Compositions – Chemiluminescent
Reexamination Certificate
2002-02-07
2004-05-25
Tucker, Philip C. (Department: 1712)
Compositions
Chemiluminescent
C585S026000, C585S425000, C570S129000, C570S183000
Reexamination Certificate
active
06740263
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an anthracene compound and a chemiluminescent composition comprising the compound, and more particularly to a novel anthracene compound which is capable of emitting a blue light of a high intensity for a prolonged period of time compared with conventional anthracene compounds used as luminescent dyes in chemiluminescent compositions emitting blue light, and a chemiluminescent composition comprising the novel compound.
2. Description of the Related Art
One example of known chemiluminescent solutions includes a mixed solution of a chemiluminescent oxalate composition comprising a luminous dye and a solution containing peroxide.
The chemiluminescent oxalate composition generally contains a luminescent dye, an oxalate and a solvent. The peroxide-containing solution contains peroxide, a catalyst and a solvent.
The color of light generated from the chemiluminescent solution is determined by the luminescent dye used in the chemiluminescent oxalate composition. As the luminescent dye emitting a blue light, an anthracene compound is known.
As the anthracene compound emitting a blue light, a 9,10-diphenylanthracene compound described in the following formula 1 and a luminescent composition comprising the compound is known.
However, there is a disadvantage that the intensity and color of light emitted from the chemiluminescent solution comprising the 9,10-diphenylanthracene compound are rendered unstable with the lapse of time.
Therefore, there have been continuous attempts to find a luminescent dye that stably emits clear blue light. In particular, due to the fact that the physical properties of the 9,10-diphenylanthracene compound change with a substituent applied to the compound, many studies have been investigated.
As one of such studies, U.S. Pat. No. 4,678,608 discloses a chemiluminescent composition using a 9,10-bis(4-methylphenyl)anthracene compound represented by the following formula 2.
However, where the 9,10-bis(4-methylphenyl)anthracene compound is used in the chemiluminescent oxalate composition, it loses a desired stability. For this reason, the compound cannot be used in products requiring that luminescence be maintained for 5 hours or more.
Also, U.S. Pat. No. 4,717,511 discloses a chemiluminescent composition using 9,10-bis(4-methoxyphenyl)-2-chloroanthracene described in the following formula 3
However, there is a disadvantage that the 9,10-bis(4-methoxyphenyl)-2-chloroanthracene compound emits pale blue light.
Therefore, the present inventor has endeavored to develop a compound that is capable of emitting a clear blue light for a prolonged period of time, and the present invention has been accomplished by such studies.
SUMMARY OF THE INVENTION
Therefore, the present invention has been made in view of the above problems, and it is an object of the present invention to provide an anthracene compound which has excellent stability over the conventional luminescent dye emitting blue light, thereby emitting a chemiluminescent light of clear deep blue.
It is another object of the present invention to provide a chemiluminescent composition and a chemiluminescent solution using the anthracene compound.
In accordance with one aspect of the present invention, there is provided an anthracene compound represented by the following formula(4):
wherein R is a alkyl group having 1-8 carbon atoms, X
1
and X
2
are independently hydrogen or halogen.
In accordance with another aspect of the present invention, there is provided a preparation method of an anthracene compound comprising:
refluxing a compound of the following formula(11) with magnesium metal in an organic solvent and cooling the refluxed solution, thereby affording a compound of the following formula(12);
mixing the obtained compound of the formula(12) and anthraquinone of the following formula(13) in an organic solvent, refluxing the resulting solution adding an aqueous acidic solution, for example, 10% hydrochloric acid solution, extracting an organic phase, and distilling the extracted organic solvent under a vacuum, thereby producing a brown solution of the following formula(14); and
adding acetic acid and a catalyst to the obtained brown solution, and refluxing the resulting solution, thereby obtaining the solid compound of the formula(4).
wherein R is an alkyl group having 1-8 carbon atoms, and X is halogen.
wherein R is an alkyl group having 1-8 carbon atoms, and X is halogen.
wherein X
1
and X
2
are independently hydrogen or halogen.
wherein R is an alkyl group having 1-8 carbon atoms, and X
1
and X
2
are independently hydrogen or halogen.
wherein R is an alkyl group having 1-8 carbon atoms, and X
1
and X
2
are independently hydrogen or halogen.
In accordance with another aspect of the present invention, there is provided a chemiluminescent composition containing the anthracene compound represented by the following formula(4):
wherein R is a alkyl group having 1-8 carbon atoms, X
1
and X
2
are independently hydrogen or halogen, the chemiluminescent composition emitting chemiluminescent light by reaction with peroxide.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present invention can be achieved by providing an anthracene compound represented by the following formula 4:
wherein R is a alkyl group having 1-8 carbon atoms, and X
1
and X
2
are independently hydrogen or halogen.
A more preferred compound of the formula 4 is an anthracene compound represented by the following formula 5, in which X
1
is hydrogen and X
2
is halogen:
wherein R is a alkyl group having 1-8 carbon atoms, and X
2
is halogen.
A more preferred compound of the formula 5 is an anthracene compound represented by the following formula 6, in which X
2
is Cl:
wherein R is a alkyl group having 1-8 carbon atoms.
A more preferred compound of the formula 6 is 9,10-bis (4-methylphenyl)-2-chloroanthracene of the following formula 7, wherein R is a methyl group; 9,10-bis(4-ethylphenyl)-2-chloroanthracene of the following formula 8,
wherein R is a ethyl group; 9,10-bis(4-propylphenyl)-2-chloroanthracene of the following formula 9, wherein R is a propyl group; or 9,10-bis(4-t-butylphenyl)-2-chloroanthracene of the following formula 10, wherein R is a t-butyl group:
To prepare effectively the anthracene compound of the formula 4, the present invention provides a preparation method comprising the steps of:
refluxing a compound of the following formula 11 with magnesium metal in an organic solvent for 3 hours or more, and cooling the refluxed solution, thereby obtaining a compound of the following formula 12;
stirring the obtained compound of the formula 12 and anthraquinone of the following formula 13 in an organic solvent for 3 hours or more, refluxing the resulting solution for 3 hours or more, stirring the resulting solution after adding an aqueous 10% hydrochloric acid solution, extracting only the organic solvent, and distilling the extracted organic solvent under a vacuum, thereby obtaining a brown solution of the following formula 14; and
adding acetic acid and a catalyst to the obtained brown solution, stirring the mixed solution for 1 hour or more, refluxing the stirred solution for 3 hours or more, stirring again the refluxed solution for 3 hours or more, and treating the resulting solution using a recrystallization method, thereby obtaining the solid compound of the formula 4.
wherein R is an alkyl group having 1-8 carbon atoms, and X is halogen.
wherein R is an alkyl group having 1-8 carbon atoms, and X is halogen.
wherein X
1
and X
2
is independently hydrogen or halogen.
wherein R is an alkyl group having 1-8 carbon atoms, X
1
and X
2
is independently hydrogen or halogen.
As described above, the compound of the formula 11 is refluxed with magnesium metal in the organic solvent for 3 hours or more. The refluxed solution is cooled. In this way, the compound of the formula 12 is obtained.
Various organic solvents can be used in this step. Anhydrous tetrahydrofuran is used as a preferred organic solvent in the present invention. The
Kim Yong Fan
Park Koon Ha
Park Min Seob
Cantor & Colburn LLP
Tucker Philip C.
Yeom Myung-Sook
LandOfFree
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