Title of Invention	"A PROCESS FOR PREPARING A DYE"
Abstract	A process for preparing a dye of the formula (1), by reacting an arylazodiamine of the formula (XV) with an equimolar proportion of each of two reactive dyes respectively of the formula and with two moles of a reactive dye of the formula (XVI) or (XVII) per mole of the diamine of the formula (XV), to obtain the dye of the formula (I).

Full Text

The present invention relates to a process for preparing a dye. GB-A-1283771 discloses a range of reactive diamine dyes of the formula (A) (Formula Removed) Where D is napthylazo-phenylene or naphthalene containing at least 3 sulphonic acid groups, R is H or an optional substituted Ci-4 alkyl group and X is specifically a phenylene, diphenylene or naphthalene nucleus. They offer a degree of fixation over a wide range of liquor to goods ratios and provide shades of very good light fastness. US-A-5149789 discloses a range of dyestuffs some of which have two or three halotrizine rings interconnected by an aromatic diamine unit or two aromatic diamine units respectively. In one such dye (Example 53), the linking diamine unit carries a phenylazo group. The dye has the formula (Formula Removed) However, in contrast to the range of dyes disclosed in GB-A-1283771 above, neither substitution on the respective halotriazinylamino groups is a chromophore as such. Accordingly such a dye does not have a particularly high dyeing strength. We have found surprisingly that if, in a dyestuff of the formula (A), the linking diamine additionally carries an arylazo group, then excellent build up properties can be achieved, as well as excellent light fastness and aqueous solubility. Moreover the dyes still offer a degree of fixation over a wide range of liquor to goods ratios. These properties manifest themselves especially when the dyes are used to exhaust dye cotton. Accordingly, there is provided a process for preparing a dye of the formula (1) (Formula Removed) wherein An is an optionally substituted arylene group; Each of D1 and D2, independently, is a chromophoric group; Ara is an optionally substituted aryl group; Each of R1, R2, R3 and R4, independently, is H or alkyl; and Each of X1 and X2, independently, is a labile atom or group. The process comprises reacting an arylazodiamine of the formula (XV) (Formula Removed) wherein each of An, Ar2, R3 and R4 is as defined, with an equimolar proportion of each of two reactive dyes respectively of the formula (Formula Removed) wherein each of D1, R1 and X1 is as defined and X3 is a labile atom or group capable of reaction with an amine and (Formula Removed) wherein each of D2, R2 and X2 is as defined and X4 is a labile atom or group capable of reaction with an amine, or when each of D1, D2, X1 and X3 is the same as D2, R2 and X2 and X4 respectively, with two moles of a reactive dye of the formula (XVI) or (XVII) per mole of the diamine of the formula (XV), to obtain the dye of the formula (I). Preferably, each of X1 and X2, independently, is a halogen atom or a pyridinium salt (typically a 3- or 4- carbosy pyridinium salt derived respectively form nicotinic and isonicotinic acid), and is more preferably F or Cl. Still more preferably, each of X1 and X2 is Cl. It is also preferred that each of R1, R2, R3 and R4, independently, is H or d-4 alkyl, more preferably hydrogen, methyl, ethyl or n- or 1-propyl. In the formula (1), it is preferred that An, be an optionally substituted phenylene, naphthalene or diphenylene group; and a still more preferred range of dyes has the formula (II) (Formula Removed) wherein: ATI is a phenylene, naphthalene or diphenylene group; Each of A11 and B11, independently, is optionally present and is a halogen atom, an alkoxy group, hydroxyl group or a sulphonic acid group or a salt thereof; and each of D1, D2 R1, R2, R3, R4, X1, X2 and Ar2 are as defined above. E is an optionally substituted aryl or heteroaryl group and when E is attached to the triazinylamino group the attachment may be from the aryl or heteroaryl group or from a substituent thereon, or E is an acetoacetamidoaryl group wherein the aryl moiety is optionally substituted and wherein the azo linkage in the formula (IV) is linked to the methylene group of the acetoacetamidoaryl group and when E is attached to the triazinylamino group the attachment may be from the aryl moiety or from a substituent thereon. Still more preferably, the group E is attached to the triazinylamino gro jp in formula (i); A is a phenyl or naphthyl group, optionally substituted by at least one of an alky], halo, cyano, hydroxy, aryloxy, alkylsulphonyl or arylsulphonyl group or a carboxylic or sulphonic acid group or salt thereof; and E is as aryl or heteroaryl group selected from phenyl, naphthyl, pyrazolyl, pyrazolonyl, pyridyl, pyridonyl and pyrimidinyl groups or is an acetoacetamidoaryl group; which said aryl or heteroaryl group or aryl moiety of the acetoacetamidoaryl group is optionally substituted by an alkyl phenyl, naphthyl or amino- (which may bear a CM alkyl group), amido- or sulphonamido-phenyl or naphthyl group and E may be attached to the triazinylamino group from the said substituted alkyl group, pheinyl or naphthy! group or phenyl or naphthyl moiety of the said substituent; which said aryl or heteroaryl group is further optionally substituted at least so as to provide the coupling component from which tie group E is derived, with sufficient electron donating capacity to allow the coupling; which said aryl moiety of the acetoacetamidoaryl group is optionally substituted, preferably by at least one of alkyl, alkoxy, halo, H 2NCONH, CH3CONH or S03H (or a salt thereof), more preferred alky! ar,d alkoxy being C1-4 alkyl and C1-4 alkoxy; and when A is an α-naphthol, which dye is optionally metallized. The group E may be a pyrazolyl, pyrazolonyl, pyridyl, pyridonyl or pyrimidinyl group and is substituted by a hydroxyl, mercapto or amino group, which amino group is optionally substituted by at least one alkyl group. However, more preferably, the group E is a phenyl or naphthyl group optionally substituted by an alkyl, alkoxy, ureido, acylamino, alkylsulphonyl, halo, hydroxyl or amino group, which amino group is optionally substituted by at least one alkyl group, or is a carboxylic or sulphonic acid group or a salt thereof. In these groups, the alkyl groups or moiety is preferably a C1-4 alkyl group. In a still more preferred range of dyes, in at least one of D1 and D2," E is an optionally substituted phenylene group such as to provide, in the dye, at least one chromophore of the formula (V) (Formula Removed) wherein: A1 is a phenyl or naphthyl group, optionally substituted by at least one of an alkyl, halo, cyano, hydroxy, aryloxy, alkylsulphonyl or arylsulphonyl group or a carboxylic or sulphonic acid group or salt thereof; the or each R6, independently, is alkyl (preferably C1-4 alkyl), alkoxy (preferably C1-4 alkoxy), halo, H2NCONH. H3CCONH or S03H (or a salt thereof); and p is zero or is 1-4, preferably zero or 1-3, more p-eferably 1 or 2. For the avoidance of doubt it is confirmed that, in the above formula (V) and in subsequent formulae the unsubstituted bond d> indicates a link to a triazinylamino in the formula (I) In one especially preferred range of dyestuffs, at least one of D1-and D2- has the formula (VI) (Formula Removed) wherein: AT is as defined above; R7 is alkyl (preferably C1-4 alkyl),alkoxy (preferably C^ alkoxy), halo, H2NCONH or H3CCONH; and Ra is H, alkyl (preferably C1-4 alkyl),alkoxy (preferably C1-4 alkoxy) or halo. Such chrornophores tend to be yellow in colour. Most preferably R7 is H2NCONH and Ra is hydrogen or R7 is CH3CONH and R8 is CH30. In the above dyes A1 is especially preferably a phenyl or naphthyl group substituted by at least one S03H group, or a salt thereof. In another preferred range of monoazo dyes, at least one and more preferably each of D1 and D2, independently, is a monoazo chromophore of the formula (VII) (Formula Removed) wherein: A1 is as defined above; and E1 is a hydroxy naphthyl group, optionally substituted by at least one sulphonlc acid group or a salt thereof, and optionally additionally substituted by halo, preferably chloro, hydroxyl, methyl or acylamino (preferably a C2-5 acylamino) group. When each of D1 and D2 is a chromophore of the formula (VII) most dyes will be red or orange in colour, More preferably, the group A1 is substituted by at least one S03H group or is a salt thereof, and also more preferably, the group E1 is substituted by at least one group selected, independently, from S03H (and salts thereof) and CH3. Still more preferably, with reference to the formula (i) given and defined above, x is zero, y is 1 and b is 2 or 3. In a more preferred range of dyes of the formula (VII), the group E' has the formula (VIII) (Formula Removed) or has the formula (IX) (Formula Removed) wherein, in each of formula (VIII) and (IX), the or each R15 is halogen, methyl, acylanino or S03H or a salt thereof and p is as defined above; and the bond © is attached to the monoazo group. In a further alternative range of preferred dyes, each of D1 and D2 is a disazo chromophore, or a metallized derivative thereof. Such chromophores may yield, for example, dyes having an especially good deep blue or navy colour. In one preferred range of disazo dyes, at least one and more preferably each of D1 and D2, independently, is a disazo chromophore of the'formula (X) (Formula Removed) wherein one of A2 and A3 is attached to the triazinylamino group and each of A2 and A2, independently, is a phenyl or naphthyl group, optionally substituted by at least one group, independently, selected from sulphonic acid (or a salt thereof), carboxylic acid (or a salt thereof), alkyl acylamino (preferably C2-5acylamino and especially acetylamino), halo, alkylsulphonyl and alkylsulphonylamlno groups (where each alkyl group or moiety is preferably C1-4alkyl); and M is a naphthalene group substituted by at least a hydroxyl and an amino group and optionally substituted by at least one sulphonic acid group. Most of such chromophores will be navy in colour, as will a dye in which each of D, and D2 is of the formula (X). More preferably, M is a group of the formula (XI) (Formula Removed) where the sulphonic acid group in the 8-amino-substituted ring is in the 5-or 6-position. In another preferred range of disazo dyes, at (east one and more preferably each of D1 and D2, independently, is a disazo chromophore of the formula (XII) (Formula Removed) wherein one of A2, M1 and E2 is attached to the triazinylamino group; A2 is as defined above; M1 is an optionally substituted 1,4-phenylene or 1,4-naphthalene group; and E2 is an optionally substituted 1,4-phenylene or 1,4-naphthalene group. For each of M1 and E2 the optional substituent, independently, is preferably at least one group selected from an alkyl (preferably C1-4alkyl), alkoxy (preferably C1-4alkoxy), halo (preferably chloro) and an acylamino (preferably C2-5acyl) group and a sulphonic acid group and a salt thereof. Most of such chromophores will be brown in colour, as will a dye in which each of D, and D2 is of the formula (XII). More preferably, each of M1 and E2, independently, is a group of the formula (XIII) (Formula Removed) wherein the or each X3 independently, is alkyl, alkoxy, acetylamino or alkylsulphonylamino (and each alkyl group or moiety is preferably C1-4alkyl), and p is zero or 1-4, more preferably zero or 1-3, still more preferably zero, 1 or 2; or a group of the formula (XIV) (Formula Removed) wherein the or each X4, independently, is alkyl (preferablyC1-:alkyl), alkoxy (preferably C1-4alkoxy), halo, sulphonic acid (or a salt thereof) or carboxyl (or a salt thereof) and r is zero or 1-4, preferably zero or 1-3, still more preferably zero, 1 or 2. A dye in accordance with the invention may be prepared by a process which, comprises reacting an arylazo diamine of the formula (XV) (Formula Removed) wherein each of Ar1 Ar2, R3 and R4 is as defined above with an equimolar proportion of each of two reactive dyes respectively of the formula (Formula Removed) wherein each of D1, R1 and X1 is as defined above and Xa is a labile atom or group capable of reaction with an arnine and (Formula Removed) wherein each of D2, R2 and X2 is as defined above and X" is a labile atom or group capable of reaction with an arnine, or when each of D1, D2, X1 and X= is the same as D2, R2, X2 and X4 respectively, with two moles of a reactive dye of the formula (XVI) or (XVII) per mole of the diamine of the formula (XV), to obtain the dye of the formula (I). The reactive dye (XVI) or (XVII) containing a chromophore (V) or (VII) "nay be prepared, for example, by diazotizing a diamine component having one protected arnine, coupling it to the coupling component, releasing the protected amine, then reacting the resultant dyestuff with a cyanuric halide, especially cyanuric chloride or fluoride. Alternatively, a diamine containing one hindered and one unhindered amine groups may be allowed to react with one equivalent of the cyanuric halide arid the resultant product diazotized and coupled to the coupling component. Preferred starting materials for providing, in a dye embodying the invention, a chromophore of the formula (V) or (VII) are (1) 3 diazotlzable amine component capable of diazotization and coupling to a coupling component and (2) a coupling component to which the diazotized amine component can couple and also containing an amino group for reaction with a cyanuric halide, especially cyanuric chloride or fluoride, for attachment of the chrornophore to the triazinylamino group. Suitable diazo components for each of the chromophores of the formulae (V) and (VII) are, for example, aniline, orthanilic acid, metanllic acid and sulphanilic acid, 2-ami;nobenzene-1,4-disulphonic acid, 2- aminobenzene-1,5-disulphonic acid, 2-amino-5-methylbenzene-1-Sulphonic acid, 2-amino-5-methoxybenzene-1-sulphonic add, 2-aminobenzoic acid and 3-chloro-4-aminobenzene-1'Sulphonicacid and α-and p-naphthylamines substituted by at least one of sulphonic acid, C2.5acylamino), cyano and aminoalkyl (especially amino C1-4alkyl), such as 2-amino nonaphthalene-1-su!phonic acid,2-aminonaphthalene-1,6" disulphonicaod, 2-aminonaphi.halene-4,8-disulphonic acid and 2-aminonaphthalene-3,6,8-trisulphonlcacid. Suitable coupling components for the yellow chromophore of the formula (V) are, for example, 3-ureidoaniline, 3-acetylaminoanlline and 2,5-disubstituted anilines in which one of the respective substituents, independently,are selected from methyl, methoxy and halo (especially chloro) and the other from rnetiyl and methoxy. Suitable coupling components for the red or orange chromophores of the formula (Vil) are, for example, l-amino-8-hydroxynaphthatene-3,6-clisulahonic acld(H-acid), 1 -amina-8-hydroxynaphthalene-2,e-dlsulphorite acid (K-acid), 2-amino-8-hydroxynaphthalene-6-sulphonIc acid(y-acid) or the corresponding N-methylderivative (Me-y-acid), 3-amino-8-hydrcxvnaphthalene-6-sulphonic acid(J acid) or the corresponding N-methyl derivative (Me-J-acid), 2-amino-8-hydroxynaphthalene-3,6- disulphonic acid,, (2R- orsulpho-v-acid) and 3-amino-8-hydroxynaphthalene-4,6-disulphonic acid (sulpho-J-acid). Preferred starting materials for providing a chromophore of the formula (X) are (1) a first diazotizable amino component for digitization and coupling to provide whichever of the groups A2 and A3 is to provide a terminal end of the dye remote from a triazinylamrno group, (2) a second dia^olizable amino component having one arnino group (or a group capable of conversion to an amino group) for diazotization and coupling to provice whichever of the groups A2 and A3 is to react with a cyanuric nalide, especially cyanuric chloride or fluoride, and additionally having another amino group (or a group capable', of conversion to an arrino group) for reaction with the cyanuric halide and (3) a coupling component to provide the group M. Especially preferred coupling components for providing the group M are 1-hydroxy-8-amino--naphtha.lene-3.5- and 3,6-disulphonic acid (K and H acids respectively). Suitable amine compounds (1) for diazotization to provide the terminal group are aniline, artthranilic acid, sulphanilamide and aniline mono- and disulphonic acids, for example, orthanilic, metanilic and sulprianic acids, 1-arnino-2,4-disulphonic acid, 1-amino-2,5-disulphonic acid. 2-..amino-5"methylbenzene-sulphorrc acid, 2-amino-4-methyl benzenesulphonic acid, 2-chloro-4-amino benzenesulphonic acid, 2-amino-3-chloro-1,5-disu!phonic acid, 2-arnino-1,5-disulphonic acid, 1-amino-3-(ßsulphatoethylsulpnonyl)benzene and 1 -amino-4- up to 4 substiluents, for exampie, 2-aminonaphthalene-1(5-disulphonlc acid, 2-amlncnaphthalene-4,8-disu3phonicacid and 2-aminoriaphthalene-3,6,8-trisulphonic acid. Suitable diamines (2) to;, on the other hand, reaction with cyanuric chloride followed by diazotization and coupling are 2,4-dIaminob9nzene-1-sulphonic acid, 2,5-diarninobenzene-1~sulphonic acid, and 2-amino-5-aminomethylnaphthalene-1 -sulphonic acid. Preferred starting materials for providing a chromophore of the formula (XII) are (1) a diazotizable amines component for diazotization and coup! ng to provide the group A3, (2) an amine compound for providing the g'pup M1 onto which the diazotized amine compound (1) is to be couplod aid which in turn is to be diazotized and coupled to a coupling component and (3) a coupling component. Whichever of components (1)-(3) is to react with a cyanuric halide, especially cyanuric chloride or fluoride, for attachment of the chromophore to the triazinylamino group will have an amin Suitable diazotizable amine components (1) for diazotization to provide the group A3 are those given above with reference to the formula (X). Suitable diazotirable amine components (2) to which the diazotized amine components (1) are coupled and which can be further diazotized are aniline, 2- or3-methyl aniline, 2,5-dirnethy! aniline, 2,5-dimethoxy aniline, 2-rnethyl-5-mel;hoxy aniline, 3-arninoacetanilide and 1-aminonaphthslene-6- and -7- sulphonic acids. When coupling component (3) is the component for further reaction with trie cyanuris halide, preferred such coupling components are 2,5-dimelhyl aniline and 1-aminonaphthalene-6-, and -7- and -8- sulphonic acids. The arylazo diamine of the formula (XV) may be prepared by diazotising an amine of the formula (XVIII) (Formula Removed) wherein Ar2 is an aryl group, and coupling the diazotized amino of the formula (X) to a diamine of the formula (XIX) (Formula Removed) wherein each of Ar1 R3 and R4 is as defined above. Preferred diazotizable amines of the formula (XVIII) are any of those given for the first diazotizable amino component (1) for A2 or A3 in formula (X), remote from the triazinylarnino group. Especially preferred are p-(fi-sulphatoethylsulphonyl)aniline, 2-amlnonaphthalene-4,3-disulphonic acid and 2-aminb-3,6,8-trlsulphonfc acid. Preferred diamines of the formula (XIX) are m-phenylendiamine, p-phenylenediamine,4-chloro-1,3-phenylenediamin«, 3,5-diaminobenzenesulphonic acid, 4-methoxy-1,3-phenyIenediamine, 2,6-diaminotoluene-4 sulphonic acid, 2,4-diaminoacetanilide, 2,3-diaminonaphthalene-4,8-disulphonic acid, 2,5-diaminobenzoic scid and 3,5-dianiinobenzoic acid. Although in this specification, dye formulae have been shown in the form of their free acid, the invention also includes dyes and processes using dyes in the salt form, particularly their salts with alkali metals such as the potassium, sodium, lithium or mixed sodium/lithium salt. The dyes may be used for dyeing, printing or ink-jet printing, for example of textile materials and paper. The process for colouration is preferably performed at a pH of 7.1 to 13, more preferably 10 to 12. pH levels above 7 can be achieved by performing the process for colouration in tie presence of an acid-binding agent. The substrate may be ary of a textile material, leather, paper, hair or film, but is preferably a natural or artificial textile material containing anino or hydroxyl groups, for example textile material such as wool, silk, pojyarnides and modified, polyacrylonltrile fibres, and more preferably a cellule sic textile material,, especially cotton, viscose and regenerated cellulese, for example, that commercially available as Tencel. For this purpose the dyes can be applied to the textile materials at a pH above 7 by, for example, exhaust dyeing, padding, or printing. Textile materials are coloured bright shades and possess gcod fastness to light and wet treatments such as washing. The new dyes are, particularly valuable for colouring cellulosic cellulosic textile material at a pH above 7 in conjunction with a treatment with an acid-binding agent. Preferred acid-binding agents include a'kali metal carbonates, bicarbonates, hydroxides, metasilicates and mixtures thereof, for example sodium bicarbonate, sodium carbonate, sodium metasilicate, sodium hydroxide and the corresponding potassium salts. The dyes benefit from excellent build-up and hiigh fixation. At least for cellulosic materials, dyeing may be carried out at a somewhat higher temperature of about 90°C, as compared with dyeing carried out with conventional monochlorotriazine exhaust dyes which are generally dyed at temperatures of about 30°C. Although more energy is required, particularly improved migration is obtained. The new dyes can be applied to textile materials containing amine groups, such as wool and polyamide textile materials, from a neutral to mildly alkaline dyebath. The dyeing procsss can be carried out at a constant or substantially constant pH, that is to say the pH of the dyebath remains constant or substantially constant during the dyeing process, or if desired the pH of the dyebath can be altered at any stage of the dyeing process. The dyes may be in liquid or solid form, for example in granular or powdured form. We find surprisingly that such dyes provide the following advantageous properties: a) excellent build-up; b) very strong dyeing; c) good robustness ':o changes in dyeing conditions, especially temperature; d) goad wash off; e) good fixation; and f) good aqueous solubility. Especially preferred embodiments of the invention will now be described in more detail with reference to the following Examples in which all parts and percentages are by weight unless otherwise stated. Although preparation and dyeing with any single dye is exemplified, particular advantages can be seen when dyeing with mixtures of dyes. 2N Sodium nitrite (27.5 mis) was added dropwise to a slurry of para-aminoben:?.ene-li-su!phatoethylsulphone (14,05g, 0.05 mo!) in ice wate- (30 mis) containing cone. HCI (6mls) maintained below 10°C. After 1 hr, excess nitrous acid was destroyed by the addition of sulphamic acid, leaving a solution of a diazonium salt. Meta-phenylenediamine (5.4g, 0,05 mol) was dissolved in water (lOOrnls) at pH4 and the above solution of the diazonium salt was added portiomvise maintaining the pH at 4. After complete addition the mixture was stirred for a further 1hr. The resulting precipitate was filtered off and dried to give a rnonoazo dye (7) containing a linking diamine (17.5g). Analytical data were in full agreement with the expected structure (7). An aqueous solution of a yellow dye (6) (0,03 mol) and the dye (7) containing 'the, diamine (0.015 mo!) in water (400 mis) was adjusted to pH £ and heated at 50°C maintaining pH6 by the addition of 2N NaaC03 for 48 hrs. The mixture was then concentrated in vacuo arid the dye precipitated by the addition of methylated spirits. The precipitate was filtered off and dried to give a reactive dyestuff (1} (24.6g); Arnax = 426nm e = 75000. Analytical data were in lull agreement with the expected .structure d). The above reaction may be represented by: (Formula Removed) Example 2 7-Amino naphthalene trisulphonic acid (28.4g, 0.05 mo!) in water (300 mis) and 2N sodium nitrite solution (27.5 mis, 0.055 mol) were mixad and the resulting solution added dropwise to a stirred mixture of ice/water (100 mis) and concentrated HCI (10 mis). After two hours excess; nitrous acid was destroyed by the addition of sulphamic acid leaving a solution of the diazonium salt. Mata-phenylene diamine (5.4g, 0.05 mol) was dissolved in water (50 mis) at pH4 and the resulting solution added slowly to the solution of the diazonium salt maintaining the pH at 4 by the addition of 2N sodium carbonate. After two hours the resulting precipitate was filtered off and dried 1o give the monoazo diamine (9) (26g). Analytical data were in full agreement wKh the expected structure. An squeous solution of yellow dye (8) (0.02 mol) and diamine (9) (0.01 rral) in water (1200 mis) at pH7 was heated at 50°C for five hours, the pH being maintained by the addition of 2N sodium carbonate, the mixture was then concentrated irrvacjyc; and the dye precipitated by the addition of methylated spirit. The precipitate was filtered off and dried to give reactive dye (2) (21 g) Amax - 428 nm ε = 64760. Analytical data were n full agreement with the expected structure, The above reaction may be represented by: (Formula Removed) Example 3 A solution of yellow dye (10) (0.02 mol) end damine (11) (0.01 mcl) in water (100 mis) was heated ta 55 C and maintained pH 7 for four and a naif hours maintaining the pH by the addition of 2N scdium carbonate. The mixture was then concantrated in vacuo and the dye precipitated by the addition of methylated spirits. The precipitate was Stared off and dried to give reacts dye (3) (16g) Amax = 46, nm t - 54300. Analytica, data were in full agreement with the expected structure. The above reaction may be represented by. (Formula Removed) Example 3 A solution of yellow dye (10) (0.02 rnol) and diamine (11) (0,01 mol) in water (100 mis) was heated to 556C and maintained at pH 7 for four and a half hours, maintaining the pH by the addition of 2N sodium car'Donate. The nvxture was then concentrated in vacuo . and the dye precipitated by the addition of methylated spirits. The precipitate was filtered off and dried to give reactive dye (3) (16g) Amax == 464 nm ε = 64300. Analytical data were in full agreement with the expected structure. The above reaction may be represented by: (Formula Removed) Example 4 An aqueous solution of the red dye (12) (0.009 mol) and the monoazo linking diamlne (13) (0.0045 mol) in water (200 mis) was adjusted to pH6 and heated at 50°C for tsn hours maintaining pH6 by the addition of 2N Na2C03. The dye was precipitated by the addition of methylated spirits and the precipitate filtered off and dried to give a yallov/ish red reactive dyestuff (4) (6.1g) Amax = 508 nm ε = 41300. All analytical data v/ere in full agreement with the expected structure (4). The above reaction may be represented by: Example 5 An aqueous solution of the navy dye (14) (0.02 mol) arid the monoazo linking dlamine (15) (0.01 mol) in water (400 mis) was adjusted to pH 6,5 and heated at 55°C for thirty hours maintaining pH 5.5 by the addition of 2N sodium carbonate solution. The dye was precipitated by to give; greenish-navy reactive dyestuff (5) (18.3g) Amax - 623 nm ε = 93(540 λ1/2 =101 nm, All analytical data was in full agreement with the expected structure (5). The above reaction may be represented by: Each of the dyes prepared in Examples 1-5 was applied to cotton by exhaust dyeing at 90°C at a liquorgoods ratio of 10:1 and in the presence of salt and soda ash. In each case, the dye was found to have excellent build-up., extremely high fixation efficiency and good fastness propelies. WE CLAIM; 1. A process for preparing a dye of the formula (1), (Formula Removed) wherein An is an optionally substituted arylene group; Each of D1 and D2, independently, is a chromophoric group; Ar2 is an optionally substituted aryl group; Each of R1, R2, R3 and R4, independently, is H or alkyl; and Each of X1 and X2, independently, is a labile atom or group. the process comprises reacting an arylazodiamine of the formula (XV) (Formula Removed) wherein each of An, Ar2, R3 and R4 is as defined, with an equimolar proportion of each of two reactive dyes respectively of the formula (Formula Removed) wherein each of D1, R1 and X1 is as defined and X3 is a labile atom or group capable of reaction with an amine and wherein each of D1, R1 and X1 is as defined and X3 is a labile atom or group capable of reaction with an amine and (Formula Removed) wherein each of D2, R2 and X2 is as defined and X4 is a labile atom or group capable of reaction with an amine, or when each of D1, D2, X1 and X3 is the same as D2, R2 and X2 and X4 respectively, with two moles of a reactive dye of the formula (XVI) or (XVII) per mole of the diamine of the formula (XV), to obtain the dye of the formula (I).

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