CH221176A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH221176A CH221176A CH221176DA CH221176A CH 221176 A CH221176 A CH 221176A CH 221176D A CH221176D A CH 221176DA CH 221176 A CH221176 A CH 221176A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- stilbene
- copper
- production
- 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 5
- 238000000034 method Methods 0.000 title claims description 5
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title claims description 5
- 235000021286 stilbenes Nutrition 0.000 title claims description 5
- 239000000975 dye Substances 0.000 claims description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 3
- 239000004922 lacquer Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 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 description 1
- 239000005749 Copper compound Substances 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
- 239000002253 acid Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 217234. Verfahren zur Darstellung eines Stilbenfarbstoifes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Stilben- farbstoffes, dadurch gekennzeichnet, dass man 4-Amino-2-methoxy-2'-oxy-5'-nitro-1,1'- azobenzol-3'-sulfonsäure,
beispielsweise her bestellt durch Kuppeln von diazotierter 4-Nitro -2 - amino -1- oxybenzol -6- sulf onsäure mit m-Anisidin, mit oder ,ohne Druck mit 4,4'-Dinitrostilben-2,2'-disulfonsäure konden siert und das Kondensationsprodukt mit kupferabgebenden Mitteln in den Kupfer lack überführt.
Der neue Farbstoff stellt getrocknet ein dunkles Pulver dar, er löst sich in Wasser mit rotbrauner, in konzentrierter Schwefel säure mit blauer Farbe und färbt Baumwolle in sehr lichtechten tiefbraunen Tönen.
Beispiel <I>1:</I> 73,6 Teile des Farbstoffes, dargestellt durch Kuppeln von diazotierter 4-Nitro-2- amino-l-oxybenzol-6-sul.fonsäure mit m-Ani- sidin in schwach la.ckmussaurer Lösung, werden mit 95 Teilen 4,4'-dinitros@tilben-2.2'- diisulfosaurem Natrium in 500 Teilen Wasser und 100 Teilen Natronlauge von 36 Be 18 Stunden in einem Rührkessel oder Rühr- autoklaven bei 100 bis<B>105'</B> kondensiert.
Nach dem Abstumpfen der Natronlauge mit Salzsäure wird der Farbstoff Hausgesalzen und filtriert.
Der noch feuchte Filterkuchen wird in zirka 3000 Teilen Wasser bei<B>80'</B> gelöst und mit einer ammoniakalisehen Kupfersulfat lösung, hergestellt aus 50 Teilen, kristalli- siertem Kupfersulfat, gelüst in 200 Teilen Wasser und 150 Teilen 25 % igem Ammoniak, 6 Stunden bei 80 bis<B>90'</B> gekupfert. Dabei wird kontrolliert, -dass bis zum Schluss Kup- ferübersehuss vorhanden ist. Die Kupfer verbindung wird ausgesalzen und filtriert.
<I>Beispiel 2:</I> 73,6 Teile des Farbstoffes, dargestellt durch Kuppeln von diazotierter 4-Nitro-2- amino-l-oxybenzol-6-sulfonsäure mit m-Ani- si din, werden mit 47,4 Teilen 4,4'-dinitro- stilben-2,
2'-dieulfosaurem Natrium in 500 Teilen Wasser und 100 Teilen Natronlauge -von<B>36'</B> B6 18 Stunden in einem Rührkessel oder Rührautoklaven bei 100 bis<B>105'</B> kon densiert. Nach dem Abstumpfen der Natron lauge, mit Salzsäure wird der Farbstoff aus gesalzen und filtriert.
Der noch feuchte Filterkuchen des Farb stoffes wird in zirka 3000 Teilen Wasser bei 80 gelöst und mit einer ammoniakalisehen Kupfersulfatlösunb, herbestellt aus 50 Teilen kristallisiertem Kupfersulfat, gelöst in 200 Teilen Wasser und 150 Teilen<I>25</I> ,3ö ibem Ammoniak, 6 Stunden bei 80 bis 90 gekup- fert. Die Kupferverbindung wird. aus- besal.zen und filtriert.
Der neue Farbstoff stellt getrocknet ein dunkles Pulver dar, er löst sieh in Wasser mit rotbrauner, in konzentrierter Schwefel säure mit blauer Farbe und färbt Baumwolle in sehr lichtechten tiefbraunen Tönen.
<B> Additional patent </B> to main patent no. 217234. Process for the production of a stilbene dye. The subject of the present patent is a process for the production of a stilbene dye, characterized in that 4-amino-2-methoxy-2'-oxy-5'-nitro-1,1'-azobenzene-3'-sulfonic acid,
for example, ordered by coupling diazotized 4-nitro -2 - amino -1-oxybenzene -6- sulfonic acid with m-anisidine, with or without pressure with 4,4'-dinitrostilbene-2,2'-disulfonic acid condensed and the condensation product is converted into the copper lacquer with copper-releasing agents.
The new dye is a dark powder when dried; it dissolves in water with a reddish brown color, in concentrated sulfuric acid with a blue color and dyes cotton in very lightfast deep brown tones.
Example <I> 1 </I> 73.6 parts of the dye, prepared by coupling diazotized 4-nitro-2-amino-1-oxybenzene-6-sulphonic acid with m-anisidine in weakly lacquer acid Solution, with 95 parts of 4,4'-dinitros @ tilben-2.2'-diisulfosaurem sodium in 500 parts of water and 100 parts of sodium hydroxide solution of 36 Be 18 hours in a stirred tank or stirred autoclave at 100 to 105 '</ B> condensed.
After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is salted in house and filtered.
The still moist filter cake is dissolved in about 3000 parts of water at 80 and with an ammoniacal copper sulphate solution made from 50 parts of crystallized copper sulphate, dissolved in 200 parts of water and 150 parts of 25% ammonia , 6 hours at 80 to <B> 90 '</B> coppered. It is checked that there is an excess of copper right up to the end. The copper compound is salted out and filtered.
<I> Example 2: </I> 73.6 parts of the dye, prepared by coupling diazotized 4-nitro-2-amino-1-oxybenzene-6-sulfonic acid with m-aniside, are 47.4 parts Share 4,4'-dinitro-stilbene-2,
2'-sodium sulphate in 500 parts of water and 100 parts of sodium hydroxide solution of 36 'B6 condensed for 18 hours in a stirred tank or stirred autoclave at 100 to 105' '. After the sodium hydroxide solution has been blunted, the dye is salted out with hydrochloric acid and filtered.
The still moist filter cake of the dye is dissolved in about 3000 parts of water at 80 and treated with an ammoniacal copper sulfate solution, obtained from 50 parts of crystallized copper sulfate, dissolved in 200 parts of water and 150 parts of <I> 25 </I>, 30% ammonia, 6 hours at 80 to 90 coppered. The copper connection will. salt out and filter.
The new dye is a dark powder when dried; it dissolves in water with a reddish brown color, in concentrated sulfuric acid with a blue color and dyes cotton in very lightfast deep brown tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH221176T | 1938-09-13 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221176A true CH221176A (en) | 1942-05-15 |
Family
ID=25725923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221176D CH221176A (en) | 1938-09-13 | 1938-09-13 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221176A (en) |
-
1938
- 1938-09-13 CH CH221176D patent/CH221176A/en unknown
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