CH190901A - Process for the production of a new anthraquinone dye. - Google Patents
Process for the production of a new anthraquinone dye.Info
- Publication number
- CH190901A CH190901A CH190901DA CH190901A CH 190901 A CH190901 A CH 190901A CH 190901D A CH190901D A CH 190901DA CH 190901 A CH190901 A CH 190901A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- production
- sulfonic acid
- anthraquinone dye
- dodecyloxyanilidoanthraquinone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000001000 anthraquinone dye Substances 0.000 title description 3
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical group [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000009963 fulling Methods 0.000 claims description 2
- 239000010446 mirabilite Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 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 claims description 2
- 235000010265 sodium sulphite Nutrition 0.000 claims description 2
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- VXMYUOSDIMLATO-UHFFFAOYSA-N 4-dodecoxyaniline Chemical compound CCCCCCCCCCCCOC1=CC=C(N)C=C1 VXMYUOSDIMLATO-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Anthrachinonfarbstofès. Wir haben gefunden, dass ein neuer Anthrachinonfarbstoff, 1-Amino-4-p-dodecyl- oxyanilidoarrthrachirron-2-sulfosäure,durch Be handlung von 1-Amirro-2-halogen-4-p-dodecyl- oxyanilidoanthr-achinon mit einem löslichen Sulfit erhalten werden kann.
Die Behandlung des 2-Halogen-l-amino- 4-p-dodecyloxyarrilidoanthrachinor)s mit Sulfit kann in Phenol vorgenommen werden.
1-Amirro-4-p-dodecyloxyanilidoanthrachi- non-2-sulfosäure ist neu. Sie ist dunkelblau und löst sich in Wasser mit blauer Farbe. Sie färbt Wolle und andere animalische Fasern aus neutralen oder leicht sauren Bädern, vorzugsweise mit dem Zusatz eines färbenden Hilfsmittels, wie Cetylnatriumsulfat oder Glaubersalz, in hellblauen Tönen von ausgezeichneter Festigkeit gegen strenges Waschen, Walken und Licht.
Beispiel: 20 Teile 1-Amirro-2-brom-4-p-dodecyloxy- anilidoanthrachinon (erhalten durch Umsetzung von Dodecylbromid mit p-Nitrophenol, Reduk tion und nachfolgender Umsetzung des resul tierenden p-Dodecyloxyanilins mit 1.3-Di- brom - 4 - aminoanthrachinon) werden in 240 Teilen geschmolzenem Phenol aufgelöst.
Die Lösung wird mit einer Lösung von 100 Teilen kristallisiertem Natriumsulfit in 120 Teilen Wasser in einen Autoklaven gebracht. Das Gemisch wird 8 Stunden lang auf 170-175 C erhitzt, dann das Phenol abgedampft, der Festkörper abgefiltert, getrocknet und durch Ausziehen der Unreinigkeiten mit kaltem Benzol gereinigt.
Process for the preparation of a new anthraquinone dye. We have found that a new anthraquinone dye, 1-amino-4-p-dodecyl oxyanilidoarrthrachirron-2-sulfonic acid, by treating 1-Amirro-2-halo-4-p-dodecyl-oxyanilidoanthr-aquinone with a soluble sulfite can be obtained.
The treatment of the 2-halo-1-amino-4-p-dodecyloxyarrilidoanthraquinor) s with sulfite can be carried out in phenol.
1-Amirro-4-p-dodecyloxyanilidoanthraquinone-2-sulfonic acid is new. It is dark blue and dissolves in water with a blue color. It dyes wool and other animal fibers from neutral or slightly acidic baths, preferably with the addition of a coloring agent such as cetyl sodium sulfate or Glauber's salt, in light blue shades of excellent resistance to severe washing, fulling and light.
Example: 20 parts of 1-amirro-2-bromo-4-p-dodecyloxy-anilidoanthraquinone (obtained by reacting dodecyl bromide with p-nitrophenol, reducing and then reacting the resulting p-dodecyloxyaniline with 1,3-di-bromine - 4 - aminoanthraquinone) are dissolved in 240 parts of molten phenol.
The solution is placed in an autoclave with a solution of 100 parts of crystallized sodium sulfite in 120 parts of water. The mixture is heated to 170-175 ° C. for 8 hours, then the phenol is evaporated off, the solid is filtered off, dried and cleaned by extracting the impurities with cold benzene.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB190901X | 1934-11-14 | ||
| CH187430T | 1935-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH190901A true CH190901A (en) | 1937-05-15 |
Family
ID=25721539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH190901D CH190901A (en) | 1934-11-14 | 1935-11-13 | Process for the production of a new anthraquinone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH190901A (en) |
-
1935
- 1935-11-13 CH CH190901D patent/CH190901A/en unknown
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