JPS5943594B2 - Method of dyeing or printing polyester fibers - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is a method for dyeing or printing polyester fibers, which is characterized by using a dye represented by the following formula (I).

Many disperse dyes are currently commercially available for dyeing polyester fibers orange.

However, these dyes all have poor performance in terms of dyeability, build-up properties, light fastness, sublimation fastness, etc.
It had a fatal flaw in some respects. For these reasons, there is a desire to develop an orange disperse dye with excellent overall performance, and with the recent emergence of highly twisted thin fabrics such as georgette, it has become necessary to improve processing technology. Nowadays, the performance of dyes themselves has come to require extremely high fastness. As a result of intensive studies on orange dyes that meet the above requirements, the present inventors found that the monoazo dye represented by the formula (I) has good dyeing properties, good build-up properties, light fastness, water fastness, and perspiration fastness. It has been found that it has overall excellent performance in terms of fastness, washing fastness, rubbing fastness, and sublimation fastness.

The dye of the present invention is characterized by particularly excellent sublimation fastness and water fastness, and the main combination is high fastness orange dye or black dye, which is in increasing demand with the recent development of dyeing technology. It is useful as one of the ingredients, and exhibits outstanding effects, especially in improving the sharpness of fine lines in textile printing.

Hereinafter, the features of the present invention will be explained in detail in relation to the prior art.

As a dye having a similar structure to the dye used in the present invention,
The following dye is known from Japanese Patent Publication No. 37-4048. Further, as dyes having a hue similar to the dye in the present invention, the following are commercially available.

In contrast to these dyes, the dyes used in the present invention have dyeability, build-up properties, light fastness, water fastness, sweat fastness,
It is extremely excellent in all of its properties, such as abrasion fastness and sublimation fastness (*), with no drawbacks. Some of the results of comparative tests are shown below.

From Tables 1 and 2, the dyes of the present invention have the best performance in all items in all fastness tests compared to the dyes of Comparative Examples 1 to 6, but
Although dye No. 6 has a similar structural formula, it has at least one fatal defect in fastness (for example, low color value or poor water fastness). I understand that.

The dye (I) used in the present invention is produced by a method known per se, which is practically undescribed in the literature.
Nitroaniline is diazotized with nitrosyl sulfate to form N-β.
- By adding cyanoethyl-N-β-phenoxyethylaniline to a mineral acid aqueous solution or an organic solvent such as alcohol at low temperature, or conversely, by adding a coupler solution to an ice-water solution of a diazo solution to couple it. Obtainable.

The coupling component can be synthesized by cyanoethylating aniline with acrylonitrile and then β-phenoxyethylating it with the corresponding ester or chloride in the presence of an acid absorbing agent in a manner known per se.

The dye (I) thus obtained is ground into fine particles in an aqueous medium together with a suitable dispersant.

It is preferable to use the dispersed dye in the form of a paste or, in some cases, to dry it by spray drying or the like and use it in the form of a powder. - The dye thus obtained is advantageously dyed in an aqueous medium in which the fibers are immersed under pressure at 105°C or higher, preferably at 110-140°C.

It is also possible to dye at a relatively high temperature, for example in the boiling state of water, in the presence of a carrier such as o-phenylphenol or trichlorobenzene. Alternatively, the dye dispersion may be padded onto cloth and heated at 150 to 230°C for 30 seconds to 10 minutes.
So-called thermosol dyeing, which involves a drying process of 1 minute, is also possible. Further, a solvent dyeing method is also possible in which dyeing is performed using a dye bath system mainly containing an organic solvent such as trichlorethylene or perchlorethylene as the solvent of the dye bath. On the other hand, in the case of printing, the dye dispersion is mixed with a suitable thickening agent such as guar-based or locust bean-based, and this is printed on cloth and treated by steaming or thermosol method to achieve the purpose.

Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.

In the examples, parts represent parts by weight. Example 1 3 parts of the dye represented by formula (I) were mixed with 3 parts of formalin condensate of naphthalene-β-sulfonic acid and 1 part of sodium ligninsulfonate.
．． A dye bath is prepared by uniformly dispersing this and 3 parts of higher alcohol sulfate in 3,000 parts of water.

100 parts of Tetoron spun yarn (polyester fiber, manufactured by Toray Industries, Inc.) was immersed in this dye bath and dyed at 130°C for 60 minutes. After reduction and washing treatment at 65° C. for 10 minutes with a treatment solution consisting of 3 parts of amphoteric surfactant and 3000 parts of water, the sample was washed with water and dried. A highly concentrated orange dyeing with excellent properties such as sunlight, sublimation and water fastness was obtained. The dye of formula (I) was synthesized as follows. First, 146 parts of N-β-cyanoethylaniline was reacted with 188 parts of β-phenoxyethyl chloride and 106 parts of anhydrous sodium carbonate at 180 to 190°C for 10 hours to produce N-β-cyanoethyl-N-β- Phenoxyethylaniline was obtained. This N-β-cyanoethyl-N-β-phenoxyethylaniline was dissolved in 50% sulfuric acid 10
00 parts to prepare a coupling component. On the other hand, 2
- Diazotize 207 parts of 6-dichloro-4-nitroaniline using nitrosyl sulfuric acid at a low temperature (10°C or lower), and couple it with the coupling component at a low temperature. After coupling, wash with water and dye (1
) obtained 460 copies. (Yield 95%) M. p. l62~
16'CλMax426 nm (in dimethylformamide) Example 2 A dye bath is prepared in the same manner as in Example 1, and 10 parts of o-phenylphenol is added as a carrier to obtain a dye bath.

In this, 100 parts of Tetoron spun yarn was immersed, and 98~
Stain for 90 minutes at 100°C. Thereafter, the dyed product was treated in the same manner as in Example 1 to obtain a highly concentrated orange dyed product with excellent properties such as sunlight, sublimation and water fastness. Example 3 A finely divided dispersion of the dye of formula (1) obtained in the same manner as in Example 1 was mixed with Typrogum NPL 2% paste (Mayha
The mixture was kneaded with Elocust Bean Gum manufactured by Ill Co., Ltd., printed on polyester fibers, and high-pressure steamed at 130° C. for 30 minutes.

Claims (1)

[Claims] 1. A method for dyeing or printing polyester fibers, characterized by using a dye represented by the following formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I).