CH122920A - Process for the preparation of an azo-related dye. - Google Patents
Process for the preparation of an azo-related dye.Info
- Publication number
- CH122920A CH122920A CH122920DA CH122920A CH 122920 A CH122920 A CH 122920A CH 122920D A CH122920D A CH 122920DA CH 122920 A CH122920 A CH 122920A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- azo
- dye
- red
- diazo compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000000987 azo dye Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 2
- 238000005554 pickling Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-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
- 150000001412 amines Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- -1 polyazo Polymers 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000000344 soap Substances 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines beizenziehenden Azofarbstoffes. . Es wurde gefunden, dass man neue, wert volle Azofarbstoffe von beizenziehendem Cha rakter erhält, wenn man zum Aufbau als Diazokomponenten solche Aminoderivate des Diphenylsulfons
EMI0001.0009
seiner Homologen oder Substitutionsprodukte verwendet,
die in dem nicht amidierten Kern orthoständig zueinander eine Hydroxyl- und eine Carboxylgruppe enthalten.
Je nach Wabl der Kupplungskomponenten, ob es sich um Mono- oder Polyazofarbstoffe handelt, werden Farbstoffe in den verschie densten Tönen erhalten. Sie eignen sich so wohl für die Wollfärberei nach dem Chromier- verfahren, als auch besonders wegen ihrer guten Seifen- und Chlorechtheit für den Baumwolldruck. Infolge der externen Stellung der beizenziehenden Gruppe zeigen sie den weiteren Vorteil, dass die chromierten Fär bungen von den direkten im Farbton nur wenig abweichen.
Das vorliegende Patent betrifft ein Ver fahren zur Herstellung eines beizenziehenden Azofarbstoffes, dadurch gekennzeichnet, dass man die Diazoverbindung des durch Kuppeln der Diazoverbindung der 2-Amino-4-sulfo-4'- oxydiphenyIsulfon - 3' - karbonsäure mit 3 - Amino-4-metboxy-toluol erhältlichen Kupp-, lüngsproduktes mit Salizylsäure kuppelt.
Der so erhältliche Farbstoff bildet trocken ein rotbraunes Pulver, das in Wasser mit orange roter Farbe löslich ist. Er ist besonders zum Chromdruek auf Baumwolle geeignet, wo ein lebhaftes Rotbraun mit vorzüglicher Licht-, Wasch- und Chlorechtheit entsteht.
<I>Beispiel:</I> Zu der Diazoverbindung aus 373 Teilen 2-Amino -4- sulfo-4'-oxydiphenylsulfon-3'-kar- bonsäure lässt man eine salzsaure Lösung von 151 Teilen o-Amino-p-kresoläther zulaufen und stumpft langsam innerhalb mehrerer Stunden mit Natriumacetat ab, bis alle Mineralsäure gebunden ist. Der entstandene 11Ionoazofarbstoff wird sodaalkalisch ausge- salzen, filtriert und in 3000 Teilen Wasser wieder gelöst.
Nach Zusatz von 69 Teilen Natriumnitrit fügt man bei 0 500 Teile Salzsäure von 19,511 B6 auf einmal zu und lässt nach beendeter Weiterdiazotierung eine neutrale Lösung von 15 Teilen Salizylsäure zufliessen. Nun gibt man in dünnem Strahle eine Mischung von 400 Teilen Natronlauge von<B>360</B> B6 und 400 Teilen Wasser zu, wobei die Temperatur immer auf 0 gehalten wird. Sobald alkalische Reaktion eintritt, ist die Kupplung beendet. Der Farbstoff wird durch Aussalzen abgeschieden. Er bildet trocken ein rotbraunes Pulver, löslich in Wasser mit orangeroter Farbe.
Er ist be sonders zum Chromdruck auf Baumwolle ge eignet," wo ein lebhaftes Rotbraun entsteht mit vorzüglicher Licht-, Wasch- und Chlor echtheit.
Process for the preparation of an azo-related dye. . It has been found that new, valuable azo dyes of commercial character are obtained if such amino derivatives of diphenyl sulfone are used as diazo components for the structure
EMI0001.0009
its homologues or substitution products are used,
which in the non-amidated core contain a hydroxyl and a carboxyl group ortho to one another.
Depending on the Wabl of the coupling components, whether it is mono- or polyazo, dyes are obtained in the most diverse shades. They are well suited for wool dyeing using the chroming process and, especially because of their good soap and chlorine fastness, for cotton printing. As a result of the external position of the affiliated group, they show the further advantage that the chromed colorations differ only slightly in color from the direct ones.
The present patent relates to a process for the production of an azo dyestuff, characterized in that the diazo compound of the 2-amino-4-sulfo-4'-oxydiphenyIsulfon - 3 '- carboxylic acid with 3 - amino-4- Metboxy-toluene available coupling product, coupling product with salicylic acid.
The dye obtainable in this way forms a red-brown powder when dry, which is soluble in water with an orange-red color. It is particularly suitable for chrome printing on cotton, where a lively reddish brown with excellent light, washing and chlorine fastness is created.
<I> Example: </I> A hydrochloric acid solution of 151 parts of o-amino-p-cresol ether is allowed to run into the diazo compound from 373 parts of 2-amino-4-sulfo-4'-oxydiphenylsulfonic-3'-carboxylic acid and slowly blunted with sodium acetate within several hours until all mineral acid is bound. The resulting 11ionoazo dye is salted out with alkaline soda, filtered and redissolved in 3000 parts of water.
After 69 parts of sodium nitrite have been added, 500 parts of hydrochloric acid of 19.511 B6 are added all at once and, when the further diazotization is complete, a neutral solution of 15 parts of salicylic acid is allowed to flow in. A mixture of 400 parts of sodium hydroxide solution of <B> 360 </B> B6 and 400 parts of water is then added in a thin stream, the temperature always being kept at 0. As soon as an alkaline reaction occurs, the coupling is complete. The dye is deposited by salting out. When dry, it forms a red-brown powder, soluble in water with an orange-red color.
It is particularly suitable for chrome printing on cotton, "where a lively red-brown is created with excellent light, washing and chlorine fastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE122920X | 1925-01-13 | ||
| CH119984T | 1925-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH122920A true CH122920A (en) | 1927-10-17 |
Family
ID=25709373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH122920D CH122920A (en) | 1925-01-13 | 1925-12-22 | Process for the preparation of an azo-related dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH122920A (en) |
-
1925
- 1925-12-22 CH CH122920D patent/CH122920A/en unknown
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