CH221178A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH221178A CH221178A CH221178DA CH221178A CH 221178 A CH221178 A CH 221178A CH 221178D A CH221178D A CH 221178DA CH 221178 A CH221178 A CH 221178A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- copper
- blue
- parts
- 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
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 229920000742 Cotton Polymers 0.000 claims description 4
- 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
- 238000007747 plating Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 6
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- AWZACWPILWGEQL-UHFFFAOYSA-M azanium;copper(1+);sulfate Chemical compound [NH4+].[Cu+].[O-]S([O-])(=O)=O AWZACWPILWGEQL-UHFFFAOYSA-M 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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 Patentes ist ein Verfahren zur Herstellung eines Stilben- farbstoffes, dadurch gekennzeichnet, dass man 4-Amino-2,5-dimethoxy-2'-oxy-1,1'-azo- benzol-5'-sulfonsäure, beispielsweise her gestellt durch Kuppeln von diazotierter 2 - Amino - 1 - oxybenzol - 4 - sulfonsäure mit 1-Amino-2,5-dimethoxybenzol mit 4,
4'-Dini- trostilben-2,2'-,disul.fonsäure kondensiert und das Kondensationsprodukt mit kupferabge benden Mitteln in den Kupferlack überführt. Der Kupferung kann zur Reinigung des Farbstoffes auch eine Behandlung mit einer Natriumhypochloritlösung vorangehen oder rachfolgen.
Der neue Farbstoff stellt getrocknet .ein schwarzes Pulver dar, er löst sich in Wasser mit blauschwarzer, in konzentrierter Schwe felsäure mit blauer Farbe und färbt Baum wolle in sehr lichtechten grauen Tönen. Beispiel: 82,3 Teile des Farbstoffes, dargestellt durch Kuppeln von diazotierter 2-Amino-l- oxybenzol-4-sulfonsä.ut"e mit 1-Amino-2,5- dimethoxybenzol in schwach saurer Lösung, werden mit 47,4 Teilen 4,4'-dinitrostilb,en- 2,2'-,
disul.fos-aurem Natrium in 500 Teilen Wasser und 100 Teilen Natronlauge von 36 Be 18 Stunden in einem Rührkessel oder Rührautokliaven bei 100 bis<B>105'</B> kondensiert. Die Kondensation kann auch in 6 Stunden bei 120 bis 125' durchgeführt werden.
Nach dem Abstumpfen der Natronlauge mit Salz säure wird der Farbstoff ausgesalzen und filtriert. \ Der noch feuchte Filterkuchen wird in zirka 2500 Teilen Wasser bei<B>80'</B> gelöst und mit einer iammonukalischen Kupfersulfat- lösung, hergestellt aus 50 Teilen kristalli siertem Kupfersulfat, gelöst in 200 Teilen Wasser und 150 Teilen 25 %o igem Ammoniak, 12 Stunden bei 80 bis<B>90'</B> gekupfert. Dabei wird kontrolliert, dass bis zum Schluss Kup- ferübeDschuss vorhanden ist.
Die Kupfer verbindung wird ausgesalzen und filtriert.
Wird der nach obigen Angaben gekupferte Farbstoff in 1000 Teilen Wasser und 20 Teilen Natronlauge<B>30'</B> B6 gelöst, dazu langsam eine Lösung von<B>300</B> Teilen Na- tri.umhypoehlorit (7 % aktiver Chlor) zu gegeben, das Ganze eine Stunde erhitzt, neu tralisiert und ausgesalzen, so wird ein Baum wolle in etwas klareren Tönen färbendes Produkt von gleicher Konstitution erhalten.
Der neue Farbstoff stellt getrocknet ein schwarzes Pulver dar, er löst sich in Wasser mit blauschwarzer, in konzentrierter Sehwe- felsäure mit blauer Farbe und färbt Baum wolle in sehr lichteehten grauen Tönen.
Additional patent to main patent no. 217234. Process for the preparation of a stilbene dye. The present patent relates to a process for the preparation of a stilbene dye, characterized in that 4-amino-2,5-dimethoxy-2'-oxy-1,1'-azobenzene-5'-sulfonic acid, for example, is produced made by coupling diazotized 2 - amino - 1 - oxybenzene - 4 - sulfonic acid with 1-amino-2,5-dimethoxybenzene with 4,
4'-Dinitrostilbene-2,2 '-, disul.fonsäure condenses and the condensation product is converted into the copper lacquer with copper-releasing agents. The copper plating can also be preceded or followed by a treatment with a sodium hypochlorite solution to clean the dye.
The new dye is a black powder when dried, it dissolves in water with blue-black, in concentrated sulfuric acid with blue color and dyes cotton in very lightfast gray tones. Example: 82.3 parts of the dye, prepared by coupling diazotized 2-amino-l-oxybenzene-4-sulfonic acid with 1-amino-2,5-dimethoxybenzene in weakly acidic solution, are 47.4 parts 4,4'-dinitrostilb, en- 2,2'-,
disul.fos-aurem sodium in 500 parts of water and 100 parts of sodium hydroxide solution of 36 Be for 18 hours in a stirred kettle or stirred autoclave at 100 to 105 °. The condensation can also be carried out in 6 hours at 120 to 125 '.
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 about 2500 parts of water at <B> 80 '</B> and mixed with an ammonium copper sulphate solution, made from 50 parts of crystallized copper sulphate, dissolved in 200 parts of water and 150 parts of 25% strength Ammonia, coppered at 80 to <B> 90 '</B> for 12 hours. It is checked that there is copper overshot until the end.
The copper compound is salted out and filtered.
If the dye, which has been copperized according to the above, is dissolved in 1000 parts of water and 20 parts of sodium hydroxide solution <B> 30 '</B> B6, then slowly add a solution of <B> 300 </B> parts of sodium hypochlorite (7% more active Chlorine) is added, the whole thing heated for an hour, neutralized and salted out, then a cotton product of the same constitution is obtained, coloring in somewhat clearer tones.
The new dye is a black powder when dried; it dissolves in water with a blue-black color, and in concentrated sulfuric acid with a blue color and dyes cotton in very light gray tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH221178T | 1938-09-13 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221178A true CH221178A (en) | 1942-05-15 |
Family
ID=25725925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221178D CH221178A (en) | 1938-09-13 | 1938-09-13 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221178A (en) |
-
1938
- 1938-09-13 CH CH221178D patent/CH221178A/en unknown
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