Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2002-07-05
2004-03-02
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S717000, C534S806000, C534S811000, C534S827000, C534S829000, C008S506000, C252S585000
Reexamination Certificate
active
06699976
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a polyazo compound or a salt thereof, and a dye-based polarization film containing the same.
Dye-based Polarization films are produced by adding a dye covering the desired wave-length region as a polarization element into a polarization film substrate such as a drawn and oriented polyvinyl alcohol-based film, an oriented polyene-based film produced by de-hydrochloric acid of a polyvinyl chloride film or dehydration of a polyvinyl alcohol film, and the like. As an example of dyes covering the region of from 500 to 580 nm, a polyazo compound represented by the following formula is known (JP-A-5-295281, Example 1).
However, polarization films produced by using the known polyazo compound mentioned above are not completely sufficient yet from the view points of initial polarization ability, etc.
The object of the present invention is to provide a polyazo compound usable for producing a dye-based polarization film covering the region of from 500 to 580 nm and particularly excellent in Initial polarization ability.
The present inventors have conducted extensive studies, and, resultantly, they have found that a specific polyazo compound or salt thereof attains the above-mentioned object. Thus, the present invention was completed.
SUMMARY OF THE INVENTION
Namely, the present invention provides a polyazo compound or salt thereof represented by the following formulae (I) or (II):
wherein,
A represents a phenyl having sulfo and/or carboxyl and optionally having a lower alkyl or lower alkoxy, or a naphthyl having 1 to 3 sulfos,
R
1
to R
6
are the same or different and represent hydrogen, lower alkyl or lower alkoxy,
m and n each independently represents 0 or 1.
R
7
represents hydrogen or sulfo,
D and E each independently represents —NHCO— or —N═N—,
G represents —CH
2
—, alkylene having 2-4 carbon atoms, phenylene or —CH═CH—,
and R
8
represents sulfo, carboxyl or lower alkoxycarbonyl, provide that, when G represent phenylene, n is 1.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
A in the above-mentioned formula (I) represents a naphthyl having 1 to 3 sulfos or a phenyl having sulfo and/or carboxyl and optionally having a lower alkyl or lower alkoxy. The lower alkyl or lower alkoxy is preferably a linear or branched group having 1 to 4 carbon atoms Specific examples of the lower alkyl include methyl, ethyl, propyl and the like. Specific examples of the lower alkoxy include methoxy, ethoxy, propoxy and the like
As the phenyl represented by A, a phenyl having sulfo and/or carboxyl wherein the total number of sulfo and carboxyl is 1 or 2 is preferred. Examples of the phenyl include 2-, 3- or 4-sulfophenyl, 2-, 3- or 4-carboxyphenyl, 2,4- or 2,5-disulfophenyl, 3,5-dicarboxyphenyl, 2-carboxy-4- or -5-sulfophenyl, 2- or 3-methyl-4-sulfophenyl, and the like. Among them, a phenyl having sulfo is preferable from the view points of dyeing and 4-sulfophenyl is particularly preferable.
Examples of the naphthyl represented by A include 5-, 6-, 7- or 8-sulfo-2-naphthyl, 4-, 5-, 6- or 7-sulfo-1-naphthyl, 1,5-, 6,8-, 4,8-, 5,7- or 3,6-disulfo-2-naphthyl, 3,6- or 4,6-disulfo-1-naphthyl, and 1,5,7-, 3,6,8- or 4,6,8-trisulfo-2-naphthyl and the like. Among them, naphthyls having 2 to 3 sulfos are preferable from the view points of dyeing, and disulfo-2-naphthyls such as 1,5-, 6,8-, 4,8-, 5,7- or 3,6-disulfo-2-naphthyl and the like are particularly preferable.
R
1
to R
6
each independently represent hydrogen, lower alkyl or lower alkoxy. The lower alkyl or lower alkoxy is preferably a linear or branched group having 1 to 4 carbon atoms. Specific examples of the lower alkyl include methyl, ethyl, propyl and the like. Specific examples of the lower alkoxy include methoxy, ethoxy, propoxy and the like.
R
1
to R
6
preferably represent hydrogen or methyl.
R
7
represents hydrogen or sulfo, and preferably hydrogen.
R
8
represents sulfo, carboxyl or lower alkoxycarbonyl, and preferably lower alkoxycarbonyl, such as —CO—OCH
3
. The lower alkoxy in the lower alkoxycarbonyl is preferably a linear or branched group having 1 to 4 carbon atoms. Specific examples of the lower alkoxy include methoxy, ethoxy, propoxy and the like. As R
8
, methoxycarbonyl and ethoxycarbonyl are preferable, and particularly methoxycarbonyl is preferable.
G represents —CH
2
—, alkylene having 2-4 carbon atoms, phenylene or —CH═CH—. Among them, —CH
2
— and ethylene are preferable, and ethylene is particularly preferable
m and n each independently represents 0 or 1, provide that, when G represent phenylene, n is 0.
A polyazo compound of the formula (I) or a salt thereof can be produced, for example, by the following method.
First, a compound of the following formula (VII):
wherein, R
1
-R
6
, A and D are as defined above are diazotized by reacting with sodium nitrite in an acidic aqueous medium under a condition of 5 to 4° C.
Then, the resulted diazo compound is reacted with an amide compound of the following formula (III):
wherein, R
7
, R
8
, E, G and n are as defined above to obtain the polyazo compound of the formula (I) or a salt thereof.
A compound of the formula (VII) wherein m=1 or a salt thereof can be produced, for example, by the following method.
First, an azo compound of the following formula (IV):
wherein, R
1
-R
4
, A and D are as defined above, is diazotized by reacting with sodium nitrite in an acidic aqueous medium under a condition of 5 to 40° C. The resulted diazotized compound is reacted with an aniline compound of the following formula (V):
wherein, R
5
and R
6
are as defined above, in an aqueous medium under conditions of 5 to 40° C. and pH from 6 to 11, to obtain a compound of the formula (VII) wherein m=1 or a salt thereof.
A compound of the formula (VII) wherein m=0 or a salt thereof can be produced, for example, by reacting a compound obtained by diazotizing a compound of the following formula (VI):
wherein, R
1
, R
2
, A and D are as defined above, with the above aniline compound of formula (V).
An amide compound of the formula (III) can be produced, for example, by reacting a naphtol compound of the following formula (IIa):
wherein E, n and R
7
are as defined above, with an acid anhydride or acid halide which is capable of; introducing —CO—G—R
8
(wherein, G and R
8
are as defined above) into —NH
2
group in the formula (IIa).
A polyazo compound of the formula (II) or a salt thereof can be produced by changing a polyazo compound of the formula (I) wherein R
6
is methoxy to a copper complex thereof according to a conventional method.
Examples of salts of polyazo compound of the formula (1) and salts of polyazo compound of the formula (II) include
and the like.
As examples of the salt of a polyazo compound (I) and the salt of a polyazo compound (II), alkali metal salts such as a lithium salt, sodium salt and potassium salt, an ammonium salt, and organic amine salts such as an ethanolamine salt and alkylamine salt, and the like are listed. When a polyazo compound of the formula (I) and/or a polyazo compound of the formula (II) is added into a polarization film substrate, a compound in the form of a sodium salt is preferably used.
When a polyazo compound of the formula (I), a polyazo compound of the formula (II) or salt thereof is added into a polarization film substrate to give a polarization film, hue can be modified and polarization ability can be improved by combination with another organic dye. As the organic dye used in this case, any dye can be used as long as it has high dichroism. A polarization film suitably used in a liquid crystal projector can be produced, using a dye excellent in light resistance.
Specific examples of such organic dyes include the following compounds expressed by Color Index Generic Name.
C. I. Direct Yellow 12
C. I. Direct Yellow 28
C. I. Direct Yellow 44
C. I. Direct Orange 26
C. I. Direct Orange 39
C. I. Direct Orange 107
C. I. Direct Red 2
C. I. Direct Red 31
C. I. Direct Red 79
C. I. Direct Red 81
C. I. Direct Red 247
The dye-based polarization film of the present inven
Ashida Toru
Hayashi Narutoshi
Ohta Yoshiteru
Powers Fiona T.
Stevens Davis Miller & Mosher L.L.P.
Sumitomo Chemical Company Limited
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