CH239329A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH239329A CH239329A CH239329DA CH239329A CH 239329 A CH239329 A CH 239329A CH 239329D A CH239329D A CH 239329DA CH 239329 A CH239329 A CH 239329A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- parts
- disazo dye
- become
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- -1 aminoazo Chemical group 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229920003043 Cellulose fiber Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 2371816. Verfahren zur Herstellung eines Bisazofarbstoifes.. Es wurde gefunden, daB ein wertvoller Disazofarbstoff hergestellt werden kann, wenn man den diazotierten Aminoazofarb- stoff der Formel
EMI0001.0009
mit 8-Ogychinolin vereinigt.
Der neue Farbstoff stellt ein dunkelrotes Pulver dar, das sich in Wasser und in ver dünnten Alkalien mit oranger, in konzen trierter Schwefelsäure mit violetter Farbe löst und Cellulosefasern in gelblichroten Tönen färbt, die beim Nachkupfern röter, licht- und waschechter werden.
Der dem vorliegenden Verfahren als Aus gangsstoff dienende Aminoazofarbstoff der obigen Formel kann z. B. durch Kuppeln von, diazotierter 4-Chlor-2-amino-l-phenogyessig- säure mit 2-(4'-Aminobenzoyl)-amino-5-ogy- naphthalin-7-sulfonsäure erhalten werden. Die Diazotierung kann in bekannter Weise z.
B. so vorgenommen werden, daB man eine Lösung bezw. Suspension des Aminoazofarb- stoffes in neutralem oder schwach alkali schem Medium mit der nötigen Menge Nitrit versetzt und dann ansäuert.
Die Kupplung der diazotierten Amino- azoverbindung mit der & -Ogychinolink-ompo- nente erfolgt.in alkalischem, beispielsweise Alkalihydrogyd und Alkalicarbonat enthal tendem Medium. <I>Beispiel:
</I> Der mit Kochsalz abgeschiedene, filtrierte und abgepreBte Aminoazofarbstoff, der aus 20,1 Teilen 4-Chlor-2-amino-l-phenoxyessig- säure durch Diazotieren und Kuppeln mit 35,8 Teilen 2-(4'-Aminobenzoyl)-amine-5-oxy- naphthalin-7-sulfonsäure in sodaalkalischem Medium in bekannter Weise erhältlich ist, wird in<B>1000</B> Teilen Wasser gelöst, mit 7 Tei len Natriumnitrit versetzt und durch Zugabe von Eis auf 4 C gekühlt. Darnach versetzt man mit 3'0 Teilen konzentrierter Salzsäure und rührt etwa 20 Stunden.
Die erhaltene Diazoverbindung versetzt man nun mit einer Lösung von 14,5 Teilen 8-Oxychinolin und 12 Teilen konzentrierter Salzsäure in 50 Tei len Wasser. Darnach gibt man 50 Teile einer 30 % igen Natronlaugelösung zu und verrührt. einige Stunden. Darnach erwärmt man auf <B>55-60'</B> C, gibt zwecks Abscheidung des Farbstoffes 200 Teile Kochsalz zu und fil triert und trocknet den abgeschiedenen Farb- stoff_
<B> Additional patent </B> to main patent no. 2371816. Process for the production of a disazo dye. It has been found that a valuable disazo dye can be produced by using the diazotized aminoazo dye of the formula
EMI0001.0009
combined with 8-ogyquinoline.
The new dye is a dark red powder that dissolves in water and in dilute alkalis with orange, in concentrated sulfuric acid with violet color and dyes cellulose fibers in yellowish-red tones, which become redder, more lightfast and washfast when re-coppering.
The aminoazo dye of the above formula serving as starting material for the present process can, for. B. by coupling, diazotized 4-chloro-2-amino-1-phenogyacetic acid with 2- (4'-aminobenzoyl) -amino-5-ogy- naphthalene-7-sulfonic acid. The diazotization can be carried out in a known manner, for.
B. be made so that one respectively a solution. Suspension of the aminoazo dye in a neutral or weakly alkaline medium mixed with the necessary amount of nitrite and then acidified.
The coupling of the diazotized amino-azo compound with the ogychinolink component takes place in an alkaline medium, for example containing alkali hydrogen and alkali carbonate. <I> example:
</I> The aminoazo dyestuff which has been separated off with common salt, filtered and squeezed out, is obtained from 20.1 parts of 4-chloro-2-amino-1-phenoxyacetic acid by diazotization and coupling with 35.8 parts of 2- (4'-aminobenzoyl) -amine-5-oxynaphthalene-7-sulfonic acid in a soda-alkaline medium is available in a known manner, is dissolved in <B> 1000 </B> parts of water, mixed with 7 parts of sodium nitrite and cooled to 4 C by adding ice . Then 3'0 parts of concentrated hydrochloric acid are added and the mixture is stirred for about 20 hours.
The diazo compound obtained is then mixed with a solution of 14.5 parts of 8-oxyquinoline and 12 parts of concentrated hydrochloric acid in 50 parts of water. Then 50 parts of a 30% sodium hydroxide solution are added and the mixture is stirred. some hours. Then it is heated to <B> 55-60 '</B> C, 200 parts of table salt are added for the purpose of separating the dye and the separated dye is filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH239329T | 1942-08-21 | ||
| CH237186T | 1943-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH239329A true CH239329A (en) | 1945-09-30 |
Family
ID=25728232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH239329D CH239329A (en) | 1942-08-21 | 1942-08-21 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH239329A (en) |
-
1942
- 1942-08-21 CH CH239329D patent/CH239329A/en unknown
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