CH146759A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH146759A CH146759A CH146759DA CH146759A CH 146759 A CH146759 A CH 146759A CH 146759D A CH146759D A CH 146759DA CH 146759 A CH146759 A CH 146759A
- Authority
- CH
- Switzerland
- Prior art keywords
- diazotized
- mol
- acid
- dye
- 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 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
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 229920002955 Art silk Polymers 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 229920000297 Rayon Polymers 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
- 230000002378 acidificating effect Effects 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
- 239000002964 rayon Substances 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 136650. Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, dass man einen neuen Farbstoff erhält, wenn man auf 1. Hol des 5,5'-Dioxy-7,7'-disulfo-1,1',2.',2- 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 Hol diazotierte 6-Nitro-2- amino-l-phenol-4-sulfosäure, hierauf 1 Hol diazotierte 1-Aminonaphthalin-4-sulfosäure einwirken lässt und den erhaltenen Farb stoff mit einem kupferabgebenden Mittel behandelt.
Der erhaltene Farbstoff ist ein dunkel- bronziges Pulver, das sich in Wasser mit roter, in verdünnten Alkalien mit blauer und in konz. Schwefelsäure mit grüner Farbe löst. Er färbt natürliche Seide. Baumwolle und Kunstseiden aus regenerier ter Zellulose aus neutralem oder schwach alkalischem Bade in sehr echten, grauen Tönen.
<I>Beispiel:</I> 47, 2 Teile 5,5'-Dioxy-7,7'-disulfo-1,1',2',2- dinaphthazin und 50 Teile Soda werden in 500 Teilen Wasser gelöst und mit Eis auf 0 bis 5 gekühlt. Darauf kuppelt man vor erst mit dem Diazokörper aus 23,4 Teilen 6-Nitro-2-amino-l-phenol-4-sulfosäure und, nachdem dieser verschwunden ist, mit dem Diazokörper aus 22,5 Teilen 1.-Aminonaph- thalin-4-sulfosäure. Nach beendeter Kupp lung wird der Farbstoff mit Kochsalz ab geschieden und filtriert.
Man löst ihn in <B>800</B> Teilen heissem Wasser und erwärmt einige Zeit zusammen mit einer wässerigen Lösung aus 24 Teilen krist. Kupfersulfat.
Additional patent 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 one takes on 1. Hol of 5,5'-dioxy-7,7'-disulfo-1,1 ', 2.', 2-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 the reaction product formed, 1 Hol diazotized 6-nitro-2- amino-l-phenol-4-sulfonic acid, then 1 Hol diazotized 1-aminonaphthalene-4-sulfonic acid can act and the dye obtained is treated with a copper donor.
The dye obtained is a dark bronze powder, which dissolves in water with red, in dilute alkalis with blue and in conc. Dissolves sulfuric acid with a green color. He dyes natural silk. Cotton and rayon made from regenerated cellulose from a neutral or slightly alkaline bath in very 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 soda are dissolved in 500 parts of water and mixed with Ice chilled to 0-5. Then you first couple with the diazo body from 23.4 parts of 6-nitro-2-amino-1-phenol-4-sulfonic acid and, after this has disappeared, with the diazo body from 22.5 parts of 1.-aminonaphthalene- 4-sulfonic acid. After coupling has ended, the dye is separated off with common salt and filtered.
It is dissolved in <B> 800 </B> parts of hot water and heated for some time together with an aqueous solution of 24 parts of crystalline. Copper sulfate.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH146759T | 1929-06-12 | ||
| CH136650T | 1929-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146759A true CH146759A (en) | 1931-04-30 |
Family
ID=25712797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146759D CH146759A (en) | 1929-06-12 | 1929-06-12 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146759A (en) |
-
1929
- 1929-06-12 CH CH146759D patent/CH146759A/en unknown
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