CH328660A - Process for the preparation of a disazo dye - Google Patents
Process for the preparation of a disazo dyeInfo
- Publication number
- CH328660A CH328660A CH328660DA CH328660A CH 328660 A CH328660 A CH 328660A CH 328660D A CH328660D A CH 328660DA CH 328660 A CH328660 A CH 328660A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- disazo dye
- oxy
- 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 2
- 239000000975 dye Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000007747 plating Methods 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 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
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 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
- UONVFNLDGRWLKF-UHFFFAOYSA-N 2,5-diaminobenzoic acid Chemical compound NC1=CC=C(N)C(C(O)=O)=C1 UONVFNLDGRWLKF-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-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
- 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—
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 310831 Verfahren zur Herstellung eines Disazofarbstoffes Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Hersfellung 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-) - phenvjamid erhältlichen Diazomonoazoverbin- dung mit 1 Mol 1-(4'-Oxy-3'-carboxy)-phenyl- 5-pyrazolon-3-carbonsäureamid kuppelt.
Im Beispiel bedeuten die Teile Gewichts- teile.
<I>Beispiel</I> 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'- acetylamino)-phenylamid erhältlichen Diazo- monoazozwischenverbindung wird innerhalb von einer Stunde in eine 30 warme Lösung aus 26,3 Teilen 1-(4'-Oxy-3'-carboxy)
phenyl- 5-pyrazolon-3-carbonsäureamid, 12 Teilen Na- triumcarbonat, 300 Teilen Pyridin und 500 Teilen Wasser gegeben. Der gebildete Disazo- farbstoff wird nach zweistündigem Rühren mittels Zusatz von Natriumchlorid abgeschie den, anschliessend filtriert und getrocknet. Er färbt Baumwolle und Fasern aus regenerier ter Cellulose im Nachkupferungsverfahren in roten Tönen von guter Licht- und Wasch echtheit.
Die oben genannte Suspension der Diazo- monoazozwischenverhindung erhält man, wenn man 28,5 Teile 1-(4'-Amino-3'-methyl)-benzoy 1= amino-4-aminobenzol-3-carbonsäiire in 800 Tei len Eiswasser anrührt und die Aufschläm- mung mit 50 Teilen 301/oiger Salzsäure und hierauf bei 0 mit 46 Teilen*30'1/oiger Natrium nitritlösung versetzt.
Der Tetrazolösung @lässt man eine Lösung von 41,5 Teilen 5-Oxy-7- sulfonaphthyl (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 Diazomonazozwischen- verbindung scheidet sich in roten Kristallen aus.
<B> Additional patent </B> to main patent No. 310831 Process for the production of a disazo dye The present invention relates to a process for the production of a disazo dye, which consists in that 1 mol of the 1- (4 ' -Amino-3'-methyl)
-benzoylamino-4-amino-benzene-3-carboxylic acid with 5-oxy- 7-sulfonaphthyl (2) -carbamic acid- (4 '- acetylamino-) - phenvjamid available diazomonoazo compound with 1 mol 1- (4'- Oxy-3'-carboxy) -phenyl-5-pyrazolone-3-carboxamide couples.
In the example, the parts mean parts by weight.
<I> Example </I> A neutralized, 8-10 cold suspension of the tetrazotized 1- (4'-amino-3'-methyl) -benzoylamino-4-aminobenzene-3- by coupling 28.5 parts carboxylic acid with 41.5 parts of 5-oxy-7-sulfonaphthyl (2) carbamic acid (4'-acetylamino) phenylamide available diazo monoazo intermediate compound is in a 30 warm solution of 26.3 parts 1- (4 '-Oxy-3'-carboxy)
phenyl-5-pyrazolone-3-carboxamide, 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 red shades with good lightfastness and washfastness using the copper plating process.
The abovementioned suspension of the diazo-monoazo intermediate compound is obtained when 28.5 parts of 1- (4'-amino-3'-methyl) -benzoy 1 = amino-4-aminobenzene-3-carboxylic acid are stirred in 800 parts of ice water and 50 parts of 301% hydrochloric acid were added to the suspension, followed by 46 parts of 30% sodium nitrite solution at 0.
A solution of 41.5 parts of 5-oxy-7-sulfonaphthyl (2) -carbamic acid- (4'-acetyl-amino) -phenylamide and 10 parts of sodium carbonate in 400 parts of water is allowed to run into the tetrazo solution, and the temperature is set the coupling compound to 8-10 and add about 20 parts of sodium bicarbonate in portions within one 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 diazomonazo intermediate compound separates out in red crystals.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH328660T | 1954-05-11 | ||
| CH310831T | 1954-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH328660A true CH328660A (en) | 1958-03-15 |
Family
ID=25735782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH328660D CH328660A (en) | 1954-05-11 | 1954-05-11 | Process for the preparation of a disazo dye |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH328660A (en) |
-
1954
- 1954-05-11 CH CH328660D patent/CH328660A/en unknown
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