JPS60151097A - Anthraquinone dye for thermal transfer recording - Google Patents

Abstract

PURPOSE:To obtain a cyan color anthraquinone dye for thermal transfer recording having a favorable hue in view of color reproduction without being pyrolyzed under the operating conditions of a thermal recording head and being resistant to light, moisture, chemicals or the like, by using a compound of a special structural formula. CONSTITUTION:A compound of formula [ I ], wherein each of R<1> and R<2> is alkyl, alkenyl, cyclohexyl, haloalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, hydroxyalkoxyalkyl, hydroxyalkylthioalkyl, cyanoalkyl, tetrahydrofurfuryl, alkenyloxxalkyl, tetrahydrofurfuryloxyalkyl, alkoxycarbonylakyl, alkylcarbonyloxyalkyl or alkoxycarbonyloxyalkyl, is used. A thermal transfer recording ink may be prepared from the dye by mixing the dye with an appropriate resin, solvent, water or the like.

Description

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

Currently, TVs and CRT color displays.

A dye sublimation thermal transfer recording method has been proposed as a method for obtaining color hard copies from 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 broken recording medium, thereby obtaining a color record.

(by adjusting the energy applied to the thermal head)
It is easy to express gradations because the sublimation of the dye can be controlled.
Compared to other recording methods, it is particularly advantageous in obtaining full-color hard copies.

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

■ Easy to operate under the operating conditions of the thermal recording head.

■ Thermal decomposition may occur under the operating conditions of the thermal recording head.

■ Must have a favorable hue for color reproduction.

■ Large molecular extinction coefficient.

■ Stable against sources, moisture, chemicals, etc.

■ Easy to synthesize.

The entire purpose of the present invention is to provide a cyan dye that satisfies (1), (2), and (3) among the necessary conditions for the dye used in the above-mentioned thermal recording method.In other words, the present invention has the following: [1] (in the formula % R1 and R2 haalkyl group, alkenyl group,
Cyclohexyl group, halogenoalkyl group, alkoxyalkyl group, alkoxyalkoxyalkyl group, hydroxyalkyl group, hydroxyalkoxyalkyl group, hydroxyalkylthioalkyl group, cyanoalkyl group, tetrahydrofurfuryl group, alkenyloxyalkyl group-tetrahydrofurfuryloxyalkyl group .

The gist thereof is an anthraquinone thread thermal transfer recording dye represented by an alkoxycarbonylalkyl group, an alkylcarbonyloxyalkyl group, or a haalkoxycarbonyloxyalkyl group.

As R1 and R2 represented by the front leg general formula (1),
Methyl group, ethyl group, n-propyl group.

1-propyl group, n-butyl group, 1-butyl group.

n-pentyl group, n-hexyl group, n-heptyl group
Alkyl groups such as n-octyl group and coethylhexyl group; allyl group, 2-methylallyl group, -monolyloallyl group, and 2-monoallyl group.

Crotyl group, 3-phenylallyl alkenyl group;
Cyclohexyl group; alkoxyalkyl groups such as methoxyethyl group, ethoxyethyl group, propoxyethyl group, but3-xyethyl group, and γ-methoxybutyl group; methoxyethoxyethyl group.

Alkoxyalkoxyalkyl groups such as ethoxyethoxyethyl group and propoxyethoxyethyl group; human tetraxyalkyl groups such as hydroxyethyl group, β-hydroxyglobyl group, /-hydroxybutyl group; chloroethyl group,
Chloroethyl group, bromoethyl group, iodoethyl group, cyclic halogenoalkyl group, dianomethyl group, cyanoethyl group, cyanopropyl-based cyanoalkyl group: tetrahydride, pylphurfuryl group: allyloxyethyl group, 5. Alkenyl such as 2-methylallyloxyethyl group Oxyalkyl group: methoxycarbonylethyl group, ethoxycarbonylethyl group.

Alkoxycarbonylalkyl groups such as propoxycarbonyl ether group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group: acetoxyethyl group, glopionyloxyethyl group.

Alkylcarbonyloxyalkyl groups such as β-acetoxypropyl group and β-acetoxybutyl group 4- group: Alkoxycarbonyloxyalkyl group such as methoxycarbonyloxyethyl group and ethoxycarbonyloxyethyl group: Tetrahydrofuryl group such as tetrahydrofurfuryloxyethyl group Furyloxyalkyl group: Hydroxyalkoxyalkyl group such as an ocular xyethoxyethyl group and hydroxypropoxyethyl group: Hydroxyalkylthioalkyl group such as hydroxyethylthioethyl group, and the like.

Particularly preferred R1 and R2 are O8-, alkyl &
% r-methoxybutyl group, chloroethyl group, methoxyethyl group, methoxyethoxyethyl group, cyanoethyl group, tetrahydrofurfuryl group, cyclohexyl group, allyloxyethyl group, tetrahydrofurfuryloxyethyl group, hydroxyethyl group, allyl group, methoxy Examples include carbonylethyl group and hydroxyethoxyethyl group.

In a method for producing a thermal transfer recording ink using the dye of the present invention, the dye is mixed with a suitable resin.

It may be mixed with a solvent, water, etc. to make an ink for recording coughs. In addition, as a thermal transfer method, the ink obtained above is spread on a suitable base material to create a transfer sheet, the sheet is placed on the recording medium, and then heated and heated from the back side of the sheet with a thermal recording head. The method of pressing can be mentioned, and if the method shown in 7 is used, the dye on the sheet is transferred onto the recording medium.

As a resin for preparing the ink mentioned above.

Anything that is used for normal printing in Φ may be used, such as rosin thread,
Phenol thread, xylene thread, petroleum-based.

Oil-based resins such as polysulfone, vinyl, polyamide, alkyd, nitrocellulose, and alkyl cellulose, or water-based resins such as maleic acid, acrylic acid, casein, shellac, and glue can be used. . In addition, as solvents for ink preparation, alcohols such as methanol, ethanol, gropanol, and butamele, methyl cellosolve,
Selonolup such as ethylselonulp, benzene, toluene, xylene natonoaromatics, esters such as ethyl acetate and butyl acetate, acetone, methyl ethyl ketone,
Ketones such as cyclohexanone, hydrocarbons such as ligroin, Schiff's hexasan, kerosene, dimethylformamide, etc. can be used, but when using water-based resin gold, use water or a mixture of water and the above solvents. You can also do it.

Suitable base materials for applying ink include thin paper such as condenser paper and glassine paper, and plastic films with good heat resistance such as polyester, polyamide, and polyimide.

These base materials suitably have a thickness of about t-10 μm in order to improve the efficiency of heat transfer from the thermal recording head to the dye.

In addition, plain paper can be used as the recording material, but in order to improve the color development of the dye, it may be coated or impregnated with a resin that is compatible with the dye, or in some cases, paper may be coated with silica gel. Added acidic fine particles such as.

Or a turtle piece laminated with a resin film.
- By using a special Kaloe paper that has been treated with acetylation, it is possible to make good recordings with excellent light resistance and image stability under high temperature and high humidity conditions. It is also possible to use films of various resins or synthetic papers made from them.

Furthermore, by heat-pressing and laminating, for example, a polyester film 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.

This is because the dye of the present invention has a clear cyan color.

For example, it is suitable for obtaining full color by combining with a yellow dye represented by the following structural formula and a magenta color dye represented by the following structural formula OH 8- .

The present invention will be explained in detail with reference to Examples below, but these Examples do not limit the present invention.Example/a) Production of dye Compound 7J represented by the following structural formula %Formula % Gluvil alcohol 60
−． Ethylamine (70% water m@') 7,,tjl
Stir in a phoneme air stream, ? The temperature was raised to Q°C and the mixture was reacted for 7 hours. Add 0.2 fl liter of sulfuric acid and remove 7 liters of air.
F-? It was injected at 0'O.

After cooling to room temperature, filter, add isopropyl alcohol 100%
- and dried to obtain crude crystalline gold. After dissolving in chloroform, purified product ay having the following structural formula was obtained by silica gel column chromatography.

The melting point of this product is 2/θ~-/-? '0), the thickest absorption wavelength was 64 tlnm (chloroform), and the mass spectrum was φ=29g.

b) 111m method for thermal transfer recording ink Above a) Dye obtained below -2 g Ethyl cellulose rg Total /θ09 By mixing the dye mixture of the above composition with a paint conditioner using glass beads for about 3θ minutes. The green onion was prepared.

C) Method for creating transfer sheet The above ink was applied to condenser paper (70 μm) using a gravure proofing machine (plate depth 3θ μm).

d) Method for making image receiving paper An aqueous dispersion of saturated polyester (Pyronal MD-42θθ manufactured by Toyobo Co., Ltd.)/θy and silica gel (manufactured by Nippon Silikani Gyo Co., Ltd., B11 psil)
B-2-20 and product name)/1 were mixed and a VI4 paint was coated on high quality paper (thickness 2008m) using a bar coater (RK
Manufactured by Pr1nt00at engineering natruments company/1
61) Coated using f.

θ) Transfer recording method Lay the ink-cleaned side of the transfer sheet on the paint-coated side of the image-receiving paper, and 2! Thermal transfer recording is performed using a thermal head with a heating resistor of θΩ at the density of Dadot/Ivy, and the color density θ is
. r! A cyan-colored record was obtained. At this time, a /rV (Q voltage) was applied to the thermal head for 6 milliseconds.

11- The color density was measured using a densitometer R manufactured by Macbeth Co., Ltd.
D-! /D type (filter: Wratten rot 2).

The color appeal was determined by the following formula: gi'xt.

Color-Degree" goo (Work 0/Work) Work 0: Intensity of reflected light from a standard white reflector. Work: Intensity of reflected light from a test object. A one-dimensionality test of the obtained record was carried out using a xenon fade meter (manufactured by Suga Test Instruments Co., Ltd.) (black panel temperature ≦ 3 degrees), but there was almost no discoloration after irradiation with aO waiting time, and it was The stability of the surface image under humidity was also good.

Example 2) Production of dye and preparation of ink using dye 2y shown in Table 7 in the same manner as in Example 1.

A transfer sheet and an image receiving paper were prepared and transfer recording was performed to obtain a cyan color record of each trout with the color performance shown in Table 1. All of these recordings were made using the same method as the FFIJ test, and showed almost no discoloration and excellent image stability under high temperature and high humidity conditions.

Table 7 Continuation of Table 1 1b- 16- Continuation of Table 7 Continuation of Table 7 Continuation of Table 1 19- Continuation of Table 7 20- Continuation of Table 1

Claims (1)

[Claims] (1) General formula (1) %Formula% (In the formula, R1 and P are an alkyl group, an alkenyl group, a cyclohexyl group, a halogenoalkyl group, an alkoxyalkyl group, an alkoxyalkoxyalkyl group, a hydroxyalkyl group. A hydroxyalkoxyalkyl group, hydroxy Alkylthioalkyl group, cyanoalkyl group, tetrahydrofurfuryl group, alkenyloxyalkyl group, tetrahydroq
An anthraquinone dye for thermal transfer recording represented by a furfuryloxyalkyl group, an alkoxycarbonyloxyalkyl group, an alkylcarbonyloxyalkyl group, or a haalkoxycarbonyloxyalkyl group.