CH292083A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH292083A CH292083A CH292083DA CH292083A CH 292083 A CH292083 A CH 292083A CH 292083D A CH292083D A CH 292083DA CH 292083 A CH292083 A CH 292083A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- water
- monoazo dye
- oxynaphthalene
- red
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 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 4
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 241000792859 Enema Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940095399 enema Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 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
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
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Monoazofarbstoff gelangt, wenn man diazotiertes 5-Nitro-2-amino-l-oxvbenzol mit 1. - Sulfacetamino - 7 - oxy naphthalin ver einigt.
Der neue Farbstoff stellt ein sehwärzliehes Pulver dar, das sich in Wasser mit violetter, in verdünnter Natronlauge mit. blauer und in konzentrierter Schwefelsäure mit roter Farbe löst und Wolle aus saurem Bade in rotvioletten Tönen färbt, welche beim Nachchromieren in ein blaustichiges Grün von guten Nassecht: heiten und vorzüglicher Lichtechtheit. über- (i.eführt werden.
Das .dem vorliegenden Verfahren als Aus- ,anrsstoff dienende 1-Sulfaeeta.mino-7-oxy- lnaplitlia.lin kann beispielsweise erhalten wer den, indem man 1-Amino-7-oxynaphthalin an der Aminogruppe mit Chloressigsäurechlorid iiionoacyliert und das erhaltene 1-Chloracetyl- amino- 7-oxy naphthalin mit schwefliger Säure bzw. mit den Salzen dieser Säure umsetzt.
Die Kupplung kann nach an sich bekann ten Methoden z. B. in alkalischem Medium erfolgen.
Beispiel: 15,.1 Teile 5-Nitro-2-amino-1-oxybenzol wer den in 22 Teilen 30 o/oiger Salzsäure und 1.50 Teilen Wasser suspendiert und bei 5 mit einer Lösung von 6,9 Teilen Natriumnitrit in 25 Teilen @V asser diazotiert.. Die so erhaltene Suspension wird mit einer Lösung von 28,1 Teilen 1-Sulfacetamino-7-oxynaphthalin, 1 Teilen Natriumhydroxycl, 5,
3 Teilen latrium- earbonat in 150 Teilen Wasser vermischt und die Kupplung bei 0 bis 5 zu Ende geführt. Nach beendeter Kupplung wird der ausge schiedene Farbstoff durch Filtration ab getrennt, mit verdünnter N atr iumehlor id- lösung gewaschen und getrocknet.
Das hierbei verwendete 1-Sulfacetamino- 7-oxynaphtha.lin kann wie folgt. hergestellt werden A. 15,9 Teile 1-Amino-7-oxynaphtalin wer den mit Hilfe von 12 Volumteilen Salzsäure lOn in 300 Teilen Wasser bei gewöhnlicher Temperatur gelöst..
Unter gutem Rühren wer den gleichzeitig eine Mischung von 13,6 Teilen Chloracetylchlorid und 30 Teilen Aceton und eine Lösung von 19,7 Teilen wasserfreiem Natriumacetat in 60 Teilen Wasser so zuge- 1 ropft, dass der Einlauf ungefähr 2 Stunden dauert und die Temperatur nicht über 30 steigt. Das Monoacetylprodukt scheidet sich als graue, teils halbfeste Masse aus. Nach be endeter Acylierung wird abfiltriert und das erhaltene Reaktionsprodukt mit Wasser ge waschen.
Durch Umkristallisieren aus Alkohol kann das 1-Chloracetamino-7-oxynaphthalin in Form von hellgrauen Blättchen erhalten wer den und zeigt dann einen Schmelzpunkt von 1.61 bis 162<B>0</B>.
B. 23,6 Teile 1-Chloracetaminö-7-oxy- naphthalin werden in 150 Teilen Aceton ge löst, mit einer Lösung von 12,6 Teilen Natriumsulfit in 75 Teilen Wasser versetzt und 18 Stunden unter Rüekfluss gekocht. Nach dem Abdestillieren des Acetons kristal- lisiert das 1-Sulfacetamino-7-oxynaphthalin in Form von glänzenden Blättchen aus, welche gewünschtenfalls durch Umkristallisieren aus heissem Wasser gereinigt werden können.
Process for the preparation of a monoazo dye. It has been found that a valuable monoazo dye is obtained if diazotized 5-nitro-2-amino-1-oxybenzene is combined with 1. - sulfacetamino - 7 - oxy naphthalene.
The new dye is a blackish powder that dissolves in water with violet, in dilute caustic soda with. blue and in concentrated sulfuric acid dissolves with red color and dyes wool from acid baths in red-violet tones, which when re-chromed to a bluish green of good wet fastness: whiteness and excellent light fastness. to be transferred
The 1-sulfaeeta.mino-7-oxy- lnaplitlia.lin, which serves as the starting material in the present process, can be obtained, for example, by ionoacylating 1-amino-7-oxynaphthalene on the amino group with chloroacetic acid chloride and the 1- Reacts chloroacetylamino- 7-oxy naphthalene with sulphurous acid or with the salts of this acid.
The coupling can by per se known methods such. B. in an alkaline medium.
Example: 15.1 parts of 5-nitro-2-amino-1-oxybenzene who suspended in 22 parts of 30% hydrochloric acid and 1.50 parts of water and at 5 with a solution of 6.9 parts of sodium nitrite in 25 parts @V water diazotized .. The suspension obtained in this way is treated with a solution of 28.1 parts of 1-sulfacetamino-7-oxynaphthalene, 1 part of sodium hydroxyl, 5,
3 parts of latrium earbonate mixed in 150 parts of water and the coupling at 0 to 5 was completed. After the coupling has ended, the dyestuff which has separated out is separated off by filtration, washed with dilute sodium chloride solution and dried.
The 1-sulfacetamino-7-oxynaphtha.lin used here can be used as follows. A. 15.9 parts of 1-amino-7-oxynaphthalene are prepared using 12 parts by volume of hydrochloric acid 10n in 300 parts of water at normal temperature.
While stirring well, a mixture of 13.6 parts of chloroacetyl chloride and 30 parts of acetone and a solution of 19.7 parts of anhydrous sodium acetate in 60 parts of water are added so that the enema takes about 2 hours and the temperature does not exceed 30 rises. The monoacetyl product separates out as a gray, partly semi-solid mass. When the acylation has ended, it is filtered off and the reaction product obtained is washed with water.
By recrystallization from alcohol, the 1-chloroacetamino-7-oxynaphthalene can be obtained in the form of light gray flakes and then has a melting point of 1.61 to 162 <B> 0 </B>.
B. 23.6 parts of 1-chloroacetamino-7-oxynaphthalene are dissolved in 150 parts of acetone, mixed with a solution of 12.6 parts of sodium sulfite in 75 parts of water and refluxed for 18 hours. After the acetone has been distilled off, the 1-sulfacetamino-7-oxynaphthalene crystallizes out in the form of shiny flakes, which, if desired, can be purified by recrystallization from hot water.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH292083T | 1950-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH292083A true CH292083A (en) | 1953-07-31 |
Family
ID=4487693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH292083D CH292083A (en) | 1950-08-01 | 1950-08-01 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH292083A (en) |
-
1950
- 1950-08-01 CH CH292083D patent/CH292083A/en unknown
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