CH184307A - Process for the preparation of a water-soluble monoazo dye. - Google Patents
Process for the preparation of a water-soluble monoazo dye.Info
- Publication number
- CH184307A CH184307A CH184307DA CH184307A CH 184307 A CH184307 A CH 184307A CH 184307D A CH184307D A CH 184307DA CH 184307 A CH184307 A CH 184307A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- preparation
- monoazo dye
- soluble monoazo
- 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 description 2
- 239000000975 dye Substances 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- IAVHKMVGTPXJIC-UHFFFAOYSA-N 2-phenylamino-ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1=CC=CC=C1 IAVHKMVGTPXJIC-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- -1 ethylene, propylene Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines wasserlöslichen Nonoazofarbstoffes. Die Erfindung bezieht sich auf ein Ver fahren zur Herstellung eines neuen, wasser löslichen, besonders zum Färben von Acetat seide wertvollen Monoazofarbstoffes.
Es wurde gefunden, dass derartige Mono- azofarbstoffe erhalten werden können durch Kuppeln eines diazotierten, weder Sulfo- noch Carboxylgruppen enthaltenden Amins der Benzolreihe mit einer Arylaminoalkylen- sulfosäure der Formel Ar-NR-Alk-SO"H, worin Ar von Sulfo- und Carboxylgruppen freies Phenyl, Toluyl und ähnliche bezeich net, R Wasserstoff,
Alkyl, Aralkyl oder Alkoxyalkyl bedeutet, und die Stelle von Alk durch Äthylen, Propylen, oder höhere Gruppen, die auch eine Hydrogylgruppe tra gen können, eingenommen ist.
Gemäss dem den Gegenstand, des vorlie genden Patentes bildenden Verfahren wird diazotiertes p-Nitranilin mit dem Natrium- salz des Phenyltaurins in wässeriger Na- triumcarbonatlösung gekuppelt.
Beispiel: Man diazotiert auf übliche Art<B>138</B> Teile p-Nitranilin und fügt die Diazolösung nach und nach zu einer eiskalten Lösung von 22,3 Teilen des Natriumsalzes von Phenyltaurin in 4000 Teilen, 208 Teile Natriumkarbonat enthaltenden Wassers. Die Kupplung geht rasch vonstatten. Nachdem sie vollendet ist, wird die Mischung auf 65 C erwärmt und der neue Farbstoff durch Aussalzen und Ab filtrieren abgesondert.
Er stellt im trockenen Zustande ein gelbes Pulver dar, welches sich in warmem Wasser mit rötlichgelber, in kon zentrierter Schwefelsäure mit orangebrauner Farbe löst. In neutraler oder alkalischer, 1 % Salz enthaltender Flotte, oder in saurer Flotte erzeugt er auf Acetatseide orange Farbtöne.
Process for the preparation of a water-soluble nonoazo dye. The invention relates to a process for the production of a new, water-soluble, particularly valuable monoazo dye for dyeing acetate silk.
It has been found that such monoazo dyes can be obtained by coupling a diazotized amine of the benzene series containing neither sulfo nor carboxyl groups with an arylaminoalkylenesulfonic acid of the formula Ar-NR-Alk-SO "H, where Ar is sulfo and carboxyl groups denotes free phenyl, toluyl and the like, R is hydrogen,
Means alkyl, aralkyl or alkoxyalkyl, and the position of alk is taken by ethylene, propylene, or higher groups which can also carry a hydrogen group.
According to the process forming the subject matter of the present patent, diazotized p-nitroaniline is coupled with the sodium salt of phenyltaurine in an aqueous sodium carbonate solution.
Example: 138 parts of p-nitroaniline are diazotized in the usual way and the diazo solution is gradually added to an ice-cold solution of 22.3 parts of the sodium salt of phenyltaurine in 4000 parts of water containing 208 parts of sodium carbonate. The coupling takes place quickly. After it is completed, the mixture is heated to 65 ° C. and the new dye is filtered off by salting out and filtering off.
In the dry state it is a yellow powder which dissolves in warm water with a reddish-yellow color, in concentrated sulfuric acid with an orange-brown color. In neutral or alkaline liquor containing 1% salt, or in acidic liquor, it creates orange shades on acetate silk.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB184307X | 1934-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH184307A true CH184307A (en) | 1936-05-31 |
Family
ID=10112322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH184307D CH184307A (en) | 1934-07-27 | 1935-07-22 | Process for the preparation of a water-soluble monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH184307A (en) |
-
1935
- 1935-07-22 CH CH184307D patent/CH184307A/en unknown
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