CH310423A - Process for producing a fluorescent benzotriazole compound. - Google Patents
Process for producing a fluorescent benzotriazole compound.Info
- Publication number
- CH310423A CH310423A CH310423DA CH310423A CH 310423 A CH310423 A CH 310423A CH 310423D A CH310423D A CH 310423DA CH 310423 A CH310423 A CH 310423A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- parts
- amino
- benzotriazole compound
- methoxy
- Prior art date
Links
- -1 benzotriazole compound Chemical class 0.000 title claims description 7
- 239000012964 benzotriazole Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- LNKBDFVSILQKSI-UHFFFAOYSA-N 4-Chloro-3-methoxyaniline Chemical compound COC1=CC(N)=CC=C1Cl LNKBDFVSILQKSI-UHFFFAOYSA-N 0.000 claims description 3
- 229920003043 Cellulose fiber Polymers 0.000 claims description 3
- 239000000987 azo dye Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QBHYFEWQILVXEN-UHFFFAOYSA-N 5-amino-2-(2-phenylethenyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=CC=C1 QBHYFEWQILVXEN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 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
- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung einer fluoreszierenden Benztriazolverbindung. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eineu fluoreszieren den Benztriazolverbindung. Das Verfahren ist dadurch gekennzeichnet, dass man diazotierte 4-Amino-stilben-2,sulfonsäure mit 1-Amino-3- methoxy-4-chlor-benzol kuppelt und den ent standenen o-Amino-azofarbstoff zur 1,2,3-Tri- azolverbindung oxydiert.
Die erhaltene neue 6-Chlor-5-methoxy-2- (stilbyl-4') -1,2,3 - benztriazol - 2' - sulfonsäure stellt in Form ihres Natriumsalzes eine schwach gelbstickige Substanz dar, die, auf Cellulosefasern ausgefärbt, eine Weisstönung von blauweisser Nuance ergibt.
<I>Beispiel:</I> Eine Lösung von 27,5 'Teilen 4-Amino- stilben - 2 - sulfonsäure, 4,1 Teilen Natrium- hydroxyd und 6,9 Teilen Natriumnitrit in 200 Teilen Wasser wird bei 8 bis 10, mit 25 Teilen konzentrierter Salzsäure indirekt diazotiert. Die Suspension der Diazoverbindung wird bei einer Temperatur von 10 bis 12 mit einer Lösung von 15,
8 'Teilen 1-Amino-3-methoxy- 4-chlorbenzol und 10 Teilen konzentrierter Salzsäure in 200 Teilen Wasser vereinigt und eine Lösung von 40 Teilen kristallisiertem Natriumacetat in 100 Teilen Wasser zuge- tropft. Nach beendeter Kupplung wird der o-Amino-azofarbatoff durch Zugabe von Koch salz vollständig ausgefällt, abfiltriert und mit verdünnter Kochsalzlösung ausgewaschen.
Der feuchte Farbstoff wird unter Zugabe von 20, Teilen 25prozentigem Ammoniak in heissem Wasser bei 90 bis 95 klar gelöst und die Mischung von 60 Teilen kristallisiertem Kup fersulfat in 240 Teilen Wasser mit 120 Teilen 25prozentigem Ammoniak zugegeben. Man hält die Temperatur auf 92 bis 95 , bis der o-Amino-azofarbstoff vollständig oxydiert ist, lässt erkalten und fällt die Benztriazolverbin- dimg durch Zugabe von Kochsalz vollständig aus.
Das Rohprodukt wird in# Gegenwart von überschüssigem Natriumsulfid in heissem Wasser oder wässerigem Alkohol gelöst, das entstandene Kupfersulfid abfiltriert, die überschüssige Alkalisulfidverbindung durch Salzsäure zersetzt und das Produkt durch Umlösen unter Zugabe von Tierkohle und Natriumhydrosulfit weiter gereinigt. Das Na- triumsalz der 6-Chlor-5-methoxy-2-(stübyl-4')- 1,2,3-benztriazol-2'-sulfönsäure wird als hell gelbe Substanz erhalten.
Diese Verbindung ist ein wertvolles Aufhellungsmittel für Celhi- losefasern, für Seifenpulver und synthetische Waschmittel. Bei guten Echtheiten zeigt die damit erhältliche Weisstönung eine blauweisse Nuance und weist eine hervorragende Chlor echtheit auf.
Process for producing a fluorescent benzotriazole compound. The present patent relates to a process for the preparation of a fluorescent benzotriazole compound. The process is characterized in that diazotized 4-amino-stilbene-2, sulfonic acid is coupled with 1-amino-3-methoxy-4-chlorobenzene and the resulting o-amino-azo dye is converted into 1,2,3-tri - azole compound oxidized.
The new 6-chloro-5-methoxy-2- (stilbyl-4 ') -1,2,3 - benzotriazole - 2' - sulfonic acid obtained is in the form of its sodium salt a slightly yellowish substance which, when dyed on cellulose fibers, is a White tint of blue and white nuance results.
<I> Example: </I> A solution of 27.5 parts of 4-amino-stilbene-2-sulfonic acid, 4.1 parts of sodium hydroxide and 6.9 parts of sodium nitrite in 200 parts of water is used at 8 to 10, indirectly diazotized with 25 parts of concentrated hydrochloric acid. The suspension of the diazo compound is at a temperature of 10 to 12 with a solution of 15,
8 parts of 1-amino-3-methoxy-4-chlorobenzene and 10 parts of concentrated hydrochloric acid are combined in 200 parts of water and a solution of 40 parts of crystallized sodium acetate in 100 parts of water is added dropwise. After the coupling has ended, the o-amino-azo carbate is completely precipitated by adding sodium chloride, filtered off and washed out with dilute sodium chloride solution.
The moist dye is dissolved with the addition of 20 parts of 25 percent ammonia in hot water at 90 to 95 and the mixture of 60 parts of crystallized copper sulfate in 240 parts of water with 120 parts of 25 percent ammonia is added. The temperature is maintained at 92 to 95 until the o-amino-azo dye is completely oxidized, allowed to cool and the benzotriazole compound is completely precipitated by adding sodium chloride.
The crude product is dissolved in hot water or aqueous alcohol in the presence of excess sodium sulfide, the copper sulfide formed is filtered off, the excess alkali metal sulfide compound is decomposed by hydrochloric acid and the product is further purified by dissolving it with the addition of animal charcoal and sodium hydrosulfite. The sodium salt of 6-chloro-5-methoxy-2- (stübyl-4 ') -1,2,3-benzotriazole-2'-sulfonic acid is obtained as a pale yellow substance.
This compound is a valuable lightening agent for cellulose fibers, for soap powder and synthetic detergents. In the case of good fastness properties, the white tinting obtainable with it shows a blue-white shade and has excellent chlorine fastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH310423T | 1952-04-30 | ||
| CH304391T | 1952-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310423A true CH310423A (en) | 1955-10-15 |
Family
ID=25734838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310423D CH310423A (en) | 1952-04-30 | 1952-04-30 | Process for producing a fluorescent benzotriazole compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310423A (en) |
-
1952
- 1952-04-30 CH CH310423D patent/CH310423A/en unknown
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