CH285996A - Process for the preparation of an anthraquinone vat dye. - Google Patents
Process for the preparation of an anthraquinone vat dye.Info
- Publication number
- CH285996A CH285996A CH285996DA CH285996A CH 285996 A CH285996 A CH 285996A CH 285996D A CH285996D A CH 285996DA CH 285996 A CH285996 A CH 285996A
- Authority
- CH
- Switzerland
- Prior art keywords
- anthraquinone
- chlorobenzoyl
- fluorobenzoyl
- amino
- vat dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 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 title claims description 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- YISSCQZDTSIXFU-UHFFFAOYSA-N NC1=C(C=C(C=2C(C3=CC=CC=C3C(C1=2)=O)=O)N)C(C1=CC=C(C=C1)F)=O Chemical compound NC1=C(C=C(C=2C(C3=CC=CC=C3C(C1=2)=O)=O)N)C(C1=CC=C(C=C1)F)=O YISSCQZDTSIXFU-UHFFFAOYSA-N 0.000 claims description 3
- -1 p-fluorobenzoyl Chemical group 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000003973 paint Substances 0.000 claims 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Anthrachinonküpenfarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Anthrachinonküpenfarbstoff ge langt, wenn man 1,4-Diamino-2-(p-fluorben- zoyl)-anthrachinon mit einem den p-Chlor- benzoylrest abgebenden Mittel behandelt.
Der neue Farbstoff, das 1-Amino-4-(p- ehlorbenzoyl-amino) -2- (p-fluorbenzoyl)-an- thrachinon, löst sich in konz. Schwefelsäure mit grüner Farbe und liefert auf Baumwolle gedruckt, echte, rotstichig blaue Töne.
Als den p-Chlorbenzoylrest abgebende Mit tel kommen vorzugsweise Halogenide. insbe sondere das Chlorid der p-Chlorbenzoesäure, in Betracht. Die Umsetzung erfolgt zweck mässig in einem organischen Lösungsmittel wie o-Dichlorbenzol und bei erhöhter Tempera tur,
gegebenenfalls unter Zusatz eines säure bindenden Mittels wie Pyridin. Nach dem vorliegenden Verfahren wird nur die in der 4-Stellung des Anthrachinonrestes befindliche Aminogruppe in der angegebenen Weise acy- liert, während die in 1-Stellung befindliche Aminogruppe zufolge der Anwesenheit der Ketogruppe in 2-Stellung unverändert bleibt.
<I>Beispiel:</I> Eine Mischung von 5 Teilen 1,4-Diamino- 2- (p-fluorbenzoyl) -anthrachinon, 3,4 Teilen p-Chlorbenzoylchlorid, 5 Volumteilen Pyri- din und 150 Volumteilen o-Diehlorbenzol wird eine Stunde lang bei 7.10 bis 115 gerührt.
Nach dem Aufarbeiten erhält man das 1- Amino - 4 - (p- chlorbenzoy lamm o) - 2 - (p - fluor- benzoyl)-anthrachinon als blauen Farbstoff.
Process for the preparation of an anthraquinone vat dye. It has been found that a valuable anthraquinone vat dye is obtained if 1,4-diamino-2- (p-fluorobenzoyl) anthraquinone is treated with an agent which releases the p-chlorobenzoyl radical.
The new dye, the 1-amino-4- (p-ehlorbenzoyl-amino) -2- (p-fluorobenzoyl) -anthrachinon, dissolves in conc. Sulfuric acid with green color and, printed on cotton, delivers real, reddish blue tones.
Halides are preferably used as the p-chlorobenzoyl radical donating. in particular the chloride of p-chlorobenzoic acid into consideration. The reaction is conveniently carried out in an organic solvent such as o-dichlorobenzene and at an elevated temperature,
optionally with the addition of an acid-binding agent such as pyridine. According to the present process, only the amino group in the 4-position of the anthraquinone residue is acylated in the manner indicated, while the amino group in the 1-position remains unchanged due to the presence of the keto group in the 2-position.
<I> Example: </I> A mixture of 5 parts 1,4-diamino-2- (p-fluorobenzoyl) -anthraquinone, 3.4 parts p-chlorobenzoyl chloride, 5 parts by volume pyridine and 150 parts by volume o-diehlobenzene is used Stirred for one hour at 7:10 to 115.
After working up, the 1 - amino - 4 - (p-chlorobenzoy lamm o) - 2 - (p - fluorobenzoyl) anthraquinone is obtained as a blue dye.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH280188T | 1948-01-30 | ||
| CH285996T | 1948-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH285996A true CH285996A (en) | 1952-09-30 |
Family
ID=25731996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH285996D CH285996A (en) | 1948-01-30 | 1948-12-29 | Process for the preparation of an anthraquinone vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH285996A (en) |
-
1948
- 1948-12-29 CH CH285996D patent/CH285996A/en unknown
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