CH299201A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH299201A CH299201A CH299201DA CH299201A CH 299201 A CH299201 A CH 299201A CH 299201D A CH299201D A CH 299201DA CH 299201 A CH299201 A CH 299201A
- Authority
- CH
- Switzerland
- Prior art keywords
- monoazo dye
- amino
- red
- preparation
- dichloro
- Prior art date
Links
- 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 5
- 239000000975 dye Substances 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 235000005811 Viola adunca Nutrition 0.000 claims description 3
- 235000013487 Viola odorata Nutrition 0.000 claims description 3
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 240000009038 Viola odorata Species 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 244000154870 Viola adunca Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Monoazo- farbstoffes. Das Verfahren ist dadurch ge kennzeichnet, dass man die Diazoverbindimg von 2-Amino-2',4-dichlor-1,1'-diphenylsulfid in saurem Mediiun mit 2-Amino-8-oxy-naphtha- lin-6-sulfonsäure kuppelt.
Der erhaltene neue Monoazofarbstoff stellt ein dunlie ötes Pulver vor, das sich in war mem Wasser mit roter und in konzentrierter Schwefelsäure mit blauvioletter Farbe löst und Wolle aus neutralem oder schwach saurem Bade in blaustichig roten Tönen färbt.
Beispiel: 27 Teile 2-Amino-2',4-dichlor-1,1'-diphenyl- sulfid werden in 135 Teilen Eisessig und 30 Teilen 30o/oiger Salzsäure gelöst und mit 6,9 Teilen Natriumnitrit diazotiert. Man verdünnt mit Wasser und lässt zur Diazolösung eine schwach essigsauer gestellte, wässerige Lösung des Natronsalzes von 24 Teilen 2-Amino-8-oxy- naphthalin-6-sulfosäure einlaufen.
Nach dem Abstumpfen der Mineralsäure mit verdünnter Natronlauge bis zur schwach lackmussauren Reaktion wird der abgeschiedene Monoazo- farbstoff der Formel
EMI0001.0032
abfiltriert, mit Kochsalzlösung gewaschen und getrocknet. Er stellt ein dunkelrotes Pulver dar, das sich in warmem Wasser mit roter und in konzentrierter Schwefelsäure mit blauvio letter Farbe löst. Der Farbstoff ergibt auf Wolle aus neutralem oder schwach saurem Bade gefärbt, blaustichig rote Töne von sehr guter Walk-, Seewasser- und guter Lichtecht heit.
Process for the preparation of a monoazo dye. The present patent relates to a process for the preparation of a monoazo dye. The process is characterized in that the diazo compound of 2-amino-2 ', 4-dichloro-1,1'-diphenyl sulfide is coupled in acidic medium with 2-amino-8-oxy-naphthalin-6-sulfonic acid.
The new monoazo dye obtained is a dark powder which dissolves in warm water with red and in concentrated sulfuric acid with a blue-violet color and dyes wool from neutral or weakly acidic baths in bluish red tones.
Example: 27 parts of 2-amino-2 ', 4-dichloro-1,1'-diphenyl sulfide are dissolved in 135 parts of glacial acetic acid and 30 parts of 30% hydrochloric acid and diazotized with 6.9 parts of sodium nitrite. It is diluted with water and an aqueous solution of the sodium salt of 24 parts of 2-amino-8-oxynaphthalene-6-sulfonic acid, which has been made weakly acidic in acetic acid, is run into the diazo solution.
After the mineral acid has been blunted with dilute sodium hydroxide solution to the point of a weak lacquer acid reaction, the deposited monoazo dye is of the formula
EMI0001.0032
filtered off, washed with brine and dried. It is a dark red powder that dissolves in warm water with red and in concentrated sulfuric acid with blue violet color. When dyed on wool from a neutral or weakly acidic bath, the dye results in bluish red shades of very good fullness, seawater and lightfastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH299201T | 1951-05-15 | ||
| CH295676T | 1951-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH299201A true CH299201A (en) | 1954-05-31 |
Family
ID=25733629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH299201D CH299201A (en) | 1951-05-15 | 1951-05-15 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH299201A (en) |
-
1951
- 1951-05-15 CH CH299201D patent/CH299201A/en unknown
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