Azo dye

Abstract

An azo dye represented by the following formula (I): wherein, in formula (I), R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, an aliphatic group, an aryl group, a halogen atom, an acyl group, a cyano group, an acylamino group, an aliphatic oxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, an aliphatic sulfonyl group, an arylsulfonyl group, a sulfamoyl group, an aliphatic oxycarbonylamino group, an aryloxycarbonylamino group, a sulfo group, a carboxyl group, a carbamoylamino group, a sulfamoylamino group, or an aliphatic- or aromatic-sulfonylamino group, wherein R 1 and R 2 and/or R 3 and R 4 may be combined with each other to form a five- or six-membered aromatic ring or non-aromatic ring; X represents a carbon atom or a nitrogen atom, wherein n is 0 when X is a nitrogen atom and n is 1 when X is a carbon atom; A, B, C, and D each represent a carbon atom or a nitrogen atom, provided that at least one of A, B, C and D represents a nitrogen atom; Y represents a substituent; and m denotes an integer from 0 to 3.

1 . An azo dye represented by the following formula (I): 
       
         
           
           
               
               
           
         
         wherein, in formula (I), R 1 , R 2 , R 3 , and R 4  each independently represent a hydrogen atom, an aliphatic group, an aryl group, a halogen atom, an acyl group, a cyano group, an acylamino group, an aliphatic oxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, an aliphatic sulfonyl group, an arylsulfonyl group, a sulfamoyl group, an aliphatic oxycarbonylamino group, an aryloxycarbonylamino group, a sulfo group, a carboxyl group, a carbamoylamino group, a sulfamoylamino group, or an aliphatic- or aromatic-sulfonylamino group, wherein R 1  and R 2  and/or R 3  and R 4  may be combined with each other to form a five- or six-membered aromatic ring or non-aromatic ring; X represents a carbon atom or a nitrogen atom, wherein n is 0 when X is a nitrogen atom and n is 1 when X is a carbon atom; A, B, C, and D each represent a carbon atom or a nitrogen atom, provided that at least one of A, B, C and D represents a nitrogen atom; Y represents a substituent; and m denotes an integer from 0 to 3. 
       
     
     
         2 . (canceled) 
     
     
         3 . (canceled) 
     
     
         4 . (canceled) 
     
     
         5 . (canceled) 
     
     
         6 . (canceled) 
     
     
         7 . (canceled) 
     
     
         8 . The azo dye as claimed in  claim 1 , which is represented by the following formula (IB): 
       
         
           
           
               
               
           
         
         wherein, in formula (IB), R 1B , R 2B , R 3B  and R 4B  each independently represent a hydrogen atom, an aliphatic group, an aryl group, a halogen atom, an acyl group, a cyano group, an acylamino group, an aliphatic oxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, an aliphatic sulfonyl group, an arylsulfonyl group, a sulfamoyl group, an aliphatic oxycarbonylamino group, an aryloxycarbonylamino group, a sulfo group, a carboxyl group, a carbamoylamino group, a sulfamoylamino group, or an aliphatic- or aromatic-sulfonylamino group, wherein R 1B  and R 2B  and/or R 3B  and R 4B  may be combined with each other to form a five- or six-membered aromatic ring or non-aromatic ring; X B  represents a carbon atom or a nitrogen atom, wherein n B  is 0 when X B  is a nitrogen atom and n 13  is 1 when X B  is a carbon atom; A B , B B , C B , and D B  each represent a carbon atom or a nitrogen atom, provided that at least one of A B , B B , C B  and D B  represents a nitrogen atom; Y B  represents a substituent; and m B  denotes an integer from 0 to 3; provided that m B  is an integer of 1 or more when A B  represents a nitrogen atom and B B , C B , and D B  each represent a carbon atom. 
       
     
     
         9 . The azo dye as claimed in  claim 8 , wherein R 1B  represents a halogen atom, a cyano group, a carbamoyl group, or an acylamino group. 
     
     
         10 . The azo dye as claimed in  claim 8 , wherein R 2B  and R 3B  each represent a halogen atom, a hydrogen atom, or an aliphatic group. 
     
     
         11 . The azo dye as claimed in  claim 8 , wherein R 4B  represents a halogen atom, a hydrogen atom, or an acylamino group. 
     
     
         12 . The azo dye as claimed in  claim 8 , wherein Y B  represents a halogen atom, a cyano group, an alkyl group, or an alkylthio group. 
     
     
         13 . The azo dye as claimed in  claim 8 , wherein X B  is a carbon atom. 
     
     
         14 . The azo dye as claimed in  claim 1 , wherein A is a nitrogen atom, B is a carbon atom, C is a nitrogen atom and D is a carbon atom.