Bipyrrolinonylidene-type compound, colorant therewith, and...

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Reexamination Certificate

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C548S518000

Reexamination Certificate

active

06740153

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to bipyrrolinonylidene-type compounds which are useful as colorants such as dyes and pigments, and relates to methods of producing the same.
2. Description of Related Art
A method of producing bipyrrolinonylidene represented by the formula (b):
by air-oxidizing pyrrolinone represented by the formula (a):
is disclosed (see Liebigs Ann. Chem., 702, 112-130 (1967)).
However, the yield in the above method is low, such as 10 to 15%, and the method is not suitable for large-scale industrial production of bipyrrolinonylidene.
Also, it was difficult to employ bipyrrolinonylidene represented by the formula (b) as dyes and pigments, or other organic chemical products or intermediates thereof because of its poor solubility in water and organic solvents.
BRIEF SUMMARY OF THE INVENTION
An object of the present invention is to provide bipyrrolinonylidene-type compounds which are useful as colorants such as dyes and pigments, or other organic chemical products or intermediates thereof, and also provides a method of producing the bipyrrolinonylidene-type compound, which is suitable for large-scale industrial production with high yield.
The present inventors have found that a bipyrrolinonylidene-type compound, which develops a vivid navy blue color and is soluble in various organic solvents, can be produced with high yield by air-oxidizing a pyrrolinone compound using a specific catalyst, and thus the present invention has been completed.
To achieve the above object, the present invention provides a bipyrrolinonylidene-type compound represented by the general formula (1):
wherein Ar
1
and Ar
2
each independently represents an aryl group, and R
1
and R
2
each independently represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 3 to 18 carbon atoms, or an aryl group.
To achieve the above object, the present invention also provides a method of producing a bipyrrolinonylidene-type compound represented by the general formula (4):
wherein Ar
3
represents an aryl group, and R represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an alkyl group, an alkoxyl group, an amino group, an alkylamino group, a cycloalkyl group, a cycloalkyloxy group, an aryl group, an alkoxycarbonyl group, a cycloalkyloxycarbonyl group, a carbamoyl group, a nitro group, a carboxyl group or a sulfonic acid group, which comprises oxidizing a pyrrolinone-type compound represented by the general formula (3):
wherein Ar
3
represents an aryl group, and R represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an alkyl group, an alkoxyl group, an amino group, an alkylamino group, a cycloalkyl group, a cycloalkyloxy group, an aryl group, an alkoxycarbonyl group, a cycloalkyloxycarbonyl group, a carbamoyl group, a nitro group, a carboxyl group or a sulfonic acid group in the presence of an anthraquinone-type catalyst.
The bipyrrolinonylidenedicarboxylic acid-type compound represented by the general formula (1) of the present invention can be used as a dye, as it is, because it develops a vivid navy blue color, or a metal salt of bipyrrolinonylidenedicarboxylic acid can be used as a pigment.
According to the method of the present invention, the bipyrrolinonylidene-type compound represented by the general formula (4) can be produced by a simple method of air-oxidizing a pyrrolinone compound in the presence of an anthraquinone-type catalyst. The bipyrrolinonylidene-type compound represented by the general formula (4) obtained by the method of the present invention is soluble in various solvents as compared with conventionally known bipyrrolinonylidene and is also useful as dyes and pigments, or other organic chemical products or intermediates thereof because it has a carboxyl group or an ester bond.
DETAILED DESCRIPTION OF THE INVENTION
The present invention will now be described.
In the bipyrrolinonylidene-type compound represented by the general formula (1) used in the present invention, Ar
1
and Ar
2
each independently represents an aryl group. Examples of the aryl group include aromatic ring groups such as a phenyl group, naphthalene group, anthracene group, phenanthrene group, pyrene group or biphenyl group; and aromatic hetero ring groups such as a pyrrole group, pyrazole group, imidazole group, pyridine group, pyrimidine group, pyrazine group, indole group, quinoline group, carbazole group, furan group or thiazole group.
Also these aromatic rings may have substituents. Examples of the substituents include a hydrogen atom, halogen atom, cyano group, hydroxyl group, alkyl group, amino group, alkylamino group, alkoxyl group, aryl group, alkoxycarbonyl group, carbamoyl group, nitro group, sulfonic acid group and sulfonate group. Among these substituents, a halogen atom or sulfonic acid group is preferred. When the substituent is a halogen, the bipyrrolinonylidenedicarboxylic acid derivative (A) tends to exhibit higher chemical stability. When the substituent is a sulfonic acid group or a sulfonic acid metal salt group, the bipyrrolinonylidenedicarboxylic acid derivative (A) tends to exhibit higher solubility in water or organic solvents.
When the aromatic ring is substituted with plural halogen atoms, halogen atoms may be the same or different. When the halogen atom is a chlorine atom or a bromine atom, the bipyrrolinonylidenedicarboxylic acid derivative (A) tends to exhibit higher chemical stability and, therefore, it is preferred.
In the general formula (1), R
1
and R
2
each independently represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 3 to 18 carbon atoms, or an aryl group. It is preferred that R
1
and R
2
each independently represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms. Examples of the alkyl group having 1 to 18 carbon atoms include alkyl groups such as a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group or n-octadecyl group; and cycloalkyl groups such as a cyclohexyl group. It is preferred that the bipyrrolinonylidene-type compound represented by the general formula (1) tends to exhibit higher heat stability when R
1
and R
2
each independently represents an alkyl group having 1 to 8 carbon atoms.
Among the bipyrrolinonylidene-type compounds represented by the general formula (1), a bipyrrolinonylidene-type compound represented by the general formula (2):
wherein X
1
, X
2
, X
3
, X
4
, X
6
, X
7
, X
8
, X
9
and X
10
each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an alkyl group, an amino group, an alkylamino group, an alkoxyl group, an aryl group, an alkoxycarbonyl group, a cycloalkyloxycarbonyl group, a carbamoyl group, a nitro group, a sulfonic acid group or a sulfonate group, and R
1
and R
2
each independently represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 3 to 18 carbon atoms, or an aryl group is preferred.
The bipyrrolinonylidene-type compound represented by the general formula (1) used in the present invention has high solubility in water or organic solvents because it has a carboxyl group or an ester bond in a molecule, and also the bipyrrolinonylidene-type compound can be used as a dye, as it is, because it develops a blue to violet color hue. Among the compounds represented by the general formula (1), a metal salt of a bipyrrolinonylidene-type compound in which R
1
and R
2
are hydrogen atoms can be used as a pigment because it is insoluble in water or organic solvents.
Among the bipyrrolinonylidene-type compounds used in the present invention, a bipyrrolinonylidene-type compound in which R
1
and R
2
are hydrogen atoms has the solubility in water and an organic solvent, and solubility suitable for the objective purposes can be imparted by reacting with a carboxyl group thereby introducing various atomic groups.
Among the bipyrrolinonylidene-type compounds represented by the general formula (1) used in the present i

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