CH226016A - Process for the preparation of a tetrakisazo dye. - Google Patents
Process for the preparation of a tetrakisazo dye.Info
- Publication number
- CH226016A CH226016A CH226016DA CH226016A CH 226016 A CH226016 A CH 226016A CH 226016D A CH226016D A CH 226016DA CH 226016 A CH226016 A CH 226016A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- amino
- nitrodiazobenzene
- combining
- Prior art date
Links
- 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 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 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
- 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 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 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 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- WDFSYFIRFAWWGG-UHFFFAOYSA-N N-(4-diazocyclohexa-1,5-dien-1-yl)acetamide Chemical compound C(C)(=O)NC1=CCC(C=C1)=[N+]=[N-] WDFSYFIRFAWWGG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 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
- 239000000987 azo dye Substances 0.000 claims 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 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000006193 diazotization reaction Methods 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
- 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
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
Verfahren zur Herstellung eines Tetrakisazofarbstoifes. Es wurde gefunden, daB man einen neuen Tetrakisazofarbstoff erhält, wenn man die Diaminoverbindung, die erhältlich ist durch Verseifen des Disazofarbstoffes, der selbst erhältlich ist durch Vereinigen von 1-Diazo- 4-acetylaminobenzol mit 1-Amino-3-methyl- benzol,
Weiterdiazotieren des so erhaltenen Monoazofarbstoffes und Vereinigen in alkali schem Medium mit der 2-Amino-8-ogynaph- thalin-6-sulfonsäure, tetrazotiert und mit 2 Mol 1,3-Diogybenzol vereinigt.
Der neue Farbstoff bildet ein. dunkles, bronzierendes Pulver, das sich in Wasser mit violetter, in konzentrierter Schwefelsäure mit grüner Farbe löst. Der Farbstoff färbt Baum wolle in violettschwarzen Tönen, die durch Behandeln mit Formaldehyd oder mit 4- Nitrodiazobenzol nachentwickelt werden kön nen.
Die mit 4-Nitrodiazobenzol erhaltenen braunschwarzen Töne sind gut waschecht und, sowohl neutral als auch alkalisch, aus gezeichnet ätzbar. <I>Beispiel:</I> 15,0 Teile 1-Amino-4-acetylaminobenzol werden in bekannter Weise diazotiert; die Diazolösung wird durch Zusatz von 20%iger Natriumacetatlösung kongoneutral gestellt; dann wird eine Lösung von 10,7 Teilen 1-Amino-3-methylbenzol, gelöst in 50 Teilen Wasser mit Hilfe von 13 Teilen 30%iger Salzsäure, zugegeben.
Nach 24 Stunden wird der unlösliche Monoazofarbstoff abfiltriert, dann mit 100 Teilen Wasser gut verpastet, mit weiteren 500 Teilen Wasser verdünnt. Dann werden eine Lösung von 6,9 Teilen Natriumnitrit und 28 Teile Salzsäure von <B>30%</B> zugegeben. Das Diazotierungsgemisch wird bei 15 bis 20 während 2 bis 21/2 Stun den gut gerührt und dann zu einer Lösung gegeben, die durch Lösen von 23,9 Teilen 2-Amino-8-ogynaphthalin-6-sulfonsäure unter Zusatz von 30 Teilen Natriumcarbonat berei tet wurde.
Nach mehrstündigem Rühren wird der schwerlösliche Disazofarbstoff abfiltriert. Der abfiltrierte Farbstoff wird mit 1000 Tei- len Wasser wieder angerührt, zum Sieden erhitzt und dann mit 140 Teilen 30%i--er Natriumhydroxydlösung versetzt und wäh rend 1 bis 11/2 Stunden unter Rühren im Sie den erhalten.
Hierauf wird mit Salzsäure neutralisiert, auf 15 abgekühlt, die Dia.mino- disazofarbstofflösung mit einer Lösung von 13,8 Teilen Natriumnitrit und 55 Teilen Salzsäure von<B>30%</B> versetzt und bei 15" wäh rend 11/2 bis 2 Stunden gerührt.
Die so er haltene Suspension wird in eine Lösung ein gerührt, die in 300 Teilen Wasser 22,0 Teile 1,3-Dioxybenzol und 60 Teile Natriumca.rbo- nat enthält. 1blan rührt einige Stunden bei Raumtemperatur, neutralisiert sorgfältig den grössten Teil des Alkalicarbonates mit Salz säure und filtriert.
Process for the preparation of a tetrakisazo dye. It has been found that a new tetrakisazo dye is obtained if the diamino compound, which is obtainable by saponifying the disazo dye, which is itself obtainable by combining 1-diazo-4-acetylaminobenzene with 1-amino-3-methylbenzene,
Further diazotization of the monoazo dye thus obtained and combining in an alkaline medium with the 2-amino-8-ogynaphthalene-6-sulfonic acid, tetrazotized and combined with 2 mol of 1,3-diogybenzene.
The new dye forms a. dark, bronzing powder that dissolves in water with purple color, in concentrated sulfuric acid with green color. The dye dyes cotton in violet-black tones, which can be developed after treatment with formaldehyde or with 4-nitrodiazobenzene.
The brown-black shades obtained with 4-nitrodiazobenzene are washable and, both neutral and alkaline, can be etched excellently. <I> Example: </I> 15.0 parts of 1-amino-4-acetylaminobenzene 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 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 pasted well with 100 parts of water and diluted with a further 500 parts of water. A solution of 6.9 parts of sodium nitrite and 28 parts of hydrochloric acid (30%) are then added. The diazotization mixture is stirred well at 15 to 20 for 2 to 21/2 hours and then added to a solution prepared by dissolving 23.9 parts of 2-amino-8-ogynaphthalene-6-sulfonic acid with the addition of 30 parts of sodium carbonate was tet.
After several hours of stirring, the sparingly soluble disazo dye is filtered off. The dyestuff filtered off is stirred up again with 1000 parts of water, heated to the boil, and 140 parts of 30% sodium hydroxide solution are added and the mixture is obtained for 1 to 11/2 hours with stirring.
It is then neutralized with hydrochloric acid, cooled to 15, the Dia.mino- disazo dye solution is mixed with a solution of 13.8 parts of sodium nitrite and 55 parts of hydrochloric acid of 30% and at 15 "for 11/2 to Stirred for 2 hours.
The suspension thus obtained is stirred into a solution which, in 300 parts of water, contains 22.0 parts of 1,3-dioxybenzene and 60 parts of sodium carbonate. 1blan stirs for a few hours at room temperature, carefully neutralizes most of the alkali metal carbonate with hydrochloric acid and filtered.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH226016T | 1942-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH226016A true CH226016A (en) | 1943-03-15 |
Family
ID=4454332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH226016D CH226016A (en) | 1942-07-17 | 1941-09-02 | Process for the preparation of a tetrakisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH226016A (en) |
-
1941
- 1941-09-02 CH CH226016D patent/CH226016A/en unknown
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