CH169948A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH169948A CH169948A CH169948DA CH169948A CH 169948 A CH169948 A CH 169948A CH 169948D A CH169948D A CH 169948DA CH 169948 A CH169948 A CH 169948A
- Authority
- CH
- Switzerland
- Prior art keywords
- red
- dye
- azo dye
- preparation
- blue
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 7
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005352 clarification Methods 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
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000010288 sodium nitrite 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
-
- 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
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paints Or Removers (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 163896. Verfahren zur Darstellung eines Azofarbstoffes. Im. Hauptpatent ist ein Verfahren zur Darstellung eines Azofarbstoffes beschrieben, bei welchem diazotiertes 2. 4 - Dinitranilin mit Bis-(ss-oxäthyl)-m-toluidin gekuppelt wird.
Es wurde nun gefunden, dass man in analoger Weise einen Azofarbstoff von wert vollen Eigenschaften erhält, wenn man di- azotiertes 2-Chlor-4-nitranilin in stark saurer Lösung kuppelt mit 3-Bis-(ss-oxäthyl)-amino- 1-toluol.
Der Farbstoff ist ein in Wasser unlös liches, dunkles Pulver, das in Alkohol mit roter, in konz. Schwefelsäure mit leuchtend blaustichig roter Farbe löslich ist und nach dem üblichen Verfahren Acetatseide in reinen, blauroten Tönen anfärbt.
Die<B>Fär-</B> bungen zeigen gute Echtheitseigenschaften und sind rein weiss ätzbar. Das neue Pro bukt ist auch ein gutes Färbemittel für Lacke. Beispiel:
86 Teile 2-Chlor-4-nitranilin werden in bekannter Weise mit 35 Teilen Natrium- nitrit und 240 Teilen konz. Schwefelsäure in verdünnter Lösung diazotiert. Die Di- azoniumlösung wird nach dem Klären mit 97,5 Teilen 3-Bis-(ss-oxäthyl)-amino-l-toluol, mit der nötigen Menge Salzsäure gelöst, bei 0 bis 5 zur Kupplung gebracht. Nach einiger Zeit ist die Farbstoffbildung beendet, die man durch Abstumpfen der stark sau ren Reaktion beschleunigen kann.
Das End produkt wird auf bekannte Weise isoliert, vergastet oder, nach dem Trocknen bei mässig hoher Temperatur, zu einem Färbepräparat verarbeitet. Es ist ein in Wasser unlösliches, dunkles Pulver, dass' sich beispielsweise in Alkohol mit roter, in konz. Schwefelsäure mit leuchtend blaustichig roter Farbe löst.
<B> Additional patent </B> to main patent no. 163896. Process for the preparation of an azo dye. The main patent describes a process for the preparation of an azo dye in which diazotized 2,4-dinitraniline is coupled with bis- (s-oxethyl) -m-toluidine.
It has now been found that an azo dye of valuable properties is obtained in an analogous manner if diazotized 2-chloro-4-nitroaniline is coupled in a strongly acidic solution with 3-bis- (s-oxethyl) -amino- 1- toluene.
The dye is a water-insoluble, dark powder that is mixed in alcohol with red, in conc. Sulfuric acid is soluble with a bright blue-tinged red color and dyes acetate silk in pure, blue-red tones using the usual method.
The <B> dye </B> exercises show good fastness properties and can be etched in pure white. The new product is also a good colorant for paints. Example:
86 parts of 2-chloro-4-nitroaniline are concentrated in a known manner with 35 parts of sodium nitrite and 240 parts. Sulfuric acid diazotized in dilute solution. The diazonium solution is after clarification with 97.5 parts of 3-bis (ss-oxäthyl) -amino-1-toluene, dissolved with the necessary amount of hydrochloric acid, brought to the coupling at 0 to 5. After some time, the dye formation is complete, which can be accelerated by dulling the strongly acidic reaction.
The end product is isolated in a known manner, gasified or, after drying at a moderately high temperature, processed into a dye preparation. It is a dark powder that is insoluble in water and that 'dissolves in alcohol with red, in conc. Sulfuric acid with a bright bluish red color.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH169948T | 1933-09-01 | ||
| CH163895T | 1933-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169948A true CH169948A (en) | 1934-06-15 |
Family
ID=25717881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169948D CH169948A (en) | 1933-09-01 | 1933-09-01 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169948A (en) |
-
1933
- 1933-09-01 CH CH169948D patent/CH169948A/en unknown
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