Heat-sensitive recording material

Details Heat-sensitive recording material Heat-sensitive recording material

1998-12-01

2001-03-06

Hess, Bruce H. (Department: 1774)

Record receiver having plural interactive leaves or a colorless

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

Identified organic electron acceptor other than phenolic resin

C503S215000, C503S217000

Reexamination Certificate

active

06197725

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a recording material utilizing the heat sensitivity of a diazonium salt compound. More particularly, the present invention relates to a novel diazo heat-sensitive recording material developing red to magenta to violet, excellent in image storability and image fixing property.
2. Description of the Related Art
A diazonium salt compound has been used for a long time as a light recording material represented by diazo copy, and further, also applied recently for a recording material for which fixing of an image is required by utilizing a property that it is decomposed to lose function by the action of a light, and there has been suggested as a representative material a light fixing type heat-sensitive recording material by which a diazonium salt compound an a coupler are heated according to an image signal to be reacted to form an image, then the image is fixed by irradiation with a light (Koji Safuji, IMAGE ELECTRON INSTITUTE BOOK, vol. 11, pp. 290 to 296 (1982).
Further, there has been technical development of a diazonium salt compound such as improvement in storability and the like, and application to a full color heat-sensitive recording material has been reported (ELECTROPHOTOGRAPHY INSTITUTE BOOK, vol 26, pp. 115 to 125 (1987), FUJIFILM Research & Development, vol. 40, p. 13 (1995), Japanese Patent Application Publication (JP-B) No. 4-10,879 and the like).
In a lot of investigations for producing a full color sensitive material, magenta pigments are produced by using diazo compound having maximum absorption near 365nm. However, with increase of the abilities of a heat-sensitive recording material, it has been found that design in which sharpness is enhanced by placing a magenta material having visual sensitivity on the top layer is effective. For this design, it is necessary to use a coupler by which a magenta pigment is formed using a diazonium salt compound which can be fixed at a wavelength around 420 nm.
As a magenta coupler which, in heating, reacts with a diazonium salt compound which can be fixed at a wavelength around 420 nm, and develops color, there was used a coupler such as 1-hydroxycumarin or the like which develops color by reacting with a diazonium salt compound having the maximum absorption around 365 nm in heating. However, in this case, a pigment exhibiting very broad and brownish color was formed disadvantageously, and a magenta material could not be formed even if the substituent on the mother nucleus was changed.
For the purpose of improving this problem, a novel diazonium salt has been suggested in Japanese Patent Application No. 9-152,414. Hue obtained from a 1-hydroxycumarin coupler has not been satisfactory though it has been improved as compared with that obtained from conventional type diazo compounds.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a coupler which provides a magenta pigment having excellent hue using a diazonium salt compound which can be fixed at a wavelength around 420 nm.
The object of the present invention can be accomplished by providing heat-sensitive recording materials shown below.
(1) A heat-sensitive recording material comprising a substrate carrying thereon a heat-sensitive recording layer containing a diazonium salt compound and a coupler which develops color by reacting with said diazonium salt compound in heating, wherein said coupler comprises at least one compound represented by the following general formula (1):
(Wherein, Y represents a carbon atom or sulfur atom. Z represents an oxygen atom or sulfur atom. R represents alkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group or amino group. n1 represents 1 when Y is a carbon atom and represents 1 or 2 when Y is a sulfur atom. When n1 represents 2, two Zs may be the same or different. X
1
, X
2
and X
3
each independently represents an atom group required for forming a 5-membered aromatic heteroring. Wherein, there is no case in which two of X
1
, X
2
and X
3
represent a carbon atom and the remaining one represents a nitrogen atom.).
(2) The heat-sensitive recording material according to (1), wherein said diazonium salt is a compound represented by the following general formula (2):
(Wherein, R
11
represents an alkylsulfenyl group, arylsulfenyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, sulfamoyl group, alkoxycarbonyl group, carbamoyl group, carboxyl group, acyl group or cyano group. R
13
and R
14
each independently represents a hydrogen atom, alkyl group or aryl group. R
12
, R
15
and R
16
each independently represents a hydrogen atom, alkyl group, aryl group, alkoxy group or halogen atom. X
−
represents an anion. R
13
and R
14
, R
12
and R
13
, or R
14
and R
15
may bond each other to form a ring.).
(3) The heat-sensitive recording material according to (1), wherein said diazonium salt is a compound represented by the following general formula (3):
(Wherein, R
11
represents an alkylsulfenyl group, arylsulfenyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, sulfamoyl group, alkoxycarbonyl group, carbamoyl group, acyl group or cyano group. R
13
and R
14
each independently represents a hydrogen atom, alkyl group or aryl group. X
−
represents an anion. R
13
and R
14
may bond each other to form a ring.).
(4) The heat-sensitive recording material according to (1) to (3), wherein said diazonium compound is encapsulated in a micro capsule.
DETAILED DESCRIPTION OF THE INVENTION
The heat-sensitive recording material of the present invention contains at least a diazonium salt compound and a coupler which develops color by reacting with said diazonium salt compound in heating on a substrate, and as said coupler, at least one compound represented by the general formula (1) is contained. The compound represented by the general formula (1) may have various tautomeric structures, and the compound represented by the general formula (1) of the present invention also include these tautomers.
The compound represented by the general formula (1) used as a coupler in the present invention will be described in detail below.
In the general formula (I), Y represents a carbon atom or sulfur atom, preferably a sulfur atom. Z represents an oxygen atom or sulfur atom, preferably, an oxygen atom. n1 represents 1 when Y is a carbon atom and represents 1 or 2 when Y is a sulfur atom. When n1 represents 2, two Zs may be the same or different. When Y is a sulfur atom, n1 represents preferably 2.
In the general formula (1), R represents an alkyl group (for example, a methyl group, isopropyl group, 2-ethylhexyl group, dodecyl group, hexadecyl group or cyclohexyl group), an aryl group (for example, a phenyl group, 1-naphthyl group or 2-naphthyl group), a heterocyclic group, an alkoxy group (for example, a methoxy group, isopropyloxy group, decyloxy group, hexadecyloxy group, 2-ethylhexyloxy group or cyclohexyloxy group), or an aryloxy group (for example, a phenoxy group, 1-naphthoxy group or 2-naphthoxy group), or an amino group (for example, an amino group, methylamino group, isopropylamino group, 1,1,3,3-tetramethylbutylamino group, 2-ethylhexylamino group, dodecylamino group, dibutylamino group, methylhexylamino group, dioctylamino group, cyclohexylamino group). The groups may further have a substituent, and examples of such substituent include an alkyl group, aryl group, alkoxy group, aryloxy group, acylamino group, sulfonylamino group, alkoxycarbonyl group, acyloxy group, carbamoyl group, sulfamoyl group, halogen atom and hydroxyl group. R represents preferably an alkyl group or aryl group. The substituent is preferably an alkyl group, alkoxy group, aryloxy group, acylamino group, sulfonylamino group, alkoxycarbonyl group, carbamoyl group or chlorine atom.
In the general formula (1), X
1
, X
2
and X
3
each independently represents an atom group required for forming a 5-membered aromatic heteroring. Wherein, there is no case in which two of X
1
, X

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