Yellow dyes and ink compositions

Abstract

Provided are novel yellow azo dyes which are useful in ink compositions, especially ink jet ink compositions. The dyes and ink compositions of the present invention exhibit a good balance of optical density, print reliability, water fastness and light fastness and exhibit improved water solubility, thus rendering the ink compositions to be especially suitable for printheads having small nozzle openings.

We claim:  
     
         1 . A compound of Formula (I):  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  comprises —SO 3 M or —CO 2 M;  
 R comprises —H, -lower alkyl, -lower alkoxy, -halogen, —NH—C(O)-lower alkyl, —SO 3 M, or —CO 2 M;  
 R 3  comprises —H, -lower alkyl, -lower alkoxy, —O-lower-alkylene-CO 2 M, -lower alkylene-CO 2 M, —NH—C(O)—CO 2 M, —NH—C(O)-lower alkyl, or —CO 2 M;  
 R 4  comprises —H, -lower alkyl, or -lower alkoxy;  
 R 5  comprises a group of the formula:  
                     —NH-lower alkylene-SO 3 M;    —NH-lower alkylene-(CO 2 M) m ;    —S-lower alkylene-SO 3 M; or    —S-lower alkylene-(CO 2 M) m ; 
 wherein 
 R 9  and R 13  comprise, independently, —SO 3 M or —CO 2 M;  
 R 10  and R 14  comprise, independently, —H, -lower alkyl, -lower alkoxy, -halogen, —NH—C(O)-lower alkyl, —SO 3 M, or —CO 2 M;  
 R 11  comprises —H, -lower alkyl, -lower alkoxy, —O-lower-alkylene-CO 2 M, -lower alkylene-CO 2 M, —NH—C(O)—CO 2 M, —NH—C(O)-lower alkyl, or —CO 2 M;  
 R 12  comprises —H, -lower alkyl, or -lower alkoxy;  
 
   
 R 6  comprises a group of the formula:  
                     —NH-lower alkylene-SO 3 M;    —NH-lower alkylene-(CO 2 M) m ;    —S-lower alkylene-SO 2 M;    —S-lower alkylene-(CO 2 M) m ; or    —NH—R 7 , 
 wherein 
 R 15  comprises —SO 3 M or —CO 2 M;  
 
 R 16  comprises —H, -lower alkyl, -lower alkoxy, -halogen, —NH—C(O)-lower alkyl, —SO 3 M, or —CO 2 M;  
 R 17  comprises —H, -lower alkyl, or —(CH 2 CHR 18 —O)—H,  
 R 18  comprises —H, —CH 3 , —CH 2 CH 3 , or —CH 2 OH,  
 m is 1 or 2;  
 M comprises —H, -Li, -Na, -K, —N(R 19 ) 4 , or —HN(R 19 ) 3 ,  
 wherein 
 R 19  comprises —H, -lower alkyl, or —(CH 2 CHR 20 —O)—H,  
 R 20  comprises —H, —CH 3 , —CH 2 CH 3 , or —CH 2 OH.  
 
   
 
     
     
         2 . The compound of  claim 1 , wherein R 1  comprises —SO 3 M.  
     
     
         3 . The compound of  claim 1 , wherein R 1  comprises —CO 2 M.  
     
     
         4 . The compound of  claim 1 , wherein R 3  and R 4  comprise, independently, hydrogen or lower alkoxy.  
     
     
         5 . The compound of  claim 1 , wherein R 5  comprises a group of the formula: 
 —NH-lower alkylene-SO 3 M;    —NH-lower alkylene-(CO2M) m ;    —S-lower alkylene-SO2M; or    —S-lower alkylene-(CO 2 M) m .    
     
     
         6 . The compound of  claim 1 , wherein the compound of Formula(I) is selected from  
       
         
           
           
               
               
           
         
       
     
     
         7 . A compound of Formula (II):  
       
         
           
           
               
               
           
         
       
       wherein: 
 R 3  comprises a lower alkoxy group;  
 R 5  comprises a group of the formula:  
                     —NH-lower alkylene-SO 3 M;    —NH-lower alkylene-(CO 2 M) m ;    —S-lower alkylene-SO 3 M; or    —S-lower alkylene-(CO 2 M) m ;    wherein 
 R 9  and R 13  comprise, independently, —SO 3 M or —CO 2 M;  
 R 10  and R 14  comprise, independently, —H, -lower alkyl, -lower alkoxy, -halogen, —NH—C(O)-lower alkyl, —SO 3 M, or —CO 2 M;  
 R 11  comprises —H, -lower alkyl, -lower alkoxy, —O-lower-alkylene-CO 2 M, -lower alkylene-CO 2 M, —NH—C(O)—CO 2 M, —NH—C(O)-lower alkyl, or —CO 2 M;  
 R 12  comprises —H, -lower alkyl, or -lower alkoxy;  
   
 R 6  comprises a group of the formula:  
                     —NH-lower alkylene-SO 3 M;    —NH-lower alkylene-(CO 2 M) m ;    —S-lower alkylene-SO 2 M;    —S-lower alkylene-(CO 2 M) m ; or    —NH—R 17 , 
 wherein 
 R 15  comprises —SO 3 M or —CO 2 M;  
 R 16  comprises —H, -lower alkyl, -lower alkoxy, -halogen, —NH—C(O)-lower alkyl, —SO 3 M, or —CO 2 M;  
 R 17  comprises —H, -lower alkyl, or —(CH 2 CHR 18 —O)—H,  
 R 18  comprises —H, —CH 3 , —CH 2 CH 3 , or —CH 2 OH,  
 m is 1 or 2;  
 M comprises —H, -Li, -Na, -K, —N(R 19 ) 4 , or —HN(R 19 ) 3 ,  
 wherein  
  R 19  comprises —H, -lower alkyl, or —(CH 2 CHR 20 —O)—H,  
  R 20  comprises-H, —CH 3 , —CH 2 CH 3 , or —CH 2 OH.  
 
   
 
     
     
         8 . An ink composition comprising: 
 (a) at least 0.1% by weight of a compound of Formula (I):                          wherein    R 1  comprises —SO 3 M or —CO 2 M;    R 2  comprises —H, -lower alkyl, -lower alkoxy, -halogen, —NH—C(O)— ower alkyl, —SO 3 M, or —CO 2 M;    R 3  comprises —H, -lower alkyl, -lower alkoxy, —O-lower-alkylene-CO 2 M, -lower alkylene-CO 2 M, —NH—C(O)—CO 2 M, —NH—C(O)-lower alkyl, or —CO 2 M;    R 4  comprises —H, -lower alkyl, or -lower alkoxy;    R 5  comprises a group of the formula:                        —NH-lower alkylene-SO 3 M;    —NH-lower alkylene-(CO 2 M) m ;    —S-lower alkylene-SO 3 M; or    —S-lower alkylene-(CO 2 M) m ; 
 wherein 
 R 9  and R 13  comprise, independently, —SO 3 M or —CO 2 M;  
 R 10  and R 14  comprise, independently, —H, -lower alkyl, -lower alkoxy, -halogen, —NH—C(O)-lower alkyl, —SO 3 M, or —CO 2 M;  
 R 11  comprises —H, -lower alkyl, -lower alkoxy, —O-lower-alkylene-CO 2 M, -lower alkylene-CO 2 M, —NH—C(O)—CO 2 M, —NH—C(O)-lower alkyl, or —CO 2 M;  
 R 12  comprises —H, -lower alkyl, or -lower alkoxy;  
 
     R 6  comprises a group of the formula:                        —NH-lower alkylene-SO 3 M;    —NH-lower alkylene-(CO 2 M) m ;    —S-lower alkylene-SO 2 M;    —S-lower alkylene-(CO 2 M) m ; or    —NH—R 17 , 
 wherein 
 R 1  comprises —SO 3 M or —CO 2 M;  
 R 16  comprises —H, -lower alkyl, -lower alkoxy, -halogen, —NH—C(O)-lower alkyl, —SO 3 M, or —CO 2 M;  
 R 17  comprises —H, -lower alkyl, or —(CH 2 CHR 18 —O)—H,  
 R 18  comprises —H, —CH 3 , —CH 2 CH 3 , or —CH 2 OH,  
 m is 1 or 2;  
 M comprises —H, —Li, —Na, —K, —N(R 19 ) 4 , or —HN(R 19 ) 3 ,  
 wherein  
  R 19  comprises —H, -lower alkyl, or —(CH 2 CHR 20 —O)—H,  
  R 20  comprises —H, —CH 3 , —CH 2 CH 3 , or —CH 2 OH.  
 
     (b) water, and    (c) at least one co-solvent.    
     
     
         9 . The ink composition of  claim 8 , wherein R 1  comprises —SO 3 M.  
     
     
         10 . The composition of  claim 8 , wherein R 1  comprises —CO 2 M.  
     
     
         11 . The composition of  claim 8 , wherein R 3  and R 4  comprise, independently, hydrogen or lower alkoxy.  
     
     
         12 . The composition of  claim 8 , wherein R 5  comprises a group of the formula: 
 —NH-lower alkylene-SO 3 M;    —NH-lower alkylene-(CO 2 M) m ;    —S-lower alkylene-SO 2 M; and    —S-lower alkylene-(CO 2 M) m .    
     
     
         13 . The composition of  claim 8 , wherein the compound of Formula (I) is selected from  
       
         
           
           
               
               
           
         
       
     
     
         14 . An ink composition comprising: 
 (a) at least 0.1% by weight of a compound of Formula (II)                          wherein:    R 3  comprises a lower alkoxy group;    R 5  comprises a group of the formula:                          —NH-lower alkylene-SO 3 M;    —NH-lower alkylene-(CO 2 M) 1 ;    —S-lower alkylene-SO 3 M; or    —S-lower alkylene-(CO 2 M) m ; 
 wherein 
 R 9  and R 13  comprise, independently, —SO 3 M or —CO 2 M;  
 R 10  and R 14  comprise, independently, —H, -lower alkyl, -lower alkoxy, -halogen, —NH—C(O)-lower alkyl, —SO 3 M, or —CO 2 M;  
 R 11  comprises —H, -lower alkyl, -lower alkoxy, —O-lower-alkylene-CO 2 M, -lower alkylene-CO 2 M, —NH—C(O)—CO 2 M, —NH—C(O)-lower alkyl, or —CO 2 M;  
 R 12  comprises —H, -lower alkyl, or -lower alkoxy;  
 
   R 6  comprises a group of the formula:                        —NH-lower alkylene-SO 3 M;    —NH-lower alkylene-(CO 2 M) m ;    —S-lower alkylene-SO 2 M;    —S-lower alkylene-(CO 2 M) m ; or    —NH—R 17 , 
 wherein 
 R 15  comprises —SO 3 M or —CO 2 M;  
 R 16  comprises —H, -lower alkyl, -lower alkoxy, -halogen, —NH—C(O)-lower alkyl, —SO 3 M, or —CO 2 M;  
 R 17  comprises —H, -lower alkyl, or —(CH 2 CHR 18 —O)—H,  
 R 18  comprises —H, —CH 3 , —CH 2 CH 3 , or —CH 2 OH,  
 m is 1 or 2;  
 M comprises —H, —Li, —Na, —K, —N(R 19 ) 4 , or —HN(R 19 ) 3 ,  
 wherein  
  R 19  comprises —H, -lower alkyl, or —(CH 2 CHR 20 —O)—H,  
  R 20  comprises —H, —CH 3 , —CH 2 CH 3 , or —CH 2 OH.  
 
     (b) water, and    (c) at least one co-solvent.    
     
     
         15 . A substrate or medium coated with the ink composition of  claim 8 .  
     
     
         16 . A substrate or medium coated with the ink composition of  claim 14 .  
     
     
         17 . The medium of  claim 15 , wherein said medium is selected from paper, projector slides and textile materials.  
     
     
         18 . The medium of  claim 16 , wherein said medium is selected from paper, projector slides and textile materials.