CH155457A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH155457A CH155457A CH155457DA CH155457A CH 155457 A CH155457 A CH 155457A CH 155457D A CH155457D A CH 155457DA CH 155457 A CH155457 A CH 155457A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- production
- dye
- oxy
- methoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 8
- 240000007817 Olea europaea Species 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000000835 fiber Substances 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000283207 Indigofera tinctoria Species 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Yerfaluen zur Herstellung eines liiipenfarbstoffes. 2.1-Naphtisatine, welche eine Alkyloxy- gruppe im Molekül enthalten, sind bis jetzt noch nicht bekannt. Es wurde nun gefunden, dass man neue wertvolle Farbstoffe erhält, wenn man Alkyloxy- 2. 1- naphtisatine mit 3-Oxy-thionaphthenen der Naphthalinreihe nach bekannten Methoden zu Thionaphthen- (2)-indol-(2')-indigos kondensiert.
Die Farbstoffe liefern je nach der Stellung der Alkyloxygruppe im 2.1-Naphtisatin-mole- kül und nach der Art der Oxy-thio-naphthene der Naphthalinreihe Färbungen von brauner bis olivgrüner gedeckter Nüance. Die Fär bungen zeichnen sich durch Fülle des Farb tones und gute Echtheitseigenschaften aus.
Die Alkyloxy-2.1-naphtisatiiie können aus den ent#prechenden Alkyloxy-ss-uaphthylauii- nen zum Beispiel nach der Methode von Sandmeyer hergestellt werden.
In der folgenden Tabelle sind eine An zahl von Kombinationen und die hiermit erhältlichen Färbungen angeführt.
EMI0001.0026
Isatin <SEP> Oxy-thionaphthen <SEP> Färbungen
<tb> auf <SEP> Baumrolle
<tb> 6-Methoxy-2.1-napbtisatin <SEP> 1.2-Napht-oxy-thioiiaphthen <SEP> grünolive
<tb> 6-Methoxy-2.1-naphtisatin <SEP> 6-blethoxy-1.2-napht-oxy- <SEP> lebhaft
<tb> thionaphthen <SEP> grünolive
<tb> 7-Methoxy-2.1-naphtisatin <SEP> 1.2-Napht-oxy-thionaphthen <SEP> violett
<tb> (F. <SEP> P.
<SEP> 280 <SEP> ) <SEP> braun
<tb> 7-Methoxy-2.1-naphtisatin <SEP> 6-Methoxy-l.2-napht-oxy- <SEP> gedecktes
<tb> thionaphthen <SEP> rotbraun
<tb> 3-Methoxy-2.1-naphtisatin <SEP> 6-Methoxy-l.2-napht-oxy- <SEP> gedecktes
<tb> thionaphthen <SEP> olivebraun Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Herstellung eines Küpen- farbstoffes, dadurch gekennzeichnet, dass man 6-1lIethoxy-2.1-naphtisatin nach Überführung in das entsprechende a-Chlorid mit 2.1-Napht- oxythiophen kondensiert.
Der so erhaltene Farbstoff ist in trockener Form ein schwarzes Pulver, das sich in kon zentrierter Schwefelsäure mit blauer Farbe löst. Aus gelber Küpe färbt er die Faser olive. <I>Beispiel:</I> 22,6 Teile 6-14Zethoxy-2.1-naphtisatiri (das aus Eisessig in dunkelrotbraunen Kristallen vom Schmelzpunkt 292 kristallisiert) wer den durch Erwärmen mit 26 Teilen Phos- phorpentachlorid in Chlorbenzol in das Isatin- a-chlorid übergeführt. Diese Lösung gibt man zu einer Lösung von 20 Teilen 2.1-Napht- oxy-thiophen in Chlorbenzol und erwärmt das Gemisch kurze Zeit.
Nach Erkalten wird der gebildete Farbstoff abgesaugt und mit Chlor benzol gewaschen.
Yerfaluen for the production of a lip dye. 2.1-naphthisatins, which contain an alkyloxy group in the molecule, are not yet known. It has now been found that new valuable dyes are obtained if alkyloxy-2.1-naphtisatins are condensed with 3-oxy-thionaphthenes of the naphthalene series by known methods to give thionaphthene (2) indole (2 ') indigos.
Depending on the position of the alkyloxy group in the 2.1-naphtisatin molecule and according to the type of oxy-thio-naphthene of the naphthalene series, the dyes produce colors ranging from a brown to olive-green shade. The dyeings are distinguished by their abundance of color and good fastness properties.
The alkyloxy-2.1-naphthatis can be produced from the corresponding alkyloxy-ss-uaphthylic lines, for example by the Sandmeyer method.
The following table lists a number of combinations and the colors available with them.
EMI0001.0026
Isatin <SEP> oxy-thionaphthene <SEP> stains
<tb> on <SEP> tree roll
<tb> 6-methoxy-2.1-napbtisatin <SEP> 1.2-naphth-oxy-thioiiaphthen <SEP> green olive
<tb> 6-methoxy-2.1-naphtisatin <SEP> 6-blethoxy-1.2-napht-oxy- <SEP> lively
<tb> thionaphthene <SEP> olive green
<tb> 7-methoxy-2.1-naphtisatin <SEP> 1.2-naphth-oxy-thionaphthen <SEP> violet
<tb> (F. <SEP> P.
<SEP> 280 <SEP>) <SEP> brown
<tb> 7-methoxy-2.1-naphtisatin <SEP> 6-methoxy-1.2-napht-oxy- <SEP> covered
<tb> thionaphthene <SEP> red-brown
<tb> 3-methoxy-2.1-naphtisatin <SEP> 6-methoxy-1.2-napht-oxy- <SEP> covered
<tb> thionaphthen <SEP> olive brown The present patent now relates to a process for the production of a vat dye, characterized in that 6-1lethoxy-2.1-naphthiophene is condensed after conversion into the corresponding α-chloride with 2.1-naphthoxythiophene .
The dye thus obtained is a black powder in dry form which dissolves in concentrated sulfuric acid with a blue color. He dyes the fiber olive from a yellow vat. <I> Example: </I> 22.6 parts of 6-14zethoxy-2.1-naphtisatiri (which crystallizes from glacial acetic acid in dark red-brown crystals with a melting point of 292) are converted into isatin a- by heating with 26 parts of phosphorus pentachloride in chlorobenzene. chloride transferred. This solution is added to a solution of 20 parts of 2,1-naphthoxy-thiophene in chlorobenzene and the mixture is heated for a short time.
After cooling, the dye formed is filtered off with suction and washed with chlorobenzene.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE155457X | 1930-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH155457A true CH155457A (en) | 1932-06-30 |
Family
ID=5677026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH155457D CH155457A (en) | 1930-08-01 | 1931-07-24 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH155457A (en) |
-
1931
- 1931-07-24 CH CH155457D patent/CH155457A/en unknown
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