CH237724A - Process for the preparation of a new monoazo dye. - Google Patents
Process for the preparation of a new monoazo dye.Info
- Publication number
- CH237724A CH237724A CH237724DA CH237724A CH 237724 A CH237724 A CH 237724A CH 237724D A CH237724D A CH 237724DA CH 237724 A CH237724 A CH 237724A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- yellow
- parts
- dye
- monoazo dye
- 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 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- CWJQQASJVVAXKL-UHFFFAOYSA-N 4-(3-Methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC=C(S(O)(=O)=O)C=C1 CWJQQASJVVAXKL-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/16—Naphthol-sulfonic acids
-
- 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 netten Honoazofarbstoffes. Die vorliegende Erfindung betrifft ein Ver fahren zur Herstellung eines neuen, sauren, zum Färben tierischer Fasern geeigneten Monoazofarbstoffes.
Erfindungsgemäss wird der neue Monoazo- farbstoff dadurch erhalten, dass 4-Amino-l- N-äthyl-a)-olilorpropionanilid diazotiert und die erhaltene Diazoverbindung mit 1-(4'-Sulfo- pheDyl)-3-methyl-5-p),razolon gekuppelt wird.
Derneue Farbstoff stellt ein gelbes Pulver dar, welches sieh in Wasser unter Bildung einer gelben Lösung und in konz. Schwefel säure unter Bildung einer grünlicli-gelben Lösung löst. Er färbtWolle aus einem Schwefel säure und Glaubersalz enthaltenden Bade in rötlich-gelben Tönen von guter Echtheit gegen starkes Waschen und Walken und guter Licht echtheit.
Die Erfindung wird durch das nachstehende Beispiel erläutert, ohne indessen darauf be schränkt zu sein. Die Teile bedeuten Gewichts teile. <I>Beispiel:</I> <B>22,65</B> Teile 4-Amino-l-N-äthyl-co-chlor- propionanilid werden in einem aus<B>320</B> Teilen Wasser und<B>25</B> Teilen 361/oiger Salzsäure bestehenden Gemisch gelöst und diese Lösung hierauf mit einer Lösung von<B>6,9</B> Teilen Na- triumnitrit in<B>50</B> Teilen Wasser versetzt.
Die Lösung der so erhaltenen Diazoverbindung wird auf<B>5-100</B> C gekühlt und innerhalb <B>10</B> Minuten zu einer auf ähnliche Weise ab gekühlten Lösung von 25,4 Teilen 1-(4'-Sulfo- phenyl)-3-methyl-5-pyrazolon in 400 Teilen Wasser, enthaltend<B>80</B> Teile Natriumchlorid und eine hinreichende Menge Natriumcarbonat, um das Kupplungsgemisch lackmusalkalisch zu erhalten, hinzugefügt.
Der Kupplungsvor gang ist rasch beendet, und der neue Farb stoff wird nach beendeter Kupplung durch allmähliche Zugabe von 120 Teilen Natrium- chlorid innerhalb einer halben Stunde aus- gefällt, hierauf filtriert, mit einer 20%igen Natriumchloridlösung gewaschen und bei 60-600 C getrocknet.
Process for making a nice honoazo dye. The present invention relates to a process for the production of a new, acidic, monoazo dye suitable for dyeing animal fibers.
According to the invention, the new monoazo dye is obtained by diazotizing 4-amino-1-N-ethyl-a) -olilorpropionanilide and treating the resulting diazo compound with 1- (4'-sulfopheDyl) -3-methyl-5-p) , razolon is coupled.
The new dye is a yellow powder, which looks in water to form a yellow solution and in conc. Sulfuric acid dissolves to form a greenish-yellow solution. It dyes wool from a bath containing sulfuric acid and Glauber's salt in reddish-yellow shades of good fastness to heavy washing and tumbling and good fastness to light.
The invention is illustrated by the following example without, however, being restricted thereto. The parts mean parts by weight. <I> Example: </I> <B> 22.65 </B> parts of 4-amino-IN-ethyl-co-chloropropionanilide are made up of <B> 320 </B> parts of water and <B > 25 parts of 361 /% hydrochloric acid mixture are dissolved and this solution is then mixed with a solution of <B> 6.9 </B> parts of sodium nitrite in <B> 50 </B> parts of water.
The solution of the diazo compound thus obtained is cooled to <B> 5-100 </B> C and within <B> 10 </B> minutes to a solution of 25.4 parts 1- (4'- Sulfophenyl) -3-methyl-5-pyrazolone in 400 parts of water, containing 80 parts of sodium chloride and a sufficient amount of sodium carbonate to obtain the coupling mixture in a litmus-alkaline manner.
The coupling process is quickly completed and the new dye is precipitated after coupling is complete by gradually adding 120 parts of sodium chloride within half an hour, then filtered, washed with a 20% sodium chloride solution and dried at 60-600 ° C .
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH231066T | 1943-12-08 | ||
| CH237724T | 1943-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH237724A true CH237724A (en) | 1945-05-15 |
Family
ID=25727536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH237724D CH237724A (en) | 1943-12-08 | 1943-12-08 | Process for the preparation of a new monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH237724A (en) |
-
1943
- 1943-12-08 CH CH237724D patent/CH237724A/en unknown
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