CH211006A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211006A CH211006A CH211006DA CH211006A CH 211006 A CH211006 A CH 211006A CH 211006D A CH211006D A CH 211006DA CH 211006 A CH211006 A CH 211006A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxy
- mol
- azo dye
- dye
- parts
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 5
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 3
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 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 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/40—Trisazo dyes ot the type the component K being a dihydroxy or polyhydroxy compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 208588. Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass ein neuer Azo- farbstoff hergestellt werden kann, wenn man 1 Mol 1,3-Dioxybenzol einerseits mit 1 Mol der Diazoverbindung aus 1-Oxy-2-aminoben- zol-4-sulfamid und anderseits mit 1 Mol der Diazoazoverbindung,
die bei der einseitigen Kupplung tetrazotierten 3,3'-Dimethoxy-4,4'- diaminodiphenyl mit 2-Oxy-l-benzoesäure entsteht, vereinigt.
Der erhaltene Farbstoff bildet ein schwärz liches Pulver, das sich in Wasser und ver dünnten Alkalien mit bräunlicher und in konz. Schwefelsäure mit rotbrauner Farbe löst. Baumwolle und regenerierte Zellulose werden aus Glaubersalz enthaltendem Bade in braunroten Tönnen gefärbt, die durch Nachbehandlung mit Metall-, insbesondere Kupfersalzen, vorzüglich licht- und wasch echt werden.
<I>Beispiel:</I> 24,4 Teile 3,3'-Dimethoxy-4,4'-diamino- diphenyl werden in bekannter Weise mit 52 Teilen konz. Salzsäure und 14 Teilen Natriumnitrit in die Tetrazoverbindung über geführt. Diese lässt man zu einer bei 4 C gehaltenen Lösung fliessen, die man aus 15 Teilen 2-Oxy-l-benzoesäure und' 50 Teilen wasserfreiem Natriumcarbonät erhalten hat.
In kurzer Zeit bildet sich die braune Diazo- azoverbindung der Formel
EMI0001.0036
Diese kombiniert man nun mit dem Mono- azofarbstoff, den man erhält, wenn man die Diazoverbindung aus 18,8 Teilen 1-Oxy-2- aminobenzol-4-sulfamid in Gegenwart von 25 Teilen wasserfreiem Natriumcarbonat mit 11 Teilen 1,3-Dioxybenzol kuppelt.
Die Kupplung zum Monoazofarbstoff ist sofort beendet. und die rote Lösung desselben wird nun zu der oben erhaltenen Diazoazoverbin- dung gegeben, worauf eine braune Fällung des Trisazofarbstoffes entsteht.
Nach 24stündigem Rühren erhitzt man auf 65 und filtrier, trocknet und pulveri siert den, sch ärzliclwn Filterrückstand.
Additional patent to main patent no. 208588. Process for the production of an azo dye. It has been found that a new azo dye can be prepared if 1 mole of 1,3-dioxybenzene is mixed with 1 mole of the diazo compound from 1-oxy-2-aminobenzene-4-sulfamide and with 1 mole of the diazoazo compound ,
the 3,3'-dimethoxy-4,4'-diaminodiphenyl tetrazotized in the one-sided coupling is formed with 2-oxy-1-benzoic acid, combined.
The dye obtained forms a blackish powder, which is in water and ver dilute alkalis with brownish and in conc. Dissolves sulfuric acid with a red-brown color. Cotton and regenerated cellulose are dyed from baths containing Glauber's salt in brownish-red shades, which are extremely lightfast and washfast after treatment with metal salts, especially copper salts.
<I> Example: </I> 24.4 parts of 3,3'-dimethoxy-4,4'-diamino-diphenyl are concentrated in a known manner with 52 parts. Hydrochloric acid and 14 parts of sodium nitrite passed into the tetrazo compound. This is allowed to flow to a solution kept at 4 ° C. which has been obtained from 15 parts of 2-oxy-1-benzoic acid and 50 parts of anhydrous sodium carbonate.
The brown diazo-azo compound of the formula is formed in a short time
EMI0001.0036
This is then combined with the monoazo dye which is obtained when the diazo compound is coupled from 18.8 parts of 1-oxy-2-aminobenzene-4-sulfamide in the presence of 25 parts of anhydrous sodium carbonate with 11 parts of 1,3-dioxybenzene .
The coupling to the monoazo dye is ended immediately. and the red solution of the same is now added to the diazoazo compound obtained above, whereupon a brown precipitate of the trisazo dye results.
After stirring for 24 hours, the mixture is heated to 65 and filtered, dried and pulverized the black filter residue.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211006T | 1938-07-22 | ||
| CH208538T | 1938-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211006A true CH211006A (en) | 1940-08-15 |
Family
ID=25724535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211006D CH211006A (en) | 1938-07-22 | 1938-07-22 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211006A (en) |
-
1938
- 1938-07-22 CH CH211006D patent/CH211006A/en unknown
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