CH287102A - 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
- CH287102A CH287102A CH287102DA CH287102A CH 287102 A CH287102 A CH 287102A CH 287102D A CH287102D A CH 287102DA CH 287102 A CH287102 A CH 287102A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromium
- releasing agent
- blue
- azo
- complex
- Prior art date
Links
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 17
- 229910052804 chromium Inorganic materials 0.000 title claims description 17
- 239000011651 chromium Substances 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 10
- 239000000987 azo dye Substances 0.000 title claims description 5
- 239000000975 dye Substances 0.000 claims description 13
- 239000003795 chemical substances by application Substances 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 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
- 230000002378 acidificating effect Effects 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 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
- -1 Azo compound Chemical class 0.000 description 1
- 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
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction 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
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 284075. Verfahren zur Herstellung eines chromhaltigen Azofarbstoües. Es wurde gefunden, dass man zu einem neuen wertvollen, chromhaltigen Azofarbstoff gelangt, wenn man auf ein Gemisch der zwei Monoazofarbstoffe, die den folgenden For rneln
EMI0001.0004
entsprechen, chromabgebende Mittel derart einwirken lässt, dass ein chromhaltiger Azö- farbstoff entsteht, der je ein Molekül der zwei Ausgangsmonoazofarbstoffe an ein Chrom atom komplex gebunden enthält.
Der neue chromhaltige Farbstoff bildet ein bronzierendes schwarzes Pulver, das sich in Wasser mit. blaugrauer und in konzentrierter Schwefelsäure mit violetter Farbe löst und Wolle aus neutralem oder schwach essigsau rem Bade in blaugrauen Tönen färbt.
Die zwei beim vorliegenden Verfahren als Ausgangsstoffe dienenden Monoazofarbstoffe können nach an sich bekannten Methoden her gestellt werden, indem man diazotiertes 5- Nitro-2-amino-l-oxybenzol mit 1-Acetylamino- 7-oxynaphthalin und diazotiertes 2-Amino-l- oxybenzol-4-sulfonsäureamid mit 1-Acetyl.- amino-7-oxynaphthalin jeweils in alkalischem Medium kuppelt.
Über die zu verwendenden chromabgeben den Mittel und Reaktionsbedingungen gibt das Hauptpatent Auskunft. <I>Beispiel:</I> 18,8 Teile 2-Amino-1.-oxybenzol-4-siLlfon- säureamid werden in 200 Teilen Wasser und 15 Volumteilen 1.0-n-Salzsäure aufgeschlämmt und bei 5 bis 10 mit 25 Volumteilen 4-n- Natriumnitritlösung diazotiert. Die- durch Zu- @,
-abe von Natriumcarbonat neutralisierte Di- azoverbindung lässt man einlaufen in eine mit Eis auf 0 abgekühlte Lösung von 20,5 Teilen 1-Acetylamino-7-oxy-naphthalin in 52 Volum- teilen 2-n-Natriumhydroxydlösttng und 50 Vo- lumteilen 2-n-Natriumcarbonatlösung. Nach beendeter Kupplung wird der abgeschiedene Farbstoff filtriert und mit verdünnter Na triumchloridlösung gewaschen und getrocknet.
40 Teile des so erhaltenen Farbstoffes und 36,6 Teile des aus 5-Nitro-2-amino-l-oxyben- zol und 1-Acetylamino-7-oxynaphthalin nach ähnlicher Methode erhaltenen Farbstoffes wer den in 3000 Teilen Wasser aufgeschlämmt und mit 220 Teilen einer Lösung von ehrom- salicyIsaurem Natrium mit einem Chromgehalt von 2,
6% versetzt. Nach 6 Stunden Kochen am R.ückflusskühler ist die Chromierung be endet. Die erhaltene Chromverbindung wird durch Natriuinchloridzugabe abgeschieden und abfiltriert.
<B> Additional patent </B> to main patent no. 284075. Process for the production of a chromium-containing azo dye. It has been found that a new valuable, chromium-containing azo dye is obtained by using a mixture of the two monoazo dyes which have the following formulas
EMI0001.0004
correspond, lets chromium-releasing agents act in such a way that a chromium-containing azo dye is created which contains one molecule of each of the two starting monoazo dyes bonded to a chromium atom in a complex.
The new chromium-containing dye forms a bronzing black powder that dissolves in water. dissolves blue-gray and in concentrated sulfuric acid with violet color and dyes wool from neutral or slightly acetic acid baths in blue-gray tones.
The two monoazo dyes used as starting materials in the present process can be prepared by methods known per se by mixing diazotized 5-nitro-2-amino-1-oxybenzene with 1-acetylamino-7-oxynaphthalene and diazotized 2-amino-1-oxybenzene -4-sulfonic acid amide couples with 1-acetyl-amino-7-oxynaphthalene in an alkaline medium.
The main patent provides information on the chromium-releasing agents and reaction conditions to be used. <I> Example: </I> 18.8 parts of 2-amino-1-oxybenzene-4-silfonic acid amide are slurried in 200 parts of water and 15 parts by volume of 1.0N hydrochloric acid and, at 5 to 10, with 25 parts by volume of 4 -n- sodium nitrite solution diazotized. Die- by Zu- @,
Azo compound neutralized by sodium carbonate is allowed to run into a solution, cooled to 0 with ice, of 20.5 parts of 1-acetylamino-7-oxynaphthalene in 52 parts by volume of 2N sodium hydroxide solution and 50 parts by volume 2- n-sodium carbonate solution. After the coupling has ended, the deposited dye is filtered off, washed with dilute sodium chloride solution and dried.
40 parts of the dye thus obtained and 36.6 parts of the dye obtained from 5-nitro-2-amino-1-oxyben- zene and 1-acetylamino-7-oxynaphthalene by a similar method who are suspended in 3000 parts of water and added to 220 parts a solution of Ehrom- salicyIsaurem sodium with a chromium content of 2,
6% offset. After 6 hours of boiling on the reflux condenser, the chroming is over. The chromium compound obtained is separated out by adding sodium chloride and filtered off.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH284075T | 1949-11-18 | ||
| CH287102T | 1949-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH287102A true CH287102A (en) | 1952-11-15 |
Family
ID=25732351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH287102D CH287102A (en) | 1949-11-18 | 1949-11-18 | Process for the preparation of a chromium-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH287102A (en) |
-
1949
- 1949-11-18 CH CH287102D patent/CH287102A/en unknown
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