METHOD FOR THE TREATMENT AND/OR PREVENTION OF DAMAGED KERATIN

Abstract

A method is described for the treatment and/or prevention of damaged keratin in a keratin-containing tissue, comprising the steps of: applying on the keratin-containing tissue a cosmetic composition comprising molecules carrying at least one light reactive functional group, and at least one photoinitiator; and leaving to process with exposure of the keratin-containing tissue to light, the light being of a wavelength suitable for activating said at least one photoinitiator. A cosmetic composition is also described comprising molecules carrying at least one light reactive functional group and at least one photoinitiator; and its use.

Claims

1-26. (canceled)

27. A method for treating and/or preventing damaged keratin in a keratin-comprising tissue, the method comprising: a) applying on the keratin-comprising tissue a cosmetic composition comprising a first molecule comprising a light-reactive functional group, and a photoinitiator; and b) allowing exposure of the keratin-comprising tissue to light, the light being of a wavelength suitable for activating the photoinitiator.

28. The method of claim 27, wherein the keratin-comprising tissue comprises human hair, animal hair, human skin, animal skin, and/or human nails.

29. The method of claim 27, wherein the keratin-comprising tissue comprises human hair and/or animal hair.

30. The method of claim 27, wherein the keratin-comprising tissue comprises human scalp hair.

31. The method of claim 27, wherein the light-reactive functional group comprises an acrylate, methacrylate, vinyl benzene, alkyne, or combination of two or more of any of these.

32. The method of claim 27, wherein the first molecule is obtained by a process comprising functionalizing an aminoacid, saccharide, fatty acid, residue thereof, or a combination of two or more of any of these.

33. The method of claim 27, wherein the first molecule is obtained by a process comprising functionalizing a synthetic polymer.

34. The method of claim 27, wherein, in the cosmetic composition in the applying a), the first molecule is present in a concentration, in weight percent based on a volume of the cosmetic composition, of at least 0.01% (w/v).

35. The method of claim 27, wherein, in the cosmetic composition in the applying a), the first molecule is present in a concentration in a range of from 0.05 to 20% (w/v).

36. The method of claim 27, wherein, in the cosmetic composition in the applying a), the first molecule is present in a concentration in a range of from 0.1 to 15% (w/v).

37. The method of claim 27, wherein, in the cosmetic composition in the applying a), the first molecule is present in a concentration in a range of from 0.5 to 10% (w/v).

38. The method of claim 27, wherein the photoinitiator is activated at a wavelength in a range of from 10 nm to 100 μm.

39. The method of claim 27, wherein the photoinitiator is activated at a wavelength in a range of from 300 to 1400 nm.

40. The method of claim 27, wherein the photoinitiator is activated at a wavelength in a range of from 360 to 800 nm.

41. The method of claim 27, wherein the photoinitiator is activated at a wavelength in a range of from 360 to 400 nm.

42. The method of claim 27, wherein the cosmetic composition further comprises: a coloring agent.

43. The method of claim 42, wherein the coloring agent is capable of emitting light when exposed to radiation having a wavelength in a range of from 10 nm and 100 μm.

44. The method of claim 27, wherein the cosmetic composition further comprises: a pigment, a dye, or a combination of two or more of any of these.

45. A cosmetic composition, comprising: a molecule comprising a light-reactive functional group; and a photoinitiator.

46. A kit of parts suitable for treating and/or preventing damaged keratin in human or animal hair, the kit comprising: a first formulation comprising a first form of the cosmetic composition of claim 45; and a second formulation comprising a second form of the cosmetic composition, different from the first form.

Description

BRIEF DESCRIPTION OF THE FIGURES

[0183] FIG. 1 is a schematic representation of keratin filaments of hair. FIG. 1a shows the effect of keratin damage on the disulphide bonds between keratin filaments. FIG. 1b shows the effect of the method of the present invention on damaged keratin where the functional groups on the reactive molecules are acrylates or methacrylates. FIG. 1c shows the effect of the method of the present invention on damaged keratin where the functional groups on the reactive molecules are alkynes.

[0184] FIG. 2 shows electron microscopic images of DTT damaged hair (2a) and repaired hair following the treatment method of the invention (2b).

[0185] FIG. 3 shows two photographs comparing a volunteer's hair before (3a) and after (3b) treatment with the method of the invention.

[0186] FIG. 4 shows a photograph of hair irradiated with UV light following application of the cosmetic composition in the treatment of the invention, wherein the composition contains a fluorescent dye.

DETAILED DESCRIPTION OF THE INVENTION

[0187] The present invention will be further described making reference to the examples provided hereafter by way of illustrative and non-limiting cases.

Example 1

Preparation of a Composition Comprising Methacrylate-Functionalised Gelatin.

[0188] 20% w/v fish gelatin (Weishardt International, France) was dissolved in distilled water to 500 ml at 55° C. The pH was adjusted to 8.5-9 using 3N Sodium Hydroxide (Sigma). Methacrylic anhydride (MAA, obtained from Sigma-Aldrich (Sweden) was added to the solution, with continuous vigorous stirring, in 3 molar excess with respect to gelatin lysine side groups (i.e. at a ratio of 1:3 of the mole percent of gelatin lysines to methacrylic anhydride) without altering the pH and the temperature to obtain the functionalisation of the gelatin with methacrylic groups on the side chains. After 1 hour of reaction, the mixture was dialysed against water (pH >8-9) for 24 hours using Dialysis Membranes (MWCO 12000-14000 kD) obtained from Spectrum Laboratories, Inc. (CA, US) at room temperature (about 25° C.), to remove any unreacted methacrylic anhydride and other side products of the reaction.

[0189] The reaction product was then freeze-dried. The degree of substitution (DS) was determined by NMR. Analyses by NMR showed a higher than 50% modification of the gelatin. In other words, more than 50% lysine amines had been replaced with methacrylate groups.

Example 2

Preparation of a Composition Comprising Acrylate-Functionalised Gelatin.

[0190] The method of Example 1 was carried out by replacing methacrylic anhydride with acrylic anhydride (MP Biomedicals, USA). Analyses by NMR showed more than 55% modification of the gelatin.

Example 3

Preparation of a Composition Comprising Glycidyl Methacrylate-Functionalised Gelatin.

[0191] The method of Example 1 was carried out by replacing methacrylic anhydride with glycidyl methacrylate (Sigma-Aldrich, Sweden)) where the pH of the solution was adjusted to 3.5-4 using 1M HCl. After this, 6 mL of glycidyl methacrylate was added into the solution dropwise. The reaction was conducted at 50° C. for 24 h and the product was purified by dialysis against Milli-Q water (Millipore Corporation, Darmstadt, Germany) with the above-mentioned dialysis membrane at 40° C. for five days. Analyses by NMR showed more than 40% modification of the gelatin.

Example 4

Preparation of a Composition Comprising Vinyl Benzene-Functionalised Gelatin.

[0192] The method of Example 1 was carried out by replacing methacrylic anhydride with 4-vinyl benzene chloride (VBC) (Sigma-Aldrich, Sweden) solubilised in 0.5M hydrochloric acid and the solution pH was neutralized to pH 7.4-8 before adding VBC in molar excess at a molar ratio of 1:5 with respect to the lysine amines in gelatin (i.e. at a ratio of 1:5 of the mole percent of gelatin lysines to VBC). The reaction was conducted at 50° C. for 24 h and the product was purified by dialysis against Milli-Q water (Millipore Corporation, Darmstadt, Germany) with the above-mentioned dialysis membrane at 40° C. for five days. Analyses by NMR showed a >30% modification of the gelatin.

Example 5

Preparation of a Composition Comprising Alkyne-Functionalised Gelatin.

[0193] The method of Example 1 was carried out by replacing methacrylic anhydride with propargyl N-hydroxysuccimide ester (Sigma-Aldrich, Sweden), solubilised in minimal quantity dimethyl sulfoxide (DMSO) (Sigma), in molar excess at a 1:5 molar ratio with respect to the mole percent of lysine amine groups in gelatin (i.e. at a ratio of 1:5 of the mole percent of gelatin lysines to propargyl N-hydroxysuccimide ester), that was added drop-wise at 50-55° C. while stirring for 3 hours. The reaction mixture was dialyzed against distilled water (>pH 8) using 12-14 kDa cutoff dialysis tubing (Spectrum Laboratories, Inc., CA, US) for 2 days to remove reaction by-products. Analyses by NMR showed a >25-30% modification of the gelatin.

Example 6

Preparation of a Hair Composition.

[0194] A 5% (w/v) composition of the product of Example 1 was prepared by dissolving appropriate amounts in distilled water mixed with 1% of photoinitiator Irgacure 2959® (supplied by Sigma Aldrich, Sweden) that had been previously dissolved in hot water at 80° C. Preservatives including Sodium benzoate and phenoxyethanol were also added as antimicrobial agents. The composition exhibited a shelf life of >12 months.

Example 7

Hair Treatment (First Method of the Invention)

[0195] Healthy hair from four volunteers was damaged by applying dithiotretiol (DTT), 200 mM, dissolved in phosphate buffered saline (PBS, pH 7.4) in an amount sufficient to cover all the hair, for two hours. The action of DTT is schematically represented in FIG. 1b The composition of Example 6 was applied on the damaged hair with combing, while shining ultraviolet light (385-400 nm) for 15 minutes using a Dibotech UV flashlight (Kjell & Company, Sweden). The composition was then rinsed off the hair with water and the hair was dried. The action of the composition is schematically represented in FIG. 1b.

[0196] An electron microscopic image was imaged of the hair after treatment using Scanning Electron Microscope. This was compared with a previously obtained image of DTT damaged hair. The results are shown in FIG. 2, where a comparison is shown between a damaged hair following DTT exposure (FIG. 2a) and a repaired hair following the treatment method of the invention (FIG. 2b). It can be seen that whereas in FIG. 2a, the cuticle has a rough and uneven surface, in FIG. 2b, the cuticle is smooth.

[0197] The appearance of the hair was also visibly glossier and shinier after the treatment. It also appeared to have increased in volume. The hair following treatment also had a silkier feel to the touch.

[0198] FIG. 3 shows a comparison of the appearance of the hair before (3a) and after (3b) treatment. It can be seen that after the treatment the hair is shinier, more uniform and not as dry.

[0199] Upon examination after 4 weeks, it was determined that the hair had maintained a healthy appearance in all volunteers.

Example 8

Follow-Up Hair Treatment (Second Method of the Invention)

[0200] After the hair treatment of Example 7, a second treatment according to Example 7 was carried out on the same four volunteers with the difference that the composition applied to the hair was a 1:5 (on a weight to weight basis) mixture of the composition of Example and a conditioning composition free of sulfates, phosphates and parabens and having the following composition: Aqua/Water/Eau, Behentrimonium Chloride, Cetearyl Alcohol, Stearamidopropyl Dimethylamine, PPG-3 Benzyl Ether Myristate, PEG-40 Castor Oil, Glycerin, Cetrimonium Chloride, Hydrolyzed Vegetable Protein PG-Propyl Silanetriol, Argania Spinosa (ARGAN) Kernel Oil, Simmondsia Chinensis (Jojoba) Seed Oil, Persea Gratissima (Avocado) Oil, Keratin Amino Acids, Hydrolyzed Keratin, Sodium PCA, Silk Amino Acids, Rosmarinus Officinalis (Rosemary) Leaf Extract, Lavandula Angustifolia (Lavender) Flower Extract, Chamomilla Recutita (Matricaria) Flower Extract, Amodimethicone, Trideceth-12, C11-15 Pareth-7, Laureth-9, Panthenol, Isopropyl Alcohol, Propylene Glycol Dicaprylate/Dicaprate, PPG-1 Trideceth-6, Hydroxypropyl Guar Hydroxypropyltrimonium Chloride, Polyquaternium-37, Propylene Glycol, Cinnamidopropyltrimonium Chloride, Disodium EDTA, Fragrance (Parfum), Phenoxyethanol, Ethylhexylglycerin, Citric Acid, Yellow 5 (CI 19140), Red 33 (CI 17200), Butylphenyl Methylpropional, Hydroxyisohexyl 3-Cyclohexene Carboxaldehyde, Linalool, Alpha-Isomethyl Ionone.

[0201] After the application of the composition, the hair was left to process for 10 minutes with exposure to radiation, as in Example 7. After the processing time, the hair was left to rest for a further 10 minutes, without exposure to radiation. The hair was then thoroughly rinsed.

[0202] Upon examination it was determined that the hair had a healthy appearance on all volunteers.

Example 9

Follow-Up Conditioning (Third Method of the Invention)

[0203] The volunteers were given a 100 ml bottle of a 1:5 (w/w) mixture of a composition prepared according to Example 6, with the difference that the reactive molecules were present in a 0.8% (w/v) concentration with EosinY; and the conditioning composition described in Example 8.

[0204] The volunteers were instructed to use the mixture once every two weeks to follow up the treatment from Example 7 and example 8.

[0205] The volunteers were instructed to apply the conditioner and expose the hair sunlight for 15 minutes, and then rinse off.

[0206] At the end of the 8 weeks, the hair of the volunteers was examined. The hair had maintained a healthy appearance in all volunteers.

Example 10

Hair Composition Containing a Fluorescent Dye

[0207] A composition was prepared according to Example 6 with the difference that Ebest Fluorescein LTC (purchased from Fastcolors, UK) was also added to the mixture (in a concentration in weight percent based on the volume of the total composition of 0.001%).

[0208] The composition was then applied to the hair of a volunteer, according to Example 7.

[0209] It was observed that, as the UV light (385-400 nm) was shined on the hair, the hair composition illuminated, making it possible to detect any areas of the hair where the composition had not been applied. See FIG. 4.

Example 11

Preparation of a Composition Comprising Alkene-Functionalised Hydrolysed Soy Protein.

[0210] 5%(w/v) hydrolysed soy protein powder (Kelisema, Italy) was dissolved in Milli Q water to 100 ml and gently stirred. The pH was adjusted to 7.5-8.5 using 2N NaOH (Sigma). Subsequently, methacrylic anhydride (Sigma-Aldrich, Sweden) was added to the solution, drop-wise at room temperature (25° C.) at a molar ratio of 5:1 with respect to the mole percent of lysine amine groups in the soy protein to modify the hydrolysed soy protein with reactive methacrylate functional groups.

[0211] After 1 hour of reaction, the mixture was dialysed against water (pH >8-9) for 24 hours using Dialysis Membranes (MWCO 100-500D) obtained from Spectrum Laboratories, Inc. (CA, US) at room temperature (about 25° C.), to remove any unreacted methacrylic anhydride and other side products of the reaction.

[0212] The reaction product was then freeze-dried. The degree of substitution (DS) was determined by NMR by comparison of the pristine hydrolysed soy protein and hydrolysed soy protein methacrylate.

[0213] Analyses by NMR showed a higher than 50% modification of the hydrolysed soy protein with methacrylic groups.

Example 12

Preparation of a Composition Comprising Alkyne-Functionalised Hydrolysed Soy Protein.

[0214] 5%(w/v) hydrolysed soy protein powder (Kelisema, Italy) was dissolved in Milli Q water to 100 ml and gently stirred. The pH was adjusted to 7.5-8.5 using 2N NaOH (Sigma). Subsequently, propargyl N-hydroxysuccimide ester (Sigma-Aldrich, Sweden) solubilised in minimal quantity dimethyl sulfoxide (DMSO, Sigma) was added to the solution, drop-wise, while stirring for three hours at room temperature (25° C.) in molar excess at a 1:5 molar ratio with respect to the mole percent of lysine amine groups in hydrolysed soy protein (i.e. at a ratio of 1:5 of the mole percent of hydrolysed soy protein lysines to propargyl N-hydroxysuccimide ester) to modify the hydrolysed soy protein with reactive methacrylate functional groups.

[0215] After 1 hour of reaction, the mixture was dialysed against water (pH >8-9) for 24 hours using Dialysis Membranes (MWCO 100-500D) obtained from Spectrum Laboratories, Inc. (CA, US) at room temperature (about 25° C.), to remove any unreacted methacrylic anhydride and other side products of the reaction.

[0216] The reaction product was then freeze-dried. The degree of substitution (DS) was determined by NMR by comparison of the pristine hydrolysed soy protein and hydrolysed soy protein methacrylate.

[0217] Analyses by NMR showed a higher than 50% modification of the hydrolysed soy protein with methacrylic groups.