Multifunctional antimicrobial dyes

Abstract

The present invention provides functional finishing dyes comprising at least one functional finishing group covalently attached to a traditional dye via a chemical linkage. More particularly, the present invention provides novel antimicrobial cationic dyes comprising a quaternary ammonium salt group covalently attached to an aminoanthraquinioid dye via a linker. The dyes are particularly useful for imparting a functional property to a polymer, such as an antimicrobial, anti-static, softening, water-repellent, fire-resistant, soil-repellent, anti-UV, or anti-chemical property, and for simultaneously dyeing and finishing a polymer.

1 . A compound having the formula:  
       
         
           
           
               
               
           
         
       
       wherein: 
 each R 1  is an independently selected quaternary ammonium salt group;  
 each R 2  is independently selected from a quaternary ammonium salt group and a substituent group;  
 m is an integer from 0 to 4; and  
 n is an integer from 1 to 4.  
 
     
     
         2 . The compound of  claim 1 , wherein said quaternary ammonium salt group has the formula:  
         —N(R 3 )-L-N + (R 4 )(R 5 )(R 6 )-X − ,  Ia  
       wherein: 
 R 3  is a member selected from the group consisting of hydrogen, an alkyl group, and an amino protecting group;  
 each of R 4 , R 5 , and R 6  is independently selected from the group consisting of hydrogen, alkyl, aryl, aralkyl, cycloalkyl, and cycloalkylalkyl;  
 L is a linker comprising a 1-12 carbon atom chain; and  
 X is a counter anion.  
 
     
     
         3 . The compound of  claim 2 , wherein: 
 R 4  and R 5  are each independently selected C 1 -C 4  alkyl groups; and    R 6  is a C 4 -C 18  alkyl group.    
     
     
         4 . The compound of  claim 3 , wherein: 
 R 4  and R 5  are methyl groups; and    R 6  is a C 4 -C 18  alkyl group.    
     
     
         5 . The compound of  claim 4 , wherein: 
 R 6  is selected from the group consisting of a butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl group.    
     
     
         6 . The compound of  claim 5 , wherein: 
 R 6  is selected from the group consisting of an octyl and dodecyl group.    
     
     
         7 . The compound of  claim 2 , wherein X is independently selected from the group consisting of F − , Cl −1 , Br −1 , I −1 , and combinations thereof.  
     
     
         8 . The compound of  claim 1 , wherein said substituent group is independently selected from the group consisting of hydrogen, alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, sulfonate, hydroxyl, alkoxyl, amino, and alkylamino.  
     
     
         9 . The compound of  claim 1 , wherein said compound has the following structure:  
       
         
           
           
               
               
           
         
       
       wherein: 
 R 4  and R 5  are each independently selected C 1 -C 4  alkyl groups;  
 R 6  is a C 4 -C 18  alkyl group;  
 R 7  is a C 1 -C 12  alkylene group optionally interrupted with a heteroatom or a —C(O)R 8  group, wherein R 8  is a C 1 -C 12  alkylene group; and  
 X is a counter anion.  
 
     
     
         10 . The compound of  claim 9 , wherein R 4  and R 5  are methyl groups.  
     
     
         11 . The compound of  claim 9 , wherein R 6  is an octyl or dodecyl group.  
     
     
         12 . The compound of  claim 9 , wherein R 7  is a —CH 2  or a —C(O)CH 2  group.  
     
     
         13 . The compound of  claim 9 , wherein X is independently selected from the group consisting of F −1 , Cl −1 , Br −1 , and I −1 .  
     
     
         14 . The compound of  claim 1 , wherein said compound has the following structure:  
       
         
           
           
               
               
           
         
       
       wherein 
 R 4 , R 5 , R 10 , and R 11  are each independently selected C 1 -C 4  alkyl groups;  
 R 6  and R 12  are each independently selected C 4 -C 18  alkyl groups;  
 R 7  and R 9  are each independently selected C 1 -C 12  alkylene groups optionally interrupted with a heteroatom or —C(O)R 8  groups, wherein R 8  is a C 1 -C 12  alkylene group; and  
 each X is an independently selected counter anion.  
 
     
     
         15 . The compound of  claim 14 , wherein R 4 , R 5 , R 10 , and R 11  are methyl groups.  
     
     
         16 . The compound of  claim 14 , wherein R 6  and R 12  are independently selected octyl or dodecyl groups.  
     
     
         17 . The compound of  claim 14 , wherein R 7  and R 9  are independently selected —CH 2  or —C(O)CH 2  groups.  
     
     
         18 . The compound of  claim 14 , wherein X is independently selected from the group consisting of F − , Cl − , Br − , and I − .  
     
     
         19 . A polymer composition comprising: 
 (a) a polymer, wherein said polymer is a member selected from the group consisting of a textile, a plastic, rubber, paint, a surface coating, an adhesive, and a combination thereof; and    (b) a compound having the formula:                          wherein:    each R 1  is an independently selected quaternary ammonium salt group;    each R 2  is independently selected from a quaternary ammonium salt group and a substituent group;    m is an integer from 0 to 4; and    n is an integer from 1 to 4.    
     
     
         20 . The composition of  claim 19 , wherein said polymer is a textile.  
     
     
         21 . The composition of  claim 20 , wherein said textile is selected from the group consisting of a fiber from a plant, a polymer from an animal, a natural organic polymer, a synthetic organic polymer, an inorganic substance, and a combination thereof.  
     
     
         22 . The composition of  claim 21 , wherein said textile is selected from the group consisting of cellulose, cotton, linen, hemp, jute, ramie, wool, mohair, vicuna, silk, rayon, lyocell, acetate, triacetate, nylon, polyester, a polyester/cellulose blend, acrylic, azlon, aramid, olefin, spandex, vinyon, vinyl, graphite, an aromatic polyamide, glass, a metallic material, a ceramic material, and a combination thereof.  
     
     
         23 . The composition of  claim 19 , wherein said polymer is a plastic.  
     
     
         24 . The composition of  claim 23 , wherein said plastic is selected from the group consisting of polyethylene, polypropylene, polystyrene, and polyvinylchloride polyamideimide, polyethersulfone, polyarylsulfone, polyetherimide, polyarylate, polysulfone, polycarbonate, polyetherketone, polyetheretherketone, polytetrafluoroethylene, nylon-6,6, nylon-6,12, nylon-11, nylon-12, acetal resin, polypropylene, polyethylene, and a combination thereof.  
     
     
         25 . A method for simultaneously dyeing and finishing a polymer, said method comprising: 
 immersing said polymer in an aqueous treating solution which comprises a compound having the formula::                          wherein:    each R 1  is an independently selected quaternary ammonium salt group;    each R 2  is independently selected from a quaternary ammonium salt group and a substituent group;    m is an integer from 0 to 4; and    n is an integer from 1 to 4.    
     
     
         26 . The method of  claim 25 , further comprising removing excess aqueous treating solution from said polymer.  
     
     
         27 . The method of  claim 26 , further comprising drying said article after removing excess aqueous treating solution to produce a dried polymer.  
     
     
         28 . The method of  claim 25 , wherein said aqueous treating solution further comprises a wetting agent.  
     
     
         29 . The method of  claim 25 , wherein said polymer is a textile.  
     
     
         30 . The method of  claim 29 , wherein said textile is selected from the group consisting of a fiber from a plant, a polymer from an animal, a natural organic polymer, a synthetic organic polymer, an inorganic substance, and a combination thereof.  
     
     
         31 . The method of  claim 30 , wherein said textile is selected from the group consisting of cellulose, cotton, linen, hemp, jute, ramie, wool, mohair, vicuna, silk, rayon, lyocell, acetate, triacetate, nylon, polyester, a polyester/cellulose blend, acrylic, azlon, aramid, olefin, spandex, vinyon, vinyl, graphite, an aromatic polyamide, glass, a metallic material, a ceramic material, and a combination thereof.  
     
     
         32 . The method of  claim 25 , wherein said polymer is a plastic.  
     
     
         33 . The method of  claim 32 , wherein said plastic is selected from the group consisting of polyethylene, polypropylene, polystyrene, and polyvinylchloride polyamideimide, polyethersulfone, polyarylsulfone, polyetherimide, polyarylate, polysulfone, polycarbonate, polyetherketone, polyetheretherketone, polytetrafluoroethylene, nylon-6,6, nylon-6,12, nylon-11, nylon-12, acetal resin, polypropylene, polyethylene, and a combination thereof.