CH261056A - Process for the preparation of a polyazo dye. - Google Patents
Process for the preparation of a polyazo dye.Info
- Publication number
- CH261056A CH261056A CH261056DA CH261056A CH 261056 A CH261056 A CH 261056A CH 261056D A CH261056D A CH 261056DA CH 261056 A CH261056 A CH 261056A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- dye
- hand
- brown
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- -1 polyazo Polymers 0.000 title description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- C09B35/50—Tetrazo dyes
- C09B35/52—Tetrazo dyes of the type
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
Verfahren zur Herstellung eines Polyazofarbatoffes. Es wurde gefunden, dass ein Polyazofarb- stoff hergestellt werden kann, wenn man 1,3-Dioxybenzol einerseits mit der Diazoazover- bindung, die beim einseitigen Kuppeln von tetrazotiertem 3,3' - Dioxy - 4,4' - diaminodi - phenyl und 1-Phenyl-3-methyl-5-pyrazolon erhalten wird,
und anderseits mit diazotier- ter 4-Nitro-l-aminobenzol-2-sulfonsäure kup pelt.
Der neue Farbstoff stellt ein dunkles Pul ver dar, das sich in Wasser mit rotbrauner, in verdünnten Soda- und Ätzalkalilösungen mit bordeauxroter und in konzentrierter Schwefelsäure mit violetter Farbe löst. Er er zeugt auf Baumwolle nach dem ein- oder zweibadigen Nachkupferungsverfahren echte braunstichige Bordeauxtöne.
3,3'-Dioxy-4,4'-diaminodiphenyl kann bei spielsweise durch Verseifen von Dianisidin mit Aluminiumchlorid erhalten werden und wird in üblicher Weise tetrazotiert. Die ein seitige Kupplung der Tetrazoverbindung mit 1-Phenyl-3-methyl-5-pyrazolon kann in alka lischem, beispielsweise Natriumkarbonat oder Natriumhydroxyd oder beide enthaltendem Medium durchgeführt werden.
Das 1,3-Dioxy- benzol wird zweckmässig zuerst mit der ge nannten Diazoverbindung und hierauf rnit der diazotierten 4-Nitro-l-aminobenzol-2-sul- fonsäure gekuppelt.
<I>Beispiel:</I> Eine aus 4,32 Teilen 3,3'-Dioxy-4,4'-di- aminodiphenyl, 10 Raumteilen 30 7o iger Salzsäure und 200 Teilen Wasser mit 2,76 Teilen Natriumnitrit hergestellte Tetrazo- ; Lösung wird mit 3,5 Teilen 1-Phenyl-3-methyl- 5-pyrazolon, gelöst in 8 Raumteilen 30 % iger Natronlauge, 10 Teilen Natriumkarbonat und 100 Teilen Wasser, vereinigt. Man rührt 2 Stunden bei 18-20 und filtriert die ent standene Diazoazoverbindung ab..
Man rührt sie hierauf mit 50 Teilen Wasser an und ver setzt mit einer Lösung von 2,2 Teilen 1,3- DioxyBenzol und 5 Teilen Natriumkarbonat in 20 Teilen Wasser. Man kuppelt unter Rühren während 1 Stunde bei 18 , setzt 10 Raumteile 30 /o ige Natronlauge zu und rührt eine weitere Stunde. Durch Zusatz von Salz säure -und Kochsalz wird der Farbstoff abge schieden.
Der abfiltrierte Disazofarbstoff wird unter Zusatz von 15 Raumteilen 30%i,-er Natronlauge in 150 Teilen Wasser gelöst und mit der in üblicher Weise darge stellten Diazolösung aus 4,36 g 4-Nitro-l- aminobenzol - 2 - sulfonsäure versetzt. Das ; Kupplungsgemisch wird 24 Stunden bei 15 bis 18 gerührt und der gebildete Farbstoff durch Kochsalz abgeschieden.
Process for the production of a polyazo carbate. It has been found that a polyazo dye can be produced if, on the one hand, 1,3-dioxybenzene is mixed with the diazoazo compound, which is formed in the one-sided coupling of tetrazotized 3,3'-dioxy-4,4'-diaminodiphenyl and 1 -Phenyl-3-methyl-5-pyrazolone is obtained,
and on the other hand with diazotized 4-nitro-1-aminobenzene-2-sulfonic acid.
The new dye is a dark powder that dissolves in water with red-brown color, in dilute soda and caustic alkali solutions with burgundy and in concentrated sulfuric acid with purple color. It produces genuine brown-tinged Bordeaux tones on cotton using the one- or two-bath re-coppering process.
3,3'-Dioxy-4,4'-diaminodiphenyl can be obtained, for example, by saponifying dianisidine with aluminum chloride and is tetrazotized in the usual way. The one-sided coupling of the tetrazo compound with 1-phenyl-3-methyl-5-pyrazolone can be carried out in alkaline medium, for example sodium carbonate or sodium hydroxide or both.
The 1,3-dioxybenzene is expediently first coupled with the diazo compound mentioned and then with the diazotized 4-nitro-1-aminobenzene-2-sulphonic acid.
<I> Example: </I> A tetrazo produced from 4.32 parts of 3,3'-dioxy-4,4'-di-aminodiphenyl, 10 parts by volume of 30% hydrochloric acid and 200 parts of water with 2.76 parts of sodium nitrite ; The solution is combined with 3.5 parts of 1-phenyl-3-methyl-5-pyrazolone, dissolved in 8 parts by volume of 30% strength sodium hydroxide solution, 10 parts of sodium carbonate and 100 parts of water. The mixture is stirred for 2 hours at 18-20 and the resulting diazoazo compound is filtered off.
They are then stirred with 50 parts of water and a solution of 2.2 parts of 1,3-dioxybenzene and 5 parts of sodium carbonate in 20 parts of water is added. Coupling is carried out at 18 for 1 hour, while stirring, 10 parts by volume of 30% sodium hydroxide solution are added and the mixture is stirred for a further hour. The dye is deposited by adding hydrochloric acid and sodium chloride.
The filtered disazo dye is dissolved in 150 parts of water with the addition of 15 parts by volume of 30% sodium hydroxide solution and the diazo solution of 4.36 g of 4-nitro-l-aminobenzene-2-sulfonic acid, prepared in the usual manner, is added. The ; The coupling mixture is stirred for 24 hours at 15 to 18 and the dye formed is deposited by means of sodium chloride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH261056T | 1941-02-18 | ||
| CH257110T | 1942-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH261056A true CH261056A (en) | 1949-04-15 |
Family
ID=25730022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH261056D CH261056A (en) | 1941-02-18 | 1941-02-18 | Process for the preparation of a polyazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH261056A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7951235B2 (en) | 2005-08-08 | 2011-05-31 | Fujifilm Imaging Colorants Limited | Black azo dyes and their use in ink jet printing |
-
1941
- 1941-02-18 CH CH261056D patent/CH261056A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7951235B2 (en) | 2005-08-08 | 2011-05-31 | Fujifilm Imaging Colorants Limited | Black azo dyes and their use in ink jet printing |
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