Monoazo disperse dye compounds, their production and their use

Abstract: A monoazo compound of the formula, wherein D is a heterocyclic or carbocyclic compound residue such as benzothiazolyl and phenyl, X is hydrogen, alkyl, alkoxy, halogeno, acylamino or the like, Y is hydrogen, halogeno, alkyl, alkoxy and the like, R₁ is alkyl, R₂ is C₂-C₄ alkylene, B is a bridging group such as - -, -O-, -S-, C₁-C₆ alkylene and the like, and W₁, W₂, W₃, Z₁, Z₂ and Z₃ are independently hydrogen, alkyl, halogeno or the like, which is useful for dyeing hydrophobic fiber materials to give dyed or printed product of a deep color excellent in fastness properties, particularly those such as washing fastness, even after various finishing treatments of the product.

Description: The present invention relates to a monoazo compound, a process for producing the same and a process for dyeing or printing hydrophobic fiber materials therewith. More specifically, the present invention relates to a monoazo compound useful as a disperse dye for dyeing or printing hydrophobic fiber materials, particularly those such as polyester fiber materials. With recent consumers' trend toward higher grade apparels, there is a great need for disperse dyes to be superior in dyeability and dye characteristics and have extensive applicability and capability of giving dyed or printed products excellent in their fastness properties. Under these circumstances, hydrophobic fiber materials or hydrophobic fiber-containing materials dyed or printed with disperse dyes have been often subjected to after-finishing treatments such as softening finish, anti-static finish, feel-improving finish and the like, thereby giving value added. However, the after-finishing treatments have been carried out usually at relatively high temperatures, so that problems such as dye bleeding are caused to lower the wet fastness, such as washing fastness. Monoazo disperse dyes having a biphenyl group linked to the diazo component residue via an amino-alkyleneoxy bridging group are disclosed in DE-A-3438849. JP-A-49-69980 describes monoazo dyes having an amino-alkylene bridging group. Further monoazo disperse dyes are, for example, monoazo dyes represented by the following formulas, as disclosed in JP-A-63-132969, a monoazo dye represented by the following formula, as disclosed in JP-A-60-112857, and a monoazo dye represented by the following formula, as disclosed in JP-A-63-156864. However, these monoazo disperse dyes are not yet sufficient to meet the needs described above, and therefore improvements are required. The present inventors have undertaken extensive studies to find a monoazo compound useful for dyeing or printing hydrophobic fiber materials, particularly those such as polyester fiber materials with superior dyeability and dye characteristics such as levelling property and extensive applicability and capability of giving dyed or printed products excellent in fastness properties such as light fastness, sublimation fastness, wet fastness and the like, particularly wet fastness such as washing fastness after the after-finishing treatments of the dyed or printed products, and as a result attained the present invention. The present invention provides a monoazo compound represented by the following formula (I), wherein D is unsubstituted or substituted phenyl; X is hydrogen, C₁- C₄ alkyl, C₁-C₄ alkoxy, acylamino, halogeno or -NH-CO-NHQ in which Q is hydrogen, C₁-C₄ alkyl or phenyl; Y is hydrogen, halogeno, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkoxy-C₁-C₄ alkyl or C₁-C₄ alkoxy-C₁-C₄ alkoxy; R₁ is hydrogen, C₁-C₆ alkyl unsubstituted or substituted by C₁-C₄ alkoxy, C₁-C₄ alkoxycarbonyl, C₁-C₄ alkylcarbonyloxy, C₁-C₄ alkoxycarbonyloxy, phenyl, phenoxybenzoyloxy or cyano, or C₃-C₅ alkenyl; or R₁ and Y are taken together with the adjacent nitrogen and two carbon atoms, respectively, to form a 5- or 6-membered ring; R₂ is straight or branched C₂-C₄ alkylene unsubstituted or substituted by hydroxy; W₁, W₂, W₃, Z₁, Z₂ and Z₃ independently of one another are each hydrogen, chloro, bromo, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkoxycarbonyl or nitro; and B is a bridging group selected from carbonyl, carbonyloxy, oxycarbonyl, imino, -O-, -S-, -CH=N-, -SO₂-, -OSO₂-, straight or branched C₁-C₆ alkylene or -A₁-E₁-A₂-E₂-A₃- in which A₁, A₂ and A₃ independently of one another are each a direct linkage, carbonyl, carbonyloxy, oxycarbonyloxy, imino, -O-, -S-, -CH=N-, -SO₂-, -OSO₂- or and E₁ and E₂ independently of one another are each a direct linkage or straight or branched C₁-C₆ alkylene, provided that E₁ is the alkylene as defined above when A₁ is not a direct linkage, E₂ is the alkylene as defined above when A₃ is not a direct linkage, and both E₁ and E₂ are not direct linkages at the same time when A₂ is a direct linkage. The present invention also provides a process for producing the compound represented by the formula (I), which comprises reacting a diazonium salt of an amine represented by the following formula (II), D - NH₂ (II) wherein D is as defined above, with a coupling component represented by the following formula (III), wherein X, Y, R₁, R₂, W₁, W₂, W₃, Z₁, Z₂, Z₃ and B are as defined above. The present invention further provides a process for dyeing or printing hydrophobic fiber materials, which comprises contacting the fiber materials with the compound represented by the formula (I). In the above formula (I), the phenyl group represented by D may be unsubstituted or substituted by C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, phenyl, halogeno (e.g. chloro, bromo), trifluoromethyl, cyano, nitro, acyl, benzoyl, C₁-C₄ alkoxycarbonyl (e.g. methoxycarbonyl, ethoxycarbonyl), C₁-C₄ alkylsulfonyl, phenylsulfonyl, phenoxysulfonyl, sulfonamide, arylazo (e.g. phenylazo) and the like, and two of these adjacent to each other may be taken together to form a fused ring such as phenyl, cyclic imide and the like. Of these residues, preferred are phenyl unsubstituted or substituted once or more by cyano, methylsulfonyl, ethylsulfonyl, chloro, bromo, formyl, acetyl, benzoyl, carbomethoxy, carboethoxy, methoxy or ethoxy. Particularly preferred are phenyl unsubstituted or substituted once, twice, three times or four times by nitro, chloro, bromo, cyano, methylsulfonyl, ethylsulfonyl or methyl. The -NH-CO-NHQ represented by X includes, for example, ureido, methylureido, ethylureido, phenylureido and the like, and the acylamino represented thereby can be represented by the formula, -NH-V-R, wherein V is -CO or -SO₂-and R is an unsubstituted or substituted alkyl or phenyl group. Examples of the acyl represented by -V-R are acetyl, propionyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, phenylcarbonyl, 2-methoxycarbonylethylcarbonyl, 2-ethoxycarbonylethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, phenoxycarbonyl, methoxyethylcarbonyl, hydroxyethylcarbonyl, methylsulfonyl, ethylsulfonyl and the like. Among those represented by X, preferred are hydrogen, methyl, methoxy, chloro, bromo, acetylamino, propionylamino, methylsulfonylamino and ureido. Of these, hydrogen, methyl, chloro and acetylamino are particularly preferred. Among those represented by Y, preferred are hydrogen, chloro, bromo, methyl, methoxy, methoxyethyl, methoxyethoxy and the like. Of these, hydrogen is particularly preferred. The C₁-C₆ alkyl represented by R₁ is straight or branched. Preferred is C₁-C₄ alkyl unsubstituted or substituted by, preferably, C₁-C₄ alkoxy (e.g. methoxy, ethoxy), C₁-C₄ alkylcarbonyloxy (e.g. methyl- or ethyl-carbonyloxy), C₁-C₄ alkoxycarbonyl (e.g. methyl- or ethyl-carbonyl), phenoxy or phenyl. The 5- or 6-membered ring which can be formed by taking R₁ and Y together with the adjacent nitrogen and two carbon atoms, respectively, may contain another hetero atom such as oxygen, and may be unsubstituted or substituted by, for example, hydroxy, methyl, methoxy, chloro, phenyl or the like. Of these, preferred are 6-membered rings unsubstituted or substituted by 1 to 4 methyl groups. Particularly preferred are dihydroquinoline and tetrahydroquinoline which may be formed by uniting the 6-membered ring and the existing benzene ring in a body, and which may be unsubstituted or substituted by 1 to 4 methyl groups. Among those represented by W₁, W₂ and W₃, preferred are independently hydrogen, chloro, methyl or methoxy. Particularly preferred is the case where W₁, W₂ and W₃ are all hydrogen. Among those represented by Z₁, Z₂ and Z₃ preferred are independently hydrogen, chloro, methyl, methoxy, methoxycarbonyl and nitro. Particularly preferred is the case where Z₁, Z₂ and Z₃ are all hydrogen. Among the bridging groups represented by B, preferred are carbonyl -O-, -S- and the alkylene as described above, and in the bridging group represented by -A₁-E₁-A₂-E₂-A₃-, A₁, A₂ and A₃ independently of one another are preferably each direct linkage, carbonyloxy and -O-. Preferred examples of the bridging group -A₁-E₁-A₂-E₂-A₃- are and the like, These examples may contain straight or branched ones. More concretely, there are exemplified -OCH₂-, -OCH₂CH₂-, (m₂' : 2-6), -OCH₂CH₂OCH₂CH₂-, -O-CH₂CH₂O-CH₂CH₂O-, and the like. The present monoazo compound represented by the formula (I) can be produced in a manner known per se. For example, the amine represented by the formula (II) can be diazotized in a conventional manner, and the resulting diazonium compound is allowed to react with the coupling component represented by the formula (III) in a conventional manner. The coupling component (III) can be produced also in a manner known per se. For example, a phenol represented by the following formula (IV), wherein W₁, W₂, W₃, B, Z₁, Z₂ and Z₃ are as defined above, is allowed to react with a dihalide represented by the following formula (V), Hal-R₂-Hal (V) wherein R₂ is as defined above, and Hal is halogen such as chlorine and bromine, thereby obtaining a halide represented by the following formula (VI), wherein Hal, R₂, W₁, W₂, W₃, B, Z₁, Z₂ and Z₃ are all as defined above. Successively, the halide (VI) is allowed to react with an aniline represented by the following formula (VII), wherein X, Y and R₁ are as defined above, thereby obtaining the desired coupling component (III). The monoazo compound of the formula (I) in accordance with the present invention is extensively applicable for a disperse dye and useful for dyeing or printing hydrophobic fiber materials, particularly those such as polyester fiber materials. In utilizing the present monoazo compound in such field, the compound (I) can be finely pulverized in an aqueous medium with the aid of naphthalenesulfonic acid/formaldehyde condensate, lignin sulfonic acid or the like, thereby obtaining a liquid dye dispersion. The liquid dye dispersion can be used as it is for the dyeing or printing of fiber materials, or formed to a powder by, for example, spray-drying it. Dyeing can be carried out by a method wherein hydrophobic fiber materials are dipped in an aqueous dye bath and heated to a temperature of 105°C or higher, preferably 110° to 140°C under increased pressure, a carrier dyeing method wherein dyeing is carried out in the presence of a carrier such as o-phenylphenol, trichlorobenzene and the like at a relatively high temperature, for example, water-boiling temperature, or a thermosol method wherein the fiber materials are padded with an aqueous dye dispersion and dry-heated at a temperature of 150° to 230°C for 30 to 60 seconds. Printing can be carried out by mixing the aqueous dye dispersion with a suitable stock paste to obtain a color paste, printing fiber materials with the color paste and then steaming or thermosol-treating the printed fiber materials. In addition, the fiber materials can also be dyed by a solvent dyeing method wherein an organic solvent such as trichloroethylene, perchloroethylene and the like is used as a dyeing medium. The dyed or printed products thus obtained can be subjected, if desired, to after-finish treatments such as softening finish, water-repellenting finish, feel-improving finish, antistatic finish, sanitary finish and the like, in a conventional manner. The present monoazo compound of the formula (I) can be characterized by the facts such that hydrophobic fiber materials, particularly those such as polyester fiber materials, can be dyed or printed in a usual manner using the present compound (I), thereby obtaining dyed or printed products excellent in various fastness properties such as light fastness, sublimation fastness, wet fastness and the like, and such fastness properties cannot be deteriorated even after heat-set treatment and after-finish treatments. For example, the fiber materials can be dyed using a high concentration of the dye to obtain dyed products of a deep color (e.g. JIS 2/l depth), and the washing fastness property thereof is robust so that it can be kept at a higher degree even after the heat-set treatments of dyed products than that of those dyed with existing disperse dyes. The present monoazo compound of the formula (I) can be characterized also by superior dyeability such as dyeing power and build-up property, and extensive applicability, so that dyed or printed products of a deep and level color can be readily obtained. Moreover, the present compound can be used in combination with other dyes to improve the dye performance and to obtain a variety of color. In consideration of the characteristic features described above, the monoazo compound of the present invention can be advantageously used particularly for the dyeing of apparels such as sportswear, which are required to be dyed usually in a deep color and have superior washing fastness because they are to be washed again and again. The present invention is illustrated in more detail with reference to the following Examples, which are only illustrative but not limitative for the scope of the present invention. In Examples, parts are by weight. Example 1 2-Chloro-4-nitroaniline (56 parts) was dispersed in 78 % sulfuric acid (100 parts), and 43 % nitrosylsulfuric acid (110 parts) was added to the dispersion, while keeping the temperature at 35° to 40°C, thereby performing diazotization. The resulting diazonium liquor was added to a glacial acetic acid-methanol (25:2) solution containing N-ethyl-N-2-(4-benzylphenoxy)ethylaniline (104 parts), while keeping the temperature at 0° to 5°C. The reaction mixture was adjusted to pH 3 by the addition of sodium carbonate, and the solid therein was collected on a filter and washed to obtain a monoazo compound of the following formula (1). The maximum absorption wave length (λmax) of the compound in dimethylformamide was found to be 514 nm. The compound obtained (1.0 part) was finely pulverized in an aqueous medium with the aid of naphthalenesulfonic acid-formaldehyde condensate (3.0 parts). The resulting dye dispersion was dried to form powder. Polyester cloth (10 parts, Tetron jersey, a product of Teijin Limited, in Japan) was dipped in a dyebath containing the powder (0.6 part), and dyeing was continued for 60 minutes at 130° to 135°C under increased pressures. The dyed cloth was subjected to reduction-rinsing treatment at 85°C for 10 minutes in a solution of sodium hydroxide (3 parts), hydrosulfite (3 parts) and a betaine amphoteric surfactant (3 parts) in water (3000 parts), washed with water and then dried, thereby obtaining a dyed product of a red color superior in light fastness, sublimation fastness and wet fastness. The dyed product thus obtained was subjected to softening and anti-static finishing in the following manner. The dyed product was dipped in a padding liquor containing a soft-finishing agent (10g/l, Sumitex Softener LK-l, a product of Sumitomo Chemical Co., Ltd., in Japan) and an anti-static agent (5g/l, Sumistat F-l, a product of Sumitomo Chemical Co., Ltd., in Japan), squeezed uniformly at a pick-up of 80 %, again dipped into the same padding liquor as above, squeezed at the same level as above, pre-dried at 80°C for 2 minutes and then subjected to heat set at 170°C for 1 minute. The thus after-finished dyed product was found to have a superior washing fastness. The N-ethyl-N-2-(4-benzylphenoxy)ethylaniline used above was prepared by heating a mixture of excess N-ethylaniline and 2-(4-benzyl)phenoxyethyl bromide, distilling the reaction mixture to remove unreacted N-ethylaniline and purifying the resulting residue. Examples 2 to 87 Compounds shown in the following table were obtained in manners similar to those of Example 1, and the color of dyed product obtained by dyeing polyester fiber with the compounds was as shown in the table, and washing fastness thereof was found to be excellent.

Claims: Claims for the following Contracting States : BE, CH, DE, FR, GB, IT, LI, NL, SE A monoazo compound represented by the following formula, wherein D is unsubstituted or substituted phenyl; X is hydrogen, C₁-C₄ alkyl, C₁-C₄ alkoxy, acylamino, halogeno or -NH-CO-CHQ in which Q is hydrogen, C₁-C₄ alkyl or phenyl; Y is hydrogen, halogeno, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkoxy-C₁-C₄ alkyl or C₁-C₄ alkoxy-C₁-C₄ alkoxy; R₁ is hydrogen, C₁-C₆ alkyl unsubstituted or substituted by C₁-C₄ alkoxy, C₁-C₄ alkoxy carbonyl, C₁-C₄ alkylcarbonyloxy, C₁-C₄ alkoxycarbonyloxy, phenyl, phenoxy, benzoyloxy or cyano, or C₃-C₅ alkenyl; or R₁ and Y are taken together with the adjacent nitrogen and two carbon atoms, respectively, to form a 5- or 6-membered ring; R₂ is straight or branched C₂-C₄ alkylene unsubstituted or substituted by hydroxy; W₁, W₂, W₃, Z₁, Z₂ and Z₃ independently of one another are each hydrogen, chloro, bromo, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkoxycarbonyl or nitro; and B is a bridging group selected from carbonyl, carbonyloxy, oxycarbonyl, imino, -O-, -S-, -CH=N-, -SO₂-, -OSO₂-, straight or branched C₁-C₆ alkylene or -A₁-E₁-A₂-E₂-A₃- in which A₁, A₂ and A₃ independently of one another are each a direct linkage, carbonyl, carbonyloxy, oxycarbonyloxy, imino, -O-, -S-, -CH=N, -SO₂- -OSO₂- or and E₁ and E₂ independently of one another are each a direct linkage or straight or branched C₁-C₆ alkylene, provided that E₁ is the alkylene as defined above when A₁ is not a direct linkage, E₂ is the alkylene as defined above when A₃ is not a direct linkage, and both E₁ and E₂ are not direct linkages at the same time when A₂ is a direct linkage. The compound according to Claim 1, wherein D is phenyl substituted by C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, chloro, bromo, trifluoromethyl, cyano, nitro, acyl, benzoyl, C₁-C₄ alkoxycarbonyl, C₁-C₄ alkylsulfonyl, phenylsulfonyl, sulfonamide, arylazo or a fused ring formed by taking adjacent two of the above together. The compound according to Claim 2, wherein D is phenyl substituted once or more times by cyano, methylsulfonyl, ethylsulfonyl, chloro, bromo, formyl, acetyl, benzoyl, carboethoxy, carbomethoxy, methoxy or ethoxy. The compound according to Claim 3, wherein D is phenyl substituted once, twice, three times or four times by nitro, chloro, bromo, cyano, methylsulfonyl, ethylsulfonyl or methyl. The compound according to any one of Claims 1 to 4, wherein X is hydrogen, methyl, methoxy, chloro, bromo, acetylamino, propionylamino, methylsulfonylamino or ureido. The compound according to any one of Claims 1 to 5, wherein Y is hydrogen, chloro, bromo, methyl, methoxy, methoxyethyl or methoxyethoxy. The compound according to any one of Claims 1 to 6, wherein R₁ is C₁-C₄ alkyl unsubstituted or substituted by C₁-C₄ alkoxy, C₁-C₄ alkylcarbonyloxy, C₁-C₄ alkoxycarbonyl, phenoxy or phenyl. The compound according to any one of Claims 1 to 7, wherein B is carbonyl, -O-, -S- or straight or branched C₁-C₆ alkylene. The compound according to any one of Claims 1 to 7, wherein B is -A₁-E₁-A₂-E₂-A₃- in which A₁, A₂ and A₃ independently of one another are each direct linkage, carbonyloxy or -O-, and E₁ and E₂ are as defined in Claim 1. A process for producing the monoazo compound according the Claim 1, which comprises diazotizing an amine represented by the following formula, D - NH₂ wherein D is as defined in Claim 1, and reacting the resulting diazonium salt with a coupling component represented by the following formula, wherein X, Y, R₁, R₂, W₁, W₂, W₃, B, Z₁, Z₂ and Z₃ are as defined in Claim 1. A process for dyeing or printing hydrophobic fiber materials, which comprises contacting the fiber materials with the monoazo compound according to any one of Claims 1 to 9. Hydrophobic fiber materials dyed or printed by the process according to Claim 11. Claims for the following Contracting State : ES A process for producing a monoazo compound represented by the following formula wherein D is unsubstituted or substituted phenyl; X is hydrogen, C₁-C₄ alkyl, C₁-C₄ alkoxy, acylamino, halogeno or -NH-CO-CHQ in which Q is hydrogen, C₁-C₄ alkyl or phenyl; Y is hydrogen, halogeno, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkoxy-C₁-C₄ alkyl or C₁-C₄ alkoxy-C₁-C₄ alkoxy; R₁ is hydrogen, C₁-C₆ alkyl unsubstituted or substituted by C₁-C₄ alkoxy, C₁-C₄ alkoxycarbonyl, C₁-C₄ alkylcarbonyloxy, C₁-C₄ alkoxycarbonyloxy, phenyl, phenoxy, benzoyloxy or cyano, or C₃-C₅ alkenyl; or R₁ and Y are taken together with the adjacent nitrogen and two carbon atoms, respectively, to form a 5- or 6-membered ring; R₂ is straight or branched C₂-C₄ alkylene unsubstituted or substituted by hydroxy; W₁, W₂, W₃, Z₁, Z₂ and Z₃ independently of one another are each hydrogen, chloro, bromo, C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkoxycarbonyl or nitro; and B is a bridging group selected from carbonyl, carbonyloxy, oxycarbonyl, imino, -O-, -S-, -CH=N-, -SO₂-, -OSO₂-, straight or branched C₁-C₆ alkylene or -A₁-E₁-A₂-E₂-A₃- in which A₁, A₂ and A₃ independently of one another are each a direct linkage, carbonyl, carbonyloxy, oxycarbonyloxy, imino, -O-, -S-, -CH=N, -SO₂-, -OSO₂- or and E₁ and E₂ independently of one another are each a direct linkage or straight or branched C₁-C₆ alkylene, provided that E₁ is the alkylene as defined above when A₁ is not a direct linkage, E₂ is the alkylene as defined above when A₃ is not a direct linkage, and both E₁ and E₂ are not direct linkages at the same time when A₂ is a direct linkage, which comprises diazotizing an amine represented by the following formula D - NH₂ wherein D is as defined above, and reacting the resulting diazonium salt with a coupling component represented by the following formula wherein X, Y, R₁, R₂, W₁, W₂, W₃, B, Z₁, Z₂ and Z₃ are as defined above. The process according to claim 1, wherein D is phenyl substituted by C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, chloro, bromo, trifluoromethyl, cyano, nitro, acyl, benzoyl, C₁-C₄ alkoxycarbonyl, C₁-C₄ alkylsulfonyl, phenylsulfonyl, sulfonamide, arylazo or a fused ring formed by taking adjacent two of the above together. The process according to claim 2, wherein D is phenyl substituted once or more times by cyano, methylsulfonyl, ethylsulfonyl, chloro, bromo, formyl, acetyl, benzoyl, carboethoxy, carbomethoxy, methoxy or ethoxy. The process according to claim 3, wherein D is phenyl substituted once, twice, three times or four times by nitro, chloro, bromo, cyano, methylsulfonyl, ethylsulfonyl or methyl. The process according to any one of claims 1 to 4, wherein X is hydrogen, methyl, methoxy, chloro, bromo, acetylamino, propionylamino, methylsulfonylamino or ureido. The process according to any one of claims 1 to 5, wherein Y is hydrogen, chloro, bromo, methyl, methoxy, methoxyethyl or methoxyethoxy. The process according to any one of claims 1 to 6, wherein R₁ is C₁-C₄ alkyl unsubstituted or substituted by C₁-C₄ alkoxy, C₁-C₄ alkylcarbonyloxy, C₁-C₄ alkoxycarbonyl, phenoxy or phenyl. The process according to any one of claims 1 to 7, wherein B is carbonyl, -O-, -S- or straight or branched C₁-C₆ alkylene. The process according to any one of claims 1 to 7, wherein B is -A₁-E₁-A₂-E₂-A₃- in which A₁, A₂ and A₃ independently of one another are each direct linkage, carbonyloxy or -O-, and E₁ and E₂ are as defined in claim 1. A process for dyeing or printing hydrophobic fiber materials, which comprises contacting the fiber materials with the monoazo compound as defined in any one of claims 1 to 9. Hydrophobic fiber materials dyed or printed by the process according to claim 10.

Inventors: HATTORI HIDEO, OMURA TAKASHI, SEKIHACHI JUNICHI, UEDA YASUYOSHI, YAMAMOTO JUN, YAMAMOTO YOSUKE, HATTORI, HIDEO, OMURA, TAKASHI, SEKIHACHI, JUNICHI, UEDA, YASUYOSHI, YAMAMOTO, JUN, YAMAMOTO, YOSUKE
Applicants: SUMITOMO CHEMICAL CO, SUMITOMO CHEMICAL COMPANY, LIMITED
Application year: 1989
Main classification: C09B29
IPC codes: C09B29, D06P1