CH302392A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH302392A CH302392A CH302392DA CH302392A CH 302392 A CH302392 A CH 302392A CH 302392D A CH302392D A CH 302392DA CH 302392 A CH302392 A CH 302392A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- sulfonic acid
- aminophenyl
- preparation
- parts
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229920003043 Cellulose fiber Polymers 0.000 claims description 2
- 240000007817 Olea europaea Species 0.000 claims description 2
- 239000003795 chemical substances by application Substances 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 239000000203 mixture Substances 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
- 239000000243 solution Substances 0.000 description 2
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 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
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- -1 sulfuric acid methylbenzthiazolesulfonic acid Chemical compound 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/36—Trisazo dyes of the type
- C09B35/366—D is diphenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Azofarbstoff gelangt, wenn man eine Diazoverbindung des Aminodisazofarb- stoffes der Formel
EMI0001.0007
mit der 2-[4'-(8"-Oxynaphthyl- [2"] -amino- plienyl) ]-6-methylbenzthiazol-X',6"-disulfon- säure kuppelt,
in welcher die in X'-Stellung befindliche Sulfonsäuregruppe dieselbe Stel lung einnimmt wie die SulfoxLsäuregruppe der durch Sulfonieren von 2-(4'-Aminophenyl)- 6-methylbenzthiazol mittels konzentrierter Schwefelsäure erhältlichen 2- (4'-Aminophe- nyl)-6-methylbenzthiazolsulfonsäure, und den so erhaltenen Trisazofarbstoff in der Weise mit kupferabgebenden Mitteln behandelt, dass, unter .Aufspaltung der 14lethoxygruppe, der o,o'-Dioxyazokupferkomplex entsteht.
Der neue Farbstoff bildet ein dunkles Pul ver, das sich in Wasser mit brauner Farbe löst und die Cellulosefaser in echten Olivbraun- tönen färbt.
<I>Beispiel:</I> 18,4 Teile 4,4'-Diaminodiphenyl werden in üblicher Weise tetrazotiert und mit 15 Teilen 1- Oxybenzol - 2 - carbonsäure in wässerig natriumearbonatalkalischer Lösung bei 10 bis 15 gekuppelt. Die entstandene gelbbraune Suspension der Zwischenverbindung wird durch Zugabe von Essigsäure neutral gestellt und hierauf mit 21,7 Teilen 1-Amino-2-meth- oxybenzol - c0 - methansulfonsäure gekuppelt.
Nach Abspaltung der co-Methansulfonsäure wird in üblicher Weise der Disazofarbstoff abfiltriert, in 1600 Teilen Wasser aufge schlämmt, mit 7,5 Teilen Natriumnitrit ver setzt und durch Zusatz von 60 Teilen 30o/oiger Salzsäure bei 5 bis 10 diazotiert. Die schwer lösliche Diazoverbindung wird abfiltriert, in Wasser wieder suspendiert und in Gegenwart von 30 Teilen Natriumcarbonat mit 55 Teilen 2-[4'-(8"-Oxynaphthyl-[2"]-aminophenyl) ]-6- methylbenzthiazol-X,
6"-disulfonsäure gekup pelt.. Der so gebildete Trisazofarbstoff wird mit Natriumehlorid ausgesalzen, abfiltriert und durch Auswaschen mit verdünnter Na- triumchlo.ridlösung von allfälligen leichter löslichen Verunreinigungen befreit.
Zur Überführung in die-komplexe Kupfer verbindung löst man den Farbstoff in 1400 Teilen Wasser und 100 Teilen Pyridin, gibt eine w ässerig-ammoniakalische Lösung von Cupritetramminsulfat zu, deren Gehalt 25 Teilen kristallisiertem Kupfersulfat entspricht, und rührt 5 Stunden bei 90 bis 95 . Durch sorgfältiges Neutralisieren des Reaktions gemisches mit Salzsäure scheidet sich der Kupferkomplex ab und wird dann abfiltriert.
Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if one uses a diazo compound of the amino disazo dye of the formula
EMI0001.0007
with the 2- [4 '- (8 "-oxynaphthyl- [2"] -amino-plienyl)] -6-methylbenzthiazole-X', 6 "-disulfonic acid,
in which the sulfonic acid group in the X'-position occupies the same position as the sulfonic acid group of 2- (4'-aminophenyl) -6- obtainable by sulfonating 2- (4'-aminophenyl) - 6-methylbenzthiazole with concentrated sulfuric acid methylbenzthiazolesulfonic acid, and the trisazo dye thus obtained is treated with copper-donating agents in such a way that, with splitting of the 14lethoxy group, the o, o'-dioxyazo copper complex is formed.
The new dye forms a dark powder that dissolves in water with a brown color and colors the cellulose fiber in real olive brown tones.
<I> Example: </I> 18.4 parts of 4,4'-diaminodiphenyl are tetrazotized in the usual way and coupled with 15 parts of 1-oxybenzene-2-carboxylic acid in an aqueous sodium carbonate-alkaline solution at 10-15. The resulting yellow-brown suspension of the intermediate compound is neutralized by adding acetic acid and then coupled with 21.7 parts of 1-amino-2-methoxybenzene - c0 - methanesulfonic acid.
After the co-methanesulfonic acid has been split off, the disazo dye is filtered off in the usual manner, slurried in 1600 parts of water, 7.5 parts of sodium nitrite are added and the mixture is diazotized at 5 to 10 by adding 60 parts of 30% hydrochloric acid. The sparingly soluble diazo compound is filtered off, resuspended in water and, in the presence of 30 parts of sodium carbonate, with 55 parts of 2- [4 '- (8 "-oxynaphthyl- [2"] - aminophenyl)] -6-methylbenzthiazole-X,
6 "-disulfonic acid coupled .. The trisazo dye formed in this way is salted out with sodium chloride, filtered off and freed from any more easily soluble impurities by washing out with dilute sodium chloride solution.
To convert it into the complex copper compound, the dye is dissolved in 1400 parts of water and 100 parts of pyridine, an aqueous-ammoniacal solution of cuprite tetrammine sulfate, the content of which corresponds to 25 parts of crystallized copper sulfate, is added, and the mixture is stirred for 5 hours at 90 to 95. By carefully neutralizing the reaction mixture with hydrochloric acid, the copper complex separates out and is then filtered off.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH285138T | 1949-08-25 | ||
| CH302392T | 1952-02-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302392A true CH302392A (en) | 1954-10-15 |
Family
ID=25732480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302392D CH302392A (en) | 1949-08-25 | 1952-02-12 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302392A (en) |
-
1952
- 1952-02-12 CH CH302392D patent/CH302392A/en unknown
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