CH130700A - Process for the preparation of polymethine dyes. - Google Patents
Process for the preparation of polymethine dyes.Info
- Publication number
- CH130700A CH130700A CH130700DA CH130700A CH 130700 A CH130700 A CH 130700A CH 130700D A CH130700D A CH 130700DA CH 130700 A CH130700 A CH 130700A
- Authority
- CH
- Switzerland
- Prior art keywords
- polymethine dyes
- preparation
- bases
- condensation
- formic acid
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical compound I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Polymethinfarbstoffen. Die Polymethinfarbstoffe werden-bekannt- lich durch Kondensieren von geeigneten Cy- clammoniumbasen (d. h. solche, die in a- oder r-Stellung eine reaktionsfähige CHs-Gruppe enthalten) beziehungsweise deren Salzen mit o-Ameisensäureester in Gegenwart von sauren und neutralen Kondensationsmitteln erhalten. 1's ist auch vorgeschlagen worden, solche Kondensationen in Pyridin durchzuführen.
Es wurde nun gefunden, dass die aroma tischen, tertiären Basen vom Typus der Dialkvlaniline als Reaktionsmedium bei dieser Kondensation sehr gut geeignet sind. Die Verwendung dieser Base gegenüber Pyridin bietet ganz wesentliche Vorteile, da diese Basen dank ihrer Eigenschaften viel leichter wasserfrei zu erhalten sind als Pyridin und auch viel bequemer regenerierbar sind.
<I>Beispiel</I> Eine Mischung von 301 Teilen 2,3,3-Tri- methylindoleniniumjodmethylat der Formel
EMI0001.0019
mit 300 Teilen o-Ameisensäureester wird nach Zugabe von 1130 Teilen Dimethylanilin unter Rühren auf 115-1201 erhitzt und 3 Stunden bei dieser Temperatur gehalten.
Die erhaltene Lösung wird nach dem Erkalten mit Wasser verdünnt, sodaalkalisch gemacht und das Dimethylanilin mit Wasserdampf abdestilliert. Der Rückstand stellt eine violettrote Lösung dar, aus der das 1,1'3,",3',3'-Hexamethyl- strepto-rnonovinylenindocyarrinjodid der For mel
EMI0001.0029
iri schönen Nadeln kristallisiert. Xaeh dem Abfiltrieren und Waschen mit Wasser erhält man den Farbstoff in sehr guter Ausbeute.
Zum gleichen Resultat führt die Verwen dung von Diäthylanilin.
Process for the preparation of polymethine dyes. The polymethine dyes are obtained, as is known, by condensing suitable cyclammonium bases (i.e. those which contain a reactive CHs group in the a or r position) or their salts with o-formic acid ester in the presence of acidic and neutral condensing agents. 1's has also been proposed to carry out such condensations in pyridine.
It has now been found that the aromatic, tertiary bases of the dialkvlaniline type are very suitable as a reaction medium in this condensation. The use of this base over pyridine offers very significant advantages, since thanks to their properties these bases are much easier to obtain anhydrous than pyridine and are also much more convenient to regenerate.
<I> Example </I> A mixture of 301 parts of 2,3,3-trimethylindoleninium iodomethylate of the formula
EMI0001.0019
with 300 parts of o-formic acid ester, after addition of 1,130 parts of dimethylaniline, the mixture is heated to 115-1201 with stirring and kept at this temperature for 3 hours.
After cooling, the solution obtained is diluted with water, made alkaline with soda and the dimethylaniline is distilled off with steam. The residue is a purple-red solution from which the 1,1'3, ", 3 ', 3'-hexamethyl-strepto-rnonovinylenindocyarrinjodid of the formula
EMI0001.0029
iri beautiful needles crystallized. After filtering off and washing with water, the dye is obtained in very good yield.
The use of diethylaniline leads to the same result.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH130700T | 1928-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH130700A true CH130700A (en) | 1928-12-31 |
Family
ID=4389013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH130700D CH130700A (en) | 1928-01-11 | 1928-01-11 | Process for the preparation of polymethine dyes. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH130700A (en) |
-
1928
- 1928-01-11 CH CH130700D patent/CH130700A/en unknown
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