US2003064051A1PendingUtilityA1

Surface active N-halamine compounds

50
Assignee: UNIV AUBURNPriority: Dec 9, 1997Filed: Sep 3, 2002Published: Apr 3, 2003
Est. expiryDec 9, 2017(expired)· nominal 20-yr term from priority
Inventors:Shelby D. WorleyMichael W. EknoianYanjun Li
C07D 263/26A01N 59/00C07D 263/20A01N 43/76C07D 233/22C07D 263/24
50
PatentIndex Score
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Claims

Abstract

N-halamine biocidal materials and coatings are provided. Monomeric oxazolidinones or hydantoins are homopolymerized or copolymerized with other monomers so as to produce materials or coatings, which upon exposure to solutions of chlorine or bromine become biocidal. The biocidal materials and coatings are effective at inactivating microorganisms upon surface contact and are regenerable following loss of efficacy upon further exposure to solutions of chlorine or bromine. Surfaces which could be treated with the materials and coatings include, but are not limited to: glass, plastic, metals, fibers, and wood for use in pool and tank liners, food wrappers, catheters, paints, tiles, shower walls, fabrics, sterile bandages, pipes, medical and dental coatings, preservatives, and the like.

Claims

exact text as granted — not AI-modified
The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:  
     
         1 . A method of using a monomer having structure I for producing a biocide that is biocidal upon halogenation with chlorine or bromine, comprising the step of:  
       
         
           
           
               
               
           
         
         preparing a precursor compound from the monomer through homopolymerization, copolymerization or grafting, wherein in STRUCTURE I, X is hydrogen; R 1  is hydroxyl, C 2 -C 4  alkyl, benzyl, alkyl-substituted benzyl, phenyl, or alkyl-substituted phenyl; and R 2 , R 3 , and R 4  are independently hydrogen, C 1 -C 4  alkyl, benzyl, substituted benzyl, phenyl, or substituted phenyl.  
       
     
     
         2 . The method of  claim 1 , wherein R 1  is ethyl, and R 2 , R 3 , and R 4  are independently hydrogen, or C 1 -C 2  alkyl.  
     
     
         3 . The method of  claim 2  wherein the monomer is 4-acryloxymethyl-4-ethyl-2-oxazolidinone.  
     
     
         4 . The method of  claim 1  further comprising the step of halogenating the compound with chlorine or bromine.  
     
     
         5 . The method of  claim 4 , wherein the step of halogenating the compound is carried out in situ by adding a solution of a stoichiometric amount of chlorine or bromine.  
     
     
         6 . The method of  claim 1 , wherein the biocide is a coating capable of being applied or adhered to a substrate.  
     
     
         7 . A method of using a monomer having structure 1 as a biocide, comprising the step of: 
 STRUCTURE I:                          inactivating a microorganism selected from the group consisting of bacteria, fungi, molds, protozoa, viruses, and algae, wherein in STRUCTURE I, X is hydrogen; R 1  is hydroxyl, C 2 -C 4  alkyl, benzyl, alkyl-substituted benzyl, phenyl, or alkyl-substituted phenyl; and R 2 , R 3 , and R 4  are independently hydrogen, C 1 -C 4  alkyl, benzyl, substituted benzyl, phenyl, or substituted phenyl.    
     
     
         8 . A monomer having structure IV:  
       
         
           
           
               
               
           
         
         wherein X is hydrogen, chlorine, or bromine; R 1  and R 2  are independently hydrogen, C 1 -C 4  alkyl, benzyl, alkyl-substituted benzyl, phenyl, or alkyl-substituted phenyl; and R 3 , R 4 , and R 5  are independently hydrogen, C 1 -C 4  alkyl, benzyl, alkyl-substituted benzyl, phenyl, or alkyl-substituted phenyl.  
       
     
     
         9 . The monomer of  claim 8 , wherein R 1  and R 2  are methyl; and R 3 , R 4 , and R 5  are independently hydrogen or methyl.  
     
     
         10 . The monomer of  claim 9 , wherein the monomer is 3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         11 . A method of using a monomer having structure IV for producing a biocide, comprising the steps of:  
       
         
           
           
               
               
           
         
         preparing a precursor compound from the monomer through homopolymerization, copolymerization or grafting, wherein in STRUCTURE IV, X is hydrogen, chlorine, or bromine; R 1  and R 2  are independently hydrogen, C 1 -C 4  alkyl, benzyl, alkyl-substituted benzyl, phenyl, or alkyl-substituted phenyl; and R 3 , R 4 , and R 5  are independently hydrogen, C 1 -C 4  alkyl, benzyl, alkyl-substituted benzyl, phenyl, or alkyl-substituted phenyl; and  
         halogentating the compound with chlorine or bromine.  
       
     
     
         12 . The method of  claim 11 , wherein the halogenated compound is the homopolymer poly-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         13 . The method of  claim 11 , wherein the halogenated compound is the homopolymer poly-1-bromo-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         14 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-acrylonitrile-co-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         15 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-acrylonitrile-co-1-bromo-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         16 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-methyl methacrylate-co-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         17 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-methyl methacrylate-co-1-bromo-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         18 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-vinyl acetate-co-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         19 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-vinyl acetate-co-1-bromo-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         20 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-ethyl acrylate-co-styrene-co-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         21 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-ethyl acrylate-co-styrene-co-1-bromo-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         22 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-vinyl acetate-co-methyl methacrylate-co-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         23 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-vinyl acetate-co-methyl methacrylate-co-1-bromo-3(-acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         24 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-vinyl acetate-co-butyl acrylate-co-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         25 . The method of  claim 11 , wherein the halogenated compound is the copolymer poly-vinyl acetate-co-butyl acrylate-co-1-bromo-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         26 . The method of  claim 11 , wherein the halogenated compound is the grafted copolymer poly-acrylonitrile-g-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         27 . The method of  claim 11 , wherein the halogenated compound is the grafted copolymer poly-acrylonitrile-g-1-bromo-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         28 . The method of  claim 11 , wherein the halogenated compound is the grafted copolymer poly-vinyl alcohol-g-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         29 . The method of  claim 11 , wherein the halogenated compound is the grafted copolymer poly-vinyl alcohol-g-1-bromo-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         30 . The method of  claim 11 , wherein the halogenated compound is the grafted copolymer cellulose-g-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         31 . The method of  claim 11 , wherein the halogenated compound is the grafted copolymer cellulose-g-1-bromo-3-(acryloxymethyl)-5,5-dimethylhydantoin.  
     
     
         32 . The method of  claim 11 , further comprising the step of: 
 introducing a diisocyanate in the presence of a tertiary amine to form a thermoset compound.    
     
     
         33 . The method of  claim 32 , wherein the diisocyanate is 4,4′-methylenebis(phenyl isocyanate) or 1,6-diisocyanatohexane.  
     
     
         34 . The method of  claim 32 , wherein the tertiary amine is dimethyl benzyl amine.  
     
     
         35 . The method of  claim 32 , wherein the thermoset compound is the copolymer poly-methyl methacrylate-co-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin-co-hydroxyethyl acrylate.  
     
     
         36 . The method of  claim 32 , wherein the thermoset compound is the copolymer poly-methyl methacrylate-co-1-bromo-3-(acryloxymethyl)-5,5-dimethylhydantoin-co-hydroxyethyl acrylate.  
     
     
         37 . The method of  claim 32 , wherein the thermoset compound is the copolymer poly-methyl methacrylate-co-1-chloro-3-(acryloxymethyl)-5,5-dimethylhydantoin-co-acrylic acid.  
     
     
         38 . The method of  claim 32 , wherein the thermoset compound is the copolymer poly-methyl methacrylate-co-1-bromo-3-(acryloxymethyl)-5,5-dimethylhydantoin-co-acrylic acid.  
     
     
         39 . The method of  claim 11 , wherein the step of halogenating the compound is carried out in situ by adding a solution of a stoichiometric amount of chlorine or bromine.  
     
     
         40 . The method of  claim 11 , wherein the biocide is a coating capable of being applied or adhered to a substrate.  
     
     
         41 . A method of using a monomer having structure IV as a biocide, comprising the step of:  
       
         
           
           
               
               
           
         
         inactivating a microorganism selected from the group consisting of bacteria, fungi, molds, protozoa, viruses, and algae, wherein in STRUCTURE IV, X is hydrogen, chlorine, or bromine: R 1  and R 2  are independently hydrogen, C 1 -C 4  alkyl, benzyl, alkyl-substituted benzyl, phenyl, or alkyl-substituted phenyl; and R 3 , R 4 , and R 5  are independently hydrogen, C 1 -C 4  alkyl, benzyl, alkyl-substituted benzyl, phenyl, or alkyl-substituted phenyl.  
       
     
     
         42 . A method of using a chemical unit having structure III for producing a monomer of a biocide, comprising the step of:  
       
         
           
           
               
               
           
         
         condensing the unit with a diisocyanate or low molecular weight polyurethane in the presence of a catalytic amount of a tertiary amine to form the monomer, wherein in STRUCTURE III, R 1  and R 2  are independently hydrogen, hydroxyl, C 1 -C 4  alkyl, benzyl, substituted benzyl, phenyl or substituted phenyl.  
       
     
     
         43 . A method of using a monomer of 4,4-dihydroxymethyl-2-oxazolidinone to produce a biocide, comprising the steps of: 
 polymerizing the monomer with a diisocyanate or low molecular weight polyurethane in the presence of a catalytic amount of a tertiary amine to form a precursor compound, and    halogenating the compound with chlorine or bromine.    
     
     
         44 . The method of  claim 43 , wherein the diisocyanate is 1,6-diisocyanatohexane.  
     
     
         45 . The method of  claim 43 , wherein the tertiary amine is dimethyl benzyl amine.  
     
     
         46 . The method of  claim 43 , wherein the diol is 1,4-butanediol.  
     
     
         47 . The method of  claim 43 , wherein the step of halogenating the compound is carried out in situ by adding a solution of a stoichiometric amount of chlorine or bromine.  
     
     
         48 . The method of  claim 43 , wherein the biocide is a polyurethane surface coating.  
     
     
         49 . A method of using a monomer of 4,4-dihydroxymethyl-2-oxazolidinone as a biocide, comprising the step of: 
 inactivating a microorganism selected from the group consisting of bacteria, fungi, molds, protozoa, viruses, and algae.    
     
     
         50 . A biocidal article, comprising: 
 a film or material made from a monomer of structure I                          wherein X is hydrogen; R 1  is hydroxyl, C 2 -C 4  alkyl, benzyl, alkyl-substituted benzyl, phenyl, or alkyl-substituted phenyl; and R 2 , R 3 , and R 4  are independently hydrogen, C 1 -C 4  alkyl, benzyl, substituted benzyl, phenyl, or substituted phenyl, and wherein the film or material is coated onto a substrate and treated with a halogen.    
     
     
         51 . The article of  claim 50 , wherein the substrate is selected from the group consisting of glass, wood, metal, plastic, concrete, and fibers.  
     
     
         52 . A biocidal article, comprising: 
 a film or material made from a monomer of structure IV.                          wherein X is hydrogen, chlorine, or bromine; R 1  and R 2  are independently hydrogen, C 1 -C 4  alkyl, benzyl, alkyl-substituted benzyl, phenyl, or alkyl-substituted phenyl; and R 3 , R 4  and R 5  are independently hydrogen, C 1 -C 4  alkyl, benzyl, alkyl-substituted benzyl, phenyl, or alkyl-substituted phenyl, and wherein the film or material is coated onto a substrate and treated with a halogen.    
     
     
         53 . The article of  claim 52 , wherein the substrate is selected from the group consisting of glass, wood, metal, plastic, concrete, and fibers.  
     
     
         54 . A biocidal article, comprising: 
 a film or material made from a monomer of structure III.                          wherein R 1  and R 2  are independently hydrogen, hydroxyl, C 1 -C 4  alkyl, benzyl, substituted benzyl, phenyl, or substituted phenyl, and wherein the film or material is coated onto a substrate and treated with a halogen.    
     
     
         55 . The article of  claim 54  wherein the substrate is selected from the group consisting of glass, wood, metal, plastic, concrete, and fibers.  
     
     
         56 . A biocidal article, comprising: 
 a film or material made from a monomer of 4,4-dihydroxymethyl-2-oxazolidinone, wherein the film or material is coated onto a substrate and treated with a halogen.    
     
     
         57 . The article of  claim 56 , wherein the substrate is selected from the group consisting of glass, wood, metal, plastic, concrete, and fibers.

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