CH294945A - Process for the preparation of a trisazo dye. - Google Patents
Process for the preparation of a trisazo dye.Info
- Publication number
- CH294945A CH294945A CH294945DA CH294945A CH 294945 A CH294945 A CH 294945A CH 294945D A CH294945D A CH 294945DA CH 294945 A CH294945 A CH 294945A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- blue
- coupling
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 235000005811 Viola adunca Nutrition 0.000 claims description 2
- 240000009038 Viola odorata Species 0.000 claims description 2
- 235000013487 Viola odorata Nutrition 0.000 claims description 2
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 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 4
- 238000009958 sewing Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- XSFHICWNEBCMNN-UHFFFAOYSA-N 2h-benzotriazol-5-amine Chemical compound NC1=CC=C2NN=NC2=C1 XSFHICWNEBCMNN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- -1 aminomonoazo Chemical group 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 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
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/16—Trisazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>I</B> eitsatzpatexit zum Ilauptpatent Nr. <B>291197.</B> Verfahren zur Herstellung eines Trisazofarbstoffes. Es wurde gefunden, dass man zu eineinwert- vollen Trisazofarbstoff gelangt, wenn man eine Diazoverbindung des Aminodisazofarb- stoffes der Formel
EMI0001.0012
mit 8-Oxyehinolin kuppelt.
Der neue Farbstoff bildet ein dunkles Pul ver, das sieh in konzentrierter Schwefelsäure mit grünblauer, in verdünnter Natriumear- bonatlösung mit blauvioletter Farbe löst und Baumwolle naeli dein ein- oder zweibadigen Nachkupferungsverfahren in wasch- und<B>1</B> eht- echten, rotstiellig marineblauen Tönen färbt.
Der Aminodisazofarbstoff der obenstehen- den Formel kann. hergestellt werden, indem man diazotiertes 6-Aminobenztriazol mit 1- Amino-2-methoxybenzol kuppelt, den erh - tenen Aminomonoazofarbstoff weiterdiazotiert und in alkalischem Medium mit 2-(4'-Amino- phenyl) <B>-</B> amino <B>-</B> 5-oxynaphthalin-7,
3"-disulion- säure vereinigt.<B>-</B> Bei der Herstelluno- des Aminodisazofarl)- stoffes nach der oben beschriebenen Methode erfolgt die Kupplung des diazotierten 6- Aminobenztriazols zweckmässig in schwach saurem, z. B. essigsaurem Medium. Die Diazo- tierung des so erhältlichen Aminomonoazofarb- stoffes kann nach üblichen Methoden vorge nommen werden, z.
B. mit Hilfe von Salz säure und Natriumnitrit. Diese Diazomono- azoverbindung wird dann in alkalischem, bei spielsweise alkaliearbona-talkalisehem Medium mit der 2-(4'-Aminophenyl)-amino-5-oxynaph- thalin-7,3'-di,s-LilfonsäLire gekuppelt.
Der Aminodisazofarbstoff wird vorteilhaft nach der sogenannten indirekten Methode di- azotiert, indem man z. B. eine Lösung oder Suspension, welche den Aminodisazofarbstoff in Form eines. Alkalisalzes und zweekmässi±,# noch einen geringen Überschuss an freiem Alkali sowie die erforderliche Menge Nitrit enthält, mit einem Überschuss an verdünnter Salzsäure vereinigt.
Die Kupplung der Aminodisazoverbind-Luip,' mit dem 8-Oxychinolin erfolgt vorzugsweise in alkalischem, z. B. alkaliearbonat- oder erd- alkalihydroxydalkalischem Medium, gegebe nenfalls unter Zusatz von kupplungsfördern den Stoffen wie Pyridin.
<I>Beispiel:</I> <B>26,8</B> Teile des Monoazofarbstoffes, der er halten wurde durch Kuppeln von diazotier- tem 6-Aminobenztriazol auf die co-31ethansul- fonsäure von 1-Aiiiilio-'-)-iiietlio-,:
vbeilzol und Abspalten der (o--,#,lethansulionsäure mit ver dünnter NatriumhydroxydlÖsung werden iri <B>500</B> Teilen Wasser unter Zusatz von<B>26</B> Tei- len a'0%i- ,e r -Natriumhy #d roxydlösung gelöst, mit<B>35</B> Teilen 201/oiger Natriumnitritlösung versetzt und durch Einstürzen von<B>60</B> Teilen )01/oiger Salzsäure,
verdünnt mit etwa<B>60</B> Teilen Wasser, diazotiert. Nach beendeter Di- azotierun- vereinigt man unter Kühlung in nat.riumearbonatalkalischer Lösung mit 41 Tei len 2-(4-Aminophenyl)-amino-5-oxyiiaphtll < i- lin-7,3 -disulfonsäure, lässt über Nacht rühren und filtriert den ausgefallenen Farbstoff ab.
Er wird auf dein Filter mit 101/oiger Na- triumehloridlösung gewaschen, bis keine Kupp - lungskomponente mehr nachweisbar ist.
Man löst ihn hierauf in 2000 Teilen Wasser und 14 Teilen<B>30</B> 1/o iger Natriumhydroxydlösung, gibt bei etwa 1011 <B>35</B> Teile 201/oige Natriunmitrit- lösung hinzu und diazotiert durch Einstürzeii von 50 Teilen 30%iger Salzsäure, verdünnt mit etwa<B>50</B> Teilen Wasser.
Nach beendeter Diazotierung gibt man vorerst eine salzsaure Lösung von 14,5 Teilen 8-Ox#-ehinolin und alsdann<B>75</B> Teile Natriuniearbonat, gelöst in 240 Teilen Wasser, hinzu. W enn die Farbstoff- bildung beendet ist, stellt man mit verdünn ter Salzsäure schwach kongosaLier und fil triert den ausgefallenen Farbstoff ab.
<B> I </B> Initial latexite for main patent no. <B> 291197. </B> Process for the production of a trisazo dye. It has been found that an invalid trisazo dye is obtained if a diazo compound of the amino disazo dye of the formula
EMI0001.0012
couples with 8-oxyehinoline.
The new dye forms a dark powder that dissolves in concentrated sulfuric acid with green-blue, in dilute sodium carbonate solution with a blue-violet color, and cotton after the one- or two-bath re-coppering process in washing and <B> 1 </B> genuine , red-streaked navy blue tones.
The amino disazo dye of the above formula can. be prepared by coupling diazotized 6-aminobenzotriazole with 1-amino-2-methoxybenzene, further diazotizing the obtained aminomonoazo dye and in an alkaline medium with 2- (4'-aminophenyl) - </B> amino < B> - </B> 5-oxynaphthalene-7,
3 "-disulionic acid combined. In the production of the aminodisazofar) - substance by the method described above, the coupling of the diazotized 6-aminobenzotriazole is expediently carried out in a weakly acidic medium, for example acetic acid. The diazotization of the aminomonoazo dye obtainable in this way can be carried out by customary methods, eg.
B. with the help of hydrochloric acid and sodium nitrite. This diazomono-azo compound is then coupled in an alkaline medium, for example alkali carbonate-talcous medium, with 2- (4'-aminophenyl) -amino-5-oxynaphthalene-7,3'-di, s-LilfonsäLire.
The amino disazo dye is advantageously diazotized by the so-called indirect method by z. B. a solution or suspension, which the amino disazo in the form of a. Alkali salt and two more, # still contains a small excess of free alkali and the required amount of nitrite, combined with an excess of dilute hydrochloric acid.
The coupling of the Aminodisazoverbind-Luip, 'with the 8-oxyquinoline is preferably carried out in alkaline, z. B. alkali carbonate or alkaline earth alkali hydroxide medium, if necessary with the addition of coupling promoting substances such as pyridine.
<I> Example: </I> <B> 26.8 </B> parts of the monoazo dye that was obtained by coupling diazotized 6-aminobenzotriazole to the co-31ethanesulfonic acid of 1-aliliio -'- ) -iiietlio- ,:
Vbeilzol and elimination of the (o -, #, lethanesulionic acid with dilute sodium hydroxide solution are carried out in 500 parts of water with the addition of 26 parts of 0% i-, er -Sodium hydroxide solution dissolved, mixed with <B> 35 </B> parts of 201 /% sodium nitrite solution and by collapsing <B> 60 </B> parts) of 01 /% hydrochloric acid,
diluted with about <B> 60 </B> parts of water, diazotized. After the end of the diazotization, the mixture is combined with 41 parts of 2- (4-aminophenyl) -amino-5-oxyiiaphthyl-i-lin-7,3-disulfonic acid with cooling in a sodium carbonate-alkaline solution, left to stir overnight and the filter is filtered precipitated dye.
It is washed on the filter with 101% sodium chloride solution until no more coupling components can be detected.
It is then dissolved in 2000 parts of water and 14 parts of 30% sodium hydroxide solution, about 1011 parts 35 parts of 201% sodium mitrite solution are added and diazotized by collapsing 50 parts of 30% hydrochloric acid, diluted with about <B> 50 </B> parts of water.
When the diazotization is complete, a hydrochloric acid solution of 14.5 parts of 8-oxy-quinoline and then 75 parts of sodium carbonate, dissolved in 240 parts of water, are added. When the formation of the dye is complete, weakly congosaLe is made with dilute hydrochloric acid and the precipitated dye is filtered off.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294945T | 1950-06-22 | ||
| CH291197T | 1950-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH294945A true CH294945A (en) | 1953-11-30 |
Family
ID=25733084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH294945D CH294945A (en) | 1950-06-22 | 1950-06-22 | Process for the preparation of a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH294945A (en) |
-
1950
- 1950-06-22 CH CH294945D patent/CH294945A/en unknown
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