1-1-Binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid compounds, met

Details 1-1-Binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid compounds, met 1-1-Binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid compounds, met

1980-05-07

1982-06-22

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 27, 546 29, 8657, 8568, C07D51900, C07D48706, C07D48716, C07D48722

Patent

active

043363830

ABSTRACT:
1,1'-Binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid compounds having the following formula: ##STR1## wherein R.sub.1 is hydrogen, halogen, or alkyl; when X is oxygen, Y is hydrogen, alkyl, a cycloalkyl, or an aryl containing at least one substituent from the group including: halogen, alkyl, or alkoxy, when X is nitrogen, Y is ##STR2## wherein R.sub.2 is hydrogen, halogen, or alkyl; Y being linked to X with the formation of a benzimidazole cycle.
The method for preparing the compounds according to the present invention resides in the treatment of that 1,1'-binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid anhydride with an alkali to give a corresponding salt which is condensed with orthophenylenediamines upon heating at reflux at a pH of from 6.3 to 6.8. The resulting benzimidazole-1,1'-binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid anhydride having the formula: ##STR3## wherein R.sub.1 is hydrogen, halogen, or alkyl, is isolated and condensed with an amine or ortho-phenylenediamines in an excess of the amine, in water or an organic solvent, followed by isolation of the desired product.
The compounds according to the present invention are employed for the synthesis of asymmetric compounds of 3,4,9,10-perylenetetracarboxylic acid, as well as for dyeing and printing of textile materials with the formation, on the material, of asymmetric compounds of 3,4,9,10-perylenetetracarboxylic acid having the following formula: ##STR4## wherein R.sub.1 is hydrogen, halogen, or alkyl; when X is oxygen, Y is hydrogen, alkyl, cycloalkyl, or aryl containing at least one substituent from the group including; halogen, alkyl, or alkoxy, when X is nitrogen, Y is ##STR5## where R.sub.2 is hydrogen, halogen, or alkyl; Y being linked with X to form a benzimidazole cycle.
The compounds according to the present invention dye textile materials to various shades of violet color.

REFERENCES:
patent: 4166181 (1979-08-01), Dokunikhin

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