CH138873A - Process for the preparation of a yellow azo dye. - Google Patents
Process for the preparation of a yellow azo dye.Info
- Publication number
- CH138873A CH138873A CH138873DA CH138873A CH 138873 A CH138873 A CH 138873A CH 138873D A CH138873D A CH 138873DA CH 138873 A CH138873 A CH 138873A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- yellow
- azo dye
- yellow azo
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000987 azo dye Substances 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 11
- 210000002268 wool Anatomy 0.000 claims description 4
- 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 3
- 239000000843 powder Substances 0.000 claims description 3
- XWTWZZFSPBHOIF-UHFFFAOYSA-N 3-amino-n-methyl-n-phenylbenzenesulfonamide Chemical compound C=1C=CC(N)=CC=1S(=O)(=O)N(C)C1=CC=CC=C1 XWTWZZFSPBHOIF-UHFFFAOYSA-N 0.000 claims 1
- MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007859 condensation product Substances 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
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- -1 O-alkyl Chemical group 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines gelben Azoiarbstoffes. Es wurde gefunden, dass man Farbstoffe von hervorragenden Echtheitseigenschaften erhält, wenn man Diazoverbindungen von Basen der allzemeinen'Formel:
EMI0001.0006
in der die beiden Arylreste nicht substituiert oder substituiert sein können, mit Pyrazolon der allgemeinen Formel:
EMI0001.0009
worin X = CHs, COOH oder C00-Alkyl und Y = H, Alkyl, 0-Alkyl, Sulfo- oder Carbonsäuregruppen bedeutet, kuppelt. Ver wendet man als Kupplungskomponente nicht sulfierte Pyrazolone, so können die Farbstoffe nachträglich sulfiert werden. Die Farbstoffe besitzen sehr gute Wasch-, Walk- und Licht echtheit und können je nach ihrer Zusammen setzung als Wollfarbstoffe, für Seide, Kunst seide oder als Lackfarbstoffe Verwendung finden.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung eines gelben Azofarbstoffes der folgenden Formel:
EMI0001.0024
welcher getrocknet ein gelbes Pulver bildet und Wolle in gelben Tönen von hervorragen der Wasch-; Walk- und Lichtechtheit färbt.
Der Farbstoff wird erhalten, indem man m- Aminobenzolsulfosäüremethyl - phenylamid diazotiert und mit 1-(4'-sulfophenyl)-3-methy l- 5-pyrazolon kuppelt.
<I>Beispiel:</I> 26,2 Gewichtsteile m-Aminobenzolsulfo- säure-methylplienylainid werden mit 48 Teilen Salzsäure 20 $e und 6,9 Grewichtsteilen Nitrit diazotiert und mit 27,6 Gewichtsteilen des Natriumsalzes des 1-(4'-Sulfophenyl)-3- methyl-5-pyrazolons in Gegenwart von über schüssiger Soda gekuppelt. Der gebildete Farbstoff wird durch Zusatz von Kochsalz abgeschieden und filtriert.
Er bildet getrock net ein gelbes Pulver und färbt Wolle in grünstichig gelben Tönen, die sich durch hervorragende Wasch-, Walk- und Licht echtheit auszeichnen. Der Farbstoff hat fol gende Formel:
EMI0002.0018
Die Darstellung des als Ausgangsmaterial verwendeten m-Aniinobenzolsulfosäui,emethyl- phenylamids der Formel:
EMI0002.0021
kann erfolgen durch Methylierung und Re- duktion des Kondensationsproduktes aus m Nitrobenzolsulfosäurechlorid und Anilin oder durch Reduktion des Kondensationsproduktes aus m-Nitrobenzolsulfochlorid und IIZethyl- anilin.
Process for the preparation of a yellow azoi agent. It has been found that dyes with excellent fastness properties are obtained if diazo compounds of bases of the general formula:
EMI0001.0006
in which the two aryl radicals cannot be substituted or substituted, with pyrazolone of the general formula:
EMI0001.0009
where X = CHs, COOH or C00-alkyl and Y = H, alkyl, O-alkyl, sulfo or carboxylic acid groups, couples. If non-sulfated pyrazolones are used as the coupling component, the dyes can be sulfated subsequently. The dyes have very good wash, boiled and light fastness and, depending on their composition, can be used as wool dyes, for silk, artificial silk or as paint dyes.
The present invention relates to a process for the preparation of a yellow azo dye of the following formula:
EMI0001.0024
which when dried forms a yellow powder, and wool in yellow tones of excellent washing; Milling and lightfastness colors.
The dye is obtained by diazotizing m-aminobenzenesulfosäüremethyl-phenylamide and coupling with 1- (4'-sulfophenyl) -3-methyl-5-pyrazolone.
<I> Example: </I> 26.2 parts by weight of m-aminobenzenesulfonic acid methylplienylamide are diazotized with 48 parts of hydrochloric acid 20% and 6.9 parts by weight of nitrite and then diazotized with 27.6 parts by weight of the sodium salt of 1- (4'- Sulfophenyl) -3-methyl-5-pyrazolones coupled in the presence of excess soda. The dye formed is separated off by adding sodium chloride and filtered.
When dry, it forms a yellow powder and dyes wool in greenish yellow tones, which are characterized by excellent fastness to washing, fulling and light. The dye has the following formula:
EMI0002.0018
The representation of the m-Aniinobenzolsulfosäui, emethylphenylamids of the formula used as starting material:
EMI0002.0021
can be carried out by methylation and reduction of the condensation product of m-nitrobenzenesulfonic acid chloride and aniline or by reduction of the condensation product of m-nitrobenzenesulfonyl chloride and IIZethylaniline.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE138873X | 1927-09-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH138873A true CH138873A (en) | 1930-03-31 |
Family
ID=5667505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH138873D CH138873A (en) | 1927-09-19 | 1928-09-17 | Process for the preparation of a yellow azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH138873A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3136752A (en) * | 1957-10-23 | 1964-06-09 | Geigy Ag J R | Aminopyrazole monoazo dyestuffs |
-
1928
- 1928-09-17 CH CH138873D patent/CH138873A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3136752A (en) * | 1957-10-23 | 1964-06-09 | Geigy Ag J R | Aminopyrazole monoazo dyestuffs |
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