CH146764A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH146764A CH146764A CH146764DA CH146764A CH 146764 A CH146764 A CH 146764A CH 146764D A CH146764D A CH 146764DA CH 146764 A CH146764 A CH 146764A
- Authority
- CH
- Switzerland
- Prior art keywords
- diazotized
- dye
- disulfo
- dioxy
- greenish
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 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
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 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
- 241000974482 Aricia saepiolus Species 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
- 239000010949 copper Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000010446 mirabilite Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DBNPDRYVYQWGFW-UHFFFAOYSA-N N.[Cu]=O Chemical compound N.[Cu]=O DBNPDRYVYQWGFW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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 Mol des 5,5'-Dioxy-7,7'-disulfo-1,1',2':,2- dinaphthazins der Formel:
EMI0001.0009
das durch saure Kupplung von diazotier- ter Sulfanilsäure mit 5;5'-Dioxy-7,7'-di- sulfo-2,2'-d.inaphthylamin und Erwärmen des gebildeten Reaktionsproduktes erhalten werden kann, 1 Mol diazotierte 4-Nitro- 2 - amino -1- phenol -:
6 . 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 dunkel- bronziges Pulver, das sich in verdünnter Sodalösung mit blauer, in verdünnter Na tronlauge und in. konz. Schwefelsäure mit grünlichblauer Farbe löst.
Er färbt vege tabilische Fasern aus neutralem oder alkali schem Glaubersalzbade in sehr echten grün lichgrauen Tönen. <I>Beispiel:</I> 47, 2 Teile 5,5'-Dioxy-7,7'-disulfo-1,1',2',2- dinaphthazin werden in Gegenwart von Soda zuerst mit dem Diazokörper aus 23,4 Teilen 4-Nitro-2-amino-l-phenol-6-sulfosäure zum Monoazofarbstoff und darauf mit dem Diazokörper aus 22,5 Teilen 1-Naphthyl- amin-5-sulfosäure zum Disazofarbstoff kom biniert.
Nach beendeter Kupplung versetzt man mit der Kupferoxydammoniaklösung aus 25 Teilen krist. Kupfersulfat, wärmt auf 80 auf und rührt einige Zeit. Dann wird ausgesalzen, filtriert und getrocknet.
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 mole of 5,5'-dioxy-7,7'-disulfo-1,1 ', 2':, 2-dinaphthazine of the formula:
EMI0001.0009
which can be obtained by acid coupling of diazotized sulfanilic acid with 5; 5'-dioxy-7,7'-disulfo-2,2'-d.inaphthylamine and heating of the reaction product formed, 1 mol of diazotized 4-nitro 2 - amino -1- phenol -:
6. 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 bronze powder that dissolves in dilute soda solution with blue, in dilute sodium hydroxide solution and in. Conc. Sulfuric acid dissolves with a greenish-blue color.
It dyes vege stable fibers from neutral or alkaline Glauber's salt bath in very real greenish-gray tones. <I> Example: </I> 47, 2 parts of 5,5'-dioxy-7,7'-disulfo-1,1 ', 2', 2- dinaphthazine are first mixed with the diazo body from 23, in the presence of soda 4 parts of 4-nitro-2-amino-1-phenol-6-sulfonic acid to the monoazo dye and then combined with the diazo body of 22.5 parts of 1-naphthylamine-5-sulfonic acid to the disazo dye.
When the coupling is complete, the copper oxide ammonia solution of 25 parts of crystalline is added. Copper sulfate, warms up to 80 and stirs for a while. Then it is salted out, filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH146764T | 1929-06-12 | ||
| CH136650T | 1929-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146764A true CH146764A (en) | 1931-04-30 |
Family
ID=25712802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146764D CH146764A (en) | 1929-06-12 | 1929-06-12 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146764A (en) |
-
1929
- 1929-06-12 CH CH146764D patent/CH146764A/en unknown
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