JPH1077424A - Monoazo compound and method for dyeing or printing hydrophobic fiber using the same - Google Patents

Abstract

(57) [Problem] To provide a clear blue disperse dye excellent in various fastnesses such as wet fastness and dyeability. SOLUTION: The following formula (I): (Wherein, X, Y and Z represent hydrogen, halogen, cyano, nitro, etc., R represents alkoxy, hydrogen, halogen, etc., and R ₁ and R ₂ represent hydrogen, unsubstituted alkyl, substituted alkyl, cyclohexyl, etc.) And a method of dyeing or printing a hydrophobic fiber using the compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a monoazo compound which, when used as a disperse dye, gives a blue dyed article having excellent properties such as light fastness and washing fastness.

[0002]

2. Description of the Related Art Japanese Unexamined Patent Publication No. 58-157863 discloses that
For example, the following equation (a)

[0003]

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[0004] A monoazo blue disperse dye represented by

[0005]

Heretofore, dyeings mainly composed of hydrophobic fibers dyed with a disperse dye have been required to have excellent basic properties such as light fastness and sublimation fastness. ing. In recent years, with the trend toward higher-grade consumer clothing, flexible processing to increase added value,
2. Description of the Related Art Various post-processing such as antistatic processing and texture improvement processing are actively performed. Since these post-processings are performed under high temperature conditions, the dyes in the fibers of the obtained dyed product bleed due to heat, and there is a problem in that the wet fastness, particularly the washing fastness, is reduced. Thus, a dyed product of a hydrophobic fiber material having excellent light fastness, sublimation fastness and wet fastness is required.For example, when dyed using the above-described monoazo-based disperse dye, the dyed product is obtained. There is a problem that the light fastness of the dyed product is insufficient.

[0006]

Means for Solving the Problems The present inventors can dye or print a hydrophobic fiber material such as polyester fiber in a deep blue color and have excellent light fastness, wet fastness, and especially washing fastness. As a result of intensive studies to find a compound that can provide a dyed product, it is found that a specific 2- (2-hydroxy-4-amino-phenylazo or 2-hydroxy-4-N-substituted amino-phenylazo) thiophene compound is effective. And completed the present invention.

That is, the present invention relates to the following formula (I)

[0008]

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[Wherein X is a hydrogen atom, a halogen atom,
Ano group, nitro group, formyl group, may be substituted
Linear or branched alkyl group, even if substituted
Good aryl group, optionally substituted alkylcarbo
A nyl group, an optionally substituted arylcarbonyl group,
An optionally substituted alkyloxycarbonyl group,
Optionally substituted carbamoyl group, optionally substituted
A good alkylsulfonyl group or an optionally substituted
Represents a reelsulfonyl group, Y is a hydrogen atom, a halogen atom
, Cyano, nitro, formyl, substituted
A straight-chain or branched alkyl group, which may be substituted
An optionally substituted aryl group, an optionally substituted hydroxyl group,
Optionally substituted mercapto group, optionally substituted
A good alkylcarbonyl group, an optionally substituted ant
Carbonyl group, optionally substituted alkyloxy
Sicarbonyl group or formula -SO_TwoK (where K is archi
Group, alkenyl group, aryl group, chlorine atom, bromine atom
Hydroxyl, an optionally substituted hydroxyl group or a substituted
Represents an optionally substituted amino group. ), Wherein Z is
Hydrogen, halogen, cyano, nitro, substituted
A linear or branched alkyl group,
Aryl group which may be substituted, which may be substituted
Alkyloxy group, optionally substituted alkyl carb
Bonyl group, arylcarbonyl which may be substituted
Group, optionally substituted alkyloxycarbonyl
Group, aryloxycarbonyl which may be substituted
Group, an optionally substituted carbamoyl group,
Optionally substituted alkylsulfonyl group or substituted
Represents a good arylsulfonyl group, wherein X, Y and Z are the same
Sometimes it is not a hydrogen atom. R is a hydrogen atom, halogen
R represents an atom or an alkoxy group; ₁ And R_TwoAre each other
Same or different, hydrogen atom, may be substituted
Linear or branched alkyl group, cyclohexyl
Group, alkenyl group which may be substituted or tetrahydrido
Represents a rofurfuryl group,₁ And R_TwoAre these combined
May form a morpholino group together with the nitrogen atom. However
Then R₁ Is a methoxycarbonylethyl group and R_Two
Is a hydrogen atom, X is a formyl group, and Y is hydrogen
An atom and Z cannot be a phenylcarbonyl group
No. Also, R₁ And R_TwoIs simultaneously an ethyl group, X
And Z are simultaneously a nitro group and Y is a hydrogen atom
X is a formyl group, Y is a methyl group and Z is
Nor is it a toxic carbonyl group. ]
Noazo compound and hydrophobic fiber material using this compound
A method for dyeing or printing a material is provided. Hereinafter, the present invention
Will be described in detail.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION As the substituents of the alkyl group, alkyloxy group, alkylcarbonyl group, alkyloxycarbonyl group and alkylsulfonyl group represented by X, Y and Z, for example, C _1-4 alkoxy group, hydroxy Groups, a phenyl group, a phenoxy group, a chlorine atom, a bromine atom and a benzyloxy group. Similarly, examples of the substituent of the aryl group, arylcarbonyl group and arylsulfonyl group represented by X, Y and Z include C _1-4
Examples include an alkyl group, a C _1-4 alkoxy group, a chlorine atom, a bromine atom and a nitro group. Further, as a substituent of the hydroxyl group, carbamoyl group, mercapto group and amino group represented by X, Y, Z and K, for example, C _1-4 alkyl group,
Examples include a hydroxy C _1-4 alkyl group, a cyclohexyl group, a phenyl group, a tolyl group, and a benzyl group.

In the above formula (I), X is a halogen atom, especially a chlorine atom or a bromine atom, a cyano group, a nitro group,
Formyl group, an optionally substituted alkylcarbonyl group, particularly an alkylcarbonyl group having a linear or branched C _1-4 alkyl, an optionally substituted arylcarbonyl group, especially a benzoyl group, Alkyloxycarbonyl groups, especially linear or branched C
An alkyloxycarbonyl group having an alkyl of _1-4 ,
An optionally substituted carbamoyl group, especially an unsubstituted carbamoyl group, an optionally substituted alkylsulfonyl group, especially a linear or branched C _1-4 alkylsulfonyl group, and an optionally substituted aryl Sulfonyl groups, especially phenylsulfonyl groups, are preferred. Among them, a cyano group, a nitro group and a formyl group are particularly preferred.

Similarly, among Y, a hydrogen atom, a halogen atom, especially a chlorine atom or a bromine atom, a linear or branched alkyl group which may be substituted, especially a C _1-4 alkyl group, A good aryl group, especially a phenyl group which may be substituted, an alkylcarbonyl group which may be substituted, particularly an alkylcarbonyl group having a linear or branched C _1-4 alkyl, which may be substituted An alkyloxycarbonyl group, particularly an alkyloxycarbonyl group having a linear or branched C _1-4 alkyl, an optionally substituted arylcarbonyl group, especially an optionally substituted phenylcarbonyl group are preferred. Among these, a hydrogen atom and a methyl group are particularly preferred.

Similarly, Z is a hydrogen atom, a cyano group, a nitro group, an optionally substituted alkylcarbonyl group, especially an alkylcarbonyl group having a linear or branched C _1-4 alkyl, An arylcarbonyl group which may be substituted, particularly an optionally substituted phenylcarbonyl group,
An optionally substituted alkyloxycarbonyl group, especially a linear or branched alkyloxycarbonyl group having a C _1-4 alkyl, and an optionally substituted aryloxycarbonyl group, especially an optionally substituted Good phenyloxycarbonyl groups are preferred. In particular cyano group Of these, nitro group, an alkyloxycarbonyl group having a linear or branched alkyl group having alkyl of C _1-4, and linear or alkyl branched C _1-4 preferable.

Among R in the formula (I), a hydrogen atom and an alkoxy group, particularly a C _1-4 alkyloxy group, are preferred, and a hydrogen atom is particularly preferred.

In the above formula (I), the groups represented by R ₁ and R ₂ include, for example, chlorine atom, bromine atom, cyano group, alkyloxy group, hydroxy group, phenoxy group,
One or two selected from the group consisting of phenyl, benzyloxy, alkoxycarbonyl, alkoxycarbonyloxy, alkanoyloxy, benzoyloxy, phenoxycarbonyloxy, alkanoyl, alkoxyalkoxycarbonyl and alkoxyalkoxy groups Linear or branched C _1-6 alkyl group which may be substituted by one substituent, a hydrogen atom,
Examples include a cyclohexyl group, an allyl group, and a tetrahydrofurfuryl group.

Among these linear or branched C _1-6 alkyl groups, unsubstituted ones include, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, Examples thereof include an i-butyl group, an n-pentyl group, an i-pentyl group, and an n-hexyl group. Further, among the linear or branched C _1-6 alkyl groups, those substituted by one substituent selected from the above-mentioned groups include, for example,
A chloro (or bromo) substituted alkyl group such as a 3-chloro (or bromo) propyl group or a 2-chloro (or bromo) ethyl group; a cyano-substituted alkyl group such as a 2-cyanoethyl group; 2- [methoxy (or ethoxy) )] Ethyl group or 3- [methoxy (or ethoxy)]
A C _1-4 alkoxy-substituted alkyl group such as a propyl group;
Hydroxy-substituted alkyl groups such as 2-hydroxyethyl group, 2- (or 3-) hydroxypropyl group and 4-hydroxybutyl group; phenoxy-substituted alkyl groups such as 2-phenoxyethyl group, phenethyl group and benzyl group or phenyl Substituted alkyl group; C such as 2-acetoxyethyl group, 4-acetoxybutyl group, 2-propionyloxyethyl group and 2-benzoyloxyethyl group;
_2-5 alkanoyloxy-substituted alkyl or benzoyloxy-substituted alkyl; alkoxy (C) such as 2- [methoxy (or ethoxy)] carbonylethyl
_1-4 ) carbonyl-substituted alkyl group; alkoxy (C _1-4 ) carbonyloxy-substituted alkyl group such as 2- [methoxy (or ethoxy)] carbonyloxyethyl group and 2-phenoxycarbonyloxyethyl group or phenoxycarbonyloxy substitution Alkyl group; _C2-5 alkanoyl-substituted alkyl group such as 2-acetylethyl group and 2-propionylethyl group; 2- (2-methoxyethoxy) ethyl, 2- (2-ethoxyethoxy) ethyl,
Alkoxy (C _1-4 ) alkoxy (C _1-4 ) -substituted alkyl groups such as-(2-butoxyethoxy) ethyl; and alkoxy (C _1-4 ) such as 2- (2-methoxyethoxycarbonyl) ethyl And alkoxy (C _1-4 ) carbonyl-substituted alkyl groups.

Further, among the linear or branched C _1-6 alkyl groups represented by R ₁ and R ₂ , those substituted by two substituents selected from the aforementioned groups include: For example, a 3-phenoxy-2-hydroxypropyl group, 3
-Methoxy-2-hydroxypropyl group, 3-butoxy-2-hydroxypropyl group, 3-methoxy-2-acetoxypropyl group and 3-ethoxy-2-acetoxypropyl group.

The monoazo compound represented by the formula (I) is, for example, a compound represented by the formula (II)

[0019]

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(Wherein, X, Y and Z have the same meanings as described above). The 2-aminothiophenes are diazotized by a conventional method, and the obtained diazotized product is then converted to the following formula (III)

[0021]

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(Wherein, R, R ₁ and R ₂ have the same meanings as described above). The formula
The 2-aminothiophenes represented by (II) are known compounds, for example, JP-A-48-81851 and JP-B-55-1871.
No. 0, JP-A-1-153668 and JP-A-6-2522
It can be produced according to the method described in Japanese Patent Publication No. 0-205.
The 3-aminophenol represented by the formula (III) is
For example, the following formula (IV)

[0023]

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(Wherein R has the same meaning as described above), a compound represented by the following formula (V) R ₁ -X ₁ (V) (wherein R ₁ has the same meaning as described above. X ₁ Represents a group which is eliminated / substituted by a nucleophilic reaction, such as a chlorine atom, a bromine atom, an iodine atom, a tosyl group and a benzenesulfonyloxy group), and the following formula (VI) R ₂ -X ₂ (VI) (wherein, R ₂ has the same meaning as described above. X ₂ is a group which is eliminated or substituted by a nucleophilic reaction such as a chlorine atom, a bromine atom, an iodine atom, a tosyl group, and a benzenesulfonyloxy group. By reacting a compound represented by the formula:

The monoazo compound of the present invention represented by the above formula (I) is useful for dyeing or printing a hydrophobic fiber material, particularly a polyester fiber material. For example, a dye dispersion is obtained by pulverizing fine particles together with a condensate of naphthalenesulfonic acid and formaldehyde or ligninsulfonic acid in an aqueous medium. The dye dispersion can be used as it is, or in the form of powder by spray-drying or the like. Dyeing, especially dip dyeing, a pH adjusting agent, a leveling agent and the like are added as necessary to a dyeing bath in which the monoazo compound of the present invention is dispersed in an aqueous medium, and then the hydrophobic fiber material is immersed. For polyester fiber,
Under pressure, usually 105 ° C. or higher, preferably 110 to 14
It can be performed in a temperature range of 0 ° C. Dyeing can also be performed at a relatively high temperature, for example, in the boiling state of water, in the presence of a carrier such as o-phenylphenol, trichlorobenzene or methylnaphthalene. Further, a so-called thermosol dyeing method in which the dye dispersion is padded on a cloth and then subjected to steaming or dry heat treatment at a temperature of 100 ° C. or higher is also applicable.

On the other hand, printing can be carried out by kneading a dye dispersion with an appropriate glue, padding it with a cloth, and performing steaming or thermosol treatment. A solvent dyeing method using an organic solvent such as trichloroethylene or perchlorethylene as a dyeing medium is also possible.

In applying the monoazo compound represented by the formula (I) of the present invention to dyeing or printing, it is needless to say that other dyes may be used in combination and dyeing may be carried out. A compounding agent may be added. Various post-processing such as softening processing, water-repellent processing, texture improvement processing, antistatic processing, and sanitary processing can also be performed on the obtained dyed product, if necessary.

The monoazo compound of the present invention represented by the formula (I) is less likely to be decomposed due to a variation in dyeing bath pH, and can dye a hydrophobic fiber material such as a polyester fiber material in a dark color with good reproducibility. Then, a clear blue dyeing obtained by dyeing or printing a hydrophobic fiber material such as a polyester fiber material using the compound is excellent in various fastnesses such as light fastness, sublimation fastness, and wet fastness. In particular, it has a feature that the washing fastness does not decrease even in heat setting or post-processing. For example, when a polyester fiber material is dyed in a dark color (JIS 2/1 density) and then heat-set, the washing fastness is lower than that of existing dyes even under test conditions (AATCC IIA method, etc.) corresponding to household washing. Notably better. In addition, when the monoazo compound of the present invention is used, ultrafine fibers such as microfibers, particularly polyester fibers having a denier of 1 denier or less, polyester fibers composed of irregular cross-section yarns, different shrinkage blended yarns or multiphase hybrid yarns, High-speed spun fibers, especially new hydrophobic fiber materials such as polyester fibers spun at a speed of 6000 m / min or more, can be dyed relatively easily in a dark color, as well as excellent robustness. Color, in particular a blue dyeing exhibiting fastness to washing.

[0029]

Industrial Applicability The monoazo compound of the present invention is suitably used for dyeing or printing a hydrophobic fiber material such as a polyester fiber. According to the method of the present invention, a dyed product of a blue color having excellent darkness and various fastnesses is obtained. Or a printed matter is obtained.

[0030]

EXAMPLES Next, the present invention will be described more specifically with reference to examples, but the present invention is not limited to the following examples. In the examples, parts are parts by weight, and% is% by weight.

Example 1 2-amino-3-cyano-5-nitrothiophene 1.6
9 parts, 2 parts of propionic acid and 8 parts of acetic acid were cooled to 5 ° C. or lower, and 2.95 parts of 43% nitrosylsulfuric acid was added dropwise to the mixture at 10 ° C. or lower. After the addition was completed, the mixture was further stirred at 5 ° C. The obtained diazo solution was added dropwise to a solution of 1.66 parts of 3-diethylaminophenol and 70 parts of methanol under ice-cooling. After completion of the dropwise addition, the reaction mixture was stirred for 1 hour under ice-cooling, and the precipitated crystals were separated by filtration, washed with methanol, and treated with the following formula.

[0032]

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A monoazo compound represented by the following formula was obtained. An ethanol solution of this compound exhibited a blue color (λmax = 603 nm).
).

Example 2 1.0 part of the monoazo compound obtained in Example 1 was dispersed and atomized in an aqueous medium together with 3.0 parts of a naphthalenesulfonic acid and a formaldehyde condensate. 10 parts of tetron jersey (polyester cloth, product of Toray Industries, Inc.) was added to a dye bath containing 0.6 part of a powder obtained by drying the dye dispersion, and the resulting mixture was pressurized at 130 to 135.
Staining was performed at 60 ° C for 60 minutes. The dyed product is then subjected to a reduction washing treatment at 85 ° C. for 10 minutes with a treatment solution consisting of 3 parts of caseide, 3 parts of hydrosulfite, 3 parts of a betaine-type amphoteric surfactant and 3,000 parts of water, followed by washing with water and drying. The bright dark blue dyeings were excellent in sublimation fastness and wet fastness. The obtained dyed product was subjected to a soft antistatic treatment according to the following method. Sumitex softener in putt tank
A pad solution having a composition consisting of 10 g / L of LK-1 (softening agent manufactured by Sumitomo Chemical Co., Ltd.) and 5 g / L of Sumistat F-1 (antistatic agent manufactured by Sumitomo Chemical Co., Ltd.) was prepared. After soaking the dyed material, it was squeezed uniformly to a weight gain of 80%. The dyed material was immersed in the solution again, squeezed in the same manner, dried in the middle at 80 ° C. for 2 minutes, and heat-set at 170 ° C. for 1 minute. The wash fastness of the dyed product after the post-processing was excellent. In addition, the light fastness of the dyed material before post-processing,
It measured according to the method of JIS L0842 using a carbon arc lamp as a light source. The results are shown in Table 1 below.

Comparative Example 1 The dye represented by the formula (a) described in JP-A-58-1557863 was dyed in the same manner as in Example 2 above, and the resulting dyed product was post-processed. The lightfastness of the previous dyed product was measured. The results are shown in Table 1 below.

[0036]

[Table 1]

Example 3 To 1.3 parts of the monoazo compound obtained in Example 1, 3.7 parts of ligninsulfonic acid was added and atomized and dispersed. 35 parts of hot water and 60 parts of a half emulsion paste having the following composition were mixed. To adjust the printing paste. 0 / W emulsion 300 parts Maypro gum NP 12% paste 694 parts Sodium chlorate 4 parts Tartaric acid 2 parts Total 1000 parts High temperature steel at normal pressure after
Steaming at 170 ° C. for 7 minutes with a marker to fix the mixture, and then performing a reduction cleaning treatment according to the method described in Example 2.
Washing, softening, and antistatic processing were performed in this order. The resulting clear dark blue dyed product was excellent in wet fastness, light fastness and sublimation fastness.

Example 4 3-Diethylaminophenol was replaced with 1.66 parts of 3-
Except that 2.8 parts of N, N-di- (2-methoxycarbonylethyl) aminophenol was used, the following formula was used in the same manner as in Example 1.

[0039]

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A monoazo compound represented by the following formula was obtained. An ethanol solution of the compound showed a blue color (λmax = 590 nm).
). The dyed product obtained by using this monoazo compound in the same manner as in Example 2 had excellent washing fastness, light fastness and sublimation fastness.

Example 5 3-N-ethyl-N- (2-phenoxyethyl) aminophenol in place of 3-diethylaminophenol
Except for using 6 parts, the following formula was used in the same manner as in Example 1.

[0042]

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A monoazo compound represented by the following formula was obtained. An ethanol solution of this compound exhibited a blue color (λmax = 600 nm).
). The dyed product obtained by using this monoazo compound in the same manner as in Example 2 had excellent washing fastness, light fastness and sublimation fastness.

Examples 6 to 112 The following Tables 2 to 3 were used in place of 3-diethylaminophenol.
In the same manner as in Example 1 except that 3-aminophenols having the substituents shown in columns 2 to 4 of 10 are used, the following formula (VII)

[0045]

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(Wherein R ₃ and R ₄ have the meanings described in Table 2 to Table 10). Ph in Tables 6 to 12 represents a phenyl group.

[0047]

[Table 2]

[0048]

[Table 3]

[0049]

[Table 4]

[0050]

[Table 5]

[0051]

[Table 6]

[0052]

[Table 7]

[0053]

[Table 8]

[0054]

[Table 9]

[0055]

[Table 10]

Example 113 The procedure of Example 1 was repeated, except that 1.86 parts of 2-amino-3-cyano-4-chloro-5-formylthiophene was used instead of 2-amino-3-cyano-5-nitrothiophene. Lower

[0057]

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A compound represented by the following formula was obtained. An ethanol solution of this compound exhibited a reddish blue color (λmax = 580 nm).
The dyed product obtained in the same manner as in Example 2 using this compound had excellent washing fastness, light fastness and sublimation fastness.

Examples 114 to 170 2-aminothiophenes represented by the formula (II) having substituents of X, Y and Z shown in columns 2 to 4 of the following table and those shown in columns 5 to 7 Is reacted with a 3-aminophenol represented by the formula (III) having substituents of R, R ₁ and R ₂ according to the method of Example 1 to obtain a monoazo compound corresponding to the general formula (I) Is obtained.

[0060]

[Table 11]

[0061]

[Table 12]

Example 171 1.0 part of the monoazo compound obtained in Example 1 was dispersed and atomized in an aqueous medium together with 3.0 parts of a formaldehyde condensate of naphthalenesulfonic acid. To a dyeing bath containing 1.2 parts of a powder obtained by drying the obtained dispersion, 10 parts of a woven fabric of polyester fibers having a fiber diameter of 2 denier and 0.01 denier was added, and 13 parts of
Stained at 0-135 ° C for 60 minutes. Next, the dyed product was treated at 85 ° C. with a treating solution consisting of 3 parts of caustic soda, 3 parts of hydrosulfite, 3 parts of a betaine-type amphoteric surfactant and 3,000 parts of water at 85 ° C.
After performing reduction washing treatment for 1 minute, washing with water and drying, a dyed material having the same color and the same density between different deniers was obtained. The resulting clear dark blue dyed product was excellent in light fastness, sublimation fastness and wet fastness.

Example 172 1.0 part of the monoazo compound obtained in Example 1 was dispersed and atomized in an aqueous medium together with 3.0 parts of a formaldehyde condensate of naphthalenesulfonic acid. A polyester woven fabric spun into a dye bath containing 0.9 parts of a powder obtained by drying the obtained dispersion.
10 parts were added and dyed under pressure at 130 DEG-135 DEG C. for 60 minutes.
Next, the obtained dyed product was treated in the same manner as in Example 172 to obtain a clear dark blue dyed product. This dyed product was excellent in light fastness, sublimation fastness and wet fastness.

Claims (6)

[Claims] (1) The following formula (I): [In the formula, X is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a formyl group, a linear or branched alkyl group which may be substituted, an aryl group which may be substituted, An optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted carbamoyl group, an optionally substituted alkylsulfonyl group or a substituted Represents an arylsulfonyl group, Y is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a formyl group, a linear or branched alkyl group which may be substituted, an aryl group which may be substituted, A hydroxyl group which may be substituted, a mercapto group which may be substituted, an alkylcarbonyl group which may be substituted, Which may be an aryl group, an optionally substituted alkyloxycarbonyl group, or the formula -SO ₂ K (here, K is an alkyl group, an alkenyl group, an aryl group, a chlorine atom, a bromine atom, substituted Z represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an optionally substituted straight-chain or branched-chain group, which represents an optionally substituted hydroxyl group or an optionally substituted amino group. Alkyl group, optionally substituted aryl group, optionally substituted alkyloxy group, optionally substituted alkylcarbonyl group, optionally substituted arylcarbonyl group, optionally substituted alkyloxy A carbonyl group, an optionally substituted aryloxycarbonyl group, an optionally substituted carbamoyl group, It is also represents an alkylsulfonyl group, or an optionally substituted arylsulfonyl group, no X, Y and Z are hydrogen atoms at the same time. R represents a hydrogen atom, a halogen atom or an alkoxy group; R ₁ and R ₂ are the same or different from each other and are a hydrogen atom, a linear or branched alkyl group which may be substituted, a cyclohexyl group, Represents an optionally substituted alkenyl group or a tetrahydrofurfuryl group, and R ₁ and R ₂ may form a morpholino group together with the nitrogen atom to which they are bonded. However, when R ₁ is a methoxycarbonylethyl group and R ₂ is a hydrogen atom, X is not a formyl group, Y is a hydrogen atom and Z is not a phenylcarbonyl group. When R ₁ and R ₂ are simultaneously ethyl groups, X and Z are not simultaneously a nitro group and Y is not a hydrogen atom, but X is a formyl group, Y is a methyl group and Z is an ethoxy group. Nor is it a carbonyl group. A monoazo compound represented by the formula: 2. X is a halogen atom, a cyano group, a nitro group,
Formyl group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted carbamoyl group, an optionally substituted alkyl A sulfonyl group or an optionally substituted arylsulfonyl group, wherein Y is a hydrogen atom, a halogen atom,
A linear or branched alkyl group which may be substituted, an aryl group which may be substituted, an alkylcarbonyl group which may be substituted, an arylcarbonyl group which may be substituted or A good alkyloxycarbonyl group, wherein Z is a hydrogen atom, a cyano group,
A nitro group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkyloxycarbonyl group or an optionally substituted aryloxycarbonyl group,
And R is a hydrogen atom or an alkoxy group.
The monoazo compound according to the above. (3) Y is a hydrogen atom, a linear or branched alkyl group which may be substituted, an aryl group which may be substituted, an alkylcarbonyl group which may be substituted or The monoazo compound according to claim 1 or 2, which is a good arylcarbonyl group. 4. A method for dyeing or printing a hydrophobic fiber material using the monoazo compound according to claim 1, 2 or 3. 5. The method according to claim 4, wherein the hydrophobic fiber material comprises polyester fibers of 1 denier or less. 6. The method according to claim 4, wherein the hydrophobic fiber material comprises polyester fibers spun at a speed of 6000 m / min or more.