GB1563415A - Azo dyestuffs - Google Patents

Azo dyestuffs Download PDF

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Publication number
GB1563415A
GB1563415A GB47176/76A GB4717676A GB1563415A GB 1563415 A GB1563415 A GB 1563415A GB 47176/76 A GB47176/76 A GB 47176/76A GB 4717676 A GB4717676 A GB 4717676A GB 1563415 A GB1563415 A GB 1563415A
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formula
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azo dye
methyl
methoxy
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Sandoz AG
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Sandoz AG
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
    • D06P1/04—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal
    • D06P1/06—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal containing acid groups
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C09B29/0011—Monoazo dyes prepared by diazotising and coupling from diazotized anilines from diazotized anilines directly substituted by a heterocyclic ring (not condensed)
    • 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
    • C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
    • 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
    • C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
    • C09B31/062—Phenols
    • C09B31/065—Phenols 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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/16—Trisazo dyes
    • C09B31/20—Trisazo dyes from a coupling component"D" containing a directive hydroxyl group
    • 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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • 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
    • C09B56/00—Azo dyes containing other chromophoric systems
    • C09B56/04—Stilbene-azo dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)
  • Coloring (AREA)

Abstract

Preparation of dyes by reacting mono- or bisdiazo compounds with certain dye intermediates (coupling components), and use of the dyes, in particular for leather.

Description

(54) AZO DYESTUFFS (71) We, SANDOZ LTD., of 35 Lichtstrasse, 4002 Basle, Switzerland, a Swiss Body Corporate, 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 present invention relates to azo dyestuffs.
More particularly, the present invention provides a process for the production of azo dyestuffs comprising coupling one or more diazo derivatives of amines of formula D-NH,, in which D is the radical of a diazo component, with a coupling component which is the product of the condensation reaction as described in British Patent Specification No. 1,507,531, with the proviso that at least one of the amines of formula DNH2 is of formula IV, V, VI, VII, VIII, IX or
in which R12, signifies hydrogen, chlorine, methyl, methoxy, sulpho, carboxy, arylamino or acetylamino, R12" signifies hydrogen, chlorine, methyl or methoxy, R1,' signifies methyl, methoxy, chlorine, sulpho, carboxy, arylamino or acetyl amino, R12IV signifies methyl, methoxy or chlorine, R1,' signifies a group of formula (a') or (b')
R13" signifies a group of formula (a"), (b"), (c"), (d") or (e")
R5, signifies hydrogen, methyl, methoxy or nitro, R6' signifies hydrogen, chlorine, methyl, methoxy, nitro or carboxy, R7' signifies hydrogen, chlorine, methyl, hydroxy, carboxy or sulpho, R8' signifies hydrogen, chlorine, methyl or nitro, R9' signifies hydroxy, chlorine, methyl, methoxy, nitro, sulpho or carboxy, each of R10' and R11', independently, signifies hydrogen, chlorine, methyl, methoxy, carboxy or sulpho, R18' signifies a group of formula (a") or R18" signifies a group of formula (c"), (c'), (d') or (e')
R19' signifies hydrogen or hydroxy, M is hydrogen or a cation equivalent, and m signifies 1, 2 or 3.
There is preferably the following relationship between the number of sulpho groups (nSO3M), carboxyl groups (nCOOM) and the number of aromatic nuclei (nA) which are present in the amines of formula D-NH2 nSO3M + nCOOM + nA + y wherein y is - 1, 0, + 1 or + 2, nSO3M is # nA and the naphthalene nucleus counts as two aromatic nuclei.
An arylamino in the amines of formula D-NH2 is preferably a group of formula
in which R8' to R10' are as defined above, preferably at least one of R8' and R9' is nitro and such arylamino group contains a single sulpho group.
Preferably at least one of the amines of formula D-NH2 is of formula IV or V.
In the amines of formula IV and V, when R13, is a radical of formula (a'), preferably R12, is hydrogen and R12,, is methoxy.
In the radicals of formula (a') and (b') Rl8" is preferably a radical of formula (c").
Preferred amines of formula IV are those of formula IV', IV" and IV"',
Preferred amines of formula V are those of formula V' and V",
Diazotisation of the amines of formula D-NH2 is carried out in manner known per se.
The reaction of the diazo compounds with the coupling components which are the products of the condensation reaction as described in British Patent Specification No.
1,507,531 may be carried out in conventional manner, for example as described in the above-mentioned specification.
The dyes obtained have an anionic character and are useful for dyeing substrates dyeable with anionic dyes, e.g. substrates consisting of or comprising natural or synthetic polyamide. In particular, the dyes are useful for dyeing leather.
The following Examples further serve to illustrate the invention. In the Examples the parts are by weight and the degrees are degrees Centigrade.
EXAMPLE 1.
276 Parts salicylic acid, 100 parts 20% sodium hydroxide solution and 42 parts paraformaldehyde are stirred at 98"C for 10 hours. The resulting viscous melt, which no longer smells of formaldehyde, is mixed with 500 parts 30% sodium hydroxide solution and made up to 1000 parts with water.
EXAMPLE 2.
276 Parts salicylic acid, 130 parts 30% sodium hydroxide solution and 51 parts paraformaldehyde are stirred for 10 hours at 98"C. The resulting viscous melt, which no longer smells of formaldehyde, is mixed with 130 parts 30% sodium hydroxide solution and is made up to 1000 parts with water.
EXAMPLE 3.
138 Parts salicylic acid, 75 parts 10% sodium hydroxide solution and 24 parts paraformaldehyde are boiled under reflux for 2 hours. 22 Parts resorcinol dissolved in 20 parts water at boiling temperature are added dropwise over the period of an hour. Subsequently, a further 4 parts of paraformaldehyde are added and the reaction mixture is boiled under reflux for 7 hours. The condensation product is mixed with 80 parts 30% sodium hydroxide solution and then made up to 500 parts with water.
EXAMPLE 4.
a) 54.3 parts of the aminomonoazo dye of formula
(obtained in conventional mannerj are suspended in 350 parts 3% hydrochloric acid and at 5", 7 parts of sodium-nitrite in the form of a 25% aqueous solution are added dropwise thereto. After diazotization the product is mixed with 22.3 parts l-aminonaphthalene-6-sulphonic acid dissolved in 140 parts 3% sodium hydroxide solution, the pH is adjusted to 5.5 by the addition of 30% sodium hydroxide solution and after completion of coupling the aminodisazo dye is salted out by adding sodium chloride and then filtered. Subsequently, the paste is suspended in 350 parts 3% hydrochloric acid and mixed with 7 parts of sodium nitrite in form of a 25% aqueous solution.After diazotisation is completed the diazo suspension is slowly added to 100 parts of the condensation product of Example 1 at 5 and at pH 13, the pH value being maintained at 13 by the addition of sodium hydroxide. A further diazo suspension obtained from diazotising 31.9 parts of 4 - amino - 4' - nitro - diphenylamine2' - sulphonic acid obtained in conventional manner is slowly added at a temperature of 5 and pH 13. The resulting dye is isolated by adding sodium chloride and hydrochloric acid and dried. The brown powder gives even dyeings of brown shades on leather.
b) A dye with similar properties is obtained when 100 parts of the condensation solution of Example 2 is used instead of that of Example 1 in accordance with the procedure given in a) above.
c) A dye with similar properties, (giving dyeings of a redder shade), is obtained when 100 parts of the condensation solution of Example 3 is used instead of that of Example 1.
Further dyes according to the invention which can be made in analogous manner to that of Example 4 are indicated in the following table. The dye shade on leather is also given. In the Table p1 = the number of mols of the first diazo component, p2 = the number of mols of salicylic acid used in the preparation of the condensation product and p, = the number of moles of the second diazo component.
o s es < 41 O O O O O O O > s C O q g g X d za 51 Q 0~ Condonsation c proparod Dye shado 3. No. p1 First diaao cotnponont o 8 An loather SO 3H CH3 5 5 + e, 9 lea 3 6 1 do. 2 Example 1 1 H2N-NH-SO3H do. NO2 e O S o do. 2 Example o o el o o roJ a x II: w w w w COO - O O B 9 B do. 2 Example 3 1 do. do. Ua 13 10 1 do. 2 Example N N H2NC\NC!I do. cJ X Z O X o" C 7 C il X Q g o o o o o o o z r go X X X X N X + V O Z h O z u7 % o ~I ea H H 7 x
s o v 3 tzo3 So X o o a ro o or o t P R'NNON=N OH2 2 Example 3 1 H2NC\flNCH3 brown O N NO2 3 r0 1 I(LN=N 0 cl 2 Example 1 - - do. at CO t R X U 03H CO W W W a N do. N Example cry N ç W f z Wf H H ~ s
s ec -c cZ o aq X g X g xs vc P oE Y = No. r1 First diazo cornponent P2 Un loather ON o o o 15 1 NflHQC2 2 Example 3 1 A= + O3 so3R SO3H H N OCH3 - P7 H t4 H H H ae aCI r, a h tre rJ a a Q) 0) O) P) Q) 18 C do. 2 Example 1 1 H2NNILO3H do. 19 do. 2 Example 3 1 Iil do. "aS ru ffi N N N OI N N ru N o W20 o o g o g ev Z te ffi z es e t ffi o S H 14
T A B L E
a rJ I > c 6 3 o g V)C C d d . ~ Qrd O 'tl a E O No. First diazo component product prepared N p1 1 according to + second diazo component on u v, g ;: O to n NO2 cr I I ri 22 1 do. 2 Example 3 en H do.
rl rl cJacn GJJ E tU O < U X Q 1 do. Example 1 W SO H CS a cu hi XN O cXn E Z O C O X e3 g ; 3 z H H Z o < n ffi N N N E W
ex5 ' 3 3O O O O o o o E Q No. First diazo component product prepared ye shade Example p1 2 according to p3 second diazo component on leather SO 3H CM3 o 1 2NCNN=NN?.j112 2 Example 1 - - brown 0 X az a0 I I rl r( r( rl rl X h O O V H m ri m ri m ri 27 X do. 2 Example 3 1 do. do.
28 o do. 2 Example W W W W W Oo U a cJ he a cu Nrucscunru 30 1 do. 2 Example 1 1 Cd;3 SO 3H do.
e sc z X ON g a xP ffi H Z C} w t X H N N N N N N n IE3 X
concniatien Dye shade o o o~ 3 O o ç o s E, to SO H CR3 CM3 oCR3 t3 1 Erl W 3 ~ oa 32 1 do. rlc(r(l I SO 3H a o HO o H z , H 1 do. 2 Example 3 e do. do.
oc:?3 35 = o;Ni-N:'N0ON-'. -t:i2 2 Example W X W N X so ii 2 SO 31I 2 36 X do. 2 N U74 É 1W1s 0 1Xs 3 sss g o r 9 o X v n v n C0n 6w {S t D ~ H H H H H O "} N > &verbar; Lf X
v o o X s Xv s o 3C g g O g 8 g n R c o to OCH o 37 1 2 Example 1 1 50 H brown 50 3H I d so 11 3 0 38 H do. 2 rcrl? 3 crl 1 do. 2 Example 1 1 H2N);=N-SO3H do.
do. 2 Example 3 1 do. do.
Ou o\ 1 1 41 O do. 2 Example R .1 wX a X ad.
CJCVO W U SO3H 42 1 do. 2 cu cu FJ (Y O. N N N N N N N 43 1 VZ N N ~ Jc= SO 3H 50 H h , 00 x O De H ~ H H ~ H 7o O rs ae o H n ~ rx EX W
o o s 6 c :n o o3 o g o V 0 E t0Zw > 0 44 1 3 3 sO U 45 1 do. 2 Example 1 1 H2N NH-NO2 do.
U ffi H H 3 NO2 m do. 2 Example 3 1 t4 n NO2 Oc C a a a a a a 49 1 !O3S-NIN=N-N-N-N! 2 ia nS 1 1 6 do.
SO3 it O k U 50 1 do. (Y CY CY CU (V N N N N N N N N J v z c 1: 11 oa &verbar;X Z a v ≈ ss o Z > x Zov X uz uz od o ffi ~ ~ H H o z o wr tn w > a o ~ sr sr w v or v n E C kXl .
Condcnr.tton Dy hade h O O 4 V ~, R g &commat; r xamplo No. First diazo component Z prcCuct prepared X Second diazo component on o o to W ≈ AU0 ú S03H m s < e. O rr cc:{3 ci 4 1 do. 2 I o do. do.
55 J O E E E E E E UCq P. N N do. 2 Example N N do. do.
O0; 9 i {XsXn O D 5tX 0 0 0 0 0 N N W v h 0O 3o :S H O H N r-. CP In TD o ur n tn tn cn u} E W
I Cononsation Dye shade o o 3 o X g X o sr o to NO Ocp 57 Z I!O3S-N\"=\'NNNI: 2 Example Z 5 H2N -NF{NO2 brown SO H N v 3 C Z f O 5:CY .
SQ3H oc CM 59 C O2NNIjN=N-\=N3N3!{2 2 Example H sn H do.
o NO2 rr SF rl rl r( GO O do. 2 Example 3 W4 W do.
o= x U Lo 61 -'5;*l~:fui----------n 5) ON UI : Z Z J: 62 Z do. 2 Xe c &verbar; x u x r (t] g z o o o Xy e n N o 0N Dz H o Z F SZ O 4 N o en uz tn E W
Con'.cnation DyL' shade a ., 3 0 o &verbar; c o p1 according to X | I I I z r o o ~~.
a I I I I a SO H H n H SO }' 3 3' fi . do. 2 re r( ri rJ E a a a a a a nule f C U S W W WX W W U H SO H . so H 3 68 1 do. 2 ~hL~hl 3 fl N do.
V 7 Z < O N 9 + tA U O z O U O o ssu ea z X l x 55 o n 0e t.
t O ffi < Z v tn O fi rXn
h X eO g X g "e Dye shade c, ml N I t N A0 1: SO H SO H o Oq SO3H | aO I I II CH o m do. 2 73 1 tT' 1 1 IU SO H do.
a v a 7 E E E E SO3H X X X X X SO ii 3 N 1 do. 2 hl 3 9 do.
s x,N eY2 > N U 7. QJ < R 7 0s ," é . ~na7 Z +0 N 2 Z 9 ~ V ~ ; 9 Ce W O i N N o < H H W zo P4 O H N CP a. w F rv b F b w
o e o o g o o o g :C Q D o m cu gm Z M to SO H OCH3 2 Example , SO H brown 75 9 0&commat; 9 o H X X 0 0 oz 2 Example 1 H 2O!I3:SO3ff do, 77 1 do.
'd u SO H 79 a '1O2{0"-S=NL'N=' & '2 2 Example o o o &commat; do.
2 SOCH SOCH 8 w 1 W W W C C 80 1 do. N N N N :o z {XsXe &commat;\0t D X , Z O X g X g v X V 0 > t a H H H H H z O H tn tD b aw o E to rs b uX
Condr.nation Dye bilade o O w3 h c X X X X X M o M No. O rirst diazo component 8 CtjPg0Pd ; econd diazo component on leathr SO H 81 1 0NCN=N 0 -N--N- 0 N. 2 Exple 1 1 HN-NHNO bron cc 22 X x x SO3H c o CR3 ffi H H < ,4 84 1 do. SO3H 2 Example 3 1 do. do.
3 o o v H ri 85 1 b Nfl-N=N.=a' < CNr'L 2 Example Q 1 do. do.
rJ -- ri r, ci c( 1 nir-e 01 a a a """ F Fi F f 8 Q B SO3H COO u ^ e N N n. N N N N N N N 87 1 do. cu F1 cY (Y N WOqY 4t0n W0Y N 9 v ss .
X O O X r O O Za 3 7- r g z o ~ H N n v 1 t E eo ea eD o- X W
Condensation Dye shade O4 Se g X o g g X X g :z o c m to SO H 0CM o" s03R 88 " 2 "0"8 3 N o 110 S g OU'-9 + 3 0CM3 2 Example X do. do.
2 2 H H H H H H < 91 1 do. 2 Example 1 1 B2N0:H3-NO2 do.
92 1 do. 2 Example 3 1 do. do.
O O rç H r( m m , P, e o o a, o s o ar 93 v iO3sO:'!IN= & ...:2? 2 R. D. D. 1 1 do. ffi a a a a a or O X X X X X X X X X 94 1 do. 2 Example 3 1 do. do.
L) C113 N N ffi do. 2 Example 1 N 2NNHSO3H do.
NO2 96 X I e Z "} 7 5 Z 4 > N O ffi H -4 H H H H H H H z o ~ em o H N E a X U
v o c) U v < uz O o o o o o < eq t r X cz < O A t 11 s F.':atr'ple 1 1 11 X 0 CH3 a a cJ o m 99 1 do. 2 Example 1 1 H2NO3N=NSO3M do.
U o.o < Y H X o ov 'v z cn o o X O U r: H H H H C v H A A z ffi c U X5 E E E E {' G O > : X X X C N 4 A S N N (S v 0 > t o, 91 fa f X X sk 09 N 0n z H o QU > a) o o E co X W.
WHAT WE CLAIM IS:1. A process for the production of an azo dye comprising coupling one or more diazo derivatives of amines of formula D-NH2, in which D is the radical of a diazo component, with a coupling component which is the product of the condensation reaction as described in British Patent Specification No. 1,507,531 with the proviso that at least one of the amines of fromula D-NH2 is of formula IV, V, VI, VII, VIII, IX or X
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (17)

  1. **WARNING** start of CLMS field may overlap end of DESC **.
    v o c) U v < uz O o o o o o < eq t r X cz < O A t 11 s F.':atr'ple 1 1 11 X 0 CH3 a a cJ o m 99 1 do. 2 Example 1 1 H2NO3N=NSO3M do.
    U o.o < Y H X o ov 'v z cn o o X O U r: H H H H C v H A A z ffi c U X5 E E E E {' G O > : X X X C N 4 A S N N (S v 0 > t o, 91 fa f X X sk 09 N 0n z H o QU > a) o o E co X W.
    WHAT WE CLAIM IS:1. A process for the production of an azo dye comprising coupling one or more diazo derivatives of amines of formula D-NH2, in which D is the radical of a diazo component, with a coupling component which is the product of the condensation reaction as described in British Patent Specification No. 1,507,531 with the proviso that at least one of the amines of fromula D-NH2 is of formula IV, V, VI, VII, VIII, IX or X
    in which R12, signifies hydrogen, chlorine, methyl, methoxy, sulpho, carboxy, arylamino or acetylamino, R12" signifies hydrogen, chlorine, methyl or methoxy, R12,,1 signifies methyl, methoxy, chlorine, sulpho, carboxy, arylamino or acetylamino, R12IV signifies methyl, methoxy or chlorine, R13, signifies a group of formula (a') or (b')
    R;;3 signifies a group of formula (a"), (b"), (c'), (d-) or (a")
    R@' signifies hydrogen, methyl, methoxy or nitro, R6, signifies hydrogen, chlorine, methyl, methoxy, nitro or carboxy, R,' signifies hydrogen, chlorine, methyl, hydroxy, carboxy or sulpho, R8' signifies hydrogen, chlorine, methyl or nitro, Ra' signifies hydroxy, chlorine, methyl, methoxy, nitro, sulpho or carboxy, each of R10' and R11', independently, signifies hydrogen, chlorine, methyl, methoxy, carboxy or sulpho, R18' signifies a group of formula (a") or (b"), R18" signifies a group of formula (c"), (c'), (d') or (e')
    R19' signifies hydrogen or hydroxy, M is hydrogen or a cation equivalent, and m signifies 1, 2 or 3.
  2. 2. A process for the production of an azo dyestuff substantially as hereinbefore described with reference to any one of Examples 4 to 100.
  3. 3. An azo dye having a coupling component as stated in Claim 1, coupled to one or more diazo derivatives of amines of formula D-NH2, as stated in Claim 1, with the proviso that at least one of the amines of formula D-NH2 is of formula IV, V, VI, VII, VIII, IX or X as stated in Claim 1.
  4. 4. An azo dye according to Claim 3 in which the relationship between the number of sulpho groups (nSO3M), carboxyl groups (nCOOM) and the number of aromatic nuclei (nA) ) which are present in the amines of formula D-NH2 is nao M + nCOOM = ns + y wherein y is - 1, 0, + 1 or + 2, nSO3M is #nA and the naphthalene nucleus counts as two aromatic nuclei.
  5. 5. An azo dye according to Claim 3 or Claim 4, in which any arylamino group is of formula
    in which R8' to R10' are as defined in Claim 1.
  6. 6. An azo dye according to Claim 5, in which at least one of R8' and R9' is nitro and such arylamino contains a single sulpho group.
  7. 7. An azo dye according to any one of Claims 3 to 6, in which at least one of the amines of formula D-NH2 is of formula IV or V.
  8. 8. An azo dye according to Claim 7, in which, when R13' is a radical of formula (a') R12' is hydrogen and R12" is methoxy.
  9. 9. An azo dye according to Claim 7 or Claim 8, in which R18" is a radical of formula (c").
  10. 10. An azo dye according to any one of Claims 3 to 9, in which the amines of formula IV are those of formulae IV', IV" and IV"',
  11. 11. An azo dye according to any one of Claims 3 to 10, in which the amines of formula V are those of formulae V' and V",
  12. 12. An azo dye according to Example 4 a).
  13. 13. An azo dye according to Example 4 c).
  14. 14. An azo dye according to any one of Examples 4 b) and 5 to 100.
  15. 15. An azo dye whenever produced by a process according to Claim 1 or Claim 2.
  16. 16. A process for dyeing leather comprising employing an azo dye according to any one of Claims 3 to 15, as dyeing agent.
  17. 17. Leather whenever dyed by a process according to Claim 16.
GB47176/76A 1975-11-14 1976-11-12 Azo dyestuffs Expired GB1563415A (en)

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CH1479375A CH617713A5 (en) 1975-11-14 1975-11-14 Process for preparing dyes

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GB1563415A true GB1563415A (en) 1980-03-26

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JP (1) JPS5263222A (en)
CH (1) CH617713A5 (en)
DE (1) DE2648370A1 (en)
ES (1) ES453289A1 (en)
FR (1) FR2331604A2 (en)
GB (1) GB1563415A (en)
IT (1) IT1080522B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2457955A1 (en) * 2010-11-30 2012-05-30 Kemira Oyj Trisazo dyes for paper dyeing
CN103228739A (en) * 2010-11-30 2013-07-31 凯米拉公司 Azo dyes
CN103237847A (en) * 2010-11-30 2013-08-07 凯米拉公司 Azo dyes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4405469C2 (en) * 1994-02-21 1996-11-07 Ciba Geigy Ag Process for the production of azo dyes

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR517124A (en) * 1920-06-14 1921-04-30 Prod Chim Rohner S A Fab De New azo dyes of triphenylmethane capable of being chromed on the fiber and process for their manufacture
GB1257581A (en) * 1969-02-19 1971-12-22

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2457955A1 (en) * 2010-11-30 2012-05-30 Kemira Oyj Trisazo dyes for paper dyeing
WO2012072635A1 (en) * 2010-11-30 2012-06-07 Kemira Oyj Azo dyes
CN103228739A (en) * 2010-11-30 2013-07-31 凯米拉公司 Azo dyes
CN103237847A (en) * 2010-11-30 2013-08-07 凯米拉公司 Azo dyes
US8734534B2 (en) 2010-11-30 2014-05-27 Kemira Oyj Azo dyes
US9023118B2 (en) 2010-11-30 2015-05-05 Kemira Oyj Azo dyes
CN103237847B (en) * 2010-11-30 2016-03-16 凯米拉公司 Azoic dyestuff
EP2457957B1 (en) * 2010-11-30 2017-08-09 Kemira Oyj Azo dyes for paper dyeing

Also Published As

Publication number Publication date
IT1080522B (en) 1985-05-16
DE2648370A1 (en) 1977-05-26
FR2331604B2 (en) 1981-12-04
JPS5263222A (en) 1977-05-25
ES453289A1 (en) 1978-02-01
CH617713A5 (en) 1980-06-13
FR2331604A2 (en) 1977-06-10

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