CH211014A - Process for the preparation of a trisazo dye. - Google Patents
Process for the preparation of a trisazo dye.Info
- Publication number
- CH211014A CH211014A CH211014DA CH211014A CH 211014 A CH211014 A CH 211014A CH 211014D A CH211014D A CH 211014DA CH 211014 A CH211014 A CH 211014A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- brown
- coupled
- trisazo dye
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- 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 4
- 229920000742 Cotton Polymers 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 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
- 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
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- LGDFHDKSYGVKDC-UHFFFAOYSA-N 8-hydroxyquinoline-5-sulfonic acid Chemical compound C1=CN=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 LGDFHDKSYGVKDC-UHFFFAOYSA-N 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
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 239000000126 substance 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
- 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)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
Zusatzpatent zum, Hauptpatent Nr. 208540. Verfahren zur Herstellung eines Trisazofarbstoffes. Es wurde gefunden, dass ein wertvoller Trisazofarbstoff hergestellt werden kann, wenn man tetrazotiertes 4,4'-Diaminodiphenyl einer seits mit 1-Oxybenzol-2-karbonsäure und an derseits mit 1-Aminonaphthalin-6-sulfonsäure kuppelt,
den so erhaltenen Disazoaminofarb- stoff diazotiert und mit 8-Oxychinolin-5-sul- fonsäure kuppelt.
Der neue TrisazofarbstofE stellt ein grau schwarzes Pulver dar, das sich in Wasser und ein 10 o/oiger Sodalösung mit brauner, in 10 o/oiger Natronlauge mit rötlichbrauner und in konzentrierter Schwefelsäure mit schwarz blauer Farbe löst. Er färbt Baumwolle in rotbraunen Tönen an, die beim Nachkupfern gut wasch- und lichtecht werden.
Bei der Durchführung des vorliegenden Verfahrens kann beispielsweise das in übli- licher Weise tetrazotierte 4,4'-Diaminodiphe- nyl zuerst in alkalischem Medium einerseits mit 1-Oxybenzol-2-karbonsäure und hierauf in schwach saurem Medium mit 1-Aminonaph- thalin-6-sulfonsäure gekuppelt werden.
Die Diazotierung des erhaltenen Disazoaminofarb- stoffes wird vorzugsweise indirekt, d. h. bei spielsweise durch Ansäuern einer mit Nitrit versetzten schwach alkalischen Lösung des Farbstoffes, vorgenommen und die Kupplung der so erhaltenen Diazoverbindung mit 8-Oxy- chinolin-5-sulfonsäure erfolgt in bekannter Weise in schwach alkalischem, beispielsweise - natriumkarbonatalkalischem Medium.
Beispiel: Man tetrazotiert 18,2 Teile 4,4'-Diamino- diphenyl auf übliche Weise und kuppelt die Tetrazoverbindung bei 6-10 o in natriumkar- bonatalkalischerLösungmit13,8Teilen 1-Oxy- benzol-2-karbonsäure. Nachdem die Tetrazo- verbindung verschwunden ist, gibt man eine mit Natriumkarbonat neutralisierte Lösung von 22,
3 Teilen 1-Aminonaphthalin-G-sulfon- säure hinzu und säuert die Reaktionsmasse mit 50 o/oiger Essigsäure an. Man kuppelt vorerst 6 Stunden unterhalb 200 und beendet die Reaktion durch 12stündiges Rühren bei 25-301. Der Disazofai#bstoff wird ohne Bei gabe von Salz abfiltriert und mit Wasser ge waschen.
Man löst hierauf den Disazofarbstoff in 800 Teilen Wasser und 10,6 Teilen wasser freiem Natriumkarbonat bei 70-80 0, setzt 6,9 Teile Natriumnitrit, in 25 Teilen Was ser gelöst, hinzu und säuert bei 5 0 mittels einer Mischung von 50 Raumteilen konzen trierter Salzsäure und 30 Teilen Wasser an. Die Diazotierüng dauert etwa 16 Stunden. Hierauf kuppelt man bei<B>10-150</B> mit 23,6 Teilen 8-Oxychinolirr-5-sulforrsäure in natrium- karbonatalkalisr,4er Lösung. Nach Beendigung der Kupplung scheidet man den Farbstoff 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 on the one hand with 1-oxybenzene-2-carboxylic acid and on the other hand with 1-aminonaphthalene-6-sulfonic acid,
the disazoamino dye thus obtained is diazotized and coupled with 8-oxyquinoline-5-sulphonic acid.
The new trisazo dye is a gray-black powder that dissolves in water and a 10% soda solution with brown, in 10% sodium hydroxide solution with reddish-brown and in concentrated sulfuric acid with a black-blue color. It dyes cotton in reddish-brown tones, which become washable and lightfast when re-coppering.
When carrying out the present process, for example, 4,4'-diaminodiphenyl, which is usually tetrazotized, can first be mixed in an alkaline medium with 1-oxybenzene-2-carboxylic acid and then in a weakly acidic medium with 1-aminonaphthalene-6 sulfonic acid are coupled.
The diazotization of the disazoamino dye obtained is preferably indirect, d. H. for example by acidifying a slightly alkaline solution of the dye to which nitrite has been added, and the coupling of the diazo compound thus obtained with 8-oxyquinoline-5-sulfonic acid is carried out in a known manner in a weakly alkaline, for example, sodium carbonate-alkaline medium.
Example: 18.2 parts of 4,4'-diaminodiphenyl are tetrazotized in the usual way and the tetrazo compound is coupled at 6-10 ° in an alkaline sodium carbonate solution with 13.8 parts of 1-oxybenzen-2-carboxylic acid. After the tetrazo compound has disappeared, a solution of 22 neutralized with sodium carbonate is added,
3 parts of 1-aminonaphthalene-G-sulfonic acid are added and the reaction mass is acidified with 50% acetic acid. The coupling is initially carried out for 6 hours below 200 and the reaction is ended by stirring at 25-301 for 12 hours. The disazo substance 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 the mixture is acidified at 50 using a mixture of 50 parts by volume trated hydrochloric acid and 30 parts of water. The diazotization takes about 16 hours. This is followed by coupling at <B> 10-150 </B> with 23.6 parts of 8-oxyquinoline-5-sulforric acid in sodium carbonate alkaline solution of 4. 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 |
|---|---|---|---|
| CH211014T | 1938-08-16 | ||
| CH208540T | 1938-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211014A true CH211014A (en) | 1940-08-15 |
Family
ID=25724543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211014D CH211014A (en) | 1938-08-16 | 1938-08-16 | Process for the preparation of a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211014A (en) |
-
1938
- 1938-08-16 CH CH211014D patent/CH211014A/en unknown
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