CH190899A - Process for the preparation of a metal-containing nitro-disazo dye. - Google Patents
Process for the preparation of a metal-containing nitro-disazo dye.Info
- Publication number
- CH190899A CH190899A CH190899DA CH190899A CH 190899 A CH190899 A CH 190899A CH 190899D A CH190899D A CH 190899DA CH 190899 A CH190899 A CH 190899A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- green
- metal
- amino
- preparation
- Prior art date
Links
- 229910052751 metal Inorganic materials 0.000 title claims description 4
- 239000002184 metal Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 239000000975 dye Substances 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 4
- -1 aminoazo Chemical group 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- ZTHAJBMPRKJFQL-UHFFFAOYSA-N [Na].C1=C(S(O)(=O)=O)C=CC2=C(N)C(OCC)=CC=C21 Chemical compound [Na].C1=C(S(O)(=O)=O)C=CC2=C(N)C(OCC)=CC=C21 ZTHAJBMPRKJFQL-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines metallhaltigen Nitro-disazofarbstoffes. Vorliegendes Patent bezieht sich auf ein Verfahren zur Herstellung eines metallhalti gen Nitro-disazofarbstoffes, dadurch gekenn zeichnet, dass man diazotiertes 1-Amino-3- nitrobenzol in essigsaurem Medium mit 1- amino - 2 - äthoxynaphthalin - 6 - sulfonsaurem Natrium kuppelt, den gebildeten Aminoazo- farbatoff weiter diazotiert,
die Diazolösung in pyridinhaltigem Medium mit 2-(3'-carboxy- phenylamino)-5-oxynaphthalin-7-sulfonsaurem Natrium kuppelt und den so erhaltenen Farb stoff mit einer wässerigen Lösung von Kupfer sulfat unter Zusatz von Essigsäure kocht.
Der neue Farbstoff bildet nach dem Trocknen ein schwarzes Pulver. Er löst sich in Wasser mit grüngrauer, in konzentrierter Schwefelsäure mit grüner Farbe und färbt Baumwolle in ausserordentlich lichtechten, grüngrauen Tönen.
<I>Beispiel:</I> 13,8 Teile 1-Ainino-3-nitrobenzol werden mit 35 Teilen Salzsäure vom spez. Gew. 1,15 und 6,9 Teilen Natriumnitrit in der üblichen Weise diazotiert. Die Diazolösung lässt man in eine mit einer Natriumacetatlösung ver setzte Lösung von 28,9 Teilen 1-amino-2- ätboxynaphthalin - 6 - sulfonsaurem Natrium einlaufen. Die Kupplung zum Aminoazofarb- stoff ist sofort beendet.
Der Farbstoff wird abfiltriert und mit etwas Salzwasser nach gewaschen. Daraufhin wird die Paste mit Eis angeschlämmt und mit 35 Teilen Salz säure und 6,9 Teilen Natriumnitrit in die Diazoverbindung übergeführt, die dann zu einer mit Pyridin versetzten Lösung von 40 Teilen 2-(3'-carboxy-phenylamino)-5-oxynaph- thalin-7-sulfonsaurem Natrium gegeben wird. Der durch Natriumchloridzusatz abgeschiedene Farbstoff wird abgesaugt und ausgewaschen.
Dann wird die Farbstoffpaste in Wasser ge löst und essigsauer mit 35 Teilen kristalli siertem Kupfersulfat durch mehrstündiges Kochen unter Rückflusskühlung und gutem Rühren in die Kupferkomplexverbindung übergeführt. Diese wird abfiltriert, mit kal tem Wasser gewaschen und dadurch von überschüssigem Kupfersulfat befreit. Die Paste wird mit verdünnter Natriumearbonat- lösungangerührt, dann der Farbstoff isoliert und getrocknet.
Process for the preparation of a metal-containing nitro-disazo dye. The present patent relates to a process for the preparation of a metal-containing nitro-disazo dye, characterized in that diazotized 1-amino-3-nitrobenzene is coupled in an acetic acid medium with 1-amino-2-ethoxynaphthalene-6-sulfonic acid sodium, the resulting Aminoazo-diazotized further,
Coupling the diazo solution in a pyridine-containing medium with 2- (3'-carboxy-phenylamino) -5-oxynaphthalene-7-sulfonic acid sodium and boiling the dye thus obtained with an aqueous solution of copper sulfate with the addition of acetic acid.
The new dye forms a black powder after drying. It dissolves in water with a green-gray color, in concentrated sulfuric acid with a green color and dyes cotton in extremely lightfast, green-gray tones.
<I> Example: </I> 13.8 parts of 1-ainino-3-nitrobenzene are mixed with 35 parts of hydrochloric acid of spec. Weight 1.15 and 6.9 parts of sodium nitrite diazotized in the usual way. The diazo solution is allowed to run into a solution of 28.9 parts of 1-amino-2-ätboxynaphthalin-6-sulfonic acid sodium in a ver with a sodium acetate solution. The coupling to the aminoazo dye is ended immediately.
The dye is filtered off and washed with a little salt water. The paste is then slurried with ice and converted into the diazo compound with 35 parts of hydrochloric acid and 6.9 parts of sodium nitrite, which is then converted into a pyridine-added solution of 40 parts of 2- (3'-carboxy-phenylamino) -5-oxynaph- sodium thalin-7-sulfonic acid is given. The dye deposited by the addition of sodium chloride is filtered off with suction and washed out.
The dye paste is then dissolved in water and converted into the copper complex compound in acetic acid with 35 parts of crystallized copper sulfate by refluxing for several hours and stirring thoroughly. This is filtered off, washed with cold water and freed from excess copper sulfate. The paste is mixed with dilute sodium carbonate solution, then the dye is isolated and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE190899X | 1934-11-06 | ||
| CH187428T | 1935-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH190899A true CH190899A (en) | 1937-05-15 |
Family
ID=25721530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH190899D CH190899A (en) | 1934-11-06 | 1935-10-15 | Process for the preparation of a metal-containing nitro-disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH190899A (en) |
-
1935
- 1935-10-15 CH CH190899D patent/CH190899A/en unknown
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