DE2211663A1 - AZO DYES WITH 2,6-DIAMINOPYRIDINES AS COUPLING COMPONENTS - Google Patents

AZO DYES WITH 2,6-DIAMINOPYRIDINES AS COUPLING COMPONENTS

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Publication number
DE2211663A1
DE2211663A1 DE19722211663 DE2211663A DE2211663A1 DE 2211663 A1 DE2211663 A1 DE 2211663A1 DE 19722211663 DE19722211663 DE 19722211663 DE 2211663 A DE2211663 A DE 2211663A DE 2211663 A1 DE2211663 A1 DE 2211663A1
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DE
Germany
Prior art keywords
red
amino
nitro
acid
ester
Prior art date
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Granted
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DE19722211663
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German (de)
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DE2211663C3 (en
DE2211663B2 (en
Inventor
Johannes Dr Dehnert
Gunther Dr Lamm
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BASF SE
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BASF SE
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Priority to DE19722211663 priority Critical patent/DE2211663C3/en
Priority to CH321773A priority patent/CH596263A5/xx
Priority to CS163973A priority patent/CS178421B2/cs
Priority to US05/338,859 priority patent/US4042578A/en
Priority to IN502/CAL/73A priority patent/IN139039B/en
Priority to DD169311A priority patent/DD106192A5/xx
Priority to NL7303378A priority patent/NL7303378A/xx
Priority to FR7308567A priority patent/FR2187857B1/fr
Priority to SU1891749A priority patent/SU521848A3/en
Priority to BE128597A priority patent/BE796542A/en
Priority to IT48707/73A priority patent/IT979789B/en
Priority to GB1140873A priority patent/GB1422650A/en
Priority to JP48027651A priority patent/JPS6139347B2/ja
Publication of DE2211663A1 publication Critical patent/DE2211663A1/en
Publication of DE2211663B2 publication Critical patent/DE2211663B2/en
Application granted granted Critical
Publication of DE2211663C3 publication Critical patent/DE2211663C3/en
Priority to US05/711,863 priority patent/USRE29640E/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C07D213/77—Hydrazine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • 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
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3639—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more amino 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
    • 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
    • C09B31/12—Disazo dyes from other coupling components "C"
    • C09B31/14—Heterocyclic components
    • C09B31/153—Heterocyclic components containing a six-membered ring with one nitrogen atom as the only ring hetero-atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
    • C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
    • C09B43/202—Aliphatic, cycloaliphatic, araliphatic carboxylic acids
    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/78—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with other reactive groups
    • C09B62/82—Azo dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Cosmetics (AREA)

Description

Azofarbstoffe mit 2,6-Diaminopyridinen als kupplungskomponenten Die Erfindung betrifft Farbstoffe der Formel I in der D den Rest einer Diazokomponente, X Cyan oder Carbonamid, einer der Reste R Phenyl und der andere Rest R Wasserstoff oder gegebenenfalls durch Hydroxy, Alkoxy, Hydroxyalkoxy oder Acyloxy substituiertes Alkyl bedeuten.Azo dyes with 2,6-diaminopyridines as coupling components The invention relates to dyes of the formula I. in which D is the radical of a diazo component, X is cyano or carbonamide, one of the radicals R is phenyl and the other radical R is hydrogen or alkyl which is optionally substituted by hydroxy, alkoxy, hydroxyalkoxy or acyloxy.

Die Reste D leiten sich z.B. von Aminen der Bensol-9 Naphthalin-, Benzthiazol-, Benzisothiazol- Thiazol-, Thiadiazol-, Thiophen-, Azobenzol- oder Anthrachinonreihe ab.The residues D are derived e.g. from amines of the Bensol-9 naphthalene, Benzthiazole, benzisothiazole, thiazole, thiadiazole, thiophene, azobenzene or Anthraquinone series.

Als Substituenten für die Reste D der Diazokomponenten sind beispielsweise zu nennen: in der Benzolreihe: Chlor, Brom, Nitro, Cyan, Trifluormethyl, Methylsulfonyl, Äthylsulfonyl, Phenylsulfonyl, Csrbomethoxy, Carbobutoxy, Carbo-ß-methoxy-äthoxy, Carbo-ß-hydroxy-äthoxy, gegebenenfalls N-mono- oder N-disubstituiertes Carbon- oder Sulfonamid, Methyl, Äthyl, Methoxy oder Äthoxy.Substituents for the radicals D of the diazo components are, for example to mention: in the benzene series: chlorine, bromine, nitro, cyano, trifluoromethyl, methylsulfonyl, Ethylsulfonyl, Phenylsulfonyl, Csrbomethoxy, Carbobutoxy, Carbo-ß-methoxy-ethoxy, Carbo-ß-hydroxy-ethoxy, optionally N-mono- or N-disubstituted carbon- or Sulfonamide, methyl, ethyl, methoxy or ethoxy.

N-Substituenten der Carbon- oder Sulfonamide sind dabei z.B.N-substituents of the carboxylic or sulphonamides are e.g.

Methyl, Äthyl, Propyl, Butyl, ß-Hydroxyäthyl, γ-Hydroxy-propyl, ß-Methoxy-äthyl, -Methoxy-propyl oder γ-Äthoxypropyl sowie das Pyrrolidid, Piperidid oder Norpholid.Methyl, ethyl, propyl, butyl, ß-hydroxyethyl, γ-hydroxy-propyl, ß-methoxy-ethyl, -methoxy-propyl or γ-ethoxypropyl and the pyrrolidide, Piperidide or norpholide.

In der Azobenzolreihe: Chlor, Brom, Nitro, Cyan, Methyl Äthyl, Methoxy oder Athoxy. In der Naphthalinreihe Nitro, in der heterocyclischen Reihe: Chlor, Brom, Nitro, Cyan9 Methyl, Methyl, Phenyl, Methoxy, Äthoxy, Methylmercapto, ß-Carbomethoxy-äthylmercapto, ß-Carboäthoxy-äthylmercapto, Carbomethoxy9 Carboäthoxy, Acetyl, Methylsulfonyl oder Äthylsulfonyl.In the azobenzene series: chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy or athoxy. In the naphthalene series nitro, in the heterocyclic series: chlorine, Bromine, nitro, cyano, methyl, methyl, phenyl, methoxy, ethoxy, methyl mercapto, ß-carbomethoxy-ethyl mercapto, ß-Carboethoxy-ethylmercapto, carbomethoxy9 carboethoxy, acetyl, methylsulfonyl or Ethyl sulfonyl.

Der Rest D leitet sich im einzelnen z.B. von folgenden Aminen ab: Anilin o-, m- oder p-Toluldin, o-, m- oder p-Nitroanilin, o-, m- oder p-Cyananilin, 2,4-Dicyananilin, o-, m- oder p-Chloranilin, o-, m- oder p-Bromanilin, 2,4,6-Tribromanilin, 2-Chlor-4-nitroanilin, 2-Brom-4-nitroanilin, 2-Cyan-4-nitroanilin, 2-Methyls-ulfonyl-4-nitroanilin, 2-Methyl-4-nitroanilin, 2-Methoxy-4-nitroanilin, 4-Chlor-2-nitroanilin, 4-Methyl-2-nitroanilin, 4-Methoxy-2-nitroanillns 1-Amino-2-trifluormethyl-4-chlorbenzol, 2-Chlor-5-amino-benzonitril, 2-Amino-5-chlorbenzonitril, 1-Amino-2-nitrobenzol-4-sulfonsäure-n-butylamid oder -ß-methoxyäthylamid, 2,4-Dinitroanilin, 2,4-Dinitro-6-chloranilin, 2,4-Dinitro-6-bromanilin, 2,4-Dinitro-6-cyananilin, i-Amino-2,4-dinitrobenzol-6-methylsulfon, 2,6-Dichlor-4-nitroanilin, 2,6-Dibrom-4-nitroanilin, 2-Chlor-6-brom-4-nitroanilin, 2,6-Dicyan-4-nitroanilin, 2-Cyan-4-nitro-6-chloranilin, 2-Cyan-4-nitro-6-bromanilin, 1-Aminobenzol-4-methylsulfon, 1-Amino-2,6-dibrom-benzol-4-methylsulfon, 1-Amino-2,6-dichlorbenzol-4-methylsulfon, 1-Amino-2,4-dinitrobenzol-6-carbonsäure-methylester oder -ß-methoxyäthylester, 3,5-Dichloranthranilsäure-propylester, 3,5-Dibromanthranilsäure-ß-methoxyäthylester, N-Acetyl-p-phenylendiamin, 4-Amino-acetophenon, 4- oder 2-Amino-benzophenon, 2- und 4-Aminodiphenylsulfon, 2-, - oder 4-Aminobenzoesäure-methylester, -äthylester, -propylester, -butylester, -isobutylester, -ß-methoxy-äthylester, -ß-äthoxy-äthylester, -methyl-diglykolester? -äthyl-diglykolester, -methyl-triglykolester, -äthyltriglykolester, -ß-hydroxyäthylester, -ß-acetoxy-äthylester, -ß-(ß'-hydroxy-äthoxy)-äthylester, -ß-hydroxy-propylester, -γ -hydroxy-propylester, -#-hydroxy-butylester, -#-hydroxy-hexylester 5-Nitro-anthranilsäure-methylester, -isobutylester, -methyl-diglykolester, -ß-methoxy-äthylester, -ß-butoxy-äthylester-, -ß-acetoxy-äthylester, - oder 4-Aminophthalsäure-, 5-Aminoisophthalsäure- oder Amino-terephthalsäure-di-methylester, -diäthyletser, ö'.i-propylestcr, -di-butylester. 3- oder 4-Aminobenzoesäure-amid, -methylamid, -propylamid, -butylamid, -isobutylamid, -cyclohexylamid, -ß-äthyl-hexylamid, -γ-methoxypropylamid, -γ-äthoxy-propylamid, 2-, 3- oder 4-Aminobenzoesäuredimethylamid, -diäthylamid, -pyrrolidid, -morpholid, N-methyl-N-ß-hydroxy-äthylamid, 5-Amino-isophthalsäurediamid, -bis-γ-methoxy -propylamid, Aminoterephthalsäure-bis-diäthylamid, 3-oder 4-Amino-phthalsäure-imid, -ß-hydroxy-äthylimid-, hydroxy-propylamid, 3-Amino-6-nitro-phthalsäure-ß-hydroxyäthylimid, 2-, 3- oder 4-Aminobenzosulfonsäure-dimethylamid, -diäthylamid, -pyrrolidid, -morpholid, Methylsulfonsäure-2'-, -3'- oder -4'-amino-phenylester, Äthylsulfonsäure-2'-, -3'-oder -4'-amino-phenylester, Butylsulfonsäure-2'-, -3'- oder -4'-aminophenylester, Benzolsulfonsäure-2'-, -3'-. oder 4' aminophenylester, 4-Amino-naphthalsäure-äthylimid, -butylimid, -ß-methoxy-äthylimid, -T-methoxy-propylimid, 4- und 5-Nitro-1-amino-naphthalin, 2-Amino-anthrachinon, 1-Amino-4-chloranthrachinon, 3- oder 4-Aminodiphenylenoxid, 2-Amino-benzthiazol, 2-Amino-6-carbonsäure-methylester-benzthiazol, 2-Amino-6-methylsulfonyl-benzthiazol, 2-Amino-6-cyanbenzthiazol, 2-Amino-6-nitro-benzthiazol, 5,6- oder 6,7-Dichlor-2-amino-benzthiazol, 4-Amino-5-brom-7-nitro-1,2-benzisothiazol, 3-Amino-5-nitro-2,1-benzisothiazol, 3-Amino-5-nitro-7-brom-2, 1-benzisothiazol, 2-Amino-thiazol, 2-Mnino-5-nitro-thiazol, 2-Amino-4-methyl-thiazol-5-carbonsäure-äthylester, 2-Amino-4-methyl-5-acetyl-thiazol, 2-Amino-3-cyan-4-methyl-thiophen5-carbonsäureester, 2-Phenyl-5-amino-1 ,3,4-thiadiazol, 3-Methylmercapto-5-amino-1,2,4-thiadiazol, 3-ß-Carbomethoxy-äthylmercapto-5-amino-1,2,4-thiadiazol.The remainder D is derived, for example, from the following amines: Aniline o-, m- or p-toluldine, o-, m- or p-nitroaniline, o-, m- or p-cyananiline, 2,4-dicyaniline, o-, m- or p-chloroaniline, o-, m- or p-bromoaniline, 2,4,6-tribromaniline, 2-chloro-4-nitroaniline, 2-bromo-4-nitroaniline, 2-cyano-4-nitroaniline, 2-methyls-sulfonyl-4-nitroaniline, 2-methyl-4-nitroaniline, 2-methoxy-4-nitroaniline, 4-chloro-2-nitroaniline, 4-methyl-2-nitroaniline, 4-methoxy-2-nitroanillns 1-amino-2-trifluoromethyl-4-chlorobenzene, 2-chloro-5-aminobenzonitrile, 2-amino-5-chlorobenzonitrile, 1-amino-2-nitrobenzene-4-sulfonic acid-n-butylamide or -ß-methoxyethylamide, 2,4-dinitroaniline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-bromaniline, 2,4-dinitro-6-cyananiline, i-amino-2,4-dinitrobenzene-6-methylsulfone, 2,6-dichloro-4-nitroaniline, 2,6-dibromo-4-nitroaniline, 2-chloro-6-bromo-4-nitroaniline, 2,6-dicyano-4-nitroaniline, 2-cyano-4-nitro-6-chloroaniline, 2-cyano-4-nitro-6-bromaniline, 1-aminobenzene-4-methylsulfone, 1-amino-2,6-dibromobenzene-4-methylsulfone, 1-amino-2,6-dichlorobenzene-4-methylsulfone, 1-Amino-2,4-dinitrobenzene-6-carboxylic acid methyl ester or β-methoxyethyl ester, 3,5-dichloroanthranilic acid propyl ester, 3,5-dibromanthranilic acid-ß-methoxyethyl ester, N-acetyl-p-phenylenediamine, 4-amino-acetophenone, 4- or 2-amino-benzophenone, 2- and 4-aminodiphenylsulfone, 2-, - or 4-aminobenzoic acid methyl ester, -äthylester, -propylester, -butylester, -isobutylester, -ß-methoxy-ethyl ester, -ß-ethoxy-ethyl ester, -methyl diglycol ester? ethyl diglycol ester, methyl triglycol ester, ethyl triglycol ester, -ß-hydroxyethyl ester, -ß-acetoxy-ethyl ester, -ß- (ß'-hydroxy-ethoxy) -ethyl ester, -ß-hydroxy-propyl ester, -γ-hydroxy-propyl ester, - # - hydroxy-butyl ester, - # - hydroxy-hexyl ester 5-Nitro-anthranilic acid methyl ester, isobutyl ester, methyl diglycol ester, -ß-methoxy-ethyl ester, -ß-butoxy-ethyl ester, -ß-acetoxy-ethyl ester, - or 4-aminophthalic acid, 5-aminoisophthalic acid- or amino-terephthalic acid dimethyl ester, diethyl ester, ö'.i-propyl ester, di-butyl ester. 3- or 4-aminobenzoic acid amide, methyl amide, propyl amide, butyl amide, isobutyl amide, -cyclohexylamide, -ß-ethyl-hexylamide, -γ-methoxypropylamide, -γ-ethoxy-propylamide, 2-, 3- or 4-aminobenzoic acid dimethylamide, diethylamide, pyrrolidide, morpholide, N-methyl-N-ß-hydroxy-ethylamide, 5-amino-isophthalic acid diamide, -bis-γ-methoxy -propylamide, Aminoterephthalic acid-bis-diethylamide, 3- or 4-amino-phthalic acid-imide, -ß-hydroxy-ethylimide-, hydroxy-propylamide, 3-amino-6-nitro-phthalic acid-ß-hydroxyethylimide, 2-, 3- or 4-aminobenzenesulphonic acid dimethylamide, diethylamide, pyrrolidide, morpholide, methylsulphonic acid 2'-, -3'- or -4'-aminophenyl ester, ethylsulfonic acid 2'-, -3'- or -4'-aminophenyl ester, Butylsulfonic acid 2'-, -3'- or -4'-aminophenyl ester, benzenesulfonic acid 2'-, -3'-. or 4 'aminophenyl ester, 4-amino-naphthalic acid-ethylimide, -butylimide, -ß-methoxy-ethylimide, -T-methoxy-propylimide, 4- and 5-nitro-1-amino-naphthalene, 2-amino-anthraquinone, 1-amino-4-chloroanthraquinone, 3- or 4-aminodiphenylene oxide, 2-amino-benzothiazole, 2-Amino-6-carboxylic acid methyl ester-benzthiazole, 2-Amino-6-methylsulfonyl-benzthiazole, 2-amino-6-cyanobenzothiazole, 2-amino-6-nitro-benzothiazole, 5,6- or 6,7-dichloro-2-aminobenzothiazole, 4-amino-5-bromo-7-nitro-1,2-benzisothiazole, 3-amino-5-nitro-2,1-benzisothiazole, 3-amino-5-nitro-7-bromo-2, 1-benzisothiazole, 2-amino-thiazole, 2-Mnino-5-nitro-thiazole, 2-amino-4-methyl-thiazole-5-carboxylic acid ethyl ester, 2-amino-4-methyl-5-acetyl-thiazole, 2-amino-3-cyano-4-methyl-thiophene-5-carboxylic acid ester, 2-phenyl-5-amino-1, 3,4-thiadiazole, 3-methylmercapto-5-amino-1,2,4-thiadiazole, 3-ß-carbomethoxy-ethylmercapto-5-amino-1,2,4- thiadiazole.

Geeignete Diazokomponenten der Aminoazobenzolreihe sind beispielsweise: 4-Aminoazobenzol, 2',3-Dimethyl-4-aminoazobenzol, 3' ,2-Dimethyl-4-aminoazobenzol, 2,5-Dimethyl-4-aminoazobenzol, 2-Methyl-5-methoxy-4-aminoazobenzol, 2-Methyl-4' ,5-dimethoxy-4-aminoazobenzol, 4'-Chlor-2-methyl-5-methoxy-4-aminoazobenzol, 4' -Nitro-2-methyl-5-methoxy-4-aminoazobenzol, 4'-Chlor-2-methyl-4-aminoazobenzol, 2,5-Dimethoxy-4-aminoazobenzol, 4'-Chlor-2,5-dimethoxy-4-aminoazobenzol, 4'-Nitro-2,5-dimethoxy-4-aminoazobenzol, 4'-Chlor-2,5-dimethyl-4-aminoazobenzol, 4'-Methoxy-2,5-dimethyl-4-aminoazobenzol, 4'-Nitro-4-aminoazobenzol, 3,5-Dibrom-4-aminoazobenzol, 2,3'-Dichlor-4-aminoazobenzol, 3-Methoxy-4-. Suitable diazo components of the aminoazobenzene series are, for example: 4-aminoazobenzene, 2 ', 3-dimethyl-4-aminoazobenzene, 3', 2-dimethyl-4-aminoazobenzene, 2,5-dimethyl-4-aminoazobenzene, 2-methyl-5-methoxy-4-aminoazobenzene, 2-methyl-4 ' , 5-dimethoxy-4-aminoazobenzene, 4'-chloro-2-methyl-5-methoxy-4-aminoazobenzene, 4 ' -Nitro-2-methyl-5-methoxy-4-aminoazobenzene, 4'-chloro-2-methyl-4-aminoazobenzene, 2,5-dimethoxy-4-aminoazobenzene, 4'-chloro-2,5-dimethoxy-4-aminoazobenzene, 4'-nitro-2,5-dimethoxy-4-aminoazobenzene, 4'-chloro-2,5-dimethyl-4-aminoazobenzene, 4'-methoxy-2,5-dimethyl-4-aminoazobenzene, 4'-nitro-4-aminoazobenzene, 3,5-dibromo-4-aminoazobenzene, 2,3'-dichloro-4-aminoazobenzene, 3-methoxy-4-.

aminoazobenzol. aminoazobenzene.

Als Reste R sind neben Phenyl und Wasserstoff z.B. zu nennen: die Alkylreste Methyl, Äthyl, Propyl oder Butyl, die Hydroxyalkylreste ß-Hydroxyäthyl oder -propyl, γ-Hydroxypropyl, #-Hydroxyhexyl, sowie die Reste der Formeln -CH2-CH2-O-CH2-CH2-OH und -(CH2)3-0-(CH2)4-OH, die Alkoxyalkylreste ß-Methoxyäthyl, t-Methoxypropyl, ß-Athoxyathyl, γ-Äthoxypropyl oder der Rest der Formel (CH2)30C2H40CH3, die Acyloxyalkylreste der Formeln CH2-CH2-O-Acyl, (CH2)3-O-Acyl, CH2-CIH-O-Acyl, (CH2 ) 6-O-Acyl, CH3 (CH2)2-O-(CH2)2-O-Acyl oder (CH2)3-O-( CH2)4-O-Acyl, wobei Acyl beispielsweise CO-H, CO-CH3, CO-CH2Cl, CO-CH2-CO-CH3, CO-CH=CH2 sein kann. In addition to phenyl and hydrogen, the following radicals R include: the Alkyl radicals are methyl, ethyl, propyl or butyl, the hydroxyalkyl radicals ß-hydroxyethyl or -propyl, γ-hydroxypropyl, # -hydroxyhexyl, and the radicals of the formulas -CH2-CH2-O-CH2-CH2-OH and - (CH2) 3-0- (CH2) 4-OH, the alkoxyalkyl radicals ß-methoxyethyl, t-methoxypropyl, ß-ethoxyethyl, γ-ethoxypropyl or the remainder of the formula (CH2) 30C2H40CH3, the acyloxyalkyl radicals of the formulas CH2-CH2-O-acyl, (CH2) 3-O-acyl, CH2-CIH-O-acyl, (CH2) 6-O-acyl, CH3 (CH2) 2-O- (CH2) 2-O-acyl or (CH2) 3-O- (CH2) 4-O-acyl, where Acyl can be, for example, CO-H, CO-CH3, CO-CH2Cl, CO-CH2-CO-CH3, CO-CH = CH2.

Zur Herstellung der Farbstoffe der Formel I kann man eine Diazoverbindung von Aminen der Formel II D-NH2 II, mit Kupplungskomponenten der Formel III umsetzen, wobei D, X und R die angegebene Bedeutung haben.To prepare the dyes of the formula I, a diazo compound of amines of the formula II D-NH2 II, with coupling components of the formula III implement, where D, X and R have the meaning given.

Die Diazotierung der Amine erfolgt wie üblich. Die Kupplung wird ebenfalls wie üblich in wäßrigem Medium, gegebenenfalls unter Zusatz von Lösungsmitteln, bei schwach bis stark saurer Reaktion durchgeführt.The amines are diazotized as usual. The clutch will also as usual in an aqueous medium, optionally with the addition of solvents weak to strongly acidic reaction carried out.

Die Herstellung der Kupplungskomponenten der Formel III ist im Prinzip in dem Patent . ... ... (Patentanmeldung P 20 62 717.2) beschrieben, die Angaben dort gelten hier sinngemäß.The preparation of the coupling components of formula III is in principle in the patent. ... ... (patent application P 20 62 717.2) describes the information apply here accordingly.

Enthalten die erfindungsgemäßen Farbstoffe der Formel I eine Estergruppe in dem Rest R, so kann die Herstellung der Verbindungen der Formel I im Prinzip nach dem angegebenen Verfahren erfolgen, wenn die entsprechende Estergruppe schon in der Kupplungskomponente enthalten ist. In manchen Fällen ist es aber auch zweckmäßig, den Säurerest (Acyl) in den fertigen Farbstoff der Formel I einzuführen. Dazu eignen sich die freien Säuren, ihre Anhydride, Chloride oder Ester, wobei zweckmäßigerweise inerte Verdünnungs- oder Lösungsmittel, wie Mono-, Di-oder Trichlorbenzol, Tetrahydrofuran, Dioxan, Dimethylformamid, N-Methylpyrrolidon oder Pyridin zugesetzt werden.If the dyes of the formula I according to the invention contain an ester group in the radical R, the preparation of the compounds of the formula I can in principle take place according to the specified procedure, if the corresponding ester group already is contained in the coupling component. In some cases, however, it is also useful to introduce the acid residue (acyl) into the finished dye of the formula I. Suitable for this the free acids, their anhydrides, chlorides or esters, with expedient inert diluents or solvents, such as mono-, di- or Trichlorobenzene, Tetrahydrofuran, dioxane, dimethylformamide, N-methylpyrrolidone or pyridine were added will.

Bei der Veresterung mit freien Säuren kann es von Vorteil sein, anorganische oder organische Katalysatoren, z.B. HCl-Gas oder p-Toluolsulfonsäure, zuzusetzen und das entstehende Wasser aus dem Reaktionsgemisch durch Verdampfen entweichen zu lassen. Werden Säureanhydride oder -chloride zur Veresterung eingesetzt, so können als Lösungsmittel in -speziellen Pällen auch die betreffenden Säuren verwendet werden. So läßt sich die Umsetzung mit Acetanhydrid in Eisessig durchführen. Bei der Verwendung von Säurechloriden als Veresterungsmittel ist es von Vorteil, dem Reaktionsgemisch säurebindende Mittel hinzuzusetzen, z.B.In the case of esterification with free acids, it can be advantageous to use inorganic acids or adding organic catalysts, e.g. HCl gas or p-toluenesulfonic acid and the resulting water escape from the reaction mixture by evaporation allow. If acid anhydrides or chlorides are used for esterification, so can The acids in question can also be used as solvents in special cases. For example, the reaction with acetic anhydride can be carried out in glacial acetic acid. When using of acid chlorides as esterifying agents, it is advantageous to add to the reaction mixture to add acid-binding agents, e.g.

Natriumcarbonat oder -acetat, Magnesiumoxid oder Pyridin. Als Veresterungsmittel seien im einzelnen beispielsweise genannt: Ameisensäure, Essigsäure, Chloressigsäure, sowie die Ester, Anhydride oder Chloride dieser Säuren, weiterhin Chlorameisensäureäthylester oder Diketen.Sodium carbonate or acetate, magnesium oxide or pyridine. As an esterifying agent may be mentioned in detail, for example: formic acid, acetic acid, chloroacetic acid, and the esters, anhydrides or chlorides of these acids, and also ethyl chloroformate or diketen.

Technisch besonders wertvoll sind Farbstoffe und Parbstoffgemische der Formel I a in der Y Nitro, Cyan, Chlor, Brom, Carbomethoxy, Carboäthoxy, Methylsulfonyl, Äthylsulfonyl, Methyl, Methoxy, Phenylazo, Y¹ Wasserstoff, Nitro, Chlor, Brom, Cyan, Methyl, Methoxy, Carbomethoxy, Carboäthoxy, Methylsulfonyl oder Äthylsulfonyl und y2 Wasserstoff, Chlor, Brom, Cyan, Methyl, Methoxy, Carbomethoxy oder Carboäthoxy, ein R¹ Phenyl und das andere 0-Hydroxyhexyl, ß-Hydroxyäthyl, ß-Hydroxypropyl, γ-Hydroxypropyl oder einen Rest der Formeln -(CH2)2-O-(CH2)2OH, (CH2)3O(CH2)4OH, C2H40CH3, C2H4OC2H5, C3H6OCH3, C3H6OC2H5, CH2CH2OCHO, CH2CH2CH2OCHO, CH2-CH2OCOCH3 oder CH2Cf12OCH2CH2OCHO bedeuten.Dyes and mixtures of paraffins of the formula I a are of particular technical value in Y nitro, cyano, chlorine, bromine, carbomethoxy, carboethoxy, methylsulfonyl, ethylsulfonyl, methyl, methoxy, phenylazo, Y¹ hydrogen, nitro, chlorine, bromine, cyano, methyl, methoxy, carbomethoxy, carboethoxy, methylsulfonyl or ethylsulfonyl and y2 hydrogen , Chlorine, bromine, cyano, methyl, methoxy, carbomethoxy or carboethoxy, one R¹ is phenyl and the other is 0-hydroxyhexyl, ß-hydroxyethyl, ß-hydroxypropyl, γ-hydroxypropyl or a residue of the formulas - (CH2) 2-O- ( CH2) 2OH, (CH2) 3O (CH2) 4OH, C2H40CH3, C2H4OC2H5, C3H6OCH3, C3H6OC2H5, CH2CH2OCHO, CH2CH2CH2OCHO, CH2-CH2OCOCH3 or CH2Cf12OCH2CH2OCHO.

Bei Farbstoffen mit Estergruppen sind solche mit ungefähr 1 bis 4 C-Atomen im Acylrest bevorzugt.For dyes with ester groups are those with about 1 to 4 C atoms in the acyl radical are preferred.

Weiterhin sind besonders wertvoll die entsprechenden Farbstoffe, die als Diazokomponenten gegebenenfalls durch Nitro, Chlor, Brom, Cyan, Methyl, Methylmercapto, ß-Carbomethoxy-äthylmercapto, Ed-Carboäthoxy-äth-lmercapto, Carbomethoxy, Carboäthoxy oder Acetyl substituiertes Benzthiazol, Penzisothiazol, Thiazol, Thiadiazol oder Thiophen enthalten.Furthermore, the corresponding dyes are particularly valuable as diazo components, if necessary by nitro, chlorine, bromine, cyano, methyl, methyl mercapto, β-carbomethoxy-ethyl mercapto, Ed-carboethoxy-ether-lmercapto, carbomethoxy, carboethoxy or acetyl-substituted benzothiazole, penzisothiazole, thiazole, thiadiazole or Contains thiophene.

Von den besonders wertvollen Diazokomponenten seien im einzelnen genannt: 4-Nitro-anilin, 2-Chlor-4-nitro-anilin, 2-Brom-4-nitroanilin, 2-Cyan-4-nitro-anilin, 2-Methoxy-4-nitro-anilin, 2-Amino-5-nitro-phenylsulfonsäuredimethylamid, 2-Amino-5-nitro-phenylsulfonsäure-butylamid, 2-Amino-5-nitro-phenylsulfonsäure-ßmethoxy-äthylamid, 2-Amino-benzonitril, 3-Chlor-4-amino-benzonitril, 2-Chlor-5-amino-benzonitril, 2-Amino-5-chlor-benzonitril, 2,5-Dichlor-4-amino-benzonitril, 1-Amino-2,4-dicyanbenzol, 1-Amino-2,4-dicyan-6-chlor-benzol, 2-chlor-4-amino-5-nitrobenzonitril, 2-Amino-3-chlor-5-nitro-benzonitril, 2-Amino-3-brom-5-nitro-benzonitril, 2,6-Dicyan-4-nitro-anilin, 2,5-Dichlor-4-nitroanilin, 2, 6-Dichlor-4-nitro-anilin, 2,6-Dibrom-4-nitroanilin, 2-Chlor-6-brom-4-nitro-anilin, 2,4-Dinitro-anilin, 2,4-Dinitro-6-chlor-anilin, 2,4-Dinitro-6-brom-anilin, 2-Amino-3,5-dinitro-benzonitril, 1-Amino-4-nitrobenzol-2-methylsulfon, 1-Amino-4-nitrobenzol-2-äthylsulfon, 4-Methylsulfonyl-anilin, 1-Amino-2-chlortenzol-4-methylsulfon, 1-Amino-2,6-dibrombenzol-4-methylsulfon, 1-Amino-2,6-dichlorbenzol-4-methylsulfon, 2-und 4-Amino-benzoesäureester, 2-Amino-5-nitro-benzoesäureester, 2-Amino-3-chlor-5-nitro-benzoesäureester, 2-Amino-3,5-dichlorbenzoesäureester, 2-Amino-3,5-dibrom-benzoesäureester, 2-Amino-3,5-dinitro-benzoesäure-methylester oder -ß-methoxy-äthylester, 2-Amino-terephthalsäure-diäthylester, 4-Amino-azobenzol, 2,3'-Dimethyl-4-amino-azobenzol, 2',3-Dimethyl-4-amino-azobenzol, 2,5-Dimethyl-4-amino-azobenzol, 3,5-Dibrom-4-amino-azobenzol, 2-Methyl-5-methoxy-4-amino-azobenzol.Some of the particularly valuable diazo components are: 4-nitro-aniline, 2-chloro-4-nitro-aniline, 2-bromo-4-nitroaniline, 2-cyano-4-nitro-aniline, 2-methoxy-4-nitro-aniline, 2-amino-5-nitro-phenylsulfonic acid dimethylamide, 2-amino-5-nitro-phenylsulfonic acid-butylamide, 2-amino-5-nitro-phenylsulfonic acid-ßmethoxy-ethylamide, 2-amino-benzonitrile, 3-chloro-4-amino-benzonitrile, 2-chloro-5-amino-benzonitrile, 2-amino-5-chloro-benzonitrile, 2,5-dichloro-4-amino-benzonitrile, 1-amino-2,4-dicyanobenzene, 1-amino-2,4-dicyan-6-chlorobenzene, 2-chloro-4-amino-5-nitrobenzonitrile, 2-Amino-3-chloro-5-nitro-benzonitrile, 2-amino-3-bromo-5-nitro-benzonitrile, 2,6-dicyano-4-nitro-aniline, 2,5-dichloro-4-nitroaniline, 2,6-dichloro-4-nitro-aniline, 2,6-dibromo-4-nitroaniline, 2-chloro-6-bromo-4-nitro-aniline, 2,4-dinitro-aniline, 2,4-dinitro-6-chloro-aniline, 2,4-dinitro-6-bromo-aniline, 2-amino-3,5-dinitro-benzonitrile, 1-amino-4-nitrobenzene-2-methylsulphone, 1-amino-4-nitrobenzene-2-ethylsulphone, 4-methylsulfonyl-aniline, 1-amino-2-chlorotenzene-4-methylsulfone, 1-amino-2,6-dibromobenzene-4-methylsulfone, 1-amino-2,6-dichlorobenzene-4-methylsulfone, 2- and 4-amino-benzoic acid ester, 2-amino-5-nitro-benzoic acid ester, 2-amino-3-chloro-5-nitro-benzoic acid ester, 2-amino-3,5-dichlorobenzoic acid ester, 2-amino-3,5-dibromo-benzoic acid ester, 2-Amino-3,5-dinitro-benzoic acid methyl ester or -ß-methoxy-ethyl ester, 2-amino-terephthalic acid diethyl ester, 4-amino-azobenzene, 2,3'-dimethyl-4-amino-azobenzene, 2 ', 3-dimethyl-4-amino-azobenzene, 2,5-dimethyl-4-amino-azobenzene, 3,5-dibromo-4-amino-azobenzene, 2-methyl-5-methoxy-4-amino-azobenzene.

Von den besonders wertvollen heterocyclischen Diazokomponenten seien erwähnt: 2-Amino-5-nitro-thiazol, 2-Amino-4-methyl-5-nitro-thiazol, 2-Amino-4-methyl-thiazol-5-carbonsäureäthylester, 2-Amino-5-phenyl-1 ,3,4-thiadiazol, 3-Phenyl-5-amino-1 ,2,4-thiadiazol, 3-Methyl-mercapto-5-amino-1 , 2,4-thiadiazol, 3-ß-Carbomethoxy-Ethylmereapto-5-amino-1,2,4-thiadlaßol, 3-ß-Carboäthoxy-äthylmercapto-5-amino-1,2,4-thiadiazol, 2-Amino-6-cyan-benzthiazol, 2-Amino-6-carbonsäuremethyl-esterbenzthiazol, 2-Amino-6-nitro-benzthiazol, 2-Amino-3-cyan-4-methyl-thiophen-5-carbonester, 3-Amino-5-nitro-2, 1-benzisothiazol, 3-Amino-5-nitro-7-chlor-2,1-benzisothiazol, 3-Amino-5-Nitro-7-brom-2,1-benzisothiazol, 4-Amino-7-nitro-1,2-benzisothiazol, 4-Amino-5-brom-1,2-benzisothiazol, 4-Amino-5-brom-7-nitro-1,2-benzisothiazol, 4-Amino-5-cyan-7-nitro-1,2-benzisothiazol, 4-Amino-5-chlor-7-nitro-1,2-benzisothiazol.Of the particularly valuable heterocyclic diazo components are mentioned: 2-amino-5-nitro-thiazole, 2-amino-4-methyl-5-nitro-thiazole, 2-amino-4-methyl-thiazole-5-carboxylic acid ethyl ester, 2-amino-5-phenyl-1, 3,4-thiadiazole, 3-phenyl-5-amino-1, 2,4-thiadiazole, 3-methyl-mercapto-5-amino-1 , 2,4-thiadiazole, 3-ß-carbomethoxy-ethylmereapto-5-amino-1,2,4-thiadlaßol, 3-ß-carboethoxy-ethylmercapto-5-amino-1,2,4-thiadiazole, 2-Amino-6-cyano-benzothiazole, 2-amino-6-carboxylic acid methyl ester-benzothiazole, 2-amino-6-nitro-benzothiazole, 2-amino-3-cyano-4-methyl-thiophene-5-carbon ester, 3-amino-5-nitro-2, 1-benzisothiazole, 3-amino-5-nitro-7-chloro-2,1-benzisothiazole, 3-amino-5-nitro-7-bromo-2,1-benzisothiazole, 4-amino-7-nitro-1,2-benzisothiazole, 4-amino-5-bromo-1,2-benzisothiazole, 4-amino-5-bromo-7-nitro-1,2-benzisothiazole, 4-amino-5-cyano-7-nitro-1,2-benzisothiazole, 4-amino-5-chloro-7-nitro-1,2-benzisothiazole.

Die neuen Farbstoffe sind gelb bis blau und eignen sich zum Färben von Textilmaterialien aus Acrylnitrilpolymerisaten, synthetischen Polyamiden, Celluloseestern, wie 2 1/2- oder Triacetat, und insbesondere von synthetischen linearen Polyestern, wie Polyäthylenglykolterephthalat oder chemisch analog aufgebauten Polymeren. Man erhält farbstarke Färbungen, die sich durch hervorragende Echtheiten auszeichnen.The new dyes are yellow to blue and are suitable for dyeing of textile materials made of acrylonitrile polymers, synthetic polyamides, cellulose esters, like 2 1/2 or triacetate, and especially of synthetic linear polyesters, such as polyethylene glycol terephthalate or chemically analogous polymers. Man receives strong dyeings which are distinguished by excellent fastness properties.

Die Angaben über Teile und Prozente beziehen sich in den folgenden Beispielen auf das Gewicht, wenn es nicht anders vermerkt ist.The data on parts and percentages relate to the following Examples on weight, unless otherwise noted.

Beispiel 1 Ein Gemisch aus 187 Teilen 2,6-Dichlor-3-cyan-4-methyl-pyridin, 200 Teilen Isopropanol und 300 Teilen Anilin wird 8 Stunden bei ungefähr 90 bis 1000C gerührt. Dann läßt man erkalten und gießt das Gemisch unter Rühren in etwa 1 500 Teile Wasser, 200 Teile konzentrierte Salzsäure und 200 Deile Sis. Man rührt noch 1 Stunde, saugt den ausgefallenen Niederschlag der wahrscheinlichen Formel ab und wäscht ihn mit Wasser neutral. Nach dem Trocknen erhält man ungefähr 240 Teile eines farblosen Pulvers, das bei 135 bis 1400C schmilzt.Example 1 A mixture of 187 parts of 2,6-dichloro-3-cyano-4-methyl-pyridine, 200 parts of isopropanol and 300 parts of aniline is stirred for 8 hours at about 90 to 1000.degree. It is then allowed to cool and the mixture is poured, with stirring, into about 1,500 parts of water, 200 parts of concentrated hydrochloric acid and 200 parts of sis. The mixture is stirred for a further 1 hour, and the precipitate of the probable formula which has separated out is sucked off and washes it neutral with water. After drying, about 240 parts of a colorless powder which melts at 135 to 1400C are obtained.

12,2 Teile dieses Pulvers werden mit 40 Teilen t-Hydroxy-propylamin 6 Stunden bei 145 bis 1600C gerührt. Dann läßt man erkalten, versetzt das Gemisch mit 100 Teilen Wasser und säuert mit Salz-.12.2 parts of this powder are mixed with 40 parts of t-hydroxypropylamine Stirred for 6 hours at 145 to 1600C. Then allowed to cool, the mixture is added with 100 parts of water and acidify with salt.

säure auf einen pH-Wert von etwa 0 bis 1 an. Man erhält - gegebenenfalls unter Zusatz von etwas Eisessig oder Dimethylformamid - eine Lösung der Kupplungskomponente der wahrscheinlichen Formel Die Lösung (oder Suspension) dieser Kupplungskomponente wird durch Zugabe von Eis auf 0 bis 30C abgekühlt, und mit einer Diazoniumsalzlösung versetzt, die man wie folgt erhält: 6,9 Teile p-Nitroanilin werden mit ungefähr 30 Teilen konzentrierter Salzsäure (30 %ig) und 80 Teilen Wasser versetzt, dann wird das Gemisch auf OOC abgekühlt und in Anteilen mit 15 Raumteilen 23 %iger Natriumnitritlösung versetzt. Man rührt 2 Stunden nach, beseitigt einen gegebenenfalls vorhandenen Überschuß an salpetriger Säure wie üblich und filtriert.acid to a pH of about 0 to 1. A solution of the coupling component of the probable formula is obtained - optionally with the addition of a little glacial acetic acid or dimethylformamide The solution (or suspension) of this coupling component is cooled to 0 to 30C by adding ice, and a diazonium salt solution is added, which is obtained as follows: 6.9 parts of p-nitroaniline are mixed with about 30 parts of concentrated hydrochloric acid (30%) and 80 parts of water are added, then the mixture is cooled to OOC and 15 parts by volume of 23% sodium nitrite solution are added. The mixture is stirred for a further 2 hours, any excess nitrous acid present is eliminated as usual and filtered.

Das Filtrat wird zum Kupplungsgemisch gegeben und man fügt dann unter Rühren nach und nach so viel Natriumacetat oder Natronlauge zu, daß der pH-Wert des Kupplungsgemisches etwa 2 bis 3 beträgt, Falls das Gemisch schwer rührbar wird, kann Eiswasser zugesetzt werden. Nach beendeter Kupplung wird das Gemisch auf 70 bis 80°C erhitzt, filtriert, mit Wasser gewaschen und getrocknet, Man erhält ungefähr 20 Teile eines rotbraunen Pulvers der wahrscheinlichen Formel das sich in Dimethylformamid mit roter Parbe löst und Polyäthylenterephthalgewebe in kräftigen, klaren scharlachroten Tönen mit hervorragenden Echtheiten färbt.The filtrate is added to the coupling mixture and sodium acetate or sodium hydroxide solution is then gradually added with stirring so that the pH of the coupling mixture is about 2 to 3. If the mixture is difficult to stir, ice water can be added. After the coupling has ended, the mixture is heated to 70 to 80 ° C., filtered, washed with water and dried. About 20 parts of a red-brown powder of the probable formula are obtained which dissolves in dimethylformamide with red color and dyes polyethylene terephthalic fabric in strong, clear scarlet shades with excellent fastness properties.

Analog der beschriebenen Verfahrensweise können die folgenden durch Diazo- und Kupplungskomponente charakterisierten Parbstoffe erhalten werden.Analogously to the procedure described, the following can be carried out Diazo and coupling component characterized paraffin can be obtained.

Tabelle 1 Kupplungskomponente: Beispiel I)iaeokomponente I H2 E'arbton Nr. 2 FOOCH, -CH3-CII,-!fI,-O-CIf, rotstichig gelb 2 COOCE3 -CH2-CB2-E2 ° 3 rotstichig gelb 3 cfl2-CH -OH goldgelb 4 -CH2-0112-C112-OH 1 ; rotstichig gelb 5 | CH2 çH ° ! rotstichig gelb 3 6 -CH2-CH2-0-CH2-CE2-OE rotat rotstichig gelb 7 -CH2-CE2-0-CH3 ; 3-CH gelb CN FN H rotstichig gelb 10NH2 -CH,-CH,-OH rotstichig gelb 9 10 | CH2 CH2 CH2 -OH rotstichig gelb 2 2 2 11 11 j bB3 | C: -CH-OH rotstichig gelb CH 3 12 -0H2-0H2-O-0H2-CH2-OH rotstichig gelb . . 13 i Fn -H rotstichig gelb 14rc -CH,-CH,-OH ' goldgelb H2 c L 16 i -CH,-CH,-OH goldgelb gelb L 17 -CH2-CH2-0-CH2-CH2-OH goldgelb L 2 18 N -CH,-CH,-OB goldgelb 19 B 4 NH2 -CH2-CH2-OH goldgelb 20 CH2 CH2 CH2 -OH goldgelb 21 -CH2-CH-OH goldgelb 22 CH3 -CH2-CH2-0-CH2-CH2-0H goldgelb Beispiel | Diazokomponente R2 Farbton Z3 1 9 E rotorange 24 \3 -CH,-CH,-OH scarlach 25 A r r2 CH2 CH2 OH scharlach 26 -CH2-CH-OH scharlach 21 CH3 27 -CH2-CH2-0-CH2-CH20H braunstichig scharlach OOOOH H rotorange 29 zu -CH2-CH2-OH scharlach 30 cl-l-CHp CH,-CH2-BH scharlach 31 Cl -GH2-CH2-0-CE2-CH2-OH scharlach 1 QII,-O-CH -CH,-OH scharlch cr 2r 33 02N o WH2 -CH2-CE2-OH æcharlaeh 34 -CH2-CH2"CH2-OCOCE) scharlach OH 35 CH2 C OH2O scharlach OH 3 36 -CH2-CH2-0-CH2-CH2-OH scharlach 37 -CH2-CH2-0-CE3 scharlach 58 -CH2-CH2-CH2-0-CH3 soharlach 39 -CH2-CH20CHO rotorange-scharlach 40 -fca,), -OH scharlach 3 42 2 4 2 -CH2-CH2-OH gelbstichig rot 43 CH2 CH2 CE2 H gelbstichig rot 44 -CH2-CH2-0-CH2-CH2-OH feuerrot 45 oOH feuerrot -Cz2-CHs 46 -CH2-CH2-CH2-0-CH3 feuerrot 47 -CH2-CH2-CH2-OCOGH3 feuerrot Beispiel Diazokomponente B Farbton Nr. Diazokoniponente 2 Farbton 48 ,~{CH3 -CH2-CH2-OH scharlach 49 02N e NE2 0112-OH 50 -CH,-CH,-O-CH,-CH,-OH scharlach C c. 51 OCH, -CH,-CH,-OH rot 52 02N'KB; L L -CII2-CH, -CH,-OH rot L 53 -CH2-CH,-O-CH2-CH,-OH rot j -CH,-CH,-CH,i)H scharlach 56 NICff.'112 -0H2-0H2-OH rotstichig gelb 57 -CH -OH -OH -OH rotstichig gelb 58 -CH,-Crr -O-CH,-CH,-OH rotstichig gelb LL LL 59 clY -CII,-CH,-OH rotorange 60 NrC-d C-CH,-CH,-OH rotorsnge QHL! H2' L 61 -CH2-CH2-O-CH,-CH -OH rotorange 2 62 -CH,-CH,-OH orange 66 C1 t RH2 -NH,- -CH,-CH 67 j -C112-OH2-OH2 -OH orange 66 -CH -CH,-CH,-CH,-O-CH, orange 69 SCP3 -CH2-CH2-OH goldgelb 70 C1 9 E2 CH2 CH2 CH2 OH goldgelb 71 -CH2-CH2-0-CH2 CH2-0 goldgelb Belsplel Diazokomponente R2 Parbton 72 CE2-CH2-OH -H goldgelb 75 N -CH2-CH2-OH orange 74 O 9 O CH2 CH2 CE2 OH orange 75 9 2 -CH2-CH2-0-CH -CH2-OH orange -CE2-cH2-°-CH3 orsnge (7 -NNE2 -CH2-cH2-cH2-°H rot 78 -CH2-CH2-0-CH2-CH2-OH rot 19 COOCH3 CE2 CH2 CH2 OH scharlach SO <r -CH2-CH2-0-CH2-CH2-OH scharlach 81 H g -CH2-CH2-OH orange 82 CH3-ff- -OH2-CH2OH2-OH orange 83 0 -CH2-CH2-0-CH2-CH2-OH orange 84 ß ? -CE2-CH2-OE orange 85 C2H5-OC t H2 -CH2-CH2-CH2-OH orange 86 CE2 C orange L CH7: s7 -CH,-CH,-O-CH2-GE[,-OH orange ss CH,-CH2-O-CH, -CH,-CH,-OB goldgelb -osange H2 -CH2-CH2-CH2-OH goldgelb -orange 90 N < zuO -CH2-CH2-0-CH2-CH2-OH goldgelb -orange Oy% Beispiel Diazokomponente 2 Farbton Nr. 91 ° OH3 O0H2OH2N2 -CH2-CH2-OH orange -OH-OH-OH -OH orange c 9j C II,-S-C,?Le[H, -CH,-Ca,-OH orange H H2 2 C 2 oranBe Tabelle 2 Kupplungskomponente: Beispiel Diazokomponente R2 Farbton Nr. Diazokoniponente R2 Farbton 95 COOCH3 -CH2-CH2-OH rotstichig gelb -O -OH -OH -OH rotstichig gelb 97 -OH -0-OH -OH -OH rotstichig gelb L gs ,CN -CH,-CH,-OH goldgelb L 99 LNH3 -CH,-CH,-CH,-OH goldgelb \Z/ C L 100 -CH,-CH -CH,-O-CH2-CH2-OH, goldgelb c2r EIY ?Oi ci NH, -CH, -CHL!-OH goldgelb ;-Ckf,-CB,-OH gsldgelb -OH2-OH2 0OH2OH2-OH scharlach von CN -CH,-CH,-CH,-OH rauns ic 107 Br-li= CH2 CH2 CH2 E 3charlach 108 3r -CH,-CH -O-CH -OH -OH braunstichig . 5 2 2 2 2 2 scharlach br 109 J l CH2 CH2 CH2 OH rot 110 02N C112 -CH,-CH,-OH 9 H2 rot rot -OH -CH,-CH,-CH,-OH CH2 ob \ goldgelb 112 L -CH, -CH2 -O -CH,-CH, -OH goldgelb 113 CH2-CH2-OH -CH2-CH2-OH orange 114 O <9 O 2 2 2 orange 115 > 2 -CH2-CH2-CH2-0-CH3 orange Beispiel 116 24,4 Teile des Umsetzungsproduktes von Anilin mit 2,6-Dichlor-3-cyan-4-methylpyridin (siehe Beispiel 1) werden mit 80 Teilen t-Methoxypropylamin 8 Stunden unter Druck bei 140 bis 160°C gerührt, dann läßt man erkalten, setzt 8 Teile 50 Xige Natronlauge zu und destilliert überschüssiges t-Methoxy-propylamin und Wasser ab. Der Rückstand wird mit 10 Teilen 85 %iger Schwefelsäure 5 Stunden bei 100°C behandelt. Nach dem Erkalten gießt man das Gemisch in eine Mischung von etwa 500 Teilen Wasser, 600 Teilen Eis und 100 Teilen 50 %iger Natronlauge, Zu dem auf OOC abgekühlten Gemisch, das die Kupplungskomponente der wahrscheinlichen Formel enthält, gibt man dann in Anteilen eine Lösung von diazotiertem 3-Amino-5-nitro-2,1-benzisothiazol, die wie folgt hergestellt wird: 19,5 Teile 3-Amino-5-nitro-2,1-benzisothiazol werden unter Rühren bei 15 bis 25°C in Portionen zu ungefähr 75 bis 85 Teilen 96 %iger Schwefelsäure gegeben und auf 0 bis 400 abgekühlt. Dann tropft man bei dieser Temperatur 32,5 Teile 23 Xige Nitrosylschwefelsäure zu. Die Diazotierung ist nach etwa 4-stündigem Rühren bei 0 bis 50 beendet. Nach dem Versetzen des Kupplungsgemisches mit der Diazoniumlösung wird der pH-Wert des Gemisches durch Zugabe eines säurebindenden Mittels wie Natriumacetat (oder Natronlauge) auf ungefähr 1,5 bis 2,5 erhöht. Um eine gute Rührung bei 0 bis 5O zu erreichen, setzt man dabei zweckmäßigerweise Eis und Eiswasser zu. Nach beendeter Kupplung wird das Gemisch auf 60 bis 80°C erwärmt, der ausgefallene Farbstoff abgesaugt und mit heißem Wasser gewaschen. Nach dem Trocknen erhält man etwa 40 Teile eines schwarzen Farbstoffpulvers der wahrscheinlichen Formel das sich in Dimethylformamid mit blauer Farbe löst und Polyäthylenterephthalatgewebe in grünstichig blauen Tönen mit sehr guten Echtheiten färbt.Table 1 coupling component: Example I) iaeo component I H2 E 'color No. 2 FOOCH, -CH3-CII, -! FI, -O-CIf, reddish yellow 2 COOCE3 -CH2-CB2-E2 ° 3 reddish yellow 3 cfl2-CH -OH golden yellow 4 -CH2-0112-C112-OH 1; reddish yellow 5 | CH2 çH °! reddish yellow 3 6 -CH2-CH2-0-CH2-CE2-OE rotat reddish yellow 7 -CH2-CE2-0-CH3; 3-CH yellow CN FN H reddish yellow 10NH2 -CH, -CH, -OH reddish yellow 9 10 | CH2 CH2 CH2 -OH reddish yellow 2 2 2 11 11 j bB3 | C: -CH-OH reddish yellow CH 3 12 -0H2-0H2-O-0H2-CH2-OH reddish yellow . . 13 i Fn -H reddish yellow 14rc -CH, -CH, -OH 'golden yellow H2 c L 16 i -CH, -CH, -OH golden yellow L. 17 -CH2-CH2-0-CH2-CH2-OH golden yellow L 2 18 N -CH, -CH, -OB golden yellow 19 B 4 NH2 -CH2-CH2-OH golden yellow 20 CH2 CH2 CH2 -OH golden yellow 21 -CH2-CH-OH golden yellow 22 CH3 -CH2-CH2-0-CH2-CH2-0H golden yellow Example | Diazo component R2 shade Z3 1 9 E red-orange 24 \ 3 -CH, -CH, -OH scarlatina 25 A r r2 CH2 CH2 OH scarlet 26 -CH2-CH-OH scarlet 21 CH3 27 -CH2-CH2-0-CH2-CH20H brownish tinge Scarlet fever OOOOH H red orange 29 to -CH2-CH2-OH scarlet 30 cl-l-CHp CH, -CH2-BH scarlet 31 Cl -GH2-CH2-0-CE2-CH2-OH scarlet 1 QII, -O-CH -CH, -OH scarlet cr 2r 33 02N o WH2 -CH2-CE2-OH æcharlaeh 34 -CH2-CH2 "CH2-OCOCE) scarlet OH 35 CH2 C OH2O scarlet OH 3 36 -CH2-CH2-0-CH2-CH2-OH scarlet 37 -CH2-CH2-0-CE3 scarlet 58 -CH2-CH2-CH2-0-CH3 soharlach 39 -CH2-CH20CHO red-orange-scarlet 40 -fca,), -OH scarlet 3 42 2 4 2 -CH2-CH2-OH yellowish red 43 CH2 CH2 CE2 H yellowish red 44 -CH2-CH2-0-CH2-CH2-OH fire red 45 oOH fire red -Cz2-CHs 46 -CH2-CH2-CH2-0-CH3 flame red 47 -CH2-CH2-CH2-OCOGH3 fiery red Example diazo component B shade No. Diazokoniponente 2 shade 48, ~ {CH3 -CH2-CH2-OH scarlet 49 02N e NE2 0112-OH 50 -CH, -CH, -O-CH, -CH, -OH scarlet C c. 51 OCH, -CH, -CH, -OH red 52 02N'KB; LL -CII2-CH, -CH, -OH red L. 53 -CH2-CH, -O-CH2-CH, -OH red j -CH, -CH, -CH, i) H scarlet 56 NICff. '112 -0H2-0H2-OH reddish yellow 57 -CH -OH -OH -OH reddish yellow 58 -CH, -Crr -O-CH, -CH, -OH reddish yellow LL LL 59 clY -CII, -CH, -OH red-orange 60 NrC-d C-CH, -CH, -OH rotor ring QHL! H2 'L 61 -CH2-CH2-O-CH, -CH -OH red orange 2 62 -CH, -CH, -OH orange 66 C1 t RH2 -NH, - -CH, -CH 67 j -C112-OH2-OH2 -OH orange 66 -CH -CH, -CH, -CH, -O-CH, orange 69 SCP3 -CH2-CH2-OH golden yellow 70 C1 9 E2 CH2 CH2 CH2 OH golden yellow 71 -CH2-CH2-0-CH2 CH2-0 golden yellow Belsplel diazo component R2 Parbton 72 CE2-CH2-OH -H golden yellow 75 N -CH2-CH2-OH orange 74 O 9 O CH2 CH2 CE2 OH orange 75 9 2 -CH2-CH2-0-CH -CH2-OH orange -CE2-cH2- ° -CH3 orsnge (7 -NNE2 -CH2-cH2-cH2- ° H red 78 -CH2-CH2-0-CH2-CH2-OH red 19 COOCH3 CE2 CH2 CH2 OH scarlet SO <r -CH2-CH2-0-CH2-CH2-OH scarlet 81 H g -CH2-CH2-OH orange 82 CH3-ff- -OH2-CH2OH2-OH orange 83 0 -CH2-CH2-0-CH2-CH2-OH orange 84 ß -CE2-CH2-OE orange 85 C2H5-OC t H2 -CH2-CH2-CH2-OH orange 86 CE2 C orange L CH7: s7 -CH, -CH, -O-CH2-GE [, - OH orange ss CH, -CH2-O-CH, -CH, -CH, -OB golden yellow -osange H2 -CH2-CH2-CH2-OH golden yellow -orange 90 N <zuO -CH2-CH2-0-CH2-CH2-OH golden yellow -orange Oy% Example diazo component 2 shade No. 91 ° OH3 O0H2OH2N2 -CH2-CH2-OH orange -OH-OH-OH -OH orange c 9j C II, -SC,? Le [H, -CH, -Ca, -OH orange H H2 2 C 2 oranBe Table 2 coupling component: Example diazo component R2 shade No. Diazokoniponente R2 shade 95 COOCH3 -CH2-CH2-OH reddish yellow -O -OH -OH -OH reddish yellow 97 -OH -0-OH -OH -OH reddish yellow L. gs, CN -CH, -CH, -OH golden yellow L. 99 LNH3 -CH, -CH, -CH, -OH golden yellow \ Z / CL 100 -CH, -CH -CH, -O-CH2-CH2-OH, golden yellow c2r EIY ? Oi ci NH, -CH, -CHL! -OH golden yellow ; -Ckf, -CB, -OH gsld yellow -OH2-OH2 0OH2OH2-OH scarlet from CN -CH, -CH, -CH, -OH rauns ic 107 Br-li = CH2 CH2 CH2 E 3charlach 108 3r -CH, -CH -O-CH -OH -OH brownish . 5 2 2 2 2 2 scarlet br 109 J l CH2 CH2 CH2 OH red 110 02N C112 -CH, -CH, -OH 9 H2 red red -OH -CH, -CH, -CH, -OH CH2 ob \ golden yellow 112 L -CH, -CH2 -O -CH, -CH, -OH golden yellow 113 CH2-CH2-OH -CH2-CH2-OH orange 114 O <9 O 2 2 2 orange 115> 2 -CH2-CH2-CH2-0-CH3 orange Example 116 24.4 parts of the reaction product of aniline with 2,6-dichloro-3-cyano-4-methylpyridine (see Example 1) are stirred with 80 parts of t-methoxypropylamine for 8 hours under pressure at 140 to 160 ° C., then left it is cooled, 8 parts of 50% sodium hydroxide solution are added and excess t-methoxypropylamine and water are distilled off. The residue is treated with 10 parts of 85% sulfuric acid at 100 ° C. for 5 hours. After cooling, the mixture is poured into a mixture of about 500 parts of water, 600 parts of ice and 100 parts of 50% strength sodium hydroxide solution, to the mixture, cooled to OOC, which contains the coupling component of the probable formula contains, a solution of diazotized 3-amino-5-nitro-2,1-benzisothiazole, which is prepared as follows, is then added in proportions: 19.5 parts of 3-amino-5-nitro-2,1-benzisothiazole are added below Stirring at 15 to 25 ° C in portions to about 75 to 85 parts of 96% sulfuric acid and cooled to 0 to 400. 32.5 parts of 23% nitrosylsulfuric acid are then added dropwise at this temperature. The diazotization is complete after stirring at 0 to 50 for about 4 hours. After the coupling mixture has been mixed with the diazonium solution, the pH of the mixture is increased to approximately 1.5 to 2.5 by adding an acid-binding agent such as sodium acetate (or sodium hydroxide solution). In order to achieve good stirring at 0 to 50, it is expedient to add ice and ice water. After the coupling has ended, the mixture is heated to 60 to 80 ° C., and the dyestuff which has precipitated is filtered off with suction and washed with hot water. After drying, about 40 parts of a black dye powder of the likely formula are obtained which dissolves in dimethylformamide with a blue color and dyes polyethylene terephthalate fabric in greenish blue tones with very good fastness properties.

Beispiel 117 122 Teile des Umsetzungaproduktes von Anilin mit 2,6-Dichlor-3-cyan-4-methylpyridin (siehe Beispiel 1) werden mit 150 Teilen N-Methylpyrrolidon und ungefähr 1000 Teilen 25 %igem Ammoniak 15 Stunden bei 1800C im Autoklaven behandelt. Nach dem Erkalten wird das ausgefallene Produkt der wahrscheinlichen Formel abfiltriert, mit Wasser gewaschen und getrocknet. Man erhält etwa 108 Teile eines farblosen Produktes.Example 117 122 parts of the reaction product of aniline with 2,6-dichloro-3-cyano-4-methylpyridine (see Example 1) are treated with 150 parts of N-methylpyrrolidone and approximately 1000 parts of 25% ammonia in an autoclave for 15 hours at 180.degree. After cooling, the failed product becomes the likely formula filtered off, washed with water and dried. About 108 parts of a colorless product are obtained.

22,4 Teile dieses Produktes werden in ungefähr 100 Teilen Eisessig gelöst, dann durch Zugabe von Eis auf 0 bis 20C abgekühlt und mit etwas Amidosulfonsäure versetzt. Zu diesem Kupplungsgemisch gibt man bei OOC in Anteilen eine Lösung von diazotiertem 2-Amino-5-nitro-benzonitril, die wie folgt hergestellt wird: 16,3 Teile 2-Amino-5-nitro-benzonitril werden in Anteilen zu einem auf 0°0 abgekühlten Gemisch von ungefähr 90 Teilen 96 %iger Schwefelsäure und 32,5 Teilen 23 %iger Nitrosylschwefelsäure gegeben. Nach 4- bis Sstündigem Rühren bei 0 bis 40C ist die Diazotierung beendet.22.4 parts of this product becomes glacial acetic acid in approximately 100 parts dissolved, then cooled to 0 to 20C by adding ice and with a little sulfamic acid offset. A solution of is added to this coupling mixture in proportions at OOC diazotized 2-amino-5-nitro-benzonitrile, which is prepared as follows: 16.3 parts 2-Amino-5-nitro-benzonitrile are added in portions to a mixture cooled to 0 ° of approximately 90 parts of 96% sulfuric acid and 32.5 parts of 23% nitrosylsulfuric acid given. After 4 to 5 hours of stirring at 0 ° to 40 ° C., the diazotization is complete.

Um die Kupplung rasch und vollständig durchzuführen, wird das Kupplungsgemisch - das mit Eis und Eiswasser verdünnt werden kann -bei 0 bis 50C durch Zugabe von Natriumacetatlösung auf den pH-Wert von etwa 2,5 eingestellt, Nach beendeter Kupplung wird das Gemisch auf etwa 80°C erhitzt, der ausgefallene Farbstoff der wahrscheinlichen Formel abfiltriert und mit heißem Wasser gewaschen. Man erhält ungefähr 38 Teile eines dunkelbraunen Pulvers, das sich in Dimethylformamid mid roter Farbe löst und Polyäthylenterephthalatgewebe mit vorzüglichen Echtheiten in kräftigen rosa bis roten Tönen färbt, Analog zu der in den Beispielen 1, 116 und 117 beschriebenen Arbeitsweise lassen o oh die in den folgenden Tabelle durch Diazo- und Kupplungskomponente charak-terisierten Farbstoffe herstellen.In order to carry out the coupling quickly and completely, the coupling mixture - which can be diluted with ice and ice water - is adjusted to a pH of about 2.5 at 0 to 50C by adding sodium acetate solution ° C, the precipitated dye of the likely formula filtered off and washed with hot water. About 38 parts of a dark brown powder are obtained which dissolves in dimethylformamide mid red and dyes polyethylene terephthalate fabric with excellent fastness properties in strong pink to red shades Prepare table of dyes characterized by diazo and coupling components.

Tabelle 3 Kupplungskomponente: Beispiel Dissokompongnte R2 Nr. Diazokomponente R2 Farbton . . . . ., . o 118 zu ON -CE2-CE2-OH rosa 119 °2§ 2 2 CE2 az2 OH rosa 120 -CH2-CE-OH rosa 2j CH3 121 -CE2-CH2°O-aH2-CH2-OE rosa 122 CE2 C 2 CH2-OCFO rosa 123 CH2OH2-O-OH3 rosa 124 (0112)6-OH rot Lv 125 -CI2-CH2-O-COCHJ P088 t 126 1 Br -CH2-CHZ-OH rot 128 -OH -OH-OH rot 21 129 Cb OH2OH2 -O-CH2OH2-OH CH2 130 -CE2-CH2-0-CH3 gelbstichig rot 2 131 J -H rubin 132 °2 < sH2 -CH2-CH2-OH rubin 133 ir 'CB2-C:-CHZ-OH rubin 154 -CH2-CH-OH \ rubin 135 -CH2-CH2-O-CH2-CH2-OH rubin- 136 -CH2-CE2-0-CH3 rubin 137 -OH -OH -OH2-O-OH 3 :H2-O-CH, rubin 138 -CH2-CH2-0-COCH3 rubin Beispiel Diazokomponente R2 Farbton Nr. 139 N -H rubin 140 2 < 2 -CH2-CH2-OH rubin 141 Ol CH2 CH2 CH2 ° rubin 142 -CH,-CH-OH rubin 2i cR3 143 -CH2-CH2-0-CH2-CH rubin 144 -CH2-CE2-0-CH3 rubin 145 -C2E5 rubin V2U5 146 02N < H2 -CE2-CH2-OH rot 147 -OH2-O112-OH2-OH rot 146 -CH2-CH2-0-CH2-CH2-OH rot 149 -CH,-CH,-OH rot 2 2 150 2 t 2 » 2 vEa w 2 rot 151 r -CH -CH2-0-CH -CH2-OH rot 152 -CH2-CH2-OH rot 0 N NH 15) 2 - 2 -OH -OH -OH -OH rot COoca3-CH,-OCI 2 2 2 154 li°2 -H rot 155 02N 4 nie2 -GH2-CH2-OH dunkelrot 156 CH2 CE2 CE2 H dunkelrot 157 -0H2-OH2-O-0H2-0H2-OH dunkelrot 15& -CH2-OH2-O-0H5 dunkelrot C1 159 Cl . -CH2-CS2-OH braunstichig rot 160 02N < NH2 I -CH2-CH2-CH2-OH braunstichig rot 161 bl -CH -CH2-0-CH2-CH2-OH braunstichig rot 162 ; -CHe-CH,-O-COCB, braunstichig rot Beispiel Diazokomponente R2 Farbton Nr. 16j 3r -CE2-CE2-OH braunstichig rot 164 0 2N112 -CH2-CH2-OH2-OH braunstichig rot 165 3r -CH2-0111-OH brsunstichig rot CH3 166 -CH2-CH2-0-CH2-CH2-OH brauxlstichig rot LL2 167 cl oII bsaunotiehig rot 167 -0H2-CH2-OH -CH rot 168 2 < CH2 CH2 2 braunstichig rot 169 3r -CH2-CH2-CE2-0-CH3 braunstichig rot LL3 170 I:cr CJ -CH2-CH2-0-H violett 171 2N H2 OH2OH20H2O11 violett 172 CN -OH -O-CII,-CH,-OH violett 173 -GH,-CH,-Cff7-o-C vioaett ~ . 74 so,N( C2Hg)2 -CH,-CH,-OH blaustichigr ot 175 c,d-w L 2- -CH,-CH,-CH,-OH blaustichig rot 176 w4°2 -CH2-CH2-OH blaustichig rot 177 N NI -CH,-CH, -CH,-OH blaustichig rot 178 cí -CE2-CH2-0-CE2-CH2-OH blaustichig rot . 179 |7l -CE2-CH2-OH orange 2 180 O4H9(n)NHO --CH--CH,-CH,-OH orange 181 £2 | -CH2-CH2-0-CH2 CH2-OE orange 3r 182 rl Bf -CH,-CH,cOH orange 49 NH 183 (n)0 11 NH-OO 3r2 -CH2-CH2-CH2-OH orange 184 -CH,-CH,-O-CH2-CH2-OH orange 185 SO OH -H blaustichig rot 186 0 2NNH223 -CH2-CH2-OH rubin 187 CH2 CH2 CH2 OH rubin - 186 -CH2-lCH-OH rubin 21 189 . CH -(CH2 )33 o-(CH234-oH rubin ro Beispiel Diazokomponente R2 Farbton aTr. 2 190 E2 -CH2-CH2-OH rotstichig blau 191 2 -0112-0112-C112-0H Dsrineblau 192 >~ v CH2-CH-OH marineblau 0113 193 -CH,-CH,-O-CH,-CH2-OH morineblau 194C1Bi6OB marinebiau 195 °(CE2)3-0-( )4-OH marineblau 196 2 Cz2-C N -O-g-CE3 rotstichig blau 197 NF -CK2-0112-O11 -O-C-OH bleu blau CU2OH2 0O112OH2-OH blau °2 9 Br(Cl) (blau) Br 198 p NH2 -CH,-CH -C2-OH rotbraun 199 t CE2"CH2-0-CH2-CH2-OH rotbraun k=I c c 200 zu NE2 -CH,-CH,-CL-OH goldgelb 201 =(OC H, C 0206115 -C N -CH2-0-CE2-CH2-OH goldgelb Q c 2 202 l -GH,-CH,-O-CH,-CH2-OH goldgelb 203 > t NHX 4 2)3 goldgelb O . NO OH -OH -OH . 2 2 2 205 -CH,-CH,-CH,-OH violett Lr- 206 1 -OH 2 violett OH 207 l -CH2-CH2-0-CH2-CH2-OH violett 3eispiel ja z okomponente R Parbton Nr. I - II------ -2 1 208 2 O2 -(CE2)3-oR violett 209 0 2N ,C -CE2 CE2-O-oE2 Cz2 violett Dr 210 N CH2 CH2 CH2 E scharlachrot 211 02N 2 > Z -0H2-OH2-O-CH2-OH2-0H scharlachrot O,NIAs 212 -GP2-CH2-CH,-BH scharlachrot 213 3 ~U S CH2-CH2-0-aE2 CE2 0 214 aTI;I -CH2-0H2-OH -OH gelbstlchlg rot 215 N 2 -OH2-0H2-O-0112-0H2-011 gelbstichig rot rbm 216 O2N''NH2 -CE2"CE2-0E rubin 217 -0H2-012-0H2-OH rubin 218 CH -OH -0-OH-OH -OH rubin C . . . . 219 -(eBt,) -Ib-(CH).-OB[ ruBin rJ 2c C1 220 -CH,-CH-CH,-OH violett 221 CB;-CH2-O-eB2-CHp-OH vi9lstt 222 -(CH,)3-O-(CIa ),-OH Piole%t CN - - IIELLI 19-iIiD1--L4LI1 226 0 °2§ 9 NH2 -CH2-CH2-0-CH2-CH2-OH violett N Beispiel Dlazokomponente R2 Farbton Nr. 22Y 02O2H -CH,-CH,-CH,-OH rubin ... . . . .. 228 OH 96 -H rotorange 229 E 4 H2 -CH2-CH2-OE scharlach -0112-0112-C112-0H scharlach 231 -C CH,-OH scherlech 22 0 -CH,-CH,-OH schariach 233 CH30-C-C2H4- 9 2OH20H -CH,-OH scharlach 234 N v -011-OH-OH scharlach -OH -O11-0-OH -OH -OH scharlach 2 236 -H rotorange 237 c -CH2-CH2-OIf violett 238 02a -CH,-CH2-CH,-OH violett c 239 -CH,-CH2-O-CH,-CH2-OH violett 241 5'YnZ CE-O-g 2 CH2 CH2 aH2 OH notvioictt 242 -CE2-CE2-0-CH2-CE2-OE rotvi olett 243 -CH2-H-OH r-otvi olett 244 CH ,CI -CII-CH,-oH rotviolett FJn - L 245 L! -CH2-CH -CH3-OH 246 -CE2-CH2-0-CH2-CH2-OH rotviol -OH -r. c2 247 NO -CH,-CH,-CH,-OH 2 2 2 -<otOt I" - CN Beispiel Diazokoniponente : Farbton Nr. NO -OH -OH -OH -OH violett 249 °2} > 2 -CH2-CH2-0-CE2-CH2-OH viQlett 250 CH3 CN -CH2-CH2-OH rotstichig blau 251 O N < KH2 CH2 CH2 CH2 OH rotstichig blau 252 2 -CH2-CE2-0-CH2-CH2-OH rotstichig blau a ) I S-eR2 -CH2-CH2 -cH2-°H blau Tabelle 4 Kupplungskomponente: - - Beispiel Diazokomponente R1 Farbton Nr . 254 bs -CH2-CH -OH rot 255 02N 4 H2 -CH2-cH2-cH2-°H rot 25b -CH2-CH2-0-CH2-CH2-OH rot ON ro 257 CN -H rosa 25ú 02N b Hz -CH2-CH2-OH rot 259 - CH2 CB2 ° C0CE3 rosa 260 CH2 CH2 CH2 OH dunkelrot 261 -CE2-CH2-o-CH2-CH2-OH rosa 22 -CH2-CH2-0-CH -CH2CCHO rosa 2b3 -(CH2)O~OH dunkelrot 4 l | Beispiel Diazokomponente R1 Farbton Nr . 264 CH, -0H2-0112-OH2-OH rubin 265 ° ei 9 2 -CH2-CE2-0-CH2-CH2-OE rubin 266 N -H rubin 267 o -0ff2-0H2-OR rubin 268 r -OH2-0H2-oH2-0H rubin 269 -CH,-CH-OH rubin 2t CH3 270 -CE2-CH2-0-CH2-CH2-OE rubin 2 2 271 Cm -CH2-CH2-OE rubin 272 02N P 2N CH2 CH2 CH2 OH rubin 273 }1 -CH-CH2-0-CH2-CH2-OH rubin Irll 274 -(CB ) -O-(CH,),-OB rubin '2 c 4 275 B02 -CH,-CH,-CH2-OH violett 02' L 277 g -CH2-CE2-0-CH2-CH2-OE rubin I;o CH 2 279 °2h < gH2 -CE2-CH2-0-CH2-CH2-OH violett 276 0'"8 Cg2-CH,-OH rubin 277 -CII,-CH,-o-CH2-CH2-oH rubin 280 02h < R2 CE2 CH2 CH2 ob mcrrineblou 281 -CH,-CH3-O-eH3-CH,-OH arineblau 282 0 O2Nffi(rSNH2 -OH2-OH2-O-OH2-OH2 -OH blau Beispiel Diazokomponente i Farbton Nr . 283 O2NN2 -CH2-CH2-0-CH2-CH2-OH blau Br 284 pro, -CH2-CB2-OH dunkelrot 285 0 MI2 -CH2-CH2CH20H dunkelrot 286 -CH,-CH,-O-CH,-CH,-OH dunkelrot r LL L I 287 02 -CH2CH3-CH,-OH violett 288 O,N-H2-O-CH2-CH2-OH violete C1 289 2 °2 -Ca -Ca2-cH2-°H violott 289 PT02 -CH2-CH,-CH2-OH violett 20 02NBB L 2 -CH,-CH,-O-CH,-CH,-OH violett 292 d-w, °2 2 O2NHH2 2 2 2 2 Tabelle 5 Kupplungskomponente: Beispiel Diaz;okolpponente R Fsrbt on Nr. Diazokomponente R2 Farbton 293 1 l -CH2-CH2-0-COCH3 rot 294 02N t a2 -CE2-CH2-CH2-0-COCH3 rot 295 -CH,-CHZ-CH2-OH rot 296 -CH2-CH2-0-CH3 rot Beispiel Diazokomponente R2 Farbton 2 297 N -OH2-OH2-OOOOH3 blaustichig rot 29o O2NH2 -CH2-CE2-CH2-OCOCH3 blaustichig rot 299 -Ci2-cH2-cH2-°i blsustichig rot 300 -O112-0H2-0-OH2-OH2-OOOOH3 blaustichig rot 301 -CH2-CE2-0-CH2-CH2-OH blaustichig rot 302 -0H2-OH2 -0-OH3 blaustichig rot 303 ON -CH2-CE2-CH2-OCOCH3 violett 304 2 -OH2-0H2-0H2-OH violett 305 Mr -CH2-CH2-0-GH2-CH2-OCOCE3 violett 306 -CH2-CE2-0-CH2-CE2-OE violett 307 -CH,-CH, violett 308 -CH2-CE2-CE2-0-CH3 violett LL I 509 2 < 2 -CH2-CH2-0-COCH2-COCH3 grunstichig blau 310 N -0H2-OH2-OOOOH3 grünstichig blau 311 -CE2-CH2-CE2-0-COCE3 grunstichig blau 312 H2-OH2-OH2-OH grünstichig blau 313 -CH2-CH2-0-CH3 grünstichig blau 314 1 -CH2-CH2-0E2-o C2E5 grünstichig blau 315 -CH2-CH2-0-CH2-CH2-OCHO grünstichig blau 2 -CH2-CH2-0-CH2-CH2-OH grünstichig blau 317 CH2 cE2 2 OH2-O-000H3 grünstichig blau r2 , 2 02N X H2 l 2 2 2 CE2 OH2-O-OOOll3 grünstichig blau 3r Tabelle 6 Kupplungskomponente: - : - Beispiel Diazokomponente R1 Farbton Nr. Diazokomponente R1 319 1 l -CH2-CH2-CH2-OCOCH3 rot 320 °2 > -OH2-CH2-0H2-OH rot c 521 > ON- -CH2-CE2-CH2-OCOCHs blaustichig rot S22 02N 9 OH2tOH2OH2 -OH blaustichig rot 325 -0H2-0H2-O-0H2-0H2-OOOOH3 blaustichig rot 324 -OH2-OH2-0-OH2-OH2COHO blaustichig rot 325 J N -0H2-OH2-OH2-0-000H3 violett 326 03NII- t r NH2 -OH3-OH2-0-OH2-OH2-OOHO violett 327 r OH2OH2 -0-OH2-0112-O-000H3 violett 328 02N e E2 -CH,-CH,-GH2-O-COCH, grünstichig blau j29IS OH2-OH2-OH2-0000H2-000H3 grünstichig blau 330 -OH2-OH2-OH2-OH grünstichig blau 531 .,CH2-CH2-0-CH2-CH2-OH grunstichig blau 332 ,CH2-CH,-O-CH,-CH2-OCHO grünstlchig blsu 33 -OCOCH? rwlstlchlg blau 334 -OH -CH2-CH2-O-CH2-CH,-OCHO grünstichig blau 335 < CH2 CE2 ° CH2 CH2 ° COCE3 grunstichig blau 336 Br -CH2-CH2-0-CH °CH2-OH grünstichig blau 337 . -- -(CH2)3-0-(CH2)4-OH grünstichig blau 2 °2h zu H2 -CH2-CE2-0-CH2-CH2-OCOCH3 grunstlchig blau 339 t -CH2-CH2-CH2-0-CH3 grunstiehig blau <1 ~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~~~~~~ Analog können die folgenden Farbstoffe hergestellt werden: Beispiel Nr O2N''- N=Ng NH49 rot NH-CH2 - CH2-O-CH2-CH2-OH H3C CN 0\\M\\'N=N\NH blaustichig rot 341 CH3°CH2CH2 N/ / NH-CH2-CH2-O-CH2-CH2 OH HC CN 9 /7 342 02m -CH,-CH,-O-CH2'CK2-OH L L WN H3 C CN 343 N=Nf$ÄffiNH#½\ scharlach NH-CH2-CH2-O-CH2-CH2-OH Beispiel 344 11 Teile des Farbstoffs der Formel (Beispiel 118) werden mit 100 Raumteilen Ameisensäure 4 Stunden unter Rückflußkühlung erhitzt. Nach dem Erkalten setzt man unter Rühren ungefähr 100 Teile Wasser zu, filtriert den ausgefallenen Niederschlag der Formel ab, wäscht ihn mit Wasser und trocknet. Man erhält ungefähr 11 Teile eines dunkelbraunen Pulvers, das sich in Dimethylformamid mit roter Farbe löst und Polyäthylenterephthalatgewebe in rosa bis roten Tönen mit hervorragenden Echtheiten färbt.Table 3 coupling component: Example dissocomposed R2 No. Diazo component R2 shade . . . . .,. O 118 for ON -CE2-CE2-OH pink 119 ° 2§ 2 2 CE2 az2 OH pink 120 -CH2-CE-OH pink 2y CH3 121 -CE2-CH2 ° O-aH2-CH2-OE pink 122 CE2 C 2 CH2-OCFO pink 123 CH2OH2-O-OH3 pink 124 (0112) 6-OH red Lv 125 -CI2-CH2-O-COCHJ P088 t 126 1 Br -CH2-CHZ-OH red 128 -OH -OH-OH red 21 129 Cb OH2OH2 -O-CH2OH2-OH CH2 130 -CE2-CH2-0-CH3 yellowish red 2 131 J -H ruby 132 ° 2 <sH2 -CH2-CH2-OH ruby 133 ir 'CB2-C: -CHZ-OH ruby 154 -CH2-CH-OH \ ruby 135 -CH2-CH2-O-CH2-CH2-OH ruby- 136 -CH2-CE2-0-CH3 ruby 137 -OH -OH -OH2-O-OH 3: H2-O-CH, ruby 138 -CH2-CH2-0-COCH3 ruby Example diazo component R2 shade No. 139 N -H ruby 140 2 <2 -CH2-CH2-OH ruby 141 Ol CH2 CH2 CH2 ° ruby 142 -CH, -CH-OH ruby 2i cR3 143 -CH2-CH2-0-CH2-CH ruby 144 -CH2-CE2-0-CH3 ruby 145 -C2E5 ruby V2U5 146 02N <H2 -CE2-CH2-OH red 147 -OH2-O112-OH2-OH red 146 -CH2-CH2-0-CH2-CH2-OH red 149 -CH, -CH, -OH red 2 2 150 2 t 2 »2 vEa w 2 red 151 r -CH -CH2-0-CH -CH2-OH red 152 -CH2-CH2-OH red 0 N NH 15) 2 - 2 -OH -OH -OH -OH red COoca3-CH, -OCI 2 2 2 154 li ° 2 -H red 155 02N 4 nie2 -GH2-CH2-OH dark red 156 CH2 CE2 CE2 H dark red 157 -0H2-OH2-O-0H2-0H2-OH dark red 15 & -CH2-OH2-O-0H5 dark red C1 159 cl. -CH2-CS2-OH brownish red 160 02N <NH2 I -CH2-CH2-CH2-OH brownish red 161 bl -CH -CH2-0-CH2-CH2-OH brownish red 162; -CHe-CH, -O-COCB, brownish red Example diazo component R2 shade No. 16j 3r -CE2-CE2-OH brownish red 164 0 2N112 -CH2-CH2-OH2-OH brownish red 165 3r -CH2-0111-OH eruptive red CH3 166 -CH2-CH2-0-CH2-CH2-OH gray-tinged red LL2 167 cl oII bsaunotiehig red 167 -0H2-CH2-OH -CH red 168 2 <CH2 CH2 2 brownish red 169 3r -CH2-CH2-CE2-0-CH3 brownish red LL3 170 I: cr CJ -CH2-CH2-0-H purple 171 2N H2 OH2OH20H2O11 purple 172 CN -OH -O-CII, -CH, -OH purple 173 -GH, -CH, -Cff7-oC vioaett ~. 74 so, N (C2Hg) 2 -CH, -CH, -OH bluish tinge ot 175 c, dw L 2- -CH, -CH, -CH, -OH bluish red 176 w4 ° 2 -CH2-CH2-OH bluish red 177 N NI -CH, -CH, -CH, -OH bluish red 178 cí -CE2-CH2-0-CE2-CH2-OH bluish red . 179 | 7l -CE2-CH2-OH orange 2 180 O4H9 (n) NHO --CH - CH, -CH, -OH orange 181 £ 2 | -CH2-CH2-0-CH2 CH2-OE orange 3r 182 rl Bf -CH, -CH, COH orange 49 NH 183 (n) 0 11 NH-OO 3r2 -CH2-CH2-CH2-OH orange 184 -CH, -CH, -O-CH2-CH2-OH orange 185 SO OH -H bluish red 186 0 2NNH223 -CH2-CH2-OH ruby 187 CH2 CH2 CH2 OH ruby - 186 -CH2-1CH-OH ruby 21 189 CH - (CH2) 33 o- (CH234-oH ruby ro Example diazo component R2 shade aTr. 2 190 E2 -CH2-CH2-OH reddish blue 191 2 -0112-0112-C112-0H Dsrine blue 192> ~ v CH2-CH-OH navy blue 0113 193 -CH, -CH, -O-CH, -CH2-OH morine blue 194C1Bi6OB marinebiau 195 ° (CE2) 3-0- () 4-OH navy blue 196 2 Cz2-C N -Og-CE3 reddish blue 197 NF -CK2-0112-O11 -OC-OH bleu blue CU2OH2 0O112OH2-OH blue ° 2 9 Br (Cl) (blue) Br 198 p NH2 -CH, -CH -C2-OH red brown 199 t CE2 "CH2-0-CH2-CH2-OH red-brown k = I cc 200 to NE2 -CH, -CH, -CL-OH golden yellow 201 = (OC H, C 0206115 -CN -CH2-0-CE2-CH2-OH golden yellow Q c 2 202 l -GH, -CH, -O-CH, -CH2-OH golden yellow 203> t NHX 4 2) 3 golden yellow O . NO OH -OH -OH. 2 2 2 205 -CH, -CH, -CH, -OH purple Lr- 206 1 -OH 2 purple OH 207 l -CH2-CH2-0-CH2-CH2-OH purple 3example yes z ocomponent R Parbton No. I - II ------ -2 1 208 2 O2 - (CE2) 3-oR purple 209 0 2N, C -CE2 CE2-O-oE2 Cz2 violet Dr 210 N CH2 CH2 CH2 E scarlet red 211 02N 2> Z -0H2-OH2-O-CH2-OH2-0H scarlet red O, NIAs 212 -GP2-CH2-CH, -BH scarlet red 213 3 ~ US CH2-CH2-0-aE2 CE2 0 214 aTI; I -CH2-0H2-OH -OH yellowish red 215 N 2 -OH2-0H2-O-0112-0H2-011 yellowish red rbm 216 O2N``NH2 -CE2 "CE2-0E ruby 217 -0H2-012-0H2-OH ruby 218 CH -OH -0-OH-OH -OH ruby C. . . . . 219 - (eBt,) -Ib- (CH) .- OB [ruBin rJ 2c C1 220 -CH, -CH-CH, -OH purple 221 CB; -CH2-O-eB2-CHp-OH vi9lstt 222 - (CH,) 3-O- (CIa), -OH piole% t CN - - IIELLI 19-iIiD1 - L4LI1 226 0 ° 2§ 9 NH2 -CH2-CH2-0-CH2-CH2-OH purple N Example Dlazo component R2 color No. 22Y 02O2H -CH, -CH, -CH, -OH ruby ... . . .. 228 OH 96 -H red orange 229 E 4 H2 -CH2-CH2-OE scarlet -0112-0112-C112-0H scarlet 231 -C CH, -OH scherlech 22 0 -CH, -CH, -OH schariach 233 CH30-C-C2H4- 9 2OH20H -CH, -OH scarlet 234 N v -011-OH-OH scarlet -OH -O11-0-OH -OH -OH scarlet 2 236 -H red orange 237 c -CH2-CH2-OIf purple 238 02a -CH, -CH2-CH, -OH purple c 239 -CH, -CH2-O-CH, -CH2-OH purple 241 5'YnZ CE-Og 2 CH2 CH2 aH2 OH notvioictt 242 -CE2-CE2-0-CH2-CE2-OE red violet 243 -CH2-H-OH r-otvolett 244 CH, CI -CII-CH, -oH red-violet FJn - L 245 L! -CH2-CH -CH3-OH 246 -CE2-CH2-0-CH2-CH2-OH red-violet -OH -r. c2 247 NO -CH, -CH, -CH, -OH 2 2 2 - <otOt I "- CN Example diazo component: color tone No. NO -OH -OH -OH -OH purple 249 ° 2}> 2 -CH2-CH2-0-CE2-CH2-OH viQlett 250 CH3 CN -CH2-CH2-OH reddish blue 251 ON <KH2 CH2 CH2 CH2 OH reddish blue 252 2 -CH2-CE2-0-CH2-CH2-OH reddish blue a) I S-eR2 -CH2-CH2 -cH2- ° H blue Table 4 coupling component: - - Example diazo component R1 color No . 254 bs -CH2-CH -OH red 255 02N 4 H2 -CH2-cH2-cH2- ° H red 25b -CH2-CH2-0-CH2-CH2-OH red ON ro 257 CN -H pink 25ú 02N b Hz -CH2-CH2-OH red 259 - CH2 CB2 ° C0CE3 pink 260 CH2 CH2 CH2 OH dark red 261 -CE2-CH2-o-CH2-CH2-OH pink 22 -CH2-CH2-0-CH -CH2CCHO pink 2b3 - (CH2) O ~ OH dark red 4 l | Example diazo component R1 color No . 264 CH, -0H2-0112-OH2-OH ruby 265 ° ei 9 2 -CH2-CE2-0-CH2-CH2-OE ruby 266 N -H ruby 267 o -0ff2-0H2-OR ruby 268 r -OH2-0H2-oH2-0H ruby 269 -CH, -CH-OH ruby 2t CH3 270 -CE2-CH2-0-CH2-CH2-OE ruby 2 2 271 cm -CH2-CH2-OE ruby 272 02N P 2N CH2 CH2 CH2 OH ruby 273} 1 -CH-CH2-0-CH2-CH2-OH ruby Irll 274 - (CB) -O- (CH,), - OB ruby '2 c 4 275 B02 -CH, -CH, -CH2-OH purple 02 'L 277 g -CH2-CE2-0-CH2-CH2-OE ruby I; o CH 2 279 ° 2h <gH2 -CE2-CH2-0-CH2-CH2-OH purple 276 0 '"8 Cg2-CH, -OH ruby 277 -CII, -CH, -o-CH2-CH2-oH ruby 280 02h <R2 CE2 CH2 CH2 ob mcrrineblou 281 -CH, -CH3-O-eH3-CH, -OH arine blue 282 0 O2Nffi (rSNH2 -OH2-OH2-O-OH2-OH2 -OH blue Example diazo component i color No . 283 O2NN2 -CH2-CH2-0-CH2-CH2-OH blue Br 284 pro, -CH2-CB2-OH dark red 285 0 MI2 -CH2-CH2CH20H dark red 286 -CH, -CH, -O-CH, -CH, -OH dark red r LL LI 287 02 -CH2CH3-CH, -OH purple 288 O, N-H2-O-CH2-CH2-OH purple C1 289 2 ° 2 -Ca -Ca2-cH2- ° H violet 289 PT02 -CH2-CH, -CH2-OH purple 20 02NBB L 2 -CH, -CH, -O-CH, -CH, -OH purple 292 dw, ° 2 2 O2NHH2 2 2 2 2 Table 5 Coupling component: Example Diaz; okolpponente R Fsrbt on No. Diazo component R2 shade 293 1 l -CH2-CH2-0-COCH3 red 294 02N t a2 -CE2-CH2-CH2-0-COCH3 red 295 -CH, -CHZ-CH2-OH red 296 -CH2-CH2-0-CH3 red Example diazo component R2 shade 2 297 N -OH2-OH2-OOOOH3 bluish red 29o O2NH2 -CH2-CE2-CH2-OCOCH3 bluish red 299 -Ci2-cH2-cH2- ° i puffy red 300 -O112-0H2-0-OH2-OH2-OOOOH3 bluish red 301 -CH2-CE2-0-CH2-CH2-OH bluish red 302 -0H2-OH2 -0-OH3 bluish red 303 ON -CH2-CE2-CH2-OCOCH3 violet 304 2 -OH2-0H2-0H2-OH purple 305 Mr -CH2-CH2-0-GH2-CH2-OCOCE3 purple 306 -CH2-CE2-0-CH2-CE2-OE violet 307 -CH, -CH, purple 308 -CH2-CE2-CE2-0-CH3 violet LL I 509 2 <2 -CH2-CH2-0-COCH2-COCH3 greenish blue 310 N -0H2-OH2-OOOOH3 greenish blue 311 -CE2-CH2-CE2-0-COCE3 greenish blue 312 H2-OH2-OH2-OH greenish blue 313 -CH2-CH2-0-CH3 greenish blue 314 1 -CH2-CH2-0E2-o C2E5 greenish blue 315 -CH2-CH2-0-CH2-CH2-OCHO greenish blue 2 -CH2-CH2-0-CH2-CH2-OH greenish blue 317 CH2 cE2 2 OH2-O-000H3 greenish blue r2, 2 02N X H2 l 2 2 2 CE2 OH2-O-OOOll3 greenish blue 3r Table 6 Coupling component: -: - Example diazo component R1 color No. Diazo component R1 319 1 l -CH2-CH2-CH2-OCOCH3 red 320 ° 2> -OH2-CH2-0H2-OH red c 521> ON- -CH2-CE2-CH2-OCOCHs bluish red S22 02N 9 OH2tOH2OH2 -OH bluish red 325 -0H2-0H2-O-0H2-0H2-OOOOH3 bluish red 324 -OH2-OH2-0-OH2-OH2COHO bluish red 325 JN -0H2-OH2-OH2-0-000H3 purple 326 03NII- tr NH2 -OH3-OH2-0-OH2-OH2-OOHO purple 327 r OH2OH2 -0-OH2-0112-O-000H3 purple 328 02N e E2 -CH, -CH, -GH2-O-COCH, greenish blue j29IS OH2-OH2-OH2-0000H2-000H3 greenish blue 330 -OH2-OH2-OH2-OH greenish blue 531., CH2-CH2-0-CH2-CH2-OH greenish blue 332, CH2-CH, -O-CH, -CH2-OCHO greenish blsu 33 -OCOCH? rwlstlchlg blue 334 -OH -CH2-CH2-O-CH2-CH, -OCHO greenish blue 335 <CH2 CE2 ° CH2 CH2 ° COCE3 greenish blue 336 Br -CH2-CH2-0-CH ° CH2-OH greenish blue 337. - - (CH2) 3-0- (CH2) 4-OH greenish blue 2 ° 2h to H2 -CH2-CE2-0-CH2-CH2-OCOCH3 greenish blue 339 t -CH2-CH2-CH2-0-CH3 green deep blue <1 ~~~~~~~~~~ ~~~~~~~~~~~~~~~~~~~~~~~~~ The following dyes can be prepared analogously: Example No. O2N '' - N = Ng NH49 red NH-CH2 - CH2-O-CH2-CH2-OH H3C CN 0 \\ M \\ 'N = N \ NH bluish red 341 CH3 ° CH2CH2 N / / NH-CH2-CH2-O-CH2-CH2 OH HC CN 9/7 342 02m -CH, -CH, -O-CH2'CK2-OH LL WN H3 C CN 343 N = Nf $ ÄffiNH # ½ \ scarlet NH-CH2-CH2-O-CH2-CH2-OH Example 344 11 parts of the dye of the formula (Example 118) are refluxed with 100 parts by volume of formic acid for 4 hours. After cooling, about 100 parts of water are added with stirring, and the precipitate of the formula which has separated out is filtered off wash it off with water and dry it. About 11 parts of a dark brown powder are obtained which dissolves in dimethylformamide with a red color and dyes polyethylene terephthalate fabric in pink to red shades with excellent fastness properties.

Claims (3)

PatentansprücheClaims 1. Azofarbstoffe mit 2,6-Diaminopyridinen als Kupplungskomponente der Formel in der D den Rest einer Diazokomponente, X Cyan oder Carbonamid, einer der Reste R Phenyl und der andere Rest R Wasserstoff oder gegebenenfalls durch Hydroxy, Alkoxy, Hydroxyalkoxy oder Acyloxy substituiertes Alkyl bedeuten.1. Azo dyes with 2,6-diaminopyridines as coupling components of the formula in which D is the radical of a diazo component, X is cyano or carbonamide, one of the radicals R is phenyl and the other radical R is hydrogen or alkyl which is optionally substituted by hydroxy, alkoxy, hydroxyalkoxy or acyloxy. 2.- Die Verwendung der Farbstoffe gemäß Anspruch 1 zum Färben von Polyamiden, Acrylnitrilpolymerisaten, Celluloseestern und Polyestern.2.- The use of the dyes according to claim 1 for dyeing Polyamides, acrylonitrile polymers, cellulose esters and polyesters. 3. Ein Verfahren zur Herstellung von Farbstoffen gemäß Anspruch 1, dadurch gekennzeichnet, daß man Diazoverbindungen von Aminen der Formel D-NH2 mit Kupplungskomponenten der Formel umsetzt und hydroxylgruppenhaltige Farbstoffe gegebenenfalls verestert.3. A process for the preparation of dyes according to claim 1, characterized in that diazo compounds of amines of the formula D-NH2 with coupling components of the formula reacted and dyes containing hydroxyl groups, optionally esterified.
DE19722211663 1970-12-19 1972-03-10 Azo dyes with 2,6-diaminopyrfdines as coupling components, process for their production and dye preparations Expired DE2211663C3 (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
DE19722211663 DE2211663C3 (en) 1972-03-10 1972-03-10 Azo dyes with 2,6-diaminopyrfdines as coupling components, process for their production and dye preparations
CH321773A CH596263A5 (en) 1972-03-10 1973-03-05
CS163973A CS178421B2 (en) 1972-03-10 1973-03-07
US05/338,859 US4042578A (en) 1972-03-10 1973-03-07 Azo dyes having 2,6-diaminopyridine derivatives as coupling components
IN502/CAL/73A IN139039B (en) 1972-03-10 1973-03-07
DD169311A DD106192A5 (en) 1972-03-10 1973-03-08
FR7308567A FR2187857B1 (en) 1972-03-10 1973-03-09
SU1891749A SU521848A3 (en) 1972-03-10 1973-03-09 The method of obtaining 2,6-diaminopyridine azo dye
NL7303378A NL7303378A (en) 1972-03-10 1973-03-09
BE128597A BE796542A (en) 1972-03-10 1973-03-09 AZOIC DYES OBTAINED FROM COPULANTS CONSISTING OF 2,6-DIAMINOPYRIDINE DERIVATIVES
IT48707/73A IT979789B (en) 1972-03-10 1973-03-09 AZOCOLORANTS WITH 2, 6 DIAMMINOPYRIDINE DERIVATIVES AS COPULATION COMPONENTS
GB1140873A GB1422650A (en) 1972-03-10 1973-03-09 Azo dyes having 2,6-diaminopyridine derivatives as coupling components
JP48027651A JPS6139347B2 (en) 1972-03-10 1973-03-10
US05/711,863 USRE29640E (en) 1970-12-19 1976-08-05 Certain substituted 2,6-diamino-4-methyl-nicotinitriles the corresponding nicotinamides and derivatives thereof

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DE19722211663 DE2211663C3 (en) 1972-03-10 1972-03-10 Azo dyes with 2,6-diaminopyrfdines as coupling components, process for their production and dye preparations

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DE2211663C3 DE2211663C3 (en) 1975-01-16

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2832020A1 (en) * 1978-07-21 1980-01-31 Basf Ag DISAZO DYES WITH PYRIDINE CLUTCH COMPONENTS
EP0042486A1 (en) * 1980-06-06 1981-12-30 BASF Aktiengesellschaft Method of colouring coating-substances, organic solvents and mineral-oil products, and dyestuffs
EP0433693A1 (en) * 1989-11-22 1991-06-26 Hoechst Mitsubishi Kasei Co., Ltd. Water-insoluble monoazo dyes and mixture thereof
EP0548715A1 (en) * 1991-12-13 1993-06-30 DyStar Japan Ltd. Disperse dye mixtures
WO1998037150A1 (en) * 1997-02-18 1998-08-27 Basf Aktiengesellschaft Trifluoromethyl-substituted azo dyes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT373930B (en) 1975-10-29 1984-03-12 Basf Ag DYE PREPARATIONS FOR DYEING AND PRINTING CELLULOSE AND CELLULOSE-CONTAINING TEXTILE MATERIAL

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2832020A1 (en) * 1978-07-21 1980-01-31 Basf Ag DISAZO DYES WITH PYRIDINE CLUTCH COMPONENTS
EP0042486A1 (en) * 1980-06-06 1981-12-30 BASF Aktiengesellschaft Method of colouring coating-substances, organic solvents and mineral-oil products, and dyestuffs
EP0433693A1 (en) * 1989-11-22 1991-06-26 Hoechst Mitsubishi Kasei Co., Ltd. Water-insoluble monoazo dyes and mixture thereof
EP0548715A1 (en) * 1991-12-13 1993-06-30 DyStar Japan Ltd. Disperse dye mixtures
US5332404A (en) * 1991-12-13 1994-07-26 Hoechst Mitsubishi Kasei Co., Ltd. Disperse dye mixtures
WO1998037150A1 (en) * 1997-02-18 1998-08-27 Basf Aktiengesellschaft Trifluoromethyl-substituted azo dyes

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BE796542A (en) 1973-09-10
DE2211663C3 (en) 1975-01-16
DE2211663B2 (en) 1974-05-30
IN139039B (en) 1976-05-01

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