Hair Color Smoothing Compositions and Methods

• US 20150034119A1
• Filed: 04/21/2014
• Published: 02/05/2015
• Est. Priority Date: 08/01/2013
• Status: Abandoned Application

• Current Assignee: Liqwd, Inc.
• Original Assignee: Liqwd, Inc.
• Inventors: Hawker, Craig J., Pressly, Eric D.
• Application Number:
  US14/257,089
• Publication Number:
  US 20150034119A1
• Time in Patent Office: Days
• US Class Current: 132/286
• CPC Class Codes: A61K 2800/882 Mixing prior to application
• CPC Class Codes: A61K 2800/884 Sequential application
• CPC Class Codes: A61K 2800/94 Involves covalent bonding to the substrate
• CPC Class Codes: A61K 8/22 Peroxides; Oxygen; Ozone
• CPC Class Codes: A61K 8/4913 having five membered rings, e.g. pyrrolidone carboxylic acid
• 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 5/08 Preparations for bleaching the hair
• CPC Class Codes: A61Q 5/10 Preparations for permanently dyeing the hair

Abstract

Compositions, kits, and methods for rebuilding the disulfide bonds in hair that is damaged due to a hair coloring treatment are disclosed. The compositions contain one or more compounds that covalently crosslink at least two thiol groups in the hair. The compositions may be applied subsequent to a hair coloring treatment or simultaneously with a hair coloring treatment. Under normal hair washing conditions, the covalent crosslinks formed are not succeptable to reduction or hydrolysis. Use of the crosslinking compositions prevent the reversion of the hair'"'"'s disulfide bonds to its reduced state, for at least one week, preferably at least three months, more preferably at least one year, most preferably at least greater than one year, after at least one application of the composition.

Claims

1. A method for coloring hair comprising:

(a) applying a first formulation comprising a hair coloring agent and a reducing agent capable of reducing the disulfide bonds in the hair to produce reduced thiol groups,

(b) applying to the hair a second formulation comprising a crosslinking agent in an effective amount to covalently crosslink the reduced thiol groups,

wherein the crosslinking agent comprises at least two reactive moieties connected through a linker, capable of reacting with the reduced thiol groups.

2. The method of claim 1, wherein steps (a) and (b) are performed simultaneously.

3. The method of claim 1, wherein steps (a) and (b) are performed sequentially, with step (a) performed prior to step (b).

4. The method of claim 2, wherein prior to step (a), the first formulation and the second formulation are mixed together.

5. The method of claim 1, wherein the crosslinking agent is represented by Formula I:

6. The method of claim 1, wherein the crosslinking agent is a polymer, wherein the linker forms the polymer backbone, and wherein the reactive moieties are covalently attached to the linker.

7. The method of claim 5, wherein each of A, B, C, and D is independently selected from the group consisting of a Michael acceptor, a succinimidyl-containing group, a maleimido-containing group, azlactone, a benzoxazinone derivative, vinyl sulfone, vinyl sulfoximine, banzoxazinonc, isocyanate, epoxide, an electrophilic moiety containing a leaving group, an electrophilic thiol acceptor, acrylate group, a methacrylate group, a styrene group, an acryl amide group, a methacryl amide group, a maleate group, a fumarate group, an itaconate group, a vinyl ether group, an allyl ether group, an allyl ester group, and a vinyl ester group.

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

S) covalent bonds.

9. The method of claim 5, wherein A, B, C, and D are the same.

10. The method of claim 5, wherein at least one of A, B, C, and D is different than the other reactive moieties.

11. The method of claim 5, wherein the crosslinking agent has a chemical structure selected from the group consisting of:

12. The method of claim 1, wherein the linker is selected from the group consisting of oxygen, sulfur, carbon, boron, nitrogen, alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, heteroaryl, ether, amine, and a polymer,

wherein the linker is optionally independently substituted with one or more substituents including 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., —

SOR₁₁), and sulfonyl group (e.g., —

SOOR₁₁);

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.

13. The method of claim 12, wherein the linker is selected from the group consisting of alkoxy, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, amine, heterocycloalkyl, and heteroaryl.

14. The method of claim 2, wherein the crosslinking agent is:

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

wherein the one or more excipients are 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.

16. The method of claim 15, wherein the crosslinking agent is present in an amount ranging from about 0.01 wt % to about 50 wt % of the second formulation, preferably from about 0.01 wt % to about 10 wt % of the second formulation.

17. The method of claim 16, wherein the crosslinking agent is present in an amount ranging from about 2.5 to 3 wt % of the second formulation.

18. The method of claim 15, wherein the pharmaceutical excipient is present in an amount ranging from about 10 wt % to about 99.99 wt % of the second formulation, preferably from about 50 wt % to about 90 wt % of the second formulation.

19. The method of claim 13, wherein the second formulation is in the form of a gel, cream, lotion, shampoo, or conditioner.

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

21. The method of claim 1, further comprising,

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

22. The method of claim 21, wherein step (c) is performed within about 10 seconds to about 30 minutes, preferably between about 1 minute and about 20 minutes, more preferably about 10 minutes after step (b).

23. The method of claim 1, wherein the coloring agent is selected from the group consisting of highlighting agents, permanent coloring agents, demi-permanent coloring agents, and semi-permanent coloring agents.

24. A kit comprising:

(a) a first formulation comprising a hair coloring agent and a reducing agent capable of reducing disulfide bonds in hair to produce reduced thiol groups, and

(b) a second formulation comprising a crosslinking agent in an effective amount to covalently crosslink reduced thiol groups in hair,

wherein the crosslinking agent comprises at least two reactive moieties capable of reacting with a thiol and optionally a linker that links the reactive moieties.

25. The kit of claim 24, further comprising a shampoo, a conditioner, instructions for use, a developer, gloves, or a combination thereof.

26. The kit of claim 24, wherein the crosslinking agent is represented by Formula I:

27. The kit of claim 24, wherein the crosslinking agent is a polymer, wherein the linker forms the polymer backbone, and wherein the reactive moieties are covalently attached to the linker.

28. The kit of claim 26, wherein each of A, B, C, and D is independently selected from the group consisting of a Michael acceptor, a succinimidyl-containing group, a maleimido-containing group, azlactone, a benzoxazinone derivative, vinyl sulfone, vinyl sulfoximine, banzoxazinone, isocyanate, epoxide, an electrophilic moiety containing a leaving group, an electrophilic thiol acceptor, acrylate group, a methacrylate group, a styrene group, an acryl amide group, a methacryl amide group, a maleate group, a fumarate group, an itaconate group, a vinyl ether group, an allyl ether group, an allyl ester group, and a vinyl ester group.

29. The kit of claim 24, wherein the reactive moieties and the thiol groups react to form carbon-sulfur (C—

S) covalent bonds.

30. The kit of claim 26, wherein the crosslinking agent has a chemical structure selected from the group consisting of: