CH302803A - Process for the production of a copper-containing azo dye of the stilbene series. - Google Patents
Process for the production of a copper-containing azo dye of the stilbene series.Info
- Publication number
- CH302803A CH302803A CH302803DA CH302803A CH 302803 A CH302803 A CH 302803A CH 302803D A CH302803D A CH 302803DA CH 302803 A CH302803 A CH 302803A
- Authority
- CH
- Switzerland
- Prior art keywords
- copper
- dye
- production
- containing azo
- azo dye
- Prior art date
Links
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 13
- 229910052802 copper Inorganic materials 0.000 title claims description 13
- 239000010949 copper Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title claims description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- -1 copper-tetrammine compound Chemical class 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000005749 Copper compound Substances 0.000 description 3
- 150000001880 copper compounds Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- UETHPMGVZHBAFB-OWOJBTEDSA-N 4,4'-dinitro-trans-stilbene-2,2'-disulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O UETHPMGVZHBAFB-OWOJBTEDSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- UETHPMGVZHBAFB-UHFFFAOYSA-N 4,4'-dinitrostilbene-2,2'-disulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1C=CC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O UETHPMGVZHBAFB-UHFFFAOYSA-N 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines kupferhaltigen Azofarbstoffes der Stilbenreihe. Es wurde gefunden, dass man zu einem wertvollen, kupferhaltigen Azofarbstoff der Stilbenreihe gelangt, wenn man auf den Farb- stoff, der erhältlich ist, indem man 4,4'-Di- nitrostilben-2,2'-disulfonsäure beidseitig mit dem Aminodisazofarbstoff der Formel
EMI0001.0011
kondensiert, kupferabgebende Mittel einwir ken lässt.
Der neue Farbstoff bildet ein dunkles Pulver, das sich in Wasser mit violettbrau- ner Farbe löst und Baumwolle in lichtechten, rotstichig braunen Tönen färbt.
Die Kondensation der 4,4'-Dinitrostilben- 2,2'-disulfonsäure mit dem Arninodisazofarb- stoff, welcher zweckmässig in Form eines Al kalisalzes verwendet wird, wird vorteilhaft in wässrigem. Medium und in Gegenwart von Alkalihydroxyd durchgeführt. Gute Ergeb nisse werden beispielsweise erhalten, wenn man die miteinander umzusetzenden Stoffe in verdünnter, z.
B. 2- bis 8%igerAlkalihydroxyd- lösung während längerer Zeit, z. B. 5 bis 24 Stunden, bei erhöhter Temperatur, z. B. in offenem Gefäss bei Siedetemperatur des Re aktionsgemisches und unter Rückflusskühlung oder bei noch höheren Temperaturen und unter Druck aiüeinader einwirken lässt, Als kupferabgebende Mittel können beim vorliegenden Verfahren z.
B. Salze des ein- , oder zweiwertigen Kupfers wie Kupfer(I).- chlorid oder Kupfer(II)-sulfat in Betracht kommen, ferner auch Verbindungen, die Kup fer in komplexer Verbindung enthalten. Ins besondere sind für diesen ZweckKupferammin- komplexe geeignet, wie z. B. die aus Ammo niak, Alkylaminen wie Äthylamin, Morpholin, Pyridin oder Piperidin erhältlichen komplexen Kupferverbindungen.
Die Behandlung. mit dem kupferabgebenden Mittel wird zweck mässig in wässrigem Medium ausgeführt. Ge gebenenfalls kann die Behandlung mit den kupferabgebenden Mitteln in Gegenwart ge eigneter Zusätze erfolgen.
Als solche seien erwähnt: Basen wie Ammoniak und organische Basen, vorzugsweise ein überschuss derjenigen Base, die bereits im Molekül des gegebenen falls verwendeten Kupferamminkomplexes ent halten ist, <I>Beispiel:
</I> 56 Teile des Disazofarbstoffes der Formel
EMI0002.0002
hergestellt aus 1 Mol diazotierter 2-Amino-l- oxybenzol-4-sidfonsäure alkalisch gekuppelt mit 1 Mol 2 -Amino - 5 - oxynaphthalin - 7 - sul- fonsäure, weiterdiazotiert und sauer gekuppelt mit 1-Amino-3-methylbenzol,
werden in ein mit Rückflusskühler versehenes und mit 1200 Teilen Wasser beschicktes Rührgefäss einge tragen und gleichzeitig mit Natriiunhydroxyd- lösung neutralisiert. Dann werden 24 Teile Dinatriumsalz der 4,4'-Dinitrostilben-2,2'-di- sulfonsäure und 120 Teile 30 % ige Natxium- hydroxydlösung zugegeben und das Reaktions gemisch unter Rühren und Rückflusskühlung 24 Stunden im Sieden erhalten.
Durch Zu gabe von Natriiunchlorid und Neutralisieren eines Teils des Alkaliüberschusses mit Salz säure kann das gebildete Kondensationspro dukt aus dem Reaktionsgemisch abgeschieden werden. Zur Überführung in die komplexe Kupfer verbindung wird das abfiltrierte Konden sationsprodukt in 1000 Teilen Wasser aufge schlämmt, durch Zugabe von 40 Teilen 25 % iger Ammoniaklösung gelöst. Dann wer den 100 Teile einer 2n-Kupfersulfatlösung und 100 Teile 25 % ige Ammoniaklösung zu gesetzt, und die Mischung wird 30 Minuten unter Rühren bei 75 gehalten.
Die kom plexe Kupferverbindung lässt sich durch Aussalzen abscheiden und abfiltrieren.
Process for the production of a copper-containing azo dye of the stilbene series. It has been found that a valuable, copper-containing azo dye of the stilbene series is obtained if the dye, which is obtainable by reacting 4,4'-di-nitrostilbene-2,2'-disulfonic acid on both sides with the amino disazo dye, is obtained formula
EMI0001.0011
condensed, copper-releasing agent can act.
The new dye forms a dark powder which dissolves in water with a violet-brown color and dyes cotton in lightfast, reddish-brown tones.
The condensation of 4,4'-dinitrostilbene-2,2'-disulfonic acid with the aminodisazo dye, which is expediently used in the form of an alkali metal salt, is advantageously carried out in aqueous. Medium and carried out in the presence of alkali hydroxide. Good results are obtained, for example, if the substances to be reacted with one another are diluted, eg.
B. 2- to 8% alkali hydroxide solution for a long time, z. B. 5 to 24 hours, at an elevated temperature, e.g. B. in an open vessel at the boiling point of the Re action mixture and under reflux cooling or at even higher temperatures and under pressure aiüeinader can act as a copper-releasing agent in the present process z.
B. salts of mono- or divalent copper such as copper (I) .- chloride or copper (II) sulfate come into consideration, and also compounds that contain Kup fer in complex compound. Copper ammine complexes are particularly suitable for this purpose, such as B. from ammonia, alkylamines such as ethylamine, morpholine, pyridine or piperidine available complex copper compounds.
The treatment. with the copper-releasing agent is expediently carried out in an aqueous medium. If necessary, the treatment with the copper-releasing agents can be carried out in the presence of suitable additives.
The following may be mentioned as such: Bases such as ammonia and organic bases, preferably an excess of that base which is already contained in the molecule of the copper amine complex, if used, <I> Example:
</I> 56 parts of the disazo dye of the formula
EMI0002.0002
produced from 1 mole of diazotized 2-amino-l-oxybenzene-4-sidfonic acid coupled alkaline with 1 mole of 2-amino - 5 - oxynaphthalene - 7 - sulfonic acid, further diazotized and acidically coupled with 1-amino-3-methylbenzene,
are carried into a stirred vessel equipped with a reflux condenser and charged with 1200 parts of water and at the same time neutralized with sodium hydroxide solution. Then 24 parts of the disodium salt of 4,4'-dinitrostilbene-2,2'-disulfonic acid and 120 parts of 30% sodium hydroxide solution are added and the reaction mixture is kept boiling for 24 hours with stirring and reflux.
By adding sodium chloride and neutralizing part of the excess alkali with hydrochloric acid, the condensation product formed can be separated out from the reaction mixture. To convert the complex copper compound, the filtered condensation product is suspended in 1000 parts of water and dissolved by adding 40 parts of 25% ammonia solution. Then who set the 100 parts of a 2N copper sulfate solution and 100 parts of 25% ammonia solution, and the mixture is kept at 75 for 30 minutes with stirring.
The complex copper compound can be separated out by salting out and filtered off.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH280185T | 1949-07-29 | ||
| CH302803T | 1949-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302803A true CH302803A (en) | 1954-10-31 |
Family
ID=25731978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302803D CH302803A (en) | 1949-07-29 | 1949-07-29 | Process for the production of a copper-containing azo dye of the stilbene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302803A (en) |
-
1949
- 1949-07-29 CH CH302803D patent/CH302803A/en unknown
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