DE849880C - Process for the production of new sulfonic acid group-free monoazo dyes of the pyrazolone series - Google Patents
Process for the production of new sulfonic acid group-free monoazo dyes of the pyrazolone seriesInfo
- Publication number
- DE849880C DE849880C DEC3558A DEC0003558A DE849880C DE 849880 C DE849880 C DE 849880C DE C3558 A DEC3558 A DE C3558A DE C0003558 A DEC0003558 A DE C0003558A DE 849880 C DE849880 C DE 849880C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- pyrazolone
- methyl
- acid group
- acid amide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title claims description 7
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 5
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- -1 metal complex compounds Chemical class 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 150000001875 compounds Chemical class 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
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung neuer sulfonsäuregruppenfreier Monoazofarbstoffe der Pyrazolonreihe Es wurde gefunden, daß man zu neuen, wertvollen sulfonsäuregruppenfreien Monoazofarbstoffen derPyrazolonreihegelangt,wennmandiazotiertes4-Nitro-6-chlor-2-amino-i-o-xybenzol mit solchen i-Phenyl-3-methyl-5-pyrazolonen vereinigt, deren Phenylrest eine Sulfonsäureamidgruppe der Zusammensetzung enthält, worin R, und R,1 Wasserstoff oder Alkylreste bedeuten. Die beim vorliegenden Verfahren als Ausgangsstoffe dienenden i-Phenyl-3-methY1-5-pyrazolone können im Phenylrest außer der Sulfonsäureamidgruppe noch weitere Substituenten, z. B. eine Methyl-oder Methoxygruppe oder i Chloratom, enthalten. Die Sulfonsäureamidgruppe kann vorzugsweise eine -SO, N 11,- Gruppe sein. Es kommen aber auch solche Sulfonsäureamidreste in Betracht, in welchen das Stickstoffatom der Sulfonsäureamidgruppe zwei oder vorzugsweise einen Alkylrest enthält. Dabei ergeben insbesondere diejenigen Sulfonsäureamide wertvolle Farbstoffe, in welchen die Gesamtzahl der Kohlenstoffatome, die in der Sulfonsäureamidgruppe vorhanden sind, nicht höher als 4 ist. Als Beispiele geeigneter Azokomponenten sind zu erwähnen: i-PhenY1-3-Metfiyl-5-pyrazolon-2'-sulfonsäureamid, i-PhenY1-3-methyl-5-pyrazolon-3'-sulfonsäureamid, i-PhenY1-3-methyl-5-pyrazolon-4'-sulfonsäureamid, i-(2'-Methyl)-phenY1-3-methY1-5-pyrazo-Ion-5'-sulfonsäureamid, i-(2'-Chlor)-phenY1-3-methyl-5-pyrazolon-5'-sulfonsäureamid, i-PhenY1-3-methyl-5-pyrazolon-3'-sulfonsäuremethylamid,i-PhenY1-3-methyl-5-pyra,zolon-3'-sulfonsäuredimethylamid, i-Phenyl-3-methY1-5-pyrazolon-3'-sulfonsäureoxy'äthylamid, i - Phenyl - 3 - methyl - 5 - pyrazolon - 3' - sulfonsäure -n - butylamid.Process for the preparation of new sulfonic acid group-free monoazo dyes of the pyrazolone series It has been found that new, valuable sulfonic acid group-free monoazo dyes of the pyrazolone series are obtained if 4-nitro-6-chloro-2-amino-io-xybenzene with such i-phenyl-3-methyl-5-zolones combined, the phenyl radical of which is a sulfonic acid amide group of the composition contains, in which R 1 and R 1 are hydrogen or alkyl radicals. The i-phenyl-3-methY1-5-pyrazolones serving as starting materials in the present process can contain other substituents in the phenyl radical in addition to the sulfonic acid amide group, e.g. B. a methyl or methoxy group or i chlorine atom contain. The sulfonic acid amide group can preferably be an —SO, N 11, - group. However, sulfonic acid amide radicals also come into consideration in which the nitrogen atom of the sulfonic acid amide group contains two or preferably one alkyl radical. In particular, those sulfonic acid amides produce valuable dyes in which the total number of carbon atoms present in the sulfonic acid amide group is not higher than four. As examples of suitable azo components are to be mentioned: i-PhenY1-3-Metfiyl-5-pyrazolon-2'-sulfonic acid amide, i-PhenY1-3-methyl-5-pyrazolone-3'-sulfonic acid amide, i-PhenY1-3-methyl- 5-pyrazolone-4'-sulfonic acid amide, i- (2'-methyl) -phenY1-3-methY1-5-pyrazo-ion-5'-sulfonic acid amide, i- (2'-chloro) -phenY1-3-methyl- 5-pyrazolone-5'-sulfonic acid amide, i-PhenY1-3-methyl-5-pyrazolone-3'-sulfonic acid methylamide, i-PhenY1-3-methyl-5-pyra, zolone-3'-sulfonic acid dimethylamide, i-phenyl-3 -methY1-5-pyrazolone-3'-sulfonic acidoxy'ethylamide, i - phenyl - 3 - methyl - 5 - pyrazolone - 3 '- sulfonic acid -n - butylamide.
Die Kupplung des diazotierten 4-Nitro-6-chlor-2-amino-i-oxybenzols mit den Pyrazolonsulfonsäureamiden der angegebenen Art kann nach üblichen an sich bekannten Methoden erfolgen, z. B. in saurem, vorzugsweise schwach saurem oder in alkalischem, vorzugsweise schwach alkalischem Mittel.The coupling of the diazotized 4-nitro-6-chloro-2-amino-i-oxybenzene with the Pyrazolonsulfonsäureamiden of the specified type can according to the usual per se known methods take place, e.g. B. in acidic, preferably weakly acidic or in alkaline, preferably weakly alkaline agent.
Die nach dem vorliegenden Verfahren erhältlichen sulfonsäuregruppenfreien Monoazofarbstoffe sind neu und entsprechen der allgemeinen Formel worin R einen aromatischen Rest der Benzolreihe bedeutet, der eine Sulfonsäureamidgruppe der Zusammensetzung enthält, worin Ri und R, Wasserstoff oder Alkylreste bedeuten.The sulfonic acid group-free monoazo dyes obtainable by the present process are new and correspond to the general formula wherein R represents an aromatic radical of the benzene series which is a sulfonic acid amide group of the composition contains, wherein Ri and R, hydrogen or alkyl radicals.
Diese neuen Produkte können zum Färben der verschiedensten Materialien verwendet werden. Besonders wertvolle Ergebnisse erhält man, wenn man die Farbstoffe mit metallabgebenden Mitteln behandelt. Diese Behandlung kann in an sich bekannter Weise in Substanz, im Färbebad oder auf der Faser vorgenommen werden. So kann die Metallisierung in Substanz z. B. mit chromabgebenden Mitteln in saurem, neutralem oder schwach alkalischem Medium, gewünschtenfalls in Anwesenheit geeigneter Zusätze, wie Säuren oder Basen oder anderer säurebindender Mittel, organischer Lösungsmittel oder weiterer die Komplexbildung fördernder Zusätze, offen oder unter Druck stattfinden.These new products can be used to dye a wide variety of materials be used. Particularly valuable results are obtained when you use the dyes treated with metal donating agents. This treatment can be known in and of itself In substance, in the dye bath or on the fiber. So can the Metallization in substance z. B. with chromium donating agents in acidic, neutral or weakly alkaline medium, if desired in the presence of suitable additives, such as acids or bases or other acid-binding agents, organic solvents or other additives that promote complex formation, take place openly or under pressure.
Die Metallisierung auf der Faser, vorzugsweise die Chromierung der auf Wolle gefärbten Farbstoffe, kann beispielsweise nach dem bekannten Nachchromierverfahren durchgeführt werden. Die Farbstoffe eignen sich aber besonders gut zum Färben nach dem Einbadchromierverfahren, d. h. zum Färben untei: Zusatz von Alkalichromaten und Ammoniumsulfat und liefern in dieserWeise gefärbt, Färbungen von sehr guten Echtheitseigenschaf ten.The metallization on the fiber, preferably the chroming of the dyes dyed on wool, can be carried out, for example, by the known post-chroming process. However, the dyes are particularly suitable for dyeing by the single-bath chroming process, i. H. for dyeing: addition of alkali chromates and ammonium sulfate and dyed in this way produce dyeings with very good fastness properties.
Die nachfolgenden Beispiele dienen zur Erläuterung der Erfindung. Dabei bedeuten, sofern nichts anderes vermerkt wird, die Teile Gewichtste:le und die Prozente Gewichtsprozente. Beispiel 25,3 Teile i'-PhenY1-3-methyl-5-pyrazolon-3'-sulfonsäureamid werden in ioo Teilen Wasser und 8 Teilen Natriumhydroxyd gelöst und bei o' mit der auf übliche Weise hergestellten Diazoverbindung aus 18,85 Teilen 6-Chlor-4-nitro-2-amino-i-oxybenzol gekuppelt. Die Kupplung sQtzt sofort ein und ist nach kurzer Zeit beendet. Nun gibt man je ioo Raumteile der so erhaltenen Farbstoffsuspension etwa io Teile Natriumchlorid zu, rührt nochmals i Stunde, filtriert den Farbstoff ab, wäscht ihn mit 50 '/,iger Natriumchloridlösung nach und trocknet ihn. Nilan erhält ein dunkelrotbraunes Pulver, das sich in heißem Wasser mit rotbrauner, in konzentrierter Schwefelsäure mit gelbbrauner Farbe löst. Der Farbstoff färbt Wolle nach dem Einbadchromierungsverfahren oder dem Nachchromierverfahren in echten Orangetönen.The following examples serve to illustrate the invention. Unless otherwise stated, the parts mean parts by weight: le and the percentages mean percentages by weight. Example 25.3 parts of i'-PhenY1-3-methyl-5-pyrazolone-3'-sulfonic acid amide are dissolved in 100 parts of water and 8 parts of sodium hydroxide and, at o ', with the conventionally prepared diazo compound from 18.85 parts of 6- Chlorine-4-nitro-2-amino-i-oxybenzene coupled. The clutch starts immediately and is terminated after a short time. About 10 parts of sodium chloride are then added to each 100 parts by volume of the dye suspension thus obtained, the mixture is stirred for another hour, the dye is filtered off, washed with 50 % sodium chloride solution and dried. Nilan receives a dark red-brown powder that dissolves in hot water with red-brown color, and in concentrated sulfuric acid with yellow-brown color. The dye dyes wool in real shades of orange using the single-bath chrome plating process or the post-chrome plating process.
Farbstoffe, die Wolle nach dem Einbadchromierverfahren ebenfalls in orangen Tönen färben, werden erhalten, wenn man im obigen Beispiel anstatt der 25,3 Teile i-Phenyl-3-MethY1-5-pyrazolon-3'-sulfonsäureamid eine äquivalente Menge einer der folgenden Verbindungen verwendet: i-PhenY1-3-methY1-5-pyrazolon-3'-sulfonsäure-N-methylamid, i-PhenY1-3-methyl-5-pyrazolon-3'-sulfonsäure-fl-oxyäthylamid, i-Phenyl-3-methyl-5-pyrazolon-4'-sulfonsäureamid, 1-(2'-Methyl)-phenY1-3-methyl-5-pyrazolon-5'-sulfonsäureamid, i-(2'-Chlor)-phenyl-3-methyl-3-pyrazolon-5'-sulfonsäureamid.Dyestuffs which also dye wool in orange shades by the single bath chroming process are obtained if, in the above example, instead of 25.3 parts of i-phenyl-3-methY1-5-pyrazolone-3'-sulfonic acid amide, an equivalent amount of one of the following compounds used: i-PhenY1-3-methY1-5-pyrazolon-3'-sulfonic acid-N-methylamide, i-PhenY1-3-methyl-5-pyrazolone-3'-sulfonic acid-fl-oxyethylamide, i-phenyl-3- methyl-5-pyrazolone-4'-sulfonic acid amide, 1- (2'-methyl) -phenY1-3-methyl-5-pyrazolone-5'-sulfonic acid amide, i- (2'-chloro) -phenyl-3-methyl- 3-pyrazolone-5'-sulfonic acid amide.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH849880X | 1949-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE849880C true DE849880C (en) | 1952-09-18 |
Family
ID=4542191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC3558A Expired DE849880C (en) | 1949-12-20 | 1950-12-17 | Process for the production of new sulfonic acid group-free monoazo dyes of the pyrazolone series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE849880C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE955800C (en) * | 1953-05-12 | 1957-01-10 | Sandoz Ag | Process for the production of chromium-containing azo dyes of the pyrazolone series |
| DE1109806B (en) * | 1958-05-24 | 1961-06-29 | Bayer Ag | Process for the preparation of chromium-containing monoazo dyes |
| DE1198780B (en) * | 1957-06-27 | 1965-08-19 | Kuhlmann Ets | Process for dyeing polyester fibers |
-
1950
- 1950-12-17 DE DEC3558A patent/DE849880C/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE955800C (en) * | 1953-05-12 | 1957-01-10 | Sandoz Ag | Process for the production of chromium-containing azo dyes of the pyrazolone series |
| DE1198780B (en) * | 1957-06-27 | 1965-08-19 | Kuhlmann Ets | Process for dyeing polyester fibers |
| DE1109806B (en) * | 1958-05-24 | 1961-06-29 | Bayer Ag | Process for the preparation of chromium-containing monoazo dyes |
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