VINYLSULFONE TYPE FIBER-REACTIVE MONOAZO COMPOUND HAVING BENZOYLAMINO-CARRYING COUPLER

Abstract: A manoazo compound represented by the follow­ ing formula in a free acid form, wherein A is phenylene unsubstituted or substituted with methyl, methoxy, chloro, carboxy or sulfo, or naphthy­ lene unsubstituted or substituted with sulfo, R₁ and R₂ are independently hydrogen, chloro, methyl, nitro, carboxy or sulfo, excepting the case where both R₁ and R₂ are hydrogen, and X is -CH=CH₂ or -CH₂CH₂Y in which Y is a splittable group by the action of an alkali, which is useful for dyeing or printing fiber materials in a deep red color, and an aqueous liquid product of which is stable chemically and physically, even when stored for a long period of time.

Description: The present invention relates to a monoazo compound, a process for producing the same, and a process for dyeing or printing fiber materials. More specifically, the present invention relates to a vinyl­ sulfone type fiber-reactive monoazo compound having a benzoylamino-carrying coupler, which is useful for dyeing or printing hydroxyl or amide group-containing fiber materials, particularly such as cellulose fiber, natural or synthetic polyamide fiber, polyurethane fiber, leather and their mixed fiber, in a red color. Fiber-reactive dyes, particularly vinyl­ sulfone type fiber-reactive dyes have been widely used for dyeing or printing fiber materials such as cellulose and polyamides in various conventional dyeing or print­ ing manners, because they can give dyed or printed products of brilliant color shade with an excellent wet fastness property. Such dyes have been described in the prior and: Publication DE-A-1 644 240 relates to water-soluble monoazo dyes of the general formula wherein R₁ and R₂ are hydrogen, halogen, alkyl or alkoxy, R₃ and R₄ are hydrogen, halogen or alkyl, X is alkylene, -NH- or -N(alkyl)-, n is 1 or 0, and Y is CH₂=CH-SO₂- or Z-CH₂-CH₂-SO₂, wherein Z is hydroxyl, dialkylamino or a group splittable by an alkali. Publication FR-A-2 119 941 relates to water-soluble monoazo dyes of the general formula wherein R and R′ are alkyl or alkoxy, R″ is hydrogen or alkyl Z is acyl, X is -SO₂-CH=CH₂ or -SO₂-CH₂-CH₂-Y, and Y is a group splittable by an alkali. Publication FR-A-1 546 089 relates to monoazo dyes of the general formula wherein R is methyl or alkyl, X is hydrogen or sulfo, and Y is acetyl, chloroacetyl, benzoyl or benzosulfo. Publication EP-A-0 124 797 relates to water-soluble monoazo dyes of the general formula wherein M is hydrogen or a metal equivalent, X is vinyl or -CH₂-CH₂-Z, wherein Z is a group splittable by an alkali. In recent years, dyeing and printing systems in a dye house have been actively mechanized and automated in many aspects, and therefore the reactive dyes have been eagerly required to be formed into a form suitable for automatic weighing and dispensing systems. An aqueous liquid dye composition is now considered to be very suitable therefor, unlike usual powder compositions, because it can be applied suitably for the automatic weighing and dispensing devices, and causes no powder-scattering on the handling, not resulting in pollution of a working environment, and moreover it can serve saving energy and labor. In order to make an aqueous liquid composition from the reactive dyes, it is required that the reactive dyes have a high solubility in aqueous medium, in addition to excellent dyeing performance, and it is moreover required that these aqueous liquid compositions are chemically and physically stable during a long storage period. However, known reactive dyes, particularly known vinylsulfone type reactive monoazo dyes of a red color are not yet sufficiently satisfactory under these aspects and improvement regarding this matter is desirable. Thus, it is the object of the invention to provide specific monoazo compounds which exhibit excellent dyeing performances such as color yield, level dyeing property and various fastness properties,and have a high water solubility and a high storage stability in an aqueous liquid state. This object has been achieved by the compounds represented by the following formula (I) in a free acid form, wherein A is phenylene unsubstituted or substituted with methyl, methoxy, chloro, carboxy or sulfo, or naphthylene unsubstituted or substituted with sulfo, R₁ is sulfo in o-position to -NHCO- and R₂ is hydrogen when A is phenylene, or R₁ and R₂ are independently hydrogen, chloro, methyl, nitro, carboxy or sulfo, excepting the case where both R₁ and R₂ are hydrogen when A is naphthylene, and X is - CH=CH₂ or -CH₂CH₂Y in which Y a splittable group by the axtion of an alkali, and its alkalis or alkaline earth metal salts. The process for producing the monoazo compound of the formula (I), which comprises subjecting a diazonium salt of an aromatic amine compound of the following formula (II), wherein A and X are as defined above, to coupling reac­ tion with a naphthalene compound of the following formula (III) in a free acid form, wherein R₁ and R₂ are as defined above. The present invention also provides a process for dyeing or printing hydroxyl or amide group-contain­ ing fiber materials, which comprises using the monoazo compound of the formula (I). Among the monoazo compounds of the formula (I) in which A is phenylene, the following monoazo compounds represented by the following formula (I)-1 in a free acid form are particularly preferred: wherein the methoxy is located at 2- or 4-position. Among those compounds (I) in which A is naphthylene those repre­ sented by the following formula (I)-2 in a free acid form are preferred: wherein R₁, R₂ and X are as defined above, more specifically by the following formulas (I)-3 and (I)-4 in their respective free acid forms, wherein R₃ is chloro, methyl, nitro, carboxy or sulfo, wherein R₃ is as defined above, much more specifically by the following formulas (I)-5 and (I)-6 in their re­ spective free acid forms, wherein the most preferred is the one having the chloro located at 2-position. Examples of the splittable group represented by Y are sulfuric acid ester group, thiosulfuric acid ester group, phosphoric acid ester group, or acetic acid ester group, and preferred X includes -CH=CH₂ and -CH₂CH₂OSO₃H. The monoazo compounds of the formula (I) may be in the form of a free acid or in the form of an alkali or alkaline earth metal salt. Of these, preferred are the lithium, sodium or potassium salts, particularly when used for the dyeing or printing of fiber materials. The monoazo compound of the formula (I) can be produced in any conventional manner, for example, by diazotizing the aromatic amine compound of the formula (II) in a conventional manner, and then coupling the resulting diazonium salt with the naphthalene compound of the formula (III) in a conventional manner. The diazotization reaction can be carried out at a temperature ranging from 0° to 40°C in the presence of a mineral acid using a small excess amount of sodium nitrite, and the coupling reaction can be carried out at a temperature ranging from 0° to 30°C and at a pH within a range of 3 to 9 in an aqueous medium. In this coupl­ ing reaction, the diazonium salt may be added to the coupling component or vice versa. The naphthalene compound of the formula (III) can be prepared in the following manner. Benzoic acid chloride (IV) or anhydride (V), wherein R₁ and R₂ are as defined above, is added to a neutral aqueous solution of 1-amino-8-hydroxynaphtha­ lene-3,6- or -4,6-disulfonic acid, and the mixture is subjected to reaction at a temperature ranging from 0° to 50°C, while controlling the pH within a range of 3 to 8, followed by hydrolysis of the O-acyl group at a temperature ranging from 40° to 100°C, while controlling the pH within a range of 8 to 10. Specific examples of the aromatic amines of the formula (II) are 1-aminobenzene-2-, -3- or -4-β-sulfatoethyl­ sulfone, 1-aminobenzene-3-β-phosphatoethylsulfone, 1-­ amino-4-methylbenzene-3-β-sulfatoethylsulfone, 1-amino­ benzene-3-β-chloroethylsulfone, 1-amino-4-methoxy­ benzene-3-β-sulfatoethylsulfone, 1-aminobenzene-4-­ β-sulfatoethylsulfone-2-sulfonic acid, 1-aminobenzene-5-­ β-sulfatoethylsulfone-2-sulfonic acid, 1-aminobenzene-5-­ β-sulfatoethylsulfone-2,4-disulfonic acid, 1-amino-2,5-­ dimethoxybenzene-4-β-sulfatoethylsulfone, 1-amino­ benzene-4-β-sulfatoethylsulfone-2-carboxylic acid, 1-­ aminobenzene-5-β-sulfatoethylsulfone-2-carboxylic acid, 1-amino-2-methoxybenzene-4-β-sulfatoethylsulfone, 1-­ amino-2-chlorobenzene-4-β-sulfatoethylsulfone, 1-amino-­ 2-methoxybenzene-5-β-sulfatoethylsulfone, 2-amino­ naphthalene-8-β-sulfatoethylsulfone, 2-aminonaphthalene-­ 8-β-sulfatoethylsulfone-6-sulfonic acid, 1-amino-2,5-­ dimethoxybenzene-4-vinylsulfone, 1-amino-2-methoxy-5-­ methylbenzene-4-β-sulfatoethylsulfone, 1-aminobenzene-5-­ vinylsulfone-2,4-disulfonic acid, 1-aminobenzene-5-β-­ phosphatoethylsulfone-2,4-disulfonic acid, 1-amino­ benzene-5-β-chloroethylsulfone-2,4-disulfonic acid, 2-­ aminonaphthalene-8-β-phosphatoethylsulfone-6-sulfonic acid, 2-aminonaphthalene-8-vinylsulfone-6-sulfonic acid, 1-amino-2-methoxy-5-methylbenzene-4-β-chloroethylsulfone, 1-aminobenzene-3- or -4-vinylsulfone, 1-aminobenzene-5-­ vinylsulfone-2-sulfonic acid, 2-aminonaphthalene-5- or -6-β-sulfatoethylsulfone-1-sulfonic acid, 2-aminonaphtha­ lene-5- or -6-vinylsulfone-1-sulfonic acid, 1-amino­ benzene-2-, -3- or -4-β-thiosulfatoethylsulfone, 1-amino-­ 4-methylbenzene-3-β-thiosulfatoethylsulfone, 1-amino-4-­ methoxybenzene-3-β-thiosulfatoethylsulfone, 1-amino­ benzene-4-β-thiosulfatoethylsulfone-2-sulfonic acid, 1-­ aminobenzene-5-β-thiosulfatoethylsulfone-2-sulfonic acid, 1-aminobenzene-5-β-thiosulfatoethylsulfone-2,4-­ disulfonic acid, 1-amino-2,5-dimethoxy benzene-4-β-thio­ sulfatoethylsulfone, 1-aminobenzene-4-β-thiosulfato­ ethylsulfone-2-carboxylic acid, 1-aminobenzene-5-β-thio­ sulfatoethylsulfone-2-carboxylic acid, 1-amino-2-­ methoxybenzene-4-β-thiosulfatoethylsulfone, 1-amino-2-­ chlorobenzene-4-β-thiosulfatoethylsulfone, 1-amino-2-­ methoxybenzene-5-β-thiosulfatoethylsulfone, 2-amino­ naphthalene-8-β-thiosulfatoethylsulfone, 2-aminonaphtha­ lene-8-β-thiosulfatoethylsulfone-6-sulfonic acid, 1-­ amino-2-methoxy-5-methylbenzene-4-β-thiosulfatoethylsulfone, 2-aminonaphthalene-5- or -6-β-thiosulfatoethylsulfone-1-­ sulfonic acid, and 2-aminonaphthalene-5- or -6- sulfatoethylsulfone. Of these, particularly preferred are 1-amino-­ 4-methoxybenzene-3-β-sulfatoethylsulfone, 1-amino-2-­ methoxybenzene-5-β-sulfatoethylsulfone, and 2-amino­ naphthalene-5- or -6-β-sulfatoethylsulfone-1-sulfonic acid. Much preferred are 1-amino-2-methoxybenzene-5-β-­ sulfatoethylsulfone and 2-aminonaphthalene-5- or -6-β­ sulfatoethylsulfone-1-sulfonic acid. Specific examples of the naphthalene compound of the formula (III) are 1-(2′,4′-dichlorobenzoyl)-amino-8-­ hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1-­ (2′,5′-dichlorobenzoyl)-amino-8-hydroxynaphthalene-3,6-or -4,6-disulfonic acid, 1-(2′,4′-dinitrobenzoyl)-amino-8-­ hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1-(2′­ methylbenzoyl)-amino-8-hydroxynaphthalene-3,6- or -4,6-­ disulfonic acid, 1-(4′-methylbenzoyl)-amino-8-hydroxy­ naphthalene-3,6- or -4,6-disulfonic acid, 1-(2′-nitro­ benzoyl)-amino-8-hydroxynaphthalene-3,6- or -4,6-­ disulfonic acid, 1-(4′-nitrobenzoyl)-amino-8-hydroxy­ naphthalene-3,6- or -4,6-disulfonic acid, 1-(3′-nitro­ benzoyl)-amino-8-hydroxynaphthalene-3,6- or -4,6-­ disulfonic acid, 1-(3′-methylbenzoyl)-amino-8-hydroxy­ naphthalene-3,6- or -4,6-disulfonic acid, 1-(2′-chloro­ benzoyl)-amino-8-hydroxynaphthalene-3,6- or -4,6-­ disulfonic acid, 1-(4′-chlorobenzoyl)-amino-8-hydroxy­ naphthalene-3,6- or -4,6-disulfonic acid, 1-(3′-chloro­ benzoyl)-amino-8-hydroxynaphthalene-3,6- or -4,6-­ disulfonic acid, 1-(2′-carboxy- or sulfobenzoyl)-amino-­ 8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1-­ (4′-carboxy- or sulfobenzoyl)-amino-8-hydroxynaphtha­ lene-3,6- or -4,6-disulfonic acid, 1-(2′, 4′-dicarboxy- or disulfobenzoyl)-amino-8-hydroxynaphthalene-3,6- or­ 4,6-disulfonic acid, and 1-(3′,4′- or 3′,5′-dichloro-benzoyl)-amino-8-hydroxynaphthalene-3,6- or 4,6-­ disulfonic acid. Of these, preferred are 1-(2′-chlorobenzoyl)­ amino-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1-(2′-methylbenzoyl)-amino-8-hydroxynaphthalene-3,6- or -4,6-disulfonic acid, 1-(4′-chlorobenzoyl)-amino-8-­ hydroxynaphthalene-3,6- or -4,6-disulfonic acid and 1-­ (2′-sulfobenzolyl)-amino-8-hydroxynaphthalene-3,6- or -­ 4,6-disulfonic acid. Much preferred are 1-(2′-chloro­ benzolyl)-amino-8-hydroxynaphthalene-3,6- or -4,6-­ disulfonic acid, 1-(4′-chlorobenzolyl)-amino-8-hydroxy­ naphthalene-3,6- or -4,6-disulfonic acid and 1-(2′­ sulfobenzoyl)-amino-8-hydroxynaphthalene-3,6- or -4,6-­ disulfonic acid. The monoazo compound (I) of the present invention is fiber-reactive and particularly useful for dyeing or printing hydroxyl group-containing and amide group-­ containing materials in a fibrous form including unmixed or mixed fiber spinning. The hydroxyl group-containing materials include natural or synthetic hydroxyl group-containing materials such as cellulose fiber materials, cellulose-­ containing fiber materials, regenerated products thereof and polyvinyl alcohol. Examples of the cellulose fiber materials are cotton and other vegetable fibers such as linen, hemp, jute and ramie fibers. Examples of the regenerated cellulose fibers are viscose staple and filament viscose. Examples of the cellulose-containing fiber materials are mixed fiber materials such as cellulose/polyester, cellulose/wool, and cellulose/acryl. The amide group-containing materials include synthetic or natural polyamide and polyurethane. Examples of the materials, particularly in the fibrous forms, are wool and other animal furs, silk, leather, polyamide-6,6, polyamide-6, polyamide-11 and polyamide-­ 4. The dyeing may be carried out in a suitable manner, which can be selected from conventional manners depending on the physical and chemical properties of said fiber materials. For example, cellulose fiber materials can be dyed using the present compound by an exhaustion dyeing, padding including cold batch-up dyeing or printing method. The exhaustion dyeing can be carried out at a relatively low temperature in the presence of an acid binding agent such as sodium carbonate, trisodium phos­ phate, sodium hydroxide and the like, if desired using a neutral salt such as sodium sulfate or sodium chloride. The padding of the fiber materials can be carried out at ambient temperature or an elevated temperature, and after drying, steaming or dry-heating the materials to perform the dye-fixation. The printing of the fiber materials can be carried out with a printing paste containing an acid binding agent such as sodium hydrogen carbonate, sodium carbonate, trisodium phosphate, sodium hydroxide and the like, urea and a paste such as sodium alginate, pre-drying the printed fiber materials and then steaming or dry-heating them at 100° to 200°C. The dyeing of natural or synthetic polyamide and polyurethane fiber materials can be carried out by performing exhaustion in an acid or weak acid bath, while controlling the pH value, and then making the bath neutral, or in some cases alkaline to perform the fixation. The dyeing temperature ranges usually from 60° to 120°C. The monoazo compound (I) of the present invention can be characterized in that it can exhibit excellent dye performances upon dyeing or printing the hydroxyl group- or amide group-containing fiber materials and high solubility in water, so that an aqueous liquid dye composition having a high storage stability over a long period of time can be readily pre­ pared in a conventional manner. The present compound is particularly useful for the dyeing or printing of cellulose fiber, and the dyed or printed products have a high color yield with excellent level dyeing properties as well as excellent fastness properties such as chlorine fastness, light fastness, perspiration-light fastness and complex fastness properties including wet resistance-detergent resistance-light resistance. 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, all parts are by weight. Example 1 A mixture of 1-amino-8-hydroxynaphthalene-4,6­ disulfonic acid (11 parts) and water (100 parts) was neutralized to form a clear solution, and o-sulfobenzoic acid anhydride (14 parts) in the form of powders was added to the clear solution little by little, while controlling the pH and the temperature within a range of 4 to 6 and 40° to 50°C, respectively. The mixture was stirred at this pH and at this temperature, until the 1-­ amino-8-hydroxynaphthalene-4,6-disulfonic acid dis­ appeared. The reaction mixture was additionally stirred at a pH of 8 to 12 and at a temperature of 80° to 100°C to perform the hydrolysis of O-acyl group. On the other hand, 1-amino-2-methoxybenzene-5-­ β-sulfatoethylsulfone (9.4 parts) was diazotized in a conventional manner, and the resulting diazonium solu­ tion was added to the above reaction solution. The mixture was stirred at a pH of 5 to 7 and at a tempera­ ture of 0° to 5°C to perform the coupling reaction. Thereafter, potassium chloride was added thereto, and the precipitate was collected on a filter and air-dried to obtain a monoazo compound of the following formula (1) in a free acid form. Example 2 Example 1 was repeated, except that 2-­ aminonaphthalene-6-β-sulfatoethylsulfone-1-sulfonic acid was used in place of 1-amino-2-methoxybenzene-5-β-­ sulfatoethylsulfone, thereby obtaining a monoazo compound of the following formula (2) in a free acid form. Example 3 Using the diazo component and the coupling component as shown in the following table in each free acid form, the corresponding monoazo compound character­ ized by the color on cellulose as shown also in the following table was obtained in a manner similar to that of Example 1. Example 4 A mixture of 1-(2′-chlorobenzoyl)-amino-8-­ hydroxynaphthalene-3,6-disulfonic acid (60 parts) and water (450 parts) was neutralized to form a clear solu­ tion. To this solution was added a diazonium salt of 2-­ aminonaphthalene-6-β-sulfatoethyldulfone-1-sulfonic acid (52 parts) prepared in advance in a conventional manner, and the mixture was stirred at a pH of 5 to 7 and at a temperature of 0° to 5°C to perform the coupling reac­ tion. Thereafter, sodium chloride was added thereto, and the precipitate was collected on a filter and air-­ dried to obtain a monoazo compound of the following formula (3) in a free acid form. Example 5 Example 4 was repeated, except that 1-(4′-­ chlorobenzoyl)-amino-8-hydroxynaphthalene-3,6-disulfonic acid was used in place of 1-(2′-chlorobenzoyl)-amino-8-­ hydroxynaphthalene-3,6-disulfonic acid, thereby obtain­ ing a monoazo compound of the following formula (4) in a free acid form. Example 6 Using the diazo component and the coupling component as shown in the following table in each free acid form, the corresponding monoazo compound character­ ized by the color on cellulose as shown also in the following table was obtained in a manner similar to that of Example 4. Example 7 Each monoazo compound (0.3 part) obtained in Examples 1, 2, 4 and 5 was dissolved in water (200 parts), and sodium sulfate (10 parts) and cotton (10 parts) were added to the solution. The bath was heated to 50°C, and 20 minutes thereafter, sodium carbonate (4 parts) was added thereto. Dyeing was continued for 1 hour at that temperature. The cotton was washed with water and soaped to obtain each dyed product of a deep red color excellent in fastness properties. Using the monoazo compounds obtained in Examples 3 and 6, dyeing was carried out in a manner similar to that described above to obtain a result similar to that of the above. Example 8 Each monoazo compound (15 parts) obtained in Examples 1, 2, 4 and 5 was dissolved in hot water (200 parts) together with urea (50 parts). To this solution were added a paste (400 parts) prepared using sodium alginate (40 parts) and water (960 parts), and then sodium hydrogencarbonate (20 parts). The paste was added to the resulting mixture to make the whole 1000 parts. Cotton cloth was printed with the printing paste obtained above, and the printed cloth was dried and then steamed for 5 minutes at 100° to 103°C, and thereafter rinsed with water and then hot water, boil-­ soaped, again rinsed and then dried to obtain each printed product of a deep red color excellent in fast­ ness properties. Each monoazo compound obtained in Examples 1 and 4 was formed into each aqueous liquid composition in a conventional manner. The composition was stored, and thereafter used for the printing in the same manner as above, then obtaining each printed product similar to that of the above. Using each monoazo compound obtained in Examples 3 and 6, the printing was carried out in a manner similar to that described above, then obtaining each result similar to that of the above.

Claims: For the Contracting States BE, CH, DE, FR, GB, IT, LI, NL, JE 1. A monoazo compound represented by the follow­ ing formula in a free acid form, wherein A is phenylene unsubstituted or substituted with methyl, methoxy, chloro, carboxy or sulfo, or naphthy­ lene unsubstituted or substituted with sulfo, R₁ is sulfo in o-position to -NHCO- and R₂ is hydrogen when A is phenylene, or R₁ and R₂ are independently hydrogen, chloro, methyl, nitro, carboxy or sulfo when A is naphtylene, excepting the case where both R₁ and R₂ are hydrogen, and X is -CH=CH₂ or -CH₂CH₂Y in which Y is a splittable group by the action of an alkali, and its alkali or alkaline earth metal salts. 2. A monoazo compound according to claim 1, which is represented by the following formula in a free acid form, wherein R₁ and R₂ are independently hydrogen, chloro, methyl, nitro, carboxy or sulfo, excepting the case where both R₁ and R₂ are hydrogen, and X is -CH=CH₂ or -CH₂CH₂Y in which Y is a splittable group by the action of an alkali, and its alkali or alkaline earth metals salts. 3. A monoazo compound according to claim 1, which is represented by the following formula in a free acid form, wherein the methoxy is located at 2- or 4-position, and its alkali or alkaline earth metal salts. 4. A monoazo compound according to claim 1, which is represented by the following formula in a free acid form, wherein R₃ is chloro, methyl, nitro, carboxy or sulfo, and its alkali or alkaline earth metal salts. 5. A monoazo compound according to claim 4, which is represented by the following formula in a free acid form, wherein R₃ is chloro, methyl, nitro, carboxy or sulfo, and its alkali or alkaline earth metal salts. 6. A monoazo compound according to claim 4, which is represented by the following formula in a free acid form, and its alkali or alkaline earth metal salts. 7. A monoazo compound according to claim 6, which is represented by the following formula in a free acid form, and its alkali or alkaline earth metal salts. 8. A monoazo compound according to claim 5, which is represented by the following formula in a free acid form, and its alkali or alkaline earth metal salts. 9. A process for producing a monoazo compound represented by the following formula (I) in a free acid form, wherein A is phenylene unsubstituted or substituted with methyl, methoxy, chloro, carboxy or sulfo, or naphthy­ lene unsubstituted or substituted with sulfo, R₁ is sulfo located at o-position to -NHCO- and R₂ is hydrogen when A is the phenylene, or R₁ and R₂ are independently hydrogen, chloro, methyl, nitro, carboxy or sulfo when A is the naphthylene, excepting the case where both R₁ and R₂ are hydrogen, and X is -CH=CH₂ or -CH₂CH₂Y in which Y is a splittable group by the action of an alkali, which comprises subjecting a diazonium salt of an aromatic amine compound of the following formula (II), wherein A and X are as defined above, to coupling reac­ tion with a naphthalene compound of the following formula (III) in a free acid form, wherein R₁ and R₂ are as defined above. 10. A process for dyeing or printing hydroxyl group- or amide group-containing fiber materials, which comprises using a monoazo compound in a free acid form, or as its alkali or alkaline earth metal salts according to any of claims 1 to 8. 11. An aqueous liquid dyeing or printing composition comprising a monoazo compound in a free acid form or as its alkali or alkaline earth metal salts according to any of claims 1 to 8. Claims for the Contracting State: ES 1. A process for producing a monoazo compound represented by the following formula (I) in a free acid form, wherein A is phenylene unsubstituted or substituted with methyl, methoxy, chloro, carboxy or sulfo, or naphth­ lene unsubstituted or substituted with sulfo, R₁ is sulfo located at o-position to -NHCO- and R₂ is hydrogen when A is the phenylene, or R₁ and R₂ are independently hydrogen, chloro, methyl, nitro, carboxy or sulfo when A is the naphthylene excepting the case where both R₁ and R₂ are hydrogen, and X is -CH=CH₂, or -CH₂CH₂Y in which Y is a splittable group by the action of an alkali, which comprises subjecting a diazonium salt of an aromatic amine compound of the following formula (II), wherein A and X are as defined above, to coupling reac­ tion with a naphthalene compound of the following formula (III) in a free acid form, wherein R₁ and R₂ are as defined above. 2. The process according to claim 1, wherein the monoazo compound is represented by the following formula in a free acid form, wherein R₁ and R₂ are independently hydrogen, chloro, methyl, nitro, carboxy or sulfo, excepting the case where both R₁ and R₂ are hydrogen, and X is -CH=CH₂ or -CH₂CH₂Y in which Y is a splittable group by the action of an alkali, and its alkali or alkaline earth metal salts. 3. The process according to claim 1, wherein the monoazo compound according to claim 1 is represented by the following formula in a free acid form, wherein the methoxy is located at 2- or 4-position, and its alkali or alkaline earth metal salts. 4. The process according to claim 1, wherein the monoazo compound is represented by the following formula in a free acid form, wherein R 3 is chloro, methyl, nitro, carboxy or sulfo, and its alkali or alkaline earth metal salts. 5. The process according to claim 4, wherein the monoazo compound is represented by the following formula in a free acid form, wherein R₃ is chloro, methyl, nitro, carboxy or sulfo, and its alkali or alkaline earth metal salts. 6. The process according to claim 4, wherein the monoazo compound is represented by the following formula in a free acid form, and its alkali or alkaline earth metal salts. 7. The process according to claim 6, wherein the monoazo compound is represented by the following formula in a free acid form, and its alkali or alkaline earth metal salts. 8. The process according to claim 5, wherein the monoazo compound is represented by the following formula in a free acid form, and its alkali or alkaline earth metal salts. 9. A process for dyeing or printing hydroxyl group- or amide group-containing fiber materials, which comprises using a monoazo compound in a free acid form, or as its alkali or alkaline earth metal salts according to any of claims 1 to 8. 10. An aqueous liquid dyeing or printing composition comprising a monoazo compound in a free acid form or as its alkali or alkaline earth metal salts according to any of claims 1 to 8.

Inventors: OMURA, TAKASHI, YAMAUCHI, NORIAKI, YOKOGAWA, KAZUFUMI
Applicants: SUMITOMO CHEMICAL COMPANY, LIMITED
Application year: 1987
Main classification: C09B62
IPC codes: C09B62, D06P1