CH181534A - Process for the preparation of a vat dye. - Google Patents
Process for the preparation of a vat dye.Info
- Publication number
- CH181534A CH181534A CH181534DA CH181534A CH 181534 A CH181534 A CH 181534A CH 181534D A CH181534D A CH 181534DA CH 181534 A CH181534 A CH 181534A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- naphthoylenedi
- vat
- arylimidazole
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- -1 aryl imidazoles Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011230 binding agent Substances 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
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Iiüpenfarbstoffes. Es wurde gefunden, dass man neue wert volle Küpenfarbstoffe erhält, wenn man aryl- aminosubstituierte 1.4.5.8-Naphthoylendi- (arylimidazole) mit sauren Kondensations mitteln, vorteilhaft Aluminiumchlorid als solches oder gemischt mit Schmelzmitteln, wie zurn Beispiel Kochsalz oder dergleichen, bei erhöhten Temperaturen, z. B. zwischen etwa 140 und 250 C, behandelt.
Die neuen Küpenfarbstoffe, deren Kon stitution nicht bekannt ist, die aber mög licherweise Carbazole darstellen, zeigen recht grosse Farbstärke und liefern Färbungen von ausgezeichneten Echtheitseigenschaften.
Die in diesem Verfahren verwendeten Ausgangsstoffe, nämlich die arylaminosub- stituierten 1.4.5.8-Naphthoylendi-(arylimid- azole) können beispielsweise nach dem Ver fahren der deutschen Patentschrift Nr. 534493 erhalten werden, beispielsweise dadurch, dass man 1.4.5.8-Naphthoylenhalogendi-(aryl- imidazole) mit Aminoverbindungen, oder dass man 1.4.5.8-Naphthoylenaminodi-(arylimid- azole) mit halogenhaltigen Verbindungen kon densiert.
Gegenstand dieses Patentes ist ein Ver fahren zur Darstellung eines güpenfarbstoffes, welches dadurch gekennzeichnet ist, dass. man das 1.4.5.8-Naphthoylendi-(arylimid- azol) folgender Formel:
EMI0001.0022
mit Aluminiumchlorid bei höherer Tem peratur behandelt. <I>Beispiel:</I> Wird der in der deutschen Patentschrift Nr. 56'7 210, Beispiel 1, beschriebene, leichter lösliche rote Farbstoff mit Halogenen, z. B.
Brom, behandelt, so werden leicht. Dihalogen- substitutionsprodukte erhalten, die sich in geeigneten Lösungsmitteln unter Zusatz säure bindender Mittel mit a-Aminoanthrachinonen umsetzen lassen.
10 Gewichtsteile des auf diese Weise mit a-Aminoanthrachinon erhaltenen Um setzungsproduktes, dem folgende Konstitution zukommt
EMI0002.0008
werden bei 130-140 in eine Schmelze von 40 Gewichtsteilen Aluminiumchlorid und 10 Gewichtsteilen Natriümchlorid eingetragen und verrührt. Die Temperatur wird dann auf 190-200 gesteigert und dort einige Stun den gehalten. Die etwas abgekühlte Schmelze wird dann in verdünnte Salzsäure einge tragen, wobei sich der Farbstoff in dunkel braunen Flocken abscheidet; er wird abge saugt, mit Wasser neutral gewaschen und getrocknet. Er stellt ein fast schwarzes Pul ver dar, das sich in - organischen Lösungs mitteln kaum löst.
Die Lösungsfarbe in kon zentrierter Schwefelsäure ist rötlichbraun. Die alkalische Hydrosulfitküpe ist braun. Baumwolle wird aus der Küpe in kräftigen, schwarzbraunen Tönen von sehr guten Echt- heiten gefärbt.
Process for the preparation of a pulp dye. It has been found that new valuable vat dyes are obtained if aryl-amino-substituted 1.4.5.8-naphthoylenedi- (arylimidazoles) with acidic condensation agents, advantageously aluminum chloride as such or mixed with fluxes, such as table salt or the like, at elevated temperatures , e.g. B. between about 140 and 250 C treated.
The new vat dyes, the constitution of which is not known, but which may represent carbazoles, show very high color strength and provide dyeings with excellent fastness properties.
The starting materials used in this process, namely the arylamino-substituted 1.4.5.8-naphthoylenedi- (arylimidazoles) can be obtained, for example, according to the method of German patent specification No. 534493, for example by using 1.4.5.8-naphthoylenedi- ( aryl imidazoles) with amino compounds, or that 1.4.5.8-Naphthoylenaminodi- (arylimidazole) condenses with halogen-containing compounds.
The subject of this patent is a process for the preparation of a high quality dye, which is characterized in that the 1.4.5.8-naphthoylenedi- (arylimidazole) of the following formula is used:
EMI0001.0022
treated with aluminum chloride at a higher temperature. <I> Example: </I> If the more easily soluble red dye described in German Patent No. 56'7 210, Example 1, is combined with halogens, e.g. B.
Bromine, treated so be easily. Dihalogen substitution products obtained, which can be reacted in suitable solvents with the addition of acid-binding agents with α-aminoanthraquinones.
10 parts by weight of the reaction product obtained in this way with a-aminoanthraquinone, which has the following constitution
EMI0002.0008
are entered at 130-140 in a melt of 40 parts by weight of aluminum chloride and 10 parts by weight of sodium chloride and stirred. The temperature is then increased to 190-200 and held there for a few hours. The slightly cooled melt is then carried into dilute hydrochloric acid, the dye separating out in dark brown flakes; it is filtered off with suction, washed neutral with water and dried. It is an almost black powder that hardly dissolves in organic solvents.
The solution color in concentrated sulfuric acid is reddish brown. The alkaline hydrosulfite vat is brown. Cotton is dyed from the vat in strong, black-brown tones of very good fastness.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE181534X | 1934-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH181534A true CH181534A (en) | 1935-12-31 |
Family
ID=5716567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH181534D CH181534A (en) | 1934-03-07 | 1935-03-06 | Process for the preparation of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH181534A (en) |
-
1935
- 1935-03-06 CH CH181534D patent/CH181534A/en unknown
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