AT44456B - Process for the preparation of dyes of the pyrazolone series. - Google Patents
Process for the preparation of dyes of the pyrazolone series.Info
- Publication number
- AT44456B AT44456B AT44456DA AT44456B AT 44456 B AT44456 B AT 44456B AT 44456D A AT44456D A AT 44456DA AT 44456 B AT44456 B AT 44456B
- Authority
- AT
- Austria
- Prior art keywords
- dyes
- preparation
- pyrazolone series
- pyrazolone
- dye
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 title description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 claims 1
- 229960000943 tartrazine Drugs 0.000 claims 1
- 235000012756 tartrazine Nutrition 0.000 claims 1
- 239000004149 tartrazine Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- WQTCZINVPXJNEL-UHFFFAOYSA-N 4-amino-3-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1N WQTCZINVPXJNEL-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- IPDZRJWASWZYQD-UHFFFAOYSA-N chloro-(2-methylphenyl)sulfamic acid Chemical compound CC1=CC=CC=C1N(Cl)S(O)(=O)=O IPDZRJWASWZYQD-UHFFFAOYSA-N 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Farbstoffen der Pyrazolonreihe.
Behandelt man die 2-Acidylamino-l-methylbenzol-5-Bu1fosü. ure in wässeriger Lösung mit Chlor und spaltet in dem erhaltenen Reaktionsprodukt die Acidylgruppe ab, so erhält man eine bisher unbekannte Chlortoluidinsulfosäure von nachstehender Konstitution :
EMI1.1
Es hat sich nun gezeigt, dass diese Aminosutfosäure von grosser Bedeutung für die Darstellung von Farbstoffen der Pyrazolonreihe ist, da dio damit hergestellten Produkte eine aussergewöhnlich grünstichig Nuance aufweisen und sich durch eine besonders gute Lichtechtheit auszeichnen.
Die grünende Wirkung des Restes
EMI1.2
tritt schon hervor, wenn derselbe einmal in das Farbstoffmo1ekül eingeführt wird und zwar gleichgiltig, ob er zum Aufbau des Pyrazotonmoleküts (Tartrazinogens) gedient hat, oder ob eine diesem Rest entsprechende Diazoverbindung zur Endkuppelung verwendet wurde.
Eine besonders grosse Verschiebung der Nuance nach Grün hin findet statt, wenn man den genannten Rest zweimal in das Farbstoffmolelzül einführt.
Beispiel 1.
11 Teile eines lOOprozontigen Natriumsalzes der Dioxyweinslillre worden mit ca. 50 Teilen Wasser angerührt und mit einer Suspension von 24 Teilen des Hydrazins der 3-Chlor- : 2-amino-l-methyl-benzol-5-sulfosäure in ca. 50 Teilen Wasser vorsetzt. Man erwärmt hierauf zunächst auf 500, später auf 70-80 , wobei allmählich vollständige Lösung eintritt. Der gebildete Farbstoff wird, wenn nötig, nach vorherigem Ansäuern mit Kochsalz oder Chlorkalium gefällt. Er wird abgesaugt, gepresst und getrocknet.
Die aus diesem Farbstoff hergestellten Lacke bezw. die damit erzeugten Färbungen zeichnen sich durch eine hervorragend reine, zitronengelbe Nuance aus, wie sie bis jetzt mit Farbstoffen dieser Klasse auch nicht annähernd erreicht worden konnte ; auch die Lichtechtheit der mit denselben hergestellten Färbungen bezw. der daraus hergestellten Lacke entspricht den höchsten Anforderungen.
<Desc/Clms Page number 2>
EMI2.1
pyrazolon-3-carbonsäure. Nach ca. halbstündigem Rühren erwärmt man auf 600 und salzt den Farbstoff, wenn nötig, nach vorherigem Ansäuern mit Kochsalz aus. Man saugt ab, presst und trocknet.
Der Farbstoff löst sich leicht mit gelber Farbe in Wasser und färbt Wolle in reinen gelben Tönen an.
EMI2.2
<Desc / Clms Page number 1>
Process for the preparation of dyes of the pyrazolone series.
If you treat the 2-acidylamino-1-methylbenzene-5-Bu1fosü. ure in aqueous solution with chlorine and splits off the acidyl group in the resulting reaction product, a previously unknown chlorotoluidinesulfonic acid is obtained with the following constitution:
EMI1.1
It has now been shown that this amino acid is of great importance for the preparation of dyes of the pyrazolone series, since the products produced with it have an exceptionally greenish shade and are characterized by particularly good lightfastness.
The greening effect of the rest
EMI1.2
already emerges when it is introduced once into the dye molecule, irrespective of whether it served to build up the pyrazotone molecule (tartrazinogen) or whether a diazo compound corresponding to this residue was used for the end coupling.
A particularly large shift in the shade towards green takes place if the remainder mentioned is introduced twice into the dye molecule.
Example 1.
11 parts of a 100 per cent sodium salt of dioxy wine glass were mixed with about 50 parts of water and a suspension of 24 parts of the hydrazine of 3-chloro: 2-amino-1-methyl-benzene-5-sulfonic acid in about 50 parts of water was added . It is then heated first to 500, later to 70-80, with complete dissolution gradually occurring. If necessary, the dye formed is precipitated after acidification with table salt or potassium chloride. It is sucked off, pressed and dried.
The paints produced from this dye BEZW. the colorations produced with it are distinguished by an extremely pure, lemon-yellow shade, which up to now could not even come close to being achieved with dyes of this class; also the lightfastness of the dyeings produced with the same respectively. the paints made from it meet the highest requirements
<Desc / Clms Page number 2>
EMI2.1
pyrazolone-3-carboxylic acid. After stirring for about half an hour, the mixture is warmed to 600 and, if necessary, after acidifying it is salted out with common salt. You vacuum, press and dry.
The dye easily dissolves in water with a yellow color and stains wool in pure yellow tones.
EMI2.2
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE44456X | 1908-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT44456B true AT44456B (en) | 1910-10-25 |
Family
ID=5624672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT44456D AT44456B (en) | 1908-11-26 | 1909-03-10 | Process for the preparation of dyes of the pyrazolone series. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT44456B (en) |
-
1909
- 1909-03-10 AT AT44456D patent/AT44456B/en active
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