CH239333A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH239333A CH239333A CH239333DA CH239333A CH 239333 A CH239333 A CH 239333A CH 239333D A CH239333D A CH 239333DA CH 239333 A CH239333 A CH 239333A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- preparation
- disazo dye
- disazo
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 5
- 238000000034 method Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 12
- -1 aminoazo Chemical group 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229920003043 Cellulose fiber Polymers 0.000 claims description 2
- 235000005811 Viola adunca Nutrition 0.000 claims description 2
- 240000009038 Viola odorata Species 0.000 claims description 2
- 235000013487 Viola odorata Nutrition 0.000 claims description 2
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- AIOLRLMFOWGSPL-UHFFFAOYSA-N chembl1337820 Chemical compound C1=CC=C2C(N=NC3=C4C=CC(=CC4=CC(=C3O)S(O)(=O)=O)S(O)(=O)=O)=CC=CC2=C1 AIOLRLMFOWGSPL-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 237186. Verfahren zur Herstellung eines Disazofarbstoffes. Es- wurde gefunden, dass ein wertvoller Disazofarbstoff hergestellt werden kann, wenn man den diazotierten Aminoazofarb- stoff der Formel
EMI0001.0007
io mit 8-Oxychinolin vereinigt.
Der neue Farbstoff stellt ein schwarz braunes Pulver dar, das sich in Wasser und in verdünnten Alkalien mit bordeauxroter, in konzentrierter Schwefelsäure mit blauviolet ter Farbe löst und Cellulosefasern in bor deauxroten Tönen färbt, die beim Nachkup fern lieht- und waschechter werden. Der dem vorliegenden Verfahren als Aus gangsstoff dienende Aminoazofarbstoff der obigen Formel kann z. B. durch Kuppeln von diazotierter 2-Amino-3-naphth.oesäure mit 2-(4'-Aminobenzoyl)-amino-5-oxynaphthalin- 7-sulfonsäure erhalten werden.
Die Diazotie- rung kann in bekannter Weise z. B. so vor genommen werden, dass man eine Lösung bezw. Suspension des Aminoazofarbstoffes in neutralem oder schwach alkalischem Medium mit der nötigen Menge Nitrit versetzt und dann ansäuert.
Die Kupplung der diazotierten Amino- azoverbindung mit der 8-Oxychino-Iinkompo- nente erfolgt in alkalischem, beispielsweise Alkalihydroxyd und Alkalicarbonat enthal tendem Medium.
Beispiel: Der mit Kochsalz abgeschiedene, filtrierte und abgepresste Aminoazofarbstoff, der aus 18,7 Teilen 2-Amino-3'-naphthoesäure durch Diazotieren und Kuppeln mit 35,8 Teilen 2-(4'- Aminol)enzoyl)-amino-5-oxynaplhtlialin- 7-sulfonsäure in natriumcarbonatalkalischem Medium in bekannter Weise erhältlich ist, wird in 100(> Teilen Wasser suspendivi-t. Dann gibt man 7 'feile Nätriumnitrit zu und kühlt mit Eis auf 4 C.
Darnach versetzt man niit 31) Teilen Izonzenti@i < @rter S@ilzsäure und rührt etwa 21) Stunden. Die erhaltene 1?iazo- verhindung versetzt man nun mit einer Lö- sung von 14,5 Teilen 8-Oxy.cliinolin, 12 Tei len konzentrierter Salzsäure in 50 Teilen Wasser.
Man gibt 5'0 Teile einer Natrium- hydroxydlösung von 30% Gehalt an Na0H zu und rührt einige Stunden. Dann erwärmt man auf 6()-65 C, gibt 200 Teile Kochsalz zu, um eine gut filtrierbare Form des Disazo- farbstoffes zii erhalten, filtriert und trocknet den Niedersehlag.
<B> Additional patent </B> to main patent no. 237186. Process for the production of a disazo dye. It has been found that a valuable disazo dye can be produced by using the diazotized aminoazo dye of the formula
EMI0001.0007
io combined with 8-oxyquinoline.
The new dye is a black-brown powder that dissolves in water and in dilute alkalis with a claret-red color, in concentrated sulfuric acid with a blue-violet color and dyes cellulose fibers in reddish red tones, which are more durable and washable when copying. The aminoazo dye of the above formula serving as starting material for the present process can, for. B. by coupling diazotized 2-amino-3-naphth.oic acid with 2- (4'-aminobenzoyl) -amino-5-oxynaphthalene-7-sulfonic acid.
The diazotization can be carried out in a known manner, for. B. be taken before that you can bezw a solution. The required amount of nitrite is added to the suspension of the aminoazo dye in a neutral or weakly alkaline medium and then acidified.
The coupling of the diazotized amino azo compound with the 8-oxychino-Iinkomponente takes place in an alkaline medium containing, for example, alkali hydroxide and alkali carbonate.
Example: The aminoazo dyestuff separated out with common salt, filtered and pressed out, which is obtained from 18.7 parts of 2-amino-3'-naphthoic acid by diazotization and coupling with 35.8 parts of 2- (4'-aminol) enzoyl) -amino-5- oxynaplhtlialin- 7-sulfonic acid in sodium carbonate-alkaline medium is available in a known manner, is suspended in 100 (> parts of water. Then 7 'of sodium nitrite is added and it is cooled to 4 ° C. with ice.
Then 31 parts of izoncentic acid are added and the mixture is stirred for about 21 hours. A solution of 14.5 parts of 8-oxy.cliinoline and 12 parts of concentrated hydrochloric acid in 50 parts of water are then added to the 1? Iazo prevention.
50 parts of a sodium hydroxide solution with 30% NaOH content are added and the mixture is stirred for a few hours. The mixture is then heated to 6 ° -65 ° C., 200 parts of sodium chloride are added in order to obtain a readily filterable form of the disazo dye, the residue is filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH239333T | 1942-08-21 | ||
| CH237186T | 1943-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH239333A true CH239333A (en) | 1945-09-30 |
Family
ID=25728236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH239333D CH239333A (en) | 1942-08-21 | 1942-08-21 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH239333A (en) |
-
1942
- 1942-08-21 CH CH239333D patent/CH239333A/en unknown
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