CH187429A - Process for the preparation of a water-insoluble azo dye. - Google Patents
Process for the preparation of a water-insoluble azo dye.Info
- Publication number
- CH187429A CH187429A CH187429DA CH187429A CH 187429 A CH187429 A CH 187429A CH 187429D A CH187429D A CH 187429DA CH 187429 A CH187429 A CH 187429A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- preparation
- insoluble azo
- azo dye
- dye
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- FBAJLZQXONMOCA-UHFFFAOYSA-N (2,2-dioxo-1,3,2,4-dioxathiazetidin-4-ium-4-ylidene)azanide Chemical compound [N-]=[N+]1OS(=O)(=O)O1 FBAJLZQXONMOCA-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines wasserunlöslichen Azofarbstoffes. Es wurde gefunden, dass man wertvolle wasserunlösliche Azofarbstoffe erhält, wenn man diazotierte 1-Amino-7-oxy-8-arylazonaph- thaline oder ihre Substitutionsprodukte mit Arylamiden von P-Ketonsäuren oder von solchen o-Oxycarbonsäuren, die in o-Stellung zur Hydroxylgruppe kuppeln, in Substanz oder auf einem Substrat vereinigt.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines wasserunlöslichen Azofarbstoffes. Es ist da durch gekennzeichnet, dass man 1-(2',3'-Oxy- naphthoylamino)-2-methoxybenzol mit diazo- tiertem 8-(2'-Nitrophenylazo)-1-amino-7-oxy- naphthalin kuppelt. Stellt man den Farbstoff auf der Faser her, so erhält man gelbstichig schwarzbraune Töne.
<I>Beispiel:</I> 293 g 1-(2',3'-Oxynaphthoylamino)-2-me- thoxybenzol (1 Mol) werden in 5 Liter Wasser angeschlämmt und mit der erforderlichen Menge Natronlauge gelöst. Aus der Lösung wird das freie Naphthol mit Essigsäure in feiner Form gefällt.
Hierzu gibt man eine essigsaure Diazolösung, die durch Auflösen von 417 g Diazosulfat des 8-(2'-Nitrophenyl- azo)-1-amino-7-oxynaphthalin (1 Mol)
EMI0001.0030
mit 120 g wasserfreiem Natriumacetat in 8 Liter Wasser unter Bildung des neutralen Sulfats erhalten wird. Nach Zusatz von 200g Natriumacetat tritt allmählich Kupp lung ein, die nach einigen Stunden beendet ist, Der gebildete Farbstoff de1'Konstitution:
EMI0002.0001
wird abgssaügt und mit Wasser gewaschen.
Nach dem Trocknen stellt er ein braun schwarzes Pulver dar. Stellt man den Farb- stoff auf der Faser her, so erhält man gelb stichig schwarzbraune Töne.
Process for the preparation of a water-insoluble azo dye. It has been found that valuable water-insoluble azo dyes are obtained if diazotized 1-amino-7-oxy-8-arylazonaphthalines or their substitution products with arylamides of P-ketonic acids or of those o-oxycarboxylic acids which are o-position to the hydroxyl group couple, in substance or combined on a substrate.
The present patent relates to a process for the preparation of a water-insoluble azo dye. It is characterized in that 1- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene is coupled with diazotized 8- (2'-nitrophenylazo) -1-amino-7-oxynaphthalene. If the dye is produced on the fiber, yellowish black-brown tones are obtained.
<I> Example: </I> 293 g 1- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene (1 mol) are suspended in 5 liters of water and dissolved with the required amount of sodium hydroxide solution. The free naphthol is precipitated in fine form from the solution with acetic acid.
For this purpose, an acetic acid diazo solution is added which, by dissolving 417 g of diazo sulfate of 8- (2'-nitrophenyl-azo) -1-amino-7-oxynaphthalene (1 mol)
EMI0001.0030
with 120 g of anhydrous sodium acetate in 8 liters of water to form the neutral sulfate. After adding 200g of sodium acetate, coupling gradually occurs, which ends after a few hours. The dye formed has the constitution:
EMI0002.0001
is sucked off and washed with water.
After drying, it turns out to be a brown-black powder. If the dye is produced on the fiber, yellow, cast black-brown tones are obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE187429X | 1934-11-14 | ||
| CH187429T | 1935-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH187429A true CH187429A (en) | 1936-11-15 |
Family
ID=25721532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH187429D CH187429A (en) | 1934-11-14 | 1935-10-31 | Process for the preparation of a water-insoluble azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH187429A (en) |
-
1935
- 1935-10-31 CH CH187429D patent/CH187429A/en unknown
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