CH180272A - Process for preparing a coloring reaction product obtained from a trisazo dye. - Google Patents
Process for preparing a coloring reaction product obtained from a trisazo dye.Info
- Publication number
- CH180272A CH180272A CH180272DA CH180272A CH 180272 A CH180272 A CH 180272A CH 180272D A CH180272D A CH 180272DA CH 180272 A CH180272 A CH 180272A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo
- product obtained
- reaction product
- dye
- nitro
- Prior art date
Links
- 239000007795 chemical reaction product Substances 0.000 title claims description 3
- 238000004040 coloring Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000010985 leather Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 239000000975 dye Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XHVFCOOFJKCIAP-UHFFFAOYSA-N 4-n-(4-nitrophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1 XHVFCOOFJKCIAP-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000991 leather dye Substances 0.000 description 1
- 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 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines ans einem Trisazofarbstoff erhaltenen, färbenden Reaktionsproduktes. Es wurde gefunden, dass ein wertvoller, brauner Farbstoff von noch unbekannter Konstitution entsteht, wenn man die Verbin dung 4-Nitro-4'-aminodiphenylamin-?-sulfon- # < lure -ftz0-1- a.minonaphthalin-6 \7-sulf onsäure Z(technisches Gemisch)-azo-1,3-dioxybenzol- azo-4-nitro-l-aminobenzol bei Gegenwart von wässerigem Ammoniak und einem Schwer metall mit Oxydationsmitteln,
vorzugsweise mit Luft, behandelt. Der neue Farbstoff stellt ein schwärzliches Pulver dar, das sich in Wasser mit brauner und in konzentrierter Schwefelsäure mit blauer Farbe löst. Im Gegensatz zum Ausgangsfarbstoff färbt er Wolle und Seide kaum mehr an, dagegen er- zeugt er auf Leder ein schönes, sattes Braun, dessen Farbton von dem Grade der Oxyda tion abhängig ist.
Diese Lederfärbungen sind t tius gezeichent durch hervorragende Echtheit gegen Licht und alkalischen Fettliquor, so wie organische und anorganische Säuren.
<I>Beispiel:</I> 31 Teile 4-Nitro-4'-aminodiphenylamin-2- sulfonsäure werden in üblicher Weise diazo- tiert und mit 23 Teilen 1- Aminonaphthalin- 6/' 7-sulfonsäure (technisches Gemisch) in essig saurer Lösung gekuppelt.
Der ausgeschiedene und abfiltrierte Monoazofarbstoff wird mit Natronlauge gelöst, in bekannter Weise in direkt diazotiert und in sodaalkalischer Lö sung in der gälte mit 11 Teilen 1,3-Dioxy- benzol vereinigt.
Wenn die Bildung des Disazofarbstoffes beendigt ist, wird er in sodaalkalischer Lösung mit der Diazoverbin- dung aus<B>13,8</B> Teilen 4-Nitro-l-aminobenzol in den Trisazofarbstoff übergeführt. Der durch Ansäuern und Aussalzen abgeschie dene Farbstoff, oder gegebenenfalls die Reaktionslösung selbst, wird mit 6 Teilen Kupfersulfat und mit soviel Ammoniak ver setzt, dass deutlich ammoniakalische Reak tion vorhanden ist und diese auch bei der weiteren Behandlung bestehen bleibt.
Mit telst einer kupfernen Dampfschlange heizt man auf 90 C auf und leitet bei dieser Tem peratur während einigen Stunden einen schwachen Luftstrom durch die Lösung. Der Farbstoff wird in der Wärme aus der an gesäuerten Lösung ausgesalzen und stellt nach dem Trocknen ein schwärzliches Pulver dar. Chromgegerbtes und vegetabilisch ge gerbtes Leder wird in tief dunkelbraunen Tönen gefärbt. Die alkalische Umwandlung des hier beschriebenen Trisazofarbstoffes führt zu einer wesentlichen Verbesserung der Alkaliechtheit. Die vorher nur mittelmässige Echtheit gegen alkalischen Fettliquor darf nach der Behandlung als sehr gut bezeichnet werden.
Die Färbungen zeigen eine Vertie fung des Farbtones von rötlichbraun nach dunkelbraun.
Process for the preparation of a coloring reaction product obtained from a trisazo dye. It has been found that a valuable, brown dye of as yet unknown constitution is formed if the compound 4-nitro-4'-aminodiphenylamine -? - sulfone- # <lure -ftz0-1- a.minonaphthalene-6 \ 7- sulfonic acid Z (technical mixture) -azo-1,3-dioxybenzene-azo-4-nitro-l-aminobenzene in the presence of aqueous ammonia and a heavy metal with oxidizing agents,
preferably with air. The new dye is a blackish powder that dissolves in water with a brown color and in concentrated sulfuric acid with a blue color. In contrast to the original dye, it hardly stains wool and silk, on the other hand it creates a beautiful, rich brown on leather, the color of which depends on the degree of oxidation.
These leather dyes are characterized by their excellent fastness to light and alkaline fatty liquor, as well as organic and inorganic acids.
<I> Example: </I> 31 parts of 4-nitro-4'-aminodiphenylamine-2-sulfonic acid are diazotized in the customary manner and with 23 parts of 1-aminonaphthalene-6/7-sulfonic acid (technical mixture) in vinegar acidic solution coupled.
The precipitated and filtered monoazo dye is dissolved with sodium hydroxide solution, diazotized directly in a known manner and combined with 11 parts of 1,3-dioxybenzene in an alkaline soda solution in the cold.
When the formation of the disazo dye is complete, it is converted into the trisazo dye in a soda-alkaline solution with the diazo compound composed of 13.8 parts of 4-nitro-1-aminobenzene. The dyestuff deposited by acidification and salting out, or optionally the reaction solution itself, is mixed with 6 parts of copper sulfate and with enough ammonia that a clear ammoniacal reaction is present and this persists during further treatment.
With a copper steam coil it is heated to 90 C and at this temperature a gentle stream of air is passed through the solution for a few hours. The dyestuff is salted out in the heat from the acidified solution and after drying it is a blackish powder. Chrome-tanned and vegetable-tanned leather is dyed in deep dark brown tones. The alkaline conversion of the trisazo dye described here leads to a substantial improvement in the alkali fastness. The previously only mediocre fastness to alkaline fatty liquor can be described as very good after the treatment.
The colorations show a deepening of the hue from reddish brown to dark brown.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE180272X | 1933-09-15 | ||
| CH177582T | 1935-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH180272A true CH180272A (en) | 1935-10-15 |
Family
ID=25720006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH180272D CH180272A (en) | 1933-09-15 | 1934-08-21 | Process for preparing a coloring reaction product obtained from a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH180272A (en) |
-
1934
- 1934-08-21 CH CH180272D patent/CH180272A/en unknown
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