CH211600A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211600A CH211600A CH211600DA CH211600A CH 211600 A CH211600 A CH 211600A CH 211600D A CH211600D A CH 211600DA CH 211600 A CH211600 A CH 211600A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminobenzene
- methyl
- azo dye
- dye
- preparation
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- ARZIPQATHCDKRF-UHFFFAOYSA-N NC(CC(Cl)=C1)(C=C1[N+]([O-])=O)Cl Chemical compound NC(CC(Cl)=C1)(C=C1[N+]([O-])=O)Cl ARZIPQATHCDKRF-UHFFFAOYSA-N 0.000 claims 1
- 229920000297 Rayon Polymers 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- UMXXOIBGEWVADR-UHFFFAOYSA-N 1-N,3-N-dichloro-5-nitrobenzene-1,3-diamine Chemical compound [N+](=O)([O-])C1=CC(=CC(=C1)NCl)NCl UMXXOIBGEWVADR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
Landscapes
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man einen wert vollen Azofarbstoff erhält, wenn man N-Di- oxäthyl-3-methyl-aminobenzol, die Diazover- bindung des 4-Nitro-2,6-dichloraminobenzols und Maleinsäureanhydrid derart aufeinander einwirken lässt, dass der saure Dimaleinsäure- ester des N-Dioxäthyl-3-methyl-aminoben- zols gebildet wird und der Diazorest in 4:
-Stellung zur tertiären Aminogruppe ein tritt.
Der so " .erhaltene Farbstoff bildet ein dunkles Pulver, das sich in, Form eines Al kalisalzes in Wasser mit brauner Farbe löst und Acetatkunstseide aus wässriger Lösung in demselben Tone färbt.
neutralisiert den entstandenen Ester mit einer verdünnten, wässrigen AmTnoniak- lösung. In diese neutrale Lösung trägt man- die Diazolösung, die man durch Diazotieren von 207 Teilen 4-Nitro-2,6-dichloraminoben- zol erhalten hat, ein.
Die Bildung des Farb stoffes wird zweckmässig durch Zugabe eines neutralisierenden Mittels, wie beispielsweise Natriumacetat oder Magnesiumhydroxyd be schleunigt. Der Farbstoff wird gegebenen falls mit Chlornatrium ausgefällt, abfiltriert und nachher durch Verrühren in Wasser und Zugabe eines Alkalis neutral gestellt: Er kann durch Versetzen mit Chlornatrium, Abfiltrieren und Trocknen isoliert werden.
Beispiel: <B>195</B> Teile N-Dioxäthyl-3-methyl-amino- benzol werden unter Rühren geschmolzen und allmählich mit 220 Teilen Maleinsäure- anhydrid versetzt. Die so entstandene vis kose Masse wird während etwa 2 Stunden bei<B>90'</B> C gerührt. Man lässt erkalten und
Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if N-dioxyethyl-3-methyl-aminobenzene, the diazo compound of 4-nitro-2,6-dichloroaminobenzene and maleic anhydride are allowed to act on one another in such a way that the acid Dimaleic acid ester of N-dioxäthyl-3-methyl-aminobenzene is formed and the diazo radical in 4:
Position to the tertiary amino group occurs.
The dyestuff obtained in this way forms a dark powder which, in the form of an alkali salt, dissolves in water with a brown color and dyes acetate artificial silk from an aqueous solution in the same shade.
neutralizes the resulting ester with a dilute, aqueous ammonia solution. The diazo solution which was obtained by diazotizing 207 parts of 4-nitro-2,6-dichloroaminobenzene is entered into this neutral solution.
The formation of the dye is expediently accelerated by adding a neutralizing agent such as sodium acetate or magnesium hydroxide. If appropriate, the dye is precipitated with sodium chloride, filtered off and then rendered neutral by stirring in water and adding an alkali: it can be isolated by adding sodium chloride, filtering off and drying.
Example: 195 parts of N-dioxethyl-3-methyl-aminobenzene are melted while stirring and 220 parts of maleic anhydride are gradually added. The resulting viscous mass is stirred at 90 ° C for about 2 hours. You let it cool down and
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH208950T | 1937-09-18 | ||
| CH211600T | 1938-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211600A true CH211600A (en) | 1940-09-30 |
Family
ID=25724592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211600D CH211600A (en) | 1937-09-18 | 1938-07-28 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211600A (en) |
-
1938
- 1938-07-28 CH CH211600D patent/CH211600A/en unknown
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