CH103139A - Process for the preparation of an indigo derivative. - Google Patents
Process for the preparation of an indigo derivative.Info
- Publication number
- CH103139A CH103139A CH103139DA CH103139A CH 103139 A CH103139 A CH 103139A CH 103139D A CH103139D A CH 103139DA CH 103139 A CH103139 A CH 103139A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfuric acid
- preparation
- thioindigo
- acid
- soluble
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- 235000000177 Indigofera tinctoria Nutrition 0.000 title description 3
- 229940097275 indigo Drugs 0.000 title description 3
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 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 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 sulfuric acid ester Chemical class 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- VIFKLIUAPGUEBV-UHFFFAOYSA-N 2-(3-hydroxy-1h-indol-2-yl)-1h-indol-3-ol Chemical compound N1C2=CC=CC=C2C(O)=C1C1=C(O)C2=CC=CC=C2N1 VIFKLIUAPGUEBV-UHFFFAOYSA-N 0.000 description 1
- WSNZLQGGHKYFAZ-UHFFFAOYSA-M [Na+].[O-]S(Cl)(=O)=O Chemical compound [Na+].[O-]S(Cl)(=O)=O WSNZLQGGHKYFAZ-UHFFFAOYSA-M 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Indigoderivates. Im Hauptpatent würde ein Verfahren be schrieben zur Herstellung eines beständigen wasserlöslichen Derivates von Indigo in fester Form, aus dem durch Oxydation der Farbstoff zurückgebildet werden kann und das wertvoll ist für die Verwendung in der Färberei und Druckerei.
Dieses Verfahren besteht darin, dass Leuko- indigo durch Behandeln mit Schwefelsäure anhydrid oder solches abgebenden Substanzen als Veresterungsmittel,zweckmässig bei Gegen wart einer tertiären Base, wie zum Beispiel Dimethylanilin, in den sauren Ester der Schwefelsäure übergeführt wird. Die nach diesem Verfahren entstehende Verbindung ist ein saurer, schwefelsaurer Ester, wahrschein lich ein Enolester des Lenkoindigo, ein Kör per der noch saure, salzbildende Gruppen enthält, die die Wasserlöslichkeit des Pro duktes bedingen.
Es wurde nun gefunden, dass dieses Ver fahren auch auf Thioindigo anwendbar ist dergestalt, dass die Leukoverbindung von Thioindigo auf die genannte Weise in den sauren Ester der Schwefelsäure übergeführt wird.
<I>Beispiel:</I> 156 gr trockener' Leukothioindigo werden einem auf 0 abgekühlten Reaktionsgemisch zugesetzt, das durch Eintragen von 134,5 gr Chlorsulfonsäure in ein Gemisch von 280 gr Dimethylanilin und 500 gr Chlorbenzol bei 011 erhalten wurde.
Man lässt die Temperatur auf Zimmerwärme steigen und erhöht nach ungefähr zwei Stunden allmählich auf 60"C. Alsdann wird mit Natronlauge alkalisch ge macht und mit Wasserdampf das Dimetbyl- anilin und Chlorbenzol abdestilliert. flus der filtrierten, eingeengten Lösung wird der neue Körper auskristallisieren gelassen.
Der erhaltene Körper ist wasserlöslich und sowohl in Substanz als auch in Lösung beständig; durch Alkali wird' die wässerige Lösung nicht verändert; durch Mineralsäure erfolgt kalt langsam, in der Hitze schneller Zersetzung des gelösten Estersalzes; gelinde Oxydationsmittel in Gegenwart von Säure bewirken Rückbildung des Farbstoffes; welche auch durch Einwirkung von Lichtstrahlen in Gegenwart von Sauerstoff erfolgen kann.
In der Anwendung kann die zu färbende Substanz, Faser usw. mit einer wässerigen Lösung des Thioindigoestersalzes ganz oder lokal imprägniert und durch Einwirkung eines geeigneten Oxydationsmittels die Färbung zur Entwicklung gebracht werden.
Dieses Thioiudigoderivat gestattet also in einfachster Weise Färbungen mit diesem Farb- stoff zu erzeugen unter Umgehung der um ständlichen Küpe.
In dem erwähnten Beispiel kann an Stelle der Chlorsulforisäure allgemein eine Halogen- sulfonsäure, ein Salz einer Halogensulfonsäure wie zum Beispiel Natriumchlorsulfonat), rauchende Schwefelsäure oder Schwefelsäure- anhydrid verwendet werden.
Process for the preparation of an indigo derivative. In the main patent, a process would be described for the production of a stable water-soluble derivative of indigo in solid form, from which the dye can be reformed by oxidation and which is valuable for use in dyeing and printing.
This process consists in converting leuco indigo into the acidic ester of sulfuric acid by treating it with sulfuric anhydride or substances that donate such as esterifying agents, expediently in the presence of a tertiary base such as dimethylaniline. The compound formed by this process is an acidic, sulfuric acid ester, probably an enol ester of Lenkoindigo, a body which still contains acidic, salt-forming groups that cause the product to be soluble in water.
It has now been found that this process can also be applied to thioindigo in such a way that the leuco compound of thioindigo is converted into the acidic ester of sulfuric acid in the manner mentioned.
<I> Example: </I> 156 grams of dry leukothioindigo are added to a reaction mixture, cooled to 0, which was obtained by adding 134.5 grams of chlorosulfonic acid to a mixture of 280 grams of dimethylaniline and 500 grams of chlorobenzene at 011.
The temperature is allowed to rise to room temperature and after about two hours gradually increased to 60 ° C. Then it is made alkaline with sodium hydroxide solution and the dimethylaniline and chlorobenzene are distilled off with steam. The filtered, concentrated solution is allowed to crystallize out the new body.
The body obtained is water-soluble and stable both in substance and in solution; the aqueous solution is not changed by alkali; Mineral acid causes slow cold decomposition of the dissolved ester salt; mild oxidizing agents in the presence of acid cause regression of the dye; which can also be done by exposure to light rays in the presence of oxygen.
In use, the substance, fiber, etc. to be dyed can be completely or locally impregnated with an aqueous solution of the thioindigoester salt and the color can be developed by the action of a suitable oxidizing agent.
This thioudigo derivative thus allows colorations with this dye to be produced in the simplest possible way, avoiding the cumbersome vat.
In the example mentioned, a halosulfonic acid, a salt of a halosulfonic acid such as, for example, sodium chlorosulfonate, fuming sulfuric acid or sulfuric acid anhydride can generally be used instead of chlorosulforic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR418487X | 1921-09-16 | ||
| CH102540T | 1922-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH103139A true CH103139A (en) | 1924-01-16 |
Family
ID=25706247
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH103138D CH103138A (en) | 1921-09-16 | 1922-09-14 | Process for the preparation of an indigo derivative. |
| CH103139D CH103139A (en) | 1921-09-16 | 1922-09-14 | Process for the preparation of an indigo derivative. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH103138D CH103138A (en) | 1921-09-16 | 1922-09-14 | Process for the preparation of an indigo derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH103138A (en) |
-
1922
- 1922-09-14 CH CH103138D patent/CH103138A/en unknown
- 1922-09-14 CH CH103139D patent/CH103139A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH103138A (en) | 1924-01-16 |
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