Photographic element containing improved pyrazolotriazole coupler

Abstract

Disclosed is photographic element comprising a light-sensitive silver halide emulsion layer containing a 1H-pyrazolo[1,5-b][1,2,4]triazole containing in the 6-position a fully substituted methyl group, in the 7-position a hydrogen atom or halogen atom, and in the 2-position a phenyl group substituted in the meta position with a sulfonamide group free of amide, sulfonamide, ureido or ester groups and bearing at least 9 (cyclo)aliphatic carbon atoms. The element exhibits improved resistance to coupler crystallization.

1 . A photographic element comprising a light-sensitive silver halide emulsion layer containing a 1H-pyrazolo[1,5-b][1,2,4]triazole containing in the 6-position a fully substituted methyl group, in the 7-position a hydrogen atom or halogen atom, and in the 2-position a phenyl group substituted in the meta position with a sulfonamide group free of amide, sulfonamide, ureido or ester groups and bearing at least 9 (cyclo)aliphatic carbon atoms.  
     
     
         2 . The element of  claim 1  wherein the sulphonamide group contains an unsubstituted alkyl group.  
     
     
         3 . The element of  claim 1  wherein the sulphonamide group contains an alkyl group substituted with an ether group.  
     
     
         4 . The element of  claim 1  containing a chloro in the 7-position.  
     
     
         5 . The element of  claim 1  wherein R 1 , R 2 , and R 3  are methyl groups.  
     
     
         6 . The element of  claim 1  wherein the coupler does not have a melting point of 140° C. or higher.  
     
     
         7 . The element of  claim 1  wherein the coupler is represented by structure (I):  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1 , R 2 , and R 3  are independently selected unsubstituted alkyl groups comprising of 3 or less carbons with the proviso that one or more of the R 1 , R 2 , and R 3  groups can be joined to form a ring;  
 R is a straight, cyclic or branched aliphatic carbon chain or carbocyclic group unsubstituted with amide, sulfonamide, ureido, or ester groups, and containing at least 9 aliphatic carbon atoms;  
 each R′ is an independently selected alkyl or halogen substituent and n is 0 to 4; and  
 X is hydrogen or halogen.  
 
     
     
         8 . The element of  claim 7  wherein R 1 , R 2 , and R 3  are methyl groups.  
     
     
         9 . The element of  claim 7  wherein X is Cl.  
     
     
         10 . The element of  claim 7  wherein R is an unbranched alkyl group.  
     
     
         11 . The element of  claim 7  wherein R is a branched alkyl group.  
     
     
         12 . The element of  claim 7  wherein R is a cycloalkyl group.  
     
     
         13 . The element of  claim 7  wherein n is 0.  
     
     
         14 . The element of  claim 7  wherein n is 1 and R′ is not an ether group.  
     
     
         15 . The element of  claim 1  provided on a reflective support.  
     
     
         16 . The element of  claim 1  wherein the silver halide is primarily a silver chloride.  
     
     
         17 . A coupler compound represented by formula (I):  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1 , R 2 , and R 3  are independently selected unsubstituted alkyl groups comprising of 3 or less carbons with the proviso that one or more of the R 1 , R 2 , and R 3  groups can be joined to form a ring;  
 R is a straight, cyclic or branched aliphatic carbon chain or carbocyclic group unsubstituted with amide, sulfonamide, ureido, or ester groups, and containing at least 9 aliphatic carbon atoms;  
 each R′ is an independently selected alkyl or halogen substituent and n is 0 to 4; and  
 X is hydrogen or halogen.  
 
     
     
         18 . A dye compound obtained by the reaction of a coupler of  claim 17  and a paraphenylenediamine developer compound.  
     
     
         19 . The dye of  claim 18  wherein the para-phenylenediamine compound is selected from the group consisting of 
 4-amino-N,N-diethylaniline hydrochloride,    4-amino-3-methyl-N,N-diethylaniline hydrochloride,    4-amino-3-methyl-N-ethyl-N-(2-methanesulfonamidoethyl)aniline sesquisulfate hydrate,    4-amino-3-methyl-N-ethyl-N-(2-hydroxyethyl)aniline sulfate,    4-amino-3-(2-methanesulfonamidoethyl)-N,N-diethylaniline hydrochloride, and    4-amino-N-ethyl-N-(2-methoxyethyl)-m-toluidine di-p-toluene sulfonic acid.