GB2307481A - Fibre-reactive triazine containing monoazo dyes and use for dyeing or textile-printing hydroxy and/or amide group containing fibre materials - Google Patents

Description

2307481 MONDAZO COMPOUND AND PROCESS FOR DYEING OR TEXTILE-PRINTING FIBER

MATERIAL USING THE SAME The present invention relates to a fiber-reactive monoazo compound, which is normally suited to be used with an organic base material having a hydroxy group and/or amide group, particularly cellulose fibers, natural or synthetic polyamide fibers, polyurethane fibers, hides or mixed fibers thereof, as a fiberreactive yellow raw material in a dyeing or printing process.

A monoazo compound having an aliphatic vinylsulfon reactive group is described in Japanese Patent Kokai (Laid-Open) No. 58-65759, Japanese Patent Kokoku No. 6017457 and the like.

Various reactive dyes have hitherto been used as a yellow dye in the fields of dyeing and printing of fiber materials. However, the current technical level is not entirely satisfactory in view of high-level requirements for dyeing properties and higher requirements for fastness of dyed articles. Particularly, build-up properties are extremely important because of increased requirements for economic efficiency of dyeing processes. Higher fixing of the dye is desirable in deep color dyeing in order to reduce the burden of coloring of waste

1 - water on dyeing.

Under these circumstances, the present inventors have studied intensively in order to find a fiberreactive compound which can be used as a novel yellow dye having performance such as high fixing property (i.e. excellent build-up properties) in deep color dyeing. As a result, it has been found that certain monoazo compounds show excellent performance. Thus, the present invention has been accomplished.

The present invention provides a monoazo compound of formula (I):

R 1 D-N=N-A-N --r-N-- ir---y- S 02Z N, N Y X wherein R represents a hydrogen atom or a Cl-C, alkyl group which is unsubstituted or substituted by a fibernonreactive group; D represents a phenyl or naphthyl group which is substituted by at least one sulfo group and optionally further substituted by a fiber-nonreactive group; A represents a group of formula (A1) or (A2):

2 2 - 11 R - L - \ A (A 1) (A 2) (S03H)m wherein R' represents a hydrogen atom, a Cl-C, alkyl group, a C,-C, alkyloxy group, a ureido group, -NHCOR3 or -NHS02R3; R3 represents a Cl-C, alkyl group which is untsubstituted or substituted by a fiber- nonreactive group. a C2-C. alkenyl group which is unsubstituted or substituted by a fiber-nonreactive group or a phenyl group which is unsubstituted or substituted by a fiber.7 nonreactive group; R 2 represents a hydrogen atom, a Cl-C, alkyl group, a Cl-C4 alkyloxy group or a sulfo group; m represents 0 or 1; and the mark indicates the bond which is attached to the azo group; Y represents a group of formula (Y1), (Y2) or (Y3) -N-W1-CH2- 1 4 R N _W2_Q_ Is R N (CH2) p- (Y 1) (Y 2) (Y 3) wherein R' represents a hydrogen atom, a Cl-C, alkyl group which is unsubstituted or substituted by a fiber- nonreactive group or -W-CH2S02Z; R5 represents a hydrogen atom or a Cl-C, alkyl group which is unsubstituted or substituted by a fiber-nonreactive group; W' represents a straight-chain or branched C,-C, alkylene group; W2 and W' independently represent a straight-chain or branched C2- C6 alkylene group; Q represents -0- or _NR6_; R 6 represents a hydrogen atom or a Cl-C4 alkyl group; p represents an integer of 1 to 6; and the mark indicates the bond which is attached to -S02Z; Z represents -CH=CH2 or -CH2CH2Z1; Z1 represents sulfate, thiosulfate, phosphate or acetate; and X represents a group of formula (X1) or (X2):

-N-R 7 1 R8 -N E (CH2)n (X 1) (X 2) wherein R represents a hydrogen atom or a C,-C, alkyl group which is unsubstituted or substituted by a fibernonreactive group; R8 represents a hydrogen atom, a Cl-C6 alkyl group which is unsubstituted or substituted by a fiber-nonreactive group, a phenyl group which is 4 unsubstituted or substituted by a fiber-nonreactive group, a naphthyl group which is unsubstituted or substituted by a fiber-nonreactive group or a C,-C, cycloalkyl group which is unsubstituted or substituted by a fiber-nonreactive group; n represents an integer of 1 to 3; E represents - 0-, -S-' -CH2-, -So-' -S02- or -NR9-; and R9 represents a hydrogen atom or a C,-C, alkyl group; or a salt thereof. The monoazo compound of formula (I) or salt thereof is hereinafter referred to as "the present compound".

The present invention also provides a process for dyeing or printing an organic base material having a hydroxy group and/or amide group, which comprises using the monoazo compound or salt thereof.

The present invention will be explained in detail, hereinafter.

Examples of the fiber-nonreactive group include alkyl, alkyloxy, alkyloxycarbonyl, alkylcarbonyloxyrphenyl, hydroxy, cyano, nitro, carbamoyl, carboxy, sulfo, sulfamoyl, sulfate and halogen. The alkyl moieties are preferably C,-C, alkyl. Halogen is preferably chloro or bromo.

In the general foriula (I), examples of the fiber-nonreactive group substituted on the C,-C, alkyl group represented by R, R4 or R' include hydroxy group, cyano group, alkyloxy group, halogen atom, carbamoyl group, carboxyl - 5 group, alkyloxycarbonyl group, alkylcarbonyloxy group, sulfo group and sulfamoyl group.

When R, R' and R' represent a C,-C, alkyl group which is unsubstituted or substituted by a fiber-nonreactive group, preferred examples thereof include methyl, ethyl, n-propyl, iso- propyl, n-butyl, iso-butyl, sec-butyl, 2-hydroxvethyl, 2-hydroxypropyl, 3-hyd--oxypropyl, 2-hydroxybutv-l, 3- hydroxybutyl, 4-hydroxybutyl, 2,3-dihydroxypropyl, 3,4- dihydroxybutyl, cyanomethyl, 2-cyanoethyl, 3-cyanopropyl, methoxymethyl, ethoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 2-hydroxy-3- methoxypropyl, chloromethyl, bromomethyl, 2-chloroethyl, 2-bromoethyl, 3-chloropropyl, 3-bromopropyl, 4-chlorobutyi, 4-bromobutyl, carboxymethyl, 2-carboxyethyl, 3carboxypropyl, 4-carboxybutyl, 1,2-dicarboxyethyl, carbamoylmethyl, 2-carbamoylethyl, 3-carbamoylpropyl, 4- carbamoylbutyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, 2-methoxycarbonylethyl, ethoxycarbonylethvl, 3-methoxycarbonylpropyl, ethoxycarbonylpropyl, 4-methoxycarbonylbutyl, 4- ethoxycarbonylbutyl, methylcarbonyloxymethyl, ethylcarbonyloxymethyl, 2-methylcarbonyloxyethyl, 2ethylcarbonyloxyethyl, 3-methylcarbonyloxypropyl, 3ethylcarbonyloxypropyl, 4-methylcarbonyloxybutyl, 4ethylcarbonyloxybutyl, sulfomethyl, 2-sulfoethyl, 3- sulfopropyl, 4-sulfobutyl, sulfamoylmethyl, 2-sulfamoylethyl, 3- sulfamoylpropyl and 4-sulfamoylbutyl.

In the present invention, R is preferably a hydrogen atom, methyl or ethyl. Among them, the hydrogen ator. is particularly preferred.

In the general formula (I), when Y is a group of the general formula (Y1), the straight-chain or branched alkylene group represented by W' is preferably methylene, e-Lhylene, methylmethylene, trimethylene or tetramethylene. Among them, methylene or ethylene is particularly preferred.

R is preferably a hydrogen atom, methyl, ethyl or a group of the general formula:

-W'-CH,SO,Z (wherein W' and z are as defined above). Among them, the hydrogen atom is particularly preferred. When R 4 is a hydrogen atom, it is particularly preferred that W' is methylene or ethylene.

When Y is a group of the general formula (Y2), the straight-chain or branched alkylene group represented by W2 or W' is preferably ethylene, trimethylene or tetramethylene. It is particularly preferred that R' is a hydrogen atom. Q is preferably -0- or -NH. Among them, -0-is particularly preferred.

When Y is a group of the general formula (Y3), p is preferably 2, 3 or 4.

In the general formula (I), when X is a group of the general formula (X1) and R' and R represent a hydrogen atom or C,-C, alkyl which is unsubstituted or substituted by a fibernonreactive group, R7 is preferably a hydrogen atom, methyl or ethyl and R' is preferably a hydrogen atom or a straight-chain or branched Cl-C, alkyl group which is unsubstituted or substituted by one or two substituents selected from C,-C, alkyloxy, sulfo, carboxy, hydroxy, sulfate, phenyl, cyano and chloro. Examples of particularly preferred R' include a hydrogen atom, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, benzyl, P-hydroxyethyl, P-sulfoethyl, Psulfate ethyl, P-carboxyethyl, P-chloroethyl, P-cyanoethyl, ycarboxypropyl, y- methoxypropyl and y-ethoxypropyl.

AS the phenyl group which is unsubstituted or substituted by a fibernonreactive group represented by RO, for example, an unsubstituted phenyl group or a phenyl group which is substituted by one or two substituents selected from C,-C, alkyl, C,-C, alkyloxy, sulfo, carboxy, chloro and bromo is preferred. As the substituent, methyl, ethyl, methoxy, chloro, sulfo or carboxy is particularly preferred. Particularly preferred examples thereof include phenyl, 2-, 3- or 4-sulfophenyl, 2,4- or 2,5-disulfophenyl, 2-, 3- or 4- carboxyphenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4- 8 - methylphenyl, 2-, 3- or 4-methoxyphenyl, 2-carboxy-4- or 5-sulfophenyl, 2-Sulfo-4- or 5-methylphenyl, 2-sulfo-4- or 5-methoxyphenyl, 2-methyl-4- or 5-sulfophenyl and 2-methoxy-4or 5sulfophenyl.

When R' is a phenyl group which is unsubstituted or substituted by a fiber-nonreactive group, R 7 is preferably a hydrogen atom or C,-C, alkyl which is unsubstituted or substituted by sulfo, carboxy, hydroxy, chloro or cyano.

As the naphthyl group which is unsubstituted or substituted by a fibernonreactive group represented by R', for example, unsubstituted naphthyl or naphthyl which is substituted by one, two or three substituents selected from the group consisting of C,-C, alkyl, C,-C, alkyloxy, sulfo, carboxy, chloro and bromo is preferred. Particularly preferred examples thereof include 2-, 3-, 4-, 5-, 6-, 7- or 8-sulfo-l-naphthyl, 1-, 5-, 6g 7- or 8-sulfo-2-naphthyl, 1,5-, 3,6-, 4,8-, 5,7- or 6,8disulfo-2-naphthyl, 3,6,8- or 4,6,8-trisulfol-naphthyl and 3,6,8or 4,6,8-trisulfo-2-naphthyl.

When Re is a C,-C, cycloalkyl group, examples of the fibernonreactive group substituted on R include C,-C, alkyl.

In the general formula (I), when X is a group of the general formula (X2), n is an integer of 1 to 3 and E is -0-, -S-, -CH2-, -So-' -S02- or -NRg- W is as defined above), it is particularly preferred that n is 2 and E is -0-, -CH,- or -S02_.

In the general formula (I), examples of the phenyl group which is substituted by at least one sulfo group and optionally further substituted by a fiber-nonreactive group, represented by D, include phenyl which is unsubstituted or substituted by one, two or three substituents selected from the group consisting of C,-C, alkyl, C,-Q, alkyloxy, carboxy, sulfo, halogeno and nitro.

Among them, a group of the following general formula (D1):

R 10 p (S03H)k (D1) (wherein R" represents a hydrogen atom, a C,-C, alkyl group, a C,-C, alkyloxy group, a halogen atom or a carboxyl group, and k represents 1 or 2) is particularly preferred. It is more preferred that W is a hydrogen atom, methyl, methoxy or carboxy.

As the naphthyl group, which is substituted by at least one sulfo group and optionally further substituted by a fibernonreactive group, represented by D, for example, a naphthyl group which is unsubstituted or substituted by one, two or three sulfo groups is preferred. Among them, a group represented by the following general formula (D2):

- 1 S03H 1 /1 (S03H)q (S03M r (D 2) (wherein q and r independently represent 0 or 1, provided that q + r > 1) is particularly preferred.

In the general formula (I), when A is a group of the general formula (A1), R' is preferably a hydrogen atom, methyl, methoxy, ureido or -NHCOR-3 (R 3 is as defired above) and, among them, methyl, ureido or -NHCOR1 (R' is as defined above) is particularly preferred. Examples of R' include C,-Q, alkyl or C,-C, alkenyl which is unsubstituted or substituted by a substituent such as sulfo, carboxy or halogeno, or phenyl which is unsubstituted or substituted by a substituent such as sulfo, carboxy, methyl or halogeno.

R' is preferably a hydrogen atom, methyl or methoxy. Among them, the hydrogen atom or methoxy is particularly preferred.

In the present invention, the monoazo compound of formula (II):

1 SO3H R S02z N=N 1ONH N NH(CH2) t R' (S03H)q (S03H)r 7 R8 R (H) wherein t represents 2 or 3, and q, r, R', R 2, R7, R' and Z are as defined above, or a salt thereof is preferred.

In the present invention, the monoazo compound of formula (III):

2 03H N=N --0 NEI---7'__N."NH(CH2).SO2Z R' NYN (M) N 1'4 (S03H)q (S03Mr (CH2)Q wherein E, t. n, q, r, R', R2 and Z are as defined above, or a salt thereof is also preferred.

The group represented by Z1 is preferably sulfate.. Z is preferably CH=CH, or -CH.CH.OSO.H, more preferably -CHCH.OSO3H.

The present compound is present in the form of a free acid or a salt thereof. An alkali metal salt is preferred, more preferably sodium salt, potassium salt or lithium salt.

The present compound can be produced, for example, in the following way. It can be produced by condensing a compound represented by the following general formula (IV):

D-N=N-A-NH 1 R (IV) [wherein D, A and R are as defined above], a compound represented by the following general formula (V-1), (V-2) or W-3):

H-Y-S02Z H-Y-SO,CH,CH,0H H-N-W - CH2 - SO,CH,CH,OH (V- 1) (V-2) (V-3) W-CH,-SO,CH2CH20H [wherein W', Y and Z are as def ined above] and a compound represented by the following general formula (VI):

H-X (VI) [wherein X is as defined above] with 2,4,6-trihalogenos-triazine in an optional order. When using an aliphatic amine represented by the general formula W-2) or (V-3), it may be esterified in a following optional stage. In the condensing reaction with 2,4,6-trihalogeno-s-triazine, the order is not specifically limited and the reaction condition is not also specifically limited. The monoazo compound represented by the general formula (I) or salt thereof can be obtained by condensing with adjusting to the temperature of -10 to 400C (pH 2-9), at the first reaction of the condensing, adjusting to the temperature of 0 to 700C (pH 2-9), at the second reaction, and adjusting to the temperature of 10 to 1000C (pH 2-7), at the third reaction.

The compound represented by the general formula (M may be synthesized by a known procedure. For example, the compound of the general formula (IV) may be obtained by diazotizing a compound represented by the following general formula (Vil):

D-NH2 (VII): [wherein D is as def ined above], diazo-coupling the resultant with a compound represented by the following general formula (VIII) RA- NH 1 R (VIII) [wherein A is as defined above].

AS the 2,4,6-trihalogeno-s-triazine, cyanuric chloride and cyanuric fluoride are preferred.

Examples of the compound represented by the general formula (VII) include 2-, 3- or 4-sulfoaniline, 2,4- or 2,5-disulfoaniline, 2-carboxy-4- or 5sulfoaniline, 2sulfo-4-methoxyaniline, 2-sulfo4-methylaniline, 2methoxy-4or 5-sulfoaniline, 2-methyl-4- or 5-sulfoaniline, 2-sulfo-4-chloro-5methylaniline, 2-methyl-4-sulfo-5- or 6-chloroaniline, 2-aminonaphthalene 1,5-, 3,6-, 4,8-, 5,7or 6,8-disulfonic acid and 2-aminonaphthalene-3,6,8or 4,6,8-trisulfonic acid. Among them, 2-, 3- or 4-sulfoaniline, 2,4- or 2,5-disulfoaniline, 2aminonaphthalene-4,8- disulfonic acid, 2aminonaphthalene-6,8-disulfonic acid and 2- - 14 aminonaphthalene-3,6,8or 4,6,8-trisulfonic acid are particularly preferred.

Examples of the compound represented by the general formula (VIII) include 1-aminonaphthalene-6-, 7- or 8sulfonic acid, aniline, o-toluidine, mtoluidine, methylaniline, 2,5-dimethylaniline, 2,5-diethylaniline, omethoxyaniline, o-ethoxyaniline, m-methoxyaniline, methoxyaniline, 2,5dimethoxyaniline, 2-methoxy-5methylaniline, 2-ethoxy-5-methylaniline, mureidoaniline, m-acetylaminoaniline, m-propionylaminoaniline, mbutyrylaminoaniline, 2-methyl-5-acetylaminoaniline, 2methoxy-5acetylaminoaniline, 2-ethoxy-5acetylaminoaniline, 3-succinylaminoaniline, 3maleinylaminoaniline, 3-benzoylaminoaniline or compounds wherein an amino group (group bonded to the benzene ring) of these compounds is Nmethylated or N-ethylated.

Examples of the compound represented by the general formula (V-1) include the following:

H,NC,H,SO2CH=CH,, H2NC2H4SO,C2H40SO3H, H2NC3H,,SO,CH=CH2' H2NC3H6SO2C2H. OSO3H, H,NC,H,SO2CH=CH21 H2NC4H,SO2C2H,OSO3H, HN(CAS02CH=CH2)21 - HN (C2H4SO2C2H.OSO3H) 2 CH3 1 HNCAS02CAOSO3H1 CH3 1 HNCASO2CH=CH,, CH3 1 HNCASO2CAOSO3H.

CH3 1 HNCAS02CH=CH21 H2NC,H,MC.H.SO2CH=CH21 H2NC2H,NHC2H4SO2C2E40SO3H, H2NCH2 CHC2H4 S02CH=CH, 1 S02CH=CH,, n HN N-CA-S02CH = CE2 L-i m HN N-CA-SO2CH2CH20SO3H Xl-i ll' HN N-CA-SO2CH = CH2 __j r-\ HN N-CA-S02CH2CH20SO3H k--d H2NC2H,OC,H,S02C2H.OSO3H 1 H2NC,H,0CASO2CH=CH., H2NCA0CASO.CH=CH2 and H,NC,H,OC3H.SO2C2H40SO3H.

Examples of the aliphatic amine represented by the general formula (V-2) include compounds wherein the group represented by -CH=CH2 or -CH2CHASO3H is changed into CH2CH20H in embodiments of the aliphatic amine represented by the above general formula (V-I).

Examples of the compound represented by the general formula (VI) include the following:

ammonia; anilines such as 1aminobenzene, 1-amino-2-, -3- or -4-methylbenzene, 1- amino-3,4- or -3,5-dimethylbenzene, 1-amino-2-, -3or -4-ethylbenzene, 1- amino-2-, -3- or 4-methoxybenzene, 1-amino-2-, -3or -4-ethoxybenzene, 1- amino-2-,,-3-, or -4-chlorobenzene, 2-,, 3- or 4aminophenol, 1-amino-3- or -4-acetylaminobenzene, 3- or 4-amino-phenylmethanesulfonic acid, 2-, 3- or 4aminobenzenesulfonic acid, 3-methylaminobenzenesulfonic acid, 3- ethylaminobenzenesulfonic acid, 4methylaminobenzenesulfonic acid, 4ethylaminobenzenesulfonic acid, 5- or 4-aminobenzene1,3-disulfonic acid, 2-aminobenzene-1,4-disulfonic acid, 4-aminobenzene-1,2-disulfonic acid, 4- amino-5methylbenzene-1, 2-disulfonic acid, 2-, 3- or 4-aminobenzo acid, 5- aminobenzene 1,3-dicarboxylic acid, 5-amino-2hydroxybenzenesulfonic acid, 4-amino-2hydroxybenzenesulfonic acid, 5-amino-2ethoxybenzenesulfonic acid, Nmethylaminobenzene, Nethylaminobenzene, N-hydroxyethylaminobenzene, Ncyanoethylaminobenzene, N-carboxyethylaminobenzene, Nrethylamino-1methylbenzene, N-ethylamino-lmethylbenzene, N-methylamino-1,2- or -3carboxybenzene, N-methylamino-1-, -2- or -3-sulfobenzene, 1-methylamino3or -4-chlorobenzene, 1-methylamino-3- or -4methylbenzene, 1-ethylamino-4chlorobenzene, 1ethylamino-3- or -4-methylbenzene, 1-(2hydroxyethyl)amino- 3 -methylbenz ene, 3- or 4 -methyl aminobenz o ic acid, 3or 4-methylaminobenzenesulfonic acid, 4-amino3carboxybenzenesulfonic acid, 3-amino-4carboxybenzenesulfonic acid, 2amino-4methylbenzenesulfonic acid, 2-amino-5methylbenzenesulfonic acid, 2amino-4methoxvbenzenesulfonic acid, 2-amino-5methoxybenzenesulfonic acid, 3-amino-4methoxybenzenesulfonic acid, 4-amino-3methoxybenzenesulfonic acid, 3-amino-4methylbenzenesulfonic acid and 4-amino5methylbenzenesulfonic acid; naphthylamines such as 2-, 3-, 4-, 5-, 6-, 7or 8aminonaphthalene-l- sulfonic acid, 1-, 4-, 5-, 6-, 7- or 8-aminonaphthalene-2-sulfonic acid, 7- ethylaminonaphthalene-2-sulfonic acid, 4-, 5-, 6-, 7- or 8- aminonaphthalene-1,3-disulfonic acid, 2-, 3- or 4- aminonaphthalene-1,5-disulfonic acid, 3-, 4-, 7- or 8aminonaDhthalene-1,6- disulfonic acid, 3- or 4- aminonaphthalene-1,7-, -2,6- or -2,7-disulfonic acid. 6-, 7- or 8aminonaphthalene-1,3,5-trisulfonic acid, 4-, 7- or 8-aminonaphthalene-1,3, 6-trisulfonic acid and 4- aminonaphthalene-1,3,7-trisulfonic acid; aliphatic amines such as cyclohexylamine, cyclopentylamine, methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec- butylamine, dimethylamine, diethylamine, methylethylamine, allylamine, 2- chloroethylamine, 2-methoxyethylamine, 2- aminoethanol, 2-methylaminoethanol, bis(2- hydroxyethyl)amine, 2-acetylaminoethylamine, 1-amino-2propanol, 3- methoxypropylamine, 1-amino-3- dimethylaminopropane, 2-aminoethanesulfonic acid, aminomethanesulfonic acid, 2-methylaminoethanesulfonic acid, 3 -amino- 1 - propanesulfonic acid, 2-sulf ate ethylamine, aminoacetic acid, methyl aminoacet ic acid, 8-alanine, aalanine, V-aminobutyric acid, E- aminocaproic acid, benzylamine, 2-, 3- or 4-chlorobenzylamine, bis(2-sulfate ethyl)amine, 4methylbenzylamine, N-methylbenzylamine, 2-, 3- or 4-sulfobenzylamine, 2phenylethylamine, Iphenylethylamine and 1-phenyl-2-propylamine; and 19 cyclic amines such as morpholine, thiomorpholine, piperidine, pyrrolidine and amines of formula (VI) in which X i selected from the groups of the following formulae:

-N S02 k 1 (CHP2 -N S02 1 (CH2)3 1 -1s = 0 (CHP2 -N S=0 -N (CH2)3 (CH2) 3 The present compound has a f iber react ivity and can be used for dyeing or textile-printing the organic material having a hydroxy group and/or an amide group. It is preferred to use the organic material in the form of a f iber material or a mixed fiber material.

Examples of the hydroxy group-containing material include natural or synthetic hydroxy group-containing material such as cellulose f iber material or a regenerated product thereof and polyvinyl alcohol. Preferred examples of the cellulose fiber material include cotton and other vegetable f ibers such as linen, hemp, jute and ramie f ibers. Examples of the regenerated cellulose f ibers include viscose staple and filament viscose.

Examples of the amide group-containing material include synthetic or natural polyamide and polyurethane, particularly wool and other animal hairs, silk, hide, polyamide-6,6, polyamide-6, polyamide-11 and polyamide-4 in the form of fibers.

The present ccmpound can used for dyeing or textile-printing the above materials, particularly above fiber materials, using a suitable process according to the physical and chemical properties of the materials.

In case of absorption dyeing of the cellulose fiber, absorption dyeing may be conducted at comparatively low temperature in the presence of an acid binder (e. g. sodium carbonate, sodium tertiary phosphate or sodium hydroxide), if necessary, using a neutral salt (e.g. mirabilite or sodium chloride) in combination with a solubilizing agent, a penetrating agent or a leveling agent. The neutral salt accelerating absorption of the dye can be added before and after reaching the proper dyeing temperature and, if necessary, it can be added in several Dortions.

In case of dyeing of the cellulose f ibers according to the padding process, the cellulose f ibers are padded at room temperature or elevated temperature, dried and then fixed by steaming or dry heat.

In case of textile printing of the cellulose fibers, the cellulose fibers may be textile-printed in one phase, for example, using a textile printing paste containing sodium hydrogencarbonate or other acid binders, and then steamed at 95 to 1600C. Alternatively, the cellulose fibers may be textile-printed in two phases, for example, using a neutral or weak acid textile printing paste, passed through a hot alkaline bath containing an electrolyte or overpadded using an alkaline electrolyte-containing padding solution, and then steamed or dry-heated.

As the textile printing paste, for example, a sizing agent or an emulsifier (e.g. sodium alginate or starch ether) can be used, optionally, in combination with a normal textile printing aid (e.g, urea) and/or a dispersing agent.

Examples of the acid binder suitable for fixing the present compound on the cellulose fiber include watersoluble basic salts of alkali metals or alkaline earth metals and inorganic or organic acids or compounds which are alkaline-liberated in the heated state, particularly hydroxides of alkali metals and alkali metal salts of inorganic or organic acids having low to moderate strength.

Among them, sodium salts and potassium salts are particularly preferred. Examples of the acid binder include sodium hydroxide, caustic potash, sodium hydrogencarbonate, sodium carbonate, sodium formate, potassium carbonate, sodium, primary phosphate, sodium secondary phosphate, sodium tertiary phosphate, sodium silicate and sodium trichloroacetate.

The synthetic and natural polyamides and polyurethane f ibers can be dyed by firstly absorbing from a weak acid dye bath with controlling the pH value and optionally changing the pH value to an alkaline pH value so as to conduct f ixing. The dyeing is normally conducted at the temperature of 60 to 1200C. It is also possible to use a normal leveling agent, e.g. condensate of cyanuric chloride and 3-f old molar amount of aminobenzenesulfonic acid or aminonaphthalenesulfonic acid or adduct of stearylamine and ethylene oxide so as to accomplish levelness.

The present compound can be used optionally after mixing with the other dyes so as to obtain the desired hue. The dye used af ter mixing is not specif ically limited and a known reactive dye can be used. Preferred examples thereof include dyes having at least one group selected f rom th e group consisting of sulf ate ethylsulf on group, vinylsulf on groupt monochlorotriazine group, monofluorotriazine group, triazine mononicotinate group, dichlorotriazine group, dif luoromonochloropyrimidine group and trichloropyrimidine group as the reactive group; dyes which are commercially available, for example, under the trade names of Sumifix, Sumifix Supra, Remazol, Levafix, Procion, Cibacron, Basilen, Drimarene, Kayacion, Kayacelon and React; and dyes described in Japanese Patent Kokai (Laid-Open) Nos. 50-178, 58-9483, 56-15481, 56-18976, 56-128380, 57-2365, 57-89679, 57-143360, 59-15451, 58191755, 59-96174, 59161463, 60-6754, 60123559, 60-229957, 60-260654, 61155469, 63-77974, 63225665, 1-185370 and 3-770.

The present compound is characterized by exhibiting excellent performance in dyeing and textile printing of the fiber material. The present compound is particularly suitable f or dyeing the cellulose f iber material and has good weathering resistance, good perspiration light resistance, excellent humidity resistance (e.g. washing resistance, peroxy-washing resistance and perspiration resistance), acid hydrolysis resistance, alkaline resistance, good chlorine resistance, rub resistance and ironing resistance.

The present compound is also characterized by having excellent build-up properties, levelness and washl-off properties as well as good solubility and absorbing/f ixing properties, and obtaining a dyed article having a stable quality without being affected by a change in dyeing temperature, amount of the neutral salt or acid binder and dye bath ratio.

Furthermore, the present compound is characterized by causing little discoloration in case of a f ixing treatment and a resin treatment of the resulting dyed article and causing little change due to contact with a basic substance in case of storing. The present compound also has a suitability for cold batch-up dyeing.

The present compound has high fixing property (i.e. excellent build-up properties) in the deep color dyeing, which are usef ul for a yellow dye for an organic base material having a hydroxy group and/or amide group.

The following Examples further illustrate the present invention in detail but are not to be construed to limit the scope thereof. In the Examples, "parts" and 11%1s11 are by weight unless otherwise stated.

Example 1

2-Aminobenzene-1,4-disulfonic acid (25.3 parts) was condensed with cyanuric chloride (18.5 parts) in an aqueous medium under the acid condition by a conventional procedure to obtain a condensate, and then a monoazo intermediate (54.3 parts) represented in the form of a free acid by the general formula (l):

SO3H N = N-P-NH, NHCOCH3 H03S S03H ( 1 synthesized by a conventional procedure, was condensed with the above condensate to obtain a compound represented in the form of a free.acid by the following formula.

H03S S03-H N N H --r-N- H03S ir- N H NN S03H NHCOCH3 cl SO3i-I The resultant compound was condensed with 3-(2 1-sulf ate ethyl sul fonyl) propyl amine (24.7 parts) in an aqueous medium (pH: 3-6, temperature: 60-80OC) to obtain a monoazo compound represented by the formula (2) in the form of a free acid. This compound showed A. max of 420 nm, and imparted a yellowish color tone on a cotton.

Example 2 A monoazo intermediate (54.3 parts) represented by the formula (1) in the

form of a free acid, synthesized by a conventional procedure, was condensed with cyanuric chloride (18.5 parts) in an aqueous medium by a conventional procedure. Then, 3-(2'-sulfate ethylsulfonyl)propylamine (24.7 parts) was added, followed by condensing under the weak acid condition and further condensing with 2- aminobenzene-1,4-disulfonic acid (25.3 parts) to obtain a monoazo compound represented in the form of a free acid by the formula (2).

fl N=N --p NH-r-N-1r-NHC3HrS02C2HASO3H N v N 1 H03S NHCOCH3 (2) SO3H H03S SO3E Example 3

A monoazo intermediate (54.3 parts) represented by the formula (1) in the form of a free acid, synthesized by a conventional procedure, was condensed with cyanuric chloride (18.5 Darts) in an aqueous medium by a conventional procedure. Then, 2-aminobenzene-1,4-disulfonic acid (25.3 parts) was added, followed by condensing under the weak acid condition and further condensing with 3-(21-sulfate ethylsulfonyl)propylamine (24.7 parts) to obtain a monoazo compound represented by the formula (2) in the form of a free acid.

Example 4.

2-Aminobenzene-1,4-disulfonic acid (25.3 parts) was condensed with cyanuric chloride (18.5 parts) in an aqueous medium under the acid condition by a conventional procedure to obtain a condensate, and then a monoazo intermediate (54.3 parts) represented by the formula (1) in the form of a free acid, synthesized by a conventional procedure, was condensed with the above condensate. Then, 3(21hydroxyethylsulfonyl)propylamine (16.7 parts) was added, followed by condensing in an aqueous medium (pH: 6-9, temperature: 50-80OC) and further sulf ate esterif ication by a conventional procedure to obtain a monoazo compound represented by the formula (2) in the form of a free acid.

Example 5

A monoazo intermediate (54.3 parts) represented by the formula (1) in the form of a free acid, synthesized by a conventional procedure, was condensed with cyanuric chloride (18.5 parts) in an aqueous medium by a conventional procedure. Then, 3-(21-hydroxyethylsulfonyl)propylamine (16. 7 parts) was added, followed by condensing in an aqueous medium (pH: 6-9, temperature: 15-60C). The resulting compound was condensed with 2aminobenzene-1,4-disulfonic acid (25.3 parts) at the pH of 2-5 at the temperature of 50-800C, followed by sulfate esterification by a conventional procedure to obtain a monoazo compound represented by the formula (2) in the form of a free acid. Example 6 A monoazo intermediate (54.3 parts) represented by the formula (1) in the form of a free acid, synthesized by a conventional procedure, was condensed with cyanuric chloride (18.5 parts) in an aqueous medium by a conventional procedure. Then, 2-aminobenzene-1,4-disulfonic acid (25.3 parts) was added, followed by condensing under the weak acid condition. The resulting compound was condensed with 3(21- hydroxyethylsulfonyl)propylamine (16.7 parts), followed by sulfate esterification by a conventional procedure to obtain a monoazo compound represented by the formula (2) in the form of a free acid.

Example 7

Monoazo compounds are synthesized in the same manner as described in Example 1, Example 2 and Example 3 except for using a compound of the following column 2, a compound of the following column 3 and a compound of the following column 4 in place of the monoazo intermediate, 2aminobenzene-1,4-disulfonic acid and 3-(21-sulfate ethylsulfonyl)propylamine used in Example 1, Example 2 and Example 3, respectively. These monoazo compounds impart the color tone shown in column 5 of the following tables on cotton.

Column Column 2 S03H N=N- Ar --- I\\ NH2 7.CC r ' OCH 3 H03S 03H S03H N=N-P-NH2 2 03H MCOCH3_ 3 SO3H 4 1 N=N-P-NH2 6ct NHCOCH3 H03S S03H S03H N=N-C, -NH, j IQ PGCONH, H03S S03H Column 3 H03 S H2WO H 2 N- nI\ 03H SO3H HO 2 6 H2N C2H5 1 HN T/ \\ -\--j Column 4 Column 5 Yellow H2NC2H4SO2C2H40SO3H fl H2NCJ-16 S02C2H40SO3H H2NC2H4SO2C2H40SO3H H3C0 H2N - bL b-3 0 cr 0 bi L.d H2NCASO2CH=CH2 Column 1 6..

7 8 9 Column 2 S03H N=N-P-NH, 6: S03H dH3 Column 3 H, N S 0 3 H S03H CH3 I. N=N-O? NH2 OaH /t CH3 S03H N==N-?\\, NH, H03S Ia.55 Nf7COCH, SO3H N=N NHI) 1. - 03H Ni7COCAC02H H03 H2N D\ H2NC2H4SO3H I-I3C '12N-:5 HI'0 \-i Column 4 H2NC2H4SO2C2H40SO3H H2NC3H6SO2C2H4OS03,1 H2NC2H4SO2C2H40SO3H HN(C2H4SO2C2H40SO3H)2 CH3 1 HNC2H4SO2C2H40SO3H Eo-lumn 5 Yellow 1 W m 1 Column Column 2 Column 3 Column Column 4 P) S03-H W N=N NH2 J-1% 11 H2N-U\ H2NC3H6S02C2H40SO3H Yellow 03H NHCOCH=CHCO2 1 - 12 S03H N==N--C\'NH, H2NC2H4CO2H )65( 1JC0-n H03S S03H S03H N= - _YNH, N CH3 13 1 H2NC2H4SO2C2H40SO3H HN-n/ H03S NHCOCH3 0C2H5 H03S 14 N=No H2 lO 3 Sj=s 0 3 11 CH3 H2S03H S03H N-N - NH2 H2NC2H40H AI /C:5i p S03H HCOCH3 1 1 Column Column 2 Column 3 Column 4 03H H02C 16 H3CO-dN=N-3-NH2 H2NC3H6SO2CAOSO3li NHCO.CH3 H2N-6-SO3H 17 -N=N-P-NH2 H 2 N-C-\- C 1 H2NC2H40C2H4SO2C21- S03H NHCOC2H4CO2H 0S03H S03H N=N-P-NH2 18 H03s S03 CH3 H2NCH3 H2NC2H4SO2CH-CH2 S03H -CH3 yt) -""f 19 1: N-N NH2 HN r--\ S02 H2NC3H6SO2C2H40SO3H H03S CH3 \-i 03HN=N-(--NH2CH3 H2NC2H4SO2C2H40SO3H H03S S03H Q\/S03H F1NCAS03H Column 5 Yellow 11 11 11 0 A 1 LAJ XL 1 Column i Column 2 Column 3 Column 4 Column S03H N=N-P-NH, 21 HN3. H2NC3H6SO2C2H40SO3H Yellow NHCOCH3 03H 22 HN(CA)2 HN -- NC2H4SO2C2H4OS0311 23 H2NC3H6CO2H H2NC2H4SO2CH=CII, S03H N N - NH, 6 24 11 H2N-0 112NC2H4SO2C2H40SO3H NHSO2CH3 S03H H2NC2B4C1 P" b3 0 am F-, 0 Ln 1 (A Ln 1 Column Column 2 Column 3 S03- H CH3 H2NCHC2H4CO2H 26 N N-01 NH2 1 r', T ir C02H H03S S03Wx-f13 S03H v bH 3 27 1 N=N NH2HN COC 1 H03S S03H COCH3 C2H5 03H H3 Q02W N=N NH2 & 28 HN-b H03S CH3 CH3 S03H 29 1 N=W/0,NH 2 HN 1 - NHCOCH3 - q_L 03H CH3 SO3H CH3 HN-6 1 _ CH3 Column 4 bolumn H2K3H6SO2CH=CH2 Yellow H2NC2H4SO2C2H40SO3H S3 p ai -1 0 0 1 W c 1 column Column 2 Column 3 1 Column 4 31 H03 S S03H H2N, -CS-N=N-P-NH2 H2K2H4SO2CAOSOsH MCONH2 03H H03S N=N NH2 32 H2NC2H4OCH3 S03H NHWCH3 H3 33 N=WO NH2 H2NC2H40SO3H H03'S S03H CH3 S03H.

34 N=N-,0-NH2 H2NCH2-n'\ H2NC3H6SO,C,H,0SQU NHCOM2 H03S; 3H S03H N=N-(--NH2 />17- H2W(=1 -OH 0 3H NHCOCH3 Column 5 Yellow 11 11 11 11 bg P) a bi 0 4 Column Column 2 Column 3 AH CH3 N=W NH9 HN-tS 3 6, 1 NHCOCH3 H 03K N=N-P7 NH2 H 37 2 N H03 S SO3H 03H S03H S03H N=W?_1 -NH2 H 5 C6 38 H2 N H03S NG02CH3 SO3H ntIt 51 \ H2N U3H N=N NH2 39 1 11 H03S H PICONH2 S03 S03H S03H j N=N-PNH2 HN H03S SO3H NHCOCH3 \_j =0 Column 4 H2NC2H4SO2C2H40SO3B m Column 5 Yellow 0 H2NC3H6SO2C2H40SO3H AO 1-3 P) cr I0 co Example 8

Monoazo compounds are synthesized in the same manner as described in Example 4, Example 5 and Example 6 except for using a compound of the following column 2, a compound of the following column 3 and a compound of the following column 4 in place of the monoazo intermediate, 2aminobenzene-1,4-disulfonic acid and 3-(21-hydroxy ethylsulfonyl)propylamine used in Example 4, Example 5 and Example 6, respectively. These monoazo compounds impart the color tone shown in column 5 of the following tables on cotton.

38 1 W ko 1 Column 1 41 42 43 44 Column 2 Column 3 SO3H 1 N=N /O-NH, H03 S 03H NHCOCH3 H2-b C2H6 H 03 H,0CH3 N=N-YNH2 H2NC2H4CO2H 03H CH3 1-12NC2H4SO3T-1 H03S H2N_ S03H Column 4 H2NC2H4SO2C2H4 OH 11 m 11 H2NC3H6SO2C21140H Column 5 Yellow b-3 P) cr 0 X0 Column 3 C02H Column Column 2 1- -1 S03H '-NH2 N=N 46 H03S SO3H NHCON112 47 V03H 48 N=WPM2 H03S SO,H MICOCH3 03H N= N- (-\\1\/ -NH2 49 1 /11" H03s CH3 S03H N=N 5 -CI-NH2 so 1 H03S SO3H NHCOCH3 H2Wn\ H2N-n\ CH3 H2NC2H5 H2NC2H4SO3II H2N-r\-CO2H Column 4 CToumn.3 0) cr Yellow H2NC2H4SO2C21-140H 11 1/ 112NC3H6SO2C2H40H /1 1 1 Column, 1 1 51 52 53 54 Column 2 Column 3 Column 4 03H N=N-y" NH2 CHCOCH H2NCA,0C2H6 H2NC2H4SO2C2H40H H03S S03H 3 02H H2W( C02H N-N-P-NH2 H02C H03 S S03H NHCOCH3. H2N-YS03H N-N NH2 Cl - PICONR2 H2Nb H03S S03H S03H N=N-f- 1 HN 0 H03S S03AHCONH2 \-i Eo-1 u imn Yellow 1.9 P) cr (D bi -1 1 Ith m 1 Column 1 56 57 58 59 Column 2 Column 3 N=N-PNH2 H2N-F\-OCH, G NHCOCH3 H03s H2NCH2 S03H F N H2 HN S S03H COCH3 S03H -N=N-P-NH2 HN) S03H NHS02CH3 N-N j C S03H N=N--C--NH, H03S /11 H2 00 NWO F-\\1 3H -U S.03H Column 4 -U-o-iumn 5 H2NC2H4SO2C2H40HYellow 1/ U H2NC3H6SO2C2H40H 11 S3 0 cr 0 bi tli 1 1 P" 1-3 0) c -i (D -A W Column 1 Column 2 Column 3 Column 4 Column S03- H OCH 61.. N=NONH2 3 H2N-C H2NC2H4SO2C2H40H Yellow H03 S SO3H CH3 S03-H OCH3 62 N=WO- NH2 H2NC2H4C1 CH3 H03 CH3 HNC2H4SO2C2H40H SO3H N = N-C' NH2 z",1 11 63 - 1 SO3H H2NCH2SO3H H2NC2H4SO2C2H40H H03.S S03H S0.3H YN 64 N=N _ H9 H2NCH2CO2H COCI n T-T COCH3 U3LI H. N - 65, 1 C2H40H 1 .4k. Dh 1 Column 1 66 67 68 69 1.1 03H N=W YNH2 H03S SO, H NHco- OW-2 S03H N-N-?' NH2 )61: ioH3 H03S SO3H N=N-C'"H2 H03 S03H NHCOCH3 Column 2 SO3H N-N-P-N-H2 03H NHCONH2 Column 3 H3C0 H2N 0 HN-0 1 - C2H4CO2H OCH3 H2NCaH6CO2H CH3 1 IINC2H4SO3H 1-12 N--<n\ Column 4 Column 5 - Yellow H2NC2H4SO2C2H40H 1/ U 11 11 3 0 c 0 -A A Dyeing Example 1 Each of monoazo compounds (0.3 parts) obtained in Examples 1 to 8 was dissolved in water (200 parts) and mirabilite (20 parts) and cotton (10 parts) were added, followed by heating to 50T. Thirty minutes after heating, sodium carbonate (4 Darts) was added, followed by dyeing at the same temperature for one hour. Af ter completion of the dyeing, the cotton was washed with water and soaped to obtain a dyed article having a deep yellow color, which has good iastness properties (particularly chlorinated fastness, light fastness and perspiration light fastness) and build-up properties.

Dyeing Example 2 Each of monoazo compounds (0.3 parts) obtained in Examples 1 to 8 was dissolved in water (300 parts) and mirablite (30 parts) and cotton (10 parts) were added, followed by heating to 60T. Twenty minutes after heating, sodium carbonate (5 parts) was added, followed by dyeing at the same temperature for one hour. After completion of the dyeing, the cotton was washed with water and soaped to obtain a dyed article having a deep yellow color, which has good fastness properties (particularly chlorinated fastness, light fastness and perspiration light fastness) and build-up properties. Dyeing Example 3 Composition of color size Each monoazo comnound obtained in Examples 1 to 8 Urea 5 Parts Sodium alginate (5%) main size 50 Parts Hot water 25 Parts Sodium hydrogencarbonate 2 Parts Balance 13 Parts A size having the above composition was imprinted on a mercerized cotton broadgood, which was interdried, steamed at 10 OOC for 5 minutes, washed with hot water, soaped, washed with hot water and then finally dried. Thus, a yellow textile-printed article having high fixing property, which has good fastness properties (particularly light fastness and perspiration light fastness) and build- up properties, was obtained. Dyeing Example 4 According to the same manner as that described in Dyeing Example 2 except for changing the amount of sodium carbonate from 5 parts to 3 parts, dyeing was conducted to obtain a dyed article of comparable quality to that of the dyed article obtained in Dyeing Example 2 with respect to each monoazo compound. Dyeing Example 5 According to the same manner as that described in Dyeing - 46 Parts Example 2 except for changing the temperature from 600C to 50C, dyeing was conducted to obtain a dyed article of comparable quality to that of the dyed article obtained in Dyeing Example 2 with respect to each monoazo compound. The same results were obtained even if the temperature was adjusted to 70T. Dyeing Example 6 According to the same manner as that described in Dyeing Example 2 except for changing the amount of mirabilite from 30 parts to 15 parts, dyeing was conducted to obtain a dyed article of comparable quality to that of the dyed article obtained in Dyeing Example 2 with respect to each monoazo compound.

Claims (18)

1. A monoazo compound of formula M:

   R 1 D- N = N-A- N Y_ S 02 Z N, N,y (I) X wherein R represents a hydrogen atom or a C,-C, alkyl group which is unsubstituted or substituted by a fiber-nonreactive group; D represents a phenyl or naphthyl group which is substituted by at least one sulfo group and optionally further substituted by a fiber-nonreactive group; A represents a group of formula (A1) or (A2):

   2 R' (A 1) 7 1\ A (SO3WM (A 2) wherein R' represents a hydrogen atom, a C,.-C, alkyl group, a C,-C, alkyloxy group, a ureido group, -NHCOR, or -NHSO,R,; R, represents a C,-C, alkyl group which is unsubstituted or substituted by a fiber-nonreactive group, a C,-C, alkenyl group which is unsubstituted or substituted by a fiber-nonreactive group or a phenyl group which is unsubstituted or substituted by 48 a fiber-nonreactive group; R' represents a hydrogen atom, a C,-C, alkyl group, a C,-Q, alkyloxy group or a sulfo group; m represents 0 or 1; and the mark indicates the bond which is attached to the azo group; Y represents a group of formula (Y1), (Y2) or (Y3):

   -N-W'-CH2- 1 4 R -N-Wg- Q_W 3 1 - R3 (CH2) p (Y 1) (Y 2) (Y 3) wherein R represents a hydrogen atom, a C,-C, alkyl group which is unsubstituted or substituted by a fiber-nonreactive group or -W-CH,SO,Z; R5 represents a hydrogen atom or a C,-C, alkyl group which is unsubstituted or substituted by a fiber-nonreactive group; W' represents a straight-chain or branched C,-C.. alkylene group; W' and W' independently represent a straight-chain or branched C2-C6 alkylene group; Q represents -0- or -NR 6 R 6 represents a hydrogen atom or a C,-C, alkyl group; p represents an integer of 1 to 6; and the mark indicates the bond which is attached to -S02Z; Z represents -CH=CH2 or -CH2CH2Z1; Z1 represents sulfate, thiosulfate, phosphate or acetate; and - 49 X represents a group of formula (X1) or (X2):

   -N-R 7 j R8 -N E (CH2)n (X 1) (X 2) wherein R' represents a hydrogen atom or a CI-C6 alkyl group which is unsubstituted or substituted by a fibernonreactive group; R8 represents a hydrogen atom, a Cl-C6 alkyl group which is unsubstituted or substituted by a fiber-nonreactive group, a phenyl group which is unsubstituted or substituted by a fiber-nonreactive group. a naphthyl group which is unsubstituted or substituted by a fiber-nonreactive group or a C,-C7 cycloalkyl group which is unsubstituted or substituted by a fiber- nonreactive group; n represents an integer of 1 to 3; E represents -0-, - S-, -CH2-, -SO-, -S02- or -NR9-; and R9 represents a hydrogen atom or a Cl-C6 alkyl group; or a salt thereof.
2. 2. A compound according to claim 1, wherein A is a group of formula (A1), or a salt thereof.
3. 3. A compound according to claim 1 or 2, wherein R is a hydrogen atom, or a salt thereof.
4. 4. A compound according to any one of claims 1 to 3, wherein Y is a group of formula (Y1), R' is a hydrogen atom and W' is methylene or ethylene, or a salt thereof.

   - so -
5. 5. A compound according to any one of claims 1 to 4, wherein X is a group of formula (X1), R' is a hydrogen atom or a methyl or ethyl group which is unsubstituted or substituted by sulfo, carboxy, hydroxy, chloro or cyano and R' is a hydrogen atom or a phenyl group which is unsubstituted or substituted by one or two substituents selected from Cl-C4 alkyl, Cl- C4 alkyloxy, sulfo, carboxy, chloro and bromo, or a salt thereof.
6. 6. A compound according to any one of claims 1 to 4, wherein X is a group of formula (X1), R' is a hydrogen atom, methyl or ethyl, R' is a hydrogen atom or a straightchain or branched Cl-C4 alkyl group which is unsubstituted or substituted by one or two substituents selected from ClC4 alkyloxy, sulfo, carboxy, hydroxy, sulfate, phenyl, cyano and chloro, or a salt thereof.
7. 7.

   A compound according to any one of claims 2 to 6, wherein R' is methyl, methoxy, ureido or -NHCOR 3, and R 3 is as defined in claim 1, or a salt thereof.
8. 8. A compound according to any one of claims 2 to 7, wherein R' is a hydrogen atom, methyl or methoxy, or a salt thereof.
9. 9. A monoazo compound according to claim 1 which is of formula (II):

   2 S03H N=N - NH-r-N-.r-NH(CH2)tS02Z 0 N, R' r, (S03H)q (S03H)r N \ 7 R8 R bi - wherein t represents 2 or 3; q and r independently 2 7 represent 0 or 1, provided that q + r > 1; and R', R, R R' and Z are as defined in claim 1, or a salt thereof.
10. 10. A monoazo compound according to claim 1 which is of formula (III):

    2 03H --i,- N N=N -0 NH- -x-NH(CH2)tSO2Z R' -N (III) (S03H)q (S03Mr (CH2)q E wherein t, q and r are as defined in claim 9 and R', R2, n and E are as defined in claim 1, or a salt thereof.
11. 11. A compound according to any one of claims 1 to 10, wherein Z is CH=CH2 or -CH2CH20SO3H, or a salt thereof.
12. 12. A compound according to any one of claims 1 to 11, wherein Z is - C,12CH20SO3H, or a salt thereof.
13. 13. A process for the preparation of a monoazo compound of formula (I) according to any one of claims 1 to 12 or a salt thereof, which process comprises condensing a compound of formula (IV):

    D-N=N-A-NH 1 R (M wherein D, A and R as defined in claim 1, a compound of formula (V-1), (V-2) or (V-3):

    H-Y-S02Z (V- 1) H-Y-S02CH2CH20H (V-2) 52 - H-N-W1 - CH2 - S02CH2CH20H 1 W1-CH2-SO2CH2CH20H W-3) wherein W', Y and Z are as def ined in claim 1, and a compound of formula (VI):

    H-X (VI) wherein X is as defined in claim 1, with a 2,4,6trihalogeno-striazine, and, when a compound of formula (V2) or (V-3) is used, carrying out an esterification step to convert the group -S02CH2CH20H into a group -S02CH2CH2Z1 wherein Z1 is as defined in claim 1, optionally followed by the conversion of the compound of formula (I) thus obtained into a salt thereof.
14. 14. A process for dyeing or textile-printing an organic base material having a hydroxy group and/or amide group, which comprises using a compound according to any one of claims 1 to 12 or a salt thereof.
15. 15. An organic base material dyed or printed with.a compound according to any one of claims 1 to 12.
16. 16. A process according to claim 13 substantially as hereinbefore described in any one of Examples 1 to 8.
17. 17. A process according to claim 14 substantially as hereinbefore described in any one of Dyeing Examples 1 to 6.
18. 18. An organic base material according to claim 15 substantially as hereinbefore described in any one of Dyeing Examples 1 to 6.