CH146758A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH146758A CH146758A CH146758DA CH146758A CH 146758 A CH146758 A CH 146758A CH 146758D A CH146758D A CH 146758DA CH 146758 A CH146758 A CH 146758A
- Authority
- CH
- Switzerland
- Prior art keywords
- mol
- dye
- dioxy
- diazotized
- 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 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-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
- 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
- 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
- 230000007935 neutral effect Effects 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
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 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 2
- 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
- 239000002253 acid 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
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
<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 Hol des 5, 5'-Dioxy-7, 7'-disulf o-1.,1', 2:'" 2 dinaphthazins der Formel:
EMI0001.0008
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 - amina -1- Phenol - 4 - sulfosäure, hierauf 1 Hol diazotiertes 4-Chlor-l-aminobenzol einwirken lässt und den erhaltenen Farbstoff mit einem kupferabgebenden Mittel behan delt.
Der erhaltene Farbstoff ist ein dunkles Pulver, das sich in Wasser, sowie ver dünnten Alkalien mit blauer und in konz. Schwefelsäure mit blaugrüner Farbe löst. Er färbt natürliche Seide, Baumwolle und Kunstseiden aus regenerierter Zellulose aus neutralem oder schwach alkalischem Bade in sehr echten grauen Tönen.
<I>Beispiel:</I> 47, 2 Teile 5,5'-Dioxy-;7,7'-disnlfo-1,1',2',2- dinaphthazin und 50 Teile Soda werden in 500 Teilen Wasser gelöst und mit Eis auf 0 bis 5 gekühl. Man kombiniert nun mit dem Di- azokörper aus 23,4 Teilen 6-Nitro-2-amino- 1-phenol-4-sulfosäure und, nachdem dieser nicht mehr nachzuweisen ist, mit dem Diazo- körper aus 12,
7 Teilen 4-Chlor-l-aminobenzol. Nach beendeter Kupplung versetzt man mit der gupferoxydammoniaklösung aus 2'4 Tei len krist. Kupfersulfat und wärmt auf<B>80'.</B> Nach einiger Zeit wird filtriert und ge 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 you add 2 dinaphthazines of the formula to 1 hol of 5, 5'-dioxy-7, 7'-disulfo-1., 1 ', 2:' "
EMI0001.0008
which can be obtained by acid coupling of diazotized sulfanilic acid with 5,5'-dioxy-7,7'-disulfo-2,2'-dinaphthylamine and heating of the reaction product formed, 1 Hol diazotized 6-nitro- 2 - amina -1-phenol-4-sulfonic acid, then 1 hol diazotized 4-chloro-l-aminobenzene is allowed to act and the dye obtained is treated with a copper-releasing agent.
The dye obtained is a dark powder that dissolves in water and dilute alkalis with blue and in conc. Sulfuric acid dissolves with a blue-green color. It dyes natural silk, cotton and rayon made from regenerated cellulose from neutral or slightly alkaline baths in very real gray tones.
<I> Example: </I> 47.2 parts of 5,5'-dioxy-; 7,7'-disnlfo-1,1 ', 2', 2-dinaphthazine and 50 parts of soda are dissolved in 500 parts of water and Chilled to 0 to 5 with ice. It is now combined with the diazo body from 23.4 parts of 6-nitro-2-amino-1-phenol-4-sulfonic acid and, after this can no longer be detected, with the diazo body from 12,
7 parts of 4-chloro-1-aminobenzene. After the coupling is complete, the gupferoxydammoniaklösung from 2'4 parts of crystalline is added. Copper sulfate and warms up to <B> 80 '. </B> After a while, it is filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH146758T | 1929-06-12 | ||
| CH136650T | 1929-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146758A true CH146758A (en) | 1931-04-30 |
Family
ID=25712796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146758D CH146758A (en) | 1929-06-12 | 1929-06-12 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146758A (en) |
-
1929
- 1929-06-12 CH CH146758D patent/CH146758A/en unknown
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