JPS6053565A - Heat-sensitive transfer recording quinophthalone coloring matter - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (Ar is phenylene or naphthylene; X is H, chlorine or bromine). EXAMPLE:A compound of formula II. USE:Coloring matter for heat-sensitive transfer recording ink manufacture, having clear yellow color, suitable for obtaining full-color through the combination with both fuchsine and cyan-colored coloring matters. PREPARATION:For example, a condensation is performed between a compound of formula III and phthalic anhydride or naphthalene-2,3-dicarboxylic acid anhydride of formula IV in an organic solvent such as o-dichlorobenzene trichlorobenzene.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a quinophthalone dye for thermal transfer recording.

Currently, a sublimation type thermal transfer recording method has been proposed as a method for obtaining color hard copies from televisions, ORT color displays, color facsimiles, magnetic cameras, and the like.

In this method, a transfer sheet coated with a sublimable dye is heated with a heat-sensitive recording head to sublimate and transfer the dye to a recording medium, thereby obtaining color recording.

5. Gradation expression is easy because the amount of dye sublimation can be controlled by adjusting the energy applied to the thermal head.
Compared to other recording methods, this method is particularly advantageous in obtaining full-color hard copies.

By the way, the dye used in this recording method must meet the following conditions.

■ Easily sublimated under the operating conditions of the thermal recording head.

■Do not thermally decompose under the operating conditions of the thermal recording head.

■ It must have a favorable hue in terms of color reproduction.

■ High molecular extinction coefficient.

■ Stable against light, moisture, chemicals, etc.

■ Easy to synthesize.

The object of the present invention is to provide a yellow dye that particularly satisfies (1), (2) and (2) among the requirements for dyes used in the above-mentioned thermal transfer recording method.

That is, in the present invention, Ar represents a phenylene group or a naphthylene group, or a hydrogen atom,
Represents a chlorine atom or a bromine atom. ) is a quinophthalone dye for thermal transfer recording.

The dye of the present invention can be prepared using a known method, for example, by combining a compound represented by the following structural formula [11] and a phthalic anhydride represented by the following general formula II (where AI is the same as defined above). Alternatively, it can be easily obtained by condensing naphthalene, J-dicarboxylic anhydride with an organic solvent such as VO-dichlorbenzene or trichlorobenzene, and filtering the precipitated target product after the reaction. Furthermore, the target compound ytq can be obtained by halogenation if necessary.

Furthermore, the target product can be purified by conventional means such as recrystallization or column chromatography, if necessary.

A method for producing a thermal transfer recording ink using the dye of the present invention is to mix one dye with a suitable resin, solvent, water, etc. to prepare the recording ink. In addition, as a thermal transfer method, the ink obtained above is applied onto a suitable base material to create a transfer sheet, and the sheet is overlaid on the Y recording material. An example of this method is a method of pressing, in which the dye on the sheet is transferred onto the recording medium.

As the resin for preparing the above ink, resins used in ordinary printing inks may be used (rosin type, phenol type, Φ silene type, 5 petroleum type, vinyl type, polyamide type, etc.).
Oil-based resins such as alkyd-based, nitrocellulose-based, alkylcellulose-based alkylcellulose, or water-based resins such as maleic acid-based, acrylic acid-based, casein, shellac, and glue can be used. In addition, as solvents for ink preparation, alcohols such as methanol, ethanol, propatool, and butanol, cellosolves such as methyl cellosolve and ethyl cellosolve, aromatics such as benzene, toluene, and xylene, ethyl acetate, butyl acetate, etc. esters such as acetone, methylethylgtone, ketones such as cyclohexanone, ligroin,
Hydrocarbon water XM such as cyclohexane and kerosene, dimethylformamide, etc. can be used, but when an aqueous resin is used for one bottle, water or a mixture of water and the above-mentioned solvents can also be used.

・Substrates for applying ink include condenser paper, thin paper such as glassine paper, polyester, polyamide,
Plastic films with good heat resistance such as polyimide are suitable, but these base materials improve the efficiency of heat transfer from the thermal recording head to the dye. A thickness of about Qμm is appropriate.

Plain paper can also be used as the recording medium, but in order to improve the color development of the dye, it may be coated or impregnated with a resin that has good compatibility with the dye, or it may be coated with a resin film ceraminate. Good recording can be achieved by using paper or special processed paper that has been treated with acetylation. It is also possible to use films of each a-resin or synthetic paper made from them.

Furthermore, by pressing and laminating, for example, a polyester film YWb on the transfer recording surface after transfer recording, it is possible to improve the color development of the dye and to stabilize the recording during storage.

Since the color of the present invention is a vivid yellow color, it is suitable for obtaining a full color by combining, for example, a magenta dye represented by the following structural formula and a cyan dye represented by the following structural formula. It can also be used in combination with other yellow pigments.

The above magenta pigment is tetracyanoethylene and N-
It can be easily produced by reacting with butyl-N-hydroxyaniline. Further, the above cyan dye can be produced by reacting /-7 minnowcocarboxy-methylaminoanthraquinone with methanol in concentrated sulfuric acid.

EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but these Examples do not limit the present invention.

Example 1 i> Method for preparing ink for thermal transfer recording (maximum absorption wavelength + pzanm: chloroborm) (melting point, 26 g to 467
The ink was prepared by mixing the pigment mixture having the above composition with a paint conditioner using Gance Beads for about 30 minutes.

11) Method for preparing transfer sheet The above ink was applied onto condenser paper (10 μm) using a gravure proofing machine (plate R, 30 μm).

111) Method for making image receiving paper 10 fl of an aqueous dispersion of saturated polyester 34 (manufactured by Toyobo Co., Ltd., Pyronal MD-7, -〇〇)
and calcium bicarbonate (Maruo Calcium Manufacturing, Super/
, 300) A; 0 weight water slug IJ -j Q fl
Coat the paint prepared by mixing Y with a bar coater (RK Pr1nt Coat) on a high-quality ink coat (thickness θ0 μm).
AC3) manufactured by Truments Inc.

IV) Transfer recording method The ink-coated surface of the above transfer sheet is placed over the paint-coated surface of the above-described paper, and thermal transfer recording is performed using a thermal head having a heating resistor ZII dot of 23θΩ at a density of Yellow records of o and qo were obtained. At this time, a voltage of /gv was applied to the thermal head for 6 milliseconds.

Nao, color i&%' [was measured using a densitometer RD-&/DA model (filter m: Utten Ada 7) manufactured by Macbeth, USA.

Color density was calculated using the following formula.

Color density "log 1o'(Eng.#/Eng.) E.tp:
Intensity of reflected light from a standard white reflector: Intensity of reflected light from a test object In addition, the light resistance test of the obtained records was performed using a carbon arc fade meter (manufactured by Suga Eken! 1 Co., Ltd.). The test was carried out under the condition of black panel temperature of 63°C.
There was almost no discoloration after irradiation for o hours.

Example 2 Using the pigment 21/' shown in Table 1, the ink was prepared, a transfer sheet and receiver paper were prepared, and transfer recording was carried out in the same manner as in Example 1. A yellow record was obtained. All of these records were subjected to a light fastness test in the same manner as in Example 1, but in this test, the records obtained using the dye of the present invention hardly changed color.

Claims (1)

[Claims] (1) A quinophthalone dye for thermal transfer recording represented by the general formula [■] (wherein Ar represents a phenylene group or a naphthylev group, and X represents a hydrogen atom, a chlorine atom, or a bromine atom).