AT52182B - Process for the preparation of indigoid dyes. - Google Patents
Process for the preparation of indigoid dyes.Info
- Publication number
- AT52182B AT52182B AT52182DA AT52182B AT 52182 B AT52182 B AT 52182B AT 52182D A AT52182D A AT 52182DA AT 52182 B AT52182 B AT 52182B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- indigoid dyes
- azenaphthenequinone
- indoxyls
- dyes
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N indoxyl Chemical group C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- OLKNXLMMZQVMDW-UHFFFAOYSA-N O=C(C(C(N1Br)=CC=C2)=C2Br)C1=O.Cl Chemical compound O=C(C(C(N1Br)=CC=C2)=C2Br)C1=O.Cl OLKNXLMMZQVMDW-UHFFFAOYSA-N 0.000 description 1
- -1 acetyl oxyl Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- COHYTHOBJLSHDF-BUHFOSPRSA-N indigo dye Chemical compound N\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-BUHFOSPRSA-N 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung indigoider Farbstoffe.
1s wurde gefunden, dass man sehr wertvolle rote bis violette indigoide Farbstoffe von guten Echtheitseigenschaften dadurch erhalten kann, dass man im Benzolkern dihalogenisierte Indoxyle oder ihre Azetylderivate mit Azenaphtenchinon kondensiert. Das Verfahren wird in der Weise ausgeführt, dass man die genannten Indoxyle, wie Dibromindoxyl, mit dem Azenaphtenchinon zusammen in einem geeigneten Lösungsmittel, zweckmässig unter Zusatz eines Kondensationsmittels, erwärmt.
In der deutschen Patentschrift Nr. 198510 sind bromhaltige Küpenfarbstoffe beschieben, welche durch Bromieren des Kondensationsproduktes von Azenaphtenchinon mit Indoxyl erhalten werden. Von diesen Produkten sind die vorliegenden Farbstoffe sowohl chemisch als auch namentlich in färberischer Beziehung durchaus verschieden. Sie ziehen besser und besitzen wesentlich klarere, vollere Nuancen und sind ausserdem ausgiebiger.
Vor dem Farbstoff der deutschen Patentschrift Nr. 206647 besitzen die Farbstoffe der vorliegenden Erfindung die eben hervorgehobenen Vorzüge des besseren Ziehens und der klareren Nuance in noch erhöhtem Masse.
Ausserdem weist das Verfahren der vorliegenden Erfindung, soweit die Azetyl- verbindungen der halogenisierten Indoxyle verwendet werden, den weiteren Vorteil auf, dass bei der Farbstoffbildung die gleichzeitige Bildung eines Indigofarbstoffes infolge der grösseren Beständigkeit des Azetylindoxylderivates gegenüber dem in der genannten Patentschrift Nr. 2066. 1, 7 benützten Indoxyl vermieden wird.
Beispiel.
375 Teile Dibromdiazetylindoxyl und 182 Teile Azenaphtenchinon werden in der nötigen Menge Nltrohen/ : ol oder Chlorbenzol heIss gelöst. Gibt man nun zu der gelben
Lösung eine geringe Menge Piperidin, so färbt sie sich momentan tiefrot und der Farbstoff kristallisiert nach kurzem Erwärmen in vorzüglicher Ausbeute aus. Er ist identisch mit dem aus Dibromisatinchlorid und Azenaphtenon erhältlichen Produkt. An Stelle des
Diazetylderivates kann auch das Monoazetylderivat oder das Dibromindoxyl selbst ver- wendet werden. werden.
Das Verfahren verläuft in analoger Weise bei Verwendung anderer im Benzolkern halogenisicrter Indoxyle. wie Bromchlorindoxyl oder Dichlorindoxyl usw.
Anstatt des Azenaphtenchinons können auch seine durch Halogen substituierten
Derivate zur Anwendung gelangen. Man erhält alsdann blauere Nuancen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of indigoid dyes.
It was found that very valuable red to violet indigoid dyes with good fastness properties can be obtained by condensing indoxyls dihalogenized in the benzene nucleus or their acetyl derivatives with azenaphthenequinone. The process is carried out in such a way that the indoxyls mentioned, such as dibromoindoxyl, are heated together with the azenaphthenequinone in a suitable solvent, advantageously with the addition of a condensing agent.
German Patent No. 198510 describes bromine-containing vat dyes which are obtained by brominating the condensation product of azenaphthenequinone with indoxyl. The present dyestuffs are entirely different from these products, both chemically and especially in terms of their coloring. They draw better and have much clearer, fuller nuances and are also more extensive.
Before the dye of German Patent No. 206647, the dyes of the present invention have the advantages of better drawing and clearer shade to an even greater extent.
In addition, if the acetyl compounds of the halogenated indoxyls are used, the process of the present invention has the further advantage that, during dye formation, the simultaneous formation of an indigo dye as a result of the greater resistance of the acetyl oxyl derivative compared to that in patent specification no. 2066.1 , 7 used indoxyl is avoided.
Example.
375 parts of dibromodiazetylindoxyl and 182 parts of azenaphthenequinone are dissolved hot in the required amount of Nltrohen /: ol or chlorobenzene. One gives now to the yellow one
Solution a small amount of piperidine, it turns deep red momentarily and the dye crystallizes out in excellent yield after brief heating. It is identical to the product obtainable from dibromoisatin chloride and azenaphtenone. Instead of
Diacetyl derivatives, the monoacetyl derivative or the dibromoindoxyl itself can also be used. will.
The process proceeds in an analogous manner when using other indoxyls halogenated in the benzene nucleus. like bromochloroindoxyl or dichloroindoxyl etc.
Instead of the azenaphtenquinone, its halogen-substituted
Derivatives are used. You then get bluer shades.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE52182X | 1910-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT52182B true AT52182B (en) | 1912-02-10 |
Family
ID=5627248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT52182D AT52182B (en) | 1910-01-17 | 1910-12-29 | Process for the preparation of indigoid dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT52182B (en) |
-
1910
- 1910-12-29 AT AT52182D patent/AT52182B/en active
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