CH220126A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH220126A CH220126A CH220126DA CH220126A CH 220126 A CH220126 A CH 220126A CH 220126D A CH220126D A CH 220126DA CH 220126 A CH220126 A CH 220126A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- preparation
- dye
- aminobenzene
- diazotized
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 4
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- -1 N-methyl-phenylamino- Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UTBUFLARLRSVFF-UHFFFAOYSA-N 3-chlorobutan-1-ol Chemical compound CC(Cl)CCO UTBUFLARLRSVFF-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Gegenstand des Hauptpatentes ist ein Ver fahren zur Herstellung eines Azofarbstoffes, gemäss welchem man 2,6-Dichlor-l-amino-4- nitrobenzol diazotiert und mit 3 (3'-Chlor- plienylamino-)butanol-(1) kuppelt.
Es wurde nun gefunden, dass man einen ebenfalls sehr wertvollen Azofarbstoff dann erhält, wenn man 4-Nitro-l-aminobenzol dia- zotiert und mit 3-(N-Methyl-phenylamino-) butanol-(1) kuppelt.
<I>Beispiel:</I> Eine aus 13,8 Teilen 4-Nitro-l-aminoben- zol auf dem üblichen Wege hergestellte Diazo- lösung lässt man unter Rühren in eine eis gekühlte Lösung von 17,9 Teilen 3-(N-1blethyl- phenylamiriobutanol-(1) (erhalten durch Kon- densation von 3-Chlorbutanol mit Methylani- lin) in 12 Teile Salzsäure von 23 Be und 800 Teile Wasser einlaufen. Hierauf wird zur Beendigung der Kupplung mit Natrium acetat abgestumpft.
Der erhaltene Farbstoff färbt Acetatseide in echten Rottönen.
Process for the preparation of an azo dye. The main patent relates to a process for the production of an azo dye, according to which 2,6-dichloro-1-amino-4-nitrobenzene is diazotized and coupled with 3 (3'-chloroplienylamino) butanol- (1).
It has now been found that a likewise very valuable azo dye is obtained if 4-nitro-1-aminobenzene is diazotized and coupled with 3- (N-methylphenylamino) butanol- (1).
<I> Example: </I> A diazo solution prepared in the usual way from 13.8 parts of 4-nitro-l-aminobenzene is poured into an ice-cooled solution of 17.9 parts of 3- (N -1-methylphenylamiriobutanol- (1) (obtained by condensation of 3-chlorobutanol with methylaniline) is poured into 12 parts of hydrochloric acid of 23 Be and 800 parts of water, followed by truncation with sodium acetate to terminate the coupling.
The dye obtained dyes acetate silk in real red tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE220126X | 1939-05-03 | ||
| CH216417T | 1940-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH220126A true CH220126A (en) | 1942-03-15 |
Family
ID=25725848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH220126D CH220126A (en) | 1939-05-03 | 1940-04-09 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH220126A (en) |
-
1940
- 1940-04-09 CH CH220126D patent/CH220126A/en unknown
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