CH221185A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH221185A CH221185A CH221185DA CH221185A CH 221185 A CH221185 A CH 221185A CH 221185D A CH221185D A CH 221185DA CH 221185 A CH221185 A CH 221185A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- copper
- dehydro
- thio
- 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 3
- 239000000975 dye Substances 0.000 claims description 15
- 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
- 239000010949 copper Substances 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 claims description 3
- 229910000906 Bronze Inorganic materials 0.000 claims description 3
- 229920000742 Cotton Polymers 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
- 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
- 239000002253 acid Substances 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
- 230000001180 sulfating effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 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
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 2
- KGZUHYIHYBDNLC-UHFFFAOYSA-N 2-(4-aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid Chemical compound S1C2=C(S(O)(=O)=O)C(C)=CC=C2N=C1C1=CC=C(N)C=C1 KGZUHYIHYBDNLC-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- 244000061775 Olea africana Species 0.000 description 2
- 235000002852 Olea africana Nutrition 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
- 239000012065 filter cake Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 238000009835 boiling Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 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, da,ss man ein Gemisch von 4-Amino-2,5-dimethoxy-2'- 5 oxy-1,1'-azobenzol-5'-sulfonsäure, beispiels weise hergestellt durch Kuppeln von diano tierter 2-Amino-l-oxybenzol-4-sulfonsäure mit 1-Amino-2,5-dimethoxybenzol,
und von De- hydro-thio-p-toluidinsulfonsäure, wie sie durch Sulfieren von Dehydro-thio-p-toluidin erhält lich ist, mit oder ohne Druck mit 4,4'-Dinitro- stilben-2,2'-disulfonsäure kondensiert und das Kondensationsprodukt mit kupferabgebenden Mitteln in den Kupferlack überführt.
Der neue Farbstoff stellt getrocknet ein dunkles Pulver dar, er löst sich in Wasser mit braunoliver, in konzentrierter Schwefel säure mit violetter Farbe und färbt Baum wolle in Bronzetönen.
Beispiel <I>1:</I> 35,3 Teile des Farbstoffes, dargestellt durch. Kuppeln von diazotierter 2-Amino-l- oYybenzol-4-sulfonsäure mit 1-Amino-2,5-di- methoxybenzol und 34 Teile dehydro-thio-p- toluidin-sulfonsaures Natrium, werden mit 47,4 Teilen 4,4'-dinitrostilben-2,2'-disulfosau- rem Natrium in 500 Teilen Wasser und 100 Teilen Natronlauge von 36 B6 18 Stunden bei Siedetemperatur kondensiert.
Nach dem Abstumpfen der Natronlauge mit Salzsäure wird der Farbstoff ausgesalzen und filtriert.
Der noch feuchte Filterkuchen wird in ca. 1500 Teilen Wasser bei<B>80'</B> 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 Stunden bei 90 bis<B>951</B> verrührt. Dabei wird kontrolliert, dass bis zum Schluss Kup- ferüberschuss vorhanden ist. Die Kupferver bindung wird ausgesalzen und filtriert.
<I>Beispiel 2:</I> 20 Teile des Farbstoffes, dargestellt durch Kuppeln von dianotierter 2-Amino-l-ogyben- zol-4-sulfonsäure mit 1-Amino-2,5-dimethogy- , Benzol, und 34 Teile dehydro-thio-p-toluidin- aulfonsaures Natrium, hergestellt durch Sul- fieren von Dehydro-thio-p-toluidin und Über führen in das Na.-salz, 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 bei Sie detemperatur kondensiert. Nach dem Ab stumpfen der Natronlauge mit Salzsäure wird der Farbstoff ausgesalzen und filtriert.
Der noch feuchte Filterkuchen des Farb stoffes wird in ca. 1500 Teilen Wasser hei 80 gelöst und mit einer ammoniakalischen Kupfersulfatlösung, hergestellt aus 16 Teilen kristallisiertem Kupfersulfat, gelöst: in 60 Teilen Wasser und 30 Teilen 25 % igem Am moniak, 6 Stunden bei 90 bis 95 verrührt. Die Kupferverbindung wird ausgesalzen und filtriert.
Der neue Farbstoff stellt getrocknet ein o dunkles Pulver dar, er löst sich in Wasser mit braunoliver, in konzentrierter Schwefel säure mit violetter Farbe und färbt Baum wolle in Bronzetönen.
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 preparation of a stilbene dye, characterized in that a mixture of 4-amino-2,5-dimethoxy-2'- 5 oxy-1,1'-azobenzene-5'- sulfonic acid, for example prepared by coupling diano-tated 2-amino-1-oxybenzene-4-sulfonic acid with 1-amino-2,5-dimethoxybenzene,
and of dehydro-thio-p-toluidinesulfonic acid, as it is obtainable by sulfating dehydro-thio-p-toluidine, condensed with or without pressure with 4,4'-dinitro-stilbene-2,2'-disulfonic acid and the condensation product is converted into the copper lacquer with copper-releasing agents.
The new dye is a dark powder when dried; it dissolves in water with brown olive, in concentrated sulfuric acid with purple color and dyes cotton in bronze tones.
Example <I> 1: </I> 35.3 parts of the dye represented by. Coupling of diazotized 2-amino-l-oYybenzene-4-sulfonic acid with 1-amino-2,5-dimethoxybenzene and 34 parts of sodium dehydro-thio-p-toluidine sulfonic acid are added with 47.4 parts of 4.4 ' -dinitrostilbene-2,2'-disulfosau- rem sodium in 500 parts of water and 100 parts of sodium hydroxide solution of 36 B6 condensed for 18 hours at the boiling point.
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 approx. 1500 parts of water at <B> 80 '</B> and treated with an ammoniacal copper sulphate solution, made from 25 parts of crystallized copper sulphate, dissolved in 100 parts of water and 60 parts of 25% ammonia 12 Stirred for hours at 90 to 951. It is checked that there is a copper surplus right up to the end. The copper compound is salted out and filtered.
<I> Example 2: </I> 20 parts of the dye prepared by coupling dianotated 2-amino-1-ogybenzene-4-sulfonic acid with 1-amino-2,5-dimethogy-, benzene, and 34 parts dehydro-thio-p-toluidine-aulfonic acid sodium, prepared by sulphating dehydro-thio-p-toluidine and converting it into the sodium salt, are mixed with 47.4 parts of 4,4'-dinitrostilbene - 2,
2 '- sodium disulfosaurem in 500 parts of water and 100 parts of sodium hydroxide solution of 36 B6 condensed for 18 hours at you 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 1500 parts of water at 80 and dissolved with an ammoniacal copper sulfate solution, made from 16 parts of crystallized copper sulfate: in 60 parts of water and 30 parts of 25% ammonia, 6 hours at 90 to 95 stirred. The copper compound is salted out and filtered.
When dried, the new dye is an o dark powder, it dissolves in water with brown olive, in concentrated sulfuric acid with a purple color and dyes cotton in shades of bronze.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH221185T | 1938-09-13 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221185A true CH221185A (en) | 1942-05-15 |
Family
ID=25725932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221185D CH221185A (en) | 1938-09-13 | 1938-09-13 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221185A (en) |
-
1938
- 1938-09-13 CH CH221185D patent/CH221185A/en unknown
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