CH393585A - Process for the production of water-insoluble, metal-containing azo dyes - Google Patents

Process for the production of water-insoluble, metal-containing azo dyes

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Publication number
CH393585A
CH393585A CH1160761A CH1160761A CH393585A CH 393585 A CH393585 A CH 393585A CH 1160761 A CH1160761 A CH 1160761A CH 1160761 A CH1160761 A CH 1160761A CH 393585 A CH393585 A CH 393585A
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Switzerland
Prior art keywords
sep
oxynaphthoylamino
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Prior art date
Application number
CH1160761A
Other languages
German (de)
Inventor
Ulrich Dr Dreyer
Werner Dr Kirst
Original Assignee
Hoechst Ag
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Filing date
Publication date
Priority claimed from DEF26196A external-priority patent/DE1086832B/en
Priority claimed from DEF28442A external-priority patent/DE1132271B/en
Application filed by Hoechst Ag filed Critical Hoechst Ag
Publication of CH393585A publication Critical patent/CH393585A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • 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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/18—Monoazo compounds containing copper
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/34—Preparation from o-monohydroxy azo compounds having in the o'-position an atom or functional group other than hydroxyl, alkoxy, carboxyl, amino or keto groups
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Herstellung von     wasserunlöslichen,        metallhaltigen        Azofarbstoflfen       Es wurde gefunden, dass man zu neuen, wert  vollen,     wasserunlöslichen,        metallhaltigen        Azofarb-          stoffen        gelangt,    wenn man     Diazoniumverbindungen     von Aminen der Formel  
EMI0001.0010     
    worin der     Benzolkern    a durch Halogenatome,       Alkyl-;

          Alkoxy-,        Arylöxy-,        Acyloxy-,        Nitro-,          Trifluormethyl-,        Carbonsäureester-(-COOR),          gegebenenfalls    substituierte     Carbonsäureamid-          (-CONH2,        -CONHR,        -CONR2),        Acyl-,          Alkylsulfon-,        Arylsulfon-,        Sulfons,äurees'ter-          (-S02R),

       gegebenenfalls substituierte     Sulfonsäureamid-          (-S02NH2,        -S02NHR,        -S02NR2),        Acylammo-          oder        Arylaminogruppen     substituiert     sein    kann, mit     Arylamiden    von aroma  tischen oder     heterocyclischen        o-0,ycarbonsäuren     oder von     Acylessigsäuren,    die frei von wasserlöslich  machenden Gruppen, wie z.

   B.     Sulfonsäure-    oder       Carbonsäuregruppen,    sind, in Substanz oder auf  einem nichttextilen Substrat kuppelt und die so er  haltenen     Farbstoffe    mit metallabgebenden     Mitteln     behandelt.  



  Die Behandlung der erfindungsgemäss     erhältlichen          wasserunlöslichen        Azofarbstoffe    mit den metallabge  benden Mitteln     kann        in    bekannter Weise erfolgen.  Als metallabgebende Mittel kommen z. B. Eisen,  Chrom, Uran, Mangan, Aluminium, Blei,     Cadmium,     Zink, insbesondere jedoch Kobalt, Kupfer und Nickel         in    Betracht, die .in Form ihrer anorganischen oder  organischen Salze oder als Komplexverbindungen zur  Anwendung gelangen können.  



  Die     Metallisierung    wird zweckmässig in organi  schen Lösungsmitteln, wie z. B. Aceton oder     Di-          methylformanlld,        in    Gegenwart geringer Mengen       Pyridin        vorgenommen.    Die so     erhältlichen    Metall  komplexverbindungen sind     ausserordentlich    farbstark       und        in    der Regel in Aceton, Alkohol oder     Nitro-          celluloseesterlacken    löslich und eignen sich     daher          zur    Herstellung gefärbter Anstriche.

   Die     Metä11-          komplexverbindungen    können ausserdem     zum    Färben  von tierischen Fasern, wie Wolle oder Seide, sowie  von     synthetischen    Fasern, wie z. B. Polyamid-,       Polyurethan-,        Acetylcellulose-    oder     Polyesterfasern,     sowie     zum    Färben von hochmolekularen plastischen  Massen, verwendet werden.  



  Bei dem erfindungsgemässen. Verfahren werden  als     Azokomponenten        Arylamide    von aromatischen  oder     heterocychschen        o-Oxycarbonsäuren    oder von       Acylessigsäuren,    beispielsweise solche der     2,3-Oxy-          naphthoesäure    oder deren in     6-Stellung    substituier  ten Derivate,  der     2-Oxyanthracen-3-carbonsäure,     der     Kresotinsäuren;

       der     Halogen-salicylsäuren,     der     4-Oxydiphenyl        3-carbonsäure,     der     2-Oxycarbazol-3-carbonsäure,     der     5-Oxy-1,2,1',2'-benzocarbazol-4-carbonsäure,     der     3-Oxydiphenylenoxyd-2-carbonsäure,     der     3-Oxydiphenylensulfid-2-carbonsäure,     der     Acetessigsäure,     der     Benzoylessigsäure    oder  der     Terephthaloyl-bis-essigsäure     verwendet.

        Als     Aminoverbindungen,    welche der obigen For  mel entsprechen und bei dem vorliegenden     Verfahren     vorteilhaft verwendet werden können, seien z. B. ge  nannt:       3-Amino-,indazol,     3     Amino-4-chlorindazol,     3     Amino-5-chlorindazol,     3     Ämino-6-chlorindazol,          3-Amino-6-methylindazol,     3     Amino-5-methoxyindazol,          3-Amino-5-methoxy-6-chlorindazol,     3     Amino-6-methoxyindazol,          3-Amino-6-äthoxyindazol,          3-Amino-5-trifluormethyl-indazol,

       3     Amino-6-trifluormethyl-indazol,          3-Amino-6-acetyl-indazol,          3-Amino-5-nitroindazol,          3-Amino-6-nitro-indazol,          3-Amino-indazol-5-sulfonsäure-diäthylamid,          3-Amino-indazol-6-carbonsäureamid,          3-Amino-5-methylsulfonyl-indazol,          3-Ammo-5-phenylsulfonyl-indazol    oder  3     Amino-5-benzoylamino-indazol.     



  Die Herstellung     dieser    in der Literatur zum Teil  noch nicht beschriebenen     Aminoverbindungen        kann     nach bekannten     Verfahren    erfolgen, beispielsweise  durch     Diazotierung    von     o-Amino-benzonitrilen,        Re-,

            duktion    der     Diazoverbindungen        mit        Zinnchlorür    und       Salzsäure        züi    den     Hydrazinverbindungen    und     Ring-          schluss    in saurem Medium     zu    den 3     Amino-indazolen.     Die so erhältlichen Verbindungen sind stabile, gut  kristallisierende Produkte, die sich in     mineralsaurer          Lösung    in der üblichen Weise     diazotieren    lassen.

    Beim     Neutralisieren    der     Diazolösungen    scheiden sich  die     Diazoverbindungen        in.    Form     schwerlöslicher,     stabiler     Anhydro-indazol-3-diazöhydroxyde    ab.  



  Die neuen     Farbstoffe    sind den aus der franzö  sischen     Patentschrift    Nr.<B>981</B>432 bekannten, durch       Kuppeln    von     diazotiertem    6- oder     7-Amino-indazol     mit     Arylamiden    der     2,3-Oxynaphthoesäure    und an  schliessende.     Metallisierung        erhältlichen    wasserunlös  lichen     Azofarbstoffen    in den Echtheitseigenschaften  überlegen.  



  <I>Beispiel</I>  36     Gewichtsteile    1- (2',3' -     Oxynaphthoylammo)-          2,4-dimethoxy-5-chlorbenzol    werden mit 0,5 Ge  wichtsteilen     eines        Einwirkungsproduktes    von etwa  20     Mol        Äthylenoxyd    auf 1     Mol        Oleylalkohol    und    36     Volumteilen    Natronlauge von 38      B6        angeteigt     und eine Viertelstunde erwärmt.

   Die Paste     wird          dann    mit 1000     Volumteilen    heissem Wasser über  gossen und durch Aufkochen in Lösung gebracht.  Die so erhaltene Lösung lässt man unter gutem  Rühren     in    eine     Diazolösung    einlaufen, die durch       Diazotierung    von 16,3 Gewichtsteilen     3-Amino-6-,          methoxyindazol        in    der     üblichen    Weise hergestellt  wurde. Durch Kühlung wird hierbei die Temperatur  der Reaktionslösung auf 25-30  gehalten. Nach Be  endigung der Kupplung wird der gebildete rote Farb  stoff abgesaugt und gewaschen.  



  Zur     überführung    in die     Kupferkomplexverbin-          dung    wird der feuchte Filterkuchen in 1000     Volum-          teilen    Aceton aufgeschlämmt und mit einer konzen  trierten     wässrigen    Lösung von 17,1 Gewichtsteilen  kristallisiertem     Kupfer-(11)-chlorid    und 25     Volum-          teilen        Pyridin    versetzt. Nach kurzem     Rühren    ist die       Metallisierung    beendet.

   Die     Reaktionsmasse    wird  mit Wasser auf etwa 3000     Volumteile    verdünnt und       mit    50     Volumteilen    Salzsäure von 20      B6    ange  säuert. Der so erhaltene Farbstoff     wird    abgesaugt,  gewaschen und     getrocknet.    Er stellt ein blaustichig  schwarzes Pulver dar, das im.     Leinölanstrich    im     Ver,          schnitt        mit    einem Weisspigment graublaue Töne lie  fert.  



  Verwendet man     .in    obigem Beispiel anstelle von  17,1 Gewichtsteilen     Kupfer-(Il)-chlorid    24 Gewichts  teile     kristallisiertes    Kobalt     (II)-chlarid    und führt die       Metallisierung    unter Rühren 5 Stunden bei     Zimmer-          temperatur    durch, so erhält man     die        Kobaltkomplex-          verbindung    in Form eines     grünlichschwarzen    Pulvers,  das im     Leinölanstrich    im Verschnitt mit einem Weiss  pigment     grüne    Töne ergibt.  



  Zur     Herstellung    der     Nickelkomplexverbindung     ersetzt     man        in    obigem Beispiel das     Kupfer-(11)-chlo#rid     durch 24 Gewichtsteile     kristallisiertes    Nickelchlorid  und führt die     Metallisierung    durch fünfstündiges  Rühren und Erhitzen unter     Rückfluss    durch.

   Man  erhält     ein        dunkles    Pulver, das sich in organischen       Lösungsmitteln    mit violetter Farbe löst und zur Her  stellung von Lacken sowie zum Färben von hoch  molekularen plastischen Massen sowie von synthe  tischen     Fasern        geeignet    ist.  



  Die nachstehende Tabelle enthält noch eine An  zahl von weiteren erfindungsgemäss verwendbaren  Komponenten sowie die Farbtöne der daraus erhält  lichen     Azofarbstoffe:       
EMI0003.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP> Kobalt- <SEP> Nickel- <SEP> Kupfer  komplex <SEP> komplex <SEP> komplex
<tb>  3-Amino-indazol <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> blaustichiges <SEP> - <SEP> Blaugrau
<tb>  2-methylbenzol <SEP> Grün
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> Violett
<tb>  2-methyl-4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> - <SEP> Blaugrün
<tb>  2-methoxy-4-chlor-5-methylbenzol
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)- <SEP> Grüngrau <SEP> blaustichiges <SEP>  
<tb>  naphthalin <SEP> Bordo
<tb>    <SEP> 1-(6'-Brom-21,31-oxynaphthoylamino)

  - <SEP> Grün <SEP> rotstichiges
<tb>  2-methoxybenzol <SEP> Dunkelblau
<tb>    <SEP> 1-(2'-Oxycarbazol-3'-carboylamino)- <SEP> - <SEP> Violettbraun <SEP> Violett
<tb>  4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Grün <SEP> Violett <SEP> Blaugrün
<tb>  2,4-dimeihoxy-5-chlorbenzol
<tb>  3 <SEP> Amino-5-chlor- <SEP> 1-(V,3'-Oxynaphthoylamino)- <SEP> - <SEP> Korinth <SEP> grünstichiges
<tb>  indazol <SEP> 2,4-dimethoxy-5-chlorbenzol <SEP> Dunkelgrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> - <SEP>   <SEP> Dunkelgrau
<tb>  naphthalin
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Dunkelgrün <SEP> - <SEP>   2-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> - <SEP> Violett <SEP> Dunkelgrau
<tb>  2-methylbenzol
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)

  - <SEP> - <SEP> dunkles <SEP> grünstichiges
<tb>  naphthalin <SEP> Rotbraun <SEP> Dunkelgrau
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)- <SEP> - <SEP> <B>D <SEP> D</B>
<tb>  3-methoxy-diphenylenoxyd
<tb>  3-Amino-6-chlor- <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Olivgrün <SEP> stumpfes <SEP> Blaugrau
<tb>  indazol <SEP> 2-methoxybenzol <SEP> Rotviolett
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> bräunliches <SEP> Bordo <SEP> rotstichiges
<tb>  2-methyl-4-chlorbenzol <SEP> Grün <SEP> Grau
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)- <SEP> Olivgrün <SEP> Korinth <SEP> Blaugrau
<tb>  naphthalin
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> blaustichiges <SEP>   <SEP>  
<tb>  2,4-dimethoxy-5-chlorbenzol <SEP> Grün
<tb>    <SEP> 1-(6' <SEP> Brom-21,3'-oxynaphthoylamino)- <SEP>   <SEP> blaustichiges <SEP> Blaugrün
<tb>  2-methoxybenzol <SEP> Violett
<tb>    <SEP> 1-(2',

  3'-Oxynaphthoylamino)- <SEP> Olivgrün <SEP> - <SEP>  "
<tb>  2-methoxy-4-chlor-5-methylbenzol
<tb>    <SEP> 1-(2'-Oxycarbazol-3'-carboylamino)- <SEP> - <SEP> - <SEP> Blauviolett
<tb>  4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Grün <SEP> - <SEP> Blaugrau
<tb>  2-methylbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> - <SEP>  
<tb>  2-methyl-4-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> - <SEP>  
<tb>  2,5-dimethoxybenzol       
EMI0004.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP> Kobalt- <SEP> Nickel- <SEP> Kupfer  komplex <SEP> komplex <SEP> komplex
<tb>  3 <SEP> Anuno-6-chior- <SEP> 1-(2';

  3'-Oxynaphthoylamino)- <SEP> Grün <SEP> - <SEP> Blaugrau
<tb>  indazol <SEP> 2-methoxy <SEP> 5-cblorbenzol
<tb>  1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> - <SEP>  
<tb>  2,5-dimethoxy-4-chlorbenzol
<tb>  1-(2',3'-Oxynaphthoylamino)- <SEP> - <SEP>   <SEP> - <SEP>  
<tb>  - <SEP> naphthahn
<tb>  > <SEP> 1-(2'-Oxyanthracen-3'-carboylamino)- <SEP>   <SEP> - <SEP> Grün
<tb>  2-methylbenzol
<tb>  _.3 <SEP> Amino-6-methyl- <SEP> 2,3-Oxynaphthoyl-aminobenzol <SEP> Olivgrün <SEP> Korinth <SEP> grünstickiges
<tb>  indazol <SEP> Graublau
<tb>    <SEP> 1-(2';

  3'-Oxynaphthoylamino)- <SEP>   <SEP> Violett <SEP>  
<tb>  2-methylbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  2,5-dimethoxy-4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> blaustichiges <SEP>  
<tb>  2-methoxybenzol <SEP> Bordo
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> Violett <SEP> <B> </B>
<tb>  2,4-dimethoxy-5-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> blaustichiges
<tb>  2-methyl-4-chlorbenzol <SEP> Bordo
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> Violett <SEP>  
<tb>  2-methoxy-4-chlor-5-methylbenzol
<tb>    <SEP> 2-(2';

  3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  naphthalin
<tb>    <SEP> 1-(2'-Oxycarbazol-3'-carboylamino)- <SEP> Dunkelgrau <SEP> Dunkelviolett <SEP> rotstickiges
<tb>  4-chlorbenzol <SEP> Dunkelblau
<tb>  3-Amino-6-methoxy- <SEP> 1-(6' <SEP> Brom-2',3'-oxynaphthoylamino)- <SEP> lebhaftes <SEP> Grün;

   <SEP> rotstickiges <SEP>   indazol <SEP> 2-methoxybenzol <SEP> Dunkelblau
<tb>  4,4' <SEP> Bis-(2",3"-oxynaphthoylamino)- <SEP> Grün <SEP> Korinth <SEP>   3,3'-dimethoxydiphenyl
<tb>    <SEP> 1-(2'-Oxyanthracen-3'-carboylamino)- <SEP> gelbstickiges <SEP> Grün <SEP>   2-methylbenzol <SEP> Grün
<tb>    <SEP> .

   <SEP> 1-(5'-Oxy-1',1",2',2"-benzocarbazol- <SEP> Dunkelbraun <SEP> Dunkelgrau <SEP>   4'-carboylamino)-4-rnethoxybenzol
<tb>  <B>s</B> <SEP> Terephthaloyl-bis-(1-acetylamino-2- <SEP> olivstichiges <SEP> Altgold <SEP>   methoxy-4-chlor-5-methylbenzol) <SEP> Gelb
<tb>    <SEP> 1-(2'-Oxycarbazol-3'-carboylamino)- <SEP> Dunkelgrau <SEP> Korinth <SEP>   4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> lebhaftes <SEP> Grün <SEP> Violett <SEP>   2,4.-dimethylbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Grün <SEP>   <SEP>   2-methylbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> gelbstickiges <SEP>   <SEP>   2 <SEP> methyl-4-chlorbenzol <SEP> Grün       
EMI0005.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP> Kobalt- <SEP> Nickel- <SEP> Kupfer  komplex <SEP> komplex <SEP> komplex
<tb>  3-Amino-6-methoxy- <SEP> 1-(2',

  3'-Oxynaphthoylamino)- <SEP> Grün <SEP> Violett <SEP>   indazol <SEP> 2-methyl <SEP> 5-chlorbenzol
<tb>    <SEP> 2,3-Oxynaphthoyl-aminobenzol <SEP> Grün <SEP> - <SEP>     <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP> gelbstickiges <SEP> Violett <SEP>   2-methoxy-4-chlor-5-methylbenzol <SEP> Grün
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>   2,5-dimethoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> _ <SEP>   <SEP>   <SEP>   2-methoxy-5-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>   naphthalin
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> Rotbraun <SEP>   4-äthoxybenzol
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> _ <SEP>   4-methylbenzol
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP>   <SEP>  
<tb>  2,3-dimethylbenzol
<tb>    <SEP> 1-Oxy-4-methylbenzol2-carbonsäure- <SEP> Olivgrün,

   <SEP> Violettgrau <SEP> grünstickiges
<tb>  phenylamid <SEP> Grau
<tb>    <SEP> 1-Oxy-4,5-dichlorbenzol-2-carbonsäure- <SEP> Grüngrau <SEP> Rotbraun <SEP> Graugrün
<tb>  phenylamid
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> gelbstickiges <SEP> Violett <SEP>   2,5-dimethoxy <SEP> 4-chlorbenzol <SEP> Grün
<tb>    <SEP> 1-(4'-Oxydiphenyl-3'-carboylamino)- <SEP> Olivgrün <SEP> Grüngrau <SEP> Grüngrau
<tb>  2-methoxybenzol
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamin(y)- <SEP> gelbstickiges <SEP> - <SEP> , <SEP>   naphthalin <SEP> Grün
<tb>  3-Amino-6-äthoxy- <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> rotstickiges <SEP> Blaugrau
<tb>  indazol <SEP> 2-methoxy <SEP> 5-chlorbenzol <SEP> Violett
<tb>  (Schmelzpunkt <SEP> 222
<tb>  bis <SEP> 224 )
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP> Grün <SEP> Violett <SEP>   2-methylbenzol
<tb>    <SEP> 1-(2',

  3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>   2-methoxybenzol
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>   2-methyl-4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>   2-methyl-4-methoxybenzol
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>   2,5-dimethoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> - <SEP>   <SEP>   <SEP>   2,5-dimethoxy-4-chlorbenzol
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP> gelbstickiges <SEP>   <SEP> Blaugrau
<tb>  2,4-dimethoxy-5-chlorbenzol <SEP> Grün       
EMI0006.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP> Kobalt- <SEP> Nickel- <SEP> Kupfer  komplex <SEP> komplex <SEP> komplex
<tb>  3-Amino-6-äthoxy- <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Grün <SEP> Violett <SEP>   indazol <SEP> 2-methoxy-4-chlor-5-methylbenzol
<tb>    <SEP> 1-(2',

  3'-Oxynaphthoylamiüo)- <SEP> <B>a</B> <SEP>   <SEP> _
<tb>  naphthalin
<tb>    <SEP> 1-(6' <SEP> Brom-2',3'=oxynaphthoylamino)- <SEP> gelbstichiges <SEP> Violettblau <SEP> Blaugrün
<tb>  2-methoxybenzol <SEP> Grün
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)- <SEP> Grün <SEP> Violett <SEP> Blaugrau
<tb>  naphthalin
<tb>  1-(2'-Oxycarbazol-3'-carboylamino)- <SEP> grünstichiges <SEP> Korinth <SEP>   4-chlorbenzol <SEP> Grau
<tb>    <SEP> 1-Oxy-4-methylbenzol2-carbonsäure- <SEP> Olivgrün <SEP> Violettgrau <SEP> Grau
<tb>  phenylamid
<tb>    <SEP> 1-Oxy-4,5-dichlorbenzol-2-carbonsäure- <SEP> Grau <SEP> Violettgrau <SEP> a
<tb>  phenylamid
<tb>  1-(4'-Oxydiphenyl-3'-carboylamino)

  - <SEP> Olivgrün <SEP> Blaugrün <SEP> grünstichiges
<tb>  2 <SEP> methoxybenzol <SEP> Grau
<tb>  _ <SEP> Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP> Eisen- <SEP> Zink- <SEP> Uran- <SEP> Cadmium  komplex <SEP> komplex <SEP> komplex <SEP> komplex
<tb>  3-Amino-6-methoxy- <SEP> 1-(2',3 <SEP> =Oxynaphthoylamino)- <SEP> Korinth <SEP> .Violett <SEP> Rotviolett <SEP> Violett
<tb>  indazol <SEP> 2 <SEP> methoxy-4-chlor-5-methylbenzol
<tb>  Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP>   Kobaltkomplex <SEP> Kupferkomplex
<tb>  3 <SEP> Ammo-4-chlor- <SEP> 2,3-Oxynaphthoylaminobenzol <SEP> Grün <SEP>   indazol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> _
<tb>  2-methylbenzol <SEP>     <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> " <SEP> _
<tb>  2-methoxybenzol
<tb>  1-(2',3'-Oxynaphthoyiamino)- <SEP> ,r <SEP> _
<tb>  2-äthoxybenzol
<tb>    <SEP> 1-(2',

  3'-Oxynaphthoylamino)- <SEP>   <SEP> _
<tb>  4-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> _
<tb>  2-methyl4-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> _
<tb>  2,5-d#imethoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylatvno)- <SEP>   <SEP> _
<tb>  4-äthoxybenzol       
EMI0007.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente
<tb>  Kobaltkomplex <SEP> Kupferkomplex.
<tb>  3-Am@ino-4-chlor- <SEP> 1-(2';3'-Oxynaphthoylanvno)- <SEP> Blaugrün <SEP>   indazol <SEP> 3-nitrobenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylanüno)- <SEP> Grün <SEP> Blaugrau
<tb>  2-methyl:

   <SEP> 4-chlorbenzol
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP>   <SEP>  
<tb>  2-methoxy-5-chlorbenzol
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP>   <SEP>  
<tb>  naphthalin
<tb>    <SEP> 1-(6'-Brom-2',3'-oxynaphthoylamino)- <SEP>   <SEP>   2-methoxybenzol
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP>   <SEP>   4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> x <SEP>   2,5-dimethoxy-4-chlorbenzol
<tb>    <SEP> 1-(2';

  3'-Oxynaphthoylaniino)- <SEP>   <SEP> grünstickiges <SEP> Blaugrau
<tb>  naphthahn <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> Blaugrau
<tb>  2-methoxy-4-chlor-5-methylbenzol
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   3-methoxydiphenylenoxyd <SEP> - <SEP> '
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   2,4-dimethylbenzol
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP> Blaugrün <SEP>   2-methyl <SEP> 5-chlorbenzol <SEP>     <SEP> 1-(21,3'-Oxynaphthoylamino)- <SEP> Grün <SEP> - <SEP>   4-methylbenzol <SEP> _
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> _.
<tb>  2,3-dimethylbenzol
<tb>    <SEP> 4,4'-Bis-(2",3"-oxynaphthoylamito)'- <SEP> Oliv <SEP>   3,3'-dimethoxydiphenyl
<tb>    <SEP> 1-(2'-Oxycarbazol-3'-carboylamino)- <SEP> Blaugrau <SEP>   4-cblorbenzol
<tb>    <SEP> 1-(2'-Oxyanthracen-3'-carboylamino)

  - <SEP> gelbstickiges <SEP> Grün <SEP>   2-methylbenzol
<tb>    <SEP> 1-(5'-Oxy-1',2',1",2"-benzocarbazol-4'- <SEP> Violettbraun <SEP>   carboylamino)-4-methoxybenzol
<tb>    <SEP> 1-(5'-Oxy-1',2',1",2"-benzocarbazol4'- <SEP> Korinth <SEP>   carboylamino)-2-methyl-4-methoxybenzol
<tb>  3-Amino-5-methoxy- <SEP> 2,3-Oxynaphthoylaminobenzol <SEP> Olivgrün <SEP> Blaugrau
<tb>  indazol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> rotstickiges <SEP> Blaugrau
<tb>  2-methylbenzal
<tb>    <SEP> 1-(2',3! <SEP> Oxynaphthoylamino)- <SEP>   <SEP> grünstickiges <SEP> Blaugrau
<tb>  2-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> Blaugrau
<tb>  2-äthoxybenzol
<tb>    <SEP> 1-(21,3'-Oxynaphthoylamino)

  - <SEP>   <SEP>  
<tb>  4-methoxybenzol       
EMI0008.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente
<tb>  Kobaltkomplex <SEP> Kupferkomplex
<tb>  3-Amino-5-methoxy- <SEP> 1-(2',,3'-Oxynaphthoylamino)- <SEP> Olivgrün <SEP> rotstichiges <SEP> Blaugrau
<tb>  indazol <SEP> 2-methyl <SEP> 4-methoxybenzol
<tb>    <SEP> 1-(2,3'-Oxynaphthoylamino)- <SEP>   <SEP> Blaugrau
<tb>  2,5-dimethoxybenzol
<tb>  1-(2',3'-Oxynaphthoylamino)- <SEP> ,> <SEP> "
<tb>  4-äthoxybenzol
<tb>    <SEP> 1-(2,3'-Oxynaphthoylamino)- <SEP> blaustichiges <SEP> Olivgrün <SEP>  
<tb>  3 <SEP> nitrobenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Olivgrün <SEP> Violettgrau
<tb>  2-methyl-4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> grünstichiges <SEP> Blaugrau
<tb>  2-methoxy-5-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)

  - <SEP>   <SEP> Blaugrau
<tb>  2,4-diniethoxy-5-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>  
<tb>  naphthalin
<tb>    <SEP> 1-(6'-Brom-2',3'-oxynaphthoylamino)- <SEP>   <SEP> grünstichiges <SEP> Blaugrau
<tb>  2-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> Blaugrau
<tb>  _4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>  
<tb>  2,5-dimethoxy-4-chlorbenzol
<tb>  2-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> grünstichiges <SEP> Blaugrau
<tb>  naphthalin
<tb>    <SEP> 1-(2,3'-Oxynaphthoylamino)- <SEP> ,> <SEP>  
<tb>  2-methoxy-4-chlor-5-methylbenzol
<tb>   - <SEP> 1-(2,3'-Oxynaphthoylamino)- <SEP> blaustichiges <SEP> Olivgrün <SEP> Blaugrau
<tb>  2-methyl-5-chlorbenzol
<tb>    <SEP> 2-(2';

  3'-Oxynaphthoylammo)- <SEP> gelbstichiges <SEP> Olivgrün <SEP> grünstichiges <SEP> Blaugrau
<tb>  3-methoxydiphenylenoxyd
<tb>    <SEP> - <SEP> 1-(2'-Oxycarbazol-3'-carboylamino)- <SEP> Grau <SEP> rotstichiges <SEP> Dunkelblau
<tb>  4-chlorbenzol
<tb>    <SEP> _ <SEP> 1-(2'-Oxyanthracen)-3'-carboylamino)- <SEP> gelbstichiges <SEP> Grün <SEP> Grün
<tb>  2-methylbenzol
<tb>    <SEP> 1-(5'-Oxy-1',2',1",2" <SEP> benzocarbazol-4'- <SEP> Braun <SEP> Violettgrau
<tb>  carboylamino)-4-methoxybenzol
<tb>    <SEP> 1-(5'-Oxy <SEP> l',2',1",2"-benzocarbazol-4'- <SEP>  . <SEP>  
<tb>  carboylamino)= <SEP> 2-methyl-4-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> blaustichiges <SEP> Olivgrün <SEP> Blaugrau
<tb>  2,4-dimethylbenzol
<tb>  3-Amino-5-methoxy <SEP> 2-(2';

  3'-Oxynaphthoylamino)-naphthalias <SEP> Blaugrün <SEP>  
<tb>  6-chlormdazol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Grün <SEP>  
<tb>  2,4-dimethoxy-5-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Olvgrün <SEP>  
<tb>  2-methoxy-5-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)-naphthalin <SEP> Grün <SEP>         
EMI0009.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente
<tb>  Kobaltkomplex <SEP> Kupferkomplex
<tb>  3-Amino-5-methoxy- <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Blaugrün <SEP> Blaugrau
<tb>  6-chlorindazol <SEP> 2-methoxy-4-chlor-5 <SEP> methylbenzol
<tb>    <SEP> 1-(6' <SEP> Brom-2',3'-oxynaphthoylamino)- <SEP> Grün
<tb>  2-methoxybenzol
<tb>    <SEP> 1-(2'-Oxycarbazol-3'-carboylaimno)- <SEP> Grau <SEP> Dunkelblau
<tb>  4-chlorbenzol
<tb>  3-Amino-6-methyl- <SEP> 1-(2',3'-Oxynaphthoylamino)

  - <SEP> Grün <SEP> rotstickiges <SEP> Blaugrau
<tb>  indazol <SEP> 2-äthoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> Blaugrau
<tb>  4-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)  2-methyl-4-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>  
<tb>  2,5-dimethoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> rotstickiges <SEP> Blaugrau
<tb>  4-äthoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> - <SEP> Blaugrau
<tb>  3-nitrobenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>  
<tb>  naphthalin
<tb>    <SEP> 1-(6'-Brom-2',3'-oxynaphthoylamino)- <SEP>   <SEP> grünstickiges <SEP> Blaugrau
<tb>  2-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> Blaugrau
<tb>  4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)

  - <SEP>   <SEP>  
<tb>  2-methyl-5-chlorbenzol
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)- <SEP> - <SEP> Olivgrün <SEP>  
<tb>  3-methoxy-diphenylenoxyd
<tb>    <SEP> 1-(2'-Oxyanthracen-3'-carboylamino)- <SEP> gelbstickiges <SEP> Grün <SEP> Grün
<tb>  2-methylbenzol
<tb>    <SEP> 1-(5'-Oxy-1',2',1",2"-benzocarbazol- <SEP> Braun <SEP> rotstichiges <SEP> Blaugrau
<tb>  4'-carboylamino)-4-methoxybenzol
<tb>    <SEP> 1-(5'-Oxy-1',2',1",2" <SEP> benzocarbazol- <SEP>   <SEP>  
<tb>  4'-carboylamino)-2-methyl-4-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Grün <SEP> gedecktes:

   <SEP> Blau
<tb>  2,4-dimethylbenzol
<tb>    <SEP> 1-(6'-Methoxy-2',3'-oxynaphthoylamino)- <SEP> gelbstickiges <SEP> Grün <SEP> Blaugrün
<tb>  2-methyl-5-chlorbenzol
<tb>    <SEP> 1-(6'-Methoxy-2',3'-oxynaphthoylamino)- <SEP>   <SEP>  
<tb>  2 <SEP> methoxybenzol       
EMI0010.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP> Kupfer- <SEP> Kobalt- <SEP> Nickel  komplex <SEP> komplex <SEP> komplex
<tb>  3-Amino-indazol5- <SEP> 2,3-Oxynaphthoylaminobenzol <SEP> Blaugrau <SEP> Grün <SEP> Bordo
<tb>  sulfonsäurediäthylamid
<tb>  1-(2',3'-Oxynaphthoylamino)- <SEP> <B>  <SEP>  </B> <SEP> Rotviolett
<tb>  2-methylbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> grünstichiges <SEP>   <SEP>  
<tb>  2-methoxybenzol <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Blaugrau <SEP>   <SEP> Bordo
<tb>  2-äthoxybenzol
<tb>    <SEP> 1-(2',

  3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  4-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> <B>  <SEP>  </B> <SEP> Rotviolett
<tb>  2-methyl-4-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> Violett
<tb>  2,5-dünethoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> <B>  <SEP>  </B> <SEP> Bordo
<tb>  4-äthoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> grünstichiges <SEP>   <SEP> Rotviolett
<tb>  3-nitrobenzol <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Blaugrau <SEP> Grün <SEP> Violett
<tb>  2-methyl-4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  2-methoxy-5-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  2,4-dimethoxy-5-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)

  -naphthalin <SEP>   <SEP> <B>  <SEP>  </B>
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> grünstichiges <SEP>   <SEP> Bordo
<tb>  4-chlorbenzol <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> rotstichiges
<tb>  2,5-dimethoxy-4-chlorbenzol <SEP> Violett
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> @  >
<tb>  2-methoxy-4-chlor-5 <SEP> methylbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Blaugrau <SEP>   <SEP> Violett
<tb>  2,4-dimethylbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> a <SEP> Bordo
<tb>  4-methylbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> Violett
<tb>  2,3-dimethylbenzol
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)- <SEP> grünstichiges <SEP> Grün <SEP> blaustichiges
<tb>  naphthalin <SEP> Blaugrau <SEP> Bordo
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)

  - <SEP> Blaugrau <SEP>   <SEP> Korinth
<tb>  3-methoxy-diphenylenoxyd
<tb>    <SEP> 4,4'-Bis-(2",3"-oxynaphthoylamino)- <SEP> Grau <SEP> Oliv <SEP> blaustichiges
<tb>  3,3'-dimethoxy <SEP> diphenyl <SEP> Bordo
<tb>    <SEP> 1-(6' <SEP> Brom-2',3'-oxynaphthoylamino)- <SEP> grünstichiges <SEP> Grün <SEP> Violett
<tb>  2-methoxybenzol <SEP> Blaugrau
<tb>    <SEP> 1-(2'-Oxyanthracen-3'-carboylamino)- <SEP> Grün <SEP> gelbstichiges <SEP> Dunkelgrün
<tb>  2-methylbenzol <SEP> Grün       
EMI0011.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP> Kupfer- <SEP> Kobalt- <SEP> Nickel  komplex <SEP> komplex <SEP> komplex
<tb>  3-Amino-indazol-5- <SEP> 1-(5'-Oxy-1',2',1",2"-benzocarbazol-4'- <SEP> violettstichiges <SEP> Braun <SEP> Grau
<tb>  sulfonsäurediäthylamid <SEP> carboylamino)-4-methoxybenzol <SEP> Grau
<tb>  3-Amino-5-trifluor- <SEP> 1-(2',

  3'-Oxynaphthoylamino)- <SEP> grünstichiges <SEP> Grün <SEP>   methylindazol <SEP> 2,5-dimethoxybenzol <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> rotstichiges <SEP>   <SEP>   2-methyl-4-chlorbenzol <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> grünstichiges <SEP>   <SEP>   2 <SEP> methoxy-5-chlorbenzol <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Blaugrau <SEP>   <SEP>   2,4-dimethoxy-5-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)-naphthalin <SEP> Blaugrau <SEP>   <SEP>   x <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>   2 <SEP> methoxy-4-chlor-5-methylbenzol
<tb>    <SEP> 1-(6'-Brom-2',3'-oxynaphthoylamino)- <SEP> grünstichiges <SEP>   <SEP>   2-methoxybenzol <SEP> Blaugrau
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)-naphthalin <SEP> Blaugrau <SEP> <B> </B> <SEP>   3-Amino-6 <SEP> trifluor- <SEP> 2,

  3-Oxynaphthoylaminobenzol <SEP>   <SEP> blaustichiges <SEP> Korinth
<tb>  methylindazol <SEP> G
<tb>    <SEP> 1-(2';3'-Oxynaphthoylamino)- <SEP>   <SEP> - <SEP> blaustichiges
<tb>  2-methoxybenzol <SEP> Bordo
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> blaustichiges <SEP> Violett
<tb>  2-methylbenzol <SEP> Grün
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> - <SEP>   2-äthoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> blaustichiges <SEP> Violettgrau
<tb>  4-methoxybenzol <SEP> Grün
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> <B>  <SEP>  </B> <SEP> rotstichiges
<tb>  2-methylL4-methoxybenzol <SEP> Violett
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> Violett
<tb>  2,5-dimethoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylaxnino)- <SEP> <B> </B> <SEP> > <SEP> Korinth
<tb>  4-äthoxybenzol
<tb>    <SEP> 1-(2',

  3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> Violett
<tb>  3 <SEP> nitrobenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> Blaugrün <SEP>  
<tb>  2-methyl-4-chlorbenzol
<tb>    <SEP> 1-(2 <SEP> ;3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> rotstichiges
<tb>  2-methoxy-5-chlorbenzol <SEP> Violett
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  2,4-di#methoxy-5-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)-naphthalin <SEP> <B>  <SEP>  </B> <SEP>  
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>   4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> rotstichiges
<tb>  2,

  5-dimethoxy-4-chlorbenzol <SEP> Violett       
EMI0012.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP> Kupfer- <SEP> Kobalt- <SEP> Nickel  komplex <SEP> komplex <SEP> komplex
<tb>  3-Amino-6-trifluor- <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Blaugrau <SEP> Blaugrün <SEP> rotstickiges
<tb>  methyhndazol <SEP> 2-methoxy-4-chlor-5-methylbenzol <SEP> Violett
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  2-methyl-5-chlorbenzol
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)-naphthalm <SEP>   <SEP>   <SEP> Korinth
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  3-methoxydiphenylenoxyd
<tb>    <SEP> 1-(6' <SEP> Bröm-2',3'-oxynaphthoylamino)- <SEP>   <SEP>   <SEP> Violett
<tb>  2-methoxybenzol
<tb>  1-(2'-Oxycarbazol-3'-carboylamino)

  - <SEP> rotstickiges <SEP> Oliv <SEP> Braun
<tb>  - <SEP> 4-chlorbenzol <SEP> Dunkelblau
<tb>  1-(2'-Oxyanthracen-3'-carboylamino)- <SEP> Grün <SEP> <B> </B> <SEP> Grau
<tb>  - <SEP> 2-methylbenzol
<tb>    <SEP> 1-(5'-Oxy-1',2',1",2"-benzocarbazol <SEP> rotstickiges <SEP> Violettgrau <SEP> Violettgrau
<tb>  - <SEP> 4'-carboylamino)-4-methoxybenzol <SEP> Grau
<tb>    <SEP> 1-(5'-Oxy-1',2',l",2"-benzocarbazol- <SEP>   <SEP>   <SEP>  
<tb>  4'-carboylamino)-2-methyl-4-methoxybenzol
<tb>  3-Amino-6-nitro- <SEP> 2;

  3-Oxynaphthoylaminobenzol <SEP> Blaugrau <SEP> gelbstickiges <SEP> Korinth
<tb>  indazol <SEP> Grün.
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> _
<tb>  2-methylbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> grünstickiges <SEP> Olivgrün <SEP> Korinth
<tb>  2-methoxybenzol <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Blaugrau <SEP>   <SEP>  
<tb>  2-äthoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> gelbstickiges <SEP>  
<tb>  4-methoxybenzol <SEP> Grün
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> Violettgrau
<tb>  2-methyl <SEP> 4-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> grünstickiges <SEP>   <SEP> rotstickiges
<tb>  2,5-dimethoxybenzol <SEP> Blaugrau <SEP> Blaugrau
<tb>  b <SEP> 1-(2',3'-Oxynaphthoylamino)

  - <SEP> Blaugrau <SEP>   <SEP> Korinth
<tb>  4-äthoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> grüngtichiges <SEP> Grün <SEP> Grau
<tb>  3-nitrobenzol <SEP> Blaugrau
<tb>    <SEP> -- <SEP> 1-(2';3'-Oxynaphthoylamino)- <SEP> Blaugrau <SEP> gelbstickiges <SEP> Blaugrau
<tb>  2-methyl-4-chlorbenzol <SEP> Grün
<tb>    <SEP> 1-(2';

  3'-Oxynaphthoylamino)- <SEP> grünstichiges <SEP> gelbstichlges <SEP> rotstickiges
<tb>  2-methoxy-5-chlorbenzol <SEP> Blaugrau <SEP> Grün <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylam-mo)-naphthalin <SEP> Blaugrau <SEP>   <SEP>  
<tb>  1-(6'-Brom-2',3'-oxynaphthoylamino)- <SEP> grünstickiges <SEP>   <SEP> Dunkelrot  2 <SEP> methoxybenzol <SEP> Blaugrau <SEP> violett
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> <B>r</B> <SEP>   <SEP> Violettgrau
<tb>  4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Blaugrau <SEP>   <SEP> Blaugrau
<tb>  2,5-dimethoxy-4-chlorbenzol       
EMI0013.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP> Kupfer- <SEP> Kobalt- <SEP> Nickel  komplex <SEP> komplex <SEP> komplex
<tb>  3-Anino-6-nitro- <SEP> 2-(2',3'-Oxynaphthoylamino)-naphthalin <SEP> Blaugrau,

   <SEP> Grün <SEP> rotstichiges
<tb>  indazol <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> - <SEP> y <SEP> gelbstichiges
<tb>  2-methoxy-4-chlor-5-methylbenzol <SEP> Grün    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> rotstichiges <SEP>  
<tb>  2-methyl-5-chlorbenzol <SEP> Blaugrau
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)- <SEP> grünstichiges <SEP> - <SEP>   3-methoxy-diphenylenoxyd <SEP> Blaugrau
<tb>    <SEP> 1-(2'-Oxycarbazol-3'-carboylamino)- <SEP> - <SEP> Grau <SEP> Violettgrau
<tb>  4-chlorbenzol
<tb>  1-(2'-Oxyanthracen-3'-carboylamino)- <SEP> Grün <SEP> Braun <SEP> Braun
<tb>  2-methoxybenzol
<tb>    <SEP> 1-(5'mOxy-11,21,1",211-benzocarbazol-4'- <SEP> - <SEP>   <SEP>   carboylamino)-4-methoxybenzol
<tb>    <SEP> 1-(5'-Oxy-1',2',1",2"-benzocarbazol-4'- <SEP> - <SEP>   <SEP>   carboylamino)-2-methyl-4-methoxybenzol
<tb>    <SEP> 1-(6' <SEP> Methoxy-2',

  3'-oxynaphthoylamino)- <SEP> Blaugrün <SEP> gelbstichiges <SEP> Grau
<tb>  2-methoxybenzol <SEP> Grün
<tb>    <SEP> 1-(6' <SEP> Methoxy-2',3'-oxynaphthoylamino)- <SEP>   <SEP>   <SEP> Blaugrau
<tb>  2-methyl-5-chlorbenzol
<tb>  3-Aminoindazol-6- <SEP> 2,3-Oxynaphthoylaminobenzol <SEP> Blaugrau <SEP> Grün <SEP> Violettgrau
<tb>  carbonsäureamid
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> stumpfes <SEP>   2-methylbenzol <SEP> Violett
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>  
<tb>  2-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  3-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> Violettgrau
<tb>  2-methyl-4-methoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> stumpfes
<tb>  2,5-dimethoxybenzol <SEP> Violett
<tb>    <SEP> , <SEP> 1-(2',

  3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  4-äthoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>  
<tb>  3-nntrobenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamno)- <SEP>   <SEP>   <SEP> Violettgrau
<tb>  2-methyl <SEP> 4-chlorbenzol <SEP> - <SEP> - <SEP> - <SEP>     <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> stumpfes
<tb>  2-methoxy-5-chlorbenzol <SEP> - <SEP> Violett
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  2,4-dimethoxy-5-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)-naphthalin <SEP>  
<tb>    <SEP> 1-(6' <SEP> Brom-2',3'-oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  2-methoxybenzol <SEP>     <SEP> 1-(2',3'-Oxynaphthoylamino)

  - <SEP>   <SEP> v
<tb>  9-chlorbenzol       
EMI0014.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP> Kupfer- <SEP> Kobalt- <SEP> Nickel  komplex <SEP> komplex <SEP> komplex
<tb>  3 <SEP> Aminoindazol-6- <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> Blaugrau <SEP> Grün <SEP> stumpfes
<tb>  carbonsäureamid <SEP> 2,5-dimethoxy-4-chlorbenzol <SEP> Violett
<tb>    <SEP> 2-(2';

  3'-Oxynaphthoylamino)-naphthalin <SEP> <B>></B> <SEP>   <SEP>  
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> <B>  <SEP>  </B> <SEP>  
<tb>  2-methoxy-4-chlor-5-methylbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphihoylamino)- <SEP> - <SEP> <B>  <SEP>  </B> <SEP>  
<tb>  2-methyl=5-chlorbenzol
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)- <SEP> <B>  <SEP> D</B> <SEP>  
<tb>  3-methoxydiphenylenoxyd
<tb>    <SEP> , <SEP> 1-(2'-Oxycarbazo1-3'-carboylamino)- <SEP> rotstichiges <SEP> Grau <SEP>  
<tb>  4-chlorbenzol <SEP> Dunkelbraun
<tb>    <SEP> 1-(2'-Oxyanthracen-3'-carboylamino)- <SEP> Grün <SEP> gelbstichiges <SEP> Dunkelgrün
<tb>  2-methylbenzol <SEP> Grün
<tb>    <SEP> 1-(6' <SEP> Methoxy-21,31-oxynaphthoylamino)- <SEP> Blaugrün <SEP>   <SEP> grünstichiges
<tb>  2-methoxybenzol <SEP> Blaugrau
<tb>    <SEP> 1-(6' <SEP> Methoxy-21,31-oxynaphthoylamino)

  - <SEP>   <SEP>   <SEP>  
<tb>  2-methyl-5-chlbrbenzol
<tb>    <SEP> I-(2,',3'-Oxynaphthoylamino)- <SEP> Graublau <SEP> Grün <SEP> Violettgrau
<tb>  2,4-dimethylbenzol
<tb>    <SEP> 1-(2';3'-Oxynaphthoylamino)- <SEP> <B>  <SEP>  </B> <SEP>  
<tb>  2,3-dimethylbenzol
<tb>  3 <SEP> Amino-5-methyl- <SEP> 2-(2',3'-Oxynaphthoylamino)-naphthalin <SEP> grünstichiges <SEP> <B>></B> <SEP> Dunkelviolett
<tb>  sulfonyl-indazol <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)-naphthalin <SEP> Blaugrau <SEP>   <SEP>  
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> grünstichiges <SEP>   <SEP> Violettgrau
<tb>  2-methyl-4-chlorbenzol <SEP> Blaugrau
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP> Dunkelviolett
<tb>  2,5-dimethoxybenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP>   <SEP>  
<tb>  2,

  4-dimethoxy-5-chlorbenzol
<tb>    <SEP> 1-(2'-Oxycarbazol-3'-carboylamino)- <SEP> schwaches <SEP> Grau <SEP>  
<tb>  4-chlorbenzol <SEP> Grau
<tb>    <SEP> 1-(2'-Oxyanthracen-3'-carboylamino)- <SEP> Grün <SEP> Gelbgrün <SEP> Olivgrau
<tb>  2-methylbenzol
<tb>    <SEP> 1-(6' <SEP> Brom-2',3'-oxynaphthoylamino)- <SEP> grünstichiges <SEP> Grün <SEP> Dunkelviolett
<tb>  2-methoxybenzol <SEP> Blaugrau
<tb>  3-Amino-5-benzoyl- <SEP> 2-(2',3'-Oxynaphthoylamino)-naphthalin <SEP> rotstichiges <SEP> blaustichiges <SEP>  
<tb>  amino-indazol <SEP> Grau <SEP> Olivgrün
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)-naphthalin <SEP>   <SEP>   <SEP> stumpfes
<tb>  Violett
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamko)- <SEP> > <SEP>   <SEP>  
<tb>  2-methyl-4-chlorbenzol
<tb>    <SEP> 1-(2',3'-Oxynaphthoylamino)- <SEP> grünstichiges <SEP> @ >
<tb>  2,

  4-dimethoxy-5-chlorbenzol <SEP> Blaugrau
<tb>    <SEP> _1-(2',3'-Oxynaphthoylamino)- <SEP>   <SEP> > <SEP>  
<tb>  2,5-dimethoxybenzol       
EMI0015.0001     
  
    Farbton
<tb>  Diazokomponente <SEP> Azokomponente <SEP> Kupfer- <SEP> Kobalt- <SEP> Nickel  komplex <SEP> komplex <SEP> komplex
<tb>  3 <SEP> Amino-5-benzoyl- <SEP> 1-(2'-Oxycarbazol-3'-carboylamino)- <SEP> Violettgrau <SEP> ' <SEP> Grau <SEP> Dunkelviolett
<tb>  amino-indazol <SEP> 4-chlbrbenzol
<tb>    <SEP> 1-(2'-Oxyanthracen-3'-carboylamino)- <SEP> gelbstichiges <SEP> Gelbolivgrün <SEP> Grüngrau
<tb>  2-methylbenzol <SEP> Grün
<tb>    <SEP> 1-(6'-Brom-2',3'-oxynaphthoylamino)- <SEP> grünstichiges <SEP> blaustichiges <SEP> stumpfes
<tb>  2-methoxybenzol <SEP> Blaugrau <SEP> Olivgrün <SEP> blaustichiges
<tb>  Violett
<tb>  3-Amino-6-acetyl- <SEP> 1-(2';

  3'-Oxynaphthoylamino)- <SEP> Blaugrau <SEP> blaustichiges <SEP> Violettgrau
<tb>  indazol <SEP> 2-methoxybenzol <SEP> Grün
<tb>    <SEP> 2-(2',3'-Oxynaphthoylamino)-naphthalin <SEP>   <SEP>   <SEP> Graubraun
<tb>    <SEP> 1-(2'-Oxycarbazol3'-carboylamino)- <SEP> Violettblau <SEP> Grau <SEP> Korinth
<tb>  4-chlorbenzol
<tb>    <SEP> 1-(2'-Oxyanthracen-3'-carboylamino)- <SEP> blaustichiges <SEP> gelbstichiges <SEP> Graugrün
<tb>  2-methylbenzol <SEP> Grün <SEP> Grün
<tb>  3 <SEP> Amino-5-phenyl- <SEP> 2,3-Oxynaphthoylaminobenzol <SEP> Blaugrau <SEP> grünstichiges <SEP>   sulfonyl-indazol <SEP> Grau



  Process for the preparation of water-insoluble, metal-containing azo dyes It has been found that new, valuable, water-insoluble, metal-containing azo dyes are obtained if diazonium compounds of amines of the formula
EMI0001.0010
    wherein the benzene nucleus a by halogen atoms, alkyl;

          Alkoxy, aryloxy, acyloxy, nitro, trifluoromethyl, carboxylic acid esters - (- COOR), optionally substituted carboxamide (-CONH2, -CONHR, -CONR2), acyl, alkylsulphone, arylsulphone, sulphone, acidic ' ter- (-S02R),

       optionally substituted sulfonic acid amide (-S02NH2, -S02NHR, -S02NR2), acylammo- or arylamino groups can be substituted with arylamides of aromatic or heterocyclic o-0, ycarboxylic acids or acyl acetic acids, which are free of water-solubilizing groups, such as.

   B. sulfonic acid or carboxylic acid groups, are coupled in bulk or on a non-textile substrate and the dyes thus obtained are treated with metal donors.



  The treatment of the water-insoluble azo dyes obtainable according to the invention with the metal-releasing agents can be carried out in a known manner. As a metal donor z. B. iron, chromium, uranium, manganese, aluminum, lead, cadmium, zinc, but especially cobalt, copper and nickel into consideration, which can be used in the form of their inorganic or organic salts or as complex compounds.



  The metallization is expedient in organic solvents, such as. B. acetone or dimethylformanlld, made in the presence of small amounts of pyridine. The metal complex compounds obtainable in this way are extraordinarily strong in color and generally soluble in acetone, alcohol or nitrocellulose ester lacquers and are therefore suitable for producing colored paints.

   The Metä11- complex compounds can also be used to dye animal fibers, such as wool or silk, and synthetic fibers, such as. B. polyamide, polyurethane, acetyl cellulose or polyester fibers, as well as for dyeing high molecular weight plastic masses can be used.



  In the inventive. Processes are used as azo components arylamides of aromatic or heterocyclic o-oxycarboxylic acids or of acyl acetic acids, for example those of 2,3-oxynaphthoic acid or their 6-substituted derivatives, 2-oxyanthracene-3-carboxylic acid, cresotinic acids;

       halosalicylic acids, 4-oxydiphenyl 3-carboxylic acid, 2-oxycarbazole-3-carboxylic acid, 5-oxy-1,2,1 ', 2'-benzocarbazole-4-carboxylic acid, 3-oxydiphenylene oxide-2- carboxylic acid, 3-oxydiphenylenesulfide-2-carboxylic acid, acetoacetic acid, benzoylacetic acid or terephthaloyl-bis-acetic acid are used.

        As amino compounds which correspond to the above formula and can be used advantageously in the present process, are, for. B. ge called: 3-amino-, indazole, 3-amino-4-chloroindazole, 3 amino-5-chloroindazole, 3-amino-6-chloroindazole, 3-amino-6-methylindazole, 3 amino-5-methoxyindazole, 3- Amino-5-methoxy-6-chloroindazole, 3-amino-6-methoxyindazole, 3-amino-6-ethoxyindazole, 3-amino-5-trifluoromethyl-indazole,

       3 amino-6-trifluoromethyl-indazole, 3-amino-6-acetyl-indazole, 3-amino-5-nitroindazole, 3-amino-6-nitro-indazole, 3-amino-indazole-5-sulfonic acid diethylamide, 3 -Amino-indazole-6-carboxamide, 3-amino-5-methylsulfonyl-indazole, 3-ammo-5-phenylsulfonyl-indazole or 3-amino-5-benzoylamino-indazole.



  These amino compounds, some of which have not yet been described in the literature, can be prepared by known processes, for example by diazotizing o-amino-benzonitriles, Re-,

            Reduction of the diazo compounds with tin chloride and hydrochloric acid to form the hydrazine compounds and ring closure in an acid medium to form the 3 amino-indazoles. The compounds obtainable in this way are stable, readily crystallizing products which can be diazotized in the usual way in mineral acid solution.

    When the diazo solutions are neutralized, the diazo compounds separate out in the form of poorly soluble, stable anhydro-indazole-3-diazoic hydroxides.



  The new dyes are those known from French patent specification no. 981 432, by coupling diazotized 6- or 7-amino-indazole with aryl amides of 2,3-oxynaphthoic acid and subsequently. Metallization is superior to water-insoluble azo dyes in terms of fastness properties.



  <I> Example </I> 36 parts by weight of 1- (2 ', 3' - oxynaphthoylammo) - 2,4-dimethoxy-5-chlorobenzene are mixed with 0.5 parts by weight of an action product of about 20 moles of ethylene oxide to 1 mole of oleyl alcohol and 36 parts by volume of 38 B6 sodium hydroxide solution made into a paste and heated for a quarter of an hour.

   The paste is then poured over 1000 parts by volume of hot water and brought into solution by boiling. The solution thus obtained is allowed to run into a diazo solution, with thorough stirring, which has been prepared in the usual way by diazotizing 16.3 parts by weight of 3-amino-6-methoxyindazole. The temperature of the reaction solution is kept at 25-30 by cooling. After the coupling has ended, the red dye formed is suctioned off and washed.



  To convert it into the copper complex compound, the moist filter cake is slurried in 1000 parts by volume of acetone and a concentrated aqueous solution of 17.1 parts by weight of crystallized copper (11) chloride and 25 parts by volume of pyridine are added. The metallization is complete after brief stirring.

   The reaction mass is diluted with water to about 3000 parts by volume and acidified with 50 parts by volume of hydrochloric acid of 20 B6. The dye thus obtained is filtered off with suction, washed and dried. It is a bluish black powder that appears in the. Linseed oil paint mixed with a white pigment provides gray-blue tones.



  If, in the above example, 24 parts by weight of crystallized cobalt (II) chloride are used instead of 17.1 parts by weight of copper (II) chloride and the metallization is carried out with stirring for 5 hours at room temperature, the cobalt complex compound is obtained in the form of a greenish-black powder which, when mixed with a white pigment, produces green tones when mixed with linseed oil.



  To produce the nickel complex compound, in the above example, the copper (11) chloride is replaced by 24 parts by weight of crystallized nickel chloride and the metallization is carried out by stirring and heating under reflux for five hours.

   A dark powder is obtained which dissolves in organic solvents with a violet color and is suitable for the manufacture of paints and for coloring high molecular weight plastic materials and synthetic fibers.



  The table below also contains a number of further components that can be used according to the invention and the color shades of the azo dyes obtained therefrom:
EMI0003.0001
  
    hue
<tb> diazo component <SEP> azo component <SEP> cobalt- <SEP> nickel- <SEP> copper complex <SEP> complex <SEP> complex
<tb> 3-Amino-indazole <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> bluish <SEP> - <SEP> blue-gray
<tb> 2-methylbenzene <SEP> green
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> violet
<tb> 2-methyl-4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> - <SEP> blue-green
<tb> 2-methoxy-4-chloro-5-methylbenzene
<tb> <SEP> 2- (2 ', 3'-oxynaphthoylamino) - <SEP> green-gray <SEP> blue-tinged <SEP>
<tb> naphthalene <SEP> Bordo
<tb> <SEP> 1- (6'-bromo-21,31-oxynaphthoylamino)

  - <SEP> green <SEP> reddish
<tb> 2-methoxybenzene <SEP> dark blue
<tb> <SEP> 1- (2'-oxycarbazole-3'-carboylamino) - <SEP> - <SEP> violet brown <SEP> violet
<tb> 4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> green <SEP> violet <SEP> blue-green
<tb> 2,4-dimeihoxy-5-chlorobenzene
<tb> 3 <SEP> Amino-5-chloro- <SEP> 1- (V, 3'-Oxynaphthoylamino) - <SEP> - <SEP> Corinth <SEP> greenish tinge
<tb> indazole <SEP> 2,4-dimethoxy-5-chlorobenzene <SEP> dark gray
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> - <SEP> <SEP> Dark gray
<tb> naphthalene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> dark green <SEP> - <SEP> 2-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> - <SEP> violet <SEP> dark gray
<tb> 2-methylbenzene
<tb> <SEP> 2- (2 ', 3'-oxynaphthoylamino)

  - <SEP> - <SEP> dark <SEP> with a green cast
<tb> naphthalene <SEP> red brown <SEP> dark gray
<tb> <SEP> 2- (2 ', 3'-Oxynaphthoylamino) - <SEP> - <SEP> <B> D <SEP> D </B>
<tb> 3-methoxy-diphenylene oxide
<tb> 3-Amino-6-chloro- <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> olive green <SEP> dull <SEP> blue-gray
<tb> indazole <SEP> 2-methoxybenzene <SEP> red-violet
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> brownish <SEP> Bordo <SEP> reddish
<tb> 2-methyl-4-chlorobenzene <SEP> green <SEP> gray
<tb> <SEP> 2- (2 ', 3'-Oxynaphthoylamino) - <SEP> olive green <SEP> Corinth <SEP> blue-gray
<tb> naphthalene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> with a blue cast
<tb> 2,4-dimethoxy-5-chlorobenzene <SEP> green
<tb> <SEP> 1- (6 '<SEP> bromo-21,3'-oxynaphthoylamino) - <SEP> <SEP> bluish <SEP> blue-green
<tb> 2-methoxybenzene <SEP> violet
<tb> <SEP> 1- (2 ',

  3'-Oxynaphthoylamino) - <SEP> Olive green <SEP> - <SEP> "
<tb> 2-methoxy-4-chloro-5-methylbenzene
<tb> <SEP> 1- (2'-oxycarbazole-3'-carboylamino) - <SEP> - <SEP> - <SEP> blue-violet
<tb> 4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> green <SEP> - <SEP> blue-gray
<tb> 2-methylbenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> - <SEP>
<tb> 2-methyl-4-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> - <SEP>
<tb> 2,5-dimethoxybenzene
EMI0004.0001
  
    hue
<tb> diazo component <SEP> azo component <SEP> cobalt- <SEP> nickel- <SEP> copper complex <SEP> complex <SEP> complex
<tb> 3 <SEP> Anuno-6-chior- <SEP> 1- (2 ';

  3'-oxynaphthoylamino) - <SEP> green <SEP> - <SEP> blue-gray
<tb> indazole <SEP> 2-methoxy <SEP> 5-chlorobenzene
<tb> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> - <SEP>
<tb> 2,5-dimethoxy-4-chlorobenzene
<tb> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> - <SEP> <SEP> - <SEP>
<tb> - <SEP> naphtha
<tb>> <SEP> 1- (2'-oxyanthracene-3'-carboylamino) - <SEP> <SEP> - <SEP> green
<tb> 2-methylbenzene
<tb> _.3 <SEP> Amino-6-methyl- <SEP> 2,3-oxynaphthoyl-aminobenzene <SEP> olive green <SEP> Corinth <SEP> greenish
<tb> indazole <SEP> gray-blue
<tb> <SEP> 1- (2 ';

  3'-oxynaphthoylamino) - <SEP> <SEP> violet <SEP>
<tb> 2-methylbenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 2,5-dimethoxy-4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> with a blue cast
<tb> 2-methoxybenzene <SEP> Bordo
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> violet <SEP> <B> </B>
<tb> 2,4-dimethoxy-5-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> bluish tint
<tb> 2-methyl-4-chlorobenzene <SEP> Bordo
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> violet <SEP>
<tb> 2-methoxy-4-chloro-5-methylbenzene
<tb> <SEP> 2- (2 ';

  3'-oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> naphthalene
<tb> <SEP> 1- (2'-oxycarbazole-3'-carboylamino) - <SEP> dark gray <SEP> dark violet <SEP> red-embroidered
<tb> 4-chlorobenzene <SEP> dark blue
<tb> 3-Amino-6-methoxy- <SEP> 1- (6 '<SEP> bromo-2', 3'-oxynaphthoylamino) - <SEP> vivid <SEP> green;

   <SEP> red-sticky <SEP> indazole <SEP> 2-methoxybenzene <SEP> dark blue
<tb> 4,4 '<SEP> bis (2 ", 3" -oxynaphthoylamino) - <SEP> green <SEP> Corinth <SEP> 3,3'-dimethoxydiphenyl
<tb> <SEP> 1- (2'-oxyanthracene-3'-carboylamino) - <SEP> yellowish <SEP> green <SEP> 2-methylbenzene <SEP> green
<tb> <SEP>.

   <SEP> 1- (5'-oxy-1 ', 1 ", 2', 2" -benzocarbazole- <SEP> dark brown <SEP> dark gray <SEP> 4'-carboylamino) -4-methoxybenzene
<tb> <B> s </B> <SEP> Terephthaloyl-bis- (1-acetylamino-2- <SEP> olive-tinged <SEP> old gold <SEP> methoxy-4-chloro-5-methylbenzene) <SEP> yellow
<tb> <SEP> 1- (2'-oxycarbazole-3'-carboylamino) - <SEP> dark gray <SEP> Corinth <SEP> 4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> vivid <SEP> green <SEP> violet <SEP> 2,4.-dimethylbenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> Green <SEP> <SEP> 2-methylbenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> yellowish <SEP> <SEP> 2 <SEP> methyl-4-chlorobenzene <SEP> green
EMI0005.0001
  
    hue
<tb> diazo component <SEP> azo component <SEP> cobalt- <SEP> nickel- <SEP> copper complex <SEP> complex <SEP> complex
<tb> 3-Amino-6-methoxy- <SEP> 1- (2 ',

  3'-oxynaphthoylamino) - <SEP> green <SEP> violet <SEP> indazole <SEP> 2-methyl <SEP> 5-chlorobenzene
<tb> <SEP> 2,3-oxynaphthoyl-aminobenzene <SEP> green <SEP> - <SEP> <SEP> 1- (21,3'-oxynaphthoylamino) - <SEP> yellowish <SEP> violet <SEP> 2 -methoxy-4-chloro-5-methylbenzene <SEP> green
<tb> <SEP> 1- (21,3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> 2,5-dimethoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> _ <SEP> <SEP> <SEP> 2-methoxy-5-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> <SEP> naphthalene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> red-brown <SEP> 4-ethoxybenzene
<tb> <SEP> 1- (21,3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> _ <SEP> 4-methylbenzene
<tb> <SEP> 1- (21,3'-oxynaphthoylamino) - <SEP> <SEP>
<tb> 2,3-dimethylbenzene
<tb> <SEP> 1-oxy-4-methylbenzene-2-carboxylic acid- <SEP> olive green,

   <SEP> violet gray <SEP> greenish
<tb> phenylamide <SEP> gray
<tb> <SEP> 1-oxy-4,5-dichlorobenzene-2-carboxylic acid <SEP> green-gray <SEP> red-brown <SEP> gray-green
<tb> phenylamide
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> yellowish <SEP> violet <SEP> 2,5-dimethoxy <SEP> 4-chlorobenzene <SEP> green
<tb> <SEP> 1- (4'-oxydiphenyl-3'-carboylamino) - <SEP> olive green <SEP> green gray <SEP> green gray
<tb> 2-methoxybenzene
<tb> <SEP> 2- (2 ', 3'-oxynaphthoylamine (y) - <SEP> yellowish <SEP> - <SEP>, <SEP> naphthalene <SEP> green
<tb> 3-Amino-6-ethoxy- <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> red sticky <SEP> blue-gray
<tb> indazole <SEP> 2-methoxy <SEP> 5-chlorobenzene <SEP> violet
<tb> (melting point <SEP> 222
<tb> to <SEP> 224)
<tb> <SEP> 1- (21,3'-oxynaphthoylamino) - <SEP> green <SEP> violet <SEP> 2-methylbenzene
<tb> <SEP> 1- (2 ',

  3'-oxynaphthoylamino) - <SEP> <SEP> <SEP> 2-methoxybenzene
<tb> <SEP> 1- (21,3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> 2-methyl-4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> <SEP> 2-methyl-4-methoxybenzene
<tb> <SEP> 1- (21,3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> 2,5-dimethoxybenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> - <SEP> <SEP> <SEP> 2,5-dimethoxy-4-chlorobenzene
<tb> <SEP> 1- (21,3'-Oxynaphthoylamino) - <SEP> yellowish <SEP> <SEP> blue-gray
<tb> 2,4-dimethoxy-5-chlorobenzene <SEP> green
EMI0006.0001
  
    hue
<tb> diazo component <SEP> azo component <SEP> cobalt- <SEP> nickel- <SEP> copper complex <SEP> complex <SEP> complex
<tb> 3-Amino-6-ethoxy- <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> green <SEP> violet <SEP> indazole <SEP> 2-methoxy-4-chloro-5 -methylbenzene
<tb> <SEP> 1- (2 ',

  3'-Oxynaphthoylamiüo) - <SEP> <B> a </B> <SEP> <SEP> _
<tb> naphthalene
<tb> <SEP> 1- (6 '<SEP> bromine-2', 3 '= oxynaphthoylamino) - <SEP> yellowish <SEP> violet-blue <SEP> blue-green
<tb> 2-methoxybenzene <SEP> green
<tb> <SEP> 2- (2 ', 3'-oxynaphthoylamino) - <SEP> green <SEP> violet <SEP> blue-gray
<tb> naphthalene
<tb> 1- (2'-Oxycarbazole-3'-carboylamino) - <SEP> greenish <SEP> Corinth <SEP> 4-chlorobenzene <SEP> gray
<tb> <SEP> 1-oxy-4-methylbenzene-2-carboxylic acid <SEP> olive green <SEP> violet gray <SEP> gray
<tb> phenylamide
<tb> <SEP> 1-oxy-4,5-dichlorobenzene-2-carboxylic acid <SEP> gray <SEP> violet gray <SEP> a
<tb> phenylamide
<tb> 1- (4'-Oxydiphenyl-3'-carboylamino)

  - <SEP> olive green <SEP> blue green <SEP> greenish
<tb> 2 <SEP> methoxybenzene <SEP> gray
<tb> _ <SEP> color tone
<tb> diazo component <SEP> azo component <SEP> iron- <SEP> zinc- <SEP> uranium- <SEP> cadmium complex <SEP> complex <SEP> complex <SEP> complex
<tb> 3-Amino-6-methoxy- <SEP> 1- (2 ', 3 <SEP> = Oxynaphthoylamino) - <SEP> Corinth <SEP>. Violet <SEP> Red-violet <SEP> Violet
<tb> indazole <SEP> 2 <SEP> methoxy-4-chloro-5-methylbenzene
<tb> shade
<tb> diazo component <SEP> azo component <SEP> cobalt complex <SEP> copper complex
<tb> 3 <SEP> ammo-4-chloro- <SEP> 2,3-oxynaphthoylaminobenzene <SEP> green <SEP> indazole
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> _
<tb> 2-methylbenzene <SEP> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> "<SEP> _
<tb> 2-methoxybenzene
<tb> 1- (2 ', 3'-Oxynaphthoyiamino) - <SEP>, r <SEP> _
<tb> 2-ethoxybenzene
<tb> <SEP> 1- (2 ',

  3'-Oxynaphthoylamino) - <SEP> <SEP> _
<tb> 4-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> _
<tb> 2-methyl4-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> _
<tb> 2,5-d # imethoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylatvno) - <SEP> <SEP> _
<tb> 4-ethoxybenzene
EMI0007.0001
  
    hue
<tb> diazo component <SEP> azo component
<tb> cobalt complex <SEP> copper complex.
<tb> 3-Am @ ino-4-chloro- <SEP> 1- (2 '; 3'-Oxynaphthoylanvno) - <SEP> blue green <SEP> indazole <SEP> 3-nitrobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylanüno) - <SEP> green <SEP> blue-gray
<tb> 2-methyl:

   <SEP> 4-chlorobenzene
<tb> <SEP> 1- (21,3'-oxynaphthoylamino) - <SEP> <SEP>
<tb> 2-methoxy-5-chlorobenzene
<tb> <SEP> 1- (21,3'-oxynaphthoylamino) - <SEP> <SEP>
<tb> naphthalene
<tb> <SEP> 1- (6'-bromo-2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> 2-methoxybenzene
<tb> <SEP> 1- (21,3'-Oxynaphthoylamino) - <SEP> <SEP> 4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> x <SEP> 2,5-dimethoxy-4-chlorobenzene
<tb> <SEP> 1- (2 ';

  3'-Oxynaphthoylaniino) - <SEP> <SEP> greenish <SEP> blue-gray
<tb> naphthahn <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> blue-gray
<tb> 2-methoxy-4-chloro-5-methylbenzene
<tb> <SEP> 2- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> 3-methoxydiphenylene oxide <SEP> - <SEP>'
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> 2,4-dimethylbenzene
<tb> <SEP> 1- (21,3'-oxynaphthoylamino) - <SEP> blue green <SEP> 2-methyl <SEP> 5-chlorobenzene <SEP> <SEP> 1- (21,3'-oxynaphthoylamino) - <SEP> Green <SEP> - <SEP> 4-methylbenzene <SEP> _
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> _.
<tb> 2,3-dimethylbenzene
<tb> <SEP> 4,4'-bis (2 ", 3" -oxynaphthoylamito) '- <SEP> olive <SEP> 3,3'-dimethoxydiphenyl
<tb> <SEP> 1- (2'-oxycarbazole-3'-carboylamino) - <SEP> blue-gray <SEP> 4-cblobenzene
<tb> <SEP> 1- (2'-oxyanthracene-3'-carboylamino)

  - <SEP> yellowish <SEP> green <SEP> 2-methylbenzene
<tb> <SEP> 1- (5'-Oxy-1 ', 2', 1 ", 2" -benzocarbazole-4'- <SEP> violet brown <SEP> carboylamino) -4-methoxybenzene
<tb> <SEP> 1- (5'-Oxy-1 ', 2', 1 ", 2" -benzocarbazole 4'- <SEP> Corinth <SEP> carboylamino) -2-methyl-4-methoxybenzene
<tb> 3-Amino-5-methoxy- <SEP> 2,3-oxynaphthoylaminobenzene <SEP> olive green <SEP> blue-gray
<tb> indazole
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> red sticky <SEP> blue-gray
<tb> 2-methylbenzal
<tb> <SEP> 1- (2 ', 3! <SEP> Oxynaphthoylamino) - <SEP> <SEP> greenish <SEP> blue-gray
<tb> 2-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> blue-gray
<tb> 2-ethoxybenzene
<tb> <SEP> 1- (21,3'-oxynaphthoylamino)

  - <SEP> <SEP>
<tb> 4-methoxybenzene
EMI0008.0001
  
    hue
<tb> diazo component <SEP> azo component
<tb> cobalt complex <SEP> copper complex
<tb> 3-Amino-5-methoxy- <SEP> 1- (2 ',, 3'-Oxynaphthoylamino) - <SEP> olive green <SEP> reddish <SEP> blue-gray
<tb> indazole <SEP> 2-methyl <SEP> 4-methoxybenzene
<tb> <SEP> 1- (2,3'-oxynaphthoylamino) - <SEP> <SEP> blue-gray
<tb> 2,5-dimethoxybenzene
<tb> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP>,> <SEP> "
<tb> 4-ethoxybenzene
<tb> <SEP> 1- (2,3'-oxynaphthoylamino) - <SEP> bluish <SEP> olive green <SEP>
<tb> 3 <SEP> nitrobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> olive green <SEP> violet gray
<tb> 2-methyl-4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> greenish <SEP> blue-gray
<tb> 2-methoxy-5-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino)

  - <SEP> <SEP> blue-gray
<tb> 2,4-diniethoxy-5-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP>
<tb> naphthalene
<tb> <SEP> 1- (6'-bromo-2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> greenish <SEP> blue-gray
<tb> 2-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> blue-gray
<tb> _4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP>
<tb> 2,5-dimethoxy-4-chlorobenzene
<tb> 2- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> greenish <SEP> blue-gray
<tb> naphthalene
<tb> <SEP> 1- (2,3'-Oxynaphthoylamino) - <SEP>,> <SEP>
<tb> 2-methoxy-4-chloro-5-methylbenzene
<tb> - <SEP> 1- (2,3'-Oxynaphthoylamino) - <SEP> bluish <SEP> olive green <SEP> blue-gray
<tb> 2-methyl-5-chlorobenzene
<tb> <SEP> 2- (2 ';

  3'-Oxynaphthoylammo) - <SEP> yellowish <SEP> olive green <SEP> greenish <SEP> blue-gray
<tb> 3-methoxydiphenylene oxide
<tb> <SEP> - <SEP> 1- (2'-oxycarbazole-3'-carboylamino) - <SEP> gray <SEP> reddish <SEP> dark blue
<tb> 4-chlorobenzene
<tb> <SEP> _ <SEP> 1- (2'-oxyanthracene) -3'-carboylamino) - <SEP> yellowish <SEP> green <SEP> green
<tb> 2-methylbenzene
<tb> <SEP> 1- (5'-Oxy-1 ', 2', 1 ", 2" <SEP> benzocarbazole-4'- <SEP> brown <SEP> violet gray
<tb> carboylamino) -4-methoxybenzene
<tb> <SEP> 1- (5'-Oxy <SEP> 1 ', 2', 1 ", 2" -benzocarbazole-4'- <SEP>. <SEP>
<tb> carboylamino) = <SEP> 2-methyl-4-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> bluish <SEP> olive green <SEP> blue-gray
<tb> 2,4-dimethylbenzene
<tb> 3-amino-5-methoxy <SEP> 2- (2 ';

  3'-oxynaphthoylamino) naphthalias <SEP> blue-green <SEP>
<tb> 6-chloromdazole
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> Green <SEP>
<tb> 2,4-dimethoxy-5-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> olive green <SEP>
<tb> 2-methoxy-5-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) -naphthalene <SEP> Green <SEP>
EMI0009.0001
  
    hue
<tb> diazo component <SEP> azo component
<tb> cobalt complex <SEP> copper complex
<tb> 3-Amino-5-methoxy- <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> blue-green <SEP> blue-gray
<tb> 6-chloroindazole <SEP> 2-methoxy-4-chloro-5 <SEP> methylbenzene
<tb> <SEP> 1- (6 '<SEP> bromo-2', 3'-oxynaphthoylamino) - <SEP> green
<tb> 2-methoxybenzene
<tb> <SEP> 1- (2'-oxycarbazole-3'-carboylaimno) - <SEP> gray <SEP> dark blue
<tb> 4-chlorobenzene
<tb> 3-Amino-6-methyl- <SEP> 1- (2 ', 3'-Oxynaphthoylamino)

  - <SEP> green <SEP> red-embroidered <SEP> blue-gray
<tb> indazole <SEP> 2-ethoxybenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> blue-gray
<tb> 4-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) 2-methyl-4-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP>
<tb> 2,5-dimethoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> red sticky <SEP> blue-gray
<tb> 4-ethoxybenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> - <SEP> blue-gray
<tb> 3-nitrobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP>
<tb> naphthalene
<tb> <SEP> 1- (6'-bromo-2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> greenish <SEP> blue-gray
<tb> 2-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> blue-gray
<tb> 4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino)

  - <SEP> <SEP>
<tb> 2-methyl-5-chlorobenzene
<tb> <SEP> 2- (2 ', 3'-Oxynaphthoylamino) - <SEP> - <SEP> Olive green <SEP>
<tb> 3-methoxy-diphenylene oxide
<tb> <SEP> 1- (2'-oxyanthracene-3'-carboylamino) - <SEP> yellowish <SEP> green <SEP> green
<tb> 2-methylbenzene
<tb> <SEP> 1- (5'-Oxy-1 ', 2', 1 ", 2" -benzocarbazole- <SEP> brown <SEP> reddish <SEP> blue-gray
<tb> 4'-carboylamino) -4-methoxybenzene
<tb> <SEP> 1- (5'-Oxy-1 ', 2', 1 ", 2" <SEP> benzocarbazole- <SEP> <SEP>
<tb> 4'-carboylamino) -2-methyl-4-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> green <SEP> muted:

   <SEP> blue
<tb> 2,4-dimethylbenzene
<tb> <SEP> 1- (6'-methoxy-2 ', 3'-oxynaphthoylamino) - <SEP> yellowish <SEP> green <SEP> blue-green
<tb> 2-methyl-5-chlorobenzene
<tb> <SEP> 1- (6'-methoxy-2 ', 3'-oxynaphthoylamino) - <SEP> <SEP>
<tb> 2 <SEP> methoxybenzene
EMI0010.0001
  
    hue
<tb> diazo component <SEP> azo component <SEP> copper- <SEP> cobalt- <SEP> nickel complex <SEP> complex <SEP> complex
<tb> 3-Amino-indazol5- <SEP> 2,3-Oxynaphthoylaminobenzene <SEP> Blue-gray <SEP> Green <SEP> Bordo
<tb> sulfonic acid diethylamide
<tb> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <B> <SEP> </B> <SEP> red-violet
<tb> 2-methylbenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> green-tinged <SEP> <SEP>
<tb> 2-methoxybenzene <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> blue-gray <SEP> <SEP> Bordo
<tb> 2-ethoxybenzene
<tb> <SEP> 1- (2 ',

  3'-oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 4-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <B> <SEP> </B> <SEP> Red-violet
<tb> 2-methyl-4-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> violet
<tb> 2,5-thin ethoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <B> <SEP> </B> <SEP> Bordo
<tb> 4-ethoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> greenish <SEP> <SEP> red-violet
<tb> 3-nitrobenzene <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> blue-gray <SEP> green <SEP> violet
<tb> 2-methyl-4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 2-methoxy-5-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 2,4-dimethoxy-5-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino)

  -naphthalene <SEP> <SEP> <B> <SEP> </B>
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> greenish <SEP> <SEP> Bordo
<tb> 4-chlorobenzene <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> reddish
<tb> 2,5-dimethoxy-4-chlorobenzene <SEP> violet
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> @>
<tb> 2-methoxy-4-chloro-5 <SEP> methylbenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> blue-gray <SEP> <SEP> violet
<tb> 2,4-dimethylbenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> a <SEP> Bordo
<tb> 4-methylbenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> violet
<tb> 2,3-dimethylbenzene
<tb> <SEP> 2- (2 ', 3'-Oxynaphthoylamino) - <SEP> greenish <SEP> green <SEP> bluish
<tb> naphthalene <SEP> blue-gray <SEP> Bordo
<tb> <SEP> 2- (2 ', 3'-oxynaphthoylamino)

  - <SEP> blue-gray <SEP> <SEP> Corinth
<tb> 3-methoxy-diphenylene oxide
<tb> <SEP> 4,4'-bis (2 ", 3" -oxynaphthoylamino) - <SEP> gray <SEP> olive <SEP> with a bluish tint
<tb> 3,3'-dimethoxy <SEP> diphenyl <SEP> Bordo
<tb> <SEP> 1- (6 '<SEP> Brom-2', 3'-oxynaphthoylamino) - <SEP> greenish <SEP> green <SEP> violet
<tb> 2-methoxybenzene <SEP> blue-gray
<tb> <SEP> 1- (2'-oxyanthracene-3'-carboylamino) - <SEP> green <SEP> yellowish <SEP> dark green
<tb> 2-methylbenzene <SEP> green
EMI0011.0001
  
    hue
<tb> diazo component <SEP> azo component <SEP> copper- <SEP> cobalt- <SEP> nickel complex <SEP> complex <SEP> complex
<tb> 3-Amino-indazole-5- <SEP> 1- (5'-Oxy-1 ', 2', 1 ", 2" -benzocarbazole-4'- <SEP> violet-tinged <SEP> brown <SEP> Gray
<tb> sulfonic acid diethylamide <SEP> carboylamino) -4-methoxybenzene <SEP> gray
<tb> 3-Amino-5-trifluoro- <SEP> 1- (2 ',

  3'-Oxynaphthoylamino) - <SEP> greenish <SEP> green <SEP> methylindazole <SEP> 2,5-dimethoxybenzene <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> reddish <SEP> <SEP> 2-methyl-4-chlorobenzene <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> greenish <SEP> <SEP> 2 <SEP> methoxy-5-chlorobenzene <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> blue-gray <SEP> <SEP> 2,4-dimethoxy-5-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) -naphthalene <SEP> Blue-gray <SEP> <SEP> x <SEP> 1- (2', 3'-Oxynaphthoylamino) - <SEP> <SEP > <SEP> 2 <SEP> methoxy-4-chloro-5-methylbenzene
<tb> <SEP> 1- (6'-bromo-2 ', 3'-oxynaphthoylamino) - <SEP> green-tinged <SEP> <SEP> 2-methoxybenzene <SEP> blue-gray
<tb> <SEP> 2- (2 ', 3'-oxynaphthoylamino) -naphthalene <SEP> blue-gray <SEP> <B> </B> <SEP> 3-amino-6 <SEP> trifluoro- <SEP> 2 ,

  3-oxynaphthoylaminobenzene <SEP> <SEP> bluish <SEP> Corinth
<tb> methylindazole <SEP> G
<tb> <SEP> 1- (2 '; 3'-Oxynaphthoylamino) - <SEP> <SEP> - <SEP> bluish tint
<tb> 2-methoxybenzene <SEP> Bordo
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> bluish <SEP> violet
<tb> 2-methylbenzene <SEP> green
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> - <SEP> 2-ethoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> bluish <SEP> violet-gray
<tb> 4-methoxybenzene <SEP> green
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <B> <SEP> </B> <SEP> reddish
<tb> 2-methylL4-methoxybenzene <SEP> violet
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> violet
<tb> 2,5-dimethoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylaxnino) - <SEP> <B> </B> <SEP>> <SEP> Corinth
<tb> 4-ethoxybenzene
<tb> <SEP> 1- (2 ',

  3'-oxynaphthoylamino) - <SEP> <SEP> <SEP> violet
<tb> 3 <SEP> nitrobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> blue-green <SEP>
<tb> 2-methyl-4-chlorobenzene
<tb> <SEP> 1- (2 <SEP>; 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> reddish
<tb> 2-methoxy-5-chlorobenzene <SEP> violet
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 2,4-di # methoxy-5-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) -naphthalene <SEP> <B> <SEP> </B> <SEP>
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> 4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> reddish
<tb> 2,

  5-dimethoxy-4-chlorobenzene <SEP> violet
EMI0012.0001
  
    hue
<tb> diazo component <SEP> azo component <SEP> copper- <SEP> cobalt- <SEP> nickel complex <SEP> complex <SEP> complex
<tb> 3-Amino-6-trifluoro- <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> blue-gray <SEP> blue-green <SEP> red-embroidered
<tb> methyhndazole <SEP> 2-methoxy-4-chloro-5-methylbenzene <SEP> violet
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 2-methyl-5-chlorobenzene
<tb> <SEP> 2- (2 ', 3'-Oxynaphthoylamino) -naphthalm <SEP> <SEP> <SEP> Corinth
<tb> <SEP> 2- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 3-methoxydiphenylene oxide
<tb> <SEP> 1- (6 '<SEP> Bröm-2', 3'-oxynaphthoylamino) - <SEP> <SEP> <SEP> violet
<tb> 2-methoxybenzene
<tb> 1- (2'-oxycarbazole-3'-carboylamino)

  - <SEP> red-embroidered <SEP> olive <SEP> brown
<tb> - <SEP> 4-chlorobenzene <SEP> dark blue
<tb> 1- (2'-Oxyanthracene-3'-carboylamino) - <SEP> Green <SEP> <B> </B> <SEP> Gray
<tb> - <SEP> 2-methylbenzene
<tb> <SEP> 1- (5'-Oxy-1 ', 2', 1 ", 2" -benzocarbazole <SEP> red sticky <SEP> violet gray <SEP> violet gray
<tb> - <SEP> 4'-carboylamino) -4-methoxybenzene <SEP> gray
<tb> <SEP> 1- (5'-Oxy-1 ', 2', 1 ", 2" -benzocarbazole- <SEP> <SEP> <SEP>
<tb> 4'-carboylamino) -2-methyl-4-methoxybenzene
<tb> 3-Amino-6-nitro- <SEP> 2;

  3-oxynaphthoylaminobenzene <SEP> blue-gray <SEP> yellow-tinged <SEP> corinth
<tb> indazole <SEP> green.
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> _
<tb> 2-methylbenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> greenish <SEP> olive green <SEP> Corinth
<tb> 2-methoxybenzene <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> blue-gray <SEP> <SEP>
<tb> 2-ethoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> yellowish <SEP>
<tb> 4-methoxybenzene <SEP> green
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> violet gray
<tb> 2-methyl <SEP> 4-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> green-tinged <SEP> <SEP> red-tinged
<tb> 2,5-dimethoxybenzene <SEP> blue-gray <SEP> blue-gray
<tb> b <SEP> 1- (2 ', 3'-oxynaphthoylamino)

  - <SEP> blue-gray <SEP> <SEP> Corinth
<tb> 4-ethoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> green-tinged <SEP> green <SEP> gray
<tb> 3-nitrobenzene <SEP> blue-gray
<tb> <SEP> - <SEP> 1- (2 '; 3'-Oxynaphthoylamino) - <SEP> blue-gray <SEP> yellowish <SEP> blue-gray
<tb> 2-methyl-4-chlorobenzene <SEP> green
<tb> <SEP> 1- (2 ';

  3'-Oxynaphthoylamino) - <SEP> greenish <SEP> yellowish <SEP> reddish
<tb> 2-methoxy-5-chlorobenzene <SEP> blue-gray <SEP> green <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylam-mo) -naphthalene <SEP> blue-gray <SEP> <SEP>
<tb> 1- (6'-bromo-2 ', 3'-oxynaphthoylamino) - <SEP> greenish <SEP> <SEP> dark red 2 <SEP> methoxybenzene <SEP> blue-gray <SEP> violet
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <B> r </B> <SEP> <SEP> violet gray
<tb> 4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> blue-gray <SEP> <SEP> blue-gray
<tb> 2,5-dimethoxy-4-chlorobenzene
EMI0013.0001
  
    hue
<tb> diazo component <SEP> azo component <SEP> copper- <SEP> cobalt- <SEP> nickel complex <SEP> complex <SEP> complex
<tb> 3-Anino-6-nitro- <SEP> 2- (2 ', 3'-Oxynaphthoylamino) -naphthalene <SEP> blue-gray,

   <SEP> green <SEP> reddish
<tb> indazole <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> - <SEP> y <SEP> yellowish
<tb> 2-methoxy-4-chloro-5-methylbenzene <SEP> green <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> reddish <SEP>
<tb> 2-methyl-5-chlorobenzene <SEP> blue-gray
<tb> <SEP> 2- (2 ', 3'-oxynaphthoylamino) - <SEP> greenish <SEP> - <SEP> 3-methoxy-diphenylene oxide <SEP> blue-gray
<tb> <SEP> 1- (2'-oxycarbazole-3'-carboylamino) - <SEP> - <SEP> gray <SEP> violet gray
<tb> 4-chlorobenzene
<tb> 1- (2'-oxyanthracene-3'-carboylamino) - <SEP> green <SEP> brown <SEP> brown
<tb> 2-methoxybenzene
<tb> <SEP> 1- (5'mOxy-11,21,1 ", 211-benzocarbazole-4'- <SEP> - <SEP> <SEP> carboylamino) -4-methoxybenzene
<tb> <SEP> 1- (5'-Oxy-1 ', 2', 1 ", 2" -benzocarbazole-4'- <SEP> - <SEP> <SEP> carboylamino) -2-methyl-4- methoxybenzene
<tb> <SEP> 1- (6 '<SEP> Methoxy-2',

  3'-oxynaphthoylamino) - <SEP> blue-green <SEP> yellowish <SEP> gray
<tb> 2-methoxybenzene <SEP> green
<tb> <SEP> 1- (6 '<SEP> methoxy-2', 3'-oxynaphthoylamino) - <SEP> <SEP> <SEP> blue-gray
<tb> 2-methyl-5-chlorobenzene
<tb> 3-Aminoindazole-6- <SEP> 2,3-oxynaphthoylaminobenzene <SEP> blue-gray <SEP> green <SEP> violet-gray
<tb> carboxamide
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> dull <SEP> 2-methylbenzene <SEP> violet
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <SEP>
<tb> 2-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 3-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> violet gray
<tb> 2-methyl-4-methoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> blunt
<tb> 2,5-dimethoxybenzene <SEP> violet
<tb> <SEP>, <SEP> 1- (2 ',

  3'-oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 4-ethoxybenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP>
<tb> 3-nntrobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamno) - <SEP> <SEP> <SEP> violet gray
<tb> 2-methyl <SEP> 4-chlorobenzene <SEP> - <SEP> - <SEP> - <SEP> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP > blunt
<tb> 2-methoxy-5-chlorobenzene <SEP> - <SEP> violet
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 2,4-dimethoxy-5-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) naphthalene <SEP>
<tb> <SEP> 1- (6 '<SEP> bromo-2', 3'-oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 2-methoxybenzene <SEP> <SEP> 1- (2 ', 3'-oxynaphthoylamino)

  - <SEP> <SEP> v
<tb> 9-chlorobenzene
EMI0014.0001
  
    hue
<tb> diazo component <SEP> azo component <SEP> copper- <SEP> cobalt- <SEP> nickel complex <SEP> complex <SEP> complex
<tb> 3 <SEP> aminoindazole-6- <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> blue-gray <SEP> green <SEP> blunt
<tb> carboxamide <SEP> 2,5-dimethoxy-4-chlorobenzene <SEP> violet
<tb> <SEP> 2- (2 ';

  3'-oxynaphthoylamino) naphthalene <SEP> <B>> </B> <SEP> <SEP>
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) - <SEP> <B> <SEP> </B> <SEP>
<tb> 2-methoxy-4-chloro-5-methylbenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphihoylamino) - <SEP> - <SEP> <B> <SEP> </B> <SEP>
<tb> 2-methyl = 5-chlorobenzene
<tb> <SEP> 2- (2 ', 3'-Oxynaphthoylamino) - <SEP> <B> <SEP> D </B> <SEP>
<tb> 3-methoxydiphenylene oxide
<tb> <SEP>, <SEP> 1- (2'-Oxycarbazo1-3'-carboylamino) - <SEP> reddish <SEP> gray <SEP>
<tb> 4-chlorobenzene <SEP> dark brown
<tb> <SEP> 1- (2'-oxyanthracene-3'-carboylamino) - <SEP> green <SEP> yellowish <SEP> dark green
<tb> 2-methylbenzene <SEP> green
<tb> <SEP> 1- (6 '<SEP> methoxy-21,31-oxynaphthoylamino) - <SEP> blue-green <SEP> <SEP> greenish
<tb> 2-methoxybenzene <SEP> blue-gray
<tb> <SEP> 1- (6 '<SEP> methoxy-21,31-oxynaphthoylamino)

  - <SEP> <SEP> <SEP>
<tb> 2-methyl-5-chlorobenzene
<tb> <SEP> I- (2, ', 3'-Oxynaphthoylamino) - <SEP> gray-blue <SEP> green <SEP> violet-gray
<tb> 2,4-dimethylbenzene
<tb> <SEP> 1- (2 '; 3'-oxynaphthoylamino) - <SEP> <B> <SEP> </B> <SEP>
<tb> 2,3-dimethylbenzene
<tb> 3 <SEP> Amino-5-methyl- <SEP> 2- (2 ', 3'-oxynaphthoylamino) -naphthalene <SEP> greenish <SEP> <B>> </B> <SEP> dark purple
<tb> sulfonyl-indazole <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-oxynaphthoylamino) -naphthalene <SEP> blue-gray <SEP> <SEP>
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> greenish <SEP> <SEP> violet gray
<tb> 2-methyl-4-chlorobenzene <SEP> blue-gray
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP> Dark purple
<tb> 2,5-dimethoxybenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP> <SEP>
<tb> 2,

  4-dimethoxy-5-chlorobenzene
<tb> <SEP> 1- (2'-oxycarbazole-3'-carboylamino) - <SEP> weak <SEP> gray <SEP>
<tb> 4-chlorobenzene <SEP> gray
<tb> <SEP> 1- (2'-oxyanthracene-3'-carboylamino) - <SEP> green <SEP> yellow green <SEP> olive gray
<tb> 2-methylbenzene
<tb> <SEP> 1- (6 '<SEP> Brom-2', 3'-oxynaphthoylamino) - <SEP> greenish <SEP> green <SEP> dark purple
<tb> 2-methoxybenzene <SEP> blue-gray
<tb> 3-Amino-5-benzoyl- <SEP> 2- (2 ', 3'-oxynaphthoylamino) -naphthalene <SEP> red-tinged <SEP> blue-tinged <SEP>
<tb> amino-indazole <SEP> gray <SEP> olive green
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) -naphthalene <SEP> <SEP> <SEP> blunt
<tb> purple
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamko) - <SEP>> <SEP> <SEP>
<tb> 2-methyl-4-chlorobenzene
<tb> <SEP> 1- (2 ', 3'-Oxynaphthoylamino) - <SEP> green-tinged <SEP> @>
<tb> 2,

  4-dimethoxy-5-chlorobenzene <SEP> blue-gray
<tb> <SEP> _1- (2 ', 3'-Oxynaphthoylamino) - <SEP> <SEP>> <SEP>
<tb> 2,5-dimethoxybenzene
EMI0015.0001
  
    hue
<tb> diazo component <SEP> azo component <SEP> copper- <SEP> cobalt- <SEP> nickel complex <SEP> complex <SEP> complex
<tb> 3 <SEP> Amino-5-benzoyl- <SEP> 1- (2'-oxycarbazole-3'-carboylamino) - <SEP> violet gray <SEP> '<SEP> gray <SEP> dark violet
<tb> amino-indazole <SEP> 4-chlorobenzene
<tb> <SEP> 1- (2'-oxyanthracene-3'-carboylamino) - <SEP> yellowish <SEP> yellow olive green <SEP> green gray
<tb> 2-methylbenzene <SEP> green
<tb> <SEP> 1- (6'-bromo-2 ', 3'-oxynaphthoylamino) - <SEP> greenish <SEP> bluish <SEP> dull
<tb> 2-methoxybenzene <SEP> blue-gray <SEP> olive green <SEP> with a bluish tint
<tb> purple
<tb> 3-Amino-6-acetyl- <SEP> 1- (2 ';

  3'-Oxynaphthoylamino) - <SEP> blue-gray <SEP> bluish <SEP> violet-gray
<tb> indazole <SEP> 2-methoxybenzene <SEP> green
<tb> <SEP> 2- (2 ', 3'-oxynaphthoylamino) -naphthalene <SEP> <SEP> <SEP> gray-brown
<tb> <SEP> 1- (2'-Oxycarbazole3'-carboylamino) - <SEP> violet blue <SEP> gray <SEP> Corinth
<tb> 4-chlorobenzene
<tb> <SEP> 1- (2'-oxyanthracene-3'-carboylamino) - <SEP> bluish <SEP> yellowish <SEP> gray-green
<tb> 2-methylbenzene <SEP> green <SEP> green
<tb> 3 <SEP> Amino-5-phenyl- <SEP> 2,3-oxynaphthoylaminobenzene <SEP> blue-gray <SEP> greenish <SEP> sulfonyl-indazole <SEP> gray

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von wasserunlöslichen metallhaltigen Azofarbstoffen, dadurch gekennzeich net, dass man Diazoniumverbindungen von Aminen der Formel EMI0015.0007 worin der Benzolkern a durch Halogenatome, Alkyl-, Alkoxy-, Aryloxy-, Acyloxy-, Nitro-, Trifluormethyl-, Carbonsäureester-, PATENT CLAIM Process for the preparation of water-insoluble metal-containing azo dyes, characterized in that one diazonium compounds of amines of the formula EMI0015.0007 wherein the benzene nucleus a by halogen atoms, alkyl, alkoxy, aryloxy, acyloxy, nitro, trifluoromethyl, carboxylic acid ester, gegebenenfalls substituierte Car- bonsäureamid-, Acyl-, Alkylsulfon-, Arylsulfon-, Sulfonsäureester-, gegebenenfalls substituierte Sulfon- säureamid-, Acylamino- oder Arylaminogruppen sub stituiert sein kann, mit Arylamiden von aromatischen oder heterocyclischen o-Oxycarbonsäuren oder von Acylessigsäuren, optionally substituted carboxylic acid amide, acyl, alkyl sulfonic, aryl sulfonic, sulfonic acid ester, optionally substituted sulfonic acid amide, acylamino or arylamino groups can be substituted with aryl amides of aromatic or heterocyclic o-oxycarboxylic acids or of acyl acetic acids, die frei von wasserlöslichmachenden Gruppen sind, in Substanz oder auf einem nicht textilen Substrat kuppelt und die so erhaltenen Farb stoffe mit metallabgebenden Mitteln behandelt. UNTERANSPRUCH Verfahren nach Patentanspruch, dadurch ge- kennzeichnet, dass man als metallabgebende Mittel Kobalt-, Nickel- oder Kupferverbindungen verwendet. which are free of water-solubilizing groups, coupled in substance or on a non-textile substrate and treated the dyes thus obtained with metal donating agents. SUBCLAIM Method according to patent claim, characterized in that cobalt, nickel or copper compounds are used as the metal releasing agent.
CH1160761A 1958-07-18 1959-07-15 Process for the production of water-insoluble, metal-containing azo dyes CH393585A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEF26196A DE1086832B (en) 1958-07-18 1958-07-18 Process for the production of water-insoluble azo dyes
DEF28442A DE1132271B (en) 1959-05-15 1959-05-15 Process for the production of water-insoluble azo dyes

Publications (1)

Publication Number Publication Date
CH393585A true CH393585A (en) 1965-06-15

Family

ID=25974148

Family Applications (2)

Application Number Title Priority Date Filing Date
CH1160761A CH393585A (en) 1958-07-18 1959-07-15 Process for the production of water-insoluble, metal-containing azo dyes
CH7581059A CH363421A (en) 1958-07-18 1959-10-01 Process for the production of water-insoluble metal-containing azo dyes on the fiber

Family Applications After (1)

Application Number Title Priority Date Filing Date
CH7581059A CH363421A (en) 1958-07-18 1959-10-01 Process for the production of water-insoluble metal-containing azo dyes on the fiber

Country Status (2)

Country Link
BE (1) BE580836A (en)
CH (2) CH393585A (en)

Also Published As

Publication number Publication date
CH363421A (en) 1962-03-30
BE580836A (en) 1960-01-18

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