Heterocyclic siloxanes for use in biocidal coatings and materials

Abstract

Heterocyclic and acyclic silane monomers and siloxane polymers, and their halogenated derivatives, are provided for the purpose of functionalizing surfaces or materials so as to render them biocidal upon exposure to oxidative halogen solutions. The biocidal function can be imparted either before or after bonding or adhesion to the surface or material. The biocidal surfaces and materials can then be used to inactivate pathogenic microorganisms such as bacteria, fungi, and yeasts, as well as virus particles, which can cause infectious diseases, and those microorganisms which cause noxious odors and unpleasant coloring such as mildew. Examples of surfaces and materials which can be rendered biocidal in this invention include, but are not limited to, cellulose, chitin, chitosan, synthetic fibers, glass, ceramics, plastics, rubber, cement grout, latex caulk, porcelain, acrylic films, vinyl, polyurethanes, silicon tubing, marble, metals, metal oxides, and silica.

1 . A compound having the structure  
         (R-L) n -Si-(R 1 ) 4-n   wherein R 1  is independently selected from a C1-C4 alkyl, aryl, C1-C4 alkoxy, hydroxy, chloro, or C1-C4 ester group, wherein at least one R1 group is a C1-C4 alkoxy, hydroxy, chloro, or C1-C4 ester group; wherein L is a linker group; wherein n=1, 2, or 3; and wherein R is at least one of an amide-linked hydantoin, imidazolidinone, oxazolidinone, isocyanurate, glycoluril, or triazinedione.    
     
     
         2 . The compound of  claim 1 , wherein L is a linker alkylene, amine, or ether group, comprised of 1-13 carbons and 0-3 nitrogen or oxygen atoms, or L is a linker alkylene group of 1-13 carbons and a carbamate, thiocarbamate, or urea functional group.  
     
     
         3 . The compound of  claim 1  having the structure  
       
         
           
           
               
               
           
         
         wherein R1, R2, and R3 are independently selected from a C1-C4 alkyl, aryl, C1-C4 alkoxy, hydroxy, chloro, or C1-C4 ester group, wherein at least one of R1, R2, or R3 is a C1-C4 alkoxy, hydroxy, chloro, or C1-C4 ester group; wherein L is a linker group; and wherein R is at least one of an amide-linked hydantoin, imidazolidinone, oxazolidinone, isocyanurate, glycoluril, or triazinedione.  
       
     
     
         4 . The compound of  claim 3 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 and R5 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         5 . The compound of  claim 3 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4, R5, R 6 , and R 7  are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         6 . The compound of  claim 3 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4, R5, R6, and R7 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         7 . The compound of  claim 3 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 at least one of a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         8 . The compound of  claim 3 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4, R5, R6, and R7 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         9 . The compound of  claim 3 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 and R5 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group; wherein X is independently selected from hydrogen or hydroxymethyl, and wherein at least one X is hydrogen.  
       
     
     
         10 . The compound of  claim 3 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein X is independently selected from hydrogen or hydroxymethyl, and wherein at least one X is hydrogen.  
       
     
     
         11 . The compound of  claim 3 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 and R5 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group; wherein X is independently selected from hydrogen or hydroxymethyl, and wherein at least one X is hydrogen.  
       
     
     
         12 . A siloxane, comprising the structure  
       
         
           
           
               
               
           
         
         wherein, n≧2; R1 is at least one of a C1-C4 alkyl, aryl, C1-C4 alkoxy, hydroxy, chloro, or C 1 -C 4  ester group; wherein L is a linker group; and wherein R is a heterocyclic amine.  
       
     
     
         13 . The siloxane of  claim 12 , wherein R is at least one of a hydantoin, imidazolidinone, oxazolidinone, isocyanurate, glycoluril, triazinedione, or piperidine.  
     
     
         14 . The siloxane of  claim 12 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 and R5 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         15 . The siloxane of  claim 12 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 and R5 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         16 . The siloxane of  claim 12 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4, R5, R6, and R7 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         17 . The siloxane of  claim 12 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4, R5, R6, and R7 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         18 . The siloxane of  claim 12 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 is at least one of a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         19 . The siloxane of  claim 12 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4, R5, R6, and R7 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         20 . The siloxane of  claim 12 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 and R5 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group; wherein X is independently selected from hydrogen or hydroxymethyl, and wherein at least one X is hydrogen.  
       
     
     
         21 . The siloxane of  claim 12 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein X is independently selected from at least one of hydrogen or hydroxymethyl, and wherein at least one X is hydrogen.  
       
     
     
         22 . The siloxane of  claim 12 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 and R5 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group; wherein X is independently selected from at least one of hydrogen or hydroxymethyl, and wherein at least one X is hydrogen.  
       
     
     
         23 . The siloxane of  claim 12 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4, R5, R6, and R7 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         24 . A modified substrate, comprising the structure 
         (R-L) n (R 1 ) m -Si-(O) p - wherein, m=0, 1, or 2; n=1, 2, or 3; p=1,2, or 3; and m+n+p=4; wherein R is a heterocyclic amine; wherein L is a linker group; and wherein R1 is a C1-C4 alkoxy, hydroxy, chloro, or C1-C4 ester group.    
     
     
         25 . The modified substrate of  claim 24 , comprising the structure  
       
         
           
           
               
               
           
         
         wherein, n≧2; L is a linker group; and wherein R is a heterocyclic amine.  
       
     
     
         26 . The modified substrate of  claim 25 , wherein R is one of at least a hydantoin, imidazolidinone, oxazolidinone, isocyanurate, glycoluril, triazinedione, or piperidine.  
     
     
         27 . The modified substrate of  claim 25 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 and R5 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         28 . The modified substrate of  claim 25 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 and R5 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         29 . The modified substrate of  claim 25 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4, R5, R6, and R7 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         30 . The modified substrate of  claim 25 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4, R5, R6, and R7 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         31 . The modified substrate of  claim 25 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 is at least one of a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         32 . The modified substrate of  claim 25 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4, R5, R6, and R7 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         33 . The modified substrate of  claim 25 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 and R5 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group; wherein X is independently selected from hydrogen or hydroxymethyl, and wherein at least one X is hydrogen.  
       
     
     
         34 . The modified substrate of  claim 25 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein X is independently selected from hydrogen or hydroxymethyl, and wherein at least one X is hydrogen.  
       
     
     
         35 . The modified substrate of  claim 25 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4 and R5 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group; wherein X is independently selected from hydrogen or hydroxymethyl, and wherein at least one X is hydrogen.  
       
     
     
         36 . The modified substrate of  claim 25 , wherein R has the structure  
       
         
           
           
               
               
           
         
         wherein R4, R5, R6, and R7 are independently selected from a C1-C4 alkyl, aryl, or hydroxymethyl group.  
       
     
     
         37 . A method for making a modified substrate, comprising: 
 applying a compound of  claim 1  and water to a substrate;    drying the substrate; and    curing the substrate at a temperature sufficient to provide a modified substrate.