CH178414A - Process for the production of a copper-containing dye. - Google Patents
Process for the production of a copper-containing dye.Info
- Publication number
- CH178414A CH178414A CH178414DA CH178414A CH 178414 A CH178414 A CH 178414A CH 178414D A CH178414D A CH 178414DA CH 178414 A CH178414 A CH 178414A
- Authority
- CH
- Switzerland
- Prior art keywords
- copper
- dye
- nitro
- production
- mol
- Prior art date
Links
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 7
- 229910052802 copper Inorganic materials 0.000 title claims description 7
- 239000010949 copper Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 3
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/18—Trisazo or higher polyazo dyes
- C09B33/24—Trisazo dyes of the type
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr.<B>174651.</B> Verfahren zur Herstellung eines kupferhaltigen Farbstoffes. Gemäss dem im Hauptpatent beschrie benen Verfahren erhält man einen kupfer haltigen Farbstoff, wenn man den Farbstoff aus dianotierter 4-Aniinoazober)zol-4'-sulfo- säure und 1-i#lethyl..4-amino-2-oxyberizol mit dianotierter 4'-Nitro-4-aminodiphenylamiri-2'- sulfosäure weiter kuppelt und das so erhal- tetie Produkt mit Verbindungen des zwei wertigen Kupfers behandelt.
Wie nun weiter. gefunden wurde, erhält man einen ähnlichen Farbstoff, wenn man 1 Mol 3-Ainitio-l-oxybenzol, 2 Mol diano tierte 4-Nitro-l-ami,iobenzol-2-sulfosäure und 1 Mol dianotierte 4'-Niti-o-4-aminodipheriyl- ainirt-2'-sulfosäure kuppelt und den erlial- terten Trisazofarbstoff mit Verbindungen des zweiwertigen Kupfers behandelt.
<I>Beispiel:</I> 43,6 Teile 4-Nitro-l-aminobenzol-2-sulfo- säure werden dianotiert und in sodaalkali- sehei, Lösung mit 10,9 Teilen 3-Amino-l- oxybenzol vereinigt. Darin lässt man unter gleichzeitigem Zulauf einer Lösung von Natriumhydroxyd eine aus 30,9 Teilen 4'- Nitro-4-ainiriodiphenylamin-2'-srilfosäure be reitete Diazoverbindung zulaufen, so dass die Reaktion deutlich alkalisch ist, und lässt einige Stunden bis zur Beendigung der Kupp lung rühren.
Während eine verdünnte Lösung des Disazofarbstoffes stumpf bordeaux ist, ist die des Trisazofarbstoffes bereits braun. Mai) erwärmt darin auf etwa 80 und lässt eine mit Ammoniak übersättigte Lösung von 55 Teilen kristallisiertem Kupfersulfat zu laufen und hält eine Stunde bei 80 . Die Farbe der Lösung schlägt hierbei in gelb braun um. Nach Filtration wird der Farb stoff durch Kochsalz zur Abscheidung ge bracht. Er färbt Chromleder und vegetabilisch gegerbtes Leder havannabraun.
Die Kupplung mit den genannten Diazo- verbindungen kann auch in umgekehrter Reihenfolge vorgenommen werden.
Additional patent to main patent no. <B> 174651. </B> Process for the production of a copper-containing dye. According to the process described in the main patent, a copper-containing dye is obtained if the dye is made from dianotated 4-aniinoazober) zol-4'-sulfonic acid and 1-i # lethyl..4-amino-2-oxyberizole with dianotated 4 '-Nitro-4-aminodiphenylamine-2'-sulfonic acid is coupled further and the product thus obtained is treated with compounds of the bivalent copper.
How now further. was found, a similar dye is obtained if 1 mole of 3-Ainitio-1-oxybenzene, 2 moles of diano-tated 4-Nitro-1-ami, iobenzene-2-sulfonic acid and 1 mol of dianotated 4'-Niti-o-4 -aminodipheriyl-ainirt-2'-sulfonic acid couples and treats the aged trisazo dye with compounds of divalent copper.
<I> Example: </I> 43.6 parts of 4-nitro-1-aminobenzene-2-sulfonic acid are dianotized and combined in a soda-alkaline solution with 10.9 parts of 3-amino-l-oxybenzene. A diazo compound prepared from 30.9 parts of 4'-nitro-4-ainiriodiphenylamine-2'-srilfonic acid is allowed to run in with a solution of sodium hydroxide, so that the reaction is clearly alkaline, and it is left for a few hours until the end of the Stir the coupling.
While a dilute solution of the disazo dye is dull burgundy, that of the trisazo dye is already brown. Mai) warms up in it to about 80 and runs an ammonia-supersaturated solution of 55 parts of crystallized copper sulfate and keeps it at 80 for one hour. The color of the solution changes to yellow-brown. After filtration, the dye is deposited using common salt. It dyes chrome leather and vegetable-tanned leather havana brown.
The coupling with the diazo compounds mentioned can also be carried out in reverse order.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH178414T | 1934-12-22 | ||
| CH174651T | 1934-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH178414A true CH178414A (en) | 1935-07-15 |
Family
ID=25719545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH178414D CH178414A (en) | 1934-12-22 | 1934-12-22 | Process for the production of a copper-containing dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH178414A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1035171A1 (en) * | 1999-03-11 | 2000-09-13 | Ciba SC Holding AG | Azodyestuffs, their production and use |
| US6310220B1 (en) | 1997-03-06 | 2001-10-30 | Ciba Specialty Chemicals Corporation | Stabilizing polycarbonates |
-
1934
- 1934-12-22 CH CH178414D patent/CH178414A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6310220B1 (en) | 1997-03-06 | 2001-10-30 | Ciba Specialty Chemicals Corporation | Stabilizing polycarbonates |
| EP1035171A1 (en) * | 1999-03-11 | 2000-09-13 | Ciba SC Holding AG | Azodyestuffs, their production and use |
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