CH138876A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH138876A CH138876A CH138876DA CH138876A CH 138876 A CH138876 A CH 138876A CH 138876D A CH138876D A CH 138876DA CH 138876 A CH138876 A CH 138876A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- acid
- cotton
- azo dye
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 7
- 229920000742 Cotton Polymers 0.000 claims description 4
- RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 claims description 2
- 229920000297 Rayon Polymers 0.000 claims description 2
- -1 nitroazo Chemical group 0.000 claims description 2
- 239000000843 powder Substances 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 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Azofarbstofes. Gegenstand vorliegender Erfindung ist ein Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man diazotierte 5-Nitro-2-aminobenzoesäure mit Acetessig-o-anisididsulfosäure kuppelt, die Nitrogruppe des so erhaltenen Nitroazokörpers reduziert und den erhaltenen p-Aminoazo- färbstoff mit Phosgen behandelt.
Die Acetessig-o-anisididsulfosäure hat fol gende Formel:
EMI0001.0013
Die Stellung der Sulfogruppe ist nicht genau bekannt. <I>Beispiel:</I> 182 Gewichtsteile 5-Nitro-2-aminobenzoe- säure werden diazotiert und mit einer soda- alkalischen Lösung von 574 Gewichtsteilen Acetessig-o-anisididsulfosäure gekuppelt. Man reduziert dann die Nitrogruppe mit einem geringen Überschuss kristallisierten Natrium sulfids und verwandelt wie üblich mittelst Phosgen in den symmetrischen Harnstoff.
Der gereinigte Farbstoff färbt Viskose und Baumwolle prächtig goldgelb. Mit Kupfer salzen auf der Baumwolle nachbehandelt, erhält man reingelbe klare Töne.
Der Farbstoff bildet trocken ein rotgelbes Pulver, das sich in Wasser und konzentrier ter Schwefelsäure mit gelber Farbe löst.
Process for the preparation of an azo dye. The present invention relates to a process for the production of an azo dye, characterized in that diazotized 5-nitro-2-aminobenzoic acid is coupled with acetoacetic-o-anisididesulfonic acid, the nitro group of the nitroazo body thus obtained is reduced and the resulting p-aminoazo dye with Phosgene treated.
Acetoacetic-o-anisidide sulfonic acid has the following formula:
EMI0001.0013
The exact position of the sulfo group is not known. <I> Example: </I> 182 parts by weight of 5-nitro-2-aminobenzoic acid are diazotized and coupled with a soda-alkaline solution of 574 parts by weight of acetoacetic-o-anisididesulfonic acid. The nitro group is then reduced with a slight excess of crystallized sodium sulfide and, as usual, converted into the symmetrical urea by means of phosgene.
The cleaned dye dyes viscose and cotton a splendid golden yellow. If the cotton is aftertreated with copper salts, pure yellow clear tones are obtained.
The dye forms a red-yellow powder when dry, which dissolves in water and concentrated sulfuric acid with a yellow color.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE138876X | 1927-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH138876A true CH138876A (en) | 1930-03-31 |
Family
ID=5667508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH138876D CH138876A (en) | 1927-02-21 | 1928-02-06 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH138876A (en) |
-
1928
- 1928-02-06 CH CH138876D patent/CH138876A/en unknown
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