CH121027A - Process for the preparation of a derivative of 4: 4'-dimethyl-6: 6'-dichloro-bis-thionaphthene indigo. - Google Patents
Process for the preparation of a derivative of 4: 4'-dimethyl-6: 6'-dichloro-bis-thionaphthene indigo.Info
- Publication number
- CH121027A CH121027A CH121027DA CH121027A CH 121027 A CH121027 A CH 121027A CH 121027D A CH121027D A CH 121027DA CH 121027 A CH121027 A CH 121027A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- dichloro
- bis
- derivative
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 235000000177 Indigofera tinctoria Nutrition 0.000 title description 4
- 229940097275 indigo Drugs 0.000 title description 4
- 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 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- -1 sulfuric acid ester Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 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 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 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 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- KNVLCWQKYHCADB-UHFFFAOYSA-N chlorosulfonyloxymethane Chemical compound COS(Cl)(=O)=O KNVLCWQKYHCADB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 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
- 238000003756 stirring Methods 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
- Indole Compounds (AREA)
Description
Verfahren zur Darstellung eines Derivates von 4:4'-Dimethyl-6:6'-dichlor-bis- thionaphtenindigo. Im Hauptpatent wurde ein Verfahren beschrieben zur Herstellung eines bestän digen, 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 Verfah ren besteht darin,, dass Leukoindigo mit Hilfe von Schwefelsäureanhydrid oder sol ches als Veresterungsmittel abgebenden Sub stanzen, zweckmässig bei Gegenwart einer tertiären Base, wie zum Beispiel Dimetliy 1 anilin, in den sauren Ester der Schwefel säure übergeführt wird.
Die nach diesem Verfahren entstehende Verbindung ist ein saurer schwefelsaurer Ester, wahrscheinlich ein Enolester des Leukoindigo, ein Körper, der noch saure salzbildende Gruppen ent hält, die die Wasserlöslichkeit des Produktes bedingen.
Es wurde in diesem Verfahren als Ver- esterungsmittel hauptsächlich Chlorsulfon- säure verwendet. Es wurde nun gefunden, dass man an deren Stelle auch einen Alkylester der Chlor sulfonsäure verwenden kann, und dass dabei der gleiche Endstoff erhalten wird wie bei Verwendung von Chlorsulf onsäure.
In Anwendung auf 4 : 4'-Dimethyl-6 : 6' dichlor-bis-thionaphtenindigo wird 'das Ver fahren erläutert durch folgendes Beispiel:, In ein Gemisch aus 300 Teilen Pyridin und 75 Teilen Chlorsulfonsäuremethylester trägt man 30 Teile Leukoverbindung des 4 : 4'-Dimethyl- 6 : 6'- dichlor-bis-thionaphten- indigo bei ,gewöhnlicher Temperatur unter gutem Rühren ein, erwärmt auf<B>90'</B> C und hält etwa eine Stunde bei dieser Tem peratur.
Nach Abkühlen auf<B>30'</B> C macht man mit Soda alkalisch und destilliert das Pyridin mit Wasserdampf ab. Das Reak tionsprodukt gewinnt man durch Gus- salzen oder Eindampfen im Vakuum. Es ist identisch mit dem Produkt des Patentes Nr. 115239. Der erhaltene Körper ist in Wasser leicht löslich und sowohl in Substanz als auch in Lösung beständig.
Durch Alkali wird die wässeiigü Lösung -nicht verändert; durch i1Ti- neralsä.ure erfolgt kalt langsam, in der Hitze schneller Zersetzung des gelösten Estersalzes. Gelinde Oxydationsmittel in Gegenwart von Säure bewirken Rückbildung des Farbstoffes.
In der Anwendung kann die zu färbende Substanz, Faser usw. mit einer wässerigen Lösung des . neuen Eitersalzes ganz oder lo kal imprägniert und durch geeignete 0x3-da- tionswirkung die Färbung rasch und glatt zur Entwicklung gebracht werden.
Dieses Derivat von 4 : 4'- Dimethyl- 6 : 6'- dichlor - bis - thionaphtenindigo gestat tet also, Färbungen mit diesem Farbstoff in einfachster Weise zu erzeugen unter Umge hung der umständlichen Küpe.
Process for the preparation of a derivative of 4: 4'-dimethyl-6: 6'-dichloro-bis-thionaphthene indigo. The main patent describes a process 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 leucoindigo into the acidic ester of sulfuric acid with the aid of sulfuric anhydride or substances releasing such as esterifying agents, expediently in the presence of a tertiary base such as dimethyl aniline.
The compound formed by this process is an acidic sulfuric acid ester, probably an enol ester of leuco indigo, a body that still contains acidic salt-forming groups that make the product soluble in water.
The main esterifying agent used in this process was chlorosulfonic acid. It has now been found that an alkyl ester of chlorosulfonic acid can also be used instead, and that the end product obtained is the same as when using chlorosulfonic acid.
In application to 4: 4'-dimethyl-6: 6 'dichloro-bis-thionaphtenindigo' the process is illustrated by the following example: In a mixture of 300 parts of pyridine and 75 parts of methyl chlorosulfonate, 30 parts of leuco compound of 4: 4 are carried '-Dimethyl- 6: 6'-dichloro-bis-thionaphten- indigo at an ordinary temperature with thorough stirring, heated to <B> 90' </B> C and held for about an hour at this temperature.
After cooling to <B> 30 '</B> C, it is made alkaline with soda and the pyridine is distilled off with steam. The reaction product is obtained by casting salts or evaporation in vacuo. It is identical to the product of patent no. 115239. The body obtained is easily soluble in water and stable both in substance and in solution.
The aqueous solution is not changed by alkali; i1Tineralä.ure takes place slowly cold, in the heat faster decomposition of the dissolved ester salt. Mild oxidizing agents in the presence of acid cause the dye to regress.
In the application, the substance, fiber, etc. to be colored can be mixed with an aqueous solution of the. new pus salt can be completely or locally impregnated and the color can be developed quickly and smoothly through a suitable 0x3-dation effect.
This derivative of 4: 4'-dimethyl- 6: 6'-dichloro - bis - thionaphtenindigo thus allows dyeing with this dye to be produced in the simplest possible way, avoiding the cumbersome vat.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH102540T | 1922-09-14 | ||
| DE121027X | 1924-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH121027A true CH121027A (en) | 1927-06-16 |
Family
ID=25706243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH121027D CH121027A (en) | 1922-09-14 | 1925-04-04 | Process for the preparation of a derivative of 4: 4'-dimethyl-6: 6'-dichloro-bis-thionaphthene indigo. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH121027A (en) |
-
1925
- 1925-04-04 CH CH121027D patent/CH121027A/en unknown
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