Hydrazone dye

Details Hydrazone dye Hydrazone dye

2000-10-10

2001-11-13

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C544S211000, C544S220000, C544S282000

Reexamination Certificate

active

06316605

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a hydrazone dye having a novel structure, and relates to a dye used in recording materials for thermal transfer recording, ink jet recording and the like, and to a colorant (composition) for use in a filter or the like.
2. Description of the Related Art
Azo dyes are dyes which are used the most; they account for more than half of the dyes which are used.
There are many publications about azo dyes. Representative among them are
Color Chemistry
(Heinrich Zollinger, Weinheim, New York, Basel, Cambridge 1987),
Synthetic Dyes
(
Gosei Senryou
) (Hiroshi Horiguchi, Sankyo Shuppan KK, 1970), and the like. Details are described in the chapters on azo dyes and azo pigments.
An azo dye is generally defined as being a structure in which a carbon having an sp
2
hybrid orbital is bonded to each of the both ends of an azo group (—N═N—).
For example, the compound azobenzene represented by the following formula falls into the category of azo dyes.
When azobenzene has a dissociated group, a tautomer is generated depending on the position of the dissociated group. For example, in an azobenzene in which —OH is substituted at the position next to the azo group, the following tautomer is generated. azo structure hydrazone structure
A detailed discussion relating to tautomers of azobenzene can be und on pages 133 through 137 of the aforementioned
Color Chemistry.
In order to improve the hue such as making the absorption of the dye sharper or the like, it is preferable to lean toward either an azo structure or a hydrazone structure. Or, structures that do not produce tautomers are preferable. However, there has still not been developed a cyan color forming azo dye resulting in a good hue.
SUMMARY OF THE INVENTION
The present invention was developed in light of the above-described circumstances, and an object thereof is to provide a hydrazone dye which forms colors in the range from magenta through cyan having excellent hues.
The following hydrazone dyes are provided in order to achieve the above-described object.
(1) A hydrazone dye comprising a compound represented by a general formula (I) as follows:
wherein Ar represents an aryl group or a heterocyclic group; R
1
through R
4
each represent a hydrogen atom, a halogen, —CN, —NH
2
, —NO
2
, —OH, —CO
2
H, —SO
3
H, a quaternary ammonium group, —CO
2
M
1

, —SO
3
M
1

, an alkyl group, alkenyl group, alkynyl group, aryl group, acyl group, carbamoyl group, sulfamoyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, alkylphosphoryl group, arylphosphoryl group, or a substituted amino group; M represents a metal atom; and n represents an integer from 1 to 4.
(2) The hydrazone dye according to the above (1), wherein the group represented by Ar is represented by a general formula (II) as follows:
wherein R
5
and R
6
each represent a hydrogen atom, an alkyl group, or an aryl group; and R
7
through R
10
are each respectively defined identical to that for R
1
through R
4
of general formula (I).
(3) The hydrazone dye according to claim
1
, wherein the group represented by Ar is represented by a general formula (III) as follows:
wherein R
11
through R
13
represent a hydrogen atom, an alkyl group or an aryl group; R
14
represents a hydrogen atom, a halogen, an alkyl group, an alkoxy group, an aryl group or an aryloxy group; and X represents O or S.
(4) The hydrazone dye according to claim
1
, wherein the group represented by Ar is represented by a general formula (IV) as follows:
wherein R
15
is a hydrogen atom, an alkyl group or an aryl group; R
16
and R
17
represent a hydrogen atom, a halogen, an alkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group or an aryl group; and Y represents O or S.
(5) A hydrazone dye comprising a compound represented by a general formula (V) as follows:
wherein Ar′ represents an aryl group or a heterocyclic group; R
18
and R
19
each represent a hydrogen atom, a halogen, —CN, —NH
2
, —NO
2
, —OH, —CO
2
H, —SO
3
H, a quaternary ammonium group, —CO
2
M
1

, —SO
3
M
1

, an alkyl group, alkenyl group, alkynyl group, aryl group, acyl group, carbamoyl group, sulfamoyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, alkylphosphoryl group, arylphosphoryl group, or a substituted amino group; R
20
represents an acyl group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonyl group, an alkylsulfonyl group, or an arylsulfonyl group; and R
21
represents a hydrogen atom, an alkyl group, an aryl group or an acyl group.
In a preferred embodiment, the group represented by Ar′ is represented by a general formula (VII) as follows:
wherein R
28
through R
30
represent a hydrogen atom, an alkyl group or an aryl group; R
31
represents a hydrogen atom, a halogen, an alkyl group, an alkoxy group, an aryl group or an aryloxy group; and X represents O or S.
In another preferred embodiment, the group represented by Ar′ is represented by a general formula (VIII) as follows:
wherein R
32
is a hydrogen atom, an alkyl group or an aryl group; R
33
and R
34
represent a hydrogen atom, a halogen, an alkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group or an aryl group; and Y represents O or S.
(6) A hydrazone dye comprising a compound represented by a general formula (IX) as follows:
wherein Ar″ represents an aryl group or a heterocyclic group; R
22
R
24
and R
25
each represent a hydrogen atom, a halogen, —CN, —NH
2
, —NO
2
, —OH, —CO
2
H, —SO
3
H, a quaternary ammonium group, —CO
2
M
1

, —SO
3
M
1

, an alkyl group, alkenyl group, alkynyl group, aryl group, acyl group, carbamoyl group, sulfamoyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, alkylphosphoryl group, arylphosphoryl group, or a substituted amino group; and R
23
represents an electron attracting group whose Hammett &sgr;
p
value is 0.25 or more.
In a preferred embodiment, the group represented by Ar″ is represented by a general formula (XI) as follows:
wherein R
45
trough R
47
represent a hydrogen atom, an alkyl group or an aryl group; R
48
represents a hydrogen atom, a halogen, an alkyl group, an alkoxy group, an aryl group or an aryloxy group; and X represents O or S.
In another preferred embodiment, the group represented by Ar″ is represented by a general formula (XII) as follows:
wherein R
49
is a hydrogen atom, an alkyl group or an aryl group; R
50
and R
51
represent a hydrogen atom, a halogen, an alkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group or an aryl group; and Y represents O or S.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present invention will be described in detail hereinafter.
As described above, in order to improve the hue such as make the absorption of the dye more sharp or the like, it is preferable to lean toward either an azo structure or a hydrazone structure, or a structure which does not produce tautomers is preferable. However, the inventors of the present invention studied techniques for fixing an azo dye having a dissociated group to a hydrazone structure. As a result, the present inventors found that it is difficult for the hydrazone dye of the present invention represented by general formula (I) to isomerize into an azo structure, and thus arrived at the present invention. The hydrazone dye of the present invention results in the formation of a cyan color which has an excellent hue and whose dye absorption is sharp.
The hydrazone dye of the present invention is represented by following general formula (I).
In general formula (I), Ar represents an aryl group or a heterocyclic group; R
1
through R
4
each represent a hydrogen ato

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