CH221181A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH221181A CH221181A CH221181DA CH221181A CH 221181 A CH221181 A CH 221181A CH 221181D A CH221181D A CH 221181DA CH 221181 A CH221181 A CH 221181A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- amino
- copper
- acid
- 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
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000843 powder Substances 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
- 239000004922 lacquer Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 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
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910000365 copper sulfate Inorganic materials 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
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- 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 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 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
- 229910021529 ammonia Inorganic materials 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 Stilbenfarbstoffes. Gegenstand des vorliegenden Patentes isst ein Verfahren zur Herstellung eines Stilben- farbstoffes, dadurch gekennzeichnet, dass-man ein Gemisch von 2-Methyl-4-amino-1,1'-azo- benzol-4'-sulfonsäure und von 4-Amino-2- methoxy-2'-oxy-1,1'-azobenzol-5'-sulfonsäure,
letztere beispielsweise hergestellt durch Kup peln von diazotierter 2-Amino-l-oxybenzol- 4-sulfonsäure mit m-Anisidin, mit oder ohne Druck mit 4,4'-Dinitrostilben-2,2'-disulfon- säure kondensiert und das Kondensationspro dukt mit kupferabgebenden Mitteln in den Kupferlack überführt.
Der neue Farbstoff stellt getrocknet ein dunkles Pulver dar, er löst sich in Wasser mit brauner, in konz. Schwefelsäure mit blauer Farbe und färbt Baumwolle in licht echten, vollen braunen Tönen.
<I>Beispiel 1:</I> 32,3 Teile des Farbstoffes, dargestellt durch Kuppeln von diazotierter 2-Amino-l- oxybenzol-4-sulfonsäure mit m-Anisidin, und ?9,1 Teile des Farbstoffes, dargestellt aus diazotierter Anilin-4-sulfosäure, gekuppelt mit m-Toluidin, werden mit 47,4 Teilen 4,4'- dinitrostilben-2,
2'-disulfosaurem Natrium in 500 Teilen Wasser und 100 Teilen Natron lauge von 36 B6 18 Stunden in einem Rühr- kessel oder Rührautoklaven bei Siedetempe ratur kondensiert. Nach dem Abstumpfen der Natronlauge mit Salzsäure wird der Farb stoff ausgesalzen und filtriert.
Der noch feuchte Filterkuchen wird in zirka 1500 Teilen Wasser bei<B>80'</B> gelöst und mit einer ammoniakalischen Kupfersulfat lösung, hergestellt aus 25 Teilen krist. Kup fersulfat, gelöst in 100 Teilen Wasser und 60 Teilen 25%igem Ammoniak, 6 Stunden bei 90 bis<B>95'</B> gekupfert. Dabei wird kon trolliert, dass bis zum Schluss Kupferüber- schuss vorhanden ist. Die zum Teil ausge fallene Kupferverbindung wird vollends aus gesalzen und filtriert.
<I>Beispiel 2:</I> 32,3 Teile des Farbstoffes, dargestellt durch Kuppeln von diazotierter 2-Amino-l- oxybenzol-4-sulfonsäure mit m- Anisidin, und <B>1.5</B> Teile des Farbstoffes, dargestellt aus di- azotierter Anilin-4-sulfonsäure, gekuppelt mit m-Toluidin, werden mit 47,4 Teilen 4,4'-di- nitrostilben-2,
2'-disulfosaurem Natrium in 500 Teilen Wasser und 100 Teilen Natron lauge von<B>36</B> Be 18 Stunden in einem Rühr kessel oder Rührautoklaven bei Siedetempe ratur kondensiert. Nach dem Abstumpfen der Natronlauge mit Salzsäure wird der Farb stoff ausgesalzen und filtriert.
Der noch feuchte Filterkuchen des Farb stoffes wird in zirka 1501) Teilen Wasser bei 80 gelöst und mit einer anrmoniakalischen Kupfersulfatlösung, hergestellt aus ?5 Teilen krist. Kupfersulfat, gelöst in 100 Teilen Wasser und 60 Teilen 25 '.,' igem .mmoniah. 6 Stunden bei 90 bis 95 gekupfert. Die Kupferverbindung wird ausgesalzen rund filtriert.
Der neue Farbstoff stellt betrocl@net ein dunkles Pulver dar, er löst sich in Wasser mit brauner, in konz. Schwefelsäure mit blauer Farbe und färbt Baumwolle in licht echten, vollen braunen Tönen.
<B> Additional patent </B> to main patent no. 217234. Process for the preparation of a stilbene dye. The subject of the present patent eats a process for the production of a stilbene dye, characterized in that a mixture of 2-methyl-4-amino-1,1'-azobenzene-4'-sulfonic acid and of 4-amino 2- methoxy-2'-oxy-1,1'-azobenzene-5'-sulfonic acid,
the latter, for example, prepared by coupling diazotized 2-amino-1-oxybenzene-4-sulfonic acid with m-anisidine, with or without pressure with 4,4'-dinitrostilbene-2,2'-disulfonic acid condensed and the condensation product with copper-releasing agents transferred into the copper lacquer.
The new dye is a dark powder when dried, it dissolves in water with brown, in conc. Sulfuric acid with a blue color and dyes cotton in light genuine, full brown tones.
<I> Example 1: </I> 32.3 parts of the dye, prepared by coupling diazotized 2-amino-l-oxybenzene-4-sulfonic acid with m-anisidine, and? 9.1 parts of the dye, prepared from diazotized Aniline-4-sulfonic acid, coupled with m-toluidine, are mixed with 47.4 parts of 4,4'-dinitrostilben-2,
Sodium 2'-disulfonate in 500 parts of water and 100 parts of sodium hydroxide solution for 36 B6 was condensed for 18 hours in a stirred kettle or stirred autoclave at boiling temperature. After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is salted out and filtered.
The still moist filter cake is dissolved in about 1500 parts of water at <B> 80 '</B> and treated with an ammoniacal copper sulfate solution, made from 25 parts of crystall Copper sulfate, dissolved in 100 parts of water and 60 parts of 25% ammonia, coppered for 6 hours at 90 to 95 '. It is checked that there is an excess of copper right up to the end. The partially precipitated copper compound is completely salted out and filtered.
<I> Example 2: </I> 32.3 parts of the dye, prepared by coupling diazotized 2-amino-l-oxybenzene-4-sulfonic acid with m-anisidine, and <B> 1.5 </B> parts of the dye , prepared from diacotized aniline-4-sulfonic acid, coupled with m-toluidine, with 47.4 parts of 4,4'-di-nitrostilbene-2,
Sodium 2'-disulfonate in 500 parts of water and 100 parts of sodium hydroxide solution of <B> 36 </B> Be condensed for 18 hours in a stirred kettle or stirred autoclave at boiling temperature. After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is salted out and filtered.
The still moist filter cake of the dye is dissolved in about 1501) parts of water at 80 and with an ammoniacal copper sulfate solution, made from? 5 parts of crystalline. Copper sulfate, dissolved in 100 parts of water and 60 parts of 25 '.,' Igem .mmoniah. 6 hours at 90 to 95 coppered. The copper compound is salted out and filtered.
The new dye is betrocl @ net a dark powder, it dissolves in water with brown, in conc. Sulfuric acid with a blue color and dyes cotton in light genuine, full brown tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH221181T | 1938-09-13 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221181A true CH221181A (en) | 1942-05-15 |
Family
ID=25725928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221181D CH221181A (en) | 1938-09-13 | 1938-09-13 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221181A (en) |
-
1938
- 1938-09-13 CH CH221181D patent/CH221181A/en unknown
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