JPS6399381A - Dyeing of hydrophobic fiber using pyridone monoazo compound - Google Patents

Abstract

(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION Industrial Utilization Public Funds The present invention relates to a hydrophobic dyeing method using a pyridone monoazo compound.

<Prior Art> Pyridone-based monoazo compounds are generally useful as dyes capable of dyeing hydrophobic fibers in vivid greenish-yellow to orange colors, and their coatings and production volumes are increasing. However, compared to quinophthalone compounds, which are often used as yellow dyes, they have insufficient stability under dyeing conditions (dye bath stability), and there are limits to their use. For example, as a pyridone-based monoazo compound for hydrophobic fibers, the following formula (
Compounds represented by a) and (cut C2H5) are in practical use, but their dye bath stability [dye bath stability is determined by the following formula: B/AX1
00 (%), however, A: Dye concentration 0.6%o-W”
f @ Dyeing density of dyed fabric when dyeing with I bath ratio 1/80% pH 7 at 180°C for 160 minutes.

B: After leaving the dye bath containing no dyed fabric at pH 7 and temperature 140°C for 80 minutes, add the dyed fabric and heat at 180°C 160°C.
Dyeing density of dyed fabric when dyed for minutes. ] However, (a) and (b) are low at 20% and 55%, respectively, and improvement thereof is strongly desired.

<Problems to be Solved by the Invention> The present inventors have conducted intensive studies on a dyeing method for hydrophobic a-fibers that provides dyed products with excellent dyeability, dye bath stability, and excellent fastness properties. They discovered that the purpose could be achieved by using a dye and completed the present invention.

<Means for solving the problem> The present invention is based on the following general formula (1) [wherein, , an alkylsulfonyl group, an arylsulfonyl group, a carbamoyl or sulfamoyl group having a substituent, or a cyano group, R is an alkylene group having 1 to 6 carbon atoms, Y is a direct bond or a divalent group, and 2 is a Hydrogen atom, halogen atom, alkyl group having 1 to 4 carbon atoms, or 1 to 4 carbon atoms
represents an alkoxy group. ] Provided is a method for dyeing hydrophobic a-fibers, which is characterized by using one or more of the pyridone-based monoazo compounds shown below.

The alkyl group in the alkyl group, alkoxy group, alkylcarbonyl group, alkyloxycarbonyl group, aralkyloxycarbonyl group and alkylsulfonyl group represented by X in the general formula Yamanaka means an alkyl group having 1 to 4 carbon atoms. The halogen atom represented by X is a salt.

Examples of the alkyl group include methyl group, ethyl group, propyl group, butyl group, etc.; examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, etc. , alkylcarbonyl groups include acetyl group, propionyl group, etc., alkyloxycarbonyl groups include methoxycarbonyl group,
Ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, etc., aralkyloxycarbonyl group such as benzyloxycarbonyl group, alkylsulfonyl group such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, etc.
Arylsulfonyl groups include phenylsulfonyl groups, carbamoyl or sulfamoyl groups which may have substituents include carbamoyl, ethylcarbamoyl, butylcarbamoyl, sulfamoyl, ethylsulfamoyl, and butylsulfamoyl groups. etc. are exemplified. Among these, X is preferably a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylsulfonyl group, an arylsulfonyl group, a cyano group, etc. Especially, hydrogen 〆0'', bromo, methyl, ethyl, methylsulfonyl, ethyl. Sulfonyl, phenylsulfonyl,
Cyano is preferred.

The divalent group represented by Y may be any group capable of connecting the phenyl group represented by A represented by R, but is preferably a group containing an oxygen atom, and the following are exemplified.

-0-*, -0-alkylene-*.

−〇−Alkylene−〇−Water.

10-0-alkylene*, -0-C-*.

-c-o-*, -o-c-o-*.

-NH5Q2-*, -NHC-*.

-O-C-NH-* (In the above, alkylene is Cl-C4 alkylene, and * means a bond with a phenyl group.) Y is preferably a direct bond or -0-*.

10-alkylene*, -0-C-*.

A divalent group such as -0-C-O-*, most preferably a direct bond.

In the cl-c6 alkylene group represented by R, methylene,
Substituents for lower alkyl groups such as ethylene and propylene include phenylalkyl groups such as benzyl group and phenethyl group, phenyloxyalkyl groups such as phenoxyethyl and phenoxypropyl groups, benzyloxyethyl group, phenethyloxyalkyl group, etc. Phenylalkyloxyalkyl groups, phenylcarbonyloxyalkyl groups such as benzoyloxyethyl groups, phenyloxycarbonyloxyalkyl groups such as phenoxycarbonyloxyethyl groups, phenyloxycarbonylalkyl groups such as phenoxycarbonylethyl groups, phenylsulfonylaminoethyl groups, etc. phenylsulfonylaminoalkyl groups such as phenylsulfonylaminoalkyl groups, phenylcarbonylaminoalkyl groups such as benzoylaminoethyl groups, phenylcarbamoyloxyalkyl groups such as phenylcarbamoyloxyethyl groups, and the like. Examples of the substituent (Z) of the phenyl group include hydrogen, chloro, bromine, methyl, ethyl, methoxy, and ethoxy.

The pyridone-based monoazo compound represented by the general formula (I) is a compound represented by the following general formula (I) (wherein, X has the above-mentioned meaning) and the following general formula (l[)C in the formula: , W represents a halogen atom, and R%Y and Z have the above-mentioned meanings. ) It can be produced by reacting with the compound shown below. This reaction is carried out in water, an organic solvent, or a mixed solvent thereof at 50 to 200°C in the presence of a deoxidizing agent.
This can be easily done by heating to .

In addition, an amine represented by the general formula (ff) (wherein, X has the above-mentioned meaning) is diazotized by a conventional method,
0) (wherein, RSY and Z have the above-mentioned meanings).
) can be obtained. This coupling reaction can be easily carried out under mildly alkaline conditions at a temperature of -10° to 10°C.

When using the compound thus obtained as a dye, it is dispersed according to a conventional method.

Dispersion can be carried out, for example, in a sand mill by dispersing naphthalene sulfonic acid formalin condensate, lignin sulfonic acid, cresol.
Using a dispersant selected from various dispersants such as anionic dispersants such as Scheffer's acid formalin condensate, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, and other nonionic dispersants, It can be carried out in an aqueous medium. The obtained disperse dye liquid can be used as it is in liquid form or after being dried and used as powder or granules.

The hydrophobic fibers used in the method of the present invention include synthetic fibers such as polyamide fibers and polyester fibers, semi-synthetic a, r* such as di- or triacetate, or mixed fiber materials of these and natural fibers. It is particularly useful for dyeing polyester fibers and their mixed ta fibers with natural or regenerated cellulose 0 H&; dyeing can be carried out in a conventional manner.

According to the method of the present invention, the dyeability, especially the color yield, is high, the dye bath stability is significantly superior to that of the above-mentioned known compounds (a) and (b), and the wet lI! It is possible to obtain a vivid greenish to reddish yellow dyed product with excellent fastness, sublimation fastness, post-processing fastness, and light fastness.

The present invention will now be explained in more detail by way of examples.

In the examples, part refers to ii room.

Example 1 21,5 parts f) p-promo 0-nitroaniline is stirred vigorously with 180 parts of water and 86 parts of 80% hydrochloric acid and 0 with a solution containing 7 parts of sodium nitrite in 60 parts of water.
28% fR clear diazo liquid, diazotized at ~5°C
Add gradually to a solution of 20.2 parts of 1-benzyl-4-methyl-6-hydroxy-pyridol-2-one dissolved in 600 parts of water containing 25 parts of caustic soda and 38 parts of sodium acetate at 0 to 5°C. Stir at temperature for 80 minutes. The mixture is then acidified, filtered, washed and dried. 29 parts of a compound represented by the following formula (1) was obtained.

CH2-<○ λmax 482 parts m (in DMF) Staining was carried out using the compound (11) thus obtained by the following procedure.

a) Preparation of dispersion Compound (1) or (2) 20 parts Anionic dispersant (Note) 20 parts Water
60 parts Total: 100 parts (Note 1) Naphthalene sulfonic acid formalin condensate The above mixture was processed in a sand mill for 10 hours to obtain a dispersion.

b) Staining 8 parts of the dispersion obtained in a) are placed in a dyeing pot together with 8000 parts of water and adjusted to pH 5 using acetic acid. Next, 100 parts of polyester fabric was added and dyed at 180° C. for 60 minutes. After the dyeing is finished, washing and rinsing are carried out in a conventional manner, followed by drying. A clear, greenish-yellow dyed product with excellent light fastness and other fastness properties was obtained.

Example 2 In Example 1, 15.2 parts of 0-nitro-p-methylaniline and 1-benzyl-
When 22.9 parts of 1-β-phenethyl-4-methyl-6-hydroxypyridol-2-one is used instead of 4-methyl-6-hydroxy-pyridol-2-one, the following formula (2) is obtained.
87.2 parts of the compound were obtained.

Also, 5-(2'-ditro-4''-methylphenylazo)-4-methyl-6-hydroxy-pyrido-2-one 2
8.8 parts, 8.5 parts of sodium carbonate, 0.5 parts of potassium iodide
1 part, β-phenethylbromide, 27.8 parts, and 1.0 part of water in 120 parts of chlorobenzene at 80°C until the raw materials disappeared. After the reaction, 120 parts of methanol was added and the precipitated crystals were dissolved. The mixture was filtered, washed and dried to obtain 88.2 parts of compound (2).

Using the compound (2) thus obtained, a polyester fabric was dyed in the same manner as in Example 1 to obtain a clear, greenish-yellow dyed product with excellent color fastness and high density.

Example 8 Using the dispersion obtained in Example 1 a), a printing paste having the following composition is prepared.

(Printing paste composition) Above dispersion 8 parts Half emulsion base paste (Note 2) 60 parts Sake Stone
Fermentation 0.8 parts Sodium chlorate 0.2 parts Total 100
Part (Note z) Hafemarji Nippon Glue Composition Kerosene Oil 70 parts Water
255 parts Total 100 parts (Note 8) Shin-Nakamura Chemical Co., Ltd. Product: Emulsifier 80 parts of Emulge Day mixed with the above in a high-speed mixer and Maypro Gum N
A half-emulsion base paste was mixed with 70 parts of P12% paste (product of Greenara Co., Ltd.) and hand-printed on polyester cloth. The cloth is then dried and subjected to superheated steam treatment at 175° C. for 7 minutes. Thereafter, washing and drying are performed using a conventional method. A strong and vivid greenish yellow printed fabric was obtained.

Examples 4 to 88 The compounds shown in the table below were synthesized in the same manner as in Example 1, and polyester fibers were each dyed in the same manner as in Example 1 to obtain the results shown in the table below.

Claims (1)

[Claims] The following general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, group, an alkylsulfonyl group, an arylsulfonyl group, a carbamoyl or sulfamoyl group which may have a substituent, or a cyano group, R is an alkylene group having 1 to 6 carbon atoms, Y is a direct bond or a divalent group, Z is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or a carbon number 1 to 4
represents an alkoxy group. ] A method for dyeing hydrophobic fibers, characterized in that one or more of the pyridone-based monoazo compounds shown below are used.