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Publication numberUS20070225360 A1
Publication typeApplication
Application numberUS 11/726,176
Publication dateSep 27, 2007
Filing dateMar 20, 2007
Priority dateMar 22, 2006
Also published asCA2582736A1, CA2582736C, EP1837056A2, EP1837056A3, US20090286874
Publication number11726176, 726176, US 2007/0225360 A1, US 2007/225360 A1, US 20070225360 A1, US 20070225360A1, US 2007225360 A1, US 2007225360A1, US-A1-20070225360, US-A1-2007225360, US2007/0225360A1, US2007/225360A1, US20070225360 A1, US20070225360A1, US2007225360 A1, US2007225360A1
InventorsSheldon R. Pinnell, Jan Zielinski, Isabelle Hansenne
Original AssigneeL'oreal
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Anti-aging composition containing phloretin
US 20070225360 A1
Abstract
An anti-aging composition containing: (a) at least one first active ingredient chosen from phloretin and its derivatives; (b) at least one second active ingredient chosen from cinnamic acid, resveratrol, retinol, ascorbic acid, tocopherol, and their derivatives; and (c) at least one non-aqueous organic solvent, with the proviso that if the composition contains ascorbic acid, water is present as a co-solvent.
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Claims(30)
1. An anti-aging composition comprising:
(a) at least one first active ingredient chosen from phloretin and its derivatives;
(b) at least one second active ingredient chosen from cinnamic acid, resveratrol, retinol, ascorbic acid, tocopherol, and their derivatives; and
(c) at least one non-aqueous organic solvent; with the proviso that, if the composition contains ascorbic acid, water is present as a co-solvent.
2. The composition of claim 1, wherein (a) is present in the composition in an amount of from about 0.1 to about 10% by weight, based on the total weight of the composition.
3. The composition of claim 1, wherein (a) is present in the composition in an amount of from about 1 to about 5% by weight, based on the total weight of the composition.
4. The composition of claim 1, wherein (a) is present in the composition in an amount of from about 0.5 to about 3% by weight, based on the total weight of the composition.
5. The composition of claim 1, wherein (a) is present in the composition in an amount of from about 1 to about 2% by weight, based on the total weight of the composition.
6. The composition of claim 1, wherein (a) is phloretin.
7. The composition of claim 1, wherein (b) is a cinnamic acid derivative.
8. The composition of claim 1, wherein (b) is ferulic acid.
9. The composition of claim 1, wherein (b) is a mixture of ferulic acid and ascorbic acid.
10. The composition of claim 8, wherein ferulic acid is present in an amount of from about 0.2 to about 5% by weight, and ascorbic acid is present in an amount of from about 5 to about 20% by weight, all weights based on the total weight of the composition.
11. The composition of claim 1, wherein (b) is resveratrol.
12. The composition of claim 1, wherein (b) is present in the composition in an amount of from about 0.1 to about 20% by weight, based on the total weight of the composition.
13. The composition of claim 1, wherein (b) is present in the composition in an amount of from about 0.2 to about 15% by weight, based on the total weight of the composition.
14. The composition of claim 1, wherein (b) is present in the composition in an amount of from about 0.2 to about 10% by weight, based on the total weight of the composition.
15. An anti-aging composition comprising:
(a) about 2% by weight, phloretin;
(b) about 0.5% by weight, ferulic acid;
(c) about 15% by weight, ascorbic acid;
(d) about 30% by weight of a glycol; and
(e) remainder, to 100%, water.
16. A process for treating radical-induced damage to skin comprising contacting the skin with a composition containing:
(a) at least one first active ingredient chosen from phloretin and its derivatives;
(b) at least one second active ingredient chosen from cinnamic acid, resveratrol, retinol, ascorbic acid, tocopherol, and their derivatives;
(c) at least one non-aqueous organic solvent;
with the proviso that if the composition contains ascorbic acid, water is present as a co-solvent.
17. The process of claim 16, wherein (a) is present in the composition in an amount of from about 0.1 to about 10% by weight, based on the total weight of the composition.
18. The process of claim 16, wherein (a) is present in the composition in an amount of from about 1 to about 5% by weight, based on the total weight of the composition.
19. The process of claim 16, wherein (a) is present in the composition in an amount of from about 0.5 to about 3% by weight, based on the total weight of the composition.
20. The process of claim 16, wherein (a) is present in the composition in an amount of from about 1 to about 2% by weight, based on the total weight of the composition.
21. The process of claim 16, wherein (a) is phloretin.
22. The process of claim 16, wherein (b) is a cinnamic acid derivative.
23. The process of claim 16 wherein (b) is ferulic acid.
24. The process of claim 16, wherein (b) is a mixture of ferulic acid and ascorbic acid.
25. The process of claim 24 wherein ferulic acid is present in the composition in an amount of from about 0.2 to about 5% by weight, and ascorbic acid is present in the composition in an amount of from about 5 to about 20% by weight, all weights based on the total weight of the composition.
26. The process of claim 16, wherein (b) is resveratrol.
27. The process of claim 16, wherein (b) is present in the composition in an amount of from about 0.1 to about 20% by weight, based on the total weight of the composition.
28. The process of claim 16, wherein (b) is present in the composition in an amount of from about 0.2 to about 15% by weight, based on the total weight of the composition.
29. The process of claim 16, wherein (b) is present in the composition in an amount of from about 0.2 to about 10% by weight, based on the total weight of the composition.
30. The process of claim 16 wherein the composition comprises: (a) about 2% by weight, phloretin; (b) about 0.5% by weight, ferulic acid; (c) about 15% by weight, ascorbic acid; (d) about 30% by weight of a glycol; and (e) remainder, to 100%, water.
Description

This application is a non-provisional application of, and claims benefit to, U.S. Provisional Application No. 60/784,571, filed Mar. 22, 2006, which is incorporated by reference in its entirety for all purposes.

BACKGROUND OF THE INVENTION

Aging skin is the result of more than just chronological age. Skin is exposed to environmental elements that cause radicals to form in the skin. These radicals attack the collagen layer of the skin and break it down, causing lines and wrinkles to appear. This process is commonly called photo-aging. Diseases and disorders of skin that also may result from radical damage include skin cancer, skin irritation or inflammation, dermatitis, allergy, psoriasis, acne, eczema, rosacea.

Application of antioxidants can help prevent radical-induced damage in skin. Applying Vitamin C, for example, to the skin can provide antioxidant protection, prevent photo-aging, and stimulate collagen production. However, not all Vitamin C formulations produce these benefits due to lack of stability.

The present invention is thus directed to a composition and process for inhibiting radical-induced damage to skin which does not suffer from conventional stability issues.

BRIEF SUMMARY OF THE INVENTION

The present invention is directed to an anti-aging composition containing:

  • (a) at least one first active ingredient chosen from phloretin and its derivatives;
  • (b) at least one second active ingredient chosen from cinnamic acid, resveratrol, retinol, ascorbic acid, tocopherol, and their derivatives; and
  • (c) at least one non-aqueous organic solvent, and with the proviso that, if the composition contains ascorbic acid, water is present as a co-solvent.

The present invention is also directed to a process for treating radical-induced damage to skin by contacting the skin with the above-disclosed composition.

DETAILED DESCRIPTION OF THE INVENTION

Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients and/or reaction conditions are to be understood as being modified in all instances by the term “about”.

The present invention is directed to the surprising discovery that by combining at least one first active ingredient chosen from phloretin, and its derivatives, with at least one second active ingredient chosen from cinnamic acid, resveratrol, retinol, ascorbic acid, tocopherol and their derivatives, an effective treatment for radical-induced damage to skin is realized.

First Active Ingredient

Phloretin is the aglucone portion of phlorizin and is a polyphenolic compound. It is split from phlorizin by acid hydrolysis. Alternatively, phloretin can be completely synthesized directly by known processes.

Suitable phloretin derivatives include, but are not limited to, dihydrochalcone derivatives, such as those disclosed in U.S. Pat. No. 6,448,232, the entire contents of which is hereby incorporated by reference.

The composition of the present invention contains the at least one first active ingredient in an amount of from about 0.1 to about 10% by weight, such as from about 0.5 to about 7% by weight, such as from about 1 to about 5% by weight, such as from about 0.5 to about 3% by weight, such as from about 1 to about 2% by weight, all weights based on the total weight of the composition.

Second Active Ingredient

The at least one second active ingredient is chosen from cinnamic acid, resveratrol, retinol, ascorbic acid, tocopherol, and their derivatives.

In one embodiment, the at least one second active is a cinnamic acid derivative, examples of which include, but are not limited to, caffeic acid, p-coumaric acid, ferulic acid, sinapinic acid, mixtures thereof, cis and trans isomers thereof, salts thereof, and equivalent derivatives thereof.

In a particularly preferred embodiment, the at least one second ingredient is a combination of ferulic acid and ascorbic acid.

The at least one second active ingredient is present in the composition in an amount of from about 0.1 to about 25% by weight, such as from about 0.2 to about 15% by weight, such as from about 0.2 to about 10% by weight, all weights based on the total weight of the composition.

The ratio by weight of first active ingredient to second active ingredient will typically be from about 0.1:10 to about 10:0.1, such as about 0.3:5, such as about 0.5:2.

Non-Aqueous Organic Solvent

Any non-aqueous organic solvent capable of solubilizing the first and second active ingredients may be employed. Examples of suitable solvents include, but are not limited to, non-aqueous polar organic solvents, and non-aqueous non-polar organic solvents.

Non-Aqueous Polar Organic Solvent

A variety of non-aqueous polar organic solvents may be used in the anti-aging composition of the present invention. Examples thereof are as follows.

Polyols

Polyols are suitable non-aqueous polar organic solvents. For purposes of this specification, polyols are defined as compounds which contain three or more hydroxyl groups per molecule. Examples of suitable polyols include glucose glutamate, glycerin, 1,2,6-hexanetriol, methyl gluceth-10, methyl gluceth-20, methyl glucose dioleate, methyl glucose sesquicaprylate/sesquicaprate, methyl glucose sesquicocoate, methyl glucose sesquiisostearate, methyl glucose sesquilaurate, methyl glucose sesquistearate, phytantriol, sorbeth-6, sorbeth-20, sorbeth-30, sorbeth-40, thioglycerin, and mixtures thereof. An especially preferred polyol is glycerin.

Polymeric or Monomeric Ethers

Also suitable as the non-aqueous polar organic solvent are homopolymeric or block copolymeric liquid ethers. Polymeric ethers are preferably formed by polymerization of monomeric alkylene oxides, generally ethylene or propylene oxides. Examples of such polymeric ethers include PEG, PPG, and derivatives thereof.

Other examples of suitable polymeric ethers include polyoxypropylene polyoxyethylene block copolymers. Such compounds are sold under the CTFA name Meroxapol 105, 108, 171, 172, 174, 178, 251, 252, 254, 255, 258, 311, 312, and 314.

Mono- and Dihydric Alcohols

Also suitable for use as to the non-aqueous polar organic solvent are mono- and dihydric alcohols of the general formula R(OH)n where n is 1 or 2 and R is a substituted or unsubstituted saturated C2-10, preferably C1-8 alkyl, or a substituted or unsubstituted alicyclic, bicyclic, or aromatic ring, with the substituents selected from halogen, alkoxy, hydroxy, and so on. Examples of suitable alcohols include monohydric alcohols such as ethanol, isopropanol, hexyldecanol, benzyl alcohol, propyl alcohol, and isopropyl alcohol, as well as dihydric alcohols such as hexylene glycol, diethylene glycol, ethylene glycol, propylene glycol, 1,2-butylene glycol, 1,5-pentanediol, triethylene glycol, dipropylene glycol, and mixtures thereof.

Sorbitan Derivatives

Sorbitan derivatives, which are defined as ethers or esters of sorbitan, are also suitable polar solvents. Examples of suitable sorbitan derivatives are the Polysorbates, which are defined as stearate esters of sorbitol and sorbitan anhydrides, such as Polysorbate 20, 21, 40, 60, 61, 65, 80, 81, and 85. Also suitable are fatty esters of hexitol anhydrides derived from sorbitol, such as sorbitan trioleate, sorbitan tristearate, sorbitan sesquistearate, sorbitan stearate, sorbitan palmitate, sorbitan oleate, and mixtures thereof.

Non-Aqueous Non-Polar Organic Solvents

A variety of non-aqueous non-polar organic solvents can be used in the composition of the invention, if so desired. Examples thereof are as follows.

Silicones

Silicones are suitable non-polar compounds. The silicones may be volatile or non-volatile. The term “volatile” means that the silicone has a measurable vapor pressure, i.e. a vapor pressure of at least 2 mm. of mercury at 20° C. If volatile, the silicone generally will have a viscosity of 0.5 to 25 centistokes at 25° C. Suitable volatile silicones include cyclic silicones, linear silicones, or mixtures thereof.

Linear and cyclic volatile silicones are available from various commercial sources including Dow Corning Corporation and General Electric. The Dow Corning volatile silicones are sold under the tradenames Dow Corning 244, 245, 344, and 200 fluids. These fluids comprise octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, hexamethyldisiloxane, and mixtures thereof.

The silicone may also be nonvolatile, and in particular water insoluble nonvolatile silicones. The term “nonvolatile” means that the silicone has a vapor pressure of less than 2 mm. of mercury at 20° C. A variety of silicones fits this definition including dimethicone, phenyl trimethicone, diphenyl dimethicone, methicone, hexadecyl methicone, stearoxydimethicone, stearyl dimethicone, cetyl dimethicone, and so on.

Cyclomethicone is a preferred silicone for use in the composition of the invention.

Esters

In addition to the sorbitan esters, other esters are also suitable as the non-aqueous non-polar organic solvent. In general such esters have the formula R1CO—OR2 wherein R1 and R2 are independently a C1-25 straight or branched chain saturated or unsaturated alkyl, alkylcarbonyloxyalkyl, or alkoxycarbonylalkyl, aryl, which may be substituted or unsubstituted with halogen, hydroxyl, alkyl, and the like.

Examples of suitable esters include alkyl acetates, alkyl behenates, alkyl lactates, alkyl benzoates, alkyl octanoates, alkyl salicylates, and in particular C12-15 alkyl benzoate. Examples of further esters are set forth on pages 502-506 of the CTFA Cosmetic Ingredient Handbook, Second Edition, 1992, which is hereby incorporated by reference.

Fats and Oils

Fats and oils are also suitable as the non-aqueous non-polar organic solvent. Preferably these materials are liquids or semi-solids at room temperature. They are generally defined as glyceryl esters of fatty acids (triglycerides), as well as the synthetically prepared esters of glycerin and fatty acids. Examples of such materials include oils such as apricot kernel oil, avocado oil, canola oil, olive oil, sesame oil, peanut oil, soybean oil, trilinolenin, trilinolein, trioctanoin, tristearin, triolein, sesame oil, rapeseed oil, sunflower seed oil, and so on.

Fatty Acids

Fatty acids are also suitable as the non-aqueous non-polar organic solvent in the compositions of the invention. Preferably the fatty acids are liquid or semi solid at room temperature. Fatty acids are the carboxylic acids obtained by hydrolysis of animal or vegetable fats and oils. Carboxylic acids having alkyl chains shorter than about seven carbon atoms are not generally considered fatty acids. Fatty acids have the general structure R3—COOH where R3 is a straight or branched chain saturated or unsaturated C7-65 alkyl. Examples of suitable fatty acids include arachidic acid, arachidonic acid, behenic acid, capric acid, caproic acid, caprylic acid, coconut acid, corn acid, cottonseed acid, hydrogenated coconut acid, hydroxystearic acid, lauric acid, linoleic acid, linolenic acid, linseed acid, myristic acid, oleic acid, palmitic acid, palm kernel acid, soy acid, tallow acid, and the like.

Fatty Alcohols

Fatty alcohols may also be used as the non-aqueous non-polar organic solvent. Fatty alcohols are generally made by reducing the fatty acid —COOH group to the hydroxyl function. They generally have the formula R4CH2OH. Examples of fatty alcohols are behenyl alcohol, C9-11 alcohol, C12-13 alcohol, C12-15 alcohol, C12-16 alcohol, caprylic alcohol, cetearyl alcohol, cetyl alcohol, coconut alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, oleyl alcohol, and the like.

Hydrocarbons

Hydrocarbons are also good non-aqueous non-polar organic solvents in accordance with the invention. Examples of suitable hydrocarbons include C7-60 isoparaffins, ethane, heptane, hexane, hydrogenated polyisobutene, isobutane, isododecane, isoeicosane, isohexadecane, isopentane, microcrystalline wax, mineral oil, mineral spirits, paraffin, petrolatum, petroleum distillates, squalene, polyethylene, and mixtures thereof. Preferred hydrocarbons are mineral oil and polyethylene.

Lanolin and Lanolin Derivatives

Also suitable as the non-aqueous non-polar organic solvent are lanolin and derivatives thereof. Examples of such materials include acetylated hydrogenated lanolin, acetylated lanolin alcohol, laneth, lanolin acid, lanolin oil, lanolin alcohol, lanolin wax, and so on.

The composition of the present invention contains at least one organic solvent in an amount of from about 1 to about 95% by weight, such as from about 1 to about 60% by weight, such as from about 5 to about 40% by weight, all weights based on the total weight of the composition.

In the event that ascorbic acid is employed in the composition of the present invention as a second active ingredient, water will be present in the composition as a co-solvent. The water will be employed in an amount at least sufficient to solubilize the ascorbic acid present in the composition.

In a preferred embodiment of the present invention, the composition is in the form of a single-phase solution, such as cosmetic serums or aerosols, for example. In another embodiment, the composition is in the form of an emulsion, such as creams or lotions, for example.

Other Ingredients

It may also be desired to include certain other ingredients in the composition of the invention, such as surfactants, waxes, colorants, preservatives, and the like.

Surfactants

Silicone Surfactants

The term “surfactant” is defined, in accordance with the invention, as a compound having at least one hydrophilic moiety and at least one lipophilic moiety. The surfactants may be silicone surfactants (also referred to as organosiloxane emulsifiers) or organic surfactants.

Suitable silicone surfactants used in the compositions of the invention may be liquid or solid at room temperature and are generally a water-in-oil or oil-in-water type surfactants which are preferably nonionic, having an Hydrophile/Lipophile Balance (HLB) of 2 to 18. Preferably the organosiloxane is a nonionic surfactant having an HLB of 2 to 12; such as 2 to 10; such as 4 to 6. The HLB of a nonionic surfactant is the balance between the hydrophilic and lipophilic portions of the surfactant and is calculated according to the following formula:


HLB=20(1−S/A)

where S is the saponification number of the surfactant and A is the acid number of the surfactant.

The silicone surfactant or emulsifier used in the compositions of the invention is a polymer containing a polymeric backbone including repeating siloxy units that may have cyclic, linear or branched repeating units, e.g. di(lower)alkylsiloxy units, preferably dimethylsiloxy units. The hydrophilic portion of the organosiloxane is generally achieved by substitution onto the polymeric backbone of a radical that confers hydrophilic properties to a portion of the molecule. The hydrophilic radical may be substituted on a terminus of the polymeric organosiloxane, or on any one or more repeating units of the polymer. In general, the repeating dimethylsiloxy units of modified polydimethylsiloxane emulsifiers are lipophilic in nature due to the methyl groups, and confer lipophilicity to the molecule. In addition, longer chain alkyl radicals, hydroxy-polypropyleneoxy radicals, or other types of lipophilic radicals may be substituted onto the siloxy backbone to confer further lipophilicity and organocompatibility. If the lipophilic portion of the molecule is due in whole or part to a specific radical, this lipophilic radical may be substituted on a terminus of the organosilicone polymer, or on any one or more repeating units of the polymer. It should also be understood that the organosiloxane polymer in accordance with the invention should have at least one hydrophilic portion and one lipophilic portion.

The term “hydrophilic radical” means a radical that, when substituted onto the organosiloxane polymer backbone, confers hydrophilic properties to the substituted portion of the polymer. Examples of radicals that will confer hydrophilicity are hydroxy-polyethyleneoxy, hydroxyl, carboxylates, sulfonates, sulfates, phosphates, or amines.

The term “lipophilic radical” means an organic radical that, when substituted onto the organosiloxane polymer backbone, confers lipophilic properties to the substituted portion of the polymer. Examples of organic radicals which will confer lipophilicity are C1-40 straight or branched chain alkyl, fluoro, aryl, aryloxy, C1-40 hydrocarbyl acyl, hydroxypolypropyleneoxy, or mixtures thereof. The C1-40 alkyl may be non-interrupted, or interrupted by one or more oxygen atoms, a benzene ring, amides, esters, or other functional groups.

Organosiloxane polymers useful in the compositions of the invention include those sold by Goldschmidt under the ABIL™ trademark including ABIL B-9806™, as well as those sold by Rhone-Poulenc under the Alkasil™ tradename. Also, organosiloxane emulsifiers sold by Amerchol under the Amersil™ tradename, including Amersil ME-358™, Amersil DMC-287™ and Amersil DMC-357™ are suitable. Dow Corning surfactants such as Dow Corning 3225C™ Formulation Aid, Dow Corning 190™ Surfactant, Dow Corning 193™ Surfactant, Dow Corning Q2-5200™, and the like are also suitable. In addition, surfactants sold under the tradename Silwet™ by Union Carbide, and surfactants sold by Troy Corporation under the Troysol™ tradename, those sold by Taiwan Surfactant Co. under the tradename Ablusoft™, those sold by Hoechst under the tradename Arkophob™, are also suitable for use in the invention.

Also suitable as surfactants are various organic surfactants such as anionic, nonionic, amphoteric, zwitterionic, or cationic surfactants.

The composition of the present invention may contain at least one surfactant in an amount of from about 0.01 to about 15% by weight, such as from about 0.5 to about 10% by weight, such as from about 1 to about 8% by weight, all weights based on the total weight of the total composition.

Waxes

Suitable waxes have a melting point of from about 35 to about 120° C., include animal waxes, plant waxes, mineral waxes, silicone waxes, synthetic waxes, and petroleum waxes.

The composition of the present invention may contain waxes in an amount of from about 0.1 to about 25% by weight, such as from about 0.5 to about 20% by weight, such as from about 1 to about 15% by weight, all weights based on the total weight of the total composition.

Branched Chain Silicone Resins

It may be desirable to include one or more branched chain silicone resins in the compositions of the invention. Examples of suitable silicone resins include, but are not limited to, siloxy silicate polymers such as those commercially available from GE silicones under the trade name of SR1000™, and silicone esters such as those commercially available from General Electric under the tradenames SF1318™ and SF1312™, and the like.

The composition of the present invention may contain branched chain silicone resins in an amount of from about 0.001 to about 20% by weight, such as from about 0.01 to about 15% by weight, such as from about 0.1 to about 10% by weight, all weights based on the total weight of the composition.

Pigments and Powders

Pigments and/or powders may be used in the composition of the present invention. If used, they may be present in an amount of from about 0.001 to about 35% by weight, such as from about 0.01 to about 20% by weight, such as from about 0.1 to about 10% by weight, all weights based on the total weight of the composition.

Sunscreens

The composition of the present invention may also contain a sunscreen. If used, they may be present in an amount of from about 0.001 to about 20% by weight, such as from about 0.01 to about 10% by weight, such as from about 0.05to about 8% by weight, all weights based on the total weight of the composition.

Preservatives

A variety of preservatives may also be employed in an amount of from about 0.0001 to about 8% by weight, such as from about 0.001 to about 6% by weight, such as from about 0.005 to about 5% by weight, all weights based on the total weight of the composition.

Vitamins

The compositions of the invention may contain vitamins and/or coenzymes. Suitable vitamins include, but are not limited to, the B vitamins such as thiamine, riboflavin, pyridoxin, as well as coenzymes such as thiamine pyrophoshate, flavin adenin dinucleotide, folic acid, pyridoxal phosphate, tetrahydrofolic acid. Also Vitamin A and derivatives thereof are suitable such as retinoic acid and retinaldehyde. Additional examples are Vitamin A palmitate, acetate, or other esters thereof, as well as Vitamin A in the form of beta carotene. Also suitable is Vitamin E and derivatives thereof such as Vitamin E acetate, nicotinate, or other esters thereof. In addition, Vitamins D and K are suitable.

The composition of the present invention may contain vitamins and/or coenzymes in an amount of from about 0.001 to about 10% by weight, such as from about 0.01 to about 8% by weight, such as from about 0.05 to about 5% by weight, all weights based on the total weight of the composition.

Alpha or Beta Hydroxy Acids, Alpha Keto Acids

It may also be desired to add one or more alpha or beta hydroxy acids or alpha ketoacids to the compositions of the invention. Suitable alpha hydroxy acids may exist in the keto acid form, or the ester form. Examples of such alpha hydroxy acids include, but are not limited to, glycolic acid, malic acid, pyruvic acid, mandelic acid, lactic acid, methyllactic acid.

Also beta hydroxy acids such as salicylic acid, and derivatives thereof may be included in the compositions of the invention.

The composition of the present invention may contain alpha or beta hydroxy acids, or alpha keto acids in an amount of from about 0.01 to about 20% by weight, such as from about 0.1 to about 15% by weight, such as from about 0.5 to about 10% by weight, all weights based on the total weight of the composition.

According to one embodiment of the present invention, there is provided an anti-aging composition containing: (a) from about 0.1 to about 10% by weight, preferably from about 0.3 to about 5% by weight of phloretin; (b) from about 0.1 to about 10% by weight, preferably from about 0.2 to about 5% by weight of ferulic acid; (c) from about 1 to about 25% by weight, preferably from about 5 to about 20% by weight of ascorbic acid; (d) from about 1 to about 60% by weight, preferably from about 5 to about 40% by weight of a glycol; and (e) remainder, water, all weights based on the total weight of the composition.

Methods of Use

The present invention is also directed to a process for treating radical-induced damage to skin by contacting the skin with the above-disclosed composition. Treating, as used herein, means prophylactic and/or therapeutic treatment of a subject. “Prophylactic” treatment is a treatment administered to a subject who does not have symptoms of radical-induced damage or has early signs of such damage, or anticipates being exposed to situations having risk of radical-induced damage. “Therapeutic” treatment is a treatment administered to a subject who has signs of radical-induced damage.

The present invention is further described in terms of the following non-limiting examples. Unless otherwise indicated, all parts and percentages are on a weight-by-weight percentage basis.

EXAMPLES

The following products were made:

Set 1

Example A 2% Phloretin

Ingredient w/w %
Phenoxyethanol 1.0
Pentylene Glycol 20.0
Pentylene Glycol 10.0
Phloretin 2.0
Alcohol Denat. 10.0
Water 56.9
Sodium Hyaluronate 0.1
Total 100.0

Example B 15% Vitamin C

Ingredient w/w %
Phenoxyethanol 1.0
Ascorbic Acid 15.0
Pentylene Glycol 20.0
Propylene Glycol 10.0
Alcohol Denat. 10.0
Water 43.9
Sodium Hyaluronate 0.1
Total 100.0

Example C Control Formulation

Ingredient w/w %
Phenoxyethanol 1.0
Pentylene Glycol 20.0
Propylene Glycol 10.0
Alcohol Denat. 10.0
Water 58.9
Sodium Hyaluronate 0.1
Total 100.0

Example D Ferulic Acid 0.5%, Phloretin 2%

Ingredient w/w %
Ferulic Acid 0.5
Phenoxyethanol 1.0
Pentylene Glycol 20.0
Propylene Glycol 10.0
Phloretin 2.0
Alcohol Denat. 10.0
Water 56.4
Sodium Hyaluronate 0.1
Total 100.0

Example E 15.3% Vitamin C, 0.5% Ferulic Acid, 1.0% Vitamin E

Ingredient w/w %
Phenoxyethanol 1.05
Pentylene Glycol 5.00
Propylene Glycol 5.00
Glycerin 3.00
Ascorbic acid 15.30
Vitamin E 1.00
Ferulic acid 0.50
Water 65.87
Sodium Hyaluronate 0.10
Antifoam 0.01
Laureth-23 3.00
Sodium Hydroxide (to pH 3) 0.18
Total 100.00

Example F 15.3% Vitamin C, 0.5% Ferulic Acid, and 2% Phloretin

Ingredient w/w %
Ferulic Acid 0.5
Phenoxyethanol 1.0
Ascorbic Acid 15.0
Pentylene Glycol 20.0
Propylene Glycol 10.0
Phloretin 2.0
Alcohol Denat. 10.0
Water 41.4
Sodium Hyaluronate 0.1
Total 100.0

Set 2

Example G 15% Vitamin C, 0.5% Ferulic Acid, 2% Phloretin, and 0.02% Vitamin E

Ingredient w/w %
Phenoxyethanol 1.00
Pentylene Glycol 20.00
Propylene Glycol 10.00
Alcohol Denat. 10.00
Ascorbic acid 15.00
Ferulic acid 0.50
Phloretin 2.00
Vitamin E 0.02
Water 41.38
Sodium Hyaluronate 0.10
Total 100.00

Example H 15% Vitamin C, and 2% Phloretin

Ingredient w/w %
Phenoxyethanol 1.0
Pentylene Glycol 20.0
Propylene Glycol 10.0
Alcohol Denat. 10.0
Ascorbic acid 15.0
Phloretin 2.0
Water 41.9
Sodium Hyaluronate 0.10
Total 100.0

Example I 0.5% Ferulic Acid

Ingredient w/w %
Phenoxyethanol 1.0
Pentylene Glycol 20.0
Propylene Glycol 10.0
Alcohol Denat. 10.0
Ferulic acid 0.5
Water 58.4
Sodium Hyaluronate 0.10
Total 100.0

Example J Control Formulation

Ingredient w/w %
Phenoxyethanol 1.0
Pentylene Glycol 20.0
Propylene Glycol 10.0
Alcohol Denat. 10.0
Water 58.9
Sodium Hyaluronate 0.1
Total 100.0

Example K 15% Vitamin C, 1% Vitamin E, and 0.5% Ferulic Acid

Ingredient w/w %
Phenoxyethanol 1.05
Pentylene Glycol 5.00
Propylene Glycol 5.00
Glycerin 3.00
Ascorbic acid 15.30
Vitamin E 1.00
Ferulic acid 0.50
Water 65.87
Sodium Hyaluronate 0.10
Antifoam 0.01
Laureth-23 3.00
Sodium Hydroxide (to pH 3) 0.18
Total 100.00

Example L 15% Vitamin C, 0.5% Ferulic Acid, and 2% Phloretin

Ingredient w/w %
Phenoxyethanol 1.0
Pentylene Glycol 20.0
Propylene Glycol 10.0
Alcohol Denat. 10.0
Ascorbic acid 15.0
Ferulic acid 0.5
Phloretin 2.0
Water 41.4
Sodium Hyaluronate 0.1
Total 100.0

A single application of each of the samples was applied on the back of 10 subjects with very fair or fair skins (6 and 4 subjects respectively) associated with a phototype II.

All products were applied at a rate of 4 mg/cm2, with a finger provided with a finger cot.

One hour and a half after application, the treated zones were exposed to 320-440 nm UVA at a dose corresponding to 2 Individual Minimal Erythemal Doses (iMED).

Colorimetric measurements and visual assessments were performed 2 hours after exposure in order to evaluate the intensity of UVA-induced erythema and that of the Persistent Pigment Darkening (PPD).

Colorimetric Measurements

The equipment used for colorimetric measurements was as follows:

  • MINOLTA CR 300 No2 COLORIMETER
  • 1600 Watts Xenon lamp ORIEL 4×4 with filters WG 335 3 mm (A) and dichroic mirror for UVA spectrum in the field 320-440 nm, was used for colorimetric measurements in compliance with the in vivo PPD method as described in the following articles: A. Chardon, D. Moyal, C. Hourseau: Persistent pigment darkening response as a method for evaluation of UVA protection assays published in “Sunscreens: development, evaluation and regulatory aspects”, 2nd edition (N. Lowe, N. Shath, M. Pathak, ed.; Marcel Dekker Inc.), pp. 559-582, 1986, and D. Moyal, A. Chardon, N. Kollias: UVA protection efficacy of sunscreens can be determined by the persistent pigment darkening (PPD) method (Part 2), published in Photo-dermatol. Photoimmunol. Photomed., 16, 250-255, 2000.
  • UV-METER PMA No5 with UVA Sensor SN 2423 used to measure and calculate the amounts of UVA received (J.cm2).
  • Balance
  • Finger cot

Evaluation Criteria

Colorimetric measurements were performed on the treated exposed zones (TEZ) and on the non-treated exposed zones (NTEZ) (2 measurements in triplicate). The measurements were expressed as L*, a*, and b* values (CIE 1976 L*a*b* also known as CIELAB). The L*, a*, and b* values obtained from the zones treated with a product were compared to the L*, a*, and b* values obtained from the zones treated with the control formulation.

The UVA-induced erythema is expressed as Δa*, which represents the difference in a* values between the treated exposed zones (TEZ) and the non-treated exposed zones (NTEZ). Δa* represents the red hue, which quantifies the intensity of the UVA-induced erythema. The larger the Δa*, the more intense the erythema.

Visual assessments of the UVA-induced erythema were performed 2 hours after exposure, and reported on a scale having 14 levels of evaluation, from 0=no pink color observed (no erythema) to 13=darkest pink color observed.

The Persistent Pigment Darkening (PPD) is reported as ΔE, which represents the total modification of the coloring of the skin.

ΔE is expressed as the square root of (Δa*2+Δb*2+ΔL*2).

The larger the ΔE, the more intense the persistent pigment darkening (PPD). ΔE may be used to represent the overall change in color.

Results

Set 1

Colorimetric Measurement of UVA Induced Erythema

Each sample was measured against sample C, which is the control formulation containing only the carrier and no active.

Sample A, containing 2% phloretin, significantly reduced the intensity of the UVA induced erythema (p=0.013).

Sample B, containing 15% vitamin C, did not significantly reduced intensity of the UVA induced erythema (p=0.240).

Sample D, containing 2% phloretin and 0.5% ferulic acid, significantly reduced the intensity of the UVA induced erythema (p=0.007).

Sample E, containing 15.3% Vitamin C, 0.5% ferulic acid and 1% Vitamin E, significantly reduced the intensity of the UVA induced erythema (p=0.023).

Sample F, containing 2% phloretin, 0.5% ferulic acid and 15.3% vitamin C, significantly reduced the intensity of the UVA induced erythema (p=0.001).

Visual Assessment of UVA Induced Erythema

Each sample was measured against sample C, which is the control formulation containing only the carrier and no active.

Sample A, containing 2% phloretin, visually significantly reduced the intensity of the UVA erythema (p=0.018).

Sample B, containing 15% vitamin C, visually significantly reduced the intensity of the UVA erythema (p=0.033).

Sample D, containing 2% phloretin and 0.5% ferulic acid, visually significantly reduced the intensity of the UVA erythema (p=0.002).

Sample E, containing 15.3% Vitamin C, 0.5% ferulic acid and 1% Vitamin E visually significantly reduced the intensity of the UVA erythema (p=0.004).

Sample F, containing 2% phloretin, 0.5% ferulic acid and 15.3% vitamin C, visually significantly reduced the intensity of the UVA erythema (p=0.006).

Persistent Pigment Darkening (PPD)

Each sample was measured against sample C, which is the control formulation containing only the carrier and no active.

Sample A, containing 2% phloretin, significantly reduced the intensity of the UVA induced Persistent Pigment Darkening (PPD) (p=0.016).

Sample B, containing 15% vitamin C, did not show significant differences in the intensity of the UVA induced Persistent Pigment Darkening (PPD) vs. the control.

Sample D, containing 2% phloretin and 0.5% ferulic acid, significantly reduced the intensity of the UVA induced Persistent Pigment Darkening (PPD) (p=0.003).

Sample E, containing 15.3% Vitamin C, 0.5% ferulic acid and 1% Vitamin E significantly reduced the intensity of the UVA induced Persistent Pigment Darkening (PPD) (p=0.018).

Sample F, containing 2% phloretin, 0.5% ferulic acid and 15.3% vitamin C, significantly reduced the intensity of the UVA induced Persistent Pigment Darkening (PPD) (p=0.000).

In summary the results for Set 1 may be expressed as follows: Student's T-Test on pairs of data (n=10):

Formula vs. control Δa* Visual ΔE
A **(p = 0.013) **(p = 0.018) **(p = 0.016)
Phloretin: 2%
B NSD **(p = 0.033) NSD
Vitamin C: 15%
D **(p = 0.007) **(p = 0.002) **(p = 0.003)
Phloretin: 2%
Ferulic Acid: 0.5%
E **(p = 0.023) **(p = 0.004) **(p = 0.018)
Vitamin C: 15.3%
Ferulic Acid: 0.5%
Vitamin E: 1%
F **(p = 0.001) **(p = 0.006) **(p = 0.000)
Vitamin C: 15.3%
Ferulic Acid: 0.5%
Phloretin: 2%
**Significant difference vs. control
*Trend
NSD: No Significant Difference

Set 2 Results

UVA Induced Erythema

Each sample was measured against sample J, which is the control formulation containing only the carrier and no active.

Sample G, containing 15% Vitamin C, 0.5% Ferulic acid, 2% Phloretin and 0.02% Vitamin E, significantly reduced the intensity of the UVA induced erythema (p=0.012).

Sample H, containing 15% Vitamin C and 2% Phloretin, did not show any significant difference at the 95% confidence level.

Sample I, containing 0.5% Ferulic acid, did not show any significant difference at the 95% confidence level.

Sample K, containing 15.3% Vitamin C, 0.5% Ferulic Acid, and 1.0% Vitamin E, significantly reduced the intensity of the UVA induced erythema (p=0.018).

Sample L, containing 15% Vitamin C, 0.5% Ferulic acid and 2% Phloretin, significantly reduced the intensity of the UVA induced erythema (p=0.026).

Visual Assessment of UVA Induced Erythema

Each sample was measured against sample J, which is the control formulation containing only the carrier and no active.

Sample G, containing 15% Vitamin C, 0.5% Ferulic acid, 2% Phloretin and 0.02% Vitamin E, visually significantly reduced the intensity of the UVA induced erythema (p=0.016).

Sample H, containing 15% Vitamin C and 2% Phloretin, visually significantly reduced the intensity of the UVA induced erythema (p=0.006)

Sample I, containing 0.5% Ferulic acid, visually significantly reduced the intensity of the UVA induced erythema (p=0.011).

Sample K, containing 15.3% Vitamin C, 0.5% Ferulic Acid, and 1.0% Vitamin E, visually significantly reduced the intensity of the UVA induced erythema (p=0.007).

Sample L, containing 15% Vitamin C, 0.5% Ferulic acid and 2% Phloretin, visually significantly reduced the intensity of the UVA induced erythema (p=0.012).

Persistent Pigment Darkening (PPD)

Each sample was measured against sample J, which is the control formulation containing only the carrier and no active.

Sample G, containing 15% Vitamin C, 0.5% Ferulic acid, 2% Phloretin and 0.02% Vitamin E, significantly reduced the intensity of the UVA induced Persistent Pigment Darkening (PPD) (p=0.002).

Sample H, containing, 15% Vitamin C and 2% Phloretin, did not show any significant difference at the 95% confidence level.

Sample I, containing 0.5% Ferulic acid, did not show any significant difference at the 95% confidence level.

Sample K, containing 15.3% Vitamin C, 0.5% Ferulic Acid, and 1.0% Vitamin E, reduced the intensity of UVA induced Persistent Pigment Darkening (PPD) (p=0.055).

Sample L, containing 15% Vitamin C, 0.5% Ferulic acid and 2% Phloretin, significantly reduced the intensity of UVA induced Persistent Pigment Darkening (PPD) (p=0.027).

In summary the results for Set 2 may be expressed as follows:

Student's T-Test on pairs of data (n=10):

Formula vs. control Δa* Visual ΔE
G **(p = 0.012) **(p = 0.016) **(p = 0.002)
Vitamin C: 15%
Ferulic Acid: 0.5
Phloretin: 2%
Vitamin E: 0.02%
H NSD **(p = 0.006) NSD
Vitamin C: 15%
Phloretin: 2%
I NSD **(p = 0.011) NSD
Ferulic Acid: 0.5%
K **(p = 0.018) **(p = 0.007) *(p = 0.055)
Vitamin C: 15.3%
Ferulic Acid: 0.5%
Vitamin E: 1%
L **(p = 0.026) **(p = 0.012) **(p = 0.027)
Vitamin C: 15.3%
Ferulic Acid: 0.5%
Phloretin: 2%
**Significant difference vs. control
*Trend
NSD: No Significant Difference

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US8568749 *Apr 2, 2010Oct 29, 2013Sesvalia Usa, LlcSystems and methods for skin rejuvenation
US20100255079 *Apr 2, 2010Oct 7, 2010Sesvalia Usa, LlcSystems and methods for skin rejuvenation
US20110077275 *Jul 27, 2010Mar 31, 2011Jan ZielinskiAntioxidant compositions for soft oral tissue and methods of formulation and use thereof
WO2010062835A1 *Nov 20, 2009Jun 3, 2010Perio Sciences, LlcAntioxidant compositions for soft oral tissue and methods of formulation and use there
WO2011162954A2 *Jun 8, 2011Dec 29, 2011NY Derm LLCMulti-active microtargeted anti-aging skin cream polymer technology
WO2013045383A1Sep 24, 2012Apr 4, 2013Dsm Ip Assets B.V.Novel compositions
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Classifications
U.S. Classification514/456, 514/569, 514/733, 514/458, 514/725, 514/474
International ClassificationA61K31/353, A61K31/192, A61K31/7048, A61K31/07, A61K31/355, A61K31/05, A61K31/375
Cooperative ClassificationA61K8/676, A61K31/07, A61K8/347, A61K31/355, A61K31/375, A61K8/678, A61K31/192, A61Q19/08, A61K8/671, A61K8/36, A61K8/365, A61Q17/04, A61K8/35, A61K31/353, A61K31/05, A61K31/7048
European ClassificationA61K8/36, A61Q17/04, A61K8/67C, A61K8/34F, A61K8/67L, A61Q19/08, A61K8/35, A61K8/365, A61K8/67H, A61K31/07, A61K31/192, A61K31/353, A61K31/375, A61K31/7048, A61K31/05, A61K31/355
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