CH228847A - Process for the preparation of a tetrakisazo dye. - Google Patents
Process for the preparation of a tetrakisazo dye.Info
- Publication number
- CH228847A CH228847A CH228847DA CH228847A CH 228847 A CH228847 A CH 228847A CH 228847D A CH228847D A CH 228847DA CH 228847 A CH228847 A CH 228847A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- amino
- acid
- red
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 16
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000006193 diazotization reaction Methods 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
- SSQQBRZUIXIPIP-UHFFFAOYSA-N 5-diazo-2-nitrocyclohexa-1,3-diene Chemical compound [O-][N+](=O)C1=CCC(=[N+]=[N-])C=C1 SSQQBRZUIXIPIP-UHFFFAOYSA-N 0.000 claims 2
- ASVJGCDMHUQIOZ-UHFFFAOYSA-N 2-[(5-diazocyclohexa-1,3-dien-1-yl)amino]-2-oxoacetic acid Chemical compound [N+](=[N-])=C1CC(=CC=C1)NC(C(=O)O)=O ASVJGCDMHUQIOZ-UHFFFAOYSA-N 0.000 claims 1
- 241000896693 Disa Species 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-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 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 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 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RNEUWLIFSPFBQF-UHFFFAOYSA-N 2-(3-aminoanilino)-2-oxoacetic acid Chemical compound NC1=CC=CC(NC(=O)C(O)=O)=C1 RNEUWLIFSPFBQF-UHFFFAOYSA-N 0.000 description 1
- IKASFIMUPSVCMG-UHFFFAOYSA-N 4-nitropyridazine Chemical compound [O-][N+](=O)C1=CC=NN=C1 IKASFIMUPSVCMG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000725 suspension Substances 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
- C09B35/50—Tetrazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 226016. Verfahren zur Herstellung eines Tetrakisazofarbstoffes. Es wunde gefunden, dass man einen neuen Tetrakisazofarbstoff erhält, wenn man :die Diaminoverbindung, die erhältlich ist;
durch Verseifen des Disazofarbstoffes, dem selbst er hältlich ist durch Vereinigen von 3-Diazo, ph enyloxaminisäure mit 1-Amino-3-methyl- benzol, Weiterdiazatieren :
des so erhaltenen Monoazofarbsto,ffes und Vereinigen in alk@ali- schem Meldium mit der 2-Amino-5-oxynapli th@alin-7-oulfo#nsäure, tetrazotiert und mit 2 Mal 1,3-Dioxybenzol vereinigt.
Der neue Farbstoff bildet ein dunkles, bronzierendes Pulver, das sich in Wasser mit rotvioletter, in; konzentrierter Schwefelsäure mit grüner Farbe löst. Der Farbstoff färbt Baumwolle in rotvioletten Tönen, die durch Behandeln mit Formaldehyd oder mit 4-Ni- tro,diazobienzo1 nachentwvekelt werden können.
Die mit 4-Nitro,diazabenzol erhaltenen brau nen Töne sind ,gut waschecht und, ,sowohl neu tral als auch alkalisch, ausgezeichnet ätzbar. Beispiel: 18,0 Teilte 3 -Aminophenyloxaminsäure werden; in bekannter Weise diazofiert;
die Diazolösung wird durch Zusatz von 20 % iger Natriumacetatlösung kongon#neutral gestellt;
.dann wird eine Lösung von 10,7 Teilen 1- Amino-3-methylbenzol, gelöst in 50 Teilen Was,s@er mit Hilfe von 13 Teilen 30%igeLr Salzsäure, zugegeben. Nach 24 Stunden wird der unlösliche Monoazofarbstoff abfiltriert,
.dann mit 600 Teilen Wasser gut verrühmt und durch Zusatz von Natriumhydroxydlösung in. d" Natriumselz verwandelt. Dann werden eine Lösung von 6,9 Teilen Natriumnitrit und 28 Teile Salzsäure von 30% zugegeben.
Das Diazotierungs@gemisch wird bei 8 bis 10 während 2 bis 21/ Stunden ,gut gerühmt und dann zu einer Lösung gegeben,,die -durch Lö sen von 23,
9 Teilen 2-Amino-5-oxynaphtha- lin-7-suMonsäuTe unter Zusatz von 30 Teilen Natriumearbonat bereitet wurde. Nach mehr- otündigem Rühren wind der Disazofarbstoff aus,-gesalzen und abfiltriert. Der abfiltrierte Farbstoff wird mit 1000 Teilen Wasser wie der angerührt, zum Sieden erhitzt und dann mit 14,
0 Teilen 30 % iger Natriumhydraxyd- lösUng versetzt und während 1 bis 11/2 Stun- ,den unter Rühren im Sieden erhalten.
Hierauf wird mit Salzsäure neutralisiert, auf 15 ab- gekühlt"dieDiaminodisazofarbstofflösung mit einer Lösung von 13,8 Teilen Natriumnitrit und 55 Teilen Salzsäure von<B>30%</B> versetzt und bei 15 während 11/2 bis 2 Stunden ge- ruh rt.
Die so erhaltene Suspension wird in eine Lösung eingerührt, die in 300 Teilen, Wasser 22,0 Teile 1,3-Dioxybenzol und 60 Teile Na- triumcarbonat enthält. Man rührt einige Stunden bei Raumtemperatur, neutralisiert sorgfältig den .grössten Teil,des Alkalicarbo- nates mit Salzsäure und filtriert.
Additional patent to main patent No. 226016. Process for the production of a tetrakisazo dye. It has been found that a new tetrakisazo dye can be obtained by: the diamino compound that is available;
by saponifying the disazo dye, which itself is available by combining 3-diazo, ph enyloxamic acid with 1-amino-3-methylbenzene, further diazation:
of the monoazo dye obtained in this way and combining in alk @ ali- shem Meldium with 2-amino-5-oxynapli th @ alin-7-sulfonic acid, tetrazotized and combined with 2 times 1,3-dioxybenzene.
The new dye forms a dark, bronzing powder that turns red-violet in water, in; concentrated sulfuric acid with a green color. The dye dyes cotton in red-violet tones, which can be redeveloped by treatment with formaldehyde or with 4-nitro, diazobienzo1.
The brown tones obtained with 4-nitro-diazabenzene are washable and, both neutral and alkaline, excellently etchable. Example: 18.0 parts of 3-aminophenyloxamic acid become; diazofed in a known manner;
the diazo solution is rendered kongon # neutral by adding 20% sodium acetate solution;
Then a solution of 10.7 parts of 1-amino-3-methylbenzene, dissolved in 50 parts of water with the aid of 13 parts of 30% strength hydrochloric acid, is added. After 24 hours, the insoluble monoazo dye is filtered off,
.then thoroughly boiled with 600 parts of water and converted into .d "sodium salt by adding sodium hydroxide solution. Then a solution of 6.9 parts of sodium nitrite and 28 parts of 30% hydrochloric acid are added.
The diazotization mixture is boiled well at 8 to 10 for 2 to 21 / hours and then added to a solution, the -by dissolving 23,
9 parts of 2-amino-5-oxynaphthalin-7-suMonsäuTe with the addition of 30 parts of sodium carbonate was prepared. After several hours of stirring, the disazo dye winds out, salted and filtered off. The filtered dye is mixed with 1000 parts of water like that, heated to boiling and then with 14,
0 parts of 30% sodium hydroxide solution are added and kept at the boil for 1 to 11/2 hours with stirring.
It is then neutralized with hydrochloric acid, cooled to 15%, the diamino disazo dye solution is admixed with a solution of 13.8 parts of sodium nitrite and 55 parts of 30% hydrochloric acid and left to rest at 15 for 11/2 to 2 hours rt.
The suspension obtained in this way is stirred into a solution which contains, in 300 parts of water, 22.0 parts of 1,3-dioxybenzene and 60 parts of sodium carbonate. The mixture is stirred for a few hours at room temperature, the largest part of the alkali carbonate is carefully neutralized with hydrochloric acid and filtered.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH228847T | 1941-09-02 | ||
| CH226016T | 1942-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH228847A true CH228847A (en) | 1943-09-15 |
Family
ID=25726956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH228847D CH228847A (en) | 1941-09-02 | 1941-09-02 | Process for the preparation of a tetrakisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH228847A (en) |
-
1941
- 1941-09-02 CH CH228847D patent/CH228847A/en unknown
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