CH146765A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH146765A CH146765A CH146765DA CH146765A CH 146765 A CH146765 A CH 146765A CH 146765D A CH146765D A CH 146765DA CH 146765 A CH146765 A CH 146765A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- mol
- disulfo
- sulfonic acid
- azo dye
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 229920000297 Rayon Polymers 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000002964 rayon Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 1
- 229950000244 sulfanilic acid Drugs 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 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 description 1
- 239000000203 mixture Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
-
- 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/12—Disazo dyes in which the coupling component is a heterocyclic compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 136650. Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, dass man einen neuen Farbstoff erhält, wenn man auf 1 Mol des 5, 5'-Dioxy-7, 7'-disulfo-1, l', 2', 2-ditiaph- thazins der Formel
EMI0001.0009
das durch saure Kupplung von diazotierter Sulfanilsäure mit 5, 5'-Dioxy-7,7'-disulfo-2,
2'-dinaphthylamin und Erwärmen des gebil deten Reaktionsproduktes erhalten werden kann, 1 Mol diazotierte 4-Nitro-2-amino-l- phenol-6-sulfosäure, hierauf 1 Mol diazotierte 2-Naphthylamin-6-sulfosäni@e einwirken lässt und den erhaltenen Farbstoff mit einem kupferabgebenden Mittel behandelt.
Der erhaltene Farbstoff ist ein dunkles Pulver, das sich in verdünnten Alkalien mit graublauer und in konzentrierter Schwefel- säure mit grüner Farbe löst. Baumwolle und Kunstseiden aus regenerierter Zellulose wer den aus schwach alkalischem Bade in sehr echten grünlicbgrauen Tönen gefärbt.
<I>Beispiel:</I> 47,2 Teile 5, 5'-Dioxy-7, 7'-disulfo-1, 1', 2', 2-dinaphthazin werden in Gegenwart von Soda mit dem Diazokörper aus 23,4 Teilen 4-Nitro-2-amino-l-phenol-6-sulfosäure zuin Monoazofarbstoff und dieser mit dem Diazo- körper aus 22,5 Teilen 2-Naphthylaniin-6- sulfosäure zum Disazofarbstoff kombiniert. Nach beendeter Kupplung scheidet man den Farbstoff ab und löst ihn in 1000 Teilen Wasser von 80---90 .
Man versetzt niit der wässerigen Lösung aus 25 Teilen kristalli siertem Kupfersulfat, rührt einige Zeit, salzt aus, filtriert und trocknet.
<B> Additional patent </B> to main patent No. 136650. Process for the production of a new azo dye. It has been found that a new dye is obtained if 1 mole of the 5,5'-dioxy-7, 7'-disulfo-1, l ', 2', 2-ditiaphthazine of the formula
EMI0001.0009
the acidic coupling of diazotized sulfanilic acid with 5, 5'-dioxy-7,7'-disulfo-2,
2'-dinaphthylamine and heating of the formed reaction product can be obtained, 1 mole of diazotized 4-nitro-2-amino-1-phenol-6-sulfonic acid, then 1 mole of diazotized 2-naphthylamine-6-sulfosäni @ e can act and obtained dye treated with a copper donor.
The dye obtained is a dark powder which dissolves in dilute alkalis with a gray-blue color and in concentrated sulfuric acid with a green color. Cotton and rayon made from regenerated cellulose are dyed in very genuine greenish-gray tones from a weakly alkaline bath.
<I> Example: </I> 47.2 parts of 5, 5'-dioxy-7, 7'-disulfo-1, 1 ', 2', 2-dinaphthazine are in the presence of soda with the diazo body from 23.4 Parts of 4-nitro-2-amino-1-phenol-6-sulfonic acid to form a monoazo dye and this combined with the diazo body of 22.5 parts of 2-naphthylaniine-6-sulfonic acid to form the disazo dye. After coupling has ended, the dye is separated off and dissolved in 1000 parts of 80-90 water.
The aqueous solution of 25 parts of crystallized copper sulfate is added, the mixture is stirred for some time, salted out, filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH146765T | 1929-06-12 | ||
| CH136650T | 1929-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146765A true CH146765A (en) | 1931-04-30 |
Family
ID=25712803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146765D CH146765A (en) | 1929-06-12 | 1929-06-12 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146765A (en) |
-
1929
- 1929-06-12 CH CH146765D patent/CH146765A/en unknown
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