AT61471B - Process for the preparation of β-phenoxylated wool dyes. - Google Patents
Process for the preparation of β-phenoxylated wool dyes.Info
- Publication number
- AT61471B AT61471B AT61471DA AT61471B AT 61471 B AT61471 B AT 61471B AT 61471D A AT61471D A AT 61471DA AT 61471 B AT61471 B AT 61471B
- Authority
- AT
- Austria
- Prior art keywords
- phenoxylated
- preparation
- wool
- wool dyes
- blue
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 6
- 210000002268 wool Anatomy 0.000 title claims description 6
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- PYOZTOXFQNWBIS-UHFFFAOYSA-N phenol;sodium Chemical compound [Na].OC1=CC=CC=C1 PYOZTOXFQNWBIS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YFQWYOYPGHECGA-UHFFFAOYSA-N 1-amino-2-bromo-4-(4-methylanilino)-9,10-dioxo-2H-anthracene-1-sulfonic acid Chemical compound NC1(C(C=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)NC1=CC=C(C=C1)C)Br)S(=O)(=O)O YFQWYOYPGHECGA-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Beispiel 3.
25 kg 1-amino-2-brom-4-p-tolylaminoanthrachinonsulfosaures Natron werden mit einer Lösung von 15 kg Kalihydrat in 100 ty Phenol solange auf 1850 erhitzt, bis eine aufgearbeitete Probe sich in konzentrierter Schwefelsäure nicht mehr wie das Ausgangs- material mit blauer, sondern mit roter Farbe löst. Man gibt nach dem Erkalten 300 kg Wasser und 140 bis 150 kg Natronlauge (300/0) zu, saugt den in glänzenden Kristallen sich abscheidenden Farbstoff ab und wäscht ihn mit verdünnter Kochsalzlösung aus. Er löst sich in Wasser schwer mit rotstichigblauer Farbe und liefert auf Wolle violettblaue Färbungen von grosser Licht-und Chromechtheit und recht guter Walkechtheit.
Beispiel 4.
EMI2.1
werden in eine Mischung aus 300 kg Phenol und 75 kg Phenolnatrium eingetragen und solange zum Sieden erhitzt, bis eine aufgearbeitete Probe sich in konzentrierter Schwefelsäure nicht mehr mit violettroter, sondern schmutzigblauer Farbe löst. Aus der wie oben angegeben aufgearbeiteten Schmelze erhält man einen Wolle blau färbenden Farbstoff.
Beispiel 5.
10 kg 1.5-diamino-4. 8-dioxy-3-bromanthrachinon-7-sulfosaures Natrium werden mit 15 kg Phenol natrium und 80 kg Phenol zirka 6 Stunden gekocht, bis der entstandene Farbstoff keinen Bromgehalt mehr erkennen lässt. Die in bekannter Weise aufgearbeitete Schmelze liefert ein Wolle in blauen Tönen färbendes Produkt.
Beispiel 6.
25 kg 1. 5-Diamino-4. 8-dioxy-3. 7-dibromantbrachinon werden mit 35 leg Phenolnatrium und 25 kg Phenol bis zum Verschwinden der Bromreaktion gekocht. Beim Verdünnen der Schmelze mit 500/oigom Alkohol scheidet sich das 1. 5-Diamino-4. 8-dioxy-3. 7-diphenoxyanthrachinon in Blättchen ab. Der Körper ist in Alkohol unlöslich, in Nitrobenzol ziemlich schwer löslich mit blauer Farbe. Die farblose Lösung in konzentrierter Schwefelsäure nimmt auf Zusatz von Borsäure eine blaue Farbe an. Durch Erwärmen mit Schwefelsäuremonohydrat auf 80 bis 900 lässt er sich in eine Wolle blau färbende Sulfosäure Überführen.
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Example 3.
25 kg of 1-amino-2-bromo-4-p-tolylaminoanthraquinone sulfonic acid soda are heated to 1850 with a solution of 15 kg of potassium hydrate in 100 ty of phenol until a processed sample is no longer in concentrated sulfuric acid like the starting material with blue but with red paint dissolves. After cooling, 300 kg of water and 140 to 150 kg of sodium hydroxide solution (300/0) are added, the dye which separates out in shiny crystals is filtered off with suction and washed out with dilute sodium chloride solution. It is difficult to dissolve in water with a reddish-tinged blue color and, on wool, produces violet-blue dyeings of great light and chrome fastness and very good milled fastness.
Example 4.
EMI2.1
are added to a mixture of 300 kg phenol and 75 kg phenol sodium and heated to the boil until a processed sample no longer dissolves in concentrated sulfuric acid with a purple-red color, but a dirty blue color. A dye which dyes blue wool is obtained from the melt worked up as indicated above.
Example 5.
10 kg 1.5-diamino-4. Sodium 8-dioxy-3-bromoanthraquinone-7-sulphonic acid is boiled with 15 kg of sodium phenol and 80 kg of phenol for about 6 hours, until the resulting color no longer shows any bromine content. The melt, worked up in a known manner, provides a product which dyes wool in blue tones.
Example 6.
25 kg 1. 5-diamino-4. 8-dioxy-3. 7-dibromantbrachinon are boiled with 35 leg of sodium phenol and 25 kg of phenol until the bromine reaction disappears. When the melt is diluted with 500 / oigom alcohol, the 1,5-diamino-4 separates. 8-dioxy-3. 7-diphenoxyanthraquinone in flakes. The body is insoluble in alcohol, rather sparingly soluble in nitrobenzene with a blue color. The colorless solution in concentrated sulfuric acid turns blue when boric acid is added. By heating it with sulfuric acid monohydrate to 80 to 900, it can be converted into a sulfonic acid that turns blue in wool.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE61471X | 1911-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT61471B true AT61471B (en) | 1913-10-10 |
Family
ID=5630953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT61471D AT61471B (en) | 1911-08-30 | 1912-08-02 | Process for the preparation of β-phenoxylated wool dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT61471B (en) |
-
1912
- 1912-08-02 AT AT61471D patent/AT61471B/en active
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