CH221175A - Process for the preparation of a stilbene dye. - Google Patents
Process for the preparation of a stilbene dye.Info
- Publication number
- CH221175A CH221175A CH221175DA CH221175A CH 221175 A CH221175 A CH 221175A CH 221175D A CH221175D A CH 221175DA CH 221175 A CH221175 A CH 221175A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- copper
- stilbene
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 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 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title claims description 4
- 235000021286 stilbenes Nutrition 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000004922 lacquer Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 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 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 6
- 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
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 2
- 239000003929 acidic solution Substances 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
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 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
- 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 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium 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
Verfahren zur Darstellung eines Stilbenfarbstoffes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Stilben- farbstoffes, dadurch gekennzeichnet, dass man 4-Amino-2-methoxy-2'-oxy-3'-chlor-1,1'- a7obenzol-5'-sulfonsäure, beispielsweise her gestellt durch Kuppeln von diazotierter 6 -Chlor- 2 - amino -1- oxybenzol -4- sulf onsäure mit m-Anisidin, mit oder ohne Druck mit 4,4'-Dinitro,stilben-2,
2'-disulfonsäure konden siert und das Kondensationsprodukt mit kupferabgebenden Mitteln in den Kupferlack überführt.
Der neue Farbstoff stehlt getrocknet ein dunkles Pulver dar, .er löst sich in Wasser mit braunroter, in konzentrierter Sch-,vefel- säure mit blauer Farbe und färbt Baum in sehr lichtechten tiefbraunen Tönen. disulfosaurem Natrium in 500 Teilen Wasser und 100 Teilen Natronlauge von 36'B6 18 Stunden in einem Rührkessel oder Rührautoklaven bei 100 bis <B>105'</B> kondensiert. Nach dem Abstumpfen der Natronlauge mit Salzsäure wird der Farbstoff vollends aus gesalzen und filtriert.
Der noch feuchte Filterkuchen wird in zirka 3000 Teilen Wasser bei<B>80'</B> gelöst und mit einer ammoniakalischen Kupfersulfat lösunb, herbestellt aus 50 Teilen kristalli sierten Kupfersulfat, gelöst in 200 Teilen Wasser und 150 Teilen 25%igem Ammoniak 6 Stunden bei 80 bis<B>90'</B> gekupfert. Dabei wird kontrolliert, dass bis zum Sehluss Kup- ferüberschuss vorhanden isst. Die Kupfer verbindung wird nusgesalzen und filtriert.
Beispiel <I>1:</I> 71,5 Teile des Farbstoffes, dargestellt durch Kuppeln von diazotierter 6-Chlor-2- amino-l-oxybenzol-4-@sulfasäure mit m-Ani- sidin in schwach lackmussaurer Lösung, werden mit 95 Teilen 4,4'-dinitrostilben-2.2'- Beispiel <I>2:
</I> 71,5 Teile des Farbstoffes, dargestellt durch Kuppeln. von diazotierter 6-Chlor-2- amino-l-oxybenzol-4-,sulfonsäure mit m-Ani- sidin in schwach lackmussaurer Lösung, , werden mit 47,4 Teilen 4,4'-dinitrostilben- \? 2'-clisulfosaurein N-,
itriuni in 500 Teilen Wasser und<B>100</B> Teilen Natronlauge von <B>W</B> Be Be 18 Stunden in einem Rührkessel ocle r Rührautokla.ven bei 100 bis 105 lzonden- siert. Nach dem Abstumpfen d=er Natron lauge mit Salzsäure wird der Farbstoff vollends ausbesalzen und filtriert.
Der noch feuchte Filterlauchen des Farb stoffes wird in zirka 3000 Teilen Wasser bei<B>80'</B> gelöst und mit einer ammoniaka- lischen Kupfersulfatlösung, hergestellt aus 50 Teilen kristallisierten Kupfersulfat, -e löst in 200 Teilen 'NVasSer und 1:
50 Teilen 25 ö igem Ammoniak, 6 Stunden bei 80 bis 90 bekupfert. Die Kupferverbindung wird aus-esalzen und filtriert.
Der neue Farbstoff stellt getrochn .et ein dunkles Pulver dar, er löst sich in 'Wasser mit braunroter, in konzentrierter Schw < fcl- sä-ure mit blauer Farbe und färbt Baum wolle in sehr lichtechten tiefbraunen Tönen.
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-methoxy-2'-oxy-3'-chloro-1,1'-a7obenzene-5'-sulfonic acid, for example made by coupling diazotized 6-chloro-2-amino -1-oxybenzene -4- sulfonic acid with m-anisidine, with or without pressure with 4,4'-dinitro, stilbene-2,
2'-disulfonic acid condenses and the condensation product is converted into the copper lacquer with copper-releasing agents.
The new dye steals a dark powder when dried, it dissolves in water with brownish-red, in concentrated sic, vefelic acid with blue color and colors the tree in very lightfast deep brown tones. sodium disulphonate in 500 parts of water and 100 parts of sodium hydroxide solution for 36 'B6 for 18 hours in a stirred tank or stirred autoclave at 100 to 105' '. After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is completely salted out and filtered.
The still moist filter cake is dissolved in about 3000 parts of water at <B> 80 '</B> and treated with an ammoniacal copper sulfate solution, made from 50 parts of crystallized copper sulfate, dissolved in 200 parts of water and 150 parts of 25% ammonia for 6 hours at 80 to <B> 90 '</B> coppered. It is checked that there is an excess of copper until the end of the day. The copper compound is nut salted and filtered.
Example <I> 1 </I> 71.5 parts of the dye, prepared by coupling diazotized 6-chloro-2-amino-1-oxybenzene-4- @ sulfic acid with m-anisidine in a weakly lacquer acidic solution with 95 parts of 4,4'-dinitrostilbene-2.2'- Example <I> 2:
</I> 71.5 parts of the dye represented by domes. of diazotized 6-chloro-2-amino-1-oxybenzene-4-, sulfonic acid with m-anisidine in a weakly lacquer acidic solution, are mixed with 47.4 parts of 4,4'-dinitrostilbene \? 2'-clisulfosaurein N-,
itriuni in 500 parts of water and <B> 100 </B> parts of sodium hydroxide solution of <B> W </B> Be Be 18 hours in a stirred tank or stirred autoclave at 100 to 105 liters. After the sodium hydroxide solution has been blunted with hydrochloric acid, the dye is completely salted out and filtered.
The still moist filter luminescence of the dye is dissolved in about 3000 parts of water at <B> 80 '</B> and mixed with an ammoniacal copper sulphate solution made from 50 parts of crystallized copper sulphate, -e dissolves in 200 parts of' NVasSer and 1:
50 parts of 25% ammonia, copper-plated at 80 to 90 for 6 hours. The copper compound is salted out and filtered.
The new dye is a dark powder when dried; it dissolves in water with a brownish-red color, and in concentrated flacic acid with a blue color, and dyes cotton in very lightfast deep brown tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH221175T | 1938-09-13 | ||
| CH217234T | 1940-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221175A true CH221175A (en) | 1942-05-15 |
Family
ID=25725922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221175D CH221175A (en) | 1938-09-13 | 1938-09-13 | Process for the preparation of a stilbene dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221175A (en) |
-
1938
- 1938-09-13 CH CH221175D patent/CH221175A/en unknown
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