AT27463B - Process for the preparation of azo dyes. - Google Patents
Process for the preparation of azo dyes.Info
- Publication number
- AT27463B AT27463B AT27463DA AT27463B AT 27463 B AT27463 B AT 27463B AT 27463D A AT27463D A AT 27463DA AT 27463 B AT27463 B AT 27463B
- Authority
- AT
- Austria
- Prior art keywords
- acid
- preparation
- azo dyes
- dyes
- blue
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title 1
- 239000002253 acid Substances 0.000 description 7
- 239000000975 dye Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 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
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JCTNVNANPZAULC-UHFFFAOYSA-N 2-methylbenzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=C(O3)C)=C3C=CC2=C1 JCTNVNANPZAULC-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 amido compound Chemical class 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Description
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sauer aufgelöst und unter gutem Rühren mit 30 Teilen fein pulverisiertem m-Nitro- benzoylcMorid and abwechselnd mit etwa Soda allmählich versetzt so dass die Reaktion der Flüssigkeit immer schwach sauer bleibt. Wenn eine herausgenommene Probe sich durch Sodazusatz an der Luft nicht mehr violett färbt, ist die Reaktion beendet. Man kocht auf, macht mit Salzsäure mineralsauer, kocht kurze Zeit, lässt erkalten und filtriert die ausgeschiedene -Nitrophenyl-1.2-naphthoxazol-5-oxy-7-sulfosäure ab.
Diese Säure vereinigt sich mit Diazoverbindungen zu klaren Farbstoffen, die etwas röter bzw. blauer färben als die entsprechenden Produkte aus der in Beispiel 1 genannten Methylnaphthoxazoloxysulfosäure.
So färben t. B. die Farbstoffe aus Tolidin oder Dianisidin und 2 Molekülen dieser Säure ungebeizte Baumwolle blaustichig violett. Beim Behandeln mit reduzierenden Agenzien geht die -Nitrophenyl-1.2-naphthoxazol-5-oxy-7-sulfosäure in die entsprechende Amidoverbindung über, für deren Darstellung folgendes Beispiel diene :
Beispiel 3. Die gemäss Beispiel 2 erhaltene Nitrosäure wird neutral aufgelöst und unter fortwährendem Rühren in ein kochendes Gemisch von 100 Teilen Eisenpulver, 500 Teilen Wasser und 3 Teilen Schwefelsäure eingetragen. Das Reaktionsgemisch soll immer schwach saner bleiben, was durch Zusatz von Schwefelsäure erreicht wird.
Nach 3stündigem Kochen wird alkalisch gemacht, abfiltriert und aus dem Filtrate die u.-Amido-
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Wird diese Säure in bekannter Weise mit Diazoverbindungen vereinigt, so entstehen klare rote, violette bis blaue Farbstoffe, die die Baumwolle direkt anfärben und auf der Faser durch aufeinander folgende Behandlung mit salpetriger Säure und ss-Naphthol in waschechte und lichtechte, klare, rote bis blaue Farbstoffe übergehen.
Der Farbstoff, erhalten durch Kuppeln des Zwischenproduktes aus Tolidin und 1 Molekül
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die aus Diazobenzoichlorid und 1-Naphthylamin-7-sulfosäure entsteht und der oben erwähnten Amidophenyloxazoloxysulfosäurefärbtviolettblau.
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Dissolve in acidic solution and gradually add 30 parts of finely pulverized m-nitrobenzoyl chloride and alternating with about soda, while stirring well, so that the reaction of the liquid always remains slightly acidic. If a sample that has been taken out no longer turns purple when exposed to soda, the reaction has ended. It is boiled up, made mineral acid with hydrochloric acid, boiled for a short time, allowed to cool and the precipitated -nitrophenyl-1,2-naphthoxazole-5-oxy-7-sulfonic acid is filtered off.
This acid combines with diazo compounds to form clear dyes which are somewhat redder or blue in color than the corresponding products from the methylnaphthoxazole oxysulfonic acid mentioned in Example 1.
So color t. B. the dyes from tolidine or dianisidine and 2 molecules of this acid unstained cotton bluish violet. When treated with reducing agents, the -nitrophenyl-1,2-naphthoxazole-5-oxy-7-sulfonic acid is converted into the corresponding amido compound, the following example serves to illustrate this:
Example 3. The nitro acid obtained according to Example 2 is dissolved neutrally and, with continuous stirring, added to a boiling mixture of 100 parts of iron powder, 500 parts of water and 3 parts of sulfuric acid. The reaction mixture should always remain slightly softer, which is achieved by adding sulfuric acid.
After 3 hours of boiling, it is made alkaline, filtered off and the u-amido-
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If this acid is combined in a known manner with diazo compounds, clear red, violet to blue dyes are formed which dye the cotton directly and turn the fibers into washfast and lightfast, clear, red to blue by successive treatment with nitrous acid and ss-naphthol Dyes pass over.
The dye obtained by coupling the intermediate of tolidine and 1 molecule
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which arises from diazobenzoichloride and 1-naphthylamine-7-sulfonic acid and the above-mentioned amidophenyloxazoloxysulfonic acid stains violet blue.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1904165102D DE165102C (en) | 1904-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT27463B true AT27463B (en) | 1907-02-11 |
Family
ID=5684909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT27463D AT27463B (en) | 1904-02-25 | 1905-10-20 | Process for the preparation of azo dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT27463B (en) |
-
1905
- 1905-10-20 AT AT27463D patent/AT27463B/en active
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