CH146753A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH146753A CH146753A CH146753DA CH146753A CH 146753 A CH146753 A CH 146753A CH 146753D A CH146753D A CH 146753DA CH 146753 A CH146753 A CH 146753A
- Authority
- CH
- Switzerland
- Prior art keywords
- diazotized
- blue
- dye
- sulfonic acid
- disulfo
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- FLIOATBXVNLPLK-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1N FLIOATBXVNLPLK-UHFFFAOYSA-N 0.000 claims description 3
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 229920002955 Art silk Polymers 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton 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
- 239000003795 chemical substances by application 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
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 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
- DVFTXJRRXYVZMY-UHFFFAOYSA-N dinaphtazin Chemical compound C1=CC=CC2=CC3=NC4=CC5=CC=CC=C5C=C4N=C3C=C21 DVFTXJRRXYVZMY-UHFFFAOYSA-N 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride 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
- C09B45/24—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)
Description
Zigsatztsatent zum Hauptpatent Nr.<B>136650.</B> Verfahren zur Herstellung eines neuen Azofarbstofes. Es wurde gefunden, dass man einen neuen Farbstoff erhält, wenn man auf 1; Mol des dinaphthazins der Formel:
EMI0001.0006
das durch saure Kupplung von diazotier- ter Sulfanilsäure mit 5,5'-Dioxy-7,7'-di- sulfo-2,2'-dinaphthylamin und Erwärmen des gebildeten Reaktionsproduktes erhalten werden kann, 1 Mol diazotierte 4-Nitro- 2 - amino -1- Phenol - 6 - sulfosäure,
hierauf 1 Mol diazotierte 2-Methoxy-l-aminobenzol- 5-sulfosäure einwirken lässt und den erhal tenen Farbstoff mit einem kupferabgeben den Mittel behandelt. Der erhaltene Farbstoff ist ein dunkles Pulver, das sich in Wasser mit rötlich blauer, in verdünnten Alkalien mit blauer und in konz. Schwefelsäure mit grüner Farbe löst. Er färbt natürliche Seide, Kunstseiden aus regenerierter Zellulose und Baumwolle in echten grauen Tönen.
<I>Beispiel:</I> 47,2 Teile 5,5'-Dioxy-7,7'-disulfo-1,1',2',2,- dinaphthazin und 50 Teile wasserfreie Soda werden in 500 Teilen Wasser gelöst und mit Eis auf 0 bis 5 gekühlt. Man kom biniert mit dem Diazokörper aus 23,4 Tei len 4 - Nitro - 2 - amino-l-phenol-6-sulfosäure und, nachdem dieser verschwunden ist, mit dem Diazokörper aus 20;
3 Teilen 2-Methoxy- 1-aminobenzol-5-sulfosäure. Nach beendeter Kupplung wird der Farbstoff abgeschieden und durch Aufkochen mit einer wässerigen Lösung von 40 Teilen krist. Kupfersulfat in die Kupferverbindung übergeführt; diese wird mit Kochsalz abgeschieden und ge trocknet.
Zigsatztsatent for main patent no. <B> 136650. </B> Process for the production of a new azo dye. It has been found that a new dye is obtained by clicking on 1; Moles of dinaphthazine of the formula:
EMI0001.0006
which can be obtained by acidic coupling of diazotized sulfanilic acid with 5,5'-dioxy-7,7'-disulfo-2,2'-dinaphthylamine and heating of the reaction product formed, 1 mol of diazotized 4-nitro-2 - amino -1- phenol-6-sulfonic acid,
then 1 mole of diazotized 2-methoxy-l-aminobenzene-5-sulfonic acid can act and the dye obtained is treated with a copper-releasing agent. The dye obtained is a dark powder which turns reddish blue in water, blue in dilute alkalis and blue in conc. Dissolves sulfuric acid with a green color. It dyes natural silk, artificial silk from regenerated cellulose and cotton in real gray tones.
<I> Example: </I> 47.2 parts of 5,5'-dioxy-7,7'-disulfo-1,1 ', 2', 2, - dinaphthazine and 50 parts of anhydrous soda are dissolved in 500 parts of water and chilled to 0-5 with ice. Combine with the diazo body from 23.4 parts of 4 - nitro - 2 - amino-1-phenol-6-sulfonic acid and, after this has disappeared, with the diazo body from 20;
3 parts of 2-methoxy-1-aminobenzene-5-sulfonic acid. After coupling is complete, the dye is deposited and crystallized by boiling with an aqueous solution of 40 parts. Copper sulfate converted into the copper compound; this is deposited with table salt and dried ge.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH146753T | 1929-06-12 | ||
| CH136650T | 1929-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146753A true CH146753A (en) | 1931-04-30 |
Family
ID=25712791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146753D CH146753A (en) | 1929-06-12 | 1929-06-12 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146753A (en) |
-
1929
- 1929-06-12 CH CH146753D patent/CH146753A/en unknown
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