A COMPOSITION INCLUDING SPARINGLY WATER-SOLUBLE ACTIVE PHENOLIC

COMPOUND AND VINYLPYRROLIDONE COPOLYMER

TECHNICAL FIELD

The present invention relates to a composition, in particular a cosmetic composition, including a sparingly water-soluble polyphenol compound, preferably for a keratinous substance such as skin.

BACKGROUND ART

Compositions, such as cosmetic or dermatological products, including sparingly water-soluble active compounds have problems in terms of poor stability and bioavailability of the active compounds if the compositions are aqueous. Up to the present date, in order to solve these problems, some prior arts describe a method for increasing water solubility of sparingly water-soluble active compounds. For example, WO2013/106,433 discloses compositions comprising cellulose esters and sparingly water-soluble drugs, in which the cellulose esters may increase solubility of the drugs as compared to the drugs alone.

In addition, WO2013/158992 discloses a composition for increasing solubility of a solute compound, comprising: a highly branched alpha-D-glucan or a modified form thereof; and a solute compound having an aqueous solubility that is greater than the aqueous solubility of the solute compound in the absence of the highly branched alpha-D-glucan.

DISCLOSURE OF INVENTION

There is still a need for a new approach to increase the solubility of a sparingly water-soluble compound in a composition including water and the sparingly water-soluble compound. This need also applies to a sparingly water-soluble polyphenol compound which may be used as a cosmetically or dermatologically active compound such as a whitening agent.

On the other hand, there is also a need for providing a composition including water and a sparingly water-soluble compound with good texture, in particular if the composition is used as a cosmetic or dermatological product. Thus, an objective of the present invention is to provide a composition including a sparingly water-soluble polyphenol compound and water with increased solubility of the sparingly water-soluble polyphenol compound, while providing the composition with good texture such as less stickiness and freshness. The above objective can be achieved by a composition comprising:

(a) at least one sparingly water-soluble polyphenol compound;

(b) at least one nonionic or cationic vinylpyrrolidone copolymer;

(c) water; and

(d) at least one basic amino acid. The (a) sparingly water-soluble polyphenol compound may have a water-solubility of less than 1% by weight, preferably less than 0.1% by weight, more preferably less than 0.01% by weight, at room temperature, without the (b) nonionic or cationic vinylpyrrolidone copolymer. The (a) sparingly water-soluble polyphenol compound may be selected from tannins and derivatives thereof, stilbenoids and derivatives thereof, and resorcinol derivatives.

The (a) sparingly water-soluble polyphenol compound may be selected from ellagic acid, resveratrol, and phenyl ethyl resorcinol.

The amount of the (a) sparingly water-soluble polyphenol compound(s) in the composition may be from 0.01 to 20% by weight, preferably from 0.03 to 10% by weight, and more preferably from 0.05 to 3%> by weight, relative to the total weight of the composition. The (b) nonionic or cationic vinylpyrrolidone copolymer may not be crosslinked.

The (b) nonionic or cationic vinylpyrrolidone copolymer may be selected from copolymers of vinylpyrrolidone and at least one monomer selected from the group consisting of

(meth)acrylic acid; (meth)acrylates; unsaturated hydrocarbons; and vinyl monomers.

The amount of the (b) nonionic or cationic vinylpyrrolidone copolymer in the composition according to the present invention may be from 0.01 to 30% by weight, preferably from 0.1 to 20% by weight, and more preferably from 1 to 10% by weight, relative to the total weight of the composition.

The weight ratio of (b) nonionic or cationic vinylpyrrolidone copolymer/(a) sparingly water-soluble polyphenol compound in the composition according to the present invention may be 50 or less, preferably 40 or less, and more preferably 30 or less. The amount of (c) water in the composition according to the present invention may be from 50 to 99% by weight, preferably from 60 to 98% by weight, and more preferably from 70 to 97% by weight, relative to the total weight of the composition.

The (d) basic amino acid may be selected from the group consisting of arginine, lysine, histidine and mixtures thereof.

The amount of the (d) basic amino acid(s) in the composition according to the present invention may be from 0.01 to 20%> by weight, preferably from 0.1 to 10% by weight, and more preferably from 0.5 to 5% by weight, relative to the total weight of the composition.

The composition according to the present invention may have a pH of from 5.5 to 8.5, preferably from, 6.0 to 8.0, and more preferably from 6.5 to 7.5.

The present invention also relates to a cosmetic process, preferably a whitening process, for a keratin substance, preferably skin, comprising the step of applying to the keratin substance the composition according to the present invention.

Another aspect of the present invention is a use of (b) at least one nonionic or cationic vinylpyrrolidone copolymer and (d) at least one basic amino acid in a composition comprising (a) at least one sparingly water-soluble polyphenol compound and (c) water, in order to increase the solubility of the (a) sparingly water-soluble polyphenol compound in the composition and to provide the composition with less stickiness and/or freshness.

BEST MODE FOR CARRYING OUT THE INVENTION

After diligent research, the inventors have discovered that it is possible to provide a composition including a sparingly water-soluble polyphenol compound and water with increased solubility of the sparingly water-soluble polyphenol compound, while providing the composition with a good texture such as less stickiness and freshness.

Thus, the composition according to the present invention comprises:

(a) at least one sparingly water-soluble polyphenol compound;

(b) at least one nonionic or cationic vinylpyrrolidone copolymer;

(c) water; and

(d) at least one basic amino acid.

The composition according to the present invention can increase the solubility in water of the sparingly water-soluble polyphenol compound. In other words^ the composition according to the present invention can increase the amount of a sparingly water-soluble polyphenol compound dissolved in water. Accordingly, the composition according to the present invention can be stable for a long period of time, because the sparingly water-soluble polyphenol compound can be dissolved in the composition even if the amount of the polyphenol compound is increased. The term "stable" here means that the sparingly water-soluble polyphenol compound can be maintained dissolved in the composition, and does not precipitate in the composition. The stable composition can be homogeneous or transparent, while the unstable composition can be heterogeneous or opaque/translucent. In addition, the composition according to the present invention can provide the improved bioavailability of the polyphenol compound.

Increasing the water solubility of polyphenol compound(s) refers to increasing the solubility of the polyphenol compound(s) in water in comparison with solubility of the polyphenol compound(s) in water in the absence of the nonionic or cationic vinylpyrrolidone copolymer and the basic amino acid.

In addition, the composition according to the present invention can have excellent texture such as less stickiness and freshness, which can be useful for cosmetic and/or dermatological products.

Also, the use according to the present invention can increase the solubility of a sparingly water-soluble polyphenol compound in a composition comprising water and the sparingly water-soluble polyphenol compound, while providing the composition with less stickiness and/or freshness.

Hereafter, the composition, use and the like according to the present invention will be described in a detailed manner.

[Composition] The composition according to the present invention comprises (a) at least one sparingly water-soluble polyphenol compound, (b) at least one nonionic or cationic vinylpyrrolidone copolymer, and (d) at least one basic amino acid.

It is preferable that the composition according to the present invention is a cosmetic or dermatological composition, more preferably a cosmetic composition, and even more preferably a cosmetic care composition for a keratin substance such as skin. In particular, the composition according to the present invention can be used as a cosmetic or

dermatological product for whitening the keratin substance such as skin.

The (a) sparingly water-soluble polyphenol compound, (b) nonionic or cationic

vinylpyrrolidone copolymer, and (d) basic amino acid as well as the other features of the composition according to the present invention will be explained below.

(Sparingly Water-Soluble Active Polyphenol Compound)

The composition according to the present invention comprises (a) at least one sparingly water-soluble polyphenol compound. Two or more the (a) sparingly water-soluble polyphenol compounds may be used in combination. Thus, a single type of the sparingly water-soluble polyphenol compound or a combination of different types of sparingly water-soluble polyphenol compounds may be used.

The term "sparingly water-soluble" here means poor solubility in water. Therefore, a sparingly water-soluble compound used herein is difficult to dissolve in water. Thus, the "sparingly water-soluble" polyphenol compound may be a compound having a

water-solubility less than 1% by weight, preferably less than 0.1% by weighty more preferably less than 0.01% by weight at room temperature (20-25°C, preferably 25°C) without the (b) nonionic or cationic vinylpyrrolidone copolymer or the (d) basic amino acid explained later. In other words, the "sparingly water-soluble" polyphenol compound may have a solubility in pure water of less than 1% by weight, preferably less than 0.1% by weight, more preferably less than 0.01% by weight at room temperature (20-25°C, preferably 25°C).

The (a) sparingly water-soluble polyphenol compound used in the present invention has two or more phenolic hydroxyl groups in one molecule. The (a) sparingly water-soluble polyphenol compound includes derivatives, such as glycoside forms, salts, acid forms, and reduction forms of polyphenol compounds.

The (a) sparingly water-soluble polyphenol compound may be an active ingredient or active compound in cosmetics or dermatological products. The term an "active" compound used herein means a compound which has a cosmetic or dermatological active property, such as anti-oxidant, whitening, and anti-bacterial effects. Preferably, the (a) sparingly water-soluble polyphenol compound used in the present invention may be a whitening agent, and thus the composition according to the present invention may be used as a whitening products or as a cosmetic composition for whitening keratin substance such as skin.

The (a) sparingly water-soluble polyphenol compounds which can be used in the present invention may be flavonoids and non-flavonoids. The flavonoids may be selected from a group consisting of chalcones, flavones, flavanones, flavanols, flavonols, dihydroflavonols, isoflavonoids, neoflavonoids, catechins, anthocyanidins, tannins, and derivatives thereof. In particular, the flavonoids may be tannins and derivatives thereof. The tannins and their derivatives may be selected from a group consisting of ellagic acid, geraniin, catechins, procyanidin, profisetinidin, prodelphinidin, and derivatives thereof.

Among these tannins, the present invention in particular may preferably use ellagic acid as the (a) sparingly water-soluble polyphenol compound, because ellagic acid has whitening effects. Ellagic acid is represented by the following chemical formula. Ellagic acid can be obtained, for example, from Minasolve (the product name: Minacare Elage).

The non-flavonoids may be selected from a group consisting of lignans, aurones, stilbenoids, curcuminoids and other phenylpropanoids, and derivatives thereof, such as resorcinol derivatives. In particular, the non-flavonoids may be selected from stilbenoids and derivatives thereof and resorcinol derivatives. The stilbenoids and derivatives may be selected from a group consisting of piceatannol, pinosylvin, resveratrol, and derivatives thereof. Among these stilbenoids, the present invention may preferably use resveratrol as the (a) sparingly water-soluble polyphenol compound, resveratrol has whitening effects. Resveratrol is represented by the following chemical formula. Resveratrol can be obtained, for example, from Symrise Corp.

The resorcinol derivative may preferably be 4-position substituted derivatives, such as 4-alkylresorcinols, more preferably phenyl ethyl resorcinol, 4-n-butylresorcinol and

4-(tetrahydro-2H-pyran-4-yl) benzene- 1, 3 -diol, and in particular phenyl ethyl resorcinol because of its whitening effect. Phenyl ethyl resorcinol is also refereed as

4-(l-phenylethyl)-l,3-benzenediol and represented by the following chemical formula.

Phenyl ethyl resorcinol can be obtained, for example, from Symrise Corp (the product name: Symwhite 377 ^® ).

As other examples of resorcinol derivatives, mention may be made of: 2-methylresorcinol, 5-methylresorcinol, 4-methylresorcinol, 4-ethylresorcinol, 2,5-dimethylresorcinol,

4,5-dimethylresorcinol, 2,4-dimethyl-l,3-benzenediol, 3,5-dihydroxybenzylamine,

5-methoxyresorcinol, 3,5-dihydroxybenzyl alcohol, 2-methoxyresorcinol,

4-methoxyresorcinol, 3,5-dihydroxytoluene monohydrate, 4-chlororesorcinol,

2-chlororesorcinol, 2',4'-dihydroxyacetophenone, 3',5'-dihydroxyacetophenone,

2,6-dihydroxy-4-methylbenzaldehyde, 4-propylresorcinol,

2,4-dihydroxy-l,3,5-trimethylbenzene, 3,5-dihydroxybenzamide, 2,6-dihydroxybenzamide,

2.4- dihydroxybenzamide, 2,4-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid,

3.5- dihydroxybenzoic acid, 2,6-dihydroxy-4-methylbenzyl alcohol, 3,5-dihydroxyanisole hydrate, 4-aminoresorcinol hydrochloride, 2-aminoresorcinol hydrochloride,

5 -aminobenzene- 1 ,3 -diol hydrochloride, 2 ' ,4 ' -dihydroxypropiophenone,

2',4'-dihydroxy-3'-methylacetophenone, (2,4-dihydroxyphenyl)acetone,

(3,5-dihydroxyphenyl)acetone, 2,6-dihydroxy-4'-methylacetophenone, 4-n-butylresorcinol,

2.4- diethyl-l,3-benzenediol, 3,5-dihydroxy-4-methylbenzoic acid,

2.6- dihydroxy-4-methylbenzoic acid, 2,4-dihydroxy-6-methylbenzoic acid,

3.5- dihydroxyphenylacetic acid, 2-ethyl-5 -methoxybenzene- 1 ,3 -diol,

4-amino-3,5-dihydroxybenzoic acid, 3,5-dihydroxyacetophenone monohydrate,

3,5-dihydroxybenzylamine hydrochloride, 4,6-dichlororesorcinol,

2 ' ,4 ' -dihydroxy-3 ' -methylpropiophenone, 1 -(3 -ethyl-2,6-dihydroxyphenyl)ethan- 1 -one, 2 ' ,6 ' -dihydroxy-4 ' -methoxyacetophenone, 1 -(2,6-dihydroxy-3 -methoxyphenyl)ethan- 1 -one, 3(2,4-dihydroxyphenylpropionic acid, and 2,4-dihydroxy-3,6-dimethylbenzoic acid.

The salts of the (a) sparingly water-soluble polyphenol compound include conventional non-toxic salts of said compounds, such as those formed from an acid or from a base.

Salts of the (a) sparingly water-soluble polyphenol compound include the following:

a) salts obtained by addition of the compound with a mineral acid, selected more particularly from hydrochloric, boric, hydrobromic, hydroic, sulphuric, nitric, carbonic, phosphoric and tetrafluoroboric acids; or

b) salts obtained by addition of the compound with an organic acid, more particularly selected from acetic, propionic, succinic, fumaric, lactic, glycolic, citric, gluconic, salicylic, tartaric, terephthalic, methylsulphonic, ethylsulphonic, benzene sulphonic, toluene sulphonic and triflic acids.

Also included are the salts obtained by addition of the (a) sparingly water-soluble polyphenol compound with a mineral base, such as aqueous sodium hydroxide and potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium, potassium or calcium carbonates or hydrogencarbonates, for example; or with an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine.

The salts of the (a) sparingly water-soluble polyphenol compounds may advantageously be selected from alkali metal salts or alkaline earth metal salts such as sodium, potassium, calcium and magnesium salts; and ammonium salts.

It may be preferable that the (a) sparingly water-soluble polyphenol compound be selected from tannins and derivatives thereof, stilbenoids and derivatives thereof, and resorcinol derivatives.

It may be more preferable that the (a) sparingly water-soluble polyphenol compound be selected from ellagic acid, resveratrol, and phenyl ethyl resorcinol.

The amount of the (a) sparingly water-soluble polyphenol compound(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.03% by weight or more, and more preferably 0.05% by weight or more, relative to the total weight of the composition. It may be even more preferable that the amount of the (a) sparingly water-soluble polyphenol compound(s) in the composition according to the present invention be 0.2% by weight or more, relative to the total weight of the composition.

On the other hand, the amount of the (a) sparingly water-soluble polyphenol compound(s) in the composition according to the present invention may be 20% by weight or less, preferably 10% by weight of less, and more preferably 3% by weight or less, relative to the total weight of the composition. It may be even more preferable that the amount of the (a) sparingly water-soluble polyphenol compound(s) in the composition according to the present invention be 2%) by weight or less, relative to the total weight of the composition.

The amount of the (a) sparingly water-soluble polyphenol compound(s) in the composition according to the present invention may range from 0.01 to 20% by weight, preferably from 0.03 to 10%) by weight, more preferably from 0.05 to 3%> by weight, relative to the total weight of the composition. It may be even more preferable that the amount of the (a) sparingly water-soluble polyphenol compound(s) in the composition according to the present invention be from 0.2%) to 2%> by weight, relative to the total weight of the composition. (Nonionic or Cationic Vinylpyrrolidone Copolymer)

The composition according to the present invention comprises (b) at least one nonionic or cationic vinylpyrrolidone copolymer. Two or more (b) nonionic or cationic vinylpyrrolidone copolymers may be used in combination. Thus, a single type of the nonionic or cationic vinylpyrrolidone copolymer or a combination of different types of nonionic or cationic vinylpyrrolidone copolymers may be used.

As the (b) nonionic or cationic vinylpyrrolidone copolymer, any type of nonionic or cationic vinylpyrrolidone copolymer may be used. However, it is preferable that the (b) nonionic or cationic vinylpyrrolidone copolymer be not crosslinked.

The term "copolymer" here includes a polymer obtained by co-polymerization of .

vinylpyrrolidone and one co-monomer other than vinylpyrrolidone, as well as a polymer obtained by co-polymerization of vinylpyrrolidone and two or more co-monomers other than vinylpyrrolidone. It may be preferable that the (b) nonionic or cationic vinylpyrrolidone copolymer is a copolymer of vinylpyrrolidone and one co-monomer. The (b) nonionic or cationic vinylpyrrolidone copolymer is not a homopolymer of vinylpyrrolidone.

The (b) nonionic or cationic vinylpyrrolidone copolymer has at least one pendant ring structure derived from the vinylpyrrolidone. On the other hand, it is preferable that the (b) nonionic or cationic vinylpyrrolidone polymer comprise no ring structure in the backbone of the polymer.

The (b) nonionic or cationic vinylpyrrolidone copolymer has no cationic/anionic moiety or has only at least one cationic moiety or group in the copolymer backbone or a pendent group or groups of the copolymer.

The (a) sparingly water-soluble polyphenol compound and the (b) nonionic or cationic vinylpyrrolidone copolymer may form a complex. The term "complex" used herein refers to a substance or a formation in which intermolecular interactions occur as a result of combining the (a) sparingly water-soluble polyphenol compound and the (b) nonionic or cationic vinylpyrrolidone copolymer. The complex can be, for example, adducts, associates, aggregates or inclusion compounds. In terms of the formation of the complex, it may be preferable that the (b) nonionic or cationic vinylpyrrolidone copolymer be a random copolymer, not a block copolymer.

The (b) nonionic or cationic vinylpyrrolidone copolymer may be selected from copolymers of vinylpyrrolidone and at least one monomer selected from the group consisting of

(meth)acrylic acid; (meth)acrylates; unsaturated hydrocarbons; and vinyl monomers.

In other words, the (b) nonionic or cationic vinylpyrrolidone copolymer may be obtained by co-polymerization of vinylpyrrolidone and at least one co-monomer selected from the group consisting of acrylic acid or methacrylic acid; acrylates or methacrylates; unsaturated hydrocarbons, preferably alkenes such as styrene, butadiene, hexadecene, eicosene, decene, and triacontene; and vinyl monomers.

As examples of the acrylates or methacrylates, mention may be made of methyl acrylate, ethyl acrylates, dimethylaminomethyl acrylate, dimethylaminoethyl acrylate, methyl methacrylate, ethyl methacrylates, dimethylaminomethyl methacrylate, dimethylaminoethyl methacrylate, quaternized dimethylaminomethyl methacrylate, quaternized dimethylaminoethyl

methacrylate, and methacrylamidopropyltrimethylammonium.

As examples of the vinyl monomers, mention may be made of vinyl alcohol, vinyl acetate, vinyl propionate, vinyl neodecanoate, vinyl pivalate, vinyl benzoate, vinyl t-butyl benzoate, vinyl caprolactam and methylvinylimidazolium.

As examples of the nonionic vinylpyrrolidone copolymer, mention may be made of:

a copolymer of vinylpyrrolidone and vinyl acetate (PVP/VA Copolymer) such as Luviskol VA64 Poudre by BASF and PVP VA E335 by ISP;

a copolymer of vinylpyrrolidone and vinyl alcohol (VP/Vinyl Alcohol Copolymer) such as Selvol Ultalux SC PVOH Copolymer by Sekisui;

a copolymer of vinylpyrrolidone and hexadecene (PVP/Hexacedene Copolymer) such as Antaron V-216 by ISP;

a copolymer of vinylpyrrolidone and triacontene (Tricontanyl PVP) such as Antaron WP-660 by ISP;

a copolymer of vinylpyrrolidone and eicosene (PVP/Eicosene Copolymer) such as Antaron V-220 by ISP;

a terpolymer of vinylpyrrolidone, vinyl acetate and vinyl propionate (PVP/VA/Vinyl

Propionate Copolymer) such as Luviskol VAP3431 and Luviskol VAP 343E by BASF;

a terpolymer of vinylpyrrolidone, vinyl caprolactam and dimethylaminoethyl methacrylate (Vinyl Caprilactam/PVP/Dimethylaminoethyl Methacrylate Copolymer) such as Copolymer VC-713 by ISP; and

a mixture thereof.

On the other hand, the cationic vinylpyrrolidone copolymer may be chosen from the group consisting of:

vinylpyrrolidone copolymers comprising dimethylaminoethyl methacrylate units, vinylpyrrolidone copolymers comprising methacrylamidopropyltrimethylammonium units, and

vinylpyrrolidone copolymers comprising methylvinylimidazolium units.

The cationic vinylpyrrolidone copolymers comprising dimethylaminoethyl methacrylate units may be chosen from:

vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers; for example, vinylpyrrolidone/dimethylaminoethyl methacrylate copolymer (20/80 by weight) sold under the trade name Copolymer 845 by the company I.S.P.,

vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers quaternized with diethyl sulphate; for example, vinylpyrrolidone/dimethylaminoethyl methacrylate copolymer quaternized with diethyl sulphate, sold under the trade names Gafquat 734, 755, 755S and 755L by the company I.S.P,

vinylpyrrolidone/dimethylaminoethyl methacrylate/hydrophilic polyurethane copolymers; for example, vinylpyrrolidone/dimethylaminoethyl

methacrylate/hydrophilic polyurethane copolymer, sold under the trade name Pecogel GC-310 by the company U.C.I. B., or under the trade names Aquamere C 1031 and C 1511 by the company Blagden Chemicals,

vinylpyrrolidone/dimethylaminoethyl methacrylate/C ₈ -C ₁₆ olefin copolymers, quaternized or non-quaternized; for example, vinylpyrrolidone/dimethylaminoethyl methacrylate/C ₈ -C ₁₆ olefin copolymer sold under the trade names Ganex ACP1050 to 1057, 1062-1069 and 1079-1086 by the company I.S.P.,

and

vinylpyrrolidone/dimethylaminoethyl methacrylate/vinylcaprolactam copolymers; for example, vinylpyrrolidone/dimethylaminoethyl methacrylate/vinylcaprolactam copolymer sold under the trade name Gaffix VC713 by the company I.S.P.

The cationic vinylpyrrolidone copolymers comprising

methacrylamidopropyltrimethylammonium (MAPTAC) units may be chosen from:

vinylpyiTolidone/methaciylamidopropyltrimethylammonium copolymers; for example, vinylpyrrolidone/MAPTAC copolymer sold under the trade names Gafquat ACP1011 and Gafquat HS100 by the company I.S.P.,

and

vinylpyrrolidone/methaciylamidopropyltrimethylammonium/vinyl caprolactam terpolymers; for example, vinylpyrrolidone/MAPTAC/vinylcaprolactam terpolymer sold under the trade names Polymer ACP 1059, 1060 and 1156 by the company I.S.P. The cationic vinylpyrrolidone copolymers comprising methylvinylimidazolium units may be chosen from

vinylpyrrolidone/methylvinylimidazolium chloride copolymers; for example, vinylpyrrolidone/methylvinylimidazolium chloride copolymer sold under the trade names Luviquat FC370, FC550, FC905 and HM552 by the company BASF, vinylpyrrolidone/methylvinylimidazolium chloride/vinylimidazole copolymers; for example, vinylpyrrolidone/methylvinylimidazolium chloride/vinylimidazole copolymer sold under the trade name Luviquat 8155 by the company BASF, vinylpyrrolidone/vinyl caprolactam/vinylimidazolium copolymers; for example, vinylpyrrolidone/vinylcaprolactam/vinylimidazolium methosulfate copolymer sold under the trade name Luviquat Hold by the company BASF,

and

vinylpyrrolidone/methylvinylimidazolium methosulphate copolymers; for example, vinylpyrrolidone/methylvinylimidazolium methosulphate copolymer sold under the trade name Luviquat MS370 by the company BASF.

It may be preferable that the cationic vinylpyrrolidone copolymer be chosen from

vinylpyrrolidone polymers comprising dimethylaminoethyl methacrylate units, more preferably chosen from vinylpyrrolidone/dimethylaminoethyl methacrylate copolymers, for example those sold under the name COPOLYMER 845-0 by the company ASHLAND.

It may be preferable that the cationic vinylpyrrolidone copolymer be chosen from

vinylpyrrolidone polymers comprising methacrylamidopropyltrimethylammonium units, and more preferably Polyquaternium-28.

It may also be preferable that the cationic vinylpyrrolidone copolymer be chosen from vinylpyrrolidone polymers comprising methylvinylimidazolium units, more preferably chosen from vinylpyrrolidone/methylvinylimidazolium copolymers, and even more preferably Polyquaternium-16 for example those sold under the trade name LUVIQUAT FC 370 by the company AROMAT.

The amount of the (b) nonionic or cationic vinylpyrrolidone copolymer(s) in the composition according to the present invention may be 0.01 % by weight or more, preferably 0.1% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition. It may be even more preferable that the amount of the (b) nonionic or cationic vinylpyrrolidone copolymer(s) in the composition according to the present invention be 2% by weight or more, relative to the total weight of the composition.

On the other hand, the amount of the (b) nonionic. or cationic vinylpyrrolidone copolymer(s) in the composition according to the present invention may be 30% by weight or less, preferably 20% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition. It may be even more preferable that the amount of the (b) nonionic or cationic vinylpyrrolidone copolymer(s) in the composition according to the present invention be 5% by weight or less, relative to the total weight of the composition.

The amount of the (b) nonionic or cationic vinylpyrrolidone copolymer(s) in the composition according to the present invention may range from 0.01 to 30% by weight, preferably from 0.1 to 20% by weight, more preferably from 1 to 10% by weight, relative to the total weight of the composition. It may be even more preferable that the amount of the (b) nonionic or cationic vinylpyrrolidone copolymer(s) in the composition according to the present invention be from 2% to 5% by weight, relative to the total weight of the composition.

The weight ratio of (b) nonionic or cationic vinylpyrrolidone copolymer/(a) sparingly water-soluble polyphenol compound in the composition according to the present invention may be 50 or less, preferably 40 or less, and more preferably 30 or less.

(Water)

The composition according to the present invention includes (c) water.

The amount of the (c) water in the composition according to the present invention may be 50% by weight or more, preferably 60% by weight or more, and more preferably 70% by weight or more, relative to the total weight of the composition. It may be even more preferable that the amount of the (c) water in the composition according to the present invention be 80% by weight or more, relative to the total weight of the composition.

On the other hand, the amount of the (c) water in the composition according to the present invention may be 99% by weight or less, preferably 98% by weight or less, and more preferably 97% by weight or less, relative to the total weight of the composition. It may be even more preferable that the amount of the (c) water in the composition according to the present invention be 96% by weight or less, relative to the total weight of the composition.

The amount of (c) water in the composition according to the present invention may be from 50 to 99% by weight, preferably from 60 to 98% by weight, and more preferably from 70 to 97% by weight, relative to the total weight of the composition. It may be even more preferable that the amount of the (c) water in the composition according to the present invention be from 80% to 96% by weight, relative to the total weight of the composition.

(Basic Amino Acid)

The composition according to the present invention comprises (d) at least one basic amino acid. Two or more basic amino acids may be used in combination. Thus, a single type of the basic amino acid or a combination of different types of basic amino acids may be used. The term "amino acid" here means a compound which is not obtained by polycondensation of identical or different amino acids. In addition, the term "amino acid" here encompasses not only an amino acid itself but also an amino acid in the form of a salt thereof. As the salt, mention may be made of sodium salt, magnesium salt, potassium salt, calcium salt, and the like.

The amino acids that may be used according to the present invention comprise at least one amine function and at least one acid function.

The acid function(s) may be carboxylic, sulfonic, phosphonic or phosphoric, and are preferably carboxylic.

The amino acids that may be used according to the present invention may be a-amino acids, β-amino acids, or γ-amino acids. Preferably, the amino acids used in the present invention are a-amino acids, i.e., they comprise an amine function and an acid function at the same carbon atom. The basic amino acid used in the present invention may have two or more amine functional groups such as amino groups and one acid functional group such as a carboxyl group, preferably two amine functional groups such as amino groups and one acid functional group such as a carboxylic group.

As basic amino acids that may be used in the present invention, mention may be made of arginine, lysine, histidine, ornithine and mixtures thereof. The amount of the (d) basic amino acid(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.1 % by weight or more, and more preferably 0.5% by weight or more, relative to the total weight of the composition. It may be even more preferable that the amount of the (d) basic amino acid(s) in the composition according to the present invention be 0.8% by weight or more, relative to the total weight of the composition.

On the other hand, the amount of the (d) basic amino acid(s) in the composition according to the present invention may be 20% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition. It may be even more preferable that the amount of the (d) basic amino acid(s) in the composition according to the present invention be 3% by weight or less, relative to the total weight of the composition.

The amount of the (d) basic amino acid(s) in the composition according to the present invention may be from 0.01 to 20% by weight, preferably from 0.1 to 10% by weight, and more preferably from 0.5 to 5% by weight, relative to the total weight of the composition. It may be even more preferable that the amount of the (d) basic amino acid(s) in the

composition according to the present invention be from 0.8% to 3% by weight, relative to the total weight of the composition.

The composition according to the present invention may have a pH of from 5.5 to 8.5, preferably ^' from, 6.0 to 8.0, and more preferably from 6.5 to 7.5.

(Other Optional Additives)

The composition according to the present invention may also comprise any other optional additive(s) usually used in the field of cosmetics, chosen, for example, from oils, anionic, cationic, amphoteric or nonionic surfactants, solvents, gums, resins, hydrophilic thickening agents, hydrophobic thickening agents, dispersants, antioxidants, film-forming agents, preserving agents, fragrances, neutralizers, pH adjusting agents, antiseptics, UV-screening agents, cosmetic active agents other than the ingredient (a), such as vitamins, moisturizers, emollients or collagen-protecting agents, and mixtures thereof.

As the pH adjusting agent, at least one acidifying agent and/or at least one basifying agent (alkaline agent) may be used.

The acidifying agents can be, for example, mineral or organic acids, for instance hydrochloric acid, phosphoric acid, carboxylic acids, for instance tartaric acid, citric acid, and lactic acid, or sulphonic acids. The acidifying agent may be present in an amount ranging from less than 5% by weight, preferably from 3% by weight or less, and more preferably from 1% by weight or less, relative to the total weight of the composition. The basifying agent or alkaline agent can be, for example, any inorganic or organic basic agents which are commonly used in cosmetic products such as ammonia; alkanolamines such as mono-, di- and tri-ethanolamine, isopropanolamine; sodium and potassium hydroxides; urea, guanidine and their derivatives; basic amino acids such as lysine or arginine; and diamines such as those described in the structure below:

wherein

R denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C ₁ -C ₄ alkyl radical, and R ₁ , R ₂ , R ₃ , and R4 independently denote a hydrogen atom, an alkyl radical, or a C1-C4 hydroxyalkyl radical, which may be exemplified by 1,3-propanediamine, and derivatives thereof. Arginine, urea, and monoethanolamine may be preferable.

The composition according to the present invention may comprise at least one water-miscible solvent such as a lower monoalcohol containing from 1 to 5 carbon atoms, C3-C4 ketones or C ₃ -C ₄ aldehydes. The water-miscible solvent that can preferably be used is ethanol. The content of water-miscible solvent can range from 0.1% to 15% by weight, and better still from 1% to 8% by weight, relative to the total weight of the composition.

It is a matter of routine operations for a person skilled in the art to adjust the nature and amount of the above optional additives which may be present in the composition in accordance with the present invention such that the desired cosmetic properties are not thereby affected.

[Preparation]

The composition according to the present invention can be prepared by mixing the above-described essential and optional ingredients in a conventional manner.

For example, the composition according to the present invention can be prepared by a process comprising the step of

mixing

(a) at least one sparingly water-soluble polyphenol compound;

(b) at least one nonionic or cationic vinylpyrrolidone copolymer;

(c) water; and

(d) at least one basic amino acid.

It is possible to further mix any of the optional ingredients.

It may be more preferable that the (a) sparingly water-soluble polyphenol compound(s) and the (c) water be mixed firstly with (d) basic amino acid(s), to prepare a mixture of the ingredient (a) to the ingredient (c), and then the mixture be further mixed with the (b) nonionic or cationic vinylpyrrolidone copolymer to obtain the composition according to the present invention.

The mixing can be performed at any temperature such as room temperature (e.g., 20-25°C, preferably at 25°C), preferably at a temperature of 30°C or more, preferably 40°C or more, and more preferably 50°C or more. It is preferable to further mix with any of the

above-described optional ingredients such as a pH adjusting agent.

The form of the composition according to the present invention is not particularly limited, and may take various forms such as a W/O emulsion, an O/W emulsion, a gel, a solution, or the like. It is preferable that the composition according to the present invention be in the form of a solution, preferably an aqueous solution, and more preferably a transparent aqueous solution. [Cosmetic Process]

The composition according to the present invention may be used as a cosmetic or

dermatologic composition, preferably a cosmetic composition, and more preferably a cosmetic composition, for a keratin substance. As the keratin substance, mention may be made of the skin, scalp, hair, mucosa such as lips, and nails.

The composition according to the present invention may be used as an anti-oxidant, whitening, or anti-bacterial product for a keratinous substance such as skin. In particular, the

composition according to the present invention may be used as a whitening product.

The composition according to the present invention may preferably be intended for

application onto a keratin substance such as the skin, scalp and/or the lips, preferably the skin.

Thus, the composition according to the present invention can be used for a cosmetic process for a keratin substance, preferably the skin. In one embodiment, the present invention relates to a cosmetic process, preferably a whitening process, for a keratin substance, preferably skin, comprising the step of applying onto the keratin substance the composition according to the present invention. The composition according to the present invention can be used as a topical cosmetic composition in the form of a lotion, a milky lotion, a cream, a gel, a paste, a serum, foam, or spray.

[Use]

The present invention also relates to a use of (b) at least one nonionic or cationic

vinylpyrrolidone copolymer and (d) at least one basic amino acid in a composition comprising (a) at least one sparingly water-soluble polyphenol compound and (c) water, in order to increase the solubility of the (a) sparingly water-soluble polyphenol compound in the composition and to provide the composition with less stickiness and/or freshness.

The explanations regarding the (b) nonionic or cationic vinylpyrrolidone copolymer(s), the (d) basic amino acid(s), and the (a) sparingly water-soluble polyphenol compound(s) for the compositions according to the present invention can apply to those used in the use according to the present invention. The composition used in the use according to the composition may include any of the optional ingredients as explained above for the compositions according to the present invention. Thus, another aspect of the present invention may be a combination of (b) at least one nonionic or cationic vinylpyrrolidone copolymer and (d) at least one basic amino acid for use in the increase of the solubility of (a) sparingly water-soluble polyphenol compound in a composition comprising the (a) sparingly water-soluble polyphenol compound and water. EXAMPLES

The present invention will be described in a more detailed manner by way of examples.

However, these examples should not be construed as limiting the scope of the present invention.

[Examples 1-7 and Comparative Examples 1-12]

[Preparation] Each of the compositions according to Examples 1-7 and Comparative Examples 1-12 was prepared by mixing the ingredients shown in Tables 1 and 2 at room temperature (20-25 °C). The numerical values for the amounts of the ingredients are all based on "% by weight" as active raw materials. Please note that the citric acid or potassium hydroxide was added to adjust the pH of the composition to around 7.0.

Tables 1 and 2 indicate the following information regarding the compositions according to Examples 1-7 and Comparative Examples 1-12.

(1) The value of pH of the composition in the line of "pH"

(2) Whether the polymer in the composition has a vinylpyrrolidone group, as Yes or No, in the line of "Presence of VP group"

(3) Whether the polymer in the composition is nonionic or cationic, as Yes or No, in the line of "Nonionic or Cationic" [Evaluation] (Stability)

The stability of each of the compositions according to Examples 1-7 and Comparative Examples 1-12 was evaluated by visual observation of the aspect of the composition which was kept at room temperature (from 20 to 25 °C) for a 1 month, based on the following criteria.

Good: Transparent

Poor: Not Transparent

The "good" here means that ellagic acid is maintained dissolved in the composition, and does not precipitate in the composition. On the other hand, the "poor" here means that ellagic acid is not maintained dissolved in the composition so that ellagic acid was precipitated or deposited in the composition.

The results of the stability evaluation are shown in Tables 1 and 2.

Examples 1-7 show that the compositions according to Examples 1-7 can maintain ellagic acid dissolved at 0.1 or 0.2% by weight relative to the total weight of the composition for a long period of time. Since the solubility in pure water of ellagic acid at room temperature is less than 0.01% by weight, Examples 1-7 show that the solubility of ellagic acid is increased by the polymer used therein. Examples 1-5 show that the VP copolymers (nonionic) can contribute to dissolve ellagic acid at 0.1 or 0.2% by weight relative to the total weight of the composition. Example 6 and 7 show that the VP copolymers (cationic) can also contribute to dissolve ellagic acid at 0.1% by weight relative to the total weight of the composition. Comparative Example 1 shows that VP copolymers (nonionic) in the amount of 4% by weight without arginine cannot contribute to dissolve ellagic acid at 0.1 % by weight, relative to the total weight of the composition.

Comparative Examples 2 and 4-12 show that the compositions according to Comparative Examples 2 and 4-12 cannot maintain ellagic acid dissolved at 0.1 or 0.2% by weight relative to the total weight of the composition for a long period of time.

Comparative Examples 2 and 4 show that PVP (VP homopolymer) in an amount of 2 or 4% by weight relative to the total weight of the composition cannot contribute to dissolve ellagic acid at 0.1 or 02% by weight, respectively, relative to the total weight of the composition. Comparative Examples 5 and 6 show that the VP copolymers (anionic) cannot contribute to dissolve ellagic acid at 0.1% by weight relative to the total weight of the composition.

Comparative Examples 7 and 8, 9 and 10, and 11 and 12 show that non-VP cationic polymers, non-VP anionic polymers and non-VP nonionic polymers, respectively, cannot contribute to dissolve ellagic acid at 0.1% by weight relative to the total weight of the composition.

(Sensory Test)

The non-stickiness and freshness of the compositions according to Example 3 and

Comparative Example 3 were evaluated by 5 panelists in accordance with the following score system.

Non- Stickiness: 1 (sticky) to 5 (not sticky)

Freshness: 1 (not fresh) to 5 (fresh)

The average of the scores was determined as the result of the sensory test. The results of the sensory test are shown in Table 3.

Table 3

Table 3 show that the composition according to Example 3 as a representative of Examples 1-7 can provide better texture in terms of non-stickiness and freshness, than that according to Comparative Example 3.

The composition according to Comparative Example 3 can maintain ellagic acid dissolved for a long period of time as shown in Table 2. However, the results shown in Table 3 show that the composition according to Comparative Example 3 cannot provide excellent texture in terms of non-stickiness and freshness, which are useful for, in particular, cosmetic or dermatological products.

Also, as Comparative Example 4 cannot dissolve 0.2% by weight of ellagic acid whereas Example 4 can, the capability of PVP (VP homopolymer) to dissolve ellagic acid is smaller than that of VP (nonionic) copolymer.