CH196653A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH196653A CH196653A CH196653DA CH196653A CH 196653 A CH196653 A CH 196653A CH 196653D A CH196653D A CH 196653DA CH 196653 A CH196653 A CH 196653A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxy
- preparation
- amino
- methylbenzene
- azo dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000987 azo dye Substances 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 7
- 210000002268 wool Anatomy 0.000 claims description 3
- 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
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
-
- 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
- C09B29/26—Amino phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoües. Es wurde gefunden, dass man zu wertvol len Azofarbstoffen dadurch gelangt, dass man diazotierte ortho-Aminophenole, welche höch-_ stens eine Nitrogruppe enthalten, mit 1-Oxy- 2-acylamino-4-alkylbenzolen kuppelt.
Als Diazokomponenten können beispiels weise verwendet werden 1-Ogy-2-amino-4- nitrobenzol, 1-Oxy-2-amino-5-nitrobenzol, 1- Oxy- 2- amino- 4 -nitro-6-methylbenzol, 1-Oxy 2-amino-4-nitro-6-chlorbenzol,1-Oxy-2-ami_no- 4-nitrobenzol-6-sulfonsäure, 1-Oxy-2-amino-6- nitro- 4 -chlorbenzol,
1- Oxy- 2 -amino- 6 -nitro- benzol-4-sulfosäure. Als Kupplungskompo nenten können beispielsweise verwendet wer den 1-Oxy-2-acetylamino-4-methylbenzol, 1 Ogy- 2 -benzoylamino-4-methylbenzol, 1-Oxy- 2 - oxalylamino- 4 -methylbenzol, 1-Oxy- 4 -me- thylbenzol-2-phtalaminsäure, ferner solche Homologen der genannten Verbindungen,
welche an Stelle der Methylgruppe in 4-Stel- lung andere Alkylreste, wie den Äthyl-, n-Propyl-, Isopropyl-, n-Butyl-, Isobutyl-, tertiär-Butyl-, n-Amyl-, sekundär- oder ter- tiär-Amylrest tragen. Die Kupplung kann gegebenenfalls unter Zusatz von Pyridin aus geführt werden.
Die so erhältlichen Farb stoffe liefern in chromierter Färbung auf Wolle volle braune Töne von sehr guten Echtheitseigenschaften.
Das vorliegende Patent betrifft ein Ver fahren zur Darstellung eines Monoazofarb- stoffes und ist dadurch gekennzeichnet, dass man 1- Oxy- 2 -amino- 4 -nitrobenzol- 6 -sulf on- säure diazotiert und mit 1-Oxy-2-acetamino- 4-methylbenzol kuppelt.
<I>Beispiel:</I> 28,4 Teile 1-O$y-2-@am@ino-4-nitrobenzal--6- sulfonsäure werden mit 6,9 Teilen Nitrit und 22 Teilen Salzsäure diazotiert und mit 16,5 Teilen 1-Oxy-2-acetamino-4-methylbenzol in Gegenwart eines säurebindenden Mittels ge kuppelt. Der isolierte und getrocknete Farb stoff stellt ein dunkles Pulver dar, welches Wolle aus saurem Bade in gelbbraunen Tönen färbt, die beim Nachchromieren in ein volles Braun übergehen.
Process for the production of an azo dye. It has been found that valuable azo dyes are obtained by coupling diazotized ortho-aminophenols, which contain at most one nitro group, with 1-oxy-2-acylamino-4-alkylbenzenes.
The diazo components can be used, for example, 1-Ogy-2-amino-4-nitrobenzene, 1-oxy-2-amino-5-nitrobenzene, 1-oxy-2-amino-4-nitro-6-methylbenzene, 1-oxy 2-amino-4-nitro-6-chlorobenzene, 1-oxy-2-ami_no- 4-nitrobenzene-6-sulfonic acid, 1-oxy-2-amino-6-nitro-4-chlorobenzene,
1- Oxy-2-amino-6-nitro-benzene-4-sulfonic acid. As coupling components, for example, whoever uses 1-oxy-2-acetylamino-4-methylbenzene, 1-oxy-2-benzoylamino-4-methylbenzene, 1-oxy-2-oxalylamino-4-methylbenzene, 1-oxy-4-me - ethylbenzene-2-phthalamic acid, also such homologues of the compounds mentioned,
which instead of the methyl group in the 4-position other alkyl radicals, such as ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl, secondary or tertiary bear tiary amyl radical. The coupling can optionally be carried out with the addition of pyridine.
The dyes obtainable in this way provide full brown tones with very good fastness properties in chromed dyeing on wool.
The present patent relates to a process for the preparation of a monoazo dye and is characterized in that 1-oxy-2-amino-4-nitrobenzene-6-sulfonic acid is diazotized and with 1-oxy-2-acetamino-4 -methylbenzene couples.
<I> Example: </I> 28.4 parts of 1-O $ y-2- @ am @ ino-4-nitrobenzal-6-sulfonic acid are diazotized with 6.9 parts of nitrite and 22 parts of hydrochloric acid and 16, 5 parts of 1-oxy-2-acetamino-4-methylbenzene coupled in the presence of an acid-binding agent. The isolated and dried dye is a dark powder that dyes wool from an acid bath in yellow-brown tones that turn into a full brown when chromium-plating.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH196653T | 1947-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH196653A true CH196653A (en) | 1938-03-31 |
Family
ID=4440481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH196653D CH196653A (en) | 1947-05-13 | 1937-04-03 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH196653A (en) |
-
1937
- 1937-04-03 CH CH196653D patent/CH196653A/en unknown
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