound represented by the general formula (11) is used as a reaction initiator to polymerize the epoxy compound represented by the formula (11). The epoxy compound represented by the general formula (12) and the epoxy compound represented by the general formula (13) are used. Polymerizing a mixture with an oxirane compound A homopolymer of an epoxy compound of the general formula (12) is obtained by using an oxygen-containing compound represented by the general formula (11) as a reaction initiator. Polymerization of oxirane compound An oxirane compound represented by the general formula (13) is obtained by using an oxygen-containing compound represented by the general formula (11) as a reaction initiator, and then a homopolymer of the oxirane compound represented by the general formula (13). After a polymerization product (in the form of a metal alkoxide) is obtained by a method such as polymerizing the epoxy compound of 12), this is neutralized with an acid such as hydrochloric acid to obtain a compound represented by the general formula (14). (In the case of b ≠ 0, both the case where the polyoxyalkylene glycol derivative represented by the general formula (14) is a random copolymer and the case where the polyoxyalkylene glycol derivative is a block copolymer) included).

Embedded image R ¹ R ¹ in the general formula (11) in the general formula (1)
And the same group.

Embedded image R ^2, R ^3, R ⁴ and R ⁵ in the general formula (12) shows the general formula of (1) to R ^2, R ^3, R ⁴ and R ⁵ the same group.

Embedded image Formula (13) represents an oxirane compound in which two hydrogen atoms bonded to any two carbon atoms in the alkylene group R ⁶ are substituted with one oxygen atom to form an alkoxy group, R ⁶ represents the same alkylene group as R ⁶ in formula (1).

Embedded image R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ in the general formula (14) represent R ¹ , R ² , R ³ , R ⁴ ,
It represents the same group as R ⁵ and R ^6, and a and b also represent the same integer as a and b in the general formula (1). Preferred examples of the epoxy compound represented by the general formula (12) include 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,
Straight or branched heptyl glycidyl ether, straight or branched octyl glycidyl ether, straight or branched nonyl glycidyl ether, straight or branched decyl glycidyl ether, straight or branched undecyl glycidyl ether Linear or branched dodecyl glycidyl ether, linear or branched tridecyl 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 or branched hexadecyl glycidyl ether, linear or branched octadecyl glycidyl ether, vinyl glycidyl ether, linear or branched propenyl glycidyl ether Linear or branched butenyl glycidyl ether, linear 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, linear or branched tetradecenyl glycidyl ether, linear or branched pentadecenyl glycidyl ether, linear or branched hexadecenyl glycidyl Ether, linear or branched heptadecenyl glycidyl ether, linear or branched Is a 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 butyl phenyl glycidyl ether, straight or branched pentyl phenyl glycidyl ether, straight or branched hexyl phenyl glycidyl ether, straight or branched heptyl phenyl glycidyl ether, straight 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 Nyl 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-2,5,1
0,13-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. Preferred examples of the oxirane compound represented by the general formula (13) include ethylene oxide, propylene oxide, isobutylene oxide, 1-butene oxide (1,2-butylene oxide), 2-butene oxide, and 1-butene oxide. Examples include pentene oxide, trimethylethylene oxide, 1-hexene oxide, and tetramethylethylene oxide. An oxygen-containing compound of the general formula (11) and a general formula (12)
Or the molar ratio when reacting a mixture of an oxygen-containing compound of the general formula (11), an epoxy compound of the general formula (12) and an oxirane compound of the general formula (13). Can be arbitrarily selected, but usually, it is preferable to react 5 to 100 mol of the epoxy compound or a mixture of the epoxy compound and the oxirane compound with respect to 1 mol of the oxygen-containing compound. The reaction temperature in the polymerization step is also arbitrary, but is usually 60 to
The temperature is preferably 180 ° C, more preferably 80 to 150 ° C. (B) Chloroformate-forming step The polyoxyalkylene glycol derivative of the general formula (14) obtained in the above-mentioned polymerization step or the metal alkoxide compound before its neutralization is treated with an excess amount of phosgene, for example, at room temperature for chloroformate. To obtain a chlorine-containing compound represented by the general formula (15).

Embedded image R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ in the general formula (15) represent R ¹ , R ² , R ³ , R ⁴ ,
It represents the same group as R ⁵ and R ^6, and a and b also represent the same integer as a and b in the general formula (1). (C) Carbonic acid esterification step General formula (1) obtained in the above-mentioned chloroformate formation step
The amine compound of the present invention can be obtained by reacting the chlorine-containing compound of 5) with an alkanolamine represented by the general formula (16).

Embedded image R ⁷ and X in the general formula (16) are represented by the general formula (1)
And the same groups as R ⁷ and X in the above. However, two Xs contained in the compound represented by the general formula (16) may have the same structure or different structures. Particularly preferred examples of the alkanolamine represented by the general formula (16) include trimethanolamine, methyldimethanolamine, ethyldimethanolamine, triethanolamine, methyldiethanolamine, ethyldiethanolamine, and tri-n-propanolamine. , Methyl-di-n-propanolamine, ethyl-di-n-propanolamine, triisopropanolamine, methyldiisopropanolamine, ethyldiisopropanolamine, tri (linear or branched) butanolamine, methyldi (linear or Branch) butanolamine, ethyldi (linear or branched) butanolamine, tri (linear or branched) pentanolamine, methyldi (linear or branched) pentanolamine, ethyldi (linear or branched) Mention may be made of alkanolamines such as ethanol amine. The molar ratio when the chlorine-containing compound of the general formula (15) is reacted with the alkanolamine of the general formula (16) in the carbonic acid esterification step can be arbitrarily selected. And at least one alkanolamine
The reaction is preferably performed in an amount of at least one mole, and more preferably 1 to 20 moles. In addition, the reaction temperature in the carbonic acid esterification step is also arbitrary, but is usually preferably −20 to 150 ° C., and more preferably −10 to 80 ° C. Alternatively, instead of employing the (B) chloroformate step and (C) carbonate esterification step described above, the (A)
Following the polymerization step, the following (D) ester group introduction step and (E)
By employing the transesterification step, the amine compound of the present invention represented by the general formula (9) can be synthesized. (D) The polyoxyalkylene glycol derivative of the general formula (14) obtained in the polymerization step of the ester group introduction step (A) or the metal alkoxide compound before neutralization thereof is represented by the following general formula (17) By reacting with a monohalocarboxylic acid ester, a compound of the general formula (1)
An ester compound represented by 8) is obtained.

Embedded image R ⁷ is R ⁷ in the general formula (17) in the general formula (1)
And R ¹⁴ represents a hydrocarbon group having 1 to 30 carbon atoms, and Y represents chlorine, bromine or iodine.

Embedded image R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ in the general formula (18)
And R ⁷ are R ¹ , R ² , R ³ , and R in the general formula (1).
^4, R ^5, R ⁶ and R ⁷ represent the same group and, R ¹⁴ in the general formula (17) indicates the same group as R ^14, identical to a and b in a and b are the general formula (1) Indicates an integer.
In the general formula (17) representing the mono-halo carboxylic ester, the R ¹⁴ is a hydrocarbon group having 1 to 30 carbon atoms, R ¹⁴ is a linear or branched alkyl group having 1 to 24 carbon atoms A straight-chain 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 having 6 to 18 carbon atoms, It is preferably any one of 19 arylalkyl groups. Preferred alkyl groups as R ¹⁴ 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,
Straight or branched nonyl group, straight or branched decyl group, straight or branched undecyl group, straight or branched dodecy group,
Straight or branched tridecyl, straight or branched tetradecyl, straight or branched pentadecyl, straight or branched hexadecyl, straight or branched heptadecyl, straight or branched octadecyl, straight Or a branched nonadecyl group, a linear or branched icosyl group, a linear or branched henicosyl group, a linear or branched docosyl group, a linear or branched tricosyl group, a linear or branched tetracosyl group, etc. . Preferred alkenyl groups for R ¹⁴ include vinyl, propenyl, isopropenyl, linear or branched butenyl, butadienyl, linear or branched pentenyl, linear or branched hexenyl, linear or branched hexenyl. Branched heptenyl, straight or branched octenyl, straight or branched nonenyl, straight or branched decenyl, straight or branched undecenyl, straight or branched dodecenyl, straight or branched tridecenyl Linear or branched octadecenyl group such as a group, linear or branched tetradecenyl group, linear or branched pentadecenyl group, linear or branched hexadecenyl group, linear or branched heptadecenyl group, oleyl group, etc. Branched nonadecenyl group, straight-chain or branched icosenyl group, straight-chain or branched henicosenyl group,
A straight or branched docosenyl group, a straight or branched tricosenyl group, a straight or branched tetracosenyl group and the like are included. Preferred cycloalkyl groups as R ¹⁴ 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), linear 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 group (including all substituted isomers), di-linear or branched propylcyclopentyl group (including all substituted isomers), linear or branched propylethylmethylcyclopentyl group (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) ), An ethyldimethylcyclohexyl group (including all substituted isomers), Chain or branched propylmethylcyclohexyl groups (including all substituted isomers), linear or branched propylethylcyclohexyl groups (including all substituted isomers), di-linear or branched propylcyclohexyl groups (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) ), An ethylcycloheptyl group (including all substituted isomers), a linear or branched propylcycloheptyl group (including all substituted isomers), and an ethylmethylcycloheptyl group (including all substituted isomers). ), Trimethylcycloheptyl group (including all substituted isomers), diethylcycloheptyl group (including All substituted isomers), ethyldimethylcycloheptyl group (including all substituted isomers), linear or branched propylmethylcycloheptyl group (including all substituted isomers), linear or branched Propylethylcycloheptyl (including all substituted isomers), di-linear or branched propylcycloheptyl (including all substituted isomers), linear or branched propylethylmethylcycloheptyl (including all substituted isomers) Cycloalkyl or alkylcycloalkyl groups, including substituted isomers). Preferred aryl groups as R ¹⁴ include a phenyl group, a naphthyl group and the like, and similarly preferred alkylaryl groups include a tolyl group (including all substituted isomers) and a 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), trimethylphenyl group (Including all substituted isomers), linear or branched butylphenyl group (including all substituted isomers), linear or branched propylmethylphenyl group (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 all substituted isomers), linear or branched hexylphenyl group (including all substituted isomers), linear or branched heptylphenyl group (Including all substituted isomers), linear or branched octylphenyl group (including all substituted isomers), linear or branched nonylphenyl group (including all substituted isomers), linear or branched Branched decylphenyl group (including all substituted isomers), linear or branched undecylphenyl group (including all substituted isomers), linear or branched dodecylphenyl group (including all substituted isomers) And the like, and preferred arylalkyl groups include a benzyl group, a methylbenzyl group (including all substituted isomers), and a dimethylbenzyl group (including all substituted isomers). Phenethyl group (including all isomers) ethylbenzyl group, (including all isomers) dimethyl phenethyl group and the like are included. Among these,
R ¹⁴ is more preferably a straight-chain or branched alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms or an alkylaryl group, particularly preferably Most preferably, it is a linear or branched alkyl group of 1 to 6, a phenyl group, or a linear or branched alkylaryl group having 7 to 9 carbon atoms. In the general formula (17), Y represents chlorine, bromine or iodine, and particularly preferably chlorine or bromine. The molar ratio in the case of reacting the polyoxyalkylene glycol derivative of the general formula (14) with the monohalocarboxylic acid ester of the general formula (17) can be arbitrarily selected. It is preferable to react one or more moles of the monohalocarboxylic acid ester with respect to 1 mole, more preferably 1 to 8 moles. The reaction temperature in the ester group introduction step is also arbitrary, but is usually preferably −20 to 150 ° C., and more preferably −10 to 80 ° C. (E) Transesterification Step The ester compound of the general formula (18) obtained in the above ester group introduction step and the alkanolamine represented by the aforementioned general formula (16) are subjected to a transesterification reaction to give a compound of the general formula The amine compound of the present invention represented by (9) can be obtained. When the ester compound of the general formula (18) is reacted with the alkanolamine of the general formula (16), the molar ratio can be arbitrarily selected. Usually, at least 1 mol of the alkanolamine is used per 1 mol of the ester compound. The above reaction is preferably performed, and more preferably 1 to 20 mol. The reaction temperature in the transesterification step is also optional, but is usually preferably from 60 to 200 ° C, more preferably from 100 to 160 ° C.

The amine compound of the present invention represented by the general formula (1) is a very useful compound as an additive for fuel oil. The term "fuel oil" as used herein means a liquid hydrocarbon mainly intended for combustion, and usually has a boiling point of 30 to 70.
0 ° C., preferably 40-600 ° C. Various kinds of liquid hydrocarbon fuel oils can be used and are not particularly limited. Specifically, for example, oil,
Any liquid hydrocarbon fuel oil derived from waste, oil shale, oil sands, coal, biomass, etc. can be used, but in the current environment it is mainly composed of crude oil or petroleum fractions Preferably, one is used. As the crude oil that can be used as the liquid hydrocarbon fuel oil of the present invention, any crude oil such as a paraffin-based crude oil, a naphthenic-based crude oil, a mixed-base crude oil, a special crude oil, or a mixture thereof can be used. The petroleum fraction that can be used as the fuel oil of the present invention means a fraction or residue obtained by appropriately performing distillation, cracking, reforming, or other refining treatment of the above crude oil or a mixture thereof. More specifically, for example, gasoline fractions represented by gasoline for automobile engines, gasoline for agricultural internal combustion engines, gasoline for forestry internal combustion engines, etc .; naphtha fractions represented by naphtha for fuels ( Light naphtha, heavy naphtha, whole range naphtha, etc.); jet fuel,
Jet fuel fractions such as aviation gasoline; kerosene fractions such as kerosene for cooling and heating, kerosene for kitchens, kerosene for petroleum engines, and kerosene for industrial fuels; light oil for automotive diesel engines, light oil for heated fuel, etc. Heavy oil fraction represented by boiler, heavy oil for building heating, heavy oil for marine diesel engine, heavy oil for ceramic industry, etc. (A heavy oil, B heavy oil, C heavy oil, etc.); and mixtures thereof And the like. Specific examples of the liquid hydrocarbon fuel oil derived from waste include those derived from decomposition, refining, and other processing of municipal waste, industrial waste, waste oil, and the like. As the fuel oil to which the amine compound of the present invention can be added, any of the above-mentioned various liquid hydrocarbon fuel oils and mixtures thereof can be used, but the amine compound of the present invention is particularly added to gasoline for internal combustion engines. In this case, the gasoline engine exhibits extremely excellent performance in cleanliness of the intake system and the combustion chamber. More specifically, as the gasoline for the internal combustion engine in this case,
Gasoline No. 1 and No. 2 gasoline specified by ISK2202 “Car Gasoline” are listed. The amount of the amine compound of the present invention to be added to the fuel oil is not particularly limited, but is usually 0.005 to 10% by mass, preferably 0.01 to 10% by mass based on the total amount of the fuel oil composition.
-5% by mass. In particular, when it is added to gasoline for internal combustion engines, the content of the amine compound is 0.1% based on the total amount of the fuel oil composition, since it exerts an excellent effect on the cleanliness of the intake system and the combustion chamber of the gasoline engine. 005 to 5% by mass, preferably 0.01 to 4%
%, More preferably 0.02 to 3% by mass.

The fuel oil composition to which the amine compound of the present invention is added has an extremely excellent effect on the cleanliness of the intake system and the combustion chamber of a gasoline engine, particularly when gasoline for an internal combustion engine is used as the fuel oil. However, known fuel oil additives can be added alone or in combination of several types for the purpose of further improving the performance. Examples of additives that can be used in combination with the additives of the present invention include alcohols such as methanol and ethanol, ethers such as isopropyl ether, methyl tertiary butyl ether and methyl tertiary amyl ether, and octane numbers represented by aromatic amines. Cetane number improver typified by nitrate ester or organic peroxide; Surface ignition inhibitor typified by organic phosphate ester, halogenated organic phosphate ester; 2,6-di-tert-butyl Phenols such as p-cresol, phenyl-α
An antioxidant represented by an aromatic amine such as naphthylamine; a metal deactivator represented by a salicylidene derivative; a metal sulfonate; a metal phenate;
Metal detergents such as metal salicylates; ashless dispersants such as alkenyl succinimides, alkyl polyamines, and polyether polyamines; anti-freezing agents such as glycol, glycerin, and glycol ethers; glycol ethers Microbial disinfectants represented by phenols, boron compounds, etc .; flame retardants represented by metal naphthenates, metal sulfonates, alcoholic sulfates, etc .; Agents; corrosion inhibitors such as aliphatic amines and alkenyl succinates; antistatic agents such as anionic, cationic and amphoteric surfactants; coloring agents such as azo dyes; The amount of these additives to be added is also optional, but usually the amount of each additive is 0.5% by mass or less, preferably 0.2% by mass or less based on the total amount of the composition.

[0020]

Next, the present invention will be described in more detail with reference to examples and comparative examples, but these examples do not limit the present invention in any way. Prior to the description of the examples, examples of the synthesis of the amine compound used in the examples are shown below. Synthesis Example 1 13.3 g (0.06 mol) of nonylphenol and 3.37 g (0.06 mol) of potassium hydroxide were placed in an autoclave having a content of 1 liter. . Thereafter, 67.07 g (0.36 mol) of 2-ethylhexyl glycidyl ether, 62.73 g (1.08 mol) of propylene oxide and 100 ml of toluene were added thereto, and the reaction temperature was 5 ° C.
Allowed to react for hours. After completion of the reaction, the reaction product solution was neutralized with hydrochloric acid, then extracted with toluene and the solvent toluene was distilled off to obtain a polyoxyalkylene compound 1
20 g were obtained. Next, to a mixed solution of 100 g of this polyoxyalkylene compound (equivalent to 0.04 mol: calculated from the weight average molecular weight) and 100 ml of toluene, 8.0 g (0.081 mol) of liquid phosgene was added at 0 ° C.,
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 102 g of a chlorine-containing compound. Next, after cooling a mixed solution of 100 ml of toluene, 100 ml of pyridine and 60 g (0.4 mol) of triethanolamine to 5 ° C., 100 g of the above chlorine-containing compound (0.
04 mol: calculated from the weight average molecular weight)
The reaction was carried out for 3 hours while maintaining the system at ° C. After completion of the reaction, unreacted triethanolamine, generated hydrochloride of pyridine, and toluene as a solvent were removed and purified, whereby 95 g of the target amine compound was obtained. This amine compound was an oily liquid having a number average molecular weight of about 2500 and exhibited a deep orange color. As a result of ¹³ C-NMR analysis, this amine compound was a random copolymer having an average structure represented by the formula (19).

Embedded image Synthesis Example 2 13.3 g (0.06 mol) of nonylphenol 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 and heated to 90 ° C. . Thereafter, 67.07 g (0.36 mol) of 2-ethylhexyl glycidyl ether, 62.73 g (1.08 mol) of propylene oxide and 100 ml of toluene were added thereto, and the reaction temperature was 5 ° C.
Allowed to react for hours. After completion of the reaction, the mixture was cooled on ice, and 13.0 g of methyl monochloroacetate (0.12 g) was kept at 0 ° C.
Mol), and the mixture was reacted at room temperature for 5 hours with stirring. After completion of the reaction, excess methyl monochloroacetate, generated inorganic salt, and toluene as a solvent were removed to obtain 130 g of an ester compound. Next, 100 g of the above ester compound (equivalent to 0.04 mol: calculated from the weight average molecular weight) was added to a mixed solution of 10 g of dehydrated p-toluenesulfonic acid, 100 ml of toluene and 60 g (0.4 mol) of triethanolamine. Was heated to 110 ° C., and a transesterification reaction was performed for 10 hours while removing generated methanol. After completion of the reaction, unreacted triethanolamine, p-toluenesulfonic acid as a catalyst and xylene as a solvent are removed and purified to obtain the desired amine compound 98.
g was obtained. This amine compound has a number average molecular weight of about 250.
0 was an oily liquid and had a dark orange color. ¹³ C-
As a result of NMR analysis, this amine compound was a random copolymer having an average structure represented by the formula (20).

Embedded image Synthesis Example 3 2-ethylhexyl glycidyl ether 67.0 using tert-butanol 4.45 g (0.06) mol instead of nonylphenol 13.3 g (0.06 mol)
Using 48.56 g (0.48 mol) of tert-butyl glycidyl ether instead of 7 g (0.36 mol),
The amount of propylene oxide used was 62.37 g (1.08
Synthesis Example 1 except that the amount of triethanolamine was changed from 76.4 g (0.4 mol) to 60 g (0.4 mol) of triethanolamine. By the same apparatus and method as in the above, 91 g of the target amine compound was obtained. This amine compound was an oily liquid having a number average molecular weight of about 2,000 and exhibited a deep orange color. As a result of ¹³ C-NMR analysis,
This amine compound was a random copolymer having an average structure represented by the formula (21).

Embedded image Synthesis Example 4 2-ethylhexyl glycidyl ether 67.07 using 3.60 g (0.06 mol) of isopropanol instead of 13.3 g (0.06 mol) of nonylphenol
g (0.36 mol) is replaced by 108 g (0.83 mol) of tert-butyl glycidyl ether, while propylene oxide is not used and 76.4 g (0.4 mol) of triisopropanolamine is used as alkanolamine. Except for the above, 102 g of the target amine compound was obtained by the same apparatus and method as in Synthesis Example 2. This amine compound was an oily liquid having a number average molecular weight of about 2,000 and exhibited a deep orange color. As a result of ¹³ C-NMR analysis, this amine compound was a polymer having an average structure represented by the formula (22).

Embedded image

Examples 1-4 and Comparative Examples 1-3 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 prepare a base gasoline having the following properties. Base gasoline properties Lead vapor pressure: 0.67 kgf / cm ² Specific gravity: 0.730 Boiling range: 30 to 190 ° C. Octane number: 98.7 The base gasoline and the amine of the present invention obtained in Synthesis Examples 1 to 4 A fuel oil composition according to the present invention was prepared using the compound and the composition shown in Table 1. The following engine evaluation tests were performed on each of these fuel oil compositions. Table 1 shows the results. [Engine evaluation test] Intake system deposit cleanliness evaluation test Using a passenger car equipped with an unused fuel injector type engine with a total displacement of 2000 ml, first, a running mode for one cycle and one hour shown below using only base gasoline. Was repeated for 200 hours, the engine was disassembled, and the amount of deposit adhering to the intake valve was measured. Driving mode Idling: 1 minute Engine speed 1500 rpm, intake negative pressure -200 mmHg: 30 minutes Engine speed 2700 rpm, intake negative pressure -300 mmHg: 20 minutes Engine stoppage: 9 minutes Next, assemble this engine without removing deposits and fuel Was replaced with the fuel oil composition of the example, and the above-mentioned traveling mode was repeated for 30 hours. After the test, disassemble the engine again and measure the amount of deposit attached to the intake valve.
The difference between the fuel oil composition of the example and the deposit amount before use was determined, and the result was evaluated as the intake system deposit cleanliness. Combustion chamber deposit cleanliness evaluation test A passenger car equipped with a fuel injection type unused engine having a total displacement of 2000 ml was used, the fuel oil composition of the example was used as fuel, the engine speed was 1500 rpm, and the intake negative pressure was −
The operation was performed for 96 hours under the operating conditions of 150 mmHg and a cooling water temperature of 50 ° C. After the test, the engine was disassembled to measure the amount of deposit in the combustion chamber, and the difference from the amount of deposit in the combustion chamber when only base gasoline was used was determined. For comparison,
The same engine was used when only the base gasoline to which no amine compound was added (Comparative Example 1) and when a polybutenylamine-based detergent was used instead of the amine compound of the present invention (Comparative Examples 2 and 3). An evaluation test was performed. The results are also shown in Table 1.

[Table 1] As is evident from the results of the engine evaluation test in Table 1, although the commercially available polybutenylamine-based detergent has a certain degree of cleanliness of the intake system deposit, the amount of the combustion chamber deposit greatly increases as compared with the case where no additive is added. Would. On the other hand, the fuel oil composition to which the amine compound of the present invention is added exhibits almost no increase in combustion chamber deposition compared to the case without addition, and exhibits an extremely excellent effect on cleanliness of the intake system deposit. Things.

 ──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Toru Yoshii 8 Chidoricho, Naka-ku, Yokohama, Japan Central R & D Laboratories

Claims (2)

[Claims] 1. A fuel oil additive comprising an amine compound represented by the following general formula (1). Embedded image In the general formula (1), R ¹ is hydrogen or a group having 1 to 3 carbon atoms.
0 represents a hydrocarbon group, and R ² , R ³ , R ⁴ and R ⁵ each independently represent hydrogen, a hydrocarbon group having 1 to 10 carbon atoms or a group represented by the following general formula (2) ( Where R ² ,
At least one of R ³ , R ⁴ and R ⁵ is a group represented by the general formula (2)), R ⁶ is an alkylene group having 2 to ⁶ carbon atoms, and R ⁷ and R ⁸ are each independently A represents an alkylene group having 1 to 6 carbon atoms, a represents an integer of 1 to 100, b represents an integer of 0 to 100, and a + b
= 1 to 200, c is 0 or 1, d and e are each independently an integer of 1 or 2, and d + e = 3, and X is the following general formula (e = 1) 3) When e = 2, at least one is a group represented by the general formula (3), and the other is a group having 1 to 30 carbon atoms.
Or a group represented by the general formula (3). Embedded image In the general formula (2), R ⁹ and R ¹⁰ are each independently hydrogen, a hydrocarbon group having 1 to 10 carbon atoms, or a hydrocarbon group having 2 to 2 carbon atoms.
R ¹¹ represents an alkylene group having 2 to 6 carbon atoms, or R 4 represents a total of 4 carbon atoms having an alkoxyalkyl group as a substituent.
R ¹² represents hydrogen or a hydrocarbon group having 1 to 30 carbon atoms; and f represents an integer of 0 to 50. Embedded image In the general formula (3), R ¹³ represents an alkylene group having 1 to 6 carbon atoms. 2. An amine compound represented by the general formula (1) is added to gasoline for an internal combustion engine in an amount of 0.
A fuel oil composition containing 005 to 5% by mass.