CH321746A - Process for the preparation of a monoazo dye - Google Patents
Process for the preparation of a monoazo dyeInfo
- Publication number
- CH321746A CH321746A CH321746DA CH321746A CH 321746 A CH321746 A CH 321746A CH 321746D A CH321746D A CH 321746DA CH 321746 A CH321746 A CH 321746A
- Authority
- CH
- Switzerland
- Prior art keywords
- monoazo dye
- preparation
- parts
- dye
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 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
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000004677 Nylon Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 229920001778 nylon Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance Substances 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)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes Es wurde gefunden, dass man zu einem neuen, wertvollen Monoazofarbstoff gelangt, wenn man eine Diazoverbindung aLts 1-Amino- benzol-4-methylsulfon mit 1-Di-(ss-oxyäthyl)- amino-3-methylbenzol vereinigt.
Der neue Farbstoff stellt ein weinrotes Pulver dar, welches Acetatseide und Nylon in orangeroten Tönen von hoher Lichteehtheit färbt.
Die Diazotierung des erwähnten Amino- 1)enzolmethvlsttlfons kann nach an sich be- 1#.annten Methoden, z. B. mit Hilfe von Mine ralsäure, insbesondere Salzsäure und Natrium nitrit erfolgen.
Die Kupplung kann ebenfalls nach an sich bekannter Weise, z. B. in neutralem bis saurem Mittel, gegebenenfalls in Gegenwart von Natriumacetat oder ähnlichen, die Kupp- lungsgesehwindigkeit beeinflussenden Puffer substanzen vorgenommen werden.
Nach erfolgter Kupplungsreaktion können die gebildeten Farbstoffe leicht, z. B. durch Filtration, abgetrennt werden. <I>Beispiel</I> 17 Teile 1-Aminobenzol-4-methylsulfon, ?5 Teile einer 4n-Natriumnitritlösung und <B>20</B> Teile Eis werden in 40 Teilen Wasser mit 25 Teilen konzentrierter Salzsäure versetzt. Durch Kühlung von aussen wird die Tempe ratur während der Diazotierung zwischen 0 bis 5 gehalten. Die Diazol'ösung ist vollständig klar und schwach goldgelb gefärbt.
Man lässt sie langsam zu 19,5 Teilen 1-Di-(ss-oxyäthyl)- amino-3-methylbenzol, welches in 40 Teilen '?n-Salzsäure gelöst ist, fliessen. Es entsteht eine dunkelrote Lösung, aus welcher der Farb stoff durch Neutralisieren mit gesättigter Na t.riumaeetatlösung ausfällt. Er wird abge- nutscht und getrocknet.
Process for the preparation of a monoazo dye It has been found that a new, valuable monoazo dye is obtained if a diazo compound in the form of 1-amino-benzene-4-methylsulfone is combined with 1-di- (β-oxyethyl) -amino-3-methylbenzene .
The new dye is a wine-red powder that dyes acetate silk and nylon in orange-red shades of high lightness.
The diazotization of the amino 1) enzolmethvlstlfons mentioned can be carried out by methods known per se, e.g. B. with the help of mine ralsäure, especially hydrochloric acid and sodium nitrite.
The coupling can also be carried out in a manner known per se, for. B. in neutral to acidic agents, optionally in the presence of sodium acetate or similar, the coupling speed influencing buffer substances are made.
After the coupling reaction, the dyes formed can easily, for. B. by filtration, are separated. <I> Example </I> 17 parts of 1-aminobenzene-4-methylsulfone, 5 parts of a 4N sodium nitrite solution and <B> 20 </B> parts of ice are mixed with 25 parts of concentrated hydrochloric acid in 40 parts of water. The temperature is kept between 0 and 5 during the diazotization by cooling from the outside. The diazole solution is completely clear and pale golden yellow in color.
It is allowed to slowly flow into 19.5 parts of 1-di- (s-oxyethyl) -amino-3-methylbenzene, which is dissolved in 40 parts of n-hydrochloric acid. A dark red solution is formed from which the dye precipitates out by neutralizing it with saturated sodium acetate solution. It is sucked off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH321746T | 1952-11-27 | ||
| CH314327T | 1956-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH321746A true CH321746A (en) | 1957-05-15 |
Family
ID=25736011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH321746D CH321746A (en) | 1952-11-27 | 1952-11-27 | Process for the preparation of a monoazo dye |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH321746A (en) |
-
1952
- 1952-11-27 CH CH321746D patent/CH321746A/en unknown
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