Controlled release biocidal salts

Abstract

A controlled release biocidal salt of a first component comprises a cation of a N α —(C 1 -C 22 )alkanoyl di-basic amino acid alkyl(C 1 -C 22 )ester cationic biocidal molecule and a second component comprising an anion of a monomeric anionic molecule having insignificant biocidal activity. The salt is characterized such that when the salt is exposed to an aqueous medium, the salt partially dissolves thereby releasing biocidal ions in an amount sufficient to exceed the MIC or MBC of a target bacteria being controlled, and further characterized as leaving a residual reservoir of undissolved salt capable of releasing more biocidal ions as the salt is consumed or otherwise removed from the environment encompassing the target bacteria. The preferred cationic biocidal molecule comprises N α -lauroyl-L-arginine ethyl ester (“LAE”).

1 . A controlled release biocidal salt of a first component comprising a cation of a N α —(C 1 -C 22 )alkanoyl di-basic amino acid alkyl(C 1 -C 22 )ester cationic biocidal molecule and a second component comprising an anion of a monomeric anionic molecule having insignificant biocidal activity, said salt being characterized such that when the salt is exposed to an aqueous medium, the salt partially dissolves thereby releasing biocidal ions in an amount sufficient to exceed the MIC or MBC of a target bacteria being controlled, and further characterized as leaving a residual reservoir of undissolved salt capable of releasing more biocidal ions as the salt is consumed or otherwise removed from the environment encompassing the target bacteria. 
     
     
         2 . The salt of  claim 1  wherein the di-basic amino acid of the first component is selected from the group consisting of arginine, lysine, histidine and tryptophan. 
     
     
         3 . The salt of  claim 2  wherein the first component comprises N α -lauroyl-L-arginine ethyl ester. 
     
     
         4 . The salt of  claim 1  wherein the salt releases at least about 2 ppm of biocidal ions when exposed to an aqueous medium. 
     
     
         5 . The salt of  claim 1  wherein the second component contains a moiety selected from the group consisting of carboxylic, hydroxycarboxylic, phenolic, pentacyclic triterpenoid, enol, acidic amino acid, a protein having a residual negative charge, phosphate moiety present on a DNA nucleotide, an anionic phospholipid, bis-phosphonate, phosphonate, sulfate, sulfonate and mixtures of the foregoing moieties. 
     
     
         6 . The salt of  claim 5  wherein the phenolic moiety comprises resorcinol. 
     
     
         7 . The salt of  claim 5  wherein the enol moiety comprises an acid selected from the group consisting of ascorbic acid, its esters and its phosphate salts, and dehydroacetic acid. 
     
     
         8 . The salt of  claim 5  wherein the carboxylic moiety comprises a carboxylic acid selected from the group consisting of adapalene; isotretinoin; pantothenic acid; benzoic acid, salicyclic acid; retinoic acid; tretinoin; an aldobionic acid; undecylenic acid; an α-hydroxycarboxylic acid; a β-hydroxycarboxylic acid; an α-ketocarboxylic acid; a β-keto carboxylic acid; and azelaic acid. 
     
     
         9 . The salt of  claim 8  wherein the a-hydroxycarboxylic acid is selected from the group consisting of glycolic, lactic, tartaric, mandelic, malic, citric, gluconic, glyceric and glyoxylic. 
     
     
         10 . The salt of  claim 5  wherein the carboxylic moiety comprises a C 8 -C 22  saturated or unsaturated fatty acid. 
     
     
         11 . The salt of  claim 10  wherein the saturated acid is selected from the group consisting of lauric, myristic, palmitic, and stearic acids. 
     
     
         12 . The salt of  claim 10  wherein the unsaturated acid is selected from the group consisting of linolenic, arachidonic, oleic, linoleic, eicosapentanoic and docosahexenoic acids. 
     
     
         13 . The salt of  claim 1  further comprising a saturated C 6 -C 14  fatty acid monoglyceride. 
     
     
         14 . The salt of  claim 13  wherein the monoglyceride comprises glycerol monolaurate. 
     
     
         15 . The salt of  claim 14  wherein the glycerol monolaurate is present in an amount of about 1 to about 10 wt. %, based on the weight of the salt. 
     
     
         16 . The salt of  claim 5  wherein the phenolic moiety comprises a polyphenol selected from the group consisting of ferulic acid, reservatrol, gallic acid, coumaric acid, catechin, caffeic acid, vanillic acid, chlorogenic acid, apianin and sinapyl arbutin. 
     
     
         17 . The salt of  claim 5  wherein the pentacyclic triterpenoid is selected from the group consisting of betulinic acid, moronic acid, ursolic acid and oleanolic acid. 
     
     
         18 . The salt of  claim 1  which is formed by a metathesis reaction between an salt of the first component and an alkali or alkaline earth metal salt of the second component. 
     
     
         19 . The salt of  claim 1  which is formed by an acid-base reaction between the first component present in the form of its free base and the second component present in the form of an undissociated molecule having a transferable proton. 
     
     
         20 . A material containing the salt of  claim 1 , said material being selected from the group consisting of a food or food product; a beverage; a preservative composition; a perishable item; a packaging; fluid-dispensing tubing; a plastic; a pharmaceutical product; a medical device, a cosmetic; a deodorant; a coating; a dental care composition; a dental care appliance; a dental hygiene product; a wound care composition; a dermatological care composition; a personal hygiene item; an adult novelty item; a sexual aid item; a sex toy item; a condom item; a pregnancy barrier item; an infant care product; a surgical soap; a surgical or hospital gown; a microbiocide; an antifungal composition; an anti-yeast composition; an anti-mold composition; an animal care product; an apparel product; a woven or nonwoven or knit fabric; a foam; a film; a paper product; wood or a wood product; a construction material; plasterboard; a rubber item; and a virucide.