CH211013A - Process for the preparation of a trisazo dye. - Google Patents
Process for the preparation of a trisazo dye.Info
- Publication number
- CH211013A CH211013A CH211013DA CH211013A CH 211013 A CH211013 A CH 211013A CH 211013D A CH211013D A CH 211013DA CH 211013 A CH211013 A CH 211013A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- acid
- coupled
- trisazo
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 235000005811 Viola adunca Nutrition 0.000 claims 1
- 240000009038 Viola odorata Species 0.000 claims 1
- 235000013487 Viola odorata Nutrition 0.000 claims 1
- 235000002254 Viola papilionacea Nutrition 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
- 239000000243 solution Substances 0.000 description 3
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/36—Trisazo dyes of the type
- C09B35/366—D is diphenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 208540 Verfahren zur Herstellung eines Tr isazofarbstoffes. Es wurde gefunden, dass ein wertvoller Trisazofarbstoff hergestellt werden kann, wenn man tetrazotiertes 4,4'-Diaminodiphenyl einerseits mit 1-Oxybenzol-2-karbonsäure und anderseits mit 1-Aminonaphthalin-6-sulfon- säure kuppelt,
den so erhaltenen Disazo- aminofarbstoff diazotiert und mit 8-Oxy- chinolin-7-sulfonsäure kuppelt.
Der neue Trisazofarbstoff stellt ein grau schwarzes Pulver dar, das sich in Wasser, in 10%iger Sodalösung und in 100%iger Na- tronlauge mit braunoranger und in konzen trierter Schwefelsäure mit schwärzlichblauvio- letterFarbe löst. ErfärbtBaumwolleinrotbrau. nen Tönen an, die beim Nachkupfern gut wasch- und lichtecht werden.
Bei der Durchführung des vorliegenden Ver fahrens kann beispielsweise das in üblicher Weise tetrazotierte 4,4'-Diaminodipheciyl zu erst in alkalischem Medium einerseits mit 1-Oxybenzol-2-karbonsäure und hierauf in schwach saurem Medium mit 1-Aminonaphtha- lin-6-sulfonsäure gekuppelt werden.
Die Diazo- tierung des erhaltenen Disazoaminofarbstoffes wird vorzugsweise indirekt, d. h. beispielsweise durch Ansäuern einer mit Nitrit versetzten schwach alkalischen Lösung des Farbstoffes, vorgenommen und die Kupplung der so er haltenen Diazoverbindung mit 8-Oxychinolin- 7-sulfonsätire erfolgt in bekannter Weise in schwach alkalischem, beispielsweise natrium- karbonatalkalischem Medium.
Beispiel: Man tetrazotiert 18,2 Teile 4,4'-Diainino- diphenyl auf übliche Weise und kuppelt die Tetrazoverbindung bei 6-1011 in natrium- karbonatalkalischer Lösung mit 13,8 Teilen 1-Oxybenzol-2-karbonsäure. Nachdem die Tetrazoverbindung verschwunden ist, gibt man eine mit Natriumkarbonat neutralisierte Lösung von 22,
3 Teilen l.-Amiiionaphthalin- 6-sulfonsäure hinzu und säuert die Reaktions- masse mit 50%iger Essigsäure an. Man kuppelt vorerst 6 Stunden unterhalb 20 0 und beendet die Reaktion durch 12 stündiges Rühren bei 25-30 0. Der Disazofarbstoff wird ohne Beigabe vori'@Salz abfiltriert und mit Wasser gewaschen.
Man löst hierauf den Disazofarbstoff in 800 Teilen Wasser und 10,6 Teilen wasser freiem Natriumkarbonat bei 70-80', setzt 6,9 Teile Natriumnitrit, in 25 Teilen Wasser gelöst, hinzu und säuert bei 50 mittels einer Mischung von 50 Raumteilen konzentrierter Salzsäure und 30 Teilen Wasser an. Die Diazotierung dauert etwa 16 Stunden. Hier auf kuppelt man bei 10-1511 mit 23,6 Tei len 8-Oxychinolin-7-srilfonsäure in natrium- karbonatalkalischer Lösung. Nach Beendi gung der Kupplung scheidet man den Farb stoff durch Beigabe von Kochsalz ab.
Additional patent to main patent no. 208540 Process for the production of a trisazo dye. It has been found that a valuable trisazo dye can be produced if tetrazotized 4,4'-diaminodiphenyl is coupled with 1-oxybenzene-2-carboxylic acid on the one hand and with 1-aminonaphthalene-6-sulfonic acid on the other,
the disazo-amino dye thus obtained is diazotized and coupled with 8-oxyquinoline-7-sulfonic acid.
The new trisazo dye is a gray-black powder that dissolves in water, in 10% soda solution and in 100% sodium hydroxide with brown-orange and in concentrated sulfuric acid with a blackish-blue-violet color. Discolored cotton red-brown. in shades that are washable and lightfast when re-coppering.
When carrying out the present process, for example, the 4,4'-diaminodipheciyl tetrazotized in the usual way can first be added in an alkaline medium with 1-oxybenzene-2-carboxylic acid and then in a weakly acidic medium with 1-aminonaphthalin-6-sulfonic acid be coupled.
The diazo- tation of the disazoamino dye obtained is preferably indirect, d. H. for example, by acidifying a slightly alkaline solution of the dye mixed with nitrite, and the coupling of the diazo compound thus obtained with 8-oxyquinoline-7-sulfonsätire is carried out in a known manner in a weakly alkaline, for example sodium carbonate-alkaline medium.
Example: 18.2 parts of 4,4'-diainino-diphenyl are tetrazotized in the usual way and the tetrazo compound is coupled to 13.8 parts of 1-oxybenzene-2-carboxylic acid at 6-1011 in an alkaline sodium carbonate solution. After the tetrazo compound has disappeared, a solution of 22 neutralized with sodium carbonate is added,
3 parts of l-amionaphthalene-6-sulfonic acid are added and the reaction mass is acidified with 50% acetic acid. The coupling is initially carried out for 6 hours below 20 ° and the reaction is ended by stirring for 12 hours at 25-30 °. The disazo dye is filtered off without the addition of salt and washed with water.
The disazo dye is then dissolved in 800 parts of water and 10.6 parts of anhydrous sodium carbonate at 70-80 ', 6.9 parts of sodium nitrite, dissolved in 25 parts of water, are added and acidified at 50 using a mixture of 50 parts by volume of concentrated hydrochloric acid and 30 parts of water. The diazotization takes about 16 hours. Here, at 10-1511, 23.6 parts of 8-oxyquinoline-7-sulfonic acid in sodium carbonate-alkaline solution are coupled. After the coupling has ended, the dye is separated off by adding sodium chloride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211013T | 1938-08-16 | ||
| CH208540T | 1938-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211013A true CH211013A (en) | 1940-08-15 |
Family
ID=25724542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211013D CH211013A (en) | 1938-08-16 | 1938-08-16 | Process for the preparation of a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211013A (en) |
-
1938
- 1938-08-16 CH CH211013D patent/CH211013A/en unknown
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