CH273617A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH273617A CH273617A CH273617DA CH273617A CH 273617 A CH273617 A CH 273617A CH 273617D A CH273617D A CH 273617DA CH 273617 A CH273617 A CH 273617A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- monoazo dye
- parts
- diazotized
- 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 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 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
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes. Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines Monoazofarbstoffes, welches dadurch gekenn zeichnet ist, dass man diazotierten 2-Amino- 4,2'-dichlor-1,1'-diphenyläther mit 1-(3'- Sulfo)-phenyl-3-methyl-5-pyrazolon kuppelt.
Der neue Farbstoff bildet ein hellgelbes Pulver, das sich in heissem -Wasser leicht löst und Wolle aus essigsaurem Bade in rotstichig gelben Tönen von sehr guter Lichtechtheit und guten Nasseehtheiten anfärbt. In konzen trierter Schwefelsäure erhält man mit diesem Farbstoff eine bräunlichrote Lösung.
<I>Beispiel:</I> Man diazotiert 25,4 Teile 2-Amino-4,2'-di- chlor-1,1'-diphenyläther mit 25 Teilen 30o/oiger Salzsäure und 6,9 Teilen Natriumnitrit in 200 Teilen Wasser bei 0 bis 50 in üblicher Weise.
Die von Verunreinigungen abfiltrierte Diazolösung tropft man bei 0 bis<B>50</B> zu einer Lösung, die man aus 200 Teilen Wasser und 25,4 Teilen 1-(3'-Sulfo)-phenyl-3-methyl-5- pyrazolon unter Zusatz von so viel Natrium- carbonat, dass auf Brillantgelbpapier schwach alkalische Reaktion eintritt, erhalten hat. Mit Vorteil setzt man hierauf Natriumacetat oder Natriumcarbonat bis zum Verschwinden der mineralsauren Reaktion zu.
Nach beendeter Kupplung wird mit Natriumcarbonat oder N atriumhydroxyd versetzt, bis die Suspension phenolphthaleinalkalisch reagiert. Der Farb stoff wird nun abfiltriert und getrocknet.
Process for the preparation of a monoazo dye. The subject of the present patent forms a process for the preparation of a monoazo dye, which is characterized in that diazotized 2-amino-4,2'-dichloro-1,1'-diphenyl ether with 1- (3'-sulfo) -phenyl- 3-methyl-5-pyrazolone couples.
The new dye forms a light yellow powder that dissolves easily in hot water and dyes wool from an acetic acid bath in reddish yellow shades of very good lightfastness and good wetness properties. A brownish-red solution is obtained with this dye in concentrated sulfuric acid.
<I> Example: </I> 25.4 parts of 2-amino-4,2'-dichloro-1,1'-diphenyl ether are diazotized with 25 parts of 30% hydrochloric acid and 6.9 parts of sodium nitrite in 200 parts Water at 0 to 50 in the usual way.
The diazo solution filtered off from impurities is added dropwise at 0 to 50 to a solution which is made up of 200 parts of water and 25.4 parts of 1- (3'-sulfo) -phenyl-3-methyl-5- Pyrazolone with the addition of enough sodium carbonate that a weakly alkaline reaction occurs on brilliant yellow paper. Sodium acetate or sodium carbonate is then advantageously added until the mineral acid reaction has disappeared.
When the coupling is complete, sodium carbonate or sodium hydroxide is added until the suspension has an alkaline phenolphthalein reaction. The dye is then filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH273617T | 1949-03-10 | ||
| CH270834T | 1949-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH273617A true CH273617A (en) | 1951-02-15 |
Family
ID=25731265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH273617D CH273617A (en) | 1949-03-10 | 1949-03-10 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH273617A (en) |
-
1949
- 1949-03-10 CH CH273617D patent/CH273617A/en unknown
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