JPS63199763A - Pyridone monoazo compound and method of dyeing hydrophobic fiber by using the same - Google Patents

Abstract

NEW MATERIAL:Pyridone monoazo compds. of formula I (wherein X is H, halogen, an alkoxy, an alkylcarbonyl, an alkyloxycarbonyl, an aralkyloxycarbonyl, an alkylsulfonyl, an arylsulfonyl, carbamoyl, sulfamoyl, cyano or the like; R is a 3-4C straight-chain or branched alkyl). USE:Dyes which have excellent dyeing quality and dyeing bath stability and can dye hydrophobic fibers such as polyamide fibers, polyester fibers, etc. clear greenish yellow to orange with excellent fastness to light, wetting, etc. PREPARATION:A compd. of formula II is reacted with a compd. of Z-R (wherein Z is halogen) to obtain the compd. of formula I. Alternatively, an amine of formula III is diazotized and then coupled with a compd. of formula IV to obtain the compd. of formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application> The present invention relates to a pyridone-based monoazo compound and its application to the dyeing of hydrophobic fibers.

<Prior Art> Pyridone-based monoazo compounds are generally useful as dyes capable of dyeing hydrophobic LA fibers in vivid greenish-yellow to orange colors, and their types and production quantities are increasing.

<Problems to be solved by the invention> However, compared to quinophthalone compounds, which are often used as yellow dyes, the stability under dyeing conditions (dye bath stability) is insufficient, and there are limits to its use. . For example, as pyridone-based monoazo compounds for hydrophobic fibers, the compounds shown by the following formula and (b) have been put into practical use, but the dye bath stability of these compounds [the dye bath stability is determined by the following formula tL Ru. B, /
Ax100 (%), however, A: Dye concentration 0.6% o, w
, f, , bath ratio 1/80. Staining density when dyeing at pH 7 at 180°C for 60 minutes. B: Dyeing bath that does not contain dyed fabric
H7: Dyeing density of the dyed fabric when it was left at a temperature of 140°C for 80 minutes, then the fabric to be dyed was added and dyed at 180°C for 60 minutes. ], but (a) and (b) are 20% and 55%, respectively.
This is low, and improvement is strongly desired.

The present inventors conducted intensive research with the aim of finding a dye with excellent dyeability, various fastness properties, and dye bath stability, and as a result, they discovered that a specific compound has the desired performance. .

Means for Solving Problems> The present invention is based on the following general formula (1), [wherein X is a hydrogen atom, a halogen atom, an alkoxy group,
Alkylcarbonyl group, alkyloxycarbonyl group,
represents an aralkyloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, a carbamoyl or sulfomoyl group which may have a substituent, or a cyano group, and R is a linear or branched chain having 8 to 4 carbon atoms. represents an alkyl group. The present invention provides a method for dyeing hydrophobic fibers, which is characterized by using a pyridone-based monoazo compound represented by the following formula, and one or more thereof.

In the general formula (1), the alkyl group in the alkoxy group, alkylcarbonyl group, alkyloxycarbonyl group, aralkyloxycarbonyl group and alkylsulfonyl group represented by X means an alkyl group having 1 to 4 carbon atoms. Examples of the halogen atom represented by Alkyloxycarbonyl groups include methoxycarbonyl group, ethoxycarbonyl group, proloxycarbonyl group, butoxycarbonyl group, etc., aralkyloxycarbonyl group includes benzyloxycarbonyl group, etc., alkylsulfonyl group includes methylsulfonyl group, Ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, etc. Arylsulfonyl group includes phenylsulfonyl group, etc. Carbamoyl or sulfomoyl group which may have a substituent includes carbamoyl group, ethylcarbamoyl group, butylcarbamoyl group , 1-moyl sulfate group, 1-moyl ethylsulfate group, 1-moyl butylsulfate group, and the like. Among these, X is a hydrogen atom, a halogen atom, an alkoxy group,
Preferred are alkylsulfonyl groups, arylsulfonyl groups, cyano groups, etc., especially hydrogen atoms, chlorine atoms,
Preferred are a bromine atom, a methyl group, an ethyl group, a methylsulfonyl group, an ethylsulfonyl group, a phenylsulfonyl group, and a cyano group.

As R, n-propyl group, iso-propyl group, n-
Examples include butyl group, iso-butyl group, and 5ec-butyl group. Among these, as R, n-propyl group/-iso-propyl group, n-butyl group, and iso-butyl group are preferable.

The pyridone-based monoazo compound represented by the general formula (1) is a compound represented by the following general formula (1) (wherein, X has the above-mentioned meaning) and the following general formula (1)% formula% 1) (In the formula, 2 represents a halogen atom, and R has the above-mentioned meaning.) It can be produced by reacting with a compound represented by the following. This reaction can be easily carried out in water, an organic solvent, or a mixed solvent thereof by heating to 50 to 200°C in the presence of a deoxidizing agent.

Further, an amine represented by the general formula (JT) (wherein, X has the above-mentioned meaning) is diazotized by a conventional method,
The compound represented by the general formula (1) can also be obtained by coupling with a compound represented by the formula (m) (wherein R has the above-mentioned meaning). This coupling reaction can be easily carried out under mildly alkaline conditions at temperatures 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 diiferic acid formalin condensates, polyoxyethylene alkyl ethers, -lyoxyethylene alkyl phenyl 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 compound (1) of the present invention is a synthetic fiber such as polyamide fiber, polyester fiber, semi-synthetic fiber such as di- or triacetate fiber, or a mixed fiber material of these and natural fiber, especially polyester m-fiber and natural or regenerated cellulose. The mixed fibers can be dyed in a vivid greenish yellow to orange color by a conventional dyeing method, continuous dyeing method, printing method, etc. The compound (1) of the present invention is also useful for transfer printing.

The compound (1) of the present invention has high dyeability, especially high color yield (and has significantly superior dye bath stability and light fastness compared to the above-mentioned known compounds (6) and (2), and
It is possible to provide dyed products with excellent wet fastness, sublimation fastness, and post-processing fastness.

Hereinafter, the present invention will be explained in more detail with reference to Examples. In the examples, parts refer to parts by weight, and color tones refer to those on polyester fibers.

Example 1 18.8 parts of 0-nitroaniline was mixed with 180 parts of water and 3
Diazotization is carried out at 0-5° C. with a solution of 7 parts sodium nitrite in 50 parts water with vigorous stirring with 6 parts of 80% hydrochloric acid. 1-n-Butyl-4 was added to 600 parts of water containing 25 parts of 28% caustic soda and 88 parts of sodium acetate.
-Methyl-6-hydroxy-pyrido-2-one 16.8
The mixture was gradually added to the solution at θ~5°C and stirred at the same temperature for 80 minutes.

The mixture was then made acidic, filtered, washed and dried to obtain a compound of formula (1) below.

λmax 481 parts (in DMF) Color #: greenish yellow Example 2 In Example t, 21.7 parts of 0-nitro-p-bromoaniline, 1-n-butyl-4- Using 16.4 parts of 1-n-propyl-4-methyl-6-hydroxy-pyrido-2-one instead of methyl-6-hydroxy-pyrido-2-one, the following formula (2
) was obtained.

RaH? -n λmax 482 nm (in DMF) Color tone 2 greenish yellow 5-(
85.8 parts of 2'-nitro-4'-bromphenylazo)-4-methyl-6-hydroxy-pyrido-2-one was mixed with 8.5 parts of sodium carbonate, 0.5 part of potassium iodide, and
71/80.0 parts of n-propy: Reacted with 1.0 part of water in 120 parts of chlorobenzene at 80°C until the raw material disappeared. After the reaction, 120 parts of methanol was added, and the precipitated crystals were filtered, washed, Compound (2) was obtained even after drying.

Example 8 Staining was carried out using the compound (I) obtained in Example 1 and the compound (2) obtained in Example 2 by the following operation.

a) Preparation of dispersion Compound (1) or (2) 20 parts Anionic dispersant (Note 1) 20 parts Water 60 parts Total 100
Part (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. It has excellent light fastness and other fastness properties, and produces a vivid, greenish-yellow dyed product with high density.

In addition, the dye bath stability was 90 for both compounds (1) and (2).
% or more.

Examples 4-27 The reaction was carried out in the same manner as in Example 2 to obtain the compounds shown in the table below.

Example 28 Using the dispersion obtained in Example 8 a), a printing paste having the following composition is prepared.

(Printing paste composition) Above dispersion 8 parts Half emulsion base paste (Note) 60 parts Tartaric acid
0.8 parts Sodium chlorate 0.2 parts Water
Total remaining 100 parts (Note 2) Half emulsion base paste composition Kerosene 70 parts Water
25 parts Viscon KM-8 (!8
) Part a total 100 parts (Note 8) Shin Nakamura Chemical ■Product: Emulsifier 91280 parts of emul obtained by mixing the above in a high-speed main mixer and Maybrogum NP 12% paste (Grinara product) 7
0 parts to form a half emulsion paste.

Using the dyeing paste thus obtained, hand printing is performed on polyester cloth. The cloth is then dried and subjected to superheated steam treatment at 176° C. for 7 minutes. Thereafter, washing and drying are performed using a conventional method. A strong and vivid greenish yellow printed fabric was obtained.

Claims (2)

[Claims] (1) General formula below▲ Numerical formulas, chemical formulas, tables, etc.▼ [In the formula, X is a hydrogen atom, a halogen atom, an alkoxy group,
Alkylcarbonyl group, alkyloxycarbonyl group,
represents an aralkyloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, a carbamoyl or sulfamoyl group which may have a substituent, or a cyano group, and R is a linear or branched alkyl group having 3 to 4 carbon atoms. represents a group. ] A pyridone-based monoazo compound represented by (2) The following general formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X is a hydrogen atom, a halogen atom, an alkoxy group,
Alkylcarbonyl group, alkyloxycarbonyl group,
represents an aralkyloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, a carbamoyl or sulfamoyl group which may have a substituent, or a cyano group, and R is a linear or branched alkyl group having 3 to 4 carbon atoms. represents a group. ] A method for dyeing hydrophobic fibers, characterized by using one or more of the pyridone monoazo compounds shown below.