GB1569062A - Disazo dyestuffs - Google Patents

Disazo dyestuffs Download PDF

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GB1569062A
GB1569062A GB7698/78A GB769878A GB1569062A GB 1569062 A GB1569062 A GB 1569062A GB 7698/78 A GB7698/78 A GB 7698/78A GB 769878 A GB769878 A GB 769878A GB 1569062 A GB1569062 A GB 1569062A
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optionally substituted
methyl
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chlorine
alkyl
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
    • C09B31/043—Amino-benzenes
    • C09B31/047—Amino-benzenes containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters

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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 provides disazo dyestuffs which contain only one acid group and which, in the form of the free acids, correspond to the formula
wherein p is 0 or 1, X denotes OH, NH-SO2-R8, N(Rg)-alkylene-OSO3H, N(R9)-alkylene-SO3H, N(R9)-arylene-SO3H, N(R9Yarylene-CH2-SO3H or N(R9)-arylene-SO2-NH-SO2-R8, Z denotes acyl, R1 and R2 denote hydrogen or non-ionic substituents, R3, R4 and R5 denote hydrogen, optionally substituted alkyl, optionally substituted aralkyl, optionally substituted aryl, halogen, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aralkoxy or optionally substituted acylamino; or R4 and R3 together denote the remaining members of a fused benzene ring, Re and R9 denote hydrogen or optionally substituted alkyl, R, denotes hydrogen, optionally substituted alkyl, optionally substituted aryl or optionally substituted aralkyl and R9 denotes optionally substituted alkyl, optionally substituted aralkyl, optionally substituted aryl or dialkylamino.
As used herein the term "non-ionic substituents" means a substituent which does not dissociate under the condition of production or use of the dyestuff.
Preferred non-ionic substituents R, and R2 are halogen, cyano, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, trifluoromethyl, nitro, thiocyano, optionally substituted carbamoyl, optionally substituted sulphamoyl, optionally substituted alkylsulphonyl and optionally substituted arylsulphonyl. Preferred substituents of the carbamoyl and sulphamoyl groups are optionally substituted alkyl, optionally substituted aralkyl and optionally substituted aryl.
Preferred acyl radicals Z and in the acylamino groups R2, R4 and R5 are optionally substituted alkylcarbonyl, optionally substituted arylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted aryloxycarbonyl, optionally substituted alkylsulphonyl, optionally substituted aralkylsulphonyl and optionally substituted arylsulphonyl.
As used herein the term "acyl" means any organic "acid group", the hydrogen atom of which is easily replaced by for example a metal atom and includes, in addition to those acyl radicals mentioned above, an activated pyrimidinyl, an alkoxycarbonyl and a triazinyl radical.
Preferred alkyl radicals R1, R2, R3, R4, R5, R6 R7, R8 and R9, in the alkylsulphonyl groups and as substituted of the carbamoyl and sulphamoyl radicals are preferably those with I to 4 carbon atoms, which may be substituted by halogen, cyano, hydroxyl or C,-C4-alkoxy.
Preferred aryl radicals R1, R2, R3, R4, R5, R7 and R8, in the arylcarbonyl and arylsulphonyl groups and as substituents of the carbamoyl and sulphamoyl groups are phenyl and naphthyl radicals which are optionally substituted by phenyl, C1-C4 alkyl, halogen nitro or C1-C4 alkoxy.
Preferred aralkyl groups R3, R4, R5, R7 and R8 in the aralkylsulphonyl groups and as substituents of the carbamoyl and sulphamoyl radicals are benzyl and 2phenylethyl, which may be substituted in the phenyl radical by C1-C4-alkyl, C1-C4 alkoxy, halogen, nitro or cyano.
Preferred alkoxy groups R1, R2, R3, R4 and R5 and in the alkoxycarbonyl groups are C1-C4 alkoxy groups, which may be optionally substituted by hydroxyl, halogen or cyano.
Preferred aryloxy radicals R3, R4 and R5 and in the aryloxycarbonyl groups are phenyloxy or naphthyloxy radicals which are optionally substituted by phenyl, C1-C4 alkyl, halogen, nitro or C1-C4 alkoxy.
Preferred aralkyloxy groups R3, R4 and $5 and in the aralkyloxycarbonyl radicals are benzyloxy and 2-phenylethoxy groups, which may be substituted in the phenyl radical by C1-C4 alkyl, C1-C4 alkoxy, halogen, nitro or cyano.
The alkylenes as a constituent of the radicals X are preferred C2-C6 alkylene groups, which may be straight-chain or branched. The arylenes as a constituent of the substituents X are preferably phenylene radicals, which may be further substituted by C1-C4 alkyl, C1-C4 alkoxy, halogen, cyano or nitro.
The alkyl groups of the dialkylamino radicals Re preferably contain I to 4 carbon atoms. Preferred halogen atoms are fluorine, chlorine and bromine, especially chlorine and bromine.
Those dyestuffs which contain an acyl group Z which is not fibre-reactive are preferred.
Preferred dyestuffs within the formula I are those in which p has the above mentioned meaning, X denotes OH, NH-SO2-Re, N(R9)-(C2-C6) alkylene OSO3H, N(R9)-(C2-C6) alkylene-SO3H, N(R9)-phenylene-SO3H, N(R9)-phenylene CH2-SO3H or N(R9)-phenylene-SO2NO-SO2-R8 wherein the phenylene may be substituted by C1-C4 alkyl, C1-C4 alkoxy, halogen, cyano or nitro.
R, and R2 independently denote hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, cyano, trifluoromethyl or phenoxy, R3, R4, R5 and R6 independently denote hydrogen, C1-C4 alkyl, C1-Cd alkoxy, C1-C4 alkylcarbonylamino, benzoylamino, C1-C4 alkylsulphonyl amino, phenylsulphonylamino c-c4 alkoxycarbonylamino or phenoxy carbonylamino, wherein the phenyl nuclei may be substituted by methyl, ethyl, methoxy, ethoxy, chlorine, bromine or cyano, R, denotes hydrogen, C1-C4 alkyl which is optionally substituted by chlorine, hydroxyl, cyano, benzyl or phenethyl, R8 denotes C1-C4 alkyl or phenyl which is optionally substituted by methyl, chlorine or bromine, R9 denotes hydrogen, methyl or ethyl and Z denotes C1-C4 alkylcarbonyl which is optionally substituted by cyano.
C1-C4 alkoxy, phenoxy or phenyl, benzoyl which is optionally substituted by C1-C4 alkyl, chlorine, bromine, nitro, cyano or C1-C4 alkoxy, C1-C4 alkyl sulphonyl, phenylsulphonyl, phenoxycarbonyl or C1-C4 alkoxycarbonyl, wherein the phenyl and phenoxy groups may be substituted by chlorine, C1-C4 alkyl, C1-C4 alkoxy or cyano.
Particularly preferred dyestuffs are those which, in the form of the free acid, correspond to the formula
wherein Z' denotes C1-C4 alkylcarbonyl, benzoyl which is optionally substituted by methyl, methoxy or chlorine, phenylacetyl which is optionally substituted by methyl, methoxy or chlorine or phenoxyacetyl which is optionally substituted by methyl, methoxy or chlorine, X' denotes CH, NH-SO2-R8', N(R9')-(C2-C4)-alkylene-OSO3H, N(R9')-(C2-C4) alkylene-SO3H or
R, and R2 independently denote hydrogen, methyl, ethyl, chlorine, bromine or trifluoromethyl R' and R4 independently denote hydrogen, methyl, ethyl, methoxy, ethoxy, acetylamino, methylsulphonylamino or phenylsulphonylamino, R5' denotes hydrogen, methyl, ethyl, methoxy, ehtoxy or acetylamino, R6' denotes hydrogen, or mehyl, R7' denotes hydrogen, methyl, ethyl, 2-cyanoethyl, 2-chloroethyl, benzyl or phenethyl, R8 denotes C1-C4 alkyl or phenyl which is optionally substituted by methyl, chlorine or bromine and Rg denotes hydrogen, methyl or ethyl.
Especially preferred compounds are those which, in the form of the freee acid, correspond to the formula
wherein X', R; and Ré have the abovementioned meaning, R'2 denotes hydrogen or methyl, R'3 denotes hydrogen, methyl or methoxy, R'4 denotes hydrogen, methyl, methoxy, ethoxy or acetylamino, R5 denotes hydrogen, methyl or acetylamino and Z" denotes acetyl, propionyl, benzoyl which is optionally substituted by methyl, methoxy or chlorine, phenylacetyl which is optionally substituted by methyl methoxy or chlorine, or phenoxyacetyl which is optionally substituted by methyl, methoxy or chlorine.
The dyestuffs of the formula (I) are prepared by coupling diazotised aminoazo compounds of the formula
wherein X, R1, R2, R3, R4 and p have the meaning already given, to amines of the formula
wherein RB, Re and R, have the meaning already given, and subsequently acylating the product, the radical Z wherein Z has the meaning already given, being introduced.
The dyestuffs according to the invention are suitable for dyeing natural and synthetic fibre materials, in particular for dyeing polyamide fibres, in level yellow to orange shades of good colour yield and very good fastness to light and wet processing. The present invention accordingly further provides a process for dyeing a natural or synthetic fibre material comprising treating the material with a dyestuff of the present invention. The dyestuffs of the present invention are already absorbed well onto polyamide fibres in a neutral to weakly acid dyebath. Polyamides are understood here, in particluar, as those consisting of synthetic polyamides, such as E-polycaprolactam, or condensation products of adipic acid and hexamethylenediamine.The dyestuffs are used here either in the form of the free acid or in the form of their salts, in particular the alkali metal salts, preferably the sodium or potassium salts, as well as the ammonium salts.
Example 1.
13.65 g of p-sulphanilic acid are dissolved in 150 ml of water with 5 g of sodium hydroxide. Thereafter, 5 g of sodium nitrite are added. The resulting solution is added dropwise into a mixture of 500 g of ice and 50 ml of concentrated hydrochloric acid. The mixture is subsequently stirred at OOC for 2 hours, theexcess nitrite is destroyed with amidosulphonic acid, and a solution of 8.8 g of 2,5dimethylaniline in 100 ml of glacial acetic acid is added dropwise. The pH value is adjusted to about 4 with saturated sodium acetate solution. Thr dyestuff which has precipitated is filtered off and dried at about 40"C.
4.4 g of the dyestuff described above are stirred in 150 ml of 50 / by weight hydrochloric acid and diazotised at room temperature with 1 g of sodium nitrite, dissolved in 10 ml of water. 1.6 g of m-toluidine are dissolved in 50 ml of glacial acetic acid and the solution is added to the diazonium salt solution. The pH value is adjusted to about 4 with saturated sodium acetate solution. The dyestuff which has precipitated is filtered off and dried at about 40"C.
3 g of the disazo dyestuff described above are stirred in 60 ml of acetic anhydride and 20 ml of glacial acetic acid at 120"C for 2 hours. The mixture is allowed to cool to room temperature and the dyestuff which has precipitated of the formula
is filtered off, rinsed and dried at 400 C.
Dyeing Example.
0.1 g of the dyestuff prepared according to Example 1 is dissolved hot in 100 ml of water, 5 ml of ammonium acetate solution are added and the mixture is diluted with water to a volume of 500 ml. 10 g of a polyamide fabric are put into the dyebath, the dyebath is brought to the boil in the course of 20 minutes, 4 ml of I strength by weight acetic acid are added and the bath is kept at the boiling point for one hour. Thereafter, the fabric is rinsed and dried at 70 to 800 C.
A yellowish-tinged orange dyeing of very good fastness to light is obtained.
Further valuable dyestuffs with the indicated colour shades according to the following tables are prepared in a manner corresponding to that in Example 1.
No. R1 R2 R3 R4 R5 R7 Z 2 H H H H 5-CH3 H -CO-CH3 reddish-tinged yellow 3 H H CH3 H 5-CH3 H -CO-CH3 " 4 H H CH3 CH3 H H -CO-CH3 " 5 H H H CH3 H H -CO-CH3 " 6 H H H CH3 5-CH3 H -CO-CH3 " 7 H H H CH3 6-CH3 H -CO-CH3 " 8 H H -O-CH3 H 5-CH3 H -CO-CH3 yellowish-tinged orange 9 H H -O-CH3 CH3 5-CH3 H -CO-CH3 " 10 H H -CH3 -O-CH3 5-CH3 H -CO-CH3 " 11 H H H -O-CH3 5-CH3 H -CO-CH3 " 12 H H H -NH-CO-CH3 5-CH3 H -CO-CH3 " 13 H H -CH3 -NH-CO-CH3 5-CH3 H -CO-CH3 " 14 H H -O-CH3 -O-CH3 5-CH3 H -CO-CH3 orange 15 H H -O-CH3 -O-CH3 6-CH3 H -CO-CH3 " No. R1 R2 R3 R4 R5 R7 Z 16 H H -O-CH3 -O-CH3 H H -CO-CH3 orange 17 2-CH3 H H CH3 H H -CO-CH3 yellowish-tinged orange 18 2-H3 H -CH3 CH3 5-CH3 H -CO-CH3 " 19 2-CH3 H -CH3 H H H -CO-CH3 " 20 2-CH3 H -CH3 -CH3 H H -CO-CH3 " 21 2-CH3 H H -O-CH3 H H -CO-CH3 " 22 2-CH3 H CH3 O-CH3 H H -CO-CH3 " 23 2-CH3 H -OCH3 CH3 5-CH3 H " " 24 2-Cl H H H H H " " 25 2-Cl H H CH3 5-CH3 H " " 26 2-Cl H CH3 CH3 5-CH3 H " " 27 2-Cl H H O-CH3 6-CH3 H " orange 28 2-Cl H H NH-CO-CH3 H H " " 29 2-Cl H OCH3 NH-CO-CH3 5-CH2 H " reddish-tinged orange 30 2-O-CH3 H CH3 CH3 5-CH3 H " reddish-tinged yellow No.R1 R2 R3 R4 R5 R7 Z
a S-o o c o 0 9 oO M CD e c ' o r O M T a 1 Q orange n 2-CH3 t.
U UN Ú 33 2-CF3 H y. CH3 5C2He H 3 yellow 8 35 2-CF3 H CH3 CH3 5-NH-C0-CH3 H ,, orange 36 H H CH3 CH3 ,, H 37 H H OCH3 CH3 ,, H .,.
U 39 2-CH3 H H CH3 , d " u u m m ) = Vw z z I yellow 42 H H CH3 CH3 6-CH3 H -CO-C3H7 U U OUUUU U 3 U V V G U V C.) =- U V U V CJ V V r U U O : = = D V NC ~ U U V U U v U V U ~ > t m sD > 00 0E 0 H N n No.R1 R2 R3 R4 R5 R7 Z
3 -3 3 ^jb 9 c E: e, M T u ' Y 3 o~S 3 30 CD O C e, M 44 H 2" yellow 45 H H tf 1 2CH3 H Qd 8 2-CH3 H H CH3 6-O-CH3 H ,, yellowish-tinged U za QJ 49 2-Cl H 3: 3: CH3 H = C X U H II v Q = Cil3 m :m CL vss lo vl 51 H H Cil3 Cil3 5-CH3 H ,' reddish-tinged orange 52 H Il H CH3 5-CR3 C113 , m v m m m m m m m ~ 8 " ' m n 30 -m O u !;J O ~ v v rD v ;;;J v R i m m m = m ZJ ~ e e v x I I e n v x ~ = x ~ x x x ~ x ~ X x m m m ~ v v v D x : N N N N x x x ~ O1 t m 95 > 00 O ~ O1 t No. R1 R2 R3 R4 R5 R7 Z
a a 1 h b .f: 3 a a .O O a u I I k 56 2-Cl H H m . a u" e3: rr ,o V V E V 'V 58 m H qx m o "o ç V X V V i le | m V = ; 3 V 1 v X z to OVX V es c1 C X = m m m m m v7
No.R1 R2 R3 R4 R5 R7 Z 60 H H H H H H CO-CH3 reddish-tinged yellow 61 H H H CH3 3-CH3 H " " 62 H H CH3 H 3-CH3 H " " 63 H H CH3 CH3 H H " " 64 H H CH3 CH3 3-CH3 H " " 65 H H CH3 O-CH3 H H " " 66 H H CH3 O-CH3 3-CH3 H " yellowish-tinged orange 67 H H O-CH3 CH3 3-CH3 H " " 68 H H O-CH3 CH3 H H " " 69 H H O-CH3 O-CH3 H H " orange 70 H H O-CH3 O-CH3 3-CH3 H " " 71 4-CH3 6-CH3 O-CH3 O-CH3 3-CH3 C2H5 " reddish-tinged orange 72 4-O-CH3 H CH3 CH3 3-CH3 C2H5 " reddish-tinged yellow No.R1 R2 R3 R4 R5 R7 Z
o E o r o o ~ m w .~ 'Ct, ' Oc a =d Ct 73 H H CR3 2-CR3 C2He CO-CR3 reddish-tinged a íf) O Q Q 75 4-Cl It 8 76 6-Cl H H H 3-0-CR3 C2H3 77 6-Cl H CR3 CH3 H C3H3 ,, reddish-tinged V t Ú e" '3 cP 3 N N 6-Cl H N o" u u" 3: 3: I u 79 U U = H -s:" H Il 3-CR3 G UU O u uu~ u v c rn H OCR3 CR3 3-CR3 C2H4Cl n a rv m O m @ I m m m m v Z X v X v X ;;J e xa xa X xa ^ xa r CC X r X v r v X C X X X = : X = Q ~ D v v v t Ç c X X rn t V} xD > X : > > > F F > x x x No. R1 R2 R3 R4 R5 R7 Z
a 8 1 o E o 4 c: h 83 H H > > M o o W > E 84 H H CH3 H Q-s"s"l 85 H 8 8 8 8 U U V . u U . U e" ae" 3 '3 '3 = V V V V V V 86 H H OCR3 U 3-CR3 C2Re u" 87 H H CR3 OCR3 H QRe -co--o cH5 88 H H OCR3 OCR3 3-CR3 C2Rs ,' orange n 2-Cl 5-Cl H Im a U U U 3: 3: U O C U a a a a a rt = a X I V v !T: v Ú V O O V O = V V X X 5: = = X N e t m F oo ofi oo oo oo oo oo oo c o No. R1 R2 R3 R4 R5 R7 Z
-cl "M 71 -ri a E S S c E E r: vl 3 r: .5 h o 90 4Cl 6-Cl H OCR3 3-O-R3 C2RB | Z N - 3: I I N 4-CR3 6-CR3 H OJ 92 4-CR3 6-CR3 CR3 CR3 3-CR3 H 8 a I I 3s c" 93 6-Br H 3: e 3: U" vl 31 H vl CR3 a a H -CO-CR2-CN reddish-tinged I I I U c; cc, m I H: 96 H H H CR3 3-CR3 H ,, 97 4-CR3 6-CR3 H = 3-CR3 xa xa 3, yellowish-tinged O O v O v v v O rr V V V v X :C a a a v v v rv x x v c xo a a xu a V v V 1= vN v t ~ X t O ~ N eP m wo > No.R, R2 R3 R4 Rs R, Z
98 4-0-II 4-o < ) H H CH3 H H Oe reddish-tinged 99 4-Ot H CH3 CH3 3-CH, H Example 100.
18.1 g of 4-(N-methylsulphonyl-amidosulphonyl)-aniline are dissolved in 150 ml of water with 5 g of sodium hydroxide. Thereafter, 5 g of sodium nitrite are added. The resulting solution is added dropwise to a mixture of 500 g of ice and 50 ml of concentrated hydrochloric acid. The mixture is subsequently stirred at OOC for 2 hours, the excess nitrite is destroyed with amidosulphonic acid, and a solution of 10.3 g of 2-methyl-5-methoxyaniline in 100 ml of glacial acetic acid is added dropwise. The pH value is adjusted to about 4 with saturated sodium acetate solution. The dyestuff which has precipitated is filtered off and dried at about 40"C.
8.7 g of the dyestuff described above are stirred in 150 ml of half-concentrated hydrochloric acid and diazotised at room temperature with I g of sodium nitrite, dissolved in 10 ml of water. 1.6 g of m-toluidine are dissolved in 50 ml of glacial acetic acid and the solution is added to the diazonium salt solution. The pH is adjusted to about 4 with saturated sodium acetate solution. The dyestuff which has precipitated is filtered off and dried at 400 C.
3.6 g of the disazo dyestuff described above are stirred in 60 ml of acetic anhydride and 20 ml of glacial acetic acid at 1200C for 2 hours. The mixture is allowed to cool to room temperature and the dyestuff, which has precipitated, of the formula
is filtered off. The dyestuff dyes polyamide fibres yellowish-tinged orange.
No.R8 R1 R2 R3 R4 R5 R7 R6 Z
-ct -cr -J s p, a -oM-oOOoo 3 , ~ 3 3 3 0 3 o ^ ^ < 3 ~ 5 vl "M LI - C L ti41 M e, b - * r c -ct E O O C) C a O u yellow o CR3 H H OCR, CR, 3-CR3 H H ,, yellowish-tinged 103 C,H3 2-CR3 H CR3 CR3 3-CR3 H 6-CR3 reddish-tinged orange = Ux H H CR3 v U U U U U 105 C3R7 2-OCR3 H CR3 H 3-CR3 H 5-CR3 ,, yellowish-tinged 0 106 C4Rq H H OC2He H 3-CR3 CR3 H u E c (4Ra 2-Cl 5-CR, x H H H H a m a a a a a a U CII, 2-Cl H H CR, 3-CR, H 6-qH, ,, reddish-tinged l yellow 3: 3: U U 5, U c.z H H CR, CR, 3-CR3 O 6-CR, v u a c a a a XN a a Xx u x v D v x x x v xa = x x x x x = m :s x a a OVI D U U = x > x > = cs u F b b os ob X X X X X X X w ~I o o o o o o o c ~ o No.R8 R1 R2 R3 R4 R5 R7 R6 Z
a a o o a bo a bo a ag s C I C P 9 6 ill CR, R H H CR, 3-CR, o W > yellow 112 | a Q U 113 CR, 2-CF, v OCR3 CR, 3-CR, I v '3m u X H : r CR, 3-CR, H X ,, reddish-tinged - Ir 115 ,, H H CR, CR, 3-CR3 H H z u 117 V I H CR, OCR, 3-CR, X H 31 31 ' e" I: 118 H v v E v v v m I n 3 3 'c^ 3n '30 v v v ,, v v CR, CR, 3-CR, c H d1d10Shtd a a a U xa = a = x O = v o kS o : ) v X n X :: X X X X X a v v C X X X = = a a v u u No R8 R1 R2 R3 R4 R5 R7 R6 Z
b X ea r e4 h e 3 r 9 120 > H CR, CR, 3-CR, R H 0 121 ,, 2-CR, 5-CR, H CR3 3C3Re C2H, H -COO%H5 122 H H CR3 CR, 3-CR, 3CRa H -CO-CR, 8 ,, H H H CR, 3-CR, 3-CR, H r X H H OCR, CR, H H H " yellowish-tinged - orange 125 2-CR, R H CR, H H H " reddish-tinged H3C yellow = a U va U OU U U 126 /\ 2-CR, H H NH-COCR, c 'r" e o) x x ::c orange a X a a a a U a 3 '3n 3 e" u e o u 128 ,, 2-Cl H CR, OCR, 3-CR3 3-CR, R -WCL a a = u x U x Ov x x x v a u v x m x x x x x m x V ' va V V Q V es rs x x x > n > > t 34 O c9 t m vD F 00 No.R8 R1 R2 R3 R4 R5 R7 R6 Z
a 3 g a ao E E s ea 3 en t 03 C 5) 9 o W O o o 4 4 N Q-d 129 H H CR, OCR, 3-CR3 3-CR, H 0logwishtined 130 , 2-CR, H CR, CR, 3-CR, 3-CR, H CO / \ yellowish-tinged - orange CL CL 131 H \b 3: \b C a 132 CL H H CR, OC,H, 3-CR, C,Re 6-CR3 -C-OC,H3 yellowish-tinged a a Q 0 E &verbar; N U I X 133 CL 2-Br H a m a a e U i3 u 3 c; u u c c: c; c; 134 CL 2-CF, H OCR, CR3 V H 6-CR, -C-CR, II m = Ct v v OCIl, CII, 3-CR, o o x x : x 5 s a a v x N :c x es es x Q > o ~ c c9 n n < No. R8 R1 R2 R3 R4 R5 R7 R6 Z
a s c CS 0 V10 CiC C al ~;d d 5, 0cl o 0 W=0 O=0 a a 137 H H CR3 CR, 3-CR, H 5-CR, CflCt3CL reddish-tinged C 3: 3: a 138 2-CR, 5-CR, II CII, 3-CR, C2H3 R -5O Ct X N - orange m a a vO U v v m a a x = ~ EJ U U D O c m D -r O Q x x V N x c9 x c oo o
No.X R1 R2 R3 R4 R5 R7 R6 Z
a a a a b F: c: I c h 4 j: 3 n X o o X t o o X bO ~ObO O t t o" CR, 3-CR, C,Re o -CO-CR, reddish-tinged U X = : ,, H X X X U ,, 2-CR, H CR, X 31 V V V U H H H C2H5 H a a a a a a V V 2-Cl V CR, OCR, UUUUUV V n HO,S-C,R4NR- X on H '5:en xa ,, H xa a U U D x x O x X c c 147 ,, H H H OCR, 3-CR, H H ,, yellowish-tinged orange 148 ,, o X 3: iieceo = x x = x x x x D v : x x o ~ t ^ t m Xo b oo No. X R1 R2 R3 R4 R5 R7 R6 Z
a a a s E 4 m o RO,C,R4l'IR- R R > OCR, o R H -CO-CM3 orange 150 ,, H H CR3 H 3-CR3 H H ,, reddish-tinged u 0 0 151 ,, H H CR, CR, 3-CR, H 6-CR, o ,, H H CR, CR, 3-CR, C2Me H a, 8 8 8 154 ,, 2-Cl H H CR, 3-CR, C3Rs H v 155 ,, 2-Cl 5-Cl H CR, 3-CR, C2R5 H ,, = orange 156 ,, 2-CM, H H CM, H C2Re H ,, reddish-tinged yellow z ,, 2-CM, H OCR, CR, H C,M1 H yellowish-tinged orange N U ''3n3n'oo' u~U uuTj, u a 159 a n H n OCR, CR, H n Ov 160 V V R H CR, NR-COCR, 3-CR, C,Me Vl -CO-CR, z a a a = a a x 5 a Q = x :c D v v x O Q v v x : = = O O O v = :c x x = t m x v x X x a a v v v v :2 x = 3 = es > > > :c x x i t CCN F 0 c7 > 0 es t m \0 > x o o No.X R1 R2 R3 R4 R5 R7 R6 Z
161 RO,S-C2R4NR- H H CR, CR, 3-CR, H H r$d1$ishtined Q ,, H H CR, OC,Rs H C2R5 H ,, yellowish-tinged orange 8 ,, 1 8 CR, OC,Rs 3-CR3 H H I = Il X = = = X = 165 ,, H H H 0C,R 3-CM, C,Re H 166 HO,S-C,R4N-CH, H H CR, CR, 3-CR3 H R , reddish-tinged yellow 167 ,, H H CR, OC,R3 3-CR3 H H ', yellowish-tinged orange 3y 330 d" 3 169 X z V = = X V 3-CR, V VN a a a a a a a U ,, 2-Cl H CR, = v v v yellow 171 ,, H II u u u a XN XN N N a N ' a s a a m x X Ç x D x x x x 172 O H II H CR3 H C2Re D : H u v ÇJ x x v v O O CJ x x = x x x x x x :c :c x x x v x cc x ~ x = : x x cs x 3 a I Xx N X U V O a x x N t m so > oo ss O < N so xo Xo q: v xo vo s Xo F rs > No.X R1 R2 R3 R4 R5 R7 R6 Z
-cr 3 P o S a e 9 6 "M 360 , > n H H H ^ ^ ^ C ' 03 0C4 CR3 o yeow 174 ,, 2-CR, 5-CR, H CR, 3-CR, H 6-CM, 'c" r ,, H ^ ^ ^ Q R03C,R4-N- H H CR, H 3-CR, C2R, H 8 ., 1 3:: x xo x 2-Cl m CR, x 3-CR3 H 5-CR, 179 RO,S-C,114-N- H H CR, CR3 3-CR, H H ,, 'a C4Ha 180 RO,SC4R9-NH- H H CR, H 3-CR, H H X ,, Q X V = X V V = V 182 a 3: 3: H -0-CR, CR, 3-CR, C,Rc H a yellowish-tinged E V 6 V V V V lD C V V 183 ,, 2-CR, H H CR, 3-CR, H H ,, reddish-tinged yellow 184 HO,S-C4R9-N- H H -0-CR, H e C2R3 x x = U U U e u u U U U u V V Q = a U U a s a a x m x x x :: :c = = x 3 = a a x N x x x vl x =1 x N v x u o I ] a I X Z~VN Z~Ut Z Z V ZV 1t n: :c ~ x R VN N N V V ut Jz ca Clm co m a a r O O O ~ w x x x r = e t m sD F oo 08 o o ~ O1 o) or No.X R1 R2 R3 R4 R5 R7 R6 Z
a c, a b ct "M b E E E I E oa eo oo , oo B 1: .E; hg E 6,0 . 0 a, " p- a d 'Ct xo o" 2 x 185 ROcC4Ra-N1 2-Cl 5-CR3 CR, v o o 3-CR, H R 7el1d10ishtined C,R7 186 RO,CR-CR-N- H H CR, CR3 3-CR3 H 6-CR3 I. I n C,Ile U -O 187 RO3O-C,R4-NR H H H CR3 3-CR3 C,Me H -CO-CR, I ,, n a e e v v 189 X NC X m $ t = X X orange 190 ,, 2-Cl H CR3 -OCR, 3-CR3 C2Re 5-CR, z I yellow M,C 192 RO,S-C4R3-N- M R H OCR3 3-CR3 C2H4CN H 3 e" = :: V V ::: V NC V $ = V 193 a, 2-CR3 H CR, OCR, a a H H a V V = = V V V V 6 E o a R0,O-CR-CR-NR- H H CR, CR3 3-CR3 H H " reddish-tinged $ c a a a ~ a U U U a U U a $a CM, 195 RO,0-CH-CR-NR- v H H CM, O C2H5 O ', X s xa C X X X xa a xa v v : :c u v v v x v v x a v v V, V V V V = I w z zx r I n &verbar; &verbar; = u U u U V VQ O G V O O M a a a a a > a s a O O O O O O O = Y 3 = x x = ur VZ > oO 0\ 0 ^ N v o 00 00 00 00 Cb No. X R1 R2 R3 R4 R5 R7 R6 Z
a -J o b 3 b 3 E 04 . oa or, C , C , c B tiS S W > . H H o CR, > II yellow R,C N CR, x ,, 2-Cl H OCR, H H H " yellowish-tinged u v 8 z , 198 RO,S-C-C-NR- H H CR, CR, H C H H ,' reddish-tinged 2 a II yellow x x v u uD X ,, H H OCR, H X X orange S 110,8-C-C-N- H H H OCR, 3-CR3 H 6-CR3 -CO-CR3 X 6 U v X X X C2Re 201 2-Cl H OC,R5 CR, a a a u v U UU U 202 llO,S-Cll-(CH,),-N- 2-CR, x x II t < ) I I yello' xa xa m = X RO,S-Cll-((l2),-N- H H CR, H 3-CR3 C,He H ,, a = I a v UN a x O v O = O x v x x r x x = X U O1 = = es a I XN a = z ~ X Zl > EJ I X X D a N fi Z C) I X &verbar; X oX X a 8 ) > U a ce = 0 i a x x v xc > oo os o ~ N fe os o o o ó No. X R1 R2 R3 R4 R5 R7 R6 Z
3 c Pc c 3 204 F; H- H H CR3 C2He 3-CR, H H -CO-CR, reddish-tinged v X ., H = N s a 206 2-Cl vl vl I " 0 I 0 0 0 U )m ' D a x x 2-OCR, H CR3 so x x = x o CL 209 c" s u" 3: U S, e Y 3: X = U X C~ > X X X (~/ X a m H n CR, 3-CR, H n -CO-CR2-O-CR, V U V V E E s va a NH 212 Il H X 0('R, H = v U yellowish-tinged < orange X t X X X X X ' xa r > v v CR, D 3-CR3 x 6-CR, D reddish-tinged x r ~ ~ x ~ x x ~ x a x x x rll x rq x x x = x $ xb U g t m so > x > o t rz < o o o o o o ~ ~ a I rq r I rs No.X R, R2 R, R4 Re R, R6 /
214 HO- H H CH3 CH3 3-CH, C2Ra 6-CH, -CO-CR, reddish-tinged yellow 215 HO- 2-C1 H OCH, CH, 3-CH, C2R5 5-CH, 216 HO 2-OCH, H CH3 OCH, 3-CH, C,R4-CN 6-CH, -CO-CR3 Example 217.
23.5 g of 3-(N-phenylsulphonylamidosulphonyl)aniline are dissolved in 150 ml of water with 5 g of sodium hydroxide. Thereafter, 5 g of sodium nitrite are added.
The resulting solution is added dropwise to a mixture of 500 g of ice and 50 ml of concentrated hydrochloric acid. The mixture is subsequently stirred at OOC for 2 hours, the excess nitrite is destroyed with amidosulphonic acid, and a solution of 8.8 g of 2,5-dimethylaniline in 100 ml of glacial acetic acid is added dropwise. The pH value is adjusted to about 4 with saturated sodium acetate solution. The dyestuff which has precipitated is filtered off and dried at about 40"C.
6.58 g of the dyestuff described above are stirred in 150 ml of 500o by weight hydrochloric acid and diazotised at room temperature with 1 g of sodium nitrite, dissolved in 10 ml of water. 1.6 g of m-toluidine are dissolved in 50 ml of glacial acetic acid and the solution is added to the diazonium salt solution. The pH is adjusted to about 4 with saturated sodium acetate solution. The dyestuff which has precipitated is filtered off and dried at 400 C.
4.1 g of the disazo dyestuff described above are stirred in 60 ml of acetic anhydride and 20 ml of glacial acetic acid at 1200C for 2 hours. The mixture is allowed to cool to room temperature and the dyestuff, which has precipitated, of the formula
is filtered off.
The dyestuff dyes polyamide fibre material orange.
No. X R1 R2 R3 R4 R5 R7 R6 Z
218 HO H H H H 3-CR, H H -CO-CR3 reddish tinged yellow 219 HO H H CR, CR, 3-CR3 H H " 220 MO H H H H H H H 221 HO H H H CR, 3-CR, H H 222 HO H H CR, CR, 3-CR, H H 223 HO H H OCR, CR, 3-CR3 H czH -CO-CR, yellowish tinged orange 224 HO ll H CR, OCR, 3-CR, H H ,' 225 HO H H v OCR, 3-CR3 H H 226 HO H H H CR, 3-CR, H H -CO-ClI, reddish tinged yellow No. X R1 R2 R3 R4 R5 R7 R6 Z
I v, + I 'E a 3 ' o ', o 3 3 - b 227 HO 2-Cl H I O N ^ I ^ ^ U 3 U 228 HO 2-OCR, H H CR, 3-CR3 H 6-CR, 229 HO 2-CR, 4-CR, 3:: 230 HO 4-OC2R3H H CR, OCR, 3-CR, H H CL 231 HO H CR, CR, 3-CR, C3R4CN H -CO-CR, u HO 4-Cl X H -OCR, 3-0-CR, M u e 3n 233 HO 4-Cl H H -NH-CO-CR, 2-CR, H H " 234 HO 4-Cl H CR, CR, 2-CR, H 6-CR, ,' reddish . X ^ D v .
v X = U SC o Z = = 235 HO 4-Cl H I CR, 3-0-CR, H C) tinged '3:" eo 3=m U C) 0, Q ol O V U U D cS es fS t + t t t t O CX t TOz r " c" N m t v^, No. X R1 R2 R3 R4 R5 R7 R6 Z
1: 8 m P 0 3 3 a b n '3 3 ' a e, o^ 5 S bD 3 Q M a I=j. E: C r d '3 o HO 2-Cl 4-Cl o CR, 3-CR, H H rtindgdeidSh 8 8 I I 237 HO 2-Cl 11 -NIl-CO = = = I tinged CR, orange 238 HO II II H CR, 3-CR, 3: H -CO-C, reddish - tinged yellow 239 110 2-CR, 4-CR3 H CR, 3-CR, H H ,' 240 MO 2-CR3 4-CR, , CR, 3-CM, H .
241 110 2-CR, 4-ClI3 CR, CR, H C,R3 H 242 HO 2-CIl3 4-CR, CR, CR, 3-CR, H 6-CR, eq HO 2-CR3 4-ClI, CR, CII, 3-CR, C2R, H ', U U 2-CR3 4-Cil, OCR, CR, 3-CR, C H ,' yellowish o orange 245 HO 2-CR, 4-Cl U CII, OCR, 3-CR, U 11 -CO o o o o c o o o o o sc F x ch o H eN er m No.X R1 R2 R3 R4 R5 R7 R6 Z
a e a .s 3 -a Y a b) 246 HO 2-CR, 4-CR, CR, > o Li 247 HO 2-CR, 4-CR, CR, CR, 3-0-CR, H H -m X, HO 2-CR, 4-CR, H å yellow 249 HO 2-CR, 4-CR, H CR, 3-CR, H ~ 250 HO N tinged orange U m = HO 3-Cl H CR3 CR, 3-CR, X ::C O U O U U U U yeIlo 252-NH- H H H CR, 3-CR, H ll ,, 253 ,, U H CR, CR, 3-CR, H V D 254 ,, H H OCR, CR, R C,Hs H ,, yellowish tinged V U 1 3 V O U c) U U U v 2 O O O O O O 4 r = v r C vG > X 0E 0 ~ N m t No.X R1 R2 R3 R4 R5 R7 R6 Z
h a .3 h .r: a L: a a C B a .I a 8 v,71 3 U SO-NH- H H CR3 OCR, 3-CR, H 6-CR3 -CO-CR3 yellowish U 8 NC =, t U H H CR, OCR, 3-CM, C2R1 H = X Z 257 ,, H H H OCR3 H H M 'a 258 ,, H M H OCR3 3-CR, H H 'a 259 2-OCR, H CR, C, 3-CR, H M 'a reddish tinged yellow 260 ,, X H CR, CR, 3-CR, H H 261 ,, H H 0CR CR3 3-CM, H H 'a yellowish tinged orange 262 ,, 2-CR, H CR, 0CM3 3-CM, M H a' a, 263 O 2-Cl Q M OCR, H H H 'a a, 264 ,, 2-Cl H H OCR, 3-CR, M H 'a a, 265 CR,-SO,-NR- H H CR, H 3-CR, H H a' reddish 5: x c | = = : x x : 266 C2Hc-S02-NR- H H CR, CR, 3-CR, C,Rc H 'a reddish tinged yellow o U U U NC 5! C X ss X NC > n = = k Z 1 C oN O V U No. X R1 R2 R3 R4 R5 R7 R6 Z
= a b 9 8 ".o o g . s = s n 3 cr 6 = M r 8 1 (d = 267 C,He-SO,NH o H Cur, CR, 3-CR, H H 3n Q u o ,, H ^ = ^ u o 8 co I o u 269 C4Rc-SO,NH H H CR, OCR, 3-CR, CH H 'a o e" z 271 2-OCR, H CR, OC,H3 3-C2H5 H H a' v N N 272 CH,-SO,NH 2-CR, 4-CR, CM, CR, 3-CR, r H U w 5 K rf X lo e K = u Q 2-CR, 4-CR, H Cur, 3-CR, C2R5 b 275 ,, 2-Cl 4-Cl H H 3-CR, H 6-CR, -C0 276 HO3SC2H4NR ,03 u = N N 10 .1 , ,4 " e 277 U H H H CR, V H U U l0 278 ,, 2-Cl H N OCR, CR, 3-OCR, Il H f0 U u 279 llO3S-O-C2ll4NR H U O U U C) = SC 'D = O U U V D U ra m V V Z Z r Z N rt SC C C C U C,) v ~ F oo o ~ > t m Xo F 50 o so qx uO b > rs b > > > > b > No.X R1 R2 R3 R4 R5 R7 R6 Z
c 3 h,, 9 .11 oo 280 HO,S-O-C2H4NH H ll o 281 ,, 2-Br Il CII, CR, 3-CR, CII, H yellow 282 Il 3: 3: 3: 3: S, CM 283 II RC = D V : V L/ L, V H C,Rc 3-CR, CII, H 30 U Z V H Ij CR, V H H H 287 HO; 3: H H ii CR, 3-CR, H V - tinged yellow 288 ,, e r CR3 CR, 3-CR, = H e C: D :: ra ~ rz t = ,&verbar;r - Z 4 o ~ N t m so F x r X rl rz rl rl rl rq rs rq No. X R1 R2 R3 R4 R5 R7 R6 Z
I Y h Ca 3 '' -J ", sg 0= 0; 289 H H CR, -OCR, 2-CR, H 6-CR, -CO-CM, reddish I I I ,8 31 OCH5 z U 292 U H Q 3-CR, H II -CO-CR, yellowish e" m ;;e V V V V V 293 ,, rew r < > 1 yellow 294 CM5NH 4-Cl H OC,Re CR, 3-OCR, H H -CO-CM orange I V U 0= t:1 V V D I 295 llO,S-C4R9-N- H H CR, CR, 3-CR, C2R, H -CO-CR, reddish I tinged C2H3 ' 3: 3: V rv = rl W LD C as c rl o. t W) co 0 > o 5 v rq rl eS rl rl rl rA No.X R1 R2 R3 R4 R5 R7 R6 Z
a9 s s M O 0 0 n I s cl C,He yellow 297 H0,C,GeN V CR, CR, 3-CR, H V S 8 Se = ; :: :C ,r N-z R5 N OH W 299 OH H H H CR, 3-CR, H H uN 300 OR H H CR, m 3-CR, H V E V II 302 HO H H OCR, CR, 3-CR, C2Rc H 'a 303 HO 4-Cl H CR, CR, 2-CR, H H yellow 304 HO 4-CR, H R OC2Rc 3-CR, H 6-CR, orange 9LX1n = V e = 3-Cl II C,H5 CR, 3-CM, H V u n t HO 2-Cl 4-Cl CR, CR, 3-CR, C2R3 v COC4Ra Q rs rl V I V V V V N + = 3 = = er q q Z rl u > l N I ~ > ZV C. D e rl Vl A O O z r o O O O O O rq o O s rn t No.X R1 R2 R3 R4 R5 R7 R6 Z
S 5 c o c Q = c o 30 a u* u o o u u 5; HO 4-OCR, X H NRCOCR, M C,R5 H COC4H5 orange 308 -NH- H M CR, CR, 3-CR, H H COCH, yellow V H3C NH X 3: 3: U U O V O = H CR, CR, 3-OCR, H H -OcH3 orange G . m V m E m m m r 3 C; V V t r Z I 4 ox F 00 0e 0 O O n0 No.X R1 R2 R3 R4 R5 R6 Z
311 a 4-Cl H CR, CR, 3-CR, C2H4CN H COCH, yellow U NH 312 C,HcSO,NH H H H CR3 H M H a' 313 C4RcSO,NR H H CII, H 3-CR, H H COOC,R B 'a 314 hO;;NH- R I! H -OCR, 3-CR, M 5-CR, COCH, orange 315 HO -CM\ H H CR OCR, 3-CR, H 6-CR, -CO-CR, yellowish u" NM 316 RO,S-C,R4-NR- H H CR, CR, 2-CR, M H ,, reddish-tinged '3m m 317 HO,S-0-C3H4-NR 4-Cl II CR, CR, 3-CR, H ,, reddish-tinged - yellow
No.A B C R7 Z
a c .O o sl Q 8x 0 - CM3 CM3 yellow I I I N 319 Z tS D e u" e e u" 321 H O a CM3 CM3 322 ,, H a a, CM3 CM3 323 ,, a' ,, H CHCM a' 324 'a C2R4CN -CO-Cl I, a' X CSo O ~ No. A B C R7 Z
b ab . O . .tn .o: ~ .~ o ,C C C E , C C C C C o o n > t ,8 Ma5s-CM/\ CM3 tinged orange 326 ID.5 1C3 H -CO-C, yellowish 505M I orange CM3 CM3 CM3 I CM CM 327 - H COCR, yellowish CC X = X = = = CM3 CM3 328 5I\ ffi\ R 8.P-s - CM3 tinged red CM 329 ,, ,, M )$a "erlglOShg CM3 CL OCH3 NCL F 1 b 7

Claims (14)

WHAT WE CLAIM IS:
1. A dyestuff which contains only one acid group and in the form of the free acid, corresponds to the general formula
in which p is 0 or 1, X denotes OH, NH-SO2-R8, N(R9)-alkylene-OSO3H, N(R9)-alkylene-SO3H, N(R9)-arylene-SO3H, N(R9)-arylene-CH2-SO3H or N(R9)-arylene-SO2-NH-SO2-R8 Z denotes acyl, R1 and Re independently denote hydrogen or a non-ionic substituent (as hereinbefore defined), Re, Re and Re independently denote hydrogen optionally substituted alkyl, optionally substituted aralkyl, optionally substituted aryl, halogen, optionally substituted alkoxy, optionally aryloxy, optionally substituted aralkyloxy or optionally substituted acylamino or, R4and R3 together denote the remaining members of a fused benzene ring.
R@ and R@ denote hydrogen or optionally substituted alkyl, R7 denotes hydrogen, optionally substituted alkyl, optionally substituted aryl or optionally substituted aralkyl and R5 denotes optionally substituted alkyl, optionally substituted aralkyl, optionally substituted aryl or dialkylamino.
2. A dyestuff according to claim 1, in which P is defined as in claim 1, X denotes OH, NH-SO2-R5, N(R9)-(C2 to C6)alkylene-OSO3H, N(R9) (C2 to C6)alkylene-SO3H, N(R@)-phenylene-SO3H, N(R9)-phenylene CH2-SO3H or N(R9)-phenylene-SO2NH-SO2-R@, wherein the phenylene may be substituted by C1 to C4 alkyl, C1 to C4 alkoxy, halogen, cyano or nitro, R1 and R2 independently denote hydrogen, chlorine or bromine, methyl, ethyl, methoxy, ethoxy, cyano, trifluoromethyl or phenoxy R3, R4, R5 and Re independently denote hydrogen, or C, to C4 alkyl, C, to C4 alkoxy, (C1 to C4 alkyl)carbonylamino, benzoylamino, C1 to C4 alkylsulphonylamino, phenylsulphonylamino, (C1 to C4 alkoxy)carbonylamino or phenoxycarbonylamino, wherein the phenyl nuclei may be substituted by methyl, ethyl, methoxy, ethoxy, chlorine, bromine or cyano.
R7 denotes hydrogen, C, to C4 alkyl group which is optionally substituted by chlorine, hydroxyl or cyano, benzyl or phenetbyl, R5 denotes C, to C4 alkyl or phenyl which is optionally substituted by methyl, chlorine or bromine, denotes hydrogen, methyl or ethyl and Z denotes a (C, to C4 alkyl)carbonyl group which is optionally substituted by cyano, C, to C4 alkoxy, phenoxy or phenyl, benzoyl which is optionally substituted by C, to C alkyl, chlorine, bromine, nitro, cyano, C, to C4 alkoxy or a C, to C4 altylsulphonyl, phenylsulphonyl, phenoxycarbonyl or C, to C4 alkoxycarbonyl group, wherein the phenyl and phenoxy groups may be substituted by chlorine, C1 to C4 alkyl, C, to C4 alkoxy or cyano.
3. A dyestuff according to claim 1 which, in the form of the free acid, corresponds to the general formula
in which Z' denotes C, to C4 alkyl)carbonyl, benzoyl which is optionally substituted by methyl, methoxy or chlorine, phenylacetyl which is optionally substituted by methyl, methoxy, or chlorine or phenoxyacetyl which is optionally substituted by methyl, methoxy or chlorine, X' denotes OH, NH-SO2-R@', N(R@')-C@ to C@ alkylene-OSO@H.
N(Re')-C2 to C4 alkylene-SO3H or
R1' and R; independently denote hydrogen, methyl, ethyl, chlorine, bromine or trifluoromethyl, R3 and R4 independently denote hydrogen, methyl, ethyl, methoxy, ethoxy, acetylamino, methylsulphonylamino or phenylsulphonylamino R5' denotes hydrogen, methyl, ethyl, methoxy ethoxy or acetylamino R6' denotes hydrogen or methyl, R7' denotes hydrogen, methyl, ethyl, 2-cyanoethyl, 2-chloroethyl, benzyl or phenethyl, R8' denotes C1 to C4 alkyl or phenyl which is optionally substituted by methyl, chlorine or bromine and R9' denotes hydrogen, methyl or ethyl.
4. A dyestuff according to claim 3 which, in the form of the free acid, corresponds to the general formula
in which X', R, and R6' are defined as in claim 3, R'2 denotes hydrogen, or methyl, R3" denotes hydrogen, methyl or methoxy, R'4 denotes hydrogen, methyl, methoxy, ethoxy or acetylamino, R'5 denotes hydrogen, methyl or acetylamino and Z" denotes acetyl or propionyl, benzoyl which is optionally substituted by methyl, methoxy or chlorine, phenylacetyl which is optionally substituted by methyl, methoxy or chlorine, or phenoxyacetyl which is optionally substituted by methyl, methoxy or chlorine, or phenoxyacetyl which i; optionally substituted by methyl, methoxy or chlorine.
5. A dyestuff according to claim 1, as hereinbefore specifically identified.
6. A process for the production of a dyestuff as claimed in claim 1, in which an aminodisazo dyestuff of the general formula
in which X, p, R1, R2, R3, R4, R5, R6 and R7 are defined as in claim 1, is acylated.
7. A process according to claim 6, in which the aminodisazo dyestuff of formula (VI) is produced by diazotosing an amino compound of the general formula
in which X, R1, Re Re, Re and p are as defined in claim 1, and coupling with an amine of the general formula
in which RB, Re and R7 are defined as in claim 1.
8. A process according to claim I, when carried out substantially as described in any one of the Examples.
9. A dyestuff as claimed in claim 1, when produced by the process of any of claims 6 to 8.
10. A process for dyeing a natural or synthetic fibre material comprising treating the material with a dyestuff as claimed in any of claims 1 to 3, 5 and 9.
I I. A process according to claim 10, when carried out substantially as described in the "Dyeing Example."
12. A natural or synthetic fibre material when dyed by the process of claim 10 or 11.
13. A process according to claim 10, in which a dyestuff as claimed in claim 4, is used.
14. A natural or synthetic fibre material when dyed by the process of claim 13.
GB7698/78A 1977-03-01 1978-02-27 Disazo dyestuffs Expired GB1569062A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4384870A (en) 1980-08-08 1983-05-24 Sandoz Ltd. Disazo compounds having a sulfo group-containing diazo component radical, a 1,4-phenylene middle component radical having a substituted amino group and a coupling component radical having a free, acylated or etherified hydroxy group
US5183881A (en) * 1990-09-04 1993-02-02 Bayer Aktiengesellschaft O-aminoazo compounds
US5527889A (en) * 1992-10-26 1996-06-18 Ciba-Geigy Corporation Disazo dyes containing an alkanoylamino group and a substituted alkoxy group
US5691459A (en) * 1995-07-21 1997-11-25 Ciba-Geigy Corporation Disazo dyes containing two carbonylamino groups processes for their preparation and their use

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1267769B (en) * 1959-03-13 1968-05-09 Du Pont Process for the preparation of water-soluble dis- and tetrakis-azo dyes
BE637176A (en) * 1963-08-07
DE1644235C3 (en) * 1967-11-30 1975-01-09 Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt Water-soluble disazo dye, process for its preparation and its use
DE1923680C3 (en) * 1969-05-09 1978-04-20 Bayer Ag, 5090 Leverkusen Disazo dyes and their use for dyeing and printing natural and synthetic fiber materials
DE2006733C3 (en) * 1970-02-14 1979-06-13 Bayer Ag, 5090 Leverkusen Disazo dyes containing a sulfo group and their use for dyeing fiber materials made from synthetic polyamides
US3823131A (en) * 1971-06-23 1974-07-09 Toms River Chemical Corp Dialkylamino disazo sulfonic acid dyestuffs
US3847895A (en) * 1971-09-30 1974-11-12 Gaf Corp Substituted sulfophenyl-azo-naphthylazo-anilide compounds
DE2159216A1 (en) * 1971-11-30 1973-06-14 Hoechst Ag NEW HYDRO-SOLUBLE DISAZO DYES AND METHODS FOR THEIR PRODUCTION
DE2324067A1 (en) * 1973-05-12 1974-11-28 Bayer Ag DISAZO DYES
NL7514577A (en) * 1974-12-20 1976-06-22 Hoechst Ag WATER SOLUBLE DISAZO COLORING AGENTS, PREPARATION AND USE.

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4384870A (en) 1980-08-08 1983-05-24 Sandoz Ltd. Disazo compounds having a sulfo group-containing diazo component radical, a 1,4-phenylene middle component radical having a substituted amino group and a coupling component radical having a free, acylated or etherified hydroxy group
US5183881A (en) * 1990-09-04 1993-02-02 Bayer Aktiengesellschaft O-aminoazo compounds
US5527889A (en) * 1992-10-26 1996-06-18 Ciba-Geigy Corporation Disazo dyes containing an alkanoylamino group and a substituted alkoxy group
US5691459A (en) * 1995-07-21 1997-11-25 Ciba-Geigy Corporation Disazo dyes containing two carbonylamino groups processes for their preparation and their use

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IT7820645A0 (en) 1978-02-24
BR7801194A (en) 1978-10-10
ES467346A1 (en) 1978-10-16
DE2708779C2 (en) 1985-09-05
FR2382484B1 (en) 1984-01-27
JPS53106728A (en) 1978-09-18
DE2708779A1 (en) 1978-09-07
FR2382484A1 (en) 1978-09-29
BE864333A (en) 1978-08-28

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