CH321748A - Process for the preparation of a monoazo dye - Google Patents
Process for the preparation of a monoazo dyeInfo
- Publication number
- CH321748A CH321748A CH321748DA CH321748A CH 321748 A CH321748 A CH 321748A CH 321748D A CH321748D A CH 321748DA CH 321748 A CH321748 A CH 321748A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- preparation
- dye
- monoazo dye
- chloro
- 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 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 9
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction 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
- 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
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 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
- 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
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- BXRFSIGOXQYNKH-UHFFFAOYSA-N CS(=O)(=O)C.NC1=CC=CC=C1 Chemical compound CS(=O)(=O)C.NC1=CC=CC=C1 BXRFSIGOXQYNKH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 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
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance 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
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes Er wurde gefunden, dass man zu einem neuen, wertvollen lionoazofarbstoff gelangt, wenn man eine Diazoverbindung aus 4-Chlor- 1 -aminobenzol 2-methylsulfon mit 1-Di-(ss-oxy- äthyl)-amino-3-methylbenzol vereinigt.
Der neue Farbstoff stellt ein weinTOtes Pulver dar, welches Acetatseide und Nylon in rotorangen Tönen von hoher Lichtechtheit färbt.
Die Diazotierung, des erwähnten Amino- benzolmethylsulfons kann nach an sich be kannten Methoden, z. B. mit Hilfe von Aiine- ralsäure, insbesondere Salzsäure und Natrium nitrit erfolgen.
Die Kupplung kann ebenfalls nach an sich bekannter Weise, z. B. in neutralem bis, sau rem Mittel, gegebenenfalls in Gegenwart von Natriumacetat oder ähnlichen, die Kupplungs ges beeinflussenden Puffersub stanzen vorgenommen werden.
Nach erfolgter Kupphingsreaktion können rlie gebildeten Farbstoffe leicht, z. B. durch Filtration, abgetrennt werden. mit 25 Teilen konzentrierter Salzsäure ver- setzt. Durch Kühlung von aussen wird die Temperatur während der Diazotierung zwi schen 0 bis 5 gehalten. Die Diazolösung 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 2n-Salzsäure gelöst ist, fliessen. Es entsteht eine dunkelrote Lösung, aus welcher der Farbstoff durch Neutralisieren mit ge sättigter Natriumaeetatlösung ausfällt. Er wird abg enutscht und getrocknet.
Process for the preparation of a monoazo dye It has been found that a new, valuable lionoazo dye is obtained if a diazo compound of 4-chloro-1-aminobenzene-2-methylsulfone with 1-di- (ss-oxy-ethyl) -amino-3 is used -methylbenzene combined.
The new dye is a WeinTOtes powder, which dyes acetate silk and nylon in red-orange shades of high lightfastness.
The diazotization of the aforementioned amino benzene methyl sulfone can be according to methods known per se, for. B. with the help of alic acid, especially hydrochloric acid and sodium nitrite.
The coupling can also according to a known manner, for. B. in neutral to, sour rem means, optionally in the presence of sodium acetate or similar, the coupling ges influencing buffer substances are made.
After the Kupphingsreaktion rlie formed dyes can easily, z. B. by filtration, are separated. 25 parts of concentrated hydrochloric acid are added. The temperature is kept between 0 and 5 during the diazotization by external cooling. The diazo solution is completely clear and pale golden yellow in color.
It is allowed to slowly flow into 19.5 parts of 1-di (, ss-oxyethyl) amino-3-methylbenzene, which is dissolved in 40 parts of 2N 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 |
|---|---|---|---|
| CH321748T | 1952-11-27 | ||
| CH314327T | 1956-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH321748A true CH321748A (en) | 1957-05-15 |
Family
ID=25736013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH321748D CH321748A (en) | 1952-11-27 | 1952-11-27 | Process for the preparation of a monoazo dye |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH321748A (en) |
-
1952
- 1952-11-27 CH CH321748D patent/CH321748A/en unknown
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