JP2556692B2 - Method for dyeing hydrophobic fiber using pyridone monoazo compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial field of application> The present invention relates to a method for dyeing a hydrophobic fiber using a pyridone monoazo compound.

<Prior Art> A pyridone-based monoazo compound is generally useful as a dye capable of dyeing a hydrophobic fiber in a bright greenish yellow to orange color, and its type and production amount are increasing.

<Problems to be Solved by the Invention> However, the stability under dyeing conditions (dye bath stability) is insufficient as compared with quinophthalone-based compounds that are often used as yellow dyes, and there is a limit in their use. . For example, as a pyridone-based monoazo compound for hydrophobic fibers,
The following formulas (a) and (b) The compounds represented by are practically used, but their dye bath stability [dye bath stability is determined by the following formula. B / A x 100
(%), But A: dye concentration 0.6% owf, bath ratio 1/30, pH7
Staining density of the mushroom cloth dyed at 130 ° C for 60 minutes. B:
Dyeing density of the dyed fabric when the dyeing bath not containing the dyed fabric is left at pH 7 and temperature of 140 ° C for 30 minutes and then the dyed fabric is put and dyed at 130 ° C for 60 minutes. ], But (a) and (b) are each 20
%, As low as 55%, and improvement is strongly desired.

The present inventors have conducted intensive studies on a dyeing method of a hydrophobic fiber which is excellent in dyeability and dye bath stability and gives a dyed product excellent in various fastnesses, and as a result, found that the purpose is suitable by using a specific dye. The present invention has been completed.

<Means for Solving Problems> The present invention has the following general formula (I). (In the formula, X represents a hydrogen atom, a chlorine atom, a methyl group or a methoxy group.) One or more pyridone-based monoazo compounds are used, and a method for dyeing a hydrophobic fiber is provided. To do.

The pyridone-based monoazo compound represented by the general formula (I) has the following general formula (II) (In the formula, X has the above-mentioned meaning.) It can be produced by reacting a compound represented by: with an alkylating agent such as ethyl iodide, toluenesulfonic acid ethyl ester and diethyl sulfuric acid. This reaction can be easily carried out by heating to 50 to 150 ° C. in the presence of a deoxidizing agent in water or an organic solvent or a mixed solvent thereof.

In addition, the general formula (III) (In the formula, X has the above-mentioned meaning.) The diazotization of the amine represented by the above-mentioned method and the coupling with 1-ethyl-4-methyl-6-hydroxy-pyrid-2-one are also common. A compound of formula (I) can be obtained. This coupling reaction can be easily carried out at a temperature of -10 ° to 10 ° C under weak alkaline conditions.

When the compound thus obtained is used as a dye, it is dispersed according to a conventional method. Dispersion is carried out, for example, in a sand mill by using an anionic dispersant such as naphthalene sulfonic acid formalin condensate, lignin sulfonic acid, cresol-schaferic acid formalin condensate or polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers and other non-dispersants. It can be carried out in an appropriate amount of an aqueous medium using a dispersant selected from various dispersants such as an ionic dispersant. The obtained disperse dye solution can be used as a powder or granules as it is or dried.

The hydrophobic fibers in the method of the present invention include synthetic fibers such as polyamide fibers and polyester fibers, semi-synthetic fibers such as di- or triacetate, or mixed fiber materials thereof with natural fibers.

The method of the present invention is particularly useful for dyeing a polyester fiber and a mixed fiber of the polyester fiber and a natural or regenerated cellulose fiber, and the dyeing is carried out by an ordinary dip dyeing method, continuous dyeing method or printing method. The method of the present invention can also be carried out by ordinary transfer printing.

According to the method of the present invention, the dyeing property, in particular, the color yield is high, and the dye bath stability and the light fastness are remarkably excellent as compared with the above-mentioned known compounds (a) and (b), and the fastness to warming, It is possible to obtain a clear greenish yellow to orange dyeing product which is excellent in fastness to sublimation and fastness to post-processing.

Hereinafter, the present invention will be described in more detail with reference to examples. In the examples, "parts" means "parts by weight".

Example 1 13.8 parts o-nitroaniline in 180 parts water and 36 parts 3
Stir vigorously with 0% hydrochloric acid and carry out diazotization at 0-5 ° C. with a solution of 7 parts sodium nitrite in 50 parts water. 0 to 5 ° C in a solution of 15.3 parts of 1-ethyl-4-methyl-6-hydroxy-pyrid-2-one in water in 600 parts of the clear diazo solution containing 25 parts of 28% caustic soda and 33 parts of sodium acetate.
Is gradually added, and the mixture is stirred at the same temperature for 30 minutes. The mixture was then acidified, filtered, washed and dried to give the compound of formula (1) below.

The compound (1) thus obtained was dyed by the following procedure.

a) Preparation of dispersion Compound (1) 20 parts Anionic dispersant 20 parts Water 60 parts Total 100 parts (Note 1) Naphthalenesulfonic acid formalin condensate The above mixture was treated in a sand mill for 10 hours to obtain a dispersion liquid. .

b) Dyeing 3 parts of the dispersion obtained in a) together with 3000 parts of water are placed in a dyeing pot and adjusted to pH 5 with acetic acid. Next, 100 parts of polyester woven fabric is added and dyeing is performed at 130 ° C. for 60 minutes. After completion of dyeing, washing and rinsing are performed by a conventional method, and then dried. A green and yellow dyed product which was excellent in various fastnesses such as light fastness and which was clear and had a high density was obtained.

Example 2 Instead of o-nitroaniline in Example 1, o-
17.3 parts of nitro-p-chloroaniline was used to obtain a compound of the following formula (2).

Also, 5- (2-nitro-4-chlorophenylazo)
-4-Methyl-6-hydroxy-pyrid-2-one 35.3
Parts of sodium carbonate, ethyl iodide 31.4 parts, and water 1.0 parts in chlorobenzene 120 parts, and reacted at 70 ° C. until the raw materials disappeared, after the reaction, methanol 120 parts was added, and the precipitated crystals were washed by excess, Drying gave compound (2).

The compound (2) thus obtained was dyed on a polyester fabric in the same manner as in Example 1 to obtain a green and yellow dyed product which was excellent in various fastnesses and had a high density.

Example 3 Using the dispersion obtained in Example 1 a), a printing paste having the following composition is prepared.

(Printing paste composition) Dispersion above 3 parts Half emulsion original paste (Note 2) 60 parts Tartaric acid 0.3 parts Sodium chlorate 0.2 parts Water Total 100 parts (Note 2) Half emulsion original paste composition Kerosene 70 parts Water 25 parts Bisukon KM-8 (Note 3) 5 parts total 100 parts (Note 3) Shin-Nakamura chemical Co. product: emulsion were mixed emulsifier above in a high speed mixer 30 parts of Meipurogamu NP12% paste (Gurinau Company) Mix with 70 parts to make a half emulsion base paste.

The polyester cloth is hand-printed with the paste thus obtained. The fabric is then dried and superheated steam treated at 175 ° C for 7 minutes. Then, washing and drying are carried out by a conventional method. A robust and vivid yellow textile print was obtained.

Example 4 Instead of o-nitroaniline in Example 1, o-
Using 15.2 parts of nitro-p-methylaniline, the compound of formula (3) below was obtained.

The compound (3) thus obtained was dyed on a polyester fabric in the same manner as in Example 1 to obtain a yellow dyed product which was excellent in various fastnesses and had a high density.

Example 5 Instead of o-nitroaniline in Example 1, o-
When nitro-p-methoxyaniline is used, the following (4)
Was obtained, and a polyester fabric was dyed in the same manner as in Example 1 to obtain a reddish yellow dyed product which was excellent in various fastnesses and had a clear and high density.

 ─────────────────────────────────────────────────── ─── Continuation of front page (56) Reference JP-A-54-7429 (JP, A) JP-A-61-106669 (JP, A) JP-A-53-84028 (JP, A) JP-A-47- 13633 (JP, A) JP-A-47-13635 (JP, A) JP-A-61-262191 (JP, A) JP-B 47-18549 (JP, B1) JP-B 47-50354 (JP, B1)

Claims (1)

(57) [Claims] 1. The following general formula (In the formula, X represents a hydrogen atom, a chlorine atom, a methyl group or a methoxy group.) One or more pyridone-based monoazo compounds represented by the formula (1) are used to dye the hydrophobic fiber.