JPH0565358B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a sublimation transfer material characterized by using a cyan dye having excellent sublimation properties. The sublimation transfer image recording method is a method of forming images by sublimating dyes using heat, and is currently attracting attention as a method of obtaining color hard copies from televisions, CRT color displays, color facsimile machines, magnetic cameras, etc. ing. As a heat source, a heating element or a laser, especially a semiconductor laser, is used. Currently, cyan dyes for sublimation transfer are selected from dyes that are close to cyan and are mainly used as disperse dyes, but all of them either have insufficient sublimation properties or the hue is not true. However, it has disadvantages such as not having a cyan color, and also having poor storage stability of recorded images. In particular, the low sublimability means that it is necessary to increase the output of the heating element or laser used as a heat source to sublimate these dyes, and as a result, the life of the heat source is shortened and the practicality of the recording device is reduced. The problem was that they were lost. For this reason, there is a strong desire to develop a dye that has good sublimation properties, excellent storage stability, and has hues of the three primary colors, cyan, magenta, and yellow, by subtractive mixing. In addition, the poor storage stability of recorded images causes the phenomenon that the recorded images change color or fade during storage, which has been a big problem in practice. An object of the present invention is to provide a cyan sublimation transfer material having good sublimation properties and excellent storage stability. That is, the present invention provides a sublimation transfer material using the sublimation transfer recording method in which a dye is sublimated by heat from an ink layer provided on a substrate to form an image on printing paper, and is provided by the following general formula (). (In the formula, R represents an alkyl group, an aralkyl group, an alkenyl group, an aryl group, or a 5- or 6-membered cycloalkyl group.) A sublimation transfer material characterized by using one or more kinds of dyes represented by the following: It is related to. In the general formula (), R is a linear or branched alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, or an aralkyl group such as a benzyl group or a phenethyl group. , allyl group, alkenyl group such as vinyl group, phenyl group, cyclopentyl group, cyclohexyl group, etc. Among these, preferable examples include methyl group,
Ethyl group, propyl group, butyl group, benzyl group,
Examples include allyl group, vinyl group, phenyl group, cyclopentyl group, and cyclohexyl group. The dye represented by the general formula () can be prepared by a known method,
For example, it is synthesized according to the reaction formula below. (In the formula, R represents the above-mentioned meaning.) A sublimation transfer material is manufactured by applying a pigment ink onto a transfer substrate. Transfer substrates are generally capacitor paper, cellophane, polyimide resins, polyester resins, polyethersulfone resins, or ribbon- or film-shaped materials treated with these resins to improve heat resistance and/or smoothness. is used. Dye ink generally consists of a sublimable dye, a binder, and, if a laser is used as a heat source, a compound that absorbs at the laser's oscillation wavelength, and is dissolved in a solvent using a ball mill or paint conditioner. Manufactured by atomization. Binders include natural resins or modified resins such as dammar, gum arabic, gum tragacanth, dextrin or casein, cellulosic resins such as methylcellulose, ethylcellulose, hydroxyethylcellulose, ethylhydroxycellulose or nitrocellulose, polyvinyl alcohol or polyvinyl acetate, etc. One kind or a mixture of two or more kinds of vinyl resins are used. Solvents for dissolving or dispersing dyes and binders include water, ethanol, propanol,
Alcohols such as butanol, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, aromatic hydrocarbons such as toluene, xylene, and monochlorobenzene, dichloroethane,
One or a mixture of two or more of chlorine solvents such as trichlorethylene and perchlorethylene, and acetate esters such as ethyl acetate, butyl acetate, and ethoxyethyl acetate are used. Compounds that absorb at the laser oscillation wavelength include carbon black, phthalocyanine pigments,
Dithiol complexes, naphthoquinones, etc. are used. The dye ink thus obtained is applied onto a transfer substrate using a bar coater, roll coater, knife coater, screen printing, gravure printing, etc. to produce a sublimation transfer body. Printing paper can be paper coated with polyester resin or polyamide resin, synthetic paper such as polypropylene, polyvinyl chloride, or polyester, or synthetic paper that has been treated to improve heat resistance, etc., as necessary. Those coated with polyester resin, polyamide resin, etc., which have a strong affinity with dyes, are used. Hereinafter, the present invention will be explained in detail with reference to Examples. In the examples, parts represent parts by weight. Example 1 6 parts of ethylcellulose, 1-amino-2,3-
Dicyano-4-methylaminoanthraquinone 5
An ink composition containing 71.2 parts of xylene, 71.2 parts of n-butanol, and 17.8 parts of n-butanol was sufficiently kneaded using a paint conditioner, and then coated on condenser paper using a bar coater and dried to obtain a sublimation transfer material.
When this transfer body was placed opposite paper coated with polyethylene terephthalate resin and heated with a heating element, a clear cyan-colored image with high density was obtained on the paper. This cyan image did not fade or change color even when exposed to sunlight, and had excellent storage stability. The dye used in this example was synthesized as follows. 1-Amino-4-bromoanthraquinone-2-
Add 180 parts of sulfonic acid, 200 parts of methylamine, 54 parts of sodium carbonate, and 5.3 parts of copper sulfate (dissolved in 25 parts of water) to water.
Mix with 4250 parts, seal tightly, raise the temperature to 80℃ in 1 hour, and keep at the same temperature for 2 hours. Thereafter, 400 parts by volume are distilled off under reduced pressure, and heated to 93° C. under normal pressure. The solution was precipitated with hydrochloric acid to precipitate crystals, filtered and washed to give 1-amino-4-methylaminoanthraquinone-2-sulfonic acid 123
part was obtained. Next, 67.5 parts of this 1-amino-4-methylaminoanthraquinone-2-sulfonic acid, 900 parts of water, and 16.5 parts of potassium carbonate were mixed, and sodium cyanide was added.
98 parts, sodium m-nitrobenzenesulfonate 45
1 part, add 7.5 parts of ammonium bicarbonate, 85-90℃
Keep warm for 6 hours. Thereafter, the mixture was cooled to 60°C, filtered, washed with water, and dried to obtain 59.1 parts of 1-amino-2,3-dicyano-4-methylaminoanthraquinone. mp.250°C or higher Sublimation starting temperature 180°C Example 2 The dyes in Table 1 were synthesized in the same manner as in Example 1, and sublimation transfer was performed on each to produce a high-density, vivid cyan with excellent storage stability. A colored image was obtained.

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Claims (1)

[Claims] 1. In a sublimation transfer body using a sublimation transfer recording method in which a dye is sublimated by heat from an ink layer provided on a substrate to form an image on printing paper, the following general formula () is used. (In the formula, R represents an alkyl group, an aralkyl group, an alkenyl group, an aryl group, or a 5- or 6-membered cycloalkyl group.) A sublimation transfer material characterized by using one or more kinds of dyes. .