CH221191A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH221191A CH221191A CH221191DA CH221191A CH 221191 A CH221191 A CH 221191A CH 221191D A CH221191D A CH 221191DA CH 221191 A CH221191 A CH 221191A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- amino
- brown
- 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
- 239000000975 dye Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229920003043 Cellulose fiber Polymers 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 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 claims description 3
- 238000004519 manufacturing process Methods 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
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 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
- PPVRMPPLECDING-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 PPVRMPPLECDING-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241001024304 Mino Species 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
- 239000002253 acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 217234. Verfahren zur Darstellung eines Stilbenfarbstoifes. 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 4-aminoazo- benzol-4'-sulfonsaures Natrium mit oder ohne Druck mit 4,4'-Dinitrostilben-2,2'-,disulfon- säure kondensiert und dass Kondensations produkt mit kupferabgebenden Mitteln in den Kupferlack überführt.
Der Farbstoff stellt ein dunkles Pulver dar, er 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 Teile 4- a.mino - azobenyol - 4' - sulfonsaures Natrium werden mit 47,4 Teilen 4,4\-dinitrostilben- 2,2'-disulfonsaurem Natrium in 500 Teilen Wasser und<B>100</B> Teilen Natronlauge von 36 B6, 12-14 Stunden bei Siedetemperatur kondensiert.
Nach dem Abstumpfen der Natronlauge mit Salzsäure wird der Farb stoff mit Kochsalz ausgefällt und filtriert.
Der noch feuchte Filterkuchen wird in 1500 Teilen Wasser heiss gelöst und mit einer Lösung, hergestellt aus 2-5 Teilen krist. Kupfersulfat in 100 Teilen Wasser und 60 Teilen 25 % igem Ammoniak, 12 Stunden bei 90-95 verrührt. Dabei wird kontrol liert, dass bis zum Schluss ein Kupferüber- sehuss vorhanden ist.
Der Farbstoff stellt ein dunkles Pulver ,dar, er löst sich in Wasser mit brauner, in konz. Schwefelsäure mit blauer Farbe und färbt Zellulosefasern in lichtechten, satten Brauntönen.
<I>Beispiel 2:</I> 20 Teile des Farbstoffes 2-Amino-l-oxy- benzol - 4 - sulfonsäure #- 1- Amino - 3 methoxy-6-methylbenzol und 30 Teile 4 amino-azobenzol-4'-sulfonsaures Natrium wer- den mit 47,4 Teilen 4,4'-dinitrostilben-2,2'- disulfonsaurem Natrium in 500 Teilen Was ser und<B>100</B> Teilen Natronlauge von 36 B6, 12-.14 Stunden bei Siedetemperatur kon densiert. Nach dem Abstumpfen der Natron lauge mit Salzsäure wird der Farbstoff mit Kochsalz ausgefällt und filtriert.
Der noch feuchte Filterkuchen wird in 1500 Teilen Wasser heiss gelöst und mit einer Lösung, herbestellt aus 1.6 Teilen krist. Kupfersulfat in 100 Teilen Wasser und 40 Teilen 25%igem Ammoniak, 12 Stunden bei 90-95' verrührt. Dabei wird kontrolliert, dass bis zum Schluss ein Kupferüberschuss vorhanden ist.
Der Farbstoff stellt ein dunkles Pulver dar, er löst sich in Wasser mit brauner, in konz. Schwefelsäure mit blauer Farbe und färbt Zellulosefasern in lichtechten, satten Brauntönen.
Additional patent to main 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 2-amino-1-oxybenzene-4-sulfonic acid,
- 1-Amino-3-methoxy-6-methylbenzene and 4-aminoazobenzene-4'-sulfonic acid sodium with or without pressure with 4,4'-dinitrostilbene-2,2 '-, disulfonic acid condensed and that condensation product transferred to the copper lacquer with copper-releasing agents.
The dye is a dark powder, it 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 parts of 4 - a.mino - azobenyol 4'-Sodium sulfonate is added with 47.4 parts of 4,4'-dinitrostilbene-2,2'-disulfonate of sodium in 500 parts of water and 100 parts of sodium hydroxide solution of 36 B6 for 12-14 hours Condensed boiling point.
After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is precipitated with sodium chloride and filtered.
The still moist filter cake is dissolved in 1500 parts of hot water and treated with a solution made from 2-5 parts of crystalline. Copper sulfate in 100 parts of water and 60 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 dye is a dark powder, it dissolves in water with brown, in conc. Sulfuric acid with a blue color and dyes cellulose fibers in lightfast, rich brown tones.
<I> Example 2: </I> 20 parts of the dye 2-amino-l-oxybenzene - 4 - sulfonic acid # - 1- amino - 3 methoxy-6-methylbenzene and 30 parts of 4 amino-azobenzene-4'- Sodium sulfonic acid is added 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 from 36 B6, 12-14 hours Boiling temperature condenses. After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is precipitated with common salt and filtered.
The still moist filter cake is dissolved in 1500 parts of hot water and treated with a solution made from 1.6 parts of crystalline. Copper sulfate in 100 parts of water and 40 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 dye is a dark powder, it dissolves in water with brown, in conc. Sulfuric acid with a blue color and dyes cellulose fibers in lightfast, rich brown tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH221191T | 1938-09-13 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221191A true CH221191A (en) | 1942-05-15 |
Family
ID=25725938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221191D CH221191A (en) | 1938-09-13 | 1938-09-13 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221191A (en) |
-
1938
- 1938-09-13 CH CH221191D patent/CH221191A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH221191A (en) | Process for the preparation of a stilbene dye. | |
| CH221192A (en) | Process for the preparation of a stilbene dye. | |
| CH221194A (en) | Process for the preparation of a stilbene dye. | |
| CH221195A (en) | Process for the preparation of a stilbene dye. | |
| CH221183A (en) | Process for the preparation of a stilbene dye. | |
| CH221189A (en) | Process for the preparation of a stilbene dye. | |
| CH221173A (en) | Process for the preparation of a stilbene dye. | |
| CH232496A (en) | Process for the preparation of a metal-containing stilbene azo dye. | |
| CH221176A (en) | Process for the preparation of a stilbene dye. | |
| CH221181A (en) | Process for the preparation of a stilbene dye. | |
| CH221193A (en) | Process for the preparation of a stilbene dye. | |
| CH221190A (en) | Process for the preparation of a stilbene dye. | |
| CH221196A (en) | Process for the preparation of a stilbene dye. | |
| CH221180A (en) | Process for the preparation of a stilbene dye. | |
| CH221177A (en) | Process for the preparation of a stilbene dye. | |
| CH221178A (en) | Process for the preparation of a stilbene dye. | |
| CH221182A (en) | Process for the preparation of a stilbene dye. | |
| CH221197A (en) | Process for the preparation of a stilbene dye. | |
| CH221187A (en) | Process for the preparation of a stilbene dye. | |
| CH145848A (en) | Process for the production of a metal-containing dye. | |
| CH221188A (en) | Process for the preparation of a stilbene dye. | |
| CH308471A (en) | Process for the preparation of a triphenylmethane dye. | |
| CH232501A (en) | Process for the preparation of a metal-containing stilbene azo dye. | |
| CH221185A (en) | Process for the preparation of a stilbene dye. | |
| CH232498A (en) | Process for the preparation of a metal-containing stilbene azo dye. |