CH209099A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH209099A CH209099A CH209099DA CH209099A CH 209099 A CH209099 A CH 209099A CH 209099D A CH209099D A CH 209099DA CH 209099 A CH209099 A CH 209099A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- preparation
- parts
- toluidine
- sulfonic acid
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 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 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000010985 leather Substances 0.000 claims description 3
- BHUUIODLTNMQLE-UHFFFAOYSA-N 2-amino-3-bromo-5-nitrobenzenesulfonic acid Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1S(O)(=O)=O BHUUIODLTNMQLE-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000002932 luster Substances 0.000 claims 1
- 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
- NEGPZGPAOPCNPD-UHFFFAOYSA-N 2-amino-3-chloro-5-nitrobenzenesulfonic acid Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1S(O)(=O)=O NEGPZGPAOPCNPD-UHFFFAOYSA-N 0.000 description 1
- NPCCPMHHNIOSHL-UHFFFAOYSA-N 3-(n-ethyl-3-methylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC(C)=C1 NPCCPMHHNIOSHL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002268 wool Anatomy 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 Äzofarbstoffes. p Gegenstand des Hauptpatentes ist ein Verfahren zur Herstellung eines Azofarb- stoffes, der Wolle und Leder in braunen Tönen anfärbt, welches dadurch gekennzeich net ist, dass man 2-Chlor-4-nitro-l-aminoben- zol-6-sulfonsäure diazotiert und mit Diogy- äthyl-m-toluidin kuppelt.
Es wurde nun gefunden, dass man einen Farbstoff mit ähnlichen Eigenschaften er hält, wenn man 2-Brom-4-nitro-l-aminoben- zol-6-sulfonsäure diazotiert und mit Ogy- äthylcyanäthyl-m-toluidin kuppelt.
<I>Beispiel:</I> 31,9 Teile 2-brom-4-nitranilin-6-sulfon- saures Natrium werden mit 100 Teilen einer etwa 18%igen Salzsäure mehrere Stunden lang in der Kugelmühle gemahlen. Danach wird der feine Kristallbrei mit 200 Teilen Wasser verdünnt und unter Eiskühlung durch Zusatz einer 20%igen Lösung von 6,9 Teilen Natriumnitrit diazotiert. Sobald nach etwa zwei Stunden die Diazotierung be endet ist,
wird die Masse im Verlauf einiger Minuten zu einer Lösung von 24 Teilen Ogy- äthylcyanäthyl - m - toluidinchlorhydrat in 500 Teilen Wasser gegeben. Der Farbstoff scheidet sieh in der stark sauren Flüssigkeit allmählich aus und wird nach mehrstündi gem Nachruhren abgesaugt, gewaschen, mit Natriumhydrogydlösuug neutralisiert und alsdann getrocknet. Er stellt ein dunkles, me tallisch glänzendes Pulver dar, das sich mit rotbrauner Farbe in Wasser spielend leicht löst und das Leder in braunen Tönen völlig durchfärbt. Die Echtheitseigenschaften sind sehr gut.
Process for the preparation of an azo dye. The main patent relates to a process for the production of an azo dye that dyes wool and leather in brown tones, which is characterized in that 2-chloro-4-nitro-1-aminobenzene-6-sulfonic acid is diazotized and coupled with diogyethyl-m-toluidine.
It has now been found that a dye with similar properties is obtained if 2-bromo-4-nitro-1-aminobenzene-6-sulfonic acid is diazotized and coupled with ogy ethylcyanoethyl-m-toluidine.
<I> Example: </I> 31.9 parts of 2-bromo-4-nitraniline-6-sulfonic acid sodium are ground with 100 parts of about 18% hydrochloric acid for several hours in a ball mill. The fine crystal slurry is then diluted with 200 parts of water and diazotized by adding a 20% strength solution of 6.9 parts of sodium nitrite while cooling with ice. As soon as the diazotization is over after about two hours,
the mass is added in the course of a few minutes to a solution of 24 parts of Ogy- äthylcyanäthyl - m - toluidine chlorohydrate in 500 parts of water. The dyestuff gradually separates out in the strongly acidic liquid and, after stirring for several hours, is filtered off with suction, washed, neutralized with sodium hydrogen solution and then dried. It is a dark, metallic, shiny powder that dissolves easily in water with a red-brown color and completely dyes the leather in brown tones. The fastness properties are very good.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE209099X | 1937-03-27 | ||
| CH203691T | 1938-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH209099A true CH209099A (en) | 1940-03-15 |
Family
ID=25723954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209099D CH209099A (en) | 1937-03-27 | 1938-01-21 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH209099A (en) |
-
1938
- 1938-01-21 CH CH209099D patent/CH209099A/en unknown
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