CH221196A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH221196A CH221196A CH221196DA CH221196A CH 221196 A CH221196 A CH 221196A CH 221196D A CH221196D A CH 221196DA CH 221196 A CH221196 A CH 221196A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- acid
- copper
- stilbene dye
- 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 17
- 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 6
- 239000010949 copper Substances 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims description 5
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 claims description 4
- 229910000906 Bronze Inorganic materials 0.000 claims description 3
- 229920003043 Cellulose fiber Polymers 0.000 claims description 3
- 244000061775 Olea africana Species 0.000 claims description 3
- 235000002852 Olea africana Nutrition 0.000 claims description 3
- 239000010974 bronze Substances 0.000 claims description 3
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 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
- 239000004922 lacquer Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 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 1
- 239000002253 acid 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
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 2
- 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 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001880 copper compounds Chemical class 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
- 239000012065 filter cake Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229950000244 sulfanilic acid Drugs 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
- 238000009835 boiling Methods 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 Flauptpatent Nr. 217234. Verfahren zur Darstellung eines Stilbenfarbstoifes. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Herstellung eines Stilbenfarbstoffes, dadurch gekennzeichnet, dass man ein Gemisch der Farbstoffe 6-Chlor- 2-amino-l-oxybenzol-4-sulfonsäure >2,5- Dimethoxyanilin und 1-Aminobenzol-4-sul- fonsäure #- m-Toluidin 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 Farbstoff stellt ein dunkles Pulver dar, er löst sich in Wasser mit braunoliven, in konzentrierter Schwefelsäure mit blauer Farbe und färbt Zellulosefasern in licht echten Bronzetönen.
<I>Beispiel.</I> 35 Teile des Farbstoffes 6-Chlor-2-amino- 1-oxybenzol-4-sulfonsäure + 2,5-Dime- thoxyanilin und 26 Teile des Farbstoffes 1- Aminobenzol-4-sulfonsäure >m-Toluidin werden mit 47,4 Teilen 4,4'-dinitrostilben- 2,2'-disulfonsaurem Natrium in 500 Teilen Wasser und 100 Teilen Natronlauge<B>36'</B> B6 14 bis 16 Stunden bei Siedetemperatur kon densiert.
Nach dem Abstumpfen der Natron lauge mit Salzsäure wird der Farbstoff mit Kochsalz ausgefällt und filtriert.
Der feuchte Filterkuchen wird mit 2000 Teilen Wasser heiss gelöst und mit einer am- moniakalischen Kupferlösung, hergestellt aus 25 Teilen kristallisiertem Kupfersulfat, ge löst in 100 Teilen Wasser und 60 Teilen 25 % igem Ammoniak, 12 bis 14 Stunden bei 90 bis 95 verrührt. Die Kupferverbindung wird ausgesalzen und abfiltriert.
<I>Beispiel 2:</I> 35 Teile des Farbstoffes 6-Chlor-2-amino- 1-oxybenzol-4-sulfonsäure > 2,5-Dime- thoxyanilin und 26 Teile des Farbstoffes 1- Aminobenzol-4-sulfonsäure >m-TOluidin werden mit 47,4 Teilen 4,4'-dinitrostilben- 2,2'-disulfonsaurem Natrium in 500 Teilen Wasser und 100 Teilen Natronlauge 36 B6 8 Stunden bei 110 bis 115 im Autoklaven kondensiert.
Nach dem Abstumpfen der Na- tronlauge mit Salzsäure wird der Farbstoff mit Kochsalz ausgefällt und filtriert.
Der feuchte Filterkuchen wird mit 2000 Teilen Wasser heiss gelöst und mit einer ammonikalischen Kupferlösung, hergestellt aus 25 Teilen kristallisiertem Kupfersulfat, gelöst in 100 Teilen Wasser und 60 Teilen 25%igem Ammoniak, 12 bis 14 Stunden bei 90 bis 95 verrührt. Die Kupferverbindung wird a.usgesalzen und abfiltriert.
Beide Farbstoffe stellen dunkle Pulver dar, sie lösen sich in Wasser mit braunoliver, in konzentrierter Schwefelsäure mit blauer Farbe und färben Zellulosefasern in licht echten Bronzetönen.
<B> Additional patent </B> to Flaupt patent no. 217234. Process for the representation of a stilbene dye. The subject of the present additional patent is a process for the production of a stilbene dye, characterized in that a mixture of the dyes 6-chloro-2-amino-1-oxybenzene-4-sulfonic acid> 2,5-dimethoxyaniline and 1-aminobenzene-4- sulphonic acid # - m-toluidine with or without pressure with 4,4'-dinitrostilbene-2,
2'-disulfonic acid condenses and the condensation product is converted into the copper lacquer with copper-releasing agents.
The dye is a dark powder, it dissolves in water with brown olives, in concentrated sulfuric acid with a blue color and dyes cellulose fibers in light bronze tones.
<I> Example. </I> 35 parts of the dye 6-chloro-2-amino-1-oxybenzene-4-sulfonic acid + 2,5-dimethoxyaniline and 26 parts of the dye 1-aminobenzene-4-sulfonic acid> m -Toluidine is condensed with 47.4 parts of 4,4'-dinitrostilbene-2,2'-disulfonic acid sodium in 500 parts of water and 100 parts of sodium hydroxide solution <B> 36 '</B> B6 for 14 to 16 hours at boiling temperature.
After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is precipitated with common salt and filtered.
The moist filter cake is dissolved with 2000 parts of hot water and stirred with an ammoniacal copper 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 hours. The copper compound is salted out and filtered off.
<I> Example 2 </I> 35 parts of the dye 6-chloro-2-amino-1-oxybenzene-4-sulfonic acid> 2,5-dimethoxyaniline and 26 parts of the dye 1-aminobenzene-4-sulfonic acid> m-TOluidin are condensed with 47.4 parts of 4,4'-dinitrostilbene-2,2'-disulfonic acid sodium in 500 parts of water and 100 parts of sodium hydroxide solution 36 B6 for 8 hours at 110 to 115 in an autoclave.
After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is precipitated with sodium chloride and filtered.
The moist filter cake is dissolved with 2000 parts of hot water and stirred with an ammonical copper 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 hours. The copper compound is salted out and filtered off.
Both dyes are dark powders, they dissolve in water with brown olive, in concentrated sulfuric acid with blue color and color cellulose fibers in light bronze tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH221196T | 1938-09-13 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221196A true CH221196A (en) | 1942-05-15 |
Family
ID=25725943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221196D CH221196A (en) | 1938-09-13 | 1938-09-13 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221196A (en) |
-
1938
- 1938-09-13 CH CH221196D patent/CH221196A/en unknown
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