CH246986A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH246986A CH246986A CH246986DA CH246986A CH 246986 A CH246986 A CH 246986A CH 246986D A CH246986D A CH 246986DA CH 246986 A CH246986 A CH 246986A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- dye
- yellow
- disazo dye
- fastness
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- -1 aminoazo Chemical group 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000004627 regenerated cellulose Substances 0.000 claims description 4
- 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
- 150000003672 ureas Chemical class 0.000 claims description 3
- 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
- WBUWHFUHWRJTGA-UHFFFAOYSA-N [N-]=[N+]=C(CC(O)=C1C(O)=O)C=C1S(O)(=O)=O Chemical compound [N-]=[N+]=C(CC(O)=C1C(O)=O)C=C1S(O)(=O)=O WBUWHFUHWRJTGA-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 2
- ORJXGTWKJKWJFU-UHFFFAOYSA-N 4-amino-2-hydroxy-6-sulfobenzoic acid Chemical compound NC1=CC(O)=C(C(O)=O)C(S(O)(=O)=O)=C1 ORJXGTWKJKWJFU-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
- PTVDYARBVCBHSL-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu] PTVDYARBVCBHSL-UHFFFAOYSA-N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Disazofarbstoffes. Es wurde gefunden, dass man wertvolle gelb bis orange färbende Disazofarbstoffe erhält, wenn man zwei Moleküle eines Aminoazofarbstoffes der allgemeinen Formel
EMI0001.0006
worin 7 Wasserstoff, Alkyl oder Alkoxy und Y Wasserstoff, Alkyl, Alkoxy oder Acyl- amino bedeuten, mittels Phosgen verkettet.
Die Färbungen dieserFarbstoffeauf Baum wolle oder regenerierter Cellulose sind sehr gut weiss ätzbar und werden durch Behand lung mit kupferabgebenden Mitteln, insbe sondere bei neutraler Reaktion und in Gegen wart von wasserlöslichen hochmolekularen Polyamino- und Polyiminoverbindungen, welche befähigt sind, die Nassechtheiten von Substantiven Farbstoffen zu verbessern, vor züglich wasch- und lichtecht.
Und zwar zeigen sie den unerwarteten Befund, dass ihre Lichtechtheit durch die kombinierte Nachbehandlung mit kupferabgebenden und nassechtheitsverbessernden Mitteln bedeutend besser wird als durch Nachbehandlung mit kupferabgebenden Mitteln allein. Erfahrungs gemäss zeigen Farbstoffe, welche zur Bildung von Metallkomplexen befähigt sind, in der Regel ein umgekehrtes Verhalten. Das vorliegende Patent betrifft ein Ver fahren zur.
Herstellung eines Disazofarbstof- fes und ist dadurch gekennzeichnet; dass der durch Kuppeln von 4-Diazo-6-sulfosalicyl- säure auf 2-Methoxy-5-methyl-l-aminobenzol erhältliche Aminoazofarbstoff durch Behan deln mit Phosgen in das Harnstoffderivat übergeführt wird.
Der Farbstoff stellt ein braunes Pulver dar. Er löst sich in Wasser mit gelber, in kon zentrierter Schwefelsäure mit blauvioletter Farbe und färbt Baumwolle und regenerierte Cellulose in rotstichig gelben, rein weiss ätz baren Tönen, welche beim Nachbehandeln mit Kupferformiat und nassechtheitsverbes- sernden hochmolekularen wasserlöslichen Basen voller und gut wasch-, Wasser- und lichtecht werden.
<I>Beispiel:</I> Der aus der Diazoverbindung von 23;3 Teilen 4-Amino-6-sulfosalicylsäure und 18,7 Teilen 2 -Methoxy- 5 -methyl-1-aminobenzol durch Kuppeln hergestellte Aminoazofarb- Stoff wird in 1000 Teilen heissem Wasser unter Zusatz von überschüssiger Soda gelöst, durch Filtration geklärt und bei neutraler; schwach alkalischer oder essigsaurer Reak tion so lange mit Phosgen behandelt, bis er sieh völlig in das Harnstoff-Derivat verwan delt hat, welches sich aus der Lösung ab scheidet.
Hierauf wird filtriert und getrock net. Der Farbstoff färbt Baumwolle und regenerierte Cellulose in rotstichig gelben, rein weiss ätzbaren Tönen, welche beim Nach- behandeln- mit gupferformiat und nassecht- heitsverbessernden hochmolekularen wasser löslichen Basen voller und gut wasch-, wasser- und lichtecht werden.
Process for the preparation of a disazo dye. It has been found that valuable yellow to orange-colored disazo dyes are obtained if two molecules of an aminoazo dye of the general formula are obtained
EMI0001.0006
wherein 7 is hydrogen, alkyl or alkoxy and Y is hydrogen, alkyl, alkoxy or acylamino, linked by means of phosgene.
The dyeings of these dyes on cotton or regenerated cellulose can be very easily etched white and are treated with copper-releasing agents, especially in the case of a neutral reaction and in the presence of water-soluble, high-molecular polyamino and polyimino compounds, which are able to improve the wet fastness of nouns dyes , especially washable and lightfast.
In fact, they show the unexpected finding that their lightfastness becomes significantly better through the combined aftertreatment with copper-releasing and wet-fastness-improving agents than through aftertreatment with copper-releasing agents alone. Experience has shown that dyes which are capable of forming metal complexes usually behave in the opposite way. The present patent relates to a process for.
Production of a disazo dye and is characterized by this; that the aminoazo dye obtainable by coupling 4-diazo-6-sulfosalicylic acid to 2-methoxy-5-methyl-1-aminobenzene is converted into the urea derivative by treatment with phosgene.
The dye is a brown powder. It dissolves in water with a yellow, in concentrated sulfuric acid with a blue-violet color and dyes cotton and regenerated cellulose in reddish yellow, pure white etchable shades, which are water-soluble when treated with copper formate and water-fastness-improving high-molecular-weight water Bases are full and washable, water and lightfast.
<I> Example: </I> The aminoazo dye produced by coupling from the diazo compound of 23; 3 parts of 4-amino-6-sulfosalicylic acid and 18.7 parts of 2-methoxy-5-methyl-1-aminobenzene is used in 1000 Parts of hot water dissolved with the addition of excess soda, clarified by filtration and neutralized; Weakly alkaline or acetic acid reaction treated with phosgene until it has completely transformed into the urea derivative, which separates out of the solution.
It is then filtered and dried. The dye dyes cotton and regenerated cellulose in reddish yellow, pure white etchable shades, which when treated with gupfer formate and water-fastness-improving high-molecular water-soluble bases become fuller and well washable, water- and lightfast.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH246986T | 1946-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH246986A true CH246986A (en) | 1947-02-15 |
Family
ID=4465917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH246986D CH246986A (en) | 1946-01-14 | 1946-01-14 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH246986A (en) |
-
1946
- 1946-01-14 CH CH246986D patent/CH246986A/en unknown
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