CH184012A - Process for the preparation of a new monoazo dye. - Google Patents
Process for the preparation of a new monoazo dye.Info
- Publication number
- CH184012A CH184012A CH184012DA CH184012A CH 184012 A CH184012 A CH 184012A CH 184012D A CH184012D A CH 184012DA CH 184012 A CH184012 A CH 184012A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- new
- monoazo dye
- greenish
- dye
- 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 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 238000009963 fulling Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- ORKQJTBYQZITLA-UHFFFAOYSA-N 4-octylaniline Chemical compound CCCCCCCCC1=CC=C(N)C=C1 ORKQJTBYQZITLA-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen Nonoazofarbstoffes. Vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung eines neuen Monoazofarbstoffes.
Der neue Monoazofarbstoff löst sich in warmem Wasser mit grünlich-gelber Farbe und in konzentrierter Schwefelsäure mit gel ber Farbe. Er färbt Wolle aus einem neu tralen oder sauren Bad in grünlich-gelben Tönen von guter Wasch- und Walkechtheit.
Gemäss der Erfindung wird p-Dodecylani- lin dianotiert, und mit 1-(2' : 5'-Dichlor-4'- sulfophenyl)-3-niethyl-5-pyrazolon gekuppelt. <I>Beispiel:</I> 26,1 Teile p-Dodecylanilin (hergestellt nach dem von Beran für p-Octylanilin angewandten Verfahren, Ber. der deutschen chem. Ges.<B>1885,</B> 18, 132)
werden 15 Minuten bei gewöhnlicher Temperatur mit 250 Teilen Salzsäure (36 %) und 300 Teilen Wasser umgerührt, worauf das Gemisch auf 50 0 C erwärmt wird, bis eine homogene Paste sich bildet. Man setzt genügend Eis zu, um das Ganze auf 6 0 C abzukühlen. Bei dieser Temperatur wird das Amin durch langsamen Zusatz von 69 Teilen einer 10 prozentigen wässerigen Lösung von Natriumnitrit dianotiert, wobei eine blasse, grünlich-gelbe Lösung erhalten wird.
Wenn die Dianotierung vollendet ist, lässt man die Diazolösung in eine Lösung von 34,6 Teilen des Natriumsalzes von 1- (2' : 5'- Dichlor- 4'- sulfophenyl)-3-methyl-5-pyrazolon und 21 Tei len Natriumkarbonat in 400 Teilen Wasser einfliessen. Die Kupplung ist rasch beendet. Man setzt das Rühren fort, bis der Farbstoff körnig geworden ist. Alsdann wird abfiltriert, mit 5 prozentiger Salzlösung gewaschen und getrocknet.
Process for the preparation of a new nonoazo dye. The present invention relates to a process for the preparation of a new monoazo dye.
The new monoazo dye dissolves in warm water with a greenish-yellow color and in concentrated sulfuric acid with a yellow color. It dyes wool from a neutral or acidic bath in greenish-yellow shades that are washable and milled fast.
According to the invention, p-dodecylaniline is dianotized and coupled with 1- (2 ': 5'-dichloro-4'-sulfophenyl) -3-diethyl-5-pyrazolone. <I> Example: </I> 26.1 parts of p-dodecylaniline (produced according to the process used by Beran for p-octylaniline, Ber. Der Deutschen chem. Ges. <B> 1885, </B> 18, 132)
are stirred for 15 minutes at normal temperature with 250 parts of hydrochloric acid (36%) and 300 parts of water, whereupon the mixture is heated to 50 ° C. until a homogeneous paste is formed. Enough ice is added in order to cool the whole thing down to 6 ° C. At this temperature, the amine is dianotized by slowly adding 69 parts of a 10 percent aqueous solution of sodium nitrite, a pale, greenish-yellow solution being obtained.
When the dianotization is complete, the diazo solution is left in a solution of 34.6 parts of the sodium salt of 1- (2 ': 5'-dichloro-4'-sulfophenyl) -3-methyl-5-pyrazolone and 21 parts of sodium carbonate pour in 400 parts of water. The coupling ends quickly. Stirring is continued until the dye has become granular. It is then filtered off, washed with 5 percent salt solution and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB184012X | 1934-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH184012A true CH184012A (en) | 1936-05-15 |
Family
ID=10111813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH184012D CH184012A (en) | 1934-06-28 | 1935-06-28 | Process for the preparation of a new monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH184012A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2471628A (en) * | 1944-08-31 | 1949-05-31 | Sandoz Ltd | Monoazo pyrazolone dyes |
-
1935
- 1935-06-28 CH CH184012D patent/CH184012A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2471628A (en) * | 1944-08-31 | 1949-05-31 | Sandoz Ltd | Monoazo pyrazolone dyes |
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