JPS6157651A - Indoaniline compound and dyestuff for heat-sensitive transfer recording - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula {X is H, (F-substituted) alkyl, alkoxy, formylamino, (F-substituted)alkylcarbonylamino, arylcarbinylamino, or halogen; Y is H, (F-substituted)1-8C alkyl; R<3> and R<4> are group shown by the formula II-VI [R<5> is (substituted)1-8C alkyl]}. EXAMPLE:A compound shown by the formula VII. USE:A dyestuff for heat-sensitive transfer recording of sublimation type. PREPARATION:For example, a phenol shown by the formula VIII and an aniline shown by the formula IX are treated with an oxidizing agent such as silver nitrate, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION OBJECT OF THE INVENTION A] Industrial Field of Application The present invention relates to a novel indoaniline compound and a dye used in dye sublimation heat-sensitive transfer recording.

(Example) Conventional technology In the past, there was a demand for T-color recording technology such as facsimile printers, copying machines, and television screens, and electrophotography,
Color recording technologies using inkjet, thermal transfer, etc. are being considered.

- The thermal transfer recording method is considered advantageous over other methods because the equipment is easy to maintain and operate, and the equipment and consumables are inexpensive.

The thermal transfer method uses a transfer sheet t in which a heat-melting ink layer is formed on a base film.

A melting method in which a thermal head heats the cutting edge to melt the ink and transfer it onto a recording medium.

There is a transfer sheet t in which an ink layer containing a sublimable dye is formed on a base film, and a sublimation method uses a heat-sensitive head to heat the dye to sublimate it and transfer it to the recording medium. By changing the energy χ applied to the head, the dye sublimation transfer i' can be controlled, which facilitates one-gradation recording, which is considered to be particularly advantageous for full-color recording.

Pano Problems to be Solved by the Invention The following conditions must be met for the dye to be applied to this recording method.

That is, it sublimates easily under the operating conditions of the thermal recording head,
What is the preferred hue for reproducing one color without thermal decomposition under the operating conditions of a thermal recording head? I have it.

It has a large molecular extinction coefficient, is stable against heat, dust, moisture, chemicals, etc., and is easy to synthesize.

It also has excellent suitability for ink production.

2) Object of the invention The object of the invention is to provide a cyan dye that satisfies the above conditions.

Structure of the Invention (a) Means for Solving Problems (1) The present invention solves the problems by solving the following problems: R1 and R1 is a hydrogen atom, C1~
represents a substituted or unsubstituted alkyl group, and R3 and R4 represent a substituted or unsubstituted alkyl group of 01 to B] and a dye for thermal transfer distribution. This is the summary.

Indian anidine represented by the general formula CI) of the present invention
1 In phosphorus compounds and dyes for thermal transfer printing, p
Examples of the substituent for the substituted argyl group for i and R6 include a halogen atom, an alkoxy group, a vinyl group, a human aq group, and an allyl group.

As for the manufacturability of the compounds and dyes of the present invention, for example, phenols represented by the following general formula CII) (wherein, R3 and R4 are the same as defined above) and the following general formula (wherein, X, Y, R1 and R2 are the same as defined above.

In the general formula [I] of the Indian compound and thermal transfer dye of the present invention, 4? Preferably, X and Y are a hydrogen atom, a methyl group, a methoxy group,
Indicates an ethoxy group, a chlorine atom, a bromine atom, or a trifluoromethyl group, R1 and an ice atom, and a human O-? Al group in sial, aralkyl group or O, ka alkyl group C1,4
Compounds and dyes represented by an alkyl group or a halogenated alkyl group may be mentioned.

When applying the compound (dye) of the present invention to a non-recording method,
It is necessary to prepare an ink by dissolving or dispersing the chemical compound in the form of fine particles in a medium together with a binder, apply the ink onto a base film, dry it, and explode the transfer sheet.

Binders for ink preparation include water-soluble resins such as cellulose, acrylic acid, and starch, acrylic resins, and methacrylic resins.

Examples include resins soluble in the organic solvent, such as polystyrene, polycarbonate, polysulfone, polyethersulfone, and ethyl cellulose. In the case of organic solvent-soluble resins, it is possible to use them not only as organic solvent solutions but also in the form of aqueous dispersions.

Besides water as a medium for ink preparation.

Methyl alcohol, isopropyl alcohol.

Alcohols such as isobutyl alcohol.

Cellosolves such as methyl cellosolve and ethyl cellosolve, aromatics such as toluene, xylene and lyalopenzene, esters such as ethyl acetate and butyl acetate, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexano 7, chloride Salt-based solvents such as methylene, chloroform, trichloroethylene, tetrahydrofuran, dioxane are ether%i, N, N
- Organic solvents such as dimethylformamide and N-methylpyrrolidone can be mentioned.

+E Photography sheet θ) As a base film for applying ink, Capacitor i.

Thin paper like glassine paper, polyester.

Films made of plastics with good sagging resistance, such as polyamide or polyimide, are suitable.

Their thickness can range from 3 to 0 μm.

How to apply the coating to the base film and how to apply it using the Shiteha, reverse roll coater, gravure coater, rod coater, or airtocco. 1 type ゛'').

Functions and Effects of the Invention Since the dye has a clear cyan color, it is suitable for obtaining a full-color record with good color reproducibility by combining it with appropriate magenta and yellow colors, and is easy to sublimate ( Because of its large molecular extinction coefficient, it is possible to obtain high-speed recording with high color density without placing a large burden on the thermal head.Furthermore, it is stable against heat, light, moisture, chemicals, etc., so it can be used during transfer recording. to be pyrolyzed into .

(The storage stability of the obtained records is also excellent.Also, since the dye of the present invention has good solubility in organic solvents and good dispersibility in water, it is possible to prepare a highly concentrated ink that is uniformly dissolved or dispersed.) By using these inks, it is possible to obtain a transfer sheet coated with one dye uniformly and at a high concentration. Therefore, by using these transfer sheets, it is possible to obtain good uniformity and color density. You can get record heat.

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! a) Production of dyes λ, 3- and Suacetoidophenol u,/fl represented by the following structural formula and an adduct represented by the following structural formula! , Jf/ to ethanol 300m/
Y 71 [1st, stirred at room temperature, then silver nitrate, y
, ttg was added dropwise to the aqueous solution g,' dissolved in 13 ml of hot water. Float 15 ml of 21% ammonia water, add dropwise silver nitrate and aqueous solution g dissolved in rgyl water to ml, and react at 3Q~aO℃ for 3 hours. After the reaction is complete, extract with chloroform and remove with 9 mortar. After that, column purification was performed using chloroform to obtain a purified product of indoaniline dye represented by the following structural formula.
I got 7g. The mass spectrum of the above dye is m/e = J At, and the maximum absorption wavelength is &, ? 4! nm (chloroform).

b) Preparation of ink N3 (jtJL; ajl Above dye log Polysulfone resin * t09 Chlorobenzene Zaof! Total ioog * Manufactured by Nissan Chemical Industries, Ltd., Needel P-1700
C Product name) Treat the mixture with the above composition with paint conditioner for 70 minutes to condition the ink! ! I did it. The pigment and resin were completely dissolved, and a uniform solution of the ink could be obtained.

C) Preparation of transfer sheet The above ink χ bar coater (RK Pr1ntcoa
After applying it on a polyimide film (/μm thick) using F5/JY manufactured by T-Natruments,
Air dry and transfer sheet? Obtained.

d) Transfer recording The ink-applied surface of the above transfer sheet was placed on the recording medium and recorded using a thermal head under the following conditions, with a clear cyan color i, 3.
It was possible to obtain a record of uniform high color density of o.

Recording conditions Main scanning and sub-scanning linear density: 4t dots/recording power
: (7.4 W/dotted head heating time: 10 maθC) The recording medium is a saturated polyester, an aqueous dispersion of 74 (manufactured by Toyobo Co., Ltd.).

Vyloner) v MD-1200, trade name) 101 and silica (manufactured by Nippon Silikani Gyo Co., Ltd.).

Was it prepared by mixing N1psil F222oA, trade name)/g'? Bar coater (RK Pint Coat Inatrume) on high quality paper (OQμm thickness) on W'
Manufactured by nts.

A3) 'r: Manufactured by applying and drying.

Color density is measured using a densitometer HD, co-produced by Macbeth Co., Ltd.
-J/Q type (filter: ratten flat)? It was measured using

The originality test of the obtained records was carried out using a carbon arc fade meter (manufactured by Suga Test Instruments Co., Ltd.) (black panel temperature: y- to ℃), but after 40 hours of irradiation, the color almost changed and faded. I didn't. Also, the transfer sheet and recording are heated.

It was stable against moisture and had excellent storage stability in the dark. ◎ Example Co. Ink was prepared in the same manner as in Example 1 using the pigments shown in Table 1 instead of the pigments used in Example 1. As a result of preparing the transfer sheet and performing the transfer recording, it was possible to obtain a clear cyan color distribution with the color density shown in Table 1.

The results of the light fastness test of the obtained record and the dark storage stability test of the transfer sheet/record were good.

Claims (4)

[Claims] (1) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼......[I] (In the formula, X is a hydrogen atom, an alkyl group optionally substituted with a fluorine atom, an alkoxy group, formyl represents an amino group, an alkylcarbonylamino group optionally substituted with a fluorine atom, an arylcarbonylamino group, or a halogen atom, and Y is a hydrogen atom, an alkyl group optionally substituted with a fluorine atom, an alkoxy group, or a halogen Represents an atom, R^1 and R^2 are hydrogen atoms, C
_1_-_8 represents a substituted or unsubstituted alkyl group, and R^3 and R^4 are ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas,
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
and R^5 and R^6 represent substituted or unsubstituted alkyl groups of C_1_-_8). (2) In the indoaniline compound according to claim 1, X and Y represent a hydrogen atom, a methyl group, a methoxy group, an ethoxy group, a chlorine atom, a bromine atom, or a trifluoromethyl group, and R^1 and R^2 is a hydrogen atom,
Hydroxyalkyl group, aralkyl group or C_1_～_
6 alkyl group, R^3 and R^4 are ▲ formula,
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R^5 and R^6 are C_
A compound represented by an alkyl group or a halogenated alkyl group of 1_ to_4. (3) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼......[I] (In the formula, X is a hydrogen atom, an alkyl group optionally substituted with a fluorine atom, an alkoxy group, formyl represents an amino group, an alkylcarbonylamino group optionally substituted with a fluorine atom, an arylcarbonylamino group, or a halogen atom, and Y is a hydrogen atom, an alkyl group optionally substituted with a fluorine atom, an alkoxy group, or a halogen Represents an atom, R^1 and R^2 are hydrogen atoms, C
_1_-_8 represents a substituted or unsubstituted alkyl group, and R^3 and R^4 are ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas,
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
and R^5 and R^6 represent substituted or unsubstituted alkyl groups of C_1_-_8). (4) In the dye for thermal transfer recording according to claim 3, X and Y represent a hydrogen atom, a methyl group, a methoxy group, an ethoxy group, a chlorine atom, a bromine atom, or a trifluoromethyl group, and R^ 1 and R^2 represent a hydrogen atom, a hydroxyalkyl group, an aralkyl group, or an alkyl group of C_1_-_6, and R^3 and R^4 have ▲a mathematical formula, a chemical formula, a table, etc.▼, ▲a mathematical formula, a chemical formula, a table, etc. There are ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas , chemical formula, table, etc. ▼ or ▲ Numerical formula, chemical formula, table, etc. available ▼, and R^5 and R^6 are C_1_-_4 alkyl groups or halogenated alkyl groups.