JPS60172591A - Anthraquinone dye for thermal transfer recording - Google Patents

Abstract

PURPOSE:To attain cyan recording affording an image having excellent light fastness and stability under a high temp. and high humidity condition, by using a specific anthraquinone dye for thermal transfer recording. CONSTITUTION:Cyan transfer recording affording an image excellent in stability under a high temp. and high humidity condition can be performed by using an anthraquinone dye for thermal transfer recording, represented by the general formula [ I ] (wherein R<1> and R<2> are each an alkyl, an alkenyl, a cyclohexyl, a halogenoalkyl, an alkoxyalkyl, an alkoxyalkoxyalkyl, a hydroxylalkyl, a hydroxylalkoxyalkyl, a hydroxyalkylthioalkyl, a cyanoalkyl, a tetrahydrofurfuryl, an alkenyloxyalkyl, a tetrahydrofurfurlyoxyalkyl, an alkoxycarbonylalkyl, an alkylcarbonyloxyalkyl, or an alkoxycarbonyloxyalkyl group).

Description

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

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

In this method, a transfer sheet coated with a sublimable dye is heated by a thermal recording head, and the dye is sublimated and transferred to the recording medium to obtain color recording, but the energy applied to the thermal head must be adjusted to A. 2) Since the amount of coloring matter can be controlled, it is easy to express gradation, and compared to other recording methods, it is particularly advantageous in obtaining full-color hard copies.

By the way, the dyes used in this [i[] recording method are:
The following conditions need to be met.

■ Af'v #Easy to sublimate under the operating conditions of the 1d recording head.

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

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

■ The molecular absorption tV1 number is large.

■ Stable against moisture, chemicals, etc. 2 things.

■ Easy to synthesize.

The object of the present invention is to provide a cyan dye that satisfies (1), (2), (2), and (2) among the necessary conditions for a dye used in the above-mentioned heat-sensitive recording method.

That is, the present invention is based on the general formula [1] (wherein R1 and R2 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, a hydroxy Alkylthioalkyl group, cyanoalkyl group, tetrahydrofurfuryl group, alkenyloxyalkyl group,
The gist thereof is an anthraquino/photothermographic transfer recording dye represented by a tetrahydrofurfuryloxyalkyl group, an alkoxycarbonylalkyl group, an alkylcarbonyloxyalkyl group, or an alkoxycarbonyloxyalkyl group.

R1 and R2 represented by the above general formula [1] include a methyl group, an ethyl group, an n-propyl group, a 1-propyl group,
n-butyl group, 1-butyl group, n-pentyl M% n-
Alkyl groups such as hexyl group, n-7'' thyl group, n-octyl group, -1ethylhexyl group, allyl group, comethylallyl group, -1chloroallyl group, copromoallyl group, crotyl group, 3-phenylallyl group Alkenyl groups such as groups; cyclohexyl groups; alkoxyalkyl groups such as methoxyethyl groups, ethoxyethyl groups, propoxyethyl groups, methoxyethyl groups, r-methoxybutyl groups: methoxyethoxyethyl groups, ethoxyethoxy nibble crystals, globoxycetyl groups; Alkoxyalkoxyalkyl-Mi such as toxyether group; hydroxyethyl group, I-hydroxypropyl group, I-hydroxybutyl) hydroxyalkyl of k71: chloroethyl/l/-jISi, chloroglovir group, furfuryl group, iodoether M 6 ( 7)”
Lognoalkyl crystal nitrogen methyl thread, cyanoethyl ha,
cyano 7''robyl group, etc.; tetrahydrofurfuryl group: 1-rukenyloxyalkyl group, such as allyloxyether group, 2-methelallyloxyenal, 15; methoxycarbonylethyl group, ethoxycarbonylethyl group , alkoxycarbonylalkyl groups such as propoxycarbonyl ether group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group: acetoxyether group,
Alkylcarbonyloxyalkyl groups such as propionyloxyether group, I-acetoxypropyl group, I-7cetoxybuter group; methoxycarbonyloxyethyl group,
1-rukoxycarbonyloxyalkyl groups such as ethoxycarbonyloxyethyl groups; tetrahydrofurfuryloxyalkyl groups such as tetrahydrofurfuryloxyethyl groups; hydroxyalkoxyalkyl groups such as hydroxyethoxyethyl and hydroxypropoxyethyl groups; Examples include hydroxyalkylthioalkyl groups such as /I/ group.

Particularly preferred R1 and R2 are Q, ~, alkyl group, r-methoxybutyl group, chloroethyl group, methoxyethyl group, methoxyethoxyethyl group, cyanoethyl group,
Examples include a tetrahydrofurfuryl group, a cyclohexyl group, an allyloxyethyl group, a tetrahydrofurfuryloxyethyl group, a hydroxyethyl group, an allyl group, a methoxycarbonylethyl group, a hydroxyethoxyethyl group, and the like.

As a method for producing a thermal transfer recording ink using the dye of the present invention, the dye may be mixed with a suitable resin, solvent, water, etc. to prepare the recording ink. In addition, as a thermal transfer method, the ink obtained above is coated on a given base I to create a transfer sheet, the sheet is overlapped with a recording medium, and then a thermal recording head is applied from the back side of the sheet to create a transfer sheet. In this method, the dye on the sheet is transferred onto the recording medium. Oil-based threads such as rosin threads, phenolic threads, xylene threads, petroleum threads, polysulfone threads, vinyl threads, polyamide threads, alkyd threads, nitrocellulose threads, and alkylcellulose alkylcephaloses may be used. or aqueous 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, propatool, butanol, cellosolves such as methyl cellosolve and ethyl seron rupunato,
Aromatics and compounds such as benzene, toluene, and xylene, esters such as ethyl acetate and butyl acetate, ketones such as acetone, methyl ether ketone, cyclohexane and Y-linone, hydrocarbons such as ligroin, cyclohexane, and kerosene, dimethyl formamide When using water-based Itoki Jjff, water or a mixture of water and the above-mentioned solvents can be used.

As a base for expanding the ink, condenser paper,
Stained M paper such as glassine paper, and thermally transparent films such as polyester, polyamide, and polyimide are suitable, but the substrates of Tl et al. j-Δ01l to improve the line
The thickness is approximately rn.

As the recording medium, suitable paper may be used, 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;
In addition, in some cases, it is possible to add acidic particles such as B') gel, or to use a laminated resin film or special processed paper that has been acetylated. And, ``good recording with excellent stability under both high temperature and high humidity conditions is possible. or.

It is also possible to use films of various resins or synthetic papers made from them.

Furthermore, by thermally 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.

Since the dye of the present invention has a clear cyan color, it is suitable for obtaining a full color when combined with, for example, a yellow pigment represented by the following structural formula and a magenta color pigment represented by the following structural formula.

The present invention will be specifically explained below based on the implementation example, but the actual implementation is not intended to limit the present IIA invention.

Examples/a) Production of dye Compound λ, 74tp, Methylcellosolve! represented by the following structural formula.
m11 etelamine (70% aqueous g)/, tg/
J/ and sodium hydrogen carbonate, 2.2/J under reflux in a nitrogen stream! Stir for hours.

Then stop introducing the hard base and add pyridine N-oxy)'
2. f 9 g was added and stirred under reflux for 75 hours.

Up to room temperature? After cooling, methanol/θame was added and p
Filtered, washed with water and dried.

Dissolved in chloroform is a silica gel column (f)
fJfi: Chloroform), 4'f of the following Seizo formula
t products/, , fl were obtained.

The melting point of Motoichi was 22.2-224t°C, the thickest absorption wavelength was 2 nm (chloroform), and the mass spectrum was rn//e = 3.26.

b) Preparation method of ink for thermal transfer sphere distribution Pigment obtained in the above item a) 2 g Ethyl cellulose The ink was prepared.

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

d) Method for making image-receiving paper Aqueous dispersion of No. 11 polyester 3 da weight (Pyronal MD-4-〇〇 manufactured by Toyobo Co., Ltd.) / Ol and silica gel (N1 psi manufactured by Nippon Silkani Industry Co., Ltd.)
A bar coater (RK
Pr1nt Coat engineering nstrumθnts company 7
F6t).

Transfer recording method Lay the ink-coated surface of the transfer/- sheet on the paint-coated surface of the receiver paper and place a 260Ω heating resistor on the Z dot/I+III.
Using a thermal head with a + density, all thermal transfer recording was performed with a color density of 0. ? ! A cyan-colored record was obtained. At this time, a voltage of iFv was applied to the thermal head for 6 milliseconds.

The color density was measured using a densitometer R manufactured by Macbeth Co., Ltd. in the United States.
It was measured using a Dj/g type (filter: Ratten, tc-23).

The chromatic a degree was calculated according to the following formula.

Color density =, tog+o (0/t) where: intensity of reflection y0 from standard white reflector plate: strength of reflected light from test object. A fade meter (manufactured by Suga Test Instruments Co., Ltd.) was used at a black panel temperature of 3±λ℃.

Example 2 2g of the dye shown in Table 1 was ejected, and the same methods as in Example 1 were used to produce the dye, prepare the ink, create a transfer sheet and receiver paper, and perform transfer recording. Color 0 shown in
A record of cyan color was obtained. All of these records showed almost no discoloration when tested for +ruJ originality in the same manner as in Examples, and had excellent image stability under high width and high humidity conditions.

Chapter/Table (Continued from Table 1) (Continuation of Table 7) (ri!, continued from 'shito) (1st y-, Norizuki) (Continued from Table 1) (Continued from Table 1) : (Continuation of Table 1) (Continuation of Table 7) (Continuation of Table 1)

Claims (1)

[Claims] (1) General formula [1] (wherein R1 and R2 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, a hydroxyalkylthioalkyl group) , cyanoalkyl group, tetrahydrogen: anthraquinone represented by rofururyl group, alknyloxyalkyl group, tetrahydrofurfuryloxyalkyl group, alkoxycarbonylalkyl group, alkylcarbonyloxyabutyl group or alkoxy7carbonyloxyalkyl group) Dye for thermal transfer recording.