CH287111A - Process for the preparation of a chromium-containing azo dye. - Google Patents
Process for the preparation of a chromium-containing azo dye.Info
- Publication number
- CH287111A CH287111A CH287111DA CH287111A CH 287111 A CH287111 A CH 287111A CH 287111D A CH287111D A CH 287111DA CH 287111 A CH287111 A CH 287111A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromium
- releasing agent
- azo dye
- dyes
- dye
- Prior art date
Links
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 14
- 229910052804 chromium Inorganic materials 0.000 title claims description 14
- 239000011651 chromium Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 10
- 239000000987 azo dye Substances 0.000 title claims description 6
- 239000000975 dye Substances 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001845 chromium compounds Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 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
- 210000002268 wool Anatomy 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 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
- 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 description 1
- -1 azo carbate Chemical compound 0.000 description 1
- 238000009835 boiling Methods 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 284075. Verfahren zur Herstellung eines ehrombaltigen Azofarbatoffes. Es wurde gefunden, dass man zu einem neuen wertvollen, ehromhaltigen Azofarbstoff gelangt., wenn man auf ein Gemiseh der zwei Monoazofarbstoffe, die den folgenden For meln
EMI0001.0010
entsprechen, chromabgebende Mittel derart einwirken lässt, dass ein ehromhaltiger Azo- farbst.off entsteht,
der je ein Molekül der zwei Ausgangsmonoazofarbstoffe an ein Chromatom komplex gebunden enthält..
Der neue chromhaltige Farbstoff bildet ein schwarzes Pulver, das sieh in Wasser mit graublauer und in konzentrierter Schwefel säure mit roter Farbe löst und Wolle aus neutralem oder schwach essigsaurem Bade in grauen Tönen färbt..
Die zwei beim vorliegenden Verfahren als Ausgangsstoffe dienenden Monoazofarb- stoffe können nach an sich bekannten Me thoden hergestellt werden, indem man diazo- tiertes 4-Nitro-2-amino-l-oxybenzol mit l.-Ace- tylamino-7-oxynaphtlialin und diazotiertes 2- Amino-l-oxvbenzol-4-sulfonsäureamid mit. 2- Oxynaphthalin jeweils in alkalischem Medium kuppelt.
Beispiel: 18,8 Teile 2-Amino-l-oxybenzol-4-sulfon- säureamid werden in 200 Teilen Wasser und 15 Volumteilen 7 0-n-Salzsä.ure aufgesehlä.mmt und bei 5 bis 10 mit 25 Volumteilen 4-n- N atriumnitritlösung diazotiert. Die durch Zu gabe von Natriumcarbonat neutralisierte Di- azoverbindung lässt man einlaufen in eine mit Fis auf 0 abgekühlte Lösung von 14,
8 Teilen 2-Oxynaphthalin in 52 Volumteilen 2-n-Na- triumhydroxydlösung und 50 Volumteilen 2- n-Natriumcarbonatlösung. Nach beendeter Kupplung wird der abgeschiedene Farbstoff filtriert und mit verdünnter Natriiunchlorid- lösung gewaschen und getrocknet.
36,6 Teile des so erhaltenen Farbstoffes und 36,6 Teile des aus 4-Nitro-2-ainino-l-oxybenzol und 1 Acetylamino-7-oxynaplithalin nach ähnlicher Methode erhaltenen Farbstoffes werden in 3000 Teilen Wasser aiügeschlämmt und mit 220 Teilen einer Lösung von ehromsalicyl- saurem Natrium mit einem Chromgehalt von ')-,61/o versetzt.. Nach 6 Stunden Kochen am Rückflusskühler ist die Chromierung beendet. Die erhaltene Chromverbindung wird durch Natriumchloridzugabe abgeschieden und ab filtriert.
<B> Additional patent </B> to main patent no. 284075. Process for the production of an azo carbate containing Ehrombus. It has been found that a new valuable, Ehrom-containing azo dye is obtained by looking at a mixture of the two monoazo dyes which have the following formulas
EMI0001.0010
corresponding, lets chromium-releasing agents act in such a way that an azo dye containing Ehrom is created,
which contains one molecule of each of the two starting monoazo dyes complexed to a chromium atom ..
The new chromium-containing dye forms a black powder that dissolves in water with a gray-blue color and in concentrated sulfuric acid with a red color and dyes wool from a neutral or slightly acetic acid bath in gray tones.
The two monoazo dyes used as starting materials in the present process can be prepared by methods known per se by diazotized 4-nitro-2-amino-1-oxybenzene with 1.-acetylamino-7-oxynaphthlialine and diazotized 2- Amino-1-oxvbenzene-4-sulfonic acid amide with. 2- Oxynaphthalene couples in an alkaline medium.
Example: 18.8 parts of 2-amino-1-oxybenzene-4-sulfonic acid amide are diluted in 200 parts of water and 15 parts by volume of 7 0 -N hydrochloric acid and, at 5 to 10, with 25 parts by volume of 4N Diazotized sodium nitrite solution. The diazo compound neutralized by adding sodium carbonate is allowed to run into a solution of 14, which has been cooled to 0 with Fis,
8 parts of 2-oxynaphthalene in 52 parts by volume of 2-n sodium hydroxide solution and 50 parts by volume of 2-n sodium carbonate solution. After the coupling has ended, the dyestuff which has separated out is filtered off, washed with dilute sodium chloride solution and dried.
36.6 parts of the dye thus obtained and 36.6 parts of the dye obtained from 4-nitro-2-ainino-1-oxybenzene and 1 acetylamino-7-oxynaplithalin by a similar method are slurried in 3000 parts of water and mixed with 220 parts of a solution of Ehromsalicylsaurem sodium with a chromium content of ') - 61 / o. After 6 hours of boiling on the reflux condenser, the chromation is complete. The chromium compound obtained is separated off by adding sodium chloride and filtered off.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH284075T | 1949-11-18 | ||
| CH287111T | 1949-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH287111A true CH287111A (en) | 1952-11-15 |
Family
ID=25732360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH287111D CH287111A (en) | 1949-11-18 | 1949-11-18 | Process for the preparation of a chromium-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH287111A (en) |
-
1949
- 1949-11-18 CH CH287111D patent/CH287111A/en unknown
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