CH177580A - Process for the preparation of a new disazo dye. - Google Patents
Process for the preparation of a new disazo dye.Info
- Publication number
- CH177580A CH177580A CH177580DA CH177580A CH 177580 A CH177580 A CH 177580A CH 177580D A CH177580D A CH 177580DA CH 177580 A CH177580 A CH 177580A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- disazo dye
- preparation
- dye
- parts
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- -1 aminoazo compound Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- JZCHVGWHSDLSRK-UHFFFAOYSA-N 5-chloro-6-diazocyclohexa-1,3-diene Chemical compound [N+](=[N-])=C1C(C=CC=C1)Cl JZCHVGWHSDLSRK-UHFFFAOYSA-N 0.000 claims description 2
- 241000974482 Aricia saepiolus Species 0.000 claims description 2
- SBXKRBZKPQBLOD-UHFFFAOYSA-N aminohydroquinone Chemical compound NC1=CC(O)=CC=C1O SBXKRBZKPQBLOD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims 1
- 230000007797 corrosion Effects 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen Disazofarbstoffes. Wir haben gefunden, dass ein neuer und wertvoller Disazofarbstoff, welcher auf Ace- tatseide kräftig grünlich blaue Töne von hoher Licht- und Waschbeständigkeit und guter Ätzbarkeit ergibt, durch Kupplung von o-Chlordiazobenzol mit Aminohydrochinon- di-(@-hydroxyäthyl)ätlier, Diazotierung der resultierenden Aminoverbindung und Kupp lung mit 1-(3-Hydroxyäthylamino)-5-naphtol in einem Säuremedium erhalten wird.
<I>Beispiel:</I> Die durch Diazotierung von 127,5 Teilen o-Chloranilin in bekannter Weise erhaltene Lösung wird bei<B>100</B> C einer Lösung von 213 Teilen Aminohydrochinon-di-(ss-hydroxy- äthyl)äther in 370 Teilen 10'/o Chlorwas- serstoffsäure und 6000 Teilen Wasser zuge setzt.
Die Kombination wird durch allmäh lichen Zusatz von genügend Acetat erleich tert, um die freie Mineralsäure des Mediums zu entfernen.. Wenn die Kombination vollen- det ist, werden 590 Teile 10'/o Chlorwas- serstoffsäure der Suspension des Hydrochlo- riden der so erhaltenen Aminoazoverbindung zugesetzt.
Das Gemisch wird auf 35 o C erhitzt und die Aminoazoverbindung durch Zusatz von 72 Teilen Natriumnitrit diazotiert. Die Mischung wird bei 3511 C umgerührt, bis die Diazotierung vollendet ist, wobei die Disazoverbindung in Lösung ist. Diese Lö sung wird, wenn nötig, gefiltert und nach Abkühlung auf 15 o C einer Lösung von 203 Teilen 1-@-Hydroxyäthylamino.5-naphthol in 370 Teilen 10'/o Chlorwasserstoffsäure und 8000 Teilen Wasser zugesetzt.
Das Gemisch wird umgerührt, bis die Kombination voll ständig ist, worauf der Farbstoff mit Na- triumcarbonat gerade noch alkalinisch ge macht, der Farbstoff filtriert, mit Wasser gewaschen und entweder als Paste aufbe wahrt oder getrocknet wird.
Er löst sich in konzentrierter Schwefel säure zu einer braunen Farbe und in Äthyl- acetat zu einer grünlich-blauen Farbe und färbt Celluloseacetat in kräftig grünblauen Tönen von hoher Licht- und Waschfestigkeit und guter Ätzbarkeit.
Process for the preparation of a new disazo dye. We have found that a new and valuable disazo dye, which on acetate silk gives strong greenish blue tones of high lightfastness and washing resistance and good etchability, by coupling o-chlorodiazobenzene with aminohydroquinone di- (@ -hydroxyethyl) ätlier, diazotization the resulting amino compound and coupling with 1- (3-hydroxyethylamino) -5-naphthol in an acid medium is obtained.
<I> Example: </I> The solution obtained by diazotizing 127.5 parts of o-chloroaniline in a known manner is at <B> 100 </B> C a solution of 213 parts of aminohydroquinone-di- (ss-hydroxy- ethyl) ether in 370 parts of 10% hydrochloric acid and 6000 parts of water is added.
The combination is facilitated by the gradual addition of enough acetate to remove the free mineral acid of the medium. When the combination is complete, 590 parts 10% hydrochloric acid of the suspension of the hydrochloride will be obtained Aminoazo compound added.
The mixture is heated to 35 ° C. and the aminoazo compound is diazotized by adding 72 parts of sodium nitrite. The mixture is stirred at 3511 ° C. until the diazotization is complete, the disazo compound being in solution. If necessary, this solution is filtered and, after cooling to 15 o C, is added to a solution of 203 parts of 1-@-Hydroxyäthylamino.5-naphthol in 370 parts of 10 '/ o hydrochloric acid and 8000 parts of water.
The mixture is stirred until the combination is complete, whereupon the dye is made alkaline with sodium carbonate, the dye is filtered, washed with water and either stored as a paste or dried.
It dissolves in concentrated sulfuric acid to a brown color and in ethyl acetate to a greenish-blue color and colors cellulose acetate in strong green-blue shades of high lightfastness and washability and good etchability.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB177580X | 1933-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH177580A true CH177580A (en) | 1935-06-15 |
Family
ID=10100697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH177580D CH177580A (en) | 1933-07-18 | 1934-07-03 | Process for the preparation of a new disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH177580A (en) |
-
1934
- 1934-07-03 CH CH177580D patent/CH177580A/en unknown
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