DE19727442A1 - Monoazo compound and process for dyeing or printing a hydrophobic fiber using the same - Google Patents

Abstract

A monoazo compound is disclosed which gives a clear blue dyed-product superior in various fastnesses (such as wet fastness and light fastness) and which is represented by the following formula (1): wherein X, Y and Z respectively represent hydrogen, halogen, cyano or nitro, etc. (see claim 1); R represents alkoxy, hydrogen or halogen; and R 1 and R 2 represent hydrogen, optionally substituted alkyl, cyclohexyl, optionally substituted alkenyl, or a tetrahydrofurfuryl group, or R 1 and R 2 , together with the nitrogen atom to which they are attached, is a morpholino group. A method for dyeing or printing a hydrophobic fiber material, comprising using the compound, is also disclosed.

Description

The present invention relates to a monoazo compound when in use as a disperse dye gives a blue colored product which is excellent in various properties, such as light fastness and wash resistance is.

For a dyed product, which mainly comprises hydrophobic fibers with dyed a disperse dye, have been good basic properties, such as Lightfastness and sublimation resistance, required. Although JP-A-58-157863 a Monoazo blue disperse dye of, for example, the following formula (a)

discloses the light fastness of a dyed product which is compatible with the monoazo blue Disperse dye was colored, insufficient.

With the recent increasing demand for textiles and fabrics higher Quality, have been reinforced various post-treatments to improve additional Features, such as treatment for softening, anti-static treatments and Treatments to improve the feel of the fabric performed. Because these Nachbe Performed at high temperature, the dye bleeds in the fibers  of the colored product due to the heat during the treatments, resulting in a Deterioration of the wet fastness, especially washing resistance, the result.

Thus, the object of the present application was to provide a connection to To provide a hydrophobic fiber material, such as polyester fibers, with dark dye or print blue dye, giving a dyed product with excellent Light fastness and wet fastness, especially wash resistance is obtained. Solved This object is achieved by finding a particular 2- (2-hydroxy-4-amino phenylazo or 2-hydroxy-4-N-substituted aminophenylazo) thiophene compound.

The present invention provides a monoazo compound represented by the following formula (I) ready:

in the X, a hydrogen atom, a halogen atom, a cyano group, a nitro group, a Formyl group, an optionally substituted straight-chain or branched alkyl rest, an optionally substituted aryl radical, an optionally substituted Alkylcarbonylrest, an optionally substituted arylcarbonyl, a given optionally substituted alkyloxycarbonyl, an optionally substituted carba moylgruppe, an optionally substituted Alkylsulfonylrest or a given when substituted arylsulfonyl, Y is a hydrogen atom, a halogen atom, a Cyano group, a nitro group, a formyl group, an optionally substituted one straight-chain or branched alkyl radical, an optionally substituted aryl radical, a optionally substituted hydroxyl group, an optionally substituted Mercapto group, an optionally substituted alkylcarbonyl, a optionally substituted arylcarbonyl radical, an optionally substituted alk yloxycarbonyl radical or a radical of the formula -SO₂K in which K is an alkyl radical, an alkenyl group, an aryl group, a chlorine atom, a bromine atom, an optionally represents substituted hydroxyl group or an optionally substituted amino group, Z is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a optionally substituted straight-chain or branched alkyl radical, a ge optionally substituted aryl radical, an optionally substituted alkyloxy radical optionally substituted alkylcarbonyl, an optionally substituted Arylcarbonylrest, an optionally substituted Alkyloxycatonylrest, a  optionally substituted aryloxycarbonyl radical, an optionally substituted car bamoyl group, an optionally substituted alkylsulfonyl or a given optionally substituted arylsulfonyl radical, with the proviso that X, Y and Z are not represents a hydrogen atom, R represents a hydrogen atom, a halogen atom or represents an alkoxy radical, and R₁ and R₂, which are the same or different from each other, each a hydrogen atom, an optionally substituted straight-chain or branched alkyl group, a cyclohexyl group, an optionally substituted Al kenylrest or a tetrahydrofurfuryl group, or R₁ and R₂ together with the nitrogen atom to which they are attached, can form a morpholino group, with with the proviso that when R₁ is a methoxycarbonylethyl group and R₂ is a What is hydrogen, not simultaneously X is a formyl group, Y is a hydrogen atom and Z is a Phenylcarbonylgruppe, and with the proviso that when R₁ and R₂ are the same represent an ethyl group, not simultaneously X is a nitro group, Y is a hydrogen atom and Z represents a nitro group and not simultaneously X is a formyl group, Y a Methyl group and Z represents an ethoxycarbonyl group.

The present invention also provides a process for dyeing or printing a hydrophobic fibrous material, which is the use of the inventive Monoazo compound.

Unless otherwise indicated, an alkyl radical in the definition of formula (I) contains generally 1-6 carbon atoms, preferably 1-4 carbon atoms; one Alkenyl radical is generally 2-6 carbon atoms, preferably 2-4 carbon atoms, and aryl radicals are preferably phenyl radicals.

Examples of Substituent of Alkyl Alkyloxy, Alkylcarbonyl, Al kyloxycarbonyl groups and alkylsulfonyl groups represented by X, Y or Z, include a C₁-C₄ alkoxy group, a hydroxyl group, phenyl group, phenoxy group, a chlorine atom, bromine atom and a benzyloxy group.

Examples of the substituent of the aryl group, arylcarbonyl group, aryloxycarbonyl group and arylsulfonyl radicals represented by X, Y or Z include a C₁- C₄-alkyl radical, C₁-C₄-alkoxy radical, a chlorine atom, bromine atom and a nitro group.

Examples of the substituent of the hydroxyl group, carbamoyl group, mercapto group and amino group, which are represented by X, Y, Z or K, close a C₁-C₄-alkyl radical, hydroxy-C₁-C₄-alkyl radical, a cyclohexyl group, phenyl group, Tolyl group and benzyl group.

Among the above mentioned by X in the formula (I) Re a halogen atom, in particular a chlorine atom or bromine atom, a cyano group, a nitro group, a formyl group, an optionally substituted alkyl carbonyl radical, in particular an alkylcarbonyl radical having a straight-chain or branched chain  C₁-C₄-alkyl radical, an optionally substituted arylcarbonyl radical, in particular a Benzoyl, an optionally substituted Alkyloxycarbonylrest, in particular one Alkyloxycarbonylrest with a straight-chain or branched C₁-C₄-alkyl radical, a optionally substituted carbamoyl group, in particular an unsubstituted Carbamoyl, an optionally substituted Alkylsulfonylrest, in particular one straight-chain or branched C₁-C₄-alkylsulfonyl radical and an optionally substituted arylsulfonyl, especially a phenylsulfonyl group, preferred. From that For example, a cyano group, a nitro group and a formyl group are particularly preferred.

Among those mentioned above, represented by Y in the formula (I) Rests are a hydrogen atom, a halogen atom, in particular a chlorine atom or Bromine, an optionally substituted straight-chain or branched alkyl radical, in particular a C₁-C₄-alkyl radical, an optionally substituted aryl radical, in particular an optionally substituted phenyl group, an optionally substituted alkyl carbonyl radical, in particular an alkylcarbonyl radical having a straight-chain or branched chain C₁-C₄-alkyl radical, an optionally substituted alkyloxycarbonyl radical, in particular a Alkyloxycarbonylrest with a straight-chain or branched C₁-C₄-alkyl radical, and a optionally substituted Arylcarbonylrest, in particular an optionally substi Phenylcarbonylgruppe tuierte, preferred. Of these, one is hydrogen and one Methyl group particularly preferred.

Among the above-mentioned Re represented by Z in the formula (I) are a hydrogen atom, a cyano group, a nitro group, an optionally substituted alkylcarbonyl radical, in particular an alkylcarbonyl radical having a straight chain or branched C₁-C₄-alkyl radical, an optionally substituted arylcarbonyl rest, in particular an optionally substituted phenylcarbonyl group, a gege optionally substituted alkyloxycarbonyl radical, in particular an alkyloxycarbonyl radical with a straight-chain or branched C₁-C₄-alkyl radical, and an optionally sub substituted aryloxycarbonyl radical, especially an optionally substituted phenyloxy carbonyl group, preferred. Among them are a cyano group, a nitro group, a Alkylcarbonylrest with a straight-chain or branched C₁-C₄-alkyl radical and a Alkyloxycarbonylrest with a straight-chain or branched C₁-C₄-alkyl radical stronger preferred and a cyano group is most preferred.

Among the above-mentioned Re represented by R in the formula (I) are a hydrogen atom and an alkoxy radical, in particular a C₁-C₄-alkyloxy radical, prefers. Among them, a hydrogen atom is particularly preferred.

In the above formula (I), examples of R₁ or R₂ include given radical is a straight-chain or branched C₁-C₆-alkyl radical or C₂-C₆- Alkenyl optionally substituted by one or two substituents selected from a  Chlorine atom, bromine atom, a cyano group, an alkyloxy group, a hydroxyl group, Phenoxy group, phenyl group, benzyloxy group, an alkoxycarbonyl group, alkoxy carbonyloxy, alkanoyloxy, benzoyloxy, phenoxycarbonyl-oxy, an alkanoyl group, an alkoxyalkoxycarbonyl group and an alkoxyalkoxy group, may be substituted, a hydrogen atom, a cyclohexyl group, an allyl group and a tetrahydrofurfuryl group. When R1 or R2 is an alkenyl radical, is a Alkyl radical preferred.

Examples of the unsubstituted C₁-C₆ alkyl represented by R₁ or R₂ radicals include a methyl group, ethyl group, n-propyl group, iso-propyl group, n- Butyl group, iso-butyl group, n-pentyl group, iso-pentyl group and n-hexyl group.

Examples of the substituted C₁-C₆ alkyl group represented by R₁ or R₂ include chlorine- or bromine-substituted alkyl radicals, such as a 3-chloro- or bromopropyl group, and 2-chloro or bromoethyl group, cyano-substituted alkyl radicals, such as a 2- Cyanoethyl group, C₁-C₄-alkoxy-substituted alkyl radicals, such as a 2- [methoxy or Ethoxy] ethyl group and 3- [methoxy or ethoxy] propyl group, hydroxy-substituted Alkyl radicals such as a 2-hydroxyethyl group, 2- or 3-hydroxypropyl group and 4-Hy hydroxybutyl group, phenoxy-substituted alkyl groups or phenyl-substituted alkyl groups, such as a 2-phenoxyethyl group, phenethyl group and benzyl group, C₂-C₅ alkanoyl oxysubstituted alkyl radicals or benzoyloxy-substituted alkyl radicals, such as a 2-acet oxyethyl group, 4-acetoxybutyl group, 2-propionyloxyethyl group and 2-benzoyl oxyethyl, alkoxy (C₁-C₄) carbonyl-substituted alkyl radicals, such as a 2- [methoxy or Ethoxy] carbonylethyl group, alkoxy (C₁-C₄) carbonyloxy-substituted alkyl radicals or phenoxycarbonyloxy-substituted alkyl radicals, such as a 2- [methoxy or ethoxy] - carbonyloxyethyl group and 2-phenoxycarbonyloxyethyl group, C₂-C₅ alkanoyl substituted alkyl radicals, such as a 2-acetylethyl group and 2-propionylethyl group, alkoxy (C₁-C₄) alkoxy (C₁-C₄) substituted alkyl radicals, such as a 2- (2-methoxyethoxy) ethyl, 2- (2- Ethoxyethoxy) ethyl and 2- (2-butoxyethoxy) ethyl group, and alkoxy (C₁-C₄) alkoxy (C₁- C₄) carbonyl-substituted alkyl radicals, such as a 2- (2-methoxyethoxycarbonyl) ethyl group, one.

Examples of represented by R₁ and R₂ C₁-C₆-alkyl radicals having two Substituents selected from the above radicals are substituted, include a 3- Phenoxy-2-hydroxypropyl group, 3-methoxy-2-hydroxypropyl group, 3-butoxy-2-hy hydroxypropyl group, 3-methoxy-2-acetoxypropyl group and 3-ethoxy-2-acetoxypropyl group.

The monoazo compound of the above formula (I) may be exemplified by Diazotization of 2-aminothiophenes of the formula (II):

in which X, Y and Z are as defined above, according to a conventional Method and coupling the resulting diazotized product with 3-aminophenols of following formula (III):

in which R, R₁ and R₂ are as defined above, can be prepared.

The 2-aminothiophenes of the formula (II) are known compounds and can for example, with one disclosed in JP-A-48-81851, JP-B-55-18710, JP-A-1-153668 or JP-A-6. 25 220 described methods are produced.

The 3-aminophenols of the formula (III) can be prepared, for example, by reacting a Compound of the formula (IV):

in which R has the meaning given above, with a compound of the following formula (V):

R₁-X₁ (V)

in which R₁ has the meaning given above, and X₁ represents a radical which is replaced by a nucleophilic reaction can be removed and substituted, such as a chlorine atom, Bromine atom, iodine atom, a tosyl group and a benzenesulfonyloxy group, and a Compound of the following formula (VI):

R₂-X₂ (VI)

in which R₂ has the meaning given above, and X₂ represents a radical which is replaced by a nucleophilic reaction can be removed and substituted, such as a chlorine atom, Bromine atom, iodine atom, tosyl group and benzenesulfonyloxy group.

The monoazo compound of the above formula (I) of the present invention is for Dyeing or printing on a hydrophobic fiber material, in particular polyester fiber material, suitable. A dye dispersion can be prepared by grinding the inventive Monoazo compound to fine particles in an aqueous medium, together with a suitable dispersants, such as a condensate of naphthalenesulfonic acid and Formaldehyde and lignosulfonic acid, according to a conventional method can be obtained. This dye dispersion may be as it is in the form of a liquid or after conversion be used in a powder by spray drying. Dyeing, in particular Dyeing can be achieved by dipping a hydrophobic fiber material in a dye bath be carried out by dispersing the monoazo compound of the invention in an aqueous medium and optionally adding a pH adjusting agent and a Dispersion leveling agent is prepared. In the case of a polyester fiber, dyeing becomes usually under elevated pressure at a temperature normally not below 105 ° C, preferably in the range of 110 to 140 ° C performed. Dyeing can also at a relatively high temperature, for. B. boiling point of water, in the presence of a carrier, such as o-phenylphenol, trichlorobenzene and methylnaphthalene. In addition, the so-called Thermosolfarbeverfahren of padding a cloth in one Dye dispersion, followed by steaming or dry heat treatment at a tem temperature of not less than 100 ° C are also applied.

On the other hand, the printing can be carried out by kneading the dye dispersion with a suitable sizing and padding a cloth using the resulting Mixture, followed by steaming or thermosol treatment. It is also possible, a solvent dyeing method using an organic Use solvent such as trichlorethylene or perchlorethylene, as a dyeing medium.

Other dyes may be used in combination with the monoazo compound of the formula (I) used for dyeing or printing. Various formulation examples  Constituents may also be added in the step of preparing the dye dispersion become.

The colored product may undergo various post-treatments, such as a treatment for softening, treatment for imparting water repellency, antistatic Treatment and treatment to improve the handle of the dyed product and Hygienic treatments (suppression of odor caused by sweat, dirt and the like, suppression of bacteria).

The degree of decomposition of the monoazo compound of the formula (I) is hardly exceeded a change in the pH in the dye bath affected. Accordingly, it is in the Use of the monoazo compound possible, the hydrophobic fiber material, such as Polyester fiber material to dye with dark color with good reproducibility. The dyed products with clear blue color, which are obtained by dyeing or printing the hy fibrous fibrous material, such as polyester fiber material, using the monoazo are obtained in different fastnesses, such as Light fastness, sublimation resistance and wet fastness. In particular, the Washing resistance not affected by heat setting or post-treatment. For example, even under the test conditions (eg AATCC, IIA method), the a washing in the household, the washing resistance when the polyesterfa Heat treatment after dyeing with dark color (JIS 2/1 Concentration) is significantly better than when a conventional dye is used. Using the monoazo compound of the present invention new hydrophobic fiber materials, for example a superfine fiber, such as microfiber, In particular, polyester fiber of 1 denier or less, polyester fiber of yarn with non-standard cross-section, mixed yarn with differential shrinkage or a mixed multiphase yarn and a fiber obtained by high-speed spinning, especially a polyester fiber obtained by spinning at a speed not below 6000 m / minute, relatively easily dyed with dark color, and a colored one Product with blue color with excellent different fastnesses, in particular Wash resistance, can be obtained.

As mentioned above, the monoazo compound of the invention is ge suitably for dyeing or printing a hydrophobic fiber material, such as poly ester fiber used. According to the method of the present invention, a blue dyed product or textile-printed product with dark color and excellent different fastnesses are obtained.

The following examples illustrate the present invention. In the Examples are, unless otherwise stated, "parts" and "%" by weight.  

example 1

A mixture of 1.69 parts of 2-amino-3-cyano-5-nitrothiophenone, 2 parts of Pro pionic acid and 8 parts of acetic acid was cooled to 5 ° C or less and then 2.95 Parts of 43% nitrosyl sulfuric acid dripped to the mixture while the temperature was kept at 10 ° C or less. Upon complete dropping, the mixture became further stirred at 5 ° C.

The resulting diazo solution became a solution of 1.66 with ice cooling Parts of 3-diethylaminophenol and 70 parts of methanol are added dropwise. After complete closing dropwise, the reaction mixture was stirred for 1 hour under ice-cooling. The shun which crystals were filtered and washed with methanol using a monoazover binding of the following formula:

was obtained. An ethanol solution of this compound showed blue color (λmax = 603 nm).

Example 2

1.0 part of the monoazo compound obtained in Example 1 was dissolved in an aq medium together with 3.0 parts of condensate of naphthalenesulfonic acid and Formaldehyde dispersed and atomized. The resulting dye dispersion was ge dried, whereby a powder was obtained. To a 6.0 parts of the powder containing Dye bath was 10 parts of Tetlon Jersey (polyester fabric, product made by Toray Co., Ltd.) and dyeing at 130 to 135 ° C under increased pressure for 60 Minutes. Then, the colored product became a reduction wash at 85 ° C for 10 minutes using a treatment solution consisting of 3 Share sodium hydroxide, 3 parts hydrosulfite, 3 parts amphoteric surfactant Betaine-type agent and 3000 parts of water were used, subjected to washing with water and dried to give a colored product of clear dark blue color. The dyed product was better in sublimation resistance and wet fastness. The The dyed product obtained was subjected to a softening-antistatic treatment according to subjected to the following procedure.

After a padding solution with a composition of 10 g / l Sumitec Softenate LK-1 (plasticizer, manufactured by Sumitomo Chemical Industries Co., Ltd.) and 5 g / l Sumistat F-1 (antistatic agent, manufactured by Sumitomo Chemical Industries  Co., Ltd.) in a pad container, the above became colored Product dipped in the container and uniformly expressed, so that the Weight gain was 80%. The dyed product was submerged, as well dried for 2 minutes at 80 ° C and then for 1 minute at 170 ° C. heat treated. The washing resistance of the obtained dyed product according to the Aftercare was excellent.

The light fastness of the dyed product before the post-treatment was under Use of a carbon arc lamp as a light source according to the method described in JIS L0842 measured procedures. The results are shown in Table 1.

Comparative Example 1

As described in Example 2, except that described in JP-A-58-157863 Dye of the above formula (a) was used, the dyeing was carried out. The light fastness of the obtained dyed product before the after-treatment was respectively measured. The results are shown in Table 1.

Table 1

Example 3

3.7 parts of the monoazo compound obtained in Example 1 were added to 3.7 parts Lignosulfonic acid and the mixture dispersed and atomized. The obtained Dispersion was mixed with 35 parts of hot water and 60 parts of a semi-emulsion simply mixed with the following composition to form a sizing agent manufacture.

O / W emulsion 300 parts Mayprogum NP 12% paste 694 parts sodium chlorate 4 parts tartaric acid 2 parts @ total 1000 parts

Using this sizing agent, Tetlon became Tropical (Polyester cloth, manufactured by Toray Co., Ltd.) printed, dyed and then 7 minutes steamed using a high-temperature damper at 170 ° C to the To fix sizing agents. Then the cloth was subjected to a reduction washing treatment, a Washing treatment, a softening treatment and an antistatic treatment, such as described in Example 2, subjected. The resulting colored product with clearer dark blue color was better in wet fastness, light fastness and sublimation permanence.

Example 4

As described in Example 1, except that 2.8 parts of 3-N, N-di (2-methoxycarbonyl ethyl) aminophenol instead of 1.66 parts of 3-diethylaminophenol were used Monoazo compound of the following formula:

receive. An ethanol solution of the compound showed blue color (λ max = 590 nm). One using this monoazo compound as described in Example 2 dyed product showed excellent washing resistance, light fastness and sublimation onsbeständigkeit.

Example 5

As described in Example 1 except that 2.6 parts of 3-N-ethyl- (2-phenoxyethyl) aminophenol instead of 3-diethylaminophenol were used, a monoazover binding of the following formula:

receive. An ethanol solution of the compound showed blue color (λ max = 600 nm). One using this Monazoverbindung as described in Example 2 obtained dyed product showed excellent washing resistance, light fastness and sublimation onsbeständigkeit.

Examples 6 to 112

As described in Example 1, except that 3-aminophenols with the in each case in column 2 to column 4 of Table 2 to Table 7 listed substituents instead of 3- Diethylaminophenol were used, each of the following formula (VII) was equivalent monoazo compound:

in the R₃ and R₄ the same meaning as defined in Table 2 to Table 10, on wise, received.

Ph in Table 2 to Table 7 represents a phenyl group.  

Table 2

Table 3

Table 4

Table 5

Table 6

Table 7

Example 113

As described in Example 1 except that 1.86 parts of 2-amino-3-cyano-4-chloro-5- Formylthiophen was used instead of 2-amino-3-cyano-5-nitrothiophene, a Compound of the following formula:

receive. An ethanol solution of the compound showed a reddish-blue color (λ max = 580 nm).

A obtained using this compound as described in Example 2, dyed product had excellent washing resistance, light fastness and Sublimation resistance.

Examples 114 to 170

When 2-aminothiophenes of the formula (II) with the in column 2 to column 4 of fol Table 8 described substituents X, Y and Z with 3-aminothiophenes of Formula (III) having the sub described in Column 5 to Column 7 of Table 8 below Substituents R, R₁ and R₂ are reacted, each of the general formula (I) ent obtained monoazo compound speaking.  

Table 8

Example 171

1.0 part of the monoazo compound obtained in Example 1 was used together with 3.0 Dividing a condensate of formaldehyde and naphthalenesulfonic acid in an aqueous Medium dispersed and atomized. The resulting dispersion was dried, taking a Powder was obtained. To a dye bath containing 1.2 parts of the powder were added 10 parts of a combined woven fabric of polyester fibers with a Fiber diameter of 2 denier and 0.01 denier and dying for 60 minutes elevated pressure at 130 to 135 ° C performed. Then the dyed product became a Reduction washing treatment using a treatment solution consisting of 3 Share sodium hydroxide, 3 parts hydrosulfite, 3 parts amphoteric surfactant Betaine-type agent and 3000 parts of water, subjected to 85 ° C for 10 minutes, with Water and dried, leaving a dyed product of the same color  property and the same concentration property between the different Fa serstärken was obtained. The resulting dyed product with a clear dark blue color was better in light fastness, sublimation resistance and wet fastness.

Example 172

1.0 part of the monoazo compound obtained in Example 1 was used together with 3.0 Parting a condensate of formaldehyde and naphthalenesulfonic acid in an aqueous Medium dispersed and atomized. The resulting dispersion was dried, whereby a powder was obtained. The dye bath containing 0.9 parts of the powder became 10 Parts of woven polyester fabric obtained by high-speed spinning, given and the dyeing was carried out under elevated pressure at 130 to 135 ° C for 60 minutes. Then the resulting dyed product was treated as described in Example 171, with a dyed product with clear dark blue color was obtained. The dyed product was better in light fastness, sublimation resistance and Wet fastness.

Claims (7)

A monoazo compound represented by the following formula (I): in the X represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a formyl group, an optionally substituted straight-chain or branched alkyl radical, an optionally substituted aryl radical, an optionally substituted alkylcarbonyl radical, an optionally substituted arylcarbonyl radical, an optionally substituted alkyloxycarbonyl radical, an optionally Y represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a formyl group, an optionally substituted straight-chain or branched alkyl group, an optionally substituted aryl group, an optionally substituted hydroxyl group, or a substituted carbamoyl group, an optionally substituted alkylsulfonyl group or an optionally substituted arylsulfonyl group optionally substituted mercapto group, an optionally substituted alkylcarbonyl, an optionally substituted arylcarbonyl, e in which optionally substituted alkyloxy carbonyl radical or a radical of the formula -SO₂K in which K represents an alkyl radical, an alkenyl radical, an aryl radical, a chlorine atom, a bromine atom, a GE optionally substituted hydroxyl group or an optionally substituted amino group, Z is a hydrogen atom, a halogen atom , a cyano group, a nitro group, an optionally substituted straight-chain or branched alkyl group, an optionally substituted aryl group, an optionally substituted alkyloxy group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted aryloxycarbonyl group, a optionally substituted carbamoyl group, an optionally substituted alkylsulfonyl radical or an unsubstituted or substituted arylsulfonyl radical, with the proviso that X, Y and Z are not gl eichzeitig represent a hydrogen atom, R represents a hydrogen atom, a halogen atom or an alkoxy radical, and R₁ and R₂, which are identical or different from each other, each represent a hydrogen atom, an optionally substituted straight-chain or branched alkyl radical, a cyclohexyl group, an optionally substituted alkenyl radical or represents a tetrahydrofurfuryl group, or R₁ and R₂ together with the nitrogen atom to which they are attached can form a morpholino group, with the proviso that when R _{1 is} a methoxycarbonylethyl group and R₂ is a hydrogen atom, then not simultaneously X is a formyl group, Y is a hydrogen atom and Z represents a phenylcarbonyl group, and provided that when R₁ and R₂ simultaneously represent an ethyl group, then X is not a nitro group, Y is a hydrogen atom and Z is a nitro group, and not simultaneously X is a formyl group, Y is a methyl group and Z is a Ethoxycarbo represents nylgruppe. 2. monoazo compound according to claim 1, in which X is a halogen atom, a cyano group, a nitro group, a formyl group, an optionally substituted one Alkylcarbonylrest, an optionally substituted Arylcarbonylrest, a gege optionally substituted alkyloxycarbonyl, optionally substituted Carbamoyl group, an optionally substituted alkylsulfonyl or a optionally substituted arylsulfonyl, Y is a hydrogen atom Halogen atom, an optionally substituted straight-chain or branched Alkyl radical, an optionally substituted aryl radical, an optionally substituted Alkylcarbonylrest, an optionally substituted Arylcarbonylrest or a optionally substituted Alkyloxycarbonylrest, Z is a hydrogen atom, a Cyano group, a nitro group, an optionally substituted alkylcarbonyl radical, an optionally substituted arylcarbonyl radical, an optionally substituted one Alkyloxycarbonylrest or an optionally substituted Aryloxycarbonylrest, and R is a hydrogen atom or an alkoxy radical. A monoazo compound according to claim 1 or 2, wherein Y is a hydrogen atom optionally substituted straight-chain or branched alkyl radical, a gege optionally substituted aryl radical, an optionally substituted alkylcarbonyl radical or an optionally substituted arylcarbonyl radical. 4. A method of dyeing or printing a hydrophobic fiber material to Grasping the use of the monoazo compound according to any one of claims 1 to Third   5. The method of claim 4, wherein the hydrophobic fiber material is a polyester fiber with not more than 1 denier. 6. The method according to claim 4, wherein the hydrophobic fiber material is a Polyester fiber, with a speed of not less than 6000 m / min. was spun. 7. A process for preparing a monoazo compound according to any one of claims 1 to 3, which comprises diazotizing 2-aminothiophene of formula II: in which X, Y and Z have the meaning given in claims 1 to 3 in a manner known per se and coupling of the resulting diazotized product with 3-aminophoenols of the following formula (III): in which R, R₁ and R₂ have the meanings given in claims 1 to 3.