CH228818A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH228818A CH228818A CH228818DA CH228818A CH 228818 A CH228818 A CH 228818A CH 228818D A CH228818D A CH 228818DA CH 228818 A CH228818 A CH 228818A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- brown
- stilbene
- copper
- Prior art date
Links
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 title claims description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title claims description 4
- 235000021286 stilbenes Nutrition 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229920003043 Cellulose fiber Polymers 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 239000007859 condensation product Substances 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
- UETHPMGVZHBAFB-OWOJBTEDSA-N 4,4'-dinitro-trans-stilbene-2,2'-disulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O UETHPMGVZHBAFB-OWOJBTEDSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- UETHPMGVZHBAFB-UHFFFAOYSA-N 4,4'-dinitrostilbene-2,2'-disulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1C=CC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O UETHPMGVZHBAFB-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution 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
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/04—Stilbene-azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Artificial Filaments (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 217234. Terfahren zur Darstellung eines Stilbenfarbstoffes. Gegenstand des vorliegenden Zusatz patentes ist ein Verfahren zur Darstellung eines Stilbenfarbstoffes, dadurch gekenn zeichnet, dass man 4,4'-Dinitrostüben-2,2'-di- sulfonsäure mit dem Azofarbstoff 4-Nitro-2- amino-l-oxybenzol -@- 2-(4-Aminophenyl)-5'- oxynaphto - 1',2':
4,5 - triazol- 7'-sulfonsäure kondensiert und das Kondensationsprodukt anschliessend mit kupferabgebenden Mitteln ,behandelt.
<I>Beispiel:</I> 52,1 Teile des Farbstoffes, hergestellt durch Kuppeln von diazotiertem 4-Nitro-2- amino-l-oxybenzol mit 2-(4-Aminophenyl)- 5'- oxynaphto-1.', 2' :
4,5-triazol- 7'-sulf onsäure in mimosaalkalischer Lösung in Gegenwart von Pyridin, werden mit 47,4 Teilen 4,4'-di- nitrostilben-2,2'-disulfonsaurem Natrium in 330 Teilen Wasser und 70 Teilen Natron lauge 36'B6 18 Stunden unter R,ückfluss bei 100-105 kondensiert. Nach dem Erkalten wird die Natronlauge neutralisiert, der Farb stoff mit Kochsalz vollends ausgefällt und filtriert.
Anschliessend wird der Farbstoff in üblicher Weise mit kupferabgebenden Mitteln. in die Kupferverbindung übergeführt. Er stellt getrocknet ein dunkles, grauviolettes Pulver dfar, löst sich in. Wasser mit orange- brauner, in konzentrierter Schwefelsäure mit violetter Farbe und färbt Cellulosefasern in gelbbraunen Tönen von sehr guter Lichtecht heit.
Additional patent to main patent no. 217234. Terfahren for the representation of a stilbene dye. The subject of the present additional patent is a process for the preparation of a stilbene dye, characterized in that 4,4'-dinitrostebet-2,2'-disulfonic acid is mixed with the azo dye 4-nitro-2-amino-l-oxybenzene - @ - 2- (4-aminophenyl) -5'- oxynaphto - 1 ', 2':
4,5-triazole-7'-sulfonic acid is condensed and the condensation product is then treated with copper-releasing agents.
<I> Example: </I> 52.1 parts of the dye prepared by coupling diazotized 4-nitro-2-amino-1-oxybenzene with 2- (4-aminophenyl) -5'-oxynaphto-1. ', 2 ':
4,5-triazole-7'-sulfonic acid in a mimosa-alkaline solution in the presence of pyridine is combined with 47.4 parts of 4,4'-di-nitrostilbene-2,2'-disulfonic acid in 330 parts of water and 70 parts of sodium hydroxide 36'B6 18 hours under reflux, condensed at 100-105. After cooling, the sodium hydroxide solution is neutralized, the dye is completely precipitated with table salt and filtered.
The dye is then used in the usual way with copper-releasing agents. converted into the copper compound. When dried, it creates a dark, gray-violet powder, dissolves in water with orange-brown, in concentrated sulfuric acid with violet color and dyes cellulose fibers in yellow-brown shades of very good lightfastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH228818T | 1939-07-03 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH228818A true CH228818A (en) | 1943-09-15 |
Family
ID=25725946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH228818D CH228818A (en) | 1939-07-03 | 1939-07-03 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH228818A (en) |
-
1939
- 1939-07-03 CH CH228818D patent/CH228818A/en unknown
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