CH119628A - Process for the production of an indigoid dye of the anthracene series. - Google Patents
Process for the production of an indigoid dye of the anthracene series.Info
- Publication number
- CH119628A CH119628A CH119628DA CH119628A CH 119628 A CH119628 A CH 119628A CH 119628D A CH119628D A CH 119628DA CH 119628 A CH119628 A CH 119628A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- dye
- anthracene series
- indigoid dye
- methylisatin
- Prior art date
Links
- 150000001454 anthracenes Chemical class 0.000 title claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- UEHZKEABUOAZSH-UHFFFAOYSA-N 7-methyl-1h-indole-2,3-dione Chemical class CC1=CC=CC2=C1NC(=O)C2=O UEHZKEABUOAZSH-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- YOCGSXQUDANSJD-UHFFFAOYSA-N C1(C(C(=CC2=CC3=CC=CC=C3C=C12)OC=1SC=CC1)=O)=O Chemical compound C1(C(C(=CC2=CC3=CC=CC=C3C=C12)OC=1SC=CC1)=O)=O YOCGSXQUDANSJD-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- RGHILYZRVFRRNK-UHFFFAOYSA-N anthracene-1,2-dione Chemical compound C1=CC=C2C=C(C(C(=O)C=C3)=O)C3=CC2=C1 RGHILYZRVFRRNK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B7/00—Indigoid dyes
- C09B7/06—Indone-thionapthene indigos
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 103649. Verfahren zur Herstellung eines indigolden Farbstoffes der Anthracenreihe. Es wurde gefunden, dass man einen neuen indigoiden Farbstoff der Anthracen- reihe erhält, wenn man das 2,1-Anthrachi- nonoxythiophen mit einem reaktionsfähigen a-Derivat des 7-Methylisatins,
wie 7-Methyl- isatin-a-toluidid oder 7-Methylisatin-a-chlo- rid, kondensiert. Der neue -Farbstoff ist in Schwefelsäure mit grünlichscliwarzer Farbe löslich; er bildet mit Hydrosulfit und Na tronlauge eine rote Küpe, aus welcher Baum wolle, in eehten graublauen Tönen gefärbt wird.
<I>Beispiel:</I> <B>28</B> Teile 2,1-Anthrachinonoxythiophen werden mit<B>30</B> Teilen 7-Methylisatin-a-tolui- did und <B>300</B> Teilen Pyridin oder Trichlor- benzol zwei Stunden unter Rückfluss ge- hocht. Der ausgeschiedene Farbstoff wird bgesaugt, gewaschen und getrocknet.
Derselbe Farbstoff entsteht auch, wenn nian statt der Oxythiophenverbindung die entsprechende Thioglykolkarbonsäure ver wendet. In diesem Falle arbeitet man in Gegenwart von Essigsäureanhydrid und Natriumacetat, wobei die Oxythioplienver- bindung zunächst entsteht und dann mit, den vorhandenen Komponenten reagiert.
Additional patent to main patent no. 103649. Process for the production of an indigolden dye of the anthracene series. It has been found that a new indigoid dye of the anthracene series is obtained if the 2,1-anthraquinoneoxythiophene is mixed with a reactive α-derivative of 7-methylisatin,
such as 7-methylisatin-a-toluidide or 7-methylisatin-a-chloride, condensed. The new dye is soluble in sulfuric acid with a greenish-clear black color; With hydrosulphite and sodium hydroxide solution, it forms a red vat from which cotton is dyed in deep gray-blue tones.
<I> Example: </I> <B> 28 </B> parts of 2,1-anthraquinone oxythiophene are mixed with <B> 30 </B> parts of 7-methylisatin-a-toluidid and <B> 300 </ B> Parts of pyridine or trichlorobenzene are refluxed for two hours. The precipitated dye is suctioned off, washed and dried.
The same dye is also produced if the corresponding thioglycolic acid is used instead of the oxythiophene compound. In this case one works in the presence of acetic anhydride and sodium acetate, whereby the oxythiopliene compound is formed first and then reacts with the existing components.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH103649T | 1923-01-24 | ||
| CH119628T | 1925-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH119628A true CH119628A (en) | 1927-04-01 |
Family
ID=25706544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH119628D CH119628A (en) | 1923-01-24 | 1925-03-18 | Process for the production of an indigoid dye of the anthracene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH119628A (en) |
-
1925
- 1925-03-18 CH CH119628D patent/CH119628A/en unknown
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