CH146760A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH146760A CH146760A CH146760DA CH146760A CH 146760 A CH146760 A CH 146760A CH 146760D A CH146760D A CH 146760DA CH 146760 A CH146760 A CH 146760A
- Authority
- CH
- Switzerland
- Prior art keywords
- mol
- diazotized
- acid
- dye
- naphthylamine
- 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
- 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
- 239000000203 mixture Substances 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
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000002253 acid Substances 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
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- CYCGXYKRUBKWHT-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)piperazine;dihydrochloride Chemical compound Cl.Cl.ClC1=CC=C(Cl)C(N2CCNCC2)=C1 CYCGXYKRUBKWHT-UHFFFAOYSA-N 0.000 description 1
- YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 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
- 239000003795 chemical substances by application 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
Zusatzpatent zum Hauptpatent Nr. <B><I>136650.</I></B> Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, dass man einen neuen Farbstoff erhält, wenn man auf<B>1</B> Mol des 5,5'-Dioxy-7,7'-disulfo-1,1',2',2-diriaphthazins der Formel
EMI0001.0006
das durch saure Kupplung von diazotierter Stilfanilsäure mit 5,5'-Dioxy-7,7'-(lisulfo-2,2'- ditiaphthylamin und Erwärmen des gebil deten Reaktionsproduktes erhalten werden kann,
<B>1</B> Mol diazotierte 6-Nitro-2-amino-l- phenol-4-sulfosäure, hierauf<B>1</B> Mol eines dia- zotierten Gemisches von 2-Naphthylamin-5- und 2-Naphthylainin-8-stilfosäLire einwirken lässt und den erhaltenen Farbstoff mit einem kupferabgebenden Mittel behandelt.
Der erhaltene Farbstoff ist ein dunkel- bronziges Pulver, das sich in Wasser sowie verdünnten Alkalien mit blauer und in kon zentrierter Schwefelsäure mit blaugrüner Farbe löst. Er färbt natürliche Seide, Baum wolle und Kunstseiden aus regenerierter Zellulose aus neutralem oder schwach alka lischem Bade in sehr echten grauen Tönen. <I>Beispiel:</I> 47,2 Teile 5,5'-Dioxy-7,7'-disulfo-1,1',2',2- dinaphthazin und<B>50</B> Teile Soda werden in <B>500</B> Teilen Wasser gelöst und mit Eis auf <B>0</B> bis<B>50</B> gekühlt.
Man kombiniert vorerst mit dem Diazokörper aus 23,4 Teilen 6-Nitro- 2-amino-l-phenol-4-stilfosätire, und nachdem dieser nicht mehr nachzuweisen ist, mit dem Diazokörper aus<B>22,5</B> Teilen eines Gemisches von 2-Naphthylamin-5- und 2-Naphthylamin- 8-sulfosäure#. Nach beendeter Kupplung ver setzt man mit der Kupferoxydammonjaklö- sung aus 24 Teilen kristallisiertern Kupfer sulfat, wärmt auf<B>80 '</B> auf, salzt den Farb stoff nach einiger Zeit aus,
filtriert und trocknet.
Additional patent to main patent no. <B><I>136650.</I> </B> Process for the production of a new azo dye. It has been found that a new dye is obtained if one uses <B> 1 </B> mol of the 5,5'-dioxy-7,7'-disulfo-1,1 ', 2', 2-diriaphthazine der formula
EMI0001.0006
which can be obtained by acidic coupling of diazotized stilfanilic acid with 5,5'-dioxy-7,7 '- (lisulfo-2,2'-ditiaphthylamine and heating of the reaction product formed,
<B> 1 </B> mol of diazotized 6-nitro-2-amino-1-phenol-4-sulfonic acid, then <B> 1 </B> mol of a diazotized mixture of 2-naphthylamine-5- and 2 -Naphthylainin-8-stilfosäLire can act and the dye obtained is treated with a copper-releasing agent.
The dye obtained is a dark bronze powder which dissolves in water and dilute alkalis with blue and in concentrated sulfuric acid with a blue-green color. It dyes natural silk, cotton and artificial silk 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'-disulfo-1,1 ', 2', 2-dinaphthazine and <B> 50 </B> parts of soda dissolved in <B> 500 </B> parts of water and cooled with ice to <B> 0 </B> to <B> 50 </B>.
It is initially combined with the diazo body made of 23.4 parts of 6-nitro-2-amino-1-phenol-4-stilfosätire, and after this can no longer be detected, with the diazo body made of 22.5 parts a mixture of 2-naphthylamine-5- and 2-naphthylamine-8-sulfonic acid #. After the coupling is complete, the copper oxide ammonia solution is added from 24 parts of crystallized copper sulfate, heated to <B> 80 '</B>, the dye is salted out after a while,
filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH146760T | 1929-06-12 | ||
| CH136650T | 1929-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146760A true CH146760A (en) | 1931-04-30 |
Family
ID=25712798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146760D CH146760A (en) | 1929-06-12 | 1929-06-12 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146760A (en) |
-
1929
- 1929-06-12 CH CH146760D patent/CH146760A/en unknown
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