CH116152A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH116152A CH116152A CH116152DA CH116152A CH 116152 A CH116152 A CH 116152A CH 116152D A CH116152D A CH 116152DA CH 116152 A CH116152 A CH 116152A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- azo dye
- parts
- naphthol
- 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 claims description 3
- 239000002253 acid Substances 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 2
- 238000005185 salting out Methods 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 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
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Azofarbstoffes. Es wurde gefunden, dass man zu einem sehr wertvollen Azofarbstoff gelangt, wenn man o-Phenetidin in üblicher Weise diazo- tiert und mit dem Dinatriumsalz der 1-(p-Toluolsulfoäthyl)-amino-8-naphthol-3,6- clisulfosäure kuppelt.
Beispiel Die in üblicher Weise aus 1,37- Teilen o- Phenetidin, 69 Teilen Natriumnitrit und der erforderlichen Menge Salzsäure hergestellte Diazolösung läuft unter Rühren in eine eis kalte Lösung von 545 Teilen des Dinatrium- salzes der 1-(p-Toluolsulfoäthyl)-amino-8- naphthol-3,6-disulfösäure in 2e000 Teile Was ser und 106 Teile Soda. Die Kupplung ist nach einigen Stunden beendet.
Der durch Aussalzen isolierte Farbstoff bildet in trocke nem Zustande ein dunkelrotes Pulver, das sich in Wasser mit bläulich-roter Farbe löst. Der Farbstoff färbt Wolle in walkechten, klaren, bläulichroten Tönen an und besitzt hervorragendes Egalisierungsvermögen.
Die 1-(p-Toluolsulfoäthyl)-amino-8-naph- thol-3,6-disulfosäure wird auf folgende Weise erhalten : 391 Teile Dinatriumsalz der 1- Äthylamino-8-naphthol-3,6-disulfosäure wur den in 2000 Teilen Wasser gelöst. Nach Zu gabe von 136 Teilen kristallisiertem Na triumacetat und 190,5 Teilen p-Toluolsulfo- ehlorid wird einige Stunden bis zum Ver schwinden des Sulfochlorids auf 70-80 er wärmt. Eine herausgenommene Probe soll dann kein Nitrit mehr aufnehmen. Eventuell wird noch Sulfochlorid und Natriumacetat nachgegeben.
Die Lösung- enthält jetzt die 1-(p-Toluolsulfoäthyl)-amino-8-naphthol-3,6- disulfosäure, die wegen ihrer ausserordent lichen leichten Löslichkeit nur schwer in rei nem Zustande daraus abzuscheiden ist. Für die Farbstoffherstellung wird die Lösung direkt verwendet.
Process for the preparation of an azo dye. It has been found that a very valuable azo dye is obtained if o-phenetidine is diazoated in the usual manner and coupled with the disodium salt of 1- (p-toluenesulfoethyl) -amino-8-naphthol-3,6-clisulfonic acid.
EXAMPLE The diazo solution prepared in the usual manner from 1.37 parts of o-phenetidine, 69 parts of sodium nitrite and the required amount of hydrochloric acid runs into an ice-cold solution of 545 parts of the disodium salt of 1- (p-toluenesulfoethyl) -amino with stirring -8- naphthol-3,6-disulfoic acid in 2e000 parts of water and 106 parts of soda. The coupling is complete after a few hours.
The dye, isolated by salting out, forms a dark red powder when dry, which dissolves in water with a bluish-red color. The dye stains wool in clear, bluish-red shades that are fast to the mill and has excellent leveling properties.
The 1- (p-toluenesulfoethyl) -amino-8-naphthol-3,6-disulfonic acid is obtained in the following manner: 391 parts of the disodium salt of 1-ethylamino-8-naphthol-3,6-disulfonic acid WUR in 2000 parts Dissolved water. After adding 136 parts of crystallized sodium acetate and 190.5 parts of p-toluenesulfo-ehlorid, it is heated to 70-80 for a few hours until the sulfochloride disappears. A sample removed should then no longer absorb nitrite. Sulphochloride and sodium acetate may also be added.
The solution now contains 1- (p-toluenesulfoethyl) -amino-8-naphthol-3,6-disulfonic acid, which is difficult to separate from it in a pure state because of its extraordinary easy solubility. The solution is used directly for dye production.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH116152T | 1926-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH116152A true CH116152A (en) | 1926-08-02 |
Family
ID=4375160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH116152D CH116152A (en) | 1926-08-02 | 1925-03-27 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH116152A (en) |
-
1925
- 1925-03-27 CH CH116152D patent/CH116152A/en unknown
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