Diazo compound and heat-sensitive recording material

Details Diazo compound and heat-sensitive recording material Diazo compound and heat-sensitive recording material

1999-11-19

2002-02-19

Hess, Bruce H. (Department: 1774)

Record receiver having plural interactive leaves or a colorless

Having a colorless color-former, developer therefor, or...

Identified color-former

C503S215000

Reexamination Certificate

active

06348433

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a diazo compound and a heat-sensitive recording material using the same. More particularly, the present invention relates to a diazo compound which is stable in light having a longer wavelength than 350 nm, and to a heat-sensitive recording material which shows good storage stability before use (storage stability of a heat-sensitive recording material before being subjected to recording) and good density of color-development upon thermal recording and is stable in light having a longer wavelength than 350 nm.
2. Description of the Related Art
Diazo compounds are compounds having very high chemical activity, and easily react with compounds called couplers, (e.g., phenol derivatives and compounds having an active methylene group) to form an azo dye, and also are light-sensitive and lose their activity when decomposed due to irradiation by light. Therefore, diazo compounds have been used as light recording materials such as diazo copies (see, “Fundamentals of Photographic Technology, Non-Silver Salt Photography Volume (Shashin Kogaku no Kiso, Higinen Shashin Hen)”, edited by Nippon Shashin Gakkai (Japan Photographic Society, Corona Co., (1982), pp. 89 to 117, and pp. 182 to 201).
Further, by utilizing the property of diazo compounds that they lose their activity due to decomposition by light, diazo compounds have recently been used in recording materials which require fixing of images. As an example, there has been proposed a light fixing type heat-sensitive recording material in which a recording material having a recording layer which includes a diazo compound and a coupler is heated in accordance with image signals and the diazo compound and the coupler are reacted to form images, and thereafter, the images are fixed by irradiation of light (Hirotsugu Sato et al., “Journal of the Image Electronics Society (Gazo Denshi Gakkai Shi)”, Vol. 11. No. 4 (1982), pp. 290 to 296, etc.).
However, these recording materials using as a color-forming element a diazo compound have a drawback in that the chemical activity of the diazo compound is extremely high, and the diazo compound thermally decomposes gradually such that the reactivity thereof is lost. Moreover, when the recording material is stored in a bright place for a long time, photolysis of the diazo compound is accelerated, and, when such a recording material is used for image recording after storing, the density of color-development of the image portion tends to be reduced.
SUMMARY OF THE INVENTION
An object of the present invention is to solve the aforementioned problems. That is, the object of the present invention is to provide a diazo compound which has a sufficiently high density of color-development and good storage stability, and a heat-sensitive recording material using the diazo compound which shows good color-developing properties, light-resistance properties, storage stability before use, and handling properties in light places.
To achieve the aforementioned object, the present invention has following features.
In a first aspect of the present invention, the present invention provides a diazo compound represented by the following general formulae (I)-(III):
wherein, in general formula (I), each of R
1
, R
2
, R
3
and R
4
independently represents any one of the groups selected from a group comprising a hydrogen atom, a halogen atom, an alkyl group, an aryl group, —OR
10
, —SR
10
, —COOR
10
, —CONR
10
R
11
, —SO
2
R
10
, —SO
2
NR
10
R
11
, —COR
10
, a nitro group and a cyano group, each of R
5
, R
6
, R
7
, R
8
and R
9
independently represents any one of the groups selected from a group comprising a hydrogen atom, a halogen atom, an alkyl group, an aryl group, —OR
12
, —COOR
12
, —CONR
12
R
13
, —SO
2
R
12
, —SO
2
NR
12
R
13
, —COR
12
, a nitro group and a cyano group, each of R
10
, R
11
, R
12
and R
13
independently represents any one of the groups selected from a group comprising a hydrogen atom, an alkyl group and an aryl group, here, at least one of the R
1
, R
2
, R
3
and R
4
represents any one of the groups selected from a group comprising —COOR
10
, —CONR
10
R
11
, —SO
2
R
10
, —SO
2
NR
10
R
11
, a nitro group and a cyano group, and at least one of the R
5
, R
6
, R7, R
8
and R
9
represents any one of the groups selected from a group comprising —COOR
12
, —CONR
12
R
13
, —SO
2
R
12
, —SO
2
NR
12
R
13
, a nitro group and cyano group.
wherein, in general formula (II), each of R
21
, R
22
, R
23
and R
24
independently represents any one of the groups selected from a group comprising a hydrogen atom, a halogen atom, an alkyl group, —OR
30
, —COOR
30
, —SO
2
R
30
, a nitro group, a cyano group and —CONR
30
R
31
, each of R
25
, R
26
, R
27
, R
28
and R
29
independently represents any one of the groups selected from a group comprising a hydrogen atom, a halogen atom, —OR
32
, —COOR
32
, —CONR
32
R
33
, —SO
2
NR
32
R
33
, a nitro group and a cyano group, each of R
30
, R
31
, R
32
, and R
33
independently represents any one of the groups selected from a group comprising a hydrogen atom, an alkyl group and an aryl group, here, at least one of the R
21
, R
22
, R
23
and R
24
represents any one of groups selected from a group comprising —CONR
30
R
31
, —COOR
30
, —SO
2
R
30
, a nitro group and a cyano group, and at least one of the R
25
, R
26
, R
27
, R
28
, and R
29
represents any one of the groups selected from a group comprising —COOR
32
, —CONR
32
R
33
, —SO
2
NR
32
R
33
, a nitro group and a cyano group.
wherein, in general formula (III), each of R
21
, R
22
, R
23
and R
24
independently represents any one of the groups selected from a group comprising a hydrogen atom, a halogen atom, an alkyl group, —OR
30
, —COOR
30
, —SO
2
R
30
, a nitro group, a cyano group and —CONR
30
R
31
, each of R
30
and R
31
independently represents any one of the groups selected from a group comprising a hydrogen atom, an alkyl group and an aryl group, R
34
represents a group selected from the following monovalent groups, each of R
35
and R
36
independently represents an alkyl group or an aryl group, here, at least one of R
21
, R
22
, R
23
, and R
24
represents —CONR
30
R
31
, —COOR
30
, —SO
2
R
30
, a nitro group and a cyano group.
In a second aspect of the present invention, the present invention provides a heat-sensitive recording material, comprising: a substrate; and a heat-sensitive recording layer provided on said substrate. Said heat-sensitive recording layer including at least: a diazo compound; and a coupler to react with said diazo compound to color said diazo compound, said diazo compound being represented by one of the general formulae (I)-(III).
In a third aspect of the present invention, said diazo compound is encapsulated in a microcapsule and said microcapsule consists of at least one of urethane or urea.
In a fourth aspect of the present invention, said coupler is a compound represented by general formula (IV) or a resonance isomer of the compound:
general formula (IV)
E
1
—CH
2
—E
2
wherein in general formula (IV), each of E
1
and E
2
independently represents an electron attractive group, and E
1
and E
2
may combine with each other to form a ring.
In a fifth aspect of the present invention, said heat-sensitive recording material having the aforementioned aspects further comprises an organic base.
In a sixth aspect of the present invention, said heat-sensitive recording material having the aforementioned aspects further comprises a color-developing assistant and a protective layer provided on said heat-sensitive recording layer for protecting said heat-sensitive recording layer.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
1. A diazo Compound Represented by General Formula (I)
In general formula (I), each of R
1
, R
2
, R
3
and R
4
independently represents any one of the groups selected from a group comprising a hydrogen atom, a halogen atom, an alkyl group, an aryl group, —OR
10
, —SR
10
, —COOR
10
, —CONR
10
R
11
, —SO
2
R
10
, —SO
2
NR
10
R
11
, —COR
10
, a nitro group and a cyano group. The haloge

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