JPH05169859A - Dyestuff for thermal transfer recording, ink composition of thermal transfer recording and transfer sheet - Google Patents

Abstract

PURPOSE:To obtain dyestuffs and an ink composition for thermal transfer recording having high sublimating speed and excellent image stability after transfer by using dyestuffs being shown in specific chemical formula and having superior solubility to an ink solvent and the low melting point as sublimating dyestuffs for thermal transfer recording. CONSTITUTION:In a thermal transfer recording system using sublimating dyestuffs, a transfer sheet, in which a base film is coated with sublimating dyestuffs, is employed, and the transfer sheet is heated selectively by a thermal head, thus conducting transfer on recording paper. Dyestuffs shown in general formula mentioned on the right are used as the sublimating dyestuffs at that time. In formula, R<1> represents a hydrogen atom, a substituted or non-substituted alkyl group, etc., R<2>, R<3> the hydrogen atom, a 1-4C alkyl group, etc., R<4> the hydrogen atom, the substituted or non-substituted alkyl group, etc., R<5>-R<8> the hydrogen atom, the 1-4C alkyl group, etc., and R<9>, R<10> the hydrogen atom, the substituted or non-substituted alkyl group, etc. The dyestuffs are kneaded with a binder resin, an organic solvent, etc., thus acquiring an ink composition for thermal transfer recording.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a dye for thermal transfer recording (hereinafter abbreviated as sublimation dye), a thermal transfer recording ink composition, and a transfer sheet which are used for color hard copy by a sublimation thermal transfer recording system. Regarding

[0002]

2. Description of the Related Art A thermal transfer method using a sublimation dye is applied to a thin condenser paper having a thickness of several microns or PET film with an inked sublimation dye, which is selectively heated by a thermal head and transferred to a recording paper. It is one of the thermal transfer printing methods and is currently used as a means for image recording (hard copy) of various image information.

The sublimation dyes used here are characterized by abundant colors, excellent color mixing properties, strong dyeing power, and relatively high stability, but the amount of dyes that sublime depends on heat energy, Since the density after dyeing can be controlled in an analog manner, it has a great feature not found in other printing methods.

[0004]

As a cyan dye for sublimation transfer, an indoaniline compound having a particularly excellent hue (Japanese Patent Laid-Open Nos. 61-22993 and 61-61991) is used.
, 31292) and the like, which have both a high sublimation rate and image stability after transfer, are extremely few, and it has been expected that a dye satisfying the optimum conditions as a sublimation dye will appear.

[0005]

Means for Solving the Problems As a result of intensive studies for solving the above problems, the present inventors have found that the above general formula (I)
The present invention has been completed by finding a compound represented by

That is, the present invention is represented by the following general formula (I)

[0007]

[Chemical 2] (In the formula, R ¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a furfuryl group, or a tetrahydrofurfuryl group, and R ² and R ³ represent Hydrogen atom, carbon number 1
To 4 alkyl groups, alkoxy groups, or halogen atoms, and R ⁴ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, or a heterocycle. , R ⁵ ~ R
⁸ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group, an alkylcarbonylamino group, an alkoxycarbonylamino group, a formylamino group, an alkylsulfonylamino group, or a halogen atom, and R ⁹ _and R ¹⁰ are A hydrogen atom, a substituted or unsubstituted alkyl group, an alkenyl group, an aralkyl group, or an aryl group is shown. ) Is used as a dye for heat-sensitive transfer recording, and further, an ink composition for heat-sensitive transfer recording containing at least the sublimation dye, a binder resin and an organic solvent and / or water, and a base sheet and The transfer sheet comprises a dye carrying layer formed on one surface of the base sheet, and the dye contained in the dye carrying layer includes the transfer sheet.

According to the studies conducted by the present inventors, generally, in sublimation transfer type dyes, the sublimation rate during transfer is generally related to the interaction between the dye molecules and the interaction between the dye molecules and the binder resin for ink. The knowledge that there is is obtained.

That is, it is preferable that the dye has good solubility in the ink solvent and has a low melting point, and that the interaction with the binder resin for the ink is small enough not to impair the storage stability after ribbon production. It became clear that it was a different pigment. The dye represented by formula (I) of the present invention has the above-mentioned various conditions and has a relatively good sublimation rate.

The present invention will be described in detail below.

The dye for thermal transfer recording of the present invention has the general formula
As shown in (I), R in the formula ¹Is a hydrogen atom,
A substituted or unsubstituted alkyl group, cycloalkyl group,
Alkenyl group, aralkyl group, aryl group, furfuryl
Group or a tetrahydrofurfuryl group.

The unsubstituted alkyl group has 1 to 1 carbon atoms.
8 are preferred, for example, methyl, ethyl, n-
Examples include propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl and the like.

The substituted alkyl group is a linear or branched alkyl group having 1 to 8 carbon atoms, and hydrogen is substituted on the alkyl group. The substituents are methoxy, ethoxy, and
n-propoxy, iso-propoxy, n-butoxy,
Alkoxy groups such as iso-butoxy, sec-butoxy, tert-butoxy and n-hexyloxy, alkoxyalkoxy groups such as methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxypropoxy, ethoxypropoxy, propoxypropoxy, phenoxy, p.
Aryloxy groups such as -methylphenoxy, m-methylphenoxy, o-methylphenoxy, p-chlorophenoxy, m-methylphenoxy and o-methylphenoxy,
Thioaryloxy groups such as thiophenoxy, p-methylthiophenoxy, m-methylthiophenoxy and o-methylthiophenoxy, methylcarbonylamino, ethylcarbonylamino, n-propylcarbonylamino, is
Alkylcarbonylamino groups such as o-propylcarbonylamino and n-butylcarbonylamino, alkoxycarbonylamino groups such as methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, iso-propoxycarbonylamino, n-butoxycarbonylamino and the like, Formylamino group, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, i
Alkylcarbonyl groups such as so-propylcarbonyl and n-butylcarbonyl, alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl and n-butoxycarbonyl, methylcarboxy, ethylcarboxy, n-propyl Alkylcarboxy groups such as carboxy, iso-propylcarboxy, n-butylcarboxy, methoxycarboxy, ethoxycarboxy, n-propoxycarboxy, iso-propoxycarboxy,
Alkylcarboxy groups such as n-butoxycarboxy, methoxycarbonylmethoxy, ethoxycarbonylmethoxy, n-propoxycarbonylmethoxy, iso-propoxycarbonylmethoxy, alkoxycarbonylalkoxy groups such as n-butoxycarbonylmethoxy, halogens such as fluorine, chlorine and bromine. Atoms, cyano groups and the like are preferred.

The cycloalkyl group has 5 to 6 carbon atoms.
Preferred examples include cyclopentyl and cyclohexyl.

The alkenyl group preferably has 3 to 6 carbon atoms, and examples thereof include allyl, 2-butenyl and 3-.
Butenyl, 3-methyl-2-butenyl and the like can be mentioned.

The aralkyl group preferably has 7 to 10 carbon atoms, and examples thereof include benzyl and phenethyl.

The aryl group is phenyl, p-tolyl, m-tolyl, o-tolyl, p-chlorophenyl, m.
-Chlorophenyl, o-chlorophenyl and the like are preferable.

R ² and R ³ represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group, or a halogen atom.

As the alkyl group, methyl, ethyl, n-
Propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl are preferred.

The alkoxy group is preferably one having 1 to 6 carbon atoms, and examples thereof include methoxy, ethoxy and n-.
Propoxy, iso-propoxy, n-butoxy, is
There are o-butoxy, sec-butoxy, tert-butoxy, n-hexyloxy and the like.

As the halogen atom, fluorine, chlorine, bromine and the like are preferable.

R ⁴ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group or a heterocycle.

Here, the unsubstituted alkyl group is methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-. Heptyl, n
-Octyl and the like are preferred.

The substituted alkyl group is a linear or branched alkyl group having 1 to 8 carbon atoms, and hydrogen is substituted on the alkyl group. The substituents are methoxy, ethoxy, and n.
-Propoxy, iso-propoxy, n-butoxy, i
Alkoxy groups such as so-butoxy, sec-butoxy, tert-butoxy and n-hexyloxy, alkoxyalkoxy groups such as methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxypropoxy, ethoxypropoxy, propoxypropoxy, phenoxy, p-
Aryloxy groups such as methylphenoxy, m-methylphenoxy, o-methylphenoxy, p-chlorophenoxy, m-methylphenoxy, o-methylphenoxy, thiophenoxy, p-methylthiophenoxy, m-methylthiophenoxy, o-methylthiophenoxy Thioaryloxy groups such as, methylcarbonylamino, ethylcarbonylamino, n-propylcarbonylamino, iso
-Propylcarbonylamino, n-butylcarbonylamino and other alkylcarbonylamino groups, methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, iso-propoxycarbonylamino, n-butoxycarbonylamino and other alkoxycarbonylamino groups, formyl Amino group, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, is
Alkylcarbonyl group such as o-propylcarbonyl, n-butylcarbonyl, etc., alkoxycarbonyl group such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, methoxycarbonylmethoxycarbonyl, ethoxycarbonylmethoxycarbonyl , Alkoxycarbonylalkoxycarbonyl groups such as n-propoxycarbonylmethoxycarbonyl, iso-propoxycarbonylmethoxycarbonyl and n-butoxycarbonylmethoxycarbonyl, halogen atoms such as fluorine, chlorine and bromine, and cyano groups.

The cycloalkyl group has 3 to 8 carbon atoms.
Preferred are cyclopentyl and cyclohexyl.

The alkenyl group is preferably allyl, 2-butenyl, 3-butenyl, 3-methyl-2-butenyl and the like.

The aralkyl group is preferably benzyl, phenethyl and the like.

Examples of the aryl group are phenyl, p-tolyl, m-tolyl, o-tolyl, p-chlorophenyl and m.
Examples include -chlorophenyl and o-chlorophenyl.

Further, examples of the heterocyclic group include furan, tetrahydrofuran, pyridine, piperidine, pyrrole, pyrrolidine, thiophene, thiazole, benzothiazole, oxazole and benzoxazole.

R ^{5 to} R ⁸ represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group, an alkylcarbonylamino group, an alkoxycarbonylamino group, a formylamino group, an alkylsulfonylamino group or a halogen atom.

Examples of the alkyl group having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, iso-propyl and n-
Butyl, iso-butyl, sec-butyl, tert-
Butyl etc.

The alkoxy group has 1 to 6 carbon atoms and is, for example, methoxy, ethoxy, n-propoxy, is.
o-propoxy, n-butoxy, iso-butoxy, s
ec-Butoxy, tert-butoxy, n-hexyloxy and the like are preferable.

The alkylcarbonylamino group has 1 to 6 carbon atoms and is preferably methylcarbonylamino, ethylcarbonylamino, n-propylcarbonylamino, iso-propylcarbonylamino, n-butylcarbonylamino or the like.

The alkoxycarbonylamino group has 1 to 6 carbon atoms and is, for example, methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, iso-propoxycarbonylamino, n.
-Butoxycarbonylamino and the like are preferred.

The alkylsulfonylamino group has 1 to 6 carbon atoms, and is methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, i.
So-propyl sulfonylamino, n-butyl sulfonylamino, etc. can be illustrated.

The halogen atom is preferably fluorine, chlorine, bromine or the like.

R ⁹ and R ¹⁰ represent a hydrogen atom, a substituted or unsubstituted alkyl group, alkenyl group, aralkyl group or aryl group.

The unsubstituted alkyl group has 1 to 8 carbon atoms, and is, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl,
sec-butyl, tert-butyl, n-pentyl, n
-Hexyl, n-heptyl, n-octyl and the like are preferable.

The substituted alkyl group is a linear or branched alkyl group having 1 to 8 carbon atoms and hydrogen is substituted, and the substituents are methoxy, ethoxy and n.
-Propoxy, iso-propoxy, n-butoxy, i
Alkoxy groups such as so-butoxy, sec-butoxy, tert-butoxy and n-hexyloxy, alkoxyalkoxy groups such as methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxypropoxy, ethoxypropoxy, propoxypropoxy, phenoxy, p-
Aryloxy groups such as methylphenoxy, m-methylphenoxy, o-methylphenoxy, p-chlorophenoxy, m-methylphenoxy, o-methylphenoxy, thiophenoxy, p-methylthiophenoxy, m-methylthiophenoxy, o-methylthiophenoxy Thioaryloxy groups such as, methylcarbonylamino, ethylcarbonylamino, n-propylcarbonylamino, iso
An alkylcarbonylamino group such as -propylcarbonylamino and n-butylcarbonylamino, an alkoxycarbonylamino group such as methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, iso-propoxycarbonylamino and n-butoxycarbonylamino, Formylamino group, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, is
Alkylcarbonyl groups such as o-propylcarbonyl and n-butylcarbonyl, alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl and n-butoxycarbonyl, methylcarboxy, ethylcarboxy, n-propyl Alkylcarboxy groups such as carboxy, iso-propylcarboxy, n-butylcarboxy, methoxycarboxy, ethoxycarboxy, n-propoxycarboxy, iso-propoxycarboxy,
an alkoxycarboxy group such as n-butoxycarboxy,
Preferred are alkoxycarbonylalkoxy groups such as methoxycarbonylmethoxy, ethoxycarbonylmethoxy, n-propoxycarbonylmethoxy, iso-propoxycarbonylmethoxy, and n-butoxycarbonylmethoxy, halogen atoms such as fluorine, chlorine and bromine, and cyano groups.

As the alkenyl group, allyl, 2-butenyl, 3-butenyl, 3-methyl-2-butenyl and the like are preferable.

Examples of the aralkyl group include benzyl and phenethyl. As the aryl group, phenyl,
P-tolyl, m-tolyl, o-tolyl, p-chlorophenyl, m-chlorophenyl, o-chlorophenyl and the like are preferable.

The dye of the present invention represented by the general formula (I) can be produced by a conventional method by oxidative coupling of a substituted aniline and a substituted phenol according to the following reaction formula.

[0043]

[Chemical 3] (X is a leaving group such as H and halogen, and R ^{1 to} R ¹⁰ are as described above.) As a method for producing a thermal transfer recording ink using the dye of the present invention, the dye is a suitable resin. The recording ink may be prepared by mixing with a solvent or the like.

In this case, the amount of the dye in the thermal transfer recording ink is usually 2 to 5% by weight.

As the thermal transfer method, the ink obtained above is applied on a suitable substrate to prepare a transfer sheet,
A method in which the sheet is superposed on a recording material and then heated and pressed from the back surface of the sheet with a thermal recording head can be mentioned, whereby the dye on the sheet is transferred onto the recording material.

The resin for adjusting the above-mentioned ink may be one used in ordinary printing inks, such as rosin type, phenol type, xylene type, petroleum type, vinyl type, polyamide type, alkyd type, nitrocellulose. Oil-based resins such as resins and alkyl celluloses, or aqueous resins such as maleic acid-based, acrylic acid-based, casein, shellac and glue can be used.

As a solvent for ink preparation, alcohols such as methanol, ethanol, propanol and butanol, cellosolves such as methyl cellosolve and ethyl cellosolve, aromatics such as benzene, toluene and xylene, ethyl acetate, Ester such as butyl acetate, acetone, methyl ethyl ketone, ketones such as cyclohexanone, hydrocarbons such as ligroin, cyclohexane, kerosene, dimethylformamide, etc. can be used, but when using an aqueous resin, water or water and the above It is also possible to use a mixture of the above solvents.

As the base material sheet to which the ink is applied, thin film paper such as condenser paper and glassine paper and plastic film having good heat resistance such as polyester, polyamide and polyimide are suitable. To improve the heat transfer efficiency from the thermal recording head to the dye 5
A thickness of about 50 μm is suitable.

The dye-carrying layer provided on the surface of the base sheet can be prepared by applying the above-mentioned ink to the base sheet.

Examples of the recording material include polyolefin resins such as polyethylene and polypropylene, halogenated polymers such as polyvinyl chloride and polyvinylidene chloride, vinyl polymers such as polyvinyl alcohol, polyvinyl acetate and polyacrylic ester, and polyethylene. Polyester resins such as terephthalate and polybutylene terephthalate, polystyrene resins, polyamide resins, copolymer resins of olefins such as ethylene and propylene with other vinyl monomers, cellulosic resins such as ionomers, cellulose diacetate and cellulose triacetate. Examples of the fiber include fibers, woven fabrics, films, sheets, and molded products made of polycarbonate, polysulfone, polyimide, and the like.

Particularly preferred are woven fabrics, sheets or films made of polyethylene terephthalate.

Further, in the present invention, plain paper coated or impregnated with a resin containing acidic fine particles such as silica gel, laminated with a resin film, or specially treated with acetylation is used. By using paper, good recording with excellent image stability under high temperature and high humidity can be performed. It is also possible to use films of various resins or synthetic papers made from them.

Further, after transfer recording, a polyester film, for example, is hot-pressed and laminated on the transfer recording surface, whereby the coloring of the dye can be improved and the storage stability of the recording can be improved.

[0054]

The cyan dye represented by the general formula (I) of the present invention can control the sublimation transfer amount of the dye by changing the energy applied to the thermal head during thermal transfer. Easy and suitable for full color recording.

Further, since it is stable against heat, light, moisture, chemicals, etc., when used as an ink composition and a transfer sheet, it is not thermally decomposed during transfer recording and the storability of the obtained record is improved. Is also excellent.

Further, since the dye of the present invention has good solubility in an organic solvent and dispersibility in water, it is easy to prepare a highly concentrated ink which is uniformly dissolved or dispersed, and as a result, a color density is improved. It is a dye that is practically valuable because it can obtain good recording quality.

[0057]

EXAMPLES The present invention will be described in detail below with reference to examples.
Parts in the examples indicate parts by weight. % Means% by weight. Example-1 4-diethylamino-o dissolved in 120 parts of methanol
-Toluidine 12 parts and 2-methoxycarbonylamino-
After adding 30 parts of 25% ammonia water to 13 parts of 5-acetylaminophenol, 25 parts of ammonium persulfate was added over about 1 hour while maintaining the liquid temperature at 20 ° C.
Reacted for hours.

After the reaction, the product was separated, washed thoroughly with water,
Purification by column chromatography gave the following compound (A).

Further, by using the compound of the following formula (A), ink adjustment, transfer sheet and recording material were prepared and transfer recording was carried out as follows.

The maximum absorption wavelength (λmax) in chloroform of the compound was 625 nm.

[0061]

[Chemical 4] (I) Ink preparation method Dye of the above formula (A) 3 parts Polybutyral resin 4.5 〃 Methyl ethyl ketone 46.25 〃 Toluene 46.25 〃 The dye mixture of the above composition is used in a glass conditioner with a paint conditioner for about 30 parts. The ink was prepared by mixing for a minute. (Ii) Method for preparing transfer sheet Using a gravure proofing machine (plate depth: 30 μm), a dry coating amount of 1.0 g / m ² was applied to a 9 μm-thick polyethylene terephthalate film whose back surface was heat-treated with the above ink. And then dried. (Iii) Preparation of recording material Polyester resin 0.8 part (Vylon 103 Toyobo Tg = 47 ° C.) EVA polymer plasticizer 0.2 part (Elvalloy 741p Mitsui Polychemical Tg = −37 ° C.) Amino-modified silicone 0.04 parts (KF-857 manufactured by Shin-Etsu Chemical Co., Ltd.) Epoxy-modified silicone 0.04 parts (KF-103 manufactured by Shin-Etsu Chemical Co., Ltd.) Methyl ethyl ketone / toluene / cyclohexane (weight ratio 4: 4: 2) 9.0 parts Then, adjust the coating liquid and make synthetic paper (Oji Yuka,
YUPO FPG 150) with a bar coater (RK Prin)
Manufactured by t Coat Instruments, N
o. 1) was applied at a rate of 4.5 g / m ² when dried, and dried at 100 ° C. for 15 minutes. (Iv) Transfer recording The above-mentioned transfer sheet and the above-mentioned recording material are superposed on each other with their respective ink application surfaces and coating liquid application surfaces facing each other, and a thermal head applied voltage of 10 V and a printing time from the back surface of the thermal transfer sheet. Recording was carried out under the condition of 0 milliseconds to obtain a cyan color recording having a color density of 1.90.

The color density is densitometer RD-514 manufactured by Macbeth, Inc. (filter: Ratten N).
o. 58).

The color density was calculated by the following formula.

Color Density = log ₁₀ (Io / I) Io = Intensity of Light Reflected from Standard White Reflector I = Intensity of Light Reflected from Test Object In addition, the light fastness test of the obtained recording was xenon faded. It was carried out at a black panel temperature of 63 ± 2 ° C. using a meter (manufactured by Suga Test Instruments Co., Ltd.), but it was not discolored by irradiation for 40 hours, and the stability of the image under high temperature and high humidity was excellent.

The fastness of the recorded image obtained was 50 ° C.
After being left for 48 hours in the atmosphere, the image was sharp and the surface was rubbed with white paper, and the color was evaluated.
The sharpness of the image did not change, the white paper was not colored, and the fastness of the recorded image was good. Example-2 11 parts of p-diethylamino-o-toluidine and 11.6 parts of 2-ethoxycarbonylamino-5-acetylaminophenol were dissolved in a mixed solution of 63 parts of methanol and 38 parts of water to prepare 25% aqueous ammonia. 31 parts was added, the liquid temperature was kept at 20 ° C., and 76.6 parts of a 25% silver nitrate aqueous solution was added dropwise thereto in about 1 hour, and the reaction was carried out at room temperature for 2 hours. After the reaction
It was extracted with chloroform, washed well with water, and purified by column chromatography to obtain the following compound (B).

The maximum absorption wavelength (λmax) of the compound in chloroform was 625 nm.

[0067]

[Chemical 5] Ink adjustment, a transfer sheet and a recording material were prepared and transfer recording was performed in the same manner as in Example 1 to obtain a cyan recording having a color density of 1.90.

All of these records were subjected to the light resistance test by the same method as in Example-1. As a result, the records showed almost no change and the stability of the image under high temperature and high humidity was excellent.

A fastness test was conducted in the same manner as in Example 1, but the sharpness of the image did not change, the white paper was not colored, and the fastness of the recorded image was good. Examples-3 to 24 The cyan dyes shown in Table-1 were produced according to the same method as in Example-1, and similarly ink adjustment, transfer sheet preparation, recording material preparation, and transfer recording were performed. Each record shown in Table-1 was obtained.

All of these recordings were subjected to the light resistance test in the same manner as in Example-1. As a result, the recordings hardly changed and the stability of the image under high temperature and high humidity was excellent.

A fastness test was conducted in the same manner as in Example 1, but the sharpness of the image did not change, the white paper was not colored, and the fastness of the recorded image was good.

Table 1 shows the measurement results of the maximum transfer density, the light fastness and the determination results of the fastness.

[0073]

[Table 1]

[0074]

[Table 2]

[0075]

[Table 3]

[0076]

[Table 4] Good results for each of the light resistance and fastness determination results were indicated by ◯, and poor results were indicated by x.

[Comparative Example] With respect to the compounds shown in Table 2, ink was prepared, a transfer sheet was prepared, a recording material was prepared, and transfer recording was carried out in the same manner as in Example-1. Further, a light resistance test and a fastness test were performed in the same manner as in Example-1. The results are shown together in Table 2.

[0078]

[Table 5] Good results for each of the light resistance and fastness determination results were indicated by ◯, and poor results were indicated by x.

Front page continuation (72) Inventor Hitoshi Koshida 12-5-510 Koshienguchi Kitamachi, Nishinomiya-shi, Hyogo (72) Inventor Keisuke Soma 300 Hirahara-cho, Omuta-shi, Fukuoka (72) Ryohei Takiguchi Tanikaga, Shinjuku-ku, Tokyo 1-1-1 Machi Dai Nippon Printing Co., Ltd. (72) Inventor Hiroshi Eguchi 1-1-1 Ichigaya Kagacho, Shinjuku-ku, Tokyo Dai-ni Printing Co. Ltd. (72) Inventor Kimiaki Kafuku Shinjuku-ku, Tokyo 1-1-1 Ichigaya Kagamachi Dai Nippon Printing Co., Ltd.

Claims (3)

[Claims] 1. The following general formula (I): (In the formula, R ¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a furfuryl group, or a tetrahydrofurfuryl group, and R ² and R ³ represent Hydrogen atom, carbon number 1
To 4 alkyl groups, alkoxy groups, or halogen atoms, and R ⁴ represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, or a heterocycle. , R ⁵ ~ R
⁸ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group, an alkylcarbonylamino group, an alkoxycarbonylamino group, a formylamino group, an alkylsulfonylamino group, or a halogen atom, and R ⁹ _and R ¹⁰ are A hydrogen atom, a substituted or unsubstituted alkyl group, an alkenyl group, an aralkyl group, or an aryl group is shown. ) A dye for thermal transfer recording represented by. 2. A heat-sensitive transfer recording ink comprising at least a heat-sensitive transfer recording dye represented by the general formula (I) according to claim 1, a binder resin, an organic solvent and / or water. Composition. 3. A base sheet and a dye-supporting layer formed on one surface of the base sheet, wherein the dye contained in the dye-supporting layer has the sensation represented by the general formula (I). A transfer sheet characterized by being a dye for thermal transfer recording.