AT45881B - Process for the preparation of sulphurous vat dyes. - Google Patents
Process for the preparation of sulphurous vat dyes.Info
- Publication number
- AT45881B AT45881B AT45881DA AT45881B AT 45881 B AT45881 B AT 45881B AT 45881D A AT45881D A AT 45881DA AT 45881 B AT45881 B AT 45881B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- sulphurous
- vat dyes
- parts
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- URXIUXOJSICGOD-UHFFFAOYSA-N 7-methoxy-1h-indole-2,3-dione Chemical compound COC1=CC=CC2=C1NC(=O)C2=O URXIUXOJSICGOD-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- 239000003086 colorant Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 description 1
- GDTUACILWWLIJF-UHFFFAOYSA-N 3-methoxy-2-nitrobenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1[N+]([O-])=O GDTUACILWWLIJF-UHFFFAOYSA-N 0.000 description 1
- DMHGXMPXHPOXBF-UHFFFAOYSA-N 5-Methoxyisatin Chemical compound COC1=CC=C2NC(=O)C(=O)C2=C1 DMHGXMPXHPOXBF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
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Verfahren zur Darstellung von schwefelhaltigen Küpenfarbstoffen.
Bekanntlich vereinigt sich das 3-0xy (l) thionaphten mit aromatischen Aldehyden, Ketonen und Diketonen zu Thioindigoniden, von welchen im D. R. P. Nr. 182260 namentlich
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Die alkoxilyerten Isatine erhält man nach den bekannten Metboden zur Darstellung von Isatin aus den entsprechenden Ausgangsmaterialien. Das in blauroten Nadeln vom Schmelzpunkt 240 bis 242 kristallisierende 7-Methoxyisatin
EMI1.4
kann sowohl durch Oxydation des bekannten (Ber. 22, Seite 2351) Dimethoxyindigo, ats auch nach dem Verfahren des D. R. P. Nr. 104693 ans dem (v) o-Nitro-m-methoxybenz- aldehyd, ferner aus dem Cyanydrin des Di-o-methoxy-carbodiphenylimid nach dem bekannten Verfahren von Geigy-Sa-n'dmeyer (D. R. P. 113979) und endlich aus dem Di-o-anisyl- oxa1imidchlorid nach dem Verfahren von J. Bauer (D. R.
P. 193fit3) gewonnen werden.
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Die Kondensation der alkoxylierten Isatine mit den 3-Oxythionaphtenen kann in wässeriger oder wässrig-alkoholischer Lösung, zweckmässig unter Zusatz von Alkalikarbonaten, oder in essigsaurer Lösung mit Salzsäure ausgeführt werden.
Beispiel I :
Zu einer heissen Lösung von 15 Teilen 3-0xy (1) thionaphten und 17-7 Teilen 7-Methoxyisatin in etwa 50%igem Alkohol gibt man eine Lösung von etwa G Teilen Soda
EMI1.8
densationsproduktes beginnt sofort und ist in kurzer Zeit beendet; es wird abfiltriert und ausgewaschen. Der Farbstoff stellt ein braunes, in den gebräuchlichen Lösungsmitteln
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unlösliches Pulver vor ; beim Behandeln mit geeigneten Reduktionsmitteln, z. B. Hydrosulfit in alkalischer Lösung, lässt er sich verküpen und scheidet sich durch Oxydation an der Luft wieder unverändert aus. Er färbt Wolle und Baumwolle in sehr echten bordeaux- roten Tönen.
Boispiel II :
23-8 Teile 6-Äthoxy-3-oxy (l) thionaphten-2-karbonsäure 17-7 Teile 7 -Methoxyisatin werden durch Erwärmen mit Essigsäure in Lösung gebracht ; nach Zugabe einer geringen Menge Salzäure beginnt sofort die Abscheidung eines orangegelb gefärbten Niederschlages ; dieser wird nach kurzem weiteren Erwärmen abfiltriert und gewaschen. Der Farbstoff zieht aus der Küpe auf Wolle und Baumwolle in sehr echten gelben Färbungen.
Beispiel III: 23-8 Teile 6-Äthoxy-3-oxy (l) thionaphten-2-karbonsäure, analog wie in Beispiel I angegeben, mit 17#7 Teilen 5-Methoxyisatin kondensiert, liefert einen Farbstoff, der Wolle und Baumwolle aus der Küpe in sehr echten braunen Tönen färbt.
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Process for the preparation of sulphurous vat dyes.
It is well known that 3-0xy (l) thionaphthene combines with aromatic aldehydes, ketones and diketones to form thioindigonides, of which in D.R.P. No. 182260 by name
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The alkoxylated isatins are obtained according to the known methods for the preparation of isatins from the corresponding starting materials. 7-methoxyisatin which crystallizes in blue-red needles with a melting point of 240 to 242
EMI1.4
can both by oxidation of the well-known (Ber. 22, page 2351) dimethoxyindigo, ats also by the method of DRP No. 104693 from the (v) o-nitro-m-methoxybenzaldehyde, also from the cyanydrin of the di-o- methoxy-carbodiphenylimide according to the known method of Geigy-Sa-n'dmeyer (DRP 113979) and finally from the di-o-anisyl-oxa1imidchlorid according to the method of J. Bauer (DR
P. 193fit3) can be obtained.
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The condensation of the alkoxylated isatins with the 3-oxythionaphthenes can be carried out in an aqueous or aqueous-alcoholic solution, expediently with the addition of alkali carbonates, or in an acetic acid solution with hydrochloric acid.
Example I:
A solution of about G parts of soda is added to a hot solution of 15 parts of 3-0xy (1) thionaphtene and 17-7 parts of 7-methoxyisatin in about 50% alcohol
EMI1.8
Densation product starts immediately and ends in a short time; it is filtered off and washed out. The dye turns brown, in common solvents
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insoluble powder before; when treating with suitable reducing agents, e.g. B. hydrosulphite in alkaline solution, it can be vat and separates out unchanged through oxidation in the air. He dyes wool and cotton in very real burgundy red tones.
Game II:
23-8 parts of 6-ethoxy-3-oxy (l) thionaphthene-2-carboxylic acid 17-7 parts of 7-methoxyisatin are brought into solution by heating with acetic acid; after adding a small amount of hydrochloric acid, an orange-yellow precipitate begins to separate; this is filtered off and washed after a short further heating. The dye pulls out of the vat on wool and cotton in very real yellow colors.
Example III: 23-8 parts of 6-ethoxy-3-oxy (l) thionaphten-2-carboxylic acid, analogously to that given in Example I, condensed with 17 parts of 5-methoxyisatin, yields a dye which is made from wool and cotton Küpe colors in very real brown tones.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE215785D | 1908-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT45881B true AT45881B (en) | 1911-01-10 |
Family
ID=5825784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT45881D AT45881B (en) | 1908-06-09 | 1909-03-29 | Process for the preparation of sulphurous vat dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT45881B (en) |
-
1909
- 1909-03-29 AT AT45881D patent/AT45881B/en active
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