CH178549A - Process for the preparation of an unsymmetrical dye of the thioindigo series. - Google Patents
Process for the preparation of an unsymmetrical dye of the thioindigo series.Info
- Publication number
- CH178549A CH178549A CH178549DA CH178549A CH 178549 A CH178549 A CH 178549A CH 178549D A CH178549D A CH 178549DA CH 178549 A CH178549 A CH 178549A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- dye
- thioindigo series
- methoxy
- dyes
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 3
- 239000000344 soap Substances 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- -1 ester salts Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines unsymmetrischen Farbstoffes der Thioüudigoreihe. Der im Handel befindliche 6.6'-Diäthoxy- thioindigo färbt und druckt bekanntlich ein lebhaftes rotstichiges Orange. Demgegenüber zeigt der 6.6'-Dimethoxythioindigo eine wesent lich gelbere und trübere Nuance; trotz seiner erhöhten Lichtechtheit kommt er infolge seiner völlig unzulänglichen Seifenechtheit praktisch nicht in Frage.
Es ist deshalb völlig überraschend, dass der 6-Methoxy-6'-äthoxythioindigo, der nach bekannten Methoden herstellbar ist, einer seits die erhöhte Lichtechtheit des Dimethoxy- t.hioindigos zeigt, anderseits eine völlig ge nügende Seifenechtheit besitzt. Überraschend ist ferner, dass die Nuance des Farbstoffes, die als etwa in der Mitte zwischen der der beiden vorgenannten Farbstoffe liegend zu er warten gewesen wäre, noch erheblich rot stichiger ist, als die des Diäthoxythioindigos.
Der Farbstoff, der sowohl zum Färben als auch zum Drucken von Textilfasern geeignet ist, kann auch vorteilhaft in Form der Ester- salze seiner Leukoverbindung zur Verwendung kommen. Das neue Produkt stellt daher eine wertvolle Bereicherung des Farbstoffsorti- ments dar.
Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Darstellung des 6-Methoxy- 6'-äthoxythioirrdigos, dadurch gekennzeichnet, dass man ein reaktionsfähiges 2-Derivat des 6 -Äthoxy- 2 .3 -diketo-dihydro-thionaphthens mit 6-Metboxy-3-oxythiorraphthen konden siert.
Der neue Farbstoff löst sich in Schwefel säure mit blauer Farbe und färbt aus gelber Küpe die Faser in lebhaften rotstichig orangen Tönen von guter Licht- und Seifenechtheit. <I>Beispiel:</I> 32,6 Teile 6-Äthoxy-2.3-diketo-dihydro- thionaphtherr-2-(p-dimethyl-aminoariil) wer den mit 18 Teilen 6-Methoxy-3-oxythionaph- then und etwa 400 Teilen Chlorbenzol ver rührt und etwa 2 Stunden auf<B>115-1200</B> erhitzt. Nach Abkühlung wird -der Farbstoff in üblicher Weise isoliert.
Process for the preparation of an asymmetrical dye of the Thioüudigo series The commercially available 6.6'-diethoxythioindigo colors and prints, as is known, a vivid reddish orange. In contrast, the 6,6'-dimethoxythioindigo shows a significantly more yellow and cloudy shade; Despite its increased lightfastness, it is practically out of the question due to its completely inadequate soapfastness.
It is therefore completely surprising that the 6-methoxy-6'-ethoxythioindigo, which can be prepared by known methods, on the one hand shows the increased lightfastness of dimethoxy-t.hioindigo, on the other hand has completely sufficient soapfastness. It is also surprising that the shade of the dye, which would have been expected to be somewhere in the middle between that of the two aforementioned dyes, is considerably more red than that of the diethoxythioindigo.
The dye, which is suitable both for dyeing and for printing textile fibers, can also be used advantageously in the form of the ester salts of its leuco compound. The new product is therefore a valuable addition to the range of dyes.
The present patent now relates to a process for the preparation of 6-methoxy-6'-ethoxythioirrdigo, characterized in that a reactive 2-derivative of 6-ethoxy-2 .3 -diketo-dihydro-thionaphthens is mixed with 6-metboxy-3 -oxythiorraphthen condensed.
The new dye dissolves in sulfuric acid with a blue color and dyes the fiber from a yellow vat in lively reddish orange shades of good light and soap fastness. <I> Example: </I> 32.6 parts of 6-ethoxy-2,3-diketo-dihydro- thionaphtherr-2- (p-dimethyl-aminoariil) with 18 parts of 6-methoxy-3-oxythionaphthene and about 400 parts of chlorobenzene are stirred and heated to <B> 115-1200 </B> for about 2 hours. After cooling, the dye is isolated in the usual way.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE178549X | 1933-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH178549A true CH178549A (en) | 1935-07-31 |
Family
ID=5706165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH178549D CH178549A (en) | 1933-08-25 | 1934-07-26 | Process for the preparation of an unsymmetrical dye of the thioindigo series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH178549A (en) |
-
1934
- 1934-07-26 CH CH178549D patent/CH178549A/en unknown
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