Decolorizable dye

Details Decolorizable dye Decolorizable dye

1999-08-26

2001-03-06

Shah, Mukund J. (Department: 1624)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S138000, C548S146000

Reexamination Certificate

active

06197968

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a decolorizable dye. More specifically, the present invention pertains to a decolorzable dye which becomes colorless rightly after solution treatment.
2. Description of the Related Art
Enormous efforts have been made for decreasing color remaining (residual color) which occurs after processing of a silver halide photographic material. Particularly in recent years, with a view to satisfying environmental countermeasures and user's needs, there has been a strong demand for processing speed enhancement and replenishment reduction of a photographic processing solution. A sensitizing dye or pigment (which will hereinafter be called “photographic dye” collectively) therefore needs a new molecular design utterly different from that of the conventional one.
It is widely known that color remaining of a photographic dye is effectively reduced by washing away the dye, which has hydrophilic property enhanced, into a processing solution upon photographic processing. The enhancement of hydrophilic property however usually impairs the adsorption property of a sensitizing dye to silver halide grains and adversely affects the performances of photograph such as sensitivity, fog and storage stability. It is therefore very difficult to attain reduction in color remaining and other photographic performances at the same time.
Investigations have been energetically carried out in order to remove the color of a photographic dye by making use of the chemical reaction between the dye and an additive of a photographic processing solution such as nucleophilic agent, electrophilic agent, oxidizing agent or reducing agent, or other chemical species. There are however not so many additives which do not worsen the photographic performances and complete suppression of color remaining by the reaction with a dye has been found to be difficult as a result of investigations so far made.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a decolorizable dye which can stably maintain color forming conditions during storage but becomes colorless immediately after solution treatment.
As a result of extensive investigations, the object of the present invention can be attained by the following means.
(1) A decolorizable dye represented by the following formula (I):
wherein R
1
represents an alkyl, aryl or heterocyclic group; R
2
and R
3
independently each represents a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group, or may be coupled together to form a ring; L
1
and L
2
independently each represents a methine group or a nitrogen atom; L
3
and L
4
independently each represents a methine group; Z represents an atomic group necessary for the formation of a 5- or 6-membered hetero ring; m stands for 0 or 1; Y represents an oxygen, sulfur, selenium or tellurium atom; V represents a monovalent group and p stands for 0, 1, 2 or 3, and when p stands for 2 or 3, plural substituents V may be the same or different, or two of said substituents V or said substituent V and R
2
or R
3
may be coupled to form a condensed ring; X represents a counterion; and n stands for 0 or greater necessary for the neutralization of an electron charge in the molecule.
(2) A decolorizable dye represented by the following formula (II):
wherein R
11
represents an alkyl group; R
12
and R
13
each independently represents a hydrogen atom or an alkyl group or may be coupled together to form a ring; L
11
and L
12
each independently represents a methine group or a nitrogen atom; Z
1
represents an atomic group necessary for the formation of a 5- or 6-membered hetero ring; Y
1
represents an oxygen or sulfur atom; V
1
represents a halogen atom or a nitro, cyano, alkyl, aryl, alkoxy, aryloxy, alkylthio, arylthio, acyl, acyloxy, carboxy, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, alkanesulfonyl, sulfo or sulfamoyl group and p
1
stands for 0, 1 or 2, and when p
1
stands for 2, two substituents V
1
may be the same or different, or two substituents V
1
, or V
1
and R
12
or V
1
and R
13
may be coupled to form a condensed ring; X
1
represents a counterion, and n
1
stands for a numeral of 0 or greater necessary for the neutralization of an electron charge in the molecule.
(3) A decolorizable dye represented by the following formula (III):
wherein R
1
1
, R
2
, R
3
, L
1
, L
2
, L
3
, L
4
, Z, m, Y, V, p, X and n have the same meanings as corresponding ones in the formula (I), respectively and A represents a group eliminative by solution treatment (i.e., a group which can be eliminated by solution treatment).
(4) A decolorizable dye represented by the following formula (IV):
wherein R
11
, R
12
, R
13
, L
11
, L
12
, Z
1
, V
1
, p
1
, X
1
and n
1
have the same meanings as corresponding ones in the formula (II), respectively and A
1
represents an acyl, alkanesulfonyl or arenesulfonyl group
From the compounds of the present invention, dye compounds which have stable color forming condition and are decolorized easily by solution treatment can be obtained.
BRIEF DESCRIPTION OF THE PREFERRED EMBODIMENTS
Compounds to be used in the present invention will next be described more specifically.
The alkyl group represented by R
1
, R
2
, R
3
, R
11
, R
12
or R
13
in the formula (I), (II), (III) or (IV) may be substituted or unsubstituted. In the present specification, Cn-m represents a group having n to m carbon atoms. Examples include unsubstituted C
1-30
, preferably C
1-18
alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, hexyl, octyl and octadecyl; and substituted C
1-36
, preferably C
1-24
alkyl groups. Examples of the substituent include carboxy group, sulfo group, cyano group, halogen atoms such as fluorine, chlorine, bromine and iodine, hydroxy group, mercapto group, C
1-7
alkoxycarbonyl groups such as methoxycarbonyl ethoxycarbonyl and benzyloxycarbonyl, C
6-12
aryloxycarbonyl groups such as phenoxycarbonyl, C
1-7
alkoxy groups such as methoxy, ethoxy and benzyloxy, C
6-12
aryloxy groups such as phenoxy and p-tolyloxy, C
1-7
acyloxy groups such as acetyloxy and propionyloxy, C
1-7
acyl groups such as acetyl, propionyl and benzoyl, carbamoyl groups such as carbamoyl, N,N-dimethylcarbamoyl, morpholinocarbonyl and piperidinocarbonyl, sulfamoyl groups such as sulfamoyl, N,N-dimethylsulfamoyl, morpholinosulfonyl and piperidinosulfonyl, C
6-12
aryl groups such as phenyl, p-chlorophenyl and p-tolyl, sulfonylcarbamoyl group and acylsulfamoyl group.
In the formula (I) or (III), the aryl group represented by R
1
, R
2
or R
3
may be substituted or unsubstituted. Examples include unsubstituted C
6-30
, preferably C
6-18
aryl groups such as phenyl, 1-naphthyl and 2-naphthyl and substituted C
6-36
, preferably C
6-24
aryl groups. Examples of the substituent include those exemplified in the description of the substituted alkyl group such as carboxy group, sulfo group, cyano group, halogen atoms, hydroxy group, mercapto group, alkoxycarbonyl groups, aryloxycarbonyl groups, alkoxy groups, aryloxy groups, acyloxy groups, acyl groups, carbamoyl groups, sulfamoyl groups, aryl groups, sulfonylcarbamoyl group and acylsulfamoyl group.
In the formula (I) or (III), the heterocyclic group represented by R
1
, R
2
or R
3
may be substituted or unsubstituted. Examples include unsubstituted C
1-30
to C
1-18
heterocyclic groups such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidyl, 2-imidazolyl, 3-pyrazolyl, 1-piperidino, 1-morpholino and 1-indolyl; and substituted C
1-36
, preferably C
1-24
heterocyclic groups. Examples of the substituent include those exemplified in the description of the substituted alkyl group such as carboxy group, sulfo group, cyano group, halogen atoms, hydroxy group, mercapto group, alkoxycarbonyl groups, aryloxycarbonyl groups, alkoxy groups, aryloxy groups, acyloxy groups, acyl groups, carbamoyl groups, sulfamoyl groups, aryl groups, sulfonylcarbamoyl group and acylsulfamoyl group.
As R
11
, more preferred are

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