CH215835A - Process for the preparation of a substantive azo dye. - Google Patents
Process for the preparation of a substantive azo dye.Info
- Publication number
- CH215835A CH215835A CH215835DA CH215835A CH 215835 A CH215835 A CH 215835A CH 215835D A CH215835D A CH 215835DA CH 215835 A CH215835 A CH 215835A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- azo dye
- mol
- preparation
- aminoazo
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 7
- -1 aminoazo Chemical group 0.000 claims description 5
- 150000001844 chromium Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 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
- 235000010288 sodium nitrite Nutrition 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
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/04—Stilbene-azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paper (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 213057. Verfahren zur Herstellung eines substantiven Azofarbstoffes. Gegenstand des Hauptpatentes ist ein Ver fahren zur Herstellung eines neuen, Substan tiven Azofarbstoffes, bei dem man den Amino- azofarbstoff der Formel COOH CH3 I I HO->-N-N-ONH2 I 503H OCH3 mit 4.4'-Dinitrostilben-2.2'-disulfosäure zu einem Farbstoff kondensiert,
der auf 1 112o1 des Aminoazofarbstoffes etwa 0,65 Mol der 4.4'-Dinitrostilben-2.2'-disulfosäure enthält. Es wurde nun gefunden, dass man einen neuen, Substantiven Azofarbstoff erhält, wenn man den Aminoazofarbstoff der Formel COOH CH3 HO -O-N=N-O-NH2 I I ö0311 CH3 mit 4.4'-Dinitrostilben-2@.2'-disulfosäüre zu einem Farbstoff kondensiert,
der auf 1 Mol des Aminoazofarbstoffes etwa 0,7 Mol der 4.4'-Dinitrostilben-2.2'-disulfosäure enthält.
Der neue Farbstoff färbt pflanzliche Fasern und regenerierte Cellulose in sehr gleich mässigen, lebhaft orangen Tönen, deren Wasch echtheit durch Nachbehandlung mit dreiwerti gen Chromsalzen noch gesteigert werden kann. <I>Beispiel:</I> Man löst 1 Mol 1-Amino-3-carboxy-4-oxy- benzol - 5 - sulfonsäure in verdünnter Natron lauge, setzt 1 Mol Natriumnitrit hinzu und lässt dann unter Rühren in Salzsäure ein laufen.
Zu der Diazoverbindung gibt man so dann eine mit verdünnter Salzsäure herge stellte Lösung von 1 Mol 1-Amino-2,5-di- methylbenzol und vereinigt zum Azofarbstoff unter langsamer Zugabe von Natriumacetat. Nach mehrstündigem Rühren säuert man schwach mit Salzsäure an und presst ab.
Dar auf kocht man den Farbstoff in ätzalkalischer Lösung 3'/2 Stunden lang unter Rückfluss mit 0,7 Mol 4.4'-Dinitrostilben-2. 2'-disulfosäure, stumpft das Alkali mit Salzsäure ab, salzt aus und prellt ab.
Der Farbstoff gibt auf Baumwolle und Kunstseide lebhafte orange Färbungen von sehr guter Lichtechtheit, die durch --'LNTaclibe- handlung mit dreiwertigen Chromsalzen eine ausgezeichnete 'Waschechtheit erlangen.
<B> Additional patent </B> to the main patent No. 213057. Process for the production of a substantive azo dye. The main patent is a process for the production of a new, substantive azo dye, in which the amino azo dye of the formula COOH CH3 II HO -> - NN-ONH2 I 503H OCH3 with 4.4'-dinitrostilbene-2.2'-disulfonic acid to one Condensed dye,
which contains about 0.65 mol of 4.4'-dinitrostilbene-2.2'-disulfonic acid per 1112o1 of the aminoazo dye. It has now been found that a new, noun azo dye is obtained if the aminoazo dye of the formula COOH CH3 HO -O-N = N-O-NH2 I I O311 CH3 is condensed with 4.4'-dinitrostilbene-2 @ .2'-disulfonic acid to form a dye,
which contains about 0.7 mol of 4.4'-dinitrostilbene-2.2'-disulfonic acid per mole of the aminoazo dye.
The new dye dyes vegetable fibers and regenerated cellulose in very even, lively orange tones, the wash fastness of which can be increased by post-treatment with trivalent chromium salts. <I> Example: </I> 1 mol of 1-amino-3-carboxy-4-oxybenzene - 5 - sulfonic acid is dissolved in dilute sodium hydroxide solution, 1 mol of sodium nitrite is added and then allowed to run into hydrochloric acid while stirring.
A solution of 1 mol of 1-amino-2,5-dimethylbenzene prepared with dilute hydrochloric acid is then added to the diazo compound and combined to form the azo dye with the slow addition of sodium acetate. After several hours of stirring, it is acidified weakly with hydrochloric acid and pressed off.
The dye is then boiled in a caustic solution for 3½ hours under reflux with 0.7 mol of 4,4'-dinitrostilbene-2. 2'-disulfonic acid, blunt the alkali with hydrochloric acid, salt out and bounce off.
The dye gives cotton and rayon lively orange dyeings of very good lightfastness, which, through treatment with trivalent chromium salts, achieve excellent washfastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE215835X | 1938-07-23 | ||
| CH213057T | 1939-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215835A true CH215835A (en) | 1941-07-15 |
Family
ID=25725352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215835D CH215835A (en) | 1938-07-23 | 1939-06-15 | Process for the preparation of a substantive azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215835A (en) |
-
1939
- 1939-06-15 CH CH215835D patent/CH215835A/en unknown
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