CH209346A - Process for the preparation of a water-soluble oxazine dye. - Google Patents
Process for the preparation of a water-soluble oxazine dye.Info
- Publication number
- CH209346A CH209346A CH209346DA CH209346A CH 209346 A CH209346 A CH 209346A CH 209346D A CH209346D A CH 209346DA CH 209346 A CH209346 A CH 209346A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- dye
- preparation
- soluble
- oxazine dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 12
- 239000010985 leather Substances 0.000 claims description 5
- 210000002268 wool Anatomy 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000001049 brown dye Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- OMRYCWIAZJHZFA-UHFFFAOYSA-N 3,4-dinitro-2H-oxazine Chemical compound [N+](=O)([O-])C1=C(NOC=C1)[N+](=O)[O-] OMRYCWIAZJHZFA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 125000003545 alkoxy group Chemical group 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B19/00—Oxazine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines wasserlöslichen Ogazinfarbstofes. Es wurde gefunden, dass man lichtechte, braune, wasserlösliche Oxazinfarbstoffe erhält, wenn man 2 . 4. 6 - Trinitrobenzol, welches einen gegen ein Aminoradikal austauschbaren Substituenten, wie zum Beispiel Chlor, Brom oder Alkyloxy, enthält, mit einem ortho- Aminophenol, welches eine oder mehrere wasserlöslichmachende Gruppen enthält, in Gegenwart eines säurebindenden Mittels,
zweckmässig durch Erwärmen der Reaktions komponenten in wässrig - alkalischer Lösung zu den entsprechenden Oxazinverbindungen kondensiert. Wasserlöslichmachende Gruppen sind die Sulfo- und Carboxylgruppe. Als 2.4.6-Trinitrobenzole können beispielsweise verwendet werden Pikrylchlorid, Pykrilbromid oder Trinitroanisol. Nach diesem Verfahren entstehen neue wasserlösliche Dinitro-oxazin- farbstoffe,
zum Beispiel solche folgender Kon stitutionsformel
EMI0001.0021
worin der Kern R eine Carboxyl- oder Sulfo- gruppe enthält, die zum Färben von Wolle und Leder verwendet werden können und sich durch ein vorzügliches Durchfärbever- mögen 'auf Leder auszeichnen. Gegenüber bekannten ähnlichen Farbstoffen zeichnen sich die Farbstoffe vorliegender Erfindung durch eine überlegene Lichtechtheit aus.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines wasser löslichen Oxazinfarbstoffes, welches darin be steht, dass man 2.4.6-Trinitro-l-chlorbenzol (Pikrylchlorid) mit 3 -Amino- 2 - oxy- 5 -sulfo- benzoesäure in Gegenwart eines säurebinden den Mittels kondensiert.
Die so erhaltene neue Verbindung ist ein brauner Farbstoff, der zum Färben von Wolle und Leder verwendet werden kann. Beispiel: In einer Lösung aus 1000 Gewichtsteilen Wasser und 132 Gewichtsteilen wasserfreier Soda werden 186,4 Gewichtsteile 3-Amino- 2-oxy-5-sulfobenzoesäure gelöst und mit 200 Gewichtsteilen 2.4.6-Trinitro-l-chlorbenzol (Pikrylchlorid) bei Wasserbadtemperatur ver rührt.
Es setzt hierbei eine ziemlich lebhafte Reaktion ein, wobei die Flüssigkeit sich braun färbt und nach einiger Zeit Salpetrigsäure- dämpfe ausgestossen werden. Die Abspaltung der salpetrigen Säure ist im wesentlichen nach etwa 8-9stüridigem Erhitzen beendet. Die so erhaltene Farbstofflösung wird einge dampft, wodurch 425 Gewichtsteile eines leichtlöslichen braunen Farbstoffes folgender Konstitution
EMI0002.0008
erhalten werden. Der Farbstoff kann zum Färben von Wolle und Leder verwendet werden.
Process for the preparation of a water-soluble ogazine dye. It has been found that lightfast, brown, water-soluble oxazine dyes are obtained if 2. 4. 6 - trinitrobenzene, which contains a substituent that can be exchanged for an amino radical, such as chlorine, bromine or alkyloxy, with an ortho-aminophenol, which contains one or more water-solubilizing groups, in the presence of an acid-binding agent,
expediently condensed to the corresponding oxazine compounds by heating the reaction components in an aqueous alkaline solution. Groups which make water soluble are the sulfo and carboxyl groups. Pikrylchloride, Pykrilbromid or Trinitroanisol, for example, can be used as 2.4.6-Trinitrobenzenes. This process creates new water-soluble dinitro-oxazine dyes,
for example those of the following constitutional formula
EMI0001.0021
in which the core R contains a carboxyl or sulfo group which can be used for dyeing wool and leather and is characterized by an excellent through-dyeing ability on leather. Compared with known similar dyes, the dyes of the present invention are distinguished by superior lightfastness.
The present patent is a process for the preparation of a water-soluble oxazine dye, which is be that 2.4.6-trinitro-1-chlorobenzene (picryl chloride) with 3-amino-2-oxy-5-sulfobenzoic acid in the presence of a acid-binding the agent condenses.
The new compound thus obtained is a brown dye that can be used to dye wool and leather. Example: 186.4 parts by weight of 3-amino-2-oxy-5-sulfobenzoic acid are dissolved in a solution of 1000 parts by weight of water and 132 parts by weight of anhydrous soda and mixed with 200 parts by weight of 2.4.6-trinitro-1-chlorobenzene (picryl chloride) at water bath temperature stirs.
A fairly vigorous reaction sets in here, the liquid turning brown and, after a while, nitrous acid vapors being emitted. The splitting off of nitrous acid is essentially complete after about 8-9 hours of heating. The dye solution thus obtained is evaporated, whereby 425 parts by weight of a readily soluble brown dye of the following constitution
EMI0002.0008
can be obtained. The dye can be used to dye wool and leather.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE209346X | 1937-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH209346A true CH209346A (en) | 1940-04-15 |
Family
ID=5794717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209346D CH209346A (en) | 1937-11-16 | 1938-09-26 | Process for the preparation of a water-soluble oxazine dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH209346A (en) |
-
1938
- 1938-09-26 CH CH209346D patent/CH209346A/en unknown
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