GB1574569A - Disazo dyestuffs - Google Patents

Description

(54) DISAZO DYESTUFFS (71) We, BAYER AKTIENGESELLSCHAFT, a body corporate organised under the laws of Federal Republic of Germany of Leverkusen, Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: The invention relates to dyestuffs, which are free from sulphonic acid groups, of the formula

wherein A denotes the radical of a diazo component, B denotes the radical of a coupling component and E denotes hydrogen or a substituent.

These radicals can be substituted by non-ionic radicals which are customary in azo dyestuff chemistry, for example by those such as are mentioned for the types of dyestuff described below as preferred.

Suitable radicals A are aromatic-carbocyclic radicals, in particular those of the naphthalene and, above all, of the benzene series.

Suitable radicals A are furthermore heterocyclic radicals, in particular those of the thiazole, benzthiazole, thiadiazole, triazole, pyrazole, indazole and thiophene series; radicals of the benzthiazole and benzisothiazole series are preferred.

Particularly suitable radicals A are those of the formula

wherein X1X3 denote hydrogen, alkyl, alkoxy, CN, NO2, CF3, alkylsulphonyl, halogen. aryl, COOH, alkoxycarbonyl, aryloxy, sulphamoyl or carbamoyl.

Suitable radicals B are those of the aniline, a-aminonaphthalene, phenol, indole, pyridone, pyrazolone and aminopyrazolone series. Aniline-type coupling components are preferred.

Particularly suitable radicals B are those of the formulae

wherein R3, R, and R8 represent hydrogen, alkyl, alkoxy, halogen, alkylsulphonyl, aralkylsulphonyl, arylsulphonyl, sulphamoyl, carbamoyl, alkoxycarbonyl or acylamino, R4, represents hydrogen, alkyl, halogen, alkoxy or acylamino, R5 and R6 represent alkyl, aralkyl or hydrogen, Rg represents hydrogen, alkyl, alkoxy or cyano, R10 represents alkyl, aryl or hydrogen, R" represents hydrogen or alkyl, R12 represents cyano, carbamoyl, alkoxycarbonyl, hydrogen, alkyl or aryl, R13 represents hydrogen, alkyl or aryl, R,4 represents hydrogen or alkyl, R,s represents hydrogen, alkyl, hydroxyl, aryl or alkoxycarbonyl and R, represents cyano, carbamoyl or alkoxycarbonyl.

Suitable radicals E are, in particular, alkyl, aryl, alkoxycarbonyl or hydrogen.

The abovementioned alkyl, aralkyl, cycloalkyl and aryl radicals can contain further non-ionic substituents.

The alkyl or alkoxy radicals mentioned above in any connection are preferably to be understood as those with 1--6 C atoms, which are preferably monosubstituted by OH, CN, halogen, phenyl, C1-C4-alkoxy, C1-C5-alkyl- carbonyloxy, C,-C,-alkoxycarbonyl, CONH2, COOH or OCONH2.

Cycloalkyl is preferably understood as cyclohexyl, which is optionally monosubstituted by C1-C4-alkyl, OH, CN, halogen or C1-C4-alkoxy.

Suitable aryl is, in particular, phenyl which is optionally monosubstituted to trisubstituted by halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, cyclohexyl or phenyl, the last three radicals mentioned preferably only occurring once.

The expression "acyl" should be understood in the broadest sense, that is to say as the radical of an organic acid; suitable acyl radicals are: formyl, alkylcarbonyl, arylcarbonyl and cycloalkylcarbonyl. C1-C4-Alkylcarbonyl radicals are preferred.

Suitable carbamoyl and sulphamoyl radicals are those of the formulae CONQ1Q2 and SO2NQ1Q2 respectively, wherein Q, denotes hydrogen, C1-C4-alkyl, phenyl, cyclohexyl or benzyl and Q2 denotes hydrogen or C1-C4-alkyl, or wherein Q1 and Q2 together form the radical of a heterocyclic compound, for example piperidinyl, morphodinyl or pyrrolidinyl.

"Bulky" radicals are in those positions where they cause no steric hindrance, for example tert.-butyl is in the m-position or p-position of a phenyl radical.

Suitable halogen is chlorine, bromine or fluorine, but preferably chlorine.

Preferred dyestuffs correspond to the formula

wherein V1 and V2 represent hydrogen, chlorine, bromine, cyano, CF3, nitro, C1-C4 alkyl, C1-C4-alkoxy, phenyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkylsulphonyl, phenylsulphonyl, benzylsulphonyl, COOH, So@NW@W@ or CONWtW2, wherein W1 and W2 = H1 C1-C4-alkyl or hydroxyethyl, V3 represents hydrogen, C1-C4 alkyl, chlorine, bromine or cyano, E1 represents hydrogen, C1-C4-alkyl, phenyl, tolyl, chlorophenyl, nitrophenyl or C1-C4-alkoxycarbonyl, and B represents the radical of a coupling component, preferably

wherein V4 represents hydrogen, C1-C4-alkyl, C1-C4-alkoxy, chlorine, bromine C1-C4-alkylcarbonylamino, hydroxyacetylamino, chloroacetylamine, cyano acetylamino, benzoylamino, toluylamino, chlorobenzoylamino, C1-C4-alkyl- sulphonylamino or phenylsulphonylamino, V5 represents hydrogen, C1-C4-alkyl, C1-C4-alkoxy, cyanoethoxy, chlorine, bromine or phenoxy, V6 represents hydrogen, C1-C4-alkyl, -CH2-C6H5, -CH2CH2OH, -CH2-CH2Cl, -CH2CH2OCOCH3, -CH2CH2OCOC2H5, -CH2CH2C6H5, -CH2CH2OCOC6H5, -CH2CH2OCOCH2C6H5, -CH2-CH2OCOCH2OC6H5, -CH2CH2OCOOCH3, -CH2CH2OCOOC2H5, -CH2CH2COOCH3, -CH2CH2COOC2H5, -CH2CH2CN, -CH2CH2OCH2CH2OH, -CH2CH2OCH2CH2OCOOCH3, -CH2-CH2OCH2CH2CN, CH2CH2OCOCOOH, -CH2CH2COOH, -CH2CH2OCOC2H4COOH or -CH2CH2OCONHW, -C2H4-OC2H5, -C2H4-OC4H9, -C2H4OC3H7 or -C2H4-OCH3 wherein W = H, 1-C4-alkyl, phenyl or cyanoethyl, and V7 represents V6 and is identical or different. Thc ,e dyestuffs of the formula II wherein E represents hydrogen, methyl or phenyl, V, represents hydrogen, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylsulphonyl, ethylsulphonyl, phenylsulphonyl, methoxycarbonyl, ethoxycarbonyl, SO2NW1W2 or CONWtW2, wherein W1 and W3 = H, methyl or ethyl, V2 represents hydrogen or chlorine, V3 represents hydrogen, methyl, chlorine or cyano, V4 represents hydrogen, methyl, ethyl. methoxy, ethoxy chlorine or acetyl amino, V5 represents hydrogen, methyl, methoxy or ethoxy, V6 represents ethyl, benzyl, phenylethyl, CH3CH2COOH,CH2CH2OH, CH2CH2CN, CH2CH2OCOCH3, CH2CH2OCOCH3, CH2CH2OCO2C2H5 or CH2CH2OCOCH2CH2COOH, C2H4-OCH3, -C2H4-O-C2H5, -C2H4-O-C4H9 or -C2H4-OC3H7, V7 represents V6 and is identical or different, or represents H, the radicals V1, V2 and V3 preferably being in the 2, 4 and 6-position, are very particularly valuable.

Dyestuffs of the formula (I) are obtained by coupling a diazotised amine of the formula A-NH2 wherein A has the abovementioned meaning, to an aminothiazole of the formula

wherein R1 and R2 have the abovementioned meaning and diazotising the resulting dyestuff of the formula

again and coupling the diazotisation product to a coupling component B-H wherein B has the abovementioned meaning.

Amines of the formula A-NH2 and coupling components BH which can be used those are compounds which are customary in the chemistry of azo disperse dyestuffs (compare, for example, British Patent Specification 1,125,683, pages 5 and 6).

The aminothiazoles are also known, or they can be obtained in a manner which is in itself known (compare "Heterocyclic Compounds", Volume 5, page 497, by R. C. Elderfield) by reacting compounds of the formula E-CO-CH3- halogen with thiourea.

The dyestuffs according to the invention are suitable for dyeing synthetic fibre materials, in particular polyamides and very particularly aromatic polyesters, such as polyethylene terephthalate and poly-1,4-cyclohexanedimethylene, from aqueous liquors or organic solvents. The types of fibre mentioned are dyed in deep violet to blue-green shades with good fastness properties in use.

Furthermore, the dyestuffs can be employed for the bulk dyeing of plastics.

EXAMPLE 1.

23.5 g of 2,4-dichloroaniline were diazotised with 300 ml of 50% strength HCI with 100 ml or 10 . strength NaNO2 solution at 0 C. The mixture is subsequently stirred at 0 C for 2 hours.

21g of 2-amino-thiazole hydrochloride are dissolved in 50 ml of H2O and the solution is introduced into 500 ml of saturated sodium acetate solution. The diazonium salt solution described above is added to this mixture at OOC. The pH is then adjusted to about 5 with sodium carbonate solution.

The dyestuff of the formula

which has precipitated is filtered off and dried at 400 C.

3.98 g of the monoazo dystuff described above was stirred in 20 ml of glacial acetic acid/20 ml of phosphoric acid at room temperature for one hour, the mixture was then cooled to OOC and the dyestuff wps diazotised with 5.2 g of nitrosylsulphuric acid. The mixture is subsequently stirred at OOC for 2 hours, 0.5 g of urea and 4.1 g of N,N-bis-(acetoxyethyl)-m-tolucidine in 30 ml of glacial acetic acid are added and the reaction mixture is introduced into ice. The dyestuff of the formula

which has precipitated is filtered off and dried at 400 C.

Dyeing Examples: 1) 1 part of the dyestuff obtained according to Example 1, which has been finely dispersed by customary processes, is stirred into 2,000 parts of water. The pH value is adjusted to 5 to 6 with acetic acid, and 4 parts of ammonium sulphate and 2 parts of a commercially available dispersing agent based on a condensation product of naphthalenesulphonic acid and formaldehyde are added. 100 parts of a polyester fabric based on polyethylene glycol terephthalate is introduced into the dye liquor thus obtained, and is dyed at l20-l300C for 1+ hours. After subsequent rinsing, reductive after-treatment with a 0.2% strength alkaline sodium dithionite solution at 60"C for 15 minutes, rinsing and drying, a reddish-tinged blue dyeing with good fastness properties, in particular good fastness to light and sublimation, is obtained.

2) 0.1 g of the well-dispersed dyestuff according to Example I is introduced, at 400 C. into I litre of water, which also contains 0.2 g of sodium dinaphthylmethanesulphonate and 0.3 g of cresotic acid methyl ester. 10 g of a fabric made of polyethylene terephthalate is introduced into this bath, the temperature of the dyebath is increased to 1000C in the course of about 20 minutes and dyeing is carried out at this temperature for 6090 minutes. A reddish-tinged blue dying with good fastness to sublimation and light is obtained.

If the procedure followed is as in Example 1 and the amines used as diazo components are the compounds listed in column 1, the aminothiazoles used are the compounds listed in column 2, and the compounds listed in column 3 of Table 1 are used as coupling components for the further diazotised monoazo dyestuffs primarily obtained, dyestuffs which dye polyamide fibres or polyester fibres in violet to greenish-tinged blue shades with good fastness to light are obtained. TABLE 1 Diazo component 1st Coupling component 2nd Coupling component

r rO e, M O C 3 . S: 1: p e s Cr13 a r 3 t el) 3 o C5 ,' ,, tU blue CI I0 u " " " " " " 'tf / \CI " slightly reddish-tinged \1In) 7) Ncaa. ', ', blue F1 z ZX Ua s 0 Z TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

a e w : 5: D 5) P w(%o0C11K3)a blue Noa 6 O = O O ^ C, e, a J D D ,, X slightly greenish-tinged '0.1 Cr13 Ii) " blue U 6 Noah & t ,, greenish-tinge4 blue z e XZo h3 CI ZX cz O ~ es en e m TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

a r ce g tr:: z il CIt3 o - iX) ' Nwa z 0 u Inl f n 20) z C113 21) ci/\CIIt ', slightly reddish-tinged 2' ',, blue CI z--i tn oJ z z s t t > oc v O ~ rl TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

r o o 8 bo c c c s a 3 ,1 r /\CINw e M o o CI u ot blue S::b, r tEi S 9 uz D W X D D u) D nl U 1 U 0 I e n t; Z w 27) 28) /\ MIta ,, slighfly greenish-tinged oN blue nr Z I- V, / r blue , (tl 0t t Z 0 t X v O a 1 rl rl N > ) TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

I c ^ o co D O O O b4 : > . = ~ cn o I"a v nl C''a s n cr, CI nss S U + -rs I C' Z Z Z ,, CP tVK 0 37) CIIa ,, ', ', ,, ,, 38) ,, Zs N C z=i, C U TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

CI e, : ^ - D E; a O Nila INI o C n t = a a a a, a CINIia 0 N/\C?iCN reddish-tinged blue C1-3 CaHs czar U t Xo N2' cu ,, ,, 43) \O " ,' " CI 44) y?ClNH " " ,, ,' Z At } Au u o ~ n n t u-, TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

o o e Ii p a b, a c ao a T .,, , N/\CJaCN reddish-tinged blue I s: I c N02 t r -a o a eX o a Noa 48) O " N/\cC:It45 CIt3 a C-C=O t o0 & g g O , e Nwa CI 51) so J: Z CIt3 Ut AX t3\2 C 6 0 sD rs x o b1 t t t sP m wr. un Diazo component 1st Coupling component 2nd Coupling component

o D o 6 H rn n " S rO r ^ ^ O 2 C a 55) N z OCH3 56) ,, , reddish-tinged blue I 1 c)=O CI Cl 1' 1 Z c1tso/\w1la Z II2 " - Cr13 58) " C4-o -C11-0CIt3)2 " ,' 0 59) C2IIts0NIta ,, ,, ZS ZA w Z f e S > t m vS b oo o C TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

a D o .~ O r a n 0 SN112 CItS ~O ^ o CH3 63) C3oIto34WIta =/f (u CM; 5 \ZX Z reddish-tinged blue 65) ', cIt;; 66) ItaC-SOaN " N/Ck4CN ,' CaIt ZZ 'D n S s 0 $ X Z 0 00 O= o=0 X 0 8 S-Z TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

o ,1 a p o b0 C . ~ Â c c a, a a, a, a 1 a, D W D Q C 70) ,, ,, NCcHs) I N < 0 I 71) CaIt5-o0C11/\ ,' N(CaIl4-oCI43)a reddish-tinged blue 72) CINIt ', blue 73) Cl 74) \Y . greenish-tinged blue c"5 75) Z ,4(cao-CIl3)a ,' ', I cn O sO ls TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

9 e, 1 1 3 c3 s c bO bn .fi < vS c c 76) I'loa H3NH2 .9 N (C-O- CM3) greenish-tinged blue c E:: e, u c o a, CIt3 77) HaC-soa ,, ,, blue NIla U g =O I S Il 0 79) C(1It2' ,, NCCaIt)a ,, ItN-C-CIt II 0 80) ,, ,, /\(ca4oCCIls) blue - II 0 HN -C-CM;; Il Z CtNIta P Zve Z U > aZZ D ut Z Diazo component 1st Coupling component 2nd Coupling component

a 3 I s e h a 82) 1F1 $ĭ1)f(Ca4OoClIC1IS)2 greenishtinged blue a, ^ 0 .0 0 0 .0 Ul D " Cl m 84) \ CM3 85) CI n CI OCalls blue (ca'It5)a z > ; blue 0CM3 87) N(Ca)a blue 'I oC3.

Z=4 Z,V) C- CM3 Il cu rl 00 t > z TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

o c a ,1 ,1 e o a 9 a a ao p, o, .~ g C | ' < 'v > a 1: h .9 .I1 a a o ru O-u-0 I U) 10 H2NCItS violet N 5 gI 0 z 8 I3, 92) CM7soaMIaa ,, \N;C:S4//o blue ""OH 93) Cl 0 0 reddish-tinged blue 0 I"-SOa WIt2 ,, ii Cl G z CH Cl P H3cĭ$ violet cu ru > zG C ? V o $ rx o < rm 3 Ct TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

o C ' = 5 C N m a .I , NC/\NIta .c: m:S C 09 Q l~ C O > O ra ~ ra U O = O = o C O > , O '5 . b . b ao m 97) No? l'l1la }){\CW bT\\ieS reddishtinged ONO CIIt3 98) Z N(C4-o c011NC5)a Sl1$htl greenish-tinged Cn3 CI"I ItO b O AP O S 99) u - CM3 blue 100) N::Ita ,, jwrio grey 101) ,' N(CaK5) greenish-tinged blue z ZA 0n 5 z sC > rx o O > v rD ro O O TABLE 1 (cont.) Diazo component 1st Coupling component 2nd Coupling component

a, o 1 1 o o N c e N H3CO NIl a .~ S .~ = 103) D D ,, blue It3C N NIta z U tn tn t I o u xZo 106) , blue 0 111 CI}&num;'\CIN11 Cli$;;1 ZA t z C C O Z Cd s Z 0 Z tX lZiZ 9 :C tJ EXAMPLE 109.

20.2 g of nitroaniline are diazotised in 300 ml of 50% strength HCI with 100 ml of 10 Ó strength NaNO2 solution at OOC. The mixture is subsequently stirred at 0 C for 2 hours.

21 g of 2-amino-thiazole hydrochloride are dissolved in 50 ml of H2O and this solution is introduced into 500 ml of saturated sodium acetate solution.

The diazonium salt solution described above is added to this mixture at 90C.

The pH is then adjusted to about 5 with sodium carbonate solution.

The dyestuff of the formula

which has precipitated is filtered off and dried at 400 C.

3.6 g of the dyestuff described above are stirred in 20 ml of phosphoric acid/20 ml of glacial acetic acid for 1 hour at OOC and then diazotised with 5.2 g of a 40% strength nitrosylsulphuric acid at OOC. The mixture is subsequently stirred at OOC for 3 hours. 1 g of urea and 3 g of N-ethyl-N-acetoxyethyl-m-toluidine, dissolved in 30 ml of glacial acetic acid, are then added to the diazonium salt solution.

The reaction mixture is introduced into ice. The dyestuff of the formula

which has precipitated is filtered off and dried at 400c.

WHAT WE CLAIM IS: 1. A disazo dyestuff which is free from sulphonic acid groups, of the general formula

in which A denotes a radical of a diazo component, B denotes a radical of a coupling component and E denotes a hydrogen atom or a substituent.

2. A disazo dyestuff according to Claim 1, in which A denotes a radical of the naphthalene, benzene, thiazole, benzthiazole, thiadiazole, triazole, pyrazole, indazole or thiophene series.

3. A diazo dyestuff according to Claim 2, in which A denotes a radical of the benzene series.

4. A disazo dyestuff according to Claim 3, in which A denotes a radical of the general formula in which

**WARNING** end of DESC field may overlap start of CLMS **.

Claims (27)

**WARNING** start of CLMS field may overlap end of DESC **. EXAMPLE 109. 20.2 g of nitroaniline are diazotised in 300 ml of 50% strength HCI with 100 ml of 10 Ó strength NaNO2 solution at OOC. The mixture is subsequently stirred at 0 C for 2 hours. 21 g of 2-amino-thiazole hydrochloride are dissolved in 50 ml of H2O and this solution is introduced into 500 ml of saturated sodium acetate solution. The diazonium salt solution described above is added to this mixture at 90C. The pH is then adjusted to about 5 with sodium carbonate solution. The dyestuff of the formula which has precipitated is filtered off and dried at 400 C. 3.6 g of the dyestuff described above are stirred in 20 ml of phosphoric acid/20 ml of glacial acetic acid for 1 hour at OOC and then diazotised with 5.2 g of a 40% strength nitrosylsulphuric acid at OOC. The mixture is subsequently stirred at OOC for 3 hours. 1 g of urea and 3 g of N-ethyl-N-acetoxyethyl-m-toluidine, dissolved in 30 ml of glacial acetic acid, are then added to the diazonium salt solution. The reaction mixture is introduced into ice. The dyestuff of the formula which has precipitated is filtered off and dried at 400c. WHAT WE CLAIM IS:

1. A disazo dyestuff which is free from sulphonic acid groups, of the general formula

in which A denotes a radical of a diazo component, B denotes a radical of a coupling component and E denotes a hydrogen atom or a substituent.

2. A disazo dyestuff according to Claim 1, in which A denotes a radical of the naphthalene, benzene, thiazole, benzthiazole, thiadiazole, triazole, pyrazole, indazole or thiophene series.

3. A diazo dyestuff according to Claim 2, in which A denotes a radical of the benzene series.

4. A disazo dyestuff according to Claim 3, in which A denotes a radical of the general formula in which

X, X2 and X3 independently denote a hydrogen atom or an alkyl, alkoxy, CN, NO2, CF3, alkylsulphonyl, halogen, aryl, COOH, alkoxycarbonyl, aryl, sulphamoyl or carbamoyl group.

5. A disazo dyestuff according to any of the foregoing claims, in which B denotes an aniline, a-aminonaphthalene, a phenol, an indole, a pyridone, a pyrazolone or an amino-pyrazolone radical.

6. A disazo dyestuff according to any of Claims 1 to 5, in which B denotes an aniline radical.

7. A disazo dyestuff according to any of Claims I to 5, in which B denotes a radical of the general formula

in which R3,R7 and R6 independently denote a hydrogen atom or an alkyl, alkoxy, halogen, alkylsulphonyl, aralkylsulphonyl, arylsulphonyl, sulphamoyl, carbamoyl, alkoxycarbonyl, or acylamino radical, R4 denotes a hydrogen atom, an alkyl group, a halogen atom or an alkoxy or acylamino group, R6 and R6 independently denote an alkyl or aralkylradical or a hydrogen atom, R9 denotes a hydrogen atom or an alkyl, alkoxy or cyano group, R10 denotes an alkyl or aryl group or a hydrogen atom, R1, denotes a hydrogen atom or an alkyl group, R.2 denotes a cyano, carbamoyl or alkoxycarbonyl group, a hydrogen atom or an alkyl or aryl group, R13 denotes a hydrogen atom or an alkyl or aryl group, R4 denotes a hydrogen atom or an alkyl group, R,s denotes a hydrogen atom or an alkyl, hydroxyl, aryl or alkoxycarbonyl group and R.6 denotes a cyano, carbamoyl or alkoxycarbonyl group, it being possible for the above mentioned radicals to be optionally substituted.

8. A disazo dyestuff according to Claim 7, in which E denotes an optionally substituted alkyl, aryl or alkoxycarbonyl radical or a hydrogen atom.

9. A disazo dyestuff according to Claim 1, which is free from sulphonic acid groups, of the general formula

in which V1 and V2 independently denote a hydrogen, chlorine or bromine atom or a cyano, CF3, nitro, C1 to C4 alkyl, C1 to C4 alkoxy, phenyl, (C1 to C4 alkyl) carbonyl, (C1 to C4 alkoxy)-carbonyl, C1 to C4 alkylsulphonyl, phenyl sulphonyl, benzylsulphonyl, COOH, SO2NW,W2 or CONW,W2 group in W, and W2 independently denote a hydrogen atom or a C, to C4 alkyl or hydroxyethyl group, V3 denotes a hydrogen atom, a C, to C4 alkyl radical, a chlorine or bromine atom or a cyano group, E, denotes a hydrogen atom or a C, to Cd alkyl, phenyl, tolyl, chlorophenyl, nitrophenyl or C1-C4-alkoxycarbonyl group and B denotes a radical of a coupling component.

10. A disazo dyestuff according to Claim 9, in which B denotes a radical of the general formula

in which V4 denotes a hydrogen atom, a C, to C4 alkyl or C17C4-atkoxy group, a chlorine or bromine atom or a (C, to C4 alkyl)-carbonylåmino, hydroxyacetyl amino, chloroacetylamino, cyanoacetylamino, benzoylamino, toluylamino, chlorobenzoylamino, C, to C4 alkylsulphonylamino or phenylsulphonylamino group, V5 denotes a hydrogen atom, a C, to C4 alkyl, C, to C4 alkoxy or cyanoethoxy group, a chlorine or bromine atom or a phenoxy group, V@ denotes a hydrogen atom or a C1 to C4 alkyl, -CH2-C6H5, -CH2CH2OH, -CH2-CH2Cl, -CH2CH2OCOCH3, -CH2CH2OCOC2H5, -CH2CHC6H5, -CH2CH2OCCOC6H5, -CH2CH2OCOCH2C6H5, -CH2-CH2OCOCH2OC6H5, -CH2CH2OCOOCH3, -CH2CH2OCOOC2H5, -CH2CH2COOCH3, -CH2CH2COOC2H5, -CH2CH2CN, -CH2CH2OCH2CH2OH, -CH2CH2OCH2CH2OCOOCH3, -CH2-CH23OCH2CH2CN, CH2CH2OCOCOOH, -CH2CH2COOH, -CH2CH2OCOC2H4COOH or -CH2CH2OCONHW, -C2H4-OC2H5, -C3H4-0C6H6, -C2H4OC3H7 or -C2H4-OCH3 group, in which W denotes a hydrogen atom or an alkyl, phenyl or cyanoethyl group and V7 has the same meanings as V6 and is identical or different.

Il. A disazo dyestuff according to Claim 10, in which E denotes a hydrogen atom or a methyl or phenyl group, V, denotes a hydrogen, chlorine or bromine atom or a cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylsulphonyl, ethylsulphonyl, phenylsulphonyl, methoxycarbonyl, ethoxycarbonyl, SO2NW,W2 or CONW1 W2 group, in which W1 and W2 independently denote a hydrogen atom or a methyl or ethyl group, V3 denotes a hydrogen or chlorine atom, V3 denotes a hydrogen atom, a methyl group, a chlorine atom or a cyano group, V4 denotes a hydrogen atom, a methyl, ethyl, methoxy or ethoxy group. a chlorine atom or an acetylamino group, V, denotes a hydrogen atom or a methyl, methoxy or ethoxy group, V6 denotes an ethyl, benzyl, phenylethyl, CH2CH2COOH, CH 2CH 2OH, CH2CH2CN, CH2CH2OCOCH3, CH2C H2OCOCH3, CH2CH2OCO2C2Hs or CH2CH2OCOCH2CH2COOH, C2H4-OCH3, -C2H4-O-C2H5, C2H4-O-C4H9 or -C2H4-OC3H7 group, V7 has the same meanings as V6 and is identical or different, or denotes a hydrogen atom.

12. A disazo dyestuff according to Claim 10 or 11, in which V6 has any of the meanings given therein other than the -C2H4-OC4H9 group.

13. The dyestuff of the formula

14. A disazo dyestuff according to Claim 1, as hereinbefore specifically identified, other than the dyestuff claimed in Claim 13 and the dyestuffs of Examples 34, 46 and 64.

15. A disazo dyestuff according to Claim 1, as hereinbefore specifically identified in any one of Examples 34, 46 and 64.

16. A process for the production of an azo dyestuff as claimed in Claim 1, in which an amine of the general formula A-NH2 in which A has the same meaning as in Claim 1, is diazotised and the diazotisation product is coupled to a compound of the general formula

in which E has the same meaning as in Claim 1, and the aminomonoazo dyestuff formed is again diazotised and the diazotisation product is coupled to a coupling component of the general formula B-H in which B has the same meaning as in Claim 1.

17. A process for the production of an azo dyestuff as claimed in Claim 1, when carried out substantially as described in any one of the Examples, other than Examples 34, 46 and 64.

18. An azo dyestuff as claimed in Claim 1, when produced by the process of Claim 16 or 17.

19. A process for the production of an azo dyestuff as claimed in Claim 1, when carried out substantially as described in any one of Examples 34, 46 and 64.

20. An azo dyestuff as claimed in Claim 1, when produced by the process of Claim 19.

21. A process for dyeing or printing a synthetic fibre material comprising treating the material with an azo dyestuff as claimed in any of Claims 1 to 7, 9 to 11, 13, 14 and 18.

22. A process according to Claim 21, when carried out substantially as described in the "Dyeing Example" in Example 1.

23. A synthetic fibre material when dyed or printed by the process of Claim 21 or 22.

24. A process according to Claim 21, in which a dyestuff as claimed in any of Claims 8, 12, 15 and 20 is used.

25. A synthetic fibre material when dyed or printed by the process of Claim 24.

26. Disazodyestuffs according to claim 1, wherein B represents an ortho-alkyl benzene radical.

27. A disazo dyestuff according to any of claims 7-11, wherein R4 and V4 respectively are CH3 or C2Hs.