AT73047B - Process for the preparation of indigoid dyes. - Google Patents
Process for the preparation of indigoid dyes.Info
- Publication number
- AT73047B AT73047B AT73047DA AT73047B AT 73047 B AT73047 B AT 73047B AT 73047D A AT73047D A AT 73047DA AT 73047 B AT73047 B AT 73047B
- Authority
- AT
- Austria
- Prior art keywords
- thionaphthene
- oxy
- preparation
- derivatives
- indigoid dyes
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- PCKPVGOLPKLUHR-UHFFFAOYSA-N indoxyl Chemical group C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N Pseudoisatin Natural products C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- -1 isatin anilide Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Indole Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung indigoider Farbstoffe.
A. Bezdzik und P. Friedlaender (Monatshefte, Bd. 2, S. 37 o) haben gezeigt, dass man durch Kondensation von Isatinanilid oder-chlorid mit 3-Oxy-l-thionaphten den 2-Indol-2-thionaphtenindigo darstellen kann. Es wurde nun gefunden, dass man zu denselben und ähnlichen Farbstoffen auf einem einfacheren Wege gelangen kann, indem man auf ein Gemenge von 3-Oxy-1-thionaphten bzw. 3-Oxy-1-thionaphten-2-karbonsäure oder deren Derivaten (im Benzolkern substituierten Abkömmlingen) mit Indoxyl bzw. Indoxylsäure oder deren Derivaten (im Benzolkern oder am Stickstoff substituierten Abkömmlingen) Oxydationsmittel einwirken lässt. Bedingung ist die gemeinsame Oxydation der Komponenten.
Man erhält so Gemenge indigoider Farbstoffe, je nach der relativen Menge der angewandten Ausgangsmaterialien von Blau bis Rotviolett. Immer ist aber der oben bezeichnete Farbstoff vorhanden.
Als Beispiel sei die Darstellung eines violetten Farbstoffes angeführt.
Die aus 10 technischer Indoxylsäure gewonnene Lösung von Indoxyl wird mit 2 g 3-Oxy-1-thionaphten, das in Eisessig gelöst ist, versetzt und mit einer Auflösung von 85 bis 9 g Ferrichlorid in Wasser oder einem anderen 1, ösungsmittel versetzt. Schon in der Kälte bildet sich ein Niederschlag. der durch Umkristallisieren von Beimengungen befreit werden kann.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of indigoid dyes.
A. Bezdzik and P. Friedlaender (MONTHS, Vol. 2, p. 37 o) have shown that the 2-indole-2-thionaphthene indigo can be produced by condensation of isatin anilide or chloride with 3-oxy-1-thionaphthene. It has now been found that the same and similar dyes can be obtained in a simpler way by using a mixture of 3-oxy-1-thionaphthene or 3-oxy-1-thionaphthene-2-carboxylic acid or their derivatives (im Benzene nucleus substituted derivatives) with indoxyl or indoxylic acid or their derivatives (in the benzene nucleus or derivatives substituted on nitrogen) allows oxidizing agents to act. The condition is the mutual oxidation of the components.
Mixtures of indigoid dyes are thus obtained, depending on the relative amount of the starting materials used, from blue to red-violet. But the dye mentioned above is always present.
An example is the representation of a violet dye.
The solution of indoxyl obtained from technical indoxylic acid is mixed with 2 g of 3-oxy-1-thionaphthene, which is dissolved in glacial acetic acid, and 85 to 9 g of ferric chloride are dissolved in water or another 1-solvent. Precipitation already forms in the cold. which can be freed from impurities by recrystallization.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT73047T | 1914-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT73047B true AT73047B (en) | 1917-02-10 |
Family
ID=3594706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT73047D AT73047B (en) | 1914-10-17 | 1914-10-17 | Process for the preparation of indigoid dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT73047B (en) |
-
1914
- 1914-10-17 AT AT73047D patent/AT73047B/en active
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