CH294564A - Process for the production of a copper-containing azo dye. - Google Patents
Process for the production of a copper-containing azo dye.Info
- Publication number
- CH294564A CH294564A CH294564DA CH294564A CH 294564 A CH294564 A CH 294564A CH 294564D A CH294564D A CH 294564DA CH 294564 A CH294564 A CH 294564A
- Authority
- CH
- Switzerland
- Prior art keywords
- copper
- azo dye
- containing azo
- production
- parts
- Prior art date
Links
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 8
- 229910052802 copper Inorganic materials 0.000 title claims description 8
- 239000010949 copper Substances 0.000 title claims description 8
- 239000000987 azo dye Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 239000000243 solution Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- -1 copper complex compound Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000725 suspension 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
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 290299. Verfahren zur Herstellung eines kupferhaltigen Azofarbstoffes. Gegenstand des vorliegenden Patentes ist. ein Verfahren zur Herstellung eines kupfer- haltigen Azofarbstoffes, welehes darin besteht, dass man 1 Mol der Aminodisazoverbindunf., der Zusammensetzung
EMI0001.0010
(Iiazotiert, den 1)
iazokörper reit 1 Mol Aeeto- ,ieet;vlaininobenzol kuppelt und den erhalte- nen Trisazofarbstoff mit einem kupferabge benden Mittel behandelt.
EMI0001.0020
werden in 3000 Teilen Wasser mit 15 Teilen Natrinnilivdi-oxvd gelöst, mit 6,9 Teilen Natriumnitrit versetzt und unter Kühlen in 75 Teile 30%ige Salzsäure gegossen. Die die Diazoverbindtuig als dunklen Niedersehlag enthaltende Suspension wird in eine Lösung von 17,7 Teilen.
Aeetoaeetylaminobenzol und 20 Teilen Natriumhy droxy d in 100 Teilen Wasser eingetragen und unter Eiskühlung so lange gerührt, bis die Kupplung beendigt ist.
Aus der Lösung fällt man dureh Zusatz von Natriumehlorid den so gewonnenen Trisazofarbstoff aus und isoliert. ihn hierauf. Er wird bei 80 bis 100 mit einer Lösung aus 47,5 Teilen Kupfersulfat, 127 Teilen 25 % igem Ammoniak und 3000 Teilen Wasser gerührt, bis sieh die Kupferkomplexverbin- dung des Farbstoffes gebildet hat,
was naeli etwa. 7.5 Stunden der Fall ist. Der neue kupferhaltige Azofarbstoff ist ein dunkles Pulver, das sieh in Wasser mit blaugrauer Farbe löst.. Er färbt Baumwolle in blaugrauen Tönen, welehe sieh dureh beaeh- tenswerte Lieht- und W aseheehtheit auszeieh- nen. Die Aniinodisazoverbindung kann derart hergestellt werden, dass tetrazotiertes 3,
3'- Dimethoxy-4,4'-cliamino-1,1'-diphenyl einer seits mit 1,8-Dioxy naphthalin-3,6-disulfonsäure und anderseits mit 2- (3'-Amino-4'-carbo- m ethoxy) -benzoylamino-5-oxynaphthalin-7-sul- fonsäure in alkalischer Lösung gekuppelt wird. Zu letzterer gelangt man, wenn man 2-Amino- 5-oxynaphthalin-7-sulfonsäure in wässeriger.
Lösung und in Gegenwart eines säurebinden den Mittels mit 3-Nitro-4-carbomethoxy-1.-ben- zoylchlorid umsetzt und im Reaktionsprodukt anschliessend die Nitrogruppe zur Amino- gruppe reduziert.
<B> Additional patent </B> to main patent no. 290299. Process for the production of a copper-containing azo dye. The subject of the present patent is. a process for the preparation of a copper-containing azo dye, which consists in adding 1 mol of the aminodisazo compound., the composition
EMI0001.0010
(Iiazotized, the 1)
iazo bodies with 1 mol of aeeto, ieet; vlaininobenzene couple and the trisazo dye obtained is treated with a copper-releasing agent.
EMI0001.0020
are dissolved in 3000 parts of water with 15 parts of Natrinnilivdi-oxvd, treated with 6.9 parts of sodium nitrite and poured into 75 parts of 30% hydrochloric acid with cooling. The suspension containing the diazo compound as a dark deposit is dissolved in a solution of 17.7 parts.
Aeetoaeetylaminobenzol and 20 parts of sodium hydroxide entered in 100 parts of water and stirred with ice cooling until the coupling is complete.
The trisazo dye thus obtained is precipitated from the solution by the addition of sodium chloride and isolated. him on this. It is stirred at 80 to 100 with a solution of 47.5 parts of copper sulfate, 127 parts of 25% ammonia and 3000 parts of water until the copper complex compound of the dye has formed,
what naeli about. 7.5 hours is the case. The new copper-containing azo dye is a dark powder that dissolves in water with a blue-gray color. It dyes cotton in blue-gray tones, which are distinguished by their excellent lightness and water resistance. The Aniinodisazoverbindungen can be prepared in such a way that tetrazotized 3,
3'-Dimethoxy-4,4'-cliamino-1,1'-diphenyl on the one hand with 1,8-dioxynaphthalene-3,6-disulfonic acid and on the other hand with 2- (3'-amino-4'-carbom ethoxy) benzoylamino-5-oxynaphthalene-7-sulphonic acid is coupled in alkaline solution. The latter can be achieved if 2-amino-5-oxynaphthalene-7-sulfonic acid is dissolved in aqueous.
Solution and in the presence of an acid-binding agent with 3-nitro-4-carbomethoxy-1-benzoyl chloride and then reduced the nitro group to the amino group in the reaction product.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294564T | 1951-02-17 | ||
| CH290299T | 1951-02-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH294564A true CH294564A (en) | 1953-11-15 |
Family
ID=25732975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH294564D CH294564A (en) | 1951-02-17 | 1951-02-17 | Process for the production of a copper-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH294564A (en) |
-
1951
- 1951-02-17 CH CH294564D patent/CH294564A/en unknown
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