CH211005A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211005A CH211005A CH211005DA CH211005A CH 211005 A CH211005 A CH 211005A CH 211005D A CH211005D A CH 211005DA CH 211005 A CH211005 A CH 211005A
- Authority
- CH
- Switzerland
- Prior art keywords
- mol
- oxy
- azo dye
- parts
- preparation
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 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
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 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
- 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
- 238000003756 stirring 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
- C09B35/38—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
Zusatzpatent zum lIauptpatent Nr. <B>208538.</B> 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 Kupplung tetrazotierten 3,3'-Dimetlioxy-4,4'- diaminodiphenyls mit 3-Methvj-2-oxy-l-ben- zoesäure entsteht, vereinigt.
Der erhaltene Farbstoff bildet ein schwärz liches Pulver, das sieh, in Wasser und ver dünnten Alkalien mit bräunlieller und in konz. Schwefelsäure mit rotblauer Farbe löst. Baumwolle und regenerierte Zellulose werden aus Glaubersalz enthaltendem Bade in braunroten Tönen gefärbt, die durch NacUbehandlung mit Metall-, insbesondere Kupfersalzen, vorzüglich licht- und wasch echt werden.
<I>Beispiel:</I> 24,4 Teile 3,3'-Dimethoxy-4,4'-diamino- diphenyl werden in bekannter Weise mit <B>52</B> Teilen konz. Salzsäure und 14 Teilen Natriumnitrit in die Tetrazoverbindung über geführt. Diese lässt man zu einer bei 4'<B>C</B> gehaltenen Lösung fliessen, die man aus<B>18</B> Teilen 3-Metliyl-2-oxy-l-benzoesäure und 55 Teilen wasserfreiem Natriumcarbonat erhal ten hat.
In kurzer Zeit bildet sieh diebraune Diazoazoverbindung der Formel
EMI0001.0037
Diese kombiniert man nun mit dem Mono- azofarbste,ff, den man erhält, wenn man die Diazoverbindung aus<B>18,8</B> Teilen 1-Oxy-2- aminobenzol-4-suliamid in Gegenwart von <B>25</B> Teilen wasserfreiem Natriumcarbonat mit <B>11</B> Teilen 1,3-1)ioxybenzol kuppelt.
Die Kupplung zum Monoazofarbstoff ist sofort beendet und die rote Lösung desselben wird nun zu der oben erhaltenen Diazoazoverbin- dung gegeben, worauf eine braune Fällung des Trisazofarbstoffes entsteht.
Nach 24stündigem Rühren erhitzt man auf<B>65 '</B> und filtriert, trocknet und pulveri siert den schwärzlichen Filterrückstand.
Additional patent to main patent no. <B> 208538. </B> Process for the production 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,
the 3,3'-dimetlioxy-4,4'-diaminodiphenyl tetrazotized in the one-sided coupling is formed with 3-methoxy-2-oxy-1-benzoic acid, combined.
The dye obtained forms a blackish powder that you see in water and dilute alkalis with brownish and in conc. Dissolves sulfuric acid with a red-blue color. Cotton and regenerated cellulose are dyed from baths containing Glauber's salt in brown-red tones, which are extremely lightfast and washfast by treatment with metal salts, especially copper salts.
<I> Example: </I> 24.4 parts of 3,3'-dimethoxy-4,4'-diamino-diphenyl are concentrated in a known manner with 52 parts. Hydrochloric acid and 14 parts of sodium nitrite passed into the tetrazo compound. This is allowed to flow to a solution kept at 4 ° C, which is obtained from 18 parts of 3-methyl-2-oxy-1-benzoic acid and 55 parts of anhydrous sodium carbonate Has.
In a short time it forms the brown diazoazo compound of the formula
EMI0001.0037
This is now combined with the monoazo color, ff, which is obtained when the diazo compound is obtained from 18.8 parts of 1-oxy-2-aminobenzene-4-suliamide in the presence of 25 Parts of anhydrous sodium carbonate with 11 parts of 1,3-1) ioxybenzene coupled.
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 trisazo dye results.
After stirring for 24 hours, the mixture is heated to <B> 65 '</B> and filtered, dried and pulverized the blackish filter residue.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211005T | 1938-07-22 | ||
| CH208538T | 1938-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211005A true CH211005A (en) | 1940-08-15 |
Family
ID=25724534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211005D CH211005A (en) | 1938-07-22 | 1938-07-22 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211005A (en) |
-
1938
- 1938-07-22 CH CH211005D patent/CH211005A/en unknown
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