CH221194A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH221194A CH221194A CH221194DA CH221194A CH 221194 A CH221194 A CH 221194A CH 221194D A CH221194D A CH 221194DA CH 221194 A CH221194 A CH 221194A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- copper
- acid
- sulfonic 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 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 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
- 229920003043 Cellulose fiber Polymers 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 229950000244 sulfanilic acid Drugs 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002966 varnish Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 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
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001880 copper compounds Chemical class 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
- 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
- UGYWBUWKASLNLO-UHFFFAOYSA-N [Na].[N+](=O)([O-])C=1C=C(C(=CC1)C=CC=1C(=CC(=CC1)[N+](=O)[O-])S(=O)(=O)O)S(=O)(=O)O Chemical compound [Na].[N+](=O)([O-])C=1C=C(C(=CC1)C=CC=1C(=CC(=CC1)[N+](=O)[O-])S(=O)(=O)O)S(=O)(=O)O UGYWBUWKASLNLO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium 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)
Description
Zusatzpatent 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 ein Gemisch der Farbstoffe 6-Chlor-2- amino-l-oxybenzol-4-sulfonsäure -> m- Anisidin und 1-Aminobenzol-4-sulfonsäure >-p-Xylidin mit oder ohne Druck mit 4,4'-Dinitrostilben-2,
2'-disulfonsäure konden siert und das Kondensationsprodukt mit kup ferabgebenden Mitteln in den gupferlaek überführt.
Der neue Farbstoff stellt ein fast schwar zes Pulver dar, er löst sich in Wasser mit brauner, in konzentrierter Schwefelsäure mit blauer Farbe und färbt Zellulosefasern in lichtechten, braunen Tönen.
Beispiel <I>1:</I> 30 Teile des Farbstoffes 6-Chlor-2-amino- 1-oxybenzol-4-sulfonsäure #- m-Anisidin und 25 Teile des Farbstoffes 1-Aminobenzol- 4-sulionsäure -> p-Xylidin werden mit 47,4 Teilen 4,4'-dinitrostilben-2,2'-disulfon- sa.urem Natrium in 500 Teilen Wasser und <B>1.00</B> Teilen Natronlauge 36 Be 14 bis 16 Stunden bei Siedetemperatur kondensiert.
Nach dem Abstumpfen der Natronlauge mit Salzsäure wird der Farbstoff aasgesalzen und filtriert. Der noch feuchte Filterkuchen wird in 2000 Teilen Wasser heiss gelöst und mit einer ammoniakalischen Kupfersulfat lösung, hergestellt aus 25 Teilen kristalli siertem Kupfersulfat, gelöst in 100 Teilen Wasser und 60 Teilen 25 %igem Ammoniak, 12 bis 14 Stunden bei 90 bis 95 verrührt. Dabei wird kontrolliert, dass bis zum Schluss ein gupferüberschuss vorhanden ist. Die Kupferverbindung wird aasgesalzen und ab filtriert.
<I>Beispiel 2:</I> 30 Teile des Farbstoffes 6-Chlor-2-amino- 1-oxybenzol-4-sulfonsäure .-> m-Anisidin und 30 Teile des Farbstoffes 1-Aminobenzol- 4-sulfonsäure <B>></B> p-Xylidin werden mit 47,4 Teilen 4,4'-dinitrostilben-2,2'-disulfon- saurem Natrium in 500 Teilen Wasser und <B>100</B> Teilen Natroulauge 36 Be 14 bis 16 Stunden bei Siedetemperatur kondensiert.
Nach dem Abstumpfen der Natronlauge mit Salzsäure wird der Farbstoff aasgesalzen und filtriert. Der noch feuchte Filterkuchen wird in 2000 Teilen Wasser heiss gelöst und mit einer ammoniakalischen Kupfersulfatlösung, hergestellt aus 25 Teilen kristallisiertem Kupfersulfat, gelöst in<B>100</B> Teilen Wasser und 60 Teilen 25%igem Ammoniak, 12 bis 14 Stunden bei 90 bis 95 verrührt. Dabei wird kontrolliert, dass bis zum Schluss ein Kupferüberschuss vorhanden ist. Die Kupfer verbindung wird ausgesalzen und abfiltriert.
Beide Farbstoffe stellen fast schwarze Pulver dar, sie lösen sich in Wasser mit brauner, in konzentrierter Schwefelsäure mit blauer Farbe und färben Zellulosefasern in lichtechten, braunen Tönen.
Additional patent to main patent no. 217234. Process for the representation of a stilbene dye. The subject of the present patent is a process for the preparation of a stilbene dye, characterized in that a mixture of the dyes 6-chloro-2-amino-1-oxybenzene-4-sulfonic acid -> m-anisidine and 1-aminobenzene-4- sulfonic acid> -p-xylidine with or without pressure with 4,4'-dinitrostilbene-2,
2'-disulfonic acid condenses and the condensation product is transferred into the gupferlaek with copper-releasing agents.
The new dye is an almost black powder, it dissolves in water with a brown color, in concentrated sulfuric acid with a blue color and dyes cellulose fibers in lightfast, brown tones.
Example <I> 1: </I> 30 parts of the dye 6-chloro-2-amino-1-oxybenzene-4-sulfonic acid # - m-anisidine and 25 parts of the dye 1-aminobenzene-4-sulionic acid -> p- Xylidine is condensed with 47.4 parts of 4,4'-dinitrostilbene-2,2'-disulfonic acidic sodium in 500 parts of water and 1.00 parts of 36 Be sodium hydroxide solution for 14 to 16 hours at the boiling point.
After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is washed with ash and filtered. The still moist filter cake is dissolved in 2000 parts of hot water and stirred with an ammoniacal copper sulfate solution, prepared from 25 parts of crystallized copper sulfate, dissolved in 100 parts of water and 60 parts of 25% ammonia, for 12 to 14 hours at 90 to 95. It is checked that there is an excess of copper right up to the end. The copper compound is carrion-salted and filtered off.
<I> Example 2: </I> 30 parts of the dye 6-chloro-2-amino-1-oxybenzene-4-sulfonic acid .-> m-anisidine and 30 parts of the dye 1-aminobenzene-4-sulfonic acid > </B> p-Xylidine is mixed with 47.4 parts of 4,4'-dinitrostilbene-2,2'-disulphonic acid sodium in 500 parts of water and <B> 100 </B> parts of sodium hydroxide solution 36 Be 14 to 16 Hours condensed at boiling temperature.
After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is washed with ash and filtered. The still moist filter cake is dissolved in 2000 parts of hot water and treated with an ammoniacal copper sulphate solution, prepared from 25 parts of crystallized copper sulphate, dissolved in 100 parts of water and 60 parts of 25% ammonia for 12 to 14 hours at 90 stirred until 95. It is checked that there is an excess of copper right up to the end. The copper compound is salted out and filtered off.
Both dyes are almost black powders, they dissolve in water with brown, in concentrated sulfuric acid with blue and dye cellulose fibers in lightfast, brown tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH221194T | 1938-09-13 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221194A true CH221194A (en) | 1942-05-15 |
Family
ID=25725941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221194D CH221194A (en) | 1938-09-13 | 1938-09-13 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221194A (en) |
-
1938
- 1938-09-13 CH CH221194D patent/CH221194A/en unknown
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