CH296534A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH296534A CH296534A CH296534DA CH296534A CH 296534 A CH296534 A CH 296534A CH 296534D A CH296534D A CH 296534DA CH 296534 A CH296534 A CH 296534A
- Authority
- CH
- Switzerland
- Prior art keywords
- violet
- parts
- monoazo dye
- amino
- acid
- 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
- 239000000975 dye Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 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
- 210000002268 wool Anatomy 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 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
- 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
- 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 dianotiertes 3,4,6-Trichlor-2-amino-l-oxy- benzol mit 1 -Sulfacetamino-7-oxynaphthalin vereinigt..
Der neue Farbstoff stellt ein dunkles Pul ver dar, das sieh in Wasser mit violetter und in konzentrierter Schwefelsäure mit rotviolet- ter Farbe löst und Wolle aus saurem Bade in violettbraunen Tönen färbt, welche beim Naehehromieren in ein Grau von guten Nass- eclitheiten und vorzüglicher Liehtechtheit übergeführt werden.
Das dem vorliegenden Verfahren als Aus gangsstoff dienende 1-Sulfaeel;amino-7-oxy- na.plitIialin kann beispielsweise erhalten wer den, indem man 1-Amino-7-oxynaphthalin an der Aminogruppe mit Chloressigsäurechlorid i orioacvliert und das erhaltene 1-Chlor-acetyl- amino=7-oxy-naphthalin mit schwefliger Säure bzw. mit. den Salzen dieser Säure unLsetzt.
Die Kupplung kann naeh an sich bekann t en Methoden. z. B. in alkalisehem lIedium, erfolgen.
Beispiel: \_'1,2.i Teile 3,4,6-Triehlor-2-amino-l-oxy- benzol werden in 22 Teilen 30 % iger Salzsäure und 150 Teilen Wasser suspendiert und bei 5 mit einer Lösung von 6,9 Teilen Natriumnitrit in 25 Teilen Wasser dianotiert.
Die so erhal tene Suspension wird mit einer Lösung von 28,1 Teilen 1-Sulfacetamino-7-oxynaphthalin, 4 Teilen Natriumhydroxyd, 5,3 Teilen Na- triumcarbonat in 150 Teilen Nasser vermischt und die Kupplung bei 0 bis 5 zu Ende ge führt. Nach beendeter Kupplung -wird der ausgeschiedene Farbstoff durch Filtration ab getrennt, mit verdünnter Natriumchlorid- lösung gewaschen und getrocknet.
Process for the preparation of a monoazo dye. It has been found that a valuable monoazo dye is obtained if dianotated 3,4,6-trichloro-2-amino-1-oxybenzene is combined with 1-sulfacetamino-7-oxynaphthalene.
The new dye is a dark powder that dissolves in water with violet and in concentrated sulfuric acid with red-violet color and dyes wool from an acid bath in violet-brown tones, which when chromed in a gray of good wetness and excellent lightfastness be transferred.
The 1-sulfaeel; amino-7-oxy- na.plitIialin serving as starting material in the present process can be obtained, for example, by orioacvlating 1-amino-7-oxynaphthalene on the amino group with chloroacetic acid chloride and the 1-chloro obtained acetyl-amino = 7-oxy-naphthalene with sulfurous acid or with. to the salts of this acid.
The coupling can be carried out using methods known per se. z. B. in alkaline medium.
Example: 1.2.1 parts of 3,4,6-triehlor-2-amino-1-oxybenzene are suspended in 22 parts of 30% strength hydrochloric acid and 150 parts of water and, at 5, with a solution of 6, 9 parts of sodium nitrite dianotized in 25 parts of water.
The suspension obtained in this way 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 is completed at 0-5. After the coupling has ended, the dyestuff 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 |
|---|---|---|---|
| CH296534T | 1950-08-01 | ||
| CH292083T | 1950-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH296534A true CH296534A (en) | 1954-02-15 |
Family
ID=25733183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH296534D CH296534A (en) | 1950-08-01 | 1950-08-01 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH296534A (en) |
-
1950
- 1950-08-01 CH CH296534D patent/CH296534A/en unknown
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