CH183895A - Process for the preparation of a dye. - Google Patents
Process for the preparation of a dye.Info
- Publication number
- CH183895A CH183895A CH183895DA CH183895A CH 183895 A CH183895 A CH 183895A CH 183895D A CH183895D A CH 183895DA CH 183895 A CH183895 A CH 183895A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- toluidino
- amino
- carbonamide
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005521 carbonamide group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- -1 m-toluidino Chemical group 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CNQQFHDRIRTZNA-UHFFFAOYSA-N 1-amino-4-(4-methylanilino)-9,10-dioxoanthracene-2-carbonitrile Chemical compound NC1=C(C=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)NC1=CC=C(C=C1)C)C#N CNQQFHDRIRTZNA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Farbstoffes. Das Hauptpatent betrifft ein Verfahren zur Herstellung eines wertvollen Farbstoffes, bei dem 1-Amino-2-cyan-4-(p-toluidino)- anthrachinon so lange mit einem sulfonierend wirkenden Mittel behandelt wird, bis das Reaktionsprodukt eben völlig wasserlöslich geworden ist, worauf die Cyangruppe zur Carbonamidgruppe verseift wird.
Es wurde nun gefunden, dass man einen ähnlich wertvollen Farbstoff erhält, wenn man 1-Amino-2-cyan-4-(m-toluidino)-anthra- chinon so lange mit einem sulfonierend wir kenden Mittel behandelt, bis das Reaktions produkt eben völlig wasserlöslich geworden ist und sodann die Cyangruppe zur Carbon- anridgruppe verseift.
Der erhaltene Farbstoff, eine Sulfonsäure des 1-Amino-4-(m-toluidino)-antrachinon-2- oarbonamids färbt Wolle aus saurem Bade in klaren bläuen Tönen.
<I>Beispiel:</I> 10 Teile 1-Amirro-2-cyan-4-(m-toluidino)- anthrachinon, erhältlich zum Beispiel aus 1- Amino-2-cyan-4-bromantbrachinon und m- Toluidin, werden in 100 Teilen Schwefelsäure monohydrat gelöst und so lange mit rauchen der Schwefelsäure, enthaltend 23"/o SOs, ver setzt, bis eine entnommene und aufgearbeitete Probe erkennen lässt, dass das Reaktionspro dukt eben völlig wasserlöslich geworden ist.
Man gibt sodann zu dem Reaktionsgemisch so viel kristallisierte Borsäure, dass das Sul- fierungsgemisch etwa 5 % davon enthält, und rührt so lange bei Zimmertemperatur, bis die Cyangruppe vollständig in die Carbonamid- gruppe übergeführt ist. Darauf giesst man das Reaktionsgemisch in Eiswasser und salzt den entstandenen Farbstoff in der üblichen Weise aus.
Process for the preparation of a dye. The main patent relates to a process for the production of a valuable dye in which 1-amino-2-cyano-4- (p-toluidino) anthraquinone is treated with a sulfonating agent until the reaction product has just become completely water-soluble, whereupon the cyano group is saponified to the carbonamide group.
It has now been found that a similarly valuable dye is obtained if 1-amino-2-cyano-4- (m-toluidino) anthraquinone is treated with a sulfonating agent until the reaction product is completely complete has become water-soluble and the cyano group is then saponified to form the carbon anride group.
The dye obtained, a sulfonic acid of 1-amino-4- (m-toluidino) -antraquinone-2-carbonamide, dyes wool from an acid bath in clear blue tones.
<I> Example: </I> 10 parts of 1-amirro-2-cyano-4- (m-toluidino) - anthraquinone, obtainable for example from 1-amino-2-cyano-4-bromantbrachinone and m-toluidine Dissolved in 100 parts of sulfuric acid monohydrate and added smoking sulfuric acid containing 23% SO 3 until a sample taken and processed shows that the reaction product has just become completely water-soluble.
Sufficient crystallized boric acid is then added to the reaction mixture that the sulphation mixture contains about 5% of it, and the mixture is stirred at room temperature until the cyano group has been completely converted into the carbonamide group. The reaction mixture is then poured into ice water and the dye formed is salted out in the usual way.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE183895X | 1933-01-21 | ||
| CH178227T | 1933-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH183895A true CH183895A (en) | 1936-04-30 |
Family
ID=25720102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH183895D CH183895A (en) | 1933-01-21 | 1933-12-20 | Process for the preparation of a dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH183895A (en) |
-
1933
- 1933-12-20 CH CH183895D patent/CH183895A/en unknown
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