CH228846A - Process for the preparation of a tetrakisazo dye. - Google Patents
Process for the preparation of a tetrakisazo dye.Info
- Publication number
- CH228846A CH228846A CH228846DA CH228846A CH 228846 A CH228846 A CH 228846A CH 228846D A CH228846D A CH 228846DA CH 228846 A CH228846 A CH 228846A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- brown
- combining
- nitrodiazobenzene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 12
- 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
- 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 description 3
- 239000000987 azo dye Substances 0.000 claims description 3
- 238000006193 diazotization reaction Methods 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 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
- 241001024304 Mino 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000203 mixture Substances 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
- 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 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
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000463 material 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
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 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 Tetrahisazofarbstoffes. Es wurde gefunden, dass man einen neuen Tetrakis#azofarbs(toff erhält, wenn man die Diaminoverbindung, die erhältlich ist durch Verseifen des @isazafaxbstoffes, der selbst .er hältlich ist durch! Vereinigen von 3-Diazophe- nyloxaminsäure mit 1-Amino-3-methylbenzol, Weiterdiazotieren :
des so erhaltenem Monoazo,- farbstoffes und Vereinigen in alkalis,chem Medium mit der 2-Amino-8-oxynaphthalin -6- sulfon:säure, tetrazotiert und mit 2 Mol 1,3- Dioxyben,ol vereinigt.
Der neue Farbstoff bildet ein dunkles, bronzierendes Pulver, das sich in Wasser mit rotbrauner, in konzentrierter Schwefelsäure mit grüner Farbre löst. Der Farbstoff färbt Baumwolle in violettbraunen Tönen,
die durch Behandeln mit Formaldehyd der mit 4-Ni trodiazoben.zol nachentwIekelt werden können. Die mit 4-Nitrodiazobenzol erhaltenen brau nen Töne ind ,gut waschecht und, sowohl neu tral als auch alkalisch, ausgezeichnet ätzbar. Beispiel,:
18,0 Teile 3-Aminophenyloxaminsäure werden in bekannter Weise diazotiert; die Diazolösung wird @dureh Zusatz von 20 % iger Natriumacetatlösung kongoneutral gestellt;
,dann wird eine Lösung von 10,7 Teilen. 1- Amino-3-methylbenzol, ,gelöist in 50 Teilen Wasser mit Hilfe von 13 Teilen 30%iger Salzsäure, zugegeben. Nach 24 Stunden wird ,der unlösliche Mono#azofarb#s#to#ff erbfiltriert,
dann mit 600 Teilen Wasser gut verrührt und durch Zusatz von Natriumhydroxydlösung in das Natriumsalz verwandelt. Dann werden eine Lösung von. 6,9 Teilen Natriumnitrit und 28 Teile Salzsäure von 30% zugegeben.
Das Diazotierungsig-emisch wird bei 8 biss 10 während 2 biss 2i/ Stunden gut gerührt und dann zu einer Lösung gegeben, die durch Lö sen von, 23;9 Teilten 2-Amino-8-oxynaphthralin- 6,-is#ulfonsäure unter Zusatz von 30 Teilen Na triumcarbonat bereitet wurde.
Nach mehr- stündigem Rühren wird der Disazofarbstoff ausgesal:zen und abfiltrie#rt. Der abfiltrierte Farbstoff wird mit 1000 Teilen Wasser wie .der angierührt,
zum Sieden erhitzt und .dann mit 140 Teilen 30 % iger Natriumhydroxyd- Lösung versetzt und während 1 bis 11/2 Stun den unter Rühren im Sieden erhalten. Hier auf wird mit Salzsäure neutralisiert, auf 15 abgekühlt, die Diaminodisazofarbstofflös!unb mit einer Lösung von 13,
8 Teilen Natrium nitrit und 55 Teilen Salzsäure von 30ö ver setzt und bei: 15 während 11/2 bis 2 Stunden gorührt.
Die :so erhaltene Suspension wird in eine Lösung eingerührt, .die in 300 Teilen Wasser 22,0 Teile 1,3@-Dioxyben@zol, und 60 Teile Na; triumcarbonat enthält. Man rührt einige Stun den bei Raumtemperatur, neutralisiert .sorg <B>fältig</B> den grössten Teil des Alkalicarbonates mit Salzsäure und filtriert.
Additional patent to main patent No. 226016. Process for the production of a tetrahisazo dye. It has been found that a new tetrakis azo color is obtained when the diamino compound, which is obtainable by saponifying the isazafax material, which itself is obtainable by combining 3-diazophenyloxamic acid with 1-amino-3 -methylbenzene, further diazotization:
of the monoazo obtained in this way - dye and combining in alkaline, chemical medium with 2-amino-8-oxynaphthalene-6-sulfone: acid, tetrazotized and combined with 2 mol of 1,3-dioxybene, ol.
The new dye forms a dark, bronzing powder that dissolves in water with a reddish-brown color and in concentrated sulfuric acid with a green color. The dye dyes cotton in violet-brown tones,
which can be developed after treatment with formaldehyde or with 4-Ni trodiazoben.zol. The brown tones obtained with 4-nitrodiazobenzene are washable and, both neutral and alkaline, excellently etchable. Example,:
18.0 parts of 3-aminophenyloxamic acid are diazotized in a known manner; the diazo solution is made congoneutral by adding 20% sodium acetate solution;
, then a solution of 10.7 parts. 1- Amino-3-methylbenzene, dissolved in 50 parts of water with the aid of 13 parts of 30% hydrochloric acid, was added. After 24 hours, the insoluble mono # azo color # s # to # ff is inherited by filtration,
then stirred well with 600 parts of water and converted into the sodium salt by adding sodium hydroxide solution. Then a solution of. 6.9 parts of sodium nitrite and 28 parts of 30% hydrochloric acid were added.
The diazotization mixture is stirred well at 8 to 10 for 2 to 2i / hours and then added to a solution which, by dissolving, 23; 9 parts, 2-amino-8-oxynaphthralin-6-isulphonic acid with addition of 30 parts of sodium carbonate was prepared.
After several hours of stirring, the disazo dye is salted out and filtered off. The filtered dye is mixed with 1000 parts of water like .der,
heated to boiling and then treated with 140 parts of 30% sodium hydroxide solution and obtained for 1 to 11/2 hours while stirring at the boil. Here on it is neutralized with hydrochloric acid, cooled to 15, the diaminodisazo dye solution with a solution of 13,
8 parts of sodium nitrite and 55 parts of 30ö hydrochloric acid are set and stirred at: 15 for 11/2 to 2 hours.
The suspension obtained in this way is stirred into a solution which, in 300 parts of water, contains 22.0 parts of 1,3 @ -Dioxyben @ zol, and 60 parts of Na; contains trium carbonate. The mixture is stirred for a few hours at room temperature, carefully neutralized, most of the alkali metal carbonate with hydrochloric acid and filtered.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH228846T | 1941-09-02 | ||
| CH226016T | 1942-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH228846A true CH228846A (en) | 1943-09-15 |
Family
ID=25726955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH228846D CH228846A (en) | 1941-09-02 | 1941-09-02 | Process for the preparation of a tetrakisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH228846A (en) |
-
1941
- 1941-09-02 CH CH228846D patent/CH228846A/en unknown
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