JPH0848082A - Heat-sensitve transfer sheet - Google Patents

Abstract

PURPOSE:To obtain a low-energy, high-density and moderate yellow color tone recorded matter, by a method wherein a coloring material layer containing a binder comprised comprised of a resin, a specific pyrazolone azo coloring matter and a specific quinophthalone coloring matter is provided on a base. CONSTITUTION:A yellow color heat-sensitive transfer sheet is formed by laminating a coloring material layer containing a binder comprised of a resin, a pyrazolone azo coloring matter and a quinophthalone coloring matter on a base. The pyrazolone azo coloring matter is represented by formula I (wherein X is a hydoxy group or an amino group, Y is H, an alkyl group, an alkoxy group or the like, R is H, an alkyl group or an alkenyl group and ring A is a non-ionic substituent group). Then, the quinophthalone coloring matter is represented by formula II[R<1> is H or a lower alkyl group, Z<1> is H or a halogen atom and Z<2> is H, -COOR<2> group or -CONR<3>R<4> group (wherein R<2>, R<3>, R<4> are each an alkyl group or an alkoxy alkyl group)].

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a heat-sensitive transfer recording sheet used for heat-sensitive transfer recording, particularly dye transfer type heat-sensitive transfer recording.

[0002]

2. Description of the Related Art A dye-transfer type heat-sensitive transfer recording is a heat-sensitive transfer sheet in which a heat-sensitive transfer sheet having a color material layer containing a heat transferable dye on a base film and an image-receiving sheet having a dye-receiving layer on the surface are superposed. Is a recording method in which recording is carried out by heating and transferring the dye in the heat-sensitive transfer sheet to the image receiving sheet. In this recording method, the transfer amount of the dye can be controlled by the amount of heating energy, so that gradation expression, which is difficult with other recording methods, can be easily performed. Therefore, a full-color image can be easily produced by using the three primary color dyes of yellow, magenta and cyan dyes, and it is applied to a video printer and the like.

[0003]

In dye transfer type thermal transfer recording, the dye used in the ink composition of the transfer sheet has a great influence on the speed of transfer recording, the image quality of recorded matter, storage stability, etc. Is important, and it is necessary to satisfy the following conditions, for example. Easy sublimation and / or heat diffusion under the operating conditions of the thermal recording head. Do not decompose under the operating conditions of the thermal recording head. It should have a favorable hue for color reproduction. Large molecular extinction coefficient. Stable against heat, light, moisture, chemicals, etc. Easy to synthesize. Excellent ink suitability. There are no safety issues.

However, a dye satisfying all the above conditions has not been found so far, and a yellow dye, in particular, has various drawbacks. In the present invention, the pyrazolone azo dye represented by the general formula (I) has excellent properties in the above items ,,,, and so on. However, since the absorption spectrum has a wide width and the long-wavelength side of the absorption spectrum is poor and has a weak absorption up to around 550 nm, the color purity as a yellow color is poor and there is a problem in color reproduction.

In the present invention, the quinophthalone type dye represented by the general formula (II) is the above-mentioned ,,,
, And the like, have a narrow absorption spectrum width and are extremely sharp, so that a yellow color having excellent color purity can be reproduced. However, since the absorption spectrum width is narrow and sharp, when expressing a black color by mixing with a magenta dye and a cyan dye,
In the absorption spectrum of the color mixture, an absorption gap is formed near the absorption boundary between the yellow dye and the magenta dye. Therefore,
When expressing a black color using the yellow dye represented by the general formula (II), it is difficult to express a black color having a high color density.

Further, since the correlation between the dye structure and the required performances as described above is not clear, it is difficult to predict the performance obtained when the dyes are used in combination, and the composition is actually adjusted. It is necessary to select a good combination from the above. As a result of intensive studies to solve such problems, the present inventors have selected a coloring material containing a pyrazolone azo dye and a quinophthalone dye having a specific skeleton selected from various possible combinations of dyes. By carrying out heat-sensitive transfer recording using a yellow-colored heat-sensitive transfer sheet having a layer, it is possible to obtain a low-energy, high-concentration medium-yellow recorded matter, and also a high density when mixed with magenta and cyan. The present invention has been completed, and it has been found that the black color of No. 2 can be obtained, and that the light resistance of the obtained recorded matter is very good in both yellow and black.

That is, an object of the present invention is to obtain a low-energy, high-concentration medium-yellow recorded material,
Further, a yellow heat-sensitive transfer sheet capable of obtaining a high-concentration black color by mixing with magenta and cyan, and having very good light resistance in both the yellow color and the black color of the recorded matter obtained. To provide.

[0008]

That is, the gist of the present invention is a heat-sensitive transfer sheet having at least a coloring material layer on a substrate, wherein the coloring material layer comprises a resin binder and the following general formula (I ) Pyrazolone azo dye

[0009]

[Chemical 3]

(In the formula, X represents a hydroxy group or an amino group, and Y represents a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, a substituted or unsubstituted amino group, an acylamino group, an alkoxycarbonyl group, a substituted or non-substituted group. Represents a substituted carbamoyl group, R represents a hydrogen atom, a substituted or unsubstituted alkyl group, an alkenyl group,
A cycloalkyl group, or a substituted or unsubstituted phenyl group, and ring A represents a benzene ring which may have a nonionic substituent), and a quinophthalone system represented by the following general formula (II) Pigment

[0011]

[Chemical 4]

(Wherein R ¹ represents a hydrogen atom or a lower alkyl group, Z ¹ represents a hydrogen atom or a halogen atom, Z ² represents a hydrogen atom, a --COOR ² group or a --CONR ³
Represents an R ⁴ group. R ² , R ³ and R ^{4 each} represent an alkyl group, an alkoxyalkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, a furfuryl group or a tetrahydrofurfuryl group), and a yellow color heat-sensitive transfer sheet, Exist in.

Hereinafter, the present invention will be described in detail. The pyrazolone azo dye represented by the general formula (I) used in the present invention can be produced by a conventionally known method. In the general formula (I), X represents a hydroxy group or an amino group, Y represents a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, a substituted or unsubstituted amino group, an acylamino group, an alkoxycarbonyl group,
Represents a substituted or unsubstituted carbamoyl group, R represents a hydrogen atom, a substituted or unsubstituted alkyl group, an alkenyl group, a cycloalkyl group or a substituted or unsubstituted phenyl group, and ring A represents a nonionic substituent Represents a benzene ring which may have.

Wherein R is a C ₁ -C ₁₂ linear or branched alkyl group; an alkoxy group, an amino group, an alkylamino group, an alkoxyalkoxy group, an aryloxy group, an allyloxy group, an aralkyloxy group, Aryl group, cyano group, hydroxy group, halogen atom, furyl group, tetrahydrofuryl group, alkoxycarbonyl group,
C _{1 to} C ₁₂ linear or branched alkyl group substituted with an allyloxycarbonyl group, an acyloxy group or the like; an alkenyl group; a cycloalkyl group; a substituted or unsubstituted phenyl group or another aryl group; a hydrogen atom Is mentioned.

Specific examples of the substituted alkyl group include an alkyl group substituted with an alkoxy group, 2-methoxyethyl group, 2-ethoxyethyl group, 2- (n) propoxyethyl group, 2- (iso) propoxyethyl group, 2
-(N) butoxyethyl group, 2- (iso) butoxyethyl group, 2- (sec) butoxyethyl group, 2- (n)
Pentyloxyethyl group, 2- (n) hexyloxyethyl group, 2- (n) octyloxyethyl group, 2- (2'-ethylhexyloxy) ethyl group, 1-methyl-2-methoxyethyl group, 1-methyl-2-ethoxyethyl group, 1 -Methyl-2- (n) propoxyethyl group,
1-methyl-2- (iso) propoxyethyl group, 1-methyl-2- (n) butoxyethyl group, 1-methyl-2
-(Iso) butoxyethyl group, 1-methyl-2- (n) hexyloxyethyl group, 1-methyl-2- (2'-ethylhexyloxy) ethyl group, 3-methoxybutyl group, 3-ethoxybutyl group, 1-ethyl-2-methoxyethyl group, 1-ethyl- Examples thereof include a 2-ethoxyethyl group, but a C ₃ -C ₈ β-alkoxyethyl group is particularly preferable. Examples of the alkyl group substituted with an amino group or an alkylamino group include a 2-aminoethyl group, a 2- (N, N-diethylamino) ethyl group and a 2- {N, N-
Examples thereof include a di (n) butylamino} ethyl group, a 3- (N, N-diethylamino) propyl group and a 3- (N, N-dimethylamino) propyl group. Examples of the alkyl group substituted with an aralkyloxy group include a 2-benzyloxyethyl group, a 1-methyl-benzyloxyethyl group, a 1-ethyl-2-benzyloxyethyl group and a 2- (β-phenylethyl) oxyethyl group. The alkyl group substituted with an allyloxy group is a 2-allyloxyethyl group, a 1-methyl-2-allyloxyethyl group,
Examples thereof include 1-ethyl-2-allyloxyethyl group. Examples of the alkyl group substituted with an aryloxy group include a 2-phenoxyethyl group, a 1-methyl-2-phenoxyethyl group and a 1-ethyl-2-phenoxyethyl group. Examples of the alkyl group substituted with an alkoxyalkoxy group include a 2- (2′-methoxyethoxy) ethyl group, a 2- (2′-ethoxyethoxy) ethyl group, and a 2- {2 ′-(n) butoxyethoxy} ethyl group. 2- {2 '-(n) hexyloxyethoxy} ethyl group, 2
-{2 '-(n) octylethoxy} ethyl group, 2- {2'-(iso) butoxyethoxy} ethyl group, 1-methyl-2- (2'-methoxyethoxy) ethyl group, 1
-Methyl-2-{2 'over (n) butoxyethoxy} ethyl, 3 over (2' over-methoxyethoxy) particularly but a butyl group, beta chromatography (beta 'over alkoxy) ethyl of C ₅ -C ₁₀ Groups are preferred. The cyano group-substituted alkyl group is a 2-cyanoethyl group, a cyanomethyl group or the like, and the hydroxy group-substituted alkyl group is a 2-hydroxyethyl group, a 3-hydroxy (n) propyl group, or a 4-hydroxy (n) butyl group. Examples of the alkyl group in which a 1-methyl-2-hydroxyethyl group, a 1-ethyl-2-hydroxyethyl group and the like are substituted with a halogen atom include a 2-chloroethyl group, a 2-bromoethyl group,
A furfuryl group is an alkyl group substituted with a furyl group such as a 2,2-trifluoroethyl group, a tetrahydrofurfuryl group is an alkyl group substituted with a tetrahydrofuryl group, and an alkyl group substituted with an aryl group is an alkyl group substituted with a tetrahydrofuryl group. Include a benzyl group, a p-chlorobenzyl group and a 2-phenylethyl group. Examples of the alkyl group substituted with an alkoxycarbonyl group or an allyloxycarbonyl group include a 2-methoxycarbonylethyl group, a 2-ethoxycarbonylethyl group, a 2- (iso) butoxycarbonylethyl group, and a 2- (n) hexyloxycarbonyl group. 1-methyl-2-methoxycarbonylethyl group, 1
-Methyl-2- (n) butoxycarbonylethyl group, 2
-Allyloxycarbonylethyl group, 1-methyl-2-allyloxycarbonylethyl group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, (iso) butoxycarbonylmethyl group, (n) hexyloxycarbonylmethyl group, 2-ethylhexyloxycarbonylmethyl group Groups and the like. Examples of the alkyl group substituted with an acyloxy group include a 2-acetoxyethyl group, a 2-propionyloxyethyl group, a 2-benzoyloxyethyl group, a 3-acetoxy (n) propyl group, a 4-acetoxy (n) butyl group, and a 1-methyl-2- Examples thereof include acetoxyethyl group and 1-ethyl-2-acetoxyethyl group.

Examples of the cycloalkyl group of R include a cyclopentyl group and a sillohexyl group. When R is a substituted phenyl group, the substituent may be a C _{1 to} C ₄ lower alkyl group, a C _{1 to} C ₄ lower alkoxy group, a halogen atom such as a fluorine atom, a chlorine atom or a bromine atom, and a C ₁ to C ₄
And lower alkoxycarbonyl group and trifluoromethyl group.

Examples of the alkenyl group for R include allyl group and vinyl group. Among the groups represented by R, particularly preferable ones are C _{1 to} C ₄ linear or branched alkyl groups and phenyl groups. In addition, the substituent that the benzene ring represented by ring A has is C
_{1 to} C ₄ linear or branched lower alkyl group, C
_{1 to} C ₄ linear or branched lower alkoxy group,
Halogen atoms such as fluorine atom, chlorine atom, bromine atom,
A nitro group, a cyano group, an alkyl group substituted with a fluorine atom such as a trifluoromethyl group, an amino group represented by -NR ¹³ R ¹⁴ , an acylamino group represented by -NHCOR ¹⁵ , a carbamate group represented by -NHCOOR ¹⁶ ; −
Sulfonamide group represented by NHSO ₂ R ¹⁷ , -CO
A carboxylic acid ester group represented by OR ¹⁸ , -CONR
Carbamoyl group represented by ^{_{19 R 20, -SO 2 NR 21}} R
Examples thereof include a sulfamoyl group represented by ²² and a sulfonate group represented by SO ₃ R ²³ . Here, R ^{13 to} R ²³ each represent a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an allyl group, a substituted or unsubstituted vinyl group, or a substituted or unsubstituted phenyl group.

Among the phenyl groups represented by ring A, particularly preferred groups are unsubstituted phenyl groups; nitro groups, trifluoromethyl groups, lower alkyl groups, lower alkoxy groups, lower alkoxycarbonyl groups, chlorine atoms and the like. Examples thereof include a substituted phenyl group. The alkyl group is a C ₁ -C ₁₀ linear or branched alkyl group; the alkoxy group is a C ₁ -C ₁₀ linear or branched alkoxy group; the aryloxy group is phenoxy. Group and C ₁ -C ₄ linear and branched alkyl groups, C
_{1 to} C ₄ linear or branched alkoxy group, chlorine atom,
A phenoxy group substituted with a bromine atom, a fluorine atom, a cyano group, a nitro group, a trifluoromethyl group, etc .; The substituted amino group is a C _{1 to} C ₈ linear or branched monoalkylamino group or dialkylamino group. A group; as an acylamino group, a C _{1 to} C ₄ alkylcarbonylamino group,
Benzoylamino group; C ₁ -C ₈ linear and branched alkoxycarbonyl group as alkoxycarbonyl group; C ₁ -C ₈ linear and branched monoalkylaminocarbonyl as substituted carbamoyl group Group or dialkylaminocarbonyl group.

Among the groups represented by Y, particularly preferred are a lower alkyl group, a lower alkoxycarbonyl group and a lower alkylaminocarbonyl group. In the present invention, the quinophthalone dye represented by the general formula (II) can be produced by a conventionally known method. In the general formula (II), R ¹ represents a hydrogen atom or a lower alkyl group, Z ¹ represents a hydrogen atom or a halogen atom, Z ² represents a hydrogen atom or —COOR.
² Or a —CONR ³ R ⁴ group, wherein R ² , R ³ and R ⁴ are each an alkyl group, an alkoxyalkyl group,
It represents a cycloalkyl group, an alkenyl group, an aralkyl group, a furfuryl group or a tetrahydrofurfuryl group.

The lower alkyl group represented by R ¹ is a C ₁ -C ₄ linear or branched alkyl group, specifically, a methyl group, an ethyl group, a (n) propyl group, (I) propyl group, (n) butyl group, (i) butyl group and the like. In addition, the above R ² , R ³ and R ⁴
Examples of the alkyl group represented by include a C _{1 to} C ₁₂ linear or branched alkyl group, and examples of the alkoxyalkyl group include a 2-methoxyethyl group and a 2-methoxyethyl group.
Ethoxyethyl group, 2- (n) propoxyethyl group, 2
-(I) propoxyethyl group, 2- (n) butoxyethyl group, 2- (i) butoxyethyl group, 2- (sec) butoxyethyl group, 2- (n) pentyloxyethyl group,
2- (n) hexyloxyethyl group, 2- (n) octyloxyethyl group, 2- (2'-ethylhexyloxy) ethyl group, 1-methyl-2-methoxyethyl group, 1
-Methyl-2-ethoxyethyl group, 1-methyl-2-
(N) propoxyethyl group, 1-methyl-2- (i) propoxyethyl group, 1-methyl-2- (n) butoxyethyl group, 1-methyl-2- (i) propoxyethyl group,
1-methyl-2- (n) hexyloxyethyl group, 1-
Methyl-2- (2'-ethylhexyloxy) ethyl group, 3-methoxybutyl group, 3-ethoxybutyl group, 1
- ethyl-2-methoxyethyl group, 1-ethyl-2-ethoxyethyl group and the like, particularly preferably C ₃ -C ₈
2-alkoxyethyl group, the aralkyl group includes a benzyl group, a 2-phenylethyl group, and the like, and the cycloalkyl group includes a cyclopentyl group, a cyclohexyl group, and the like. Examples of the halogen atom represented by Z ¹ include a fluorine atom, a chlorine atom and a bromine atom.

The groups represented by R ² , R ³ and R ⁴ are
An alkyl group of C ₁ -C _8, particularly suitable when Z ¹ is a hydrogen atom or a bromine atom. Typical examples of the compounds represented by the above general formulas (I) and (II) are shown in Tables 1 and 2, but the compounds used in the present invention are not limited to these specific examples unless the gist thereof is exceeded. Not something.

[0022]

[Table 1]

[0023]

[Table 2]

[0024]

[Table 3]

[0025]

[Table 4]

[0026]

[Table 5]

[0027]

[Table 6]

[0028]

[Table 7]

[0029]

[Table 8]

[0030]

[Table 9]

[0031]

[Table 10]

[0032]

[Table 11]

[0033]

[Table 12]

[0034]

[Table 13]

In the present invention, the general structural formulas (I) and (I
By mixing and using the dye of I), the above-mentioned drawbacks of the dyes (I) and (II) can be eliminated, and a transfer sheet excellent in all properties can be obtained. The mixing ratio of the dyes (I) and (II) is appropriately in the range of 2: 8 to 8: 2 (weight ratio). When the coloring material layer is formed on the heat-sensitive transfer sheet of the present invention by using the above-mentioned dye, the method is not particularly limited, and the dye represented by the general structural formulas (I) and (II) is used as a medium together with the binder. It can be carried out by preparing an ink by dissolving it in the form of fine particles or dispersing it in the form of fine particles, and applying the ink to a base film and drying it according to a conventional method.

As the binder for preparing the ink, water-soluble resins such as cellulose-based, acrylic acid-based, starch-based and epoxy-based resins and acrylic resins, methacrylic resins, polystyrene, polycarbonate, polysulfone, polyether sulfone, polyvinyl are used. Examples thereof include resins soluble in organic solvents such as butyral, ethyl cellulose, acetyl cellulose, polyester, AS resin, and phenoxy resin.

As a medium for preparing the ink, in addition to water, alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol and isobutyl alcohol, cellosolves such as methyl cellosolve and ethyl cellosolve, and aromatic compounds such as toluene, xylene and chlorobenzene. Group, esters such as ethyl acetate and butyl acetate, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, methylene chloride,
Chlorine-based solvents such as chloroform and trichlorethylene,
Ethers such as tetrahydrofuran and dioxane,
Organic solvents such as N, N-dimethylformamide and N-methylpyrrolidone can be mentioned.

In addition to the above components, organic or inorganic non-sublimable fine particles, a dispersant, an antistatic agent, an antifoaming agent, an antioxidant, a viscosity modifier and the like are added to the above ink. be able to. As a base film for applying the ink for producing the transfer sheet, condenser paper, thin paper such as glassine paper, polyester, polycarbonate,
Films of plastics having good heat resistance such as polyamide, polyimide and polyaramid are suitable, and the thickness thereof can be in the range of 3 to 50 μm.

Of the above base films, the polyethylene terephthalate film is particularly advantageous in consideration of mechanical strength, solvent resistance, economy and the like. However, in some cases, the polyethylene terephthalate film does not always have sufficient heat resistance and the running property of the thermal head is insufficient, so that heat resistance that includes a lubricant, heat-resistant particles with high lubricity, etc. on the opposite surface of the color material layer. A thermal head having improved running properties can be used by providing a layer of a functional resin according to a conventional method.

The method for applying the ink to the base film is not particularly limited, but it can be carried out using, for example, a gravure coater, a reverse roll coater, a rod coater, an air doctor coater, etc. The thickness may be applied so as to be in the range of 0.1 to 5 μm after drying. The heat-sensitive transfer sheet of the present invention can use not only a thermal head but also infrared rays, laser light, etc. as a heating means. Further, it is also possible to use it as an electrically conductive dye transfer sheet by using an electrically conductive heat generating film that generates heat by applying electricity to the base film itself.

[0041]

EXAMPLES The present invention will be described in detail below with reference to examples, but the examples are not intended to limit the present invention. (Example 1) a) Preparation of ink

[0042]

[Table 14] 1) Preparation of ink (A) The dye NO. 1-54 3 g The dye NO. 2-17 4 g Cellulose acetate 10 g (Product name L-30; manufactured by Daicel Chemical Industries, Ltd.) Methyl ethyl ketone 80 g ──────────────────────────── ───── Total 97 g The mixture having the above composition was treated with a paint conditioner for 10 minutes to prepare an ink.

2) Preparation of Ink (B) (Magenta Ink) Magenta ink was prepared in the same manner as Ink (A) except that 6 g of magenta dye having the following structure was used instead of the dye used in Ink (A). (B) was prepared.

[0044]

Embedded image

3) Preparation of Ink (C) (Cyan Ink) Cyan ink is the same as Ink (A) except that 6 g of cyan dye having the following structure is used instead of the dye used in Ink (A). (C) was prepared.

[0046]

[Chemical 6]

B) Preparation of transfer sheet Each of the above inks (A), (B) and (C) was applied onto a polyethylene terephthalate film (6 μm thick) having a heat-resistant back surface treated with a wire bar and dried. (Dry film thickness about 1 μm) Transfer sheet (A),
(B) and (C) were obtained. In addition, the polyethylene terephthalate film is subjected to the heat-resistant lubricity treatment by applying the following formula

[0048]

[Chemical 7]

Having a repeating structural unit represented by
8 parts by weight of a polycarbonate resin having a reduced viscosity η _sp / C of 0.55 dl / g measured in a 6 g / dl methylene chloride solution at 20 ° C., a phosphate ester surfactant (product name PRYSURF A-208B; It was carried out by applying a liquid composed of 1 part by weight of Ichigo Seiyaku Co., Ltd. and 91 parts by weight of toluene and drying (dry film thickness: about 1 μm). c) Preparation of image receptor 10 parts of vinyl chloride-vinyl acetate resin (product name VYHD; manufactured by Union Carbide), amino-modified silicone (product name KF-393; manufactured by Shin-Etsu Chemical Co., Ltd.)
A liquid consisting of 5 parts, 15 parts of methyl ethyl ketone, and 15 parts of xylene was coated on a synthetic paper (product name YUPO FPG150; manufactured by Oji Yuka Co., Ltd.) with a wire bar and dried (dry film thickness about 5 μm), and further in an oven. It was prepared by treating at 80 ° C. for 30 minutes. d) Transfer recording 1) Yellow color transfer recording The ink application surface of the transfer sheet (A) is overlaid on the image receiver,
Recording was performed using a thermal head under the following conditions to obtain a medium-colored yellow tone recorded matter. Table 3 shows the color density of the recorded matter and the color measurement results.

[0050]

[Table 15] Recording conditions Recording density for main scanning and sub scanning: 6 dots / mm Recording power: 0.21 W / dot Energization time: 10 ms For color measurement, use a color difference meter SZ-Σ80 manufactured by Nippon Denshoku Industries Co., Ltd. It was measured. Color density was measured with a Macbeth densitometer TR-927.

2) Black color transfer recording The transfer sheets (A), (B), and (C) described above were transferred and recorded in this order on the same image receptor under the same recording conditions as in 1) above, and black was recorded. A color record was obtained. The results of measuring the color density of this recorded product are shown in Table 3. e) Light fastness test The light fastness test of the obtained yellow and black color recordings was performed with a xenon lamp fade meter (Suga Test Instruments Co., Ltd.).
Manufactured by K.K. (black panel temperature: 63 ± 2)
℃), degree of discoloration and fading of recorded matter after irradiation for 80 hours {△ E
(L ^* a ^* b ^* )} is shown in Table-3.

Comparative Example 1 Instead of the mixed dye used in the preparation of the ink (A) of Example 1, one of the components of the mixed dye, the above-mentioned dye NO. 1-5
Ink preparation, transfer sheet preparation, and transfer recording were carried out in the same manner as in Example 1 using 6 g of the dye of No. 4 only. Table 3 shows the yellow color transfer recording results, the black color transfer recording results, and the light resistance test results.

COMPARATIVE EXAMPLE 2 Instead of the mixed dye used in the preparation of the ink (A) of Example 1, one of the components of the mixed dye, the above-mentioned dye NO. 2-1
Ink preparation, transfer sheet preparation, and transfer recording were carried out in the same manner as in Example 1 using 8 g of the dye of No. 7 only. Table 3 shows the yellow color transfer recording results, the black color transfer recording results, and the light resistance test results.

Example 2 The dye No. 1 used in Example 1 was used. Dye N instead of 1-54
O. 1-37 as dye NO. Dye N instead of 2-17
O. 2-61 was used in the same manner as in Example 1 to prepare an ink, a transfer sheet, an image receptor, transfer recording, and a light resistance test, and the results shown in Table 3 were obtained.

Comparative Example 3 The dye NO. Dye N instead of 1-54
O. Using 1-37, in the same manner as in Comparative Example 1, ink was prepared, a transfer sheet was prepared, an image receptor was prepared and transferred and recorded, and a light resistance test was conducted, and the results shown in Table 3 were obtained.

Comparative Example 4 The dye NO. Dye N instead of 2-17
O. Using 2-61, in the same manner as in Comparative Example 2, ink preparation, transfer sheet preparation, image receptor preparation and transfer recording, and a light resistance test were conducted, and the results shown in Table 3 were obtained.

Example 3 Using the ink prepared by the following method instead of the ink used in Example 1, a transfer sheet was prepared, an image receptor was prepared and transferred, and a light resistance test was conducted in the same manner as in Example 1. As a result, it was possible to obtain a recorded product having a medium yellow color tone and a black recorded product having a high color density. The light resistance of the obtained recorded matter and the storage stability of the transfer sheet in the dark were both good.

[0058]

[Table 16] Ink preparation Same pigment as in Example 1 7 g AS resin 10 g (product name DENKA AS-S; Denki Kagaku Kogyo KK) Toluene 70 g Cyclohexanone 10 g ────────────── ────────────── Total 97g

[0059]

[Table 17]

[0060]

When the heat-sensitive transfer sheet of the present invention is used,
It is possible to obtain a low-energy, high-concentration medium-yellow recorded matter, and to obtain a high-concentration black color by mixing with magenta and cyan. Is very good.

Claims (1)

[Claims] 1. A heat-sensitive transfer sheet having at least a color material layer on a substrate, wherein a binder made of a resin in the color material layer, a pyrazolone azo dye represented by the following general formula (I): 1] (In the formula, X represents a hydroxy group or an amino group,
Y represents a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, a substituted or unsubstituted amino group, an acylamino group, an alkoxycarbonyl group, a substituted or unsubstituted carbamoyl group, and R represents a hydrogen atom, a substituted or unsubstituted Alkyl group, alkenyl group, cycloalkyl group,
Or a substituted or unsubstituted phenyl group,
Represents a benzene ring which may have a nonionic substituent), and a quinophthalone dye represented by the following general formula (II): (In the formula, R ¹ represents a hydrogen atom or a lower alkyl group, and Z ¹
Represents a hydrogen atom or a halogen atom, and Z ² represents a hydrogen atom, a —COOR ² group or a —CONR ³ R ⁴ group.
R ² , R ³ and R ⁴ are an alkyl group, an alkoxyalkyl group,
A yellow color heat-sensitive transfer sheet containing a cycloalkyl group, an alkenyl group, an aralkyl group, a furfuryl group or a tetrahydrofurfuryl group).