DE2304356C3 - Azo disperse dyes, process for their preparation and their use - Google Patents

Azo disperse dyes, process for their preparation and their use

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Publication number
DE2304356C3
DE2304356C3 DE2304356A DE2304356A DE2304356C3 DE 2304356 C3 DE2304356 C3 DE 2304356C3 DE 2304356 A DE2304356 A DE 2304356A DE 2304356 A DE2304356 A DE 2304356A DE 2304356 C3 DE2304356 C3 DE 2304356C3
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Germany
Prior art keywords
same
hydrogen
general formula
disperse dyes
cyano
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Expired
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DE2304356A
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German (de)
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DE2304356B2 (en
DE2304356A1 (en
Inventor
Klaus Dr. Therwil Körte
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Sandoz Patent GmbH
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Sandoz Patent GmbH
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Publication of DE2304356B2 publication Critical patent/DE2304356B2/en
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Classifications

    • 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
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
    • C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—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
    • 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
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • 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
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
    • C09B29/0832—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino having -N-alkylene-heterocyclic ring
    • 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
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms 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
    • C09B29/3691—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing nitrogen and 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
    • C09B29/34—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
    • C09B29/3695—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing other heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/40—Cellulose acetate
    • D06P3/42—Cellulose acetate using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/40—Cellulose acetate
    • D06P3/46—Cellulose triacetate
    • D06P3/48—Cellulose triacetate using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Gegenstand der Erfindung sind in Wasser schwer einen Substituenten der FormelThe invention relates to a substituent of the formula difficult in water

lösliche Aminoazoverbindungen, deren Aminogruppesoluble aminoazo compounds, their amino group

O-O-

/ -CH1-CH / -CH 1 -CH

-CH, CH3 -CH, CH 3

CH, —CH, -

trägt insbesondere durch gutes Ziehvermogen sowie gutecarries particularly good pulling ability as well as good

Diese neuen Verbindungen finden als Dispersions- 20 Licht- undThermofixierechtheit aus.These new compounds are found to be dispersion, light and heat-setting fastness.

farbstoffe, zum Färben oder Bedrucken von Fasern oder Die neuen Verbindungen entsprechen der allgemei-dyes, for dyeing or printing fibers or The new compounds correspond to the general

Fäden aus voll- oder halbsynthetischen, hochmolekula- nen Formel ren organischen Stoffen Verwendung und zeichnen sichThreads made from fully or semi-synthetic, high-molecular formula Renal organic materials use and stand out

D-N=N-K-ND-N = N-K-N

CH2 \CH 2 \

CH2-CH CH2 CH 2 -CH CH 2

CH2-OCH 2 -O

D einen zumindest einmal durch Chlor, Brom, Cyan, Nitro, Alkylsulfonyl, Alkylcarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Alkylaminosulfonyl, Dialkylaminosuifonyl, Phenylsulfonyl oder Phenylazo substituierten Phenylrest, einen durch Nitro, Methylsulfonyl oder Acetyi substituierten Thiazolyl-, Benzthiazolyl-, Benzisothiazolyl- oder Thienylrest oder einen Phenylthiadiazolylrest,D one at least once by chlorine, bromine, cyano, nitro, alkylsulfonyl, alkylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminosulfonyl, Dialkylaminosulfonyl, phenylsulfonyl or phenylazo substituted phenyl radical, one by nitro, Methylsulfonyl or acetyl substituted thiazolyl, benzthiazolyl, benzisothiazolyl or thienyl radical or a phenylthiadiazolyl radical,

K gegebenenfalls durch Methyl, Alkylcarbonylamino, Chloralkylcarbonylamino, Bromalkylcarbonylamino, Alkoxyalkylcarbonylamino, Alkoxycarbonylamino, Alkoxycarbonylalkylcarbonylamino oder K optionally by methyl, alkylcarbonylamino, chloroalkylcarbonylamino, bromoalkylcarbonylamino, alkoxyalkylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylcarbonylamino or

4545 Alkyisulfonyiamino in 2-SteIIung zur Azogruppe und gegebenenfalls durch Alkoxy in 5-StelIung zur Azogruppe substituiertes 1,4-Phenylen oder unsubstituiertes 1,4-Naphthylenu?.dAlkyisulfonyiamino in the 2-position to the azo group and 1,4-phenylene which is optionally substituted by alkoxy in the 5-position to the azo group or unsubstituted 1,4-naphthylene and the like

Ri Wasserstoff oder gegebenenfalls durch Hydroxyl, Cyan, Alkylcarbonyloxy, Alkoxycarbonyl, Alkoxycarbonyloxy oder Alkylaminocarbonyloxy substituiertes AlkylRi hydrogen or optionally by hydroxyl, Cyan, alkylcarbonyloxy, alkoxycarbonyl, alkoxycarbonyloxy or alkylaminocarbonyloxy substituted alkyl

bedeuten, mit der Maßgabe, daß die bei D, K oder Ri genannten Alkylreste (worunter auch die Alkoxyreste fallen) 1 oder 2 Kohlenstoffatome enthalten.mean, with the proviso that the at D, K or Ri mentioned alkyl radicals (which also include the alkoxy radicals) contain 1 or 2 carbon atoms.

Besonders bevorzugt sind die Verbindungen der allgemeinen FormelnThe compounds of the general formulas are particularly preferred

O2NO 2 N

O CH2 O CH 2

(Ia)(Ia)

CH, C H,

CH2-OCH 2 -O

O >—NU—CH,--CHO> -NU-CH, -CH

(IhI(IhI

R2 Wasserstoff, Nitro oder Cyan,R 2 hydrogen, nitro or cyano,

R3 Wasserstoff, Chlor, Brom, Cyan oder Methylsulfonyl, R 3 hydrogen, chlorine, bromine, cyano or methylsulfonyl,

R4 Wasserstoff, Methoxy oder Äthoxy,
Rs Wasserstoff, Äthyl oder Cyanäthyl und
R6 Methyl oder Äthyl bedeuten.R4 hydrogen, methoxy or ethoxy,
Rs hydrogen, ethyl or cyanoethyl and
R 6 is methyl or ethyl.

Die neuen Verbindungen werden durch Diazotieren eines Amins der allgemeinen FormelThe new compounds are made by diazotizing an amine of the general formula

D-NH2 (II)D-NH 2 (II)

wobei D die bei der Formel I genannte Bedeutung hat, und Kuppeln der erhaltenen Diazoniumverbindung mit einer Verbindung der allgemeinen Formelwhere D has the meaning given for formula I, and coupling of the diazonium compound obtained with a compound of the general formula

H — K — NH - K - N

-CH,-CH,

CH1 — CH
\CH 1 - CH
\

CH2-OCH 2 -O

CH.CH.

(HD(HD

in der K und Ri die bei der Formel I genannte Bedeutung besitzen, hergestelltin the K and Ri those mentioned in the formula I. Have meaning, established

Die Diazotierung und das Kuppeln werden nach allgemein, zum Teil über 100 Jahre bekannten Methoden durchgeführt Im allgemeinen wird die Kupplung in saurem, gegebenenfalls gepuffertem Medium, z. B. im pH-Bereich unter 5, und unter Kühlung, z. B. bei Temperaturen unter 200C, vorzugsweise zwischen -5° und +50C durchgeführt Als Puffersubstanzen kommen vorzugsweise Alkalimetallsalze von niedrigmolekularen Alkansäuren, z. B. Essigsäure oder Propionsäure, insbesondere Natriumacetat, in Betrr-ht.The diazotization and the coupling are carried out according to methods which are generally known, some of which have been known for over 100 years. B. in the pH range below 5, and with cooling, z. B. carried out at temperatures below 20 0 C, preferably between -5 ° and +5 0 C. The buffer substances are preferably alkali metal salts of low molecular weight alkanoic acids, z. B. acetic acid or propionic acid, especially sodium acetate, in Betrr-ht.

Die Herstellung der Kupplungskomponente der Formel (III) erfolgt durch Umsetzung eines Amins der allgemeinen FormelThe coupling component of the formula (III) is prepared by reacting an amine general formula

Η —Κ —ΝΗ —Κ —Ν

(IV)(IV)

mit 2-Chlor- oder 2-BromäthyIglycidyläther. nach an sich bekannten Verfahren, z. B. in Gegenwart von wenig Wasser, bei etwa 1000C und anschließendem Kochen in einem Methanol/Wasser-Gemisch, in Gegenwart von Kaliumhydroxid.with 2-chloro or 2-bromoethyl glycidyl ether. according to methods known per se, e.g. B. in the presence of a little water, at about 100 0 C and subsequent boiling in a methanol / water mixture, in the presence of potassium hydroxide.

Die Verarbeitung der neuen Verbindungen der Formel (I) zu Färbepräparaten eriolgt auf allgemein bekannte Weise, z. B. durch Mahlen in Gegenwart von Diüpefgief- und/öder Füllmitteln. Mit den gegebenenfalls im Vakuum oder durch Zerstäuben getrockneten Präparaten kann man. nach Zugabe von mehr oder weniger Wasser, in sogenannter langer oder kurzer Flotte färben, klotzen oder bedrucken.The processing of the new compounds of the formula (I) into coloring preparations is a general one known way, e.g. B. by grinding in the presence of Diüpefgief- and / or fillers. With the possibly Preparations dried in a vacuum or by atomization can be used. after adding more or less water, dye, pad or print in a so-called long or short liquor.

Die Farbstoffe ziehen aus wäßriger Suspension ausgezeichnet auf Textilmaterial aus vollsynthetischen oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen auf. Besonders geeignet sind sie zum Färben oder Bedrucken von Textilmaterial aus linearen, aromatischen Polyestern, sowie aus Cellulose-2 >/2-acetat, Cellulosetriacetat und synthetischen PoIyamiden. The dyes are excellent on textile material made of fully synthetic materials from aqueous suspension or semi-synthetic, hydrophobic, high molecular weight organic substances. They are particularly suitable for dyeing or printing textile material made of linear, aromatic polyesters and cellulose-2 > / 2-acetate, cellulose triacetate and synthetic polyamides.

Man färbt oder bedruckt nach an sich bekannten, z. B. dem in der französischen Patentschrift Nr. 14 45 371 beschriebenen Verfahren.One dyes or prints according to known, z. B. the method described in French Patent No. 14 45 371.

Die erhaltenen Färbungen besitzen gute Allgemein-The dyeings obtained have good general

Hi echtheiten; hervorzuheben sind die Lichtechtheit, die Thermofixier-, Subliniier- und Plissierechtheit Sie sind hervorragend naßecht, z. B. wasser-, meerwasser-, wasch- und schweißecht, lösungsmittelecht, insbesondere trockenreinigungsecht, schmälzmittel-, reib-, überfärbe-, ozon-, rauchgas- und chlorecht; sie sind äußerst beständig gegen die Einwirkung der verschiedenen Permanentpreßverfahren und der sogenannten »Soil-Release«-Ausrüstungen. Die Ätzbarkeit, die Reduktionsbeständigkeit (beim Färben mit Wolle) und dieHi realities; to be emphasized are the lightfastness, the Thermofixing, sublining and pleating fastness. B. water, sea water, wash- and sweat-proof, solvent-proof, in particular dry cleaning fast, lubricant, rubbing, over dyeing, ozone, smoke and chlorine law; they are extremely resistant to the action of the various Permanent pressing process and the so-called "soil release" equipment. The etchability, the reduction resistance (when dyeing with wool) and the

:<> Reserve von Wolle und Baumwr^e sind gut: <> Reserves of wool and cotton are good

Gegenüber den nächstvergleichbaren, aus der US-Patentschrift 22 27 977 bekannten Farbstoffen, besitzen die erfindungsgemäßen Farbstoffe ein besseres Ziehvermögen auf Polyesterfasermaterial.Compared to the next comparable, from US Pat. No. 22 27 977 known dyes the dyes according to the invention have a better drawability on polyester fiber material.

JTi In den folgenden Beispielen bedeuten die Teile Gewichtsteile, die Temperaturen sind in Celsiusgraden angegeben.JTi In the following examples, the parts mean Parts by weight, the temperatures are given in degrees Celsius.

Beispiel 1example 1

so 173 Teile I-Amino-2-Chlor-4-nitrobenzol werden in 250 Teilen konzentrierter Salzsäure und 350 Teilen Eiswasser angerührt und bei 0° bis 5° mit einer Lösung von 69 Teilen Natriumnitrit in 250 Teilen Wasser diazotiert Die so erhaltene Diazoniurnsalziösung wird mit einerso 173 parts of I-amino-2-chloro-4-nitrobenzene are in 250 Parts of concentrated hydrochloric acid and 350 parts of ice water and stirred at 0 ° to 5 ° with a solution of 69 Parts of sodium nitrite in 250 parts of water are diazotized. The diazonium salt solution thus obtained is treated with a

Lösung von 221 Teilen N-Äthyl-N-[(l,4-dioxacyclohexyl-2)-methyI]-anilin und 25 Teilen Harnstoff in 350 Teilen Eisessig bei 0° bis 5° vereinigt Durch Zugabe von Natriumacetat bis zum Erreichen von pH 4 wird die Kupplung rasch zu Ende geführt Der ausgefallene Farbstoff wird abfiltriert, mit Wasser gewaschen und getrocknet. Er färbt Polyesterfasermaterial in brillanter, roter Nuance mit ausgezeichneten Echtheiten.Solution of 221 parts of N-ethyl-N - [(1,4-dioxacyclohexyl-2) -methyI] -aniline and 25 parts of urea combined in 350 parts of glacial acetic acid at 0 ° to 5 ° by addition of sodium acetate until pH 4 is reached, the coupling is quickly brought to an end. The precipitated Dye is filtered off, washed with water and dried. It dyes polyester fiber material in a brilliant, red shade with excellent fastness properties.

AnwendungsbeispielApplication example

7 Teile des nach Beispiel 1 hergestellten Farbstoffs werden mit 4 Teilen dinaphthylmethandisulfonsaurem Natrium, 4 Teilen Natriumcetylsulfat und 5 Teilen wasserfreiem Natriumsulfat in einer Kugelmühle 38 Stunden zu einem feinen Pulver gemahlen.7 parts of the dye prepared according to Example 1 are mixed with 4 parts of dinaphthylmethandisulfonsaurem Sodium, 4 parts of sodium cetyl sulfate and 5 parts of anhydrous sodium sulfate in a ball mill 38 Ground to a fine powder for hours.

1 Teil des so erhaltenen Färbepräparats wird mit wenig Wasser angeteigt und die erhaltene Suspension durch ein Sieb einem 2 Teile Natriumlaurylsulfat in 4000 leuen Wasser erhaltenden Färbebad zugesetzt Das1 part of the dye preparation obtained in this way is made into a paste with a little water and the suspension obtained added through a sieve to a dyebath containing 2 parts sodium lauryl sulfate in 4000 leuen water

)5 Flottenverhältnis beträgt 1 :40. Man gibt nun 100 Teile gereinigtes Polyestergewebe bei 50—30° in das Bad, gibt 20 Teile eines chlorierten Benzols in Wasser emulgiert zu, erwärmt das Bad langsam auf 100° und färbt 1-2 S'-inden bei 95-100°. Das rot gefärbte) 5 liquor ratio is 1:40. You now give 100 parts cleaned polyester fabric at 50-30 ° in the bath, are 20 parts of a chlorinated benzene emulsified in water, the bath is slowly heated to 100 ° and stains 1-2 S'-indene at 95-100 °. The red colored one

mi Gewebe wird gewaschen, geseift, erneut gewaschen und getrocknet. Die egäle, färbsläfke Färbung ist ausgezeichnet licht-, überfärbe-, wasch-, v/asser-, meerwasser-, schweiß-, sublimier-, rauchgas-, thermofixier-, plissier- und permanent-preßecht. The fabric is washed, soaped, washed again and dried. The leveling, dyestuff dye is extremely light, overdyeing, wash, water, sea water, perspiration, sublimation, smoke gas, thermosetting, pleating and permanent press-fast.

""> In der folgen "ten Tabelle sind weitere Farbstoffe der Formel (I) angegeben, sie sind durch die Symbole D, K, Ri und ihre Nuance auf Polvesterfasermaterial gekennzeichnet. ""> In the following table are further dyes of the Formula (I) indicated, they are identified by the symbols D, K, Ri and their nuance on Polvester fiber material.

Libelledragon-fly

Ii!Ii!

".N -.. ν.) (Π.. CW. CN hhiii".N - .. ν.) (Π .. CW. CN hhiii

(V NllCOCIl·(V NllCOCIl

KiKi

; ON ,lcsd ,Ι,.,μΙ SI„|C|, ; ON, lcsd, Ι,., ΜΙ SI „| C | ,

\( I\ (I

OC-IIOC-II

-1'.'-IiI ■ Il in.irinebl.iii-1 '.'- IiI ■ Il in.irinebl.iii

NH(OC IlNH (OC Il

; '--■-' -Ie^l C H1(O(K II. iii.iiinebl.iu ; '- ■ -' -Ie ^ l CH 1 (O (K II. Iii.iiinebl.iu

■'■ON (H. h|„,,■ '■ ON (H. h | ",,

(N NIICOCII(N NIICOCII

OCHOCH

ι-·--·; - ~ .-■■ C"H;- CH-O-C C H iii.irincN.H.ι- · - ·; - ~ .- ■■ C "H ; - CH-OC CH iii.irincN.H.

NHCO(H.NHCO (H.

(IN- — 1 -— Ii blau(IN- - 1 -— II blue

NO-NO-

:e^-i — Z ,.— — C II.- — CH;- OH violett: e ^ -i - Z ,. - - C II.- - CH; - OH purple

NHCOCH:NHCOCH:

ae-id — Z ;— -CH1-CH-CN violettae-id - Z ; - -CH 1 -CH-CN purple

NHC OCH; —OCH.NHC OCH; —OCH.

r'.N— - - — ^ .— —CH;—CH;—CN ro! r '.N— - - - ^ .— —CH; —CH; —CN ro!

NHCOCH-CiNHCOCH-Ci

lorisol/uim)lorisol / uim)

ClCl

< ο ν-<ο ν-

ClCl

( ,-^V—N ( , - ^ V-N

\/ S\ / S

--λ ο Υ"'--λ ο Υ "'

(1H,( 1 H,

NIICOCINIICOCI

NH(OCII;NH (OCII;

IOIO

CII- (II- O C CJI. rotCII- (II- O C CJI. Red

CII- (II- O ( ICII- (II- O (I

-CII--CH, CN-CII - CH, CN

Ii I.inIi I.in

inin

I7 O-NI 7 ON

CNCN

SO2CH,SO 2 CH,

18 desgl.18 the same.

19 desel.19 desel.

-CH CH--CN blau-CH CH - CN blue

NHCOCH- — CH, — ONHCOCH- - CH, - O

CIl,CIl,

NHCOCH;NHCOCH;

desgl. desgl.the same.

desg!.desg !.

CH;CH;

blaublue

blau blaublue blue

20 desel.20 desel.

21 desal.21 desal.

NHCOCiH1OCH..NHCOCiH 1 OCH ..

desgl.the same

-CH,--CH, -

blaublue

blaublue

,1,1

1212th

CN 22 O,N < O ΝCN 22 O, N <O Ν

CN 2.1 dcsgl.CN 2.1 dcsgl.

24 dc su I.24 dc su I.

25 desgl.25 the same.

HrMr

2(. O,N -■( O2 (. O, N - ■ (O

"Τ (N "Τ (N

21 21 ilcsiil.ilcsiil.

NO,NO,

28 O, N—;' O28 O, N-; ' O

ClCl

29 desgl.29 the same.

NO,NO,

BrBr

ClCl

32 desgl.32 the same.

33 desgl.33 the same.

C!C!

MK(K H1(KMK (KH 1 (K

^ IK (H Il^ IK (H Il

dc sydc sy

desul.desul.

NHCOC-H1OCH,NHCOC-H 1 OCH,

OC Ml.OC Ml.

NHCOCH.NHCOCH.

OCII.OCII.

o"O"

NHCOCH,NHCOCH,

NHCOC2H4-OCHjNHCOC 2 H 4 -OCHj

desgi. desgl. (.1 desgi. the same. (.1

(Mi.(Wed

-C2H4-OH-C 2 H 4 -OH

Nil.IIHVNil.IIHV

hl. inSt. in

hl.iuhl.iu

hl.iiihl.iii

hl.iuhl.iu

bl.iubl.iu

hhiuhhiu

ni.iniK'hlauni.iniK'hlau

marineblaunavy blue

marineblaunavy blue

gelbbraunyellow-brown

C2H4OCOCHj gelbbraunC 2 H 4 OCOCHj yellow-brown

-C2H4OCONHC2Hj gelbbiaun-C 2 H 4 OCONHC 2 Hj yellow biaun

1313th

ι l-drtscl/uni!)ι l-drtscl / uni!)

IKr I)IKr I)

4 C,II, -N-N < O >4 C, II, -N-N <O>

c.:i. · νc.:i. · Ν

N ; N ;

411 desgl.411 the same.

4 1 dosgl.4 1 dosgl.

4 2 desgl.4 2 the same.

43 desgl.43 the same

44 desgl.44 the same.

45 desgl. 4(i desgl.45 as well. 4 (i desgl.

4" desel.4 "desel.

N — NN - N

48 CHc-48 CHc-

49 desgl.49 the same.

50 desgl.50 the same.

51 desgl.51 the same.

52 desel.52 desel.

53 desal.53 desal.

desgl.the same

desgl. desgl. dosül.the same. the same. dosül.

O > — O > -

NHCOCH.NHCOCH.

dosgl. desgl. dosgl.dosgl. the same. dosgl.

OC-H,OC-H,

NHCOCH.NHCOCH.

desgl. desgl. desgl. desgl. desel.the same. the same. the same. desel.

1414th

-CMI,
Il-CMI,
Il

-CMI,
■- CMI1CN-CMI,
■ - CMI 1 CN

-CMI. COOCMI,-CMI. COOCMI,

doss:!.doss:!.

-C2H5 -C 2 H 5

-C2H4CN-C 2 H 4 CN

-C2H4OCOCH3 -C 2 H 4 OCOCH 3

desgl.the same

— CH4COOCH,- CH 4 COOCH,

NiiiiiK-cNiiiiiK-c

sch:irljif hsch: irljif h

SL'h;irhu:h l'dlSL'h; irhu: h l'dl

ScharlachScarlet fever

scharlach scharlach scharlach Scharlachscarlet scarlet scarlet scarlet fever

rolrol

CC. MlMl 4OCOCH,4OCOCH, rotRed HH rotRed —- CC. :H:H .CN.CN -)t-) t CC. :H:H 4COOCH;4COOCH; rotRed

violettviolet

scharlachScarlet fever

scharlach scharlach scharlach Scharlach scharlachscarlet scarlet scarlet scarlet scarlet fever

1515th

l-'nristM/ung) 16 l-'nristM / ung) 16

Nuancenuance

Ν — ΝΝ - Ν

54 Cn H ,-4 .'L54 C n H, -4 .'L

55 desgl.55 the same.

56 desgl.56 the same.

5" dem!.5 "dem !.

NHCOCH-, itesel.NHCOCH-, itesel.

58 desel.58 desel.

ίο!
ο,ν 41
desgl. ίο!
ο, ν 41
the same C —
il
NC -
il
N NHCOCHNHCOCH 59
6059
60 desgl.the same desgl.the same 6161 desgl.the same desgl.the same 6262 desgl.the same desgl.the same 6363 -/öV-- / public transport

64 desgl.64 the same

65 desgl.65 the same

! ->Ί N! -> Ί N

66 C H-.SO.—\~'\ _}— 66 C H-.SO.— \ ~ '\ _} -

6 7 dt6 7 German

NHCOCH, desgl.NHCOCH, desgl.

NHCOC2HjOCH,NHCOC 2 HjOCH,

CH,CH,

desgl. -CiH4OCOCH.,the same. -CiH 4 OCOCH.,

— C2H4COOC2H5 - C 2 H 4 COOC 2 H 5

-CMh-CMh

rotRed

rotRed

rotRed

rotRed

violettviolet

rotRed

-C2H5 -C 2 H 5 rotRed -C2HaCOOC2H5 -C 2 HaCOOC 2 H 5 rotRed -C2H4OCOCH3 -C 2 H 4 OCOCH 3 rotRed desgl.the same blaustichigbluish tint rotRed HH blaustjchigbluish rotRed HH bhuistichigbhuistichig rotRed

hrillantros; brillanlros;hrillantros; brillanlros;

230 216/14230 216/14

1717th

(Fortsetzung) 18 (Continued) 18

Bsp.E.g.

NuancNuanc

69 N-SO69 N-SO

CH3 CH 3

70 desgl.70 the same.

71 desgl.71 the same.

73 · desgl.73 the same

74 desgl.74 the same.

75 desgl.75 the same

76 O2N76 O 2 N

77 desgl.77 the same

78 desgl.78 the same.

79 desgl.79 the same.

80 desgl.80 the same

81 desgl.81 the same.

82 desgl.82 the same.

CNCN

desgl.the same

desgl.the same

desgl.the same

desgl.the same

NHCOCrH5 desgl.NHCOCrH 5 like.

blaublue

rotRed

HH C2H5 C 2 H 5 ScharlachScarlet fever —- C2H5 C 2 H 5 ScharlachScarlet fever C2H4COOC2H5 C 2 H 4 COOC 2 H 5 gelbyellow gelbyellow HH -C2H4COOC2H,-C 2 H 4 COOC 2 H, ScharlachScarlet fever ScharlachScarlet fever

rubinruby

-C2H5 -C 2 H 5 rubinruby -C2H4CN-C 2 H 4 CN rubinruby -C2H1OCOOC2H5 -C 2 H 1 OCOOC 2 H 5 rubinruby -C2H4COOCjH5 -C 2 H 4 COOCjH 5 rubinruby HH bordeauxbordeaux

violettviolet

83 desel.83 desel.

— Γ,Η,ΓΝ- Γ, Η, ΓΝ

violettviolet

84 desgl.84 the same.

-CMI1(KOCII,-CMI 1 (KOCII,

NiolettNiolett

2020th

(Fortseizung) Bsp. P(Continuation) E.g. P

Nuancenuance

ClCl

85 O3N-^85 O 3 N- ^

86 desgl.86 the same.

87 desgl.87 the same.

88 desgl.88 the same.

89 desgl.89 the same.

90 desgl.90 the same.

NO2 NO 2

91 O2N-<91 O 2 N- <

92 desgl.92 the same.

CNCN

93 O2N —< Ο93 O 2 N - <Ο

94 OjN94 OjN

97 O,N -97 O, N -

NHCOOCH3 NHCOOCH 3

NHCOC2H4OCH,NHCOC 2 H 4 OCH,

/ S / S

NHCOCH,NHCOCH,

O >—<O > - <

desgl.the same

desgl.the same

desgl.the same

desgl.the same

ilesgl.ilesgl.

C2H,C 2 H,

NHCOCH3 NHCOCH 3 — C2FLOCOCH3 - C 2 FLOCOCH 3 rotRed desgl.the same -C2H4COOCH--C 2 H 4 COOCH- rotRed desgl.the same -C2H4OCOOC2Hs-C 2 H 4 OCOOC 2 Hs rotRed desgl.the same

2121

(Portsei/une)(Portsei / une)

2222nd

Hsp.Hsp.

ClCl

98 H1CNHSO3 98 H 1 CNHSO 3

ClCl

ClCl

99 H5C2SO2-f O99 H 5 C 2 SO 2 -f O

ClCl

100 H5C1SO2—< O Cl100 H 5 C 1 SO 2 - <O Cl

101 H5C2NHCO-^. O101 H 5 C 2 NHCO- ^. O

102 (CHOiNCO-C O102 (CHOiNCO-CO

103 O2N —< O103 O 2 N - <O

104 desgl.104 the same.

105 O2N105 O 2 N

106 O,N106 O, N

ClCl

O ΠO Π

NHCOCH.,NHCOCH.,

de.gl.de.gl.

desnl.desnl.

desgl.the same

NHCOCH,NHCOCH,

desgl.the same

o y— o y— ηη

NHCOCH-CHX-OOCH,NHCOCH-CHX-OOCH,

rotRed

gelbyellow

gelbyellow

rotRed

rotRed

rotRed

-CH2CH2OCOC6H5 rot-CH 2 CH 2 OCOC 6 H 5 red

-CH2CH2OC6H5 gelbbraun-CH 2 CH 2 OC 6 H 5 yellow-brown

rotRed

Claims (4)

Patentansprüche: 1. Azo-Dispersionsfarbstoffe der allgemeinen FormelClaims: 1. Azo disperse dyes of the general formula D-N=N-K-ND-N = N-K-N CH,— CHCH, - CH CH,CH, CH3-OCH 3 -O D einen zumindest einmal durch Chlor, Brom, Cyan, Nitro, Alkylsulfonyl, Alkylcarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Alkylaminosulfonyl, Dialkylaminosulfonyl, Phenylsulfonyl oder Phenylazo substituierten Phenylrest, einen durch Nitro, Methylsulfonyl oder Acetyl substituierten Tiazolyl-, Benzthiazolyl-, Benzisothiazolyl- oder Thienylrest oder einen Phenylthiadiazolylrest,D one at least once by chlorine, bromine, cyano, nitro, alkylsulfonyl, alkylcarbonyl, alkylaminocarbonyl, Dialkylaminocarbonyl, alkylaminosulfonyl, dialkylaminosulfonyl, phenylsulfonyl or phenylazo substituted phenyl radical, one by nitro, methylsulfonyl or Acetyl substituted tiazolyl, benzthiazolyl, Benzisothiazolyl or thienyl radical or a phenylthiadiazolyl radical, K gegebenenfalls durch Methyl, Alkylcarbonylamino, Chloralkylcarbonylamino, Bromalkylcarbonylamino, Alkoxyalkylcarbonylamino,K optionally by methyl, alkylcarbonylamino, Chloroalkylcarbonylamino, bromoalkylcarbonylamino, Alkoxyalkylcarbonylamino, 15 Alkoxycarbonylamino, Alkoxycarbonylalkylcarbonylamino oder Alkylsulfonylamino in 2-StelIung zur Azogruppe und gegebenenfalls durch Alkoxy in 5-Stellung zur Azogruppe substituiertes 1,4-Phenylen oder unsubstituiertes 1,4-NaphthyIenund 15 alkoxycarbonylamino, alkoxycarbonylalkylcarbonylamino or alkylsulfonylamino in the 2-position to the azo group and optionally 1,4-phenylene substituted by alkoxy in the 5-position to the azo group or unsubstituted 1,4-naphthylene and Ri Wasserstoff oder gegebenenfalls durch Hydroxyl, Cyan, Alkylcarbonyloxy, Alkoxycarbonyl, Alkoxyearbonyloxy oder Alkylaminocarbohyloxy substituiertes AlkylRi hydrogen or optionally by hydroxyl, cyano, alkylcarbonyloxy, alkoxycarbonyl, Alkoxyearbonyloxy or alkylaminocarbohyloxy substituted alkyl bedeuten, mit der Maßgabe, daß die bei D, K und Ri genannten Alkylreste stets 1 oder 2 Kohlenstoffatome enthalten.mean, with the proviso that the alkyl radicals mentioned for D, K and Ri always have 1 or 2 carbon atoms contain. 2. Azo-DispersionsfarbstofTe nach Anspruch 1, der allgemeinen Formel2. Azo disperse dyes according to Claim 1, of the general formula O2NO 2 N N = NN = N R5 ΟR 5 Ο -CH2 -CH 2 NHCOR6 NHCOR 6 CH2-CHCH 2 -CH CH2-OCH 2 -O R2 Wasserstoff, Nitro oder Cyan,R 2 hydrogen, nitro or cyano, Rj Wasserstoff. Chlor. Brom, Cyan oder Methylsulfonyl.Rj hydrogen. Chlorine. Bromine, cyano or methylsulfonyl. R4 Wasserstoff, Methoxy oder Äthoxy,R 4 hydrogen, methoxy or ethoxy, R5 Wasserstoff. Äthyl oder Cyanäthyl undR 5 is hydrogen. Ethyl or cyanoethyl and R6 Methyl oder Äthyl bedeuten.R 6 is methyl or ethyl. 3. Azo-Dispersionsfarbstofle nach Anspruch I, der allgemeinen Formel3. Azo disperse dyes according to claim I, of the general formula CH2 CH 2 O2NO 2 N O-O- -CH2
\-CH 2
\ CH2 CH 2 R2 Wasserstoff. Nitro oder Cyan undR 2 is hydrogen. Nitro or cyan and Rj Wasserstoff. Chlor. Brom, Cyan oder Methylsulfonyl bedeuten.Rj hydrogen. Chlorine. Mean bromine, cyano or methylsulfonyl. 4. Verfahren zur Herstellung von Azo-Dispersionsfarbstoffen der allgemeinen Formel gemäß Anspruch 1, dadurch gekennzeichnet, daß man ein Amin der allgemeinen Formel4. Process for the preparation of azo disperse dyes of the general formula according to Claim 1, characterized in that an amine of the general formula dung mit einer Verbindung der allgemeinen Formelwith a compound of the general formula II —Κ —ΝII —Κ —Ν O CH1 O CH 1 D-NH2 D-NH 2 wobei D die im Anspruch I angegebene Bedeutung hat, diazotiert und die erhaltene Diazoniumverbin-CH1-CH where D has the meaning given in claim I, diazotized and the resulting diazonium compound -CH 1 -CH CH,CH, CII2-OCII 2 -O in der K und Ri die im Anspruch 1 angegebene Bedeutung besitzen, kuppelt.in the K and Ri specified in claim 1 Possess meaning, coupling. 5, Verwendung der Azo-Dispersionsfarbstoffe nach den Ansprüchen i bis 3, zum Färben oder Bedrucken von Fasern oder Fäden oder daraus5, use of the azo disperse dyes according to claims i to 3, for dyeing or Printing on or from fibers or threads hergestellten Materialien aus voll- oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen.materials made from fully or semi-synthetic, hydrophobic, high-molecular organic substances.
DE2304356A 1972-02-02 1973-01-30 Azo disperse dyes, process for their preparation and their use Expired DE2304356C3 (en)

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US2816898A (en) * 1954-09-30 1957-12-17 Union Carbide Corp Aryl halogen substituted dioxanes and dioxins and processes
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ES411158A1 (en) 1976-04-01
GB1419822A (en) 1975-12-31
FR2170118B1 (en) 1976-05-14
BR7300754D0 (en) 1973-09-13
AR195316A1 (en) 1973-09-28
JPS4888118A (en) 1973-11-19
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IT977125B (en) 1974-09-10
NL7301216A (en) 1973-08-06
DE2304356B2 (en) 1981-06-25
DE2304356A1 (en) 1973-08-09

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