Azomethine compound and oily magenta ink

Abstract

An azomethine compound is represented by the formula (I). and R 1 , L 1 , L 2 , R 3 and R 4 have 20 to 50 carbon atoms in total.

1 . An azomethine compound represented by the formula (I):  
       
         
           
           
               
               
           
         
       
       R 1  is an alkyl group having 1 to 16 carbon atoms; R 2  is a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an amido group having 2 to 20 carbon atoms, an alkoxycarbonylamino group having 2 to 20 carbon atoms, nitro or cyano; R 3  is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxyalkyl group having 7 to 30 carbon atoms or an alkoxycarbonylalkyl group having 3 to 30 carbon atoms; R 4  is an alkyl group having 1 to 16 carbon atoms; L 1  is an alkylene group having 1 to 30 carbon atoms or an arylene group having 6 to 30 carbon atoms; L 2  is —CO—NH—, —SO 2 —NH—, —O—, —O—CO—or —O——CO—NH—; X is cyano, an alkoxycarbonyl group having 2 to 19 carbon atoms, an alkylsulfonyl group having 1 to 18 carbon atoms, an arylsulfonyl group having 6 to 26 carbon atoms, sulfamoyl, an alkylsulfamoyl group having 1 to 18 carbon atoms or an arylsulfamoyl group having 6 to 26 carbon atoms; Y is hydrogen, a halogen atom, hydroxyl, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms or an acyloxy group having 2 to 20 carbon atoms; m is 1, 2, 3 or 4; n is an integer of 1 to 18; p is 0, 1, 2, 3 or 4; and R 1 , L 1 , L 2 , R 3  and R 4  have 20 to 50 carbon atoms in total.  
     
     
         2 . The azomethine compound as defined in  claim 1 , wherein R 1  is an alkyl group having 1 to 12 carbon atoms.  
     
     
         3 . The azomethine compound as defined in  claim 1 , wherein R 2  is a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an amido group having 2 to 12 carbon atoms, an alkoxycarbonylamino group having 2 to 12 carbon atoms, nitro or cyano.  
     
     
         4 . The azomethine compound as defined in  claim 1 , wherein R 3  is an alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 25 carbon atoms, an aryloxyalkyl group having 7 to 25 carbon atoms or an alkoxycarbonylalkyl group having 3 to 25 carbon atoms.  
     
     
         5 . The azomethine compound as defined in  claim 1 , wherein R 4  is an alkyl group having 1 to 12 carbon atoms.  
     
     
         6 . The azomethine compound as defined in  claim 1 , wherein L 1  is an alkylene group having 1 to 25 carbon atoms or an arylene group having 6 to 25 carbon atoms.  
     
     
         7 . The azomethine compound as defined in  claim 1 , wherein X is cyano or an alkoxycarbonyl group having 2 to 19 carbon atoms.  
     
     
         8 . The azomethine compound as defined in  claim 1 , wherein Y is hydrogen.  
     
     
         9 . The azomethine compound as defined in  claim 1 , wherein m is 1, 2 or 3.  
     
     
         10 . The azomethine compound as defined in  claim 1 , wherein n is an integer of 1 to 14.  
     
     
         11 . The azomethine compound as defined in  claim 1 , wherein p is 0, 1, 2 or 3.  
     
     
         12 . The azomethine compound as defined in  claim 1 , wherein R 1 , L 1 , L 2 , R 3  and R 4  have 25 to 45 carbon atoms in total.  
     
     
         13 . An azomethine compound represented by the formula (I a ):  
       
         
           
           
               
               
           
         
       
       wherein R 1  is an alkyl group having 1 to 16 carbon atoms; R 2  is a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an amido group having 2 to 20 carbon atoms, an alkoxycarbonylamino group having 2 to 20 carbon atoms, nitro or cyano; R 3  is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxyalkyl group having 7 to 30 carbon atoms or an alkoxycarbonylalkyl group having 3 to 30 carbon atoms; L 1  is an alkylene group having 1 to 30 carbon atoms or an arylene group having 6 to 30 carbon atoms; L 2  is —CO—NH—, —SO 2 —NH—, —O—, ——O —CO—or —O—CO—NH—; X is cyano, an alkoxycarbonyl group having 2 to 19 carbon atoms, an alkylsulfonyl group having 1 to 18 carbon atoms, an arylsulfonyl group having 6 to 26 carbon atoms, sulfamoyl, an alkylsulfamoyl group having 1 to 18 carbon atoms or an arylsulfamoyl group having 6 to 26 carbon atoms; Y is hydrogen, a halogen atom, hydroxyl, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms or an acyloxy group having 2 to 20 carbon atoms; m is 1, 2, 3 or 4; n is an integer of 1 to 18; p is 0, 1, 2, 3 or 4; and R 1 , L 1 , L 2 , R 3  and R 4  have 20 to 50 carbon atoms in total.  
     
     
         14 . An oily magenta ink in which an azomethine dye represented by the formula (I) is dissolved in an organic solvent:  
       
         
           
           
               
               
           
         
       
       R 1  is an alkyl group having 1 to 16 carbon atoms; R 2  is a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an amido group having 2 to 20 carbon atoms, an alkoxycarbonylamino group having 2 to 20 carbon atoms, nitro or cyano; R 3  is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxyalkyl group having 7 to 30 carbon atoms or an alkoxycarbonylalkyl group having 3 to 30 carbon atoms; R 4  is an alkyl group having 1 to 16 carbon atoms; L 1  is an alkylene group having 1 to 30 carbon atoms or an arylene group having 6 to 30 carbon atoms; L 2  is —CO—NH—, —SO 2 —NH—, —O—, —O—CO—or —O—CO—NH—; X is cyano, an alkoxycarbonyl group having 2 to 19 carbon atoms, an alkylsulfonyl group having 1 to 18 carbon atoms, an arylsulfonyl group having 6 to 26 carbon atoms, sulfamoyl, an alkylsulfamoyl group having 1 to 18 carbon atoms or an arylsulfamoyl group having 6 to 26 carbon atoms; Y is hydrogen, a halogen atom, hydroxyl, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms or an acyloxy group having 2 to 20 carbon atoms; m is 1, 2, 3 or 4; n is an integer of 1 to 25 18; p is 0, 1, 2, 3 or 4; and R 1 , L 1 , L 2 , R 3  and R 4  have 20 to 50 carbon atoms in total.