CH272483A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH272483A CH272483A CH272483DA CH272483A CH 272483 A CH272483 A CH 272483A CH 272483D A CH272483D A CH 272483DA CH 272483 A CH272483 A CH 272483A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- red
- blue
- preparation
- dye
- Prior art date
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
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
-
- 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/16—Naphthol-sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- 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
- C09B29/3652—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 containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—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 containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Azofarbstoff gelangt, wenn man diazotierten 4'-Tertiäramyl Z-amino-diphenyl- äther mit 1-Acetylamino-8-oxynaphtlialin-3,6- < lisulfonsäure vereinigt.
Der neue Farbstoff bildet ein rotes Pul ver, das sich in Wasser mit blauroter Farbe löst. und Wolle aus essigsaurem Bade in blau roten Tönen färbt.
Der beim vorliegenden Verfahren als Aus gangsstoff dienende 4'-Tertiiiramyl-2-amino- dipheny lädier kann nach an sieh bekannter :Methode durch Kondensation von 4-Tertiär- amyl -1- oxybenzol. mit 1- Chlor-2-nitrobenzol Und nachfolgende Reduktion der Nitrogruppe des erhaltenen 4'-Tertiäramyl-2-nitrodiphenyl- äthers zur Aminogruppe hergestellt werden.
Die Diazotierung kann wie üblich, z. B. mit Salzsäure und Natriumnitrit, durchge führt werden.
Die Kupplung erfolgt mit Vorteil in alka- liscliem, vorzugsweise alkaliearbonatalkali- schein Medium, gewünsehtenfalls unter Ver wendung geeigneter, die Kupplungsreaktion befördernder Zusätze, wie Alkohol, Pyridin usw.
<I>Beispiel:</I> 25,5 Teile 4'-Tertiärainyl-2-amino-1,7'-cli- phenyläther werden mit 46 Teilen konz. Salz- säure verrieben. Nach einer Stunde wird die Suspension des Chlorhydrates mit 120 Teilen einer gesättigten Natriumchloridlösung ange- sehlämmt und hierauf unterhalb + 50 allmäh lich mit einer konzentrierten wässerigen Lö sung von 7,2 Teilen Natriumnitrit versetzt.
Die schwach gelb gefärbte Diazolösung wird bei 00 mit cler Lösung von 41 Teilen des Di- natriumsalzes der l.-Acetyl-amino-8-oxynaph- tlialin-3,6-disulfonsäure in 330 Teilen einer gesättigten Natriumcarbonatlösung vermischt. Nacli einigen Stunden wird der blaurote Farb stoff abfiltriert und hierauf in heissem Was ser gelöst.
Die Lösung wird von allfälligen geringen Verunreinigungen abfiltriert und mit so viel Natriumchlorid versetzt, dass die Hauptmenge des Farbstoffes gefällt wird. Dieser wird abfiltriert, mit verdünnter Na triumchloridlösung gewasehen und getrocknet.
Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if diazotized 4'-tertiaryamyl-Z-aminodiphenyl ether is combined with 1-acetylamino-8-oxynaphthalene-3,6- <isulphonic acid.
The new dye forms a red powder that dissolves in water with a blue-red color. and dyes wool from acetic acid bath in shades of blue and red.
The 4'-tertiary amyl-2-aminodipheny used as starting material in the present process can be used according to a known method: method by condensation of 4-tertiary amyl-1-oxybenzene. with 1- chloro-2-nitrobenzene and subsequent reduction of the nitro group of the 4'-tertiaryamyl-2-nitrodiphenyl ether obtained to the amino group.
The diazotization can as usual, for. B. with hydrochloric acid and sodium nitrite, Runaway leads.
The coupling is advantageously carried out in alkali, preferably alkali carbonate alkaline medium, if desired using suitable additives that promote the coupling reaction, such as alcohol, pyridine, etc.
<I> Example: </I> 25.5 parts of 4'-Tertiärainyl-2-amino-1,7'-cliphenyl ether are concentrated with 46 parts. Hydrochloric acid triturated. After one hour, the suspension of the chlorohydrate is lamed with 120 parts of a saturated sodium chloride solution, and a concentrated aqueous solution of 7.2 parts of sodium nitrite is then gradually added below + 50.
The pale yellow colored diazo solution is mixed at 00 with a solution of 41 parts of the disodium salt of 1.-acetyl-amino-8-oxynaphthalene-3,6-disulfonic acid in 330 parts of a saturated sodium carbonate solution. After a few hours, the blue-red dye is filtered off and then dissolved in hot water.
Any minor impurities are filtered off from the solution and so much sodium chloride is added that most of the dye is precipitated. This is filtered off, washed with dilute sodium chloride solution and dried.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH272483T | 1948-02-26 | ||
CH270538T | 1948-02-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH272483A true CH272483A (en) | 1950-12-15 |
Family
ID=25731194
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH272483D CH272483A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of an azo dye. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH272483A (en) |
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1948
- 1948-02-26 CH CH272483D patent/CH272483A/en unknown
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