CH258762A - Process for the preparation of a new monoazo dye. - Google Patents
Process for the preparation of a new monoazo dye.Info
- Publication number
- CH258762A CH258762A CH258762DA CH258762A CH 258762 A CH258762 A CH 258762A CH 258762D A CH258762D A CH 258762DA CH 258762 A CH258762 A CH 258762A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfuric acid
- new
- preparation
- parts
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 3
- 230000001180 sulfating effect Effects 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- -1 sulfuric acid ester Chemical class 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen Monoazofarbstoffes. Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines neuen Nonoazofarbstoffes, gemäss welchem diazo- tierter p-Aminophenyl-fl-oxyäthyläther, 8- Chlor-2-oxydiphenylenoxyd und ein Sulfa- t.ierungsmittel miteinander derart umgesetzt werden,
dass die Oxyäthylgruppe in die ent sprechende Schwefelsäureestergruppe über geführt wird und der Diazorest in 1-Stellung des Diphenylenoxydkernes tritt.
Der neue Farbstoff ist ein braunes Pul ver, welches sich in Wasser mit rötlich- ora.nger Farbe und in Schwefelsäure mit karmesinroter Farbe löst.
Die Überführung der Oxyäthylgruppe in die entsprechende Schwefelsäureestergruppe mit Hilfe des Sulfatierungsmittels, bei pieleweise mit Hilfe von Schwefelsäure, kann vor oder nach der Kupplung erfolgen.
Die Methode zur Numerierung des Di- phenylenoxydringsystems in dieser Beschrei bung erfolgt nach The Ring Index von A. M. Patterson & L. T. Capell (Reinhold Publishing Corporation, New York) 1940, Seite 234, Nr. 1719, das heisst das Sauerstoff atom wird mit 5 bezeichnet.
<I>Beispiel:</I> 23,3 Teile p-Aminophenyl-fl-oxyäthyl- 'sither-Schw efelsäureesterwerdenin300Teilen Wasser, enthaltend 25 Teile 36%iger Salz säure, durch Zugabe einer Lösung von 6,9 Teilen Natriumnitrit in 50 Teilen Wasser diazotiert. Die entstandene Diazolösung wird unter Rühren einer gekühlten Lösung von 21,9 Teilen 8-Chlor-2-oxydiphenylenoxyd, gelöst in 400 Teilen Wasser und 4 Teile Natriumhydroxyd und 40 Teile wasserfreies Natriumcarbonat enthaltend, zugegeben.
Nach beendeter Kupplung versetzt man das Kupplungsgemisch mit 40 Teilen Kochsalz und rührt während 3 Stunden. Hierauf wird der Farbstoff abfiltriert, mit. Wasser ge waschen und getrocknet.
Process for the preparation of a new monoazo dye. The present invention relates to a process for the preparation of a new nonoazo dye, according to which diazotized p-aminophenyl-fl-oxyethyl ether, 8-chloro-2-oxydiphenylene oxide and a sulfating agent are reacted with one another in such a way that
that the oxyethyl group is passed into the corresponding sulfuric acid ester group and the diazo radical occurs in the 1-position of the diphenylene oxide nucleus.
The new dye is a brown powder that dissolves in water with a reddish orange color and in sulfuric acid with a crimson color.
The conversion of the oxyethyl group into the corresponding sulfuric acid ester group with the aid of the sulfating agent, possibly with the aid of sulfuric acid, can take place before or after the coupling.
The method for numbering the diphenylene oxide ring system in this description is based on The Ring Index by A.M. Patterson & L.T. Capell (Reinhold Publishing Corporation, New York) 1940, page 234, no. 1719, that is, the oxygen atom is denoted by 5.
<I> Example: </I> 23.3 parts of p-aminophenyl-fl-oxyethyl- 'sither sulfuric acid ester are added to 300 parts of water containing 25 parts of 36% hydrochloric acid by adding a solution of 6.9 parts of sodium nitrite in 50 parts Water diazotized. The resulting diazo solution is added with stirring to a cooled solution of 21.9 parts of 8-chloro-2-oxydiphenylene oxide dissolved in 400 parts of water and 4 parts of sodium hydroxide and 40 parts of anhydrous sodium carbonate.
After the coupling has ended, 40 parts of sodium chloride are added to the coupling mixture and the mixture is stirred for 3 hours. The dye is then filtered off, with. Wash water and dry.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB258762X | 1945-07-26 | ||
| CH252531T | 1946-07-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH258762A true CH258762A (en) | 1948-12-15 |
Family
ID=25729628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH258762D CH258762A (en) | 1945-07-26 | 1946-07-25 | Process for the preparation of a new monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH258762A (en) |
-
1946
- 1946-07-25 CH CH258762D patent/CH258762A/en unknown
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