CH235456A - Process for the preparation of a water-soluble monoazo dye. - Google Patents
Process for the preparation of a water-soluble monoazo dye.Info
- Publication number
- CH235456A CH235456A CH235456DA CH235456A CH 235456 A CH235456 A CH 235456A CH 235456D A CH235456D A CH 235456DA CH 235456 A CH235456 A CH 235456A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- preparation
- monoazo dye
- soluble monoazo
- sulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 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 claims description 3
- 239000000975 dye Substances 0.000 claims description 8
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 3
- QBLCRXSRSFKFFQ-UHFFFAOYSA-N 4-amino-3-chloro-5-nitrobenzenesulfonic acid Chemical compound [N+](=O)([O-])C=1C=C(C=C(C1N)Cl)S(=O)(=O)O QBLCRXSRSFKFFQ-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 1-amino-2-chloro-6-nitrobenzene-4-sulfonic acid sodium Chemical compound 0.000 description 1
- NEGPZGPAOPCNPD-UHFFFAOYSA-N 2-amino-3-chloro-5-nitrobenzenesulfonic acid Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1S(O)(=O)=O NEGPZGPAOPCNPD-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines wasserlöslichen Monoäzofarbstoffes. Nach dem im Hauptpatent beschriebenen Verfahren erhält man einen Leder in gelb braunen Tönen einheitlich durchfärbenden Farbstoff von guter Licht-, Säure- und Wasserechtheit, wenn man 1-Amino-2-chlor- 4-nitrobenzol-6-sulfosäure diazotiert und die Diazoverbindung mit Phenylaminodi (äthan- sulfonsäure der Formel
EMI0001.0009
kuppelt.
Wie nun weiter gefunden wurde, erhält man einen Farbstoff von ähnlichen Eigen schaften, wenn man 1-Amino-2-chlor-6-nitro- benzol-4-sulfosäure diazotiert und die Diazo- verbindung mit der Phenylaminodi (äthan- sulfonsäure) kuppelt.
Beispiel: 27,5 Teile 1-amino-2-chlor-6-nitrobenzol- 4-sulfonsaures Natrium werden in 200 Teilen warmem Wasser gelöst und unter Rühren auf Eis und 50 Teile Salzsäure von 12'B6 gegossen. Bei einer Temperatur von 0-5 giesst man eine wässrige Lösung von 7 Teilen Natriumnitrit dazu. Die Diazotierung ist in etwa 1/2 Stunde beendet.
Hierauf giesst man die Diazoverbindung in eine mit Eis ver setzte, wässrige Lösung des Natriumsälzes der Phenylaminodi (äthansulfonsäure) und stumpft zur Beendigung der Kupplung mit Natriumacetat ab. Der Farbstoff färbt Leder in braunroten Tönen wasserecht durch.
Process for the preparation of a water-soluble monoazo dye. The process described in the main patent gives a leather in yellow-brown shades uniformly through-dyed dye of good light, acid and water fastness, if 1-amino-2-chloro-4-nitrobenzene-6-sulfonic acid is diazotized and the diazo compound with phenylaminodi (ethane sulfonic acid of the formula
EMI0001.0009
clutch.
As has now been further found, a dye with similar properties is obtained if 1-amino-2-chloro-6-nitrobenzene-4-sulfonic acid is diazotized and the diazo compound is coupled with the phenylamino di (ethane sulfonic acid).
Example: 27.5 parts of 1-amino-2-chloro-6-nitrobenzene-4-sulfonic acid sodium are dissolved in 200 parts of warm water and poured onto ice and 50 parts of hydrochloric acid of 12'B6 with stirring. At a temperature of 0-5, an aqueous solution of 7 parts of sodium nitrite is poured in. The diazotization is complete in about 1/2 hour.
The diazo compound is then poured into an aqueous solution of the sodium salt of phenylamino di (ethanesulphonic acid) set with ice and blunted with sodium acetate to terminate the coupling. The dye dyes leather in brown-red tones water-fast.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE235456X | 1939-08-24 | ||
| CH232888T | 1942-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH235456A true CH235456A (en) | 1944-11-30 |
Family
ID=25727770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH235456D CH235456A (en) | 1939-08-24 | 1942-12-11 | Process for the preparation of a water-soluble monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH235456A (en) |
-
1942
- 1942-12-11 CH CH235456D patent/CH235456A/en unknown
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