SKINCARE COMPOSITION

FR3140546B1Active Publication Date: 2025-08-22LOREAL SA
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Patent Information

Application Number
FR2022010221
Authority / Receiving Office
FR · FR
Patent Type
Patents
Current Assignee / Owner
Priority Date
2022-08-31
Filing Date
2022-10-06
Publication Date
2025-08-22
Estimated Expiration
2042-10-06
Patent Text Reader

Abstract

SKINCARE COMPOSITION The present invention relates to a skincare composition, comprising: a) at least one elastin degradation inhibitor; b) at least one ester oil; c) nicotinamide or a derivative thereof; and d) at least one tetrahydropyrimidine compound of formula (I): (I) wherein R is a hydrogen atom or a hydrocarbon radical comprising up to eight carbon atoms, R′ is hydrogen, OH or OR′′ and R′′ is R or COR, R having the same meaning as mentioned above. The present invention also relates to a non-therapeutic skincare method, comprising applying said composition to the skin. Figure for abstract: none
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Description

Title of the invention: SKIN CARE COMPOSITION Technical field

[0001] The present invention relates to a cosmetic composition. In particular, the present invention relates to a skin care composition. The present invention also relates to a non-therapeutic method of skin care. RELATED ART

[0002] Skin is composed of collagen, a protein that polymerizes to form a three-dimensional network of fibers throughout the dermis. Fibroblasts bind to the collagen fibers and cross-link them to generate a strong and stable network. Over time, the attachment points of the cells to the matrix eventually weaken, reducing the ability of the fibroblasts to contract the collagen fibers and resulting in a loss of skin firmness.

[0003] Elastin is another fiber-building protein that makes skin elastic. It gives skin the ability to stretch in response to force and then spring back once the force is removed. Elastin polymers are held together by bonds that are formed between amino acid residues found in peptide chains. The flexibility of the skin depends on this highly cross-linked network of elastic fibers.

[0004] Skin aging results from the effects of intrinsic and extrinsic factors on the skin.

[0005] During the aging process, a harmful change in the structure and functions of the skin occurs. The main clinical signs due to these changes in skin metabolism are the appearance of wrinkles and fine lines, the cause of which is sagging and loss of elasticity of the tissues.

[0006] Furthermore, intrinsic aging, which causes changes in the skin, notably results in a slowdown in the renewal of skin cells, which essentially results in the appearance of harmful clinical changes, such as the reduction of subcutaneous adipose tissue and the appearance of small wrinkles or fine lines, and in histopathological changes, such as an increase in the number and thickness of elastic fibers, a loss of vertical fibers of the elastic tissue membrane, and the presence of large irregular fibroblasts in the cells of this elastic tissue.

[0007] In general, aging of the skin leads to loss of elasticity and smoothness of the skin as well as visible pores on the skin.

[0008] Thus, there is still a need to formulate cosmetic products for skin care, which can improve the elasticity and smoothness of the skin, reduce the visibility of pores on the skin, in order to achieve a relatively youthful skin finish. Summary of the invention

[0009] The inventors have now discovered that it is possible to formulate skin care compositions, which can improve the elasticity and smoothness of the skin, reduce the visibility of pores on the skin, in order to provide a relatively youthful skin finish.

[0010] Therefore, in a first aspect, the present invention provides a skin care composition comprising:

[0011] a) at least one elastin degradation inhibitor;

[0012] b) at least one ester oil;

[0013] c) nicotinamide or a derivative thereof; and

[0014] d) at least one tetrahydropyrimidine compound of formula (I):

[0015] in which R is a hydrogen atom or a hydrocarbon radical comprising up to eight carbon atoms, R' is hydrogen, OH or OR" and R" is R or COR, R having the same meaning as above.

[0016] In a second aspect, the present invention provides a non-therapeutic method of skin care, comprising applying the composition according to the first aspect of the present invention to the skin.

[0017] It has been found that with the combination of components a) to d), the composition of the present invention can improve the elasticity and smoothness of the skin, reduce the visibility of pores on the skin, thereby providing a relatively youthful skin finish.

[0018] The inventors unexpectedly found that component c) and component d) have a synergistic effect in terms of improving the elasticity and softness of the skin.

[0019] Other advantages of the present invention will appear more clearly on reading the description and examples which follow. DETAILED DESCRIPTION OF THE INVENTION

[0020] Unless otherwise indicated, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art in the field to which the present invention relates. When the definition of a term of the present invention conflicts with the meaning commonly understood by those skilled in the art in the field to which the present invention relates, the definition described in the present invention will apply.

[0021] As used herein, unless otherwise indicated, the limits of a range of values ​​are included within that range, particularly in the expressions "between...and..." and "from...to...".

[0022] Furthermore, the expression “at least one” used in the present description is equivalent to the expression “one or more”.

[0023] Throughout the present application, the term "comprising" should be interpreted to encompass all of the specifically mentioned features as well as optional, additional, unspecified features. As used herein, the use of the term "comprising" also discloses the embodiment in which no features other than the specifically mentioned features are present (i.e., "consisting of").

[0024] For the purposes of the present invention, the term "keratinous materials" is intended to cover human skin and mucous membranes such as the lips. Facial skin is particularly considered according to the present invention.

[0025] In the present invention, all percentages refer, unless otherwise indicated, to a weight percentage. Elastin degradation inhibitors

[0026] According to the first aspect, the composition of the present invention comprises at least one elastin degradation inhibitor.

[0027] In the presence of an elastin degradation inhibitor, the activity of elastase, which is an elastin decomposition enzyme, is inhibited, thereby preventing the destruction of elastic fibers in the skin and reducing skin damage caused by exposure to ultraviolet rays, thereby helping to improve skin elasticity.

[0028] Exemplary elastin degradation inhibitors include glycine soja protein, pyrus malus extract, calluna vulgaris extract, hydrolyzed potato protein, pisum sativum extract, acetylarginyltriptophyl diphenylglycine, dipalmitoyl hydroxyproline, juglans regia (walnut) seed extract, dextran, trifluoroacetyl tripeptide-2, frankincense (boswellia serrata) extract, and mixtures thereof.

[0029] For the purposes of the present invention, preferably, the elastin degradation inhibitor is glycine soja protein.

[0030] Advantageously, the elastin degradation inhibitor is present in an amount ranging from 0.01% by weight to 10% by weight, preferably from 0.1% by weight to 8% by weight. weight, preferably from 0.5% by weight to 8% by weight, relative to the total weight of the composition. Ester oils

[0031] According to the first aspect, the composition of the present invention comprises at least one ester oil.

[0032] As used herein, the term "ester oil" means an oil that is liquid at room temperature (25°C) comprising at least one ester function in its molecule. The ester oil may be, for example, a monoester.

[0033] The ester oil may, for example, be chosen from monoesters of formula RiCOOR2 in which:

[0034] Riest chosen from linear and branched hydrocarbon chains comprising from 4 to 40 carbon atoms, preferably from 4 to 30 carbon atoms and more preferably from 7 to 20 carbon atoms, and

[0035] R2 is chosen from branched hydrocarbon chains comprising from 3 to 40 carbon atoms, preferably from 10 to 30 carbon atoms, and more preferably from 16 to 26 carbon atoms.

[0036] Non-limiting examples of ester oils that may be mentioned include isodecyl neopentanoate, isocetyl octanoate, isononyl isononanoate, isodecyl isononanoate, tridecyl isononanoate, hexyl laurate, 2-hexyldecyl laurate, isopropyl myristate, isocetyl myristate, isotridecyl myristate, 2-octyldodecyl myristate, isopropyl palmitate, 2-ethylhexyl palmitate, isooctyl palmitate, isocetyl palmitate, isodecyl palmitate, isostearyl palmitate, 2-octyldecyl palmitate, isopropyl isostearate, 2-octyldodecyl stearate, isostearyl isostearate, 2-octyldodecyl erucate, and mixtures thereof.

[0037] Advantageously, the ester oil is present in the composition of the present invention in an amount ranging from 0.1% by weight to 10% by weight, preferably from 1% by weight to 5% by weight, more preferably from 1% by weight to 3% by weight, relative to the total weight of the composition. Nicotinamide or nicotinamide derivatives

[0038] According to the first aspect, the composition of the present invention comprises at least nicotinamide or a derivative thereof.

[0039] Nicotinamide, also known as vitamin B3, is a compound with the following formula:

[0040] Nicotinamide derivatives that may be cited include, for example, nicotinic acid, nicotinyl alcohol, nicotinuric acid, nicotinyl hydroxamic acid, nicotinic acid esters such as tocopherol nicotinate, amides derived from niacinamide by substitution of the hydrogen groups of -CONH2, products resulting from a reaction with carboxylic acids and amino acids, esters of nicotinyl alcohol and carboxylic acids such as acetic acid, salicyclic acid, glycolic acid or palmitic acid.

[0041] The following derivatives may also be mentioned: 2-chloronicotinamide, 6-methylnicotinamide, 6-aminonicotinamide, N-methylnicotinamide, N,N-dimethylnicotinamide, N-(hydroxymethyl)nicotinamide, quinolinic acid imide, nicotinanilide, N-benzylnicotinamide, N-ethylnicotinamide, nifenazone, nicotinaldehyde, isonicotinic acid, methylisonicotinic acid, thionicotinamide, nialamide, 2-mercaptonicotinic acid, nicomol and niaprazine, methyl nicotinate and sodium nicotinate.

[0042] Advantageously, the nicotinamide or its derivative is present in the composition according to the present invention in an amount of 0.001% by weight to 1% by weight, preferably of 0.01% by weight to 0.5% by weight, more preferably of 0.02% by weight to 0.2% by weight, relative to the total weight of the composition. Tetrahydropyrimidine compounds

[0043] According to the first aspect, the composition of the present invention comprises at least one tetrahydropyrimidine compound of formula (I):

[0044] in which R is a hydrogen atom or a hydrocarbon radical comprising up to eight carbon atoms, R' is hydrogen, OH or OR" and R" is R or COR, R having the same meaning as above.

[0045] Preferably, the tetrahydropyrimidine compound is selected from (4S)-1,4,5,6-tetrahydropyrimidine-4-carboxylic acids and their derivatives. Tetrahydropyrimidine carboxylic acids may have a hydrocarbon group of up to eight carbon atoms in the 2-position, for example an alkyl group or a methyl group. In addition, in the 5,1a-position tetrahydropyrimidine may be substituted with a hydroxy group, in particular a (5S) hydroxy group. The hydroxy group may be etherified or esterified.

[0046] Preferably, the tetrahydropyrimidine compound is selected from (4S)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid, (4S)-3,4,5,6-tetrahydropyrimidine-4-carboxylic acids and hydroxyectoine, (4S, 5S)-5-hydroxy-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid.

[0047] More preferably, the tetrahydropyrimidine compound is selected from (4S)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid, (4S)-3,4,5,6-tetrahydropyrimidine-4-carboxylic acids and hydroxyectoine, and a combination thereof.

[0048] (4S) 2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid meets the following structure: Absolute

[0049] Advantageously, the tetrahydropyrimidine compound is present in the composition in an amount ranging from 0.01% by weight to 10% by weight, preferably from 0.1% by weight to 8% by weight, more preferably from 0.5% by weight to 8% by weight, relative to the total weight of the composition. Aqueous phase

[0050] The composition of the present invention may comprise an aqueous phase.

[0051] Said aqueous phase comprises water.

[0052] Preferably, the continuous aqueous phase comprises a water-miscible organic solvent (at room temperature to 25°C) chosen from glycols and polyols comprising from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferably from 2 to 6 carbon atoms, such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; and mixtures thereof, so as to provide a hydration effect.

[0053] If present, advantageously, the water-miscible organic solvent selected from glycols and polyols is present in the composition in a amount ranging from 0.5% by weight to 20% by weight, preferably from 1% by weight to 10% by weight, relative to the total weight of the composition.

[0054] Preferably, the aqueous phase of the composition of the present invention comprises water and glycerin.

[0055] Advantageously, the aqueous phase is present in the composition of the present invention in an amount of 50% to 95% by weight, preferably 70% to 80% by weight, relative to the total weight of the composition. Oily phase

[0056] The composition of the present invention comprises an oily phase.

[0057] Said oily phase may comprise an additional oil in addition to the ester oil mentioned above.

[0058] The additional oil may be volatile or non-volatile.

[0059] The term "oil" denotes a non-aqueous, water-immiscible compound which is liquid at room temperature (25°C) and atmospheric pressure (760 mmHg). The expression "non-volatile oil" denotes an oil which can remain on keratinous materials, for example the skin, at room temperature and atmospheric pressure for at least several hours and which in particular has a vapor pressure of less than 103 mmHg (0.13 Pa). A non-volatile oil may also be defined as having an evaporation rate such that, under the conditions defined above, the amount evaporated after 30 minutes is less than 0.07 mg / cm2.

[0060] The additional oils may be of vegetable, mineral or synthetic origin.

[0061] Said additional oil may be selected from hydrocarbon, silicone or fluorinated oils.

[0062] The expression “hydrocarbon oil” designates an oil formed essentially or even consisting of carbon and hydrogen atoms, and possibly of O and N atoms, and free of Si and F heteroatoms. This oil may contain alcohol, an ester, an ether, carboxylic acid, an amine and / or amide groups.

[0063] The expression “silicone oil” designates an oil containing at least one silicon atom, in particular Si-O groups.

[0064] The expression “fluorinated oil” designates an oil containing at least one fluorine atom.

[0065] Preferably, the additional oil is selected from hydrocarbon oils and silicone oils, such as dimethicone.

[0066] Advantageously, the oily phase is present in the composition of the present invention in an amount ranging from 1% by weight to 20% by weight, preferably from 2% by weight to 10% by weight, relative to the total weight of the composition of the present invention. Additional cosmetic active ingredients

[0067] The composition of the present invention may comprise an additional cosmetic active ingredient.

[0068] As examples of cosmetic active ingredients, mention may be made of vitamins such as vitamin A (retinol), vitamin E (tocopherol), vitamin C (ascorbic acid), vitamin B5 (panthenol), vitamin B3 (niacinamide) and derivatives of said vitamins (in particular, esters) and mixtures thereof; urea; caffeine; C-glycosides such as hydroxypropyl tetrahydropyrantriol; salicylic acid and its derivatives; alpha-hydroxy acids such as lactic acid or glycolic acid and their derivatives; sunscreens; enzymes; moisturizing agents such as sodium hyaluronate and sodium acetylated hyaluronate, agents acting on microcirculation, and mixtures thereof.

[0069] It is easy for a person skilled in the art to adjust the amount of the additional cosmetic active ingredient based on the end use of the composition according to the present invention. Additional adjuvants or additives

[0070] The composition of the present invention may comprise conventional cosmetic adjuvants or additives, for example perfumes, chelating agents (such as trisodium ethylenediamine disuccinate), preservatives (such as chlorphenesin, phenoxyethanol) and bactericides, thickeners (such as xanthan gum, acrylamide / sodium acryloyldimethyltaurate copolymer), pH regulators (such as triethanolamine, citric acid and sodium hydroxide), surfactants and their derivatives.

[0071] A person skilled in the art can choose the amount of additional adjuvants or additives so as not to have a negative impact on the final use of the composition according to the present invention.

[0072] According to a particularly preferred embodiment, the present invention provides a skin care composition comprising, relative to the total weight of the composition:

[0073] a) from 0.5% by weight to 8% by weight of glycine soja protein;

[0074] b) from 1% by weight to 3% by weight of at least one monoester of formula RiCOOR2, in which Ri is chosen from linear and branched hydrocarbon chains comprising from 7 to 20 carbon atoms, and R2 is chosen from branched hydrocarbon chains comprising from 16 to 26 carbon atoms;

[0075] c) from 0.02% by weight to 0.2% by weight of nicotinamide; and

[0076] d) from 0.5% by weight to 8% by weight of (4S)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid and / or (4S)-3,4,5,6-tetrahydropyrimidine-4-carboxylic acids. Dosage form and process

[0077] The composition of the present invention may be in the form of a gel, cream, lotion or emulsion.

[0078] The composition of the present invention can be used for skin care, particularly for improving the elasticity and smoothness of the skin, reducing the visibility of pores on the skin and making the skin appear younger.

[0079] According to the second aspect, the present invention provides a non-therapeutic method of skin care, comprising applying the composition according to the first aspect of the present invention to the skin.

[0080] The following examples serve to illustrate the present invention without, however, being limiting in nature. EXAMPLES

[0081] The main raw materials used, trade names and their suppliers are listed in Table 1.

[0082] [Tables 1] INCI name Trade name Supplier Ectoin ECTOIN RONACARE® MERCK Niacinamide NIACINAMIDE PC (CODE 5016013) DSM NUTRITIO NAL PRODUCTS Isononyl isononanoate WICKENOL 151 ALZO Glycine soya protein ELESERYL HGP LS 98 74 BASF BEAUTY CARE SOLUTION Glyceryl stearate (and) P EG-100 stearate SIMULSOL™ 165 SEPPIC Acrylamide / sodium acr yloyldimethyltaurate copolymer SIMULGEL™ 600 SEPPIC Dimethicone XIAMETER™ PMX-200 SILICONE FLUID 10 CS T DOW CORNING Inventive Example 1 and Comparative Examples 1-2

[0083] The compositions of Inventive Example (IE) 1 and Comparative Examples (CE) 1-2 were prepared on the basis of the amounts given in Table 2. The amounts are given in % by weight of active ingredient relative to the total weight of the composition.

[0084] [Tables2] Components El. 1 EC. 1 EC. 2 Ectoin 0.101 / / Niacinamide 0.101 2 / Isononyl isononanoate 2.52 1 2.52 Glycine soja protein 5 0.9 5 Glycerin 2 8 2 Glyceryl Stearate (and) PEG-100 Stearate 0.27 0.27 0.27 Phenoxyethanol 0.4 0.5 0.4 Acrylamide / Sodium acryloyld imethyltaurate copolymer 0.34 0.34 0.34 Dimethicone 1 1 1 Triethanolamine 0.064 0.08 0.1 Water QS100 QS100 QS100

[0085] The composition of inventive example 1 represents compositions according to the present invention.

[0086] The composition of Comparative Example 1 does not comprise a tetrahydropyrimidine compound.

[0087] The composition of Comparative Example 2 does not include tetrahydropyrimidine compound and nicotinamide.

[0088] Preparation process:

[0089] The above compositions were prepared as follows, taking as an example the composition of inventive formula 1:

[0090] 1). Add glycerin, phenoxyethanol and water to a blender main and heat the mixture to 65-85°C with stirring to obtain a homogeneous mixture,

[0091] 2). add isononyl isononanoate, glyceryl stearate (and) oil of PEG-100 stearate into the main mixer and heat the resulting mixture to 65-85°C with stirring to obtain a homogeneous mixture,

[0092] 3). Add dimethicone to the main mixer and shake to obtain a homogeneous mixture at 55-75°C,

[0093] 4). add the acrylamide / sodium acryloyldimethyltaurate copolymer into the main mixer at 45-65°C with stirring to obtain a homogeneous mixture and lower the temperature,

[0094] 5). add ectoine, niacinamide, glycine soja protein and triethanolamine into the main mixer when the temperature inside the main mixer is below 40°C, stir the mixture to obtain a homogeneous composition. Assessment

[0095] The performance of the compositions of Inventive Example 1 and Comparative Examples 1-2 was evaluated as follows.

[0096] 62 consumers aged 20 to 45 were invited to apply the composition. And they were evaluated every day morning and evening for 4 weeks, and they were asked to complete the questionnaire in terms of softness and elasticity immediately after application of the composition to be evaluated (instantaneous), softness and appearance (including a younger appearance and visible pores) after one week of application of the composition to be evaluated (TIW) according to their satisfaction.

[0097] The performance level was given based on the following standard according to whether (i) the skin appears softer, (ii) the skin appears more elastic, (iii) the skin appears younger, and (iv) the pores are less visible.

[0098] [Tables4] Consumer satisfaction rate (%) Performance level 90 and above Excellent 80-90 Very good 70-80 Good 60-70 Moderate below 60 No obvious effectiveness

[0099] The results of the consumer satisfaction rate and performance level have been summarized in Table 3 below.

[0100] [Tables3] El. 1 EC. 1 EC. 2 Instant Softness Excellent Moderate Moderate Elasticity Very good Moderate No evident effectiveness TIW Appearance more youthful Very good Moderate / Softness Excellent Good / Visible pores Very good Moderate /

[0101] It can be seen from Table 3, in comparison with the compositions of Comparative Examples 1-2, that the composition of the present invention can significantly improve the elasticity and smoothness of the skin, reduce the visibility of pores on the skin, and can provide a relatively youthful skin finish.

Claims

Claims

1. A skin care composition comprising, relative to the total weight of the composition: a) from 0.5% by weight to 8% by weight of glycine soja protein; b) from 1% by weight to 3% by weight of at least one monoester of formula R1COOR2 in which R1 is selected from linear and branched hydrocarbon chains comprising from 7 to 20 carbon atoms, and R2 is selected from branched hydrocarbon chains comprising from 3 to 26 carbon atoms; c) from 0.02% by weight to 0.2% by weight of nicotinamide; and d) from 0.5% by weight to 8% by weight of (4S)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid and / or (4S)-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid.

2. A composition according to claim 1, wherein the ester oil is isononyl isononanoate.

3. A non-therapeutic method of skin care, comprising applying the composition according to any one of claims 1 to 2 to the skin.