DE2409754A1 - Heat-stable dyes of 2,6-diamino-pyridine series - for dyeing thermoplastics in the melt - Google Patents

Heat-stable dyes of 2,6-diamino-pyridine series - for dyeing thermoplastics in the melt

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DE2409754A1
DE2409754A1 DE2409754A DE2409754A DE2409754A1 DE 2409754 A1 DE2409754 A1 DE 2409754A1 DE 2409754 A DE2409754 A DE 2409754A DE 2409754 A DE2409754 A DE 2409754A DE 2409754 A1 DE2409754 A1 DE 2409754A1
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amino
methyl
cyano
phenyl
nitro
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German (de)
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Johannes Dipl Chem Dr Dehnet
Gunther Dipl Chem Dr Lamm
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BASF SE
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BASF SE
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Priority to DE2409754A priority Critical patent/DE2409754A1/en
Priority to US05/551,493 priority patent/US3974123A/en
Priority to IT7548395A priority patent/IT1029901B/en
Priority to JP2410875A priority patent/JPS539780B2/ja
Priority to FR7506343A priority patent/FR2262681B1/fr
Priority to BE153897A priority patent/BE826160A/en
Priority to NL7502419A priority patent/NL7502419A/en
Priority to GB8384/75A priority patent/GB1499181A/en
Publication of DE2409754A1 publication Critical patent/DE2409754A1/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C09B29/0011—Monoazo dyes prepared by diazotising and coupling from diazotized anilines from diazotized anilines directly substituted by a heterocyclic ring (not condensed)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0018—Monoazo dyes prepared by diazotising and coupling from diazotized aminopolycyclic rings
    • C09B29/0022—Monoazo dyes prepared by diazotising and coupling from diazotized aminopolycyclic rings from diazotized aminoanthracene
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    • 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
    • C09B29/0059—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only sulfur as heteroatom
    • 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
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
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    • 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
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
    • C09B29/0081—Isothiazoles or condensed isothiazoles
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    • 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
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
    • C09B29/0085—Thiazoles or condensed thiazoles
    • C09B29/0088—Benzothiazoles
    • 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
    • C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
    • C09B29/0092—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with two nitrogen and one sulfur as heteroatoms
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Thermoplastics are coloured with dyes of formula (I): where A' is a gp. A or a gp. (II) D is the residue of a diazo component, R is H, alkyl or (methyl)phenyl, X is H, carbamoyl or CN, Z is a (cyclo) alkylene, aralkylene or arylene gp., where the alkylene gp. may be interrupted by O, S or N-substd. imino, and A is H, (substd.) (cyclo)alkyl, aralkyl, phenyl or acyl or may together form a 5-7 membered heterocyclic ring with N. (I) are used for dyeing thermoplastics in bulk at is not >300 degrees C, e.g polystyrene, hard PVC, polyethylene, polyamides, polyesters, polycarbonates, styrene-butadiene copolymers and ABS copolymers. (I) are stable to heat. They have up to 3.5 x the colour strength of dyes normally used for dyeing in bulk.

Description

Thermoplastfarbstoffe Die Erfindung betrifft die Verwendung von Farbstoffen der Formel 1 in der D den Rest einer Diazokomponente, R Wasserstoff, Alkyl, Methylphenyl oder Phenyl, X Wasserstoff, Carbamoyl oder Cyan und die Reste A unabhängig voneinander Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl, Aralkyl, Phenyl oder Acyl bedeuten, zum Färben von Thermoplasten.Thermoplastic dyes The invention relates to the use of dyes of the formula 1 in which D is the radical of a diazo component, R is hydrogen, alkyl, methylphenyl or phenyl, X is hydrogen, carbamoyl or cyano and the radicals A are independently hydrogen, optionally substituted alkyl, cycloalkyl, aralkyl, phenyl or acyl, for dyeing thermoplastics.

Die Reste-D leiten sich insbesondere von Aminen der Benzol, Benzthiazol-, Benzisothiazol-, Thiazol-, Thiadiazol-, Thiophen-, Azobenzol- oder Anthrachinonreihe ab.The radicals-D are derived in particular from amines of benzene, benzothiazole, Benzisothiazole, thiazole, thiadiazole, thiophene, azobenzene or anthraquinone series away.

Als Substituenten für die Reste D der Diazokomponenten sind beispielsweise zu nennen: In der Benzolreihe: Chlor, Brom, Vitro, Cyan, Trifluormethyl, Methyl sulfonyl, Äthylsulfonyl, Phenylsulfonyl, Carbomethoxy, Carbobutoxy, Carbo-B-methoxyäthoxy, Carbo-B-hydroxyäthoxy, gegebenenfalls N-mono-oder N-disubstituiertes Carbon- oder Sulfonamid, Methyl, Äthyl, Butyl, Octyl, Hexyl, Methoxy oder Äthoxy.Substituents for the radicals D of the diazo components are, for example to be mentioned: In the benzene series: chlorine, bromine, vitro, cyano, trifluoromethyl, methyl sulfonyl, ethylsulfonyl, phenylsulfonyl, carbomethoxy, carbobutoxy, carbo-B-methoxyethoxy, Carbo-B-hydroxyethoxy, optionally N-mono- or N-disubstituted carbon- or Sulfonamide, methyl, ethyl, butyl, octyl, hexyl, methoxy or ethoxy.

N-Substituenten der Carbon- oder Sulfonamide sind dabei z. B. Methyl, Äthyl, Propyl, Butyl, B-Hydroxyäthyl, y-Hydroxypropyl, ß-Methoxyäthyl, y-Methoxypropyl oder y-Äthoxypropyl sowie das Pyrrolidid, Piperidid oder Morpholid.N-substituents of the carbon or sulfonamides are z. B. methyl, Ethyl, propyl, butyl, B-hydroxyethyl, γ-hydroxypropyl, ß-methoxyethyl, γ-methoxypropyl or γ-ethoxypropyl and the pyrrolidide, piperidide or morpholide.

In der Azobenzolreihe: Chlor, Brom, Nitro, Cyan, Methyl, Äthyl, Methoxy oder Äthoxy.In the azobenzene series: chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy or ethoxy.

In der heterocyclischen Reihe: Chlor, Brom, Nitro, Cyan, Methyl, Äthyl, Phenyl, Methoxy, Äthoxy, Methylmeroapto, ß-Carbomethoxyäthylmercapto, ß-Carboäthoxyäthylmercapto, Carbomethoxy, Carboäthoxy, Acetyl, Nethylsulfonyl oder Äthylsulfonyl.In the heterocyclic series: chlorine, bromine, nitro, cyano, methyl, ethyl, Phenyl, methoxy, ethoxy, methyl meroapto, ß-carbomethoxyethyl mercapto, ß-carboethoxyethyl mercapto, Carbomethoxy, Carboethoxy, Acetyl, Nethylsulfonyl or Ethylsulfonyl.

Bevorzugt sind Diazokomponenten mit mindestens einem Substituenten wie Methylsulfonyl, Phenylsulfonyl, Äthylsulfonyl, Carbalkoxy, gegebenenfalls N-substituiertes Carbamoyl und insbesondere Nitro oder Cyan.Diazo components with at least one substituent are preferred such as methylsulfonyl, phenylsulfonyl, ethylsulfonyl, carbalkoxy, optionally N-substituted Carbamoyl and especially nitro or cyano.

Der Rest D leitet sich im einzelnen z. B. von folgenden Aminen ab: o-, m- oder p-Nitroanilin, o-, m- oder p-Cyananilin, 2,4-Dicyananilin, 2,4,6-Tribromanilin, 2-Chlor-4-nitroanilin, 2-Brom-4-nitroanilin, 2-Cyan-4-nitroanilin, 2-Methylsulfonyl-4-nitroanilin, 2-Methyl-4-nitroanilin, 2-Methoxy-4-nitroanilin, 4-Chlor-2-nitroanilin, 4-Methyl-2-nitroanilin, 2-Hexyl-4-nitroanilin, 4-Methoxy-2-nitroanilin, 1-Amino-2-trifluormethyl-4-chlorbenzol, 2-Chlor-5-aminobenzonitril, 2-Amino-5-chlor-benzonitril, 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, 1-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-dibrombenzol-4-methylsulfon, 1-Amino-2, 6-dichlorbenzol-4-methylsulfon, 1-Amino-2, 4-dinitrobenzol-6-carbonsäuremethylester oder -ß-methoxyäthylester, 3,5-Dichloranthranilsäurepropylester, 3,5-Dibromanthranilsäure-ß-methoxyäthylester, N-Acetyl-p-phenylendiamin, 4-Aminoacetophenon, 4- oder 2-Aminobenz 0-phenon, 2- und 4-Aminodiphenylsulfon, 5-Nitroanthranilsäuremethylester, -isobutylester, -methyldiglykolester, -ß-methoxyäthylester, -ß-butoxyäthylester, -ß-acetoxyäthylester, 3- oder 4-Aminophthalsäure-, 3-Amino-6-nitrophthalsäure-ß-hydroxyäthylamid, Methylsulfonsäure-2'-, -3'- oder -4'-aminophenylester, Äthylsulfonsäure-2'-, -3'- oder-4'-aminophenylester, Butylbulfonsäure-2' -, -3'- oder -4'-aminophenylester, Benzolsulfonsäure-2'-, -3'- oder -4'-aminophenylester, 2-Aminoanthrachinon, 1 -Amino-4-chloranthrachinon, 2-Aminobenzthiazol, 2-Amino-6-carbonsäuremethylesterbenzthiazol, 2-Amino-6-methylsulfonylbenzthiazol, 2-Amino-6-cyanbenzthiazol, 2-Amino-6-nitrobenzthiazol, 5,6- oder 6,7-Dichlor-2-aminobenzthiazol, 4-Amino-5-brom-7-nitro-1,2-benzisothiazol, 3-Amino-5-nitro-2, 1-benzisothiazol, 5-Amino-5-nitro-7-brom-2, 1-benzisothiazol, 2-Aminothiazol, 2-Amino-5-nitrothiazol, 2-Amino-4-methylthiazol 5-carbonsäureäthylester, 2-Amino-4-methyl-5-acetylthiazol, 2-Amino-3-cyan-4-methylthiphen-5-carbonsäureester, 2-Phenyl-5-amino-1,3,4-thiadiazol, 3-Methylmercapto-5-amino-1,2,4-thiadiazol, 3-ß-Carbomethoxyäthylmercapto-5-amino-1,2,4-thiadiazol, 2,4-Dicyan-3,5-dimethylanilin. The remainder D is derived in detail z. B. from the following amines: o-, m- or p-nitroaniline, o-, m- or p-cyananiline, 2,4-dicyananiline, 2,4,6-tribromaniline, 2-chloro-4-nitroaniline, 2-bromo-4-nitroaniline, 2-cyano-4-nitroaniline, 2-methylsulfonyl-4-nitroaniline, 2-methyl-4-nitroaniline, 2-methoxy-4-nitroaniline, 4-chloro-2-nitroaniline, 4-methyl-2-nitroaniline, 2-hexyl-4-nitroaniline, 4-methoxy-2-nitroaniline, 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, 1-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 -ß-methoxyethyl ester, 3,5-dichloroanthranilic acid propyl ester, 3,5-dibromanthranilic acid-ß-methoxyethyl ester, N-acetyl-p-phenylenediamine, 4-aminoacetophenone, 4- or 2-aminobenz 0-phenone, 2- and 4-aminodiphenylsulfone, 5-nitroanthranilic acid methyl ester, -isobutyl ester, -methyldiglycol ester, -ß-methoxyethyl ester, -ß-butoxyethyl ester, -ß-acetoxyethyl ester, 3- or 4-aminophthalic acid, 3-amino-6-nitrophthalic acid-ß-hydroxyethylamide, Methylsulfonic acid 2'-, -3'- or -4'-aminophenyl ester, ethylsulfonic acid 2'-, -3'- or 4'-aminophenyl ester, butyl sulfonic acid 2 ', -3'- or -4'-aminophenyl ester, Benzenesulfonic acid 2'-, -3'- or -4'-aminophenyl ester, 2-aminoanthraquinone, 1 -Amino-4-chloroanthraquinone, 2-aminobenzothiazole, 2-amino-6-carboxylic acid methyl ester benzothiazole, 2-amino-6-methylsulfonylbenzthiazole, 2-amino-6-cyanobenzothiazole, 2-amino-6-nitrobenzthiazole, 5,6- or 6,7-dichloro-2-aminobenzothiazole, 4-amino-5-bromo-7-nitro-1,2-benzisothiazole, 3-Amino-5-nitro-2, 1-benzisothiazole, 5-amino-5-nitro-7-bromo-2, 1-benzisothiazole, 2-aminothiazole, 2-amino-5-nitrothiazole, 2-amino-4-methylthiazole, 5-carboxylic acid ethyl ester, 2-amino-4-methyl-5-acetylthiazole, 2-amino-3-cyano-4-methylthiphen-5-carboxylic acid ester, 2-phenyl-5-amino-1,3,4-thiadiazole, 3-methylmercapto-5-amino-1,2,4-thiadiazole, 3-ß-carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole, 2,4-dicyano-3,5-dimethylaniline.

Geeignete Diazokomponentsn 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-aminobenzol, 2-Methyl-4',5-dimethoxy-4-aminoazobenzol, 4'-Ohlor-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-aminobenzol, 4'-Chlor-2,5-dimethyl-4-aminobenzol, 4'-Methoxy-2,5-dimethyl-4-aminoazobenzol, 4'-Nitro-4-aminoazobenzol, 3,5-Dibrom-4-aminoazobenzol, 2,3'-Dichlor-4-aminoazobenzol, 3-Nethoxy-4-aminoazobenzol, 4'-Hydroxy-2'-methyl-4-aminoazobenzol.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-aminobenzene, 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-aminobenzene, 4'-chloro-2,5-dimethyl-4-aminobenzene, 4'-methoxy-2,5-dimethyl-4-aminoazobenzene, 4'-nitro-4-aminoazobenzene, 3,5-dibromo-4-aminoazobenzene, 2,3'-dichloro-4-aminoazobenzene, 3-Nethoxy-4-aminoazobenzene, 4'-hydroxy-2'-methyl-4-aminoazobenzene.

Reste R sind neben Wasserstoff beispielsweise Äthyl, n- oder i-Propyl, Butyl, Pentyl, a-Äthylpentyl, Phenyl oder Methylphenyl und vorzugsweise Methyl.In addition to hydrogen, radicals R are, for example, ethyl, n- or i-propyl, Butyl, pentyl, a-ethylpentyl, phenyl or methylphenyl and preferably methyl.

Neben Wasserstoff kommen für A z. B. die folgenden Substituenten in Betracht: Alkyl mit 1 bis 8 C-Atomen, gegebenenfalls durch Hydroxy, Cyan, Alkoxy mit 1 bis 8 C-Atomen, Phenoxy, Phenoxyäthoxy oder Benzyloxy substituiertes Alkyl, Cyclohexyl, Norbornyl, Benzyl, Phenyläthyl, Phenylhydroxyäthyl, Phenylpropyl, Phenylbutyl, gegebenenfalls durch Chlor, Methyl, Methoxy oder Äthoxy substituiertes Phenyl, Polyalkoxyalkyl, Hydroxypolyalkoxyalkyl, Alkanoyloxyalkyl oder Alkoxycarbonylalkyl, sowie Alkanoyl, Aralkanoyl, Aroyl, Alkylsulfonyl oder Arylsulfonyl.In addition to hydrogen, A z. B. the following substituents in Consideration: alkyl having 1 to 8 carbon atoms, optionally through hydroxy, cyano, alkoxy alkyl substituted with 1 to 8 carbon atoms, phenoxy, phenoxyethoxy or benzyloxy, Cyclohexyl, norbornyl, benzyl, phenylethyl, phenylhydroxyethyl, phenylpropyl, phenylbutyl, phenyl, polyalkoxyalkyl, optionally substituted by chlorine, methyl, methoxy or ethoxy, Hydroxypolyalkoxyalkyl, alkanoyloxyalkyl or alkoxycarbonylalkyl, as well as alkanoyl, Aralkanoyl, aroyl, alkylsulfonyl or arylsulfonyl.

Als Reste A kommen im einzelnen außer den schon genannten z. B. in Betracht: 1. gegebenenfalls substituierte Alkylreste: CH3, C2H5, n- oder i-C3H7, n- oder i-C4H9, C6H13, CH2CH2OH, (CH2)3OH, (CH2)40H, (CH2)60H, (CH2)2O(CH2)2OH, (CH2)3O(CH2)4OH, (CH2)3OC2H4OH, (CH2)2CN, (CH2)5CN, (CH2)6CH, (CH2)7CN, (CH2)2O(CH2)2CN, (CH2)3O(CH2)2CN (CH2)2O(CH2)2O(CH2)2CN, (CH2)3OC2H4OCH3, (CH2)3OC2H4OC2H5, (CH2)3O(CH2)6OH, (CH)3OC2H4OCH(CH3)2, (CH2)3OC2H4OC4H9, (CH2)3OC2H4OCH2C6H5, (CH2)3OC2H4OC2H4C6H5, (CH2)3OC2H4OC6H5, (CH2)3OCHCH2OC4H9, CH3 die entsprechenden Reste, bei denen die Gruppierungen oder -OCH-OH2-zwei- oder dreimal vorhanden sind; CH2CH2OCH3, CH2CH2OC2H5, CH2CH2OC3H7, CH2CH2OC4H9, CH2CH2OC6H5, (CH2)3OCH3, (CH2)3OC2H5, (CH2)3OC3H7, (CH2)3OC4H9, (CH2)3OC6H13, (CH2)3OC8H17, (CH2)3O-, (CH2)3OCH2C6H5, (CH2)3OC2H4C6H5, (CH2)3OC6H5, 2. gegebenenfalls substituierte Cyclo- und Polycycloalkylreste: 3. Aralkylreste: CH2C6H5, C2H4C6H5, sowie C6H4CH3 anstelle von C6H5; 4. gegebenenfalls substituierte Phenylreste: C6H5, C6H4CH3, C6H3(CH3)2, C6H4OCH3, C6H4OC2H5, C6H4OCH2CH2OH oder C6H4Cl; 5. CH2CH=CH2, (CH2)5COOCH3, wobei n = 2, 3, 4 oder 6 ist, C2H4OCOCH3, C2H4OCHO, C2H4OCOCH3,(C2H4O)2COCH3, (C2H4O)2CHO, (CH2)3OCOCH3, (CH2)3OCHO.As radicals A come in detail apart from those already mentioned z. B. possible: 1. optionally substituted alkyl radicals: CH3, C2H5, n- or i-C3H7, n- or i-C4H9, C6H13, CH2CH2OH, (CH2) 3OH, (CH2) 40H, (CH2) 60H, (CH2) 2O (CH2) 2OH, (CH2) 3O (CH2) 4OH, (CH2) 3OC2H4OH, (CH2) 2CN, (CH2) 5CN, (CH2) 6CH, (CH2) 7CN, (CH2) 2O (CH2) 2CN, (CH2) 3O (CH2) 2CN (CH2) 2O (CH2) 2O (CH2) 2CN, (CH2) 3OC2H4OCH3, (CH2) 3OC2H4OC2H5, (CH2) 3O (CH2) 6OH, (CH) 3OC2H4OCH (CH3) 2 , (CH2) 3OC2H4OC4H9, (CH2) 3OC2H4OCH2C6H5, (CH2) 3OC2H4OC2H4C6H5, (CH2) 3OC2H4OC6H5, (CH2) 3OCHCH2OC4H9, CH3 the corresponding residues in which the groupings or -OCH-OH2-are present two or three times; CH2CH2OCH3, CH2CH2OC2H5, CH2CH2OC3H7, CH2CH2OC4H9, CH2CH2OC6H5, (CH2) 3OCH3, (CH2) 3OC2H5, (CH2) 3OC3H7, (CH2) 3OC4H9, (CH2) 3OC6H13, (CH2) 3OC8H17, (CH2) 3O-, (CH2) 3OCH2C6H5, (CH2) 3OC2H4C6H5, (CH2) 3OC6H5, 2. optionally substituted cyclo- and polycycloalkyl radicals: 3. Aralkyl radicals: CH2C6H5, C2H4C6H5, as well as C6H4CH3 instead of C6H5; 4. optionally substituted phenyl radicals: C6H5, C6H4CH3, C6H3 (CH3) 2, C6H4OCH3, C6H4OC2H5, C6H4OCH2CH2OH or C6H4Cl; 5. CH2CH = CH2, (CH2) 5COOCH3, where n = 2, 3, 4 or 6, C2H4OCOCH3, C2H4OCHO, C2H4OCOCH3, (C2H4O) 2COCH3, (C2H4O) 2CHO, (CH2) 3OCOCH3, (CH2) 3OCHO.

6. CHO, CH3CO, C2H5CO, C3H7CO, C2H5CO, CH3C6H4CO, C6H5CH2CO, C6H5OCH2CO, CH3SO2, C2H5SO2, C6H5SO2 oder CH3C6H4SO2.6. CHO, CH3CO, C2H5CO, C3H7CO, C2H5CO, CH3C6H4CO, C6H5CH2CO, C6H5OCH2CO, CH3SO2, C2H5SO2, C6H5SO2 or CH3C6H4SO2.

Bevorzugte Substituenten A sind beispielsweise: Wasserstoff, CH3, C2H5, n- oder i-C3H7, n- oder i-O4H9, C6H13, OH2CH2OH, (CH2)30H, (CH2)4OH, (CH2)6OH, (CH2)2O(CH2)2OH, (CH2)3O(CH2)2OH, (CH2)3O(CH2)4OH, (CH2)3O(CH2)6OH, CH2CH2OCH3, CH2CH2OC2H5, CH2CH2OC4H9, (CH2)3OCH3, (CH2)3OC2H5, (CH2)3OC3H7, (CH2)3OC4H9, (CH2)3OC2H4OCH3, (CH2)3OC2H4OC4H9, (CH2)3OC2H4OC6H5, CH2C6H5, C2H4C6H5, C6H5, C6H4CH3, C6H4OCH3 oder C6H4OC2H4OH.Preferred substituents A are, for example: hydrogen, CH3, C2H5, n- or i-C3H7, n- or i-O4H9, C6H13, OH2CH2OH, (CH2) 30H, (CH2) 4OH, (CH2) 6OH, (CH2) 2O (CH2) 2OH, (CH2) 3O (CH2) 2OH, (CH2) 3O (CH2) 4OH, (CH2) 3O (CH2) 6OH, CH2CH2OCH3, CH2CH2OC2H5, CH2CH2OC4H9, (CH2) 3OCH3, (CH2) 3OC2H5, (CH2) 3OC3H7, (CH2) 3OC4H9, (CH2) 3OC2H4OCH3, (CH2) 3OC2H4OC4H9, (CH2) 3OC2H4OC6H5, CH2C6H5, C2H4C6H5, C6H5, C6H4CH3, C6H4OCH3 or C6H4OC2H4OH.

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, R, X und A die angegebene Bedeutung haben.To prepare the dyestuffs of the formula I, a diazo compound of amines of the formula II D-NH2 II can be used with coupling components of the formula III implement, where D, R, X and A 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 stark bis schwach 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 strongly to weakly acidic reaction carried out.

Die Herstellung der Farbstoffe der Formel I ist in dem Patent (Patentanmeldung P 20 62 717.2) beschrieben, die Angaben dort gelten hier sinngemäß.The preparation of the dyes of the formula I is described in the patent (patent application P 20 62 717.2), the information there applies accordingly.

Technisch besonders wertvoll sind Farbstoffe und Farbstoffgemische der Formel I a in der B Nitro, Cyan, Chlor, Brom, Trifluormethyl, Carbomethoxy, Carboäthoxy, ß-Methoxyearbäthoxy, Methylsulfonyl, Äthylsulfonyl, Methyl, Methoxy oder Phenylazo, B1 2'asserstoff, Nitro, Chlor, Brom, Cyan, Methyl, Methoxy, Carbomethoxy, Phenylsulfonyl, Carboäthoxy, Methylsulfonyl oder Äthylsulfonyl und B2 Wasserstoff, Chlor, Brom, Cyan oder Methyl und A unabhängig voneinander Wasserstoff gegebenenfalls substituiertes Alkyl, Cycloalkyl, Aralkyl, Phenyl oder Acyl bedeuten.Dyes and dye mixtures of the formula I a are particularly useful industrially in B nitro, cyano, chlorine, bromine, trifluoromethyl, carbomethoxy, carboethoxy, ß-methoxyearbethoxy, methylsulfonyl, ethylsulfonyl, methyl, methoxy or phenylazo, B1 2'hydrogen, nitro, chlorine, bromine, cyano, methyl, methoxy, carbomethoxy, Phenylsulfonyl, carboethoxy, methylsulfonyl or ethylsulfonyl and B2 denote hydrogen, chlorine, bromine, cyano or methyl and A independently denote hydrogen, optionally substituted alkyl, cycloalkyl, aralkyl, phenyl or acyl.

Sauerstoffhaltige Reste A, insbesondere solche mit Alkoxygruppen, sind bevorzugt.Oxygen-containing radicals A, in particular those with alkoxy groups, are preferred.

Weiterhin sind besonders wertvoll die entsprechenden Farbstoffe, die als Diazokomponenten gegebenenfalls durch Nitro, Chlor, Brom, Cyan, Methyl, Methylmercapto, ß-Carbomethoxyäthylmercapto, ß-Carboäthoxyäthylmercapto, Carbomethoxy, Carboäthoxy oder Acetal substituiertes Benzthiazol, Benzisothiazol, Thiazol, Thiadia7,ol oder Thiophen enthalten.Furthermore, the corresponding dyes are particularly valuable as diazo components, if necessary by nitro, chlorine, bromine, cyano, methyl, methyl mercapto, ß-Carbomethoxyäthylmercapto, ß-Carboethoxyäthylmercapto, Carbomethoxy, Carboethoxy or acetal substituted benzothiazole, benzisothiazole, thiazole, thiadia7, ol or Contains thiophene.

Von den besonders wertvollen Diazokomponenten seien im einzelnen genannt: 4-Nitroanilin, 2-Chlor-4-nitroanilin, 2-Brom-4-nitroanilin, 2-Cyan-4-nitroanilin, 2-Methoxy-4-nitroanilin, 2-Amino-5-nitrophenylsulfonsäuredimethylamid, 2-Amino-5-nitrophenylsulfonsäurebutylamid, 2-Amino-5-nitrophenylsulfonsäure-B-methoxyäthylamid, 2-Aminobenzonitril, 3-Chlor-4-aminobenzonitril, 2-Chlor-5-aminobenznitril, 2-Amino-5-chlorbenzonitril, 3,5-Dichlor-2-aminobenzonitril, 1 -Amino-2,4-dicyanbenzol, 1-Amino-2,4-dicyan-6-chlorbenzol' 2-Chlor-4-amino-5-nitrobenzonitril, 2-Amino-3-chlor-5-nitrobenzonitril, 2-Amino-3-brom-5-nitrobenzonitril, 2,6-Dicyan-4-nitroanilin, 2,5-Dichlor-4-nitroanilin, 2,6-Dichlor-4-nitroanilin, 2,6-Dibrom-4-nitroanilin, 2-Chlor-6-brom-4-nitroanilin, 2,4-Dinitroanilin, 2,4-Dinitro-6-chloranilin, 2,4-Dinitro-6-bromanilin, 2-Amino-3, 5-dinitrobenzonitril, 1 -Amino-4-nitrobenzol-2-methylsulfon, 1-Amino-4-nitrobenzol-2-äthylsulfon, 4-Methylsulfonylanilin, 1-Amino-2-chlorbenzol-4-methylsulfon, 1-Amino-2,6-dibrombenzol-4-methylsulfon, 1-Amino-2,6-dichlorbenzol-4-methylsulfon, 2-Amino-diphenylsulfon, 2-Amino-5-nitrobenzoesäure ester, 2-Amino-3-chlor-5-nitrobenzoesäureester, 2-Amino-3,5-dichlorbenzoesäureester, 4-Aminoazobenzol, 2,3'-Dimethyl-4-aminoazobenzol, 2',3-Dimethyl-4-aminoazobenzol, 2,5-Dimethyl-4-aminoazobenzol, 3,5-Dibrom-4-aminoazobenzol, 2,4-Dicyan-3,5-dimethylanilin, 2-Trifluormethylanilin, 2-Trifluormethyl-4-chloranilin.Some of the particularly valuable diazo components are: 4-nitroaniline, 2-chloro-4-nitroaniline, 2-bromo-4-nitroaniline, 2-cyano-4-nitroaniline, 2-methoxy-4-nitroaniline, 2-amino-5-nitrophenylsulfonic acid dimethylamide, 2-amino-5-nitrophenylsulfonic acid butylamide, 2-amino-5-nitrophenylsulfonic acid-B-methoxyethylamide, 2-aminobenzonitrile, 3-chloro-4-aminobenzonitrile, 2-chloro-5-aminobenzonitrile, 2-amino-5-chlorobenzonitrile, 3,5-dichloro-2-aminobenzonitrile, 1-amino-2,4-dicyanobenzene, 1-amino-2,4-dicyan-6-chlorobenzene ' 2-chloro-4-amino-5-nitrobenzonitrile, 2-amino-3-chloro-5-nitrobenzonitrile, 2-amino-3-bromo-5-nitrobenzonitrile, 2,6-dicyan-4-nitroaniline, 2,5-dichloro-4-nitroaniline, 2,6-dichloro-4-nitroaniline, 2,6-dibromo-4-nitroaniline, 2-chloro-6-bromo-4-nitroaniline, 2,4-dinitroaniline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-bromaniline, 2-amino-3, 5-dinitrobenzonitrile, 1-amino-4-nitrobenzene-2-methylsulfone, 1-amino-4-nitrobenzene-2-ethylsulfone, 4-methylsulfonylaniline, 1-amino-2-chlorobenzene-4-methylsulfone, 1-amino-2,6-dibromobenzene-4-methylsulfone, 1-amino-2,6-dichlorobenzene-4-methylsulfone, 2-amino-diphenylsulfone, 2-amino-5-nitrobenzoic acid ester, 2-amino-3-chloro-5-nitrobenzoic acid ester, 2-amino-3,5-dichlorobenzoic acid ester, 4-aminoazobenzene, 2,3'-dimethyl-4-aminoazobenzene, 2 ', 3-dimethyl-4-aminoazobenzene, 2,5-dimethyl-4-aminoazobenzene, 3,5-dibromo-4-aminoazobenzene, 2,4-dicyano-3,5-dimethylaniline, 2-trifluoromethylaniline, 2-trifluoromethyl-4-chloroaniline.

Von den besonders wertvollen heterocyclischen Diazokomponenten seien erwähnt: 2-Amino-5-nitrothiazol, 2-Amino-4-methyl-5-nitrothiazol, 2-Amino-4-methylthiazol-5-carbonsäureäthylester, 2-Amino-5-phenyl 1,3,4-thiadiazol, 3-Phenyl-5-amino-1,2,4-thiadiazol, 3-Methylmercapto-5-amino-1,2,4-thiadiazol, 3-ß-Carbomethoxyäthylmercapto-5-amino-1,2,4-thiadiazol, 3-ß-Carboäthoxyäthylmercapto-5-amino-1,2,4-thiadiazol, 2-Amino-6-cyanbenzthiazol, 2-Amino-6-carbonsäuremethylesterbenzthiazol, 2-Amino-6-nitrobenzthiazol, 2-Amino-3-cyan-4-methylthiophen-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-benzi 8 othiazol, 4-Aminobenzisothiazol.Of the particularly valuable heterocyclic diazo components are mentioned: 2-amino-5-nitrothiazole, 2-amino-4-methyl-5-nitrothiazole, 2-amino-4-methylthiazole-5-carboxylic acid ethyl ester, 2-amino-5-phenyl 1,3,4-thiadiazole, 3-phenyl-5-amino-1,2,4-thiadiazole, 3-methylmercapto-5-amino-1,2,4-thiadiazole, 3-ß-Carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole, 3-ß-Carboethoxyethylmercapto-5-amino-1,2,4-thiadiazole, 2-amino-6-cyanobenzothiazole, 2-amino-6-carboxylic acid methyl ester benzothiazole, 2-amino-6-nitrobenzthiazole, 2-amino-3-cyano-4-methylthiophene-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-benzi 8 othiazole, 4-aminobenzisothiazole.

Überraschenderweise eignen sich die Farbstoffe der Formel I zum Färben zu von Thermoplasten in der Masse, bei Temperaturen von bis ungefähr 300 00. Dieses Verhalten war bei den Azofarbstoffen der Formel I nicht vorhersehbar, da Dispersions-Azofarbstoffe normalerweise nicht so temperaturstabil sind. Insbesondere überrascht es, daß die Azo-Farbstoffe beim Einschmelzen in Polyamid hoch temperaturstabil sind. Färbbare Thermoplasten sind beispielsweise Polystyrol, Hart-Polyvinylchlorid, Polyäthylen, Polyamid, Polyester, Polypropylen, sowie Styrol-Butadien Gemische oder Acrylnitril-Butadien-Styrol Gemische. Man erhält Färbungen mit vorzüglichen Echtheiten, insbesondere Licht-, Wetter- und Weichmacherechtheiten. Die Weichmacherechtheiten lassen sich zudem durch die Wahl der Reste A steuern, die Lichtechtheit hängt im wesentlichen von D und X ab.Surprisingly, the dyes of the formula I are suitable for dyeing to of thermoplastics in bulk, at temperatures of up to about 300 00. This The behavior of the azo dyes of the formula I could not be foreseen, as dispersion azo dyes are usually not as temperature stable. In particular, it is surprising that the Azo dyes are highly temperature stable when melted in polyamide. Dyeable Thermoplastics are, for example, polystyrene, hard polyvinyl chloride, polyethylene, Polyamide, polyester, polypropylene, as well as styrene-butadiene mixtures or acrylonitrile-butadiene-styrene Mixtures. The dyeings obtained have excellent fastness properties, in particular light, Weather and plasticizer fastnesses. The plasticizer fastnesses can also be passed through control the choice of the radicals A, the light fastness depends essentially on D and X off.

In den folgenden Beispielen beziehen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht.In the following examples, parts and percentages relate to unless otherwise noted, by weight.

Beispiel 1 29,5 Teile 2-Aminobenzonitril werden bei Raumtemperatur in 800 Raumteilen Wasser und 80 Raumteilen 30 zeiger Salzsäure gelöst. Dann setzt man 750 Teile Eis und bei 0 bis 5 0 77 Baumteile einer 23 zeigen Natriumnitritlösung auf einmal zu. Nach zwei Stunden Rühren bei 0 bis 5 0 wird die klare bis trübe Diazoniumsalzlösung mit folgender Suspenion versetzt: 66,0 Teile 2,6-Bis-(ß-methoxyäthylamino)-5-cyan-4-methylpyridin werden in 80 Raumteilen Dimethylformamid unter Erwärmen gelöst, dann setzt man 12,5 Teile eines Anlagerungsproduktes von etwa 23 Mol Äthylenoxyd an 1 Mol Spermölalkohol zu und gibt die Lösung unter Rühren zu einem Gemisch aus 30 Raumteilen 30 %iger Salzsäure und 10Q0 Raumteilen Wasser.Example 1 29.5 parts of 2-aminobenzonitrile are at room temperature dissolved in 800 parts by volume of water and 80 parts by volume of 30 pointers hydrochloric acid. Then sets 750 parts of ice and 0 to 5 0 77 tree parts of a 23 show sodium nitrite solution at once to. After two hours of stirring at 0 to 50, the clear to cloudy diazonium salt solution becomes mixed with the following suspension: 66.0 parts of 2,6-bis (ß-methoxyethylamino) -5-cyano-4-methylpyridine are dissolved in 80 parts by volume of dimethylformamide with heating, then 12.5 are added Parts of an adduct of about 23 moles of ethylene oxide with 1 mole of sperm oil alcohol and adds the solution with stirring to a mixture of 30 parts by volume of 30% strength Hydrochloric acid and 10Q0 parts by volume of water.

lö sung Die Kupplungswird mit etwa 500 bis 1000 Teilen Eis und dann mit etwa 65 Teilen 50 %iger Natronlauge versetzt, bis der pE-wert des Gemisches 2,5 bis 3,2 ist. Nach beendeter Kupplung wird das Gemisch auf 70 OC erwärmt, abfiltriert und mit heißem Wasser gewaschen. Nach dem Trocknen erhält man etwa 97 bis 98 Teile eines gelben Pulvers der Formel das sich in Dimethylformamid mit gelber Farbe löst.solution The coupling is mixed with about 500 to 1000 parts of ice and then with about 65 parts of 50% sodium hydroxide solution until the pE value of the mixture is 2.5 to 3.2. After the coupling has ended, the mixture is heated to 70 ° C., filtered off and washed with hot water. After drying, about 97 to 98 parts of a yellow powder of the formula are obtained which dissolves in dimethylformamide with a yellow color.

0,5 Teile dieses Farbstoffes werden mit 1000 Teilen Polystyrolgranulat oder -Pulver nach bekanntem Verfahren intensiv vermischt. Anschließend wird das Gemisch geschmolzen. Der Farbstoff löst sich dabei und ist in der Schmelze bis 300 0 stabil. Nach dem Erstarren erhält man eine kräftig gelb gefärbte Polystyrolmasse mit vorzüglicher Lichtechtheit.0.5 parts of this dye are mixed with 1000 parts of polystyrene granules or powder mixed intensively according to a known method. Then the Melted mixture. The dye dissolves in the process and is up to 300 in the melt 0 stable. After solidification, a bright yellow colored polystyrene mass is obtained with excellent lightfastness.

Der Farbstoff läßt sich ebenso temperaturstabil in Polyamid einschmelzen.The dye can also be melted into polyamide in a temperature-stable manner.

Auch diese Massefärbung ist sehr gut lichtecht. Weiterhin ist er sehr gut zur Massefärbung von Polypropylen, Polyäthylen, Polyvinylchlorid und Polyester geeignet.This mass coloring is also very lightfast. Furthermore, he is very good for mass coloring polypropylene, polyethylene, polyvinyl chloride and polyester suitable.

Beispiel 2 78 Teile 1-Amino-2-trifluormethyl-4-chlor-benzol werden bei 0 bis 20 °C in 400 Teilen96 der Schwefelsäure ist. Man kühlt das Gemisch auf 0 - 4 °C ab, setzt 130 Teile 45 %ige Nitrosylschwefelsäure zu und rührt 3 Stunden bei 0 bis 5 00. Dann wird das Gemisch unter Rührern auf 1200 Teile Eis gegeben, 30 Minuten nachgerührt und filtriert. Nach Zerstörung von überschüssiger salpetriger Säure wird die Diazoniumsalzlösung mit 117 Teilen der Kupplungskomponente der Formel versetzt und der pH-Wert der Kupplungslösung durch Zusatz von Natronlauge bei 0 bis 50C auf 2 bis 3 angehoben. Nach beendeter Kupplung saugt man den ausgefallenen Farbstoff der Formel ab, wäscht ihn mit Wasser und trocknet.Example 2 78 parts of 1-amino-2-trifluoromethyl-4-chlorobenzene are dissolved in 400 parts of sulfuric acid at 0 to 20 ° C. The mixture is cooled to 0-4 ° C., 130 parts of 45% strength nitrosylsulfuric acid are added and the mixture is stirred for 3 hours at 0-5,000. The mixture is then poured onto 1200 parts of ice with stirring, stirred for 30 minutes and filtered. After excess nitrous acid has been destroyed, the diazonium salt solution with 117 parts of the coupling component of the formula added and the pH of the coupling solution was raised to 2 to 3 by adding sodium hydroxide solution at 0 ° to 50 ° C. After the coupling has ended, the dyestuff of the formula which has precipitated out is sucked off wash it off with water and dry it.

Färbt man 1 000 Teile Polystyrol mit 0,5 Teilen dieses Farbstoffs analog Beispiel 1, so erhält man eine gelb gefärbte Polystyrolmasse mit sehr guter Lichtechtheit.1,000 parts of polystyrene are dyed with 0.5 part of this dye analogously to Example 1, a yellow-colored polystyrene composition with a very good color is obtained Lightfastness.

In gleicher Weise kann man auch die in den folgenden Tabellen durch Angabe der Substituenten gekennzeichneten Farbstoffe zur Massefärbung verwenden, wobei man die ebenfalls angegebenen Farbtöne erhält.In the same way you can also go through those in the following tables Use indication of the substituents marked dyes for mass coloring, whereby the color shades also given are obtained.

Tabelle 1 Bsp, R1 B2 R4 R5 Farbt. der Nr. Nasnefärbun s. Polystyrol 3 CH2CH20CH3 (CH2)2ocH3 C3H7 ON E gelb 4 n ( 2)3 3 CH3 OH in n n 3 5 n n n n Cl n 6 n 02115 n n H n 7 n CE3 u n n n 8 II (Cz2)30C(CH3)2 n n zu n n 9 02115 (0H2)200113 n n n n 10 CH2CH20H n 1 1 u 1 2 2011 11 n 1' n II N n 12 CH2CH20H (0112)300113 0113 Cl n Cl 13 02115 X2H5 1 ON 11 n 14 " n n CF) H n 15 1 1 1 1 Bsp. R1 R2 R3 R4 R5 Farbt. der Nr. Massefärbung v Polystyrol 16 C2H5 CH2CH2OH CH3 CN H gelb 17 " (CH2)3OH " " " " 18 " " " CF3 Cl " 19 CH2CH2OCH3 CH2CH2OCH3 " " H " 20 C6H5 H " " " " 21 " CH2CH2OCH3 " " " " 22 C2H5 C2H5 " COOCH3" " 23 " CH2CH2OCH3 " " " " 24 " " " " Cl " 25 C4H9(n) " " CN " " 26 (CH2)3OCH(CH3)2 (CH2)3OCH(CH3)2 " CF3 H " 27 C6H13(n) CH2CH2OH " " " " 28 H C2H5 " CN Cl " 29 " " C3H7 " " " 30 " " " CF3 H " 31 " CH2CH2OCH3 CH3 " " " 32 " " " CN " " 33 " " " COOCH3 Cl " Bsp. R1 2 R3 R4 L5 Farbt. der Nr. j Massefärbung v. Polystyrol 7 34 jCH2Cll2OCH3 H CH3 CK H gelb 35 II II OF H n 3 36 tCH2CH2CH2°CH3 CH2CH2CH20CH3 " OCH3 CN H 37 | II ll H S02C6i {5" ll 38 CH2 CH2-C6H5 CH2CH20H CH3 CN ,. 39 ,l CH2CH20CH3 a It lt II 40 ,l n 0 3H7 lt II 41 II ,l CH3 " Cl 42 II CH,CH,CH,OCH, " 43 II CH2OH2C6H5 II lt II II 44 " II tl lt Cl 45 CH2CE-O-C6H5 CH2CH2OH2OCH3 II n H CH3 46 CH2CH2CH20C 6H5 OH2OH2OH lt :1 lt 47 CH2-C1H-C6H5 CH2CH2c;H20CH3 n " n , OH 48 (CH2)30CH2C6 H5 lt t lt lt n lt II 49 II OH2CH2 OH n s e II II Bsp. R1 R2 R3 R4 R5 Farbt. der Nr. Massefärbung v. Polystyrol 50 (CH2)30CH2C6H5 OH2-OH-OH3 CH3 CN H gelb OH 51 ( CH2)30CH2CH20C6H5 CH2CH20H n n ll 52 (CH2)30(CH2)40H 1 n n n tt 53 l(cH2) 30(CH2)20C4H9 " n 11 n n 54 O6H5 CH2CH2CH20CH3 n n n goldgelb 55 " II II C1 orange 56 6 4 3 II II H n 57 (OH2)6N$) n II n II gelb CH3 OH 13 58 -OH( II 1 II II n tt 1 0111 r 3( 3 OH3 59 OH2 0112001120112011 1' 1 1 11 60 i(CH,),O e CH2CH2°CH3 II n n n 61 0112011200113 II 11 SO2C6H5 1 L L 2 o c, 63 1(CH2)30CHCH20CH3 ON II n 63 J(CH),OCHCH,OCH, II 11 1' CH3 0113 64 (CH2)3°CH2C§H°C6H5 CH2CH20H n n n CH3 Bsp. 111 R2 R3 R4 R5 Farbt. der Nr. Massefärbung v. Polystyrol 65 (0112)6011 CH2CE2GH20CH3 3 ON H gelb 66 i(cE2)5-cg , , " , 67 |CH2CE2OCH3 n 06115 n II n 68 | II CII2CH20CH, - II CF3 C1 69 X II n H II II 02115 ON 1 70 l.oHsoooo 11 0113 CN n 1' 71 -(CH,) l 'l 72 1(CE2)5COOC2ff5 1 1 1 1 II II 73 (CH2)5sooc3X7 II n II II n 74 (CH2)5aOOC4Eg . * n s 75 CH2CH2-N CH2CH20CH, II II II n 0 76 CH2CE=CE2 n n n II II 77 CH2Cti=CEi2 CIfCH=CH2 II II n n 78 CZ2c32CH2°H (0112)300113 n n n n 79 CH2iH-C6E5 CE2CH20H o II II s ch-3 80 | C0I2CH2CH20C 5020113 n n a n Bsp. R1 R2 R3 R4 R5 Farbt. der Nr. Massefärbung v. l Polystyrol 81 CH2CH2CH2OCH3 COC6H5 CH3 CN H gelb 82 " SO2C6H5 " " " " 83 CH2CH2OCH3 " " " " " Tabelle 2 Bsp. R1 R2 R3 R4 R5 Farbt. der Nr. Massefärbung v. Polystyrol 84 H C2H5 H NO2 H goldgelb 85 " (CH2)3OCH3 " " " " 86 " (CH2)3OCH(CH3)2 " " " " 87 " (CH2)3OCH3 CH3 " " orange 88 " " OCH3 " " rotorange 89 C2H5 C2H5 " " " scharlach 90 n n H II " orange 91 " " CN " " scharlach 92 " C3H7(n) " " " " 93 " " " " Cl blaustichig rot 94 " C2H5 " " " " 95 (CH2)3OCH3 " " " " " 96 " " " " " scharlach Bsp. R1 R2 R3 R4 R5 Farbt. der Nr. Massefärbung v. Polystyrol 97 (CH2)3OCH3 C2H5 Cl NO2 H gelbstichig rot 98 H " " " " orange 99 " (CH2)3OCH3 " " " " 100 " " NO2 " " rot 101 C2H5 " " " " blaustichig rot 102 " " CN " Br " 103 CH2CH2OCOCH3 C2H5 " H H gelb 104 C2H5 CH2CH2OCOCH3 " " " " 105 CH2CH2OC6H5 CH2CH2CH2OCH3 Cl NO2 " orange 106 " " CN " " scharlach 107 CH2CH2CH2OC6H5 " " " " " 108 " " Cl " " orange 109 (CH2)3OCH2C6H5 " " " " " 110 (CH2)3OCH2C6H5 " CN " " scharlach 111 " " " " Cl blaustichig rot 112 " " " " Br " 113 " CH2CH2OH " " " " Bsp. R1 R2 R3 R4 R5 Farbt. der Nr. Massefärbung v. Polystyrol 114 (CH2)3OCH2C6H5 CH2CH2OH Cl NO2 H orange 115 " " CN " " scharlach 116 (CH2)3OCH2CH2C6H5 " " " " " 117 (CH2)3OCH2CH2OC6H5 " " " " " 118 " " Cl " " orange 119 " CH2CH2OCH3 " " " " 120 " " CN " " scharlach 121 " " NO2 " " rot 122 " CH2CH2OH " " " " 123 " " Br " " rotorange 124 " " COOCH3 " " " 125 " " H " " orange 126 " " SO2CH3 " " rot 127 " " CH3 " " orange 128 n n OCH3 " n n 129 " " SO2CH3 Cl " goldgelb 130 " CH2CH2OCH3 CN NO2 NO2 blaustichig rot 131 " " " " CN " 132 " " Cl " Cl gelbbraun Bsp. R1 R2 R3 R4 R5 Farbt. der Nr. Massefärbung v. Polystyrol 133 (CH2)3OCH2CH2OC6H5 CH2CH2OCH3 H SO2CH3 Cl gelb 134 " " Cl " H " 135 n n Br N02 Br gelbbraun 136 " CH2CH2OH COOCH3 Cl Cl gelb 137 " " Cl SO2C6H5H " 138 " " CN CN " orange 139 " " Cl Cl Cl gelb 140 CH2CH2CH2OCH3 CH2CH2CH2OCH3 " " " " 141 " " " SO2CH3 " " 142 " " H N=N-C6H5 H orange 143 CH2CH2OCH3 CH2CH2OCH3 " " " " 144 " " Cl SO2CH3 " gelb Tabelle @ Bsp. D R1 R2 X Farbt. der Nr. Massefärbung v. Polystyrol 145 u N CH2CH2CH20CH3 CH2CH2CH20CE3 CN rotstichig blau N 146 n .. . , ZONE2 blau 147 II n 11 148 II ( 2)3 4 9 OH2 011200113 CN violett 1130 ON 149 Ii 1 lt rot 0113 rot II n 150 lt (CH2)3oCB26 5 II In 151 N l,i lt ,I n blaustichig rot iS 152 lt CH2CH2CH20CH3 CH2CH2CH20CH3 lt tt Bsp. D R1 R2 X Farbt. der Nr. Massefärbung v. Polystyrol C113S 153 S CH2CH2CH20CH3 CH2CH2CH20CH3 CN orange 154 lt CE2CH20CH3 CH2CH20CH3 n II 155 n 06H5 n n scharlach 156 lt CH2CH2a6E5 CH2CH20H n orange 157 n n n H rot 158 n CE2CE2c6E5 CH2CE2a6R5 ON orange 011 00002118 159 1 1 II 160 n CH2CH20CH3 CE2CH20CH3 n n 161 1' CH2CH2o65 CH2CH2e65 lt n ON 162 02N 4 CH2CH20CE3 CH2CH20CH3 00NH2 rot 163 n II n H n 164 n CH2CH2CH20CH3 CH2CH2CE20CH3 n n 165 CN n n CONE2 n OH 166 2 4 l n n n blauetichig rot 167 lt n n H n Bsp. D R1 R2 X Farbt. der Nr. Massefärbung v. Polystyrol CN 168 02N 4 CE2CH2CH20CH3 CH2CH20H CONH2 blaustichig rot 169 lt CH2CE2 C6E5 . n n 170 a > CH2CH20CH3 CH2CH20CH3 CN scharlach 171 n CH2CH2CH20CH3 CH2CH2CH20CH3 lt N 172 Cl I, II n n 173 n CH2CH20CH3 CH2CE20CE3 lt 174 M n n rot 175 " lt CH2CH2CE20CE3 CH2CH2CH20CH3 tt lt °2 176 e u n n blaustichig rot 177 tt CEi2CH20CH, CH2CH20CH3 n a 3 178 lt lt lt n n n gelb O 179 n CH2CH2CH20CH3 CH2CH2CH20CH3 II II B8p. D R1 R2 X F2rBt der Bsp. D R1 R2 X Farbt0 der Nr. XLssefärbung v. Polystyrol S02CB, 180 02N V CH2CH2CH20CH3 CH2CH2CH20CH3 CN rot 181 lt n 1' CONH lt 182 H n II 11 183 4 lt C4Hs(") C4Hg(n) n lt 0 184 n CH2CH2CH20CH3 CH2CH2CH20CH!; CN braun 185 n 11 (0112)300211400113 n gelbbraun 186 S02 H H n gelb öiD 187 02NW lt lt 1' orange C6E13(n) CHi: (n) 188 02N lt lt lt 1 00113 189 BN=+ U n ON rot OCH3 Bsp. D R1 R2 X Farbt. der Nr. Massefärbung v. Polystyrol 0113 190 ß H2cH2°aE3 CH2CE2 CE3 ON | rot 0113 191 0lN 1- 1 t scharlach 0113 0113 192 1 Wß n CH,CH,OH lt lt 0113 0011 110 193 J 512 rot 193 TrsrlJ - 12 193 (n)11 0 9 4 194 11 11 orange 0113 1130 195 CE3 4 2CH2°cH3 CH2CH20CH3 CN scharlach Ol 196 02N d (CH2)6 (0E2)6°H n n 197 n (0112)300113 CH2CH208CH, II orange 0 B8p- D R1 R2 X Farbt. der Nr. Ngss rbung v. Polystyrol ON 198 6 CH2CH2CH20CH3 CH2CHOCOCH20C6E5 CN gelb 199 lt lt ,I lt tt 200 lt (CH2)2CE20COCE3 (CH2)2CH20COCE3 .. II 201 02N < (CH2)6oH (CH2)6oH " rot cl ?2115 CE2CEC4H9(n) 202 02N C1120H200113 CH2CH2°CH) n orange orange 203 2 < n n n n Cl 1 204 | Cl/c -(CH2)30CH3 i (CH2))0CH) 1l ),OCH, rotstichig C1 205 ' lt 06115 tt tt orange Cl 206 Cl' (CH2)30CH3 lt ri 3 | rotstichig Cl gelb 207 C tl II II lt Cl Tabelle 4 Bsp. D R R2 Farbt. der . MassefSrbung v. Polystyrol Cl 208 2 4 11 orange 209 lt CH2CH2CH20CH, CH2CH2CE20Cb rot 210 >N 11 11 orange 211 n CH2CH20CH3 CH2CE20CH3 rot 011 212 Cl e N~N > E H n 0113 2i3 " CH2CH20CH, 0112011200113 II Table 1 E.g. R1 B2 R4 R5 color. the No. nasal staining s. Polystyrene 3 CH2CH20CH3 (CH2) 2ocH3 C3H7 ON E yellow 4 n (2) 3 3 CH3 OH in nn 3 5 nnnn Cl n 6 n 02115 nn H n 7 n CE3 unnn 8 II (Cz2) 30C (CH3) 2 nn to nn 9 02115 (0H2) 200113 nnnn 10 CH2CH20H n 1 1 u 1 2 2011 11 n 1 'n II N n 12 CH2CH20H (0112) 300 113 0113 Cl n Cl 13 02115 X2H5 1 ON 11 n 14 "nn CF) H n 15 1 1 1 1 E.g. R1 R2 R3 R4 R5 color. the No. Mass coloring v Polystyrene 16 C2H5 CH2CH2OH CH3 CN H yellow 17 "(CH2) 3OH"""" 18 """CF3Cl" 19 CH2CH2OCH3 CH2CH2OCH3 "" H " 20 C6H5 H """" 21 "CH2CH2OCH3"""" 22 C2H5 C2H5 "COOCH3"" 23 "CH2CH2OCH3"""" 24 """" Cl " 25 C4H9 (n) "" CN "" 26 (CH2) 3OCH (CH3) 2 (CH2) 3OCH (CH3) 2 "CF3 H" 27 C6H13 (n) CH2CH2OH """" 28 H C2H5 "CN Cl" 29 "" C3H7 """ 30 """CF3H" 31 "CH2CH2OCH3 CH3""" 32 """CN"" 33 """COOCH3Cl" E.g. R1 2 R3 R4 L5 color. the No. J mass coloring v. Polystyrene 7th 34 jCH2Cll2OCH3 H CH3 CK H yellow 35 II II OF H n 3 36 tCH2CH2CH2 ° CH3 CH2CH2CH20CH3 "OCH3 CN H 37 | II ll H SO2C6i {5 "ll 38 CH2 CH2-C6H5 CH2CH20H CH3 CN,. 39, l CH2CH20CH3 a It lt II 40, ln 0 3H7 according to II 41 II, 1 CH3 "Cl 42 II CH, CH, CH, OCH, " 43 II CH2OH2C6H5 II lt II II 44 "II tl according to Cl 45 CH2CE-O-C6H5 CH2CH2OH2OCH3 II n H CH3 46 CH2CH2CH20C 6H5 OH2OH2OH lt: 1 lt 47 CH2-C1H-C6H5 CH2CH2c; H20CH3 n "n, OH 48 (CH2) 30CH2C6 H5 lt t lt lt n lt II 49 II OH2CH2 OH nse II II E.g. R1 R2 R3 R4 R5 color. the No. Mass coloring v. Polystyrene 50 (CH2) 30CH2C6H5 OH2-OH-OH3 CH3 CN H yellow OH 51 (CH2) 30CH2CH20C6H5 CH2CH20H nn ll 52 (CH2) 30 (CH2) 40H 1 nnn tt 53 l (cH2) 30 (CH2) 20C4H9 "n 11 nn 54 O6H5 CH2CH2CH20CH3 nnn golden yellow 55 "II II C1 orange 56 6 4 3 II II H n 57 (OH2) 6N $) n II n II yellow CH3 OH 13th 58 -OH (II 1 II II n tt 1 0111 r 3 ( 3 OH3 59 OH2 0112001120112011 1 '1 1 11 60 i (CH,), O e CH2CH2 ° CH3 II nnn 61 0112011200113 II 11 SO2C6H5 1 LL 2 oc, 63 1 (CH2) 30CHCH20CH3 ON II n 63 J (CH), OCHCH, OCH, II 11 1 'CH3 0113 64 (CH2) 3 ° CH2C§H ° C6H5 CH2CH20H nnn CH3 Ex. 111 R2 R3 R4 R5 colors. the No. Mass coloring v. Polystyrene 65 (0112) 6011 CH2CE2GH20CH3 3 ON H yellow 66 i (cE2) 5-cg,, ", 67 | CH2CE2OCH3 n 06115 n II n 68 | II CII2CH20CH, - II CF3 C1 69 X II n H II II 02115 ON 1 70 l.oHsoooo 11 0113 CN n 1 ' 71 - (CH,) l'l 72 1 (CE2) 5COOC2ff5 1 1 1 1 II II 73 (CH2) 5sooc3X7 II n II II n 74 (CH2) 5aOOC4Eg. * ns 75 CH2CH2-N CH2CH20CH, II II II n 0 76 CH2CE = CE2 nnn II II 77 CH2Cti = CEi2 CIfCH = CH2 II II nn 78 CZ2c32CH2 ° H (0112) 300113 nnnn 79 CH2iH-C6E5 CE2CH20H o II II s ch-3 80 | C0I2CH2CH20C 5020113 nnan E.g. R1 R2 R3 R4 R5 color. the No. Mass coloring v. l polystyrene 81 CH2CH2CH2OCH3 COC6H5 CH3 CN H yellow 82 "SO2C6H5"""" 83 CH2CH2OCH3 """"" Table 2 E.g. R1 R2 R3 R4 R5 color. the No. Mass coloring v. Polystyrene 84 H C2H5 H NO2 H golden yellow 85 "(CH2) 3OCH3"""" 86 "(CH2) 3OCH (CH3) 2"""" 87 "(CH2) 3OCH3 CH3""orange 88 "" OCH3 "" red-orange 89 C2H5 C2H5 """scarlet 90 nn H II "orange 91 "" CN "" scarlet 92 "C3H7 (n)"""" 93 """" Cl bluish red 94 "C2H5"""" 95 (CH2) 3OCH3 """"" 96 """""scarlet E.g. R1 R2 R3 R4 R5 color. the No. Mass coloring v. Polystyrene 97 (CH2) 3OCH3 C2H5 Cl NO2 H yellowish red 98 H """" orange 99 "(CH2) 3OCH3"""" 100 "" NO2 "" red 101 C2H5 """" bluish red 102 "" CN "Br" 103 CH2CH2OCOCH3 C2H5 "HH yellow 104 C2H5 CH2CH2OCOCH3 """" 105 CH2CH2OC6H5 CH2CH2CH2OCH3 Cl NO2 "orange 106 "" CN "" scarlet 107 CH2CH2CH2OC6H5 """"" 108 "" Cl "" orange 109 (CH2) 3OCH2C6H5 """"" 110 (CH2) 3OCH2C6H5 "CN""scarlet 111 """" Cl bluish red 112 """" Br " 113 "CH2CH2OH"""" E.g. R1 R2 R3 R4 R5 color. the No. Mass coloring v. Polystyrene 114 (CH2) 3OCH2C6H5 CH2CH2OH Cl NO2 H orange 115 "" CN "" scarlet 116 (CH2) 3OCH2CH2C6H5 """"" 117 (CH2) 3OCH2CH2OC6H5 """"" 118 "" Cl "" orange 119 "CH2CH2OCH3"""" 120 "" CN "" scarlet 121 "" NO2 "" red 122 "CH2CH2OH"""" 123 "" Br "" red orange 124 "" COOCH3 """ 125 "" H "" orange 126 "" SO2CH3 "" red 127 "" CH3 "" orange 128 nn OCH3 "nn 129 "" SO2CH3 Cl "golden yellow 130 "CH2CH2OCH3 CN NO2 NO2 bluish red 131 """" CN " 132 "" Cl "Cl yellow-brown E.g. R1 R2 R3 R4 R5 color. the No. Mass coloring v. Polystyrene 133 (CH2) 3OCH2CH2OC6H5 CH2CH2OCH3 H SO2CH3 Cl yellow 134 "" Cl "H" 135 nn Br N02 Br yellow-brown 136 "CH2CH2OH COOCH3 Cl Cl yellow 137 "" Cl SO2C6H5H " 138 "" CN CN "orange 139 "" Cl Cl Cl yellow 140 CH2CH2CH2OCH3 CH2CH2CH2OCH3 """" 141 """SO2CH3"" 142 "" HN = N-C6H5 H orange 143 CH2CH2OCH3 CH2CH2OCH3 """" 144 "" Cl SO2CH3 "yellow Tabel @ Ex. D R1 R2 X color. the No. Mass coloring v. Polystyrene 145 u N CH2CH2CH20CH3 CH2CH2CH20CE3 CN reddish blue N 146 n ... , ZONE2 blue 147 II n 11 148 II (2) 3 4 9 OH2 011200113 CN purple 1130 ON 149 Ii 1 lt red 0113 red II n 150 lt (CH2) 3oCB26 5 II In 151 N l, i lt, I n bluish red iS 152 lt CH2CH2CH20CH3 CH2CH2CH20CH3 lt dt Ex. D R1 R2 X color. the No. Mass coloring v. Polystyrene C113S 153 S CH2CH2CH20CH3 CH2CH2CH20CH3 CN orange 154 lt CE2CH20CH3 CH2CH20CH3 n II 155 n 06H5 nn scarlet 156 lt CH2CH2a6E5 CH2CH20H n orange 157 nnn H red 158 n CE2CE2c6E5 CH2CE2a6R5 ON orange 011 00002118 159 1 1 II 160 n CH2CH20CH3 CE2CH20CH3 nn 161 1 'CH2CH2o65 CH2CH2e65 according to n ON 162 02N 4 CH2CH20CE3 CH2CH20CH3 00NH2 red 163 n II n H n 164 n CH2CH2CH20CH3 CH2CH2CE20CH3 nn 165 CN nn CONE2 n OH 166 2 4 inside blue-tinged red 167 lt nn H n Ex. D R1 R2 X color. the No. Mass coloring v. Polystyrene CN 168 02N 4 CE2CH2CH20CH3 CH2CH20H CONH2 bluish red 169 according to CH2CE2 C6E5. nn 170 a> CH2CH20CH3 CH2CH20CH3 CN scarlet 171 n CH2CH2CH20CH3 CH2CH2CH20CH3 acc N 172 Cl I, II nn 173 n CH2CH20CH3 CH2CE20CE3 acc 174 M nn red 175 "according to CH2CH2CE20CE3 CH2CH2CH20CH3 tt according to ° 2 176 eunn bluish red 177 tt CEi2CH20CH, CH2CH20CH3 na 3 178 lt lt lt nnn yellow O 179 n CH2CH2CH20CH3 CH2CH2CH20CH3 II II B8p. D R1 R2 X F2rBt der E.g. D R1 R2 X color 0 der No. XLsse coloring v. Polystyrene S02CB, 180 02N V CH2CH2CH20CH3 CH2CH2CH20CH3 CN red 181 lt n 1 'CONH lt 182 H n II 11 183 4 lt C4Hs (") C4Hg (n) n lt 0 184 n CH2CH2CH20CH3 CH2CH2CH20CH !; CN brown 185 n 11 (0112) 300 211 400 113 n yellow-brown 186 S02 HH n yellow öiD 187 02NW lt lt 1 'orange C6E13 (n) CHi: (n) 188 02N lt lt lt 1 00113 189 BN = + U n ON red OCH3 Ex. D R1 R2 X color. the No. Mass coloring v. Polystyrene 0113 190 ß H2cH2 ° aE3 CH2CE2 CE3 ON | Red 0113 191 0lN 1- 1t scarlet 0113 0113 192 1 Wß n CH, CH, OH according to 0113 0011 110 193 J 512 red 193 TrsrlJ - 12 193 (n) 11 0 9 4 194 11 11 orange 0113 1130 195 CE3 4 2CH2 ° cH3 CH2CH20CH3 CN scarlet Oil 196 02N d (CH2) 6 (0E2) 6 ° H nn 197 n (0112) 300113 CH2CH208CH, II orange 0 B8p- D R1 R2 X color. the No. Ngss rbung v. Polystyrene ON 198 6 CH2CH2CH20CH3 CH2CHOCOCH20C6E5 CN yellow 199 lt lt, I lt tt 200 lt (CH2) 2CE20COCE3 (CH2) 2CH20COCE3 .. II 201 02N <(CH2) 6oH (CH2) 6oH "red cl ? 2115 CE2CEC4H9 (n) 202 02N C1120H200113 CH2CH2 ° CH) n orange orange 203 2 <nnnn Cl 1 204 | Cl / c - (CH2) 30CH3 i (CH2)) 0CH) 1l), OCH, reddish C1 205 'lt 06115 tt tt orange Cl 206 Cl '(CH2) 30CH3 lt ri 3 | reddish Cl yellow 207 C tl II II acc Cl Table 4 E.g. DR R2 color. the . Mass coloring v. Polystyrene Cl 208 2 4 11 orange 209 lt CH2CH2CH20CH, CH2CH2CE20Cb red 210> N 11 11 orange 211 n CH2CH20CH3 CH2CE20CH3 red 011 212 Cl e N ~ N> EH n 0113 2i3 "CH2CH20CH, 0112011200113 II

Claims (2)

PatentansprUche Verwendung von Farbstoffen der Formel in der D den Rest einer Diazokomponente, R Wasserstoff, Alkyl, Methylphenyl oder Phenyl, X Wasserstoff, Carbamoyl oder Cyan und die Reste A unabhängig voneinander Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl, Aralkyl, Phenyl oder Acyl bedeuten, zum Färben von Thermoplasten.Patent claims use of dyes of the formula in which D is the radical of a diazo component, R is hydrogen, alkyl, methylphenyl or phenyl, X is hydrogen, carbamoyl or cyano and the radicals A are independently hydrogen, optionally substituted alkyl, cycloalkyl, aralkyl, phenyl or acyl, for dyeing thermoplastics. 2. Verwendung von Farbstoffen der Formel in der B Nitro, Cyan, Chlor, Brom, Trifluormethyl, Carbomethoxy, Carboäthoxy, ß-Metholcycarbäthoxy, Methylsulfonyl, Äthyl sulfonyl, Methyl, Methoxy oder Phenylazo, B1 Wasserstoff, Nitro, Chlor, Brom, Cyan, Methyl, Methoxy, Carbomethoxy, Phenylsulfonyl, Carboäthoxy, Methylsulfonyl oder Äthylsulfonyl und B2 Wasserstoff, Chlor, Brom, Cyan oder Methyl und A unabhängig voneinander Wasserstoff, gegebenenfalls substituiertes Alkyl, Cycloalkyl, Aralkyl, Phenyl oder Acyl bedeuten gemäß Anspruch 1.2. Use of dyes of the formula in B nitro, cyano, chlorine, bromine, trifluoromethyl, carbomethoxy, carboethoxy, ß-Metholcycarbäthoxy, methylsulfonyl, ethyl sulfonyl, methyl, methoxy or phenylazo, B1 hydrogen, nitro, chlorine, bromine, cyano, methyl, methoxy, carbomethoxy, phenylsulfonyl , Carboethoxy, methylsulphonyl or ethylsulphonyl and B2 are hydrogen, chlorine, bromine, cyano or methyl and A are independently hydrogen, optionally substituted alkyl, cycloalkyl, aralkyl, phenyl or acyl according to claim 1.
DE2409754A 1974-03-01 1974-03-01 Heat-stable dyes of 2,6-diamino-pyridine series - for dyeing thermoplastics in the melt Pending DE2409754A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DE2409754A DE2409754A1 (en) 1974-03-01 1974-03-01 Heat-stable dyes of 2,6-diamino-pyridine series - for dyeing thermoplastics in the melt
US05/551,493 US3974123A (en) 1974-03-01 1975-02-20 Dyes for thermoplastics
IT7548395A IT1029901B (en) 1974-03-01 1975-02-28 DYES FOR THERMOPLASTS
JP2410875A JPS539780B2 (en) 1974-03-01 1975-02-28
FR7506343A FR2262681B1 (en) 1974-03-01 1975-02-28
BE153897A BE826160A (en) 1974-03-01 1975-02-28 PROCESS FOR COLORING THERMOPLASTIC RESINS
NL7502419A NL7502419A (en) 1974-03-01 1975-02-28 THERMOPLAST DYES.
GB8384/75A GB1499181A (en) 1974-03-01 1975-02-28 Dyes for thermoplastics

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DE2409754A DE2409754A1 (en) 1974-03-01 1974-03-01 Heat-stable dyes of 2,6-diamino-pyridine series - for dyeing thermoplastics in the melt

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DE2409754A1 true DE2409754A1 (en) 1975-10-16

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DE2409754A Pending DE2409754A1 (en) 1974-03-01 1974-03-01 Heat-stable dyes of 2,6-diamino-pyridine series - for dyeing thermoplastics in the melt

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0009299A1 (en) * 1978-07-03 1980-04-02 Imperial Chemical Industries Plc Colour stabilized organic material

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0009299A1 (en) * 1978-07-03 1980-04-02 Imperial Chemical Industries Plc Colour stabilized organic material

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