CH146762A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH146762A CH146762A CH146762DA CH146762A CH 146762 A CH146762 A CH 146762A CH 146762D A CH146762D A CH 146762DA CH 146762 A CH146762 A CH 146762A
- Authority
- CH
- Switzerland
- Prior art keywords
- blue
- acid
- disulfo
- dioxy
- dye
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 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
- 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
- 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
- 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
- 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
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 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
- 239000002253 acid Substances 0.000 claims 2
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000974482 Aricia saepiolus 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
- 229950000244 sulfanilic acid Drugs 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)
Description
Verfahren zur Herstellung eines neuen Azofarbstof%s. 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:
EMI0001.0006
das durch saure Kupplung von dianotier ter Sulfanilsäure mit 5,5'-Dioxy-7,7'-di- sulfo-2,2'-dinaphthylamin und Erwärmen des gebildeten Reaktionsproduktes erhalten werden kann, 1 Mol dianotiertes 4,6-Di- nitro-2-amino-l-phenol, hierauf 1 Mol di- azotiert@ 1-Aminobenzöl-2,5-disulfosäure ein wirken lässt und den erhaltenen Farbstoff mit einem kupferabgebenden Mittel be handelt.
Der erhaltene Farbstoff ist ein schwarz- bronziges Pulver, das sich in Wasser mit blauer, in verdünnten Alkalien mit grünlicli- blauer und in konz. Schwefelsäure mit blau grüner Farbe löst. Er färbt natürliche Seide. Baumwolle und Kunstseiden aus regenerier ter Zellulose aus neutralem oder schwach alkalischem Glaubersalzbade in echten grauen Tönen.
<I>Beispiel:</I> 4"7, 2 Teile 5,5'-Dioxy-7,7'-disulfo-l,l',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 20 Teilen 4,6-Dinitro-2-amino-l-phenol und, nachdem dieser verschwunden ist, mit dem Diazokör- per aus 29 Teilen 1-Aminobenzol-2,
5-di- sulfosäure. Nach beendeter Kupplung ver setzt man mit der Kupferoxydammoniak- lösung aus 24 Teilen krist. Kupfersulfat, wärmt auf<B>80'</B> auf und filtriert und trocknet.
Process for the preparation of a new azo dye% s. 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:
EMI0001.0006
which can be obtained by acidic coupling of dianotated sulfanilic acid with 5,5'-dioxy-7,7'-disulfo-2,2'-dinaphthylamine and heating of the reaction product formed, 1 mol of dianotated 4,6-dinitro -2-amino-l-phenol, then 1 mol azotized @ 1-aminobenzol-2,5-disulfonic acid can act and treat the dye obtained with a copper-releasing agent.
The dye obtained is a black-bronze powder which turns blue in water, greenish-blue in dilute alkalis and in conc. Sulfuric acid with a blue green color dissolves. He dyes natural silk. Cotton and artificial silk made from regenerated cellulose from neutral or weakly alkaline Glauber's salt bath in real gray tones.
<I> Example: </I> 4 "7, 2 parts of 5,5'-dioxy-7,7'-disulfo-l, l ', 2', 2-dinaphthazine and 50 parts of anhydrous soda are in 500 parts of water dissolved and cooled with ice to 0 to 5. It is combined with the diazo body from 20 parts of 4,6-dinitro-2-amino-1-phenol and, after this has disappeared, with the diazo body from 29 parts of 1-aminobenzene -2,
5-disulfonic acid. After coupling is complete, the copper oxide ammonia solution of 24 parts of crystalline is added. Copper sulfate, warms up to <B> 80 '</B> and then filtered and dries.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH146762T | 1929-06-12 | ||
| CH136650T | 1929-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146762A true CH146762A (en) | 1931-04-30 |
Family
ID=25712800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146762D CH146762A (en) | 1929-06-12 | 1929-06-12 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146762A (en) |
-
1929
- 1929-06-12 CH CH146762D patent/CH146762A/en unknown
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