CH185594A - Process for the preparation of an unsymmetrical pentacarbocyanine dye. - Google Patents
Process for the preparation of an unsymmetrical pentacarbocyanine dye.Info
- Publication number
- CH185594A CH185594A CH185594DA CH185594A CH 185594 A CH185594 A CH 185594A CH 185594D A CH185594D A CH 185594DA CH 185594 A CH185594 A CH 185594A
- Authority
- CH
- Switzerland
- Prior art keywords
- condensation agent
- alkaline
- alkaline condensation
- dye
- pentacarbocyanine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 238000009833 condensation Methods 0.000 claims description 18
- 230000005494 condensation Effects 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 4
- XGZVPYGIUMLWIE-UHFFFAOYSA-N ethyl hypoiodite Chemical compound CCOI XGZVPYGIUMLWIE-UHFFFAOYSA-N 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- -1 propene compound Chemical class 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- LVIYTMFDCXRSDL-UHFFFAOYSA-N 5-methoxy-2-methyl-1,3-benzoselenazole Chemical compound COC1=CC=C2[se]C(C)=NC2=C1 LVIYTMFDCXRSDL-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000000298 carbocyanine Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 150000003839 salts Chemical group 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical compound [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 206010070834 Sensitisation Diseases 0.000 description 4
- 230000008313 sensitization Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
Description
Verfahren zur Herstellung eines unsymmetrischen Pentacarbocyaninfarbstoffes. Gegenstand der Erfindung ist ein Ver fahren zur Flerstellung eines unsymme trischen Penta:carbocyaninfarbstoffes, wonach äquivalente Mengen von 5-Methoxy-2-methyl- benzselenazoljodäthylat mit einem quartären Salz einer Propenverbindung der allgemeinen Formel
EMI0001.0009
worin R.1 Wasserstoff oder ein organisches Radikal, R,. Aryl,
X einen Säurerest bedeu ten, in Gegenwart von alkalischen Konden- sationsmitteln zu einem Tetramethinfarbstoff umgesetzt werden und dieser mit der äqui valenten Menge p-Toluchinaldinjodäthylat in Gegenwart eines alkalischen Kondensations- mittels zum unsymmetrischen Pentacarbo- cyaninfarbstoff, ,dem 1,1'-Diäthyl-6-Methoxy- benzseleno - 2'(6' - Methylchino)
pentacarbo- cyaninjodid kondensiert wird. Der Farbstoff kristallisiert aus Alkohol in kleinen kupfer farbigen verwachsenen Tafeln.
Absorptionsmaximum 6900 AE (in alko holischer Lösung), Sensibilisierungsmagimum <B>7300 AB,</B> Sensibilisierungsgebiet 6100 bis 8100 AE.
Als alkalische Kondensationsmittel sind beispielsweise geeignet primäre, sekun däre und tertiäre Amine, wie Methylamin, Diäthylamin, Trimethylamin, Triäthylamin, Äthanolamin, Triäthanolamin, Piperidin, Pyridin oder Natriumäthylat. Das Konden sationsmittel wird vornehmlich in einer Menge verwendet, die der Menge der ange wandten Base höchstens äquivalent ist,
weil mit zunehmender Menge des Kondensations mittels die Bildung des symmetrischen Farb stoffes begünstigt wird, von dem das Zwi schenprodukt gewöhnlich durch physikalische Mittel (Kristallisation, Auskochen) getrennt werden muss. Die für die Reaktion geeig- n eiste Menge an Kondensationsmitteln kann leicht durch Versuche ermittelt werden.
Kon densationsmittel, welche unter Umständen im Überschuss angewendet werden können, so dass trotzdem die Bildung des Zwischen produktes in genügender Ausbeute erfolgt, sind tertiäre cyklische Amine. So kann bei Verwendung von Pyridin oder ähnlichen Kondensationsmitteln, welche gleichzeitig als Lösungsmittel dienen, natürlich das Konden- sationsmittel im Überschuss verwendet werden. Es ist ratsam, von der Propenverbindung mehr als die der Base äquivalente Menge zu verwenden.
Vornehmlich verwendet man einen Überschuss von mehr als 10 %, um mög lichst die unerwünschte Bildung des symme trischen Farbstoffes zu vermeiden. <I>Beispiel:</I> Das Zwischenprodukt der wahrschein lichen Formel
EMI0002.0014
wird durch Erhitzen von a-Phenylamido-y- Phenylimidopropenhydrochlorid und 5-Me- thogy - 2 - Methylbenzselenazoljodäthylat in Gegenwart eines Lösungsmittels und eines alkalischen Kondensationsmittels, zum Bei spiel Triäthanolamin, erhalten. Aus.
Alkohol kristallisiert ein dunkelbraunes Kristall pulver, das in alkoholischer Lösung ein Ab sorptionsmaximum von 5400-AE. zeigt. 1 g des Zwischenproduktfarstoffes wird gemeinsam mit 0;6 p - Toluchinaldinjod- äthylat in 10 cm' Alkohol nach Zusatz von 0,4 ein- Triäthanolamin bis zur Dunkelgrün färbung erhitzt. Das sich beim Erkalten aus scheidende 1,1'-Diäthyl-6-M.ethogybenzseleno- 2'(6'-Methylchino)pentacarbocyaninjodid der wahrscheinlichen Formel
EMI0002.0030
kristallisiert aus Alkohol in kleinen kupfer farbigen verwachsenen Tafeln.
Absorptionsmaximum 6900 AE (in alko holischer Lösung), Sensibilisierungsmagimum 7300 AE, Sensibilisierungsgebiet 6100 bis 8100 AE.
Process for the preparation of an unsymmetrical pentacarbocyanine dye. The invention is a process for the production of an unsymmetrical penta: carbocyanine dye, according to which equivalent amounts of 5-methoxy-2-methylbenzselenazole iodoethylate with a quaternary salt of a propene compound of the general formula
EMI0001.0009
wherein R.1 is hydrogen or an organic radical, R ,. Aryl,
X means an acid residue, converted in the presence of alkaline condensation agents to a tetramethine dye and this with the equivalent amount of p-toluchinaldinjodäthylat in the presence of an alkaline condensation agent to the unsymmetrical pentacarbocyanine dye, the 1,1'-diethyl 6-methoxybenzseleno - 2 '(6' - methylchino)
Pentacarbo-cyanine iodide is condensed. The dye crystallizes from alcohol in small, copper-colored, fused tablets.
Absorption maximum 6900 AU (in alcoholic solution), sensitization maximum <B> 7300 AU, </B> sensitization area 6100 to 8100 AU.
Suitable alkaline condensing agents are, for example, primary, secondary and tertiary amines, such as methylamine, diethylamine, trimethylamine, triethylamine, ethanolamine, triethanolamine, piperidine, pyridine or sodium ethylate. The condensation agent is mainly used in an amount that is at most equivalent to the amount of the applied base,
because as the amount of condensation increases, the formation of the symmetrical dye is favored, from which the intermediate product usually has to be separated by physical means (crystallization, boiling). The most suitable amount of condensing agent for the reaction can easily be determined by experiments.
Condensation agents, which under certain circumstances can be used in excess so that the intermediate product is nevertheless formed in sufficient yield, are tertiary cyclic amines. Thus, when using pyridine or similar condensation agents which also serve as solvents, the condensation agent can of course be used in excess. It is advisable to use more of the propene compound than the amount equivalent to the base.
An excess of more than 10% is mainly used in order to avoid the undesirable formation of the symmetrical dye as possible. <I> Example: </I> The intermediate product of the probable formula
EMI0002.0014
is obtained by heating α-phenylamido-γ-phenylimidopropene hydrochloride and 5-methogy - 2 - methylbenzselenazole iodoethylate in the presence of a solvent and an alkaline condensing agent, for example triethanolamine. Out.
Alcohol crystallizes a dark brown crystal powder, which in alcoholic solution has a maximum absorption of 5400-AU. shows. 1 g of the intermediate dye is heated together with 0.6 p-toluchinaldinjodethylate in 10 cm 'of alcohol after adding 0.4 triethanolamine until it turns dark green. The 1,1'-diethyl-6-M.ethogybenzseleno-2 '(6'-methylchino) pentacarbocyanine iodide of the probable formula which separates on cooling
EMI0002.0030
crystallized from alcohol in small copper-colored fused tablets.
Absorption maximum 6900 AU (in alcoholic solution), sensitization maximum 7300 AU, sensitization area 6100 to 8100 AU.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE185594X | 1933-06-03 | ||
| DE260534X | 1934-05-26 | ||
| CH182405T | 1934-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH185594A true CH185594A (en) | 1936-07-31 |
Family
ID=27177698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH185594D CH185594A (en) | 1933-06-03 | 1934-06-02 | Process for the preparation of an unsymmetrical pentacarbocyanine dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH185594A (en) |
-
1934
- 1934-06-02 CH CH185594D patent/CH185594A/en unknown
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