JPS6028453A - Styryl compound and coloring matter for heat-sensitive transfer recording comprising the same - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (R and R' are each aryl, methyl, ethyl, propyl, or butyl). EXAMPLE:3-chloro-4-(beta',beta'-dicyanovinyl)-N,N-dimethylaniline. USE:Yellow colored titled matter capable of sublimation; which is capable of transfer recording of 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 novel styryl compound and a dye for thermal transfer recording using the same.

Currently, a sublimation type thermal transfer recording method is being considered as a method for obtaining color hard copies from televisions, ORT 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.

The object of the present invention is to provide a novel styryl compound and a dye for yellow sublimation type heat-sensitive transfer recording using the same. The purpose of this invention is to provide a recording dye.

That is, the present invention provides the general formula C.L. (In the formula, R and R' are an allyl group or a methyl group.

The gist of the invention is a styryl compound represented by an ethyl group, a linear or branched propyl group, or a butyl group, and a dye for thermal transfer recording using the styryl compound.

Specific examples of the styryl compound (dye) of the present invention include the following.

3-chloro-cou(β',β'-dicyanovinyl)Bl
, N-dimethylaniline.

3-chloro-ter(β',β'-dicyanovinyl)N,
N-diethylaniline.

3-chloro-cou(β',β'-dicyanovinyl)-N
, N-di0propylaniline.

3-chloro-cou(β',β'-dicyanovinyl)-N
, N-di(ieo)propylaniline.

3-chloro-cou(β',β'-dicyanovinyl)N,
N-di(n)butylaniline, 3-chloro-cou(β',β'-dicyanovinyl)N
, N-di(iso)butylaniline,! -po
o -47-(βl, β'-dicyanovinyl)-N-methyl-N-ditylaniline.

3-chloro-cou(β',β'-dicyanovinyl)-N
-Methyl-N = (n) Furopylaniline, 3-chloro-ter(β',β'-dicyanovinyl)-N-methyl-N-(ro)butylaniline, 3-chloroo-41-(
β′, β′-dicyanovinyl)-N −x chill-y
-(n) 7'ropylaniline, 3-chloro-cou (β
', β'-dicyanovinyl)-N-ethyl-N -(n
) Butylaniline.

3-chloro-cou(β',β'-dicyanovinyl)-N
-Allyl-N-methylaniline.

3-chloro-gu(β',β'-dicyanovinyl)-N
-Allyl-N-ethylaniline, 3-chloro-cou(β',β'-dicyanovinyl)-N
-Allyl-N-(n)-propylaniline, 3-chloro-cou(β',β'-dicyanovinyl)-N-allyl-
N-(iso)-propylaniline, 3-chloro(β),β'-dicyanovinyl)7-N-arylN-(n)-butylaniline.

3-Chloro-ter(βl, β'-dicyanovinyl)-N
-Allyl-N-(iso)-butylaniline, these compounds (dyes) of the present invention can be produced by the following general formula (wherein R and R' have the same meanings as in the above general formula (I)). The anilines represented by the formula (I) are treated with phosphorus oxychloride in N,N-dimethylformamide to give the following formula (wherein R and R' have the same meanings as in the general formula (I)): After obtaining aldehydes,
It can be easily obtained by reacting this product with malonitrile.

A method for producing a thermal transfer recording ink using a styryl compound (dye) of the present invention is as follows.

The recording ink may be prepared by mixing the pigment with a suitable resin, solvent, water, etc. In addition, as for the thermal transfer method, the ink obtained above is applied onto a suitable base material to create a transfer sheet, the sheet is overlapped with the recording medium, and then a thermal recording head is applied from the back surface of the sheet. A method of heating and pressurizing can be mentioned, and in this way, the dye on the sheet is transferred onto the recording medium.

The resin 7 for preparing the above ink may be those used in ordinary printing inks, such as rosin-based, phenol-based, xylene-based, petroleum-based, vinyl-based, polyamide-based, alkyd-based, and nitrocellulose-based. , alkylcellulose, oil-based resins such as alkylcellulose, maleic acid-based, acrylic acid-based, casein, shellac,
Water-based resins such as glue can be used. or.

Methanol as a solvent for ink preparation.

Alcohols such as ethanol, globanol, and butanol; cellosolders such as methyl cellosolve and ethyl cellotrufuna; aromatics such as benzene, toluene, and xylene; esters such as ethyl acetate and butyl acetate; and ketones such as acetone, methyl ethyl ketone, and cyclohexanone. Hydrocarbons such as ligroin, cyclohexane, kerosene, dimethylformamide, etc. can be used.
When using an aqueous resin, water or a mixture of water and the above-mentioned solvents can be used.

Suitable substrates for applying ink include thin paper such as condenser paper and glassine paper, and films made of plastics with good heat resistance such as polyester, polyamide, and polyimide. To improve heat transfer efficiency to the pigment! A thickness of approximately lθμm is appropriate.

Also, 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 has good compatibility with the dye. Good recording can be achieved by using film linings or special processed paper treated with acetylation. 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.

The styryl compound (yellow color) of the present invention has much better sublimation properties than the above-mentioned dye for polyester fiber transfer printing, and has a large molecular absorption coefficient V, so it does not place a large burden on the 5M & thermal recording head. Transfer recording with practically sufficient color density is possible. Furthermore, since the compound (dye) of the present invention has a vivid yellow color, it is suitable for obtaining full color by combining with iM-like magenta and cyan dyes. Furthermore, since the light resistance is very good, durable recording can be obtained.

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

Example/1) Production of styryl compound (dye) 3-chloro-Z-formyl-N,N-diethylaniline, 2/, 2f was charged into Impropanol 10θ, and malonitrile 72 After adding, piperidine θ,! -7 and reacted under reflux for 7 hours. After cooling to room temperature, the precipitated yellow crystals were treated with P, washed with methanol and water, and dried to produce a styryl compound (dye) with the following structural formula: /? I got 2.

L This material has a melting point of /-2j~/kt°C and m/θ=2. Parent ion peaks were shown at g/ and 2!2. In addition, the visible absorption spectrum in chloroform showed a maximum absorption value of θ nm K.

■) How to break down ink for thermal transfer recording Ethyl cellulose J'? The ink was prepared by mixing the pigment mixture having the above composition with a paint conditioner using glass beads for about 3θ minutes.

111) Method for creating transfer sheet The above ink was applied to condenser paper (10 μm) using a gravure proofing machine (plate depth 3θ μm).

lv) Method for making receiver paper Aqueous dispersion of saturated polyester j4 (Pyronal MD-/, 5oo, manufactured by Toyobo Co., Ltd.)/θ2 and calcium bicarbonate (Super/, manufactured by Maruo Calcium Co., Ltd.)
! θθ)! O weight 9 water slurry! θ2 and the prepared paint was coated on high-quality paper (thickness, 200 μm) using a bar coater (RK Pr1nt-Coat instruments).
It was coated using a commercially available MA-t.

■) Transfer recording method The ink-dispersed side of the transfer sheet is placed on the paint-applied side of the image-receiving paper, and a thermal head having a 230Ω heating resistor at a density of Z dots/square is used to perform thermal transfer recording in one color. A yellow color record of density/2θ was obtained. At this time, a voltage of /jV was applied to the thermal head for 6 milliseconds.

The color density was measured using a densitometer RD manufactured by Macbeth Corporation in the United States.
-674 was measured using a mold (filter m: Utsuten Ap7).

Color density was calculated using the following formula.

Color density -'Og+o (work 0/work) work. Intensity of reflected light from two standard white reflectors: Intensity of reflected light from test objects In addition, the light fastness test of the obtained records was performed using a carbon arc fade meter (manufactured by Suga Test Instruments Co., Ltd.). (black panel temperature: 63±Jtl), but there was almost no discoloration after 70 hours of irradiation.

Example λ Using dye 22 shown in Table 1, ink was prepared, a transfer sheet and image receiving paper were prepared, and transfer recording was carried out in the same manner as in Example. - Obtained a color record. All of these records showed almost no discoloration when tested for light resistance in the same manner as in Examples.

In place of this, the following structural formula dye (A/Disperse Yellow! Da) 22 was used to prepare ink, create a transfer sheet, and perform transfer recording in the same manner as in Example/. The obtained color value of yellow is θ,! It was below.

Sender: Mitsubishi Chemical Industries, Ltd. Representative Patent Attorney Hase - Others/names

Claims (2)

[Claims] (1) A styryl compound represented by the general formula (wherein R and R' represent an allyl group or a methyl group, an ethyl group, a linear or branched propyl group, or a butyl group). (2) Dye for thermal transfer recording represented by the general formula (wherein R and R' represent an allyl group, a methyl group, an ethyl group, a linear or branched propyl group, or a butyl group) .