CH211925A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211925A CH211925A CH211925DA CH211925A CH 211925 A CH211925 A CH 211925A CH 211925D A CH211925D A CH 211925DA CH 211925 A CH211925 A CH 211925A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- azo dye
- amino
- nitrobenzene
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 8
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- -1 maleic acid ester Chemical class 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 241000872198 Serjania polyphylla Species 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002955 Art silk Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 239000000203 mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/08—Preparation of azo dyes from other azo compounds by reduction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man einen wert vollen Azofarbstoff erhält, wenn man die Diazoverbindung des 1-Amino-4-nitrobenzols mit dem sauren Maleinsäureester des N-Äthyl- oxäthylaminobenzols vereinigt und die Nitro- gruppe dieses Farbstoffes mit reduzierenden Mitteln in die Aminogruppe überführt.
Der so erhältliche Farbstoffe bildet ein dunkel rotes Pulver, das sich als Alkalisalz in Wasser löst und das Acetatkunstseide in orange Tönen färbt, die sich auf der Faser durch Diazotieren und Entwickeln mit 2- Oxynaphthalin-3-carbonsäure zu einem ech ten Schwarz entwickeln lassen.
Beispiel: 43,4 Teile des durch Kuppeln von diazo- tiertem 1-Amino-4-nitrobenzol und dem sau ren Maleinsäureester des N-Äthyl-oxäthyl- aminobenzols erhältlichen Farbstoffes werden in 1150 Teilen Wasser gelöst. Man gibt bei 60 bis 70 eine wässrige Lösung von 8,5 bis 9,5 Teilen reinem Natriumsulfhydrat zu und rührt während etwa 10 Minuten bei dieser Temperatur.
Nachdem die Reduktion beendet ist, lässt man erkalten und isoliert den Farb stoff durch Zusatz von Natriumchlorid. Der Farbstoff wird erbfiltriert und getrocknet.
Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if the diazo compound of 1-amino-4-nitrobenzene is combined with the acidic maleic acid ester of N-ethyl oxethylaminobenzene and the nitro group of this dye is converted into the amino group with reducing agents.
The dye that can be obtained in this way forms a dark red powder that dissolves as an alkali salt in water and dyes the acetate artificial silk in orange tones, which can be developed into a real black on the fiber by diazotizing and developing with 2-oxynaphthalene-3-carboxylic acid.
Example: 43.4 parts of the dye obtainable by coupling diazotized 1-amino-4-nitrobenzene and the acidic maleic acid ester of N-ethyl-oxethyl aminobenzene are dissolved in 1150 parts of water. At 60 to 70, an aqueous solution of 8.5 to 9.5 parts of pure sodium sulfhydrate is added and the mixture is stirred at this temperature for about 10 minutes.
After the reduction is complete, it is allowed to cool and the dye is isolated by adding sodium chloride. The dye is filtered off and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211925T | 1939-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211925A true CH211925A (en) | 1940-10-31 |
Family
ID=4447563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211925D CH211925A (en) | 1939-03-10 | 1939-03-10 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211925A (en) |
-
1939
- 1939-03-10 CH CH211925D patent/CH211925A/en unknown
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