JPS6112392A - Reddish-hue thermal transfer coloring material - Google Patents

Abstract

PURPOSE:To obtain a reddish-hue thermal transfer coloring material favorable in various kinds of fastness and having a high color value and favorable thermal stability at the time of transferring, by using a coloring material of a specified formula. CONSTITUTION:A coloring material of general formula( I ), wherein X is chlorine or bromine, R<1> is lower alkyl, lower alkoxyalkyl, allyloxyalkyl, tetrahydrofurfuryl or cyanoalkyl R<2> is lower alkyl, lower alkoxyalkyl, allyloxyalkyl, tetrahydrofurfuryl, cyanoalkyl or hydrogen, and R<3> is methyl or ethyl, is used. In a method of using the coloring material for thermal transfer type recording, the coloring material is finely dispersed or dissolved in a liquid, the resultant liquid is applied to a thin base to produce a color sheet, and by using the sheet, images are transfer recorded on a printing paper by a thermal head.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to compounds of the general formula (I) [wherein, R represents a lower alkyl group, a lower alkoxyalkyl group, an allyloxyalkyl group, a tetrahydrofurfuryl group, a cyanoalkyl group, or a hydrogen atom, and R represents a methyl group or Representing an ethyl group] This invention relates to a red coloring material for thermal transfer.

The red coloring material for thermal transfer according to the present invention is applied to a transfer printing method for synthetic fibers [References K, ``Th by NKATARAMAN''
e Chemistry of 5yntheticl
) yesf Volume 1, page 191], or the transfer type thermal recording method, which is a means of recording information [References 6 Nikkei Electronics, February 13, 1984 issue, 11 Journal of the Institute of Electronics, Volume 12, No. 1, page 18; It is a red coloring material that is useful as a coloring material used in "6 Television Society Journal" Vol. 37, No. 7, p. This is clear.

BACKGROUND ART Conventional red dyes for transfer printing include anthraquinone dyes represented by formula (2) [References: Azo dyes represented by Extra Large (3)] [References: JP-A-Sho et al. Moreover, among the red coloring materials for transfer type heat-sensitive recording, there is no one that is excellent in various fastnesses including transferability and light fastness.

The problem to be solved by the invention is that when using a two-red coloring material in a transfer type recording system, the important quality is the storage stability of the record, that is, the fastness to sunlight, the ease with which it can be removed by masatsu, etc. In addition to thermal stability during transfer, color value and thermal stability during transfer are important, but no coloring materials to date have been well-balanced.

Means for Solving the Problems In order to solve the above problems, the inventors of the present invention have conducted intensive studies and found that the coloring material represented by the general formula (I) has good fastness of various types, high color value, and is suitable for transfer during transfer. has good thermal stability,
In addition, it was discovered that it has the necessary properties as a coloring material for transfer dry heat recording, and the present invention was achieved.

Transfer methods are known, for example, from FR 1 223 330 and DE 1769 757; dye preparations and auxiliary carriers for this are known from DE 1771 813 and DE 1771 812. The coloring material of formula (I) according to the present invention can be used for transfer printing by a known method.

In addition, the method of using the coloring material of the present invention in thermal transfer recording involves finely dispersing or dissolving the coloring material, applying it to a thin base material, using a color sheet, and transferring it to print paper using a thermal head to create an image. .

In the coloring material represented by the general formula (I) of the present invention, examples of the lower alkyl group represented by R and R include a methyl group, an ethyl group, a propyl group, a butyl group, and a lower alkoxyalkyl group. Examples of the group include methoxyethyl group, ethoxyethyl group, propoxyethyl group, butoxyethyl group, etc. Examples of the allyloxyalkyl group include allyloxyethyl group, and examples of the cyanoalkyl group include cyanogen. Examples include a methyl group and a 7-ethyl group.

Examples will be shown below, in which "part" and "chi" mean weight.

[Example-1] Printing on paper by flexographic printing method using a colorant consisting of 10 parts of a coloring material of the following formula, 5 parts of ethyl cellulose, 70 parts of ethyl alcohol, 20 parts of ethyl acetate, and 5 parts of ethyl glycol, and then printing. Dry. The printed side of the paper is placed on a polyester knitted fabric and these are passed together through a calendar at 200°C for 30 seconds. At this time, the dye migrated onto the knitted fabric, resulting in a red print on a white background. This dyed fabric has a light fastness level of 6-7 (according to rIS, LO842-1971. The same method applies to the following examples), a sublimation fastness level of 3 (based on Sumitex Resin UN-1 (product of Sumitomo Chemical Co., Ltd.)). After processing, JIS, LO879-1975 (180℃
Measured by contamination of Tetron cloth tested by 30 seconds).

), water fastness grade 4 (JIS, LO846 after resin processing with Sumitex Resin UN-1 (product of Sumitomo Chemical Co., Ltd.)
-1976 (Method B 16 hours), the contamination of nylon cloth was measured. ), washing fastness was grade 4-5 (contamination of nylon cloth was measured by testing by AATCCIrA method after resin processing with Sumitex Resin UN-1 (product of Sumitomo Chemical Co., Ltd.)).

The coloring material of the above formula is 2-amino-5-bromo-1°3.4
- 18 parts of thiadiazole at 0°C with 160 parts of glacial acetic acid, 8
It was added to a mixed solution of 80 parts of 9% phosphoric acid and 130 parts of 13% nitrosyl sulfuric acid, and diazotization reaction was carried out at 0° C. for 2 hours. Subsequently, 294 parts of 3-CN, N-di(ethoxyethyl)aminocoacetanilide was dissolved in the acidic solution and added at 0°C. It was obtained by adjusting the pH to 5 with caustic soda, filtering, washing with water, and drying. Maximum loading of this dye (in acetone) was 516 nm.

[Example-2] 5 parts of coloring material of the following formula, 20 parts of styrene polymer, and 8 parts of dolol
A colorant consisting of 0 parts is used to print on paper using the copper gravure printing process and the print is dried. The paper print pattern was then transferred onto the polyacrylonitrile fabric at 190'C for 25 seconds in the same manner as in Example 1, resulting in a red print on a white background.

The coloring material of the above formula was synthesized in the same manner as in Example-1.

λmaX (in acetone) 508 nm.

[Example-3] 20 parts of dye of the following formula, 380 parts of water, 400 parts of 10% locust powder ether thickener, and 20 parts of 10% starch ether thickener
The paper is printed using a single roll film printing process using 0 parts of color material and the print is dried. Next, Example-1
The paper print pattern was transferred onto a polyester fabric at 210° C. for 30 seconds in a manner similar to the method of 210° C., resulting in a red print on a white background.

The coloring material of the above formula was synthesized in the same manner as in Example-1. λ
maX (in acetone) = 518 nm.

[Example-4] 10 parts of a coloring material of the following formula, and a composition of 40 parts of colophonium resin modified with phenol, 20 parts of vegetable drying oil, 10 parts of long-oil alkyd resin, 25 parts of mineral oil, 10 parts of Aerosil, and cobalt-based A coloring material consisting of 90 parts of varnish with 2 parts of desiccant is used to print the desired 75 turns on the transfer paper by offset printing. The printed side of the dried print was placed on a polyacrylonitrile fabric and processed on a sheet-fed press for 25 seconds at 205°C to yield a red-on-white pudding 1- with lightfastness and wetfastness. Ta.

The coloring material of the above formula was synthesized in the same manner as in Example-1. λm
ax (in acetone) = 523 nm.

[Example-5] Using 10 parts of a coloring material of the following formula and 90 parts of a varnish whose composition is 10 parts of ethyl cellulose, 75 parts of ethyl alcohol, 20 parts of ethyl acetate, and 5 parts of ethyl glycol,
Print on paper using the intaglio printing method. Place the printed side of the dried print on the polyester fabric and place them together for 20 minutes.
Calendar for 30 seconds at 0°C. At this time, the colorant migrated onto the polyester fabric, resulting in a red print on a white background that was fast to light and fast to washing.

The coloring material of the above formula was obtained in the same manner as in Example-1. λm
ax (in acetone) = 520 nm.

[Example-6] Printing was carried out on paper by a rotary film printing method using a coloring material consisting of 20 parts of a coloring material of the following formula, 280 parts of water, and 700 parts of an 8% locust bean powder ether thickener. dry. The paper print pattern was then transferred onto the polyester fabric at 210° C. for 20 seconds as in Example 2, resulting in a red-on-white print with wet fastness.

[Example 7] A red color sheet was prepared by applying a coloring material of the following formula to paper, and a clear image was obtained when an image was created using a printer.

Claims (1)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^2 represents a lower alkyl group, a lower alkoxyalkyl group, an allyloxyalkyl group, a tetrahydrofurfuryl group, a cyanoalkyl group, or a hydrogen atom, and R represents a methyl group or an ethyl group. ] A red coloring material for thermal transfer indicated by .