Fluoran carboxylic acids and esters thereof

Details Fluoran carboxylic acids and esters thereof Fluoran carboxylic acids and esters thereof

C - Chemistry, Metallurgy

07

D

42/13, 260/306.5

C07D 493/10 (2006.01) B41M 5/145 (2006.01) B41M 5/327 (2006.01) C09B 11/24 (2006.01)

Patent

CA 1145341

ABSTRACT OF THE DISCLOSURE 1-R0-2-R4-3-R1-6-amino-5'/6-carboxyfluorans of the formula Image wherein R represents non-tertiary C1 to C4 alkyl; R0 and R1 represent hydrogen or non-tertiary C1 to C4 alkyl; R4 represents hydrogen or -N(R5)(R6) in which R5 represetns hydrogen, non-tertiary C1 to C18 alkyl, benzyl or benzyl substituted by halo, nitro, non- tertiary C1 to C4 alkyl or non-tertiarry C1 to C4 alkoxy, R6 repersetns hydrogen, phenyl, non-tertiary C1 to C18 alkyl, benzyl, benzyl substituted by halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy or acyl, or R5 and R6 taken together with the nitrogen represent 2,5-(R7)2-1-pyrrolyl in which R7 represents hydrogen or non-tertiary C1 to C4 alkyl; Y represents OR2 in which R2 represents hydrogen, non- tertiary C1 to C18 alkyl, benzyl, benzyl substituted by halo, nitro, non-tertiary C1 to C4 alkyl or by non- tertiary C1 to C4 alkoxy, or R2 represents an alkali metal cation or ammonium cation, with the proviso that R2 is not an alkali metal cation or ammonium cation when R4 is hydrogen, useful as colour formers, particularly in carbonless duplicating and thermal marking systems, are prepared by the interaction of 4/5-carboxy-2-(4-dialkylamino-substituted-2-hydroxybenzoyl)benzoic acids and substituted diphenylamides to produce the phthalides which are then subjected to ring closure to produce the carboxyfluorans and by the interaction of 4/5-carboxy-2-(4- dialkylamino-substituted-2-hydroxybenzoyl)benzoic acids and substituted 4-hydroxyacetanilides or alkyl phenols which are esterfied with alkyl halides or dialkyl sulfates.

351838

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