CH176231A - Process for the preparation of a triarylmethane dye. - Google Patents
Process for the preparation of a triarylmethane dye.Info
- Publication number
- CH176231A CH176231A CH176231DA CH176231A CH 176231 A CH176231 A CH 176231A CH 176231D A CH176231D A CH 176231DA CH 176231 A CH176231 A CH 176231A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- leuco compound
- triarylmethane dye
- oxidized
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000001003 triarylmethane dye Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 6
- AHVBXTGAXQKXSS-UHFFFAOYSA-N 3-anilinoheptane-3-sulfonic acid Chemical compound C(CCC)C(CC)(S(=O)(=O)O)NC1=CC=CC=C1 AHVBXTGAXQKXSS-UHFFFAOYSA-N 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 3
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 3
- BQLIKPMVSGIFQB-UHFFFAOYSA-N 2-(n-butylanilino)ethanesulfonic acid Chemical compound CCCCN(CCS(O)(=O)=O)C1=CC=CC=C1 BQLIKPMVSGIFQB-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical group CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Tr iarylmeth anfarbstoifes. In dem Hauptpatent 163012 ist ein Ver fahren zur Darstellung eines Triarylmethan- farbstoffes beschrieben. Es ist dadurch ge kennzeichnet, dass man 1 Mol p-Chlorbenzal- dehy d und 2 Mol Butylphenyltauriri zur Triplienylmethanverbindung kondensiert, zum Farbstoff oxydiert und den so erhaltenen Farbstoff mit p-Phenetidin umsetzt.
Es wurde weiter gefunden, dass man zu ähnlichen wertvollen Farbstoffen gelangt, wenn man statt dem im Hauptpatent 163012 verwendeten Buthylphenyltaurin Aminoalkyl- sulfonsäuren benutzt, in denen der an die Sulfonsäuregruppe gebundene Äthanrest durch eine höhere Alkylgruppe ersetzt ist.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung eines Triaryl- methanfarbstoffes. Es ist dadurch gekenn zeichnet, dass man 2 Mol Butylphenylamino- propansulfonsäure mit 1 bl=ol p-Chlorbenzal- dehyd zur Leukoverbindung kondensiert, die Leukoverbindung zum Farbstoff oxydiert und diesen bei höherer Temperatur mit p-Phene- tidin umsetzt.
<I>Beispiel</I> Man kondensiert 54 Gewichtsteile Butyl- phenylaminopropansulfonsäure
EMI0001.0036
mit 15 Gewichtsteilen p-Chlorbenzaldehyd in 200 Gewichtsteilen Wasser zur Leuko- verbindung. Diese wird in bekannter Weise zu einem leicht löslichen sehr klaren Farb stoff oxydiert. 22 Gewichtsteile dieses Farb stoffes werden bei<B>700</B> allmählich in zirka 40 Gewichtsteile p-Phenetidin eingetragen und dann während mehreren Stunden auf zirka 100-105 gehalten, bis die grüne Farbe in ein reines Blau übergegangen ist.
Man trägt die Reaktionsmasse darauf in verdünnte überschüssige Salzsäure ein, wäscht den als Harz ausgefallenen Farbstoff mehrmals mit salzsaurem Wasser aus und erhält daraus durch Neutralisieren mit Alkali, Lösen und Aussalzen ein Blau als schwach bronzierendes Pulver, welches die Faser in sehr klaren grünstickig blauen Tönen anfärbt.
Process for the preparation of a Tr iarylmeth anfarbstoifes. In the main patent 163012 a process is described for the preparation of a triarylmethane dye. It is characterized in that 1 mole of p-chlorobenzaldehyde and 2 moles of butylphenyltaurine are condensed to the triplienylmethane compound, oxidized to give the dye and the dye thus obtained is reacted with p-phenetidine.
It has also been found that similar valuable dyes are obtained if, instead of the buthylphenyltaurine used in the main patent 163012, aminoalkylsulfonic acids are used in which the ethane residue bound to the sulfonic acid group is replaced by a higher alkyl group.
The present patent is a process for the preparation of a triaryl methane dye. It is characterized in that 2 moles of butylphenylaminopropanesulfonic acid are condensed with 1 bl = ol p-chlorobenzaldehyde to give the leuco compound, the leuco compound is oxidized to form the dye and this is reacted with p-phenetidine at a higher temperature.
<I> Example </I> 54 parts by weight of butylphenylaminopropanesulfonic acid are condensed
EMI0001.0036
with 15 parts by weight of p-chlorobenzaldehyde in 200 parts by weight of water to form the leuco compound. This is oxidized in a known manner to a readily soluble, very clear dye. 22 parts by weight of this dye are gradually added to around 40 parts by weight of p-phenetidine at <B> 700 </B> and then held at around 100-105 for several hours until the green color has turned into a pure blue.
The reaction mixture is then poured into dilute excess hydrochloric acid, the dye which has precipitated out as resin is washed several times with hydrochloric acid and, by neutralizing with alkali, dissolving and salting out, a blue is obtained as a weakly bronzing powder, which colors the fiber in very clear greenish blue tones .
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE176231X | 1932-06-25 | ||
| CH163012T | 1932-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH176231A true CH176231A (en) | 1935-03-31 |
Family
ID=25717693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH176231D CH176231A (en) | 1932-06-25 | 1933-06-03 | Process for the preparation of a triarylmethane dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH176231A (en) |
-
1933
- 1933-06-03 CH CH176231D patent/CH176231A/en unknown
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