CH296528A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH296528A CH296528A CH296528DA CH296528A CH 296528 A CH296528 A CH 296528A CH 296528D A CH296528D A CH 296528DA CH 296528 A CH296528 A CH 296528A
- Authority
- CH
- Switzerland
- Prior art keywords
- blue
- parts
- monoazo dye
- oxynaphthalene
- preparation
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 240000007817 Olea europaea Species 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
- 210000002268 wool Anatomy 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 5
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 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
- 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 6-Nitro-4-chlor-2-amino-l- oxybenzol mit 1-Sulfacetamino-7-oxynaphtha- lin vereinigt.
Der neue Farbstoff. stellt ein schwärzliches Pulver dar, das sich in Wasser mit blauer, in verdünnter Natronlauge mit grünblauer und in konzentrierter Schwefelsäure mit. roter Farbe löst und Wolle aus saurem Bade in blauen Tönen färbt, welche beim Nachchro- mieren in ein Oliv von guten Nassechtheiten und vorzüglicher Lichtechtheit übergeführt werden.
Das dem vorliegenden Verfahren als Aus gangsstoff dienende 1-Sulfacetamino-7-oxy- naphthalin kann beispielsweise erhalten werden, indem man 1-Amino - 7 - oxynaph- thalin an der Aminogruppe mit Chloressig- säureehlorid monoacyliert und das erhal tene 1-Chloracetylamino-7-oxynaphthalin mit schwefliger Säure bzw. mit. den Salzen dieser Säure umsetzt.
Die Kupplung kann nach an sich bekann ten Methoden, zum Beispiel in alkalischem Medium, erfolgen.
<I>Beispiel.:</I> 16,0 Teile 6-Nitro-4-chlor-2-amino-l-oxy- benzol werden in 22 Teilen 30 % iger Salz- säure und 150 Teilen Wasser suspendiert und bei 5 mit einer Lösung von 6,9 Teilen Na triumnitrit in 25 Teilen Wasser diazotiert. Die so erhaltene Suspension.
wird mit einer Lö sung von<B>28,1.</B> Teilen 1-Sulfacetamino-7-oxy- naphthalin, 4 Teilen Natriumhydroxyd, 5,3 Teilen Natriumcarbonat in 150 Teilen Wasser vermischt und die Kupplung bei 0 bis 5 zu Ende geführt. Nach beendeter Kupplung wird der ausgeschiedene Farbstoff durch Filtra tion abgetrennt, mit verdünnter Natriumchlo- ridlösung gewaschen und getrocknet.
Process for the preparation of a monoazo dye. It has been found that a valuable monoazo dye is obtained if diazotized 6-nitro-4-chloro-2-amino-l-oxybenzene is combined with 1-sulfacetamino-7-oxynaphthalene.
The new dye. is a blackish powder that is mixed in water with blue, in dilute caustic soda with green-blue and in concentrated sulfuric acid with. red color dissolves and dyes wool from an acid bath in blue tones, which are converted into an olive with good wet fastness and excellent light fastness when re-chromed.
The 1-sulfacetamino-7-oxynaphthalene used as starting material for the present process can be obtained, for example, by monoacylating 1-amino-7-oxynaphthalene on the amino group with chloroacetic acid chloride and the 1-chloroacetylamino-7 obtained -oxynaphthalene with sulphurous acid or with. converts the salts of this acid.
The coupling can be carried out by methods known per se, for example in an alkaline medium.
<I> Example: </I> 16.0 parts of 6-nitro-4-chloro-2-amino-1-oxybenzene are suspended in 22 parts of 30% strength hydrochloric acid and 150 parts of water and added at 5 diazotized a solution of 6.9 parts of sodium nitrite in 25 parts of water. The suspension thus obtained.
is mixed with a solution of 28.1 parts of 1-sulfacetamino-7-oxynaphthalene, 4 parts of sodium hydroxide, 5.3 parts of sodium carbonate in 150 parts of water and the coupling at 0 to 5 is added End led. When the coupling has ended, the dye which has separated out is separated off by filtration, washed with dilute sodium chloride solution and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH292083T | 1950-08-01 | ||
| CH296528T | 1950-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH296528A true CH296528A (en) | 1954-02-15 |
Family
ID=25733177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH296528D CH296528A (en) | 1950-08-01 | 1950-08-01 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH296528A (en) |
-
1950
- 1950-08-01 CH CH296528D patent/CH296528A/en unknown
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