DE2363676A1 - AZO DYES - Google Patents

AZO DYES

Info

Publication number
DE2363676A1
DE2363676A1 DE19732363676 DE2363676A DE2363676A1 DE 2363676 A1 DE2363676 A1 DE 2363676A1 DE 19732363676 DE19732363676 DE 19732363676 DE 2363676 A DE2363676 A DE 2363676A DE 2363676 A1 DE2363676 A1 DE 2363676A1
Authority
DE
Germany
Prior art keywords
dyes
formula
azo dyes
compounds
azo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DE19732363676
Other languages
German (de)
Inventor
Klaus Dr Leverenz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to DE19732363676 priority Critical patent/DE2363676A1/en
Priority to NL7416004A priority patent/NL7416004A/en
Priority to IT3077874A priority patent/IT1027849B/en
Priority to JP14509374A priority patent/JPS5096624A/ja
Priority to CH1695274A priority patent/CH583767A5/xx
Priority to FR7442291A priority patent/FR2255353B3/fr
Priority to BE151776A priority patent/BE823672A/en
Priority to GB5514374A priority patent/GB1449399A/en
Publication of DE2363676A1 publication Critical patent/DE2363676A1/en
Pending legal-status Critical Current

Links

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
    • C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
    • C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals

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

Description

20. Dezember 197320th December 1973

Die vorliegende Erfinduing betrifft Azofarbstoffe der allgemeinen FormelThe present invention relates to azo dyes in general formula

in der R^, R2 und R,'unabhängig voneinander C.-Cr-Alkyl-in which R ^, R2 and R, 'independently of one another C.-Cr-Alkyl-

reste bedeuten,remnants mean

sowie deren Herstellung und Verwendung. .as well as their manufacture and use. .

Die Herstellung der Farbstoffe erfolgt nach an sich bekannten Verfahren durch Kupplung von diazotierten 2-Amino-3,5-dinitrobenzonitril mit Verbindungen der allgemeinen FormelThe dyes are prepared by processes known per se by coupling diazotized 2-amino-3,5-dinitrobenzonitrile with compounds of the general formula

rc Iirc ii

NH-C-O-R3
in der R^, R2 und R, die obige Bedeutung haben,NH-COR 3
in which R ^, R2 and R, have the above meaning,

oder durch Austausch des Halogensubstituenten X in Farbstoffen der allgemeinen Formelor by replacing the halogen substituent X in dyes of the general formula

IIIIII

Le A 15 451Le A 15 451

509827/0892509827/0892

worinwherein

X .für Chlor oder Brom steht undX stands for chlorine or bromine and

R^, Rp und R, die oben angegebene Bedeutung haben,R ^, Rp and R, have the meanings given above,

gegen einen Cyansubstituenten, in dem man Verbindungen der Formel III mit CuCN oder CuCN-bildenden Verbindungen in vorzugsweise aprotischen·organischen Lösungsmitteln bei Temperaturen von 50 bis 1500C, vorzugsweise 80 bis 1200C umsetzt (vgl. Britische Patentschrift 1 125 683 = US-Patentanmeldung S.N. 282471against a cyano substituent, in the compounds of the formula III forming CuCN with CuCN or compounds in a preferably aprotic · organic solvents at temperatures of 50 to 150 0 C, preferably 80 to 120 0 C. (cf.. British Patent Specification 1125683 = US -Patent application SN 282471

Geeignete Lösungsmittel sind Dimethylformamid, Dimethylacetamid, N,N-Diäthylharnstoff, Dimethylsulfoxid, N-Methylpyrrolidon u.a., denen zweckmäßigerweise ein aromatischer N-Heterocyclus, z.B. Pyridine und Chinoline, im Gewichtsverhältnis von z.B. 5 : 1 bis 20 : 1 zugesetzt werden.Suitable solvents are dimethylformamide, dimethylacetamide, N, N-diethylurea, dimethyl sulfoxide, N-methylpyrrolidone and others, which are conveniently an aromatic N-heterocycle, e.g. Pyridines and quinolines, in a weight ratio of e.g. 5: 1 to 20: 1, can be added.

Die erfindungsgemäß herstellbaren Farbstoffe eignen sich zum Färben und Bedrucken von synthetischen Fasermaterialien, insbesondere solchen aus Cellulosetriacetat und Polyestern in klaren blauen Tönen. Die Farbstoffe zeichnen sich durch hohe Farbstärke und gutes Aufbauvermögen, die Färbungen durch gute Allgemeinechtheiten, insbesondere gute Lichtechtheit aus.The dyes which can be prepared according to the invention are suitable for dyeing and printing synthetic fiber materials, in particular those made of cellulose triacetate and polyester in clear blue tones. The dyes are characterized by high color strength and good build-up capacity, the dyeings are characterized by good all-round fastness properties, in particular good lightfastness.

Die Farbstoffe gelangen einzeln, in Mischung untereinander oder in Mischung mit anderen Farbstoffen bevorzugt in fein dispergierter Form zur Anwendung.The dyes arrive individually, as a mixture with one another or as a mixture with other dyes, preferably in finely dispersed form Form for application.

Das Färben und Bedrucken kann nach bekannten Verfahren, z.B. bei 95 - 1000C unter Normaldruck in Gegenwart von Carriern, nach dem HT- oder dem Thermosolverfahren durchgefürhrt werden.The dyeing and printing may be prepared by known methods, for example at 95-100 0 C under normal pressure in the presence of carriers are durchgefürhrt after HT or the thermosol.

Le A 15 451 - 2 - Le A 15 451 - 2 -

509827/0892509827/0892

Beispiel. 1Example. 1

10r6 g 2-Amino-3,5-dinitro-benzonitril werden unter Rühren bei max. O0C in eine Mischung aus 65 ml 96 %iger-H2SO^ und 35 ml 85 %±ger Η^ΡΟλ eingetragen. Bei -5 bis -2°C werden 8,6 ml Nitroiylschwefelsäure (2,45 ml entsprechen 1 g NaNO9) tropfenweise zugefügt und die Mischung anschließend 5 Stunden bei max. 00G gerührt.10 r 6 g of 2-amino-3,5-dinitro-benzonitrile are introduced into a mixture of 65 ml of 96% H 2 SO ^ and 35 ml of 85 % ger Η ^ ΡΟλ with stirring at max. 0 ° C. At -5 to -2 ° C 8.6 ml Nitroiylschwefelsäure 0 0 G (2.45 ml corresponding to 1 g NaNO 9) added dropwise and then the mixture for 5 hours at max. Stirring.

12,5 g . 1-(N,N-Diäthylamino)-.p-(methoxycarbonylamino)-benzol werden unter Zusatz von 5 ml'48 %iger H2SO^ in 150 ml Eiswasser gelöst. Nach Zugabe von 0,5 g Amidosulfonsäure fügt man die obige Diazotierung tropfenweise zu und hält die Temperatur dabei durch Einwurf von Eis unter O0C. Die Kupplung ist nach kurzer Zeit beendet. Der ausgefallene Farbstoff der Formel12.5 g. 1- (N, N-diethylamino) -.p- (methoxycarbonylamino) benzene are dissolved in 150 ml of ice water with the addition of 5 ml of 48% H 2 SO ^. After adding 0.5 g of sulfamic acid, the above diazotization is added dropwise and the temperature is kept below 0 ° C. by throwing in ice. The coupling is complete after a short time. The unusual dye of the formula

NH-COOCH3 NH-COOCH 3

wird abgesaugt, neutral gewaschen und getrocknet. Das erhaltene dunkle Pulver färbt Polyesterfasern in lichtechten klaren blauen Tönen.is filtered off with suction, washed neutral and dried. The dark powder obtained dyes polyester fibers in lightfast clear blue tones.

Beispiel 2Example 2

29,5 g des Farbstoffs der Formel " ■29.5 g of the dye of the formula "■

(C2H5)2
NH-COOC2H5 (C 2 H 5 ) 2
NH-COOC 2 H 5

hergestellt durch Diazotierung von 2,4-Dinitro-6-brom-anilin und Kupplung auf 1-(N,N-Diäthylamino)-3-(äthoxycarbonylamino)-benzol werden in 50ml DMF unter Zusatz von 5 ml Pyridin mit 5,2 g CuCN bei 85 - 900C umgesetzt. Die Reaktionsprodukte werdenprepared by diazotization of 2,4-dinitro-6-bromo-aniline and coupling to 1- (N, N-diethylamino) -3- (ethoxycarbonylamino) benzene are mixed with 5.2 g in 50 ml of DMF with the addition of 5 ml of pyridine CuCN at 85 - 90 0 C implemented. The reaction products are

Le A 15 451 - 3 - Le A 15 451 - 3 -

509827/0892509827/0892

mit Wasser gefällt und zur Entfernung von Cu(I)-salzen in eine Lösung von 10,4 g FeCIjJ in 150 ml 10 %iger Salzsäure eingetragen. Nach Rühren über Nacht wird der Farbstoff der Formelprecipitated with water and to remove Cu (I) salts in a Introduced a solution of 10.4 g FeCljI in 150 ml 10% hydrochloric acid. After stirring overnight the dye becomes of the formula

NH-COOC2H5 NH-COOC 2 H 5

abgesaugt und mit Wasser neutral gewaschen. Nach dem Trocknen erhält man ein dunkles Pulver, das Fasern aus Polyäthylenterephthalat in klaren blauen Tönen mit sehr guter Lichtechtheit färbt.Sucked off and washed neutral with water. After drying, a dark powder is obtained, the fibers of polyethylene terephthalate dyes in clear blue tones with very good lightfastness.

Ersetzt man in diesen Beispielen die Kupplungskomponente durch die nachstehend genannten Verbindungen, so erhält man blaue Farbstoffe mit ähnlichen Eigenschaften.If the coupling component in these examples is replaced by the compounds mentioned below, blue ones are obtained Dyes with similar properties.

NHCOOCH,NHCOOCH,

-CH2CH2CH,-CH 2 CH 2 CH,

/--CH0-CH,/ - CH 0 -CH,

NHCOOCH,NHCOOCH,

""CHp-CHpCH,"" CHp-CHpCH,

NHCOOCOHNHCOOC O H

NHCOOCH,NHCOOCH,

-CH,
-CH2CH,-CH,
-CH 2 CH,

-CH,-CH,

CHpCHpCHpCH-CHpCHpCHpCH-

Le A 15 451Le A 15 451

509827/0892509827/0892

Claims (4)

PatentansprücheClaims 1. Azofarbstoffe der Formel1. Azo dyes of the formula O2N-O 2 N- CN NH-C-O-R, δ' 3 CN NH-COR, δ ' 3 worin R^, R2 und R, unabhängig voneinander fürwherein R ^, R 2 and R, independently of one another, represent Al^yI stehen.Al ^ yI stand. 2. Azofarbstoff der Formel2. Azo dye of the formula O2NO 2 N NO2 NO 2 7 \7 \ CN NHCOOCHCN NHCOOCH 3. Verfahren zur Herstellung von Azofarbstoffen, dadurch gekennzeichnet, daß man entweder diazotiertes 2-Amino-3,5-dinitrobenzonitril mit Verbindungen der Formel3. Process for the production of azo dyes, characterized in that that either diazotized 2-amino-3,5-dinitrobenzonitrile with compounds of the formula ■N;■ N; •R• R NHCOOR-NHCOOR- kuppelt,clutch, worin R^, R2 und R, die in Anspruch 1 genannte Bedeutungwherein R ^, R 2 and R, the meaning given in claim 1 haben, oder daß man in Verbindungen der Formelhave, or that one in compounds of the formula worin X für Chlor oder Brom steht und R1-R, die in An spruch 1 genannte Bedeutung haben. Le A 15 451 - 5 -wherein X is chlorine or bromine and R 1 -R, which have the meaning mentioned in claim 1 to. Le A 15 451 - 5 - 509827/0892509827/0892 den Halogensubstituenten X gegen einen Cyansubstituenten in an sich bekannter Weise austauscht.replaces the halogen substituent X with a cyan substituent in a manner known per se. 4. Verfahren zum Färben und Bedrucken von synthetischen Fasermaterialien, dadurch gekennzeichnet, daß man Farbstoffe des Anspruchs 1 einsetzt.4. Process for dyeing and printing synthetic fiber materials, characterized in that the dyes of claim 1 are used. Le A 15 451Le A 15 451 S09827/0892S09827 / 0892
DE19732363676 1973-12-21 1973-12-21 AZO DYES Pending DE2363676A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DE19732363676 DE2363676A1 (en) 1973-12-21 1973-12-21 AZO DYES
NL7416004A NL7416004A (en) 1973-12-21 1974-12-09 AZO DYES.
IT3077874A IT1027849B (en) 1973-12-21 1974-12-19 AZOIC COCORANTS
JP14509374A JPS5096624A (en) 1973-12-21 1974-12-19
CH1695274A CH583767A5 (en) 1973-12-21 1974-12-19
FR7442291A FR2255353B3 (en) 1973-12-21 1974-12-20
BE151776A BE823672A (en) 1973-12-21 1974-12-20 PRODUCTION AND APPLICATION OF NEW AZOIC COLORANTS
GB5514374A GB1449399A (en) 1973-12-21 1974-12-20 Azo dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19732363676 DE2363676A1 (en) 1973-12-21 1973-12-21 AZO DYES

Publications (1)

Publication Number Publication Date
DE2363676A1 true DE2363676A1 (en) 1975-07-03

Family

ID=5901460

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19732363676 Pending DE2363676A1 (en) 1973-12-21 1973-12-21 AZO DYES

Country Status (8)

Country Link
JP (1) JPS5096624A (en)
BE (1) BE823672A (en)
CH (1) CH583767A5 (en)
DE (1) DE2363676A1 (en)
FR (1) FR2255353B3 (en)
GB (1) GB1449399A (en)
IT (1) IT1027849B (en)
NL (1) NL7416004A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4257944A (en) * 1978-04-05 1981-03-24 Imperial Chemical Industries Limited Process for the manufacture of cyano azo dyes

Also Published As

Publication number Publication date
CH583767A5 (en) 1977-01-14
IT1027849B (en) 1978-12-20
GB1449399A (en) 1976-09-15
FR2255353A1 (en) 1975-07-18
BE823672A (en) 1975-06-20
FR2255353B3 (en) 1977-09-23
NL7416004A (en) 1975-06-24
JPS5096624A (en) 1975-07-31

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