Non-Petrochemically Derived Cationic Emulsifiers and Related Compositions and Methods

Abstract

The invention includes a neutralized amino acid ester emulsifier, emulsions and compositions containing the emulsifier, and related methods. The emulsifier is a neutralized amino acid ester that is a reaction product of a neutral amino acid with a fatty alcohol and is represented by formula (I): wherein R 1 is an alkyl group that has 6 to 24 carbon atoms; R 2 is an alkyl group that has 6 to 36 carbon atoms; and the amine group of the amino acid is neutralized with an acid. The emulsifier 1.0 is cationic. Also included are stable emulsions and compositions, preferably personal care compositions, that include the emulsifier and which may have pH levels of 5.5 or greater. Encompassed within the scope of the invention are methods of increasing the substantivity of a composition to a negatively charged substrate using the emulsifier, methods of emulsifying and methods of preparing a personal care composition using the emulsifier.

1 . A method of increasing the substantivity of a composition to a negatively charged substrate comprising preparing a composition comprising at least one phase and an effective amount of an amino acid ester that is a reaction product of a neutralized amino acid esterified with a fatty alcohol and is represented by formula (I): 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is an alkyl group that has 6 to 24 carbon atoms; 
         R 2  is an alkyl group that has 6 to 36 carbon atoms; and the amine group of the amino acid is neutralized with an acid prior to esterification, 
         wherein the composition exhibits increased substantivity to a negatively charged surface relative to the substantivity of an identical composition that does not contain the amino acid ester. 
       
     
     
         2 . The method of  claim 1 , wherein the composition is an emulsion. 
     
     
         3 . (canceled) 
     
     
         4 . The method of  claim 1 , wherein the composition has a pH of about 5.5 to about 8.5. 
     
     
         5 . The method of  claim 1 , wherein the alkyl group of R 1  is selected from a branched alkyl group or a linear alkyl group. 
     
     
         6 . The method of  claim 1 , wherein the alkyl group of R 1  comprises at least one unsaturated carbon atom. 
     
     
         7 . (canceled) 
     
     
         8 . The method of  claim 1 , wherein the alkyl group of R 1  is selected from groups having 6, 7, 8, 9, and 10 carbon atoms. 
     
     
         9 . The method of  claim 1 , wherein the alkyl group of R 1  is selected from groups having 11, 12, 13, 14, 15, 16 and 17 carbon atoms. 
     
     
         10 . The method of  claim 1 , wherein the alkyl group of R 1  is selected from groups having 18, 19, 20, 21, 22, 23 and 24 carbon atoms. 
     
     
         11 . The method of  claim 1 , wherein the alkyl group of R 1  is linear and has 11 carbon atoms. 
     
     
         12 . The method of  claim 1 , wherein the neutral amino acid is obtained from vegetable matter. 
     
     
         13 . The method of  claim 1 , wherein the alkyl group of R 2  is selected from a branched alkyl group or a linear alkyl group. 
     
     
         14 . The method of  claim 1 , wherein the alkyl group of R 2  comprises at least one unsaturated carbon atom. 
     
     
         15 . The method of  claim 1 , wherein the alkyl group of R 2  comprises all unsaturated carbon atoms. 
     
     
         16 . The method of  claim 1 , wherein the alkyl group of R 2  is selected from groups having 6, 7, 8, 9, and 10 carbon atoms. 
     
     
         17 . The method of  claim 1 , wherein the alkyl group of R 2  is selected from groups having 11, 12, 13, 14, 15, 16 and 17 carbon atoms. 
     
     
         18 . The method of  claim 1 , wherein the alkyl group of R 2  is selected from groups having 18, 19, 20, 21, 22, 23 and 24 carbon atoms. 
     
     
         19 . The method of  claim 1 , wherein the alkyl group of R 2  is selected from groups having 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, and 36 carbon atoms. 
     
     
         20 . The method of  claim 1 , wherein the fatty alcohol is selected from the group consisting of capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, lignoceryl alcohol, isostearyl alcohol, and mixtures thereof. 
     
     
         21 . The method of  claim 1 , wherein the fatty alcohol is selected from the group consisting of 3-methyl-3 pentanol, ethchlorvynol, 1-octanol, 2-ethyl hexanol, 1-nonanol, undecanol, tridecanol, pentadecyl alcohol, palmitoleyl alcohol, heptadecyl alcohol, nonadecyl alcohol, Heneicosyl alcohol, erucyl alcohol, ceryl alcohol, 1-hepracosanol, cluytyl alcohol, 1-nonacosanol, myricyl alcohol, 1-dotriacontanol, geddyl alcohol and mixtures thereof. 
     
     
         22 - 28 . (canceled) 
     
     
         29 . A method of preparing an emulsified composition that exhibits substantivity to a negatively charged substrate comprising combining an effective amount of an emulsifier, a first phase and a second phase, wherein the emulsifier is an effective amount of an amino acid ester that is a reaction product of a neutralized amino acid esterified with a fatty alcohol and is represented by formula (I): 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is an alkyl group that has 6 to 24 carbon atoms; 
         R 2  is an alkyl group that has 6 to 36 carbon atoms; and the amine group of the amino acid is neutralized with an acid prior to esterification, 
         wherein the emulsifier serves to emulsify the first and the second composition to form an emulsion. 
       
     
     
         30 . The method of  claim 29 , wherein the first phase is an aqueous phase and the second phase is a non-aqueous phase. 
     
     
         31 - 35 . (canceled) 
     
     
         36 . An emulsifier for the preparation of a stable emulsion comprising a neutralized amino acid ester that is a reaction product of a neutral amino acid with a fatty alcohol and is represented by formula (I): 
       
         
           
           
               
               
           
         
         wherein R 1  is an alkyl group that has 6 to 24 carbon atoms; 
         R 2  is an alkyl group that has 6 to 36 carbon atoms; and 
         the amine group of the amino acid is neutralized with an acid and the emulsifier is cationic. 
       
     
     
         37 - 45 . (canceled) 
     
     
         46 . A method of emulsifying a personal care composition having an aqueous phase and a non-aqueous phase comprising incorporating the aqueous phase and a non-aqueous phase with each other in the presence of an effective amount of the emulsifier of claim  35 . 
     
     
         47 . The method of  claim 46 , wherein each of the aqueous phase and the non-aqueous phase is substantially free of petrochemicals and/or derivatives of petrochemical materials. 
     
     
         48 . A composition prepared by the method of  claim 1 . 
     
     
         49 . A stable emulsion comprising an aqueous component, a non-aqueous component and the emulsifier of  claim 36 . 
     
     
         50 . The emulsion of  claim 49 , wherein the emulsion exhibits increased substantivity to a negatively charged surface relative to the substantivity of an emulsion that does not contain the amino acid ester. 
     
     
         51 - 56 . (canceled)