COMPOSITION AND PROCESS FOR THE CARE OF KERATINOUS MATERIALS

A composition with hexapeptides, dipeptides, and Laminaria digitata extract stimulates collagen IV production, addressing the inadequacies of existing anti-aging products by enhancing skin radiance and reducing wrinkles.

FR3158886B3Active Publication Date: 2026-02-13LOREAL SA
View PDF 0 Cites 0 Cited by

Patent Information

Application Number
FR2024002097
Authority / Receiving Office
FR · FR
Patent Type
Utility models
Current Assignee / Owner
Priority Date
2024-02-05
Filing Date
2024-03-01
Publication Date
2026-02-13
Estimated Expiration
2034-03-01

AI Technical Summary

Technical Problem

Existing cosmetic products are inadequate in effectively resisting skin aging due to insufficient stimulation of collagen production.

Method used

A composition comprising hexapeptides, dipeptides, Laminaria digitata extract, and polyhydroxy acids is formulated to stimulate collagen IV production, providing an anti-aging effect on keratinous materials.

Benefits of technology

The composition effectively resists skin aging by enhancing collagen production, improving skin radiance and reducing wrinkles and ptosis.

✦ Generated by Eureka AI based on patent content.
Patent Text Reader

Abstract

COMPOSITION AND METHOD FOR THE TREATMENT OF KERATINOUS MATERIALS The present invention relates to a composition comprising: (i) at least one hexapeptide; (ii) at least one dipeptide; (iii) Laminaria digitata extract; and (iv) at least one polyhydroxy acid. The present invention also relates to a non-therapeutic method for treating keratinous materials, comprising applying said composition to the keratinous materials. Figure for the abstract: none
Need to check novelty before this filing date? Find Prior Art

Description

Title of the invention: COMPOSITION AND METHOD FOR THE CARE OF KERATINOUS MATERIALS technical field

[0001] The present invention relates to a composition. In particular, the present invention relates to a composition for the care of keratinous materials. The present invention also relates to a non-therapeutic method for the care of keratinous materials. PRIOR TECHNOLOGY

[0002] Human skin consists of three compartments, namely a superficial compartment, which is the epidermis, the dermis and a deep compartment, which is the hypodermis.

[0003] The dermis is primarily composed of fibroblasts and an extracellular matrix (ECM). This extracellular matrix consists of various macromolecules responsible for the skin's mechanical resistance, suppleness, tone, and elasticity, as well as physiologically important functions (hydration, thermoregulation, and regulation of skin permeability). These macromolecules include, in particular, collagens, elastin, and glycoconjugates (glycoproteins and proteoglycans).

[0004] Collagens represent 70% of the proteins in the ECM. Naturally, collagens are constantly renewed, but this renewal decreases with age, resulting in thinning of the dermis.

[0005] A wide variety of cosmetic products are used to care for the skin, for example, to resist skin aging by stimulating collagen production. However, some cosmetic products on the market are not satisfactory in terms of resisting skin aging.

[0006] Thus, there is always a need to formulate a skincare composition that can effectively resist skin aging. Summary of the invention

[0007] An object of the present invention is therefore to develop a skin care composition which can effectively resist skin aging.

[0008] Another object of the present invention is to propose a cosmetic skin care process.

[0009] The inventors have now discovered that the composition of the present invention can effectively resist skin aging.

[0010] Consequently, in a first aspect, the present invention proposes a composition comprising: i. at least one hexapeptide; ii. at least one dipeptide; iii. of the extract of Laminaria digitata; and iv. at least one polyhydroxy acid.

[0011] The inventors have discovered that the composition of the present invention can effectively resist skin aging by stimulating the production of collagen IV.

[0012] In a second aspect, the present invention proposes a non-therapeutic method for the treatment of keratinous materials, comprising the application of the composition according to the first aspect of the present invention to the keratinous materials.

[0013] In a third aspect, the present invention proposes a use of the composition according to the first aspect of the present invention to provide an anti-aging effect on keratinous materials.

[0014] Other subjects, features, aspects, and advantages of the invention will become even clearer upon reading the description and examples that follow. DETAILED DESCRIPTION OF THE INVENTION

[0015] 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 in the field covered by 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 in the field covered by the present invention, the definition described herein shall apply.

[0016] 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...".

[0017] Moreover, the expression "at least one" used in this description is equivalent to the expression "one or more".

[0018] 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").

[0019] 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". Accordingly, unless otherwise stated, the numerical values ​​and parameters described These are approximate values ​​which, if necessary, can be changed according to the desired objective.

[0020] 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 considered in particular according to the present invention.

[0021] In the present invention, all percentages refer, unless otherwise specified, to a percentage by weight.

[0022] According to the first aspect, the composition of the present invention comprises: i. at least one hexapeptide; ii. at least one dipeptide; iii. of the extract of Laminaria digitata; and iv. at least one polyhydroxy acid. Hexapeptides

[0023] The composition of the present invention comprises at least one hexapeptide.

[0024] Preferably, the hexapeptide is any type of hexapeptide containing the sequence -Glu-Glu-Met-Gln-Arg-Arg-.

[0025] More preferably, the hexapeptide is chosen from those of formula (I):

[0026] Ri-Glu-Glu-Met-Gln-Arg-Arg-R2(I)

[0027] in which • Ri is selected from H, a polyethylene glycol-derived polymer, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl, aralkyl and R5-CO-, in which R5 is selected from H, a non-cyclic aliphatic group, alicyclyl, aryl, aralkyl, heterocyclyl and heteroarylalkyl; • R2 is chosen from the group consisting of -NR3R4, -OR3, -SR3, in which R3 and R4 are chosen independently from H, a polyethylene glycol-derived polymer, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl, and aralkyl; and • Ri and R2 are not amino acids.

[0028] As used herein, the term "non-cyclic aliphatic group" includes linear (i.e., straight-chain and unbranched) or branched, saturated or unsaturated hydrocarbyl groups such as alkyl, alkenyl, and alkynyl. The non-cyclic aliphatic group may be substituted (monosubstituted or polysubstituted) or unsubstituted.

[0029] As used here, the term "alkyl" includes both linear and saturated branched alkyl groups, which may be substituted (monosubstituted or polysubstituted) or unsubstituted. The alkyl group is linked to the rest of the molecule by a single bond. The alkyl group has from 1 to 24, preferably from 1 to 16, more preferably from 1 to 14, even more preferentially from 1 to 12, but even more preferentially 1, 2, 3, 4, 5 or 6 carbon atoms. The term 'alkyl' includes, for example, methyl, ethyl, isopropyl, isobutyl, tert-butyl, 2-methylbutyl, heptyl, 5-methylhexyl, 2-ethylhexyl, octyl, decyl, dodecyl, lauryl, hexadecyl, octadecyl and amyl.

[0030] As used herein, the term "alkenyl" refers to a group containing one or more carbon-carbon double bonds, which may be linear or branched and substituted (monosubstituted or polysubstituted) or unsubstituted. Preferably, it has 1, 2, or 3 carbon-carbon double bonds. If more than one carbon-carbon double bond is present, the double bonds may be conjugated or nonconjugated. Preferably, the alkenyl group has from 2 to 24, preferably from 2 to 16, more preferably from 2 to 14, even more preferably from 2 to 12, but still more preferably 2, 3, 4, 5, or 6 carbon atoms. The alkenyl group is linked to the rest of the molecule by a single bond. The term "alkenyl" includes, for example, the vinyl(-CH2=CH2), allyl(-CH2-CH=CH2), prenyl, oleyl, linoleyl and similar groups.

[0031] The term "alkynyl" designates a group containing one or more carbon-carbon triple bonds and which may be linear or branched, and substituted (monosubstituted or polysubstituted) or unsubstituted. Preferably, the alkynyl group has 1, 2, or 3 carbon-carbon triple bonds. The triple bonds may be conjugated or nonconjugated. The alkynyl group has from 2 to 24, preferably from 2 to 16, more preferably from 2 to 14, even more preferably from 2 to 12, but still more preferably 2, 3, 4, 5, or 6 carbon atoms. The alkynyl group is bonded to the rest of the molecule by a single bond. The term "alkynyl" includes, for example and without limitation, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, pentynyl, such as 1-pentynyl, and similar compounds.The alkynyl group may also contain one or more carbon-carbon double bonds, and alkynyl groups include, for example but not limited to, but-l-en-3-ynyl and pent-4-en-l-ynyl groups, and similar ones.

[0032] The term "alicyclyl" is used here to cover, for example, but not limited to, aliphatic cyclic (alicyclic) groups such as cycloalkyl, cycloalkenyl, or cycloalkynyl groups. The term "alicyclyl" designates a monoradical that contains one or more rings of carbon atoms; the rings may be saturated (e.g., cyclohexyl) or unsaturated (e.g., cyclohexenyl), provided they are not aromatic. More specifically, alicyclic groups contain three or more cyclic carbon atoms, from 3 to 24, from 3 to 12, or from 6 to 12. The alicyclic group may be a monocyclic, bicyclic, or tricyclic system, and the rings may, for example, be fused or bonded. by a single bond or a bonding group such as a methylene group or another alkylene group. The alicyclic group may be substituted (monosubstituted or polysubstituted) or unsubstituted. In one embodiment, the alicyclyl group is a 6- to 12-membered cyclic system consisting of carbon atoms and optionally containing one or two double bonds.

[0033] The term "cycloalkyl" designates a saturated monocyclic or polycyclic alkyl group that may be substituted (monosubstituted or polysubstituted) or unsubstituted. The cycloalkyl group has from 3 to 24, preferably from 3 to 16, more preferably from 3 to 14, even more preferably from 3 to 12, but still more preferably 3, 4, 5, or 6 carbon atoms. The cycloalkyl group is linked to the rest of the molecule by a single bond. Cycloalkyl groups include, for example, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, methyl cyclohexyl, dimethyl cyclohexyl, octahydroindene, decahydronaphthalene, dodecahydrophenene, and the like.

[0034] The term "cycloalkenyl" designates a non-aromatic monocyclic or polycyclic alkenyl group that may be substituted (monosubstituted or polysubstituted) or unsubstituted. The cycloalkenyl group has from 5 to 24, preferably from 5 to 16, more preferably from 5 to 14, even more preferably from 5 to 12, but still more preferably 5 or 6 carbon atoms. The cycloalkenyl group is linked to the rest of the molecule by a single bond. Preferably, the cycloalkenyl group contains 1, 2, or 3 carbon-carbon double bonds. If more than one carbon-carbon double bond is present, the double bonds may be conjugated or nonconjugated. Cycloalkenyl groups include, for example, but are not limited to, the cyclopent-1-en-l-yl group and similar groups.

[0035] The term "cycloalkynyl" designates a non-aromatic monocyclic or polycyclic alkynyl group that may be substituted (monosubstituted or polysubstituted) or unsubstituted. The cycloalkynyl group has from 8 to 24, preferably from 8 to 16, more preferably from 8 to 14, even more preferably from 8 to 12, but still more preferably 8 or 9 carbon atoms and is linked to the rest of the molecule by a single bond. Preferably, the cycloalkynyl group contains 1, 2, or 3 carbon-carbon triple bonds, conjugated or nonconjugated. Cycloalkynyl groups include, for example, but are not limited to, the cyclooct-2-yn-l-yl group and similar groups. Cycloalkynyl groups may also contain one or more carbon-carbon double bonds, including, for example but not limited to, the cyclooct-4-en-2-ynyl group and similar ones.

[0036] As used herein, the term "heterocyclyl" or "heterocyclic" designates a hydrocarbon cyclic system of 3 to 10 members, in which one or more of the atoms of the ring or rings is a heteroatom (i.e., is not a carbon atom). Thus, "heterocyclyl" or "heterocyclic" designates a cyclic group in which the ring atoms consist of carbon and one or more heteroatoms. To satisfy the valence, the heteroatom may be bonded to hydrogen or substituent groups. Preferably, 1, 2, or 3 of the ring carbon atoms are heteroatoms. Each heteroatom may be independently chosen from the group consisting of O, N, S, P, and B, or the group consisting of O, N, and S. The heterocyclyl group may be substituted (monosubstituted or polysubstituted) or unsubstituted. The heterocyclyl group may be a monocyclic, bicyclic, or tricyclic system, and the rings may, for example, be fused or linked by a single bond or a bonding group such as a methylene group or another alkylene group.The nitrogen, carbon, or sulfur atoms present in the heterocyclyl radical may optionally be oxidized, and the nitrogen atom may optionally be quaternized. The heterocyclyl radical may be unsaturated or partially or completely saturated. The heterocyclyl radical may be aliphatic or aromatic. In one embodiment, the heterocyclyl is aliphatic (also known as a heteroalicyclyl) and is a 3- to 10-membered cyclic system where the atoms of the ring(s) consist of carbon atoms and 1 to 4, or 1, 2, or 3 heteroatoms. In another embodiment, the heterocyclyl group is a 6- to 10-membered cyclic system where the atoms of the ring(s) consist of carbon atoms and 1 to 4 heteroatoms, and where the cyclic system optionally contains one or two double bonds.In one embodiment, the heterocyclyl is aromatic (also known as a heteroaryl) and is a 6- to 10-membered cyclic system where the ring or rings consist of carbon atoms and 1 to 4, or 1, 2, or 3 heteroatoms. The term heterocyclyl is preferred for a 5- or 6-membered ring. Examples of saturated heteroalicyclyl groups include dioxane, piperidine, piperazine, pyrrolidine, morpholine, and thiomorpholine. Examples of aromatic heterocyclyl groups include pyridine, pyrrole, furan, thiophene, benzofuran, imidazoline, quinoline, pyridazine, and naphthyridine.

[0037] The term "aryl group" refers to an aromatic group having from 6 to 30, preferably from 6 to 18, more preferably from 6 to 10, but even more preferably 6 or 10 carbon atoms. The aryl group may comprise 1, 2, 3, or 4 aromatic rings, which may be linked by a carbon-carbon bond or fused, and which includes, for example, but not limited to, phenyl, naphthyl, diphenyl, indenyl, phenanthryl, or antranyl, among others. The aryl group may be substituted (monosubstituted or polysubstituted) or unsubstituted.

[0038] The term "aralkyl group" refers to an alkyl group substituted by an aromatic group, comprising from 7 to 24 carbon atoms and including, for example, and without to limit ourselves to it, -(CH2)i_6-phenyl, -(CH2)i_6-(l-naphthyl), -(CH2)i_6-(2-naphthyl), -(CH2)i_6 -CH(phenyl)2 and similar.

[0039] The term "heteroarylalkyl" refers to an alkyl group substituted by a heteroaryl group (also known as an aromatic heterocyclic) as defined above, the alkyl group having from 1 to 6 carbon atoms and the heteroaryl group having from 2 to 24 carbon atoms and 1 to 3 heteroatoms. Heteroarylalkyl groups include, for example and without limitation, the -(CH2)i.6-imidazolyl, -(CH2)i_6-triazolyl, -(CH2)i_6-thienyl, -(CH2)i_6-furyl, -(CH2)i.6-pyrrolidinyl, and similar groups.

[0040] As is understood in this technical field, there may be a certain degree of substitution of the aforementioned groups. In particular, there may be substitution in any of the groups identified above when this is explicitly stated. The substituted groups (radicals) mentioned above are groups (or radicals) that are substituted in one or more available positions by one or more substituents. Preferably, the substitution takes place in position 1, 2, or 3, more preferably in position 1 or 2, but even more preferably in position 1.Suitable substituents include, for example, but not limited to: Ci-C4 alkyl; hydroxyl; Ci-C4 alkoxyl; amino; CrC4 amino alkyl; CrC4 carbonyloxyl; CrC4 oxycarbonyl; halogen such as fluoride, chlorine, bromine, and iodine; cyano; nitro; azide; Ci-C4 alkylsulfonyl; thiol; CrC4 alkylthio; aryloxy such as phenoxyl; -NRb(C=NRb)NRbRc in which Rbet and Rc are independently chosen from H, Ci-C4 alkyl, C2-C4 alkenyl, alkynyl, C3-Ci0 cycloalkyl, C6-C18 aryl, C7-Ci7 aralkyl, 3- to 10-membered heterocyclyl, or an amino group protecting group.

[0041] Preferably, in formula (I), Ri is selected from H, a polyethylene glycol-derived polymer of a molecular weight between 200 and 35000 Daltons and R5 -CO-, in which R5 is selected from CrC24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, C3-C24 cycloalkyl, C5-C24 cycloalkenyl, C8-C24 cycloalkynyl, C6-C30 aryl, C7-C24 aralkyl, a 3- to 10-membered heterocyclyl ring, and a heteroarylalkyl containing 2 to 24 carbon atoms and 1 to 3 heteroatoms, in which the alkyl group has 1 to 6 carbon atoms. In one embodiment, Ri is chosen from H and R5-CO-, in which R5 is chosen from CrCi8 alkyl, C2-C24 alkenyl, C3-C24 cycloalkyl or chosen from Ci-Ci6 alkyl, C2-Ci8 alkenyl, C3-C7 cycloalkyl.The R5-CO- group includes alkanoyl groups such as acetyl (CH3-CO-, abbreviated here as "Ac-"), myristoyl (CH3-(CH2)12-CO-, abbreviated here as "Myr-") and palmitoyl (CH3-(CH2)14-CO-, abbreviated here as "Palm-"). In one embodiment, Ri is selected from H and acetyl, tert-butanoyl, prenyl, . Hexanoyl, 2-methylhexanoyl, cyclohexane carboxyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, oleoyl, and linoleoyl. In one embodiment, Ri is selected from H and R5-CO-, wherein R5 is selected from CrCi6 alkyl or C2-Ci8 alkenyl. In another embodiment, RI is selected from H, acetyl, myristoyl, or palmitoyl.

[0042] Preferably in formula (I), R2 is selected from -NR3R4, -OR3, and -SR3, in which R3 and R4 are independently selected from H, a polyethylene glycol-derived polymer, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, C3-C24 cycloalkyl, C5-C24 cycloalkenyl, C8-C24 cycloalkynyl, C6-C30 aryl, C7-C24 aralkyl, a 3- to 10-membered heterocyclyl ring, and a heteroarylalkyl containing 2 to 24 carbon atoms and 1 to 3 heteroatoms, in which the alkyl group has 1 to 6 carbon atoms. Optionally, R3 and R4 can be joined by a saturated or unsaturated carbon-carbon bond, forming a ring with the nitrogen atom. In one embodiment, R2 is -NR3R4 or -OR3. In another embodiment, R3 and R4 are independently selected from H, a polyethylene glycol-derived polymer with a molecular weight between 200 and 35,000 Daltons, methyl, ethyl, hexyl, dodecyl, and hexadecyl.In one embodiment, R3 and R4 are independently selected from H and Ci-Ci6 alkyl groups. In another embodiment, R3 is H and R4 is selected from H and Ci-Ci6 alkyl groups, including methyl, ethyl, hexyl, dodecyl, and hexadecyl. According to one embodiment, R2 is selected from -NR3R4 and -OR3, in which R3 and R4 are independently selected from H and Ci-Ci6 alkyl groups. In another embodiment, R2 is selected from -OH, -NH2, and -NH4, where R4 is a Ci-Ci6 alkyl group. R4 may be a C6 alkyl group, i.e., -C6Hn, or a Ci6 alkyl group, i.e., -Ci6H33.

[0043] More preferably, Ri is chosen from H and R5-CO-, in which R5 is chosen from CrCi8 alkyl, C2-C24 alkenyl, and C3-C24 cycloalkyl; and R2 is -NR3R4 or -OR3 in which R3 and R4 are chosen independently from H and Ci-Ci6 alkyl. In one exemplary embodiment, R3 is H and R4 is chosen from H and C1-C16 alkyl; for example, R2 is chosen from -OH, -NH2, and -NHR4 where R4 is CrC16- alkyl.

[0044] Even more preferably, R1 is chosen from H and R5-CO-, in which R5 is chosen from a Ci-Ci6 alkyl or a C2-Ci8 alkenyl; and R2 is -NR3R4 or -OR3 in which R3 and R4 are independently chosen from H and a Ci-Ci6 alkyl. In one exemplary embodiment, R3 is H and R4 is chosen from H and a CrCi6 alkyl; for example, R2 is chosen from the group consisting of -OH, -NH2, and -NHR4 where R4 is a Ci-Ci6 alkyl.

[0045] Even more preferably, Ri is chosen from H and acetyl, tert-butanoyl, prenyl, hexanoyl, 2-methylhexanoyl, cyclohexane carboxyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, oleoyl, and linoleoyl; and R2 is -NR3R4 or -OR3, in which R3 and R4 are independently selected from H and C1-C16 alkyl groups. In one exemplary embodiment, R3 is H and R4 is selected from H and C1-C16 alkyl groups; for example, R2 is selected from -OH, -NH2, and -NHR4, where R4 is a C1-C16 alkyl group. 16-

[0046] Even more preferably, Ri is chosen from H, acetyl, myristoyl, or palmitoyl; and R2 is -NR3R4 or -OR3, in which R3 and I are chosen independently from H and Ci-Ci6 alkyl. In one exemplary embodiment, R3 is H and R4 is chosen from H and Ci-Ci6 alkyl; for example, R2 is chosen from the group consisting of -OH, -NH2, and -NHR, where R is Ci-Ci6 alkyl.

[0047] More preferably, the composition according to the present invention comprises a hexapeptide with the sequence Ac-Glu-Glu-Met-Gln-Arg-Arg-NH2, which is also referred to as acetyl hexapeptide-8.

[0048] Advantageously, the hexapeptide is present in the composition of the present invention in a quantity of dry matter ranging from 0.1 ppm to 100000 ppm, preferably from 0.1 ppm to 10000 ppm, more preferably from 1 ppm to 1000 ppm, even more preferably from 2 ppm to 500 ppm, most preferably from 5 ppm to 50 ppm relative to the total weight of the composition. Dipeptides

[0049] The composition of the present invention comprises at least one dipeptide.

[0050] For the purposes of the present invention, preferably, the dipeptide is chosen from those of formula (II):

[0051] in which • n represents 0, 1 or 2, • R1 and R4, independently of each other, represent H, alkyl in Ci-C6 optionally substituted, • R2 represents H or an optionally substituted Ci-C6 alkyl group, • R3 represents alkoxy in Ci-Ci2, alkylamino in Ci-Ci2, aryl-Ci-C6 -alkylamino optionally substituted, heteroaryl-Ci-C6-alkylamino optionally substituted, aryl-Ci-C6-alkoxy optionally substituted or heteroaryl-Ci-C6-alkoxy optionally substituted and • R6 represents H or amino acid.

[0052] in the form of racemates or pure enantiomers, as well as their salts.

[0053] The substituents of the optionally substituted alkyl residues and of the groups containing these residues are, for example, halogen, amino, guanidino, hydroxy, alkoxy in Ci-C6, alkylthio in Ci-C6, carboxy, carbamoyl, optionally substituted phenyl, optionally substituted benzyl, imidazolylmethyl, indolylmethyl and cyano.

[0054] The optionally substituted substituents of the aryl and heteroaryl groups are, for example, halogen, C6-alkyl, hydroxy, C6-alkoxy, C6-alkoxycarbonyl, CN, amino, C6-alkylamino, di-C6-alkylamino, aminocarbonyl, C6-alkylaminocarbonyl, di-C6-alkylaminocarbonyl, aminocarbonyl, C6-alkylaminocarbonyl, di-C6-C6-alkylaminocarbonyl, C6-alkylthio, C6-alkylsulfoxyl, C6-alkylsulfonyl, optionally substituted benzyl, optionally substituted phenyl, optionally substituted phenoxy, or optionally substituted phenyl, whereby the aforementioned aromatic rings may be substituted by 1 to 3 identical or different substituents selected from the group comprising halogen, cyano, C6-alkyl, alkoxy in Ci-C6, hydroxy, amino, alkylamino in Ci-C6, di-Ci-C6-alkylamino and alkoxycarbonyl in CrC 6-

[0055] By "halogen" is meant fluorine, chlorine, bromine and iodine, with fluorine and chlorine being preferred.

[0056] Preferably in formula (II), R1 represents H, R2 represents H or methyl, R3 represents phenyl-Ci-C6-alkylamino and n represents 0 or 1, R4 represents H or alkyl in Ci-C4, R6 represents H or amino.

[0057] More preferably, the composition according to the present invention comprises a dipeptide with the sequence H-Beta-Ala-Pro-Dab-NH-Bzl, which is also referred to as dipeptide diaminobutyroyl benzylamide diacetate.

[0058] Advantageously, the dipeptide is present in the composition of the present invention in an amount ranging from 0.5 ppm to 200000 ppm, preferably from 0.5 ppm to 50000 ppm, preferably from 5 ppm to 5000 ppm, more preferably from 10 ppm to 1000 ppm, most preferably from 25 ppm to 100 ppm, relative to the total weight of the composition. Extract from Laminaria digitata

[0059] The composition of the present invention comprises an extract of Laminaria digitata.

[0060] Laminaria digitata is a large, dark brown, iodine- and sodium-rich seaweed. It is found in cold seas and oceans, particularly in the North Sea and the North Atlantic. It is found in abundance along the coasts of Great Britain and Ireland, Iceland, Russia, and Brittany.

[0061] The extract of Laminaria digitata is preferably obtained by water leaching, filtration and concentration by reverse osmosis.

[0062] As an example of commercial products of Laminaria digitata extract, one can cite those sold under the name PHYCOJUVENINE DIG ALG147 by the company CODIF.

[0063] Advantageously, the extract of Laminaria digitata is present in the composition of the present invention in an amount ranging from 0.0001% by weight to 20% by weight, preferably from 0.0001% by weight to 5% by weight, more preferably from 0.001% by weight to 0.1% by weight, even more preferably from 0.002% by weight to 0.05% by weight, most preferably from 0.005% by weight to 0.02% by weight, relative to the total weight of the composition. Polyhydroxy acids

[0064] The composition according to the present invention comprises at least one polyhydroxy acid.

[0065] The term "polyhydroxy acid" here refers to an organic compound having at least one carboxyl group and a plurality of hydroxyl groups. The number of carboxyl groups in the polyhydroxy acid is not limited, but one or two carboxyl groups are preferable, and a single carboxyl group is even more preferable. The number of hydroxyl groups in the polyhydroxy acid is also not limited, but 2 to 10 are preferable, and 2 to 6 are even more preferable. The number of carbon atoms in the polyhydroxy acid is not limited, but 3 to 11 are preferable, and 3 to 8 are even more preferable.

[0066] The above organic compound may be aliphatic or aromatic. In other words, the polyhydroxy acid may be chosen from aliphatic and aromatic polyhydroxy acids. Preferably, the aliphatic polyhydroxy acid may be chosen from sugar acids.

[0067] Examples of polyhydroxy acids include dihydroxypropanoic acid such as glyceric acid; trihydroxybutanoic acid such as erythronic acid and threonic acid; tetrahydroxypentanoic acid such as ribonic acid, arabinoic acid, xylonic acid and lyxonic acid; pentahydroxyhexanoic acid such as allonic acid, altronic acid, gluconic acid, mannoic acid, gulonic acid, idonic acid, galactonic acid and talonic acid; hexahydroxyheptanoic acid such as glucoheptanoic acid, galactoheptonic acid; tartaric acid; lactobionic acid, maltobionic acid and mixtures thereof.

[0068] It is preferable for the polyhydroxy acid to be in the form of a lactone. The lactone ring of the polyhydroxy acid in the form of a lactone can be saturated. Examples of polyhydroxy acids include gluconolactone, ribonolactone, and mixtures thereof.

[0069] Preferably, the polyhydroxy acid is chosen from lactones with 2 to 6 hydroxyl groups.

[0070] Advantageously, the polyhydroxyacid is chosen from lactones with 2 to 6 hydroxyl groups and 3 to 8 carbon atoms.

[0071] It is more preferable that the polyhydroxy acid be gluconolactone, which corresponds to the following structure.

[0072] Advantageously, the protein is present in the composition of the present invention in an amount ranging from 0.5% by weight to 20% by weight, preferably from 1% by weight to 15% by weight, more preferably from 2% by weight to 10% by weight, even more preferably from 3% by weight to 8% by weight, relative to the total weight of the composition. Nicotinamide and / or its derivatives

[0073] Preferably, the composition of the present invention comprises nicotinamide and / or one of its derivatives.

[0074] Nicotinamide, also known as vitamin B3, is a compound with the following formula:

[0075] 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 nicotinamide by substitution of the H of -CONH2, products from a reaction with carboxylic acids and amino acids, esters of nicotinyl alcohol and carboxylic acids such as acetic acid, salicylic acid, glycolic acid or palmitic acid.

[0076] Other 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.

[0077] Advantageously, nicotinamide and / or one of its derivatives is present in the composition of the present invention in an amount ranging from 0.5% to 20% by weight, preferably from 1% to 15% by weight, more preferably from 2% to 10% by weight, even more preferably from 3% to 8% by weight, relative to the total weight of the composition. Aqueous phase

[0078] The composition of the present invention may include an aqueous phase.

[0079] Preferably, the aqueous phase comprises water.

[0080] Advantageously, water is present in the composition of the present invention in an amount ranging from 50% by weight to 99.99% by weight, preferably from 70% by weight to 99.99% by weight, more preferably from 80% by weight to 99.6% by weight, relative to the total weight of the composition.

[0081] Optionally, the aqueous phase comprises an organic solvent miscible with water (at room temperature at 25 °C) selected from monoalcohols, glycols and polyols having from 2 to 20 carbon atoms, such as octyldodecanol, glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; and mixtures thereof.

[0082] Advantageously, the aqueous phase is present in the composition of the present invention in an amount ranging from 60% by weight to 99.99% by weight, preferably from 70% by weight to 99.99% by weight, more preferably from 80% by weight to 99.6% by weight, relative to the total weight of the composition. Additional cosmetic active ingredients

[0083] The composition of the present invention may include an additional cosmetic active ingredient in addition to the cosmetic active ingredients as defined above.

[0084] A person skilled in the art can adjust the type and quantity of additional cosmetic active ingredients according to the end use of the composition according to the present invention. Additional adjuvants or additives

[0085] The composition of the present invention may also include conventional cosmetic adjuvants or additives, for example, perfumes, chelating agents, preservatives and bactericides, surfactants, thickeners, pH regulators, and mixtures thereof.

[0086] A person skilled in the art can choose the quantity 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.

[0087] According to a particularly preferred embodiment, the present invention proposes a composition comprising, relative to the total weight of the composition: i. from 2 ppm to 500 ppm of acetyl hexapeptide-8; ii. from 10 ppm to 1000 ppm of dipeptide diaminobutyroyl benzylamide diacetate; iii. from 0.002% by weight to 0.05% by weight of Laminaria digitata extract; iv. from 2% by weight to 10% by weight of gluconolactone; and v. optionally, from 2% by weight to 10% by weight of nicotinamide.

[0088] According to a preferred embodiment, the present invention proposes a composition comprising, relative to the total weight of the composition: i. 5 ppm to 50 ppm of acetyl hexapeptide-8; ii. 25 ppm to 100 ppm of dipeptide diaminobutyroyl benzylamide diacetate; iii. 0.005 wt% to 0.02 wt% of Laminaria digitata extract; iv. from 3% by weight to 8% by weight of gluconolactone; and v. optionally, from 3% by weight to 8% by weight of nicotinamide. pharmaceutical form and process

[0089] The composition of the present invention is in the form of an emulsion, a cream, a lotion or a hydrogel, and can be used as a toner, a lotion, a light cream, a nourishing cream, a night mask or an eye cream.

[0090] The composition of the present invention can be used for the care of keratinous materials. In particular, the composition of the present invention can provide benefits for skin radiance, forehead wrinkles, fine lines in the nasolabial area, and ptosis of the lower part of the face.

[0091] According to the second aspect, the present invention proposes a non-therapeutic method for the care of keratinous materials, comprising the application of the composition according to the first aspect of the present invention to the keratinous materials.

[0092] In certain embodiments, the present invention proposes a non-therapeutic anti-aging process for keratinous materials, comprising the application of the composition according to the first aspect of the present invention on keratinous materials.

[0093] In particular, keratinous material is the skin, especially facial skin.

[0094] In a third aspect, the present invention proposes a use of the composition according to the first aspect of the present invention to provide an anti-aging effect on keratinous materials.

[0095] In particular, keratinous material is the skin, especially facial skin. EXAMPLES

[0096] The following examples are given by way of non-limiting illustrations of the present invention.

[0097] The main raw materials used, their trade names and suppliers are listed in Table 1.

[0098] [Table 1]

[0099] [Tables 1] INCI name Trade name Supplier Acetyl hexapeptide-8 ARGIRELINE AMPLIFIED P EPTIDE SOLUTION LIPOTEC Dipeptide diaminobutyroyl benzylamide diacetate SYN-AKE DSM NUTRITIONA L PRODUCTS Gluconolactone GLUCONO-DELTA-LACTO NE F5010 PERSONAL CAR JUNGBUNZLAUER Niacinamide NIACINAMIDE PC (CODE 5 016013) DSM NUTRITIONAL PRODUCTS Laminaria digitata extract PHYCOJUVENINE DIG ALG 147 CODIF

[0100] Inventive examples 1 and 2 and comparative examples 1 to 4

[0101] Compositions of Inventive Examples (EI) 1 and 2 and Comparative Examples (CE) 1 to 4 were prepared on the basis of the quantities of ingredients given in Table 2. The quantities are given in weight of each active ingredient relative to the total weight of the composition.

[0102] [Table 2]

[0103] [Tables2] Components El. 1 DI 2 EC. 1 EC. 2 EC. 3 EC. 4 Acetyl hexapeptide-8 (ppm) 10 10 10 10 10 10 Dipeptide diaminobutyroyl b enzylamide diacetate (ppm) 50 50 50 50 50 50 Laminaria digitata extract (%) 0.01 0.01 0.01 0.01 - - Nicotinamide (%) 5 - 5 - 5 - Gluconolactone (%) 5 5 - - - 5 Water (%) QS100 QS100 QS100 QS100 QS100 QS100

[0104] The compositions of Inventive Examples 1 and 2 represent compositions according to the present invention.

[0105] The compositions of Comparative Examples 1 and 2 do not include at least one polyhydroxy acid.

[0106] The composition of Comparative Example 3 does not include Laminaria digitata extract and at least one polyhydroxy acid.

[0107] The composition of Comparative Example 4 does not include an extract of Laminaria digitata.

[0108] Preparation process:

[0109] The compositions listed above were prepared as follows: adding acetyl hexapeptide-8, dipeptide diaminobutyroyl benzylamide diacetate, Laminaria digitata extract (where applicable), nicotinamide (where applicable) and gluconolactone (where applicable) slowly into water with stirring at room temperature to obtain a homogeneous mixture. Assessment

[0110] The effect of the above-prepared compositions on the production of collagen IV was tested as follows. 1. Cell inoculation:

[0111] The fibroblasts were revived, and when the pose rate reached approximately 60%, the cells were seeded into 6-well plates and cultured overnight in an incubator with CO2 (37°C, 5% CO2). 1. Preparing the solution:

[0112] The working solutions were prepared according to the test groups listed in Table 3.

[0113] [Table 3]

[0114] [Tableaux3] Sample Groups Indicator Testing Methods Blank control (BC) / Collagen IV + Immunofluorescence Negative control (NC) / Positive control (PC) VC +VE Test samples Compositions of Inventive Examples 1 and 2 and Comparative Examples 1 to 4

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] 1. Administration: The groups were administered according to Table 3. Culture medium was added to each well for the blank control group and the negative control group. The same volume of culture medium containing VE and VC was added to each well for the positive control group. The same volume of culture solution containing the corresponding concentration of active ingredients in the culture medium was added to each well for the test sample groups. 1. UVA irradiation: all groups except the blank control group were subjected to UVA irradiation. After irradiation, they were placed in an incubator with CO2 (37 °C, 5% CO2) for subsequent culture. 2. Immunofluorescence detection and gene expression detection were performed. The rate of improvement and the rate of over-regulation were calculated according to the following equations: Improvement rate (%) = (test group - NC group) / NC group * 100% The statistical analysis was conducted using the t-test method; with respect to the BC group, significance is represented by #, the value p<0.05 is represented by #, the value p<0.01 is represented by ##; with respect to the NC group, significance is represented by *, the value p<0.05 is represented by *, and the value p<0.01 is represented by **. The PCR data for collagen IV have been summarized in Table 4. [Table 4] [Tables 4] Mean AND P-value Improvement Rate (%) BC 1.00 0.10 / / NC 0.34 0.02 0.000## / PC 0.95 0.05 0.000** 179.41 Composition of El. 1 1.12 0.04 0.000** 229.41 Composition of El. 2 1.07 0.13 0.001** 214.71 Composition of EC. 1 0.86 0.08 0.000** 152.94 Composition of EC. 2 0.83 0.03 0.000** 144.12 Composition of EC. 3 0.79 0.05 0.000** 132.35 Composition of EC. 4 0.89 0.03 0.000** 161.76

[0122] It can be seen from Table 4 that the composition of Inventive Example 1 has a better stimulating effect on the production of collagen IV compared to the compositions of Comparative Examples 1 and 3.

[0123] It can also be seen from Table 4 that the composition of Inventive Example 2 has a better stimulating effect on the production of collagen IV compared to the compositions of Comparative Examples 2 and 4.

Claims

Demands

1. Composition comprising: (i) at least one hexapeptide; (ii) at least one dipeptide; (iii) Laminaria digitata extract; and (iv) at least one polyhydroxy acid.

2. Composition according to claim 1, wherein the hexapeptide is selected from those of formula (I): Ri-Glu-Glu-Met-Gln-Arg-Arg-R2(I) in which Ri is selected from H, a polyethylene glycol-derived polymer, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl, aralkyl and R5-CO-, in which R5 is selected from H, a non-cyclic aliphatic group, alicyclyl, aryl, aralkyl, heterocyclyl and heteroarylalkyl; R2 is selected from the group consisting of -NR3R4, -OR3, -SR3, in which R3 and R4 are selected independently from H, a polyethylene glycol-derived polymer, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl and aralkyl; and Ri and R2 are not amino acids.

3. Composition according to any one of claims 1 and 2, wherein the hexapeptide is present in a dry matter amount from 0.1 ppm to 100000 ppm, preferably from 0.1 ppm to 10000 ppm, more preferably from 1 ppm to 1000 ppm, even more preferably from 2 ppm to 500 ppm, most preferably from 5 ppm to 50 ppm relative to the total weight of the composition.

4. Composition according to any one of claims 1 to 3, wherein the dipeptide is selected from those of formula (II): n H (II) H ff* RL ï R" ZN / f C 0 A.........7 in which - n represents 0, 1 or 2, - R1 and R4, independently of each other, represent H, optionally substituted Ci-C6 alkyl, - R2 represents H or optionally substituted Ci-C6 alkyl, - R3 represents C1-C12 alkoxy, C1-C12 alkylamino, optionally substituted aryl-Ci-C6-alkylamino, optionally substituted heteroaryl-Ci-C6-alkylamino, optionally substituted aryl-Ci-C6-alkoxy or optionally substituted heteroaryl-Ci-C6-alkoxy and - R6 represents H or amino, in the form of racemates or pure enantiomers, as well as their salts.

5. Composition according to any one of claims 1 to 4, wherein the polyhydroxy acid is selected from aliphatic polyhydroxy acids and aromatic polyhydroxy acids, preferably selected from lactones with 2 to 6 hydroxyl groups and 3 to 8 carbon atoms, more preferably, the polyhydroxy acid is gluconolactone.

6. Composition according to any one of claims 1 to 5 wherein the polyhydroxyacid is present in an amount from 0.5% by weight to 20% by weight, preferably from 1% by weight to 15% by weight, more preferably from 2% by weight to 10% by weight, even more preferably from 3% by weight to 8% by weight, relative to the total weight of the composition.

7. Composition according to any one of claims 1 to 6, further comprising nicotinamide and / or a derivative thereof, wherein the nicotinamide derivative is selected from 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, niaprazine, methyl nicotinate, sodium nicotinate and mixtures thereof; Preferably, said nicotinamide and / or one of its derivatives is present in an amount ranging from 0.5% by weight to 20% by weight, preferably from 1% by weight to 15% by weight, more preferably from 2% by weight to 10% by weight. weight, even more preferably from 3% by weight to 8% by weight, relative to the total weight of the composition.

8. The composition according to claim 1, comprising, by weight of the total composition: (i) 5 ppm to 50 ppm acetyl hexapeptide-8; (ii) 25 ppm to 100 ppm dipeptide diaminobutyroyl benzylamide diacetate; (iii) 0.005 wt% to 0.02 wt% Laminaria digitata extract; (iv) 3 wt% to 8 wt% gluconolactone; and (v) optionally, 3 wt% to 8 wt% nicotinamide

9. Non-therapeutic method for the treatment of keratinous materials, comprising the application of the composition according to any one of claims 1 to 8 on keratinous materials.

10. Use of the composition according to any one of claims 1 to 8 to provide an anti-aging effect to keratinous materials.