CH204242A - Process for the production of a new dye. - Google Patents
Process for the production of a new dye.Info
- Publication number
- CH204242A CH204242A CH204242DA CH204242A CH 204242 A CH204242 A CH 204242A CH 204242D A CH204242D A CH 204242DA CH 204242 A CH204242 A CH 204242A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- new
- production
- pyrazolone
- new dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 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
- 239000000987 azo dye Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 230000001180 sulfating effect Effects 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
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000007796 conventional method 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
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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
das in bekannter Weise aus der durch Stil- fieren von Dehydrothiotoluidin mit Schwefel säure erhältlichen Sulfonsäure hergestellt werden kann, mit diazotierter 1-Amino-4- sulfobenzol-2-carbonsäure 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
EMI0001.0014
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 Diazoverbindung aus 21,7 Teilen 1-Ainino- 4-sulfobenzol-2-carbonsäure.
Nach beendigter Kupplung wird das Ge misch auf etwa<B>60'</B> aufgewärmt, der teil weise ausgefallene Farbstoff vollends ausge- salzen und nach dein Erkalten abgenutscht.
Das zur Farbstoffherstellung verwendete Pyrazolonderivat kann zum Beispiel durch Kondensation von 4 - N iti-obenzol -1- earbon- säurechlorid mit dem Alonosulfierungsprodukt aus Dehydrothioparatoluidin, Reduktion der Nitro- zur Aminogruppe, Hydrazinierung der letzteren nach üblichen Methoden und über führung des Hydrazins durch Kondensation mit Acetessigester in das entsprechende 3-Methyl-5-pyrazolon,
oder auch durch Kon densation in Gegenwart eines Phosphorchlo- rides von 1-I'lieriyl-3-niethyl-5-pyi-azolon-4'- carbonsäure finit dem iIonosulfierungsprodulzt aus Deliydi o-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
which can be prepared in a known manner from the sulfonic acid obtainable by styling dehydrothiotoluidine with sulfuric acid, 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 fibers, which are made lightfast and washfast by re-coppering.
<I> Example: </I> 52.1 parts of the pyrazolone of the formula
EMI0001.0014
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 from 21.7 parts of 1-amino-4-sulfobenzene-2-carboxylic acid.
When the coupling is complete, the mixture is warmed up to about <B> 60 '</B>, the partially precipitated dye is completely salted out and suction filtered after it has cooled.
The pyrazolone derivative used for dye production can, for example, by condensation of 4 - N iti -obenzol -1-earbon- säurechlorid with the Alonosulfierungsprodukt from dehydrothioparatoluidine, reduction of the nitro to the amino group, hydrazination of the latter by conventional methods and over leadership of the hydrazine by condensation with Acetoacetic ester into the corresponding 3-methyl-5-pyrazolone,
or else by condensation in the presence of a phosphorus chloride of 1-I'lieriyl-3-diethyl-5-pyi-azolone-4'-carboxylic acid finitely obtained from the ionosulfurization product from Deliydi o-p-toluidine.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH204242T | 1937-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH204242A true CH204242A (en) | 1939-04-30 |
Family
ID=4444062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH204242D CH204242A (en) | 1937-05-22 | 1937-05-22 | Process for the production of a new dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH204242A (en) |
-
1937
- 1937-05-22 CH CH204242D patent/CH204242A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH204242A (en) | Process for the production of a new dye. | |
| CH212117A (en) | Process for the production of a new dye. | |
| CH211800A (en) | Process for the production of a new dye. | |
| CH212118A (en) | Process for the production of a new dye. | |
| CH211801A (en) | Process for the production of a new dye. | |
| CH210997A (en) | Process for the production of a new dye. | |
| DE728886C (en) | Process for the preparation of copper complex compounds of substantive azo dyes | |
| DE860388C (en) | Process for the preparation of acidic disazo dyes | |
| CH128905A (en) | Process for the production of a new dye. | |
| CH306253A (en) | Process for the production of a cobalt-containing azo dye. | |
| CH238336A (en) | Process for the preparation of a new disazo dye. | |
| CH199188A (en) | Process for the preparation of an azo dye. | |
| CH220750A (en) | Process for the production of a new azo dye. | |
| CH223710A (en) | Process for the production of a new azo dye. | |
| CH249552A (en) | Process for the preparation of a polyazo dye. | |
| CH146753A (en) | Process for the production of a new azo dye. | |
| CH304279A (en) | Process for the production of a cobalt-containing azo dye. | |
| CH306260A (en) | Process for the production of a cobalt-containing azo dye. | |
| CH303521A (en) | Process for the production of a cobalt-containing azo dye. | |
| CH128912A (en) | Process for the production of a new dye. | |
| CH133805A (en) | Process for the preparation of an azo dye. | |
| CH306252A (en) | Process for the production of a cobalt-containing azo dye. | |
| CH259329A (en) | Process for the preparation of an azo dye. | |
| CH128911A (en) | Process for the production of a new dye. | |
| CH297840A (en) | Process for the production of a cobalt-containing azo dye. |