JPH0823112B2 - 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 the formula (3) have been put into practical use, and 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 when stained at 130 ° C for 60 minutes. B: Dyeing density of the dyed fabric when the dyeing bath containing no dyed fabric was left at pH 7 and a temperature of 140 ° C for 30 minutes, and then the dyed fabric was added and dyed at 130 ° C for 60 minutes. ] However, (a) and (b) are as low as 20% and 55%, respectively, and their improvement is strongly desired.

The present inventors have conducted diligent research for the purpose of developing a dyeing method that is not easily affected by fluctuations in the pH and temperature of a dyeing bath and that can obtain a deep-colored dyeing excellent in various fastnesses. As a result, they have found that the above object can be achieved when a specific compound is used as a dye, and completed the present invention.

<Means for Solving the Problem> The present invention has the following general formula (I): [In the formula, X represents a hydrogen atom, a halogen atom, an alkoxy group,
Alkylcarbonyl group, alkyloxycarbonyl group,
Represents an aralkyloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, an optionally substituted carbamoyl or sulfamoyl group, or a cyano group, and R represents a linear or branched alkyl group having 3 to 4 carbon atoms. Represents a 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.

An alkoxy group represented by X in the general formula (I),
Alkylcarbonyl group, alkyloxycarbonyl group,
The alkyl group in the aralkyloxycarbonyl group and the alkylsulfonyl group means an alkyl group having 1 to 4 carbon atoms. Examples of the halogen atom represented by X include chlorine atom, bromine atom, iodine atom, fluorine atom and the like, alkoxy group as methoxy group, ethoxy group, propoxy group, butoxy group and the like, and alkylcarbonyl group as acetyl group and propionyl group. Groups, such as alkyloxycarbonyl groups, methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, etc., aralkyloxycarbonyl groups, benzyloxycarbonyl group, etc., alkylsulfonyl groups, methylsulfonyl group, ethylsulfonyl group, etc. Group, propylsulfonyl group, butylsulfonyl group, etc., arylphenyl group as phenylsulfonyl group, etc., carbamoyl or sulfamoyl group optionally having substituents as carbamoyl group, ethylcarbyl group Sulfamoyl group, butylcarbamoyl group, a sulfamoyl group, an ethyl sulfamoyl group, a butyl sulfamoyl groups. Of these, X is preferably a hydrogen atom, a halogen atom, an alkoxy group, an alkylsulfonyl group, an arylsulfonyl group, a cyano group or the like, and particularly, a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, a methylsulfonyl group. , Ethylsulfonyl group, phenylsulfonyl group and cyano group are preferred.

R is n-propyl group, iso-propyl group, n
-Butyl group, iso-butyl group, sec-butyl group and the like. Of these, R is preferably an n-propyl group, an iso-propyl group, an n-butyl group or an iso-butyl group.

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.), And the following general formula (III) ZR (III) (In the formula, Z represents a halogen atom and R has the above-mentioned meaning. ) It can manufacture by reacting with the compound shown by. This reaction can be easily carried out by heating to 50 to 200 ° C. in the presence of a deoxidizing agent in water or an organic solvent or a mixed solvent thereof.

In addition, the general formula (IV) (In the formula, X has the above-mentioned meaning.) The amine represented by the formula (V) is prepared by diazotizing the amine by a conventional method. (In the formula, R has the above-mentioned meaning.) The compound represented by the general formula (I) can also be obtained by coupling with the compound represented by the formula. 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 13.8 parts of o-nitroaniline was added to 180 parts of water and 36 parts of 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. A clear diazo solution was added to a solution prepared by dissolving 16.8 parts of 1-n-butyl-4-methyl-6-hydroxy-pyrid-2-one in 600 parts of water containing 25 parts of 28% caustic sword and 33 parts of sodium acetate. ~
Add slowly at 5 ° C and stir at the same temperature for 30 minutes. The mixture is then acidified, filtered, washed, dried and dried according to formula (I)
Was obtained.

λmax 431 nm (in DMF) Color tone: greenish yellow Reference Example 2 In Reference Example 1, instead of o-nitroaniline, o-
Nitro-p-bromoaniline 21.7 parts, 1-n-butyl-
Instead of 4-methyl-6-hydroxy-pyrid-2-one, 15.4 parts of 1-n-propyl-4-methyl-6-hydroxy-pyrid-2-one were used to give the compound of formula (2) below. Obtained.

λmax 432nm (in DMF) Color tone: greenish yellow 5- (2-nitro-4-bromophenylazo) -4-
35.3 parts of methyl-6-hydroxy-pyrid-2-one, 8.5 parts of sodium carbonate, 0.5 part of potassium iodide, 30.0 parts of i-n-propyl iodide: 120 parts of chlorobenzene together with 1.0 part of water,
The reaction was continued at 80 ° C. until the raw materials disappeared, 120 parts of methanol was added after the reaction, and the precipitated crystals were filtered, washed and dried to obtain the compound (2).

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

a) Preparation of dispersion Compound (1) or (2) 20 parts Anionic dispersant (Note 1) 20 parts Water 60 parts Total 100 parts (Note 1) Naphthalenesulfonic acid formalin condensate The above mixture is placed in a sand mill for 10 hours. Processed to obtain a dispersion.

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. Excellent fastness such as light fastness, and clear and dense green-yellow dyeing can be obtained.

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

Examples 4 to 27 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 28 Using the dispersion obtained in Example 1 a), a printing paste having the following composition is prepared.

(Printing paste composition) Above 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: emulsifiers above 30 parts emulsion were mixed in a high speed mixer and Meipurogamu NP12% paste (Gurinau Company) 70 parts And are mixed to form 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 green-yellow printing fabric was obtained.

 ─────────────────────────────────────────────────── --Continued from the front page (56) References JP-A 61-262191 (JP, A) JP-A 47-13635 (JP, A) JP-A 47-13633 (JP, A) JP-A 54- 7429 (JP, A) JP 47-18549 (JP, A) JP 47-50354 (JP, A) JP 53-84028 (JP, A) JP 61-106669 (JP, A)

Claims (1)

[Claims] 1. The following general formula [In the formula, X represents a hydrogen atom, a halogen atom, an alkoxy group,
Alkylcarbonyl group, alkyloxycarbonyl group,
Represents an aralkyloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, an optionally substituted carbamoyl or sulfamoyl group, or a cyano group, and R represents a linear or branched alkyl group having 3 to 4 carbon atoms. Represents a 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.