Disazo Acid Dyes

Abstract

Compounds of the general formula (I) a process for their preparation and their use for dyeing and/or printing organic substrates.

1 . A compound of the general formula (I) 
     
       
         
         
             
             
         
       
     
     wherein
 R 1 , R 2 , R 9  and R 10  are independently selected from the group consisting of: unsubstituted unbranched C 1-6 alkyl, unsubstituted branched C 3-6 alkyl, substituted unbranched C 1-6 alkyl, substituted branched C 3-6 alkyl, aryl, and —(CH 2 ) p -aryl wherein p=1, 2, 3 or 4, 
 R 3  and R 8  is selected from the group consisting of: hydrogen, unsubstituted unbranched C 1-6 alkyl, unsubstituted branched C 3-6 alkyl, substituted unbranched C 1-6 alkyl, substituted branched C 3-6 alkyl, unsubstituted unbranched C 1-6 alkoxy, unsubstituted branched C 3-6 alkoxy, substituted unbranched C 1-6 alkoxy, substituted branched C 3-6 alkoxy, halogen, —NHCO—(C 1-6 alkyl) with an unbranched C 1-6 alkyl group, which is substituted or unsubstituted, —NHCO—(C 3-6 alkyl) with a branched C 3-6 alkyl group, which is substituted or unsubstituted, and —NHCONH 2 , 
 BR is a bridge of the formula -A-B-A- wherein
 A is selected from the group consisting of: substituted phenyl, substituted naphthyl, unsubstituted phenyl, and unsubstituted naphthyl, and 
 B is a bridging —[(CR 6 R 7 )— (CR 6′ R 7′ ) m —(CR 6″ R 7″ ) n —(CR 6′″ R 7′″ ) o ]— where m, n and o are independently 1 or 0, and R 6 , R 7 , R 6′ , R 7′ , R 6″ , R 7″ , R 6′″  and R 7′″  are independently selected from the group consisting of: hydrogen, unsubstituted unbranched C 1-6 alkyl, substituted unbranched C 1-6 alkyl, substituted branched C 3-6 alkyl, unsubstituted branched C 3-6 alkyl, unsubstituted unbranched C 1-6 alkoxy, unsubstituted phenyl, and substituted phenyl, or 
 B is a bridging sulphon, or 
 B is a bridging sulphonamide, or 
 B is a bridging carboxamide, or 
 B is a bridging 
 
 
     
       
         
         
             
             
         
       
     
     and
 the compound of the formula (I) contains 1, 2 or 3 sulpho groups and wherein there are no anionic groups in the bridging member BR. 
 
   
   
       2 . A compound according to  claim 1  wherein
 R 1  and R 9  are independently selected from the group consisting of: unsubstituted unbranched C 1-6 alkyl, unsubstituted branched C 3-6 alkyl, substituted unbranched C 1-6 alkyl, and substituted branched C 3-6 alkyl,   R 2  and R 10  are independently aryl, or —(CH 2 ) p -aryl wherein p is 1, 2, 3 or 4,   R 3  and R 8  are independently selected from the group consisting of: hydrogen, unsubstituted unbranched C 1-6 alkyl, unsubstituted branched C 3-6 alkyl, substituted unbranched C 1-6 alkyl, substituted branched C 3-6 alkyl, unsubstituted unbranched C 1-6 alkoxy, unsubstituted branched C 3-6 alkoxy, substituted unbranched C 1-6 alkoxy, and substituted branched C 3-6 alkoxy,   BR is a bridge of the formula -A-B-A- wherein
 A is selected from the group consisting of: substituted phenyl, substituted naphthyl, unsubstituted phenyl, and unsubstituted naphthyl, and 
 B is a bridging —[(CR 6 R 7 )—(CR 6′ R 7′ ) m —(CR 6″ R 7″ ) n —(CR 6′″ R 7′″ ) o ]— where m, n and o are independently 1 or 0, and R 6 , R 7 , R 6′ , R 7′ , R 6″ , R 7″ , R 6′″  and R 7′″  are independently selected from the group consisting of: hydrogen, unsubstituted unbranched C 1-6 alkyl, substituted unbranched C 1-6 alkyl, substituted branched C 3-6 alkyl, unsubstituted branched C 3-6 alkyl, unsubstituted unbranched C 1-6 alkoxy, unsubstituted phenyl, and substituted phenyl or, or 
 B is a bridging sulphon, or 
 B is a bridging sulphonamide, or 
 B is a bridging carboxamide, or 
 B is a bridging 
   
     
       
         
         
             
             
         
       
     
     and
 the compound of the formula (I) contains 1, 2 or 3 sulpho groups. 
 
   
   
       3 . A compound according to  claim 1  wherein the compound of the formula (I) contains 2 sulpho groups. 
   
   
       4 . A compound according to  claim 1  wherein the bridge BR is selected from the group consisting of 
     
       
         
         
             
             
         
       
     
     wherein
 R 4 , R 4′ , R 5  and R 5′  are independently selected from the group consisting of: hydrogen, unsubstituted unbranched C 1-6 alkyl, unsubstituted branched C 3-6 alkyl, substituted unbranched C 1-6 alkyl, substituted branched C 3-6 alkyl, unsubstituted unbranched C 1-6 alkoxy, unsubstituted branched C 3-6 alkoxy, substituted unbranched C 1-6 alkoxy, substituted branched C 3-6 alkoxy, halogen, —NHCO—(C 3-6 alkyl) with an unbranched C 1-6 alkyl group, which is substituted or unsubstituted, —NHCO—(C 3-6 alkyl) with a branched C 3-6 alkyl group, which is substituted or unsubstituted, and —NHCONH 2    
 R 6 , R 7 , R 6′ , R 7′ , R 6″ , 
 R 7″ , R 6′″  and R 7′″  are independently selected from the group consisting of: hydrogen, unsubstituted unbranched C 1-6 alkyl, unsubstituted unbranched C 1-6 alkoxy, unsubstituted phenyl and substituted phenyl, or 
 m, n and o are independently of 1 or 0. 
 
   
   
       5 . A process for preparing a compound of the formula (I) according to  claim 1 , comprising the step of diazotizing and coupling both the amine functions of a compound of the formula (II)
   H 2 N—BR—NH 2   (II)   
     onto a total of two equivalents of a compound of the formula (IIIa) and of a compound of the formula (IIIb) 
     
       
         
         
             
             
         
       
     
     wherein the substituents are each as defined above. 
   
   
       6 . A process for dyeing and/or printing an organic substrate comprising the step of contacting at least one compound of the formula (I) according to  claim 1  with the organic substrate. 
   
   
       7 . A process for dyeing and/or printing a substrate comprising wool, silk and/or synthetic polyamide comprising the step of contacting at least one compound of formula (I) according to  claim 1  with the substrate comprising wool, silk and/or synthetic polyamide. 
   
   
       8 . A process for preparing a printing ink, comprising the step of adding at least one compound of formula (I) according to  claim 1 , to at least one further component of a printing ink. 
   
   
       9 . A process for preparing an inkjet printing ink, comprising the step of adding at least one compound of formula (I) according to  claim 1 , to at least one further component of a inkjet printing ink. 
   
   
       10 . An inkjet printing ink, comprising at least one compound of formula (I) according to  claim 1 . 
   
   
       11 . A printing ink, comprising at least one compound of formula (I) according to  claim 1 . 
   
   
       12 . A substrate dyed and/or printed by the process according to  claim 6 .