CH328659A - Process for the preparation of a disazo dye - Google Patents
Process for the preparation of a disazo dyeInfo
- Publication number
- CH328659A CH328659A CH328659DA CH328659A CH 328659 A CH328659 A CH 328659A CH 328659D A CH328659D A CH 328659DA CH 328659 A CH328659 A CH 328659A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- disazo dye
- methyl
- preparation
- amino
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 238000007747 plating Methods 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000725 suspension Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/28—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Disazofarbstoffes Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung eines Dis- azofarbstoffes, -welches darin besteht, dass man 1 Mol der durch Kuppeln von tetrazotierter 1-(4'-Amino-3'-methyl)-benzoylamino-4-amino- benzol-3-carbonsäure mit 5-Oxy-7-sulfo- naphthyl (2) -carbaminsäure- (4' - acetylamino)
- phenylamid erhältlichen Diazomonoazoverbin- dung mit 1 Mo11-Phenyl-3-methyl-5-pyrazolon- 3'-sulfonsäüre kuppelt. , Im Beispiel bedeuten die Teile Gewichts teile.
Beispiel Eine neutralgestellte, 8-10 kalte Suspen sion der durch Kuppeln von 28,5 -Teilen tetra- zotierter 1-(4'-Amino-3'-methyl)-benzoylamino- 4-aminobenzol-3-carbonsäure mit 41,5 Teilen 5--Oxy-7-sulfonaphthyl(2) -carbaminsäure- (4'- acetyiamino)
-phenyla.mid erhältlichen Diazo- monoazozwischenverbindung wird innerhalb von einer Stunde in eine 30 warme Lösung aus 28 Teilen 1-Phenyl-3-methyl-5-pyrazolon- 3'-sulfonsäure, 12 Teilen Natriumcarbonat, 300 Teilen Pyridin und 500 Teilen Wasser gegeben.
Der gebildete Disazofarbstoff wird nach zweistündigem Rühren mittels Zusatz von Natriumchlorid abgeschieden, anschlie ssend filtriert und getrocknet. Er färbt Baum- wolle und Fasern aus regenerierter Cellulose im Naehkupferungsverfahren in scharlach roten Tönen von guter Licht- und Waschecht heit.
Die oben genannte Suspension der Diazo- monoazozwischenverbindiing erhält man, wenn man 28,5 Teile 1-(4'-Amino-3'-methyl)-benzoyl- amino-4-aminobenzol-3-carbonsäure in 800 Tei len Eiswasser anrührt und die Aufschläm- mung mit 50 Teilen 30o/oiger Salzsäure und hieraiü bei 0 mit 46 Teilen 30%iger Natrium- nitritlösung versetzt.
Der Tetrazolösung lässt man eine Lösung von 41,5 Teilen 5-0xy-7- suHonaphthyl (2) - carbaminsäure - (4' - acetyl- amino)-phenylamid und 10 Teilen Natrium carbonat in 400 Teilen Wasser zulaufen, stellt die Temperatur der Kupplungsmasse auf 8-10 und gibt ihr innerhalb von einer Stunde portionenweise ungefähr 20 Teile Na- triumbicarbonat zu.
Nachdem die Masse neu tralgestellt worden: ist, rührt man sie noch 2 Stunden lang bei 8-10 weiter. Dabei kup pelt nur die am Benzoylrest sitzende Diazo- gruppe. Die entstandene Diazomonoazozwi- schenverbindung scheidet sich in orangeroten Kristallen aus.
Process for the preparation of a disazo dye The present invention relates to a process for the preparation of a disazo dye, which consists in that 1 mol of 1- (4'-amino-3'-methyl) -benzoylamino-4-benzoylamino-4 -amino- benzene-3-carboxylic acid with 5-oxy-7-sulfonaphthyl (2) -carbamic acid- (4 '- acetylamino)
- Phenylamide available diazomonoazo compound with 1 Mo11-phenyl-3-methyl-5-pyrazolone-3'-sulfonic acid. , In the example, the parts mean parts by weight.
Example A neutralized, 8-10 cold suspension of the 1- (4'-amino-3'-methyl) -benzoylamino-4-aminobenzene-3-carboxylic acid tetrazotized by coupling 28.5 parts with 41.5 parts 5 - Oxy-7-sulfonaphthyl (2) -carbamic acid- (4'-acetyiamino)
-phenyla.mid available diazo monoazo intermediate compound is added within one hour to a warm solution of 28 parts of 1-phenyl-3-methyl-5-pyrazolone-3'-sulfonic acid, 12 parts of sodium carbonate, 300 parts of pyridine and 500 parts of water .
After stirring for two hours, the disazo dye formed is precipitated by adding sodium chloride, then filtered and dried. It dyes cotton and fibers from regenerated cellulose in the sewing process in scarlet red shades of good lightfastness and washfastness.
The above-mentioned suspension of the diazo monoazo intermediate compound is obtained if 28.5 parts of 1- (4'-amino-3'-methyl) -benzoylamino-4-aminobenzene-3-carboxylic acid are stirred in 800 parts of ice water and the 50 parts of 30% strength hydrochloric acid were added to the suspension, followed by 46 parts of 30% strength sodium nitrite solution at 0.
The tetrazo solution is allowed to run a solution of 41.5 parts of 5-0xy-7-suHonaphthyl (2) -carbamic acid - (4 '- acetyl-amino) -phenylamide and 10 parts of sodium carbonate in 400 parts of water, and the temperature of the coupling compound is set to 8-10 and add about 20 parts of sodium bicarbonate in portions within an hour.
After the mass has been neutralized, it is stirred for a further 2 hours at 8-10. Only the diazo group on the benzoyl radical couples. The resulting diazomonoazo intermediate compound precipitates in orange-red crystals.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH328659T | 1954-05-11 | ||
| CH310831T | 1954-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH328659A true CH328659A (en) | 1958-03-15 |
Family
ID=25735781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH328659D CH328659A (en) | 1954-05-11 | 1954-05-11 | Process for the preparation of a disazo dye |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH328659A (en) |
-
1954
- 1954-05-11 CH CH328659D patent/CH328659A/en unknown
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