Dyes derived from dihydro-carbazolium salts

Details Dyes derived from dihydro-carbazolium salts Dyes derived from dihydro-carbazolium salts

1998-08-05

1999-04-06

Ramsuer, Robert W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546176, C07D20986

Patent

active

058920560

ABSTRACT:
2-Methyl-4,4a-dihydro-3H-carbazolium salts that are useful as dye precursors and dyes derived from those precursors are disclosed. The salts are described by the formula ##STR1## wherein R.sup.1 represents an alkyl, aryl, sulfoalkyl, carboxyalkyl, sulfatoalkyl, alkoxyalkyl, acyloxyalkyl, dialkylaminoalkylene, cycloaminoalkylene, acyl, or alkenyl group having from 1 to 18 carbon atoms; R.sup.2 represents an alkyl group having up to 18 carbon atoms; R.sup.3 represents hydrogen or an alkyl group having from 1 to 18 carbon atoms; R.sup.4 represents hydrogen or an alkyl group having from 1 to 18 carbon atoms; R.sup.5 represents hydrogen, nitro, carboxyl, sulfo, hydroxy, halogen, phospho, or an alkoxy, thioalkoxy, oxyalkyl, acyl, alkyl, aryl, or amino group having up to 18 carbon atoms; wherein any two groups R.sup.5, or R.sup.4 and a group R.sup.5, or R.sup.1 and R.sup.4 may together form a substituted or unsubstituted aryl, heteroaryl, aliphatic, or heteroaliphatic ring; X represents an anion; and a and b represent positive integers such that a equals b.
The salts have a partially saturated ring system that rigidifies the chromophore in the precursor and in dyes derived from it. The rigidified chromophores have narrowed absorption bands relative to corresponding non-rigid chromophores. Dyes prepared from the dye precursors of the invention typically have good solubility in non-polar solvents.

REFERENCES:
patent: 4749718 (1988-06-01), Coates

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