CH211800A - Process for the production of a new dye. - Google Patents
Process for the production of a new dye.Info
- Publication number
- CH211800A CH211800A CH211800DA CH211800A CH 211800 A CH211800 A CH 211800A CH 211800D A CH211800D A CH 211800DA CH 211800 A CH211800 A CH 211800A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- new
- production
- new dye
- pyrazolone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
-
- 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 neuen Farbstoffes. Es wurde gefunden, dass man einen neuen Farbstoff erhält, wenn man das Pyrazolon der Formel
EMI0001.0003
mit diazotierter 1-Amino-4-sulfobenzol-2-car- bonsäure behandelt.
Der neue Pyrazolonazofarbstoff stellt ge trocknet ein braunes Pulver dar. Er erzeugt auf der vegetabilen Faser gelbe Färbungen, die durch Nachkupfern gut licht- und wasch echt werden. <I>Beispiel:</I> 52,1 Teile des Pyrazolons der Formel
EMI0001.0011
werden in 26 Teilen Natronlauge von 36 B6 und 400 Teilen Wasser gelöst.
In die fil trierte Lösung gibt man 33 Teile Natrium- bicarbonat und etwas Eis und hierauf die Di- azoverbindung aus<B>21,7</B> Teilen 1-Amino-4- sulfobenzol-2-carbonsäure.
Nach beendigter Kupplung wird das Ge misch auf zirka<B>60'</B> aufgewärmt, der teil weise ausgefallene Farbstoff vollends aus gesalzen -und nach dem Erkalten abgenutscht.
Das zur Farbstoffherstellung verwendete Pyrazolonderivat kann zum Beispiel durch Kondensation von 4-Nitrobenzol-l-ca,rbon- säurechlorid mit Dehydrothioparatolizidin. Reduktion de r Nitro- zur Aminogruppe, Hy- drazinierung der letzteren nach üblichen DIe- thoden,
und Vberführung des Hydrazins durch Kondensation mit Acetessigester in das entsprf.chende 3-Methyl-5-hyrazolon, oder auch durch Kondensation in Gegenwart eines Phosphorchlorides von 1-Phenyl-3-methyl-5- pyrazolon-4'-carbonsäure mit dem Dehydro- thio-p-toluidin erhalten werden.
Process for the production of a new dye. It has been found that a new dye is obtained by using the pyrazolone of the formula
EMI0001.0003
treated with diazotized 1-amino-4-sulfobenzene-2-carboxylic acid.
The new pyrazolonazo dye is a brown powder when dried. It produces yellow colorations on the vegetable fiber, which are made lightfast and washfast by re-coppering. <I> Example: </I> 52.1 parts of the pyrazolone of the formula
EMI0001.0011
are dissolved in 26 parts of sodium hydroxide solution of 36 B6 and 400 parts of water.
33 parts of sodium bicarbonate and a little ice are added to the filtered solution, followed by the diazo compound composed of 21.7 parts of 1-amino-4-sulfobenzene-2-carboxylic acid.
After the coupling is complete, the mixture is warmed up to about <B> 60 '</B>, the partially precipitated dye is completely salted out - and sucked off after cooling.
The pyrazolone derivative used to produce the dye can be produced, for example, by condensation of 4-nitrobenzene-1-ca, carbonic acid chloride with dehydrothioparatolizidine. Reduction of the nitro to the amino group, hydration of the latter according to conventional methods,
and conversion of the hydrazine by condensation with acetoacetic ester into the corresponding 3-methyl-5-hyrazolone, or by condensation in the presence of a phosphorus chloride of 1-phenyl-3-methyl-5-pyrazolone-4'-carboxylic acid with the dehydro- thio-p-toluidine.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211800T | 1937-05-22 | ||
| CH204242T | 1937-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211800A true CH211800A (en) | 1940-10-15 |
Family
ID=25724032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211800D CH211800A (en) | 1937-05-22 | 1937-05-22 | Process for the production of a new dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211800A (en) |
-
1937
- 1937-05-22 CH CH211800D patent/CH211800A/en unknown
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