Hair care compositions and methods of treating hair

Abstract

The present invention provides compositions, kits and methods for treating scalp hair. The compositions include fluorinated (but not perfluorinated), non-polymeric compounds in a suitable excipient to provide beneficial effects on hair.

What is claimed is: 
     
         1 . A method of treating scalp hair comprising the step of:
 applying to said hair a non-toxic composition comprising a non-perfluorinated, non-polymeric compound of formula (I) with a cosmetically acceptable excipient   
       
         
           
           
               
               
           
         
         wherein X is selected from the group consisting of CH 2 , CHCH 3 , and CCH 3 CH 3    
         wherein R 1  and R 2  are independently selected from the group consisting of: hydrogen; cyclic or acyclic C 1 -C 20  aliphatic; cyclic or acyclic C 1 -C 20  heteroaliphatic; cyclic or acyclic C 1 -C 20  acyl; C 1 -C 20  aryl; C 1 -C 20  heteroaryl; —OC(═O)R, wherein R is an alkenyl radical; —COOR A ; —C(═O)R A ; —OH; —NR B R C , and —CONR B R C , wherein R A , R B  and R C  are independently selected from the group consisting of: hydrogen; cyclic or acyclic C 1 -C 20  aliphatic; cyclic or acyclic C 1 -C 20  heteroaliphatic; cyclic or acyclic C 1 -C 20  acyl; C 1 -C 20  aryl; and C 1 -C 20  heteroaryl, which groups may be substituted or unsubstituted, and 
         wherein R 1  and R 2  may be substituted or unsubstituted, provided that R 1  and R 2  taken together contain at least three carbon atoms; R 1  and R 2  taken together are substituted with a total of at least four fluorine atoms; and R 1  and R 2  taken together contain no more than one aromatic ring structure; provided that the compound of formula (I) does not contain an Si—O bond; is not a polyether, a fluorinated acid, an oxyacetamide, or a carbonate. 
       
     
     
         2 . The method according to  claim 1 , wherein at least one of R 1  and R 2  is substituted with at least one of —COOR A , —C(═O)R A , —OH, —NR B R C  or —CONR B R C ,
 wherein R A , R B  and R C  are independently selected from the group consisting of: hydrogen; cyclic or acyclic C 1 -C 20  aliphatic; cyclic or acyclic C 1 -C 20  heteroaliphatic; cyclic or acyclic C 1 -C 20  acyl; C 1 -C 20  aryl; and C 1 -C 20  heteroaryl, which groups may be substituted or unsubstituted. 
 
     
     
         3 . The method according to  claim 1 , wherein the compound is a compound according to formula (II): 
       
         
           
           
               
               
           
         
         wherein R 11  is hydrogen or methyl optionally substituted with up to two fluorine atoms; and 
         R 12  is a methylene containing radical selected from the group consisting of: cyclic or acyclic C 1 -C 20  aliphatic; cyclic or acyclic C 1 -C 20  heteroaliphatic; cyclic or acyclic C 1 -C 20  acyl; C 1 -C 20  aryl; and C 1 -C 20  heteroaryl. 
       
     
     
         4 . The method according to  claim 1 , wherein the compound is selected from the group consisting of 2,2,3,3,4,4,5,5-octafluoro-1,6-hexyl dimethacrylate; 2,2,3,3,4,4,5,5-octafluoro-1,6-hexyl diacrylate; 1H,1H,11H-eicosafluoroundecyl acrylate; 1H,1H,11H-eicosafluoroundecyl methacrylate; 2,2,3,3,4,4,5,5-octafluoro-1,6-hexyldiacrylate; 2,2,3,3,4,4,5,5-octafluoro-1,6-hexyldimethacrylate; 2,2,3,3,4,4,5,5-octafluoropentyl methacrylate; 2,2,3,3,4,4,5,5-octafluoropentyl acrylate; 2,2,3,3,4,4-hexafluoro-1,5-pentyl diacrylate; 2,2,3,3,4,4-hexafluoro-1,5-pentyl dimethacrylate; 1H,1H,7H-dodecafluoroheptyl acrylate; and 1H,1H,7H-dodecafluoroheptyl methacrylate. 
     
     
         5 . The method according to  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         6 . The method according to  claim 1 , wherein the compound does not substantially polymerize on the hair. 
     
     
         7 . The method according to  claim 1 , wherein said method does not employ a step consisting of rinsing said hair after applying said composition. 
     
     
         8 . The method according to  claim 1 , wherein the method does not further employ a step of (i) applying a composition containing more than about 0.1% weight/weight of a uv-activated free radical initiator that is activated under ambient light, or (ii) applying a composition containing more than about 0.01% weight/weight of a free radical initiator selected from the group consisting of a heat-activated initiator that is activated at or above ambient temperature and an initiator that is active at ambient temperature. 
     
     
         9 . A non-toxic hair care composition comprising
 a non-perfluorinated, non-polymeric compound of formula (I) and an excipient comprising a rheology modifier and a non-ionic emulsifier,   
       
         
           
           
               
               
           
         
         wherein X is selected from the group consisting of CH 2 , CHCH 3 , and CCH 3 CH 3    
         wherein R 1  and R 2  are independently selected from the group consisting of: hydrogen; cyclic or acyclic C 1 -C 20  aliphatic; cyclic or acyclic C 1 -C 20  heteroaliphatic; cyclic or acyclic C 1 -C 20  acyl; C 1 -C 20  aryl; C 1 -C 20  heteroaryl; —OC(═O)R, wherein R is an alkenyl radical; —COOR A ; —C(═O)R A ; —OH; —NR B R C ; and —CONR B R C , wherein R A , R B  and R C  are independently selected from the group consisting of: hydrogen; cyclic or acyclic C 1 -C 20  aliphatic; cyclic or acyclic C 1 -C 20  heteroaliphatic; cyclic or acyclic C 1 -C 20  acyl; C 1 -C 20  aryl; and C 1 -C 20  heteroaryl, which groups may be substituted or unsubstituted, and 
         wherein R 1  and R 2  may be substituted or unsubstituted, provided that R 1  and R 2  taken together contain at least three carbon atoms; R 1  and R 2  taken together are substituted with a total of at least four fluorine atoms; and R 1  and R 2  taken together contain no more than one aromatic ring structure; provided that the compound of formula (I) does not contain an Si—O bond; is not a polyether, a fluorinated acid, an oxyacetamide, or a carbonate. 
       
     
     
         10 . The hair care composition according to  claim 9 , wherein at least one of R 1  and R 2  is substituted with at least one of —COOR A , —C(═O)R A , —OH, —NR B R C  or —CONR B R C ;
 wherein R A , R B  and R C  are independently selected from the group consisting of: hydrogen; cyclic or acyclic C 1 -C 20  aliphatic; cyclic or acyclic C 1 -C 20  heteroaliphatic; cyclic or acyclic C 1 -C 20  acyl; C 1 -C 20  aryl; and C 1 -C 20  heteroaryl, which groups may be substituted or unsubstituted. 
 
     
     
         11 . The hair care composition according to  claim 9 , wherein the rheology modifier is selected from the group consisting of glyceryl polyacrylate, sodium polyacrylate, carbomer, acrylates copolymer, acrylic acid/vp crosspolymer, and xanthan gum; and the non-ionic emulsifier is selected from the group consisting of Laureth-23, Ocyldodeceth-20, Oleth-10, Peg-40 Hydrogenated Castor Oil, Polaxomer 127, Polysorbate 20, and Ceteareth-20. 
     
     
         12 . The hair care composition according to  claim 9 , wherein the compound is a compound according to formula (II): 
       
         
           
           
               
               
           
         
         wherein R 11  is hydrogen or methyl optionally substituted with up to two fluorine atoms; and 
         R 12  is a methylene containing radical selected from the group consisting of: cyclic or acyclic C 1 -C 20  aliphatic; cyclic or acyclic C 1 -C 20  heteroaliphatic; cyclic or acyclic C 1 -C 20  acyl; C 1 -C 20  aryl; and C 1 -C 20  heteroaryl; 
         and wherein the compound does not substantially polymerize on the hair. 
       
     
     
         13 . The hair care composition according to  claim 9 , wherein the compound is selected from the group consisting of 2,2,3,3,4,4,5,5-octafluoro-1,6-hexyl dimethacrylate; 2,2,3,3,4,4,5,5-octafluoro-1,6-hexyl diacrylate; 1H,1H,11H-eicosafluoroundecyl acrylate; 1H,1H,11H-eicosafluoroundecyl methacrylate; 2,2,3,3,4,4,5,5-octafluoro-1,6-hexyldiacrylate; 2,2,3,3,4,4,5,5-octafluoro-1,6-hexyldimethacrylate; 2,2,3,3,4,4,5,5-octafluoropentyl methacrylate; 2,2,3,3,4,4,5,5-octafluoropentyl acrylate; 2,2,3,3,4,4-hexafluoro-1,5-pentyl diacrylate; 2,2,3,3,4,4-hexafluoro-1,5-pentyl dimethacrylate; 1H,1H,7H-dodecafluoroheptyl acrylate; and 1H,1H,7H-dodecafluoroheptyl methacrylate. 
     
     
         14 . The hair care composition according to  claim 9 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         15 . A method according to  claim 1 , wherein hair treated with the composition resists moisture penetration, characterized by at least 4 percent decreased moisture flux. 
     
     
         16 . A method according to  claim 1 , wherein hair treated with the composition resists dirt, characterized by no more than 15 percent weight gain. 
     
     
         17 . A method according to  claim 1 , wherein hair treated with the composition results affords a weightless feeling on the hair, characterized by at least 50% weight loss.