CH218079A - Process for the preparation of a new anthrapyridone dye. - Google Patents
Process for the preparation of a new anthrapyridone dye.Info
- Publication number
- CH218079A CH218079A CH218079DA CH218079A CH 218079 A CH218079 A CH 218079A CH 218079D A CH218079D A CH 218079DA CH 218079 A CH218079 A CH 218079A
- Authority
- CH
- Switzerland
- Prior art keywords
- bluish
- butylaniline
- dye
- red
- new
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- XBNVWXKPFORCRI-UHFFFAOYSA-N 2h-naphtho[2,3-f]quinolin-1-one Chemical compound C1=CC=CC2=CC3=C4C(=O)CC=NC4=CC=C3C=C21 XBNVWXKPFORCRI-UHFFFAOYSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 4
- 238000009963 fulling Methods 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- HGUMYMRHRBCLIU-UHFFFAOYSA-N N1=CC=CC2=C(C=C3C(CC(C=C3)=O)=C3)C3=CC=C21 Chemical compound N1=CC=CC2=C(C=C3C(CC(C=C3)=O)=C3)C3=CC=C21 HGUMYMRHRBCLIU-UHFFFAOYSA-N 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- -1 9 -anthrapyridon-disulfonic acid Chemical compound 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Anthrapyridonfarbstoffes. Die vorliegende Erfindung betrifft ein jTerfahren zur Herstellung eines neuen An- thrapyri:donfarbstoffes, nämlich von 6-p-n- Butylanilin- 3 -p-n-butylrphenyl-1 :
9 -anthTa- pyridon-disulfosäure, gemäss welchem man 1:4-Di-p-n-butylanilinanthraehinon mono- aeetyliert, durch Ringschluss in 6-p-n-Butyyl- anili,n-3-p-n-buty'lphenyl-1 : 9 -anthrapyrid@on überführt und letzteres disulfoniert.
Der neue Farbstoff ist bläulichrot und löst sich in konzentrierter Schwefelsäure mit bläulichroter Farbe. Er löst sich in Wasser mit einer bläulichroten Färbung und färbt Wolle in hellen, bläulichroten Tönen von sehr guter Wasch-, Walk-, Schweiss- und Licht echtheit.
<I>Beispiel:</I> 100 Teile 1 : 4-Di-p-n-butylanilinanthra- chinon, 1.00 Teile Eisessig, 50 Teile Essig säureanhydrid und 0, 75 Teile 100 % ige Schwe felsäure -erden während 15 Minuten bei 98 bis 100 C gerührt. Die tiefrote Lösung wird auf 20' C gekühlt und mit 600 Teilen ,B- Äthogyäthyla!lkohol und 100 Teilen Wasser verdünnt. 150 Teile Natriumhydrogydpulver werden bei 20 bis<B>50'</B> C unter gutem Rüh ren hinzugefügt und das Gemisch wird wäh rend 1 Stunde auf 98 bis<B>100'</B> C erhitzt.
Nach Abkühlen auf 20' wird das Produkt filtriert, ferner mit Äthylalkohol und hier auf mit Wasser gewaschen und getrocknet. Durch Erhitzen mit 800 Teilen Ligroin (Sdp. 80 biss <B>100'</B> C) mit naehherigem Küh len, Filtrieren und Waschen wird das Pro dukt gereinigt.
Das bläulichrote kristallini sche Produkt, das 6-p-n-Butylanilin-3-p-n- butylphenyl-1 :9-anthrapyrid-on wird durch Lösen in 10 Teilen 10%igem Oleum sulfo- niert, während es eine halbe Stunde bei <B>35'</B> C gerührt wird.
Nach Einrühren,des Ge misches in Eis und Wasser wird das sulfo- nierte Produkt filtriert, in Wasser bei 80 bis <B>90'</B> C mit Natriumcarbonat neutralisiert und aus der Lösung mit Salz gefällt. Nach dem Abfiltrieren und Trocknen erhält man als re sultierenden Farbstoff die 6-p-n-Butyla.nilin- 3-p-n-butylphenyl-1 :
9 -anthrapyridon-disul- fosäure in Form des Natriumsalzes. Der Farbstoff färbt Wolle aus neutralem oder schwachsaurem Bade in hellen, bläülichroten Tönen von sehr guter Wasch-, Walk-, Schweiss- und. Lichtechtheit.
Process for the preparation of a new anthrapyridone dye. The present invention relates to a process for the production of a new anthrapyridone dye, namely 6-p-n-butylaniline-3-p-n-butylrphenyl-1:
9 -anthtapyridon-disulfonic acid, according to which 1: 4-di-pn-butylanilineanthraehinone is monoethylated by ring closure in 6-pn-butyylanili, n-3-pn-butylphenyl-1: 9 -anthrapyrid @on transferred and the latter disulfonated.
The new dye is bluish red and dissolves in concentrated sulfuric acid with a bluish red color. It dissolves in water with a bluish-red color and dyes wool in light, bluish-red tones that are very fast to washing, fulling, perspiration and light.
<I> Example: </I> 100 parts of 1: 4-di-pn-butylaniline anthraquinone, 1.00 part of glacial acetic acid, 50 parts of acetic anhydride and 0.75 parts of 100% sulfuric acid earth for 15 minutes at 98 to 100 C stirred. The deep red solution is cooled to 20 ° C. and diluted with 600 parts of B-Ethogyäthyla! Lkohol and 100 parts of water. 150 parts of sodium hydrogen powder are added at 20 to 50 ° C with thorough stirring and the mixture is heated to 98 to 100 ° C for 1 hour.
After cooling to 20 'the product is filtered, further washed with ethyl alcohol and here with water and dried. The product is cleaned by heating with 800 parts of ligroin (bp. 80 to <B> 100 '</B> C) with subsequent cooling, filtering and washing.
The bluish-red crystalline product, the 6-pn-butylaniline-3-pn-butylphenyl-1: 9-anthrapyrid-one, is sulfonated by dissolving it in 10 parts of 10% oleum, while it is at 35 for half an hour 'C is stirred.
After stirring the mixture into ice and water, the sulfonated product is filtered, neutralized in water at 80 to 90 ° C. with sodium carbonate and precipitated from the solution with salt. After filtering off and drying, the resulting dye is 6-p-n-Butyla.nilin-3-p-n-butylphenyl-1:
9 -anthrapyridon-disulfonic acid in the form of the sodium salt. The dye dyes wool from neutral or weakly acidic baths in light, bluish-red shades of very good washing, fulling, sweating and. Lightfastness.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB218079X | 1939-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH218079A true CH218079A (en) | 1941-11-30 |
Family
ID=10169156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH218079D CH218079A (en) | 1939-02-15 | 1940-02-06 | Process for the preparation of a new anthrapyridone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH218079A (en) |
-
1940
- 1940-02-06 CH CH218079D patent/CH218079A/en unknown
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