JP3229103B2 - Heat-sensitive sublimation transfer recording sheet using anthraquinone-based magenta dye - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a heat-sensitive sublimation transfer recording sheet using a novel anthraquinone compound as a magenta dye. The novel anthraquinone compound of the present invention has a good hue as a magenta dye, is excellent in solubility in a binder resin, and is also excellent in light resistance or heat resistance. It exhibits excellent effects when used in a heat-sensitive sublimation transfer recording sheet.

[0002]

2. Description of the Related Art In recent years, the use of electronic images, including computer graphics, has rapidly increased. Therefore, it has been required to record electronic images such as video movies and television images of electronic still cameras as color hard copies. Have been. The so-called thermal sublimation transfer recording method, in which a dye for sublimation transfer is applied to a base sheet to form a thermal transfer sheet, which is selectively heated by a thermal head and transferred to a dyeable recording paper, is a so-called thermal sublimation transfer recording method. As an important recording method for obtaining a full-color image having excellent properties and color reproducibility.

As these thermal transfer sheets, three primary colors of yellow, magenta and cyan are usually used. However, the conventionally proposed dyes are required for thermal sublimation transfer recording, which are (1) hue, (2) solubility or compatibility with ink solvent and ink binder resin, (3) heat resistance, Very few satisfy all of (4) transferability and (5) light fastness, and the appearance of dyes satisfying the optimum conditions as dyes for thermal sublimation transfer recording has been expected. Above all, many anthraquinone compounds, which are inherently stable to light, heat, temperature, etc. and have excellent robustness, have been studied in many ways to control the absorption wavelength as a magenta dye and to dissolve in solvents or resins. ing.

For example, Japanese Patent Application Laid-Open No. 60-122192,
JP-A-60-131293, JP-A-60-15909
No. 1, JP-A-61-227093, JP-A-60-25
No. 3595, JP-A-62-25092, JP-A-62-25092
97886, JP-A-61-227093, JP-A-62-27093
3-288787, JP-A-63-288788, JP-A-63-288789, JP-A-1-174490
No. 1-amino-4-
Magenta dyes having various functional groups introduced at the 2-position of the hydroxy-anthraquinone compound are disclosed. However, although some have solubility, the absorption wavelength or light resistance is not satisfactory.

[0005]

SUMMARY OF THE INVENTION The present invention has been made in view of the above-mentioned circumstances of the prior art. That is,
An object of the present invention is to provide (1) a hue required as a magenta dye in a thermal sublimation transfer recording sheet, (2) solubility or compatibility with an ink solvent and a binder resin for an ink, (3) heat resistance, and (4) transferability. And (5) to provide a dye satisfying all the conditions of light fastness.

[0006]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, the following general formula (I):

[0007]

Embedded image

[0008] wherein, X is -COOR (wherein, R represents an alkyl group having 1 to 12 carbon atoms), - CN, or represents -NO _2; Y is 1 to 4 carbon atoms Z represents an alkyl group, alkoxy having 1 to 4 carbon atoms or halogen;
W represents a fluorine atom; p represents an integer of 0 to 2; q represents an integer of 0 to 5; and m is the number of fluorine atoms at positions 5 to 8 of the quinizarin skeleton. And an integer of 0 to 3] have been found to be suitable as a magenta dye in a heat-sensitive sublimation transfer recording sheet, thereby completing the present invention.

[0009]

DETAILED DESCRIPTION OF THE INVENTION In the present invention, an alkoxy group having 1 to 4 carbon atoms means a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group and a tertiary group. It means a butyloxy group. The alkoxy group having 1 to 12 carbon atoms means, in addition to the above-mentioned alkoxy group, a linear or branched pentyloxy group, a linear or branched hexyloxy group, a linear or branched heptyl group. An oxy group, a straight or branched octyloxy group, a straight or branched nonyloxy group, a straight or branched decyloxy group, a straight or branched undecyloxy group, and a straight or branched It means a branched dodecyloxy group.

An alkyl group having 1 to 4 carbon atoms means a methyl group, an ethyl group, an n-propyl group, an isopropyl group,
It means an n-butyl group, an isobutyl group, and a tert-butyl group. The alkyl group having 1 to 12 carbon atoms means, in addition to the above-mentioned alkyl groups, a linear or branched pentyl group, a linear or branched hexyl group, a linear or branched heptyl group. A straight or branched octyl group,
A straight or branched nonyl group, a straight or branched decyl group, a straight or branched undecyl group, and a straight or branched dodecyl group are meant.

An alkylthio group having 1 to 8 carbon atoms means a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, a tertiary butyloxy group, a linear or branched alkylthio group. It means a branched pentylthio group, a straight or branched hexylthio group, a straight or branched heptylthio group, a straight or branched octylthio group. Halogen means a fluorine atom, a chlorine atom or a bromine atom, and is preferably a fluorine atom. Particularly, by imparting a fluorine atom, the effect on the solubility in a solvent or a resin can be promoted.

In the present invention, any one of the (a) -type or (b) -type anilino-based substituents is specifically listed at any of the 5, 6, 7 and 8-positions in the skeleton of a quinizarin compound which is a kind of anthraquinone compound. Is introduced, and if necessary, other substituents are introduced.

[0013] (a) Type anilino group, o- ethoxycarbonyl anilino group, p-
Ethoxycarbonylanilino group, m-ethoxycarbonylanilino group, o-butoxycarbonylanilino group, p
-Butoxycarbonylanilino group, m-butoxycarbonylanilino group, o-cyanoanilino group, p-cyanoanilino group, m-cyanoanilino group, o-nitroanilino group, p-nitroanilino group, m-nitroanilino group, o
-Methoxyanilino group, p-methoxyanilino group, m-
A methoxyanilino group,

O-methylanilino, p-methylanilino, m-methylanilino, o-tert-butylanilino, p-tert-butylanilino, m-tert-butylanilino, o-fluoroanilino Group, p
-Fluoroanilino group, m-fluoroanilino group, 2,
3,5,6-tetrafluoroanilino group, 4-cyano-
2,3,5,6-tetrafluoroanilino group,

2-methyl-6-cyanoanilino group, 2-
Methyl-6-nitroanilino group, 2-methyl-6-carboxyanilino group, 2-methyl-6-methoxycarbonylanilino group, 2-methyl-4-cyanoanilino group, 2-
Methyl-4-nitroanilino group, 2-methyl-4-carboxyanilino group, 2-methyl-4-methoxycarbonylanilino group, 2-butyl-4-nitroanilino group, 2
-Butyl-4-carboxyanilino group, 2-methoxy-
4-cyanoanilino group, 2-methoxy-4-nitroanilino group, 2-methoxy-4-carboxyanilino group, 2
-Methoxy-4-methoxycarbonylanilino group;

(B) Type 2,6-dimethylanilino group, 2,6-diethylanilino group, 2,6-dipropylanilino group, 2,6-diisopropylanilino group, 2,6-dibutylaniline Lino group,
2,6-diisobutylanilino group, 2,6-di-tert-butylanilino group, 2,6-dimethoxyanilino group,
2,6-diethoxyanilino group, 2,6-dipropoxyanilino group, 2,6-diisopropoxyanilino group,
2,6-dibutoxyanilino group, 2,6-isobutoxyanilino group, 2,6-ditert-butoxyanilino group, 2,6-dichloroanilino group, 2-chloro-6-methylanilino group,

4-cyano-2,6-dimethylanilino group, 4-cyano-2,6-diethylanilino group, 4-cyano-2,6-dipropylanilino group, 4-cyano-
2,6-diisopropylanilino group, 4-cyano-2,
6-dibutylanilino group, 4-cyano-2,6-diisobutylanilino group, 4-cyano-2,6-di-tert-butylanilino group, 4-cyano-2,6-dimethoxyanilino group, 4- Cyano-2,6-diethoxyanilino group, 4-cyano-2,6-dipropoxyanilino group, 4
-Cyano-2,6-diisopropoxyanilino group, 4-
Cyano-2,6-dibutoxyanilino group, 4-cyano-
2,6-diisobutoxyanilino group, 4-cyano-2,
A 6-ditabutoxyanilino group,

4-nitro-2,6-dimethylanilino group, 4-nitro-2,6-diethylanilino group, 4-nitro-2,6-dipropylanilino group, 4-nitro-
2,6-diisopropylanilino group, 4-nitro-2,
6-dibutylanilino group, 4-nitro-2,6-diisobutylanilino group, 4-nitro-2,6-ditert-butylanilino group, 4-nitro-2,6-dimethoxyanilino group, 4- Nitro-2,6-diethoxyanilino group, 4-nitro-2,6-dipropoxyanilino group, 4
-Nitro-2,6-diisopropoxyanilino group, 4-
Nitro-2,6-dibutoxyanilino group, 4-nitro-
2,6-diisobutoxyanilino group, 4-nitro-2,
6-tert-butoxyanilino group,

4-ethoxycarbonyl-2,6-dimethylanilino group, 4-ethoxycarbonyl-2,6-diethylanilino group, 4-diethoxycarbonyl-2,6-
Dipropylanilino group, 4-ethoxycarbonyl-2,
6-diisopropylanilino group, 4-ethoxycarbonyl-2,6-dibutylanilino group, 4-ethoxycarbonyl-2,6-diisobutylanilino group, 4-ethoxycarbonyl-2,6-ditert-butylanilino group ,

4-ethoxycarbonyl-2,6-dimethoxyanilino group, 4-ethoxycarbonyl-2,6-diethoxyanilino group, 4-ethoxycarbonyl-2,6
-Dipropoxyanilino group, 4-ethoxycarbonyl-
2,6-diisopropoxyanilino group, 4-ethoxycarbonyl-2,6-dibutoxyanilino group, 4-ethoxycarbonyl-2,6-diisobutoxyanilino group, 4
An ethoxycarbonyl-2,6-ditert-butoxyanilino group.

These substituents are substituted with 5, 5 of the quinizarin skeleton.
By introducing one at the sixth, seventh or eighth place, it is possible to control to a magenta hue. The (b) type substituent can also impart solubility at the same time, and thus can be used as it is as a dye for thermal sublimation transfer recording. As the substituent of the type (a), it is preferable to introduce one or two substituents of the following type (c) at the 5, 6, 7 or 8 positions of the quinizarin skeleton at the same time. These can improve the solubility.

[0022] (c) type main butoxy group, an ethoxy group, n- propoxy group, isopropoxy group, butoxy group, isobutoxy group, tertiary butoxy group, hexyloxy group, octyloxy group, nonyloxy group, decyloxy group, dodecyloxy Base.

The residue after the introduction of (a), (b) and / or (c) type substituents as necessary at the 5, 6, 7 and / or 8 positions of the quinizarin skeleton is a fluorine atom.
I am a child. In particular, by imparting a fluorine atom, an effect can be exerted on solubility in a solvent or a resin.

[0024] Specific prior Symbol anthraquinone compounds of general formula (I), for example include the following compounds.

(1) 7-butoxy-6-anilino-5
8-Difluoroquinizarin (2) 7-butoxy-6- (o-ethoxycarbonylanilino) -5,8-difluoroquinizarin (3) 7-butoxy-6- (p-ethoxycarbonylanilino)- 5,8-Difluoroquinizarin (4) 7-butoxy-6- (m-ethoxycarbonylanilino) -5,8-difluoroquinizarin (5) 7-octyloxy-6- (o-ethoxycarbonylani Reno) -5,8-difluoroquinizarin

(6) 7-octyloxy-6- (p-ethoxycarbonylanilino) -5,8-difluoroquinizarin (7) 7-octyloxy-6- (m-ethoxycarbonylanilino) -5 , 8-Difluoroquinizarin (8) 7-octyloxy-6- (o-butoxycarbonylanilino) -5,8-difluoroquinizarin (9) 7-octyloxy-6- (p-butoxycarbonylani (Rino) -5,8-difluoroquinizarin (10) 7-octyloxy-6- (m-butoxycarbonylanilino) -5,8-difluoroquinizarin

(11) 7-butoxy-6- (o-nitroanilino) -5,8-difluoroquinizarin (12) 7-butoxy-6- (m-nitroanilino)-
5,8-difluoroquinizarin (13) 7-butoxy-6- (p-nitroanilino)-
5,8-Difluoroquinizarin (14) 7-octyloxy-6- (p-nitroanilino) -5,8-difluoroquinizarin (15) 7-butoxy-6- (o-cyanoanilino)-
5,8-difluoroquinizarin

(16) 7-butoxy-6- (m-cyanoanilino) -5,8-difluoroquinizarin (17) 7-butoxy-6- (p-cyanoanilino)-
5,8-Difluoroquinizarin (18) 7-octyloxy-6- (p-cyanoanilino) -5,8-difluoroquinizarin (19) 7-methoxy-6- (2,6-dimethylanilino) -5,8-Difluoroquinizarin (20) 7-butoxy-6- (2,6-dimethylanilino) -5,8-difluoroquinizarin

(21) 7-octyloxy-6- (2,
6-dimethylanilino) -5,8-difluoroquinizarin (22) 7-methoxy-6- (2,6-diethylanilino) -5,8-difluoroquinizarin (23) 7-butoxy-6 -(2,6-diethylanilino) -5,8-difluoroquinizarin (24) 7-octyloxy-6- (2,6-diethylanilino) -5,8-difluoroquinizarin (25) 7-methoxy-6- (2-nitro-6-dimethylanilino) -5,8-difluoroquinizarin

(26) 7-butoxy-6- (2-nitro-6-dimethylanilino) -5,8-difluoroquinizarin (27) 7-octyloxy-6- (2-nitro-6
(Dimethylanilino) -5,8-difluoroquinizarin (28) 7-octyloxy-6- (2-carboxy-
6-dimethylanilino) -5,8-difluoroquinizarin (29) 5-anilino-6,7-dibutoxy-8-fluoroquinizarin (30) 5-anilino-6,7-dioctoxy-8-
Fluoroquinizarin

(31) 5- (o-ethoxycarbonylanilino) -6,7-dibutoxy-8-fluoroquinizarin (32) 5- (p-ethoxycarbonylanilino)-
6,7-dibutoxy-8-fluoroquinizarin (33) 5- (m-ethoxycarbonylanilino)-
6,7-dibutoxy-8-fluoroquinizarin (34) 5- (p-butoxycarbonylanilino)-
6,7-dibutoxy-8-fluoroquinizarin (35) 5- (o-nitroanilino) -6,7-dibutoxy-8-fluoroquinizarin

(36) 5- (p-nitroanilino)-
6,7-dibutoxy-8-fluoroquinizarin (37) 5- (m-nitroanilino) -6,7-dibutoxy-8-fluoroquinizarin (38) 5- (o-cyanoanilino) -6,7- Dibutoxy-8-fluoroquinizarin (39) 5- (p-cyanoanilino) -6,7-dibutoxy-8-fluoroquinizarin (40) 5- (m-cyanoanilino) -6,7-dibutoxy-8- Fluoroquinizarin

(41) 6- (m-ethoxycarbonylanilino) -5,7-dimethoxy-8-fluoroquinizarin (42) 6- (m-butoxycarbonylanilino)-
7,8-dibutoxy-5-fluoroquinizarin (43) 6- (p-butoxycarbonylanilino)-
7,8-dioctyloxy-5-fluoroquinizarin (44) 6- (m-ethoxycarbonylanilino)-
5,7,8- Toributoki Shiki Nizarin (45) 6- (2,6-dimethyl anilino) 5,7,
8-trifluoroquinizarin

(46) 6- (2,6-diethylanilino) -5,7,8-trifluoroquinizarin (47) 6- (2,6-dibutylanilino) -5,7,
8-trifluoroquinizarin (48) 6- (2-methyl-6-nitroanilino)-
5,7,8-trifluoroquinizarin (49) 6- (2-methyl-6-carboxyanilino)
-5,7,8-trifluoroquinizarin (50) 6- (2,6-dichloroanilino) -5,7,
8-trifluoroquinizarin (51) 6- (2-chloro-6-methylanilino)-
5,7,8-trifluoroquinizarin (52) 6- (2,3,5,6-tetrafluoroanilino) -5,7,8-trifluoroquinizarin.

The anthraquinone compounds represented by the general formula (I) include, for example, at positions 5, 6, 7 and 8;
Positions 5 and 6; 6 and 7; quinizarine substituted at position 5 and 8 or at position 5 and 7 by halogen, depending on the substituents to be introduced, A reaction nucleophile selected from a series of amino compounds, aliphatic amino compounds, aromatic hydroxy compounds, aliphatic hydroxy compounds, aromatic mercapto compounds, or aliphatic mercapto compounds, individually or sequentially, It can be synthesized by nucleophilic substitution of a halogen atom.

At this time, the reaction is usually carried out in an organic solvent.
As the organic solvent, nitrobenzene, acetonitrile,
An inert solvent such as benzonitrile, or pyridine,
N, N-dimethylacetamide, N-methyl-2-pyrrolidone, triethylamine, tri-n-butylamine,
An aprotic polar solvent such as dimethyl sulfone and sulfolane can be used. Alternatively, the reaction nucleophile itself such as the above-mentioned amino compound or hydroxy compound can be used as a solvent without using the organic solvent.

As the condensing agent, organic bases such as triethylamine and tri-n-butylamine and inorganic bases such as potassium fluoride, potassium hydroxide, potassium carbonate, sodium hydroxide and sodium carbonate are preferably used.
It is also possible to use a nucleophilic substitution reagent such as aniline, toluidine, anisidine, n-butylamine and n-octylamine as a condensing agent. Alternatively, when the reaction nucleophile itself such as the amino compound has properties as a condensing agent, it is not always necessary to use the condensing agent.
The reaction temperature is preferably in the range of room temperature to 200 ° C.

According to another production method, a part or all of the benzene nucleus of phthalic anhydride is substituted with the final compound according to a generally well-known so-called Friedel-Crafts reaction (for example, JP-A-61-112041). Depending on the group, a substituent selected from a halogen atom, an aromatic amino group, an aliphatic amino group, an aromatic hydroxy group, an aliphatic hydroxy group, an aromatic mercapto group, or an aliphatic mercapto group Phthalic anhydride or a derivative of phthalic acid (preferably a derivative of phthalic anhydride) and a hydroquinone such as hydroquinone or dimethoxyhydroquinone (preferably dimethoxyhydroquinone). The anthraquinoline compound used in the present invention can be produced by the methods described in Japanese Patent Application Nos. 5-14834 and 6-7686.

As a method for preparing a transfer sheet using the coloring matter of the present invention, a thermal transfer recording ink composed of a coloring matter, a binder resin and a solvent is applied to a transfer sheet substrate and dried. The concentration of the dye in the ink is usually 1
~ 5% by weight. As the binder resin for preparing the ink, any of conventionally known binder resins can be used, preferably ethyl cellulose, hydroxyethyl cellulose,
Cellulose resins such as ethylhydroxycellulose, hydroxypropylcellulose, methylcellulose, and cellulose acetate, and vinyl resins such as polyvinylbutyral, polyvinylacetoacetal, polyvinylpyrrolidone, and polyacrylamide. Of these, polyvinyl butyral is particularly preferred from the viewpoint of heat resistance, dye transferability, and the like.

Examples of the medium for preparing the ink include aromatics such as toluene, xylene and chlorobenzene, esters such as ethyl acetate and butyl acetate, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, methanol and ethanol. , Alcohols such as propanol and butanol, cellosolves such as methyl cellosolve and ethyl cellosolve, and hydrocarbons such as ligroin, cyclohexane and kerosene.

As the base material of the transfer sheet to which the ink is applied, any known base material having good heat resistance and strength can be used, but polyester films, polystyrene films, polypropylene films, polysulfone films, polycarbonate films, and polycarbonate films are preferred. Aramid film, polyvinyl alcohol film, cellophane, etc., and particularly preferred are polyester films. The appropriate thickness is about 2 to 20 μm. As a method of applying the ink to the transfer sheet substrate, a bar coater, a roll coater, a gravure coater, a knife coater, or the like can be used, and the thickness of the applied layer of the ink is 0.1 to 5 μm after drying, preferably. Is preferably 0.4 to 2.0 μm.

Examples of the recording material include polyolefin resins such as polyethylene and polypropylene; halogen polymers such as polyvinyl chloride and polyvinylidene chloride; vinyl polymers such as polyvinyl alcohol, polyvinyl acetate and polyacrylic acid; Polyester resins such as terephthalate and polybutylene phthalate; polystyrene resins, polyamide resins, copolymer resins of olefins such as ethylene and propylene and other vinyl polymers; cellulose resins such as ionomers and cellulose diacetate; polycarbonate, polysulfone, and polyimide Fibers, woven fabrics, films, sheets, molded products, and the like made of such materials. Particularly preferred are fibers, woven fabrics, films, sheets, processed paper and the like made of polypropylene or polyethylene terephthalate.

[0043]

The anthraquinone dye represented by (I) used in the construction of the magenta color sublimation transfer sheet of the present invention has a substituent at a specific position as compared with the conventional anthraquinone dye, so that the dye Has excellent solubility in solvents and binder resins, has excellent hue as a magenta color, and has a quinizarin skeleton, so it has excellent light resistance, heat resistance, and excellent transferability. Have.

[0044]

Now, the present invention will be described in further detail with reference to Production Examples and Examples. In the examples, "parts" represents parts by weight. The dye numbers are the same as those of the above compounds.

Production Example 1 6- (m-ethoxycarboni
Luanilino) -5,7,8-trifluoroquinizarin
In a synthetic 500 cc four-necked flask, 400 cc of acetonitrile and 3 g of 5,6,7,8-tetrafluoroquinizarin (9.
61 mmol) and about 3.2 g of ethyl m-aminobenzoate
(19.4 mmol) and 1.34 g of potassium fluoride (2
3.1 mmol) and reacted under reflux for about 24 hours. After completion of the reaction, potassium fluoride was filtered off, and acetonitrile was distilled off. Then, the resultant was poured into an aqueous hydrochloric acid solution, the generated solid was filtered, washed with water and dried to obtain 4.3 g of a crude product.
Thereafter, column purification was performed using silica gel (Wakogel C-200) to give 6- (m-ethoxycarbonylanilino)-.
1.42 g (yield 32.3 mol%) of 5,7,8-trifluoroquinizarin was obtained.

Production Example 2 Synthesis of Dye (7) In a 500 cc four-necked flask, 400 cc of octyl alcohol and 6- (m-ethoxycarbonylanilino) -5,7,8-trifluoroquinizarin obtained in the same manner as in Production Example 1 above. 3 g (6.56 mmol) and 0.368 g (6.56 mmol) of potassium hydroxide were charged, and 120 ° C.
For about 5 hours. After completion of the reaction, the solution was transferred to a separating funnel, water was added thereto, and the mixture was shaken and separated. Thereafter, octyl alcohol in the organic layer was distilled off, and the obtained solid was dried to obtain 3.62 g (yield: 97.2 mol%) of the dye (7).

Visible absorption spectrum (in chloroform) λ _max ; 531 nm (ε: 12400) Mass spectrometry spectrum m / e = 567 (M ⁺ , 70) m / e = 454 (M ⁺ -113,100) Element Analytical value C (%) H (%) N (%) F (%) Theoretical value 65.60 5.50 2.47 6.69 Analytical value 65.67 5.50 2.51 6.62 Next, the present invention will be described in more detail with reference to Examples.
In the examples, "parts" indicates parts by weight. The dye numbers are the same as those of the above compounds.

Embodiment 1 (1) Preparation method of ink composition Dye (7) 3 parts Polyvinyl butyral resin (BLS-S manufactured by Sekisui Chemical) 4 parts Methyl ethyl ketone 47 parts Toluene 47 parts Using a glass bead, the dye mixture having the above composition is used with a paint shaker. For about 30 minutes to prepare the ink.

(2) Method for preparing transfer sheet The above ink was heat-treated with a silicone graft copolymer (manufactured by Nippon Shokubai Co., Ltd.) (about 1 μm) on its back surface to 5.7 μm.
Thick polyethylene terephthalate film (EMBLE
T, manufactured by Unitika Ltd.) so as to have a dry film thickness of about 1 μm and dried. (3) Transfer material The transfer material is a Mitsubishi Video Print Pack (CK-10
P, manufactured by Mitsubishi Electric Corporation).

(4) Transfer Recording The ink-coated surface of the transfer sheet and the dye-receiving surface of the material to be transferred are overlapped with each other.
Recording was performed with a thermal head under the conditions of 0 V and a printing time of 4.0 msec, and the results shown in Table 1 were obtained. The color density was measured using a densitometer RD-914 manufactured by Macbeth Co., USA.

[0051] (5) light resistance resulting recorded image xenon lamp lightfastness tester (SU
A light fastness test was performed using NTEST CPS Heraeus (black panel temperature: 63 ° C.), and the remaining color density after 200 hours was evaluated. (6) Storage stability The obtained recorded image was allowed to stand in an atmosphere at 50 ° C. for 50 hours, and the results of observing changes in the image are shown in Table 1. The sharpness of the image did not change, and even when the surface was rubbed with white paper, the white paper was not colored and the storage stability was good.

Embodiments 2 to 15 Preparation of an ink composition, preparation of a transfer sheet, and transfer recording were performed in the same manner as in Example 1 except that the dye was changed to the dye shown in Table 1. Table 1 shows the results. Further, the light resistance was measured in the same manner as in Example 1, and the storage stability was observed. Table 1 shows the results.

[0053]

[Table 1]

Continuation of the front page (56) References JP-A-62-97886 (JP, A) JP-A-63-62774 (JP, A) JP-A-2-258298 (JP, A) JP-A 60-177251 (JP JP-A-62-64595 (JP, A) JP-A-62-199655 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) B41M 5/38-5/40 CAPLUS (STN) REGISTRY (STN)

Claims (1)

(57) [Claims] 1. The following general formula (I): [Wherein, X is -COOR (where R is a group having 1 to 1 carbon atoms)
Represent 12 alkyl group), - CN, or -NO ₂
Y represents an alkyl group having 1 to 4 carbon atoms, alkoxy or halogen having 1 to 4 carbon atoms;
Z represents an optionally substituted alkoxy group having 1 to 12 carbon atoms; W represents a fluorine atom;
Q represents an integer of 0 to 5; and m represents the number of fluorine atoms at positions 5 to 8 of the quinizarin skeleton, and is an integer of 0 to 3]. A heat-sensitive sublimation transfer recording sheet using at least one species as a magenta dye.