CH272479A - Process for the preparation of a dye of the stilbene series. - Google Patents
Process for the preparation of a dye of the stilbene series.Info
- Publication number
- CH272479A CH272479A CH272479DA CH272479A CH 272479 A CH272479 A CH 272479A CH 272479D A CH272479D A CH 272479DA CH 272479 A CH272479 A CH 272479A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- stilbene series
- mol
- acid
- Prior art date
Links
- 238000000034 method Methods 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
- 239000000975 dye Substances 0.000 claims description 7
- JOLPMPPNHIACPD-ZZXKWVIFSA-N (e)-3-(4-aminophenyl)prop-2-enoic acid Chemical compound NC1=CC=C(\C=C\C(O)=O)C=C1 JOLPMPPNHIACPD-ZZXKWVIFSA-N 0.000 claims description 3
- 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 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229920003043 Cellulose fiber Polymers 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 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 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material 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
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/04—Stilbene-azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum. Hauptpatent Nr.<B>2269177.</B> Verfahren zur Herstellung eines Farbstoffes der Stilbenreihe. Es wurde gefunden, dass man zu einem wertvollen Farbstoff der Stilbenreihe gelangt, wenn man 1 Mol 4,4'-Dinitrostilben-2,2'-di- sulfonsäure mit 2 Mol 4-Aminozimtsäure kondensiert.
Der neue Farbstoff bildet ein braunes Pul ver, das sich in Wasser mit gelber Farbe löst und die Cellulosefaser in orangegelben Tönen färbt.
Die Kondensation wird zweckmässig in wässerigem Medium und in Gegenwart von Alkalihydroxyd durchgeführt, indem man beispielsweise die miteinander umzusetzen den Ausgangsstoffe in verdünnter, z. B. etwa 5%iger Natriumhydroxydlösung während längerer Zeit, z. B. 24 bis 48 Stunden, bei Siedetemperatur des Reaktionsgemisches auf einander einwirken lässt.
<I>Beispiel</I> 43 Teile 4,4'-Dinitrostilben-2,2'-disulfon- säure und 49 Teile 4-Aminozimtsäure werden mit 800 Vol.-Teilen Wasser unter Zusatz von 150 Vol.-Teilen 30%iger Natriumhydroxyd- lösung gelöst. Diese Lösung wird während 24 Stunden unter Rühren und Rückfluss- kühlung im Sieden erhalten.
Dann wird durch Zugabe von Salzsäure der Überschuss an Natiiumhydroxyd neutralisiert und durch Zugabe von 100 Teilen Natriumchlorid das Kondensationsprodukt abgeschieden; dieses wird abfiltriert und getrocknet.
Additional patent for. Main patent no. <B> 2269177. </B> Process for the production of a dye of the stilbene series. It has been found that a valuable stilbene series dye is obtained if 1 mole of 4,4'-dinitrostilbene-2,2'-disulfonic acid is condensed with 2 moles of 4-aminocinnamic acid.
The new dye forms a brown powder that dissolves in water with a yellow color and dyes the cellulose fiber in orange-yellow tones.
The condensation is conveniently carried out in an aqueous medium and in the presence of alkali metal hydroxide, for example by reacting the starting materials in dilute, z. B. about 5% sodium hydroxide solution for an extended period of time, e.g. B. 24 to 48 hours, at the boiling point of the reaction mixture can act on each other.
<I> Example </I> 43 parts of 4,4'-dinitrostilbene-2,2'-disulfonic acid and 49 parts of 4-aminocinnamic acid are mixed with 800 parts by volume of water with the addition of 150 parts by volume of 30% strength Sodium hydroxide solution dissolved. This solution is obtained for 24 hours with stirring and reflux cooling at the boil.
Then the excess of sodium hydroxide is neutralized by adding hydrochloric acid and the condensation product is separated out by adding 100 parts of sodium chloride; this is filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH272479T | 1948-09-03 | ||
| CH269177T | 1948-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH272479A true CH272479A (en) | 1950-12-15 |
Family
ID=25731055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH272479D CH272479A (en) | 1948-09-03 | 1948-09-03 | Process for the preparation of a dye of the stilbene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH272479A (en) |
-
1948
- 1948-09-03 CH CH272479D patent/CH272479A/en unknown
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