AT46374B - Process for the preparation of penta- and hexabromo-substituted indigo dyes. - Google Patents
Process for the preparation of penta- and hexabromo-substituted indigo dyes.Info
- Publication number
- AT46374B AT46374B AT46374DA AT46374B AT 46374 B AT46374 B AT 46374B AT 46374D A AT46374D A AT 46374DA AT 46374 B AT46374 B AT 46374B
- Authority
- AT
- Austria
- Prior art keywords
- hexabromo
- penta
- preparation
- indigo dyes
- substituted
- Prior art date
Links
- 235000000177 Indigofera tinctoria Nutrition 0.000 title claims description 7
- 229940097275 indigo Drugs 0.000 title claims 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 claims description 4
- 238000000034 method Methods 0.000 title claims 3
- 239000000975 dye Substances 0.000 title claims 2
- 241001062009 Indigofera Species 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- LRBZENFZSJNJCR-UHFFFAOYSA-N 5-bromo-2-(5-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one Chemical compound [O-]c1c([nH]c2ccc(Br)cc12)C1=[NH+]c2ccc(Br)cc2C1=O LRBZENFZSJNJCR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Description
<Desc/Clms Page number 1>
EMI1.1
EMI1.2
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EMI2.1
fahren, dass man die Brommenge erhöht, z. B. an Stelle der in Beispiel I angewandten Menge Brom za. 30 oder mehr Teile Brom anwendet, wobei man eine höhere End-Bromierungs-Temperatur z. B. 20-300 wählen kann, dass man sodann das erhaltene Produkt mit Bisulfit und Eis zersetzt und kleine Mengen Sulfosäure durch Auskochen mit Natronlauge und Sprit entfernt. Der so erhaltene Farbstoff zeigt (besonders in der Abendfarbe) einen noch wesentlich grüneren Ton als der nach Beispiel I erhaltene.
Man kann in den vorliegenden Beispielen an Stelle der reinen Chlorsulfonsäure auch z. B. Mischungen von Chlorsulfonsäure mit Monohydrat, oder z. B. von Chlorsulfonsäure mit Nitrobenzol verwenden.
Ferner kann man an Stelle der bromsubstituierten Indigos auch die durch Substitution von Indigo oder Bromindigo mit Chlor erhältlichen chlor- oder chlorbromsubstituierten Indigos verwenden.
<Desc / Clms Page number 1>
EMI1.1
EMI1.2
<Desc / Clms Page number 2>
EMI2.1
drive that the amount of bromine is increased B. in place of the amount of bromine used in Example I za. 30 or more parts of bromine apply, using a higher final bromination temperature z. B. 20-300 can choose that you then decompose the product obtained with bisulfite and ice and remove small amounts of sulfonic acid by boiling with sodium hydroxide solution and fuel. The dye thus obtained shows (especially in the evening color) an even significantly greener shade than that obtained according to Example I.
In the present examples, instead of the pure chlorosulfonic acid, z. B. mixtures of chlorosulfonic acid with monohydrate, or z. B. use of chlorosulfonic acid with nitrobenzene.
Furthermore, instead of the bromine-substituted indigos, the chlorine- or chlorobromo-substituted indigos obtainable by substituting indigo or bromoindigo with chlorine can be used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE45879X | 1908-06-12 | ||
| DE46374X | 1908-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT46374B true AT46374B (en) | 1911-02-10 |
Family
ID=25749023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT46374D AT46374B (en) | 1908-06-12 | 1909-03-24 | Process for the preparation of penta- and hexabromo-substituted indigo dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT46374B (en) |
-
1909
- 1909-03-24 AT AT46374D patent/AT46374B/en active
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