Keratin treatment formulations and methods

Abstract

Formulations, kits, and methods for rebuilding the disulfide bonds in keratin found in hair, skin, or nails. Hair that is damaged due to a hair coloring treatment and/or other reducing treatment, such as during a permanent wave, can be treated with the formulations containing one or more active agents. The formulations may be applied subsequent to a hair coloring treatment or simultaneously with a hair coloring treatment. Use of the active agent formulations during a permanent wave treatment prevents the reversion of the hair to its previous state, for at least one week, preferably at least three months, more preferably at least one year, most preferably greater than one year, after one or more than one application of the formulation. Application of the active agent formulation to skin or nails can help repair damaged disulfide bonds due to natural wear and tear or natural aging.

1 - 29 . (canceled) 
     
     
         30 . A method of treating hair, the method comprising the steps of:
 (i) applying a first formulation comprising a reducing agent to hair; and   (ii) applying a second formulation comprising an active agent to the hair, wherein the active agent has the formula:   
       
         
           
           
               
               
           
         
         wherein Z is a linker or is absent; 
         m and n are each an integer independently selected from 1-6, and the sum of m+n is equal to or greater than 2; 
         B is a functional group capable of forming a covalent bond with a nucleophile; and 
         A is an ionizable functional group. 
       
     
     
         31 . The method of  claim 30 , wherein method of treating hair is a hair waving and/or hair curling method and the method further includes a step of setting the hair on rods. 
     
     
         32 . The method of  claim 30 , wherein method of treating is a hair straightening method. 
     
     
         33 . The method of  claim 30 , wherein B is independently selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       wherein R is independently selected from the group consisting of hydrogen, C 1-6  alkyl groups, aryl groups, or an ionizable functional groups; Z′ is oxygen (O), NH or is absent, and G is carbon (C) and g is 1, or G is sulfur (S) and g is 2; and
 A is independently selected from the group consisting of: —COOH, —SO 3 H, —PO 3 H 2 , —N(R 1 ) 2 , —N(R 1 ) 3 ; wherein R 1  is independently selected from the group consisting of a hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl and heteroaryl groups; wherein each R 1  is independently unsubstituted or substituted with one or more substituents. 
 
     
     
         34 . The method of  claim 30 , wherein the linker Z is an alkyl group, alkenyl group, cycloalkyl group, cycloalkenyl group, aryl group, heterocycloalkyl group, or heteroaryl group,
 wherein the alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, or heteroaryl group, is unsubstituted or substituted one or more times by a halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy, oxo, formyl, acyl, carboxylic acid, —C(O)R 1 , —C(O)OR 1 , —COO − , primary amide, secondary amide, —C(O)NR 1 R 2 , —NR 1 R 2 , —NR 1 S(O) 2 R 2 , —NR 1 C(O)R 2 , —S(O) 2 R 2  , —S(O) 2 NR 1 R 2 , —SOR 1 , or —SOOR 1 ;   wherein R 1  and R 2  are each independently selected from the group consisting of a hydrogen, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group, heterocycloalkyl , and heteroaryl group, wherein each of R 1  and R 2  is independently unsubstituted or substituted with one or more substituents.   
     
     
         35 . The method of  claim 30 , wherein the active agent is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         36 . The method of  claim 30 , wherein the active agent is present in an amount ranging from about 1 wt % to about 10 wt % of the second formulation, optionally from about 0.5 to 3 wt % of the second formulation. 
     
     
         37 . The method of  claim 30 , wherein the reducing agent is selected from the group consisting of thioglycolic acid, thiolactic acid, dihydrolipoate, thioglycerol, mercaptopropionic acid, sodium bisulfite, ammonium bisulfide, zinc formaldehyde sulfoxylate, sodium formaldehyde sulfoxylate, sodium metabisulfite, potassium borohydride, pegylated thiols, and hydroquinone. 
     
     
         38 . The method of  claim 30 , further comprising:
 (iii) applying an aqueous oxidizing solution comprising hydrogen peroxide to the hair, wherein step (iii) occurs subsequent to steps (i) and (ii).   
     
     
         39 . The method of  claim 30 , wherein the second formulation further comprises one or more cosmetically acceptable excipients selected from the group consisting of water, surfactants, vitamins, natural extracts, preservatives, chelating agents, perfumes, preservatives, antioxidants, proteins, amino acids, humectants, fragrances, emollients, penetrants, thickeners, viscosity modifiers, hair fixatives, film formers, emulsifiers, opacifying agents, propellants, liquid vehicles, carriers, salts, pH adjusting agents, neutralizing agents, buffers, hair conditioning agents, anti-static agents, anti-frizz agents, anti-dandruff agents, and combinations thereof. 
     
     
         40 . The method of  claim 39 , wherein the one or more cosmetically acceptable excipients are present in an amount ranging from about 40 wt % to about 99 wt % of the second formulation. 
     
     
         41 . The method of  claim 30 , wherein following step (ii) breakage of the hair is decreased by at least about 5%, 10%, 20%, 40%, or 50%, as compared to the hair of an individual treated with the second formulation in the absence of the active agent. 
     
     
         42 . A hair spray comprising a hair repair formulation,
 the hair repair formulation comprising:
 an active agent having the formula: 
   
       
         
           
           
               
               
           
         
         
           wherein Z is a linker or is absent; 
           m and n are each an integer independently selected from 1-6, and the sum of m+n is equal to or greater than 2; 
           B is a functional group capable of forming a covalent bond with a nucleophile; 
           A is an ionizable functional group; 
         
         a cosmetically acceptable carrier; and 
         an optional propellant. 
       
     
     
         43 . The hair spray of  claim 42 , wherein the cosmetically acceptable carrier is water or a mixture of water and an alcohol. 
     
     
         44 . The hair spray of  claim 42 , wherein the hair repair formulation comprises an antioxidant, fragrance, preservative, sunscreen agent, anti-static agent, vitamin, protein, peptide, plant extract, humectant, oil, emollient, lubricant, thickener, hair conditioning agent, polymer, and/or surfactant. 
     
     
         45 . The hair spray of  claim 42 , wherein the propellant is present and selected from the group consisting of a liquefiable gas propellant, a halogenated propellant, a dimethyl ether propellant, a hydrocarbon propellant (such as propane, n-butane, iso-butane), CFC-replacement propellants, compressed air, and combinations thereof. 
     
     
         46 . The hair spray of  claim 42 , wherein B is independently selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein R is independently selected from the group consisting of hydrogen, C 1-6  alkyl groups, aryl groups, or an ionizable functional groups; Z′ is oxygen (O), NH or is absent, and G is carbon (C) and g is 1, or G is sulfur (S) and g is 2; and 
         A is independently selected from the group consisting of: —COOH, —SO 3 H, —PO 3 H 2 , —N(R 1 ) 2 , —N(R 1 ) 3 ; wherein R 1  is independently selected from the group consisting of a hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl and heteroaryl groups; wherein each R 1  is independently unsubstituted or substituted with one or more substituents. 
       
     
     
         47 . The hair spray of  claim 42 , wherein the linker Z is an alkyl group, alkenyl group, cycloalkyl group, cycloalkenyl group, aryl group, heterocycloalkyl group, or heteroaryl group,
 wherein the alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, or heteroaryl group, is unsubstituted or substituted one or more times by a halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy, oxo, formyl, acyl, carboxylic acid, —C(O)R 1 , —C(O)OR 1 , —COO − , primary amide, secondary amide, —C(O)NR 1 R 2 , —NR 1 R 2 , —NR 1 S(O) 2 R 2 , —NR 1 C(O)R 2 , —S(O) 2 R 2  , —S(O) 2 NR 1 R 2 , —SOR 1 , or —SOOR 1 ;   wherein R 1  and R 2  are each independently selected from the group consisting of a hydrogen, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group, heterocycloalkyl , and heteroaryl group, wherein each of R 1  and R 2  is independently unsubstituted or substituted with one or more substituents.   
     
     
         48 . The hair spray of  claim 41 , wherein the active agent is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         49 . A hair coloring kit comprising:
 (a) a first formulation comprising a hair coloring agent and a reducing agent capable of reducing disulfide bonds in hair to produce free thiol groups, and   (b) a second formulation comprising an active agent, wherein the active agent has the formula:   
       
         
           
           
               
               
           
         
         wherein Z is a linker or is absent; 
         m and n are each an integer independently selected from 1-6, and wherein the sum of m+n is equal to or greater than 2; 
         B is a functional group capable of forming a covalent bond with a nucleophile; and 
         A is an ionizable functional group.