JPS61181865A - Pyridone monoazo compound - Google Patents

Abstract

NEW MATERIAL:Pyridone monoazo compounds of formula I, wherein X is H, lower alkyl; V is CN, CONH2; Y is alkyl, aralkyl; W is halogen; Q is a group of formula II or III (wherein R<1> is H, lower alkyl; R<2> is alkylene; R<3> is alkyl; A<-> is an anion). USE:Dyes which can dye simultaneously both a hydroxyl group-contg. fiber and an anionic group-contg. fiber by the use of only one dye, when a fiber blend of them is to be dyed. Fibers (yellow) which are clearly are uniformly dyed and have good fastness to wetting can be obtd. PREPARATION:A pyridone monoazo compd. of formula IV is reacted with an s-triazine compd of formula V (wherein Q' is a group of formula VI or VII) to prepare a monoazo compd. of formula VIII. The monoazo compd. is reacted with an alkylating agent of the formula R<1>-A to obtain the desired compd.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to pyridone-based monoazo compounds.

Conventional technology Conventionally, anionic water-soluble dyes having -803Ha groups have been used to dye fibers containing hydrosilyl groups such as cellulose fibers, or fibers containing amino groups such as wool and synthetic boria. When dyeing anionic group-containing fibers such as acrylic fibers and cationically dyeable polyester fibers, cationic water-soluble dyes having dated nitrogen atoms are used.

When dyeing mixed fibers of these, fibers containing silyl groups, etc., and fibers containing anionic groups, two types of dyes, the above-mentioned anionic water-soluble dyes and cationic water-soluble dyes, must be used. Therefore, the dyeing conditions are different for each, making it impossible to dye both of the above fibers at the same time.
There were problems such as the formation of a complex between the anionic water-soluble dye and the cationic water-soluble dye, resulting in poor dyeing.

Problems to be Solved by the Invention The present invention aims at dyeing mixed fibers of hydroxyl group-containing fibers or amino group-containing fibers and anionic group-containing fibers using laI dyes. The purpose of the present invention is to provide a pyridone-based monoazo compound that can be dyed simultaneously.

Means for Solving the Problems The present invention provides the following general formula CI) (in which - or represents a hydrogen atom or a lower alkyl group,
-V represents an -ON group or a -○01ill group, -Y represents a substituted or unsubstituted alkyl group or an aralkyl group, -W represents a halogen atom or a lower alkyl group, and the difference is an alkylene group. , R3 represents an alkyl group, and 80 represents an anion. The gist is pyridone-based monoazo compounds represented by the following.

In the above general formula CI), examples of the lower alkyl group represented by -X or -R1 include a methyl group, an ethyl group, a linear or branched propyl group, and a butyl group.

Examples of the unsubstituted alkyl group represented by -Y include a methyl group, an ethyl group, a linear or branched alkyl group having 3 to lt carbon atoms, and examples of the substituted alkyl group include methoxyethyl methoxyethoxyethyl group, diethyl group in ethoxyethyl group, lower alkoxyalkoxyalkyl group in butoxyethoxyethyl group substituted with 3-hydroxy group or cyano group; and alkyl groups.

Examples of unsubstituted aral 1,000 groups include benzyl groups and phenethyl groups, and examples of substituted aral 1,000 groups include alkylbenzyl groups such as methylbenzyl groups, halogenated benzyl groups such as chlorobenzyl groups, and methoxybenzyl groups. Examples include alkoxybenzyl groups.

The halogen atom represented by -W includes a fluorine atom, a chlorine atom, and a bromine atom, and particularly preferably a fluorine atom.

Examples of the alkyl group represented by R1 or -Hs include methyl group and ethyl group, examples of the alkylene group represented by Bp include ethylene group and propylene group, and examples of the anion represented by Ao include halogen anion and methyl group. Examples include anions such as sulfate anion and ethyl sulfate anion.

The pyridone monoazo compound of the present invention represented by the general formula (I) is represented by the following general formula [■]C formula, where -X, -'I and -Y are as defined above. By reacting a pyridone-based monoazo compound represented by the following general formula (1) and -W with an 8-triazine compound represented by the same symbol as the above definition, the following general formula (C) is obtained: -X, -Y, - V, -W and -Q' are the same as the above definitions. ] A monoazo compound represented by the formula is produced, and then the monoazo compound and the general formula R3-A are combined.
・・・・・・・・・・・・・・・(V) (-Hs, A is the same as the above definition) and the alkylating agent represented by Q, It can be produced by heating and reacting for 3 to 3 hours, cooling the resulting reaction product system, and then filtering the resulting precipitate.

Examples of the alkali-containing agent represented by the above general formula [■] include dimethyl sulfate, diethyl sulfate, methyl bromide/', ethyl JL, methyl iodide, ethyl iodide, p-toluenesulfonic acid methyl ester,') A, acid triethyl ester, etc.

The amount of the alkylating agent to be used may range from 1,Q to 1.1 times the mole of the monoazo compound represented by the above general formula.

Further, examples of the organic solvent used in the above manufacturing method include acetone, methyl ethyl ketone, dioxane, tetrahydrofuran, toluene, chlorobenzene, dichlorobenzene, nitrobenzene, and the like.

Fibers that can be dyed with the uninvented pyridone-based monoazo compound represented by the above general formula CI) include natural fibers such as cotton and hemp, and semi-synthetic fibers such as viscose life rayon and copper ammonia rayon, which contain hydroxyl groups. Examples include amino-based fibers such as wool, silk, synthetic polyamide and polyurethane fibers, and anionic group-containing fibers such as acrylic fibers and cationically dyeable polyester fibers.

In particular, blended products, mixed fiber products, and mixed products of the above-mentioned hydroxyl group-containing fibers or amino group-containing fibers and anionic group-containing fibers are mentioned.

In carrying out dyeing, the aqueous solution of Ill can be used as it is as a dye bath in the dip dyeing method, as a padding bath in the padding dyeing method, and in combination with a sizing agent as a dark color paste in the textile printing method. Can be used heavily.

When carrying out padding dyeing or printing of mixed fibers of hydrocarbon fibers or amino group-containing fibers and acrylic fibers, it is necessary to use urea or polyhydric alcohols, or to combine dyes with human mixyl groups or amine groups. It is desirable to use an acid binder to accelerate the reaction.

The polyhydric alcohols have an average molecular weight of 200 to 3.
Examples include those in which the terminal hydroxyl group of a polyhydric alcohol such as polyethyl V glycol and polyp a pyrene glycol having a Qθ degree is dimethylated or diacetylated so as not to react with the dye.

Also,! ! As the binder, an alkali precursor compound that generates an alkali when heated in the presence of water, such as sodium acetate, is desirable.

The amount of urea or polyhydric alcohol to be used is approximately 3 to 30% by weight for the padding bath or printing dyeing paste, and the amount of sodium trichloroacetate used is based on the reactivity when W is a fluorine atom in the general formula [I'']. Since it is high, it is 0.3 to 0.3% by weight, and 1.Q to t3 for chlorine or bromine atoms.
Weight-degree is desirable.

The dye fixing method is 95℃ in the dip dyeing method.
Jθ~60 minutes at ~/30°C. For padding dyeing or textile printing, after drying, heat treatment with saturated steam at 100~IJQ°C for 3 minutes~IO minutes, or with hot air or superheated steam at 140~110°C for 30 seconds~IO minutes. Good.

Subsequently, by washing with hot water containing a common surfactant, a vivid and uniformly dyed product with good wet fastness can be obtained.

EXAMPLES Hereinafter, the present invention will be explained in more detail through examples.
The present invention is not limited to the following examples.

Implementation f! l! Compound S, Col shown by the following structural formula, and 3 g of dimethyl sulfate T, are reacted in 100 nl of dioxane at 30°C for 3 hours, and after cooling, the precipitated crystals are filtered to obtain a compound shown by the following structural formula. 6.0 g of pyridone monoazo compound of the present invention
I got it.

λmaw (I 0% methanol water) of this product is l
It was m.

Composition of printing dyeing paste Pyridone monoazo compound of the present invention t
ge% carboxyethyl cellulose water soluble a
zsg tetraethylene glycol dimethyl ether
tII sodium trichloroacetate
asp water
3! 1 total ioo g A printing dyeing paste with the above composition was prepared, and an acrylic/cotton (mixing ratio SO/!10) blended fabric was printed using a screen printing machine, and after intermediate drying for 3 minutes at go℃, superheated steam was applied. was used for 7 minutes at 10°C. After washing the product with water, it was soaped for 20 minutes at qo°C at a bath ratio of i:so using a cleaning solution containing 21/l of a nonionic surfactant (manufactured by Kao Soap Co., Ltd., (trademark) Scoremeal+e00).

In this way, a uniform yellow dyeing with excellent wet fastness was obtained.

EXAMPLE A pyridone-based monoazo compound of the present invention represented by the following structural formula was produced according to the method described in Example.

The λmax (0% methanol water) of this product is Dako snm.
Met.

Composition of padding bath Pyridone monoazo compound of the present invention with the above structure
I diethylene glycol thioether
tI! i! Sodium trichloroacetate
QJfi Zeng Total
A padding bath containing 100 g of the above composition was prepared and impregnated into an acrylic/6-nylon (mixing ratio of 7 to 0) blended fabric, which was squeezed to a squeezing rate of sθ% and fixed by steaming at 100° C. for 7 minutes. When this material was treated according to the method described in Example No., a yellow dyed product was obtained which was uniform, bright, and had excellent wet fastness.

Example 3 According to the method described in Example 1, a pyridone-based monoazo compound of the present invention represented by the following structural formula was produced.

This product's λma3c (g 0% methanol water) is DaJ
/nm.

Acrylic/wool (mixing ratio zo7z
o) The mixed fiber product was treated with QTC for 1 hour and then washed with hot water. A more uniform yellow dyed product with no irritation was obtained than with K.

Dyeing was carried out according to the method described in Example 1, except that the fibers used in Example 1 were changed to an acrylic/wool (mixing ratio of 3Q/0) blended fabric, resulting in a uniform yellow color with excellent wet fastness. A dyed product was obtained.

Example When dyeing was carried out according to the method described in Example 1 except that the fibers used in Example 1 were replaced with cotton cloth, a yellow dyed product with excellent wet fastness was obtained.

Packaging Example 6 The method described in Example 3 was followed except that the fibers and cone used in Example 3 were changed to cationically dyeable polyester/wool (mixing ratio 0/!0) blended fabric. [When dyed, a uniform yellow dyed product with excellent wet fastness was obtained.

Example 7 Dyeing was performed according to the method described in Example 7, except that the fibers used in Example 8 and 7 were changed to cotton/nylon/acrylic (mixing ratio 3θ/30/20) mixed woven fabric, resulting in uniform wet fastness. A uniform yellow dyeing with excellent strength was obtained.

Example g Using the pyridone-based monoazo compound of the present invention as shown in Table 7 below, which was prepared according to the method described in Example 1, the C10% methanol water) shown in Table 1 was prepared according to the method described in Example G. .

Claims (1)

[Claims] (1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
...... [I] (wherein -X represents a hydrogen atom or a lower alkyl group, -V represents a -CN group or -CO
NH_2 group, -Y represents a substituted or unsubstituted alkyl group or aralkyl group, -W represents a halogen atom, -Q represents a ▲mathematical formula, chemical formula, table, etc.▼ group or ▲mathematical formula, chemical formula, table, etc. etc. ▼ represents a group, R^1 represents a hydrogen atom or a lower alkyl group, and R^2
represents an alkylene group, R^3 represents an alkyl group, and A^■ represents an anion. ) A pyridone-based monoazo compound.