CH263525A - Process for the preparation of a chromium-containing azo dye. - Google Patents
Process for the preparation of a chromium-containing azo dye.Info
- Publication number
- CH263525A CH263525A CH263525DA CH263525A CH 263525 A CH263525 A CH 263525A CH 263525D A CH263525D A CH 263525DA CH 263525 A CH263525 A CH 263525A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromium
- dye
- amino
- azo dye
- containing azo
- Prior art date
Links
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 12
- 229910052804 chromium Inorganic materials 0.000 title claims description 12
- 239000011651 chromium Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- MJWDIGUUVRCTFY-UHFFFAOYSA-N 6-methoxynaphthalen-2-amine Chemical compound C1=C(N)C=CC2=CC(OC)=CC=C21 MJWDIGUUVRCTFY-UHFFFAOYSA-N 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical class [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 241001453233 Doodia media Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 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
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
- 230000008673 vomiting Effects 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Verfahren zur Herstellung eines chromhaltigen</B> Azofarbstoffes. Es wurde gefunden, dass ein wertvoller chromhaltiger Azofarbstoff hergestellt wer den kann, wenn man den aus diazotierter 2- Amino-4-nitro-l-phenol-6-sulfonsäure und 2- Amino-6-methoxynaphthalin erhältlichen Farb stoff mit chromabgebenden Mitteln behan delt.
Der neue chromhaltige Farbstoff ist ein schwärzliches Pulver, das sich in Wasser und in verdünnter Sodalösung mit graugrüner und in kotz. Schwefelsäure mit bordeauxroter Farbe löst und Wolle aus schwefelsaurem Färbebade in gleichmässigen grünen Tönen färbt, die gut licht- und walkecht sind.
Der dem vorliegenden Verfahren als Aus gangsstoff dienende Farbstoff kann aus den angegebenen Komponenten in bekannter Weise, z. B. durch Kupplung in saurem Me dium, oder auch in Gegenwart von Pyridin, erhalten werden. Als chromabgebende Mittel wählt man zweckmässig solche, die das Chrom in dreiwertiger Form enthalten und daher keine schädliche Oxydationswirkung besitzen, insbesondere Chrom-(III)-Salze. Die Umset zung kann in an sich bekannter Weise in sau rem, neutralem oder alkalischem Medium, mit oder ohne Zusätze z. B. von Neutralsalzen, gegebenenfalls komplexbildender Art, organi schen Lösungsmitteln, wie Alkohol oder Pyri- din, offen oder unter Druck durchgeführt werden.
<I>Beispiel:</I> 23,4 Teile 4-Nitro-2-amino-l-phenol-6-sul- fonsäure werden in bekannter Weise diazo- tiert und mit 18 Teilen 2-Amino-6-methoxy- naphthalin bei Gegenwart von Pyridin ge kuppelt. Der abfiltrierte Farbstoff wird in 1800 Teilen Wasser bei Siedehitze gelöst und mit einer Chromformiatlösung versetzt, die eine 8,4 Teilen Chromoxyd entsprechende Menge Chrom enthält. Man erhitzt unter Rückflusskühlung längere Zeit zum Sieden und filtriert die erhaltene, in Wasser schwer lösliche Chromverbindung ab.
Sie wird durch Lösen in verdünnter Natronlauge in eine leicht lösliche Form übergeführt und ge trocknet.
<B> Process for the production of a chromium-containing </B> azo dye. It has been found that a valuable chromium-containing azo dye can be produced if the dye obtainable from diazotized 2-amino-4-nitro-1-phenol-6-sulfonic acid and 2-amino-6-methoxynaphthalene is treated with chromium-releasing agents .
The new chromium-containing dye is a blackish powder, which in water and in dilute soda solution turns gray-green and in puke. Sulfuric acid with a burgundy color dissolves and dyes wool from a sulfuric acid dye bath in even green tones that are lightfast and whackfast.
The present process as starting material from serving dye can be prepared from the specified components in a known manner, for. B. medium by coupling in acidic Me, or in the presence of pyridine, can be obtained. As chromium-releasing agents, it is expedient to choose those which contain chromium in trivalent form and therefore have no harmful oxidizing effect, in particular chromium (III) salts. The implementation can be carried out in a known manner in acidic, neutral or alkaline medium, with or without additives such. B. of neutral salts, possibly complex-forming type, organic solvents such as alcohol or pyridine, can be carried out openly or under pressure.
<I> Example: </I> 23.4 parts of 4-nitro-2-amino-1-phenol-6-sulphonic acid are diazotized in a known manner and with 18 parts of 2-amino-6-methoxynaphthalene coupled in the presence of pyridine. The filtered dye is dissolved in 1800 parts of water at boiling point and a chromium formate solution is added which contains an amount of chromium corresponding to 8.4 parts of chromium oxide. The mixture is heated to boiling with reflux for a long time and the chromium compound obtained, which is sparingly soluble in water, is filtered off.
It is converted into an easily soluble form by dissolving it in dilute sodium hydroxide solution and then dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH263525T | 1943-12-02 | ||
| CH258297T | 1948-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH263525A true CH263525A (en) | 1949-08-31 |
Family
ID=25730162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH263525D CH263525A (en) | 1943-12-02 | 1943-12-02 | Process for the preparation of a chromium-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH263525A (en) |
-
1943
- 1943-12-02 CH CH263525D patent/CH263525A/en unknown
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