Azomethine yellow dye compound

Details Azomethine yellow dye compound Azomethine yellow dye compound

2002-09-26

2003-09-16

Ramsuer, Robert W. (Department: 1752)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C546S309000, C548S265400, C548S558000, C549S480000, C554S045000, C558S394000, C558S416000, C560S013000, C562S047000, C562S052000, C564S082000, C564S086000, C564S099000, C564S164000, C564S165000

Reexamination Certificate

active

06620933

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an azomethine yellow dye compound having an aryl group bonded to a carbon atom in an azomethine moiety thereof, which is useful as yellow dye for silver halide photographic photosensitive materials, yellow dye for printing materials used in inkjet or thermal transfer printing or the like, yellow dye for toner in electrophotography, yellow dye for prints, yellow dye for color proofs, yellow dye for optical memory media, yellow dye for organic electroluminescence elements, filter dye for solid-state image pickup tubes or color liquid-crystal televisions, and also as an intermediate in the production thereof.
2. Description of the Related Art
Many types of yellow azomethine dyes are generally known and are used as yellow dye compounds used for silver halide photographic photosensitive materials and also as dyes or colorants for other various purposes. Especially for silver halide photographic photosensitive materials, azomethine dyes having an aniline derivative bonded to the nitrogen atom in an azomethine moiety thereof and having an acyl group, a carbamoyl group, an alkoxycarbonyl group or the like bonded to a carbon atom in said moiety are widely known. These dyes can be formed by reacting an active methylene compound (generally a yellow coupler) provided in a silver halide photographic photosensitive material with an oxide product of a p-phenylenediamine based developing agent when the photographic photosensitive material is developed, and these dyes have been used as photographic dye.
However, these yellow azomethine dyes are problematic in that an absorption coefficient thereof is small and a hydrolysis stability thereof against acid is low. As one means for solving these problems, use of azomethine yellow dye compounds having an aryl group and a carbamoyl group both bonded to a carbon atom in an azomethine moiety thereof has been taken into consideration. Some azomethine compounds having an aryl group and a carbamoyl group both bonded to a carbon atom in an azomethine moiety thereof are described in, for example,
Farmaco
, 54, 39 (1999);
Pestic. Sci
., 44, 49 (1995);
J. Pract. Chem
., 128, 1 (1930),
Zh. Obshch. Khim
., 26, 1169 (1956); and
Zh. Obshch. Khim
., 26, 2019 (1956). In all of these azomethine dye compounds described therein, however, a nitrogen atom in the carbamoyl group bonded to the carbon atom in the azomethine moiety is bonded to the aryl group that is bonded to the carbon atom in the azomethine moiety either directly or via a linking group, such as carbonyl group, provided therebetween. Further, these dye compounds are still problematic in that a color hue thereof is not good. These azomethine dye compounds described above are not those of a type having a hydrogen atom bonded to the nitrogen atom in the carbamoyl group therein.
On the other hand, some other azomethine compounds having an aryl group and a carbamoyl group, which has a hydrogen atom bonded to a nitrogen atom thereof, with both groups being bonded to a carbon atom in the azomethine moiety thereof, as described, for example, in
J. Org. Chem. USSR
, 10, 609 (1974);
J. Pract. Chem
., 114, 332
; Tetrahedron Lett
., 1967, 3291
; Justus Liebigs Ann. Chem
., 442, 266 (1926);
J. Pract. Chem
., 114, 332 (1926);
J. Chem. Soc
., 1929, 1198; and
Bull. Chem. Soc. Jpn
., 69, 25 (1996), are known. However, these compounds do not have an amino group at a para-position of a phenyl group bonded to the nitrogen atom in the azomethine moiety thereof, and furthermore, since a maximum absorption wavelength thereof is short, they con not be used as yellow dye.
As described above, an azomethine yellow dye having a p-aminophenyl group bonded to the nitrogen atom in an azomethine moiety thereof, and having an aryl group and a carbamoyl group both bonded to a carbon atom in the azomethine moiety thereof with the carbamoyl group having a hydrogen atom bonded to a nitrogen atom in the carbamoyl group, is completely unknown.
SUMMARY OF THE INVENTION
An object of the present invention is to provide an azomethine yellow dye compound that has a large absorption absorption coefficient and is stable against acid hydrolysis. The dye compound has a p-aminophenyl group bonded to a nitrogen atom in an azomethine moiety thereof and has an aryl group and a carbamoyl group both bonded to a carbon atom in the azomethine moiety thereof. The carbamoyl group has a hydrogen atom bonded to a nitrogen atom thereof.
Having assiduously studied the problems noted above, the present inventors have found that these problems can be solved by the following method.
A first aspect of the present invention is an azomethine yellow dye compound represented by the following general formula (I).
General formula (I)
In the general formula (I), R
1
and R
2
each independently represent a hydrogen atom or a substituent; R
3
represents a a substituent; m indicates an integer from 0 to 3; when m is 2 or greater, R
3
's may be the same as or different from each other, and the R
3
's may be bonded to each other to form a condensed ring; R
3
's may be bonded to R
1
or R
2
to form a condensed ring; R
4
represents an aryl group or a heterocyclic group; R
5
and R
6
each independently represent a hydrogen atom or a substituent; R
7
represents a substituent; n indicates an integer from 0 to 4; and when n is 2 or greater, R
7
's may be the same as or different from each other, and the R
7
's may be bonded to each other to form a condensed ring; R
7
may be bonded to R
5
or R
6
to form a condensed ring; and R
5
and R
6
may be bonded to each other to form a ring.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The compound of the present invention, which is represented by the following general formula (I), is described in detail below.
General formula (I)
In the formula (I), R
1
and R
2
each independently represent a hydrogen atom or a substituent; R
3
represents a substituent; m indicates an integer from 0 to 3; and when m is 2 or greater, R
3
's may be the same as or different from each other, and the R
3
's may be bonded to each other to form a condensed ring; R
3
may be bonded to R
1
or R
2
to form a condensed ring; R
4
represents an aryl group or a heterocyclic group; R
5
and R
6
each independently represent a hydrogen atom or a substituent; R
7
represents a substituent; n indicates an integer from 0 to 4; when n is 2 or greater, R
7
's may be the same as or different from each other, and the R
7
's may be bonded to each other to form a condensed ring; R
7
may be bonded to R
5
or R
6
to form a condensed ring; and R
5
and R
6
may be bonded to each other to form a ring. Herein, “substituent” means a substituting group other than a hydrogen atom.
In general formula (I), R
1
and R
2
each independently represent a hydrogen atom or a substituent. Examples of the substituent include ahalogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic-oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group (examples of which include an alkylamino group, an arylamino group and a heterocyclic amino group), an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkylsulfonylamino group, arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic-thio group, a sulfamoyl group, a sulfo group, an alkylsulfinyl group, arylsulfinyl group, an alkylsulfonyl group, arylsulfonyl group, an aryloxysulfinyl group, an alkoxysulfinyl group, an aryloxysulfonyl group, an alkoxysulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an aryl or heterocyclic-azo group, an imido group, a phosphino gr

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