Fuel and related compositions – Liquid fuels – Organic nitrogen compound containing
Reexamination Certificate
2000-12-26
2003-02-04
Toomer, Cephia D. (Department: 1714)
Fuel and related compositions
Liquid fuels
Organic nitrogen compound containing
C564S248000, C540S001000, C540S450000, C540S467000, C540S470000, C540S484000, C540S544000, C540S605000, C544S001000, C544S063000, C544S106000, C544S358000, C546S001000, C546S184000
Reexamination Certificate
active
06514298
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to fuel additives and more particularly to fuel additives having excellent solubility in fuel and detergency in intake systems and combustion chambers of gasoline engines and in nozzles of diesel engines. This invention also relates to fuel compositions containing such additives.
2. Description of the Prior Art
Sludge or other objectionable deposits if formed in internal combustion engine fuel systems or combustion chambers of automobiles are responsible for engine trouble of abnormal rise in carbon monoxide and unburned hydrocarbon concentrations in the exhaust gases. It has thus far been proposed to use certain fuel additives, typically a gasoline detergent such as a polyetheramine-based or polyolefin-based detergent for removing or otherwise preventing deposits in the carburetors, electronic fuel injections, intake valves and other operative parts of automobiles.
Fuel additives to this end are disclosed in U.S. Pat. Nos. 4,247,301 and 4,160,648 wherein a polyether-based gasoline detergent is recited as being effective in removing or preventing deposits particularly on the fuel intake valves.
Intensive research efforts have been made in the automobile industry to eliminate or alleviate the adverse effect of exhaust gases upon human body and the environment together with the effort for fuel consumption reduction. However, since the conventional polyether amine-based or polyolefin-based gasoline detergents which can exhibit superior performances in removing or preventing deposits in intake valves but have tendency to increase deposits in combustion chambers, an overall improvement in exhaust gas has not been achieved yet. With this background in view, there has been a growing demand for more effective and advantageous fuel additives which are more excellent in detergency in the intake system and combustion chamber of a gasoline engine and which can exhibit a detergent capability even when the engine is under cold conditions.
It has also been pointed out that in a diesel engine deposits formed in the injection nozzles cause changes and delays in fuel flow rate, resulted in deteriorated running performance and exhaust gas. Therefore, there has also been demanded for fuel additives for diesel engines having superior detergent effects as well.
In view of the foregoing current situations, the present invention is intended to provide a novel fuel additive which exhibits superior performances over those of the conventional gasoline detergents and excels in detergency in the injection nozzles of a diesel engine as well as being itself free from becoming sludge.
BRIEF SUMMARY OF THE INVENTION
After intensive research and efforts made to develop a fuel additive having superior detergency in the intake system and combustion chamber of a gasoline engine as well as in the injection nozzles of a diesel engine, it was found that a compound having a group represented by formula (1) below exhibits superior performances to conventional gasoline detergents.
According to the present invention, there is provided a fuel additive which comprises a compound having a group represented by formula (1) below. According to another aspect of the present invention, there is provided a fuel composition which is obtained by adding a fuel additive comprising a compound having a group of formula (1) below to an internal combustion fuel
>C═=N— (1)
DETAILED DESCRIPTION OF THE INVENTION
The present invention is described in more detail below.
The fuel additive of the present invention comprises a compound having a group represented by the formula
>C═=N— (1)
A compound having a group of formula (1) is usually obtained by reacting a primary amine and a carbonyl compound.
The compound having a group of formula (1) is exemplified by ones represented by the formula
In formula (2), R
1
and R
2
are each independently either hydrogen or a hydrocarbon group having 1 to 30 carbon atoms. X is a group selected from groups of X1, X2, and X3. Y is a group selected from groups of Y1, Y2, Y3, and Y4. “a” is an integer of 0 or 1.
X1 is a group represented by the formula
—(AO)
b
—R
3
(3)
wherein A is an alkylene group having 1 to 18 carbon atoms, b is an integer from 0 to 200, R
3
is either hydrogen or a hydrocarbon group having 1 to 300 carbon atoms.
X2 is a nitrogen-containing group represented by the formula
wherein R
4
is an alkylene group having 2 to 6 carbon atoms, R
5
is either hydrogen, an alkyl group having 1 to 4 carbon atoms, or a group of formula (3) provided that b is not 0, R
6
is either hydrogen, a hydrocarbon group having 1 to 300 carbon atoms, or a group of formula (3) wherein b is not 0, and c is an integer from 1 to 5.
X3 is a group having a nitrogen-containing cyclic compound residue represented by the formula
wherein R
7
is an alkylene group having 2 to 6 carbon atoms, the cyclic compound may have oxygen other than hydrogen, carbon, and nitrogen, and d is an integer of 0 or 1.
Y1 is a group represented by the formula
wherein R
12
is an alkylene group having 2 to 6 carbon atoms, and e is an integer of 0 or 1.
Y2 is a group represented by the formula
wherein R
13
is an alkylene group having 2 to 6 carbon atoms, and f is an integer of 0 or 1.
Y3 is a group represented by the formula
wherein R
14
is an alkylene group having 2 to 6 carbon atoms, g is an integer from 1 to 5, and h is an integer of 0 or 1.
Y4 is a group represented by the formula
wherein R
15
and R
16
are each independently an alkylene group having 2 to 6 carbon atoms, and i is an integer from 0 to 5.
In formula (2), R
1
and R
2
are each independently hydrogen or a hydrocarbon group having 1 to 30 carbon atoms but is preferably a straight or branched alkyl group having 1 to 24 carbon atoms, a cycloalkyl or alkylcycloalkyl group, i.e., cycloalkyl substituted by alkyl, having 5 to 13 carbon atoms, a straight or branched alkenyl group having 2 to 24 carbon atoms, an aryl or alkylaryl group, i.e., aryl substituted by alkyl, having 6 to 18 carbon atoms, or an arylalkyl group, i.e., alkyl substituted by aryl, having 7 to 19 carbon atoms.
Preferred alkyl groups for R
1
and R
2
are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, straight or branched pentyl, straight or branched hexyl, straight or branched heptyl, straight or branched octyl, straight 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 pentadecil, straight or branched hexadecyl, straight or branched heptadecyl, straight or branched octadecyl, straight or branched nonadecyl, straight or branched eicosyl, straight or branched heneicosyl, straight or branched docosyl, straight or branched tricosyl, and straight or branched tetracosyl groups.
Preferred cycloalkyl groups for R
1
and R
2
are cyclopentyl, cyclohexyl, and cycloheptyl groups.
Preferred alkylcycloalkyl groups are metylcyclopentyl, dimethylcyclopentyl (including all positional isomers), ethylcyclopentyl (including all positional isomers), straight or branched propylcyclopentyl (including all positional isomers), ethylmethylcyclopentyl (including all positional isomers), trimethylcyclopentyl (including all positional isomers), diethylcyclopentyl (including all positional isomers), ethyldimethylcyclopentyl (including all positional isomers), straight or branched propylmethylcyclopentyl (including all positional isomers), straight or branched propylethylcyclopentyl (including all positional isomers), straight or branched dipropylcyclopentyl (including all positional isomers), straight or branched propylethylmethylcyclopentyl (including all positional isomers), methylcyclohexyl (including all positional isomers), dimethylcyclohexyl (including all positional isomers), ethylcyclohexyl (including all positional isomers), straight or branched propylcyclohexyl (including all positional isomers), ethylmethylcyclohe
Haji Katsuhiko
Nagao Masaki
Sone Tadahide
Akin Gump Strauss Hauer & Feld L.L.P.
Nippon Mitsubishi Oil Corporation
Toomer Cephia D.
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