JP7358474B2 - Composition for brightening or whitening keratin substances - Google Patents

Description

The present invention relates to cosmetic compositions. The invention particularly relates to compositions for brightening or whitening keratin materials, especially human skin.

Human skin color depends on various factors, especially season, race, and gender, and is determined primarily by the nature and concentration of melanin produced by melanocytes. Melanocytes are specialized cells that synthesize melanin through specific organelles called melanosomes. In addition, some individuals experience the appearance of dark and/or pigmented spots on the skin, especially on the hands, at different times in life, which causes unevenness in the skin.

In particular, for various reasons related to better wearing comfort (softness, softening properties, etc.), keratin materials, especially compositions currently used for skin care and/or make-up, are usually in a continuous phase. An oil-in-water (O/W) emulsion consists of an aqueous phase (dispersion medium) and an oil phase (dispersoid), or an oil-in-water (O/W) emulsion consisting of an oil phase (dispersion medium) and an oil phase (dispersoid), or It is in the form of a water-in-oil (W/O) emulsion, consisting of an aqueous phase (quality).

O/W emulsions are most sought after in the cosmetics field because they contain an aqueous phase as the external phase and therefore provide a fresher, less sticky, and lighter feel than W/O emulsions when applied to the skin.

However, due to their properties, conventional oil-in-water emulsions are not completely satisfactory, especially with regard to skin brightening or skin whitening.

Efforts have been made to incorporate silicone resins, styrenic copolymers in combination with pigments and whitening actives into oil-in-water emulsions. However, the inventors have found that it is difficult to obtain a composition that has a good brightening or whitening effect on the skin, while not affecting the wearing comfort.

Efforts have also been made to incorporate skin whitening ingredients into oil-in-water emulsions. Unfortunately, this whitening ingredient causes the resulting emulsion to become sticky, thereby somewhat degrading the feel of the emulsion.

Lee J. et al., "Hydrotropic Solubilization of Paclitaxel: Analysis of Chemical Structures for Hydrotropic Property," Pharmaceutical Research, Vol. 20 (2003), No. 7 Hodgon T.K., Kaler E.W., "Hydrotropic Solutions", Current Opinion in Colloid and Interface Science, Vol. 12 (2007), pp. 121-128. Meylan and Howard, "Atom/Fragment contribution method for estimating octanol-water partition coefficients," J. Pharm. Sci, Vol. 84 (1995), pp. 83-92. "Exploring QSAR: hydrophobic, electronic and steric constants", ACS professional reference book (1995) http://esc.syrres.com/interkow/kowdemo.htm

Therefore, it is necessary to formulate compositions that overcome the above-mentioned difficulties.

In particular, it is necessary to formulate a composition in the form of an emulsion, which contains an oil phase dispersed in an aqueous phase and has a brightening or whitening effect on keratin substances, while retaining a good feeling of use. .

The inventors have discovered that such needs can be met by the present invention.

According to one aspect, the invention therefore provides a composition in the form of an emulsion for brightening or whitening keratinous substances, comprising an oil phase dispersed in an aqueous phase;
(i) at least one skin brightening or whitening active ingredient selected from flavonoids;
(ii) at least one hydrotrope; and
(iii) Compositions comprising at least one polymer derived from 2-acrylamidomethylpropanesulfonic acid.

The compositions of the present invention are advantageous in several respects.

Firstly, the composition of the invention has a brightening or whitening effect on keratin substances, especially human skin.

In particular, in the present invention, "brightening or whitening effect" refers to the brightening or whitening effect on keratin substances, which refers to the brightening or whitening effect of the composition of the invention on the skin 16 hours after application to the substrate. Demonstrated by the bioavailability of whitening active ingredients.

In addition, the composition of the present invention provides a good feeling of use, such as moisturizing, nourishing, softness and/or anti-dullness.

The composition of the invention has a viscosity of less than 50 UD (Deviation Units), preferably from 17 UD to 35 UD, measured at 25° C. using a Rheomat 180 viscometer with spindle M2 rotating at 200 rpm. .

According to another aspect, the invention further relates to a cosmetic method for brightening or whitening keratinous materials, in particular human skin, comprising applying a composition of the invention to the keratinous materials. .

For the purposes of the present invention, the term "keratinous material" is intended to encompass human skin, mucous membranes such as the lips, and nails. Human skin, especially facial skin, is most prominently considered in the present invention.

Other subjects, features, aspects and advantages of the invention will become clearer from reading the following detailed description and examples.

In the following, limits of value ranges are included within this range, in particular in the expressions "between" and "range between", unless otherwise specified.

Furthermore, as used herein, the phrase "at least one species" is synonymous with the phrase "one or more species."

Throughout this application, the term "comprising" is intended to be interpreted to include all specifically mentioned features, as well as any additional, unspecified features. As used herein, use of the term "comprising" also discloses embodiments that are free of (ie, "consist of") features other than those specifically recited.

According to one aspect, the invention provides a composition in the form of an emulsion for brightening or whitening keratinous substances, comprising an oil phase dispersed in an aqueous phase;
(i) at least one skin brightening or whitening active ingredient selected from flavonoids;
(ii) at least one hydrotrope; and
(iii) at least one polymer derived from 2-acrylamidomethylpropanesulfonic acid (hereinafter referred to as "AMPS polymer");
A composition comprising:

Antioxidant or Skin Whitening Active Ingredient The composition of the present invention comprises at least one skin brightening or whitening active ingredient selected from flavonoids.

Flavonoids Flavonoids are a specific group of polyphenols and the most abundant group of polyphenolic compounds, making up approximately two-thirds of the total phenols in the consumed feed. Flavonoids are further classified by chemical structure into chalcones, flavones, flavanones, flavanols, flavonols, dihydroflavonols, isoflavonoids, neoflavonoids, catechins, anthocyanidins, and tannins. More than 4,000 flavonoids have been identified, many of which are present in fruits, vegetables and beverages (tea, coffee, beer, wine and fruit drinks). Flavonoids are reported to have antiviral, antiallergic, antiplatelet, antiinflammatory, antitumor and antioxidant activities. Flavonoids protect lipids and living cell components from damaging oxidative stress by efficiently scavenging free radicals.

Preferably, the flavonoids used are flavones.

Baicalin, a component of the Chinese medicinal herb Scutellariae (Huang-chin), is a flavone, a type of flavonoid. Baicalin is a powerful antioxidant that exhibits powerful effects against oxidative stress diseases, inflammation, allergies, cancer, bacterial infections, etc.

Baicalin is found in several species of the genus Scutellaria, including Scutellaria baicalensis and Blue Skullcap (Scutellaria lateriflora). Marsh skullcap (Scutellaria galericulata) leaves contain 10 mg/g of baicalin. Baicalin is also present in Oroxylum indicum bark isolate.

In one embodiment of the invention, baicalin is used in the form of Scutellaria root extract.

Preferably, the flavonoids are present in an amount ranging from 0.1% to 2%, preferably from 0.1% to 1%, more preferably from 0.1% to 0.5% by weight, relative to the total weight of the composition.

Hydroxylated diphenylmethane derivatives According to a preferred embodiment of the invention, the composition further comprises at least one hydroxylated diphenylmethane derivative as skin brightening or whitening ingredient.

Hydroxylated diphenylmethane derivatives that can be used in the compositions of the invention preferably have the following formula (I):

(In the formula,
R ₁ is selected from a hydrogen atom, a methyl group, a saturated or unsaturated linear or branched hydrocarbon chain having 2 to 4 carbon atoms, an -OH group, and a halogen;
R ₂ is selected from hydrogen atoms, methyl groups, and saturated or unsaturated straight or branched hydrocarbon chains having 2 to 5 carbon atoms;
R ₃ is selected from a methyl group or a saturated or unsaturated straight or branched hydrocarbon chain having 2 to 5 carbon atoms;
R ₄ and R ₅ are independently from each other a hydrogen atom, a methyl group, a saturated or unsaturated linear or branched hydrocarbon chain having 2 to 5 carbon atoms, an -OH group, or a halogen selected from compounds represented by

The -OH, R ₁ , R ₄ and R ₅ groups may be in the ortho, meta or para position to the bond formed by the carbon linking the two aromatic nuclei to each other.

According to a preferred embodiment of the invention, a compound of formula (I) comprising:
During the ceremony,
- R ₁ , R ₂ , R ₄ and R ₅ represent hydrogen atoms,
- R ₃ is a methyl group,
Compounds are used in which the -OH group is in the ortho and para positions to the bond formed by the carbon linking the two aromatic nuclei to each other.

This compound is 4-(1-phenylethyl)-1,3-benzenediol, or 4-(1-phenylethyl)-1,3-dihydroxybenzene, also known as phenylethylresorcinol, or phenylethylbenzenediol, or styrylresorcinol. Formula (II) below, known as:

corresponds to This compound has CAS number 85-27-8. This compound is sold by Symrise under the trade name Symwhite 377® or Bio 377.

When present, the hydroxylated diphenylmethane derivative is present in an amount ranging from 0.1% to 2%, more preferably from 0.1% to 1%, even more preferably from 0.1% to 0.5% by weight relative to the total weight of the composition. exists in

Hydrotrope The composition of the present invention comprises at least one hydrotrope.

One type of hydrotrope may be used, but it is also possible to use a combination of two or more different types of hydrotropes.

Hydrotropes (or hydrotropes) are a distinct class of compounds characterized by an amphiphilic molecular structure and the ability to dramatically improve the solubility of organic molecules that are sparingly soluble in water. Good too. Many hydrotropes have an aromatic structure with an ionic moiety, while others have linear alkyl chains, as described in the table below. Although hydrotropes are very similar to surfactants and have the ability to lower surface tension, their small hydrophobic units and relatively short alkyl chains distinguish them from amphiphiles. It is distinguished as a class of

Common hydrotrope molecules include sodium 1,3-benzenedisulfonate, sodium benzoate, sodium 4-pyridinecarboxylate, sodium salicylate, sodium benzenesulfonate, caffeine, sodium p-toluenesulfonate, and butyl monosodium. Sodium glycol sulfate, 4-aminobenzoic acid HCl, sodium cumene sulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethylphosphorylcholine, resorcinol, butyl urea, pyrogallol , N-picolilacetamide 3,5, procaine HCl, proline HCl, nicotinamide, pyridine, 3-picolylamine, ibuprofen sodium, sodium xylene sulfonate, ethyl carbamate, pyridoxal hydrochloride, sodium benzoate, 2-pyrrolidone, ethyl Mention may be made of urea, N,N-dimethylacetamide, N-methylacetamide and isoniazid. Hydrotropes are described in Lee J. et al., "Hydrotropic Solubilization of Paclitaxel: Analysis of Chemical Structures for Hydrotropic Property", Pharmaceutical Research, Vol. 20 (2003), No. 7, and Hodgon T.K., Kaler E.W., "Hydrotropic Solutions", Current Opinion in Colloid and Interface Science, Volume 12 (2007), pages 121-128.

Cosmetically acceptable hydrotropes are preferred hydrotropes that can be used in cosmetic compositions. Hydrotropes represent a broad class of molecules used in various fields, but their use in cosmetics has been limited due to safety and tolerance constraints. Preferred hydrotropes in cosmetics are as described below.

The suitability of a hydrotrope for use in cosmetic compositions may be determined using tests for determining the effects of compounds on the skin and bioavailability methods known in the art. I can do it.

The advantage of using hydrotropes is that once a stable solution is obtained, further dilution does not affect the stability of the solution. This is very different from the organic solvents commonly used to improve the water solubility of actives. Generally, when an organic solvent in which an active substance is dissolved is diluted with water, crystallization or precipitation occurs.

The log P of the hydrotrope may be between -0.7 and 6, preferably between -0.7 and 1.0, preferably between -0.5 and 0.7 for non-ionic hydrotropes and for ionic hydrotropes (e.g. acidic hydrotropes). It may preferably be between -0.7 and 5.5.

The pH will be adjusted by the formulator to achieve the best clarity with hydrotropes.

The log P value is the value of the base 10 logarithm of the apparent partition coefficient of octan-1-ol/water. The log P value is known and determined by a standard test that measures the concentration of compound (c) in octan-1-ol and water. log P is calculated according to the method described in the article by Meylan and Howard, "Atom/Fragment contribution method for estimating octanol-water partition coefficients", J. Pharm. Sci, Vol. 84 (1995), pp. 83-92. be able to. This value may be calculated using a number of commercially available software packages. These software packages measure log P as a function of the structure of the molecule. As an example, we can mention the Epiwin software from the US Environmental Agency.

This value may be calculated using, in particular, the ACD (Advanced Chemistry Development) Solaris software V4.67, and this value may also be found in "Exploring QSAR: hydrophobic, electronic and steric constants", ACS professional reference book (1995 ) can also be obtained. There is also an Internet site that provides estimates (address: http://esc.syrres.com/interkow/kowdemo.htm).

Hydrotropes include oxothiazolidine carboxylic acids, vitamin B3 and its derivatives, preferably niacinamide, xanthine bases, preferably caffeine, camphorbenzalkonium methosulfate, ellagic acid, hydroxyphenoxypropionic acid, diethylrutidinate, tere Pharylidene dicamphorsulfonic acid, ferulic acid, salicylic acid, phloretin, acetyltrifluoromethylphenylvalylglycine, resveratrol, 4-butylresorcinol, apigenin, phenylethylresorcinol, prasterone, benzophenone-3, butylmethoxydibenzoylmethane, Preferably, it is selected from the group consisting of capryloylsalicylic acid, ethylhexyl salicylate, and jasmonic acid derivatives, preferably sodium tetrahydrojasmonate. More preferred are vitamin B3 and its derivatives, xanthine bases such as caffeine, and jasmonic acid derivatives, which are explained in more detail below.

(vitamin B3 and its derivatives)
Vitamin B3 is also referred to as vitamin PP and is a compound of the following formula (III).

In the formula, R is -CONH ₂ (niacinamide), -COOH (nicotinic acid or niacin), or CH ₂ OH (nicotinyl alcohol), -CO-NH-CH ₂ -COOH (nicotinuric acid), or CO- It may be NH-OH (nicotinyl hydroxamic acid), preferably niacinamide.

Vitamin B3 derivatives that may be mentioned include, for example, nicotinic acid esters such as tocopherol nicotinate, amides derived from niacinamide by substitution of the hydrogen group of _-CONH2 , products from the reaction of carboxylic acids with amino acids, Includes esters of nicotinyl alcohol and carboxylic acids (such as acetic acid, salicylic acid, glycolide acid or palmitic acid).

Derivatives of: 2-chloronicotinamide, 6-methylnicotinamide, 6-aminonicotinamide, N-methylnicotinamide, N,N-dimethylnicotinamide, N-(hydroxymethyl)nicotinamide, quinolinimide, nicotine Anilide, N-benzylnicotinamide, N-ethylnicotinamide, nifenazone, nicotinaldehyde, isonicotinic acid, methylisonicotinic acid, thionicotinamide, niaramide, 2-mercaptonicotinic acid, nicomol and niaprazine, methyl nicotinate, and nicotine Mention may also be made of sodium acids.

Other vitamin B3 derivatives that may likewise be mentioned include their inorganic salts, such as the chlorides, bromides, iodides or carbonates, and their organic salts, such as the salts obtained by reaction with carboxylic acids, such as the acetates, Includes salicylates, glycolates, lactates, malates, citrates, mandelates, tartrates, etc.

The log P of vitamin B3 or its derivative is preferably -0.7 to 6, preferably -0.6 to 5, more preferably -0.5 to 4.

(xanthine base)
Among the xanthine bases that can be used in the present invention, caffeine, theophylline, theobromine, acephylline, xantinol nicotinate, diniprophylline, diprophylline, etamiphylline and its derivatives, etophylline, proxyphylline, pentophylline, propentophylline, pyridophylline , and bamiphylline, without being limited to this list.

Preferably, the xanthine base is selected from the group consisting of caffeine, theophylline, theobromine, acephylline, and mixtures thereof. These xanthine bases are known to be inhibitors of phosphodiesterase, an enzyme involved in cAMP degradation. By increasing the intracellular content of cAMP, these xanthine bases promote lipolytic activity and thus constitute an excellent slimming active agent.

As examples of plant extracts containing xanthine bases, mention may be made in particular of tea, coffee, guarana, yerba mate and kola tree extracts, without being limited to this list.

The log P of the xanthine base is preferably -0.7 to 6, preferably -0.6 to 5, more preferably -0.5 to 4, and even more preferably -0.3 to 2.

(Jasmonic acid derivative)
The jasmonic acid derivative has the following formula (IV):

(wherein R ₁ represents a COOR ₃ group, R ₃ represents a hydrogen atom or a C ₁ -C ₄ alkyl group optionally substituted with one or more hydroxyl groups, and R ₂ represents a direct (representing a saturated or unsaturated hydrocarbon group having a chain shape and having 1 to 18 carbon atoms, or a branched or cyclic shape having 3 to 18 carbon atoms), as well as its optical isomers and A compound selected from the corresponding salts.

Preferably, R ₁ is -COOH, -COOMe (Me: methyl group), -COO-CH ₂ -CH ₃ , -COO-CH ₂ -CH(OH)-CH ₂ OH, -COOCH ₂ -CH ₂ - Represents a group selected from _CH2OH or _COOCH2 -CH(OH) _-CH3 . Preferably R ₁ represents a -COOH group.

Preferably, R ₂ represents a saturated or unsaturated linear hydrocarbon group, preferably having 2 to 2 carbon atoms. Specifically, R ₂ may be a pentyl group, a pentenyl group, a hexyl group or a heptyl group.

According to one embodiment, the compound of formula (I) is selected from 3-hydroxy-2-[(2Z)-2-pentenyl]cyclopentaneacetic acid or 3-hydroxy-2-pentylcyclopentaneacetic acid, preferably 3-Hydroxy-2-pentylcyclopentaneacetic acid.

Salts of the compounds that can be used in the invention include, in particular, alkali metal salts, such as sodium or potassium salts; alkaline earth metal salts, such as calcium, magnesium or strontium salts; metal salts, salts of ammonium of the formula NH ₄ ⁺ ; quaternary ammonium salts; organic amine salts, such as methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2-hydroxyethylamine , bis(2-hydroxyethyl)amine, or tris(2-hydroxyethyl)amine; or a salt of lysine or arginine. Preference is given to using salts selected from sodium, potassium, calcium, magnesium, strontium, copper, manganese or zinc salts.

The following compound (Mexoryl SBO) is preferably used as the jasmonic acid derivative.

The log P of the jasmonic acid derivative is preferably -0.7 to 6, preferably -0.6 to 5, more preferably -0.5 to 4.

Preferably, the hydrotrope is present in an amount ranging from 0.1% to 10%, preferably from 0.5% to 8%, more preferably from 1% to 5% by weight, relative to the total weight of the composition.

AMPS Polymer The AMPS polymer used in the present invention comprises at least acrylamide-2-methylpropanesulfone in a partially or totally neutralized form with an inorganic base other than ammonia, such as sodium hydroxide or potassium hydroxide. Crosslinked or non-crosslinked homopolymers or copolymers containing acid monomers.

These AMPS polymers are preferably fully neutralized or substantially fully neutralized, ie, at least 90% neutralized.

These AMPS polymers in the present invention may be crosslinked or non-crosslinked.

If the polymer is crosslinked, the crosslinking agent can be selected from polyolefinically unsaturated compounds commonly used for crosslinking polymers obtained by free radical polymerization.

Examples of crosslinking agents that may be mentioned are divinylbenzene, diallyl ether, dipropylene glycol diallyl ether, polyglycol diallyl ether, triethylene glycol divinyl ether, hydroquinone diallyl ether, ethylene glycol or tetraethylene glycol di(meth)acrylate, Trimethylolpropane triacrylate, methylenebisacrylamide, methylenebismethacrylamide, triallylamine, triallyl cyanurate, diallylmaleate, tetraallylethylenediamine, tetraallyloxyethane, trimethylolpropane diallyl ether, allyl (meth)acrylate, sugar Included are allyl ethers of alcohols, or allyl or vinyl ethers of other polyfunctional alcohols, and allyl esters of phosphoric and/or vinylphosphonic acid derivatives, or mixtures of these compounds.

According to one embodiment of the invention, the crosslinking agent is selected from methylene bisacrylamide, allyl methacrylate and trimethylolpropane triacrylate (TMPTA). The degree of crosslinking usually ranges from 0.01 mol% to 10 mol%, more particularly from 0.2 mol% to 2 mol%, based on the polymer.

The AMPS polymer in the present invention is water-soluble or water-dispersible. In this case, the polymer is
- "homopolymers" containing only AMPS monomers and, if crosslinked, containing one or more crosslinkers such as those defined above;
- or a copolymer obtained from AMPS and one or more hydrophilic or hydrophobic ethylenically unsaturated monomers and, if crosslinked, one or more crosslinkers such as those defined above. Either. If the copolymer contains hydrophobic ethylenically unsaturated monomers, these monomers are free of fatty chains and are preferably present in small amounts.

For the purposes of this invention, the term "fatty chain" means any hydrocarbon-based chain containing at least 7 carbon atoms.

The term "water-soluble or water-dispersible" means that at 25 °C, when introduced into the aqueous phase to a mass concentration equal to 1%, a macroscopically homogeneous and transparent solution is obtained, i.e. through a 1 cm thick sample at a wavelength equal to 500 nm. , means a polymer that makes it possible to obtain a solution with a maximum light transmittance of at least 60%, preferably at least 70%.

The "homopolymer" in the present invention is preferably crosslinked and neutralized, and can be obtained according to a preparation method including the following steps.
(a) A monomer such as AMPS in free form is dispersed or dissolved in a tert-butanol solution or an aqueous tert-butanol solution.
(b) The solution or dispersion of the monomers obtained in (a) is added to the monomer or Neutralize using multiple inorganic or organic bases, preferably ammonia _NH3
(c) Adding a crosslinking monomer to the solution or dispersion obtained in (b)
(d) Standard free radical polymerization is carried out in the presence of a free radical initiator at temperatures ranging from 10 to 150°C to precipitate the polymer into a tert-butanol-based solution or dispersion. .

The AMPS homopolymer in the present invention is an optionally crosslinked and/or neutralized 2-acrylamido-2-methylpropanesulfonic acid homopolymer, for example under the trade name Hostacerin AMPS® (CTFA name: ammonium polysulfonic acid) by Clariant. Preferably, it is poly(2-acrylamido-2-methylpropanesulfonic acid) sold as acrylic dimethyltauramide).

The water-soluble or water-dispersible AMPS copolymers of the present invention contain water-soluble ethylenically unsaturated monomers, hydrophobic monomers, or mixtures thereof.

Water-soluble comonomers may be ionic or non-ionic.

Among the ionic water-soluble comonomers, examples that may be mentioned include the following compounds and their salts:
- (meth)acrylic acid,
- styrene sulfonic acid,
- vinylsulfonic acid and (meth)allylsulfonic acid,
- vinylphosphonic acid,
- maleic acid,
- itaconic acid,
- crotonic acid,
- The following formula (V):

(In the formula,
- _R1 is selected from _H , _-CH3 , _-C2H5 and _{-C3H7 ,
-X1}
- -OR Alkyethers of type ₂ (R ₂ is a straight-chain or branched, saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms and at least one sulfone ( -SO ₃ -) and/or substituted with sulfate (-SO ₄ -) and/or phosphate (-PO ₄ H ₂ -) groups).

Among the nonionic water-soluble comonomers, examples that may be mentioned include:
- (meth)acrylamide,
- N-vinylacetamide and N-methyl N-vinylacetamide,
- N-vinylformamide and N-methyl N-vinylformamide,
- maleic anhydride,
- vinylamine,
- N-vinyllactams containing cyclic alkyl groups containing 4 to 9 carbon atoms, such as n-vinylpyrrolidone, N-butyrolactam and N-vinylcaprolactam,
- vinyl alcohol with the formula CH ₂ =CHOH,
- The following formula (VI):

(In the formula,
- _R15 is selected from _H , _-CH3 , _-C2H5 and _{-C3H7 ,}
- x ₂
- Alkyl ethers of type OR ₁₆ (R ₁₆ is a straight-chain or branched, saturated, containing from 1 to 6 carbons, optionally substituted with a halogen atom (iodine, bromine, chlorine or fluorine) or unsaturated hydrocarbon-based groups), hydroxyl groups (-OH), and ethers).

Examples include glycidyl (meth)acrylate, hydroxyethyl methacrylate, and (meth)acrylates of ethylene glycol, diethylene glycol, or polyalkylene glycol.

Among hydrophobic comonomers that do not contain fatty chains, examples that may be mentioned include:
- styrene and its derivatives, such as 4-butylstyrene, α-methylstyrene and vinyltoluene,
- vinyl acetate, with formula _CH2 =CH- _OCOCH3 ,
- vinyl ethers of the formula CH ₂ =CHOR, where R is a straight-chain or branched, saturated or unsaturated hydrocarbon group having 1 to 6 carbons;
- Acrylonitrile,
- caprolactone,
- Vinyl chloride and vinylidene chloride,
- silicone derivatives that polymerize to give silicone polymers, such as methacryloxypropyltris(trimethylsiloxy)silane and silicone methacrylamide;
- Formula (VII) below:

(In the formula,
- _R23 is selected from H _{, -CH3} , _-C2H5 and _{-C3H7 ,
-X3}
- Hydrophobic of alkyl ethers of type -OR ₂₄ (R ₂₄ is a linear or branched, saturated or unsaturated hydrocarbon group containing from 1 to 6 carbon atoms) Contains vinyl monomers.

Examples include methyl methacrylate, ethyl methacrylate, n-butyl (meth)acrylate, tert-butyl (meth)acrylate, cyclohexyl acrylate, isobornyl acrylate, and 2-ethylhexyl acrylate.

The water-soluble or water-dispersible AMPS polymers of the present invention have a concentration in the range of 50,000 g/mol to 10,000,000 g/mol, preferably 80,000 g/mol to 8,000,000 g/mol, more preferably 100,000 g/mol to 7,000,000 g/mol. It is preferred to have a molar mass.

Examples of water-soluble or water-dispersible AMPS homopolymers according to the invention that may be mentioned include acrylamide-2-, such as the polymer used in the commercial product Simulgel™ 800 (CTFA name: Sodium polyacryloyldimethyltaurate). Crosslinked or non-crosslinked polymers of sodium methylpropanesulfonate are included.

Examples of water-soluble or water-dispersible AMPS copolymers according to the invention that may be mentioned include:
- Copolymers of AMPS and vinylpyrrolidone or vinylformamide, such as those used in the commercial products sold by Clariant under the name Aristoflex AVC (CTFA name: ammonium acryloyldimethyltaurate/VP copolymer), but with sodium hydroxide or copolymer, which is neutralized with potassium hydroxide,
- Copolymers of AMPS and sodium acrylate, for example used in the commercial product sold under the trade name Simulgel(TM) EG by the company SEPPIC (CTFA name: acrylamide/sodium acryloyldimethyltaurate/isohexadecane/polysorbate-80). AMPS/sodium acrylate copolymers such as
- AMPS, such as copolymers of AMPS and hydroxyethyl acrylate, such as those used in the commercial product sold under the trade name EMT 10 by the company SEPPIC (CTFA name: Hydroxyethyl acrylate/sodium acryloyldimethyltaurate copolymer) /Hydroxyethyl acrylate copolymer.

A preferred polymer is more particularly a copolymer of optionally crosslinked and/or neutralized AMPS and hydroxyethyl acrylate.

The AMPS polymer accounts for 0.1% to 5%, preferably 0.5% to 3%, more preferably 0.6% to 1.5% by weight of the total weight of the oil-in-water emulsion composition.

Nonionic Surfactant In a preferred embodiment, the composition of the invention comprises at least one nonionic surfactant selected from oxyalkylenated sorbitan fatty acid esters.

Surfactants of this type that may be mentioned are more specifically (INCI names) polysorbate 20, polysorbate 40, polysorbate 60, polysorbate 65, polysorbate 80, polysorbate 85, PEG-5 sorbitan isostearate, PEG Oxyethylenated sorbitan fatty acid esters such as -20 sorbitan triisostearate, PEG-20 sorbitan isostearate, PEG-40 sorbitan septaoleate, PEG-20 sorbitan tetraoleate and PEG-20 sorbitan trioleate are included.

Mention may be made of polysorbate 20, such as that sold by the company Croda under the trade name Tween 20-LQ-(AP).

When present, the nonionic surfactant is present in an amount effective to ensure stability of the compositions of the invention.

When a nonionic surfactant selected from oxyalkylenated sorbitan fatty acid esters is present, the compositions of the invention are stable over time.

After storage at different temperatures (T=4°C, room temperature, 40°C and 45°C) for a period of 2 months, the macroscopic or microscopic appearance and physicochemical properties (droplet size, pH, The emulsion is stable if no change is observed in the viscosity).

Preferably, the nonionic surfactant is present in an amount ranging from 0.1% to 3%, preferably from 0.1% to 1.5%, more preferably from 0.1% to 1% by weight relative to the total weight of the composition. May be present in amounts.

Aqueous Phase The compositions of the invention include at least one continuous aqueous phase.

The aqueous phase of the compositions of the invention comprises water and optionally one or more water-miscible or at least partially water-miscible compounds, such as C ₂ -C ₈ lower polyols, or ethanol and isopropanol. Contains monoalcohols.

The term "polyol" is to be understood to mean any organic molecule containing at least two free hydroxyl groups. Examples of polyols that may be mentioned include glycols such as butylene glycol, propylene glycol, isoprene glycol, caprylyl glycol, glycerol (ie glycerin) and polyethylene glycol.

The aqueous phase may further include any conventional water-soluble or water-dispersible additives as described below.

The aqueous phase is 30% to 98% by weight, preferably 30% to 95% by weight, more preferably 50% to 90% by weight, even more preferably 60% to 90% by weight, based on the total weight of the composition. It may account for %.

Oil Phase The composition of the invention comprises at least one oil phase dispersed in the aqueous phase described above.

The nature of the oil phase in the compositions of the invention is not critical.

Specifically, the oil phase includes at least one oil.

The term "oil" refers to any fat body that is in liquid form at room temperature (20-25° C.) and atmospheric pressure. These oils may be of animal, vegetable, mineral or synthetic origin.

Oils may be volatile or non-volatile.

The term "volatile oil" refers to any non-aqueous medium that can evaporate from the skin or lips in less than 1 hour at room temperature (20-25° C.) and atmospheric pressure (760 mmHg). Volatile oils are volatile cosmetic oils that are liquid at room temperature. More particularly, the volatile oil has an evaporation rate between 0.01 and 200 mg/cm ² /min (inclusive).

The term "fixed oil" is intended to mean an oil that remains on the keratin material at ambient temperature and atmospheric pressure. More specifically, fixed oils have evaporation rates strictly below 0.01 mg/cm ² /min.

To determine this evaporation rate, 15 g of the oil or oil mixture to be tested are introduced into a 7 cm diameter crystallizer, 0.3 m thermostatted to a temperature of 25°C and humidified to a relative humidity of 50%. ^3. Place on a balance placed in a large chamber. Directly above the crystallizer containing the solvent, with the liquid left to stand, a fan (PAPST - MOTOREN, reference name 8550N, rotating at 2,700 rpm) to evaporate naturally without stirring. The mass of oil remaining in the crystallizer is measured at regular intervals. Evaporation rate is expressed in mg of oil evaporated per unit surface area (cm ² ) and per unit time (minute).

Oils suitable for the present invention are not limited and may be hydrocarbon-based, silicone-based or fluorine-based.

In the present invention, the term "silicone oil" refers to an oil containing at least one silicon atom, in particular at least one Si-O group.

The term "fluorinated oil" refers to an oil that contains at least one fluorine atom.

The term "hydrocarbon oil" refers to oils containing primarily hydrogen and carbon atoms.

The oil may optionally contain oxygen, nitrogen, sulfur and/or phosphorus atoms, for example in the form of hydroxyl or acid groups.

The oil phase may be present in an amount ranging from 1% to 70% by weight, preferably from 10% to 70% by weight, more preferably from 10% to 40% by weight, relative to the total weight of the composition. .

As mentioned above, the amount of oil phase does not include the amount of emulsifier.

Additives In a known manner, the compositions of the invention can also contain one or more additives customary in cosmetics or dermatology.

Examples of auxiliary agents that may be mentioned include emulsifiers, gelling agents, activators, preservatives, antioxidants, fragrances, sunscreens (=UV blockers), additional pigments, basic agents (triethanol amines, diethanolamine or sodium hydroxide) or acidic agents (citric acid), or lipid vesicles or any other type of vector (nanocapsules, microcapsules, etc.), and mixtures thereof.

These additives are used in the usual proportions in the cosmetics field, for example 0.01% to 30% of the total mass of the composition, and depending on the nature of the additive, they can be added to the aqueous or oily phase of the composition, or to vesicles or optionally introduced into other types of vectors.

These additives and their concentrations should not alter the desired properties of the compositions of the present invention.

According to a preferred embodiment, the invention provides a composition in the form of an emulsion for brightening or whitening keratinous substances, comprising an oil phase dispersed in an aqueous phase, with respect to the total weight of the composition:
(i) As a skin brightening or whitening active ingredient,
0.1% to 0.5% by mass of at least one flavone and the following formula (I):

(In the formula,
- R ₁ , R ₂ , R ₄ and R ₅ represent hydrogen atoms,
- R ₃ is a methyl group,
- -OH groups are in the ortho and para positions to the bond formed by the carbon linking the two aromatic nuclei to each other)
0.1% to 0.5% by weight of at least one hydroxylated diphenylmethane derivative selected from the compounds of
(ii) oxothiazolidine carboxylic acids, vitamin B3 and derivatives thereof, preferably niacinamide, xanthine bases, preferably caffeine, camphorbenzalkonium methosulfate, ellagic acid, hydroxyphenoxypropionic acid, diethylrutidinate, terephthalate; Redene dicamphorsulfonic acid, ferulic acid, salicylic acid, phloretin, acetyltrifluoromethylphenylvalylglycine, resveratrol, 4-butylresorcinol, apigenin, phenylethylresorcinol, prasterone, benzophenone-3, butylmethoxydibenzoylmethane, capri 1% to 5% by weight of at least one hydrotrope selected from roylsalicylic acid, ethylhexyl salicylate, and jasmonic acid derivatives, preferably sodium tetrahydrojasmonate;
(iii) 0.6% to 1.5% by weight of at least one optionally crosslinked and/or neutralized 2-acrylamido-2-methylpropanesulfonic acid copolymer; and
(iv) Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 65, Polysorbate 80, Polysorbate 85, PEG-5 Sorbitan Isostearate, PEG-20 Sorbitan Triisostearate, PEG-20 Sorbitan Isostearate, PEG-40 Sorbitan 0.1% to 1% by weight of at least one nonionic surfactant selected from septaoleate, PEG-20 sorbitan tetraoleate and PEG-20 sorbitan trioleate
A composition comprising:

Preferably, the composition of the invention is in the form of an oil-in-water emulsion, such as a lotion, cream, gel or liquid foundation, and is prepared according to conventional methods in the cosmetics field.

The composition of the invention has a viscosity of less than 50 UD (Deviation Units), preferably from 17 UD to 35 UD, measured at 25° C. using a Rheomat 180 viscometer with spindle M2 rotating at 200 rpm. .

As mentioned above, viscosity is measured at 25° C. using a ProRheo R180 viscometer from ProRheo with spindle M2 rotating at 200 rpm.

Methods and Applications The compositions of the invention are intended for topical application and may particularly constitute compositions intended for brightening or whitening keratinous substances, especially human skin.

Therefore, according to another aspect, the invention relates to a cosmetic method for brightening or whitening keratinous substances, in particular skin, comprising applying a composition as defined above to the keratinous substances. .

The invention is illustrated in more detail by the examples described below, which are given by way of non-limiting illustration.

The percentages are percentages by weight of active ingredient or substance.

In the examples below, the weight percentages are given relative to the total weight of the composition.

(Example 1)
Preparation of compositions according to the inventive formulations and comparative formulations Compositions were prepared according to the inventive formulations (inv.) 1-2 and the comparative formulations (comp.) as described in the table below.

Preparation method:
1. Preparation of aqueous phase: Add hydrotrope ingredients (niacinamide and/or caffeine) to water and stir until completely dissolved, then add Scutellaria root extract and stir until completely dissolved. , keep the temperature at 75℃.
2. Preparation of oil phase: Mix phenylethyl resorcinol and oil and heat to 75°C to completely dissolve phenylethyl resorcinol, then optionally add polysorbate 20.
3. Add the oil phase to the water phase and homogenize with a VMI type homogenizer at 1,000 rpm for 10 minutes.
Cool to below 4.60°C, optionally add hydroxyethyl acrylate/sodium acryloyldimethyltaurate copolymer, stir until well dispersed, then add sodium hydroxide to adjust pH to 5.0.

(Example 2)
Evaluation of the inventive and comparative formulations The stability, viscosity and cosmetic properties of the inventive and comparative formulations of the compositions prepared in Example 1 were determined.

Stability tests for two months at room temperature (25°C), 40°C, and 45°C were conducted on compositions according to the formulation of the present invention and the comparative formulation. The test was carried out using a Binder (USA) oven by leaving the inventive and comparative formulations in the oven for 2 months.

The cosmetic compositions according to the formulation of the present invention and the comparative formulation were left in the refrigerator for 2 months using a refrigerator manufactured by Zhongke Meiling (YC-260L, China) to obtain a 2-month period of stability at 4°C. A stability test was conducted.

A 24 hour photostability test was performed using ATLAC (AMETEK Measurement and Calibration Technologies).

Finally, freeze-thaw stability testing was performed over 10 cycles using a Binder (USA) oven. In each cycle, the temperature is gradually changed from 20°C to -20°C over 24 hours.

The viscosity is measured at 25° C. using a ProRheo R180 viscometer from ProRheo with spindle M2 rotating at 200 rpm.

Stability and viscosity results for compositions with inventive and comparative formulations are described below.

It can be seen that the viscosity of the composition with the comparative formulation is too low, which is undesirable.

It can also be seen that the composition according to formulation 1 of the invention has good stability at various temperatures.

The brightening or whitening effect of the composition according to Formulation 1 of the present invention was carried out using the following ex-vivo procedure.
- Franz cell upper pig skin (external ear)
- 5mg/cm ² of each composition (applicable area: 1.77cm ² )
- Applicable at 32℃ for 16 hours (application time in real life)
- Cleaning after continued application
- Applied 1 to 2 times per cell (10 cells per process)
- Receptor fluid (PBS)
- Stripping was performed with Dsquame® discs
- LC-MS/MS quantification of stratum corneum (SC), skin (epidermis + dermis), and receptor fluid (RF) during washing

The bioavailability results are listed in the table below.

Consumer panel testing (n=60) showed that compared to compositions with comparative formulations, compositions with formulations 1 and 2 of the present invention provided better moisturization, nutrition, softness, and anti-dullness to the skin. It can be seen that it brings about

Claims (10)

A composition in the form of an emulsion for brightening or whitening keratinous substances, comprising an oil phase dispersed in an aqueous phase, based on the total weight of said composition:
(i) 0.1% to 2% by weight of at least one skin brightening or whitening active ingredient selected from flavones ;
(ii) 0.1% to 10% by weight of at least one hydrotrope ;
(iii) At least one type derived from 0.1% to 5% by mass of 2-acrylamidomethylpropanesulfonic acid selected from a copolymer of AMPS and hydroxyethyl acrylate, which may be crosslinked and/or neutralized. polymer ; and
Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 65, Polysorbate 80, Polysorbate 85, PEG-5 Sorbitan Isostearate, PEG-20 Sorbitan Triisostearate, PEG-20 Sorbitan Isostearate, PEG-40 Sorbitan Septaoleate , 0.1% to 3% by weight of at least one nonionic surfactant selected from , PEG-20 sorbitan tetraoleate, and PEG-20 sorbitan trioleate ;
The hydrotrope is oxothiazolidine carboxylic acid, vitamin B3, niacinamide, xanthine base, caffeine, camphorbenzalkonium methosulfate, ellagic acid, hydroxyphenoxypropionic acid, diethylrutidinate, terephthalylidene dicamphorsulfonic acid , from the group consisting of ferulic acid, salicylic acid, phloretin, acetyltrifluoromethylphenylvalylglycine, resveratrol, apigenin, prasterone, benzophenone-3, butylmethoxydibenzoylmethane, capryloylsalicylic acid, ethylhexyl salicylate, sodium tetrahydrojasmonate selected,
composition . 2. The composition of claim 1, wherein the nonionic surfactant is selected from polysorbate 20, polysorbate 40, polysorbate 60, polysorbate 65, polysorbate 80, and polysorbate 85. Composition according to claim 1 or 2, wherein the non-ionic surfactant is present in an amount ranging from 0.1% to 1 % by weight relative to the total weight of the composition. Composition according to any one of claims 1 to 3, wherein the flavonoid is present in an amount ranging from 0.1% to 1 % by weight, relative to the total weight of the composition. 5. A composition according to any one of claims 1 to 4, wherein the hydrotrope is selected from the group consisting of vitamin B3 , niacinamide , and caffeine . Composition according to any one of claims 1 to 5, wherein the hydrotrope is present in an amount ranging from 1 % to 5 % by weight relative to the total weight of the composition. 7. According to any one of claims 1 to 6, the polymer derived from 2-acrylamidomethylpropanesulfonic acid is present in an amount ranging from 0.5 % to 3 % by weight relative to the total weight of the composition. Compositions as described. As a skin whitening ingredient, the following formula (I):
(In the formula,
R ₁ is selected from a hydrogen atom, a methyl group, a saturated or unsaturated linear or branched hydrocarbon chain having 2 to 4 carbon atoms, an -OH group, and a halogen;
R ₂ is selected from hydrogen atoms, methyl groups, and saturated or unsaturated straight or branched hydrocarbon chains having 2 to 5 carbon atoms;
R ₃ is selected from a methyl group or a saturated or unsaturated straight or branched hydrocarbon chain having 2 to 5 carbon atoms;
R ₄ and R ₅ are independently from each other a hydrogen atom, a methyl group, a saturated or unsaturated linear or branched hydrocarbon chain having 2 to 5 carbon atoms, an -OH group, or a halogen selected)
8. The composition according to any one of claims 1 to 7, further comprising a hydroxylated diphenylmethane derivative selected from the compounds of . A composition in the form of an emulsion for brightening or whitening keratinous substances, comprising an oil phase dispersed in an aqueous phase, based on the total weight of said composition :
(i) As a skin brightening or whitening active ingredient,
0.1% to 0.5% by mass of at least one flavone ; and
Formula (I) below:
(In the formula,
- R ₁ , R ₂ , R ₄ and R ₅ represent hydrogen atoms,
- R ₃ is a methyl group,
- -OH groups are in the ortho and para positions to the bond formed by the carbon linking the two aromatic nuclei to each other)
0.1% to 0.5% by weight of at least one hydroxylated diphenylmethane derivative selected from the compounds ;
(ii ) 1% to 5% by weight of at least one hydrotrope selected from vitamin B3 , niacinamide, and caffeine ;
(iii) 0.6% to 1.5% by weight hydroxyethyl acrylate/sodium acryloyldimethyltaurate copolymer; and
(iv) 0.1% to 1% by weight of at least one nonionic surfactant selected from polysorbate 20, polysorbate 40, polysorbate 60, polysorbate 65, polysorbate 80, and polysorbate 85;
A composition comprising . 10. A cosmetic method for brightening or whitening a keratin material, the method comprising applying a composition according to any one of claims 1 to 9 to the keratin material.