CH208538A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH208538A CH208538A CH208538DA CH208538A CH 208538 A CH208538 A CH 208538A CH 208538D A CH208538D A CH 208538DA CH 208538 A CH208538 A CH 208538A
- Authority
- CH
- Switzerland
- Prior art keywords
- mol
- azo dye
- oxy
- parts
- dye
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 5
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 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 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid 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
- 150000001879 copper Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 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
- C09B35/38—Trisazo dyes ot the type
- C09B35/40—Trisazo dyes ot the type the component K being a dihydroxy or polyhydroxy compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass ein neuer Azo- farbstoff hergestellt werden kann, wenn man <B>1</B> Mol 1,3-Dioxybenzol einerseits mit<B>1</B> Mol der Diazoverbindung aus 1-Oxy-2-aminoben- zol-4-sulfamid und anderseits mit<B>1</B> Mol der Diazoazoverbindung, die bei der einseitigen Kupplungtetrazotierten4,
4'-DiaminodipheDyls mit 2-Oxy-l-beiizoesäure entsteht, vereinigt.
Der erhaltene Farbstoff bildet ein dunkel gefärbtes Pulver, das sich in Wasser und verdünnten Alkalien mit bräunlieber und in konzentrierter Schwefelsäure mit rotvioletter Farbe löst. Baumwolle und regenerierte Zel lulose werden aus Glaubersalz enthaltendem Bade in braunen Tönen gefärbt, die durch Nachbehandlung mit Metall-, insbesondere Kupfersalzen, vorzüglich licht- und wasch echt werden.
<I>Beispiel:</I> 18,4 Teile 4,4'-Diaminodiphenyl werden in bekannter Weise mit 52 Teilen konzen trierter Salzsäure und 14 Teilen Natrium- nitrit in die Tetrazoverbindung übergeführt. Diese lässt man zu einer bei 4<B>0</B> C gehaltenen Lösung fliessen, die man aus<B>15</B> Teilen 2-Oxy- 1-benzoesäure und<B>50</B> Teilen wasserfreiem Natriumcarbonat erhalten hat.
In kurzer Ut bildet sich die gelbe Diazoazoverbindung der Formel
EMI0001.0027
Diese kombiniert man nun mit dem Mono- azofarbstoff, den man erhält, wenn man die Diazoverbindung aus<B>18,8</B> Teilen 1-Oxy-2- aminobenzol-4-sLilfamid in Gegenwart von <B>25</B> Teilen wasserfreiem Natriumearbonat mit <B>11</B> Teilen 1,3-Dioxybenzol kuppelt.
Die Kupp lung zum Monoazofarbstoff ist sofort beendet, und die rote Lösung desselben wird nun zu der oben erhaltenen Diazoazoverbinclung ge geben, worauf eine braune Fällung des Tris- azofarbstoffes entsteht.
Man rührt nun<B>10-15</B> Stunden, erwärmt darauf auf<B>60 '</B> und gibt 200 Teile einer <B>15</B> Oi'oigen Kochsalzlösung zu, um eine gut filtrierbare Form des Farbstoffes zu erhalten. Man filtriert noch warm, trocknet und pul- verigiert den schwärzlicben Filterrückstand.
Process for the preparation of an azo dye. It has been found that a new azo dye can be produced if <B> 1 </B> mol 1,3-dioxybenzene on the one hand with <B> 1 </B> mol of the diazo compound from 1-oxy-2- aminobenzene-4-sulfamide and on the other hand with <B> 1 </B> mol of the diazoazo compound, which is tetrazotized in the one-sided coupling4,
4'-DiaminodipheDyls formed with 2-oxy-l-beiizoic acid, combined.
The dye obtained forms a dark-colored powder which dissolves in water and dilute alkalis with a brownish color and in concentrated sulfuric acid with a red-violet color. Cotton and regenerated cellulose are dyed from baths containing Glauber's salt in brown tones, which are extremely lightfast and washfast after treatment with metal salts, especially copper salts.
<I> Example: </I> 18.4 parts of 4,4'-diaminodiphenyl are converted into the tetrazo compound in a known manner with 52 parts of concentrated hydrochloric acid and 14 parts of sodium nitrite. This is allowed to flow to a solution kept at 4 ° C., which is made up of <B> 15 </B> parts of 2-oxy-1-benzoic acid and <B> 50 </B> parts of anhydrous Received sodium carbonate.
The yellow diazoazo compound of the formula is formed in brief Ut
EMI0001.0027
This is now combined with the monoazo dye that is obtained when the diazo compound is obtained from <B> 18.8 </B> parts of 1-oxy-2-aminobenzene-4-s-lilfamide in the presence of <B> 25 B> parts of anhydrous sodium carbonate coupled with <B> 11 </B> parts of 1,3-dioxybenzene.
The coupling to the monoazo dye is ended immediately, and the red solution of the same is now added to the diazoazo compound obtained above, whereupon a brown precipitate of the tris azo dye is formed.
The mixture is then stirred for <B> 10-15 </B> hours, then heated to <B> 60 '</B> and 200 parts of a <B> 15 </B> Oi'oigen saline solution are added to make it easy to filter To obtain the form of the dye. It is filtered while still warm, dried and the blackish filter residue is pulverized.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH208538T | 1938-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH208538A true CH208538A (en) | 1940-02-15 |
Family
ID=4446111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH208538D CH208538A (en) | 1938-07-22 | 1938-07-22 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH208538A (en) |
-
1938
- 1938-07-22 CH CH208538D patent/CH208538A/en unknown
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