JPH0819626B2 - Method for dyeing or printing hydrophobic fiber using pyridone monoazo compound - Google Patents

Description

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

<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 calculated by the following formula, B / A × 100
(%), But A: dye concentration 0.6% owf, bath ratio 1/30, pH7
Dyeing density of dyed fabric when dyed at 130 ℃ 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 for the purpose of developing a dyeing method that is not easily affected by the fluctuations in the pH and temperature of the dyeing bath, and that provides a dyed product with excellent concentration in various fastnesses. The present invention has been completed by finding that the above object can be achieved when a specific compound is used as a dye.

<Means for Solving the Problem> The present invention has the following general formula (I). [In the formula, X is a bromine, iodine or fluorine atom, and has 2 to 4 carbon atoms.
Represents an alkyl or alkoxy group, an alkylcarbonyl group, an alkyloxycarbonyl group, an aralkyloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, an optionally substituted carbamoyl or sulfamoyl group, or a cyano group. ] A method for dyeing or printing a hydrophobic fiber, characterized by using a dispersion of one or more pyridone monoazo compounds represented by the above in an aqueous medium.

In the general formula (I), the alkyl group in the alkylcarbonyl group, the alkyloxycarbonyl group, the aralkyloxycarbonyl group and the alkylsulfonyl group represented by X means an alkyl group having 1 to 4 carbon atoms. The alkyl group having 2 to 4 carbon atoms represented by X is an ethyl group,
Examples thereof include a propyl group and a butyl group, an alkoxy group such as an ethoxy group, a propoxy group and a butoxy group, an alkylcarbonyl group such as an acetyl group and a propionyl group, and an alkyloxycarbonyl group such as a methoxycarbonyl group and an ethoxycarbonyl group. , A propoxycarbonyl group, a butoxycarbonyl group, etc., an aralkyloxycarbonyl group, a benzyloxycarbonyl group, etc., an alkylsulfonyl group, a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, etc., and an arylsulfonyl group. Examples of the carbamoyl or sulfamoyl group which may have a substituent such as a phenylsulfonyl group include a carbamoyl group, an ethylcarbamoyl group, a butylcarbamoyl group, a sulfamoyl group and an ethylsulfate group. Amoiru group, a butyl sulfamoyl groups. Of these, X is a bromine atom,
Alkyl and alkoxy groups having 2 to 4 carbon atoms, alkylsulfonyl groups, arylsulfonyl groups, cyano groups and the like are preferable, and bromine atom, ethyl group, methylsulfonyl group, ethylsulfonyl group, phenylsulfonyl group and cyano group are particularly preferable.

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 is carried out in water or an organic solvent, or a mixed solvent thereof,
It can be easily carried out by heating to 50 to 150 ° C. in the presence of a deoxidizer.

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 compound (I) used in the present invention is a synthetic fiber such as polyamide fiber or polyester fiber, a semi-synthetic fiber such as di- or triacetate, or a mixed fiber material thereof with a natural fiber, particularly a polyester fiber and a natural or regenerated cellulose thereof. The mixed fiber with the fibers can be dyed in a clear greenish yellow to orange color by a usual dip dyeing method, continuous dyeing method or printing method. The compound (I) used in the present invention is also useful for transfer printing.

The compound (I) used in the present invention is dyeable,
The color yield is high, and the above-mentioned known compound (a),
It is possible to give a dyed product which is remarkably excellent in dye bath stability and light fastness as compared with (b), and is also excellent in wet fastness, sublimation fastness and post-processing fastness.

Hereinafter, the present invention will be described in more detail with reference to Examples. In the examples, "parts" means "parts by weight" and "color tone" means that on polyester fiber.

Reference Example 1 21.7 parts of o-nitro-p-bromo-aniline was vigorously stirred with 180 parts of water and 36 parts of 30% hydrochloric acid, and a solution containing 7 parts of sodium nitrite in 50 parts of water was added to 0-5. Diazotization is performed at ℃. 0 to 5 ° C in a solution prepared by dissolving 15.3 parts of 1-ethyl-4-methyl-6-hydroxy-pyrid-2-one in 600 parts of water 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.

λmax 432 nm (in DMF) Color tone: greenish yellow Reference Example 2 In Reference Example 1, 16.6 parts of o-nitro-p-ethylaniline was used instead of o-nitro-p-bromo-aniline, and the compound of the following formula (2) was used. Got

λmax 436nm (in DMF) Color tone: yellow 5- (2'-nitro-4'-ethylphenylazo)-
After reacting 30.2 parts of 4-methyl-6-hydroxy-pyrid-2-one with 8.5 parts of sodium carbonate, 31.4 parts of ethyl iodide and 1.0 part of water in 120 parts of chlorobenzene at 70 ° C. until the raw material disappears, and after the reaction Then, 120 parts of methanol was added, and the precipitated crystals were filtered, washed and dried to obtain the compound (2).

Example 1 The compound (1) obtained in Reference Example 1 and the compound (2) obtained in Reference Example 2 were dyed by the following procedure.

a) Adjustment compound dispersion (1) or (2) 20 parts anionic dispersing agent (Note 1) 60 parts Total 100 parts 20 parts Water (1) naphthalenesulfonic acid-formalin condensate above mixture in a sand mill 10 It was treated for a time to obtain a dispersion liquid.

b) Dyeing 3 parts of the dispersion obtained in a) together with 3000 parts of water are put 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 clear, high-density greenish-yellow dyed product having excellent fastnesses including light fastness was obtained.

The dye bath stability is 90 for both compounds (1) and (2).
% Or more.

Examples 4 to 18 Reaction was carried out in the same manner as in Reference Example 2 to obtain the compounds shown in the table below. Dyeing was performed in the same manner as in Example 1 using each of these compounds.

Example 19 Using the dispersion obtained in Example 1 a), a printing paste having the following composition is prepared.

(Printing paste composition) Dispersion 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. Washing and drying were carried out by a conventional method to obtain a robust and vivid green-yellow printing cloth.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-54-7429 (JP, A) JP-A-53-84038 (JP, A) JP-A-61-106669 (JP, A) JP-B 47- 18549 (JP, B1) JP-B 47-50354 (JP, B1)

Claims (1)

[Claims] 1. The following general formula [In the formula, X is a bromine, iodine or fluorine atom, and has 2 to 4 carbon atoms.
Represents an alkyl or alkoxy group, an alkylcarbonyl group, an alkyloxycarbonyl group, an aralkyloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, an optionally substituted carbamoyl or sulfamoyl group, or a cyano group. ] A method for dyeing or printing a hydrophobic fiber, which comprises using a dispersion liquid of one or more kinds of the pyridone-based monoazo compound represented by: in an aqueous medium.