CH210501A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH210501A CH210501A CH210501DA CH210501A CH 210501 A CH210501 A CH 210501A CH 210501D A CH210501D A CH 210501DA CH 210501 A CH210501 A CH 210501A
- Authority
- CH
- Switzerland
- Prior art keywords
- reddish
- preparation
- dye
- yellow
- 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
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- HFBZLHDBQUONLH-UHFFFAOYSA-N 3-amino-N-dodecyl-N-phenylbenzamide Chemical compound NC=1C=C(C(=O)N(C2=CC=CC=C2)CCCCCCCCCCCC)C=CC=1 HFBZLHDBQUONLH-UHFFFAOYSA-N 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
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005695 Ammonium acetate Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 235000019257 ammonium acetate Nutrition 0.000 claims description 2
- 229940043376 ammonium acetate Drugs 0.000 claims description 2
- 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
- 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
- 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000019248 orcein 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
- 238000003756 stirring Methods 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 1Vtonoazo-Farbstoffes. Vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung eines neuen Monoazo-Farbstoffes.
Gemäss vorliegender Erfindung wird der neue Monoazo-Farbstoff dadurch erhalten, dass man diazotiertes N-(3-Aminobenzoyl)- N-dodecylanilin mit 1-(4'-SuHophenyl)-3- methyl-5-pyrazolon kuppelt.
Der neue Farbstoff ist ein rötlich-gelbes Pulver, das sich in heissem Wasser und in konzentrierter Schwefelsäure löst und rötlich gelbe Lösungen ergibt. Er färbt Wolle in einem sauren Bad oder in einem Bad das 2 Ammoniumazetat enthält, in rötlich-gelben Tönungen mit vorzüglicher Wasch-, Walk und Lichtechtheit.
Beispiel: Ein Gemisch von 38 Teilen N-(3-Amino- benzoyl) - N - dodecylanilin (Schmelzpunkt <B>63'</B> C), 500 Teile Wasser und 25 Teile 36%ige Salzsäure wird auf<B>80'</B> C erhitzt und dann unter Umrühren auf 15 C ab gekühlt.
Die Base wird dann diazotiert durch Zu gabe von 6,9 Teilen Natriumnitrit, wobei die Diazoverbindung als Lösung erhalten wird. DiE Diazolösung wird, wenn erforderlich, nach Filtration auf 5 C abgekühlt und einer ebenfalls gekühlten Lösung von 25,4 Teilen 1-(4'-Sulfophenyl)-3-methyl-5-pyrazo- lon in 400 Teilen Wasser, das genügend Na triumkarbonat enthält,
die Kupplung alka lisch (Lacmusprobe) zu erhalten, zugesetzt. Wenn die Kupplung erfolgt ist, wird der Farbstoff durch Zugabe von 5 % Natrium chlorid (Volumgewicht) isoliert, abfiltriert und getrocknet.
Process for the preparation of a 1Vtonoazo dye. The present invention relates to a process for the preparation of a new monoazo dye.
According to the present invention, the new monoazo dye is obtained by coupling diazotized N- (3-aminobenzoyl) -N-dodecylaniline with 1- (4'-SuHophenyl) -3-methyl-5-pyrazolone.
The new dye is a reddish-yellow powder that dissolves in hot water and in concentrated sulfuric acid and gives reddish-yellow solutions. It dyes wool in an acidic bath or in a bath containing ammonium acetate in reddish-yellow tones with excellent wash, milled and lightfastness.
Example: A mixture of 38 parts of N- (3-aminobenzoyl) - N - dodecylaniline (melting point <B> 63 '</B> C), 500 parts of water and 25 parts of 36% hydrochloric acid is converted to <B> 80 '</B> C and then cooled to 15 C while stirring.
The base is then diazotized by adding 6.9 parts of sodium nitrite, the diazo compound being obtained as a solution. The diazo solution is, if necessary, cooled to 5 C after filtration and a likewise cooled solution of 25.4 parts of 1- (4'-sulfophenyl) -3-methyl-5-pyrazolone in 400 parts of water containing sufficient sodium carbonate contains,
to obtain the coupling alkaline (lacmus sample), added. When the coupling has taken place, the dye is isolated by adding 5% sodium chloride (volume weight), filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB210501X | 1937-05-26 | ||
| CH207510T | 1938-05-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210501A true CH210501A (en) | 1940-07-15 |
Family
ID=25724416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210501D CH210501A (en) | 1937-05-26 | 1938-05-05 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210501A (en) |
-
1938
- 1938-05-05 CH CH210501D patent/CH210501A/en unknown
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