CH259718A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH259718A CH259718A CH259718DA CH259718A CH 259718 A CH259718 A CH 259718A CH 259718D A CH259718D A CH 259718DA CH 259718 A CH259718 A CH 259718A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- monoazo dye
- red
- dye
- preparation
- Prior art date
Links
- 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 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000000975 dye Substances 0.000 claims description 8
- LXCVLSLSFYLNIB-UHFFFAOYSA-N 2-[2-[[2-(2-aminophenyl)-4-chlorophenyl]methoxymethyl]-5-chlorophenyl]aniline Chemical compound ClC1=CC(=C(COCC2=C(C=C(C=C2)Cl)C2=C(C=CC=C2)N)C=C1)C1=C(C=CC=C1)N LXCVLSLSFYLNIB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- UJZOHHSRILPGAX-UHFFFAOYSA-N 5-chloro-2-phenylmethoxyaniline Chemical compound NC1=CC(Cl)=CC=C1OCC1=CC=CC=C1 UJZOHHSRILPGAX-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Verfahren zur Herstellung eines</B> Monoazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Monoazofarbstoff gelangt, wenn man diazotierten 4-Chlor-2-aminophenyl-ben- zyläther in saurem Medium mit 2-Amino-8-oxy- naphthalin-6-sulfonsäure vereinigt.
Der neue Farbstoff stellt in trockenem Zu- stand ein rotbraunes Pulver dar, das sich in Wasser mit roter Farbe löst und Wolle aus essigsaurem Bade in etwas blaustichig roten Tönen von guten Echtheitseigenschaften färbt.
Der als Ausgangsstoff verwendete 4-Chlor- 2-aminophenyl-benzyläther kann z. B. nach an sich bekannter Methode durch Umsetzen von Benzylchlorid mit einem Alkalisalz des 4-Chlor- 2-nitro-l-oxybenzols und anschliessende Re duktion der Nitrogruppe zur Aminogruppe hergestellt werden. Die Diazotierung des 4-Chlor-2-aminophenyl-benzyläthers geschieht in üblicher, an sich bekannter Weise.
Die Kupplung des diazotierten 4-Chlor- 2-aminophenyl-benzyläthers erfolgt in saurem, beispielsweise mineralsaurem, Medium. Ge- wünschtenfalls kann die überschüssige Mi neralsäure in an sich bekannter Weise, z. B. durch Zusatz von Natriumacetat, abgestumpft werden.
Beispiel: 23,4 Teile 4-Chlor-2-aminophenyl-beiizyl- äther werden mit 30 Teilen 30%iger Salz- säure in das Chlorhydrat übergeführt. Nach Verdünnen mit 60 Teilen Eiswasser wird bei 0 bis 5 mit einer Lösung von 7 Teilen Natrium nitrit in 50 Teilen Wasser diazotiert und nach beendigter Reaktion von allfälligen Verunreini gungen abfiltriert. Die Diazolösung wird bei 0 bis 5 in eine Suspension eingetropft, die man durch Zugabe von 20 Teilen Essigsäure zu einer neutralen Lösung von 26,
1 Teilen des Natriumsalzes der 2-Amino-8-oxynaphtha- lin-6-sulfonsäure in 200 Teilen Wasser erhal ten hat. Man stumpft die frei werdende Mi neralsäure mit einer Natriumacetatlösung ab, erwärmt zum Schluss einige Zeit auf 40 bis <B>501,</B> neutralisiert nach beendeter Kupplung mit Natriumcarbonat und filtriert den Farb stoff ab.
<B> Process for the production of </B> a monoazo dye. It has been found that a valuable monoazo dye is obtained if diazotized 4-chloro-2-aminophenylbenzyl ether is combined with 2-amino-8-oxynaphthalene-6-sulfonic acid in an acidic medium.
When dry, the new dye is a red-brown powder which dissolves in water with a red color and dyes wool from an acetic acid bath in somewhat bluish red shades with good fastness properties.
The 4-chloro-2-aminophenyl benzyl ether used as starting material can, for. B. by a known method by reacting benzyl chloride with an alkali salt of 4-chloro-2-nitro-1-oxybenzene and subsequent reduction of the nitro group to the amino group. The 4-chloro-2-aminophenyl-benzyl ether is diazotized in a customary, known manner.
The coupling of the diazotized 4-chloro-2-aminophenyl-benzyl ether takes place in an acidic medium, for example a mineral acid medium. If desired, the excess mineral acid can be used in a manner known per se, for. B. by adding sodium acetate to be blunted.
Example: 23.4 parts of 4-chloro-2-aminophenyl-beiicyl-ether are converted into the hydrochloride with 30 parts of 30% strength hydrochloric acid. After dilution with 60 parts of ice water, diazotization is carried out at 0 to 5 with a solution of 7 parts of sodium nitrite in 50 parts of water and, after the reaction has ended, any impurities are filtered off. The diazo solution is dripped into a suspension at 0 to 5, which is made by adding 20 parts of acetic acid to a neutral solution of 26,
1 part of the sodium salt of 2-amino-8-oxynaphthalin-6-sulfonic acid in 200 parts of water has received. The mineral acid released is blunted with a sodium acetate solution, finally heated to 40 to 501 for some time, neutralized with sodium carbonate after coupling is complete and the dye is filtered off.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH254805T | 1945-10-04 | ||
| CH259718T | 1945-10-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH259718A true CH259718A (en) | 1949-01-31 |
Family
ID=25729854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259718D CH259718A (en) | 1945-10-04 | 1945-10-04 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH259718A (en) |
-
1945
- 1945-10-04 CH CH259718D patent/CH259718A/en unknown
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