CH264493A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH264493A CH264493A CH264493DA CH264493A CH 264493 A CH264493 A CH 264493A CH 264493D A CH264493D A CH 264493DA CH 264493 A CH264493 A CH 264493A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- dye
- parts
- methyl
- acid
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 5
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- ZDTXQHVBLWYPHS-UHFFFAOYSA-N 4-nitrotoluene-2-sulfonic acid Chemical compound CC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O ZDTXQHVBLWYPHS-UHFFFAOYSA-N 0.000 claims description 3
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 claims 2
- 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 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- BRKFTWHPLMMNHF-UHFFFAOYSA-N 5-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C=C1S(O)(=O)=O BRKFTWHPLMMNHF-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- WPGVQDHXOUAJBW-UHFFFAOYSA-N 2-methyl-5-nitrobenzenesulfonyl chloride Chemical compound CC1=CC=C([N+]([O-])=O)C=C1S(Cl)(=O)=O WPGVQDHXOUAJBW-UHFFFAOYSA-N 0.000 description 1
- CILBUASZXQAPBO-UHFFFAOYSA-N 7-amino-8-phenylnaphthalene-1-sulfonic acid Chemical compound NC1=CC=C2C=CC=C(S(O)(=O)=O)C2=C1C1=CC=CC=C1 CILBUASZXQAPBO-UHFFFAOYSA-N 0.000 description 1
- XSSOPENHXIOIEM-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid;sodium Chemical compound [Na].C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 XSSOPENHXIOIEM-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 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
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000000725 suspension 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/053—Amino naphthalenes
- C09B31/057—Amino naphthalenes containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 259444. <B>Verfahren zur Herstellung eines</B> Disazofarbstoffes. - Es wurde gefunden, dass man zu einem wertvollen Disazofarbstoff gelangt, wenn man die Diazoverbindung des Monoazofarbstoffes der Formel
EMI0001.0005
worin die Sulfonsäuregruppe dieselbe Stel lung einnimmt wie die Sulfonsäuregruppe in der durch Sulfonierung von 6-Methyl-3-nitro- benzol-sulfonsäure-(1)-N-methylanilid erhält lichen 6-Methyl-3-nitrobenzol-sulfonsäure-(1)
- [N-methylanilid-sulfonsäure], mit 1-Phenvl.- aminonaphthalin-8-sulfonsäure vereinigt.
Der neue Farbstoff stellt in trockenem Zustand ein blaues Pulver dar, das sich in Wasser mit blauer Farbe löst und Wolle aus essigsaurem Bade in marineblauen Tönen färbt.
Der als Ausgangsstoff dienende Monoazo- farbstoff der obenstehenden Formel kann in an sich bekannter Weise hergestellt werden, indem man zum Beispiel diazotierte 6-Methyl- 3 - aminobenzol-sulfonsäure-(1) - [N-methylani- lid-sulfonsäure] mit 1-Aminonaphthalin ver einigt.
6 -Methyl-3 -aminobenzol-sulfonsäure-(1)- [N-methylanilid-sulfonsäure] kann ebenfalls nach an sich bekannten Methoden hergestellt werden, indem man zum Beispiel 6-Methyl-3- nitrobenzol-l-sulfonsäurechlorid mit N-Me- thylanilin umsetzt, das entstandene 6-Methyl- 3 -nitrobenzol-sulfonsäure- (1) -N-methylanilid sulfoniert und hierauf die Nitrogruppe zur Aminogruppe reduziert.
Die Diazotierung des als Ausgangsstoff dienenden Monoazofarbstoffes der obenstehen- den Formel kann zum Beispiel so erfolgen, dass man eine schwach alkalisch reagierende Lösung des Monoazofarbstoffes zuerst mit einem überschuss an Natriumnitritlösung, hierauf mit einem Überschuss an Mineralsäure, z. B. Salzsäure, versetzt. und die entstandene, schwer lösliche Diazoazoverbindung durch Fil tration isoliert.
Die Kupplung der Diazoazoverbindung mit der 1-Phenylaminonaphthalin-8-sulfon- säure geschieht vorzugsweise in saurem, z. B. essigsaurem, Medium. Beispiel: 35,6 Teile 6-Methyl-3-aminobenzol-sulfon- säure-(1)-[N-methylanilid-sulfonsäure] wer den in 200 Teilen Wasser durch Zusatz von 4 Teilen Natriumhydroxyd gelöst und mit 7 Teilen Natriumnitrit versetzt. Nach Zugabe von 30 Teilen Eis werden 30 Teile konz. Salz säure eingestürzt.
Die entstehende weisse Sus pension der Diazoverbindung wird wie üblich mit 14,3 Teilen 1-Aminonaphthalin gekuppelt, worauf der rotviolette Farbstoff_ abgesaugt und mit verdünnter Salzsäure gewaschen wird. Hierauf wird er in 900 Teilen Wasser suspendiert und durch Zusatz von Natrium hydroxyd gelöst.
Die sehwach alkalische Lö sung wird mit 8 Teilen Natriiunnitrit versetzt und durch Einstürzen von 60 Teilen konz. Salzsäure diazotiert. Die braune Diazoverbin- dung wird nach einigen Stunden isoliert,
mit verdünnter Salzsäure gewaschen und mit 200 Teilen Wasser angeschlämmt. Dieser Brei wird mit einer Lösung von 32 Teilen 1-phe- nylaminonaphthalin-8-sulfonsaurem Natrium, 20 Teilen krist. Natriumacetat und 4 Teilen Essigsäure in 400 Teilen Wasser vermischt. Nach einigen Stunden ist die Kupplung voll ständig.
Aus der nach Neutralisieren mit Na- triumcarbonat entstehenden tiefblauen Lösung wird der Farbstoff bei<B>700</B> durch Zugabe von Natriumchlorid ausgefällt. Er wird abgesaugt, mit verdünnter Natriumchloridlösung gewa schen und getrocknet.
<B> Additional patent </B> to main patent No. 259444. <B> Process for the production of </B> a disazo dye. - It has been found that a valuable disazo dye is obtained by using the diazo compound of the monoazo dye of the formula
EMI0001.0005
in which the sulfonic acid group has the same position as the sulfonic acid group in 6-methyl-3-nitrobenzenesulfonic acid (1) obtained by sulfonation of 6-methyl-3-nitrobenzenesulfonic acid (1) -N-methylanilide
- [N-methylanilide-sulfonic acid], combined with 1-phenyl-aminonaphthalene-8-sulfonic acid.
When dry, the new dye is a blue powder that dissolves in water with a blue color and dyes wool from an acetic acid bath in navy blue tones.
The starting material used as the monoazo dye of the above formula can be prepared in a manner known per se by, for example, diazotized 6-methyl- 3 - aminobenzenesulfonic acid- (1) - [N-methylanilide-sulfonic acid] with 1- Aminonaphthalene united.
6 -Methyl-3-aminobenzene-sulfonic acid- (1) - [N-methylanilide-sulfonic acid] can also be prepared by methods known per se by, for example, 6-methyl-3-nitrobenzene-1-sulfonic acid chloride with N-Me - Thylaniline converts, the resulting 6-methyl-3-nitrobenzene-sulfonic acid- (1) -N-methylanilide sulfonated and then reduced the nitro group to the amino group.
The diazotization of the starting monoazo dye of the formula above can be carried out, for example, by first treating a weakly alkaline solution of the monoazo dye with an excess of sodium nitrite solution, then with an excess of mineral acid, e.g. B. hydrochloric acid added. and the resulting, sparingly soluble diazoazo compound isolated by Fil tration.
The coupling of the diazoazo compound with the 1-phenylaminonaphthalene-8-sulfonic acid is preferably done in acidic, e.g. B. acetic acid medium. Example: 35.6 parts of 6-methyl-3-aminobenzene-sulfonic acid (1) - [N-methylanilide-sulfonic acid] are dissolved in 200 parts of water by adding 4 parts of sodium hydroxide and 7 parts of sodium nitrite are added. After adding 30 parts of ice, 30 parts of conc. Hydrochloric acid collapsed.
The resulting white suspension of the diazo compound is coupled as usual with 14.3 parts of 1-aminonaphthalene, whereupon the red-violet dye is suctioned off and washed with dilute hydrochloric acid. It is then suspended in 900 parts of water and dissolved by adding sodium hydroxide.
The weakly alkaline solution is mixed with 8 parts of sodium nitrite and concentrated by collapsing 60 parts. Hydrochloric acid diazotized. The brown diazo compound is isolated after a few hours,
Washed with dilute hydrochloric acid and suspended with 200 parts of water. This slurry is with a solution of 32 parts of 1-phenylaminonaphthalene-8-sulfonic acid sodium, 20 parts of crystalline. Sodium acetate and 4 parts of acetic acid mixed in 400 parts of water. The clutch is complete after a few hours.
From the deep blue solution formed after neutralization with sodium carbonate, the dye is precipitated at <B> 700 </B> by adding sodium chloride. It is filtered off with suction, washed with dilute sodium chloride solution and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH259444T | 1946-12-20 | ||
| CH264493T | 1946-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH264493A true CH264493A (en) | 1949-10-15 |
Family
ID=25730260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH264493D CH264493A (en) | 1946-12-20 | 1946-12-20 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH264493A (en) |
-
1946
- 1946-12-20 CH CH264493D patent/CH264493A/en unknown
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