CH280730A - Process for the preparation of an azo dye derivative. - Google Patents
Process for the preparation of an azo dye derivative.Info
- Publication number
- CH280730A CH280730A CH280730DA CH280730A CH 280730 A CH280730 A CH 280730A CH 280730D A CH280730D A CH 280730DA CH 280730 A CH280730 A CH 280730A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- preparation
- azo dye
- oxybenzene
- dye derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 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 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
- 210000002268 wool Anatomy 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000975 dye Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- -1 azo carbate Chemical compound 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005254 chromizing Methods 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
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbatoffes. Es wurde gefunden, das man zu einem wertvollen Monoazofarbstoff gelangt, wenn man 2-Oxynaphtlialin-6-sulfonsäure-phenyl- ester mit diazotierter 2-Amino-l-oxybenzol-4- sulfonsäure vereinigt.
Der neue Farbstoff bildet ein dunkles Pul ver, das sich in heissem Nasser mit violetter und in konzentrierter Schwefelsäure mit roter Farbe löst und das Wolle nach dem Nacliehro- mierungsverfahren in blaustichigen Bordeaux tönen färbt.
Der beim vorliegenden Verfahren als Aus gangsstoff zu verwendende 2-Oxynaphtlialin- 6-sulfonsäure-phenylester kann aus 2-Oxy- naphthalin-6-sulfonsäureehlorid-l-carbonsäure durch Umsetzung mit Oxy Benzol und nach trägliche Abspaltung der Carboxylgruppe her gestellt werden.
Die Diazotierung der 2-Amino-l-oxybenzol- 4-sulfonsäure kann in bekannter Weise zum Beispiel mittels Salzsäure und Natriumnitrit vorgenommen werden.
Die Kupplung wird zweckmässig in alka.Ii- sehem, z. B. in Natriumhydroxyd enthalten dem Medium dureligeführt. Die Aufarbeitung des entstandenen Farbstoffes kann in üblicher Weise erfolgen.
Beispiel: 30 Teile 2-OxynaphtIialin-6-sulfonsäure- plienylester (dargestellt durch Umsetzung von 2 - Oxy naphthalin- 6 -sulfonsäurechlor id -1-ear- bonsäure mit Oxybenzol in Gegenwart.
von Natriumhydroxyd und Abspaltung der Car- boxylgruppe durch Erhitzen in wässerigem, neutralem bis saurem Medium) werden in 200 Teilen MTasser, 4 Teilen Natriumhydroxyd und 32 Teilen n-Butanol unter leichtem Erwärmen klargelöst und mit der auf übliche Weise aus 19 Teilen 2-Amino-l-oxybenzol-4-sidfonsäure hergestellten und mit Natriumcarbonat neu tralisierten Diazoverbindung bei 0 bis 10 ver einigt. Die Kupplung setzt sofort ein und ist in einigen Stunden beendet.
Der so erhaltene Farbstoff wird abfiltriert, mit Natriumchlorid- lösung gewaschen und getrocknet.
Process for the production of an azo carbate. It has been found that a valuable monoazo dye is obtained if 2-oxynaphthlialine-6-sulfonic acid phenyl ester is combined with diazotized 2-amino-1-oxybenzene-4-sulfonic acid.
The new dye forms a dark powder that dissolves in hot water with violet color and in concentrated sulfuric acid with red color and dyes the wool in blue-tinged bordeaux tones using the natural chromizing process.
The 2-oxynaphthalene-6-sulfonic acid phenyl ester to be used as starting material in the present process can be prepared from 2-oxynaphthalene-6-sulfonic acid chloride-1-carboxylic acid by reaction with oxybenzene and subsequent cleavage of the carboxyl group.
The diazotization of 2-amino-1-oxybenzene-4-sulfonic acid can be carried out in a known manner, for example by means of hydrochloric acid and sodium nitrite.
The coupling is useful in alka.Ii- sehem, z. B. in sodium hydroxide contained the medium dureligefelte. The dye formed can be worked up in a customary manner.
Example: 30 parts of 2-oxynaphthalene-6-sulfonic acid plienyl ester (prepared by reacting 2-oxynaphthalene-6-sulfonic acid chloride-1-earboxylic acid with oxybenzene in the presence.
sodium hydroxide and cleavage of the carboxyl group by heating in an aqueous, neutral to acidic medium) are dissolved in 200 parts of water, 4 parts of sodium hydroxide and 32 parts of n-butanol with gentle heating and with the usual way of 19 parts of 2-amino L-oxybenzene-4-sidfonsäure produced and neutralized with sodium carbonate diazo compound at 0 to 10 united ver. The clutch starts immediately and is completed in a few hours.
The dye thus obtained is filtered off, washed with sodium chloride solution and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH276720T | 1949-04-06 | ||
| CH280730T | 1949-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH280730A true CH280730A (en) | 1952-01-31 |
Family
ID=25731722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH280730D CH280730A (en) | 1949-04-06 | 1949-04-06 | Process for the preparation of an azo dye derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH280730A (en) |
-
1949
- 1949-04-06 CH CH280730D patent/CH280730A/en unknown
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