DE2500019C3 - Monoazo dye, process for its preparation and its use - Google Patents
Monoazo dye, process for its preparation and its useInfo
- Publication number
- DE2500019C3 DE2500019C3 DE19752500019 DE2500019A DE2500019C3 DE 2500019 C3 DE2500019 C3 DE 2500019C3 DE 19752500019 DE19752500019 DE 19752500019 DE 2500019 A DE2500019 A DE 2500019A DE 2500019 C3 DE2500019 C3 DE 2500019C3
- Authority
- DE
- Germany
- Prior art keywords
- dye
- potassium
- monoazo dye
- preparation
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 14
- 238000007792 addition Methods 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 4
- 239000003792 electrolyte Substances 0.000 claims description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M Potassium bicarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 3
- 230000001808 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
- 239000011736 potassium bicarbonate Substances 0.000 claims description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 3
- 229940094025 potassium bicarbonate Drugs 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 150000003112 potassium compounds Chemical class 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000012970 cakes Nutrition 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- QZEDXQFZACVDJE-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 QZEDXQFZACVDJE-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N Sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Description
Gegenstand der Erfindung ist der Farbstoff der FormelThe invention relates to the dye of the formula
KO3SKO 3 S
ClCl
Der Farbstoff wird bevorzugt in Mischungen mit wasserlöslichen Nichtelektrolyten wie Dextrin, Zucker, Polyvinylpyrrolidon, Harnstoff oder anionischen Dispergiermitteln wie Ligninsulfonsäuren, Alkylnaphthalinsulfonsäuren, Kondensationsprodukte aus Naphthalin, Formaldehyd und Schwefelsäure, Alkyl- oder Alkylarylsulfonsäuren, und Monoschwefelsäureester von Alkanolen eingesetzt Darüber hinaus werden häufig geringe Mengen Entstaubungsmittel wie öle, Phthalsäureester oder nichtionogene Tenside zugesetztThe dye is preferred in mixtures with water-soluble non-electrolytes such as dextrin, sugar, Polyvinylpyrrolidone, urea or anionic dispersants such as ligninsulphonic acids, alkylnaphthalenesulphonic acids, Condensation products of naphthalene, formaldehyde and sulfuric acid, alkyl or Alkylarylsulfonic acids, and monosulfuric acid esters of alkanols are also used often small amounts of dedusting agents such as oils, phthalic acid esters or non-ionic surfactants are added
Fasermaterialien aus natürlichen oder synthetischen Polyamiden.Fiber materials made from natural or synthetic polyamides.
Gegenstand der vorliegenden Erfindung ist weiterhin ein Verfahren zur Herstellung des Farbstoffs gemäß S Anspruch 1, dadurch gekennzeichnet, daß man eine wäßrige Lösung oder Dispersion der nach der Kupplung isolierten freien Sulfonsäure durch Zugabe von alkalisch reagierenden Kaliumverbindungen, insbesondere Kaliumhydroxid, Kaliumcarbonat oder Kaliumbicarbonat auf einen pH-Wert >4, bevorzugt 5—7 stellt und gegebenenfalls mach Zusatz von Nichtelektrolyten oder anionischen Dispergiermitteln trocknetThe present invention furthermore relates to a process for the preparation of the dye according to S claim 1, characterized in that an aqueous solution or dispersion according to the Coupling isolated free sulfonic acid by adding alkaline potassium compounds, in particular Potassium hydroxide, potassium carbonate or potassium bicarbonate to a pH value> 4, preferably 5-7 and optionally with the addition of non-electrolytes or anionic dispersants
Die Trocknung kann z. B. in einem Umluftschrank, mit Walzentrocknen; Schaufeltrockner, bevorzugt jedoch durch Sprühtrocknung mit einer Einstoff- oder Zweistoffdüse oder Zerstäuberdüse erfolgen. Es ist auch möglich, daß man die trockene Sulfonsäure mit Kaliumhydroxid, Kaliumcarbonat oder Kaliumbicarbonat gegebenenfalls unter Zusatz von Nichtelektrolyten oder anionischen Dispergiermitteln mischtThe drying can, for. B. in a circulating air cabinet, with roller drying; Paddle dryer, but preferably by spray drying with a single-component or Two-substance nozzle or atomizer nozzle take place. It is also possible that you can use the dry sulfonic acid Potassium hydroxide, potassium carbonate, or potassium bicarbonate optionally with the addition of non-electrolytes or anionic dispersants
Das erfindungsgemäße Farbstoffkaliumsalz zeichnet sich gegenüber dem Natriumsalz durch die überraschend höhere Löslichkeit in Wasser aus.The dye potassium salt according to the invention is surprisingly distinguished from the sodium salt higher solubility in water.
37 g 2,5-DichlorsuUanilsäure werden in 270 ml Wasser und mit 50 g 32%iger Salzsäure und 36 g 30%iger Natriumnitritlösung bei 10— 15° C diazo tier t Nach einer halben Stunde Rühren bei 10—15°C wird der Überschuß an Nitrit mit Amidosulfonsäure zerstört 28 g 5-ImJno-3-methyl-l-phenyl-2-pyrazolin werden in 180 ml Wasser und 25 g 32%iger Salzsäure gelöst und mit 5 g Aktivkohle geklärt Diese Lösung wird auf 830 ml bei 15° C aufgefüllt. Die kalte Lösung des diazotierten Amins wird zugegeben, gefolgt durch die Zugabe von ungefähr 250 ml 20%iger wäßriger Natriumacetatlösiiing zu Einstellung von pH 4. Nach Beendigung der Kupplung wird der Farbstoff gegebenenfalls unter Zusatz von Wasser durch Erhitzen gelöst und nach Zugabe von Aktivkohle geklärt Anschließend wird das noch heiße Filtrat mit 30% Salzsäure auf pH 03—I gestellt, 15—30 Minuten auf 80—90°C erhitzt und anschließend der Farbstoff abgesaugt37 g of 2,5-dichlorosuUanilic acid are dissolved in 270 ml of water and with 50 g of 32% hydrochloric acid and 36 g of 30% sodium nitrite solution at 10-15 ° C diazo tier t Stirring for half an hour at 10-15 ° C, the excess nitrite is destroyed with sulfamic acid 28 g of 5-ImJno-3-methyl-1-phenyl-2-pyrazoline are in 180 ml of water and 25 g of 32% hydrochloric acid dissolved and clarified with 5 g of activated charcoal. This solution is dissolved 830 ml made up at 15 ° C. The cold solution of the diazotized amine is added, followed by the Add about 250 ml of 20% aqueous sodium acetate solution to adjust pH 4. After At the end of the coupling, the dye is dissolved by heating, if appropriate with the addition of water and clarified after the addition of activated charcoal. Then the still hot filtrate is adjusted to pH with 30% hydrochloric acid 03-1, heated to 80-90 ° C for 15-30 minutes and then sucked off the dye
Man kann aber auch den Farbstoff bei pH 4 isolieren, den Preßkuchen mit Wasser anrühren, mit verdünnter Salzsäure auf pH 1 stellten, 15—30 Minuten auf 80—9O0C erhitzen, die Farbstoffsäure anschließend absaugen.One can also isolate the dye at pH 4, touch the press cake with water, set with dilute hydrochloric acid to pH 1, 15-30 minutes at 80-9O 0 C Heat, then aspirate the dye acid.
188 g wäßriger Preßkuchen der Farbstoffsäure (entsprechend 136 g Trockenfarbstoff) werden mit 600 ml Wasser angerührt, mit verdünnter Kalilauge auf pH 6 gestellt (ca. 22 g KOH), anschließend mit 38 g Dextrin und 4 g Natriumsalz der Dibutylnaphthalinsulfonsäure vermischt Diese Mischung wird mit einer Zweistoffdüse sprühgetrocknet, wobei die Temperatur der eingehenden Luft im Sprühtrockner 180° C und die der ausgehenden Luft 8O0C beträgt Man erhält ein gelbes Farbstoffpulver mit einer sehr guten Löslichkeit in heißem und kaltem Wasser. In 250 ml Wasser lösen sich bei Zimmertemperatur mindestens 7,5 g des Farbstoffpulvers.188 g of aqueous press cake of the dye acid (corresponding to 136 g of dry dye) are mixed with 600 ml of water, adjusted to pH 6 with dilute potassium hydroxide solution (about 22 g of KOH), then mixed with 38 g of dextrin and 4 g of the sodium salt of dibutylnaphthalenesulfonic acid a two-fluid nozzle spray drying, wherein the temperature of the incoming air in the spray drier 180 ° C and the outgoing air is 8O 0 C, giving a yellow dye powder with a very good solubility in hot and cold water. At least 7.5 g of the dye powder dissolve in 250 ml of water at room temperature.
Claims (3)
1. Monoazofarbstoff der FormelPatent claims:
1. Monoazo dye of the formula
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752500019 DE2500019C3 (en) | 1975-01-02 | Monoazo dye, process for its preparation and its use | |
| GB4263475A GB1490139A (en) | 1975-01-02 | 1975-10-17 | Water-soluble monoazo dyestuffs |
| FR7600032A FR2296669A1 (en) | 1975-01-02 | 1976-01-02 | AZOIC COLORANTS, THEIR OBTAINING AND THEIR APPLICATION |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752500019 DE2500019C3 (en) | 1975-01-02 | Monoazo dye, process for its preparation and its use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2500019A1 DE2500019A1 (en) | 1976-07-15 |
| DE2500019B2 DE2500019B2 (en) | 1977-03-17 |
| DE2500019C3 true DE2500019C3 (en) | 1977-11-24 |
Family
ID=
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