Hair care compositions and methods of treating hair

1. A method of treating scalp hair comprising the step of:

applying to said hair a non-toxic composition comprising a fluorinated, non-polymeric compound with a cosmetically acceptable excipient,

wherein the compound is according to one of the formulae:

wherein R 1′ is —CO 2 R B′ ; and wherein R B′ is

wherein n is an integer between 0 and 20, inclusive; and m is an even or odd integer between 1 and 6, inclusive; and

R 2′ is selected from the group consisting of hydrogen; halogen; substituted or unsubstituted cyclic C 3 -C 20 aliphatic; substituted or unsubstituted, branched or unbranched acyclic C 1 -C 20 aliphatic; substituted or unsubstituted cyclic C 3 -C 20 heteroaliphatic; substituted or unsubstituted, branched or unbranched acyclic C 1 -C 20 heteroaliphatic; substituted or unsubstituted, branched or unbranched C 1 -C 20 acyl; substituted or unsubstituted C 6 -C 14 aryl; substituted or unsubstituted heteroaryl; —OR A′ ; —C(O)R A′ ; —CO 2 R A′ ; —C(O)N(R A′ ) 2 ; —SR A′ ; —SOR A′ ; —SO 2 R A′ ; —NR A′ ; —N(R A′ ) 2 ; —NHC(O)R A′ ; and —C(R A′ ) 3 ;

wherein heteroaryl is selected from the group consisting of pyridyl, pyrazinyl, pyrimidinyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, isooxazolyl, thiadiazolyl, oxadiazolyl, thiophenyl, furanyl, quinolinyl, and isoquinolinyl,

and wherein each occurrence of R A′ is independently selected from a group consisting of hydrogen, substituted or unsubstituted cyclic C 3 -C 20 aliphatic; substituted or unsubstituted, branched or unbranched acyclic C 1 -C 20 aliphatic; substituted or unsubstituted cyclic C 3 -C 20 heteroaliphatic; substituted or unsubstituted, branched or unbranched acyclic C 1 -C 20 heteroaliphatic; substituted or unsubstituted, branched or unbranched C 1 -C 20 acyl; substituted or unsubstituted C 6 -C 14 aryl; substituted or unsubstituted heteroaryl; alkoxy; aryloxy; alkylthio; arylthio; amino; alkylamino; dialkylamino; heteroaryloxy; and heteroarylthio,

wherein heteroaryl is as defined above;

provided that the non-toxic composition and method do not employ a free radical initiator, a polymerization initiator or a polymerization catalyst.

2. The method according to claim 1 , wherein the compound is selected from the group consisting of 1H,1H,11H-eicosafluoroundecyl acrylate; 1H,1H,11H-eicosafluoroundecyl methacrylate; 2,2,3,3,4,4,5,5-octafluoropentyl methacrylate; 2,2,3,3,4,4,5,5-octafluoropentyl acrylate; 1H,1H,7H-dodecafluoroheptyl acrylate; and 1H,1H,7H-dodecafluoroheptyl methacrylate.

3. The method according to claim 1 , wherein the compound is:

4. The method according to claim 1 , wherein said method does not employ a step consisting of rinsing said hair after applying said composition.

5. 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.

6. A non-toxic hair care composition comprising

a fluorinated, non-polymeric compound and a cosmetically acceptable excipient,

wherein the compound is according to one of the formulae:

wherein R 1′ is —CO 2 R B′ ; and wherein R B′ is

wherein n is an integer between 0 and 20, inclusive; and m is an even or odd integer between 1 and 6, inclusive; and

R 2′ is selected from the group consisting of hydrogen; halogen; substituted or unsubstituted cyclic C 3 -C 20 aliphatic; substituted or unsubstituted, branched or unbranched acyclic C 1 -C 20 aliphatic; substituted or unsubstituted cyclic C 3 -C 20 heteroaliphatic; substituted or unsubstituted, branched or unbranched acyclic C 1 -C 20 heteroaliphatic; substituted or unsubstituted, branched or unbranched C 1 -C 20 acyl; substituted or unsubstituted C 6 -C 14 aryl; substituted or unsubstituted heteroaryl; —OR A′ ; —C(O)R A′ ; —CO 2 R A′ ; —C(O)N(R A′ ) 2 ; —SR A′ ; —SOR A′ ; —SO 2 R A′ ; —NR A′ ; —N(R A′ ) 2 ; —NHC(O)R A′ ; and —C(R A′ ) 3 ;

wherein heteroaryl is selected from the group consisting of pyridyl, pyrazinyl, pyrimidinyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, isooxazolyl, thiadiazolyl, oxadiazolyl, thiophenyl, furanyl, quinolinyl, and isoquinolinyl,

and wherein each occurrence of R A′ is independently selected from a group consisting of hydrogen, substituted or unsubstituted cyclic C 3 -C 20 aliphatic; substituted or unsubstituted, branched or unbranched acyclic C 1 -C 20 aliphatic; substituted or unsubstituted cyclic C 3 -C 20 heteroaliphatic; substituted or unsubstituted, branched or unbranched acyclic C 1 -C 20 heteroaliphatic; substituted or unsubstituted, branched or unbranched C 1 -C 20 acyl; substituted or unsubstituted C 6 -C 14 aryl; substituted or unsubstituted heteroaryl; alkoxy; aryloxy; alkylthio; arylthio; amino; alkylamino; dialkylamino; heteroaryloxy; and heteroarylthio,

wherein heteroaryl is as defined above;

provided that the non-toxic hair care composition does not contain a free radical initiator, a polymerization initiator or a polymerization catalyst.

7. The non-toxic hair care composition according to claim 6 , wherein the cosmetically acceptable excipient comprises a rheology modifier and a non-ionic emulsifier, wherein the rheology modifier is selected from the group consisting of gyceryl 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.

8. The non-toxic hair care composition according to claim 6 , wherein the compound is selected from the group consisting of 1H,1H,11H-eicosafluoroundecyl acrylate; 1H,1H,11H-eicosafluoroundecyl methacrylate; 2,2,3,3,4,4,5,5-octafluoropentyl methacrylate; 2,2,3,3,4,4,5,5-octafluoropentyl acrylate; 1H,1H,7H-dodecafluoroheptyl acrylate; and 1H,1H,7H-dodecafluoroheptyl methacrylate.

9. The non-toxic hair care composition according to claim 6 , wherein the compound is:

10. The method according to claim 1 , wherein hair treated with the composition resists moisture penetration, characterized by at least 4 percent decreased moisture flux as measured according to DVS Protocol I.

11. The method according to claim 1 , wherein hair treated with the composition resists dirt, characterized by no more than 15 percent weight gain when subjected to Starch Test I.

12. The method according to claim 1 , wherein the composition has at least 50% weight loss when subjected to Weightless Test I.

13. The method according to claim 1 , wherein said composition is an aerosol spray, a hair spray, non-aerosol spray, pumpable hair spray, serum, wax, emulsion, suspension, lotion, mousse, solution, gel, pomade, cream, conditioner, or shampoo.

14. A method of treating scalp hair comprising the step of applying to said hair a non-toxic composition comprising a fluorinated, non-polymeric compound and a cosmetically acceptable excipient, 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;

2,2,3,3,4,4-hexafluoro-1,5-pentyl diacrylate; and

2,2,3,3,4,4-hexafluoro-1,5-pentyl dimethacrylate;

provided that the composition and method do not employ a free radical initiator, a polymerization initiator or a polymerization catalyst.

15. The non-toxic hair care composition according to claim 6 , wherein the composition is an aerosol spray, a hair spray, non-aerosol spray, pumpable hair spray, serum, wax, emulsion, suspension, lotion, mousse, solution, gel, pomade, cream, conditioner, or shampoo.

16. A non-toxic hair care composition comprising a fluorinated, non-polymeric compound and a cosmetically acceptable excipient, 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;

2,2,3,3,4,4-hexafluoro-1,5-pentyl diacrylate; and

2,2,3,3,4,4-hexafluoro-1,5-pentyl dimethacrylate;

provided that the composition does not contain a free radical initiator, a polymerization initiator or a polymerization catalyst.

17. The method according to claim 1 , wherein hair treated with the composition has at least 4% decreased moisture flux as measured according to DVS Protocol I and no more than 15% weight gain when subjected to Starch Test I.

18. The method according to claim 1 , wherein hair treated with the composition has at least 4% decreased moisture flux as measured according to DVS Protocol I and no more than 15% weight gain when subjected to Starch Test I and the composition has at least 50% weight loss when subjected to Weightless Test I.

19. The non-toxic hair care composition according to claim 6 , wherein the cosmetically acceptable excipient is selected from the group consisting of alcohol, PEG-40 Hydrogenated Castor Oil, Fragrance, VP/Vinyl Caprolactam/DMAPA Acrylates Copolymer, PVP/VA, Cetrimonium chloride, PPG-2 Myristyl Ether Propionate, Glycereth-7, Polysorbate 80, Isohexadecane, Acrylamide/Sodium Acryloyldimethyltaurate Copolymer, Phenoxyethanol, Methylparaben, Propylparaben, Polysorbate 20, Polyacrylate-13, Polyisobutene, Ethylhexyl Stearate, Caprylyl Glycol, Sorbic acid, Cetyl alcohol, Cetearyl alcohol, Glyceryl Stearate, Ceteareth-20, Stearyl alcohol, Laureth-23, Laureth-4, Behenyl alcohol, Ceteth-10, PEG-40 Stearate, Hydroxypropyltrimonium Hydrolyzed Corn Starch, PPG-3 Benzyl Ether Myristate, Carbomer, Triethanolamine, Behentrimonium Chloride, PPG-2 Myristyl Propionate, VP/Acrylates/Lauryl Methacrylate Copolymer, Polyquaternium-28, Sodium Polyactylate, Preservative, PEG-4M, Steareth-21, Steareth-20, C10-40 Isoalkylamidopropyl Ethyldimonium Ethosulfate, Cosmetic Fluid CF-76 Cosmetic fluid CF-61, Oleic acid, Sorbitan Oleate, Glyceryl Polyacrylate, Glycerin, Phenoxyethanol, Methylisothiazolinone, Paraffin blend, Acrylic Acid/VP Crosspolymer, Aminomethyl Propanol, SiClone SR-5, Myristyl alcohol, VP/Dimethylaminoethyl Methacrylate Copolymer, PEG-100 Stearate, PEG-40 Stearate, Polyacrylate-13, Acrylamide/Sodium Acryloyldimethyltaurate Copolymer, Isohexadecane, Polyisobutene, Linoleum Acid, Oleth-20, Oleth-2, PEG-8 Beeswax, Capric/Caprylic Triglyceride, Polyquaternium-46, PVP, Cocamidopropylbetaine, Lauramide Oxide, Trideceth-12, PEG-8 Stearate, Fatty acid, Hydroxyethylcellulose, Xanthan Gum, PEG-150 Distearate, Sarcosinate Acid, Glyceryl Oleate, PEG-90M, Hydroxypropylcellulose, PEG-24M, Denatured alcohol, C 10-40 Isoalkylamidopropyl ethyldimonium Ethosulfate, Dipropylene Glycol, Octyl Stearate, VP/VA Copolymer, Cocamidopropylamine Oxide, Cocamidopropyl Betaine, Sodium Lauroyl Sarcosinate, PG-Hydroxyethyl Cellulose Cocodimonium Chloride, PEG-150 Pentaerythrityl Tetrastearate, PEG-6 Caprylic/Capric Glycerides, Polyquaternium-70, Hydrolyzed Wheat Protein, and Citric acid.

20. The method according to claim 1 , wherein n is an integer between 1 and 20, inclusive.

21. The method according to claim 1 , wherein n is an integer between 1 and 20, inclusive; and m is 1.

22. The non-toxic hair care composition according to claim 6 , wherein n is an integer between 1 and 20, inclusive.

23. The non-toxic hair care composition according to claim 6 , wherein n is an integer between 1 and 20, inclusive; and m is 1.