CH221179A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH221179A CH221179A CH221179DA CH221179A CH 221179 A CH221179 A CH 221179A CH 221179D A CH221179D A CH 221179DA CH 221179 A CH221179 A CH 221179A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- stilbene
- parts
- amino
- 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 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 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 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
- 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
- 239000004922 lacquer Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- CLVIIRIMEIEKOQ-OWOJBTEDSA-N 4,4'-Dinitrostilbene Chemical compound C1=CC([N+](=O)[O-])=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1 CLVIIRIMEIEKOQ-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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002966 varnish 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 217234. Verfahren zur Darstellung eines Stilbenfarbstoffes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Stilben- farbstoffes, dadurch gekennzeichnet, dass man 4-Amino -<B>2,5</B> - dimethoxy- 2'- oxy - 3'- methyl- 1,1'-azobenzol-5'-sulfonsäure, beispielsweise hergestellt durch Kuppeln von diazotierter 2 -Amino-6-methyl-l-oxybenzol-4-sulfonsäure mit 1-Amino-2,
5-dimethoxybenzol, mit 4,4'- Dinitrostilben- 2,2'-disulfonsäure kondensiert und das Kondensationsprodukt mit kupfer abgebenden Mitteln in den Kupferlack über führt.
Der neue Farbstoff stellt getrocknet ein dunkles Pulver dar, er löst sich in Wasser mit braunschwarzer, in konzentrierter Schwe felsäure mit blauer Farbe und färbt Baum wolle in lichtechten, grünlichgrauen Tönen.
<I>Beispiel</I> r: 73,4 Teile des Farbstoffes, dargestellt durch Kuppeln von diazotierter 2-Amino-6- methyl - 1 - oxybenzol - 4 - sulfonsäure mit 1- Amino-2,5-dimethoxybenzol in schwach lack mussaUrer Lösung, werden mit 47,4 Teilen 4,4'- dinitrostilben - 2,
2'- disulfosaurem Na trium in 500 Teilen Wasser und 100 Teilen Natronlauge von 36 B6 18 Stunden in einem Rührkessel oder Rührautoklaven bei 100 bis 105 kondensiert. Nach dem Abstumpfen der Natronlauge mit Salzsäure wird der Farbstoff ausgesalzen und filtriert.
<I>Beispiel 2:</I> 73,4 Teile des Farbstoffes, dargestellt durch Kuppeln von diazotierter 2-Amino-6- methyl -1 - oxybenzol - 4 - sulfonsäure mit 1- Amino-2,5-dimethoxybenzol, werden mit 95 Teilen 4,4'-dinitrostilben-2,2'-disulfosaurem Natrium in 500 Teilen Wasser und 100 Tei len Natronlauge von 36 B6 18 Stunden in einem Rührkessel oder Rührautoklaven bei 100 bis 105 kondensiert.
Nach dem Ab stumpfen der Natronlauge mit Salzsäure wird der Farbstoff ausgesalzen und filtriert.
Der noch feuchte Filterkuchen des nach Beispiel 1 oder 2 ,erhaltenen Farbstoffes wird in. ca. 2500 Teilen Wasser bei 80 gelöst und mit einer ammoniakalischen Kupfersulfat- lösung, hergestellt aus 50 Teilen kristallisier- tem Kupfersulfat, gelöst in 200 Teilen Was ser und 150 Teilen 25 % igem Ammoniak, 6 Stunden bei 80 bis<B>900</B> gekupfert. Die Kupferverbindung wird ausgesalzen und fil triert.
Der neue Farbstoff stellt getrocknet ein dunkles Pulver dar, er löst sich in Wasser mit braunschwarzer, in konzentrierter Schwe felsäure mit blauer Farbe und färbt Baum wolle in lichtechten, grünlichgrauen Tönen.
Additional patent to main patent No. 217234. Process for the preparation 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 - <B> 2.5 </B> - dimethoxy- 2'-oxy - 3'-methyl-1,1 ' -azobenzene-5'-sulfonic acid, prepared for example by coupling diazotized 2-amino-6-methyl-1-oxybenzene-4-sulfonic acid with 1-amino-2,
5-dimethoxybenzene, condensed with 4,4'-dinitrostilbene-2,2'-disulfonic acid and the condensation product with copper-releasing agents in the copper lacquer.
The new dye is a dark powder when dried; it dissolves in water with a brownish-black color, in concentrated sulfuric acid with a blue color and dyes cotton in lightfast, greenish-gray tones.
<I> Example </I> r: 73.4 parts of the dye, produced by coupling diazotized 2-amino-6-methyl-1-oxybenzene-4-sulfonic acid with 1-amino-2,5-dimethoxybenzene in a weak varnish In a must-acid solution, 47.4 parts of 4,4'- dinitrostilbene - 2,
2'- disulfosaurem Na trium 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 100-105. After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is salted out and filtered.
<I> Example 2: </I> 73.4 parts of the dye, prepared by coupling diazotized 2-amino-6-methyl -1-oxybenzene-4-sulfonic acid with 1-amino-2,5-dimethoxybenzene, are with 95 parts of 4,4'-dinitrostilben-2,2'-disulfosaurem sodium in 500 parts of water and 100 Tei len sodium hydroxide solution of 36 B6 condensed in a stirred tank or stirred autoclave at 100-105 for 18 hours.
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 obtained according to Example 1 or 2 is dissolved in approx. 2500 parts of water at 80 and with an ammoniacal copper sulfate solution, prepared from 50 parts of crystallized copper sulfate, dissolved in 200 parts of water and 150 parts 25% ammonia, 6 hours at 80 to <B> 900 </B> coppered. The copper compound is salted out and filtered.
The new dye is a dark powder when dried; it dissolves in water with a brown-black color, in concentrated sulfuric acid with a blue color and dyes cotton in lightfast, greenish-gray tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH221179T | 1938-09-13 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221179A true CH221179A (en) | 1942-05-15 |
Family
ID=25725926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221179D CH221179A (en) | 1938-09-13 | 1938-09-13 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221179A (en) |
-
1938
- 1938-09-13 CH CH221179D patent/CH221179A/en unknown
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