CH308763A - Process for the preparation of a metal-containing azo dye. - Google Patents
Process for the preparation of a metal-containing azo dye.Info
- Publication number
- CH308763A CH308763A CH308763DA CH308763A CH 308763 A CH308763 A CH 308763A CH 308763D A CH308763D A CH 308763DA CH 308763 A CH308763 A CH 308763A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- azo dye
- metal
- containing azo
- dye
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 239000002184 metal Substances 0.000 title claims description 4
- 229910052751 metal Inorganic materials 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 150000004699 copper complex Chemical class 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- OXQJOAGKNHVOAI-UHFFFAOYSA-N 5-amino-6-methoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(N)C(OC)=CC=C21 OXQJOAGKNHVOAI-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 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 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/16—Trisazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines metallhaltigen Azofarbstoffes. Es wurde gefunden, dass man zii einem wertvollen, metallhaltigen Azofarbstoff ge langt, wenn man den Azofarbstoff der Formel
EMI0001.0006
in der Weise mit kupferabgebenden Mitteln behandelt, da.ss unter Aufspaltung der Alkoxy- gruppe der Komplex entsteht, welcher zwei Atome komplex gebundenes Kupfer im Mole- kill enthält.
Der neue Farbstoff bildet ein dunkles Pulver, das sieh in Wasser mit grünoliver Farbe löst und Baumwolle in grünoliven Tönen färbt.
<I>Beispiel:</I> 2'1,7 Teile 1-Aminobenzol-2-carbonsäure-4- Sulfonsäure werden in 150 Teilen Wasser mit 11 Teilen wasserfreiem Natriumcarbonat ge löst, mit 25 Teilen 3üprozentigerSalzsäure angesäuert und bei 5 bis 1o mit- @6,9 eilen Natriumnitrit, gelöst in 50 Teilen Wasser, dianotiert.
Die Diazoverbindung wird in na t.riumbie.arbonatalkalischer Lösung mit 43 T'ei- len 1-(4"-Aminostilben[4'] )-3L-methyl-5-pyra- zolon-2',2"-disulfonsäure gekuppelt.
Das über- sehüssige Natriumbicarbonat wird mit Salz säure neutralisiert, die Lösung mit 6,9 Teilen Natriumnitrit versetzt und der Monoazofarb- Stoff durch Eingiessen von 40, Teilen 30pro- zentiger Salzsäure wieder diazotiert. Nach 2_ bis 3stündigem Rühren bei Raumtempera tur stumpft man mit Natriumacetat ab und kuppelt mit 25,3 'Teilen 1-Amino-2-methoxy- naphthalin-6-sulfonsäure,
gelöst als Natrium salz mit 20 'Teilen Natriumacetat in 2.00 Tei len Wasser. Durch allmähliche Zugabe von 40 Teilen 10prozentiger Natriumcarbonat- lösung wird die Kupplung beschleunigt. Nach beendeter Kupplung wird das Kupplungs- gemisch mit Na.triumearbonat alkalisch ge macht, der Disazofarbstoff ausgesalzen und abfiltriert. Die F'arbstoffpaste wird in 1500 Teilen Wasser unter Zusatz von Natrium hydroxydlösung gelöst,
mit 7 Teilen Natrium nitrit versetzt und durch Eingiessen von 40 Teilen 30prozentiger Salzsäure dianotiert. Man rührt etwa 1 Stunde bei Raumtempera tur und trägt die abfiltrierte und in 150'0 :Teilen Eiswasser wieder verrührte Dia.zover- bindung in eine auf 5 gekühlte Lösung aus 22,4 Teilen 2-Oxynaphthalin - 6 - sulfonsäure, 25 Teilen Natriumbicarbonat und<B>150</B> 'Teilen Pyridin in 200, Teilen Wasser ein.
Nach be endeter Kupplung wird der D:isazofarbstoff aasgesalzen, abfiltriert und zur Überführung in den Kupferkomplex mit 50 Teilen kristalli siertem Kupfersulfat und 40 Teilen Natrium acetat in 3000 Teilen Wasser 10 Stunden am Rückfluss gekocht. Der Kupferkomplex wird alsdann aasgesalzen, abfiltriert und nach üb- lieher Methode fertiggestellt.
Process for the preparation of a metal-containing azo dye. It has been found that one reaches a valuable, metal-containing azo dye if one uses the azo dye of the formula
EMI0001.0006
Treated with copper-releasing agents in such a way that, with splitting of the alkoxy group, the complex is formed which contains two atoms of complex-bound copper in the mole- kill.
The new dye forms a dark powder that dissolves in water with a green-olive color and dyes cotton in green-olive tones.
<I> Example: </I> 2'1.7 parts of 1-aminobenzene-2-carboxylic acid-4-sulfonic acid are dissolved in 150 parts of water with 11 parts of anhydrous sodium carbonate, acidified with 25 parts of 3% hydrochloric acid and at 5 to 10 with - @ 6.9 hours sodium nitrite, dissolved in 50 parts of water, dianotized.
The diazo compound is coupled with 43 parts of 1- (4 "-amino-stilbene [4 ']) -3L-methyl-5-pyrazolone-2', 2" -disulphonic acid in a sodium bicarbonate-alkaline solution.
The excess sodium bicarbonate is neutralized with hydrochloric acid, 6.9 parts of sodium nitrite are added to the solution and the monoazo dye is diazotized again by pouring in 40 parts of 30 percent hydrochloric acid. After stirring for 2 to 3 hours at room temperature, the mixture is blunted with sodium acetate and coupled with 25.3 parts of 1-amino-2-methoxynaphthalene-6-sulfonic acid,
dissolved as sodium salt with 20 parts of sodium acetate in 2.00 parts of water. The coupling is accelerated by the gradual addition of 40 parts of 10 percent sodium carbonate solution. After the coupling has ended, the coupling mixture is made alkaline with sodium carbonate, the disazo dye is salted out and filtered off. The dye paste is dissolved in 1500 parts of water with the addition of sodium hydroxide solution,
mixed with 7 parts of sodium nitrite and dianotized by pouring in 40 parts of 30 percent hydrochloric acid. The mixture is stirred for about 1 hour at room temperature and the Dia.zover- compound, which has been filtered off and stirred again in 150,000 parts of ice water, is added to a solution of 22.4 parts of 2-oxynaphthalene-6-sulfonic acid, 25 parts of sodium bicarbonate and cooled to 5 <B> 150 </B> 'parts pyridine in 200 parts water.
After coupling has ended, the disazo dye is ash salted, filtered off and refluxed for 10 hours with 50 parts of crystallized copper sulfate and 40 parts of sodium acetate in 3000 parts of water to convert it into the copper complex. The copper complex is then salted, filtered off and finished according to the usual method.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308763T | 1951-11-08 | ||
| CH304039T | 1952-10-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308763A true CH308763A (en) | 1955-07-31 |
Family
ID=25734707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308763D CH308763A (en) | 1951-11-08 | 1951-11-08 | Process for the preparation of a metal-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308763A (en) |
-
1951
- 1951-11-08 CH CH308763D patent/CH308763A/en unknown
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