DE1544373A1 - Process for the preparation of an azo dye - Google Patents

Process for the preparation of an azo dye

Info

Publication number
DE1544373A1
DE1544373A1 DE19651544373 DE1544373A DE1544373A1 DE 1544373 A1 DE1544373 A1 DE 1544373A1 DE 19651544373 DE19651544373 DE 19651544373 DE 1544373 A DE1544373 A DE 1544373A DE 1544373 A1 DE1544373 A1 DE 1544373A1
Authority
DE
Germany
Prior art keywords
parts
dye
preparation
azo dye
solution
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.)
Withdrawn - After Issue
Application number
DE19651544373
Other languages
German (de)
Inventor
Lange Dr Guenter
Wippel Dr Hans Guenter
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to US775959A priority Critical patent/US3544260A/en
Publication of DE1544373A1 publication Critical patent/DE1544373A1/en
Withdrawn - After Issue legal-status Critical Current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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

BADISCHE ANILIN- & SODA-FABRIK AGBADISCHE ANILIN- & SODA-FABRIK AG

544373544373

Unser Zeichen: O. Z. 2J> 63k Hp/Dtt Ludwigshafen/Rhein, den 7-5.1965Our reference: OZ 2J> 63k Hp / Dtt Ludwigshafen / Rhein, 7-5.1965

Verfahren zur Herstelllang eines AzofarbstoffsProcess for the production of an azo dye

Die Erfindung betrifft den Farbstoff der FormelThe invention relates to the dye of the formula

NHCOCH3 NHCOCH 3

Dieser Farbstoff wird in an sich bekannter Weise durch Kupplung der Diazoverbindung von 2-Amino-j5-brom~5-nitrobenzonitril mit N,N~Dihydroxyäthyl-m-acetylaminoanilin erhalten.This dye is in a known manner by coupling the Diazo compound of 2-amino-j5-bromo ~ 5-nitrobenzonitrile with N, N ~ dihydroxyethyl-m-acetylaminoaniline obtain.

Der neue Farbstoff eignet sich, besonders in feinverteilter Form, hervorragend zum Färben von Texti!materialien aus synthetischen linearen Polyestern, vorzugsweise nach dem sogenannten Hochtemperaturverfahren. Er liefert Färbungen in klaren blauen Farbtönen mit sehr guten Echtheitseigenschaften, insbesondere ausgezeichneten thermischen Echtheiten. Ferner eignet er sich zum Färben von Textilmaterialien aus Celluloseacetat und synthetischen linearen Polyamiden.The new dye is suitable, especially in finely divided form, excellent for dyeing textile materials made of synthetic materials linear polyesters, preferably using the so-called high-temperature process. It provides colors in clear blue tones with very good fastness properties, in particular excellent thermal fastness properties. It is also suitable for dyeing Textile materials made from cellulose acetate and synthetic linear polyamides.

Die im folgenden Beispiel genannten Teile sind Gewiohtsteile.The parts mentioned in the following example are parts by weight.

Beispielexample

In eine Lösung bestehend aus 50 Teilen konzentrierter Schwefelsäure und 14,5 Teilen Nitrosylschwefelsäure mit einem Gehalt von In a solution consisting of 50 parts of concentrated sulfuric acid and 14.5 parts of nitrosylsulfuric acid with a content of

9 0 9 8 19/1112 ~2~9 0 9 8 19/1112 ~ 2 ~

13,1$ an freiem Distickstofftrioxyd, werden bei 0 biß 5°C 12,1 Teile 2-Amino-3-brom-5-nitrobenzonitril eingetragen und diese Lösung drei Stunden bei 0 bis 5°C gerührt» Die so erhaltene klare Diazolösung läßt man allmählich in eine Lösung, bestehend aus 11,9 Teilen 3-Acetylamino-N,N-di-i-(ß-hydroxyäthyl)-aniinobenzol, 25 Teilen Wasser, β Teilen konzentrierter Salzsäure, 100 Teilen Eis und 1 Teil Amidosulfonsäuren einfließen. Nach einstündigem Rühren wird eine Lösung von 41 Teilen Natriumacetat in 200 Teilen Wasser zugesetzt, der kristalline Farbstoff abgesaugt, mit Wasser neutral gewaschen und bei 40°C unter vermindertem Druck getrocknet·13.1 $ of free dinitrogen trioxide, 12.1 parts of 2-amino-3-bromo-5-nitrobenzonitrile are introduced at 0 to 5 ° C. and this solution is stirred for three hours at 0 to 5 ° C. The clear diazo solution thus obtained is left gradually flow into a solution consisting of 11.9 parts of 3-acetylamino-N, N-di- i - (ß-hydroxyethyl) -aniinobenzene, 25 parts of water, β parts of concentrated hydrochloric acid, 100 parts of ice and 1 part of sulfamic acids. After stirring for one hour, a solution of 41 parts of sodium acetate in 200 parts of water is added, the crystalline dye is filtered off with suction, washed neutral with water and dried at 40 ° C under reduced pressure.

-3-909819/1 1 12-3-909819 / 1 1 12

Claims (2)

15*437315 * 4373 PatentansprücheClaims 1· Verfahren zur Herstellung eines Monoaaofarbstoffs, kennze lohnet j daß man diazotiertes 2-Amino-3-Dro»n-5-iiitrobenzonitril mit 3-Acetylamino-NiN-di*(ß-hydroxyäthyl)~aminobenzol kuppelt.1 · A process for the production of a mono-ao dye, ken n ze is worthwhile, that one coupling diazotized 2-amino-3-dro »n-5-nitrobenzonitrile with 3-acetylamino-N , N-di * (β-hydroxyethyl) ~ aminobenzene. 2. Der Farbstoff der Formel2. The dye of the formula BADISCHE ANILIN- & SODA-FABRIK AGBADISCHE ANILIN- & SODA-FABRIK AG 9 0 9819/11129 0 9819/1112
DE19651544373 1965-05-08 1965-05-08 Process for the preparation of an azo dye Withdrawn - After Issue DE1544373A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US775959A US3544260A (en) 1965-05-08 1968-11-14 Process for dyeing synthetic linear polyester fibrous textile material blue shades and the dyed material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB0081830 1965-05-08

Publications (1)

Publication Number Publication Date
DE1544373A1 true DE1544373A1 (en) 1969-05-08

Family

ID=6981259

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19651544373 Withdrawn - After Issue DE1544373A1 (en) 1965-05-08 1965-05-08 Process for the preparation of an azo dye

Country Status (6)

Country Link
AT (1) AT255611B (en)
BE (1) BE680689A (en)
CH (1) CH458579A (en)
DE (1) DE1544373A1 (en)
GB (1) GB1140214A (en)
NL (2) NL6605986A (en)

Also Published As

Publication number Publication date
AT255611B (en) 1967-07-10
GB1140214A (en) 1969-01-15
BE680689A (en) 1966-11-07
NL6605986A (en) 1966-11-10
CH458579A (en) 1968-06-30
NL129035C (en)

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Legal Events

Date Code Title Description
E77 Valid patent as to the heymanns-index 1977
8330 Complete disclaimer