JPS6028451A - Styryl-based coloring matter for heat-sensitive transfer recording - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (X is OH, cyano or chlorine; R is aryl, methyl, ethyl, propyl or butyl). EXAMPLE:3-methyl-4-(beta',beta'-dicyanovinyl)-N-(beta'-hydroxyethyl)-N -methylaniline. USE:Yellow-colored titled matter capable of sublimation; which is capable of transfer recording with adequate color concentration without heavy loading on heat-sensitive recording head because of large molecular extinction. Suitable for obtaining full-color by the combination with fuchsine and cyan coloring matters. PREPARATION:An aniline of formula II is made to react, in DMF, with phosphorus oxychloride to form an aldehyde of formula III, which is then made to react with malonitrile.

Description

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

Currently, a sublimation type thermal transfer recording method is being considered as a method for obtaining color hard copies from televisions, CRT color displays, color facsimiles, magnetic cameras, and the like. For this recording method, dyes for transfer printing of polyester fibers have been considered, but it is difficult to obtain sufficient color density with the thermal energy of a normal thermal recording head.

An object of the present invention is to provide a yellow sublimation styryl thermal transfer recording dye, and further to provide a yellow sublimation styryl thermal transfer recording dye that provides high color density. The purpose is to

That is, the present invention relates to the general formula CI) H3 (wherein, X represents a hydroxy group, a cyano group, or a chlorine atom, and R represents an allyl group, a methyl group, an ethyl group, a linear or branched propyl group, or a butyl group) The gist of this invention is a styryl-based thermal transfer recording dye represented by the following formula.

Specific examples of the color chart of the present invention include the following.

3-Methyl-cou (β', β'-dicyanovinyl-N
-(β'-hydroxyethylJ-N-methylaniline, 3-methyl-ter(β',β'-dicyanovinyl)-N
-(β'-hydroxyethyl)-N-ethylaniline, 3-methyl-cou(β',β'-dicyanovinyl)-N
-(β'-hydroxyethyl) -N -(n) propylaniline, 3-methyl-cou(β',β'-dicyanovinyl)-N
-(β'-Hydroxyethyl)v) -N -(n)Butylaniline 3-methyluda-(β',β'-dicyanovinyl)-N
-(β'-cyanoethyl, AI) -N-methylaniline, 3-methyl-cou(β-β'-dicyanovinyl)-N-
(β'-cyanoethyl)-N-ethylaniline, 3-methyl-+-(β', β'-dicyanovinyl)-N
-(β'-cyanoethyl) -N -(n)propylaniline, 3-methyl-cou(β',β'-dicyanovinyl)-3
-Methyl-ter(β-β′-dicyanovinyl)-N-(
β'-cyanoethyl) -N -(n, l butylaniline, 3-1fk-+-(β', β'-dicyanovinyl no N
-(β'-cyanoethyl)-N-(i day 0) butylaniline, 3-methyl-cou(β-β'-dicyanovinyl)-N-
(β'-chloroethyl)-N-methylaniline, 3-methyl-ter(β1β'-dicyanovinyl)-N-
(β'-chloroethyl)-N-ethylaniline.

3-Methyl-Q(β-β′-dicyanovinyl)-N-(
β'-Chloroethylb-N-(n)propylaniline, 3-methyl-ter(β1β'-dicyanovinyl)-N
(β'-chloroethyl-N-(isO)propylaniline, 3-methyl-(β',β'-dicyanovinyl-N
-(β'-chloroethyl) -N -(n)butylaniline, 3-methyl-ter(β',β'-dicyanovinyl)-N
-(β'-hydroxyethyl)-N-allylaniline, 3-methyl-ter(β',β'-dicyanovinyl)-N
-(β'-cyanoethyl)-N-allylaniline, The method for producing these dyes is the following general formula CI [] (wherein, X and R represent the same meanings as in the above general formula CI). The anilines represented by are treated with phosphorus oxychloride in N,N-dimethylformamide,
After obtaining aldehydes represented by the following general formula (where X and R have the same meanings as in the above general formula CIO),
It can be easily obtained by treating this product with malonitrile.

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 applied onto a suitable base material to create a transfer sheet, and the sheet is stacked on the recording medium.Then, the sheet is heated and pressed from the back side with a thermal recording head. In this way, the dye on the sheet is transferred onto the recording medium.

As a resin for preparing the above ink.

Any ink used in normal printing ink may be used, such as rosin-based ink,
Phenol-based, xylene-based, petroleum-based.

Oil-based resins such as vinyl, polyamide, alkyd, nitrocellulose, alkylcellulose, maleic acid, acrylic acid,
Water-based resins such as casein, shellac, and glue can be used. Also, methanol is used as a solvent for ink preparation.

Alcohols such as ethanol, propatool, butanol, cellosolves such as methylcelonelupe and ethyl cellosolve, aromatics such as benzene, toluene, and xylene, esters such as ethyl acetate and butyl acetate, acetone, methyl ethyl ketone, cyclohexanone, etc. Ketones, hydrocarbons such as ligroin, cyclohexane, and kerosene, and dimethylformamide can be used, but
When using an aqueous resin, water or a mixture of water and the above-mentioned solvents can be used.

Suitable substrates for applying the ink include thin paper such as condenser paper and glassine paper, and heat-resistant plastic films such as polyester, polyamide, and polyimide.

These base materials suitably have a thickness of about 3 to 50 μm in order to improve the efficiency of heat transfer from the thermal recording head to the dye.

Plain paper can also be used as the recording medium, but in order to improve the color development of the dye, paper should be coated or impregnated with a resin that is compatible with the dye, or laminated with a resin film. Good recording can be achieved by using a special processed paper that has been treated with acetylation.Also, films of various resins or synthetic paper made from them can also be used.

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.

The yellow dye of the present invention has much better sublimation properties than the dye for polyester fiber transfer printing described above and has a large molecular absorption coefficient, so it can produce a color that is practically sufficient without imposing a large burden on the thermal recording head. Transfer recording of density is possible. Furthermore, since the dye of the present invention has a vivid yellow color, it is suitable for obtaining full color by combining with appropriate magenta and cyan dyes. Furthermore, since the light resistance is very good, durable recording can be obtained.

EXAMPLES The present invention will be specifically explained below with reference to Examples, but these Examples are not intended to limit the present invention.

Example/1) Method for preparing ink for thermal transfer recording H3 The above dye 2 g Ethylcellulose gg Total 100ji The ink was prepared by mixing the dye mixture af/J having the above composition with a paint conditioner using glass beads for about 30 minutes. was prepared.

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

11 () How to make image receiving paper Water-reducing liquid of Sowa polyester 3 da weight (manufactured by Toyobo Co., Ltd., Pyronal MD-/, 200) 10jJ and calcium bicarbonate (Maruo Calcium Shinzo, Super/,
Left θθ)s.

Mix the water slurry left by weight and apply the prepared paint to high-quality paper (thickness, 200 μm) using a bar coater (PK Pr).
It was coated using a coater manufactured by int-Coat Instruments.

IV) Transfer recording method Lay the ink-coated surface of the transfer sheet on the paint-coated surface of the image-receiving paper and apply a heating resistor f17 dots/mm of 1.2 and 0Ω.
Thermal transfer recording was carried out using a thermal head having a density of 20, and a yellow color recording with a color density of /20 was obtained. At this time, a voltage of /7V was applied to the thermal head for 6 milliseconds.

The color density was measured using De/Sitometer RD manufactured by Macbeth Corporation in the United States.
Reflection color density was measured using -A-/4 (type (filter; Ratten Ji6da7)).

The color a degree was calculated using the following formula.

Color density = logioC O/tech] Process O: 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 record was performed using a carbon arc fade meter ( (manufactured by Suga Test Instruments Co., Ltd.) (black panel temperature 3±2°C), but there was almost no discoloration after 90 hours of irradiation.

Example 2 Using 2 g of the pigment shown in Table 1, in the same manner as in Example 1, preparation of ink, creation of transfer sheet and receiver paper,
Transfer recording was performed to obtain yellow recordings with the color densities shown in Table 1.

When a light fastness test was carried out on these records in the same manner as in Example 1 using a 1 m sample, almost no discoloration occurred.

Table 1 Comparative Example/Instead of the dye used in Example 1, color X of the following structural formula
(C process/disperse yellow St)-g was used to prepare ink, create a transfer sheet, and perform transfer recording in the same manner as in Example/, but the color density of the yellow color obtained was less than 00g. Met.

Applicant: Mitsubishi Chemical Industries, Ltd. Agent Patent Attorney Hase - 1 other person

Claims (1)

[Claims] (1) General formula [■] In formula C, or represents a hydroxy group, cyano group or chlorine atom, R represents an allyl group, methyl group, ethyl group, linear or branched propyl group or butyl group ] A styryl-based heat-sensitive transfer recording dye.