DE741465C - Process for the preparation of copper-containing disazo dyes - Google Patents
Process for the preparation of copper-containing disazo dyesInfo
- Publication number
- DE741465C DE741465C DEG104213D DEG0104213D DE741465C DE 741465 C DE741465 C DE 741465C DE G104213 D DEG104213 D DE G104213D DE G0104213 D DEG0104213 D DE G0104213D DE 741465 C DE741465 C DE 741465C
- Authority
- DE
- Germany
- Prior art keywords
- copper
- parts
- disazo dyes
- amino
- dyes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 17
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 8
- 229910052802 copper Inorganic materials 0.000 title claims description 8
- 239000010949 copper Substances 0.000 title claims description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- AIOLRLMFOWGSPL-UHFFFAOYSA-N chembl1337820 Chemical compound C1=CC=C2C(N=NC3=C4C=CC(=CC4=CC(=C3O)S(O)(=O)=O)S(O)(=O)=O)=CC=CC2=C1 AIOLRLMFOWGSPL-UHFFFAOYSA-N 0.000 description 1
- 150000001880 copper compounds Chemical class 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 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
- 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
- C09B33/08—Disazo dyes in which the coupling component is a hydroxy-amino compound
- C09B33/10—Disazo dyes in which the coupling component is a hydroxy-amino compound in which the coupling component is an amino naphthol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von kupferhaltigen Disazofarbstoffen Es wurde gefunden, daß man neue wertvolle Farbstoffe erhält, wenn man i Mol diazotierte Aminobenzol-2-carbonsäure und i Mol diazotierte i-Amino-2-oxy-3-chlorbenzol-5-sulfonsäure und i Mol 5, 5'-Dioxy-2, 2'-dinaphthylharnstoff-7, 7'-disulfonsäure einwirken läßt und die Farbstoffe in üblicher Weise mit kupferabgebenden Mitteln behandelt. An Stelle der i-Aminobenzol-2-carbonsäure können auch deren Substitutionsverbindungen ohne weitere löslichmachende Gruppen, wie i-Amino-4-chlorbenzol-2-carbonsäure oder i-Amino-4-nitroberizol-2-carbonsäure, verwendet werden.Process for the preparation of copper-containing disazo dyes Es it has been found that new valuable dyes are obtained if one mole is diazotized Aminobenzene-2-carboxylic acid and 1 mole of diazotized i-amino-2-oxy-3-chlorobenzene-5-sulfonic acid and i mole of 5, 5'-dioxy-2, 2'-dinaphthylurea-7, 7'-disulfonic acid is allowed to act and the dyes treated in the usual manner with copper donors. At Substitution compounds can also be substituted for the i-aminobenzene-2-carboxylic acid without further solubilizing groups, such as i-amino-4-chlorobenzene-2-carboxylic acid or i-Amino-4-nitroberizole-2-carboxylic acid can be used.
Vor den bekannten kupferhaltigen Farbstoffen, welche man dadurch herstellt, daß man i Mol 5, 5'-Dioxy-2, 2'-dinaphthylharnstOff-7, 7'-disulfonsäure mit i Mol diazotierter i-Aminobenzol-2,-carbonsäure und mit i Mol diazotierter i -Amino-2-oxybenzol-5-sulfOnsäure-3-carbonsäure oder mit 2 Mol diazotierter i-Amino-2-0xy-3-chlorbenzol-5-sulfonsäure kuppelt und anschließend auf die Disazofarbstoffe kupferabgebende Mittel einwirken läßt, zeichnen sich die Farbstoffe nach der vorliegenden Erfindung dadurch aus, daß sie in Faserstoffgemischen, welche Cellulosefasern und Acetatseidenkunstseidefasern enthalten, die letzteren nicht anschmutzen, wie dies die bekannten Farbstoffe tun.Before the well-known copper-containing dyes, which are produced by that one mole of 5, 5'-dioxy-2, 2'-dinaphthylurestOff-7, 7'-disulfonic acid with i mole diazotized i-aminobenzene-2-carboxylic acid and i-amino-2-oxybenzene-5-sulfonic acid-3-carboxylic acid diazotized with one mole or with 2 moles of diazotized i-amino-2-0xy-3-chlorobenzene-5-sulfonic acid and then let copper-donating agents act on the disazo dyes, draw the dyes according to the present invention are characterized in that they are in fiber mixtures, which contain cellulosic fibers and acetate silk synthetic fibers, the latter do not stain like the known dyes do.
Beispiel i 223,5 Teile i Amino-2-oxy-3-chlorbenzol-5-sülfonsäure werden in üblicher Weise diazotiert. Die Diazoverbindung wird zu einer Lösung von 5o4 Teilen 5, 5'-Dioxy-2, z -dinaphthylharnstoff-7, 7'-disülfonsäure in 5000 Teilen Wasser und Zoo Teilen Natriumcarbonat gegeben. Nach einigen Stunden ist die Kupplung beendet. Es werden nun noch 22o Teile Natriumcarbonat und bei 5 bis 8° 137 Teile diazotierte i-Aminobenzol-2-carbonsäure zugegeben. Nach beendigter Farbstoffbildung wird mit- Kochsalz ausgefällt und der Farbstoff. abfiltrert.Example i 223.5 parts of i amino-2-oxy-3-chlorobenzene-5-sulphonic acid are diazotized in the customary manner. The diazo compound is added to a solution of 504 parts of 5,5'-dioxy-2, z-dinaphthylurea-7,7'-disulfonic acid in 5000 parts of water and zoo parts of sodium carbonate. The coupling is complete after a few hours. 220 parts of sodium carbonate and, at 5 to 8 °, 137 parts of diazotized i-aminobenzene-2-carboxylic acid are now added. After the formation of the dye is complete, it is precipitated with sodium chloride and the dye. filtered off.
Man löst den feuchten Filterkuchen nun in 20 ooo Teilen Wasser bei 8o°, versetzt die Lösung mit 28o Teilen Natriumacetat krist. und läßt 5oo Teile Kupfersulfat krist. in Form einer 2o°%igen Lösung bei 8o bis 85' zufließen. Es wird etwa a Stunden bei 8o bis 85° gerührt und dann die Kupferverbindung des Farbstoffes mit Kochsalz ausgefällt.The moist filter cake is now dissolved in 20,000 parts of water at 80 °, and 28o parts of crystalline sodium acetate are added to the solution. and leaves 500 parts of copper sulfate crystalline. in the form of a 20% solution at 8o to 85 ' . It is stirred for about a hour at 80 to 85 ° and then the copper compound of the dye is precipitated with sodium chloride.
Der getrocknete Farbstoff stellt ein schwärzlich violettes Pulver dar. Er löst sich in Wasser mit blauroter Farbe und färbt Cellulosefasern in sehr lichtechten bordoroten Tönen.The dried dye turns into a blackish purple powder It dissolves in water with a blue-red color and stains cellulose fibers very much lightfast bordeaux red tones.
Selbstverständlich kann die Kupferung auch ohne vorangehende Abtrennung des Farbstoffes, also unmittelbar anschließend an die Kupplung, vorgenommen werden.Of course, the copper plating can also be done without prior separation of the dye, i.e. immediately following the coupling.
Beispiel a 28z Teile i-Amino-.1-nitrobenzol-2-carbonsäure werden in bekannter Weise dianotiert. Das Diazotierungsgemisch läßt man zu einer neutralen Lösung von 5o4 Teilen 5, 5'-Dioxy-2, 2'-dinaphthylharnstoff-7, 7'-disulfonsäure in Sooo Teilen Wasser und 25o Teilen N atriumacetat krist. bei 5° zufließen. Nach beendigter Kupplung wird mit einer io°%igen Sodalösung neutralisiert. Dann werden 22o Teile wasserfreie Soda zugegeben. Man kühlt wieder auf 5° und läßt eine Lösung von 223,5 Teilen dianotierter r-Amino-2-oxy-3-chlorbenzol-5-sulfonsäure zufließen. Nach beendigter Kupplung wird die Kupferverbindung, wie in Beispiel .i beschrieben, hergestellt.Example a 28z parts of i-amino-.1-nitrobenzene-2-carboxylic acid are dianotized in a known manner. The diazotization mixture is allowed to add to a neutral solution of 504 parts of 5,5'-dioxy-2, 2'-dinaphthylurea-7,7'-disulfonic acid in sooo parts of water and 250 parts of crystalline sodium acetate. flow in at 5 °. When the coupling is complete, it is neutralized with an 10% strength soda solution. Then 220 parts of anhydrous soda are added. It is cooled again to 5 ° and a solution of 223.5 parts of dianotized r-amino-2-oxy-3-chlorobenzene-5-sulfonic acid is allowed to flow in. After the coupling is complete, the copper connection is produced as described in Example .i.
Der getrocknete Farbstoff stellt ein violettschwarzes Pulver dar. Er löst sich in Wasser mit blauroter Farbe und färbt Cellulosefasern in sehr lichtechten bordoroten Tönen.The dried dye is a purple-black powder. It dissolves in water with a blue-red color and dyes cellulose fibers in a very lightfast manner Bordeaux tones.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH741465X | 1941-09-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE741465C true DE741465C (en) | 1943-11-11 |
Family
ID=4533197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG104213D Expired DE741465C (en) | 1941-09-19 | 1941-10-12 | Process for the preparation of copper-containing disazo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE741465C (en) |
-
1941
- 1941-10-12 DE DEG104213D patent/DE741465C/en not_active Expired
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