Methods for fixing hair and skin

• US 9,095,518 B2
• Filed: 08/13/2014
• Issued: 08/04/2015
• Est. Priority Date: 08/01/2013
• Status: Active Grant

• Current Assignee: Olaplex, Inc.
• Original Assignee: Liqwd, Inc.
• Inventors: Pressly, Eric D., Hawker, Craig J.
• Primary Examiner(s): FISHER, ABIGAIL L
• Application Number:
  US14/459,012
• Publication Number:
  US 20150034117A1
• Time in Patent Office: 356 Days
• US Class Current: 1/1
• CPC Class Codes: A61K 2800/42 Colour properties
• CPC Class Codes: A61K 2800/596 Mixtures of surface active compounds
• CPC Class Codes: A61K 2800/70 Biological properties of the composition as a whole
• CPC Class Codes: A61K 2800/884 Sequential application
• CPC Class Codes: A61K 2800/94 Involves covalent bonding to the substrate
• CPC Class Codes: A61K 8/0204 Specific forms not provided for by any of groups A61K8/0208 - A61K8/14
• CPC Class Codes: A61K 8/0216 Solid or semisolid forms
• CPC Class Codes: A61K 8/22 Peroxides; Oxygen; Ozone
• CPC Class Codes: A61K 8/36 Carboxylic acids; Salts or anhydrides thereof
• CPC Class Codes: A61K 8/362 Polycarboxylic acids
• CPC Class Codes: A61K 8/365 Hydroxycarboxylic acids; Ketocarboxylic acids
• CPC Class Codes: A61K 8/40 containing nitrogen quinones containing nitrogen A61K8/355
• CPC Class Codes: A61K 8/41 Amines
• CPC Class Codes: A61K 8/447 containing sulfur
• CPC Class Codes: A61K 8/45 Derivatives containing from 2 to 10 oxyalkylene groups
• CPC Class Codes: A61K 8/46 containing sulfur A61K8/44 takes precedence
• CPC Class Codes: A61Q 19/007 Preparations for dry skin
• CPC Class Codes: A61Q 5/002 Preparations for repairing the hair, e.g. hair cure
• CPC Class Codes: A61Q 5/004 Preparations used to protect coloured hair
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: A61Q 5/04 : Preparations for permanent waving or straightening the hair
• CPC Class Codes: A61Q 5/08 : Preparations for bleaching the hair
• CPC Class Codes: A61Q 5/10 : Preparations for permanently dyeing the hair
• CPC Class Codes: A61Q 5/12 : Preparations containing hair conditioners

Abstract

Compositions, kits, and methods for repairing bonds, for example, disulfide bonds, in hair or on the skin are disclosed. The compositions provide improved conditioning benefit for dry hair or moisturize the skin. The compositions also provide a long lasting moisturized feel and smooth feel to the skin or hair, without feeling greasy. The compositions contain one or more compounds that covalently bind at least two thiol groups in the hair or on the skin. Use of the binding compositions prevents reversion of the repaired bonds to their free thiol state, for at least one week or one month, or more, after a single application of the composition. Improved methods of styling hair, for example permanent hair waving, hair curling, hair coloring or highlighting, and hair straightening, are also provided.

Claims

1. A method for treating hair, wherein the hair comprises two or more free thiol groups, comprising:

(a) applying to the hair a formulation comprising a binding agent of Formula I

2. The method of claim 1, wherein the reactive moieties and the thiol groups react to form carbon-sulfur (C—

S) covalent bonds.

3. The method of claim 1, wherein A, B, C, and D are the same.

4. The method of claim 1, wherein at least one of A, B, C, and D is different than the other reactive moieties.

5. The method of claim 1, wherein the linker is a polyfunctional molecule or polymer,

wherein the linker is optionally independently substituted with one or more substituents selected from the group consisting of hydrogen, halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy, formyl, acyl, carboxylic acid (—

COOH), —

C(O)R¹, —

C(O)OR¹, carboxylate (—

COO⁻

), primary amide (e.g., —

CONH₂), secondary amide (e.g., —

CONHR₁₁), —

C(O)NR¹R², —

NR¹R², —

NR¹S(O)₂R², —

NR¹C(O)R², —

S(O)₂R², —

SR¹, and —

S(O)₂NR¹R², sulfinyl group (e.g., —

SOR¹), and sulfonyl group (e.g., —

SOOR¹);

wherein R¹ and R² may each independently be hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl and heteroaryl;

wherein each of R¹ and R² is optionally independently substituted with one or more substituents selected from the group consisting of halogen, hydroxyl, cyano, nitro, amino, alkylamino, dialkylamino, alkyl optionally substituted with one or more halogen or alkoxy or aryloxy, aryl optionally substituted with one or more halogen or alkoxy or alkyl or trihaloalkyl, heterocycloalkyl optionally substituted with aryl or heteroaryl or ═

O or alkyl optionally substituted with hydroxyl, cycloalkyl optionally substituted with hydroxyl, heteroaryl optionally substituted with one or more halogen or alkoxy or alkyl or trihaloalkyl, haloalkyl, hydroxyalkyl, carboxy, alkoxy, aryloxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, and dialkylaminocarbonyl.

6. The method of claim 1, wherein the binding agent is:

7. The method of claim 1, wherein the formulation further comprises one or more pharmaceutically acceptable excipients,

wherein the one or more excipients are selected from the group consisting of water, surfactants, vitamins, natural extracts, preservatives, chelating agents, perfumes, preservatives, antioxidants, chelating agents, hair coloring agents, 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-fizz agents, anti-dandruff agents, and combinations thereof.

8. The method of claim 7, wherein the binding agent is present in an amount ranging from about 0.01 wt % to about 50 wt % of the formulation.

9. The method of claim 7, wherein the pharmaceutical excipient is present in an amount ranging from about 10 wt % to about 90 wt % of the formulation.

10. The method of claim 1, wherein the formulation is in the form of a gel, cream, lotion, shampoo, or conditioner.

11. The method of claim 1, wherein step (a) is repeated one or more times.

12. The method of claim 11, wherein step (a) is repeated after about 1 minutes to 20 minutes after the first application of the formulation.

13. The method of claim 1, further comprising,

(b) rinsing, shampooing, and/or conditioning the hair, wherein step (b) occurs subsequent to step (a).

14. The method of claim 13, wherein step (b) is performed within about 10 seconds or within about 30 minutes after step (a).

15. The method of claim 1, further comprising the step of:

applying a first formulation comprising a reducing agent capable of reducing the disulfide bonds in the hair to produce free thiol groups,

wherein the step is performed prior to step (a).

16. The method of claim 15, wherein the reducing agent is selected from the group consisting of thioglycolic acid and its derivative salts and esters, thiolactic acid and its derivative salts and esters, cysteine and its derivatives, cysteamine and its derivatives, inorganic sulfites, sodium metabisulfite, other inorganic bisulfites, dithiothreitol, dithioerythritol, organic phosphines, and Japanese relaxers.

17. The method of claim 1, wherein the thiols remain bound for at least one week.

18. The method of claim 1, wherein the molecular weight of the binding agent is less than about 500 Daltons.

19. The method of claim 1, further comprising prior to or simultaneous with step (a),

applying to the hair a formulation comprising a hair coloring agent and a reducing agent capable of reducing the disulfide bonds in the hair to produce free thiol groups.

20. The method of claim 19, wherein prior to step (a), the formulation comprising the hair coloring agent and the reducing agent is applied to the hair.

21. The method of claim 1, further comprising prior to or simultaneous with step (a), applying to the hair a formulation comprising a bleaching agent to lighten the hair and produce free thiol groups.

22. The method of claim 21, wherein prior to step (a), the formulation comprising the bleaching agent is applied to the hair.

23. The method of claim 1, wherein the linker is an alkyl group which is optionally substituted by one or more substituents selected from the group consisting of a halogen, cyano, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, amine, hydroxy, formyl, acyl, carboxylic acid (—

COOH), —

C(O)R¹, —

C(O)OR¹, carboxylate (—

COO⁻

), primary amide, secondary amide, —

C(O)NR¹R², —

NR¹R², —

NR¹S(O)2R², —

NR¹C(O)R², —

S(O)²R², —

SR¹, and —

S(O)₂NR¹R², sulfinyl group, and sulfonyl group;

wherein R¹ and R² may each independently be hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocycloalkyl and heteroaryl;

wherein each of R¹ and R² is optionally independently substituted with one or more substituents selected from the group consisting of halogen, hydroxyl, cyano, nitro, amino, alkylamino, dialkylamino, alkyl optionally substituted with one or more halogen or alkoxy or aryloxy, aryl optionally substituted with one or more halogen or alkoxy or alkyl or trihaloalkyl, heterocycloalkyl optionally substituted with aryl or heteroaryl or ═

O or alkyl optionally substituted with hydroxyl, cycloalkyl optionally substituted with hydroxyl, heteroaryl optionally substituted with one or more halogen or alkoxy or alkyl or trihaloalkyl, haloalkyl, hydroxyalkyl, carboxy, alkoxy, aryloxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, and dialkylaminocarbonyl.

24. The method of claim 23, wherein the alkyl group is substituted within the carbon backbone by one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur, and combinations thereof.