CH303902A - Process for the preparation of an acidic monoazo dye. - Google Patents
Process for the preparation of an acidic monoazo dye.Info
- Publication number
- CH303902A CH303902A CH303902DA CH303902A CH 303902 A CH303902 A CH 303902A CH 303902D A CH303902D A CH 303902DA CH 303902 A CH303902 A CH 303902A
- Authority
- CH
- Switzerland
- Prior art keywords
- monoazo dye
- acidic
- dye
- preparation
- parts
- Prior art date
Links
- 230000002378 acidificating effect Effects 0.000 title claims description 8
- 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 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 238000007747 plating Methods 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 238000004532 chromating Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- -1 2-methylaminonaphthalene-6-sulfonic acid methoxide Chemical compound 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension 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
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
-
- 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
- C09B45/38—Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfabren zur Herstellung eines sauren Monoazofarbstoffes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines sauren Monoazofarbstoffes, welches darin besteht, dass man ein Mol der Diazoverbindung aus 2- Ami tio-3'-carboxy-4'-oxy -1,
1'-diphenyisulfon-4- sulfonsäui-ephenylaniid mit einem Mol 2-3Ie- tliylamirlonaphthalin-6-sulfonsäuremetbylamid in dessen 1-Stellung kuppelt.
Ini nachfolgenden Beispiel bedeuten die Teile Ge wiehtsteile und die Prozente CTe- wiebtsprozente.
Beispiel: 44,8 Teile \?-Amino-3'-eai-boxy-4'-oxy-1,1'- cliplienylsulfon-4-sulfonsäui@ephenylamid wer den in 500 Teilen Wasser mit Hilfe von Na triumlivclroxyd neutral gelöst. Man versetzt die Lösung mit 36 Teilen 20o/oiger Natrium nitritlösung und lässt sie innerhalb von einer halben Stunde bei höchstens 10 zu einer Mi- schuli- von 40 Teilen konzentrierter Salzsäure und 200 Teilen Wasser einlaufen.
Die gelb- lieiie Diazoverbindung scheidet sieh nahezu c-ollständig aus. Nach beendigter Diazotierung wird die überschüssige salpetrige Säure zer stört. Zu der Diazosuspension lässt man inner halb von 10 Minuten bei 10 eine Lösung von '5 Teilen 2-Methylaminonaphthalin-6-sulfon- Säuremethvlamid in 200 Teilen Wasser und 15 Teilen konzentrierter Salzsäure zulaufen.
Die Kupplung beginnt sofort, und der rote Mono- azofarbstoff scheidet sich aus. Nach einstündi- ;em Rühren wird die Kupplungsmasse durch 7utropfen einer konzentrierten Natriumace- tatlösung kongoneutral gestellt., Der Farbstoff @"ird abfiltriert und mit Wasser gewaschen. Zur Umwandlung in das leicht lösliche Na triumsalz wird er in warmer Natriumcarbo- natlösung gelöst.
Man klärt die Lösung nöti genfalls von Verunreinigungen, salzt aus ihr den Farbstoff mittels Natriumc'hlorid aus, fil triert ihn ab und trocknet ihn.
Der neue saure Monoazofarbstoff ist ein rotes Pulver, löst sich leicht in heissem Wasser und färbt Wolle aus neutralem oder schwach saurem Bad in leuchtend roten Tönen, die sich beim Nachchromieren nur wenig ändern. Der Farbstoff eignet sich vorzüglich zum Färben nach dem Einbadchromierungsverfahren. Die Färbungen sind sehr gut. licht-, walk- itnd car- bonisierecht.
Process for the production of an acidic monoazo dye. The present patent is a process for the preparation of an acidic monoazo dye, which consists in that one mole of the diazo compound from 2- Ami tio-3'-carboxy-4'-oxy -1,
1'-diphenyisulfon-4-sulfonsäui-ephenylaniid with one mole of 2-3Ie- tliylamirlonaphthalin-6-sulfonsäuremetbylamid couples in its 1-position.
In the example below, the parts mean weighted parts and the percentages mean CTe weighted percentages.
Example: 44.8 parts of \? - Amino-3'-eai-boxy-4'-oxy-1,1'-cliplienylsulfon-4-sulfonsäui @ ephenylamide who dissolved neutrally in 500 parts of water with the help of sodium hydroxide. The solution is mixed with 36 parts of 20% sodium nitrite solution and allowed to run within half an hour at a maximum of 10 to a mixture of 40 parts of concentrated hydrochloric acid and 200 parts of water.
The yellowish diazo compound separates out almost completely. When the diazotization is complete, the excess nitrous acid is destroyed. A solution of 5 parts of 2-methylaminonaphthalene-6-sulfonic acid methoxide in 200 parts of water and 15 parts of concentrated hydrochloric acid is allowed to run into the diazo suspension within 10 minutes at 10.
Coupling begins immediately and the red monoazo dye is precipitated. After stirring for one hour, the coupling mass is rendered Congo-neutral by dropping a concentrated sodium acetate solution. The dye is filtered off and washed with water. In order to convert it into the easily soluble sodium salt, it is dissolved in warm sodium carbonate solution.
If necessary, the solution is cleared of impurities, the dye is salted out using sodium chloride, filtered off and dried.
The new acidic monoazo dye is a red powder that dissolves easily in hot water and dyes wool from a neutral or weakly acidic bath in bright red tones that change only slightly when chromium plating. The dye is particularly suitable for dyeing using the single-bath chrome plating process. The colorations are very good. light, walk itnd carbonization right.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH303902T | 1952-01-09 | ||
| CH301445T | 1952-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH303902A true CH303902A (en) | 1954-12-15 |
Family
ID=25734386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH303902D CH303902A (en) | 1952-01-09 | 1952-01-09 | Process for the preparation of an acidic monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH303902A (en) |
-
1952
- 1952-01-09 CH CH303902D patent/CH303902A/en unknown
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