Dye and image recording material, and thermal transfer...

Details Dye and image recording material, and thermal transfer... Dye and image recording material, and thermal transfer...

1999-06-24

2002-02-05

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031430, C106S031470, C106S031490

Reexamination Certificate

active

06344075

ABSTRACT:

BACKGROUND OF THE INVENTION
Conventionally, in order to obtain high-quality full color images employing a simple apparatus, is known a method in which a thermal transfer material is employed. In this method, dyes employed for forming color images are most essential and affect the performance of a variety of areas such as color reproduction of color images, various types of fastness, maximum density, thermal sensitivity, etc. Hitherto, various dyes such as styryl series, pyridoneazo series, pyrazoleazo series, anthraquinone series, naphthoquinone series, azomethine series, indoaniline series, and the like, have been investigated. However, dyes which exhibit satisfactory fastness, specifically in light fastness, have not been found yet.
In recent years, dyes, in which the aniline structure part of azomethine dyes and indoaniline dyes is altered to a heterocycle, have been investigated and the light fastness has been improved. For example, known regarding pyridine series dyes, are Japanese Patent Publication Open to Public Inspection Nos. 4-89287, 5-239367, 6-73009, 6-80638, 7-232482, etc. Regarding thiazole series dyes, are known Japanese Patent Publication Open to Public Inspection Nos. 3-93862, 4-234860, 4-338592, 5-309954, 8-283591, etc. Regarding thiophene series dyes, are known Japanese Patent Publication Open to Public Inspection Nos. 6-143838 and 6-143839. In addition, azomethine dyes having a 5-membered unsaturated heterocyclic structure are disclosed in Japanese Patent Publication Open to Public Inspection No. 6-219057.
As described above, many types of dyes have been investigated so far, but dyes having satisfactory light fastness have not been discovered. Thus, further improvement in the light fastness is being sought.
In ink-jet recording, conventionally employed azo series dyes, xanthene series dyes, triphenylmethane series dyes, etc. do not exhibit satisfactory fastness, specifically in light fastness. Among azomethine dyes, recently, those, in which the aniline structure part is altered to a heterocycle, have been investigated to improve the light fastness. For example, regarding pyridine series dyes, Japanese Patent Publication Open to Public Inspection No. 9-150572 is known. However, at present, dyes having satisfactory light fastness have not yet been discovered. Further improvement in the light fastness is demanded.
Similarly, in color electrophotography, dyes exhibiting satisfactory fastness, specifically in light fastness have not been found in the same way as have thermal transfer materials and ink-jet recording liquids.
As described above, in a variety of image recording materials, improvement in image fastness, specifically in light fastness is demanded, however, there are no image recording materials which exhibit satisfactory properties. This is largely due to the fact that dyes having sufficient fastness, specifically in light fastness have not been discovered.
Japanese Patent Publication Open to Public Inspection No. 6-80900 discloses dyes composed of aminophenol compounds and couplers. However, the resulting dyes exhibit insufficient light fastness.
U.S. Pat. No. 2,895,825 discloses that 4-aminopyrazolone compounds are employed as a developing agent for silver halide color photosensitive photographic materials. However, in that document, no description is given on isolation of dyes employing the developing agent, or application of dyes employing the developing agent to thermal transfer materials, to ink-jet recording or to a color toner for electrophotography, and the technique only disclose a method in which the resulting compounds are employed as a developing agent for silver halide photosensitive color photographic material to form images. Accordingly, nothing is described on the fastness of color images on the media employed for the thermal transfer recording or ink-jet recording.
SUMMARY OF THE INVENTION
An object of the present invention is to provide novel dyes which are excellent in fastness, specifically in light fastness, and image recording materials, thermal transfer materials, and ink-jet recording liquids employing said dyes.
The present invention and embodiments thereof will now be described.
A dye represented by formula (1)
B═N—A  (1)
wherein A represents a metal-free atomic group necessary to form a condensed ring having —NR
1
R
2
as a substituent on the ring, except for one ring in which a carbon atom on the ring combines with the nitrogen atom in the formula, and B represents a coupler component and combines with a nitrogen atom in the formula at the coupling position of the coupler component. R
1
and R
2
each independently represents a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, and a heterocycle which may have a substituent, and R
1
and R
2
may combine with each other to form a ring.
A dye described above in which A represents a metal-free atomic group necessary to form an aromatic condensed ring composed of two rings having —NR
1
R
2
as a substituent on a ring except for, one ring in which a carbon atom on the ring combines with the nitrogen atom in the formula.
A dye represented by formula (2)
B═D—A  (2)
wherein A represents a metal-free atomic group necessary to form a condensed ring having —NR
1
R
2
as a substituent on the ring, except for one ring in which a carbon atom on the ring combines with D, and B represents a coupler component and combines with D at the coupling position of the coupler component. R
1
and R
2
each independently represents a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, and a heterocycle which may have a substituent, and R
1
and R
2
may combine with each other to form a ring. D represents a nitrogen atom or CR
3
. R
3
represents a hydrogen atom or a substitutable group.
A dye represented by formula (I)
Y═G—X  (I)
wherein X and Y each independently represents a coupler component, and G combines with a coupler component at the coupling position. G represents a nitrogen atom or C—R
X
, in which R
X
represents a hydrogen atom or a substitutable group, however except that at least one of X and Y is phenol, and may also have a substituent.
In the formula (I) Y is preferably not a cyan coupler component.
In the formula (I) either X or Y is preferably a magenta coupler component.
In the formula (I) both X and Y are preferably magenta coupler components.
A dye represented by formula (2-1)
 A
2
—N═B
2
  (2-1)
wherein B
2
represents a coupler component and combines with the nitrogen atom at the coupling position of the coupler component. A
2
represents a heterocycle composed of a single ring containing at least one nitrogen atom in the ring or a condensed ring having at least two rings containing at least one nitrogen atom in the rings, and at least one nitrogen atom in the heterocycle is a conjugated terminal and a conjugated chain is completed with —N═B
2
. However, cases are excluded when the heterocycle in A
2
is substituted with an amino group, and when the coupler component represented by B
2
is phenol which may have a substituent.
In preferable examples of dye of the formula (2-1), A
2
represents a heterocycle composed of a single ring containing at least one nitrogen atom in the ring or a condensed ring having at least two rings containing at least one nitrogen atom in the rings, and at least one nitrogen atom in the heterocycle is a conjugated terminal and a conjugated chain is completed with —N═B
2
, and the nitrogen atom of —N═B
2
is substituted on a ring containing the nitrogen atom which is the conjugated terminal (however, cases are excluded when the heterocycle represented by A
2
is substituted with an amino group, and when the coupler component represented by B
2
is phenol which may have a substituent.
In the formula (2-1) a heterocycle represented in A
2
is preferably a single ring compound.
In the formula (2-1) the heterocycle represented by A
2
is a condensed polycyclic compou

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