CLEANSING AND / OR MAKE-UP REMOVAL COMPOSITION FOR KERATINOUS MATERIALS

A composition with acyl and alkali amino acids addresses dripping and foam issues in makeup removers, ensuring effective and pleasant skin cleansing.

FR3167297A3Pending Publication Date: 2026-04-17LOREAL SA
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Patent Information

Authority / Receiving Office
FR · FR
Patent Type
Utility models
Current Assignee / Owner
LOREAL SA
Filing Date
2024-11-15
Publication Date
2026-04-17

AI Technical Summary

Technical Problem

Existing makeup removers often suffer from dripping issues and fail to produce a rich foam, which is undesirable for consumers.

Method used

A composition comprising at least 3% by weight of acyl amino acids and at least one alkali amino acid, along with optional polyols and water, is formulated to prevent dripping and generate a rich foam.

Benefits of technology

The composition effectively prevents dripping and produces a rich foam, enhancing the user experience by providing effective makeup removal without oil residue accumulation.

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Abstract

CLEANSING AND / OR MAKE-UP REMOVER COMPOSITION FOR KERATINOUS MATERIALS The present invention relates to a composition, preferably for cleansing and / or removing makeup from keratinous materials, comprising: at least 3% by weight of at least one acyl amino acid of formula (I), relative to the total weight of the composition: (I) in which, - R1 represents hydrogen, -(CH2)m-NH2, -(CH2)n-COOH, -(CH2)p-OH, or a linear or branched C1-C20 alkyl, m, n and p are independently an integer from 0-10; - R2 represents a linear or branched, saturated or unsaturated hydrocarbon-based group, preferably selected from an alkyl or alkenyl; and (ii) at least one alkaline amino acid.The present invention also relates to a method for cleaning and / or removing makeup from keratinous materials, particularly skin, comprising applying the composition according to the present invention to the keratinous materials, particularly skin, and rinsing off said composition after an optional period. Figure for the abstract: none.
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Description

Title of the invention: CLEANSING AND / OR MAKE-UP REMOVAL COMPOSITION FOR KERATINOUS MATERIALS technical field

[0001] The present invention relates to a composition, preferably for cleaning and / or removing makeup from keratinous materials. The present invention also relates to a method for cleaning and / or removing makeup from keratinous materials using said composition. STATE OF THE ART

[0002] Cleansing the skin or removing makeup is very important for skin care. In particular, it is very important for makeup users to have an effective makeup remover available. It must be as effective as possible because oily residues, such as dirt, excess sebum, remnants of daily cosmetics, and makeup products, especially waterproof ones, accumulate in skin folds, can clog pores, and lead to the appearance of blemishes.

[0003] Several types of skin cleansing or makeup-removing products are known, for example, rinse-off anhydrous oils and gels, foaming creams and lotions.

[0004] Rinse-off anhydrous oils and gels have a cleansing or makeup-removing action due to the oils present in these formulations. These oils dissolve oily residues and disperse makeup pigments.

[0005] However, some cleaners on the market are not satisfactory, for example, they will have a problem of dripping or will not be able to produce a rich foam, which is unpleasant for consumers.

[0006] Therefore, there is a need to formulate compositions, preferably for cleansing and / or removing makeup from keratinous materials, which do not present a problem of dripping and can produce a rich foam. Summary of the invention

[0007] An object of the present invention is to propose a composition, preferably for cleaning and / or removing makeup from keratinous materials, which does not present a problem of dripping and can produce a rich foam.

[0008] Thus, according to a first aspect, the present invention relates to a composition, preferably for cleaning and / or removing makeup from keratinous materials, comprising: i. at least 3% by weight of at least one acyl amino acid of formula (I), relative to the total weight of the composition:

[0009] [Chem.l] H o R2 OH OR RI (I)

[0010] in which,

[0011] - RI represents hydrogen, -(CH2)m-NH2, -(CH2)n-COOH, -(CH2)P-OH, or an alkyl in linear or branched CrC2o, m, n and p are independently an integer from 0-10;

[0012] - R2 represents a linear or branched, saturated hydrocarbon-based group or unsaturated, preferably chosen from an alkyl or alkenyl; and i. at least one alkali amino acid.

[0013] The inventors discovered that with the combination of at least 3% by weight of at least one acyl amino acid and at least one alkaline amino acid, the composition does not present a problem of dripping and can produce a rich foam.

[0014] According to a second aspect, the present invention proposes a method for cleaning and / or removing makeup from keratinous materials, in particular from the skin, comprising applying the composition according to the present invention to the keratinous materials, in particular to the skin, and rinsing off said composition after an optional period.

[0015] Other subjects, features, aspects, and advantages of the present invention will be presented in the following description and will be partly evident from the description or may be learned through practice of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0016] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as that commonly understood by a person skilled in the art of the present invention. Where the definition of a term in this description conflicts with the meaning commonly understood by a person skilled in the art of the present invention, the definition described herein shall apply.

[0017] In what follows and unless otherwise indicated, the limits of a range of values ​​are included in that range, in particular in the expressions "between...and..." and "from...to...".

[0018] Furthermore, the expression "at least one" used in this description is equivalent to the expression "one or more".

[0019] Throughout this application, the term "including" shall be interpreted as encompassing all the features specifically mentioned as well as optional, additional, unspecified features. As used here, the use of the term "including" also discloses the embodiment in which no features other than those specifically mentioned are present (i.e., "consisting of").

[0020] Unless otherwise specified, all numerical values ​​expressing a quantity of ingredients and the like used in the description and claims shall be understood as modified by the term "approximately". Consequently, unless otherwise indicated, the numerical values ​​and parameters described herein are approximate values ​​which, if necessary, may be changed according to the desired purpose.

[0021] For the purposes of the present invention, the term "keratinous material" is intended to cover human skin and mucous membranes such as the lips. Facial skin is particularly considered in the context of the present invention.

[0022] In the present invention, all percentages refer, unless otherwise specified, to a percentage by weight.

[0023] According to the first aspect, the composition of the present invention comprises: i. at least 3% by weight of at least one acyl amino acid of formula (I), relative to the total weight of the composition:

[0024] [Chem.2] H o R2, AA OH It 1 OR RI (I)

[0025] in which,

[0026] - RI represents hydrogen, -(CH2)m-NH2, -(CH2)n-COOH, -(CH2)P-OH, or an alkyl in linear or branched CrC2o, m, n and p are independently an integer from 0-10;

[0027] - R2 represents a linear or branched, saturated hydrocarbon-based group or unsaturated, preferably chosen from an alkyl or alkenyl group; and i. at least one alkali amino acid. Acyl amino acids

[0028] The composition comprises at least 3% by weight of at least one acyl amino acid of formula (I) mentioned above.

[0029] Preferably, in formula (I), RI represents hydrogen, -(CH2)m-NH2, -(CH2)n-COOH, -(CH2)P-OH, a linear alkyl in C1-C6, m, n and p are independently a an integer from 1-6, R2 represents a linear or branched C7-C2i alkyl or alkenyl

[0030] More preferably, in formula (I), RI represents hydrogen, -(CH2)m-NH2, -(CH2)n-COOH, -(CH2)P-OH, a linear C1-C4 alkyl, m, n and p are independently an integer from 1-4, R2 represents a linear or branched C7-C19 alkyl or alkenyl.

[0031] Even more preferably, in formula (I), RI represents hydrogen, -(CH2)m-NH2, -(CH2)n-COOH, -(CH2)P-OH, a linear alkyl in Ci-C4, m, n and p are independently an integer from 2-4, R2 represents a linear or branched alkyl or alkenyl in C7-Ci7.

[0032] Furthermore, more preferably, in formula (I), RI represents hydrogen, -(CH2)4-NH2 -(CH2)2-COOH, -(CH2)4-OH, or -CH3, R2 represents a linear or branched C7 alkyl or alkenyl -Ci7.

[0033] Examples of acyl amino acids include cocoyl glutamic acid, lauroyl glutamic acid, stearoyl glutamic acid, myristoyl glutamic acid, palmitoyl glutamic acid, oleoyl glutamic acid, cocoyl alanine, lauroyl alanine, stearoyl alanine, myristoyl alanine, palmitoyl alanine, oleoyl alanine, cocoyl glycine, lauroyl glycine, stearoyl glycine, myristoyl glycine, palmitoyl glycine, oleoyl glycine, cocoyl lysine, lauroyl lysine, stearoyl lysine, myristolysine, palmitoyl lysine, oleoyl lysine, and their combinations.

[0034] More preferably, the acyl amino acid is chosen from cocoyl alanine, lauroyl alanine, stearoyl alanine, myristoyl alanine, palmitoyl alanine, oleoyl alanine, and their combinations.

[0035] Most preferably, the composition according to the present invention comprises lauroyl alanine.

[0036] Advantageously, acyl acyl amine is present in the composition according to the present invention in an amount ranging from 3% by weight to 30% by weight, preferably from 6% by weight to 25% by weight, more preferably from 8% by weight to 20% by weight, relative to the total weight of the composition. Alkaline amino acids

[0037] The composition comprises at least one alkali amino acid.

[0038] As used here, the expression "alkaline amino acid" is different from the acyl amino acid mentioned above.

[0039] The expression "alkaline amino acid" means an amino acid comprising more basic functions than acidic functions, in particular proteinogenic amino acids, the side chain of which includes a basic function.

[0040] Preferably, the alkaline amino acid is chosen from glycine, arginine, histidine, lysine, sarcosine, ornithine and citrulline, and mixtures thereof.

[0041] More preferably, the alkali amino acid is chosen from glycine, arginine, ornithine, and mixtures thereof.

[0042] Most preferably, the composition according to the invention comprises arginine, in particular L-arginine.

[0043] Advantageously, the alkali amino acid is present in the composition according to the present invention in an amount ranging from 0.1% by weight to 30% by weight, preferably from 0.5% by weight to 20% by weight, more preferably from 1% by weight to 15% by weight, even more preferably from 3% by weight to 10% by weight, relative to the total weight of the composition. Polyols

[0044] Preferably, the composition of the present invention comprises at least one polyol.

[0045] Preferably, the polyol has from 2 to 6 carbon atoms.

[0046] More preferably, the polyol is chosen from glycerol, diglycerol, propanediol, isoprene glycol, dipropylene glycol, butylene glycol, hexylene glycol, pentylene glycol, and their combinations.

[0047] Most preferably, the composition of the present invention comprises 1,3-propanediol.

[0048] Advantageously, the polyol is present in the composition according to the present invention in an amount ranging from 1% by weight to 40% by weight, preferably from 5% by weight to 35% by weight, preferably from 10% by weight to 30% by weight, relative to the total weight of the composition. Water

[0049] Preferably, the composition of the present invention comprises water.

[0050] Advantageously, water is present in the composition according to the present invention in an amount ranging from 10% by weight to 90% by weight, preferably from 30% by weight to 85% by weight, preferably from 50% by weight to 80% by weight, relative to the total weight of the composition. Additional ingredients

[0051] The composition according to the present invention may include one or more additional ingredients, chosen from those classically used in skin care cleansers.

[0052] The composition according to the present invention may include, for example, one or more of the following: pH correcting agents; antibacterial agents, perfumes, and thickeners.

[0053] A person skilled in the art can adjust the type and quantity of additional ingredients present in the compositions according to the present invention by means of routine operations, so that the desired properties of these compositions are not negatively affected by the additional ingredients.

[0054] Preferably, the composition is oil-free.

[0055] As used herein, the term "oil" refers to a fatty substance that is liquid at room temperature (25 °C) and atmospheric pressure (760 mmHg).

[0056] As used herein, the term "oil-free" refers to a composition that contains 1% by weight or less, preferably 0.5% by weight or less, of oil, relative to the total weight of the composition.

[0057] Preferably, the composition has a pH not exceeding 6.5. More preferably, the composition has a pH not exceeding 6.0, even more preferably, the composition has a pH of 4.5 to 6.0.

[0058] According to a preferred embodiment, the present invention relates to a composition, preferably for cleansing and / or removing makeup from keratinous materials, comprising, relative to the total weight of the composition: i. from 8% by weight to 20% by weight of at least one acyl amino acid selected from cocoyl alanine, lauroyl alanine, stearoyl alanine, myristoyl alanine, palmitoyl alanine, oleoyl alanine, and combinations thereof; and ii. from 3% by weight to 10% by weight of at least one alkaline amino acid chosen from glycine, arginine, omithine, and mixtures thereof. Method and use

[0059] Preferably, the composition according to the present invention is used in a process for cleaning and / or removing makeup from keratinous materials, such as skin, in particular the face, by being applied to the keratinous materials.

[0060] It can be used as a daily facial cleanser and / or as a makeup remover.

[0061] Preferably, the composition of the present invention is a rinse-off product. Thus, such a composition can be applied to the skin (namely, the face and / or body), and then rinsed off with running water.

[0062] The composition according to the invention can be applied by any means allowing uniform distribution, in particular with a finger, or a cotton ball, and can be removed by rinsing with water.

[0063] Thus, according to the second aspect, the present invention proposes a method for cleaning and / or removing makeup from keratinous materials, in particular from the skin, comprising applying the composition according to the present invention to the keratinous materials, in particular to the skin, and rinsing off said composition after an optional period. EXAMPLES

[0064] The following examples are given by way of illustration of the present invention and shall not be construed as limiting the scope.

[0065] The main raw materials used, their trade names and their suppliers have been listed in Table 1.

[0066] [Tables 1] INCI Name Trade Name Supplier Lauroyl alanine AMINIOSURFACT LA SUZHOU WEIMEI Arginine L-ARGININE AJINOMOTO Inventive Example#! and Comparative Examples#l-4

[0067] The compositions of inventive example (EL) 1 and comparative examples (EC.) 1-4 were prepared with the components listed in Table 2 (the contents were expressed as percentages by weight relative to the total weight of each composition):

[0068] [Tables2] Components E.1.1 EC 1 EC 2 EC 3 EC 4 Lauroyl alanine 10 2 0 10 10 Sodium cocoyl alaninate 0 0 10 0 0 Arginine 6.4 6.4 0 0 0 1,3-propanediol 20 20 20 20 20 Citric acid Adjust pH Adjust pH Adjust pH Same as EI 1 * 0 Sodium hydroxide 0 0 0 0 Adjust pH Water QS100 QS100 QS100 QS100 QS100 pH 5.5 5.5 5.5 ND 5.5

[0069] ND: not subject to testing.

[0070] * : the quantity of citric acid in comparative example 3 is the same as the quantity of citric acid in inventive example 1.

[0071] The composition of inventive example 1 represents the composition of the present invention.

[0072] The composition of comparative example 1 comprises only 2% by weight of acyl amino acid.

[0073] The composition of comparative example 2 does not include at least one acyl amino acid and at least one alkali amino acid.

[0074] The composition of comparative example 3 does not include at least one alkali amino acid.

[0075] The composition of comparative example 4 includes sodium hydroxide rather than an alkali amino acid. Preparation process

[0076] The above compositions were prepared as follows.

[0077] All raw materials, with the exception of the pH adjusting agent used (citric acid or sodium hydroxide), were mixed to obtain a premix. The premix was then heated to 80°C with stirring, and the pH adjusting agent was added to the premix to obtain a mixture, which was then cooled to 25°C to obtain a corresponding composition. Assessment

[0078] The viscosity of each composition prepared above and the resulting volume of foam were evaluated. Viscosity

[0079] The viscosity of each of the above compositions was measured at 25°C using a Rheomat RI80 viscometer equipped with an M4 spindle. The measurement was taken after 10 minutes of spindle rotation in the composition under test (after which viscosity stabilization was observed), at a shear speed of 200 rpm. The results are summarized in Table 3.

[0080] According to the present invention, when the viscosity is > 900 mPa.s, there is no problem of dripping. Foam volume

[0081] The volume of foam achieved by each composition prepared above was evaluated by 5 skin experts as follows.

[0082] 1 g of a test sample was placed on wet hands by the 5 experts in skin individually. Then, 1 mL of water was added to the test sample using a pipette, then a hand rub was performed 20 times, an additional 1 mL of water was added, then a rub was performed 20 more times, then the resulting foam was collected in a palm to assess the foam volume.

[0083] The volume of foam was noted by the 5 skin experts according to the following standards.

[0084] 5: around a palm

[0085] 4: more than half a palm but less than a palm

[0086] 3: bubble larger than 1 / 4 of a palm but less than half a palm

[0087] 2: bubble equal to or less than 1 / 4 of a palm

[0088] 1: no foam.

[0089] The higher the score value, the higher the volume of foam, where scores > 3 are preferable.

[0090] The scores for the foam volume were given by the 5 skin experts for each composition of inventive example 1 and comparative examples 1-4 and were averaged and rounded, then summarized in Table 3.

[0091] [Tables3] EI1 EC 1 EC 2 EC 3 EC 4 Viscosity (mPa.s) 1363 <10 <10 ND* 1572 Foam volume 5.0 2.8 3.7 ND 1.0

[0092] ND* means that the composition under test is heterogeneous and that there are solid particles suspended in the aqueous phase so that the viscosity cannot be determined.

[0093] ND: not determined.

[0094] It can be seen in Table 3 that the composition according to the present invention has an appropriate viscosity so that it does not present any dripping problems, and can produce a rich foam.

Claims

Demands

1. Composition, preferably for cleansing and / or removing makeup from keratinous materials, comprising: i. at least 3% by weight of at least one acyl amino acid of formula (I), relative to the total weight of the composition: [Chem. 3] H 0 R2 x oh Il 1 0H 0 RI (I) in which, - RI represents hydrogen, -(CH2)m-NH2, -(CH2)n-COOH, -(CH 2)P-OH, or a linear or branched Ci-C20 alkyl, m, n and p are independently an integer from 0-10; - R2 represents a linear or branched, saturated or unsaturated hydrocarbon-based group, preferably selected from an alkyl or alkenyl; and (ii) at least one alkali amino acid.

2. Composition according to claim 1, wherein, in formula (I), RI represents hydrogen, -(CH2)m-NH2, -(CH2)n-COOH, -(CH2)P-OH, a linear CrC6 alkyl, m, n and p are independently an integer from 1-6; R2 represents a linear or branched C7-C2i alkyl or alkenyl; Preferably, RI represents hydrogen, -(CH2)m-NH2, -(CH2)n-COOH, -(CH2)P-OH, a linear CrC4 alkyl, where m, n, and p are independently integers from 1 to 4. R2 represents a linear or branched C7-Ci9 alkyl or alkenyl. More preferably, RI represents hydrogen, -(CH2)m-NH2, -(CH2)n-COOH, -(CH2)P-OH, a linear Ci-C4 alkyl, where m, n, and p are independently integers from 2 to 4. R2 represents a linear or branched C7-C[7] alkyl or alkenyl. Even more preferably, RI represents hydrogen, -(CH2)4-NH2, -(CH2)2-COOH, -(CH2)4-OH, or -CH3. R2 represents a linear C7-C[7] alkyl or alkenyl. or branched.

3. Composition according to claim 1 or 2, wherein the amino acyl acid is selected from cocoyl alanine, lauroyl alanine, stearoyl alanine, myristoyl alanine, palmitoyl alanine, oleoyl alanine, and combinations thereof.

4. Composition according to any one of claims 1 to 3, wherein the acyl amino acid is present in an amount from 3% by weight to 30% by weight, preferably from 6% by weight to 25% by weight, more preferably from 8% by weight to 20% by weight, relative to the total weight of the composition.

5. Composition according to any one of claims 1 to 4, wherein the alkali amino acid is selected from glycine, arginine, histidine, lysine, sarcosine, omithine, citrulline, and mixtures thereof, preferably the alkali amino acid is selected from glycine, arginine, ornithine, and mixtures thereof.

6. Composition according to any one of claims 1 to 5, wherein the alkali amino acid is present in an amount from 0.1% by weight to 30% by weight, preferably from 0.5% by weight to 20% by weight, more preferably from 1% by weight to 15% by weight, and even more preferably from 3% by weight to 10% by weight, relative to the total weight of the composition.

7. Composition according to claim 1, comprising, in relation to the total weight of the composition: (i) 8% by weight to 20% by weight of at least one acyl amino acid selected from cocoyl alanine, lauroyl alanine, stearoyl alanine, myristoyl alanine, palmitoyl alanine, oleoyl alanine, and combinations thereof; and (ii) 3% by weight to 10% by weight of at least one alkali amino acid selected from glycine, arginine, ornithine, and mixtures thereof.

8. Composition according to any one of claims 1 to 7, which is oil-free.

9. Composition according to any one of claims 1 to 9, having a pH not exceeding 6.5, preferably not exceeding 6.0, more preferably from 4.5 to 6.

0.

10. A method for cleaning and / or removing makeup from keratinous materials, in particular from the skin, comprising applying to the keratinous materials, in particular to the skin, the composition according any one of claims 1 to 9, and rinsing said composition after an optional period.