DE415534C - Process for the preparation of polymethine dyes - Google Patents

Process for the preparation of polymethine dyes

Info

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
Application number
DEF54598D
Other languages
German (de)
Inventor
Dr Alfred Bloemer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Farbenfabriken Vorm Friedr Bayer and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Farbenfabriken Vorm Friedr Bayer and Co filed Critical Farbenfabriken Vorm Friedr Bayer and Co
Application granted granted Critical
Publication of DE415534C publication Critical patent/DE415534C/en
Expired legal-status Critical Current

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

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)

PATENT-ANSPRUCH: Abänderung des durch das Hauptpatent geschützten Verfahrens zur Darstellung von Polymethinfarbstoffen, darin bestehend, daß man auf Cyklammoniumverbindungen mit reaktionsfähigen, d. h. in a- oder Y-Stellung zum Stickstoff stehenden Methylgruppen statt Orthoameisensäureester Salze der Ameisensäure einwirken läßt. PATENT CLAIM: Modification of the process for the preparation of polymethine dyes, which is protected by the main patent, consists in allowing formic acid salts to act on cyclammonium compounds with reactive methyl groups, ie in a- or Y-position to the nitrogen, instead of orthoformic acid ester.
DEF54598D 1924-03-11 1923-08-24 Process for the preparation of polymethine dyes Expired DE415534C (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (2)

* Cited by examiner, † Cited by third party
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
FR578435A (en) 1924-09-25
GB232740A (en) 1925-04-30

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