Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2001-11-21
2003-02-25
Davis, Brian (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S503000, C564S504000, C564S505000, C510S185000, C044S433000
Reexamination Certificate
active
06525221
ABSTRACT:
CROSS REFERENCE TO RELATED APPLICATIONS
This application is based on application No. 10-1999-0018908 filed in the Korean Industrial Property Office on May 25, 1999, the content of which is incorporated hereinto by reference.
BACKGROUND OF THE INVENTION
(a) Field of the Invention
The present invention relates to hydropolyoxyalkylene oxyalkyl amine compounds useful as a novel fuel oil detergent, more particularly to hydropolyoxyalkylene oxyalkyl amine compounds useful as a novel fuel oil detergent, which can efficiently inhibit both the formation of deposits in the carburetor, injector and intake valve of internal combustion engines and octane number required value increases (ORI) by incorporating the active detergent into the fuel, and a process for preparing the same and a fuel oil composition comprising the same.
(b) Description of the Related Art
It has been known that deposits are formed on the surface of injectors, intake valves, carburetors, etc., of internal combustion engines by the oxidation of the fuel and lubricant oil. These deposits formed in the intake valve block a mixed gas flow which enters a combustion chamber, thereby causing severe drive-ability problems such as misfire and poor acceleration and can significantly increase an automobile's fuel consumption and produce harmful exhaust pollutants. Furthermore, the deposits formed in a combustion chamber can create mechanical damage to a piston, piston ring, engine head, etc.
Conventionally, an aliphatic amine compound based on long-chained hydrocarbons has been developed and used as a fuel oil detergent in order to inhibit the formation of these deposits. It is disclosed in U.S. Pat. Nos. 3,438,757 and 3,574,576 that hydrocarbyl amines having a molecular weight of 425 to 10,000, preferably 450 to 5,000, are useful as a fuel oil detergent or a lubricating oil dispersing agent of internal combustion engines. Furthermore, it is disclosed in European Patent No. 476,485 A that polybutylaminoalcohol prepared by reacting amine with polybutene epoxide obtained by epoxidizing polybutene is useful as a detergent for the gasoline and as an additive to the lubricant oil. The polybutylaminoalcohol is produced by a nucleophilic substitution reaction of polybutene epoxide with amine.
However, there are problems in that the octane number required value of an engine increases since the above detergents increase the formation of deposits in a combustion chamber, although they have effects of inhibiting the formation of deposits on the surface of the intake valve. Deposits formed on the combustion chamber surface increase the temperature of a combustion chamber by hindering heat transfer between an engine cooling system and the combustion chamber, provoking engine knock by inducing pre-ignition.
Furthermore, a high compression ratio occurs resulting in an engine knock since the volume of the combustion chamber is decreased when deposits are formed on the surface of the combustion chamber. Knocking phenomena can cause damage to pistons, connecting rods, bearings, cam pushrods, etc., if it continues for a long period of time and (it can cause) energy inefficiency.
As described in the above, an octane number required value increase phenomena of an engine occurs when deposits are formed in the combustion chamber, and a fuel having a high octane number should be used so as to prevent the knocking phenomena from occurring in case of an engine having a high octane number required value increase. However, the knocking phenomena can be prevented without using a fuel having a high octane number when the octane number required value increase of the engine is decreased by inhibiting or preventing the formation of deposits in the combustion chamber.
SUMMARY OF THE INVENTION
Therefore, it is an object of the present invention to provide a hydropolyoxyalkylene oxyalkyl amine compound as a novel fuel oil detergent which has superior intake valve cleaning effects and inhibits or prevents octane number required value increases.
Furthermore, it is another object of the present invention to provide a process for preparing the hydropolyoxyalkylene oxyalkyl amine compounds.
In order to accomplish the above objects, the present invention provides a hydropolyoxyalkylene oxyalkyl amine compound as a novel fuel oil detergent.
Furthermore, the present invention provides a fuel oil concentrate comprising the hydropolyoxyalkylene oxyalkyl amine compound.
Furthermore, the present invention provides a fuel oil composition comprising the hydropolyoxyalkylene oxyalkyl amine compound and/or concentrate.
Furthermore, the present invention provides a preparation process in which the hydropolyoxyalkylene oxyalkyl amine compound is prepared.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
In the following detailed description, only the preferred embodiments of the invention have been shown and described, simply by way of illustration of the best mode contemplated by the inventor(s) of carrying out the invention. As will be realized, the invention is capable of modification in various obvious respects, all without departing from the invention. Accordingly, the description is to be regarded as illustrative in nature, and not restrictive.
The present invention is described in detail as follows.
As a hydropolyoxyalkylene oxyalkyl amine compound, a novel fuel oil detergent of the present invention has a structure such as the following Chemical Formula 1 of which the molecular weight is preferably from 200 to 6,000.
where m is an integer from 1 to 10, preferably an integer from 1 to 2;
n is an integer from 1 to 80, preferably an integer from 1 to 50;
r and s, each of which can be the same or different, are each independently an integer from 0 to 10, preferably an integer from 0 to 3;
R
1
is an alkyl derived from polyolefin having a molecular weight from 200 to 5,000, preferably an alkyl derived from polyolefin having a molecular weight from 200 to 2,500;
R
2
, R
4
, and R
5
, each of which can be the same or different, are each independently hydrogen or alkyl having 1 to 10 carbon atoms, preferably alkyl having 1 to 2 carbon atoms;
R
3
, as a repetition unit of a polymer chain which can be the same or different between repetition units, is alkylene having 2 to 10 carbon atoms, preferably alkylene having 2 to 5 carbon atoms;
R
6
and R
9
, each of which can be the same or different, are each independently hydrocarbons comprising aromatic chains having 6 to 10 carbon atoms or alkylenes having 2 to 10 carbon atoms, preferably alkylenes having 2 to 6 carbon atoms; and
R
7
, R
8
, R
10
, and R
11
, each of which can be the same or different, are each independently hydrogen, hydrocarbons comprising aromatic chains having 6 to 10 carbon atoms, alkyls having 1 to 10 carbon atoms, or hydropolyoxyalkylene(oxyalkylene) of the following Chemical Formula 2:
&Parenopenst;R
12—O&Parenclosest;
p
H
where p is an integer from 0 to 80, preferably an integer from 0 to 50; and
R
12
, as a repetition unit of polymer chains which can be the same or different between repetition units, is a hydrocarbon comprising aromatic chains having 6 to 10 carbon atoms or alkylenes having 2 to 10 carbon atoms, preferably alkylene having 2 to 5 carbon atoms.
A process for preparing a hydropolyoxyalkylene oxyalkyl amine based compound of the present invention consists of reacting hydroxyalkyl amine of the following Chemical Formula 3 with alkyleneoxide having 2 to 10 carbon atoms, preferably 2 to 5 carbon atoms:
where m is an integer from 1 to 10, preferably an integer from 1 to 2;
r and s, each of which can be the same or different, are each independently an integer from 0 to 10, preferably an integer from 0 to 3;
R
1
is alkyl derived from polyolefin having a molecular weight from 200 to 5,000, preferably alkyl derived from polyolefin having a molecular weight from 200 to 2,500;
R
2
, R
4
, and R
5
, each of which can be the same or different, are each independently a hydrogen or alkyl having 1 to 10 carbon atoms, preferably alkyl having 1 to 2 carbon atoms;
R
6
and R
9
, each of which can be the s
Kim Myeong-Seok
Lim Byeong-Gyu
Sohn Byung-Keel
Uhm Jae-Hoon
Youn Hyun-Ki
Daelim Industrial Co., Ltd.
Davis Brian
Staas & Halsey , LLP
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