DE415534C - Process for the preparation of polymethine dyes - Google Patents
Process for the preparation of polymethine dyesInfo
- Publication number
- DE415534C DE415534C DEF54598D DEF0054598D DE415534C DE 415534 C DE415534 C DE 415534C DE F54598 D DEF54598 D DE F54598D DE F0054598 D DEF0054598 D DE F0054598D DE 415534 C DE415534 C DE 415534C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- polymethine dyes
- acid ester
- main patent
- dyes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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)
- Coloring (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Polymethinfarbstoffen. In dem Hauptpatent ist ein Verfahren zur Darstellung von Polymethinfarbstoffen beschrieben, welches darin besteht, daß man auf Cyklammoniumsalze mit reaktionsfähigen, d. h. in a- oder -(-Stellung zum Stickstoff stehenden Methylgruppen Orthoameisensäureester bzw. j3-Alkoxyakroleinacetal, zweckmäßig bei Gegenwart von sauren oder neutralen Kondensationsmitteln, wie Essigsäureanhydrid, Chlorzink und Lösungsmitteln, wie Nitrobenzol, Tetrachloräthan usw. einwirken läßt.Process for the preparation of polymethine dyes. In the main patent describes a method for the preparation of polymethine dyes, which consists in that one on cyclammonium salts with reactive, d. H. in a- or - (- position to the nitrogen methyl groups orthoformic acid ester or j3-alkoxyacrolein acetal, expedient in the presence of acidic or neutral condensing agents, such as acetic anhydride, Zinc chloride and solvents such as nitrobenzene, tetrachloroethane, etc. can act.
Bei der weiteren Verfolgung dieses Arbeitsgebietes wurde nun die überraschende Beobachtung gemacht, daß der in dem Hauptpatent verwendete Orthoameisensäureester durch die leichter zugänglichen Salze der Ameisensäure, beispielsweise Natriumformiat, ersetzt werden kann. Diese Arbeitsweise hat den weiteren Vorteil, daß die Reaktion bereits bei wesentlich niedrigerer Temperatur verläuft, als bei der Verwendung von Orthoameisensäureester, wodurch der Reinheitsgrad der Farbstoffe günstig beeinflußt wird. Beispiel. 7,2 Gewichtsteile Trimethylindoleniniumjodmethylat -werden mit 6,8 Gewichtsteilen trokkenem Natriumformiat und 15 Gewichtsteilen Essigsäureanhydrid gemischt und unter Rühren einige Zeit auf 7o bis 8o° erhitzt. Nach Beendigung der Kondensation wird der Farbstoff durch Zersetzung des überschüssigen Essigsäureanhydrids direkt mit heißem Wasser abgeschieden, abgesaugt und getrocknet. Der Farbstoff ist identisch mit dem im Beispiel i des Hauptpatents beschriebenen.In the further pursuit of this field of work, the surprising observation has now been made that the orthoformic acid ester used in the main patent can be replaced by the more easily accessible salts of formic acid, for example sodium formate. This procedure has the further advantage that the reaction takes place at a much lower temperature than when using orthoformic acid ester, which has a favorable effect on the degree of purity of the dyes. Example. 7.2 parts by weight of trimethylindolenium iodomethylate are mixed with 6.8 parts by weight of dry sodium formate and 15 parts by weight of acetic anhydride and heated to 70 ° to 80 ° for some time while stirring. After the condensation has ended, the dyestuff is deposited directly with hot water by decomposing the excess acetic anhydride, filtered off with suction and dried. The dye is identical to that described in Example i of the main patent.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB624124A GB232740A (en) | 1924-03-11 | 1924-03-11 | The manufacture of polymethine dyestuffs |
Publications (1)
Publication Number | Publication Date |
---|---|
DE415534C true DE415534C (en) | 1925-06-22 |
Family
ID=9810960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF54598D Expired DE415534C (en) | 1924-03-11 | 1923-08-24 | Process for the preparation of polymethine dyes |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE415534C (en) |
FR (1) | FR578435A (en) |
GB (1) | GB232740A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19911421A1 (en) * | 1999-03-11 | 2000-10-05 | Dyomics Gmbh | Laser compatible NIR marker dyes |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3105778A1 (en) * | 1981-02-17 | 1982-09-02 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING TRIMETHINE DYES |
US5120858A (en) * | 1991-03-25 | 1992-06-09 | Miles Inc. | Process for the preparation of trimethine dyestuffs |
-
1923
- 1923-08-24 DE DEF54598D patent/DE415534C/en not_active Expired
-
1924
- 1924-03-11 GB GB624124A patent/GB232740A/en not_active Expired
- 1924-03-11 FR FR578435D patent/FR578435A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19911421A1 (en) * | 1999-03-11 | 2000-10-05 | Dyomics Gmbh | Laser compatible NIR marker dyes |
DE10080558B4 (en) * | 1999-03-11 | 2008-09-25 | Dyomics Gmbh | Laser-compatible NIR marker dyes |
Also Published As
Publication number | Publication date |
---|---|
GB232740A (en) | 1925-04-30 |
FR578435A (en) | 1924-09-25 |
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