CH221192A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH221192A CH221192A CH221192DA CH221192A CH 221192 A CH221192 A CH 221192A CH 221192D A CH221192D A CH 221192DA CH 221192 A CH221192 A CH 221192A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- dye
- amino
- copper
- stilbene
- 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
- 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
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 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
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 229950000244 sulfanilic acid Drugs 0.000 claims description 3
- 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 claims description 2
- 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
- 239000000835 fiber Substances 0.000 claims 2
- 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
- 235000011121 sodium hydroxide Nutrition 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 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- RPJXLEZOFUNGNZ-UHFFFAOYSA-N 5-methoxy-2-methylaniline Chemical compound COC1=CC=C(C)C(N)=C1 RPJXLEZOFUNGNZ-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 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
- 239000012065 filter cake 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 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002178 crystalline material Substances 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 Stilbenfarbstoffes. Gegenstand des vorliegenden Zusatzpa tentes ist ein Verfahren zur Herstellung eines Stilbenfarbstoffes, dadurch gekennzeichnet,
dass man ein Gemisch der Farbstoffe 2-Amino- 1-oxybenzol-4-sulfonsäure -> 1-Amino-3- methoxy-6-methylbenzol und 1-Aminobenzol- 4-sulfonsäure --> p-Xylidin mit oder ohne Druck mit 4,4'-Dinitrostilben-2,2'-disulfon- säure kondensiert und das Kondensations produkt mit kupferabgebenden Mitteln in den Kupferlack überführt.
Der Farbstoff stellt ein dunkles Pulver dar, löst sich in Wasser mit brauner, in konz. Schwefelsäure mit blauer Farbe und färbt Zellulosefasern in lichtechten, satten Brauntönen.
<I>Beispiel 1:</I> 34 Teile des Farbstoffes 2-Amino-l-oxy- benzol - 4 - sulfonsäure --> - 1 - Amino - 3- methoxy-6-methylbenzol und 30,5 Teile des Farbstoffes 1-Aminobenzol-4-sulfonsäure p - Xylidin werden mit 47,4 Teilen 4,4'-dinitrostilben-2,
2'-disulfonsaurem Na- trium in 500 Teilen Wasser und 100 Teilen Natronlauge von 36 B6 12-14 Stunden in einem Rührkessel oder Rührautoklaven bei Siedetemperatur kondensiert. Nach dem Ab stumpfen der Natronlauge mit Salzsäure wird der Farbstoff ausgesalzen und filtriert.
Der noch feuchte Filterkuchen wird in 1500 Teilen Wasser heiss gelöst und mit einer ammoniakalischen Kupfersulfatlösung, her gestellt aus 25 Teilen krist. Kupfersulfat, ge löst in 100 Teilen Wasser imd 55 Teilen 25 % igem Ammoniak, 12 Stunden bei 90-95 verrührt. Dabei wird kontrolliert, dass bis zum Schluss ein Kupferüberschuss vorhanden ist. Die Kupferverbindung wird ausgesalzen und abfiltriert.
<I>Beispiel 2:</I> 17 Teile des Farbstoffes 2-Amino-l- oxybenzol-4-sulfonsäur.e -> 1-Amino-3- methoxy-6-methylbenzol und 30,5 Teile des Farbstoffes 1 - Aminobenzol - 4 - sulfonsäure p-Xylidin werden mit 47,4 Teilen 4,4' dinitrostilben-2,2'-disulfons,aurem Natrium in 500 Teilen Wasser und 100 Teilen Natron lauge von 36 B6 l2-14 Stunden in einem Rührkessel oder Rührautoklaven bei Siede temperatur kondensiert.
Nach dem Abstump fen der Natronlauge mit Salzsäure wird der Farbstoff ausgesalzen und filtriert..
her noch feuchte I'iltcrkuchen wird in 1500 Teilen Wasser heiss gelöst und mit. einer ammoniakalischen Kupfersulfatlösun--, her gestellt aus 13 Teilen krist. Kupfersulfat, ge löst in<B>100</B> Teilen Wasser und 30 Teilen 25 % igem Ammoniak, 12 Stunden bei<B>90-95</B> verrührt. Dabei wird kontrolliert, dass bis zum Sehluss ein lLupferüberschuss vorhanden ist. Die Kupferverbindung wird aus gesalzen und abfiltriert.
Beide Farbstoffe stellen dunkle Pulver dar, lösen sich in Wasser mit brauner, in konz. Schwefelsäure mit blauer Farbe und färben Zellulosefasern in lichtechten, satten Brauntönen.
Additional patent to the main patent No. 217234. -Process for the preparation of a stilbene dye. The subject of the present Zusatzpa tentes is a process for the production of a stilbene dye, characterized in that
that a mixture of the dyes 2-amino-1-oxybenzene-4-sulfonic acid -> 1-amino-3-methoxy-6-methylbenzene and 1-aminobenzene-4-sulfonic acid -> p-xylidine with or without pressure with 4 , 4'-Dinitrostilben-2,2'-disulfonic acid is condensed and the condensation product is transferred to the copper lacquer with copper-releasing agents.
The dye is a dark powder, dissolves in water with brown, in conc. Sulfuric acid with a blue color and dyes cellulose fibers in lightfast, rich brown tones.
<I> Example 1: </I> 34 parts of the dye 2-amino-1-oxybenzene - 4 - sulfonic acid -> - 1 - amino - 3-methoxy-6-methylbenzene and 30.5 parts of the dye 1 -Aminobenzene-4-sulfonic acid p - Xylidine with 47.4 parts of 4,4'-dinitrostilben-2,
2'-disulfonic acid sodium in 500 parts of water and 100 parts of sodium hydroxide solution for 36 B6 12-14 hours in a stirred tank or stirred autoclave at boiling point condensed. 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 1500 parts of hot water and treated with an ammoniacal copper sulfate solution made from 25 parts of crystalline material. Copper sulfate, dissolved in 100 parts of water imd 55 parts of 25% ammonia, stirred for 12 hours at 90-95. It is checked that there is an excess of copper right up to the end. The copper compound is salted out and filtered off.
<I> Example 2: </I> 17 parts of the dye 2-amino-l-oxybenzene-4-sulfonsäur.e -> 1-amino-3-methoxy-6-methylbenzene and 30.5 parts of the dye 1-aminobenzene - 4 - sulfonic acid p-xylidine with 47.4 parts of 4,4 'dinitrostilbene-2,2'-disulfone, acidic sodium in 500 parts of water and 100 parts of sodium hydroxide solution for 36 B6 12-14 hours in a stirred kettle or stirred autoclave Boiling temperature condenses.
After blunting the caustic soda with hydrochloric acid, the dye is salted out and filtered.
The still moist filter cake is dissolved in 1500 parts of hot water and mixed with. an ammoniacal copper sulphate solution, made from 13 parts of crystalline Copper sulfate, dissolved in <B> 100 </B> parts of water and 30 parts of 25% ammonia, stirred for 12 hours at <B> 90-95 </B>. It is checked that there is an excess of oil up to the close. The copper compound is salted out and filtered off.
Both dyes are dark powders, dissolve in water with brown, in conc. Sulfuric acid with a blue color and dye cellulose fibers in lightfast, rich brown tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH221192T | 1938-09-13 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221192A true CH221192A (en) | 1942-05-15 |
Family
ID=25725939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221192D CH221192A (en) | 1938-09-13 | 1938-09-13 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221192A (en) |
-
1938
- 1938-09-13 CH CH221192D patent/CH221192A/en unknown
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