JPH051151B2 - - Google Patents

Description

[Detailed Description of the Invention] Industrial Application Field The present invention relates to the general formula () [Wherein, X represents a chlorine atom or a bromine atom,
R ¹ represents a lower alkyl group, a lower alkoxyalkyl group, an allyloxyalkyl group, a tetrahydrofurfuryl group, or a cyanoalkyl group, and R ²
is a lower alkyl group, a lower alkoxyalkyl group,
Represents an allyloxyalkyl group, a tetrahydrofurfuryl group, a cyanoalkyl group, or a hydrogen atom, and R ² represents a methyl group or an ethyl group.

The red coloring material for thermal transfer according to the present invention can be applied to a transfer printing method for synthetic fibers [Reference K.
Written by VENKATARAMAN “The Chemistry of
Synthetic Dyes, Vol. 191], or the transfer thermal recording method, which is a means of recording information [References: Nikkei Electronics, February 13, 1984, Journal of the Institute of Image Electronics Engineers, Vol. 12, No. 1, p. 18 It is a red coloring material useful as a coloring material used in "Television Society Journal" Vol. 37, No. 7, p. This is clearly the case.

Conventional technology Conventional red dyes for transfer printing include anthraquinone dyes represented by formula (2) [Reference JP-A-52-27890]; Azo dye represented by formula (3) [Reference JP-A-Sho
53−134974〕 Among the red coloring materials for transfer-type heat-sensitive recording, there is no one that has excellent transferability, light fastness, and other fastness properties.

Problems to be Solved by the Invention When using a red coloring material in a transfer type recording system, the important quality is the storage stability of the record, that is, the fastness such as sunlight fastness, ease of removal due to masatsu, etc. Thermal stability during transfer and color value are important, but no coloring material has been well-balanced so far.

Means for Solving the Problems In order to solve the above problems, the present inventors have made extensive studies and found that the coloring materials represented by the general formula () have good fastness, high color value, and The present invention was accomplished by discovering that it has good thermal stability and has the necessary properties as a coloring material for transfer dry heat recording.

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 () 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 printing paper using a thermal head to create an image. .

In the coloring material represented by the general formula () of the present invention, examples of the lower alkyl group represented by R ¹ and R ² 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 Examples include cyanomethyl group and cyanoethyl group.

Examples will be shown below, and parts and % in the examples mean weight.

Example 1st order formula A colorant consisting of 10 parts of ethyl cellulose, 5 parts of ethyl cellulose, 70 parts of ethyl alcohol, 20 parts of ethyl acetate and 5 parts of ethyl glycol was used to print on paper by the flexographic method and the print was dried. The printed side of this paper is placed on a polyester knit 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 cloth has a light fastness of 6-7
(according to JIS, L0842-1971. The following examples are also the same method), sublimation fastness grade 3 (according to JIS, L0879-1975 (180℃ 30 Measured by contamination of Tetron cloth tested by Sec.) Water fastness grade 4 (Sumitex Resin UN-1 (Sumitomo Chemical product)
After resin processing by JIS, L0846-1976 (B method 16
time) to test and measure the contamination of nylon cloth. ) Washing fastness grade 4-5 (Sumitex Resin
After resin processing with UN-1 (Sumitomo Chemical product)
Tested using the AATCCA method to measure contamination of nylon cloth. ).

The coloring material of the above formula is 2-amino-5-bromo-
18 parts of 1,3,4-thiadiazole were mixed at 0°C with 160 parts of glacial acetic acid, 80 parts of 89% phosphoric acid and 13% nitrosyl sulfuric acid.
The mixture was added to 130 parts of the mixed solution, and diazotization reaction was carried out at 0°C for 2 hours. Subsequently, 29.4 parts of 3-[N,N-di-(ethoxyethyl)amino]acetanilide was added to the acidic solution at 0°C. with caustic soda
After adjusting the pH to 5, it was obtained by filtering, washing with water, and drying. The dye had a λmax (in acetone) of 516 nm.

Example Quadratic equation A colorant consisting of 5 parts of colorant, 20 parts of a styrene polymer, and 80 parts of toluene is used to print on paper by copper gravure printing, and the print is dried. Then, in the same manner as in Example 1, at 190°C for 25 seconds,
Transferring the paper print pattern onto the polyacrylonitrile fabric resulted 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) 508nm.

Example cubic formula 20 parts of dye, 380 parts of water, 400 parts of 10% locust bean powder ether thickener and 200 parts of 10% starch ether thickener
The paper is printed using a rotary film printing method using a colorant consisting of 100% of the colorant, and the print is dried. Then, in the same manner as in Example 1, at 210°C for 30 seconds,
Transferring the paper print pattern onto the polyester fabric resulted 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) = 518 nm.

Example 4th equation 10 parts of colorant, as well as 40 parts of colophonium resin whose composition has been modified with phenol, and 20 parts of vegetable drying oil.
The desired pattern is printed on the transfer paper by offset printing using a colorant consisting of 90 parts of varnish, 10 parts of long oil alkyd resin, 25 parts of mineral oil, 10 parts of Aerosil and 2 parts of cobalt desiccant. Place the printed side of the dried print onto the polyacrylonitrile fabric;
Then, when processed at 205℃ for 25 seconds on a single-fed press,
A red-on-white print was obtained that was lightfast and wetfast.

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

Example 5 Next formula 10 parts of colorant, and composition of 10 parts of ethyl cellulose
75 parts of ethyl alcohol, 20 parts of ethyl acetate and 90 parts of varnish of 5 parts of ethyl glycol. Place the printed side of the dried print onto the polyester fabric and pass them together through a calendar at 200°C for 30 seconds. 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. λmax (in acetone) = 520nm.

Example 6 Formula 20 parts of colorant, 280 parts of water and 700 parts of 8% locust bean flour ether thickener are printed on paper by rotary film printing and the print is dried. Then, in the same manner as in Example 2, 210
Transferring the paper print pattern onto the polyester fabric for 20 seconds at 0C resulted in a red-on-white print with wet fastness.

Example 7 The following formula When the coloring material was applied to paper to create a red color sheet and an image was created using a printer, a clear image was obtained.

Claims (1)

[Claims] 1 (1) General formula [Wherein, X represents a chlorine atom or a bromine atom,
R ¹ represents a lower alkyl group, a lower alkoxyalkyl group, an allyloxyalkyl group, a tetrahydrofurfuryl group, a cyanoalkyl group,
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 ³ represents a methyl group or an ethyl group. ] A red coloring material for thermal transfer indicated by .