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

A composition with N-acyl alanine, surfactants, and oil enhances rinsing speed and smoothness, addressing the inefficiencies of existing makeup removers.

FR3167295A3Pending 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 do not effectively balance high rinsing speed with delivering a smooth skin texture, particularly when dealing with waterproof products.

Method used

A composition comprising N-acyl alanine and/or its salts, at least one surfactant with a sugar fraction, and at least 2% oil, which can be applied to keratinous materials to enhance rinsing speed and provide a smooth skin texture.

Benefits of technology

The composition achieves rapid rinsing and leaves the skin feeling smooth, effectively removing makeup residues including waterproof products.

✦ Generated by Eureka AI based on patent content.
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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: (iii) N-acyl alanine and / or its salts; (iii) at least one surfactant with at least one sugar fraction; and (iii) at least 2% by weight of at least one oil, relative to the total weight of the composition. The present invention also relates to a method for cleansing and / or removing makeup from keratinous materials, particularly from the skin, comprising applying the composition according to the present invention to the keratinous materials, particularly the 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 consumers of makeup products to have an effective makeup remover available. It must be as effective as possible because oily residues, such as dirt, excess sebum, remnants of cosmetics used daily, and makeup products, especially waterproof products, 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 cleansers on the market are not satisfactory in terms of rinsing speed or the feeling delivered to the skin, for example, smooth texture.

[0006] Therefore, there is a need to formulate compositions, preferably for cleansing and / or removing keratinous materials, which have a high rinsing speed and can deliver a good smooth texture to the skin. Summary of the invention

[0007] An object of the present invention is to propose a composition, preferably for cleansing and / or removing makeup from keratinous materials, which has a high rinsing speed and can deliver a good smooth texture to the skin.

[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. N-acyl alanine and / or its salts; ii. at least one surfactant with at least one sugar fraction; and iii. at least 2% by weight of at least one oil, relative to the total weight of the composition.

[0009] The inventors discovered that the composition has a high rinsing speed and can deliver a good smooth texture to the skin.

[0010] 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.

[0011] Other subjects and 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

[0012] 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.

[0013] 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...".

[0014] Furthermore, the expression "at least one" used in this description is equivalent to the expression "one or more".

[0015] Throughout this application, the term "including" shall be interpreted as encompassing all the specifically mentioned features as well as optional, additional, unspecified features. As used herein, the use of the term "including" also discloses the embodiment in which no features other than the specifically mentioned features are present (i.e., "consisting of").

[0016] 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, can be changed according to the desired purpose.

[0017] 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.

[0018] In the present invention, all percentages refer, unless otherwise specified, to a percentage by weight.

[0019] According to the first aspect, the composition of the present invention comprises: i. N-acyl alanine and / or its salts; ii. at least one surfactant with at least one sugar fraction; and iii. at least 2% by weight of at least one oil, relative to the total weight of the composition. N-acyl alanine and its salts

[0020] The composition according to the present invention comprises N-acyl alanine and / or its salts.

[0021] Preferably, N-acyl alanine and / or its salts are chosen from the compounds represented by formula (1)

[0022] wherein RI represents a linear or branched, saturated or unsaturated hydrocarbon-based group, preferably selected from an alkyl or alkenyl, more preferably selected from a C7-C21 alkyl or alkenyl, even more preferably selected from a C7-C17 alkyl or alkenyl,

[0023] M represents an alkali metal, an alkaline earth metal, ammonium or hydrogen, preferably chosen from the alkali metals and hydrogen, more preferably chosen from sodium, potassium and hydrogen. More preferably, N-acyl alanine and / or its salts are chosen from cocoyl alanine, lauroyl alanine, stearoyl alanine, myristoyl alanine, palmitoyl alanine, oleoyl alanine, sodium cocoyl alaninate, sodium lauroyl alaninate, sodium stearoyl alaninate, sodium myristoyl alaninate, sodium palmitoyl alaninate, sodium oleoyl alaninate, potassium cocoyl alaninate, potassium lauroyl alaninate, potassium stearoyl alaninate, potassium myristoyl alaninate, potassium palmitoyl alaninate, potassium oleoyl alaninate, and their combinations.

[0024] More preferably, N-acyl alanine and / or its salts are selected from cocoyl alanine, lauroyl alanine, sodium cocoyl alaninate, potassium cocoyl alaninate, sodium lauroyl alaninate, potassium lauroyl alaninate, and their combinations.

[0025] Most preferably, the composition according to the present invention comprises lauroyl alanine.

[0026] Advantageously, N-acyl alanine and / or its salts are 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 1.5% by weight to 10% by weight, most preferably from 2% by weight to 8% by weight, relative to the total weight of the composition. Surfactants with at least a sugar fraction

[0027] The composition according to the present invention comprises at least one surfactant with at least one sugar fraction.

[0028] Preferably, the surfactant with at least a sugar fraction is non-ionic.

[0029] Preferably, the surfactant with at least a sugar fraction is chosen from the sucrose esters, sorbitan esters, and mixtures thereof.

[0030] Examples of sucrose esters include mono- or polyester sucrose, preferably mono-, di-, or triesters, comprising at least one saturated or unsaturated C8-C24 group. Preferably, sucrose esters do not contain an alkoxy group (in particular, an ethoxylated or propoxylated group). Suitable sucrose esters include, for example, sucrose cocoate, sucrose laurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose distearate, sucrose oleate, sucrose behenate, or sucrose tristearate, alone or in mixtures.

[0031] Preferably, the sucrose ester is chosen from sucrose laurate, sucrose palmitate, or mixtures thereof.

[0032] With regard to sorbitan esters, examples include sorbitan mono- or polyesters, preferably mono-, di-, or triesters, comprising at least one saturated or unsaturated C8-C24 group. Preferably, sorbitan esters do not contain an alkoxy group (in particular, an ethoxylated or propoxylated group). Suitable sorbitan esters include, for example, sorbitan stearate, sorbitan isostearate, sorbitan tristearate, sorbitan laurate, sorbitan oleate, sorbitan sesquioleate, sorbitan trioleate, and sorbitan palmitate, as well as mixtures thereof.

[0033] More preferably, the surfactant with at least a sugar fraction is chosen from among the esters of sucrose and fatty acids in C8-C24.

[0034] More preferably still, the surfactant with at least a sugar fraction is chosen from sucrose cocoate, sucrose laurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose oleate, sucrose behenate, and mixtures thereof.

[0035] Most preferably, the composition according to the invention comprises at least one surfactant selected from sucrose laurate, sucrose palmitate, and mixtures thereof.

[0036] Advantageously, the surfactant with at least a sugar fraction is present in the composition according to the present invention in an amount ranging from 0.1% by weight to 20% by weight, preferably from 0.2% by weight to 10% by weight, more preferably from 0.4% by weight to 6% by weight, even more preferably from 0.8% by weight to 3% by weight, relative to the total weight of the composition. Oils

[0037] The composition according to the present invention comprises at least 2% by weight of at least one oil, relative to the total weight of the composition.

[0038] The oil may be volatile or non-volatile, preferably the oil is non-volatile.

[0039] The term "oil" refers to a non-aqueous compound immiscible with water that is A non-volatile oil is a liquid at room temperature (25 °C) and atmospheric pressure (760 mmHg). The term "non-volatile oil" means an oil that can remain on keratinous materials at room temperature and atmospheric pressure for at least several hours and, in particular, has a vapor pressure of less than 10³ mmHg (0.13 Pa). A non-volatile oil can 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.

[0040] These oils may be of vegetable, mineral or synthetic origin.

[0041] Said oil can be chosen from hydrocarbon-based oils, silicone oils and fluorinated oils.

[0042] The expression "hydrocarbon-based oil" means an oil formed essentially, or even constituted, by carbon and hydrogen atoms, and optionally by O and N atoms, and free from Si and F heteroatoms. Such an oil may contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.

[0043] The expression "silicone oil" means an oil containing at least one silicon atom, including Si-O groups.

[0044] The expression "fluoridated oil" means an oil containing at least one fluorine atom.

[0045] Preferably, the oil is chosen from hydrocarbon-based oils.

[0046] More preferably, the oil is chosen from linear or branched C10-C28 alkanes, preferably chosen from C12-C24 alkanes.

[0047] Even more preferably, the oil is chosen from among the C15-C19 alkanes.

[0048] Most preferably, the composition comprises a C15-C19 alkane, for example, that sold under the name EMOGREEN™ L19 by the company SEPPIC.

[0049] Advantageously, the oil is present in the composition according to the present invention in an amount ranging from 2% by weight to 90% by weight, preferably from 2.5% by weight to 85% by weight, more preferably from 3% by weight to 80% by weight, relative to the total weight of the composition. Aqueous phase

[0050] Preferably, the composition of the present invention comprises an aqueous phase.

[0051] The aqueous phase is preferably present in an amount ranging from 5% by weight to 95% by weight, more preferably from 10% by weight to 90% by weight, relative to the total weight of the composition.

[0052] Preferably, the aqueous phase comprises at least one water-miscible organic solvent at an ambient temperature of 25 °C, such as monoalcohols having 2 to 6 carbon atoms such as ethanol, isopropanol; polyols having 2 to 6 carbon atoms, such as glycerin, propylene glycol, butylene glycol, pentylene glycol; glycol ethers (having in particular 3 to 16 carbon atoms) such as mono-, di- or tri-propylene glycol (C1-C4 alkyl) ethers, mono-, di- or tri-ethylene glycol (C1-C4 alkyl) ethers; and mixtures thereof.

[0053] Advantageously, the composition comprises an organic solvent, preferably glycerin, present in an amount ranging from 0.5% by weight to 30% by weight, preferably from 2% by weight to 25% by weight, more preferably from 8% by weight to 20% by weight, relative to the total weight of the composition.

[0054] Advantageously, the aqueous phase comprises water, preferably in an amount ranging from 1% by weight to 90% by weight, preferably from 2% by weight to 85% by weight, relative to the total weight of the composition.

[0055] In some preferred embodiments, the aqueous phase comprises water and a polyol having 2 to 6 carbon atoms, preferably glycerin.

[0056] In some preferred embodiments, the composition of the present invention comprises 2% by weight to 85% by weight of water and 8% by weight to 20% by weight of glycerin, relative to the total weight of the composition. Additional ingredients

[0057] The composition according to the present invention may include one or more additional ingredients, chosen from those classically used in skin care cleansers.

[0058] 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.

[0059] 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.

[0060] Preferably, the composition of the present invention has a pH not exceeding 6.5, preferably not exceeding 6.0, more preferably from 4.5 to 6.0.

[0061] 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 2% by weight to 8% by weight of N-acyl alanine and / or its salts selected from cocoyl alanine, lauroyl alanine, sodium cocoyl alaninate, potassium cocoyl alaninate, sodium lauroyl alaninate, potassium lauroyl alaninate, and their combinations; ii. from 0.8% by weight to 3% by weight of at least one surfactant selected from sucrose laurate, sucrose palmitate, and mixtures thereof; and iii. from 3% by weight to 80% by weight of at least one oil chosen from linear or branched C12-C24 alkanes. Method and use

[0062] The composition according to the present invention can be used in a process of cleaning and / or removing makeup from keratinous materials, such as skin, in particular the face, by being applied to the keratinous materials.

[0063] Preferably, the composition according to the present invention is in the form of an emulsion, preferably an oil-in-water emulsion or a water-in-oil-in-water emulsion, more preferably an oil-in-water emulsion.

[0064] It can be used as a daily facial cleanser and / or as a makeup remover.

[0065] 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.

[0066] 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.

[0067] 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

[0068] The following examples are given by way of illustration of the present invention and shall not be construed as limiting the scope.

[0069] The main raw materials used, their trade names and their suppliers have been listed in Table 1.

[0070] [Tables 1] INCI Name Trade Name Supplier Lauroyl alanine AMINIOSURFACT LA SUZHOU WEIMEI C15-19 Alkane EMOGREEN™ L19 SEPPIC

[0071] Inventive Examples 1-2 and Comparative Examples 1-3

[0072] The compositions of the inventive examples (El.) 1-2 and the comparative examples (EC.) 1-3 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).

[0073] [Tables2] El. 1 EL 2 EC. 1 EC.2 EC.3 Lauroyl alanine 5 5 0 5 5 Potassium cocoyl glycinate 0 0 5 0 0 Sucrose laurate 0.65 0.65 0.65 0 0.65 Sucrose palmitate 0.65 0.65 0.65 0 0.65 Polyglyceryl-5 laurate 0 0 0 1.3 0 C15-C19 alkane 70 4 70 70 1 Glycerin 14 14 14 14 14 pH adjusting agent pH5.5 pH5.5 pH5.5 pH5.5 pH5.5 Water QS100 QS100 QS100 QS100 QS100

[0074] The compositions of inventive examples 1-2 represent compositions of the present invention.

[0075] The composition of comparative example 1 includes potassium cocoyl glycinate instead of N-acyl alanine and / or its salts.

[0076] The composition of comparative example 2 includes polyglyceryl-5 laurate instead of a surfactant with at least a sugar fraction.

[0077] The composition of comparative example 3 includes only 1% oil. Preparation process

[0078] The above compositions were prepared as follows.

[0079] First, sucrose laurate and sucrose palmitate (or polyglyceryl-5 laurate), water, glycerin and lauroyl alanine (or potassium cocoyl glycinate) were mixed and heated to 80 °C to melt in an autoclave.

[0080] Next, the C15-C19 alkane heated to 80 °C was slowly added to the autoclave.

[0081] Next, a pH correcting agent was added in the autoclave and the resulting mixture was cooled to room temperature. Assessment

[0082] The rinsing speed of each composition prepared above and the smooth texture of the skin thus delivered were evaluated. Quick rinsing and smooth skin texture

[0083] The rinsing speed of each composition prepared above and the smooth texture of the skin thus delivered were evaluated by 5 skin experts as follows.

[0084] 1 g of a test sample was placed on dry hands individually by the 5 skin experts. Next, 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 hands were rinsed with water.

[0085] The rinsing speed was noted by the 5 skin experts according to the number of hand rinses required until a squeaking sensation appeared, according to the following standard:

[0086] 5: approximately 1 time

[0087] 4: approximately 2 to 3 times

[0088] 3: approximately 4 to 5 times

[0089] 2: approximately 6 to 7 times

[0090] 1: approximately 8 to 10 times

[0091] As used here, the "squeaking sensation" means a sort of astringent and unlubricated sensation.

[0092] The higher the score value, the greater the rinsing speed, with a score > 3.5 being preferable.

[0093] Next, the smooth texture of the skin was noted by the 5 skin experts 2 minutes after towel drying according to the following standard:

[0094] 5: smooth, very hydrated

[0095] 4: Smooth

[0096] 3: slightly rough

[0097] 2: rough

[0098] 1: Dry, pulling, interrupted sensation.

[0099] The higher the score value, the better the smoothness of the skin texture, with a score > 3.5 being preferable.

[0100] The rinsing speed and skin smoothness scores given by the 5 skin experts for each composition of inventive examples 1-2 and comparative examples 1-3 were averaged and rounded, then summarized in Table 3.

[0101] [Tables3] Level 1 Level 2 EC. 1 EC.2 EC.3 Rinse-off speed 3.8 4.4 2.9 1.4 3.4 Skin smoothness 4.4 3.9 3.5 4.6 2.4

[0102] It can be seen from Table 3 that the composition according to the present invention has a high rinsing speed and can deliver a smooth feeling on the skin.

Claims

Demands

1. Composition, preferably for cleansing and / or removing makeup from keratinous materials, comprising: (i) N-acyl alanine and / or its salts; (ii) at least one surfactant with at least one sugar fraction; and (iii) at least 2% by weight of at least one oil, relative to the total weight of the composition.

2. Composition according to claim 1, wherein N-acyl alanine and / or its salts are selected from the compounds represented by the formula (1) H 0 (1) R1 x X ô in which - RI represents a linear or branched, saturated or unsaturated hydrocarbon-based group, preferably selected from an alkyl or alkenyl, preferably selected from a C7-C21 alkyl or alkenyl, more preferably selected from a C7-C17 alkyl or alkenyl; - M represents an alkali metal, an alkaline earth metal, ammonium or hydrogen, preferably selected from the alkali metals and hydrogen, more preferably selected from sodium, potassium and hydrogen.

3. Composition according to claim 1 or 2, wherein N-acyl alanine and / or its salts are selected from cocoyl alanine, lauroyl alanine, sodium cocoyl alaninate, potassium cocoyl alaninate, sodium lauroyl alaninate, potassium lauroyl alaninate, and combinations thereof.

4. Composition according to any one of claims 1 to 3, wherein N-acyl alanine and / or its salts are 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, even more preferably from 1.5% by weight to 10% by weight, most preferably from 2% by weight to 8% by weight, relative to the total weight of the composition.

5. Composition according to any one of claims 1 to 4, wherein the surfactant with at least a sugar fraction is chosen from sucrose esters, sorbitan esters, and mixtures thereof, preferably chosen from C8-C24 fatty acid sucrose esters, more preferably chosen from sucrose cocoate, sucrose laurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose oleate, sucrose behenate, and mixtures thereof, even more preferably chosen from sucrose laurate, sucrose palmitate, and mixtures thereof.

6. Composition according to any one of claims 1 to 5, wherein the oil is selected from hydrocarbon-based oils, preferably, the oil is selected from linear or branched C10-C28 alkanes, more preferably, the oil is selected from C12-C24 alkanes, even more preferably, the oil is selected from C15-C19 alkanes.

7. Composition according to any one of claims 1 to 6, wherein the oil is present in an amount from 2% by weight to 90% by weight, preferably from 2.5% by weight to 85% by weight, more preferably from 3% by weight to 80% by weight, relative to the total weight of the composition.

8. Composition according to claim 1, comprising, relative to the total weight of the composition: (i) 2% by weight to 8% by weight of N-acyl alanine and / or its salts selected from cocoyl alanine, lauroyl alanine, sodium cocoyl alaninate, potassium cocoyl alaninate, sodium lauroyl alaninate, potassium lauroyl alaninate, and combinations thereof; (ii) 0.8% by weight to 3% by weight of at least one surfactant selected from sucrose laurate, sucrose palmitate, and mixtures thereof; and (iii) 3% by weight to 80% by weight of at least one oil selected from C12-C24 linear or branched alkanes.

9. Composition according to any one of claims 1 to 8, 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 to any one of claims 1 to 9, and rinsing off said composition after an optional period.