CH308765A - 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
- CH308765A CH308765A CH308765DA CH308765A CH 308765 A CH308765 A CH 308765A CH 308765D A CH308765D A CH 308765DA CH 308765 A CH308765 A CH 308765A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- dye
- azo dye
- metal
- preparation
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 239000002184 metal Substances 0.000 title claims description 4
- 229910052751 metal Inorganic materials 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 10
- 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
- 240000007817 Olea europaea Species 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
- 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 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
- 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
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000000203 mixture Substances 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
- 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
- 239000012670 alkaline solution Substances 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
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 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
<B>Zusatzpatent</B> zum Hauptpatent Nr. 304039. Verfahren zur Herstellung eines metallhaltigen Azofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen, metallhaltigen Azofarbstoff ge langt, wenn man den Azofarbstoff der Formel
EMI0001.0005
in der Weise mit kupferabgebenden Mitteln behandelt, dass unter Aufspaltung der Alkoxy- gruppe der Komplex entsteht, welcher zwei Atome komplex gebundenes Kupfer im Mole kül enthält.
Der neue Farbstoff bildet ein dunkles Pulver, das sich in Wasser mit olivgrüner Farbe löst und Baumwolle in lichtechten, olivgrünen Tönen färbt.
Der als Ausgangsstoff dienende Farb stoff der obigen Formel wird zweckmässig durch Kupplung von diazotierter 1-Amino- benzol-2-carbonsäure-4-sulfonsäure mit 1-(4" Am.inostilben[4'] )--3-methyl -,5-pyrazolon-2,2'- disulfonsäure, Weiterdiazotierung und Kupp lung mit einer 1-Amino-2ralkoxynaphthalin-6- sulfonsäure, vorzugsweise 1-Amino-\?-methoxy- oder -2-äthoxynaphthalini6-sulfonsäure,
noch malige Diazotierung und Kupplung mit 2- Acetylamino - 5 - oxynaphthalin-7-sulfonsäure erhalten.
<I>Beispiel:</I> <B>21,7</B> Teile 1-Aminobenzol-2-carbonsäure-4- sulfonsäure werden in 150 eilen Wasser mit 11 Teilen wasserfreiem Natriumcarbonat ge löst, mit<B>25</B> Teilen 30prozentiger Salzsäure angesäuert und bei 5 bis 10 mit 6,9 Teilen Natriumnitrit, gelöst in<B>5</B>0 Teilen Wasser, diazotiert. Die Diazoverbindung wird in na- triumbiearbonatalkalischer Lösung mit 43, Tei len 1-(4"-Aminostilben[4'] )-3-methyl-5-pyra- zolon-2',
2"-disulfonsäure gekuppelt. Das über schüssige 1\Tatriumbicarbonat wird mit 'Salz- säure neutralisiert, die Lösung mit 6,9 Tei len Natriumnitrit versetzt und der Monoazo- farbstoff durch Eingiessen von 40 'Teilen 30- prozentiger Salzsäure wieder diazotiert. Nach 2= bis '3stündigem Rühren bei Raumtempera tur stumpft man mit Natriumacetat ab und kuppelt mit 2;
5y3 Teilen 1-Amino-2'-methoxy- naphthalin-6-sulfonsäure oder 2!6y7 'Teilen 1- Amino-2-äthoxynaphtha.Iin-6-sulfonsäure, ge löst als Natriumsalz mit 20 Teilen Natrium acetat in 200 Teilen Wasser: Durch allmäh liche Zugabe von 40 Teilen 10prozentiger Na- triumearbonatlösung wird die Kupplung be schleunigt.
Nach beendeter Kupplung wird das Kupplungsgemisch mit Natriumcarbonat alkalisch gemacht, der Disazofarbstoff ausge- salzen und abfiltriert. Die Färbstoffpaste wird in 1500 Teilen Wasser unter Zusatz von Natriumhydroxydlösung gelöst, mit 7 Teilen Natriumnitrit versetzt und durch Eingiessen von 40 Teilen 3prozentiger Salzsäure diazo- tiert. Man rührt etwa 1 Stunde bei Raum temperatur und trägt die abfiltrierte und in 15,
00 Teilen Eiswässer wieder verrührte Di- azoverbindung in eine auf 5 gekühlte Lö sung aus 28 Teilen 2 Acetylamino-5-oxy- naphthalin-7-sulfonsäure, 25 Teilen Natrium bicarbonat und 1'50 'Teilen Pyridin in 200 Teilen Wasser ein.
Nach beendeter Kupplung wird der Disazofarbstoff ausgesaIzen, abfil- triert und zur Überführung in den Kupfer komplex mit 50 Teilen kristallisiertem Kup fersulfat und 40 Teilen Natriumacetat in 3000, Teilen Wasser<B>10</B> Stunden am Rückfluss gekocht. Der Kupferkomplex wird alsdann ausgesalzen, abfiltriert und nach üblicher Me thode fertiggestellt.
<B> Additional patent </B> to main patent no. 304039. Process for the production of a metal-containing azo dye. It has been found that a valuable, metal-containing azo dye is obtained if one uses the azo dye of the formula
EMI0001.0005
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-bonded copper in the molecule.
The new dye forms a dark powder that dissolves in water with an olive green color and dyes cotton in lightfast, olive green tones.
The starting material dye of the above formula is expediently prepared by coupling diazotized 1-aminobenzene-2-carboxylic acid-4-sulfonic acid with 1- (4 "Am.inostilben [4 ']) - 3-methyl -, 5 -pyrazolone-2,2'-disulfonic acid, further diazotization and coupling with a 1-amino-2ralkoxynaphthalene-6-sulfonic acid, preferably 1-amino - \? - methoxy or -2-ethoxynaphthalenesulfonic acid,
repeated diazotization and coupling with 2-acetylamino - 5 - oxynaphthalene-7-sulfonic acid.
<I> Example: </I> <B> 21.7 </B> parts of 1-aminobenzene-2-carboxylic acid-4-sulfonic acid are dissolved in 150 parts of water with 11 parts of anhydrous sodium carbonate, with <B> 25 < / B> parts of 30 percent hydrochloric acid acidified and diazotized at 5 to 10 parts with 6.9 parts of sodium nitrite dissolved in 5 parts of water. The diazo compound is dissolved in sodium carbonate-alkaline solution with 43, parts 1- (4 "-Aminostilben [4 ']) -3-methyl-5-pyrazolon-2',
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 = stirring for 3 hours at room temperature is blunted with sodium acetate and coupled with 2;
5y3 parts of 1-amino-2'-methoxynaphthalene-6-sulfonic acid or 2! 6y7 'parts of 1- amino-2-ethoxynaphtha.Iin-6-sulfonic acid, dissolved as the sodium salt with 20 parts of sodium acetate in 200 parts of water: The clutch is accelerated by gradually adding 40 parts of 10 percent sodium carbonate solution.
After the coupling has ended, the coupling mixture is made alkaline with sodium carbonate, and 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, 7 parts of sodium nitrite are added and 40 parts of 3% hydrochloric acid are poured in to diazotise. The mixture is stirred for about 1 hour at room temperature and the filtered off and in 15,
00 parts of ice water re-stirred diazo compound in a solution, cooled to 5, of 28 parts of 2-acetylamino-5-oxynaphthalene-7-sulfonic acid, 25 parts of sodium bicarbonate and 1'50 parts of pyridine in 200 parts of water.
After coupling has ended, the disazo dye is salted out, filtered off and refluxed with 50 parts of crystallized copper sulfate and 40 parts of sodium acetate in 3000 parts of water for 10 hours to convert it into the copper complex. The copper complex is then salted out, filtered off and finished according to the usual method.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308765T | 1951-11-08 | ||
| CH304039T | 1952-10-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308765A true CH308765A (en) | 1955-07-31 |
Family
ID=25734709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308765D CH308765A (en) | 1951-11-08 | 1951-11-08 | Process for the preparation of a metal-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308765A (en) |
-
1951
- 1951-11-08 CH CH308765D patent/CH308765A/en unknown
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