JP2022523617A - Composition for brightening or whitening keratin substances - Google Patents

Abstract

The present invention is a composition in the form of an emulsion for brightening or whitening a keratin substance, comprising an oil phase dispersed in an aqueous phase, and (i) at least one antioxidant selected from phenolic compounds. Or a composition comprising a skin whitening active ingredient, (ii) at least one hydrotrope, and (iii) at least one polymer derived from 2-acrylamide methylpropane sulfonic acid. The present invention further relates to keratin substances, particularly cosmetological methods for brightening or whitening human skin.

Description

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

Human skin color depends on a variety of factors, especially season, race, and gender, and is primarily determined 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 colored spots on the skin, especially on the hands, at different times of life, which causes unevenness in the skin.

In particular, for a variety of reasons related to better comfort (softness, softness, etc.), keratin substances, especially compositions currently used to care for and / or make up the skin, are usually in continuous phase. An oil-in-water (O / W) emulsion consisting of an aqueous phase as a (dispersion medium) and an oil phase as a discontinuous phase (dispersible), or an oil phase and a discontinuous phase (dispersion) as a continuous phase (dispersion medium). It is in the form of a water-in-oil (W / O) type emulsion consisting of an aqueous phase that is (quality).

O / W emulsions contain an aqueous phase as an external phase and are therefore most sought after in the cosmetics field because they are more refreshing, non-greasy and lighter than W / O emulsions when applied to the skin.

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

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

Efforts have also been made to introduce skin whitening ingredients into oil-in-water emulsions. Unfortunately, this whitening ingredient causes the resulting emulsion to become sticky, which somewhat deteriorates the usability 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 a composition that overcomes the above 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, has a brightening or whitening effect on a keratin substance, and at the same time retains a good usability. ..

The present inventors have found that such a need can be achieved by the present invention.

Therefore, according to one aspect, the present invention is a composition in the form of an emulsion for brightening or whitening a keratin substance, which comprises 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) Containing a composition comprising at least one polymer derived from 2-acrylamide methylpropane sulfonic acid.

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

First, the compositions of the present invention have a brightening or whitening effect on keratinous substances, especially human skin.

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

In addition, the compositions of the present invention provide good usability such as moisturizing, nourishing, softness and / or dullness prevention.

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

According to another aspect, the present invention further relates to a cosmetological method for brightening or whitening a keratin substance, particularly human skin, which comprises the step of applying the composition of the present invention to the keratin substance. ..

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

Other subjects, features, embodiments, and advantages of the invention will become clearer by reading the embodiments and examples for carrying out the invention below.

In the following, unless otherwise specified, the limit value of the value range is included in this range, especially in the expressions "between" and "...-... range".

Further, the expression "at least one (species)" as used herein is synonymous with the expression "one (species) or plural (species)".

Throughout the present application, the term "including" is to be construed to include any, additional, unspecified features as well as all features specifically mentioned. As used in the present invention, the use of the term "contains" also discloses embodiments that have no features (ie, "consisting of") other than those specifically mentioned.

According to one aspect, the invention is a composition in the form of an emulsion for brightening or whitening a keratin substance, 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-acrylamide methylpropane sulfonic acid (hereinafter referred to as "AMPS polymer"),
With respect to the composition comprising.

Antioxidant or Skin Whitening Active Ingredient The composition of the 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 polyphenol compounds, making up about two-thirds of the total phenol in the consumed feed. Flavonoids are further classified according to their chemical structure into chalcones, flavones, flavanones, flavanols, flavonols, dihydroflavonols, isoflavonoids, neoflavonoids, catechins, anthocyanidins, and tannins. Over 4,000 flavonoids have been identified, many of which are found in fruits, vegetables and beverages (tea, coffee, beer, wine and fruit beverages). Flavonoids have been reported to have antiviral, antiallergic, antiplatelet, anti-inflammatory, antitumor and antioxidant activity. Flavonoids protect lipids and living cell components from damaging oxidative stress by efficiently removing free radicals.

Preferably, the flavonoid used is a flavon.

Baicalin, a component of the Chinese herb Huang-chin, is a flavonoid, flavon. Baicalin is a powerful antioxidant that exhibits a strong effect on oxidative stress diseases, inflammation, allergies, cancer, bacterial infections and the like.

Baicalin is found in several species of the genus Skullcap (genus Scutellaria), including Scutellaria baicalensis and the blue skullcap (Scutellaria later iflora). The leaves of the Marsh Skullcap (Scutellaria galericulata) have 10 mg / g of baicalin. Baicalin is also present in Oroxylum indicum bark isolates.

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

Preferably, the flavonoids are present in an amount in the range of 0.1% by weight to 2% by weight, preferably 0.1% by weight to 1% by weight, more preferably 0.1% by weight to 0.5% by weight, based on 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 a skin brightening or whitening component.

The hydroxylated diphenylmethane derivative that can be used in the composition of the present invention preferably has the following formula (I) :.

(During the ceremony,
R ₁ is selected from hydrogen atoms, methyl groups, saturated or unsaturated linear or branched hydrocarbon chains with 2-4 carbon atoms, -OH groups, and halogens.
R ₂ is selected from saturated or unsaturated linear or branched hydrocarbon chains with hydrogen atoms, methyl groups, and 2-5 carbon atoms.
R ₃ is selected from a saturated or unsaturated linear or branched hydrocarbon chain with a methyl group or 2-5 carbon atoms.
R ₄ and R ₅ are independent of each other from hydrogen atoms, methyl groups, saturated or unsaturated linear or branched hydrocarbon chains with 2-5 carbon atoms, -OH groups, or halogens. (Selected) is selected from the compounds represented by.

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

According to a preferred embodiment of the present invention, the compound of formula (I) is
During the ceremony
--R ₁ , R ₂ , R ₄ and R ₅ represent hydrogen atoms
--R ₃ is a methyl group,
--- For the OH group, compounds at the ortho and para positions are used for the bonds formed by the carbons that connect 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. Known as the following equation (II):

Corresponds to. This compound has CAS numbers 85-27-8. This compound is marketed by Symrise under the trade name Symwhite 377® or Bio 377.

In the presence of the hydroxylated diphenylmethane derivative, an amount in the range of 0.1% by weight to 2% by weight, more preferably 0.1% by weight to 1% by weight, still more preferably 0.1% by weight to 0.5% by weight, based on the total weight of the composition. Exists in.

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

One type of hydrotrope may be used, but two or more different types of hydrotropes may be used in combination.

Hydrotropes (or hydrotropes) are a different class of compounds characterized by an amphipathic molecular structure and the ability to dramatically improve the solubility of organic molecules that are sparingly soluble in water. May be good. Many hydrotropes have an aromatic structure with ionic moieties, while others have linear alkyl chains, as described in the table below. Hydrotropes are very similar to surfactants and have the ability to reduce surface tension, but because of their small hydrophobic units and their relatively short alkyl chains, they are amphipathic. Distinguished as a class of.

Common hydrotrophic molecules include sodium 1,3-benzenedisulfonate, sodium benzoate, sodium 4-pyridinecarboxylate, sodium salicylate, sodium benzenesulfonate, caffeine, sodium p-toluenesulfonate, butylmono. Sodium glycol glycol sulfate, 4-aminobenzoic acid HCl, sodium cumenesulfonate, N, N-diethylnicotinamide, N-picorylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethylphosphorylcholine, resorcinol, butylurea, pyrogallol , N-picorylacetamide 3,5, prokine HCl, proline HCl, nicotine amide, pyridine, 3-picorylamine, ibuprofen sodium, sodium xylene sulfonate, ethyl carbamate, pyridoxal hydrochloride, sodium benzoate, 2-pyrrolidone, ethyl Examples include urea, N, N-dimethylacetamide, N-methylacetamide and isoniazide. Hydrotrope is described by 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., Karer E.W., "Hydrotropic Solutions", It can be found in Current Opinion in Colloid and Interface Science, Vol. 12, (2007), pp. 121-128.

A cosmetically acceptable hydrotrope is a preferred hydrotrope that can be used in a cosmetic composition. Hydrotropes correspond to a wide class of molecules used in various fields, but their use as cosmetics will be limited due to safety and resistance constraints. Preferred hydrotropes in cosmetics are as described below.

The suitability of hydrotropes for use in cosmetic compositions shall be determined using tests known in the art for determining the effects of compounds on the skin and methods of bioavailability. Can be done.

The advantage of using a hydrotrope 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 active substances. Usually, 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 -0.7 to 6, preferably -0.7 to 1.0, preferably -0.5 to 0.7 for nonionic hydrotropes, and -0.5 to 0.7 for ionic hydrotropes (eg, acidic hydrotropes). It may preferably be -0.7 to 5.5.

The compounder will adjust the pH to maximize the transparency with the hydrotrope.

The log P value is the logarithmic value of the apparent partition coefficient of octane-1-ol / water with a base of 10. The log P value is known and is measured by standardized tests to measure the concentration of (c) compound in octane-1-ol and water. log P is calculated according to the method described in the paper "Atom / Fragment contribution method for estimating octanol-water partition coefficients" by Meylan and Howard, 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 molecular structure. An example is Epiwin software from the US Environment Agency.

This value may be calculated using ACD (Advanced Chemistry Development) Solaris software V4.67 in particular, and this value is also available in "Exploring QSAR: hydrophobic, electronic and steric constants", ACS professional reference book (1995). ) Can also be obtained. Some internet sites provide estimates (address: http://esc.syrres.com/interkow/kowdemo.htm).

Hydrotropes include oxothiazolidin carboxylic acid, vitamin B3 and derivatives thereof, preferably niacinamide, xanthin base, preferably caffeine, camphorbenzalconium metosulfate, ellagic acid, hydroxyphenoxypropionic acid, diethyllutidinate, tele. Phthaliridendicampharsulfonic acid, ferulic acid, salicylic acid, floretin, acetyltrifluoromethylphenylvalylglycine, resveratrol, 4-butylresorcinol, apigenin, phenylethylresorcinol, plasterone, benzophenone-3, butylmethoxydibenzoylmethane, It is preferably selected from the group consisting of capryloyl salicylic acid, ethylhexyl salicylate, and jasmonic acid derivatives, preferably sodium tetrahydrojasmonate. Vitamin B3 and its derivatives described in more detail below, xanthine bases such as caffeine, and jasmonic acid derivatives are more preferred.

(Vitamin B3 and its derivatives)
Vitamin B3, also called vitamin PP, 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 (nicotin uric acid), or CO- It may be NH-OH (nicotinylhydroxamic acid), preferably niacinamide.

Examples of vitamin B3 derivatives include nicotinic acid esters such as tocopherol nicotinate, amides derived from niacinamides by substitution of the hydrogen group of -CONH ₂ , and products from the reaction of carboxylic acids with amino acids. Esters of nicotinyl alcohol and carboxylic acid (acetic acid, salicylic acid, glycolidic acid, palmitic acid, etc.) are included.

The following derivatives: 2-chloronicotinamide, 6-methylnicotinamide, 6-aminonicotinamide, N-methylnicotinamide, N, N-dimethylnicotinamide, N- (hydroxymethyl) nicotinamide, quinophosphateimide, nicotin Anilide, N-benzylnicotinamide, N-ethylnicotinamide, niphenazone, nicotinaldehyde, isonicotinic acid, methylisonicotinic acid, thionicotinamide, nearramid, 2-mercaptonicotinic acid, nicomol and nearprazine, methyl nicotinate, and nicotin Sodium acid acid can also be mentioned.

Other vitamin B3 derivatives that can be similarly mentioned include its inorganic salts such as chlorides, bromides, iodides or carbonates and its organic salts such as salts obtained by reaction with carboxylic acids such as acetates. Includes salicylate, glycolate, lactate, malate, citrate, mandelate, tartrate and the like.

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

(Xanthine base)
Among the xanthine bases that can be used in the present invention, caffeine, theophylline, theobromine, acephyllin, xanthinol nicotinate, diniprophylline, diprophylline, ethamiphyllin and its derivatives, etophylline, proxiphyllin, pentophylline, propentophilin, pyridophyllin. , As well as bamiphyllin, but is not limited to this enumeration.

The xanthine base is preferably selected from the group consisting of caffeine, theophylline, theobromine, acephyllin, and mixtures thereof. These xanthine bases are known as inhibitors of phosphodiesterase, an enzyme involved in the degradation of cAMP. By increasing the intracellular content of cAMP, these xanthine bases promote lipolytic activity and thus constitute an excellent slimming activator.

Examples of plant extracts containing xanthine bases include, but are not limited to, tea, coffee, guarana, mate tea, and koranoki extracts.

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):

(In the equation, R ₁ represents ₃ COOR groups, R ₃ represents a hydrogen atom or a C ₁ to C ₄ alkyl group optionally substituted with one or more hydroxyl groups, and R ₂ is direct. A compound corresponding to a saturated or unsaturated hydrocarbon group (representing a saturated or unsaturated hydrocarbon group having 1 to 18 carbon atoms in a chain, or having 3 to 18 carbon atoms in a branched or cyclic form), and its optical isomers and optical isomers thereof. 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 CH ₂ OH or COOCH ₂ -CH (OH) -CH ₃ . 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 can 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] cyclopentane acetic acid or 3-hydroxy-2-pentylcyclopentane acetic acid, preferably 3-hydroxy-2-pentylcyclopentane acetic acid. 3-Hydroxy-2-pentylcyclopentane acetic acid.

The salt of the compound that can be used in the present invention is specifically an alkali metal salt, for example, a salt of sodium or potassium; an alkaline earth metal salt, for example, a salt of calcium, magnesium, or strontium; a metal salt, For example, salts of zinc, aluminum, manganese, or copper; salts of ammonium of formula NH ₄₊ ; quaternary ammonium salts; organic amine salts such as methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2 ^- hydroxyethylamine. , Salts such as bis (2-hydroxyethyl) amine, or tris (2-hydroxyethyl) amine; or salts of lysine or arginine. It is preferable to use a salt selected from salts of sodium, potassium, calcium, magnesium, strontium, copper, manganese or zinc.

It is preferable to use the following compound (Mexoryl SBO) as the jasmonic acid derivative.

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

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

AMPS Polymer The AMPS polymer used in the present invention is at least acrylamide-2-methylpropanesulfonate in a form partially or totally neutralized with an inorganic base other than ammonia, such as sodium hydroxide or potassium hydroxide. A crosslinked or non-crosslinked homopolymer or copolymer containing an acid monomer.

These AMPS polymers are preferably completely or substantially completely neutralized, i.e. at least 90% neutralized.

These AMPS polymers in the present invention may or may not be crosslinked.

When the polymer is cross-linked, the cross-linking agent can be selected from polyolefin-based unsaturated compounds commonly used for cross-linking the polymer obtained by free radical polymerization.

Examples of cross-linking agents that may be mentioned include 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, Trimethylol Propanetriacrylate, Methylenebisacrylamide, Methylenebismethacrylicamide, Triallylamine, Triallyl cyanurate, Dialylmaleate, Tetraallylethylenediamine, Tetraallyloxyetane, Trimethylolpropanedialyl ether, Allyl (meth) acrylate, Sugar Includes allyl ethers of alcohols, or allyl ethers or vinyl ethers of other polyfunctional alcohols, and allyl esters of phosphate derivatives and / or vinylphosphonic acid derivatives, or mixtures of these compounds.

According to one embodiment of the invention, the cross-linking agent is selected from methylenebisacrylamide, allylmethacrylate and trimethylolpropane triacrylate (TMPTA). The degree of cross-linking is usually in the range of 0.01 mol% to 10 mol%, more specifically 0.2 mol% to 2 mol% with respect to the polymer.

The AMPS polymer in the present invention is water-soluble or water-dispersible. In this case, the polymer is
—— “Homopolymer” containing only AMPS monomers and, if crosslinked, one or more crosslinkers such as those defined above,
--Or, a copolymer obtained from AMPS and one or more hydrophilic or hydrophobic ethylene-based unsaturated monomers and, if crosslinked, one or more cross-linking agents such as those defined above. Is one of. When the copolymer contains a hydrophobic ethylene-based unsaturated monomer, these monomers do not contain a fat chain and are preferably present in a small amount.

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

The term "water-soluble or water-dispersible" means that when introduced into an aqueous phase to a mass concentration equal to 1% at 25 ° C, a macroscopically uniform and transparent solution, i.e., through a 1 cm thick sample with a wavelength equal to 500 nm. Means a polymer that makes it possible to obtain a solution having 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) Disperse or dissolve a free form of a monomer such as AMPS in a tert-butanol solution or a tert-butanol solution.
(b) In an amount that allows the solution or dispersion of the monomer obtained in (a) to be obtained in the range of 90% to 100% of the neutralization degree of the sulfonic acid functional group of the polymer. Neutralize with multiple inorganic or organic bases, preferably ammonia NH ₃ .
(c) Add the cross-linking monomer to the solution or dispersion obtained in (b).
(d) In the presence of a free radical initiator, standard free radical polymerization is performed at temperatures in the range 10-150 ° C. to precipitate the polymer in a tert-butanol-based solution or dispersion. ..

The AMPS homopolymers in the present invention are optionally crosslinked and / or neutralized 2-acrylamide-2-methylpropanesulfonic acid homopolymers, eg Hostacerin AMPS® by Clariant (CTFA name: ammonium poly). It is preferably a poly (2-acrylamide-2-methylpropanesulfonic acid) sold in (acrylic dimethyltauramid).

The water-soluble or water-dispersible AMPS copolymer in the present invention contains a water-soluble ethylene-based unsaturated monomer, a hydrophobic monomer, or a mixture thereof.

The water-soluble comonomer may be ionic or nonionic.

Among the ionic water-soluble comonomer, examples thereof include the following compounds and salts thereof.
-(Meta) acrylic acid,
--Styrene sulfonic acid,
--Vinyl sulfonic acid and (meth) allyl sulfonic acid,
--Vinyl phosphonic acid,
--Maleic acid,
--Itaconic acid,
--Crotonic acid,
--The following formula (V):

(During the ceremony,
--R ₁ is selected from H, -CH ₃ , -C ₂ H ₅ and -C ₃ H ₇
--X ₁ is
--- OR type ₂ Archiether (R ₂ is a linear or branched, saturated or unsaturated hydrocarbon group, having 1 to 6 carbon atoms and at least one sulfone (R 2). A water-soluble vinyl monomer selected from -SO _3- ) and / or sulfate (-SO _4- ) and / or phosphate (replaced by a -PO ₄ H _2- ) group).

Among the nonionic water-soluble comonomer, examples that can be mentioned include
-(Meta) 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 4-9 carbon atoms, such as n-vinylpyrrolidone, N-butyrolactam and N-vinylcaprolactam,
--Formula CH ₂ = CHOH vinyl alcohol,
--The following formula (VI):

(During the ceremony,
--R ₁₅ is selected from H, -CH ₃ , -C ₂ H ₅ and -C ₃ H ₇
--X ₂ is
--OR ₁₆ type alkyl ether (R ₁₆ is a linear or branched, saturated with 1 to 6 carbons optionally substituted with a halogen atom (iodine, bromine, chlorine or fluorine). Alternatively, it contains a water-soluble vinyl monomer (selected from unsaturated hydrocarbon-based groups), hydroxyl groups (-OH), and ethers).

For example, glycidyl (meth) acrylate, hydroxyethyl methacrylate, and (meth) acrylate of ethylene glycol, diethylene glycol, or polyalkylene glycol can be mentioned.

Among the hydrophobic comonomer that does not contain fat chains, an example that can be mentioned is
--Styrene and its derivatives such as 4-butylstyrene, α-methylstyrene and vinyltoluene,
--Vinyl acetate of equation CH ₂ = CH-OCOCH ₃ ,
--Vinyl ether of formula CH ₂ = CHOR (in the formula, R is a linear or branched, saturated or unsaturated hydrocarbon group having 1 to 6 carbons),
--Acrylonitrile,
--Caprolactone,
--Vinyl chloride and vinylidene chloride,
--Silicone derivatives, such as methacryloxypropyltris (trimethylsiloxy) silane and silicone methacrylamide, that polymerize to give a silicone polymer.
--The following equation (VII):

(During the ceremony,
--R ₂₃ is selected from H, -CH ₃ , -C ₂ H ₅ and -C ₃ H ₇
--X ₃ is
--- Hydrophobic of OR ₂₄ type alkyl ether (R ₂₄ is selected from linear or branched, saturated or unsaturated hydrocarbon-based groups containing 1 to 6 carbon atoms). Contains sex vinyl monomers.

Examples thereof 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 polymer of the present invention ranges from 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 preferably has a molar mass.

Examples of water-soluble or water-dispersible AMPS homopolymers in the present invention include acrylamide-2- such as the polymer (CTFA name: polyacryloyldimethyltaurine sodium) used in the commercial product Simulgel ™ 800. Includes crosslinked or non-crosslinked polymers of sodium methylpropanesulfonate.

Examples of water-soluble or water-dispersible AMPS copolymers in the present invention that can be mentioned include:
--Used in copolymers of AMPS with vinylpyrrolidone or vinylformamide, eg commercial products (CTFA name: acryloyldimethyltaurine ammonium / VP copolymer) sold by Clariant under the trade name Aristoflex AVC, but with sodium hydroxide or Copolymer neutralized with potassium hydroxide,
--Used in copolymers of AMPS and sodium acrylate, such as commercial products (CTFA name: acrylamide / acryloyldimethyltaurine sodium / isohexadecane / polysorbate-80) sold by SEPPIC under the trade name Simulgel ™ EG. AMPS / sodium acrylate copolymers such as copolymers,
--AMPS such as copolymers of AMPS and hydroxyethyl acrylate, for example, copolymers used in commercial products (CTFA name: hydroxyethyl acrylate / sodium acryloyldimethyltaurine copolymer) sold by SEPPIC under the trade name of EMT 10. / Includes hydroxyethyl acrylate copolymer.

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

The AMPS polymer accounts for 0.1% by mass to 5% by mass, preferably 0.5% by mass to 3% by mass, and more preferably 0.6% by mass to 1.5% by mass, based on the total mass of the oil-in-water emulsified composition.

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

More specifically, this type of surfactant that can be mentioned includes (INCI name) polysorbate 20, polysorbate 40, polysorbate 60, polysorbate 65, polysorbate 80, polysorbate 85, PEG-5 sorbitan isostearate, PEG. Oxyethylene 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 included.

Polysorbate 20 such as those sold by Croda under the trade name of Tween ™ 20-LQ- (AP) can be mentioned.

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

In the presence of a nonionic surfactant selected from oxyalkyleneized sorbitan fatty acid esters, the compositions of the invention are stable over time.

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

Preferably, the nonionic surfactant is in the range of 0.1% by weight to 3% by weight, preferably 0.1% by weight to 1.5% by weight, more preferably 0.1% by weight to 1% by weight, based on the total weight of the composition. It may be present in quantity.

Aqueous phase The composition of the present invention comprises at least one aqueous phase that is a continuous phase.

The aqueous phase of the composition of the invention is water and optionally one or more miscible or at least partially miscible compounds such as C ₂ to C ₈ lower polyols, or ethanol and isopropanol and the like. Contains mono-alcohol.

The term "polyol" should be understood to mean any organic molecule containing at least two free hydroxyl groups. Examples of polyols that can 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 contain any conventional water-soluble or water-dispersible additive described below.

The aqueous phase is 30% by weight to 98% by weight, preferably 30% by weight to 95% by weight, more preferably 50% by weight to 90% by weight, and even more preferably 60% by weight to 90% by weight, based on the total weight of the composition. May occupy%.

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

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

Specifically, the oil phase contains at least one oil.

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

The oil 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 an 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 specifically, volatile oils have an evaporation rate between 0.01 and 200 mg / cm ² / min (including both ends of the range).

The term "nonvolatile oil" is intended to mean oil that remains in the keratinous material at ambient temperature and atmospheric pressure. More specifically, non-volatile oils have an evaporation rate of exactly below 0.01 mg / cm ² / min.

To measure this evaporation rate, 15 g of the oil or oil mixture to be tested was introduced into a 7 cm diameter crystallizer, temperature controlled to 25 ° C and humidity controlled to 50% relative humidity 0.3 m. Place on a balance located in the large chamber of ³ . A fan (PAPST) placed vertically above the crystallizer containing the solvent, with the blade facing the crystallizer and at a distance of 20 cm from the base of the crystallizer, leaving the liquid to stand. -Ventilated using MOTOREN, reference name 8550N, rotated at 2,700 rpm) to evaporate spontaneously without agitation. The mass of oil remaining in the crystallizer is measured at regular intervals. Evaporation rate is expressed in mg of evaporated oil per unit surface area (cm ² ) and unit time (minutes).

The oil suitable for the present invention is 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, particularly at least one Si-O group.

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

The term "hydrocarbon oil" refers to an oil that mainly contains 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 in the range of 1% by weight to 70% by weight, preferably 10% by weight to 70% by weight, more preferably 10% by weight to 40% by weight, based on the total weight of the composition. ..

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

Additives In known methods, the compositions of the invention may also contain one or more additives commonly used in cosmetics or dermatology.

Examples of auxiliaries that can be mentioned are emulsifiers, gelling agents, activators, preservatives, antioxidants, fragrances, sunscreens (= UV blocking agents), additional pigments, basic agents (triethanol). Includes amines, diethanolamine or sodium hydroxide) or acid 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, eg 0.01% to 30% of the total mass of the composition, depending on the nature of the additive, the aqueous or oil phase of the composition, or the vesicle or optional. Introduced into other types of vectors.

These additives and their concentrations should not change the properties desired for the compositions of the invention.

According to a preferred embodiment, the invention is a composition in the form of an emulsion for brightening or whitening a keratin substance, comprising an oil phase dispersed in an aqueous phase, relative to the total mass of the composition.
(i) As a skin brightening or whitening active ingredient
At least one type of flavone from 0.1% by mass to 0.5% by mass, and the following formula (I):

(During the ceremony,
--R ₁ , R ₂ , R ₄ and R ₅ represent hydrogen atoms
--R ₃ is a methyl group,
--- The OH group is in the ortho and para positions with respect to the bond formed by the carbon connecting the two aromatic nuclei to each other).
At least one hydroxylated diphenylmethane derivative selected from the compounds of 0.1% by weight to 0.5% by weight,
(ii) Oxothiazolidin carboxylic acid, vitamin B3 and its derivatives, preferably niacinamide, xanthin base, preferably caffeine, camphorbenzalconium metosulfate, ellagic acid, hydroxyphenoxypropionic acid, diethyllutidinate, terephthali. Redendican fur sulfonic acid, ferulic acid, salicylic acid, floretin, acetyltrifluoromethylphenylvalylglycine, resveratrol, 4-butylresorcinol, apigenin, phenylethylresorcinol, plasterone, benzophenone-3, butylmethoxydibenzoylmethane, capri At least one hydrotrope selected from loylsalicylic acid, ethylhexyl salicylate, and jasmonic acid derivatives, preferably sodium tetrahydrojasmonate, 1% to 5% by mass,
(iii) At least one optionally crosslinked and / or neutralized 2-acrylamide-2-methylpropanesulfonic acid copolymer 0.6% to 1.5% by weight, 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 At least one nonionic surfactant selected from ceptaoleate, PEG-20 sorbitan tetraoleate and PEG-20 sorbitan trioleate 0.1% by mass to 1% by mass
With respect to the 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, prepared according to conventional methods in the cosmetics field.

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

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

Methods and Applications The compositions of the present invention are for topical application and can specifically constitute keratin substances, especially compositions intended to brighten or whiten human skin.

Accordingly, according to another aspect, the present invention relates to a cosmetological method for brightening or whitening a keratin substance, particularly skin, comprising the step of applying the composition defined above to the keratin substance. ..

The present invention will be illustrated in more detail by the examples described below, but the examples are shown as non-limiting examples.

Percentage is the mass percentage of the active ingredient or active substance.

In the following examples, the mass percentage is shown relative to the total mass of the composition.

(Example 1)
Preparation of Composition by Formulation of the Present Invention and Comparative Formulation The compositions according to the formulas (inv.) 1-2 and the comparative formula (comp.) Of the present invention described in the following table were prepared.

Preparation method:
1. Preparation of aqueous phase: Add hydrotrope component (niacinamide and / or caffeine) to water and stir until completely dissolved, then add ginger root extract and stir until completely dissolved. , Keep the temperature at 75 ° C.
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 aqueous phase and homogenize with a VMI homogenizer at 1,000 rpm for 10 minutes.
4. Cool to less than 60 ° C., optionally add hydroxyethyl acrylate / acryloyldimethyltaurine sodium copolymer, stir until well dispersed, then add sodium hydroxide to adjust the pH to 5.0.

(Example 2)
Evaluation of Formulations of the Present Invention and Comparative Formulations The stability, viscosity and cosmetic properties of the compositions prepared in Example 1 with the formulations of the present invention and the comparative formulations were measured.

The composition of the present invention and the composition for comparison was subjected to a stability test at room temperature (25 ° C.), 40 ° C., and 45 ° C. for 2 months. The test was performed using a Binder (USA) oven by allowing the formulations and comparative formulations of the invention to stand in the oven for 2 months.

Using a Zhongke Meiling refrigerator (YC-260L, China), the cosmetic composition according to the formulation of the present invention and the comparative formulation was left in the refrigerator for 2 months for 2 months at 4 ° C stability. Stability test was carried out.

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

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 in 24 hours.

Viscosity is measured at 25 ° C. using a ProRheo ProRheo R180 viscometer equipped with a spindle M2 rotating at 200 rpm.

The stability and viscosity results for the compositions of the present invention and comparative formulations are described below.

It turns out that the viscosity of the composition in the comparative formulation is too low, which is not desirable.

It can also be seen that the composition according to Formulation 1 of the present 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.
--Franzsel upper pig skin (outer ear)
--Each composition 5 mg / cm ² (applicable range: 1.77 cm ² )
--Applicable for 16 hours at 32 ° C (applicable time in real life)
--Washing after continuing application
--Apply once or twice per cell (10 cells per process)
--Receptor fluid (PBS)
--Stripping was performed on Dsquame® discs
--LC-MS / MS quantification in stratum corneum (SC), skin (epidermis + dermis), and receptor fluid (RF) during washing

The results of bioavailability are listed in the table below.

According to a consumer panel test (n = 60), the compositions according to Formulations 1 and 2 of the present invention have better moisturizing, nourishing, flexibility and dullness prevention to the skin compared to the compositions according to the comparative formula. It turns out that it brings.

Claims (13)

A composition in the form of an emulsion for brightening or whitening a keratin substance, 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) A composition comprising at least one polymer derived from 2-acrylamide methylpropane sulfonic acid. The composition according to claim 1, further comprising at least one nonionic surfactant selected from oxyalkyleneized sorbitan fatty acid esters. The nonionic surfactants are polysorbate 20, polysorbate 40, polysorbate 60, polysorbate 65, polysorbate 80, polysorbate 85, PEG-5 sorbitan isostearate, PEG-20 sorbitan triisostearate, PEG-20 sorbitan isosteer. The composition according to claim 2, wherein the composition is selected from the rate, PEG-40 sorbitan septaoleate, PEG-20 sorbitan tetraoleate, and PEG-20 sorbitan trioleate. The amount of the nonionic surfactant in the range of 0.1% by mass to 3% by mass, preferably 0.1% by mass to 1.5% by mass, more preferably 0.1% by mass to 1% by mass, based on the total mass of the composition. The composition according to claim 2 or 3, which is present in. The composition according to any one of claims 1 to 4, wherein the flavonoid is selected from carcon, flavon, flavanone, flavanol, flavonol, dihydroflavonol, isoflavonoid, neoflavonoid, catechin, anthocyanidin, tannin and the like. .. Claimed that the flavonoids are present in an amount in the range of 0.1% by weight to 2% by weight, preferably 0.1% by weight to 1% by weight, more preferably 0.1% by weight to 0.5% by weight, based on the total weight of the composition. The composition according to any one of Items 1 to 5. The hydrotrope is oxothiazolidin carboxylic acid, vitamin B3 and its derivatives, preferably niacinamide, xanthin base, preferably caffeine, camphorbenzalconium metosulfate, ellagic acid, hydroxyphenoxypropionic acid, diethyllutidinate, Terephthalylidenedicampharsulfonic acid, ferulic acid, salicylic acid, floretin, acetyltrifluoromethylphenylvalylglycine, resveratrol, apigenin, plastolone, benzophenone-3, butylmethoxydibenzoylmethane, capryloyl salicylic acid, ethylhexyl salicylate, and The composition according to any one of claims 1 to 6, selected from the group consisting of a jasmonic acid derivative, preferably sodium tetrahydrojasmonate. The hydrotrope is present in an amount in the range of 0.1% by weight to 10% by weight, preferably 0.5% by weight to 8% by weight, more preferably 1% by weight to 5% by weight, based on the total weight of the composition. The composition according to any one of claims 1 to 7. The polymer derived from the 2-acrylamide methyl propane sulfonic acid is
(i) optionally crosslinked and / or neutralized 2-acrylamide-2-methylpropanesulfonic acid homopolymer,
(ii) optionally crosslinked and / or neutralized 2-acrylamide-2-methylpropanesulfonic acid copolymer, and
(iii) The composition according to any one of claims 1 to 8, which is selected from these mixtures. The polymer derived from the 2-acrylamide methylpropane sulfonic acid is 0.1% by mass to 5% by mass, preferably 0.5% by mass to 3% by mass, more preferably 0.6% by mass to 1.5% by mass, based on the total mass of the composition. The composition according to any one of claims 1 to 9, which is present in an amount in the range of% by mass. As a skin whitening ingredient, the following formula (I):

(During the ceremony,
R ₁ is selected from hydrogen atoms, methyl groups, saturated or unsaturated linear or branched hydrocarbon chains with 2-4 carbon atoms, -OH groups, and halogens.
R ₂ is selected from saturated or unsaturated linear or branched hydrocarbon chains with hydrogen atoms, methyl groups, and 2-5 carbon atoms.
R ₃ is selected from a saturated or unsaturated linear or branched hydrocarbon chain with a methyl group or 2-5 carbon atoms.
R ₄ and R ₅ are independent of each other from saturated or unsaturated linear or branched hydrocarbon chains with hydrogen atoms, methyl groups, 2-5 carbon atoms, -OH groups, or halogens. (Selected)
The composition according to any one of claims 1 to 10, further comprising a hydroxylated diphenylmethane derivative selected from the compounds of the above. A composition in the form of an emulsion for brightening or whitening a keratin substance, comprising an oil phase dispersed in an aqueous phase, with respect to the total mass of the composition.
(i) As a skin brightening or whitening active ingredient
At least one type of flavone from 0.1% by mass to 0.5% by mass, and the following formula (I):

(During the ceremony,
--R ₁ , R ₂ , R ₄ and R ₅ represent hydrogen atoms
--R ₃ is a methyl group,
--- The OH group is in the ortho and para positions with respect to the bond formed by the carbon connecting the two aromatic nuclei to each other).
At least one hydroxylated diphenylmethane derivative selected from the compounds of 0.1% by weight to 0.5% by weight,
(ii) Oxothiazolidin carboxylic acid, vitamin B3 and its derivatives, preferably niacinamide, xanthin base, preferably caffeine, camphorbenzalconium metosulfate, ellagic acid, hydroxyphenoxypropionic acid, diethyllutidinate, terephthali. Redendican fur sulfonic acid, ferulic acid, salicylic acid, floretin, acetyltrifluoromethylphenylvalylglycine, resveratrol, 4-butylresorcinol, apigenin, phenylethylresorcinol, plasterone, benzophenone-3, butylmethoxydibenzoylmethane, capri At least one hydrotrope selected from loylsalicylic acid, ethylhexyl salicylate, and jasmonic acid derivatives, preferably sodium tetrahydrojasmonate, 1% to 5% by mass,
(iii) At least one optionally crosslinked and / or neutralized 2-acrylamide-2-methylpropanesulfonic acid copolymer 0.6% to 1.5% by weight, 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 At least one nonionic surfactant selected from ceptaoleate, PEG-20 sorbitan tetraoleate and PEG-20 sorbitan trioleate 0.1% by mass to 1% by mass
A composition comprising. A cosmetological method for brightening or whitening a keratin substance, particularly human skin, comprising the step of applying the composition according to any one of claims 1 to 12 to the keratin substance.