CH146763A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH146763A CH146763A CH146763DA CH146763A CH 146763 A CH146763 A CH 146763A CH 146763D A CH146763D A CH 146763DA CH 146763 A CH146763 A CH 146763A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- dye
- disulfo
- dioxy
- diazotized
- 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 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- DQNAQOYOSRJXFZ-UHFFFAOYSA-N 5-Amino-1-naphthalenesulfonic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1S(O)(=O)=O DQNAQOYOSRJXFZ-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
- 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
- 150000003839 salts Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 239000002253 acid Substances 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 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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- DBNPDRYVYQWGFW-UHFFFAOYSA-N N.[Cu]=O Chemical compound N.[Cu]=O DBNPDRYVYQWGFW-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 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
- 238000003756 stirring Methods 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
Zusatzpatent zum Hauptpatent Nr. 136650. Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, dass man einen neuen Farbstoff erhält, wenn man auf 7. Mol des 5,5'-Dioxy-7,7'-disulfo-1,1',2'j,2- dinaphthazins der Formel:
EMI0001.0009
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 6-Nitro- 2 - amino -1- Phenol - 4 - sulfosäure,
hierauf 1 Mol diazotierte 1-Naphthylamin-5-sulfo- säure einwirken lässt und den erhaltenen Farbstoff mit einem kupferabgebenden Mittel behandelt. Der erhaltene Farbstoff ist ein dunkles Pulver, das sich in Wasser, sowie ver dünnten Alkalien mit blauer und in konz. Schwefelsäure mit grünblauer Farbe löst.
Er färbt natürliche Seide, Baumwolle und Kunstseide aus regenerierter Zellulose aus neutralem oder schwach alkalischem Glau- bersalzbade in sehr echten grünlichgraue n Tönen.
Beispiel: 47, 2 Teile 5,5'-Dioxy-t7,7'-disulfo-1,1.',2',?- dinaphthazin werden in Gegenwart von Soda mit dem Diazokörper aus 23,4 Teilen 6-Nitro-2-amino-l-phenol-4-sulfosäure zum Monoazofarbstoff und darauf mit dem Di- azokörper aus 22,5 Teilen 1-Naphthylamin- 5-sulfosäure zum Disazofarbstoff kombiniert.
Nach beendeter Kupplung versetzt man mit der Kupferoxydammoniaklösung aus 25 Teilen krist.Kupfersulfat, wärmt unter Rüh ren auf 80 auf, salzt aus, filtriert und trocknet.
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 when one uses 7th mole of 5,5'-dioxy-7,7'-disulfo-1,1 ', 2'j, 2-dinaphthazine of the formula:
EMI0001.0009
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 6-nitro-2 - amino -1-phenol-4-sulfonic acid,
then 1 mol of diazotized 1-naphthylamine-5-sulfonic acid 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 green-blue color.
It dyes natural silk, cotton and rayon made from regenerated cellulose from a neutral or weakly alkaline goat salt bath in very genuine greenish-gray tones.
Example: 47.2 parts of 5,5'-dioxy-t7,7'-disulfo-1,1. ', 2',? - dinaphthazine are converted in the presence of soda with the diazo body from 23.4 parts of 6-nitro-2 -amino-1-phenol-4-sulfonic acid to the monoazo dye and then combined with the diazo body of 22.5 parts of 1-naphthylamine-5-sulfonic acid to form the disazo dye.
After coupling is complete, the copper oxide ammonia solution of 25 parts of crystalline copper sulfate is added, heated to 80 with stirring, salted out, filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH146763T | 1929-06-12 | ||
| CH136650T | 1929-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146763A true CH146763A (en) | 1931-04-30 |
Family
ID=25712801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146763D CH146763A (en) | 1929-06-12 | 1929-06-12 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146763A (en) |
-
1929
- 1929-06-12 CH CH146763D patent/CH146763A/en unknown
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